Porn Videos
Katja Kassin & Alan Stafford in My First Sex Teacher
After class, Alan casually walks up to Professor Katja Kassin and asks her to attend a gallery opening with him. The...
Who: Teacher
Categories: Anal, Big Ass, Big Tits, Blow Job, Cum on Ass, Fake Tits, Foreign Accent, High Heels, Mature, Piercings, Red Head, Shaved, Stockings, Tattoos
Released: January 17, 2012
Julia Ann & Ethan Hunt in My First Sex Teacher
Ethan Hunt has a hot date tonight with whom he's supposed to get to second base, but he doesn't even know what first...
Who: Professor
Categories: Ass licking, Ball licking, Big Ass, Big Dick, Big Fake Tits, Big Tits, Blonde, Blow Job, Curvy, Deepthroating, Facial, Fake Tits, High Heels, Interracial, Mature, Shaved, Stockings, Swallowing, Tattoos
Released: January 13, 2012
Jenla Moore & Kris Slater in My First Sex Teacher
Professor Jenla Moore has a sit-down with her student Kris because there's a problem … he keeps making sexual...
Who: Teacher
Categories: Ass smacking, Ball licking, Big Tits, Blow Job, Brunette, Facial, Fake Tits, Mature, MILFs, Petite, Shaved
Released: January 11, 2012
Ariella Ferrera & Johnny Castle in My First Sex Teacher
Professor Ariella Ferrera is having a bad week. She's trying to grade Johnny's test, but her pen ran out of ink, her...
Categories: 69, Ass licking, Ball licking, Big Dick, Big Fake Tits, Big Tits, Blonde, Brunette, Cum on Tits, Facial, Fake Tits, Glasses, Hairy Pussy, Masturbation, Mature, MILFs, Stockings, Titty Fucking
Released: January 06, 2012
Nikki Sexx & Danny Wylde in My First Sex Teacher
Danny notices that his teacher, Professor Nikki Sexx, has had low energy the entire week, so he confronts her about...
Who: Professor
Categories: Ass smacking, Ball licking, Big Ass, Big Dick, Big Fake Tits, Big Tits, Blonde, Blow Job, Deepthroating, Facial, Fake Tits, Glasses, Hairy Pussy, High Heels, Mature, Piercings, Stockings
Released: December 30, 2011
Carolyn Reese & Kris Slater in My First Sex Teacher
Kris Slater is sneaking around Professor Carolyn Reese's classroom because he wants to take pictures of test answers...
Who: Bad Girl, Professor, Teacher
Categories: Ball licking, Big Ass, Big Tits, Blonde, Blow Job, Facial, High Heels, Mature, MILFs, Shaved, Tattoos, Titty Fucking
Released: December 16, 2011
Diana Prince & Dane Cross in My First Sex Teacher
Professor Diana Prince is holding a poetry contest for her English class, and Dane is so inspired that he writes her...
Who: Professor
Categories: Big Tits, Blow Job, Brunette, Facial, Fake Tits, Glasses, High Heels, Mature, Shaved, Stockings
Released: December 05, 2011
Anita Blue & Johnny Castle in My First Sex Teacher
Professor Anita Blue spends time with Johnny, tutoring him after class so he can do well on his business test. After...
Categories: Ass licking, Big Ass, Big Fake Tits, Big Tits, Blonde, Curvy, Deepthroating, Facial, Glasses, High Heels, Mature, Stockings, Tattoos
Released: November 30, 2011
Jada Fire & Michael Vegas in My First Sex Teacher
Professor Jada Fire is surprised to see her student Michael pop in her classroom when nobody is around. But she's not...
Who: Professor
Categories: Big Ass, Big Tits, Black, Black Hair, Blow Job, Fake Tits, High Heels, Piercings, Stockings, Tattoos
Released: November 28, 2011
Lyla Storm & Kris Slater in My First Sex Teacher
Professor Lyla Storm is leaving her job for a tenure-track position at another school in Delaware, but when her best...
Who: Bad Girl, Friend, Teacher
Categories: Blow Job, Brunette, Deepthroating, Facial, Natural Tits, Shaved, Small Tits
Released: November 24, 2011
Taylor Wane & Alan Stafford in My First Sex Teacher
Professor Taylor Wane has received word from the dean that some of her students are complaining she's inappropriate...
Categories: Ass licking, Big Ass, Big Tits, Blonde, Facial, Foreign Accent, Glasses, High Heels, Lingerie, Mature, Shaved, Stockings
Released: November 21, 2011
Nyomi Banxxx & Kris Slater in My First Sex Teacher
Professor Nyomi Banxxx keeps her student Kris after class, but not because he's flunking her course. He's her top...
Categories: Ass smacking, Big Ass, Big Fake Tits, Big Tits, Black, Black Hair, Blow Job, Cum on Tits, Deepthroating, Fake Tits, High Heels, Shaved, Stockings, Tattoos
Released: November 14, 2011
Eva Karera & Bruce Venture in My First Sex Teacher
Professor Eva Karera has Bruce come in during office hours because he's not doing well in her French class. She says...
Categories: Big Dick, Big Fake Tits, Black Hair, Blow Job, Facial, Fake Tits, Foreign Accent, High Heels, Mature, Stockings, Tattoos
Released: November 07, 2011
Francesca Le & Seth Gamble in My First Sex Teacher
Professor Francesca Le´is working late grading papers and is surprised when she sees her student Seth walk into her...
Who: Bad Girl, Stripper, Teacher
Categories: 69, Ball licking, Big Ass, Big Fake Tits, Big Tits, Brunette, Deepthroating, Facial, Fake Tits, Hairy Pussy, Latina, Mature, MILFs, Petite, Piercings, Stockings, Swallowing, Tattoos, Titty Fucking
Released: November 04, 2011
Lacie James & Danny Wylde in My First Sex Teacher
Danny is studying for his test, but he never knew how complicated the female anatomy could be. His smoking hot...
Categories: Ass smacking, Big Ass, Big Dick, Big Fake Tits, Big Tits, Black Hair, Blow Job, Cum on Tits, Facial, Fake Tits, Glasses, High Heels, Mature, MILFs, Piercings, Shaved, Stockings, Tattoos, Titty Fucking
Released: October 31, 2011
Janet Mason & Daniel Hunter in My First Sex Teacher
Janet is a college counselor/tutor that helps students get back on track when their performance begins to drop. She...
Where: Couch, Living room
Categories: Big Tits, Blow Job, Facial, Fake Tits, Hand Job, Mature, MILFs, Red Head, Shaved, Stockings
Released: October 24, 2011
Serena Marcus & Giovanni Francesco in My First Sex Teacher
Professor Marcus returns to her classroom to find Giovanni passed out on her classroom floor from studying so hard...
Who: Teacher
Categories: Big Ass, Big Tits, Blonde, Blow Job, Cum on Ass, Curvy, Deepthroating, Fake Tits, Glasses, Piercings, Shaved, Tattoos
Released: October 20, 2011
Charlee Chase & Daniel Hunter in My First Sex Teacher
Daniel was called into Miss Chase office because Daniel and his friends were acting inappropriate around the college...
Who: Teacher
Categories: Big Tits, Blonde, Blow Job, Cum on Tits, Deepthroating, Facial, Fake Tits, Glasses, High Heels, Shaved, Tattoos, Titty Fucking
Released: October 17, 2011
Dee Siren & Johnny Castle in My First Sex Teacher
Ms. Siren has bad news for Johnny, he failed the test. Johnny knows this will bring down his GPA and might hurt him...
Categories: Ass smacking, Ball licking, Big Tits, Blonde, Blow Job, Facial, Foot Fetish, Glasses, Hand Job, Lingerie, Natural Tits, Shaved, Stockings, Titty Fucking
Released: October 12, 2011
Brandi Love & Bruce Venture in My First Sex Teacher
Bruce is shocked to learn the news that Ms. Love has been recently fired. Ms. Love knows it was his big mouth that...
Categories: Ass smacking, Big Dick, Big Tits, Blonde, Blow Job, Deepthroating, Facial, Fake Tits, Hand Job, Mature, Stockings, Swallowing, Tattoos
Released: October 03, 2011
Diana Doll & Johnny Castle in My First Sex Teacher
Johnny meets with Diana, the dean of his school, to see if she can help him get into a class, but before that, she...
Categories: Ass licking, Ball licking, Big Tits, Blonde, Blow Job, Deepthroating, Facial, Fake Tits, Foot Fetish, Foreign Accent, Glasses, High Heels, Mature, MILFs, Natural Tits, Petite, Stockings, Tattoos
Released: September 28, 2011
Veronica Avluv & Danny Wylde in My First Sex Teacher
Ms. Avluv is appauled at the lack of studying that jock, Danny, is doing. She doesn't understand how he's passing any...
Categories: Ass smacking, Big Tits, Blow Job, Brunette, Deepthroating, Facial, Fake Tits, Glasses, Hand Job, High Heels, Mature, Shaved, Squirting, Stockings
Released: September 26, 2011
Shyla Stylez & Daniel Hunter in My First Sex Teacher
Professor Shyla speaks with Daniel after class to discuss his poor work performance. Shyla can turn his F into an A+...
Categories: Titty Fucking
Released: September 16, 2011
Tara Holiday & Johnny Castle in My First Sex Teacher
Johnny was planning on dropping Ms. Holiday's Chilean Studies class to explore the Brazilian culture instead, but...
Categories: Ass licking, Ass smacking, Ball licking, Big Tits, Blow Job, Brunette, Facial, Fake Tits, Foot Fetish, Latina, Mature, MILFs, Shaved, Stockings, Tattoos
Released: September 14, 2011
Diamond Jackson & Kris Slater in My First Sex Teacher
Ms. Jackson steps out of the room for a quick second & Kris, the class clown, decides to write what he really likes...
Categories: Ball licking, Big Tits, Black, Black Hair, Blow Job, Cum on Glasses, Deepthroating, Facial, Fake Tits, Glasses, High Heels, Interracial, Piercings, Shaved, Stockings
Released: September 08, 2011
Darla Crane & David Loso in My First Sex Teacher
Ms. Crane meets with David because he is falling behind in class. It turns out his class performance is dropping...
Who: Teacher
Categories: Big Tits, Blonde, Blow Job, Dominant, Facial, Fake Tits, Mature, MILFs, Shaved, Tattoos, Titty Fucking
Released: September 05, 2011
Angela Attison & Kris Slater in My First Sex Teacher
Kris has a big audition coming up so he goes to his drama professor, Ms. Attison, to help him out. It's a love scene...
Categories: Ass smacking, Big Tits, Blonde, Blow Job, Facial, Fake Tits, Hand Job, High Heels, Shaved
Released: September 01, 2011
Emma Starr & Giovanni Francesco in My First Sex Teacher
Professor Starr holds Gio after class and tells him that he seemed distracted during the day's session. He tells her...
Categories: Big Tits, Blonde, Blow Job, Cum on Tits, Fake Tits, Glasses, High Heels, Mature, Shaved, Stockings, Tattoos
Released: August 26, 2011
Jessica Jaymes, Tiffany Brookes & Johnny Castle in My First Sex Teacher
Johnny and Tiffany were ordered to Ms. Jaymes's Saturday detention session because, according to her, the principal...
Who: Professor, Student, Teacher
Categories: 69, Ass licking, Ass smacking, Ball licking, Big Tits, Blow Job, Brunette, Facial, Fake Tits, High Heels, Mature, Natural Tits, Piercings, Shaved, Tattoos, Threesome BGG
Released: August 22, 2011
Evita Pozzi & Danny Wylde in My First Sex Teacher
Danny is going on vacation to Italy but before he goes, he wants to learn the Italian language. Danny has heard Italy...
Who: Bad Girl, Stranger, Teacher
Categories: Big Dick, Big Tits, Blonde, Blow Job, Cum on Tits, Fake Tits, Foreign Accent, Mature, MILFs, Shaved, Tattoos, Titty Fucking
Released: August 15, 2011
India Summer & Ryan Blaze in My First Sex Teacher
Professor Summer calls Ryan into her classroom during after-hours to explain to him why he got an F- on his paper....
Where: Desk
Categories: Big Ass, Blow Job, Brunette, Deepthroating, Facial, Glasses, Hairy Pussy, High Heels, Mature, Natural Tits, Small Tits, Tattoos
Released: August 11, 2011
Shay Sights & Bill Bailey in My First Sex Teacher
Professor Sights calls Bill into her classroom after hours and tells him that he's not doing so well in her course....
Categories: Big Dick, Big Tits, Black Hair, Blow Job, Deepthroating, Facial, Fake Tits, Hand Job, Lingerie, Mature, Shaved, Stockings, Tattoos, Titty Fucking
Released: August 05, 2011
Karen Kougar & Tim Cannon in My First Sex Teacher
Tim's taking guitar lessons from Karen, and based on her reaction, he has improved quite a bit. According to Karen,...
Where: Couch, Living room
Categories: Big Tits, Blow Job, Brunette, Cum on Tits, Deepthroating, Fake Tits, Glasses, High Heels, Mature, Stockings
Released: July 27, 2011
Lezley Zen & Johnny Castle in My First Sex Teacher
Professor Zen is investigating the egging of her car, which she thinks was done by her student, Johnny. He tells her...
Categories: Ass licking, Ass smacking, Ball licking, Big Tits, Blow Job, Brunette, Facial, Fake Tits, Hand Job, High Heels, Mature, Piercings, Tattoos, Titty Fucking
Released: July 18, 2011
Karen Fisher & Danny Wylde in My First Sex Teacher
Professor Fisher is leaving her post as the Cultural Anthropology professor and wants to have a little fun with her...
Who: Friend, Professor, Teacher
Where: Couch, Living room
Categories: Ass smacking, Big Ass, Big Tits, Blonde, Blow Job, Curvy, Deepthroating, Facial, Fake Tits, Glasses, High Heels, Lingerie, Mature, Stockings, Titty Fucking, Voluptuous
Released: July 06, 2011
Lya Pink & Tim Cannon in My First Sex Teacher
Tim is nothing but a spoiled rich kid and he’s not sure why learning from books will teach him anything because all...
Where: Couch, Floor, Living room
Categories: Big Dick, Big Tits, Blow Job, Cum on Tits, Deepthroating, Glasses, High Heels, Mature, MILFs, Natural Tits, Piercings, Red Head, Shaved, Tattoos
Released: June 29, 2011
Zoey Holloway & Johnny Castle in My First Sex Teacher
Johnny's teacher Ms. Holloway left her job and he's helping her bring her books home. She tells him she'll be...
Where: Couch, Living room
Categories: Ass licking, Ass smacking, Ball licking, Big Dick, Big Tits, Black Hair, Blow Job, Deepthroating, Dominant, Facial, Fake Tits, High Heels, Mature, MILFs, Squirting, Tattoos
Released: June 13, 2011
Tyler Faith & Johnny Castle in My First Sex Teacher
Johnny was able to repair Ms. Faith's hard drive over the weekend, and he brings it into her while she's grading...
Who: Friend, Professor, Teacher
Categories: Ass licking, Ass smacking, Big Tits, Blonde, Blow Job, Facial, Fake Tits, High Heels, Mature, Shaved, Tattoos, Titty Fucking
Released: May 23, 2011
Alia Janine & Kris Slater in My First Sex Teacher
Kris stops in to see his new college counselor because he wants to change his courses. He tells her that he wants to...
Who: Counselor, School Faculty (other than professor)
Categories: Ass licking, Ball licking, Big Tits, Black Hair, Blow Job, Cum on Tits, Deepthroating, Dominant, Facial, Hand Job, High Heels, Natural Tits, Piercings, Tattoos, Titty Fucking
Released: May 16, 2011
Diamond Foxxx & Kris Slater in My First Sex Teacher
Professor Foxxx excuses everybody from class, except for Kris. She keeps him behind and tells him that she's heard...
Categories: Ass licking, Ass smacking, Big Ass, Big Tits, Blow Job, Brunette, Deepthroating, Facial, Fake Tits, High Heels, Mature, Shaved, Stockings
Released: May 06, 2011
Tanya Tate & Anthony Rosano in My First Sex Teacher
Anthony returns to the states from his anthropology trip and shows Professor Tate some of the artifacts he collected,...
Categories: Ass licking, Ball licking, Big Dick, Big Tits, Blonde, Blow Job, Deepthroating, Facial, Fake Tits, Foot Fetish, Foreign Accent, High Heels, Lingerie, Mature, MILFs, Piercings, Shaved, Stockings, Swallowing, Tattoos, Titty Fucking
Released: April 29, 2011
Brittany O'Neil & Xander Corvus in My First Sex Teacher
Xander is taking his semester exam and clearly isn't very concerned about it. It seems this class is not one of...
Categories: Ass smacking, Ball licking, Big Ass, Big Dick, Big Tits, Blonde, Blow Job, Cum on Tits, Curvy, Facial, Fake Tits, Glasses, Hand Job, Lingerie, Mature, Stockings, Titty Fucking, Voluptuous
Released: April 28, 2011
Brandi Love & Xander Corvus in My First Sex Teacher
Xander comes into Prof. Love's classroom to find her groggy and sleepy. It seems her boyfriend kicked her out of her...
Who: Cougar, Professor, Teacher
Where: Chair, Classroom, Couch
Categories: Ass licking, Ass smacking, Big Ass, Big Tits, Blonde, Blow Job, Deepthroating, Facial, Fake Tits, Foot Fetish, High Heels, Mature, MILFs, Shaved, Tattoos
Released: April 26, 2011
Nicki Hunter & Xander Corvus in My First Sex Teacher
Freshman Xander is trying to get his college courses worked out, but he’s really struggling. The thing is that he...
Who: Bad Girl, Counselor, School Faculty (other than professor)
Categories: Ball licking, Big Tits, Blow Job, Cum on Tits, Deepthroating, Facial, High Heels, Lingerie, Piercings, Red Head, Shaved, Stockings, Titty Fucking
Released: April 14, 2011
Claudia Valentine & Will Powers in My First Sex Teacher
Will is on academic probation and he's worried he's going to lose his lacrosse scholarship, so he goes to see his...
Who: School Faculty (other than professor)
Categories: Ass smacking, Big Tits, Blow Job, Brunette, Deepthroating, Fake Tits, High Heels, Latina, Mature, Shaved, Swallowing, Tattoos
Released: April 11, 2011
Hunter Bryce & Bruce Venture in My First Sex Teacher
Bruce enters Prof. Bryce's class and just stands there waiting for her to acknowledge him. She is very preoccupied,...
Categories: Big Dick, Big Tits, Blow Job, Brunette, Deepthroating, Dominant, Facial, Fake Tits, Shaved, Squirting
Released: April 07, 2011
Shay Fox & Seth Gamble in My First Sex Teacher
Seth comes into Prof. Fox classroom and kisses her lightly on the lips. They are having an illicit affair, but its...
Who: Friend, Girlfriend, MILF, Professor
Categories: Ass smacking, Big Tits, Black Hair, Blow Job, Facial, Fake Tits, Glasses, Mature, MILFs, Piercings, Shaved, Stockings, Tattoos
Released: March 28, 2011
Taylor Wane & Xander Corvus in My First Sex Teacher
Professor Wane is having a party and is asks her party boy student to borrow a beer keg bur when Xander asks to be...
Where: Counter, Kitchen, Kitchen counter
Categories: Ball licking, Big Tits, Blonde, Blow Job, Deepthroating, Fake Tits, Glasses, High Heels, Mature, Shaved, Stockings
Released: March 21, 2011
Amber Lynn & Anthony Rosano in My First Sex Teacher
Amber expects Anthony to give her a good deal on her new floors because he used to be her student but times are rough...
Where: Couch, Living room
Categories: Ball licking, Big Tits, Blonde, Blow Job, Cum on Tits, Fake Tits, Hairy Pussy, Hand Job, High Heels, Mature, Titty Fucking
Released: March 14, 2011
Vanilla DeVille & Dane Cross in My First Sex Teacher
Dane has come after class to Prof. Deville's class because she wanted him to get some studying done. The Professor...
Categories: Big Tits, Black Hair, Blow Job, Brunette, Deepthroating, Facial, Fake Tits, Foot Fetish, Mature, Shaved, Stockings, Tattoos, Titty Fucking
Released: March 07, 2011
Britney Amber & Johnny Castle in My First Sex Teacher
Prof. Britney Amber isn't going to let Johnny play in the big game this weekend because his grades are horrible....
Categories: Ass smacking, Big Tits, Blonde, Blow Job, Deepthroating, Facial, Fake Tits, High Heels, Shaved, Tattoos
Released: February 28, 2011
India Summer & Tim Cannon in My First Sex Teacher
India is helping her student with his graduation speech because he’s her favorite so she must give him a good...
Where: Couch, Dining Room
Categories: Ball licking, Black Hair, Blow Job, Cum on Tits, Deepthroating, Facial, High Heels, Mature, Natural Tits, Small Tits, Stockings
Released: February 03, 2011
Sienna West & Dane Cross in My First Sex Teacher
Prof. West is making some hot tea in some really inclement weather. She hears a knock at her door and its Dane...
Where: Couch, Living room
Categories: Ball licking, Big Tits, Black Hair, Blow Job, Cum on Tits, Fake Tits, High Heels, Latina, Mature, Piercings, Shaved, Tattoos, Titty Fucking
Released: January 13, 2011
Michelle Lay & Xander Corvus in My First Sex Teacher
Michelle is excited to see how much her graduate student has grown up and now he’s come to ask for a favor from her...
Who: Professor
Categories: Big Dick, Blow Job, Brunette, Deepthroating, Facial, Glasses, Mature, Natural Tits, Stockings, Swallowing
Released: December 29, 2010
Torrey Pines & Kris Slater in My First Sex Teacher
Kris wants to get in touch with his artistic side and his art professor has agreed to give him private lessons and he...
Who: Professor
Categories: Ass smacking, Ball licking, Big Tits, Blonde, Blow Job, Cum on Tits, Deepthroating, Facial, Fake Tits, High Heels, Piercings
Released: December 14, 2010
Lisa Ann & Alan Stafford in My First Sex Teacher
Lisa Ann pays her student a visit to ask him to change the negative evaluation which has put her job on the line but...
Who: Professor
Where: Couch, Living room
Categories: Big Ass, Big Tits, Blow Job, Brunette, Cum on Tits, Curvy, Fake Tits, High Heels, Lingerie, Mature, Stockings
Released: November 29, 2010
Carmen Hayes & Michael Vegas in My First Sex Teacher
Michael is making up a test that he missed in Prof. Hayes class. While attempting to concentrate on the test, Prof....
Categories: Big Ass, Big Tits, Black, Black Hair, Blow Job, Cum on Tits, Deepthroating, Glasses, Interracial, Natural Tits, Piercings, Shaved, Tattoos
Released: November 16, 2010
Indianna Jaymes & Chad Alva in My First Sex Teacher
When Chad unexpectedly stops coming to class Professor Jaymes looks into the matter and finds out that he's dropping...
Who: Professor
Categories: Big Tits, Black Hair, Blow Job, Curvy, Deepthroating, Facial, Fake Tits, Hairy Pussy, Mature, MILFs, Voluptuous
Released: November 08, 2010
Ariella Ferrera & Mr. Pete in My First Sex Teacher
Ariella wants to end the sexual relationship she’s having with her student but this young cock just won’t give up...
Who: Professor
Where: Couch, Living room
Categories: Ass smacking, Big Tits, Blow Job, Brunette, Deepthroating, Fake Tits, Hairy Pussy, Stockings, Titty Fucking
Released: October 29, 2010
Syren De Mer & Danny Wylde in My First Sex Teacher
Danny missed his midterm, but Prof De Mer is letting him make it up after class. He goes up to ask her a question,...
Who: Teacher
Categories: Anal, Big Ass, Big Dick, Big Tits, Blow Job, Brunette, Cum on Glasses, Curvy, Deepthroating, Facial, Fake Tits, Glasses, High Heels, Mature, Piercings, Stockings, Swallowing, Tattoos, Titty Fucking
Released: October 22, 2010
Jezebel Jones & Seth Gamble in My First Sex Teacher
Seth is trying to finish up his fantasy football draft before his study session with Prof Jones. She puts a stop to...
Who: Teacher
Categories: Ball licking, Big Ass, Big Tits, Blonde, Blow Job, Deepthroating, Facial, Fake Tits, Glasses, High Heels, Mature, Shaved, Stockings, Tattoos, Titty Fucking
Released: October 20, 2010
Amanda Blow & Anthony Rosano in My First Sex Teacher
Anthony is in trouble. He hasn’t been able to get an erection since his wedding night, and his young horny new wife...
Who: Doctor
Categories: Ass licking, Ass smacking, Ball licking, Blonde, Blow Job, Cum on Tits, Deepthroating, High Heels, Lingerie, Mature, Natural Tits, Small Tits, Stockings, Tattoos
Released: October 14, 2010
Nyomi Banxxx & Danny Wylde in My First Sex Teacher
There seems to be a huge misunderstanding with these two but at the end of it all they both end up very satisfied...
Who: Teacher
Where: Couch, Living room
Categories: Ass smacking, Ball licking, Big Ass, Big Dick, Big Tits, Black, Black Hair, Blow Job, Deepthroating, Facial, Fake Tits, Interracial, Shaved, Tattoos, Titty Fucking
Released: October 05, 2010
Charlie James & Jenner in My First Sex Teacher
Charlie is a bored driving school instructor but her young student has a nice young cock for her to have a little...
Categories: Ball licking, Blow Job, Brunette, Facial, Glasses, High Heels, Natural Tits, Stockings, Tattoos
Released: September 20, 2010
Esperanza Gomez & Chris Johnson in My First Sex Teacher
Prof. Esperanza Gomez has a new student and he's a handful. He's got a short attention span and has trouble...
Categories: Big Tits, Blonde, Blow Job, Facial, Fake Tits, Foreign Accent, High Heels, Latina, Shaved
Released: September 17, 2010
Shay Morgan & Dane Cross in My First Sex Teacher
Prof. Morgan comes into her room to find her new TA Dane on the phone with one of his buddies making fun of her. She...
Categories: Ass smacking, Big Ass, Big Dick, Big Tits, Blonde, Blow Job, Cum on Tits, Curvy, Deepthroating, Facial, Fake Tits, Glasses, High Heels, Masturbation, Piercings, Shaved, Stockings, Tattoos
Released: September 01, 2010
Janet Mason & Chad Alva in My First Sex Teacher
Prof. Mason is out an about and ran into one of her students who is having trouble deciding on a major. She gives him...
Where: Couch, Living room
Categories: Big Tits, Blow Job, Facial, Fake Tits, High Heels, Mature, Piercings, Red Head, Stockings, Swallowing
Released: August 23, 2010
Ava Addams & Seth Gamble in My First Sex Teacher
Professor Adams' new TA, Kaci, has been trying to get laid by Seth, one of the professor's struggling students. Seth...
Categories: Ass smacking, Big Ass, Big Tits, Black Hair, Blow Job, Facial, Glasses, MILFs, Natural Tits, Tattoos, Titty Fucking
Released: August 13, 2010
Alexis Golden & Danny Mountain in My First Sex Teacher
Professor Golden is surprised to see one of her problem students show up early for the last day of class. He thought...
Who: Teacher
Categories: Ass smacking, Ball licking, Big Ass, Big Dick, Big Tits, Blonde, Blow Job, Facial, Fake Tits, High Heels, Mature, MILFs, Piercings, Shaved, Stockings, Voluptuous
Released: July 12, 2010
Diana Prince & Alex Gonz in My First Sex Teacher
Alex is a janitor in the expensive school where Diana teaches and he’s doing his job when he walks into her...
Categories: Ass licking, Ass smacking, Ball licking, Big Ass, Big Dick, Big Tits, Black Hair, Blow Job, Deepthroating, Facial, Fake Tits, Hairy Pussy, Hand Job, High Heels, Mature, Swallowing
Released: July 05, 2010
Dyanna Lauren & Alan Stafford in My First Sex Teacher
Dyanna is a giving professor and it seems a student in the school needs her help. She’s going to show this sad...
Categories: Big Tits, Blonde, Blow Job, Deepthroating, Facial, Fake Tits, High Heels, Mature, Stockings, Swallowing, Tattoos
Released: July 01, 2010
Zoey Holloway & Rocco Reed in My First Sex Teacher
Zoey Holloway is a photography teacher who encourages her students to push the limits of their artistic expression....
Who: Teacher
Categories: Ass smacking, Ball licking, Big Tits, Black Hair, Blow Job, Facial, Fake Tits, High Heels, Mature, Shaved, Stockings, Tattoos
Released: June 28, 2010
Samantha Ryan & James Deen in My First Sex Teacher
Samantha is a piano teacher who is visited by James. James wants to learn to play the piano to impress his...
Who: Teacher
Categories: Ass licking, Ass smacking, Blow Job, Brunette, Deepthroating, High Heels, Masturbation, Natural Tits, Piercings, Small Tits, Tattoos
Released: June 14, 2010
Phoenix Marie & Mark Wood in My First Sex Teacher
Prof. Phoenix Marie is so excited to be starting her summer off the right way: no school or significant other to tie...
Who: Co-worker, Professor, Teacher
Categories: Anal, Ass licking, Ass smacking, Ball licking, Big Ass, Big Dick, Big Tits, Blonde, Blow Job, Cum on Ass, Curvy, Deepthroating, Fake Tits, Hand Job, High Heels, Lingerie, Piercings, Shaved, Stockings, Tattoos, Titty Fucking, Voluptuous
Released: June 07, 2010
India Summer & Kris Slater in My First Sex Teacher
Professor Summer doesn't want to give Kris an extension on his paper but she decides that this will be the one time...
Categories: Black Hair, Blow Job, Deepthroating, Facial, High Heels, Lingerie, Mature, MILFs, Natural Tits, Small Tits, Stockings
Released: May 31, 2010
Sara Jay & Chris Johnson in My First Sex Teacher
Prof Jay has called Mr. Johnson in for a second interview. He wants to be her new TA. She knows him very well and...
Who: Teacher
Categories: Ass smacking, Big Ass, Big Dick, Big Tits, Blonde, Blow Job, Cum on Tits, Curvy, Deepthroating, Fake Tits, Glasses, Hand Job, High Heels, Lingerie, Mature, MILFs, Piercings, Shaved, Stockings, Tattoos, Titty Fucking, Voluptuous
Released: May 24, 2010
Velicity Von & Bill Bailey in My First Sex Teacher
Velicity has dismisses her class for spring break but has asked one of her young hot looking students to stay behind...
Categories: Ass smacking, Big Ass, Big Dick, Big Tits, Blonde, Blow Job, Cum on Ass, Curvy, Deepthroating, Fake Tits, Hairy Pussy, High Heels, Mature, MILFs, Piercings, Tattoos
Released: May 21, 2010
Persia Pele & Danny Wylde in My First Sex Teacher
Professor Pele called in a student to find out why he sent her flowers to the school because that's something that...
Categories: Big Tits, Black Hair, Blow Job, Facial, Fake Tits, High Heels, Latina, Mature, MILFs, Tattoos
Released: May 10, 2010
Amber Irons & Scott Stone in My First Sex Teacher
Scott is taking forever to finish his Final and Prof Irons is getting pissed off. Her Hawaii vacation can't start...
Categories: Ass smacking, Ball licking, Big Tits, Blonde, Blow Job, Facial, Fake Tits, Mature, Piercings, Shaved
Released: May 03, 2010
Lyla Storm & Alan Stafford in My First Sex Teacher
Lyla is a TA and has offered extra credit to all the students as instructed by the professor but she’s surprised to...
Who: School Faculty (other than professor)
Categories: Black Hair, Blow Job, Cum on Ass, Deepthroating, High Heels, Natural Tits, Piercings, Shaved, Small Tits, Stockings
Released: April 26, 2010
Angel Dark & Jordan Ash in My First Sex Teacher
Professor Dark is a difficult colleague to get along with and when a new TA shows up, he finds this out the hard way....
Categories: Anal, Ass licking, Ass smacking, Big Ass, Black Hair, Blow Job, Cum on Tits, Foreign Accent, Glasses, High Heels, Natural Tits, Stockings
Released: April 19, 2010
Robbye Bentley & Danny Wylde in My First Sex Teacher
Professor Bentley is filling out a March Madness bracket but she doesn't know where to start. One of her students...
Categories: Ball licking, Big Ass, Big Tits, Blonde, Blow Job, Curvy, Facial, Fake Tits, Hairy Pussy, Hand Job, High Heels, Mature, Titty Fucking
Released: April 12, 2010
Sincerre Lemmore & Danny Wylde in My First Sex Teacher
Danny Wylde is really late for his Female Empowerment class and admits to Professor Lemmore that he's only there to...
Categories: Ass smacking, Big Ass, Big Tits, Black, Black Hair, Blow Job, Facial, Fake Tits, High Heels, Interracial, Shaved, Stockings, Tattoos
Released: April 05, 2010
Ava Devine & Will Powers in My First Sex Teacher
Will Powers walks into the wrong class that Ava Devine is teaching and tells her he wants to be the head of the...
Categories: Asian, Ball licking, Big Ass, Big Dick, Big Tits, Blow Job, Brunette, Deepthroating, Facial, High Heels, MILFs, Shaved, Stockings, Tattoos
Released: April 02, 2010
Klarisa Leone & James Deen in My First Sex Teacher
James Deen needs help with his Anatomy class and he goes to Klarisa Leone's house. She doesn't know how to speak...
Where: Couch, Living room
Categories: Ass smacking, Big Tits, Blonde, Blow Job, Deepthroating, Facial, Fake Tits, High Heels, Piercings, Shaved, Swallowing, Tattoos
Released: March 25, 2010
Kayla Kleevage & Chris Johnson in My First Sex Teacher
Chris Johnson wants his reward for graduating from Kayla Kleevage but she just can't give him because the school...
Who: Teacher
Categories: Anal, Big Ass, Big Tits, Blonde, Blow Job, Deepthroating, Facial, Fake Tits, Glasses, High Heels, Mature, MILFs, Shaved, Stockings, Titty Fucking, Voluptuous
Released: March 04, 2010
Alia Janine & Dane Cross in My First Sex Teacher
Dane Cross is late for class and starts to have problems seeing out of his glasses. He can't seem to get his eyes...
Who: Professor
Categories: Ass smacking, Ball licking, Big Tits, Blow Job, Brunette, Facial, Glasses, Mature, MILFs, Natural Tits, Piercings, Shaved, Stockings, Tattoos, Titty Fucking
Released: February 15, 2010
Brittanie Lane & Seth Gamble in My First Sex Teacher
Seth turns his midterm exam in way too early. Prof. Lane wants to know why. When she examines his phone, she sees...
Who: Professor
Categories: Ass smacking, Ball licking, Big Dick, Big Tits, Blonde, Blow Job, Facial, Fake Tits, Foot Fetish, Glasses, Lingerie, Piercings, Shaved, Stockings
Released: February 11, 2010
Julia Ann & Shane Diesel in My First Sex Teacher
Prof. Diesel is concerned about his fellow Professor Julia's state of mind. She is mopy and sad and it shows in her...
Who: Co-worker, Friend, MILF, Professor
Categories: Ass licking, Big Dick, Big Tits, Blonde, Blow Job, Facial, Fake Tits, High Heels, Interracial, Mature, MILFs, Shaved, Stockings, Tattoos
Released: February 04, 2010
Sienna West & Danny Wylde in My First Sex Teacher
Sienna West is being accused of sexual harassment and she's venting out her frustrations to Danny Wylde. She admits...
Who: Boss, Co-worker, Friend, Professor, Teacher
Categories: Big Tits, Black Hair, Blow Job, Facial, Fake Tits, Glasses, High Heels, Latina, Shaved, Tattoos
Released: January 22, 2010
Marilyn Scott & Scott Stone in My First Sex Teacher
Marilyn Scott is having a difficult time during her first day of TAing. She doesn't have a pen or know where the...
Who: Professor, School Faculty (other than professor)
Categories: Ass smacking, Big Dick, Big Tits, Black Hair, Blow Job, Cum on Glasses, Facial, Fake Tits, Glasses, High Heels, Piercings, Shaved
Released: January 11, 2010
Persia Monir & Danny Mountain in My First Sex Teacher
Danny Mountain is taking a CPR class and the Professor, Persia Monir, is trying to teach him more than mouth to...
Categories: Big Dick, Big Tits, Blow Job, Brunette, Facial, Fake Tits, Hairy Pussy, High Heels, Mature, MILFs, Stockings
Released: January 04, 2010
Julia Ann & Rocco Reed in My First Sex Teacher
Rocco Reed turns in his video game thesis and Julia Ann is pissed about it. She tells him that he has to fuck her in...
Who: Professor
Categories: Ass licking, Big Tits, Blonde, Blow Job, Facial, Fake Tits, Glasses, Hand Job, High Heels, Mature, Shaved, Swallowing, Tattoos, Titty Fucking
Released: December 28, 2009
Claudia Valentine & Dane Cross in My First Sex Teacher
Professor Valentine just found out that her boyfriend is cheating on her with one of the school's cheerleaders. After...
Who: Professor
Categories: Black Hair, Blow Job, Deepthroating, Facial, Fake Tits, Shaved
Released: December 16, 2009
Flower Tucci & Chris Johnson in My First Sex Teacher
Chris is trying to get ahead in class by getting his paper done early and turns it in to Professor Tucci. She's so...
Who: Professor
Categories: Anal, Ass smacking, Ball licking, Big Ass, Big Dick, Blonde, Blow Job, Cum on Ass, Curvy, Deepthroating, High Heels, Natural Tits, Tattoos
Released: December 14, 2009
Monique Fuentes & Alec Knight in My First Sex Teacher
Professor Monique Fuentes is confronted by Prof. Knight about a failing student. The student is failing Prof....
Categories: Big Dick, Big Tits, Blow Job, Brunette, Cum on Tits, Facial, Fake Tits, Foreign Accent, High Heels, Latina, MILFs
Released: December 07, 2009
Jewels Jade & Seth Gamble in My First Sex Teacher
Seth Gamble is trying to study some vocabulary words but he notices that they all have the word "anal" in it. It's...
Who: Professor
Categories: Anal, Ass smacking, Big Tits, Black Hair, Blow Job, Deepthroating, Facial, Fake Tits, Shaved, Tattoos
Released: November 30, 2009
Lisa Ann & Chris Johnson in My First Sex Teacher
Chris Johnson is trying to finish up his notes for Business class but Lisa Ann is asking him to do all sorts of...
Who: Professor
Where: Classroom
Categories: Big Ass, Big Tits, Black Hair, Blow Job
Released: November 23, 2009
Darla Crane & James Deen in My First Sex Teacher
James is taking too long on his final and Professor Crane wants her vacation to start. She pleads with him to finish...
Who: Professor
Categories: Ass licking, Ass smacking, Big Ass, Big Dick, Big Tits, Blow Job, Fake Tits, Glasses, High Heels, Mature, Red Head, Shaved, Tattoos, Titty Fucking
Released: November 16, 2009
Sienna West & Rocco Reed in My First Sex Teacher
Professor West is trying to grade some papers when a neighboring Professor wanders into her class to warn her about...
Who: Professor
Categories: Ass smacking, Big Tits, Black Hair, Blow Job, Facial, Fake Tits, Glasses, Hand Job, Shaved, Tattoos, Uniform
Released: November 09, 2009
Diamond Foxxx & Mikey Butders in My First Sex Teacher
Mikey is getting a lecture from Diamond Foxxx about his evaluation. He can't learn anything when Diamond is always...
Who: Professor
Categories: Big Tits, Blonde, Blow Job, Cum on Tits, Facial, Fake Tits, High Heels, Mature, Piercings, Shaved, Titty Fucking
Released: November 02, 2009
Shay Sights & Danny Wylde in My First Sex Teacher
Danny is coming to class tired because he has been clubbing all night and Shay Sights doesn't want any excuse. He's...
Who: Professor
Categories: Ball licking, Big Tits, Black Hair, Blow Job, Cum on Tits, Deepthroating, Fake Tits, Mature, Shaved, Tattoos
Released: October 26, 2009
Kasey Grant & Rocco Reed in My First Sex Teacher
Professor Grant is a strict disciplinarian. Even when a student shows up late for a final, she will not let him make...
Who: Professor
Categories: Big Tits, Blonde, Blow Job, Cum on Tits, Fake Tits, Mature, Piercings, Tattoos, Titty Fucking
Released: October 19, 2009
Camryn Cross & Pike Nelson in My First Sex Teacher
Professor Cross is calming down a student who ran to her classroom in a panic. Apparently his girlfriend thinks he...
Categories: Big Dick, Big Tits, Blonde, Blow Job, Facial, Fake Tits, Hand Job, High Heels, Mature, Piercings, Tattoos
Released: October 12, 2009
Lezley Zen & Seth Gamble in My First Sex Teacher
Seth's dorm room buddies have played another practical joke on him. Lezley tells him that he needs to stand up for...
Categories: Big Tits, Black Hair, Blow Job, Cum on Ass, Fake Tits, Mature, MILFs, Piercings, Tattoos
Released: October 05, 2009
Montana Skye & Mikey Butders in My First Sex Teacher
Mikey is trying to take his final but his professor is absent and his "assistant" Montana is there instead. He soon...
Categories: Ass smacking, Big Tits, Blow Job, Brunette, Facial, Fake Tits, High Heels, Mature, MILFs, Tattoos
Released: September 28, 2009
Vanilla DeVille & Danny Wylde in My First Sex Teacher
Professor DeVille just got word from the dean that she no longer has a position at the university where she worked...
Categories: Ass smacking, Ball licking, Big Dick, Big Tits, Black Hair, Brunette, Deepthroating, Facial, Fake Tits, Glasses, Hand Job, High Heels, Lingerie, Mature, Stockings, Swallowing, Tattoos
Released: September 21, 2009
Dylan Ryder & Pike Nelson in My First Sex Teacher
Dylan is surprised to see one of the students has given all the professors a bad review. This ex professor now turned...
Who: Professor, School Faculty (other than professor)
Categories: Ass licking, Big Ass, Big Dick, Big Tits, Black Hair, Blow Job, Curvy, Fake Tits, High Heels, Lingerie, Shaved, Stockings, Voluptuous
Released: September 14, 2009
Val Malone & Joey Brass in My First Sex Teacher
Professor Malone is meeting with a student to discuss changing his major to human sexuality. She doesn't think...
Who: School Faculty (other than professor)
Categories: Ball licking, Big Tits, Blonde, Blow Job, Facial, Fake Tits, Shaved, Tattoos
Released: September 07, 2009
Taylor Mayde & Seth Gamble in My First Sex Teacher
Since Taylor is no longer coming back to teach next semester she is now ready to have her fantasies become a reality...
Who: Professor
Categories: Blow Job, Brunette, Facial, High Heels, Natural Tits, Shaved, Small Tits, Tattoos
Released: August 31, 2009
Roxanne Hall & Will Powers in My First Sex Teacher
Roxanne is trying to help Will with the delivery of his lines but he's just not getting it. Even though Will's not...
Who: Professor
Where: Couch, Living room
Categories: Big Dick, Big Tits, Blonde, Blow Job, Facial, Fake Tits, Foreign Accent, Mature, MILFs, Swallowing, Tattoos
Released: August 24, 2009
Leah Lust & Aaron Wilcoxxx in My First Sex Teacher
Professor lust is disappointed with the thesis Aaron submitted and wants a rewrite. Since there are only two weeks...
Categories: Ball licking, Big Dick, Big Tits, Blonde, Blow Job, Cum on Tits, Fake Tits, Piercings, Shaved, Tattoos
Released: August 17, 2009
Sarah Bricks & Pike Nelson in My First Sex Teacher
Sarah Bricks breaks some bad news to her student that he's losing his scholarship. So she offers him options to get...
Who: Professor
Categories: Ball licking, Big Dick, Blow Job, Brunette, Facial, Fake Tits, Hand Job, High Heels, Mature, MILFs, Piercings, Shaved, Stockings, Swallowing
Released: August 10, 2009
Monique Alexander & Alan Stafford in My First Sex Teacher
Monique Alexander has recently become a teacher’s assistant and she’s taking her position seriously. When Alan...
Who: Co-ed, College Girl, Friend, School Faculty (other than professor)
Categories: Blonde, Blow Job, Facial, High Heels, Petite, Piercings, Small Tits, Tattoos
Released: August 03, 2009
Rhylee Richards & Bill Bailey in My First Sex Teacher
Professor Richards is administering a mid-term to a student who couldn’t make it to class on time. But he’s more...
Who: Professor
Categories: Ball licking, Big Tits, Blonde, Blow Job, Facial, Fake Tits, Glasses, High Heels, Tattoos
Released: July 27, 2009
Piper Austin & Gabriel D'Alessandro in My First Sex Teacher
Professor Austin is having such a difficult time keeping up with her busy schedule that she showed up late for a...
Who: Professor
Categories: Big Tits, Blow Job, Brunette, Cum on Tits, High Heels, Natural Tits, Piercings, Stockings
Released: July 14, 2009
Diana Prince & Pike Nelson in My First Sex Teacher
When Professor Prince catches her student cheating on an exam, her immediate reaction is to fail him. But when he...
Categories: Big Dick, Black Hair, Blow Job, Cum on Tits, Fake Tits, MILFs
Released: July 09, 2009
Aurora Snow & Dane Cross in My First Sex Teacher
Professor Snow needs to see one of her students after class. He’s struggling in her acting class and Aurora asks if...
Categories: Ass smacking, Blonde, Blow Job, Deepthroating, Facial, Hand Job, High Heels, Natural Tits, Shaved, Small Tits, Stockings
Released: June 29, 2009
Camryn Cross & Ralph Long in My First Sex Teacher
Professor Cross is teaching the nude female form to her art class but one of her students seems distracted by the...
Categories: Big Dick, Big Tits, Blonde, Blow Job, Facial, Fake Tits, Glasses, High Heels, Mature, MILFs, Piercings, Shaved, Stockings, Tattoos
Released: June 23, 2009
Roxanne Hall & JMac in My First Sex Teacher
Professor Hall has some questions for one of her frat boy students. She wants to know what goes on at their parties....
Categories: Big Dick, Big Tits, Blonde, Blow Job, Facial, Fake Tits, Foreign Accent, High Heels, Mature, MILFs, Shaved, Tattoos
Released: June 18, 2009
Becca Blossoms & Scott Stone in My First Sex Teacher
Professor Blossoms just caught one of her students cheating and she’s going to report him to the dean. He’ll do...
Who: Professor
Categories: Blonde, Blow Job, Facial, Glasses, Natural Tits, Piercings
Released: June 04, 2009
Diamond Foxxx, Indianna Jaymes & Danny Mountain in My First Sex Teacher
Professor Foxxx is staying after class to try and help a struggling student. When her colleague and lover, Professor...
Categories: Big Tits, Blonde, Blow Job, Brunette, Cum Swapping, Fake Tits, Glasses, High Heels, Mature, MILFs, Piercings, Shaved, Stockings, Threesome BGG, Titty Fucking
Released: June 02, 2009
Princess Donna & Danny Mountain in My First Sex Teacher
Professor Donna is hearing some rumors from her colleagues. She plans on making a certain student retake an exam but...
Who: Professor
Categories: Black Hair, Blow Job, Facial, Natural Tits, Shaved, Tattoos
Released: May 26, 2009
Holly Sampson & Danny Mountain in My First Sex Teacher
Professor Sampson doesn’t know it yet but she’s on a very special list. One of her students has a plan to sleep...
Categories: Big Tits, Blonde, Blow Job, Facial, Fake Tits, Glasses, High Heels, MILFs, Stockings
Released: May 20, 2009
Sinnamon Love & Mikey Butders in My First Sex Teacher
Professor Love is so happy with the captain of the debate team that she’s treating him to an all inclusive stay in...
Categories: Anal, Big Ass, Black, Black Hair, Blow Job, Facial, Glasses, High Heels, MILFs, Natural Tits, Shaved, Stockings
Released: May 11, 2009
Holly Halston & Joey Brass in My First Sex Teacher
Professor Halston is in a sticky situation. The students in her night-class keep transferring out because they’re...
Who: Professor
Categories: Big Tits, Blonde, Blow Job, Facial, Fake Tits, High Heels, MILFs, Piercings, Shaved, Swallowing, Tattoos, Titty Fucking
Released: May 04, 2009
Zoey Holloway & Alan Stafford in My First Sex Teacher
Professor Holloway has an obnoxious drummer in her music theory course. He's not interested in theory and...
Categories: Black Hair, Blow Job, Facial, Glasses, MILFs, Natural Tits, Shaved, Small Tits, Tattoos
Released: April 27, 2009
Gina Rome & James Deen in My First Sex Teacher
Professor Rome is teaching chemistry but James is having trouble following because of her exotic accent. Since words...
Categories: Big Ass, Blow Job, Brunette, Facial, Glasses, Hairy Pussy, Mature, MILFs, Natural Tits
Released: April 20, 2009
Sunshine Seiber & Rocco Reed in My First Sex Teacher
Professor Seiber is staying late to administer a midterm to the star basketball player. He’s not taking the test or...
Categories: Big Ass, Big Tits, Blow Job, Brunette, Curvy, Facial, Fake Tits, Glasses, Mature, MILFs, Piercings, Shaved, Tattoos, Titty Fucking
Released: April 13, 2009
Brandi Love & Danny Wylde in My First Sex Teacher
Professor Love hates when students waste her time. One student missed his anatomy final so Professor Love decides to...
Who: Professor
Categories: Big Tits, Blow Job, Brunette, Facial, Fake Tits, Hand Job, Mature, MILFs, Piercings, Stockings, Tattoos
Released: April 06, 2009
Max Mikita & Scott Stone in My First Sex Teacher
Professor Mikita is helping a struggling student understand the Marquis de Sade’s literature. He didn’t...
Categories: Anal, Asian, Black Hair, Blow Job, Facial, Hairy Pussy, Mature, MILFs, Natural Tits, Stockings
Released: March 30, 2009
Nikki Sinn & Chris Johnson in My First Sex Teacher
Nikki Sinn is meeting with a student who submitted second-rate erotica for homework. If the young man wants to pass...
Who: Professor
Categories: Big Dick, Big Tits, Blow Job, Fake Tits, Mature, MILFs, Red Head, Shaved, Tattoos
Released: March 23, 2009
Tina Tyler & Danny Wylde in My First Sex Teacher
Professor Tyler will not tolerate cell phones in her class room. But that doesn’t stop Danny from using it. When...
Who: Professor
Categories: Big Dick, Blow Job, Brunette, Facial, Glasses, Hairy Pussy, Mature, MILFs, Stockings
Released: March 16, 2009
Becca Blossoms & Joey Brass in My First Sex Teacher
Professor Blossoms is trying to engage a student in English Lit. Since he’s an art student, he doesn’t appreciate...
Who: Professor
Where: Chair, Classroom, Table
Categories: Blow Job, Facial, Mature, MILFs, Natural Tits, Piercings, Shaved
Released: March 12, 2009
Emma Starr & Billy Glide in My First Sex Teacher
Mrs. Starr is a hot-to-trot teacher who doesn’t mind failing her students. And when she fails the star quarterback,...
Who: Co-worker
Where: Couch, Living room
Categories: Big Dick, Big Tits, Blonde, Blow Job, Facial, Fake Tits, Mature, MILFs, Piercings, Tattoos
Released: March 05, 2009
Indianna Jaymes & Joey Brass in My First Sex Teacher
Professor Jaymes is fed up with her most disruptive student. She’s called him into her office for one last chance...
Who: Professor
Categories: Big Ass, Big Tits, Blow Job, Brunette, Cum on Tits, Fake Tits, Glasses, Hairy Pussy, Mature, MILFs, Stockings
Released: February 24, 2009
Mrs. Jewell, Erica Lauren & Christian in My First Sex Teacher
Mrs. Jewell and Mrs. Lauren are in a mood to celebrate because their students won the debate competition. They thank...
Categories: Big Ass, Blonde, Blow Job, Facial, Fake Tits, Hairy Pussy, Mature, MILFs, Natural Tits, Shaved, Stockings, Threesome BGG
Released: February 17, 2009
Raquel Devine, Dani Jensen & Talon in My First Sex Teacher
Professor DeVine stayed after class to give a re-test to Dani Jensen, but she never showed up. When Ms. DeVine finds...
Who: Athlete, Co-worker, MILF, Student
Where: Bleachers, Chair, Floor, Gym
Categories: BGG, Big Tits, Blow Job, Brunette, Fake Tits, Mature, MILFs, Natural Tits, Petite, Piercings, Red Head, Small Tits, Tattoos, Threesome
Released: February 12, 2009
Mason Storm, Ashli Orion & Chris Johnson in My First Sex Teacher
Professor Storm tells one struggling student to see her after class -- and to bring his girlfriend, Ashli Orion. Ms....
Who: Girlfriend, Professor
Categories: Big Dick, Big Tits, Black Hair, Blow Job, Cum on Tits, Latina, Mature, MILFs, Piercings, Shaved, Small Tits, Tattoos, Threesome BGG
Released: February 02, 2009
Michelle Lay, Kacey Villainess & Ram in My First Sex Teacher
Kacey Villainess has caught the eye of her professor Michelle Lay. Even though Kacey has low test scores, Ms. Lay...
Who: Girlfriend, Student
Where: Couch, Living room
Categories: Blonde, Blow Job, Brunette, Facial, Mature, MILFs, Shaved, Small Tits, Tattoos, Threesome BGG
Released: January 30, 2009
Trisha Lynne & Jerry in My First Sex Teacher
Professor Trisha Lynne has an unexpected visit from a former student. He wants Trisha to be his mentor and she's...
Categories: Blow Job, Brunette, Facial, Fake Tits, Hairy Pussy, Mature, MILFs
Released: January 26, 2009
Brittany O'Connell & Chris Johnson in My First Sex Teacher
Professor O’Connell is looking for a new teaching assistant. She’s surprised to find one of her underachieving...
Categories: Big Fake Tits, Big Tits, Blow Job, Facial, Hairy Pussy, Mature, MILFs, Red Head, Stockings, Tattoos
Released: January 20, 2009
Nikita Devine & Alan Stafford in My First Sex Teacher
Professor Devine is all set for graduation. But two of her students have something they need to accomplish before...
Who: Professor
Categories: Big Tits, Blonde, Blow Job, Facial, Lingerie, Tattoos, Threesome BBG
Released: January 16, 2009
Janet Mason & Will Powers in My First Sex Teacher
Professor Mason won't put up with her TA fucking one of the students. She lets him know that if he's going to fuck...
Who: Professor
Categories: Big Tits, Blow Job, Cum on Tits, Facial, Fake Tits, Mature, MILFs, Petite, Piercings, Red Head, Stockings
Released: January 12, 2009
Magdalene St. Michaels & Mikey Butders in My First Sex Teacher
Professor St. Michaels gets turned on by intelligence, and she gets wet when one of her students comes up with a new...
Who: Professor
Categories: Big Tits, Brunette, Facial, Fake Tits, Mature, MILFs, Shaved, Stockings
Released: January 05, 2009
Sinnamon Love & CJ Wright in My First Sex Teacher
Sinnamon Love just got an assistant teaching position and her boyfriend wants to celebrate. They can't wait to get...
Who: Girlfriend
Categories: Ass smacking, Big Ass, Black, Blow Job, Brunette, Facial, Hairy Pussy, Stockings
Released: January 02, 2009
Mrs. Jewell & Alan Stafford in My First Sex Teacher
Mrs. Jewell is a hands-on art teacher. She loves becoming one with her materials and subjects, especially when she...
Categories: Big Ass, Blow Job, Facial, Lingerie, Mature, MILFs, Natural Tits, Shaved, Stockings
Released: December 29, 2008
India Summer, Janet Mason & Alan Stafford in My First Sex Teacher
Professors Summer and Mason have no need for an assistant. But when an ambitious student asks them about an opening,...
Where: Chair, Table, Teacher\'s lounge
Categories: Big Tits, Black Hair, Blow Job, Facial, Fake Tits, Hairy Pussy, Mature, MILFs, Natural Tits, Petite, Piercings, Red Head, Small Tits, Stockings, Threesome BGG
Released: December 23, 2008
Austin Kincaid & Jarrod Steed in My First Sex Teacher
Professor Austin Kincaid can finally relax. The school year is over and she’s reminiscing with her most improved...
Who: Professor
Categories: Big Ass, Big Fake Tits, Brunette, Facial, Shaved
Released: December 08, 2008
Joclyn Stone & Jenner in My First Sex Teacher
Professor Joclyn Stone is a great listener. When one of her students reveals his recent break up with his girlfriend,...
Who: Professor
Categories: Big Ass, Big Natural Tits, Blonde, Hairy bush, Tattoos
Released: December 01, 2008
Charlie James & Johnny Sins in My First Sex Teacher
Professor Charlie James is at the end of her rope. She is trying to tutor a struggling student, but he doesn't...
Who: Professor
Categories: Big Natural Tits, Brunette, POV, Tattoos
Released: November 26, 2008
Brandi Love & Chris Johnson in My First Sex Teacher
Professor Brandi Love is excited because her student aced his latest exam. She'd been tutoring him for some time, but...
Who: Professor
Categories: Big Ass, Big Fake Tits, Blonde, Piercings, Stockings, Tattoos
Released: November 26, 2008
KC Kelly & Christian in My First Sex Teacher
Professor Kelly will help her students however she can. But she won’t do it without getting something in return....
Who: Professor
Categories: Big Ass, Big Fake Tits, Blonde, MILFs, Piercings, POV, Shaved, Stockings
Released: November 24, 2008
Ginger Lynn & Johnny Sins in My First Sex Teacher
Professor Ginger Lynn has her own way of doing things. If a student needs help, she knows how to get through to him....
Categories: Big Ass, Big Natural Tits, Blonde, MILFs, Shaved
Released: November 10, 2008
Lynn LeMay & Danny Wylde in My First Sex Teacher
Professor Lynn LeMay doesn’t screw around. When she catches her student pulling a prank in her classroom for his...
Who: Professor
Categories: Big Natural Tits, Blonde, MILFs, Shaved, Stockings, Tattoos
Released: November 03, 2008
Holly Sampson & David Loso in My First Sex Teacher
Professor Holly Sampson is a tempting teacher. She’s always there for her students. When one student asks her...
Who: Professor
Categories: Big Fake Tits, Blonde, Tattoos
Released: October 27, 2008
Felony Foreplay & David Loso in My First Sex Teacher
Professor Felony Foreplay is a horny teacher. She hides it during class, but underneath her stern appearance she just...
Who: Professor
Categories: Big Fake Tits, MILFs, Piercings, Red Head, Shaved
Released: October 17, 2008
Janet Mason & Chris Johnson in My First Sex Teacher
Professor Janet Mason is losing a student. He’s leaving for community college to pursue different disciplines. But...
Who: Professor
Categories: Big Fake Tits, MILFs, Piercings, Red Head, Shaved, Stockings
Released: October 13, 2008
Deauxma & Alan Stafford in My First Sex Teacher
Professor Deauxma has a problem student. After hours of tutoring, he isn’t retaining any of the material. She...
Categories: Big Fake Tits, Brunette, MILFs, Stockings
Released: October 06, 2008
Cherokee & Alan Stafford in My First Sex Teacher
Professor Cherokee is a flirt. She isn’t afraid to use her killer curves to get what she wants. And she wants to...
Who: Professor
Categories: Big Ass, Big Fake Tits, Brunette, Shaved
Released: September 29, 2008
Alexis Silver & Rocco Reed in My First Sex Teacher
Professor Alexis Silver can’t stand bungling students. And there’s one in particular she can’t figure out. But...
Who: Professor
Categories: Big Natural Tits, Black, Brunette, Piercings, Shaved, Stockings, Tattoos
Released: September 22, 2008
Katja Kassin & Danny Wylde in My First Sex Teacher
Professor Katja Kassin is a beautifully busty teacher. After a student excelled beyond her wildest expectations, she...
Who: Professor
Categories: Big Ass, Big Fake Tits, Red Head, Shaved, Stockings
Released: September 15, 2008
Vannah Sterling & Jenner in My First Sex Teacher
Professor Vannah Sterling is finishing up an exhausting couple of hours of student orientation. As she’s about to...
Who: MILF, Professor, Stranger
Categories: Big Ass, Big Fake Tits, Brunette, Shaved, Tattoos
Released: September 08, 2008
Melissa Monet & Chris Johnson in My First Sex Teacher
Professor Melissa Monet is furious. A student is catching up on some sleep in her classroom and Melissa has had...
Who: MILF, Professor, School Faculty (other than professor)
Categories: Big Ass, Big Fake Tits, Brunette, MILFs, Stockings
Released: September 02, 2008
Teri Weigel, Holly Morgan & Danny Wylde in My First Sex Teacher
Professor Teri Weigel stayed after class to answer some of Holly Morgan’s questions. Teri is teaching human...
Who: College Girl, Girlfriend, MILF, Stranger
Categories: BGG, Big Fake Tits, Blonde, Brunette, MILFs, Petite, Shaved, Tattoos, Threesome
Released: August 25, 2008
Raquel Devine & Mikey Butders in My First Sex Teacher
Professor Raquel DeVine just caught one student participating in a cheating ring. He claims the papers look similar...
Who: Professor
Categories: Big Fake Tits, Brunette
Released: August 18, 2008
Sunshine Seiber & Jarod Diamond in My First Sex Teacher
Sunshine Seiber is coach of the women’s soccer team. The assistant coach of the men’s team isn’t happy there,...
Who: Co-ed, College Girl, Student
Categories: Big Ass, Big Fake Tits, Piercings, Shaved, Tattoos
Released: August 11, 2008
Emma Starr, Nika Noir & Derrick Pierce in My First Sex Teacher
Mrs. Starr and Nika Noir are ending another class. Before they leave, they notice a student arguing over the phone....
Who: Co-worker, Professor, School Faculty (other than professor)
Categories: BGG, Big Fake Tits, Blonde, Brunette, Foreign Accent, MILFs, Small Tits, Tattoos
Released: August 04, 2008
& Adriana Deville in My First Sex Teacher
Professor Adriana Deville is a little mixed up. She sent her EMT class an email canceling class then another calling...
Who: Professor
Categories: Blonde, Shaved, Small Tits
Released: August 01, 2008
Heidi Mayne & Will Powers in My First Sex Teacher
Professor Heidi Mayne is busy. Between teaching and coaching, she never has time to find a man. So when one of her...
Who: Professor
Categories: Big Ass, Big Fake Tits, Blonde, Piercings, Shaved, Tattoos, Uniform
Released: July 28, 2008
Sami Scott & Alan Stafford in My First Sex Teacher
Professor Sami Scott is out of options. She’s been trying to teach one of her students English Lit., but he just...
Who: Married Woman, Professor
Categories: Big Fake Tits, Brunette, Stockings
Released: July 21, 2008
Charlie James & Jarod Diamond in My First Sex Teacher
Professor Charlie James is beginning her career. On her first day, her first student walks in and it it’s her old...
Who: Professor
Categories: Big Ass, Big Natural Tits, Brunette
Released: July 07, 2008
Lila James, Tiry Wild & Jarod Diamond in My First Sex Teacher
Professor Tiry Wild must settle a dispute. Lila James and her classmate made a movie but no one showed up for the...
Who: Classmate, Co-ed, College Girl, Professor
Categories: BGG, Blonde, Brunette, MILFs, Petite, Piercings, Shaved, Small Tits, Tattoos
Released: June 30, 2008
Jordan Kingsley & Will Powers in My First Sex Teacher
Professor Jordan Kingsley knows how to relate to students. She doesn’t mind when a student approaches her in the...
Who: Professor
Where: Chair, Table, Teacher\'s lounge
Categories: Big Natural Tits, Blonde, Tattoos
Released: June 23, 2008
Anjanette Astoria & Alan Stafford in My First Sex Teacher
Anjanette Astoria doesn’t mess around. While she waited for a student to finish an exam, she caught him playing...
Who: Professor, School Faculty (other than professor)
Categories: Big Ass, Big Fake Tits, Black, Brunette, Piercings, Shaved, Stockings
Released: June 16, 2008
Sophia Lomeli & Will Powers in My First Sex Teacher
Professor Lomeli is suspicious. She believes that her best student is writing papers for other students in her class....
Who: Professor
Categories: Big Fake Tits, Brunette, Latina, Piercings, Shaved
Released: June 12, 2008
June Summers & Will Powers in My First Sex Teacher
June Summers just caught a student cheating. He wanted the results of a biology report but never expected his teacher...
Who: Professor
Categories: Big Fake Tits, Brunette, MILFs, Shaved
Released: June 09, 2008
Max Mikita & Jordan Ash in My First Sex Teacher
Max Mikita is getting a shower in the locker room. A student sneaks in to steal her panties for a scavenger hunt. Max...
Who: Professor
Where: Bench, Locker Room
Categories: Asian, Brunette, Hairy bush, Petite, Small Tits
Released: June 02, 2008
Adrenalynn & Danny Mountain in My First Sex Teacher
Professor Adrenalynn is preparing for botany class. A new student arrives early to discover he stood her up at a...
Who: Professor
Categories: Asian, Big Ass, Big Fake Tits, Brunette, Piercings, Shaved, Tattoos
Released: May 30, 2008
Ayana Angel & Mikey Butders in My First Sex Teacher
Professor Angel is excited to be teaching new age healing methods. She invited her best student to her house to...
Where: Couch, Living room
Categories: Big Ass, Big Fake Tits, Black, Brunette, Piercings, Tattoos
Released: May 27, 2008
Kendra Secrets & Alan Stafford in My First Sex Teacher
Professor Secrets is staying late again. She’s slammed with work and more irritated when her intern brings the...
Categories: Big Fake Tits, Brunette, MILFs, Piercings, Stockings, Tattoos
Released: May 19, 2008
Joey Lynn & Jerry in My First Sex Teacher
Professor Lynn knows that the only way to teach anatomy is with anatomy. So when Jerry isn’t doing so well in her...
Categories: Blonde, MILFs, Piercings, Shaved, Small Tits, Stockings, Tattoos
Released: May 05, 2008
Brenda James & Rocco Reed in My First Sex Teacher
A former student drops by to see Brenda James. He lost his letter of recommendation and needs another copy. She has...
Categories: Anal, Big Fake Tits, Blonde, Glasses, MILFs, Shaved
Released: April 28, 2008
Bridgette Monroe, Scarlett Pain & Otto Bauer in My First Sex Teacher
Professor Monroe is fed up with Scarlett Pain and her antics. She’s constantly causing trouble in her class, so...
Categories: BGG, Big Fake Tits, Big Natural Tits, Blonde, MILFs, Petite, Piercings, Red Head, Shaved, Tattoos, Threesome
Released: April 21, 2008
Kasandra Blue & Mikey Butders in My First Sex Teacher
Mrs. Blue is fed up with Mikey falling asleep in her class. She reminds him that he’s not doing well and needs to...
Where: Classroom
Categories: Big Ass, Brunette, Small Tits
Released: April 14, 2008
Morgan Reigns & Derrick Pierce in My First Sex Teacher
When Professor Reigns asked her students to write erotic literature, she was expecting PG-13, but Derrick’s was...
Categories: Big Ass, Big Fake Tits, Piercings, Red Head, Shaved, Tattoos
Released: April 07, 2008
Rae Rodgers & Jenner in My First Sex Teacher
Professor Rodgers really cares about her students in sociology 101. When they are doing well, she gives them positive...
Where: Classroom
Categories: Brunette, Small Tits, Stockings
Released: March 31, 2008
Emilianna & Brad Hardy in My First Sex Teacher
Dean Emilianna can’t believe Brad has been sent to see her again. How many times can one student get in trouble in...
Where: Classroom
Categories: Blonde, Small Tits
Released: March 24, 2008
Syren De Mer & Chris Johnson in My First Sex Teacher
After hearing Chris sing, Professor De Mer advises him to pursue a career in acting or modeling. She knows people...
Where: Desk
Categories: Brunette, Glasses, Small Tits, Stockings
Released: March 18, 2008
Michelle Lay & James Deen in My First Sex Teacher
When James stops by after hours to speak to Professor Lay, he admits he’s not doing too well in class because he...
Categories: Brunette, Glasses, MILFs, Small Tits, Stockings, Tattoos
Released: March 10, 2008
Ava Devine & Jordan Ash in My First Sex Teacher
Jordan’s been having some problems with his girlfriend, so when he fails his math test, he asks Professor Devine if...
Categories: Asian, Big Fake Tits, Brunette, Glasses, Stockings
Released: March 03, 2008
Desi Foxx & Alan Stafford in My First Sex Teacher
Professor Foxx is reassuring Alan that it’s natural and normal for a college guy to have sex on the mind. How could...
Categories: Big Fake Tits, Glasses, MILFs, Piercings, Red Head, Stockings, Tattoos
Released: February 25, 2008
Joclyn Stone & Alan Stafford in My First Sex Teacher
Election Day is coming so Professor Stone is urging all her students to vote, but she doesn’t know how to convince...
Categories: Big Ass, Big Natural Tits, Blonde, Curvy, Hairy bush, MILFs, Stockings, Tattoos
Released: February 11, 2008
Jaycie Lane & Chris Johnson in My First Sex Teacher
Chris is a very serious student and a bit aggressive when it comes to his education. So when he approaches Professor...
Categories: Big Ass, Big Natural Tits, Blonde, Glasses, Stockings
Released: February 04, 2008
Brenda James & Mikey Butders in My First Sex Teacher
Mikey’s a cocky frat boy who thinks he can get away with skipping class, but Professor Brenda James is a...
Categories: Big Fake Tits, Blonde, Glasses, MILFs, Shaved
Released: January 28, 2008
Velvet Licx & Rocco Reed in My First Sex Teacher
Counselor Velvet Licx won’t tolerate misbehavior in her students, so when Rocco is sent to her office for passing...
Categories: Brunette, Glasses, Shaved, Small Tits
Released: January 21, 2008
Lisa Sparxxx & Zane in My First Sex Teacher
Professor Lisa Sparxxx has had it with her failing students, so she’s decided to take their education into her own...
Categories: Big Ass, Big Natural Tits, Brunette, MILFs, Shaved, Tattoos
Released: January 15, 2008
Emma Starr & Zane in My First Sex Teacher
Emma Starr is back! So Zane wants to be the first of her students to welcome her back to campus. She tells him...
Categories: Big Fake Tits, Blonde, Glasses, MILFs, Piercings, Shaved, Stockings
Released: January 07, 2008
Kylie Ireland & Derrick Pierce in My First Sex Teacher
Derrick can never stay awake in Professor Kylie Ireland’s class, and things become awkward when he dreams of her...
Categories: Big Ass, Big Natural Tits, Hairy bush, MILFs, Piercings, Red Head, Tattoos
Released: December 30, 2007
& Debbie Dial in My First Sex Teacher
Long after Professor Debbie Dial dismisses class, she’s surprised to see Jenner still sitting there. He seems to be...
Categories: Big Ass, Blonde, Glasses, MILFs, Small Tits, Tattoos
Released: December 25, 2007
India Summer & Zane in My First Sex Teacher
Zane is India Summer’s favorite student. He makes good grades, he never misses class, and he always pays attention....
Where: Desk
Categories: Brunette, Glasses, MILFs, Small Tits, Stockings
Released: December 17, 2007
Penny Porsche & Derrick Pierce in My First Sex Teacher
Derrick has no idea why Professor Penny Porsche kept him after class. He's one of her top students and got a 98 on...
Categories: Big Natural Tits, Blonde, Glasses, MILFs
Released: December 10, 2007
Emilianna & Alan Stafford in My First Sex Teacher
Campus Cop Emilianna knows Alan pulled that fire alarm, so she's either going to expel him or blackmail him. And we...
Where: Desk
Categories: Big Ass, Big Natural Tits, Blonde, Stockings
Released: December 03, 2007
Demi Delia & Bridgett Lee in My First Sex Teacher
Bridgett Lee's flattered when she finds a love letter in her mailbox, but then she finds out Demi Delia's getting the...
Where: Couch, Public Place
Categories: BGG, Big Fake Tits, Big Natural Tits, Blonde, Brunette, Glasses, Latina, MILFs, Petite, Piercings, Shaved, Tattoos, Threesome
Released: November 27, 2007
Carmella Bing & Alan Stafford in My First Sex Teacher
Carmella Bing is regularly nailing the Dean, but she's got her eye on her dorky TA Alan. He's extremely awkward in...
Categories: Big Ass, Big Fake Tits, Brunette, Glasses, MILFs, Shaved
Released: November 12, 2007
& Brooke Haven in My First Sex Teacher
Derrick’s having a hard time concentrating in Brooke Haven’s class … seriously, a very hard time. So he makes...
Who: Professor
Categories: Big Fake Tits, Blonde, Glasses, Petite, Tattoos
Released: November 05, 2007
Joslyn James, Zane & Lance Strong in My First Sex Teacher
Professor Joslyn James gets busted by some students for going to a rave over the weekend, and they have pictures of...
Categories: BBG, Big Ass, Big Fake Tits, Brunette, Glasses, MILFs, Petite, Tattoos, Threesome
Released: October 29, 2007
Sophia Lomeli & Jordan Ashley in My First Sex Teacher
Te amo, maestra, but, to be honest, I don't really care about school or this class. So Professor Sophia Lomeli is...
Categories: Big Fake Tits, Brunette, Glasses, Latina, MILFs, Piercings, Stockings
Released: October 22, 2007
Sky Taylor & Will Powers in My First Sex Teacher
Professor Sky Taylor takes her technology class very seriously, so when her student Will is fucking around making...
Categories: Big Fake Tits, Brunette, Glasses, MILFs, Shaved, Stockings
Released: October 15, 2007
Misty Vonage & Mikey Butders in My First Sex Teacher
Mikey has to admit. He didn't sign up for Misty Vonage's design class because he loves fashion. His outfit alone can...
Categories: Big Fake Tits, Blonde, Glasses, MILFs, Piercings, Shaved
Released: October 08, 2007
Cali Chase, Kitti Lynxxx & Mikey Butders in My First Sex Teacher
Mikey's been hearing around campus that TA Kitti Lynxxx has been sleeping around with faculty and students, but she...
Where: Desk
Categories: BGG, Big Ass, Big Fake Tits, Blonde, Glasses, MILFs, Piercings, Red Head, Shaved, Tattoos, Threesome
Released: October 02, 2007
Kitty Caulfield, Alex Gonz & Jack Venice in My First Sex Teacher
Jack had so much fun with Counselor Kitty Caulfield at his last appointment that, for this one, he brings a friend...
Where: Desk
Categories: BBG, Big Ass, Big Fake Tits, Glasses, MILFs, Petite, Red Head, Stockings, Threesome
Released: September 25, 2007
Panther, Vivica Coxx & Johnny Sins in My First Sex Teacher
These two fine ladies have it all figured out. When they're in the mood for young cock, Professor Ms. Panther calls...
Categories: BGG, Big Ass, Big Natural Tits, Black, Brunette, Petite, Shaved, Small Tits, Stockings, Threesome, Uniform
Released: September 21, 2007
Arianna LaBarbara & Jerry in My First Sex Teacher
It's Arianna LaBarbara's first day on the job, and she's already starting trouble. She got fired from her last job...
Categories: Big Fake Tits, Brunette, Glasses, MILFs, Shaved
Released: September 17, 2007
Puma Swede & Marcos Leon in My First Sex Teacher
Marco has a ski trip to Sweden coming up, so he signs up for a Swedish class, taught by the amazingly lovely Puma...
Categories: Big Fake Tits, Blonde, Glasses, MILFs, Shaved
Released: September 10, 2007
Carmella Bing, Shyla Stylez & Johnny Sins in My First Sex Teacher
Carmella Bing can't believe that Shyla Stylez would cheat on her ... with a student! And a guy student at that! But...
Who: Friend's Girlfriend, Professor, Student
Categories: BGG, Big Ass, Big Fake Tits, Blonde, Brunette, Glasses, MILFs, Shaved, Tattoos, Threesome
Released: September 04, 2007
Kayla Synz & Alex Gonz in My First Sex Teacher
Alex missed the book signing for Professor Kayla Synz's new book, so when he asks her to sign it after class, he...
Categories: Big Ass, Big Fake Tits, Blonde, Glasses, MILFs, Petite, Piercings, Shaved
Released: August 27, 2007
Morgan Ray & CJ Ryder in My First Sex Teacher
What a deal! Nurse Morgan Ray from the university's Health Services loves young college cock, and CJ thinks naughty...
Where: Desk
Categories: Big Fake Tits, Blonde, MILFs, Shaved, Stockings, Tattoos, Uniform
Released: August 20, 2007
Brooke Banner, Julia Ann & Justice Young in My First Sex Teacher
Over coffee one day in the teachers' lounge, Professors Julia Ann and Brooke Banner are discussing a student who is...
Categories: BGG, Big Fake Tits, Big Natural Tits, Blonde, Glasses, MILFs, Shaved, Tattoos, Threesome
Released: August 13, 2007
Druuna & Jack Venice in My First Sex Teacher
When Professor Druuna's summer fling walks in as a new student in her class, the tension is high but the sparks are...
Categories: Anal, Brunette, Glasses, Small Tits, Stockings
Released: August 06, 2007
Carolyn Reese, Samantha Ryan, Lexi Lamour & Jack Venice in My First Sex Teacher
When Jack is caught in the women's locker room, he gets in trouble with both Ms. Carolyn Reese and Ms. Lexi Lamour...
Who: Friend, Professor, Student
Where: Desk
Categories: Big Fake Tits, Big Natural Tits, Blonde, Foursome, Glasses, MILFs, Petite, Piercings, Shaved, Small Tits, Stockings, Tattoos
Released: July 30, 2007
Sarah Jessie & Trent Soluri in My First Sex Teacher
Trent's not doing so well in his math class, so he stays after class with his professor, Sarah Jessie. But when she...
Categories: Big Fake Tits, Blonde, Glasses, Latina, Piercings, Shaved, Stockings
Released: July 23, 2007
Lisa DeMarco & Alex Gonz in My First Sex Teacher
When Alex's parents won't pay for college, he goes to Financial Aid to see if Ms. Lisa DeMarco can help him pay his...
Where: Desk
Categories: Big Fake Tits, Blonde, MILFs
Released: July 20, 2007
Trina Michaels, Lachelle Marie & James Deen in My First Sex Teacher
This scene gives new meaning to "May I see you after class?" Too bad Clever and GOC don't get held after, too, but...
Who: Friend, Professor, Student
Categories: BGG, Big Ass, Big Fake Tits, Blonde, Brunette, Glasses, MILFs, Petite, Piercings, Shaved, Tattoos, Threesome
Released: July 13, 2007
Cameron Keys & Anthony Rosano in My First Sex Teacher
Professor Cameron Keys can't believe how poorly Anthony did on his final project when he says he spent 3 weeks on it...
Categories: Big Ass, Big Fake Tits, Blonde, Glasses, Piercings
Released: July 06, 2007
Liz Summers & Marcos Leon in My First Sex Teacher
Cooking 101 teacher Mrs. Summers has never seen a more inept student than Marcos, but he wants to learn how to cook...
Categories: Big Natural Tits, Blonde, MILFs, Shaved, Tattoos
Released: June 27, 2007
Kitty Caulfield & Jack Venice in My First Sex Teacher
Counselor Kitty Caulfield knows exactly what to do to help Jack get his grades up. His girlfriend dumped him and he...
Where: Desk
Categories: Big Ass, Big Fake Tits, Glasses, MILFs, Red Head, Stockings
Released: June 18, 2007
Tyann Mason & Kurt Lockwood in My First Sex Teacher
Aloha, Mr. Hand. Um, I mean ... Ms. Tyann Mason. Surfer guy Kurt figures if he has to stay after class, he might as...
Categories: Big Fake Tits, Blonde, Glasses, MILFs, Petite, Stockings
Released: June 13, 2007
Ava Devine, Kayden Faye & Christian in My First Sex Teacher
Of course Ava Devine is a Human Sexuality professor, and Kayden Faye is her protégé. And what do you know? Christian...
Categories: Asian, BGG, Big Ass, Big Fake Tits, Brunette, MILFs, Piercings, Shaved, Small Tits, Stockings, Tattoos, Threesome
Released: June 11, 2007
Sindy Lange, Roxy Anne & Mikey Butders in My First Sex Teacher
Professor Roxy Anne calls librarian Sindy Lange into her classroom to ask about the ridiculous help she's been giving...
Categories: BGG, Big Ass, Big Fake Tits, Blonde, Glasses, MILFs, Piercings, Shaved, Stockings, Tattoos, Threesome
Released: June 04, 2007
Katrina Isis, Christina Noir & Alex Gonz in My First Sex Teacher
What's better than fucking your English teacher? Fucking her and your Chemistry teacher at the same time! Alex goes...
Where: Public Place
Categories: BGG, Big Natural Tits, Brunette, Glasses, MILFs, Petite, Piercings, Red Head, Shaved, Small Tits, Tattoos, Threesome
Released: May 22, 2007
Darryl Hanah, Alana Evans & Kris Slater in My First Sex Teacher
Sharing is caring! When Professor Alana Evans walks in on Professor Daryl Hanah nailing a student in her classroom,...
Who: Friend's Girlfriend, MILF, Professor, Student
Categories: BGG, Big Fake Tits, Blonde, Glasses, MILFs, Petite, Small Tits, Stockings, Tattoos, Threesome
Released: May 16, 2007
Victoria Valentina & Derrick Pierce in My First Sex Teacher
Derrick's not too happy when he has to miss football practice to meet with his art teacher, Victoria Valentino, but...
Categories: Big Fake Tits, Brunette, MILFs, Piercings
Released: April 23, 2007
Carmella Bing, Aubrey Addams & Alan Stafford in My First Sex Teacher
When Alan can't make the grade to go on the Spring Break trip, he tries to seduce Professor Bing so she'll help him...
Categories: BGG, Big Ass, Big Fake Tits, Blonde, Brunette, Glasses, MILFs, Piercings, Shaved, Small Tits, Threesome
Released: April 16, 2007
Liv Wylder, Kara Nox & Alex Gonz in My First Sex Teacher
When Professor Kara Nox walks in on her students Liv Wylder and Alex going through her desk and realizes they've...
Categories: BGG, Big Natural Tits, Blonde, Glasses, MILFs, Red Head, Shaved, Small Tits, Stockings, Threesome
Released: April 11, 2007
Gabriella Rossi & Scott Nails in My First Sex Teacher
Scott feels he has the right to be a little cocky. After all, he has an influential father and a huge fucking cock,...
Categories: Big Fake Tits, Brunette, Glasses, MILFs
Released: April 03, 2007
Porscha Ride & Anthony Rosano in My First Sex Teacher
Anthony is working very hard as Porscha Ride's student teacher, so he hasn't even had time to fuck his girlfriend....
Categories: Blonde, Piercings, Shaved, Tattoos
Released: March 19, 2007
Kimberly Kole & Derrick Pierce in My First Sex Teacher
Professor Kimberly Kole is one sexy teacher who's feeling a lot of stress in her new job, but her student Derrick...
Categories: Big Fake Tits, Brunette, Glasses, Shaved
Released: March 12, 2007
Isabella Manelli & Trent Soluri in My First Sex Teacher
Professor Isabella Manelli loves that Trent spends so much time studying for her class, but he's blowing off his...
Categories: Big Ass, Big Fake Tits, Brunette, Glasses, MILFs, Shaved, Stockings, Tattoos
Released: March 06, 2007
& Summer Storm in My First Sex Teacher
Jordan has a crush on Professor Summer Storm, so he hides a secret message in his research paper, thinking she's too...
Categories: Big Ass, Blonde, Glasses, Small Tits, Stockings, Tattoos
Released: March 03, 2007
Lisa Sparxxx & Jerry in My First Sex Teacher
Jerry doesn't think it's right to fuck his teacher, but it's hard to refuse an ultimatum from his sexy mature teacher...
Categories: Big Natural Tits, Brunette, Glasses, MILFs, Shaved, Tattoos
Released: February 27, 2007
& Kylie Worthy in My First Sex Teacher
Jack's in a rush to get to his fraternity rush, so he has no time to help Professor Worthy, even though he's her TA....
Categories: Big Ass, Big Fake Tits, Blonde, Glasses, MILFs, Piercings, Shaved, Stockings
Released: February 12, 2007
& Heidi Mayne in My First Sex Teacher
Professor Mayne notices that Jack hasn't been motivated in class lately, so she whips out her big yummy breasts for...
Categories: Big Ass, Big Fake Tits, Blonde, Glasses, Piercings, Shaved, Tattoos
Released: February 09, 2007
Aline & Scott Nails in My First Sex Teacher
Professor Aline thinks that if Scott is going to miss tests and expect to make them up, he needs to give her...
Categories: Big Fake Tits, Blonde, MILFs, Piercings, Shaved, Stockings, Tattoos
Released: January 29, 2007
Carolyn Reese & Derrick Pierce in My First Sex Teacher
Professor Reese likes having naughty little boys do things for her, so when she catches Derrick cheating, she doesn't...
Categories: Big Ass, Big Natural Tits, Blonde, Glasses, MILFs, Stockings, Tattoos
Released: January 22, 2007
Mika Tan & Jeremy in My First Sex Teacher
Professor Mika Tan's been known to "pass for ass" so when John misses a week of class, he can either study hard to...
Categories: Asian, Big Fake Tits, Brunette, Stockings
Released: January 16, 2007
& Katrina Isis in My First Sex Teacher
Katrina Isis thinks Tommy is way too high strung to be her TA, but she has a great idea for how he can channel all...
Who: MILF, Professor, Stranger's Girlfriend, Student
Categories: Brunette, Glasses, Stockings
Released: January 08, 2007
Haley Paige, Milan & Trent Soluri in My First Sex Teacher
Haley Paige and Trent have an open relationship, so when they go into Professor Milan's class to make up a test, all...
Who: Married Woman, Professor, Student
Categories: BGG, Big Ass, Big Fake Tits, Big Natural Tits, Blonde, Brunette, Glasses, Hairy bush, Latina, MILFs, Piercings, Tattoos, Threesome
Released: January 02, 2007
& Adriana Anelise in My First Sex Teacher
Mikey is doing ok in Spanish, but he needs some extra help from Professor Analese. After a little vocabulary...
Categories: Big Fake Tits, Brunette, Glasses, MILFs, Shaved
Released: December 26, 2006
Alexis Silver & Alex Gonz in My First Sex Teacher
Music teacher Alexis Silver knows her student Alex has no talent for singing because he's tone deaf, but she thinks...
Categories: Big Ass, Big Natural Tits, Black, Brunette, MILFs, Piercings, Shaved, Stockings
Released: December 18, 2006
Diana Prince & Derrick Pierce in My First Sex Teacher
Derrick blames Professor Diana Prince for his bad grade because she always looks so sexy in class. How can he...
Categories: Big Fake Tits, Brunette, Glasses, MILFs, Piercings
Released: December 11, 2006
Austin Kincaid & Jeremy Holmes in My First Sex Teacher
There's that Jeremy, back in trouble again. This time he threw a frat party and has to become a teacher's assistant....
Categories: Big Fake Tits, Brunette, Glasses, MILFs
Released: December 04, 2006
Adriana Deville & Derrick Pierce in My First Sex Teacher
Mrs. Adriana Deville has the "hots" for the head coach and thinks the team's quarterback can help her out. Oh, he'll...
Who: Married Woman, MILF, Professor, Student
Categories: Brunette, Glasses, Piercings, Shaved, Small Tits, Tattoos
Released: November 27, 2006
Maya Divine & Alex Gonz in My First Sex Teacher
Wendy Divine can't wait for Alex to graduate because she has wanted to get her hands on him since day one. He thinks...
Categories: Big Ass, Big Fake Tits, Brunette, MILFs, Piercings, Stockings
Released: November 14, 2006
Amber Lynn & Jack Venice in My First Sex Teacher
Professor Amber Lynn is flattered that all the boys are running around campus acting like fools trying to impress...
Categories: Big Fake Tits, Blonde, MILFs
Released: November 06, 2006
& Devon Lee in My First Sex Teacher
It's Halloween, and who can resist a serenading penis doing the penis shuffle dance? Certainly not Professor Lee, who...
Categories: Big Ass, Big Fake Tits, Blonde, Glasses, MILFs, Piercings
Released: October 31, 2006
& Kayla Raynes in My First Sex Teacher
Professor Raynes was told she would have a TA while substituting, so she thought she would get some help grading...
Categories: Big Natural Tits, Brunette, Curvy, Glasses, MILFs, Stockings
Released: October 23, 2006
& India Summer in My First Sex Teacher
Kris just transferred from community college and it's his first day at a real four year school. He wants Mrs. Summer...
Categories: Brunette, MILFs, Piercings, Small Tits
Released: October 16, 2006
& Milan in My First Sex Teacher
Milan just made the jump from Elementary to Higher Education and is a little nervous ...she's never been surrounded...
Categories: Big Fake Tits, Blonde, Glasses, MILFs, Piercings, Stockings, Tattoos
Released: October 10, 2006
& Amber Star in My First Sex Teacher
Aaron has a year of school under his belt and has adjusted his priorities from being brainy to babes and booze! Amber...
Categories: Blonde, Glasses, MILFs, Shaved, Small Tits
Released: October 02, 2006
& Baby Jayne in My First Sex Teacher
Baby Jane's "teacher of the year" expos' leads Jeremy to ask her out. As a responsible educator, Baby Jane will only...
Categories: Big Ass, Big Fake Tits, Brunette, Glasses, Piercings, Stockings
Released: September 25, 2006
Sara Jay & Danny Wylde in My First Sex Teacher
Sara Jay is a pretty giving professor so she's been letting Daniel "cat nap" in her classroom since his dorm mates...
Who: MILF, Professor, Stranger's Girlfriend, Student
Categories: Big Ass, Big Fake Tits, Blonde, Glasses, MILFs, Shaved, Tattoos
Released: September 18, 2006
Gina Lynn & Derrick Pierce in My First Sex Teacher
Derrick never gives Gina Lynn problems in her class but when she hears how unruly he is in her husband's class she's...
Who: Married Woman, Professor, Student
Categories: Big Ass, Big Fake Tits, Blonde, Glasses, Petite, Stockings
Released: September 11, 2006
TJ Hart & Derrick Pierce in My First Sex Teacher
Professor Hart can't figure out why Derrick stays after class for tutoring when he aces all the tests, but she soon...
Categories: Big Fake Tits, Blonde, Glasses, MILFs, Stockings
Released: September 05, 2006
Adriana Deville & Scott Nails in My First Sex Teacher
When you're a professor as tan and as fit as Adriana Deville, you could give a fuck when your man isn't putting 110%...
Categories: Brunette, Glasses, Piercings, Shaved, Small Tits, Tattoos
Released: August 28, 2006
Selena Steele, Christie Lee & Matt Bixel in My First Sex Teacher
How many times do a couple of Professors let the student body in on their personal sexploit, much less bring them...
Who: Friend, Professor, Student
Categories: BGG, Big Fake Tits, Brunette, Glasses, Hairy bush, MILFs, Small Tits, Stockings, Threesome
Released: August 14, 2006
& Nicole Moore in My First Sex Teacher
Mrs. Moore is upset because her favorite student has been saying she's a huge pushover. Well, the only way to solve...
Categories: Big Natural Tits, Blonde, Glasses, MILFs, Piercings, Shaved
Released: August 07, 2006
& Simone Riley in My First Sex Teacher
Kris can't take his mind off of pussy but Professor Simone Riley is going to help him find some balance and teach him...
Categories: Big Fake Tits, Brunette, Glasses, MILFs, Stockings
Released: July 31, 2006
Lori Lust & Anthony Rosano in My First Sex Teacher
There're people who go to college to get drunk and laid. There're people who go for the education. And then there're...
Categories: Big Fake Tits, Blonde, Glasses, MILFs
Released: July 24, 2006
& Rachel Luv in My First Sex Teacher
Mrs. Luv is the teacher and Kris is the student, it's that simple. He needs to pass this class and she needs to get...
Categories: Brunette, MILFs, Piercings, Shaved, Small Tits
Released: July 17, 2006
Shannon Kelly & Alex Gonz in My First Sex Teacher
Mrs. Shannon Kelly doesn't like the way Alex tries to dominate her class. She's gonna' teach him a lesson he'll...
Categories: Big Fake Tits, MILFs, Petite, Piercings, Red Head, Tattoos
Released: July 11, 2006
Anjelica Lauren & Jeremey Holmes in My First Sex Teacher
Jeremy Holmes is habitually tardy and Professor Anjelica Lauren has had it up to her eyeballs with all his bullshit....
Categories: Anal, Big Fake Tits, Brunette, Glasses, MILFs, Shaved, Stockings, Tattoos
Released: July 06, 2006
Trisha & Jeremy Holmes in My First Sex Teacher
The "newbie" always gets roughed up ... even the new professor. Professor Trisha knows this and solicits the help of...
Categories: Big Fake Tits, Brunette, Glasses, Hairy bush
Released: June 26, 2006
Andrea Jaxxx & Trent Soluri in My First Sex Teacher
Trent has come a long way in class and is now quite the cunning linguist. Professor Andrea Jaxxx finds this to be...
Categories: Big Fake Tits, Blonde, MILFs, Petite
Released: June 19, 2006
& Devon Michaels in My First Sex Teacher
Tyler Knight just received his teaching credentials and, as luck would have it, landed a position at his old Alma...
Categories: Big Fake Tits, Brunette, MILFs, Petite
Released: June 12, 2006
Chelsea Zinn & Donny Long in My First Sex Teacher
The nerve of some students - thinking that they can skate thru class because the teacher is a family friend. Chelsea...
Who: MILF, Mom's Friend, Professor, Student
Categories: Blonde, Glasses, Petite, Shaved, Small Tits
Released: June 05, 2006
Niki Wylde & TJ Cummings in My First Sex Teacher
TJ Cummings is the university's "big baller" and is taking advantage of that and the fact that his uncle is the dean....
Categories: Big Fake Tits, Blonde, Glasses, Shaved, Stockings
Released: May 30, 2006
Regan Anthony & Alex Gonz in My First Sex Teacher
Mrs. Anthony is sick and tired of being taken advantage of. She needs help around the classroom and Alex is going to...
Categories: Anal, Big Fake Tits, Blonde, Glasses, MILFs, Stockings
Released: May 22, 2006
India Summer & TJ Cummings in My First Sex Teacher
TJ Cummings has been attending college for 7 years now and Mrs. India Summer is determined to motivate him to get the...
Categories: Brunette, Glasses, MILFs, Small Tits, Stockings
Released: May 15, 2006
& Ludy in My First Sex Teacher
Mrs. Ludy is very jealous that Jack is taking out another teacher. She is pretty hot and is very good at sucking...
Categories: Asian, Big Fake Tits, Blonde, Glasses, Petite, Piercings, Tattoos
Released: May 08, 2006
Tyler Faith & Scott Nails in My First Sex Teacher
Scott has a really bad hangover and it's not the first time! Mrs. Faith has realized one thing and that is this -...
Categories: Big Fake Tits, Blonde, Glasses, Petite, Piercings, Stockings, Tattoos
Released: May 01, 2006
Lauren Kain & Donny Long in My First Sex Teacher
Mrs. Kain is really disappointed with her student Donny. He thinks just because he fucked Mrs. Kain and her...
Categories: Big Fake Tits, Blonde, Glasses, MILFs, Piercings, Shaved
Released: April 24, 2006
Veronica Rayne & Alex Gonz in My First Sex Teacher
Alex will never get Professor Veronica Rayne's class and she isn't offering any extra credit but she may consider a...
Categories: Big Natural Tits, Brunette, Curvy, MILFs, Piercings
Released: April 17, 2006
Cynthia Pendragon & Travis Lee in My First Sex Teacher
Professor Pendragon conducts her classroom with old-school flair. So when Travis Lee is disobedient it's off to the...
Categories: Big Fake Tits, Brunette, Glasses, MILFs
Released: April 10, 2006
Carrie Ann & Travis Lee in My First Sex Teacher
Poor Travis Lee got dumped and is having a hard time maintaining focus in class. Professor Carrie Ann runs her...
Categories: Big Ass, Big Fake Tits, Brunette, Glasses, MILFs, Piercings, Shaved, Tattoos
Released: April 03, 2006
Carmen Hayes & Justin Syder in My First Sex Teacher
Professors Carmen Hayes and Justin Syder are having a secret affair. Unfortunately, a mouthy student catches Carmen...
Categories: BBG, Big Ass, Big Natural Tits, Black, Brunette, Glasses, Shaved, Stockings, Tattoos, Threesome
Released: March 27, 2006
Lauren Kain & Darryl Hanah in My First Sex Teacher
Professors Lauren Kin and Darryl Hannah have all kinds of secrets - most notably, a lesbian love affair. But that...
Categories: BGG, Big Fake Tits, Blonde, Glasses, Petite, Piercings, Shaved, Small Tits, Tattoos, Threesome
Released: March 20, 2006
& Devon Lee in My First Sex Teacher
Will is on the ball team and is dating Professor Devon Lee's niece. Professor Lee doesn't approve of this and is...
Categories: Big Ass, Big Fake Tits, Blonde, Glasses, MILFs, Piercings
Released: March 16, 2006
Sandy Simmers & Donny Long in My First Sex Teacher
For Professor Sandy Simmers, manners and respect for authority and your peers is just as important as your GPA. Donny...
Categories: Big Fake Tits, Blonde, Glasses, MILFs, Shaved
Released: March 09, 2006
Danielle Derek & Trent Soluri in My First Sex Teacher
Trent has dreams of a career in the medical field but is failing miserably in Anatomy 101. Professor Danielle Derek...
Categories: Big Fake Tits, Blonde, Glasses, MILFs, Petite, Shaved
Released: March 03, 2006
Ginger Lea & Vincent Vega in My First Sex Teacher
Professor Ginger Lea taught Vincent everything he knows about couple's counseling. Well, at least that's what he...
Categories: Big Fake Tits, MILFs, Petite, Red Head, Shaved
Released: February 23, 2006
Bailey O'dare & Johnny Irons in My First Sex Teacher
Johnny Irons has missed two weeks of Mrs. Bailey O'Dare's class and has no excuses except that his girlfriend keeps...
Categories: Big Fake Tits, Glasses, MILFs, Piercings, Red Head, Shaved, Stockings
Released: February 16, 2006
Lisa Ann & Derrick Pierce in My First Sex Teacher
Mrs. Ann has all kinds of bones to pick with one particular student, Derrick. From his grades to his attitude to the...
Categories: Big Ass, Big Fake Tits, Brunette, Glasses, MILFs, Piercings
Released: February 02, 2006
& Saskia in My First Sex Teacher
Mrs Saskia is looking for some young cock to fuck and she's in the perfect position to get what she wants. She sees a...
Categories: Big Tits, Blow Job, Brunette, Facial, Fake Tits, High Heels, MILFs
Released: January 27, 2006
Diana Doll & Anthony Rosano in My First Sex Teacher
Mid-terms are just around the corner but Anthony is going to be his best friend's best man that same week. This poses...
Categories: Big Ass, Big Natural Tits, Blonde, Foreign Accent, MILFs, Tattoos
Released: January 26, 2006
Selena Steele & Trent Soluri in My First Sex Teacher
Trent sucks at History; so does his History professor, Mrs. Steele ... literally! You'll wish all your professors...
Categories: Big Fake Tits, Brunette, Glasses, Hairy bush, MILFs, Stockings
Released: January 19, 2006
Midori & Kyle Moore in My First Sex Teacher
What's all the fuss about not making an 'A?' Everyone knows that the 'A' students work for the 'B' students and 'C'...
Categories: Big Fake Tits, Black, Brunette, MILFs, Petite, Shaved, Stockings
Released: January 12, 2006
& Veronica Rayne in My First Sex Teacher
Professor Rayne is tired of the dating scene. All she wants is to get laid but no one is putting out. Maybe she...
Where: Classroom
Categories: Big Natural Tits, Brunette, MILFs, Piercings, Small Tits
Released: January 05, 2006
& Allison Kilgore in My First Sex Teacher
Ladies are attracted to a certain type of attitude. Usually, that's the smug, arrogant type. Mrs. Wesley doesn't...
Categories: Big Tits, Blonde, Fake Tits
Released: December 19, 2005
& Adrianna Nicole in My First Sex Teacher
Showing up late to class, disruptive behavior and not turning in assignments is a guaranteed formula for disaster at...
Categories: BBG, Big Ass, Big Natural Tits, Blonde, Glasses, Shaved, Stockings, Tattoos, Threesome
Released: December 15, 2005
& Bianca in My First Sex Teacher
Will drops by Mrs. B's office to thank her for inspiring him to pursue an exciting career in Social Work. He also has...
Categories: Big Ass, Blonde, Glasses, MILFs, Petite, Shaved, Small Tits
Released: December 08, 2005
& Emma Starr in My First Sex Teacher
Will is having a difficult time interpreting business trends; ups and downs of the Market. Lucky for him, Mrs. Starr...
Categories: Big Fake Tits, Blonde, MILFs, Piercings, Stockings, Tattoos
Released: December 01, 2005
Kitty Lee & Kyle Moore in My First Sex Teacher
Mrs. Lee has watched Kyle oogle her tits and walk around with a hard-on for them since the first day of class. Well,...
Who: MILF, Professor, Stranger's Girlfriend, Student
Categories: Big Ass, Big Natural Tits, Blonde, Glasses, MILFs
Released: November 23, 2005
& Chelsea Zinn in My First Sex Teacher
magine Mrs. Zinn's dismay when she discovers that her favorite student, whom she has been grooming since freshman...
Categories: Blonde, Glasses, Petite, Shaved, Small Tits, Stockings
Released: November 17, 2005
& Mason Storm in My First Sex Teacher
Frank is a star athlete and BIG man on campus but needs a date for the awards ceremony. He has his eye set on...
Where: Classroom
Categories: BGG, Big Fake Tits, Brunette, MILFs, Petite, Piercings, Shaved, Small Tits, Threesome
Released: November 10, 2005
& April Blossom in My First Sex Teacher
Kris has been concentrating on his band, not class. Mrs. Blossom, reminiscing about her reckless youth, figures a...
Categories: Big Natural Tits, Brunette, Glasses, Petite, Tattoos
Released: November 03, 2005
Stephanie Tripp & Trent Soluri in My First Sex Teacher
When Trent shows up to Saturday Detention with just a pillow it sends Mrs. Tripp over the edge. She tacks on an...
Categories: Big Fake Tits, Brunette, Glasses, Petite
Released: October 27, 2005
Davia Ardell & Jason Cox in My First Sex Teacher
Professor Ardell gets more student cock than the football locker room ... all except for the overachieving Jason...
Categories: Anal, Big Fake Tits, Blonde, Petite, Piercings, Tattoos
Released: October 20, 2005
& Serena Sinn in My First Sex Teacher
Serena has been participating in extracurricular activities with the dean's son, Kyle. For fear of wrecking her...
Who: Married Woman, MILF, Professor, Student
Categories: Big Fake Tits, Blonde, Glasses, Tattoos
Released: October 13, 2005
Jezebelle Bond & Veronica Stone in My First Sex Teacher
Mrs. Bond is disappointed in her student, Veronica, because she has been failing her classes. Once an "A"...
Categories: BGG, Brunette, Glasses, Petite, Shaved, Small Tits, Tattoos, Threesome
Released: October 06, 2005
Loni & Phoenix Ray in My First Sex Teacher
Loni's leaving her position as Mrs. Phoenix's assistant. They need to replace Loni with a person equal to her...
Categories: Asian, BGG, Big Natural Tits, Blonde, Brunette, Glasses, MILFs, Piercings, Threesome
Released: September 22, 2005
& Betty O. in My First Sex Teacher
Mrs. O has a little problem on her hands. It seems one of her students is dating her daughter and he is also cheating...
Categories: Brunette, Glasses, MILFs, Shaved, Small Tits, Stockings
Released: September 15, 2005
& Trixie in My First Sex Teacher
Mrs. Trixie just got a job as a teacher but she also works as a stripper. She has to keep this quiet. One of her...
Categories: Big Fake Tits, Brunette, Glasses, Shaved
Released: September 08, 2005
& Isabella Love in My First Sex Teacher
Mrs. Love is going through a tough divorce and it's really affecting her teaching. Her favorite student came by to...
Categories: Big Ass, Brunette, Glasses, Small Tits
Released: September 01, 2005
& Charlee Chase in My First Sex Teacher
Andrew got some information from his frat buddy and goes to the teacher to confess something but it turns out that...
Categories: Big Ass, Big Fake Tits, Blonde, Glasses, MILFs, Shaved
Released: August 04, 2005
Jennifer Steele & Trent Soluri in My First Sex Teacher
Trent feels like he got ripped off because he only recieved a "B". But, just like Mrs. Steele says...
Categories: Anal, Big Ass, Big Fake Tits, Blonde, Hairy bush, MILFs, Petite, Stockings, Tattoos
Released: July 28, 2005
Allison Kilgore & James Deen in My First Sex Teacher
Mrs. Wesley is a little upset. The student she's privately "tutoring" brought one of his friends in to get...
Who: Friend, MILF, Professor, Student
Categories: BBG, Big Tits, Blonde, Fake Tits, Glasses, MILFs, Stockings, Threesome
Released: July 21, 2005
Devon Michaels & Matt Bixel in My First Sex Teacher
Mrs. Michael's is furious because one of her students got her sex buddy fired. Now what's she supposed to do. She...
Where: Classroom
Categories: Big Fake Tits, Brunette, Glasses, MILFs, Petite, Stockings
Released: July 14, 2005
& Bethany Sweet in My First Sex Teacher
Mrs. Sweet's student is really turned on by her and he was just wondering if he could have sexual relations with her....
Who: Married Woman, MILF, Professor, Student
Where: Classroom
Categories: Blonde, Glasses, MILFs
Released: July 07, 2005
& Angelica Sin in My First Sex Teacher
Mrs. Sanders had a late night last night and forgot about her tutoring lessons. She can make it up to her students by...
Where: Bedroom
Categories: BBG, Big Fake Tits, Brunette, MILFs, Threesome
Released: June 30, 2005
& Leigh in My First Sex Teacher
Mrs. Leigh is playing a little joke on one of her students. She really brought him in because she's so horny and...
Where: Classroom
Categories: Big Fake Tits, Blonde, Glasses, MILFs, Shaved
Released: June 23, 2005
& Mason Storm in My First Sex Teacher
Mrs. Storm doesn't want her prize student to lose his 4.0 grade average bacause of his poor attendence. So, she...
Categories: Big Fake Tits, Brunette, MILFs, Shaved, Tattoos
Released: June 16, 2005
& Charlee Chase in My First Sex Teacher
Mrs. Chase is upset with Jake for lying about being at a funeral during a test, and she also caught him cheating...
Categories: Big Fake Tits, Blonde, MILFs, Shaved
Released: June 09, 2005
& Regan Starr in My First Sex Teacher
Jake thinks that he will be able to pass Mrs.Starr's physiology class because she's best friends with his aunt. Well...
Categories: Blonde, Glasses, Shaved
Released: May 26, 2005
& Eden in My First Sex Teacher
Mrs. Eden see's that her student is really having a tough time with the opposite sex and she's willing to help. He's...
Where: Couch, Living room
Categories: Big Ass, Big Natural Tits, Glasses, MILFs, Red Head, Stockings
Released: May 12, 2005
& Jennifer Steele in My First Sex Teacher
Mrs. Steele's student has barley been to class and he also forgot to turn in his paper. He doesn't want to do any of...
Who: Married Woman, MILF, Professor, Student
Where: Classroom
Categories: Big Fake Tits, Blonde, Hairy bush, MILFs, Petite, Stockings, Tattoos
Released: May 05, 2005
Jada Fire & Trent Soluri in My First Sex Teacher
It looks like Mrs. Fire is finally getting married, but she has really grown attached to one of her students. It's...
Who: Friend, Professor, Student
Where: Classroom
Categories: Anal, Big Ass, Big Tits, Black, Brunette, Fake Tits, Piercings, Tattoos
Released: April 28, 2005
& Dillan Lauren in My First Sex Teacher
Mrs. Lauren has a little problem on her hands. One of her students is disrespecting her! It's total garbage. He...
Who: Professor
Categories: Big Ass, Black Hair, Blow Job, Deepthroating, Facial, Foot Fetish, MILFs, Piercings, Tattoos
Released: April 25, 2005
Lezley Zen & James Deen in My First Sex Teacher
It seems one of Mrs. Zen's students just took her class because he heard it's easy. Well to pass Mrs. Zen's class you...
Categories: Big Fake Tits, Brunette, Glasses, Hairy bush, MILFs, Tattoos
Released: April 21, 2005
Ava Ramon & Trent Soluri in My First Sex Teacher
Mrs. Ramon is very upset with her current student. He's walking around campus with this "Ivy leauge"...
Categories: Brunette, Glasses, Latina, Piercings, Small Tits
Released: April 18, 2005
& Mya Luanna in My First Sex Teacher
Mrs. Luanna has agreed to help one of her students raise his GPA. She also finds him to be quite fuckable. He is...
Where: Couch, Living room
Categories: Asian, Brunette, Small Tits, Tattoos
Released: April 14, 2005
Kylie Worthy & Trent Soluri in My First Sex Teacher
Mrs. Worthy is very upset, it seems one of her students has been looking at her in a very naughty way. She's not...
Categories: Big Ass, Big Fake Tits, Blonde, Glasses, MILFs, Shaved, Stockings
Released: April 11, 2005
& Angelina Hart in My First Sex Teacher
Jim is really in a jam today, he hasn't studied for the midterm and he really needs to pass. He desides to steal the...
Categories: Blonde, Shaved, Small Tits
Released: March 31, 2005
Ms. Leigh & Sergio in My First Sex Teacher
Ms. Leigh is doing some student teaching evaluations, and it looks like one of her students isn't going to pass. He...
Categories: Anal, Blonde, MILFs, Shaved
Released: March 24, 2005
& Sara Jay in My First Sex Teacher
Ms. Jay's math student is early for his lesson this week. He's going to have to wait because she's finishing up in...
Where: Bathroom
Categories: Big Ass, Big Fake Tits, Blonde, MILFs, Shaved, Tattoos
Released: March 17, 2005
Lori Lust & Christian in My First Sex Teacher
Mrs. Lust has a new student who's having trouble with history class. Instead of teaching him history she would rather...
Where: Couch, Living room
Categories: Big Ass, Big Fake Tits, Blonde, MILFs
Released: March 10, 2005
Jennifer Steele & Christian in My First Sex Teacher
Mrs Steele is looking for a date, so she calls an escort service. A former student from the local community college...
Where: Bedroom
Categories: Big Fake Tits, Blonde, Hairy bush, MILFs, Stockings
Released: February 24, 2005
Ivory Anderson & Trent Soluri in My First Sex Teacher
Mrs Anderson is making a serious attempt to help her student study for an exam. Too bad that her student is making a...
Who: Married Woman, MILF, Professor, Student
Where: Couch, Living room
Categories: Blonde, Glasses, MILFs, Shaved, Small Tits, Stockings
Released: February 17, 2005
Angelica Sin & Trent Soluri in My First Sex Teacher
One of Mrs. Sanders' male students is having a private tutoring session with her and she can tell how shy he is. To...
Where: Couch, Living room
Categories: Big Fake Tits, Brunette, MILFs
Released: February 03, 2005
Chennin Blanc & Trent Soluri in My First Sex Teacher
Mrs. Clemens brings in a student who she feels has been having personal problems which is reflecting his school work....
Categories: Big Ass, Big Fake Tits, Blonde, Glasses, MILFs, Piercings, Tattoos
Released: January 20, 2005
& Brandee in My First Sex Teacher
A student in Mrs. Swartz's sex ed class isn't doing well so she asks a fellow teacher for some advice. It turns out...
Where: Office, Public Place
Categories: Big Fake Tits, Brunette, Glasses, MILFs, Stockings
Released: January 06, 2005
Emma Starr, Harmony & Trent Soluri in My First Sex Teacher
A cheerleader in Mrs. Starr's class hasn't been attending and she wants to get her grades up. Luckily, another...
Categories: Big Fake Tits, Blonde, Foursome, MILFs, Small Tits
Released: December 16, 2004
& Lexi Lamour in My First Sex Teacher
Jack is getting an A in Mrs. Lamour's physics class, but books aren't the only thing he wants to tackle. Watch Mrs....
Categories: Big Fake Tits, Blonde, MILFs, Tattoos
Released: December 02, 2004
& Carmen Hayes in My First Sex Teacher
After catching her student sleeping in class, Mrs. Hayes decides to let her student make it up to her by giving her...
Categories: Big Ass, Big Natural Tits, Black, Brunette, Glasses, Piercings, Shaved
Released: November 04, 2004
Mason Storm & Jassie in My First Sex Teacher
Mrs. Storms student is told to take some notes but when she pulls out what she thought was a pen, Mrs. Storm gets...
Categories: Asian, Big Fake Tits, Brunette, MILFs, Shaved, Small Tits, Tattoos
Released: October 21, 2004
& Cynthia Pendragon in My First Sex Teacher
Mrs. Pendragon decides to "help" a student get better grades in class!
Who: Friend's Girlfriend, MILF, Professor, Student
Categories: Big Fake Tits, Brunette, GG, Girl on Girl, Lesbian, MILFs, Shaved, Small Tits
Released: October 14, 2004
& Stacy Fillmore in My First Sex Teacher
Mrs. Filmore is feeling a little apprehensive. Her husband has been hounding her lately, he wants to try anal. She...
Categories: Anal, Big Fake Tits, Glasses, MILFs, Red Head, Shaved, Stockings
Released: October 01, 2004
& Mrs. Cummings in My First Sex Teacher
Mrs. Cummings gets invited to lunch by a student, but it turns into a little more the just a simple lunch break! See...
Categories: Big Ass, Big Fake Tits, Brunette, Glasses, Hairy bush, MILFs, Piercings
Released: September 16, 2004
& McQueen in My First Sex Teacher
Relaxation - I was feeling really stressed out about the debate that was comming up. I felt like I just wasn't...
Categories: Big Natural Tits, Brunette, Piercings
Released: July 15, 2004
& Stacy Fillmore in My First Sex Teacher
She really needs some sexual relief so after giving him an F on his paper she lets him make it up to her!
Who: Married Woman, MILF, Professor, Student
Categories: Big Fake Tits, Glasses, MILFs, Red Head, Shaved, Stockings
Released: July 04, 2004
& Dana Hayes in My First Sex Teacher
Raising Grades - My friend and I were trying to raise his grade in Mrs. Hayes class. I've had my experience with her...
Categories: BBG, Big Natural Tits, Blonde, Glasses, Hairy bush, MILFs, Stockings, Threesome
Released: June 24, 2004
& Mason Storm in My First Sex Teacher
Spanish #2 - I went to see Mrs. Storm to see if she could help me out with my Spanish. She agreed to give me a little...
Categories: Big Fake Tits, Brunette, MILFs, Shaved, Tattoos
Released: June 10, 2004
& Lisa Sparxxx in My First Sex Teacher
Mrs. Cannon is another one of those teachers. Trying to get me caught up. She said I cheated on an exam and my...
Where: Classroom
Categories: Big Natural Tits, Blonde, MILFs, Shaved, Tattoos
Released: June 01, 2004
& Frost in My First Sex Teacher
Lack Of Focus - Another day another teacher complaining about my lack of focus in her class. Ms. Frost is my Spanish...
Categories: Big Ass, Big Natural Tits, Blonde, Glasses, MILFs
Released: May 21, 2004
& Angelica Sin in My First Sex Teacher
Just Rewards - Mrs. Sanders is a psychology teacher trying to get me to better understand BF Skinner and his theories...
Categories: Anal, Big Fake Tits, MILFs, Stockings
Released: May 07, 2004
& Stock in My First Sex Teacher
Desk Work - Mrs. Stock was giving me a hard time with class as usual. I came to have a meeting with her, hopefully it...
Categories: Blonde, Hairy bush, MILFs
Released: April 16, 2004
& Taft in My First Sex Teacher
Jack is bombing out of his web design class. He was too shy to ask Mrs. Taft for the extra help that he obviously...
Categories: Big Natural Tits, Blonde, MILFs, POV, Shaved
Released: April 12, 2004
Lisa DeMarco & James Deen in My First Sex Teacher
Lisa has a new student drop by the gym, she's supposed to help loosen him up for track. The track coach said he is...
Where: Gym, Public Place
Categories: Big Fake Tits, Blonde, MILFs, Piercings, Tattoos
Released: April 09, 2004
& Emma Starr in My First Sex Teacher
Double Major - We were getting ready for practice and Mrs. Starr came to talk to us about our grades. Damn why is she...
Categories: BBG, Big Fake Tits, Blonde, Glasses, MILFs, Piercings, Stockings, Tattoos, Threesome
Released: April 02, 2004
& Dana Hayes in My First Sex Teacher
Everyone loved Mrs. Hayes, even though she was a lot older than some of the other teachers, she was totally cool!...
Categories: Big Natural Tits, Blonde, Glasses, Hairy bush, MILFs, Stockings
Released: March 26, 2004
& Lisa Sparxxx in My First Sex Teacher
I never liked going to Mrs Cannons class, too much other work I'd always have to do. And then she thought she caught...
Where: Classroom
Categories: Big Ass, Big Natural Tits, Blonde, Glasses, MILFs, Shaved, Tattoos
Released: March 19, 2004
Emma Starr & Samantha in My First Sex Teacher
Lounge Lezbos - We were just sitting there studying, when all of a sudden she starts talking about being with other...
Where: Classroom, Couch, Teacher\'s lounge
Categories: BGG, Big Fake Tits, Blonde, MILFs, Piercings, Tattoos, Threesome
Released: March 12, 2004
Ms. Charms & Billy Banks in My First Sex Teacher
After Class - Ms. Charms has been riding me about my grades for sometime now. She didn't realize how hard it is to be...
Categories:
Released: March 05, 2004
& Diamond Foxxx in My First Sex Teacher
Geography X - Ya know, it always pissed me off that Mrs. Diamond kept me after class... I wasn't that much of a fuck...
Categories: Big Fake Tits, Blonde, Glasses, MILFs, Stockings
Released: February 20, 2004
Samantha St. James & James in My First Sex Teacher
Mrs. James was always breaking my balls and I couldn't figure out why. So one day after class I decided to ask her...
Categories: Big Ass, Big Fake Tits, Brunette, Glasses, Hairy bush, Stockings
Released: February 13, 2004
& Candy Vegas in My First Sex Teacher
Mr. Hanson has missed 35 days this semester and graduation is in 2 weeks. This class is a requirement for all...
Categories: Big Fake Tits, Brunette, Latina, MILFs, Shaved, Stockings
Released: February 06, 2004
& Raven Wolfe in My First Sex Teacher
Hard Bargain - I was totally fucked, like my ass stuck in accounting forever fucked! 5 Days till end of semester and...
Categories: Brunette, POV, Shaved, Tattoos
Released: January 30, 2004
& Emma Starr in My First Sex Teacher
Categories: Big Fake Tits, Blonde, MILFs, Shaved
Released: January 23, 2004
& Sammy Sparks in My First Sex Teacher
Make Up Work - Ms. Sparx is a tough teacher, and I guess that's why I never knew she had such a killer body. When I...
Categories: Big Fake Tits, Blonde, MILFs, Petite, Piercings, POV, Stockings
Released: January 16, 2004
& Michelle in My First Sex Teacher
Janitor Duties - Being a janitor has it's perks, tons of free stuff, all the gossip, and no one ever bugging you! So...
Where: Classroom, Desk, Office
Categories: Big Fake Tits, Blonde, Glasses, MILFs, Shaved
Released: January 09, 2004
& Vicki Vogue in My First Sex Teacher
Sex Ed Tutor - Man I must be a real idiot! I study and still I'm failing French Class! Well I needed to pass the...
Who: Married Woman, MILF, Professor, Student
Categories: Big Tits, Blonde, Blow Job, Facial, Fake Tits, Glasses, Mature, MILFs, Stockings
Released: December 26, 2003
& Emma Starr in My First Sex Teacher
Home Tutor - Failing a class is a real bitch. I needed a tutor fast. Luckily Mrs. Starr offered in home sessions, so...
Who: Married Woman, MILF, Professor, Student
Where: Bedroom, Couch, Living room
Categories: Big Fake Tits, Blonde, Glasses, MILFs
Released: December 19, 2003
& Sunny Shores in My First Sex Teacher
Health Class - Health class used to suck ass until Mrs. Shores took over! I must have a serious throb for older...
Categories: Big Natural Tits, Blonde, Glasses, MILFs, Tattoos
Released: December 12, 2003
& Smith in My First Sex Teacher
Study Hall - Study Hall has got to be the biggest waste of time... A man can go crazy sitting in there for too long!...
Categories: Blonde, MILFs, Piercings, Shaved, Small Tits, Stockings
Released: December 05, 2003
& Chennin Blanc in My First Sex Teacher
Detention - I always wondered if Mrs. Clemens wore panties under her short skirts, I couldn't tell, even when she sat...
Where: Desk
Categories: Blonde, MILFs, Tattoos
Released: November 28, 2003
& Nicole Moore in My First Sex Teacher
Mrs. Moore has wanted to fuck her son's friend Travis for a long time. When Travis brings home her son's car, she...
Categories: Big Natural Tits, Blonde, Glasses, MILFs, Shaved, Stockings
Released: November 14, 2003
& Cynthia Pendragon in My First Sex Teacher
Understanding - Mrs. Pendragon was trying to get me to understand literature and the great films of all time. I don't...
Categories: Big Ass, Big Fake Tits, Brunette, Hairy bush, MILFs
Released: November 07, 2003
& Dana Hayes in My First Sex Teacher
Deep Throat - Everyone loved Mrs. Hayes, even though she was a lot older than some of the other teachers, she was...
Categories: Big Natural Tits, Blonde, Glasses, MILFs, Shaved, Stockings
Released: November 07, 2003
& Carol in My First Sex Teacher
Pussy Licking - She used to say "If you can't use your mouth correctly, then no one will listen!" We all...
Categories: Big Ass, Brunette, MILFs, Shaved, Small Tits, Stockings, Tattoos
Released: October 31, 2003
& Rubee Tuesday in My First Sex Teacher
Missionary - Mrs. Nichol was a well seasoned teacher. She's instructed at the school for a good many years. Allot of...
Where: Classroom
Categories: Big Ass, Big Natural Tits, MILFs, Red Head, Stockings
Released: October 15, 2003
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