Sort by
Relevancy

Free Stories

83%
Teacher Student Confidentiality
It was raining cats and dogs outside as Ms. Catherine Walker (Cat by her friends) graded her Accelerated Integrated Geometry test scores. Her was long and flowing and her sweater was purposely pulled low to embarrass the male teachers with her cleavage. Her cock twitched as she shifted her leg to a ... Read full Story
shemale lover 2012-02-11 14,597 anal Blowjob black fiction
100%
The Biology of Music - I fucked my trans substitute teacher
I was never strong in school. I wasn't very interested in what we were being taught, and the teachers liked me enough to not give me too hard a time about it. I attended an all boys school. It was actually quite a religious school which makes this story all the more surprising. I was in the middle c... Read full Story
terrifictim 2022-01-03 4,321 Creampie Guy Fucks Shemale feet licking first time with a tranny teacher student
50%
Eromenon vs mature whore
An eromenon for a mature whore When I looked up to see whose mannequin hands was serving my, I was surprised to find a girly-boy: ‘Something else,’ (s)he smiled, dragging his/her long, colourless varnished fingers across the tablecloth. I couldn't hold myself: ‘You've got the most beautiful ... Read full Story
hippocampus_171 2024-11-09 689 anal Crossdresser Amateur Blowjob Sex Toys Mature small cock big ass sissy femboy Ass to Mouth cum in mouth teen (18+)
61%
The Teacher and Me
Funniest and hottest story of my life right here: Growing up in a small, redneck community, I wasn't going to come out of the closet anytime soon. I had to find an outlet for my sexual desires, even if just for a single night. I resorted to Craig's List the day I turned 18. So there I was on c... Read full Story
shemale lover 2014-09-05 8,767 shemales gay male Mature
80%
Karen, My School Teacher Part 1
The Meet By FoxyHosed It all started when we got a new class teacher. Her name was Karen. She was a mature lady and had dark red hair to her shoulders. That first day she wore some short dark blue jeans and a brown blouse. My other classmates started whispering about her. “He-he! Have you seen t... Read full Story
FoxyHosed 2021-01-29 9,415 Crossdresser Fetish redhead pantyhose Mature pantyhose cd
95%
Hot for Teacher
Jack was enjoying his going away celebration, as he prepared to move from teaching high school to college. He had spoken with many of his former students, and found it endearing that so many of them cared enough to show up at the party. By the end of the evening, though, there was still one young wo... Read full Story
shemale lover 2013-01-05 17,004 sucking Blowjob Big Cock handjob
50%
La bonne chair masculine…
La bonne chair masculine… La brise caressait mes mamelons gonflés me donnant des frissons agréables. Les deux verres de Riesling avaient également contribué à mon excitation. Mon entre-jambe brûlait comme si le soleil qui disparaissait avait soufflé toute son énergie thermique dans mon intérieur... Read full Story
hippocampus_171 2023-04-23 1,369 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminization cum in mouth gaycd virile
50%
eromène contre vieille pétasse
Une eromène baise une vieille pétasse Lorsque je levai la tête pour découvrir à qui appartenaient ces mains de mannequin qui me servaient, j'ai été surpris de tomber sur un girly-boy. "Autre chose" sourit-t-il/elle en traînant ses longs doigts vernis incolores sur la nappe. Je n'ai pas pu m'... Read full Story
hippocampus_171 2024-11-09 200 anal Small Tits Amateur Creampie Sex Toys Mature small cock big ass sissy femboy Ass to Mouth cum in mouth teen (18+)
100%
delicious virile male flesh
Tasted delicious virile male flesh… The breeze caressed my swollen nipples giving me pleasant shivers. The two glasses of Riesling had also contributed to my excitement. My crotch was burning as if the disappearing sun had blown all its thermal energy into me. Under my fine lace panties, purple o... Read full Story
hippocampus_171 2023-04-23 5,481 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminisation cum in mouth gaycd virile
100%
The Big Mature Shemale Next Door
The Big Mature Shemale Next Door SugarandSalt "Please can I just wear my old swimming trunks?" Warren begged. "No!" his mom yelled back from the other room. "Barbara purchased that for you. It was expensive so you better remember to thank her." Warren looked at himself in the full length mir... Read full Story
Gwapo67 2022-05-03 8,713 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
80%
What I like
I like cum from cocks, a copious creampie dripping from a pussy, or licked off a warm body. I'm an older guy but I'm still fit, active and horny all the time. I like to masturbate while looking at porn with a prostate stimulator up my ass, wearing nipple clamps and a cock ring after smoking some pot... Read full Story
SylvesterLeChat 2023-08-15 5,111 Masturbation Creampie Blowjob Big Cock Ladyboy Mature small cock sissy cum in mouth
50%
An alumni gathering like no other; 2/2
... I opened my eyes, sobered up from the alcohol and my lust. Simo had already left. I had to get ready for the party, and I had to do it like a man! BUT, slut that I am, to make my breasts more prominent under my dark purple tank top, I tightened a transparent strap around my waist. You never kno... Read full Story
hippocampus_171 2024-06-16 2,846 anal Amateur Creampie Blowjob Sex Toys Mature small cock big ass cum in mouth
100%
the orgiastic fever of a trans-milf
Simulating a woman, or the orgiastic fever of a trans-milf It's been two months since I moved to the megapolis, where I've discovered several places where the third gender goes. One of my first explorations was a huge lingerie shop in a MALL; I wanted to buy some sexy stuff without being noticed ... Read full Story
hippocampus_171 2024-09-04 2,752 anal Amateur Cumshot Creampie Shemale Fucks Guy Latex Sex Toys Mature small cock
100%
screwed as a bitch
screwed as a bitch All kinds and ways of sex, I said in my profile... When I half-opened the door the panting mutt was circling in the middle of the room. Licking his lips, cock throbbing, no doubt he was waiting for the bitch that I am. I got down on all fours and pushed the door open with my s... Read full Story
hippocampus_171 2024-10-02 1,890 anal Amateur Bareback Creampie Fetish domination Mature small cock cum in mouth
76%
Louise's Bedroom
The dark and humid night consumed the street surroundings, the rain pattered softly against the car window as Scott pulled outside Louise’s house. Louise had never agreed to let Scott visit before and he knew that this would be the only opportunity to make a good impression and be with her in the fu... Read full Story
Master VeeJay 2017-12-12 9,763 Amateur Bareback Creampie Blowjob Guy Fucks Shemale Mature
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 12,464 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
83%
Black Love: Transsexual Edition
My name is Steve Vincent. A big and tall young Black man living in the city of Brockton, Massachusetts. Currently, I'm a graduate student at the University of Massachusetts in downtown Boston. When I'm not in class, I work for the Department of Corrections. I'm openly bisexual, and love to have fun.... Read full Story
shemale lover 2012-06-27 4,427 anal sex Creampie Big Cock oral sex Interracial
100%
Emily and Steve Part 10
It took me a long time to get over Emily, but like all pain, eventually it past and I started to want to get into a relationship again. Before Emily, I had gone out and hooked up with t-girls from the local scene a few times, but never thought of anything serious. My time with Emily had taught me... Read full Story
shemale lover 2012-04-08 3,814 anal sex Latina Creampie tgirl
40%
Dating all whole my life
Julia and Ilya, together 10 years It was more than 10 years and 2 children ago. In December 2005, we agreed to meet at the gate of my office after a working day. I did not go out godlessly for a long time (40 minutes from the appointed time), but he still waited. I hope he does not regret it ... Read full Story
PornoDating 2019-08-15 4,446 Crossdresser Amateur Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock Asian gangbang domination Guy Fucks Shemale Interracial sex Mature Futanari Frottage Compilation Ass to Mouth Cartoon cum in mouth double anal dating life in Mars? life
100%
A Strong Man at Work
In life, some people seem to get pleasure out of pissing others off. I think you know what I mean. We've all been there. The first time I laid eyes upon Joan, I thought she was a low-class, boring and obnoxious person. Where I come from, people like that are pretty common. Who am I? Stefan. A tall a... Read full Story
shemale lover 2012-07-05 3,787 anal Creampie shemale
50%
She also conquered my soul...
Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... Read full Story
hippocampus_171 2022-11-22 4,469 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
90%
Freshman Surprise
Hey guys, you wouldn't believe what happened to me last weeks I went from being a virgin 19 year old to having the hottest girl on campus as my lover! I won't tell you her or my name of course, this is the internet It started out last week, the start of my first semester at a community college... Read full Story
shemale lover 2011-09-19 4,802 Cumshot licking sucking
100%
Me & Miss Cocker
A few weeks ago, I moved into the final year of school. Our English teacher had left at the end of the previous school year, and we had a new teacher, Miss Cocker. Now to say Miss Cocker is a babe is an understatement, she is about 6.2' tall and she has long voluptuous legs, which are usually sto... Read full Story
shemale lover 2011-10-30 4,292 Creampie transsexual ass licking oral sex
0%
Mike and Chris Together
Mike's sex life had taken a definite series of turns for the worse. When he called one of his favorite partners, Stella, she apologized for not returning his earlier calls, and told him she had been very busy lately. "I'm really sorry, Mike. I've had some great times with you, and I will alw... Read full Story
shemale lover 2012-02-07 5,576 anal sex Creampie Shemale Fucks Guy Guy Fucks Shemale
100%
A Schoolgirl Story Chapter 2
I must apologise for the amount of time that it has taken for the second chapter of this story to come out. I have to admit that I had kind of abandoned it, but all your lovely feedback comments made me decide that I couldn't leave this one hanging. So thank you to everyone who wanted more of Wendy,... Read full Story
shemale lover 2012-06-05 8,967 Group Sex Cumshot oral sex assfucking
50%
Hard Decisions by Elaine © 2020
Hard Decisions by Elaine © 2020 No one in this story is based on anyone alive or dead. It is a work of fiction and should not be read by minors. I appreciate the kind efforts of many of my friends who cast a welcoming glance over the initial writings. I owe you all a big debt of thanks. Prolog... Read full Story
Elainetguk 2023-09-06 5,280 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
93%
Homework
Daniel was a 15 year old teenager, like any boy his age, he was full of hormones and sexual fantasies for every pretty girl that passed in front of him. In the last weeks of the school year, the history teacher had a child and was absent from school, being replaced by teacher Marlene, a trans woman.... Read full Story
haroldãosanguebom 2024-01-09 7,921 Shemale Fucks Guy Big Cock Mature
100%
Tasting the good FLESH
I am no longer Virgin, en bon et du forme Thing never dared since I taste the enjoyment by all the senses and in all its senses... I discovered her when she smiled at me as a thank-you for giving her the way to the small-town supermarket where I was on business. Sandals at her feet of Cinderell... Read full Story
hippocampus_171 2022-11-10 5,241 Amateur Creampie Shemale Fucks Guy Guy Fucks Shemale Mature Ass to Mouth cum in mouth
75%
Tales of Old China
This is a true story by the way. It doesn't matter too much, but I guess it's worth you knowing that. My name is….. Well my name isn't important. What's important is that I'm now in my late 20's, male, tall, fit, dark haired, blue eyed and have been told that I'm good looking. Got that in ... Read full Story
shemale lover 2011-09-30 3,945 anal sex asshole Creampie
100%
The Seductive Seed of a Tranny MILF
The Seductive Seed of a Tranny MILF SugarandSalt Jackson got home and immediately curled up in bed. He didn't want to move for the rest of the weekend. He'd finally worked up the courage to ask a co-worker out at work. She politely rejected the invitation. Then later on in the day, Jackson spo... Read full Story
Gwapo67 2022-05-03 8,361 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 9,617 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
94%
Southern Hospitality Ch. 01
XtinaSmith2017 Ash gawped at his mother, incredulous as to what she had just said. He understood the basic premise of what had happened, but the reasoning she must have had absolutely baffled him. "Why?! Why would you do that?!" He pleaded, voice light and desperate. She shrugged, looking acr... Read full Story
Gwapo67 2022-05-16 7,686 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature
91%
Lake Surprise
After finals of my first year in college in a northern university, I was ready for some real relaxation back home in the warm south. During finals I had started thinking how nice it would be to borrow my brothers boat and hit the lake for a week. I talked my roommate into making the trip home ... Read full Story
shemale lover 2011-12-08 11,062 anal Group Sex Creampie
100%
sex-agenarian's onanic lust
An onanic lust of a sex-agenarian that I am; I'M IN BIG HEAT; it's the season of bodily reunions in nature... I'm like an elephant(e) waiting to be satisfied. My cloaca is starting to titillate at the mere sight (look hah!) of a guy's swollen crotch on the street... I activated all my sensors to sa... Read full Story
hippocampus_171 2024-03-09 4,804 anal solo Amateur Masturbation Creampie Sex Toys Mature small cock
50%
Luxure onanique
Luxure onanique du sex-agénaire que je suis... JE SUIS EN GRANDES CHALEURS; c'est la saison des retrouvailles corporelles dans la nature... je suis comme une éléphante qui attend d'être satisfaite. Mon cloaque commence à titiller rien qu'à voir (regarder hah!) l'entrejambe gonflé d'un mec dans l... Read full Story
hippocampus_171 2024-03-09 757 anal solo Amateur Masturbation Creampie Sex Toys Mature small cock
50%
Rassemblement d'alumni pas comme les autres; 2/2
... J'ai ouvert les yeux, dessoûlé de l'alcool et mais aussi de mes sensations de luxure. Simo était déjà parti. Je devais me préparer pour la fête, et ce, en homme!!! MAIS, la salope que je suis, pour rendre mes seins plus proéminents sous mon débardeur pourpre foncé, j'ai serré un sangle transpa... Read full Story
hippocampus_171 2024-06-17 399 anal Amateur Cumshot Creampie Blowjob Sex Toys Mature small cock Ass to Mouth cum in mouth