Sort by
Relevancy

Free Stories

75%
Caught IV
The next day Aunt Teresa woke me early and asked me to wait in the living room. She went through my room while I waited. When she came out she was holding the magazine of naked men. She smirked at me and said" I see you're interested in stud magazines"? I stuttered, "no, Auntie, I don... Read full Story
shemale lover 2012-07-02 2,298 Fetish transvestite crossdressing
94%
Tortured by the T-Girl Tutor
Duncan didn't quite know how to handle it. He'd planned on a quiet Winter Break. Sleeping til noon, watching too much television and eating tons of junk food. That kind of stuff. He had a whole two weeks off from community college. At school, he was an outcast. They say life gets better after hi... Read full Story
shemale lover 2012-12-18 33,874 Big Tits shemale Big Cock Lingerie domination
100%
A Love of My Very Own
In the eyes of the world, I am many things. She-male. Tranny. Chick with dick. Those are the names they've got for me. What do I call myself? I call myself Angela Shay. Anyone looking at me would see a five-foot-nine, curvy Black woman in her mid-thirties with a nice rack, wide hips and a big round ... Read full Story
shemale lover 2013-03-13 4,525 tranny ass shemale Interracial softcore
66%
Becoming an identical twin part I
My name is Cody and I recently turned 19 years old along with my twin sister Cassidy. She is older by 4 minutes and is the apple of our parent's eyes. She is in almost every aspect a goddess. Her beauty, intelligence, humor, sex appeal, and just about any other trait you can think of she is flawless... Read full Story
Chloe6942 2018-08-23 7,315 Teen (18+) Amateur Fetish
50%
MISTRESS'S TERROR
The night had ended EXTREMELY PLEASUREABLE with BILLY, RYAN & PETER in a literal BANG and I was HAPPY. BITCH I was going to ask to be my wife as LESBIAN LOVERS. We were perfect together, Aunt Susie had groomed me into a SHEMALE DOMINATRIX and BITCH became my SUBMISSIVE. From the early days when I wa... Read full Story
BITCHGURLvr 2024-06-05 1,745 cock transsexuals smoking cigarette
100%
First Cock Came From Old Friend
It was Saturday and I had nothing to do so I decided to go for a drive. I got into my car and headed out of the city in no particular direction. After driving for a while I realized I was close to Jim's house. We have been great friends for years but have not seen each other for a long time. I decid... Read full Story
shemale lover 2011-10-03 4,666 asshole oral sex teasing
100%
Five Years Gone
"Five Years Gone" "Hi, this is Maribel." Her voice was a little more throaty and lower than I had envisioned, but that along with her Spanish accent made her even more alluring. I kept running her photos through my mind while I answered: "Hey Maribel, I was hoping t... Read full Story
shemale lover 2011-10-13 3,650 asshole Blowjob asslicking
96%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 30,625 strapon porn
33%
A Certain Perception
Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... Read full Story
shemale lover 2012-02-23 8,064 Fetish transformation dildo
83%
Elaine & Me
- Chapter One – Our First Meeting - I had two weeks to go before the final degree exams and I was working hard. Perhaps too hard, because I desperately needed a break from the hours and hours of revision. It felt like I just couldn't take in any more detail about Quantum Mechanics or Solid ... Read full Story
shemale lover 2012-03-31 11,223 sucking Fetish transsexual
83%
Five Years Gone
"Five Years Gone" "Hi, this is Maribel." Her voice was a little more throaty and lower than I had envisioned, but that along with her Spanish accent made her even more alluring. I kept running her photos through my mind while I answered: "Hey Maribel, I was hoping t... Read full Story
shemale lover 2012-11-07 3,547 Cumshot oral ass licking
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 13,430 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
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 3,769 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
54%
hi is me
im happy later of much time im a verified model , because other person have much videos of me and is not good look your videos in other page is not your .... thanks shemale for give me the chance to be verified love you... Read full Story
Kimberly Polizzi 2019-08-21 3,297 Amateur Latina Big Cock Shemale and Girl Compilation webcams
66%
Verführung!!!
Verführung!!! stelle mir vor, du kommst zu mir, wir setzen und an den Tisch und trinken Kaffee, wir führen eine zweideutige Unterhaltung, dann streichle ich über deine Hose, ich spüre wie dein Schwanz in meiner Hand ganz hart wird, wir Küssen uns sanft, während ich dir die Hose auf mache und deinen... Read full Story
Jaque böses Mädchen 2020-08-13 2,573 Crossdresser Amateur Cumshot Bareback Creampie Blowjob domination Guy Fucks Shemale Homemade Compilation cum in mouth
100%
Ich und der Kommissar
Ich und der Kommissar, nach einer Vergewaltigung wollte ich mein Erlebnis einem Polizei Kommissar schildern. Wir saßen im Wohnzimmer auf meiner Couch, er sagte zu mir ich solle ihm meiner Erlebnis schildern, er merkte das ich etwas gehemmt und schüchtern war, er bot sich auch als Statist an, er sag... Read full Story
Jaque böses Mädchen 2020-08-13 2,502 Crossdresser Amateur Cumshot Bareback Creampie Fetish Blowjob Big Cock domination Guy Fucks Shemale Compilation Ass to Mouth cum in mouth
0%
Cheeze or Sleaze ? , Chat up Shite
You Know what will look Good on You ? Me ! Wanna know what I like the most in you ? My Cock I’m not a weather man, but you should expect over a few inches tonight. I think there’s a mirror in your pants? Coz I can see myself in them Hi, can I buy you quite a lot of drinks? I can cook ... Read full Story
Lucy❤ 2021-05-05 1,360 Compilation Humour
87%
My best night at a gloryhole and theater.
Hello, this is an account of what I consider my best night of my life; I was living in Baltimore, MD, Essex area at the time. A little background on me is that I am married now and at the time of this night but not that happy at the time. I was married for about 8 years and my wife and I decide to f... Read full Story
jenniferboobs 2021-11-12 5,105 Crossdresser Cumshot gangbang Compilation cum in mouth gloryholes theater
50%
Why Do Guys do this?
Why do guys on the porn, dating sites and social media sites I'm on want to chat live on video all the time? And if I don't agree they unfriend and even block me. Why? Aren't my videos and pixies good enough? They are of me...they ae real, and not photoshopped (except for sharpness and clarity.) I h... Read full Story
Chrissy Tunnell 2022-03-14 2,495 Crossdresser solo Amateur Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Frottage Homemade pov Compilation
50%
SOUS LA DIRECTION DE MAMAN
Jaime n'avait jamais eu beaucoup de chance avec les filles du lycée. C'était venu et reparti, et maintenant il en profitait un l'été dernier avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un crétin ou un crétin, c'est juste que la vie et la... Read full Story
Femboy 2021 2023-01-06 1,149 Teen (18+) Crossdresser Amateur Fetish Lingerie
50%
PRIS DANS UNE NOUVELLE VIE
C'était mardi soir, ce qui signifiait que Lena se préparait pour son cours d'aérobic. Bien qu'elle ne travaillait pas, elle était certainement occupée à construire et à maintenir une vie sociale et à faire en général les choses qu'elle voulait. Il n'y avait pas un jour où Lena n'avait pas fait qu... Read full Story
Femboy 2021 2023-01-19 1,128 Stockings Crossdresser Amateur Fetish Big Cock Lingerie
50%
SOUS LA DIRECTION DE MAMAN
Jaime n'avait jamais eu beaucoup de chance avec les filles du lycée. C'était venu et reparti, et maintenant il en profitait un l'été dernier avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un crétin ou un crétin, c'est juste que la vie et la... Read full Story
Femboy 2021 2023-01-26 1,296 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
100%
C'EST LA PATRONNE
Le rêve est mort. L'écriture était ma passion, mais cela n'a jamais servi à rien. La réalité a une mauvaise façon de vous rattraper, déchiquetant vos désirs dans son sillage. Ce cycle d'épargne et de vie de ces économies s'est progressivement révélé intenable et maintenant, à ving... Read full Story
Femboy 2021 2023-02-06 1,311 Stockings Shemale Fucks Guy Fetish Futanari cum in mouth shemale + shemale
0%
SOUMISSION CIEL ⚧️ ⚧️
J'ai regardé les pieds de ma mère se frotter lentement les uns contre les autres, les nylons de ses collants produisant ce son distinct et délicieux pour lequel j'étais si faible. *Suisse* Un pied posé sur l'autre, bougeant doucement et lentement, se caressant dans un mouvement hyp... Read full Story
Femboy 2021 2023-03-18 677 Crossdresser Cumshot Masturbation Shemale and Girl domination Ass to Mouth
50%
SOUS LA DIRECTION DE MAMAN ⚧️ ⚧️
Jaime n'avait jamais eu beaucoup de chance avec les filles au lycée. C'était venu et reparti, et maintenant il profitait d'un dernier été avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un salaud ou un douchebag, c... Read full Story
Femboy 2021 2023-03-18 925 Teen (18+) Crossdresser Cumshot domination Sex Toys cum in mouth
50%
C'EST LA PATRONNE ⚧️ ⚧️
Le rêve est mort. L'écriture était ma passion, mais cela n'a jamais servi à rien. La réalité a une mauvaise façon de vous rattraper, déchiquetant vos désirs dans son sillage. Ce cycle d'épargne et de vie de ces économies s'est progressivement révélé intenable et maintenant, à vingt-cinq ans, j'ai... Read full Story
Femboy 2021 2023-03-30 1,066 Big Tits Cumshot Creampie Blowjob Big Cock domination cum in mouth analsex femme plus âgée Futanari futa sur femme
50%
My erotic dream
Over the past few years I have been thinking about one very important thing.To jerk off all the time and to think about beautiful, sexy trannies who want you to fuck them for the rest of your life. I give in to temptation and when I see cum on my face, that's when a strong orgasm calls to action. In... Read full Story
Kalio 2024-03-06 3,418 Cumshot Masturbation Shemale Fucks Guy Blowjob big ass Compilation
100%
Alexis Season Part 5
Alexis sucked the head, then put a little more in her mouth, licking his dick inside her mouth, getting it wet with her saliva. She could taste precum dripping out, and she gladly let it swish in her mouth as she sucked him. She then took his dick back out and licked the bottom of the shaft, look... Read full Story
shemale lover 2011-11-28 2,512 orgasm oral sex stroking
75%
Candy Pink
Life pretty much sucked. I was the son of Ralph and Cindy Cassella. They named me Ralph Junior and my dad was thrilled to have a son he could raise to live out his past glory. My dad wasn't a bad guy and never abused me but I knew he was disappointed. He worked as a contractor in the present but he ... Read full Story
shemale lover 2011-12-08 4,874 taboo Fetish crossdressing
71%
Headmistress' Favorite Sport Part 2
Over the next week the twins trained him further. He was taught how to apply make-up and how to behave in a properly feminine and submissive manner and they trained his movements to be properly feminine. So as not to wear the skin of his ass, the twins introduced a new punishment tool for these trai... Read full Story
shemale lover 2011-12-12 4,772 torture toys bondage and discipline heavy
50%
I am Baaack! Part 11
Now Rose upped her sincerity level. "I want that kind of friendship with you, Joan! I believe we are kindred spirits. If two manipulative bitches like us CAN be friends, I think we should be. I did this little scenario today as a show of skill, inclination, and sincerity. Could I do to other me... Read full Story
shemale lover 2011-12-17 2,476 anal erotic encounters consensual
100%
A Flash of Lace
The insistent ringing of the phone broke my concentration and with great annoyance, I climbed off the bed and picked up the receiver. "Hey little brother!" My sister's sparkling voice filled my ear. "Di, Is that you?" I exclaimed happily "Got any more sisters I don'... Read full Story
shemale lover 2012-03-03 5,958 Stockings Fetish dressing
100%
A New Girl
Still half-asleep, I purred happily when I heard the curtains being drawn. I could hear the sound of rain beating against the outside of the window, but the poor weather was the last thing on my mind. Still barely able to believe my luck, I slid my hand down the side of my smooth thigh, delighting i... Read full Story
shemale lover 2012-04-05 4,330 fingering oral sex small breasts cum swallowing
83%
The Making of A Sissy Part 6
Roberts took full advantage of his few minutes alone with Bella, as Aunt Jane attended to the caller at the door; he wiped her soft lips clean of his sticky semen and sat her tenderly on his lap, careful to let her sore little cheeks hang over; he caressed the soft white flesh and softly kissed her ... Read full Story
shemale lover 2012-05-27 2,958 fingering little cock sissy
100%
Caught III
In I & II I was caught dressing by Mum and sent to Aunt Teresa for adjudication. Within minutes of Teresa leaving for church and her meeting, I was dolled up and putting on my face. I was parading about the living room, dreaming of men trying to hit on me, when I heard, "Well, well, well&qu... Read full Story
shemale lover 2012-07-02 2,292 Fetish transvestite crossdressing
66%
Caught V
Synopsis: Mummy caught me cross dressing and sent me to stay with Auntie Teresa to address the problem. Auntie caught me two days later and interrogated me into confessing my desire to dress like a woman and my interest in men. Aunt Teresa ordered me to the living room. She said, "I have dec... Read full Story
shemale lover 2012-07-02 2,179 Fetish transvestite crossdressing
50%
Butterflies
There were a lot of good reasons to be out this early, but none as wonderful as seeing this first Giant Swallowtail awakening, and John smiled as it moved. Magnificent, he whispered, in awe of this giant as it slowly unfurled it's Forewings against the sun's morning warmth. It was, as they always we... Read full Story
shemale lover 2012-09-30 5,632 taboo transformation sex
100%
CD And Trucker
At least four things went through my mind the moment I heard Hank ask me to go along with him. - One my wife was gone for at least 2 weeks so that was no problem. - Two, with wireless connection and my laptop I could take my job on the road. - Three, I had hardly any clothes in my bag that I was ... Read full Story
shemale lover 2013-04-30 9,405 Cumshot fingering domination spanking cd
49%
My first sex teacher..!
I must be about 16 or 17 and we were staying at our ancestral home and there was no TV there. So, I used to go to my aunt’s house to watch TV. Her name is Sheela. I am not sure when my aunt started to seduce me, but one day when I was at her place and none was around, she asked me whether I like t... Read full Story
Manusha Tranny 2021-10-18 23,657 Teen (18+) Mature Homemade
100%
Continua mi mundo Tv
Como les decía a mis 20 años ya era otro mundo, ya compraba mi propia ropa intima femenina mas que todo ropita muy chica, pues siempre he sido muy delgad@, a esta edad aun era virgen pero con hombres ya que aproximadamente a los 17 le robe un consolador a una tía, "les admito que ha sido uno de ... Read full Story
Carla Travesti 2018-12-10 2,491 Small Tits solo Amateur Latina Masturbation Fetish Ebony Sex Toys morena flaca venezolana deportista morbosa
87%
Girl from Uncle
Tonight, I have to tell it all. It’s no secret that my uncle and I had a very special bond he had been eyeing me with those adventurous eyes from the time that I was 14 years old. And frankly I enjoy his ogling. I could feel my nipples get so hard when he looked through me with those alert and spark... Read full Story
Regina10 2024-02-14 4,676 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
100%
Uncle sweet Lover
Uncle Barney called me this morning and wanted me to keep my evening free. He wanted to meet me at the motel with a surprise for me. I was so excited and could hardly wait. I had to decide on something to wear, but when I thought about it, I realized that I wanted to wear something special. He would... Read full Story
Regina10 2024-02-19 4,188 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
90%
A TV in the Shoe Store
I work at a ladies shoe store at a large metropolitan mall. My name is Jillian, though my friends all call me Jilly. Those same friends also say that I am blessed with a beautiful face, and an athletic body! Pretty heady for a 30 year old woman whose ideas of athletics never got beyond sports i... Read full Story
shemale lover 2015-08-27 10,610 first time sucking shemale
84%
The Making of Erica - Sperm Loving Crossdresser
Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I have only sucked cocks, but over a hundred at my las... Read full Story
shemale lover 2015-09-03 16,440 shemales Masturbation Fetish
57%
Carrie
Four years ago as a 14 year old the girl trapped inside my body was screaming to be released from her prison. I had showed up at school on the first day of my freshman year wearing a dress from my sister's closet. I've never worn boys clothing since. Carrie became my new persona replacing Todd. P... Read full Story
shemale lover 2011-09-21 3,540 first time asshole dildo nipples
93%
The Babysitter's Secret Part 2
Two months had passed since Jenny and I had first made love on that fateful, snowy night. At least once a week, occasionally many more, Jenny and I had found time to be alone and indulge in our secret affair. I had never believed any sexual experience could be greater than our first time together bu... Read full Story
shemale lover 2011-10-24 6,520 Stockings shemale oral sex bisexual
87%
Headmistress' Favorite Sport Part 3
There was no more time for Denise and Susanna to get over their chemically induced bout of incestuous activity as Denise was being sent to school. This was of course part of the plan. Slaves should always feel guilty about something and once their slave training was over, neither would be able to ma... Read full Story
shemale lover 2011-12-12 6,146 toys bondage and discipline chastity belt
50%
Headmistress' Favorite Sport Part 8
For Denise her life as a fully trained slave began with a stay at Mistress Rachel's house before joining the twins' household. Since it was their idea to turn her into the sissy she now was, it was agreed that she would be their slave. But as the twins were moving out of Mistress Rachel's house and ... Read full Story
shemale lover 2011-12-13 5,754 torture toys bondage and discipline chastity belt
50%
I am Baaack! Part 8
Robbie remained behind. She waited till the paper smoldered and then finally caught fire, then she went back into the den and put on her dress. She mussed her hair and smudged her makeup as if she had been sleeping. She looked back into the living room, and seeing that the fire was spreading from th... Read full Story
shemale lover 2011-12-16 2,052 crossdressing erotic encounters fantastic
50%
I am Baaack! Part 10
She turned back to Dainie, and spoke to her like a proud parent. "Dainie, honey, I am so proud of you! I'm so sorry I had to speak harshly to you earlier, but you do know that you deserved that, don't you?" Dainie nodded yes. "And don't you feel so much better, now?" Dainie shyly... Read full Story
shemale lover 2011-12-17 1,788 crossdressing erotic encounters fantastic
100%
Selene and the Shemale
I had been friends with Selene for six years - we had met in our first year at university - at a film society party. I was a science major specialsing in partying. She was a music student. She had a sultry, sexy singing voice that was perfect for jazz and blues and even back then, she was earning a ... Read full Story
shemale lover 2011-12-21 3,360 shemales Masturbation Fetish
100%
Debbie Part 8
Moira sat in her booth at the entrance to the subway station and saw people pass by. She sat there every day selling tickets, and although several thousand people passed her during a shift, she could now recognize many of the regulars and she even knew when to expect them. It was now almost 9 o'cloc... Read full Story
shemale lover 2011-12-23 7,153 transgender toys bondage and discipline heavy
57%
Debbie Part 9
It soon turned out that Debbie wasn't destined to spend the rest of her life as a whore. As she returned to the apartment one night one of Mistress' men was waiting for her. She had only just opened the door, when without a word he cuffed her hands behind her back, gagged her and put a collar and le... Read full Story
shemale lover 2011-12-23 6,243 transgender toys bondage and discipline heavy
50%
Debbie Prologue
John had finally made it through high school and escaped from the confines of his hometown. And now he had made it to the big city. OK, he had no real friends and no family, but at least he wasn't harassed as much any more. Back home in high school he was always picked on for being too small and too... Read full Story
shemale lover 2011-12-23 1,654 transgender toys bondage and discipline heavy
100%
A Special Girl Part 2
Well, Mummy says she always knew I was really a girl. Even though she tried to deny it at first. In fact for the first few years of my life she tried to force me to be a boy. My dad had died just after I was born. He was in the army you see and there was some sort of training accident. So that left ... Read full Story
shemale lover 2011-12-24 3,379 shemales taboo panties
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 13,796 anal Blowjob black fiction