Sort by
Relevancy

Free Stories

100%
The most recent time I had sex..
So I had been getting these messages on a hook up app from this guy who looked very muscular and his messages seemed decent.I like decent nice normal people who aren't super crude about words and who treat me nicely so I ended up making plans with him.I met him at his apartment later that week.I was... Read full Story
beth graves 2024-08-12 3,224 blowjobs crossdress casual sex jack off Hook up meet up
66%
Showing Off For My Wife's Pleasure
There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my f... Read full Story
shemale lover 2011-10-25 5,769 anal asshole shemale
75%
Birthday Party
It was now about 11 pm and Sue and I have been at it for the past 3 hours. Sue had me get up and go into the bathroom. As I stood in the shower I thought of what we did. Sue knew how to pull the right strings on me or in me. And she knew what pleased me. I washed all over. I had no idea of what was ... Read full Story
shemale lover 2012-06-14 3,964 anal sex Cumshot fingering oral sex jacking off
92%
My First Time
I have done wallpapering for about 5 years. I do this on the side for pin money. Also to pay for some of the woman I have on the side. I have been married for a few years and my wife does not enjoy the kinky and sexy things I do. So that only leaves picking up woman. I was sitting home alone on a Sa... Read full Story
shemale lover 2011-11-27 5,547 first time facial mouth fucking jacking off
88%
Stepdaughter's Transexual Surprise Part 2
As I ended the first chapter of my love story, my Stepdaughter Dawn and I were returning from loading a Ryder truck with her possessions. We were to spend the night at home, then continue on to her new place in the morning. We had stopped on the way and enjoyed committing acts of sin by Dawn seducin... Read full Story
shemale lover 2011-12-04 7,348 anal cum facefucking jacking off
100%
Cathy's Friend, Transsexual Mary
I have told you about my daughter Cathy. She is a stripper at a nude club. She has sucked me and I have got to fuck her in her ass. All this in front of her friend Bill and Mary. Bill is Bi, like me and Mary is a transsexual. I'm also a cross dresser. Just two weeks ago I found out that my daught... Read full Story
shemale lover 2012-06-05 4,247 anal sex shemale facefucking jacking off
88%
A Walk In The Park
Each day I spend my lunch down at the park in town. It is down by the lake. I sit and eat my lunch and watch the people walk by. I watch them and they watch me. Then when I’m done I go for a long walk. Each day that I go I start my walk about the same time. At 12:30 pm I start my walk. I like ... Read full Story
shemale lover 2012-07-20 5,035 Cumshot shemale oral jacking off
100%
The new girl in town
It all started when i was a teenager. I was like every teenage boy, i looked at porn on the internet and masturbated a lot. i love to watch lesbian porn it was sooo hot watching to girl have sex. i soon after that i got into the anal sex, watching the girl have orgasm after orgasm while she has a hu... Read full Story
shemale lover 2012-05-06 5,028 anal sex Blowjob handjob jacking off
75%
My Week last Week
So it was pretty good. I never met a guy this fucking horny before, literally came three times. So I was wearing my black wig, awesome makeup, plad miniskirt, thigh highs/w knee high gogo boots, and cute top with my forms in. So I start sucking this guy who is rock hard when i step out of the bath... Read full Story
shemale lover 2012-04-05 2,319 anal sex cum crossdressing jacking off
100%
I`ve been so horny lately
I`ve been so horny lately I found one of my first pair of heels I have ever bought and I also bought leggings recently and even sexy gloves. Those leggings match very nicely with those heels. Before gloves would make me cum after stroking my cock for 1 minute or less. Now I want to enjoy it and act... Read full Story
shemale lover 2012-09-24 2,278 Fetish cum jerking off
60%
Be Careful in the Park
One was jet black; he looked the oldest, wearing white rugby style shorts and a black T. The youngest looking was also coloured, more a coffee colour, in his case wearing denim shorts and a polo shirt. The others were white but standing more in the shadow so I couldn't make them out so clearly at th... Read full Story
shemale lover 2012-05-03 3,173 anal sex Cumshot jacking off
100%
My first time wearing sexy lingerie Part 2
I could not wait to get home from school the next day after wearing my moms sexy panties the night before. No one was home so i could have fun. As soon as i got into my room i took off all my clothes and went into my moms bed room to see what I could put on. With my mom working at Macy's in... Read full Story
shemale lover 2012-09-15 5,840 first time Cumshot Lingerie jacking off
100%
Jack & Jill - his first time with a transexual
Jack and Jill meet It was when I went to the patio to enjoy a cigar after dinner that we met. On the road for business, I found a decent bar and grill near my hotel where I was welcome to enjoy a fine smoke. I had dinner and then moved outside for a relaxing smoke in the cool weather. I lighte... Read full Story
shemale lover 2012-04-09 5,709 anal sex oral sex cum swallowing deep throating
100%
Darlene, Jack and I Part One
I was driving home from a local peep theater when my car broke down luckily I knew a couple from work that lived nearby. I called my road service company who told me they were unable to help me before Monday since it was a three day holiday weekend. Luckily, when I arrived at their home someone was ... Read full Story
shemale lover 2012-02-20 2,638 suck deepthroating porn
92%
Darlene, Jack & I Part One
I was driving home from a local peep theater when my car broke down luckily I knew a couple from work that lived nearby. I called my road service company who told me they were unable to help me before Monday since it was a three day holiday weekend. Luckily, when I arrived at their home someone was ... Read full Story
Quib 2017-01-23 7,772 Crossdresser suck ass fucking cumming threesomes
100%
About Jack and Diane
Thanksgiving was over the college kids are returning to school and Las Vegas has slowed down from the busy restaurants and overcrowded casinos. It’s the best time of year to see a nice show for less. Jack’s friends had all taken off with families and he had time to think about how lonely he really w... Read full Story
Jon Paul 2023-12-20 7,836 anal Cumshot Bareback Fetish threesome Lingerie Guy Fucks Shemale small cock shemale fucks shemale cum in mouth shemale + shemale
50%
Baby Face Jack's Biggest Fight
The referee held his gloved hand high in the air. The crowd was hushed as the ring announcer spoke, "Ladies and Gentlemen, the winner of this World Featherweight Championship Boxing Match to unify the title, by technical knockout, and still undefeated; Baby-face Jack Mc Coy." The crowd scr... Read full Story
shemale lover 2012-02-08 7,562 fuck oral
82%
Bikini Boy
I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage... Read full Story
shemale lover 2012-06-12 15,980 Cumshot Fetish oral sex crossdressing
100%
A Close Encounter of the...
Another great tape and another great yank of the crank. Yea, she-males were pretty hot, Tom thought as he hit the eject bottom on the tape deck, but where on earth would he really find one? He had little doubt that if he did find a place where they hung out that there would be more than a few with a... Read full Story
shemale lover 2011-11-13 5,379 Cumshot Blowjob massage
69%
My aunt made me a transvestite
My aunt and uncle lived two doors down from me when I was growing up. They had a son one year younger than me. We played together all the time and I was at his house or him at mine all during the summer months. My aunt was a big woman, she was 6ft. tall and weighed around 165. She was even taller in... Read full Story
shemale lover 2013-08-09 29,723 Teen (18+) suck oral Lingerie make up
100%
Ill take all the cum I can get
I'm so horny today. I need some dick bad. So I dress up, I put on a sexy push up bra, a slutty lace top, a naughty little g string, and lacy thigh highs with a garter belt. Before getting dressed I showered and gave myself an enema. After I showered, I used some fds so I smelled sooo good after ... Read full Story
spreadforalldik 2024-07-09 3,956 anal Crossdresser Group Sex Cumshot Creampie Blowjob ass fucking Ass to Mouth cum in mouth spitroast
100%
Little cock convention
They came from all over the nation to downtown LA convention center. It was the "Little Cock Convention" I watched as men from all races and status came in. Sometimes they came with their wives,friends,Mistresses,lovers, or even their boyfriends. I was on Guard duty and walking the conven... Read full Story
shemale lover 2014-07-07 7,493 shemales hardcore sex humor
100%
Birthyday Party Chapter 2
It was now about 11 pm and Sue and I have been at it for the past 3 hours. Sue had me get up and go into the bathroom. As I stood in the shower I thought of what we did. Sue knew how to pull the right strings on me or in me. And she knew what pleased me. I washed all over. I had no idea of what was ... Read full Story
shemale lover 2012-06-24 2,551 anal sex Cumshot shemale fingering oral sex
100%
After Church
I was just horny. All of the time. I just wanted to fuck someone in the worst way. 18 years old, never had a date. Too skinny, too weird. I wore my hair long, not a very hairy body, not very athletic. Just a skinny kid who didn't get any attention. Lot of church girls in the bible belt but they were... Read full Story
shemale lover 2012-08-19 6,378 Teen (18+) Fetish oral sex crossdressing
84%
Shool teen crossdresser first time sex
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest f... Read full Story
shemale lover 2014-11-21 20,151 first time suck fingering Lingerie ass fucking cd
100%
JoeAnn
I don't often travel for my job, actually it was over two years since the last time. The slow economy that caused the housing market to crumble, was a golden opportunity for our small realty firm. Properties in Florida were being dumped onto the market- and we had the necessary commodity, cash. I... Read full Story
shemale lover 2011-10-30 3,800 anal cum oral
100%
Dressing and driving
A little about me, I'm married, and wife doesn't have a clue I like to dress up. I would love to have her know and accept it, but I don't think she would. I do cam and love to get instructions from people that are watching on cam. Am I a sub? I think I am. I like to drive dressed. When I take a driv... Read full Story
SandyCrossdresser 2018-11-26 5,995 Amateur Outdoor crossdressing driving Reast area
50%
Bikini garçon
J'étais le garçon que mon père avait espéré après 3 filles avant moi. La vie dans notre maison à deux étages de la classe moyenne de banlieue était aussi normale que celle de n'importe qui d'autre. Mon père était un père aimant qui m'élevait et faisait les choses qu'un père aime faire avec son fils ... Read full Story
Femboy 2021 2023-01-24 1,467 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale
50%
LE NOUVEAU SISSY CLUB ⚧️ ⚧️
Il y a de nombreuses années, lorsque Craigslist était populaire pour les rencontres et les rencontres sexuelles, j'aimais lire les publicités. Je suis tombé sur une annonce dans la rubrique "Hommes à la recherche d'hommes". Il s'intitulait "Sissy Club Forming". Le titre m'a intrigué et quand j'ai cl... Read full Story
Femboy 2021 2023-04-13 1,374 Stockings Fetish Lingerie homosexual sissy
75%
Kidnapped (Adult Fiction)
Kidnapped I remember being normal. I was a young man in my 20's living in my parent's house struggling to get by. I was online more than I probably should have, but it was an escape from the harsh reality of my life. I didn't feel fulfilled or like a success, I felt like a failure on many differe... Read full Story
Vennom 2019-06-17 25,319 Fetish transformation fiction pov mind control drug interaction mind mindfuck change
60%
Booty and the Blue Pill
This is my account of the first time I took a Viagra. At 40 years old I have thankfully never had to go that route but you know curiosity killed the cat. Or in this case opened up my ass! After telling the guys at work how I planned on staying in while my wife was out of town visiting her sister,... Read full Story
shemale lover 2012-04-15 4,582 Cumshot sucking jerking gangbang Interracial
0%
Brother of the Bride
“What in the ‘Get Out’ hell is going on here,” quizzed the warm, brownish-red woman with the Bantu knots as soon as they were safe inside the gold 1970 Deuce and a Quarter. “I don’t even know,” chuckled the driver as he jerked his head to get his short dreadlocks out of his line of sight. “Wel... Read full Story
Faggyboi and Puzziboi 2023-07-15 5,693 anal Crossdresser Guy Fucks Shemale Interracial sissy femboy faggot sissy crossdresser BB jack of spades bblbuttcd bbl
100%
Cast a Sexy Spell
I love my body. From my long red hair that drapes over my shoulders to my firm breasts to my slender arms, legs to my round ass. Most of all I love my cock. Yes, I have a cock. It swings between my legs at around 5 inches when not in use and stands proudly at eight and a half when hard. And when I'm... Read full Story
shemale lover 2012-03-28 3,666 anal sex Creampie jacking off
85%
Crossdresser At XXX Movie
It was hot and the sun felt like it was going to melt me. I was walking home from work. I never drive that much and I just got off the bus for a fast beer. I walked past this XXX Movie house and thought what the fuck, it has air and it is so hot. So in I go. I should say that I'm somewhat Bi. Tha... Read full Story
shemale lover 2012-03-30 4,312 anal sex Creampie handjob rimjob
100%
First pair of nylons
When I was working at a machine shop I had to stand all day and my legs would ache at night. My wife told me she was talking to a friend that was a nurse about it and she told her she should buy me some support hose. So one day when I was getting out of the shower and getting ready for work my... Read full Story
shemale lover 2012-11-27 3,156 first time Fetish nylons
78%
How I Became the Sissy Slut
It all started when I was about 11. I was a very petite and short and had long straight brown hair with whispy bangs as a child. I was often mistaken for a girl. I have a sister who was 6 years older than me about my size she used to dress pretty sexy with the tight jeans and the skin tight sailor b... Read full Story
Tvtrinity 2016-08-29 72,823 Teen (18+) Crossdresser transgender sissy slut.trinity
80%
My black fetish
It all started when the boys in class started calling me sissy...so what if I liked panties and nylons and bras who cared....when mum and dad were at work...I would wear mum’s heels and tights and her double D bra...I was tiny and had long blond curly hair and just the beginning of an o so lar... Read full Story
bigtranslover 2014-02-03 6,343
90%
Daddy’s Little Girl
Tony was a beautiful baby boy. Perfectly healthy and well formed. The mother, Susan remarked to her husband James that Tony got a little stiffy everytime she nursed him and wondered if that was normal. They all slept together and that night as soon as Tony started to nurse he sprang a boner. Susa... Read full Story
shemale lover 2011-11-10 9,142 cum oral crossdressing
50%
Lost Girlfriend Part 2
I was in a pretty pissed off mood for a few days, having just lost my latest hot Tg girlfriend, Kelli to Alesha, a well hung black Tg, and decided to go to my favorite exotic dancers club. I recently had some interesting adventures with several of the dancers, I wrote that up in a 2 part short ... Read full Story
shemale lover 2011-12-03 6,597 Ebony transsexual domination
97%
Stepdaughter's Transexual Surprise
I've been through two marriages in the past. My first wife died at an early age of 29 from a massive heart attack and my second marriage was a nightmare from hell, that I'm now free of. When I met Jeanie, I knew I had to take it slow and easy. Jeanie was a very nice lady in her early 40's. I myse... Read full Story
shemale lover 2011-12-04 14,014 anal Fetish transexual
100%
First Time With a Shemale
I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality. I'd been with a few girls growing up, but nothing ridiculous. I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we... Read full Story
shemale lover 2012-02-12 6,562 first time Cumshot sucking
100%
Darla's Diary: Slutfest 1993
Vacation Day One At last!! Another fantastic two weeks of freedom...the freedom to do as I pleased and dress as I pleased because it was my VACATION TIME!!! This year was better than other years because it was the first time my wife and I had two weeks vacation each. Just like she does every othe... Read full Story
shemale lover 2012-07-14 4,175 oral facial cum swallowing anus
100%
Francis Meets a Black Stud
First some background: I am a male, about 5'5', athletic and have long light brown hair and fair skin. I was on the swim team in high school and college. In college I had started shaving my legs and arms to cut down on drag in the water. My girlfriend at the time liked and eventually talked me i... Read full Story
shemale lover 2012-11-20 5,373 Stockings heels self sucking
66%
The Dark Backwards
Let me begin by saying that I am fascinated with shemales! I AM IN LOVE WITH SHEMALES! How did this love affair begin? For me it started back in 1984 when I saw a shemale magazine lying on my high school campus. Someone left it behind or it fell out of a bookbag. That image of a redheaded shemale le... Read full Story
Bryanferryfan 2015-11-16 4,014 orgasm sex transsexuals erotica
100%
THE DARK BACKWARDS
Let me begin by saying that I am fascinated with shemales! I AM IN LOVE WITH SHEMALES! How did this love affair begin? For me it started back in 1984 when I saw a shemale magazine lying on my high school campus. Someone left it behind or it fell out of a bookbag. That image of a redheaded shemale le... Read full Story
Bryanferryfan 2015-11-16 3,004 tranny orgasm hard dick transsexuals erotica
100%
Decisions, decisions.
So if you have read my stuff I’ve posted before I was with a tranny named Nicole for awhile but she left for work last year so after she left I actually started dating normal again went back to girls but never forgot her. I’ve hid the dildo and all my secrets from my current girlfriend for almost a ... Read full Story
Duke04 2019-07-25 8,238 Shemale Fucks Guy Fetish Blowjob Big Cock cum in mouth
100%
Why I’m a Cock Whore!
Hello Love, The summer before my freshman year in high school. I found a VHS porno video right next to a dumpster behind our local video store. Brought it home. Couldn’t watch it until my family left to use the VHS player. It turned out to be a she male porno at first I felt weird but after watch... Read full Story
Samantha Cummins 2023-04-18 6,696 anal Stockings Cumshot Creampie Lingerie femboy Ass to Mouth cum in mouth
100%
Secrets
Jon had invited me to spend another weekend at his place with another of his friends. I always find his friends to be interesting so I accepted. Jon had given me a garage door opener and a key to his home after my first visit. He met me as I parked my car in the garage. He was wearing his usual skim... Read full Story
shemale lover 2011-11-01 6,545 anal Blowjob transvestite
85%
Alpha Gamma's Secret
Molly woke up to the sound of her alarm clock beeping. She opened her eyes slowly and looked at the time. It was 7:00 AM. She groggily reached over to shut it off, pulled away her blankets, and stepped out of bed. She walked from the bed room which she shared with her sorority sister Gina to the ... Read full Story
shemale lover 2011-11-02 4,882 Small Tits asshole transsexual
100%
Force Feminized up Asshole
"Yea I thought the singing was OK but I don't really go for that style too much" "And the girls?" Brian prompted me. "Oh come on Brian leave him alone we all know he's not really interested in girls." "Give him a chance, people can change! Perhaps Carl's d... Read full Story
shemale lover 2012-02-13 7,034 anal Group Sex Fetish cum feminisation
60%
Amy's Surprise 2: Enter Karissa
What did you think? Amy asked. Well, let's see, I started to answer, You gave me the best blowjob I've ever gotten, sucking your dick was about the best thing ever, and sharing your cum with you was incredible.all in all, I'd say it went well. Amy smiled and walked over to sit with me on the couc... Read full Story
shemale lover 2012-05-08 4,918 anal sex shemale Sex Toys
100%
Fender Bender Chapter 9
My name is Robert, I have been cross dressing since I was 14. I turned 18 last summer and this story takes place during my senior year in High School. I am 5'9" 160 pounds, blonde hair and blue eyes. When I am dressed I call myself Vicki. __________ I had met Julie at a recent party. Well... Read full Story
shemale lover 2012-07-27 3,740 Group Sex Cumshot Sex Toys
100%
Sabbatical or Continuous Gang Bang?
My twin sister Laura had already left to go back to college this fall season, but I had decided to take off a semester as I was totally burnt out on school and needed a break. We were twins but not identical though we did look a lot alike and roughly the same size me being a few inches taller. My... Read full Story
shemale lover 2012-08-28 5,904 Crossdresser Cumshot Fetish Blowjob gangbang
83%
My girl in threesome with two shemales
As I watched my girl on the dance floor bumping and grinding with her friends, I was wondering if I would get lucky tonight. Little did I know, I was in for a night of my life. My girl, Lisa was sandwiched between two of the most beatiful blondes alive. Their hips swayed from side to side and as the... Read full Story
shemale lover 2014-04-17 6,888 pussy shemale
100%
Helping a friend
Anna has been working in my office for a year now. I have never heard her talk about a boy or girl firend. Anna is 5'7'', long legs, light brown hair almost to her waist, very pretty. I have always talked to her, had lunch, but she had never opened up until she needed some help..... Anna had boug... Read full Story
shemale lover 2011-09-27 3,363 anal shemales gay male
100%
Connie at an Adult Bookstore
Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * Let me start by i... Read full Story
shemale lover 2011-09-30 4,642 Cumshot Blowjob crossdressing