Sort by
Relevancy

Free Stories

60%
Daniel, Dani, Dana
After an hour of some hot steamy role playing online I got up from my computer. This newest and best chat friend ever was helping me enjoy this private time more than ever. My feminine alter ego seemed to flourish and delight when I spent time with him in chat. Wearing a little more risque under thi... Read full Story
shemale lover 2012-06-08 4,954 Fetish crossdressing sissy
80%
Bisexual Black Man's Paradise
The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... Read full Story
shemale lover 2012-06-24 5,600 big dick tranny anal sex Cumshot orgy facial oral sex
75%
Bitch Maker Chapter 3
"Alex bring me some juice." Sammie said, rolling over in bed and hugging her pillow. "Yes mistress!" I replied, with enthusiasm. I crawled out of bed and walked down the hall, on the way past Tim's room I looked in on him. He lay there silent, his cock trapped in it's new c... Read full Story
shemale lover 2012-06-24 3,266 anal sex Cumshot jerking oral sex
80%
Becoming Alanna Part 2
Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... Read full Story
shemale lover 2012-07-12 4,039 sucking Fetish Ladyboy rimjob
100%
A Visit To an Adult Store
I remember how jealous my older sister always got when I was little and my mother would brush my straight, thick blond hair. "You should have been a girl, Robin," Sis would say, shaking her frizzy, dirty-blond locks. It bothered me because I was not a girl. I was a boy. Mom would sig... Read full Story
shemale lover 2012-07-19 7,679 Fetish dildo Sex Toys fantasies
100%
Fantastic Weekend - First Touch
It finally worked! After a year of posting ads on Craigslist, and what I'd decided was my last attempt, I got results. It was short and to the point, "Panty Sub Seeks Oral Top." As is normally the case, I got a lot of one-line responses and picture requests, but buried in there were two gu... Read full Story
shemale lover 2012-08-31 3,461 Stockings Crossdresser Cumshot Blowjob Lingerie
90%
On the Run
“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... Read full Story
shemale lover 2012-09-01 11,531 Crossdresser Cumshot Blowjob jerking pantyhose
100%
Roberta, Molly and Ed
Friday "Commander Cromartie?" Lt. Commander Edward Cromartie, USN, turned toward the voice that had spoken his name. He saw two female naval officers, a tall willowy light-skin Black woman, and a short Asian one. The Black one was wearing the uniform of a full commander, the Asian of... Read full Story
shemale lover 2012-09-04 5,584 Cumshot threesome Blowjob Big Cock condom sex
100%
Vacation Alone
All packed with a few special items just in case, I'm off to the mountains for a late summer vacation. I'm leasing a small cabin on the lake for just myself. After an exhausting drive I decide to start a bath, light a few candles. I pour a glass of chardonnay. All alone for a weeklong relaxation tim... Read full Story
shemale lover 2012-09-08 3,524 Stockings Cumshot threesome Big Cock cum swallowing
92%
First Times
A little background is in order. During my teen years, I became involved with a woman that helped me discover the pleasures of my female side. Sue helped me to dress and act in a very feminine manner. We were almost like sisters in the way we became so close. She would sometimes describe how good... Read full Story
shemale lover 2012-11-02 4,039 first time Cumshot sucking
50%
Dream Lovers Part 2
Chapter 2 Christine Moves In, Brings Her Roommate Matt could not wait to give Christine long awaited good news. He entered her room and did not immediately see her. He noticed the open bathroom door and saw the woman of his dreams stark naked at the sink bushing her teeth. Her ass wiggled as ... Read full Story
shemale lover 2012-11-15 3,385 Cumshot shemale oral facial
72%
For Want of a Heel
"Shit, shit, SHIT." Sally glared at her right foot. The heel of her shoe was broken off, still caught in the chink of the cobblestone walkway she was standing on. She carefully set the bag holding her laptop down and reached down to pull the heel free. "Two hundred dollars," S... Read full Story
shemale lover 2012-11-15 3,623 tranny Cumshot oral sex
100%
An Invitation
"Oh come on,Sarah. There has to be a way." An innocuous enough statement, but that's how it all started. I'd just received an invite to Cressida's annual Christmas party which, maybe not on the Hollywood A list, was within the cognoscenti an occasion not to be missed. The soirees of ... Read full Story
shemale lover 2012-11-16 4,772 Fetish oral sissy
100%
Emergence of Josette
It was a few years ago when I admitted to my wife that I love dressing in women's clothing. It was after she found a stash of some of my panties. They weren't her size, so it was an immediate red flag for her. She didn't immediately believe me. So I gave her an impromptu fashion show. She seemed unc... Read full Story
shemale lover 2013-01-22 4,950 hardcore Cumshot threesome ass fucking Sex Toys
96%
How I Really Got My BA In College
I was living in an off-campus apartment building two months into my first semester of a two year BA program. I lived on the 22nd floor and my three friends Ray,Jim and Dan lived together on the 13th. As it was Friday night I threw a couple loads of laundry into the wash and went downstairs to cadge ... Read full Story
shemale lover 2013-02-12 6,350 Cumshot sucking Blowjob ass fucking swallowing
71%
TGirl Initiation by 3 BIG BLACK 12
In my teen years I was often told that I was quite feminine.The high school punks always told me that I filled out the back of my jeans in a girly way. After taking a shower one day I did notice that they were right, I had a nice white bubble butt. Not to mention that my lips were also quite girly. ... Read full Story
TgirlJill4BBC 2013-06-04 9,283 Stockings Cumshot suck Big Cock Lingerie Interracial Latex
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 29,513 Teen (18+) suck oral Lingerie make up
85%
True story, TS 3-way
This is a true story. It was a typical night in Pattaya Thailand and I'm still recovering from the 25 hour flight from Tennessee to Bangkok that I flew just days before. After a few days in BKK, I arrange for a hotel car to me to Pattaya, a seedy explosion of lights, blaring music and drunken ... Read full Story
Thailover 2014-03-11 9,946 Cumshot threesome jerking ass fucking facial stroking
31%
Mothers fashion mags
I think looking at womens' fashion mags when I was young must have fueled my crossdress fetish later in life. My mother back in the 80's used to get fashion mags in the post. I used to look through them and flick to the under wear section and see pictures of women in bras and pantys and go... Read full Story
Saoirse1973 2017-05-08 3,473 Teen (18+) Amateur
94%
My first Shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe that started my intere... Read full Story
SachinJoy 2018-10-04 32,987 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy cum in mouth
50%
I and the old man's story 后面中文
I am from Chongqing, a boy who loves his father. When I was young, my neighbor aunt always said I looked like my sister, like a beautiful girl. At that time, my family was relatively poor. My Sister, my parents, and my family of four lived in public rental housing of less than 30 square meters. Star... Read full Story
Oldslut Sissy 2024-04-15 9,382 Crossdresser Amateur Masturbation Asian Ladyboy Guy Fucks Shemale Mature small cock Homemade sissy chinese teen (18+)
80%
Getting Fucked by Sasquatch
Bill was about to show up, I had known him from a chat room for years now. I was in his town for work and we had set up this date so we could finally meet each other. I heard a hard knock at the door and when I swung it open, I just stood there in awe. It wasn’t the big beard or really long hair tha... Read full Story
pennypenny 2020-08-21 6,194 Crossdresser Bareback Creampie Fetish Blowjob Big Cock redhead domination Guy Fucks Shemale pov Ass to Mouth cum in mouth
100%
Casino Girl
I had been working as a casino dealer for several years and would occasionally meet some very attractive women and chat. Asian women have always been attractive to me, whether the exotic appearance or maybe because my Mom was Pacific Islander, and a lot of people thought I was Asian. Mia was a bit... Read full Story
Jon Paul 2022-01-03 3,121 Stockings Cumshot Bareback Blowjob Asian Ladyboy Guy Fucks Shemale
100%
First Time Buying Lingerie
As a youngster, I couldn't help but notice the carousels of hosiery on display in various shops that my mother would visit. Displays of stockings and tights (pantyhose) for the discerning housewife. Brands like Pretty Polly, images of nylon clad legs on the glossy cardboard and a see through window... Read full Story
Daddybear71 2023-09-13 6,787 Stockings Crossdresser Amateur Masturbation Lingerie teen (18+)
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 4,278 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
50%
Oggi in ufficio è arrivata la moglie del capo
In ufficio sono abitualmente usata da mio capo, ogni volta che ha voglia viene da me o mi chiama nel suo ufficio e mi usa per svuotare le sue palle, oggi arriva accompagnato da un biondona CIAO HELENA buongiorno LEI E’ MIA MOGLIE senza che io possa rispondere mi alza la gonna e le mostra la ... Read full Story
helentrav 2023-10-07 4,608 anal Crossdresser Cumshot threesome Blowjob blonde domination Guy Fucks Shemale sissy cum in mouth
100%
Wife got suspicious...
Wife got suspicious... I ended up having a relationship with a married man I'll call Tom. I didn't know he was married until he told me we had to stop kind of like dating because his wife was getting suspicious. We met online, he was a guy who liked crossdressers like me. He was pretty cute... Read full Story
Kellygirl81 2024-06-18 2,793 Stockings Crossdresser Cumshot Lingerie Frottage cum in mounth
85%
Whores and Pimps - Part I
Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm h... Read full Story
shemale lover 2012-05-13 8,239 Stockings Crossdresser Cumshot Fetish oral sex pantyhose
92%
Caught in High Heels
I couldn't believe the feeling as I slipped the pantyhose on over my legs. This was an absolute dream come true and I was living it right now. My friend Julie had gone out for the night with her 15yo daughter and she'd given me the spare keys to her house. She'd had a tradesman doing some work an... Read full Story
shemale lover 2012-10-12 5,956 Cumshot Fetish crossdressing
100%
Daddys Little Slut
I have been living with my dad for the last year after my mum who is Indian, found out that I was doing lots of drugs, and that I was bi and also a cross dresser. We never talked about it as for me, the cross dressing was on and off and usually when i was high. When i turned 25, I tried meth, and fo... Read full Story
aishacox 2023-01-31 5,618 Crossdresser Cumshot Fetish Blowjob Latex
100%
Hose and Heels in the Bedroom
Liza giggled as she sat back down on the sofa, a mischeivous smile on her face. "Whats so funny I asked?" wondering what had tickled her fancy. After all the only thing that had happened was that she'd just been to the toilet to relieve the pressure that the 3 or 4 glasses of wine tha... Read full Story
shemale lover 2012-05-15 4,193 anal sex Cumshot Fetish fingering pantyhose heels
60%
A Sissy Boy is Made
By any measuring stick Greg Martin was a wimp, and a very submissive wimp at that. His wife of 14 years, Jaclyn, had discovered this even before the two of them were married. Actually, Jaclyn wouldn't have taken a second look at Greg, as most women didn't, had it not been for his submissive nature. ... Read full Story
shemale lover 2012-06-15 8,643 Cumshot oral sex sissy
100%
David to Dee
"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... Read full Story
shemale lover 2012-07-29 12,819 Cumshot Masturbation oral sex
100%
Shemale Fantasy - Suck Fest
This story is completely fictional - in fact it is a fantasy of mine that I will describe in great detail, contact details are at the bottom if you want to make this a reality! I arrive at your house on the evening. You let me in and show me to the spare bedroom. I walk in and close the door behi... Read full Story
shemale lover 2011-09-13 5,475 Cumshot jerking off pantyhose
60%
The Clinic
I got out of my cab and looked up at the Clinic. It was a small, nondescript hospital. I was still pretty nervous about this treatment since I wasn't even sure of the details. But it was either this or go under the knife. This problem had to be dealt with. I picked up my bag and went into the lobby.... Read full Story
shemale lover 2012-05-02 6,111 Cumshot Big Cock jerking off oral sex cum swallowing
71%
A Schoolgirl's First Time
I’d been emailing and phoning Dan for several weeks when he first suggested that we meet up. It was very exciting and I couldn’t wait. My every waking hour was spent thinking about it. The only odd thing was the request he’d made. “Can I ask you a bit of a kinky favour?&rd... Read full Story
shemale lover 2012-06-10 4,489 Cumshot Fetish Uniform oral sex crossdressing
100%
Head Cheerleader Mikki Part 4 Mikki wants a Boyfriend
This is part 4 of Mikki's story. Please read the previous chapters. After Monday night at Tommy's house I came to the conclusion that I want to be with Donna when I'm Mick and guy when I'm Mikki . It's Friday night and Donna is coming over . My dad is coming home on Sunday so my mother wants to s... Read full Story
shemale lover 2012-06-16 2,716 first time Cumshot oral sex double penetration
100%
Throat fucked by two black photographers
Well for a very long time i would go to a hotel room to dress up in my sexy outfits and set my camera on auto and take my own pics .After a while i got bored with that and wanted to do a photoshoot with a photographer so i rang around and found a guy who would take my pics .I went out and brought th... Read full Story
shemale lover 2012-08-01 2,636 Cumshot Fetish oral sex
50%
Polish Maid
'You want to get tips,' I explained to Marek, our Polish cleaner, 'You should be more a maid more like her.' Across the street was a girl of about 19, dressed in a fancy dress French maid's costume stumbling home, presumably from a party the night before. She was dressed in a tiny black dress, l... Read full Story
shemale lover 2012-09-01 5,016 Stockings Crossdresser Cumshot sucking heels
84%
Lesser of Two Evils
My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... Read full Story
shemale lover 2013-03-27 23,033 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
94%
Flight cancelled
I was on my way back from a long business trip to Chattanooga, Tennessee and deciding to hit the airport bar during my layover. As I walked up to the bar I noticed there was only one seat open. I took it. I ordered my favorite drink, an old fashioned neat with makers mark. As I sat there waiting for... Read full Story
Jsmithsub 2019-10-31 24,666 big dick Group Sex Bareback Shemale Fucks Guy Fetish Blowjob Big Cock pissing Ebony domination cum in mouth monster cock gang bang
100%
From accidental trans porn addiction to a cum filled booty
One night when I was around 30 or so I was watching some porn, nothing unusual for a guy like me, aka a sex addict. Sex addiction is great if you’re Tiger Woods and swimming in poon, but for guys like me - regular, awkward, slightly handsome in a very boyish way, weirdos — it’s not that fun. We... Read full Story
CDJaneBooty 2022-04-01 10,517 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
100%
I got anal creampied at the beach!
As soon as we got onto shore, I knew it was the perfect place. The hot sun was beating down on us and my body was tense with anticipation. Finally, we were going to be alone out in the wilderness with nobody around and could enjoy each other thoroughly. My hunky date and his monster cock were going ... Read full Story
Madison Heights 2022-12-01 5,086 Cumshot Outdoor Creampie Fetish Blowjob Big Cock Ebony Guy Fucks Shemale public bbc massive
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 16,824 shemales Masturbation Fetish
75%
Backseat T-Girls
A few months ago I had another one of those hot encounters that only adult film stars/models such as myself seem to have. It was one of those spontaneous, animalistic, “got-to-have-it-now” type encounters. For those of you who do not know me I am a transgender (male to female) adult v... Read full Story
shemale lover 2012-02-09 3,200 Cumshot suck Big Cock fuck
100%
A Discovery
The booze and caffiene had turned from a warm buzz into a slightly annoying headache in Miles' psyche. He watched as his live-in girlfriend Mary danced and ground against a tall blonde that could have been her younger sister. Club Inferno was at the point of orgasmic rush when the standing room only... Read full Story
shemale lover 2012-04-29 4,384 Cumshot shemale Big Cock oral sex
66%
A Perfect Cuckoldress Wife
My wife rose slowly, before lowering herself down his length again. Her head tipped back, she squeezed her breasts, playfully teasing her own nipples. Her eyes opened, lustfully admiring the chiseled ebony body of her lover. Balanced skillfully on her stockinged toes, she began picking up the tempo ... Read full Story
shemale lover 2012-04-30 5,327 Cumshot Creampie Fetish crossdressing
100%
Danielle's First Meeting
Daniel stood on the front porch and waited for his date to arrive. Well, Daniel at this particular time was actually Danielle. You see, Daniel was a crossdresser. Danielle was his female alter ego. He was 37 years old, medium build, average you might say and stood 5-feet-10-inches tall, weighing in ... Read full Story
shemale lover 2012-06-18 4,453 Stockings Crossdresser Cumshot shemale oral sex
100%
A Ski Bunny is Born Chapter 2
My first real man. Hugs and kisses to everyone who contacted Kim and I expressing how much you enjoyed our first episode. This is the second part of our life story so far, and is the first follow up to 'A New Ski Bunny is born'. It recalls the first time that Kim and I included guys in our ... Read full Story
shemale lover 2012-06-21 5,066 anal sex Cumshot oral sex rimjob
100%
A Slut Is Born
I've always had a magnetic attraction to slender pointy hi-heel stilettos since way back when. And then these wonderful sensual sexy feelings between my thighs every time I see a young lady strutting and teetering around on these fabulously erotic pointy heels. It all started in the 1950s era. The e... Read full Story
shemale lover 2012-06-23 3,355 Cumshot Masturbation Fetish
100%
A Special Friend
I met Charlene in my freshman year of college, about eight years ago. Back then she wasn't what I would consider very attractive. She was kind of tall and had very little curves to her body. Her hair was straight and un-styled; she had a flat chest, wore black rimmed glasses and had very oily skin. ... Read full Story
shemale lover 2012-06-27 3,313 anal Cumshot shemale oral
100%
A Tale of Cum and Passion
It was an anonymous meeting, set up through a popular Internet site. The profile specified I was looking for a transsexual or a transgender woman with nice legs and feet. Basically I was looking for a chick with a cock to satisfy my fetishes for legs, stockings, feet, cock, and cum. Victoria walk... Read full Story
shemale lover 2012-07-06 4,225 anal sex Cumshot shemale oral sex
100%
Blossoming Shemale
My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to prove it now, and to be honest, I didn't really have the desire. That was all before. I have to ... Read full Story
shemale lover 2012-08-01 5,214 Cumshot shemale Big Cock oral sex
100%
S is for Selena
"His name is Ken," my friend Isabella had told me as she recounted her own encounter and that of her friend. "I got to first base with him that first time he came in the club. Just a quick snog and then he seemed to take fright." "Were you wearing that red dress, the one ... Read full Story
shemale lover 2012-08-27 3,985 anal Cumshot blonde
100%
Retail Therapy
It began, as many of these stories do, with a pair of panties. I love lingerie as much as the next girl, but never overly indulge, as money was a little tight. My new husband Alexander and I had finally settled into our post-college lives and were reasonably well off, but had a plan to pay off colle... Read full Story
shemale lover 2012-08-31 3,980 Crossdresser Cumshot Blowjob jerking Lingerie
100%
Brianne in her College Days
In my early days of x-dressing, when I was just getting the feel for what to do and where to go, I was a bit nervous. Maybe more so nervous than excited to be doing what I was doing, but not one event that changed things was when I stumbled upon a bookstore that was just a mile or so from my dorm in... Read full Story
shemale lover 2012-09-21 3,015 Cumshot sucking Fetish crossdressing