Sort by
Relevancy

Free Stories

93%
The Hot Girl at the Bar
My girlfriend and I broke up the week before, so I was pretty depressed. The guys at work decided to take me out to the bar after work to get wasted cause that’s what we do. So we all packed into the truck and headed to the bar. When we got there we were the first ones in that night so we sa... Read full Story
shemale lover 2015-10-01 10,376 anal suck Creampie
94%
My Girlfriend's Cock
I have had many girlfriends over the years but the one I have now is very different. Her name is Kim and she has a cock that is as big around as a beer can and about 8 ½ inches long. Kim is a beautiful woman with a cock. When we first started dating I had know idea that Kim was packing a b... Read full Story
shemale lover 2011-09-08 6,780 asshole Creampie fingering
100%
Susan's First Time Part 3: Susan's First Party
The chauffer passed through a gate in the high brick fence just as the sun started to slide behind the distant snow capped mountains. The cobblestone driveway that wandered toward the main house must have been a mile or more long. Susan admired the immaculately landscaped grounds as they drove throu... Read full Story
shemale lover 2011-10-13 2,599 anal Group Sex Creampie oral
95%
Interesting Suprise
This all happened several years ago when I was in the Navy in San Diego. One payday weekend I was in a partying mood so I thought I would head down to Tijuana for some fun. Being I was about 20 at the time I headed for one of the clubs where a lot of the college kids hung out hoping that I might g... Read full Story
bjw_6 2011-10-23 7,718 suck Bareback Shemale Fucks Guy Guy Fucks Shemale 69
50%
Man or Mandy? Part 3
We showered together, washing each other. We spent as much time kissing as watching. I was spending much of my time on her incredible tits, getting them all soaped up, and then rinsing them off. We got dressed, hopped on my Harley and roared off towards an auto parts store. As went into the mainl... Read full Story
shemale lover 2011-11-26 2,218 anal sucking Creampie ass licking
100%
Just One of Those Days Part 2
Hello again. My name is Amanda, though sometimes I use the shortened version Mandy, when the mood suits me. I'm 33 and have stayed single for three years, since I discovered that Richard, my boyfriend, was not only cheating on me with dozens of women, some my so called friends but was al... Read full Story
shemale lover 2011-12-09 3,262 cum massage shemale sex
75%
Permanent Stay in Mastersville Part 5
When I woke up, I was so sore that I could hardly move. My body was a mass of pain and as I removed the blanket, I saw how bruised and ugly all the abuse had made me. The sight of my battered body made me sob with self-pity. I lay quietly waiting for Master to arrive. I didn't feel rested, but at le... Read full Story
shemale lover 2012-01-08 3,853 toys bondage and discipline heavy reluctant
100%
After the Gala
Climbing into Jack's car, I shook my head in disbelief, was I really going to join him for more drinks? We had just met that evening at the Board of Trustee's year end gala. I knew he had been involved with the administration for some time, I was a lowly secretary for the grounds crew supervisor; bu... Read full Story
shemale lover 2012-02-07 3,196 anal Creampie fuck
100%
My brother's biggest surprise!
Lilly did not like her new step-brother at all, Todd was the worst sort of punk, bad attitude, cocky, arrogant and he thought he was God's gift to women. His father had married her mother nearly a month ago, and Lilly hated it. He called her names like "teentwat","shitster" and ... Read full Story
shemale lover 2012-04-08 5,234 hardcore anal sex Creampie oral sex
100%
Bar bang
I must start out by saying I love to turn guys on. I decided to go out with a few girlfriends to a bar this weekend. When we walked in a few heads turned and noticed us. After a few drinks I was feeling very horny and turned on and so I started looking around the bar and someone caught my eye. They ... Read full Story
shemale lover 2012-05-21 2,343 anal sex Creampie handjob
75%
My shemale GF Part 2
So today she, her name is Christy, she wanted to do something kinky, very kinky I said that's fine. We cleaned up, she went into her closet, which was filled with dildos, butt plugs, sexy clothing, fleshlights, cock rings, paddles, lube, videos, magazines, bdsm things, and a fuck machine. She came o... Read full Story
shemale lover 2012-07-04 3,660 anal sex Creampie shemale Latex rimjob
100%
Female Seduces Shemale Chapter 2
I wake up to your soft kisses on my throat. I open my eyes to see you fully nude laying over top of me with your hands on both sides of my chest holding yourself up. You look down and smile at me seductively. You lean down for a kiss. I feel your hot tongue parting my lips. I open my mouth slightly ... Read full Story
shemale lover 2012-07-07 2,692 anal sex Creampie fingering Shemale and Girl facefucking
66%
Your Waitresses
You begin your evening by taking a long luxurious bubble bath followed by taking the time to apply your makeup at a beautiful white makeup table and mirror from the 1920's. You then slide a sheer pair of black stockings up each leg and attach them to your black and red lace garter belt. You then run... Read full Story
shemale lover 2012-08-10 3,783 Fetish cum crossdressing
83%
Abducted and Turned Out Chapter 1
About four years ago, I decided to go out for the evening to a local club that tgurls hung out at. I was a regular there, and had been going there for some time with a regular circle of TG/CD girlfriends that I hang out with. I was already excited when I started to prepare myself in the late afte... Read full Story
shemale lover 2012-08-10 5,254 Crossdresser blonde oral sex cum swallowing
100%
One Night of Lust
Hi, my name is Kelly and I've been a tranny for 3 years now. I'm 22 and just got a stunning boob job, 34C. After three and a half years of taking female hormones, I can turn the heads of any and all straight men on the street. I am also a cage dancer at an erotic club in Atlanta for people of all wa... Read full Story
shemale lover 2012-09-02 3,366 Stockings Big Cock ass licking Interracial heels
90%
In Hose and Heels for Daddy
It was shortly after my 14th birthday when I made the decision to seduce my Daddy. I mean, all of my girlfriends were having naked fun with their daddies. I didn't wanna be left out ;-) After all, me and my BFF, Ashley, had been getting naked and having fun with her daddy for 2 whole years now...and... Read full Story
shemale lover 2012-09-30 7,449 Fetish jerking crossdressing
100%
Amy's Awakening Chapter 3
We fell asleep in each other's arms and I purred like a kitten getting its belly rubbed. I couldn't believe how I felt or what I was going to do. Was I to stay in my marriage and continue seeing Sandy on the side whenever I could or leave my wife and become Sandy's full time? Of course I didn't know... Read full Story
shemale lover 2012-10-30 2,311 anal sex sucking Creampie
100%
The dream that became real
ok wear should i start? I guess we could start while I was at work. While I was at work at the movies i walked in on my coworkers haven sex only iut wasnt normal sex i had no idia latoya was a hermaprodite. They didnt notice me cuse i was watching them all of a sudden i seen a 13inch cock go i... Read full Story
shemale lover 2012-11-06 3,305 anal Creampie oral
100%
CD new sex friend
Tyrone is a tall skinny black guy 22 years old and his Mel is short and pudgy. I am an older white sissy. I wear female clothing under my regular clothes all the time. Saturday morning I went to the small house they rent and brought an overnight bag. Tyrone opened the door and I walked in. I s... Read full Story
shemale lover 2014-07-31 4,952 Creampie ass fucking ass licking Interracial cd
100%
Claudia Coming out adventure part 1
*Author's Note: This story starts off being told in First person and after awhile the story shifts to third person* Hello everyone, my name is Claudia I am a Cross dresser who one day hopes to be transgendered, although I do not want the surgery, I am looking to eventually live my life full... Read full Story
MissClaudia 2015-01-04 5,970 tranny Stockings suck Creampie ass fucking doggy style Latex
84%
The One That Got Away
I was out on a Friday night seriously just looking for a couple beers and a burger. I had a lot of work to do around the yard and house on Saturday and was having some guests for brunch on Sunday. Full weekend, tired from the week. I went downtown to a new gastro pub I’d seen reviewed in the local p... Read full Story
Giantsquid 2017-05-15 5,714 Amateur Bareback Lingerie guy on shemale
80%
Ann and I
Last night I had an awesome experience. I was down in Fort Worth to meet a tranny I had been talking to on squirt. I got off work early, took a shower and shaved my cock and balls and dressed in jeans and a t-shirt and headed down to Club Changes to meet her at four. The bar was pretty empty, Thu... Read full Story
Giantsquid 2017-10-13 13,983 Small Tits Amateur Bareback Guy Fucks Shemale Ass to Mouth cum in mouth
85%
Gay Cumslut
I was busy at work and Robert a guy I work with needed a little help. I told him to come into the lab and I locked the door behind us as I wanted to get some work done undisturbed and then go home. I leaned over one of the computers that I had been working on most of the day. And after a couple of m... Read full Story
MARKUS6969 2018-04-23 12,391 first time Bareback gay sex cumslut sissy slut
84%
Becoming Zoe
My soon to be wife Annie had taken a job out of town and I only saw her every two weeks or so. I was so missing her. She and I had become long distance lovers. She was scheduled for a flight home on Friday night. I was going to pick up her son Zakk from his dorm and the two of us were going to p... Read full Story
Zöe from Kingston 2018-08-09 9,240 Stockings Teen (18+) Crossdresser Cumshot Bareback Blowjob blonde Big Cock Lingerie Mature cum in mouth
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,513 Big Tits Cumshot Masturbation Uniform Frottage
100%
Masturbation fantasies 2: Looking for Amanda
Previously: William, a young lawyer who has no luck with women, decide he needs some relief from a live girl. Scared of going with a prostitute, he decides to try out a peep show first. Without knowing that the stripper he chose is kind of special, he ends up in a show with a shemale called Amanda w... Read full Story
ThatEroticWriter 2019-07-24 8,929 Big Tits Cumshot Masturbation threesome Frottage
62%
My Brother and I.
HI, I am Farzana,(have set my name recently,before that my name was Raja). I am Bangladeshi. I have been leaving with my family.Now I live with my Dad only.Some times, He invite his friends also. I will tell You about this later. I am 27 years old.The story I am sharing with You is about ...14 year... Read full Story
Esrat 2019-11-26 9,593 Crossdresser Group Sex Cumshot Creampie Fetish Blowjob Big Cock Asian gangbang domination Homemade cum in mouth
84%
First Time: How I Love Cock
The first time I ever sucked a dick was when I was around 12 years old. I was at a sleep over with a friend. We were camped out in his backyard in a tent and he started things out tentatively by asking about my luck with the ladies, which was non-existent. Then he suggested that since neither of us ... Read full Story
wickeddogg 2019-12-11 33,822 Teen (18+) Cumshot Bareback Blowjob cum in mouth
77%
Slut indiscretion
At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... Read full Story
Regina10 2020-09-16 5,488 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth
100%
First intercourse with a man
If you read my previous story, “First time with a man”, I gave my first blowjob. What I didn’t mention at the time, was that I was on my way to work about 2pm in the afternoon, (I worked the swing shift). That afternoon meet up was just to see each other, talk and maybe meet again later. But my e... Read full Story
Mistysis 2020-10-23 7,246 Crossdresser Amateur Bareback
100%
Sissy gets her Prezzie
Justina woke up on Monday morning and was already tired, she had been dogging till 3 and her little ass was a little bit sore. She made her way to the bathroom and had a pee, brushed her teeth then headed for the kitchen to make coffee. As she was walking her phone went off, she had a text from ... Read full Story
Samantha Jewels 2022-01-06 3,254 Stockings Crossdresser Cumshot Bareback Blowjob Big Cock gangbang domination Mature Homemade Ass to Mouth
100%
He Could Have R*ped Me!
This guy was so big, taller than me and I'm 6 feet, and bigger, not fat, just right for his big size, and I am so skinny, except for my tummy, that he could have pinned me down and forced himself onto and into me against my will, and no matter how much I'd struggle with him and fight back, he could ... Read full Story
Chrissy Tunnell 2022-02-02 2,842 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
100%
How I Became His Office Fucktoy
Until this job ended last year, every day at my lunch break I would service one of my many Daddies in his office in the building where I worked. He'd always slip me a few bucks, a $20 or even $50 afterwards, not as a payment for sex, but as a "tip" "for all the hard work you do here," he says. I wor... Read full Story
Chrissy Tunnell 2022-02-18 3,791 Crossdresser Amateur Fetish Blowjob Ladyboy domination Guy Fucks Shemale Mature cum in mouth
100%
Shopping plus extras!!!
Hi, so as you can probably imagine I buy a lot of underwear and have a few favourite places to shop. My favourite by far is Ann Summers. The range is great and the staff are so helpful . Anyway back to the story. So I decided to go get some new underwear to see in the new year, I got myself up and d... Read full Story
Samantha Jewels 2023-01-06 4,400 Crossdresser Amateur Cumshot Fetish threesome Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Ass to Mouth cum in mouth
50%
My friend Barbara,
My friend Barbara, I look forward to welcoming Barbara. She is a lovely brunette with blue eyes who likes to make love without taboos. She knows how to bring our fantasies to life by imagining exciting role-playing games. - You're going to fall in love when you discover my underwear, she assur... Read full Story
sandratvtg 2024-07-04 1,316 Stockings Bareback Fetish transsexual Lingerie Sex Toys travesti Vintage rosebud plug gonflable gode xxl
81%
First time in Bangkok
If you have read my story about the first time I was with a TS girl then you know my experience was limited to just a few times. So about 4 years ago I went to Thailand to visit my buddy who was working there in a high profile job with the Thai government. We stayed in his apartment on the 40th floo... Read full Story
shemale lover 2015-01-13 13,675 shemales hardcore Group Sex
42%
Bambii's New World Part 2
There I was filled with cum. I had just been fucked and used like the total whore I was turned into. And even though I thought it was wrong in my mind, other parts of me were saying it was right. My cock wanted to explode, but my sheath wouldn't allow it. My pimp, James, said I'd be able to relea... Read full Story
shemale lover 2011-10-07 4,565 anal sex asshole Creampie
100%
My New Outfit
My sister knows that I have been dressing in girls clothes for four years now ever since she caught me in her black string bikinis and white patterned tights when I was 14. Needless to say, I freaked out but she was completely cool with it. Ever since, we go shopping for new clothes together wheneve... Read full Story
shemale lover 2011-10-26 3,246 anal Creampie crossdressing
100%
The Birthday Gift
I wasn't really looking forward to my 25th birthday. It's not that I was worried about getting old. Trust me, I'm not one of those guys who go looking for new gray hairs every week. Besides, I was pretty damn happy with my body at the time. I stood about 6' 2" and had a pretty muscular build. I... Read full Story
shemale lover 2011-12-29 4,838 cum transgender bondage and discipline
100%
Forever like this
It's late, and the night of dancing has left us exhilarated; tired in that way that makes you feel more alive than you do any other time. We wave goodnight to my housemates and shut my bedroom door. Sam grins her impish grin at me. She'd gone for a goth look, this evening, ladling on heavy eye ma... Read full Story
shemale lover 2012-01-31 3,295 anal Creampie Shemale Fucks Guy
100%
Barbie Jo Adventures Part 6
Saturday When I woke up, I was alone in Harley's bed. I went to the bathroom for the usual thing when you first wake up in the morning. I looked at myself in the mirror and saw me, a guy. I felt embarrassed being in Harley's house with no makeup on. I had a quick shower, borrowed Harley's razor t... Read full Story
shemale lover 2012-02-18 4,382 cum oral face fucking
100%
A Job in the Theatre Chapter 9
What a difference a weekend could make Paula thought sitting up in bed that Monday morning. In just two short days her life had changed completely. She had discovered cock. Playing with hers was fun, but playing with others was even better. And there was a world full of cocks just waiting for her to... Read full Story
shemale lover 2012-03-13 4,755 shemale cock sucking
100%
Carrie Ann's Delight
Chapter One It was a Friday afternoon that seemed of little consequence. I got up, shaved, cleaned and pampered my body. After my underwear was in place I wore my usual boots, boot socks, jeans and a plaid shirt. The bar at Fulton Street was busy that afternoon when I arrived about 2:00 and every... Read full Story
shemale lover 2012-03-19 6,429 cum domination transvestite rimjob
100%
A Natural Sissy Part 2
The Party Just before we reached the entrance, which was manned by a doorman, I said, "Now remember, Stacy, you just do what I tell you, and everything will be fine." "Ok... okay." His nervousness was showing, but that was to be expected. He had no idea what was going to me... Read full Story
shemale lover 2012-03-24 4,305 anal sex Creampie oral sex sissy
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 4,060 anal sex Creampie handjob rimjob
100%
Fill'er Up
It had been nearly a year since it had all started. The emails back and forth, late night text messages, and the pictures…Ohhhh, the pictures. It had taken me nearly 2 months to get her to send me one. Well, one like I wanted. I remember the very first one she had sent. She was gorgeous. Blac... Read full Story
shemale lover 2012-04-04 3,676 anal Creampie oral
100%
Rachel and Chris - followup for Crissy
“Crissy!” I shouted at you as you peered out of the closet door. “What in the hell are you doing spying on Rachel and me?” I asked. Before you could answer, you saw my hard cock pull out of your sister’s pussy, covered in shiny sweet juice. You knew you wanted it ... Read full Story
shemale lover 2012-04-10 2,567 Creampie cum swallowing crossdressing
100%
Crissie Fucks the Neighbor
It was a Saturday afternoon and I was all alone in the apartment as my roommate Kelly had gone home to visit her mother for the weekend. I hadn't had a date or been more importantly been laid in several weeks. Needless to say I was very horny. I quickly flipped through the TV channels and as usual... Read full Story
shemale lover 2012-06-07 3,973 anal sex Creampie oral sex facefucking
100%
Fender Bender Chapter 6
My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I had just turned 18. Mom and Curt had been home form their vacation for almost a week and I hated it. Sure I was glad to see my Mom but with them around I had to revert back to bei... Read full Story
shemale lover 2012-07-26 3,397 Cumshot oral sex cum swallowing sissy
100%
Brad and Tina
It started a year ago; I would get on the AOL chat rooms in hopes of meeting local dominant men. I was seeing a guy named Dan from time to time, just a fuck, nothing serious. Mistress Olivia was an incredible woman and the Domme I was currently serving. She satisfied most of my cravings to be ... Read full Story
shemale lover 2012-08-20 2,455 Cumshot sucking orgasm cum swallowing
100%
Thai Ladyboy goddes in Tokyo and a cheap love hotel
This is a real account of my meeting last week with a beautiful Thai ladyboy working at a flashy show at a night club in Tokyo. Written as a not to her. Hope you like it. You sexy ladyboy goddess, I must say you have the most beautiful body. When we first started drinking wine and talking ... Read full Story
lblover77 2012-10-09 9,858 anal Ladyboy oral
100%
Wife Converts Husband Chapter 3
After about a month of being dressed up and acting as a female, trying out all the different outfits we had purchased and Shelley feeding her strap on cock to my willing mouth and ass every chance she got. My ass and mouth was now well and truly broken in. Shelley came home one arvo with a flyer ... Read full Story
shemale lover 2012-10-18 5,520 anal sex sucking cum swallowing
100%
Donna is Donna but John is Joan
I’m an average size guy. Five ten, almost thin, and at thirty years of age, very little facial hair. My beautiful wife was four inches shorter than me, thinner and as she had pointed out many times before, my arms were as skinny as hers. She always talked about me dressing up girly with her be... Read full Story
shemale lover 2012-10-28 3,471 anal Creampie facial oral sex
91%
The Dinner Party
The clock above the kitchen sink read 7:48 when I heard the metallic snap of Aya's key unlocking the front door. I opened the oven door and was rewarded with a blast of steam that smelled like a lazy August afternoon, all rich garden spices and earthy head. Inside was a boxy cookie sheet covered in ... Read full Story
shemale lover 2013-01-11 5,409 hardcore Cumshot sucking Creampie ass fucking
88%
Caught Crossdressing by a Real Man
This story is a continuation of night club cum slut. Ever since I first wore panties for a boyfriend, I had built up a collection of lingerie. I gradually worked up from panties to the most erotic lingerie I could find. My fascination with cross dressing went a little further with a new fetish f... Read full Story
shemale lover 2013-01-17 35,551 Crossdresser sucking Lingerie ass fucking ass fingering
93%
I Am My Wife's Best Girlfriend
I was standing in our bedroom, my wife was on her way out the door. I was holding her slip up against my naked body. It felt very sensual. I pictured myself, for just a moment, as a real woman, with large breasts, big blonde hair, and smooth, hairless skin. I rubbed the fabric against me, sighing. S... Read full Story
shemale lover 2013-01-18 7,245 Crossdresser Cumshot Creampie Blowjob ass fucking