Sort by
Relevancy

Free Stories

100%
Crossdresser gets dick for first time
I was so tired of just watching porn. So tired of the sissy hypno threads that made me crave men, crave cock, crave being weak, crave being the bitch...only to cum and do nothing about it. But the desire to transition from fantasy to reality was growing stronger and stronger. I decided it was ti... Read full Story
Sissy Ava 2022-10-11 7,805 Stockings Crossdresser Amateur Bareback Big Cock Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Proud To Be A Sissy Chapter 1
I had just turned eighteen and only had two months of high school left. My marks were good and already had a possible placement in a university where I hoped to get a new start. I was so looking forward to getting away from all the shit that life had forced on me in this little hick town. Usuall... Read full Story
shemale lover 2012-12-23 11,871 Stockings Crossdresser Big Cock ass fucking ass licking
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 10,005 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
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 4,007 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
100%
Shawshank affair
Courtrooms can be a scary place. They smell like older leather, the wood paneling has been polished with oil and each sound penetrates your body like a loud smack from a cap pistol, which echoes in the forest, especially the gavel smacking on a block from the Judge. I felt strongly that I would be f... Read full Story
Jon Paul 2018-08-20 6,575 Stockings Crossdresser Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Property To Be Pimped
It had been weeks since I'd brought to light my idea of my wife, Suzie, strapping on a big dildo and taking me dressed as Desiree, the Hot to Trot Transvestite. While at first she teased me with possible participation, it never came to be, despite me bringing it up on several occasions. She really d... Read full Story
shemale lover 2013-01-17 7,229 Stockings Crossdresser sucking dildo Interracial
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 7,242 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
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 3,949 Crossdresser Amateur Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock Asian gangbang domination Guy Fucks Shemale Interracial sex Mature Futanari Frottage Compilation Ass to Mouth Cartoon cum in mouth double anal dating life in Mars? life
100%
Two CD's the first time we meet.....
We are meeting for the first time since talking online. I want to dress for you gurl, I want to feel as you do, I want to be your slut, your slave of desire. My panties are a sheer white, my hard cock can be seen ever so pressing against them, I rub myself for you as you watch, drooling now. Hand... Read full Story
kelliecdgirl 2024-04-10 3,808 Stockings Crossdresser Cumshot Masturbation Fetish blonde Big Cock Lingerie pantyhose Frottage sissy femboy shemale + shemale
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 13,823 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
100%
From a 50's virgin to a Mature good for all
***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... Read full Story
hippocampus_171 2023-01-11 4,319 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
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 1,293 Stockings Crossdresser Cumshot Lingerie Frottage cum in mounth
100%
Beryl's birthday suit
I tried on my sister's panties when I was 12. They looked so cute, so sexy.. I couldn't help myself. I tucked my dick between my legs and pulled them over my hips, delicately positioning them just like a girl. They felt yummy! When I saw the shiny, lacy pink briefs in the mirror - snug, flat pu... Read full Story
Beryl 2023-12-12 7,119 first time Stockings Crossdresser Bareback Blowjob Big Cock Lingerie redhead sissy cum in mouth
100%
A Win-Win
A Win-Win By Sabrina G. Langton *** Author's Note: Hi, just a quick, crazy story about a wife actively participating in her CrossDresser husbands sex life. Just a bit of fluff, hope YOU like it.) *** We were laying in bed, sex was done, my wife could now relax for the rest of the month ... Read full Story
Brina Giselle 2024-03-31 3,860 anal Stockings Crossdresser Blowjob pantyhose kissing salon
92%
My Neighbor
When I got divorced and was finally living alone I had many fun times getting fucked all I could by both men and women. I was always dressed when home and loved to stay that way all weekend long and would just put on some pants over my outfit to go shopping sometimes with a coat or shirt over my ope... Read full Story
crossdresser55 2019-10-29 16,500 Stockings Crossdresser
33%
Old Folks Chapter 1
I had been cross-dressing for some years, but I had never been with another man. I had been talking on a gay chat site for some months when I found someone who I got on with well. We exchanged photos I was happy with his and he was happy with mine. Deciding to get together, we arranged a date and ti... Read full Story
shemale lover 2012-12-21 4,228 Stockings Crossdresser Lingerie Mature cd
100%
Camming down the rabbit hole Ch5
I was jolted out of my sleep by the phone on my bedside table vibrating, bleary eyed I picked it up and saw a message from the couriers that a package would be delivered today around 4pm. The realisation that this was the package I had been waiting for and I could finally wear something else in my s... Read full Story
Dani_does_Dallas 2021-09-29 5,002 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade cum in mouth webcams
100%
Junior's Department
Junior’s Department The long-haired young male browsing alone in the ladies’ junior’s department caught his eye and he stopped walking to the store exit. He stepped behind a display rack across the aisle, then watched him approach a mirror and scan the area before holding the skirt and blouse up ... Read full Story
AuthorJordanSkythe 2022-01-20 2,707 first time Stockings Crossdresser romance femboi
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 4,255 Stockings Crossdresser Cumshot shemale oral sex
81%
My First Sissy Meet Up
I had posted an add on craigslist asking people to let me suck them off at my place. After sorting out all the answers that I got I found a guy, John, that was incredibly eager, we agreed a time and date. The day came and I woke up so nervously. But I was determined to not let it show so I got... Read full Story
Felicia Smith 2016-06-08 12,085 Crossdresser Big Cock cumming cd sissy
100%
New Game by Jordan Skythe
New Game Alan tossed his game controller, then reclined on the bed and sighed. “I’m bored.” He nodded in agreement. “So am I.” He wasn’t, but wanted to see where the declaration could lead. “We need to do something new.” He felt his breathing increase, wondering if this was the moment he could... Read full Story
AuthorJordanSkythe 2022-01-24 2,098 first time Stockings Crossdresser Bareback Uniform seduction Lap dance
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 3,292 Stockings Crossdresser Cumshot Blowjob Lingerie
94%
Crossing lines
It had always been a fantasy of mine. I have very feminine features and long natural straight brown hair. Which recently I had shortened to chin length. I have been dressing in womens clothing now for many months and had decided that this was the night in which I get made up totally and head ou... Read full Story
Zöe from Kingston 2019-02-04 11,068 Stockings Crossdresser Cumshot Outdoor Bareback Shemale Fucks Guy Blowjob Big Cock Ebony Guy Fucks Shemale Interracial
100%
Camming down the rabbit hole Ch3
Slowly stirring from my sleep, I stretched under the covers and a pleasant sensation spread across my torso, remembering what I was wearing when I went to bed I smiled at the caress of the fabric on my skin. It was a strangely comforting feeling, the pressure from the bra, panties and nightie felt l... Read full Story
Dani_does_Dallas 2021-08-18 5,180 Stockings Crossdresser solo Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade
85%
The Sex Club
When I got divorced back in 1987 I was a very horny man that had not had sex in many years. I had always liked to dress up in nylons etc and learned long ago that I was Bi and liked cocks and pussy. When I finally got my own place after the divorce I almost always would lay around the house dressed ... Read full Story
crossdresser55 2019-09-11 9,784 Stockings Crossdresser Lingerie Sex Toys
100%
Camming down the rabbit hole Ch6
In the morning I decided to give the running a miss and do a long session with the DVD, my legs had become a little sore and tight so some extra stretches and yoga would really help. I once again surprised myself with how much more flexible I had become, the plug still in my ass giving me occasional... Read full Story
Dani_does_Dallas 2021-10-11 4,858 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade pov cum in mouth webcams
83%
the start of what to cum
I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often mo... Read full Story
oliviabecket23 2023-07-04 6,715 Crossdresser Lingerie domination Sex Toys femboy forced webcams
100%
Crossdresser Caught in Act
I do not consider myself gay, nor do I think I am bisexual, but I do enjoy a nice big cock. I am not attracted to men at all and under normal circumstances find any and all homosexual activities quite disgusting, until I get really horny that is. When I get all hot and hard, I can't help but want a ... Read full Story
shemale lover 2012-03-31 5,617 Masturbation Sex Toys crossdressing vibrator
100%
Camming Down the Rabbit Hole Ch. 09
As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night ... Read full Story
Dani_does_Dallas 2022-03-22 3,398 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
100%
Sweet Encore
I was alone tonight and feeling just a bit paranoid as I listened to the soft music. The soothing sounds put me in a seductive mood, but It seemed that all my lovers were too busy for me, or they had other plans. Uncle Barney and my detective were probably home being dutiful husbands. Bo was under h... Read full Story
Regina10 2024-05-09 2,788 Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass Ass to Mouth
94%
Proud To Be A Sissy Chapter 2
As I reached down to retrieve my clothes that Mr. Clark had thrown at me there was a bright flash of light. Without thinking I turned my head towards him only to be blinded by another flash from his Polaroid camera. "What are you doing?" I asked. "Just wanted to capture the m... Read full Story
shemale lover 2012-12-23 7,901 Crossdresser sucking ass fucking domination ass fingering
100%
A Religious Experience
A Religious Experience by Sabrina G. Langton *Stories from the real world 2 This story is kinda autobiographical. I was twenty-two in 1987. You couldn't just order anything you wanted on the computer, with no social interaction, and get whatever you wanted. You had to go out in the real w... Read full Story
Brina Giselle 2023-09-13 4,770 Crossdresser pantyhose transgender bisexual footjob dress
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 7,980 Stockings Crossdresser Cumshot Fetish oral sex pantyhose
100%
Highway in Heels
Highway in Heels By Sabrina G. Langton *Stories from the real world 1 This story is autobiographical. When I was 20 years old I used to drive a van for my parents from Brooklyn to Tarrytown New York once a week to drop off merchandise for retail shops in the area. I always had a full van on ... Read full Story
Brina Giselle 2023-08-28 4,654 Crossdresser blonde pantyhose kissing transgender
81%
Forced Entry
Danny sat at the bar of the Holiday Inn nursing his fourth double scotch, espousing to the man beside him the reasons why his company was the best designer and distributor of accounting software in the world. Danny was a large man in his forties and was running to fat. He was dressed in a travel-... Read full Story
shemale lover 2012-11-16 15,749 Big Cock oral transvestite forced sex
37%
First time Crossdressing
I am a bisexual man, meeting straight, bisexual or gay men for our sexual pleasures. I post messages on various message boards that allow members profiles and posting messages. I also post to local groups in my area that allows one to post messages to a small geographical area or to a distant user g... Read full Story
shemale lover 2013-07-17 6,081 first time Crossdresser Fetish Mature bisexual
100%
TO BE OR NOT TO BE – PART 6
TO BE OR NOT TO BE – PART 6 by Spanky de Bautumn Part 5. Sunny and Antonio got frisky at the bar, Sunny moved in with Mel and Shari, and opening night was a success The only other dress that I brought was one that I hoped I would get a chance to wear but didn't think I would. It was a black ... Read full Story
SpankydeBautumn 2021-02-26 2,407 Stockings Small Tits Crossdresser Cumshot Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
TO BE OR NOT TO BE – PART 6
TO BE OR NOT TO BE – PART 6 by Spanky de Bautumn Part 5. Sunny and Antonio got frisky at the bar, Sunny moved in with Mel and Shari, and opening night was a success The only other dress that I brought was one that I hoped I would get a chance to wear but didn't think I would. It was a black ... Read full Story
SpankydeBautumn 2021-02-26 2,421 Crossdresser Cumshot Masturbation Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
72%
Longtime friends
*** This a work of fiction but wishful thinking. Beau and Stephen had been long-time friends, they often spent time together playing golf, gym, and fishing. Stephen had a secret crush on Beau for quite a long time or it was Stephanie, Stephens' alter ego that did have a crush on Beau. He found hi... Read full Story
Stephanie_logan 2020-02-21 4,461 Stockings Crossdresser Fetish Lingerie
100%
I Love To Love You
I Love To Love You Baby By Sabrina G. Langton Author's note: I have published this story on two other sites. I always said it was slightly aurobiographical, but reading it back it is a pretty accurate account of my summer of '88. There are only 3 things that I changed. 2 are itsy bitsy tiny deta... Read full Story
Brina Giselle 2023-09-24 4,983 anal Crossdresser Blowjob kissing transgender virgin romantic earrings
63%
Julie's First CD Night on the Town
There was a parking lot that was out of the way where I changed into my set of girl clothes for my night of adventure. The nylon underwear was tight and sleek, I had a raging hard on as I drove into town. I had been planning this night out for quite a long time and was hoping to get my butt well ... Read full Story
shemale lover 2012-09-10 4,412 Crossdresser Cumshot condom sex heels
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 33,739 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
72%
ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn
Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... Read full Story
SpankydeBautumn 2021-01-29 11,335 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
100%
Karen, My School Teacher Part 4
Meeting my other teacher By FoxyHosed Next morning as I woke up, I jumped in my clothes and got myself a coffee, and went to school. I got in 15 minutes early because I didn't want to run into Karen. As I entered the door to the school, I saw some of my classmates. I thought the coast was clea... Read full Story
FoxyHosed 2021-02-17 7,791 Crossdresser Cumshot Masturbation Fetish Blowjob Big Cock redhead pantyhose feet toes legs cock ass pantyhose legs
100%
Lady In The House Ch. 02
A story by Michele Nylons, Part II "She's all yours Eddie. She looks beautiful." I heard Carmel say as 'she' disappeared down the corridor, her high heels clicking on the tiled floor. Eddie appeared at the door to the cell, he stepped inside and closed the door behind him. "So what do yo... Read full Story
✘Transensual✘ 2019-01-11 4,761 Stockings Crossdresser Fetish Big Cock Uniform Lingerie domination PRISON PUNK prison sex Prisonboycum Prison Bitch
76%
Nylon teasers
They came into the video store where I worked as a clerk. Almost every day. Teasers. Both of them. What made it both great and terrible for me was that it fed my deepest fetish -- stockings -- as it denied me any fulfillment other than frequent and frantic "self-gratification."... Read full Story
shemale lover 2012-01-30 9,890 Stockings Big Tits fucking foot 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 3,046 Cumshot suck Big Cock fuck
100%
Lady In The House Ch. 07
A story by MicheleNylons (Carmel and Charlotte want theirs.) From Part VI "You look gorgeous Michele," Carmel whispers through the bars. I wondered if she had read my mind when I was standing in front of the mirror admiring myself. "Well, I have to say you girls are looking something spe... Read full Story
✘Transensual✘ 2019-02-25 3,339 Crossdresser domination prisoner shemale lesbians Prison Bitch
76%
Woman of my dreams is making me the woman of my dreams (pt 1)
I met Amber one day while I was out at the beach. She was so far out of my league – a 5’4” slender and toned stance and exquisitely tanned body with a bikini that left very little to the imagination. She was unbelievably hot, so it was no surprise that I was tongue tied when she walked past me and s... Read full Story
jenrip 2021-03-29 7,561 Stockings panties crossdresser lingerie woman on shemale
100%
Alex Two: The Next Time
Part Two of ??? (there is another series I'll start too, Hopefully its not too repetitive and my fetishes aren't showing too strongly. heh. That is sort of a prequel to this, I guess. I had forgotten about it till just now when I found it in a misnamed folder.) Alex Two: The Next Time.... Read full Story
AlexShouse 2012-07-12 3,205 tranny Crossdresser Masturbation
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 35,471 Crossdresser sucking Lingerie ass fucking ass fingering
100%
TO BE OR NOT TO BE – PART 3
TO BE OR NOT TO BE – PART 3 by Spanky de Bautumn Part 2. At the hotel in New York City, Sunny meets the bellhop, Antonio, and they go out for a drink when he gets off of work. The call came at exactly seven. I had woke up about five minutes before and was watching Antonio sleep. All of the oth... Read full Story
SpankydeBautumn 2021-02-23 2,490 Small Tits Crossdresser Amateur Cumshot Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
The Best Valentine's Gift
The Best Valentine's Gift By Sabrina G. Langton *** Author's note: Hi, just a little sexy story... cocktails, a three-way and some role play... the usual, I hope YOU like it... *** Ding dong. "Hello," "Sabrina hi, come on in, you are all dressed up and looking fabulous already... Read full Story
Brina Giselle 2024-05-22 2,272 Crossdresser pantyhose transgender high heels bbc three way
100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 9,072 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
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 7,165 Crossdresser Amateur Bareback
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,620 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth