Sort by
Relevancy

Free Stories

90%
Collette's Property
I've been Collette's lover for four years now and this gorgeous, incredibly kinky woman still continues to amaze me. Our sex life would be unimaginable to most people, even those who live lives embracing BDSM and other fetishes, and it's Collette who makes it happen. Of course everything is a trade ... Read full Story
shemale lover 2012-12-19 7,865 anal Crossdresser Blowjob domination ass fingering
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 7,818 Crossdresser sucking ass fucking domination ass fingering
93%
Proud To Be A Sissy Chapter 7
"You're being really dirty little sissy slut today," daddy chuckled and asked, "What's gotten into you?" "Making up for the last few days I guess," I giggled hugging him tightly, "and I missed you too." "I missed my little sissy too." He repl... Read full Story
shemale lover 2012-12-24 7,466 Crossdresser Cumshot Blowjob Big Cock ass fucking
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 7,139 Crossdresser Cumshot Creampie Blowjob ass fucking
93%
New School, New Life
Part of my father's job is on-campus recruiting, so when it was time for him to spend a week at the university where I was enrolled for the following fall, we decided that I should go with him and familiarize myself with the campus. We left on a Friday morning to ensure I'd have a full week on ca... Read full Story
shemale lover 2013-02-06 8,664 Teen (18+) Crossdresser Cumshot sucking ass fucking
86%
Hotel Heaven or Nightmare
You've enjoyed a relaxing bubble bath, you're smooth skinned and perfumed. You dress with your new purchases, Gio seamed stockings, leather mini skirt and Carvela heels with sexy peep toes. You take time to apply your make up while you contemplate what the evening will hold for you. There's nothing ... Read full Story
shemale lover 2013-03-12 5,889 sex toy Crossdresser Cumshot Big Cock Lingerie
88%
Ivana Pushing Sissy's Limits
"You look ravishing," my wife Ivana said as I stood before her in a short red velvet dress with white tights and black Blahnik mary janes heels. She walked over to put a hair band in my long black hair. It was down to my shoulders now, flat-ironed straight. We stood together in front of... Read full Story
shemale lover 2013-03-19 6,567 Crossdresser Cumshot sucking Creampie ass fucking
87%
A girl called Eddie
Carrie had always treated me like her little sister, even though we were only third cousins. Though she was only two years older than I was and not of exceptional physical stature, I had allowed her to dominate me for as long as I could remember. Not that she was exceptionally cruel or abusive in an... Read full Story
shemale lover 2013-07-19 4,596 Crossdresser Cumshot sucking domination spanking
100%
A surprise for John
It was a busy day at work when I got a text message from John asking what I was doing that night. I replied that I had no plans. He told me he was leaving work early, if I wanted to stop by for a lil bit I was more than welcome. I told him I would. I did want to talk to him about a small trip I was ... Read full Story
shemale lover 2013-07-21 7,973 Crossdresser anal sex Cumshot oral sex kissing
71%
The Training of Julie
The story of the successul aiteration of a good looking youn man into a stunning, talented, ultra feminine boy/girl John was about to learn obedience in the strietbatt sense of the word. his whole life style was about to be changed, The rather alightly built, pretty boy of 17 was to become Julie,... Read full Story
shemale lover 2013-08-09 8,041 Crossdresser oral sex massage handjob cd
56%
Blow Job
My e-mail is: My rusted, green Toyota Tercel pulls into the mall parking lot. I pick a spot at the back, beyond where even employees park. The next car is a blue pickup 20 spots away. No one parks here, except at Christmas. But I know that I'll soon need the privacy. I'm a freak, a cross-dresser... Read full Story
shemale lover 2013-08-09 6,825 Crossdresser Masturbation Lingerie stripping party
93%
Halloween Surprise, Pt 1
It’s been a while since this happened but I remember it like it was yesterday. I had just turned 17a few days before my favorite holiday. I’m a good looking guy, 5’6” maybe 140 lbs. Not the biggest guy in HS but not the smallest either. I have what I call camouflage colored eyes. Sometimes thei... Read full Story
spencer_320 2013-12-08 7,797 anal Crossdresser Blowjob fingering cheerleader
100%
Dress like a bitch then fuck like one
Tyrone and Lamar were a couple guys I had met in a bar last weekend. Lamar called me and asked me if I would unlock a cell phone for him. I agreed and just as soon as my wife left I packed a small over night bag and drove to his house. Last night I spent the night with a couple friends. We drank... Read full Story
Rocky Wachenheim 2014-09-17 5,035 Crossdresser Cumshot suck Big Cock deep throat
84%
Abi's Virginity taken by Intruders
Abi got very little time to be herself, A closet TV, sharing a small two bedroom flat with a male friend, it was only once every few months or so she got the flat to herself and could dress up sexy and be her proper girly self, and tonight was one of those nights! Although she had no plans to mee... Read full Story
AbiTV 2015-03-18 6,319 Crossdresser threesome sex fantasy virgin
80%
A New Spin On Role Playing Games
A New Spin on Role Playing Games By: Shawna Summers shawnavinylltv@gmail.com I've always been something of a geek. I love sci-fi and fantasy books and movies; I can recite countless bits of useless trivia back to you about all kinds of movies. So, it was no real surprise that I took to rol... Read full Story
shawnavinyltv 2018-06-14 10,602 Crossdresser anal sex Blowjob gangbang Lingerie bondage
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 9,068 Stockings Teen (18+) Crossdresser Cumshot Bareback Blowjob blonde Big Cock Lingerie Mature cum in mouth
92%
A Sissys new start
I only ever told my father one lie. That was about the boots. I was about to turn 18, jobless, directionless and pretty screwed up to be honest. There had been rows, fights, shouting matches and long frustated silences about what i was doing with my life, but i had formulated a plan. Kind of. Tw... Read full Story
SissyDani31 2018-10-04 5,421 Teen (18+) Crossdresser Amateur
66%
wishing
When I would get off the bus from after school activities, I would always walk through this truck stop on I-94 east of the Twin Cities. I would always look at the truckers parked for the night in the back. I always wondered what would happen if I brought my desires and fantasies to life for one of... Read full Story
cd4fun715 2019-01-08 2,771 Crossdresser Amateur
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 10,970 Stockings Crossdresser Cumshot Outdoor Bareback Shemale Fucks Guy Blowjob Big Cock Ebony Guy Fucks Shemale Interracial
100%
Lady In The House Ch. 04
A story by MicheleNylons ( Prisoner's transformation continues.) From Part III Steve's orgasm started to subside and he continued to rub his cock all over my face. He smeared his spend all over me, it combined with my lipstick and makeup to make a hot sticky film that covered my face. Steve ... Read full Story
✘Transensual✘ 2019-02-25 3,840 Crossdresser prison sex Prison Bitch
100%
Lady In The House Ch. 05
A story by MicheleNylons (Crossdressed prisoner is forced into prostitution.) From Part IV Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread th... Read full Story
✘Transensual✘ 2019-02-25 4,405 Crossdresser domination PRISON prison sex
100%
Lady In The House Ch. 06
A story by MicheleNylons (Michele continues to be used by prison inmates.) From Part V Harry leant over me and kissed me full on the lips. "That was worth every penny; you are one hot nurse," he laughed. Harry grabbed a handful of my clean white skirt and wiped his cock on it. The silver... Read full Story
✘Transensual✘ 2019-02-25 3,653 Crossdresser domination prisoner prison sex Prison Bitch
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 3,267 Crossdresser domination prisoner shemale lesbians Prison Bitch
100%
Lady In The House Ch. 11
A story by MicheleNylons ( Next instalment of reluctant transvestite prison whore. ) A few minutes later I was still in a daze, trying to rationalise to myself what had just happened. I was operating on automatic pilot, rifling through the drawers of my closet looking for a pair of nylons to repl... Read full Story
✘Transensual✘ 2019-02-27 3,292 Crossdresser domination PRISON FUCKBOY prisoner prison sex Prison Bitch
75%
Lady In The House Ch. 13
A story by MicheleNylons ( Transvestite prison prostitute gets a visit from the Warden. ) I awoke in my cell the next morning unaware of the terrible fate that had befallen my sister Angie. I knew that Steve had sent his henchman Danny to do something to her in retribution for my recalcitrance bu... Read full Story
✘Transensual✘ 2019-02-27 5,290 Crossdresser domination PRISON FUCKBOY PRISON PUNK prisoner prison sex Prison Bitch
88%
Who's She?
School had been a bore for Tony. He was a bright lad and didn't have to work too hard to get through classes unnoticed by the teachers and class mates. He had plenty of friends but no one close. He didn't excel in sports or academically. He had picked up a few good exam results but had decided that ... Read full Story
Vinny_A 2019-07-08 11,538 Teen (18+) Crossdresser Amateur Big Tits Bareback Blowjob Lingerie
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 16,389 Stockings Crossdresser
76%
The Guy At The Pool
The Guy At The Pool Stepping out of my hotel room for a smoke I saw two young guys at the swimming pool which my room overlooked. One of them was standing outside the pool speaking to the other guy who was in the pool. The guy beside the pool immediately caught my attention, his shirtless bo... Read full Story
pennypenny 2019-10-21 6,581 Crossdresser Bareback Creampie Blowjob redhead Guy Fucks Shemale Ass to Mouth cum in mouth
92%
Showing my femininity
When I was still little guy, my stepfather always told me I wasn't a real boy, but I was his little girl. One day, he was drinking beer with his friends, so he grabbed me by the arm, pulled my shorts down and showed off my teeny cock to them. I remember that all of them laughed at me. They made fun ... Read full Story
Shemale Dill 2020-04-27 7,840 Crossdresser Amateur Group Sex Blowjob Big Cock gangbang Lingerie
90%
Special Delivery
This is a short work of fiction, but as with all good tales, there is an element of truth in there, as well. In my mid to late twenties, I started a new job as a delivery driver for a well known company, delivering mail order items and such to customers homes. My route would take in several count... Read full Story
Daddybear71 2020-07-20 3,845 Crossdresser
66%
a day in the life of Amber SissyZofen 264
And the days had passed one after the other and now it was the day of my date. He sent me a txt at 8.30 on Saturday morning to say he was coming And you remember he was leaving his phone at home in case his wife called You know I had sent him my address, parking advice and left the gate ajar. ... Read full Story
amberdoll 2020-09-15 2,577 Stockings Small Tits Crossdresser Amateur Masturbation Bareback Creampie blonde Lingerie Homemade cum in mouth
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 11,220 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
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 3,516 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
100%
Horny Writing A Strange Habit
I enjoy watching videos which I can Vicariously live. This is nothing more than my horny hobby, an amalgamation of various thoughts. My form of hands free edging. Spell checked only, "No I haven't proof read a first draft, not trying to publish masterful works here." Hope to hear from those w... Read full Story
Araina 2021-03-08 2,643 Crossdresser Amateur Big Tits Cumshot Bareback Fetish Blowjob Big Cock Guy Fucks Shemale Frottage Homemade Ass to Mouth cum in mouth
50%
a conversation
> Good morning Amber > Thanks for the videos. > I’m a little envious of that gentleman but it was lovely to see you be the perfect slut that you are.Very special to watch you suck a cock.You look fabulous as you worship it and surrender yourself to be used for pleasure. I would love to have you al... Read full Story
amberdoll 2021-03-18 2,185 Small Tits Crossdresser Amateur blonde Lingerie Homemade
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 1,991 first time Stockings Crossdresser Bareback Uniform seduction Lap dance
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 3,299 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
100%
Camming Down the Rabbit Hole Ch. 11
I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hopin... Read full Story
Dani_does_Dallas 2022-04-25 4,077 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth
100%
Chapter 1 - My Cuckold Life
I have a small penis. In fact, I have a very small penis. I’ve been in permanent chastity for over 7 years. My wife and her lovers call it my “caged clitty” and that’s about right as far as it being a useful penis. I suppose I should start at the beginning. I’ve never been much of a man. I’m ... Read full Story
Sissy Annabelle 2022-08-23 5,966 Crossdresser Interracial sissy chastity Cuckold Husband
0%
Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
Alicexiao 2023-01-06 4,191 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
100%
Kelly's First Encounter With Alessia
I jumped nervously with a start, as the doorbell rang. It was Alessia – I had been waiting for her all morning, and was gradually getting more nervous as time passed. This was to be our first encounter, and I’d been looking forward to it all week. Opening the door, I saw that she was taller tha... Read full Story
Alessia Travestita 2023-01-31 4,224 Crossdresser Blowjob blonde Big Cock Mature
100%
I Fooled Everyone But the Black Pimp Part 4
Fuck. I said I wasn’t going to do any drugs and I’m drinking this Gatorade that I know has something in it. Trish said it would help my nerves, and it has, I feel loose…and very horny. When I’m usually horny my cock is hard but right now, I’m putting lotion on my body and I’m going really slow over ... Read full Story
cdtampa4u 2023-05-17 4,911 Crossdresser Blowjob Interracial sissy bbc
100%
Alessia Travestita’s Adventures – Game, Set and Match
Chapter 1 – A chance meeting? Alessia sipped her double-espresso slowly, savouring the strong flavour and the sweet aroma as she gazed absent-mindedly out of the window, watching the passers-by on the walkway outside the coffee shop. It was approaching mid-day so she had chosen to sit inside out of... Read full Story
Alessia Travestita 2023-07-20 4,503 Crossdresser Blowjob Big Cock Shemale and Girl cum in mouth
100%
Alessia and the Twins
Alessia and the Twins When the politician David Smallwood awoke that morning his thoughts immediately turned to Alessia, and he started to daydream about her, as he was wont to do now. He had several meetings scheduled for that day, including a rally promoting restrictions on gay and trans-gender... Read full Story
Alessia Travestita 2023-07-21 5,113 Crossdresser Blowjob Big Cock Shemale and Girl shemale fucks female
100%
Becoming Kacey
I indulged my crossdressing opportunities as often as I could, but as time went on, the chances grew further and further apart. Although I couldn't play dress up in my alone time, the fantasies never seemed to cease. When I entered high school, I dated girls and enjoyed the young passions that teena... Read full Story
KaceyKlarissa 2024-01-16 3,885 first time Crossdresser Amateur Homemade sissy femboy shemale + shemale romantic teen (18+)
100%
Edging lessons for Hannah
Hannah and I began spending our weekends together. She didn't have a job and I was always free those days so every Friday or Saturday night became sleep over night where we could be two 18 year old sissies, doing each others makeup, playing dress up and sharing our deepest desires. Now that our rela... Read full Story
KaceyKlarissa 2024-01-25 3,624 Crossdresser Amateur Cumshot Masturbation Fetish Big Cock kissing Homemade sissy romantic cum swap edging teen (18+)
100%
A Series of Perverse Dreams, Part 1
My relationship with Hannah had always been mutual in the idea that neither one of us was ever truly the dominant one. It was an equal, balanced relationship of mutual fucking and sucking. However, I had REALLY enjoyed being made into a submissive sissy slut by Nikki. Something changed in me after o... Read full Story
KaceyKlarissa 2024-02-24 4,932 anal Small Tits Crossdresser Group Sex Big Tits Outdoor Big Cock gangbang domination sissy femboy Ass to Mouth cum in mouth
100%
A Series of Perverse Dreams, Part 2
Three or four days had passed since my torrid alley way dream. Hannah had recently come over to share a few glasses of wine and a steamy fuck session in the shower. She had definitely embraced the ways of edging I had shown her because when she came in my mouth I could barely contain the massive amo... Read full Story
KaceyKlarissa 2024-02-29 3,926 Crossdresser Big Tits Cumshot Bareback Fetish Blowjob blonde Big Cock big ass Futanari bukkake sissy cum in mouth
100%
Glory Hole Memories
The Glory Hole Fun Begins Locking the car I look towards the building. The entrance is open, but from my position it isn’t possible to see inside, the bright sunshine making the entrance look black. My heels click on the tarmac as I approach, my legs beginning to tremble with fear and excitement.... Read full Story
Sexy Michelle 2024-03-13 3,779 Stockings Crossdresser Outdoor Blowjob Big Cock Lingerie
100%
Sex With Not Just 1, But 3 Females
When I was 18 years old, I was still occasionally going to the Highbridge toilets in Lincoln on a Saturday and getting paid for having sex with guys be it sucking cocks or being sucked off, dirty chats, wanking them off or giving or taking anally. I never turned down any form of payment, money or... Read full Story
Linda Tiffany Vista 2024-05-07 1,393 Stockings Crossdresser Amateur Lingerie cum in mouth teen (18+)
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 5,537 Masturbation Sex Toys crossdressing vibrator
100%
Emily and Steve Part 1
As I pulled my cock out of Emily's ass and shot my load onto her flat stomach, where my cum mixed with the load the beautiful blonde cross-dresser had just shot from her throbbing cock a moment before, I thought to myself that work was suddenly going to be a lot more fun. My name is Steve and I w... Read full Story
shemale lover 2012-04-06 3,606 Crossdresser anal sex blonde
100%
Party Surprise - First sex as a Crossdresser
This is a work of Fantasy. I hope you enjoy. Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly s... Read full Story
shemale lover 2012-05-21 7,280 first time hardcore anal sex Cumshot oral sex crossdressing
100%
Caught by Dave!
Let me start out by saying that I was very much in the closet about my dressing and the fun I have when I'm dressed. No one I know even suspects that I'm a slut at heart or that I am the least bit bi. But more and more I keep fantasizing about one of my male friends. He's very good looking and keeps... Read full Story
shemale lover 2012-06-15 3,417 Crossdresser Cumshot Fetish Blowjob cum swallowing
100%
Fender Bender Chapter 5
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 my Step Dad were away on vacation leaving me home alone. The past several days I had been very lazy and sleeping almost to noon. So it was no surprise ... Read full Story
shemale lover 2012-07-26 3,073 Crossdresser Cumshot Fetish oral sex cum swallowing
55%
Dawn's Diary Chapter 3
Back at home it took nearly a week before I was able to sit comfortably after my encounter with Sam and her huge dildo. My thoughts constantly drifted back to her. I continued to keep my body cleanly shaven and regularly wore the outfit that I had worn that evening with Sam around the house. I bough... Read full Story
shemale lover 2012-07-31 2,915 Crossdresser Cumshot oral sex