Sort by
Relevancy

Free Stories

66%
Debbie Part 10
Debbie might have lived out the rest of her life if it hadn't been for some events, which started back at Mistress' mansion. Several years after selling Debbie, Mistress Helen Chamberlain still ran her ruthless slaving operation. Giselle was still her favorite slave, constantly restrained and regula... Read full Story
shemale lover 2011-12-23 5,239 transgender toys bondage and discipline heavy
76%
Mistress
My wife (Airlia) and I are open minded when it comes to sex. We are pretty much into everything, but at the moment we found ourselves going to a mistress for a bit of fun. We have been to our mistress four or five times so far and we both enjoy watching the other getting abused, especially Airlia wh... Read full Story
shemale lover 2012-04-22 4,673 anal Group Sex oral fingering domination Sex Toys
100%
Been Caught Cheating Chapter 2
I awoke in the morning to voices. It was Angela and her sister Heather! I could here them in the next room talking, but couldn't make out the words. Everything was still dark though. And I was still bound to the bed, and gagged. I had stayed like that all nightlong. Trying to move, I also found that... Read full Story
shemale lover 2012-04-23 3,661 Cumshot domination Sex Toys rimjob
100%
David to Dee Chapter 2
His nipples had grown considerably over the last two months. Gina had been putting those little nipple suckers on him twice a day. Dave wouldn't be going to the gym anymore. Well, it had been a long time since he'd gone to the gym, anyway. Since Gina had had him shave his entire body, last spring... Read full Story
shemale lover 2012-07-30 6,012 anal sex Cumshot oral sex rimjob
100%
Desiree and Big John
It had been only a week since I'd introduced "Desiree, the Hot to Trot Transvestite" to my girlfriend Suzie, leaving me not a bit surprised that she chose not to spend the very next weekend at my place. While she hadn't freaked out, she was concerned I was gay since I was so convincing but... Read full Story
shemale lover 2012-08-20 4,680 first time anal sex transvestite cum swallowing
100%
Dress Up
I don't know how to explain it. I am not gay although I may be passive bi. I have had sex with men, but not a lot and I have always been the one receiving, you know once a friend showed me a pack of pictures of his wife from fully dressed in conservative suit to complete nude with some action photos... Read full Story
shemale lover 2012-11-17 4,757 Fetish cum oral sex Sex Toys cum swallowing
62%
White Sissies on Black Dicks
Sunni inhaled the marijuana, held it in for a few moments, and then released a puff of smoke in the air. The effeminate white man with a platinum blonde Mohawk pressed the number two button on his phone to listen to the message. He heard a deep-voiced Black man say he needed his dick sucked and woul... Read full Story
shemale lover 2014-09-11 12,767 ass suck Big Cock oral sex Interracial cd
100%
My Sissy, his first time
My fella has always been happy to dress and be a slut for me, suck my dick and take a small dildo in his pussy. Until now I hadn't fucked him properly as he was to nervous. Recently we had been following the exploits of a CD friend through his blog and I knew they really excited my husband. When the... Read full Story
Aplane1 2021-11-01 3,765 Stockings Crossdresser Amateur Cumshot Lingerie Sex Toys
100%
Danielle's First Time
Danielle was born in the winter to 1976, but she was born a male by the name of Daniel. Daniel looked like a normal male child aside from liking girly things. Whenever Daniel would play dress-up he'd always dress in his mother's or his aunt's clothes and his parents thought that was cute until Danie... Read full Story
shemale lover 2012-02-03 5,764 cum dildo fingering
91%
Mature crossdresser & 18 year old
Myself being a fulltime crossdresser and wear mini skirt and dresses all the time an high heels. A few weeks ago some new people move in across the street from me to be extact it was a woman and her 18 yr son.I talked to her few times and she was very nice and in our talks asked her if it bother he... Read full Story
shemale lover 2012-04-12 11,715 Crossdresser Cumshot oral sex
100%
Been Caught Cheating Chapter 3
I awoke in pain. I had slept bound all night. And it also seemed that I had been hit with something to wake me up. Angela was standing over me with one hand on her hip and the other holding my bounds that I slept in. She was already dressed and ready to go. I looked around to make sure we were alone... Read full Story
shemale lover 2012-04-23 4,320 Fetish domination crossdressing
75%
Exhibition Fantasy
We are away at the exhibition we are attenting for work and we have had a few drinks throughout the evening with the others. The excited tension between us has got progressively stronger as the nights gone on, we both hardly wait for what we know is coming. We all start to head off for bed and we... Read full Story
shemale lover 2012-04-23 2,823 Creampie Fetish cum Sex Toys fantasy
100%
Fender Bender Chapter 7
The main Characters are as followed: 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 turned 18 a few months ago. Gary is almost 6', 185 pounds. He has short blonde hair and dark blue eyes. He has a nice tasty 7 1/2 inch cock... Read full Story
shemale lover 2012-07-27 3,327 Creampie ass fucking domination 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 12,920 Cumshot Masturbation oral sex
100%
Leila My Hermaphrodite Lover
I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most. It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before. I'd stayed over at a friend's house and after a ni... Read full Story
shemale lover 2012-12-17 4,594 taboo Cumshot shemale Mature
96%
New Job, New Life as as Sissy Slut Chapter 2
I was left lying on the floor, my face completely covered in cum. I was wearing lingerie and a dog collar and I had just been fucked long and hard by my "boss." My virginity had been forcefully taken. The thing is that I loved it. I loved being manhandled by this muscular man and I really ... Read full Story
shemale lover 2012-12-23 7,655 Cumshot Uniform Lingerie ass fucking domination
100%
My Life as a Shemale Part8
It was on my way home when I decided not to tell Tim about Sin. This was very private and it was already bad enough that I knew, also, I had no idea what Tim might say or do. I did want to stay friends with her, now more than ever. It was friday morning, the day after Sin was ****d and I was eager ... Read full Story
shemale lover 2015-02-27 4,021 tranny licking Big Cock Lingerie stroking
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 9,087 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
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 5,533 Cumshot jerking off pantyhose
100%
An unexpected kiss under the rain
Army Bear left that morning leaving me horny as hell. I couldn't go back to bed without playing with myself for a while. I opened my Pandora box and I took out my 9 inches, big dildo. I played with it for a few long minutes, burying it all deep in me thinking of him. Doing a few hits of poppers, I f... Read full Story
HotVersatileTs 2011-10-05 4,935 sucking domination foreplay cd
0%
Headmistress' Favorite Sport Part 9
When Denise returned from the academy all this was taking place without her knowing about it. She started her new life as a maid in Mistress Rachel and Master Tony's house alongside her mother, Susanna. Susanna had in the meantime developed into a complete slave, craving punishment and humiliatio... Read full Story
shemale lover 2011-12-13 5,777 torture toys bondage and discipline chastity belt
80%
Debbie Part 7
As Debbie was led into Dr. Jacobsen's office, she saw that Mistress was already there waiting for her. "Your property Miss Chamberlain", the doctor proclaimed, indicating Debbie. Debbie's heart began to flutter with love and submissive fantasies as she saw Mistress. Mistress was dressed in... Read full Story
shemale lover 2011-12-23 9,862 transgender toys bondage and discipline heavy
75%
Memoranda From Mr. P
Mr. Reddie used to call me Petro, as a short familiar name; his sly friendly way of reminding the two of us of my thick lengthy cock. Mr. Reddie maintained, when it was hard and erect, my cock looked and felt as lovely as Italian marble, hence the contraction of the Italian for stone: Petro. Whi... Read full Story
ColonelSaint 2012-03-19 3,814 Group Sex cum oral femboy
83%
Becoming Missy
It all started back in 1973 in Seattle, Washington. I was 21, living on the south side with a couple of buddies while we were all stationed at area military bases. One Friday night we had a party at our apt. I was standing outside by my car smoking a joint when this guy pulls up in his pick-up. &quo... Read full Story
shemale lover 2012-03-31 3,972 Fetish cum oral sex crossdressing rimjob
100%
Epiphany
My girlfriend Tonya was out of town for the weekend. She was meeting some college friends and going shopping and carousing in the city. A typical girls' weekend. I kissed her good bye at about 4:30 pm on Friday. We had become pretty close in the year that we had been dating. She was a cute blonde wi... Read full Story
shemale lover 2012-04-17 9,619 Stockings Cumshot oral sex crossdressing
100%
The Bitch Bites Back
Pamela stood huddled in the dark doorway, halfway down the back alley. It was cold and a light drizzle had settled in, the sheets of fine rain just discernible in the dull light of the single working lamp halfway down the alley. Pamela was in her mid forties and fighting a losing battle against t... Read full Story
shemale lover 2012-05-12 7,744 anal sex Cumshot oral sex wanking cum swallowing
83%
Yes Sir
I've been meaning to write this story for some time. It could have easily happened had I taken the initiative but instead, I chickened out. It remains a favorite fantasy of 'what if' though. I hope you enjoy. Saturday evening and I'm sitting in the living room of my small mobile home. Nothing to ... Read full Story
shemale lover 2012-08-21 3,953 domination crossdressing
100%
The Developing of Emma Part 3
She awoke to the sickly smell of a woman’s perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence. “Hello again ‘Emma’; that’s a very pretty name y... Read full Story
shemale lover 2012-08-26 2,940 Cumshot oral sex sissy
100%
R Is for Rita
After my debts began to mount, college fees and all that, one of my mates from Brum suggested I try to earn a little extra cash. I was surprised when he told me how. He said he'd done it and ended up with a couple of hundred extra most weeks, sometimes just for an evening's work. "It's easy,... Read full Story
shemale lover 2012-09-05 5,526 Stockings Big Tits Masturbation Big Cock Mature
40%
Kitten: A Pantyboy StoryKitten: A Pantyboy Story
It's easy now to look back and play armchair psychiatrist and see where my fetish for school uniforms and cute cotton panties started, but it wasn't until I met MISTRESS that I realized exactly how deep that fetish was ingrained in my mind and soul. Mistress knew I was a pantyboy after the first ... Read full Story
shemale lover 2012-09-10 7,312 Crossdresser fingering Sex Toys handjob 69
100%
First Date With Daddy
My Dream Date. It hasn't happened yet, but a girl can hope, this story is very short story based on my fantasy's. It was Sunday night and I had my first date lined up with daddy. We hadn't met, but we had spoken online at depth and exchanged numbers. I had sent him a couple of pic... Read full Story
SEXYBADGIRL 2023-03-17 5,328 Crossdresser Bareback Creampie domination
100%
The House of Lesslie Part 2
I. I woke up. Even after having taken over the House of Lesslie weeks ago, each morning was still the same, and came with the same feeling of disorientation, in need of a few moments to adjust to the realities around me, as new as they were. The bedroom around me was still darkened by heavy... Read full Story
shemale lover 2011-10-14 4,863 Fetish domination nipples
50%
Healthy Behavior
"Uhh…is Mr. Stanford around?" "One moment dear…ooh, damn heels. Makes it impossible to walk through doorways. Here I am ma'am. So, did the maid get you here alright? Hello? Earth to…" "I can't believe this…" "Oh, the heels? Yeah... Read full Story
shemale lover 2011-10-19 4,176 Big Tits transsexual oral
100%
Our special trip
John and I were having a nice relaxing afternoon cuddled up on the couch watching TV. Our relationship was shifting from all about great sex to enjoying the time we spent together just being ourselves, with me dressed up of course, and the sex seemed to me to be more loving. I'd still seduced him at... Read full Story
shemale lover 2012-02-22 3,235 Fetish cum fuck wig dressing
85%
My first experience
I had been dressing for a while but kept it very secret. I am a 5’11, 175 lb gurl who feels very sexy when I was dressed up. When I was alone in my dorm room I would put on sexy little outfits, make-up, and a wig and play with dildos that I had hidden in my dresser. No one in the dorm knew tha... Read full Story
shemale lover 2012-05-18 3,132 facial oral sex Sex Toys handjob crossdressing
100%
A Visit To The Booths
I walk nervously into the booths area. My heels clacking on the floor, as I enter the darkness. I pull my dress down, as its already riding up my ass. There are a few men waiting in the first hallway, checking me out as I walk past. I smile and head into the bigger area around the corner. There are ... Read full Story
shemale lover 2012-07-20 3,924 anal sex Group Sex crossdressing facefucking slut
0%
A Working Sissy Girl
I look up at my boots. Cute! Received delivery just day before yesterday, my boy friend hasn't even seen them yet. He'll like them, know he will. 3" spike heel ankle boots, very shiny patent leather, I look up at the one on my right foot. I run my hand down the thigh-high lace top seamed nylon ... Read full Story
shemale lover 2012-07-29 4,024 Cumshot oral sex sissy
100%
Finding A New Purpose Chapter 1
It had all started when I had lost some stupid bet over a video game. "Loser has to jerk the winner off," my friend Mike said jokingly while warming his trigger finger up on his controller. "Ha, funny." During the game I tried staying focused on beating him soundly so I ... Read full Story
shemale lover 2012-08-07 4,537 oral sex masturbating toys
50%
Tutoring Darla
"Professor ..." I glance up from my computer to see Darla, a sweet girl who unfortunately talks a mile a minute for far too many minutes at a time. I immediately wish her away—I'm too busy to pretend to listen to her prattle on today. Still, she means well enough and, anyway, I'm ... Read full Story
shemale lover 2012-09-08 4,036 Big Tits threesome ass licking domination
50%
Al Fresco: An Erotic Sci Fi Tale
"Thank goodness for modern science," Ali said as she smoothed her tight black skirt across her shapely hips. The tall brunette turned this way and that in front of her mirror, admiring her taut, toned, and trim figure. Her hands moved up from her hips to cup the twin handfuls at her chest,... Read full Story
shemale lover 2012-09-19 7,412 Cumshot ass fucking oral sex cum swallowing
100%
Dream Bride Tranny
My niece Avril and I rushed along the ground floor corridor of the hotel and made sure none of our relatives were watching us as we disappeared into the room. Inside, we were met by Miss Anne of the Kinky Brides Group, who immediately ordered Avril to strip me naked. "Please, not today,&q... Read full Story
shemale lover 2012-11-13 5,776 anal cum oral Lingerie
100%
FMDM Inc - The Interview
I had just finished a therapy session and was glad to get back to my office and relax. I'd have to lay off the cinnamon stix in the morning, my bustier was tighter than usual. My mini-frig offered a variety of drinks and I grabbed the pitcher of iced tea and poured a glass. Settling into the rich... Read full Story
shemale lover 2012-11-14 3,510 Cumshot Fetish domination
100%
White TV + Black Gangsta - 1st Date
I was having another somewhat boring evening alone. My name is Jill (when I put on women's clothes, that is) I was sitting at my computer, checking out the chat rooms on AOL. Just moments before, I had shed my male persona and taken a long hot bath, followed by a sensuous body shave that had left me... Read full Story
shemale lover 2012-11-19 3,577 anal sex cum oral sex kissing
100%
Fun With Friends Chapter 5
When I got home, I spent the rest of the evening thinking about how in a few hours I had gone from a closet cross dresser to a full on cock sucking, bend over and take it up the ass slut who was then shown to a group of strangers as a latex and high heel-wearing sissy. I'm not sure when I fell as... Read full Story
shemale lover 2012-12-12 3,400 Stockings sucking Sex Toys crossdressing heels
100%
Fun With Friends Chapter 7
After filling Kyle's mouth with cum his humiliation continued that night with the girls picking out a sexy little outfit for him to wear before Hannah & Steph took it in turns to fuck him with a huge rubber cock as we all watched on. At first he was a little unsure trying to walk in the 5" ... Read full Story
shemale lover 2012-12-12 3,185 Group Sex oral Sex Toys humiliation
85%
Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
metamafia 2012-12-21 119,653 hardcore Cumshot sucking bdsm domination
54%
Only Genetic Girl Close To A Trans Women
I rustle for something in my large purse. I pull out and hand me a set of heels. "put them on". You answer "Now?" "yes slut!" I answer back, I want you looking pretty when I fuck you. Well I will guess your heart skips a beat and your cock swells. You awkwardly slip o... Read full Story
KevLoc 2015-03-13 3,181 sex toy strapon spanking dominant
100%
Online Mistress Chapter 1
My name is Kayla Andrews, I’m a closet sissy gurl who loves the color pink and everything femme! Nobody knows about my little secret except for my private online world. Recently I put out a craigslist ad for an online mistress and I got a response from a beautiful blonde woman who was looking for a... Read full Story
CandyShopKayla 2016-02-16 5,648 bdsm cum trans sissy crosdressing
100%
Zoe procures a sissy..Chapter 1.
Zoe Viper sat back on her sofa extremely pleased with how her Friday night was shaping up. Wearing lace top stockings,a tight,black,latex miniskirt with a red satin corset and elbow length,black latex gloves,she took a drag on her blunt. Blowing out the smoke through perfectly painted red lips,she... Read full Story
Jasonlovesatin 2024-06-28 3,157 Lingerie domination sissy
75%
Mistress
My wife (Airlia) and I are open minded when it comes to sex. We are pretty much into everything, but at the moment we found ourselves going to a mistress for a bit of fun. We have been to our mistress four or five times so far and we both enjoy watching the other getting abused, especially Airlia wh... Read full Story
shemale lover 2011-08-27 6,548 fingering Sex Toys facefucking
0%
The Surprise Call
"Thanks for the wonder full time we had together last night Army Bear, it was awesome! I hope, we keep in touch as we both agreed," I sent my toy boy an email the day after our Valentines date. I was still thinking about of our hot night/morning together, I couldn't keep him out of my mind... Read full Story
HotVersatileTs 2011-10-04 4,379 sucking domination ts foreplay
75%
All Night Forced Sex Part 2
When I woke up I was in a darkened room and a woman was standing in front of me she was the most stunningly beautiful woman I'd ever seen before in my life. She's statuesque, about 30ish, with long red hair almost down to her perfectly shaped ass. She's wearing all black - a vest that pushes her bea... Read full Story
shemale lover 2011-10-09 3,589 shemale domination spanking
57%
Debbie Part 9
It soon turned out that Debbie wasn't destined to spend the rest of her life as a whore. As she returned to the apartment one night one of Mistress' men was waiting for her. She had only just opened the door, when without a word he cuffed her hands behind her back, gagged her and put a collar and le... Read full Story
shemale lover 2011-12-23 6,615 transgender toys bondage and discipline heavy
25%
As Mistress Commands
I remember the first time I was exposed to this world. I was 20, and in my 2nd year of college, majoring in aviation technology. I had been studying my brains out for a paper when I decided to take a break and have some good naughty fun online. I took out the notebook and was goofing off in the chat... Read full Story
shemale lover 2012-01-04 6,313 bdsm cum oral humiliation
100%
Becoming A She-Males Bitch Part 2
After last nights ordeal I was given something to drink and taken to a bedroom upstairs. What I drank must have had some kind of drug in it because I was knocked out. I bet I was asleep in just a couple of minutes. I barely even remember lying down. When I woke up I was naked, sore as hell and fe... Read full Story
shemale lover 2012-01-04 9,097 cum oral domination
100%
Siisy Bride gets what she deserves
I had Ben on a contact site and we live surprisingly close together in Manchester. Ben is a 6’2” black man who has a large sex drive and likes women and girly trannys. I am a slim white guy who likes to dress like a smart woman, not a slut. I haven’t worn a wig for over 6 years ... Read full Story
shemale lover 2012-01-05 4,670 shemales interracial sex bdsm