Sort by
Relevancy

Free Stories

77%
More Than A Woman
Doctor Carter surveyed the gathering of ladies before him. Something wasn't quite right, but he just couldn't put his finger on what it was. He had been invited to speak on Female Reproductive Health but the women were neither the charity driven older matrons or eager young housewives that he exp... Read full Story
shemale lover 2011-11-17 2,788 cum oral
100%
Guard Duty
Susan Denton was apprehensive as she approached the airport security station. She didn't like having to set her purse on the black conveyor belt that transported it - and the personal effects it contained - through the X-ray machine that rendered ghost images of her personal effects. On one occasion... Read full Story
shemale lover 2011-12-09 3,543 hardcore chick with dick domination
0%
Magician's Assistant - Friends & Lovers Part 5
Magician's Assistant - Friends & Lovers takes place in the Magatrix the Magnificent Universe, which was first introduced in my serialized seven-part story, Magician's Assistant. The premise upon which both that story and this story are based revolves around the fact that Magatrix the Magnificent... Read full Story
shemale lover 2011-12-26 3,905 femdom erotic encounters fantastic erotic
100%
End of the Beginning
Jamie stood there with her mouth hung open for a moment. She was utterly shocked. How could it be true? Chloe and Josh met at basic, how could they be engaged? It had only been a month since Jamie left. Tears stood in her eyes but refused to fall. This was not at all what she had envisioned. “... Read full Story
shemale lover 2012-04-14 2,539 anal Creampie oral
100%
Double Take Chapter 3
Sandy and Ashley switched off the television and stared at one another in disbelief. Normally, they didn't stay up to watch the network telecast of Wet Girls, which came on at 10:00 on the west coast. After all, they had to get up at 5:00 the next morning. But they knew the entire country would be t... Read full Story
shemale lover 2012-11-03 3,093 Stockings Fetish feminization
100%
Friday, March 11
I am wet. We are in a cab. The taste of Marlboro and whisky on his breath as we kiss, his hand runs under my t-shirt, fumbling for the release of my bindings. My hand is on his cock, over his tight jeans... he is hard, hot under my fumbling fingers. I rub him through the coarse fabric, as his ... Read full Story
shemale lover 2012-11-29 1,786 anal Cumshot sucking
85%
Fucking with Gina!
Hi! Here I am with my own story! I’m a young white guy, a good looking son of a bitch! When I was a college student, one of those numerous young people who always rush for something, then I was a focus of interest for lots of chicks around! But then something changed. Changed a lot. As I remem... Read full Story
shemale lover 2014-05-13 6,696 tranny asshole Blowjob
100%
Trans State Private School
Tommy heard a rumor that the Trans State cheer leading squad (even though it had the prettiest, sexiest girls in the state), all had cocks hidden in their cheerleader panties. His school was playing Trans State that day, and Tommy had to find out if it was true. The squad was on the fie... Read full Story
shemale lover 2012-01-04 5,330 shemales gangbang cheerleader
61%
Massage parlor surprise
I have to admit one of my biggest turn ons are shemales/ladyboys. In all my little ventures to asian massage parlors for some relaxing relief only once did I get a total surprise. About a year ago I visited one of my favorit little places and Mama said I should try her new girl....I might like her. ... Read full Story
shemale lover 2012-02-06 21,614 deepthroating jizz jacking off
100%
Can I Be This Lucky? Chapter 2
As we rode towards her place, she told me a little more of her story. Her name was Alex. She was one of those little boys who never felt right. She always liked playing with the girls, with dolls & dressing up. She always felt like a girl in a boys body. I totally remembered the boys we called &... Read full Story
shemale lover 2012-03-03 2,907 tranny anal sex cum stroking
90%
My first time with three shemales
This is a true story it happened to me back in 1988 when i was still bi i was in a local gay bar it was shemale night close to midnight when i saw this very tall gurl walk in with some friends she was hot about 6' 2" tall with 6" heels" all legs and ass she was blond and so senual wit... Read full Story
shemale lover 2012-09-20 3,853 first time anal sex Group Sex Blowjob
72%
My Ts Escorts Favorite Memories 1
I tend to turn to my dirty secret once a week. I had been searching for months for the sexiest escort to call when I finally got the nerve to call the ads on backpage. My most recent one was for a Cuban Goddess with a 9 inch FF verse, tall slim big titty small waist tight booty.. When I got to ... Read full Story
Ur Papi Chulo 2016-01-20 5,690 sucking fucking ts escorts ts stories
95%
First TS sex
I think I was near my 35Th birthday and, believe it or not I had never had experience with a transsexual. I had plenty adventures with men and liked it very much as well as with women. Decidedly I was completely bi. As I wrote in previous stories, I’m writing about near 30 years ago. It was... Read full Story
shemale lover 2014-08-11 5,908 shemales gay male wanking
86%
A Great night in by myself
I love dressing up in women's cloths they feel so smooth and sexy against my skin. A backless pinstripe lycra dress shows off my shoulders and back stretched tight over my peachy round buttocks. A little pair of white lace boxers underneath just visible as the skirt rides my thighs when I admire mys... Read full Story
shemale lover 2017-04-28 4,218 anal shemales Masturbation
50%
His sexy flies catches my eye
Another routine day was passing as I carried my shopping bags back home. Turning up a side street the late afternoon sun shining I suddenly encountered the most sexy guy I had ever seen. He was so cool that I hadn't even seen guys on TV as cool and good looking as that. He was an Asian guy in his... Read full Story
shemale lover 2011-09-16 2,961 anal shemales interracial sex
100%
Wish cum true
My wife and I have had a strong and open relationship from the start. We have accepted each other and all our wild passions, and we have always been open about our sexual desires. Having said this I will try to express what happened the other night with the same intensity I experienced. I came ho... Read full Story
shemale lover 2011-09-26 6,380 anal first time shemales
100%
A Real Fantasy
It was a boring Wednesday evening. I was away from home on business. With nobody to talk to and nothing good on the TV I decided to go for a walk. I walked for a few blocks and noticed the neighborhood was changing from hotels and bars to strip clubs and adult bookstores. I had never been to a strip... Read full Story
shemale lover 2012-05-28 5,729 anal sex Cumshot Creampie facial oral sex
100%
Hidden Surprise
After staring at Angela's crotch for what seemed to be forever, the shocked young woman asked, "I-is that what I think it is???" "I guess it depends on what you think it is," Angela replied softly. "But how, why???" Midori asked. " I mean you have a cock for christ... Read full Story
shemale lover 2012-09-17 2,982 Cumshot oral sex
100%
Deep trouble
I'm at a bar, it must've been a weeknight because it was sparsely crowded. I'm having a few drinks (more than a few but), there is music playing, people are kinda dancing. This beautiful blonde about maybe 5'7'' comes in all alone. Sexy little thing with big dick sucking lips, huge breasts squashed ... Read full Story
shemale lover 2012-11-01 4,354 anal sex Fetish Latex Sex Toys
100%
An Afternoon with Cara
Even though I was expecting it, the knock on the door startled me. Cara was a few minutes late so I had been fussing with the apartment, making certain that everything was arranged just so. Two martini glasses, a shaker and a small shallow bowl with stuffed olives sat poised on the counter that sepa... Read full Story
shemale lover 2012-11-08 2,989 oral deepthroating stroking
100%
Starcrossed Sleepover
I never was one to push my sexuality upon others... I have always felt.... unrequired in that area. so much so, that I lack the ability to be discrimitive to people, regardless of there beliefs... there origin... there sexuality... or even there religious or politcal views... in the end. I felt we a... Read full Story
shemale lover 2011-10-01 3,152 anal shemales gay male
71%
Caught by my wife
I was stuck, I couldn't move, literally in headlights... I dress up okay? you caught me, I guess your the master now... I used to control my wives life and for good reason I pleased her, and she pleased me the best she could... well now that's changed.. she came home from work early last Tuesday and... Read full Story
shemale lover 2011-12-07 4,482 first time shemales Group Sex
66%
Sissy lola gets a treat
Last night was my first night as a sissy maid for my beautiful goddess maureen and i have been instructed to tell you what a dirty little cock sucking whore i have been. I have known goddess maureen for a while now, she has been giving me instructions via webcam. She would make me flog myself or ... Read full Story
shemale lover 2012-01-03 2,284 shemales gay male Fetish bdsm
100%
Can I Be This Lucky?
I had just broken up with my wife of 4 years. So I was definitely not feeling good about myself. My time in the Navy was just about up, & not a second too soon. Now that I was done with my wife, I had no reason to stick around here anyway. I decided to go check out a movie to get my mind off thi... Read full Story
shemale lover 2012-03-03 3,771 tranny cum condom sex
62%
Floor Crossdressing Whore
Hey i'm 6'0" 160 and it was my first year in college and I turned 19 over the summer.I am living in an all guy dorm, and I was very nervous to be in a new place, but i knew how i could relax. I set up my computer and went to my favorite website. The site had crossdressing men who got fucked by ... Read full Story
shemale lover 2012-04-08 2,957 Crossdresser Creampie blonde cum swallowing
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 2,300 anal sex Creampie handjob
100%
Meeting a guy from online Part 1
I had been talking to a guy Jim online for a few months he was white 47 and we got into some very erotic conversations on line and even had phone sex together a few time then we decided to meet,I was all too excited thinking about seeing him in anticipating what both of us knew what was going to hap... Read full Story
shemale lover 2012-06-03 3,095 Crossdresser Cumshot Ebony oral sex
100%
Fantasy Reversal Chapter 4
I looked each way as I exited the room. Thankfully, the elevator was only about four doors down and the hall was quiet. With my bag in tow I walked to the elevator pushing the button, my reflection in full view in the polished elevator door. I stood there, for a few moments as if in a trance as I... Read full Story
shemale lover 2012-06-29 2,673 anal sex Creampie crossdressing
80%
Unexpected payback
Tanja woke up from the muffled moaning at the end of her bed. She lazily stretched her muscles stroked a hand through her long blond hair and examined herself. Hmmmm she moaned she had fallen asleep wearing the clothes she wore last night: Thighigh leather boots, leather skirt, leather bustier and o... Read full Story
shemale lover 2012-10-20 3,240 anal shemales oral sperm
100%
An Amazingly Intense Encounter
The front doorbell ringing woke me from a pleasant nap on my living room sofa. It was late in the evening, and I wasn't expecting anyone to drop by. When I opened the door, there you stood. From your long, pulled back hair, to the red leather bustier, ultra mini black leather skirt(so revealing... Read full Story
coldasicefire 2018-03-04 3,582 Bareback domination
60%
A Sissy's Long Night
We were to meet at a hotel, the seedy kind where nobody respectable would go. I was to meet him in his room, just down the hall from mine. I was very nervous. This was my first time meeting someone like this. Usually, I knew the person before hand, and always met at private parties where other peopl... Read full Story
shemale lover 2012-02-17 3,402 Fetish domination sissy
76%
My uncle
The other day I was dressing up in my sisters tight little black dress, I know I'm passable bit I had no idea how much... Well anyway I always heard I would look like my sister if I had a dress on and believe me I did. So on this day I had some free time, or so I thought... I spent the day procurrin... Read full Story
shemale lover 2012-06-08 4,288 anal sex Cumshot Fetish crossdressing
100%
Feminine Fantasy Come True
One Saturday morning I wake up and decide to go shopping for some really sexy and feminine girls clothes. I'm what I guess you could call, a "closet cross dresser." Although I have always been too shy to try and pass as a girl in public, I have been dressing up as one in secret ever since ... Read full Story
shemale lover 2012-07-07 4,001 Fetish crossdressing
100%
Break-Up Surprise
I was 18 and had been dressing up for two years before anyone had learned of my little hobby. I had no intention of telling anyone until I saw a friend in need. I was perfectly content getting dressed up in sexy clothes and having fun with someone on the internet from the privacy of my house. My ... Read full Story
shemale lover 2012-08-29 3,524 Cumshot Fetish doggy style oral sex crossdressing
50%
Polish Maid
'You want to get tips,' I explained to Marek, our Polish cleaner, 'You should be more a maid more like her.' Across the street was a girl of about 19, dressed in a fancy dress French maid's costume stumbling home, presumably from a party the night before. She was dressed in a tiny black dress, l... Read full Story
shemale lover 2012-09-01 4,782 Stockings Crossdresser Cumshot sucking heels
100%
Sex with strangers in public bathroom
I always had a sexual fantasy of dressing up as a chunky sexy slut tranny and visiting a known public mens bathroom close to my house and giving oral sex and what ever they wanted me to do for them sexually.Well I finally got up the courage to do it and before I go into my true first time experience... Read full Story
shemale lover 2012-10-01 4,871 anal hardcore Creampie Fetish oral fingering
66%
Alley Fuck
I lay on the ground on my side in the alley listening to the grunts and moans. My skirt was too low and was restricting movement so I lifted it up a bit, then reached back down to my panties and continued rubbing my cock through the lace. My head bobbed up and down, my wig bounced its bangles agains... Read full Story
shemale lover 2012-10-13 3,042 cum oral jerking off
88%
Book Store Bop By Cumhunger
A lady friend of mine Kelly had been riding to work with me for the past week and every evening on the drive home we past an adult book store.I mentioned something to her in passing that the lot always seemed to be full.She looked at me with a mischivous grin and said... yeah all the guys who's w... Read full Story
shemale lover 2012-10-14 3,229 anal Creampie voyeur
100%
An Evening with Delia
THE WAY SHE IS NOW It had been ages since I last saw Delia and I was trembling with excitement to see her again after all this time. I climbed the stairs to her small flat and by the time I reached the top landing, I was breathless both from the physical exertion of climbing the stairs and the an... Read full Story
shemale lover 2012-11-14 3,226 anal sex Cumshot oral sex
100%
Transvestite in trouble Part 3
I felt his stiff cock at my asshole. I shuffled my legs a little further apart, partly to prevent him ramming it into me and it hurting, and partly bacause I just wanted him to fuck me! "you fuckin dirty slut" he whispered...he'd noticed my little subtle movement " you want my cock... Read full Story
shemale lover 2011-09-26 2,434 anal shemales bdsm
100%
Head Cheerleader Mikki Part 4 Mikki wants a Boyfriend
This is part 4 of Mikki's story. Please read the previous chapters. After Monday night at Tommy's house I came to the conclusion that I want to be with Donna when I'm Mick and guy when I'm Mikki . It's Friday night and Donna is coming over . My dad is coming home on Sunday so my mother wants to s... Read full Story
shemale lover 2012-06-16 2,568 first time Cumshot oral sex double penetration