Sort by
Relevancy

Free Stories

54%
Michael’s Visitation
I was on my way to the airport to catch my flight to Miami. I thought to myself that my seat mate like a little in flight entertainment. I decided to wear my platinum blonde hair pulled back in a pony with some wispy bangs, dangly floral ear rings, light eye make up, but heavy on the lipstick (alway... Read full Story
shemale lover 2017-08-22 12,487 Cumshot Masturbation ass fucking
100%
Far Eastern Adventure
He was transferred to the Far East with no real choice in the matter. His boss never took no for an answer and rarely gave him the opportunity to try. She had been acting strangely for the last few weeks, eyeing him oddly as if trying to unravel some hidden mystery within him. This strange perusa... Read full Story
shemale lover 2019-10-20 8,128 Cumshot tgirl nipples
93%
Horny Aerobic Instructor
Carla is big on aerobic workouts and she loved watching her instructor's muscles as he worked out hard with them. His hot sweaty muscular body did wonders for Carla's sexual appetite. She puffed around the room when he did, did step-ups when he did them she always worked out at the front of the c... Read full Story
shemale lover 2011-08-13 5,905 Cumshot licking oral sex
50%
The Sexiest Shemales Part 1
When I wake up in the morning, I wake up next to the sexiest shemale in the world...right after me, of course. I woke up this morning next to Holly, my beautiful shemale girlfriend. She was still sleeping in our big bed. The sun was shining in on our bed with our white sheets and white comforter. ... Read full Story
shemale lover 2011-09-03 2,810 anal Cumshot sucking
100%
Connie at an Adult Bookstore
Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * Let me start by i... Read full Story
shemale lover 2011-09-30 4,179 Cumshot Blowjob crossdressing
100%
Susan's First Time
Stan/Susan wondered how he/she could have gotten herself into this particular fix. This week Stan was at Sue's posh apartment so was living as a woman. The large good-looking gentleman kneeling between her spread legs was very firm about what he wanted her to do. "After you suck my cock I'm ... Read full Story
shemale lover 2011-10-13 3,694 first time Cumshot oral
100%
Tranny Attack
Tears of pain pricked my eyes as Julia drove her huge black cock into my ass. In my wildest dreams I had never expected myself, an all-American straight white male to be in this situation, beaten, bound, and being ass-fucked by a transsexual with a huge cock. I am a normal sort of person, happily... Read full Story
shemale lover 2011-10-15 7,041 anal Cumshot Big Cock Ebony
100%
Robin's Adventure
I wanted him to have me completely and totally. I couldn't believe I was feeling like this as I sat in the passenger seat of his car. His cock felt so large in my hands. I.... well I guess I'd better explain who "I" am. My name is Robin Daniels, I'm transgendered. I guess I've known it ... Read full Story
shemale lover 2011-10-25 2,993 Cumshot sucking handjob transgender
100%
How I Became a Tranny Whore
When I was 30 with children at home I would get dressed in the bedroom. When it was time to leave the wife would take the children off for ice cream and as soon as they were out of the drive way I would head for my car. Of course when I returned home the children would be a sleep. The plan worked fo... Read full Story
shemale lover 2011-11-07 4,534 anal Cumshot cum swallowing
77%
Caramel And Devin
I began crossdressing at 12, but it wasn’t until I was 17 when I dressed up completely for the first time. When my parents went away for the weekend to Atlantic City, I took advantage of the opportunity to explore my feminine side to the fullest. As soon as they left the house that summer morn... Read full Story
shemale lover 2011-11-10 4,181 Cumshot sucking fingering
100%
A Close Encounter of the...
Another great tape and another great yank of the crank. Yea, she-males were pretty hot, Tom thought as he hit the eject bottom on the tape deck, but where on earth would he really find one? He had little doubt that if he did find a place where they hung out that there would be more than a few with a... Read full Story
shemale lover 2011-11-13 4,908 Cumshot Blowjob massage
50%
The Sweetest Taboo
"Hey sis! Remember me?" Tisha Roberts stood at the door in complete shock looking at the person in front of her, the latest KaySlay CD whispering its aural presence in the background. She scanned the person in front of her, trying to figure out what was going on. The woman in front of h... Read full Story
shemale lover 2011-11-14 5,258 Cumshot cum swallowing handjob
75%
Becoming A She-Males Bitch Part 3
When my alarm went off, it woke me up abruptly and scared me. My heart was pounding so I took a minuet and got myself together. I went into the bathroom and removed my collar. I took a shower, shaved and applied my make-up. I grabbed a thong from my dresser; I picked out a pair of heels from my clos... Read full Story
shemale lover 2012-01-04 3,502 Cumshot domination humiliation
50%
Ghosts Chapter 2
"Good morning my dear jamie. Have a good nights rest?" my captor speaks, invisible as ghosts are. I am as I was when he left me. I have invisible ghost restraints on my wrists and ankles. I'm lying on my back, spread so my arms and legs form an X shape. The cum that my ghost captor m... Read full Story
shemale lover 2012-01-25 2,856 Cumshot licking sucking fucking
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 2,982 Cumshot suck Big Cock fuck
100%
First Time With a Shemale
I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality. I'd been with a few girls growing up, but nothing ridiculous. I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we... Read full Story
shemale lover 2012-02-12 6,018 first time Cumshot sucking
100%
A Dickgirl Part 2
Ginny was mortified. For the first time in her life she hated her body. Why the fuck did she have so little self-control? Why couldn't she hold her body back? Why couldn't she be like normal girls? She cried all the way home, her tears drenching her shirt. She stopped by the time she got home, bu... Read full Story
shemale lover 2012-02-27 6,486 Cumshot sucking Big Cock Shemale and Girl
100%
A Hot Time with Sheila
He was sitting there sipping on his third rum and coke of the evening when he saw her. She was about 5'5'' tall, with long blonde hair and green eyes. She was staring at him and he realized that she had been for sometime now. She got up and started to sashay towards him. He allowed himself to tak... Read full Story
shemale lover 2012-03-10 2,463 Stockings Cumshot oral sex
100%
E is for Erica
I was surprised. Very surprised. I mean, in those circumstances, in that situation. Late in the evening, in a hotel just outside Cardiff, I was there for an interview. I mean, the interview was the next day. TKB were a big firm, still are. I could have driven to their Head Office early the next morn... Read full Story
shemale lover 2012-03-30 2,727 Crossdresser Cumshot Lingerie cum swallowing 69 position
100%
A New Dawn Chapter 4
After their little escapade in the office toilets, Tom and Dawn had decided to be a bit more careful at work. As enjoyable and exciting as it had been for both of them, it wasn't worth risking their jobs over. Besides, it just meant that it was all the more pleasurable when they finally got home tog... Read full Story
shemale lover 2012-03-31 3,321 Group Sex Cumshot oral fingering
100%
A New Dawn Chapter 5
Tom's life was going well. He had a job he enjoyed, and apartment he was comfortable in and he had Dawn. He watched her in the mirror from the bed they shared as she applied her make up and smiled. Yep, things were pretty good. Dawn saw him watching her and grinned. "What are you smiling abo... Read full Story
shemale lover 2012-03-31 2,963 Big Tits Cumshot oral fingering cum swallowing
100%
A New Experience
I had been sat in the hotel lobby for a couple of hours, bored, just watching people come and go. I hated these business trips. There I was in a strange city, knowing nobody, hanging around waiting for business meetings. Out of all the people I had seen there were such a variety of people. Pensioner... Read full Story
shemale lover 2012-04-01 2,491 Cumshot Creampie Big Cock
100%
Emily and Steve Part 2
I was sitting at my desk with my office phone pressed against my ear, supporting myself with my left hand and trying not to fall asleep. On the other end, someone from Gooseman Paper Products droned on about terms of payment and invoice formats. It was a typical Thursday afternoon. Just then, an ... Read full Story
shemale lover 2012-04-06 2,902 Crossdresser anal sex Cumshot blonde rimjob
100%
A New Life Part 2
The next few days I spent packing and repacking. I would need to watch what I packed as I was taking a plain to meet Sara and Tom. Most if not all my toys would either need to be mailed or stay behind. I had packed five suit cases all of them filled with female clothing and shoes. My carry on was pa... Read full Story
shemale lover 2012-04-13 3,011 Cumshot Sex Toys cum swallowing sissy
90%
Becoming Roberta
Years ago, I went out with a girl who was very kinky. I can't use her real name, because she is married now, but I will call her Christine. I liked a lot of the kinky stuff we did, especially being dominated and humiliated. She always wanted to see me have sex with another man, but I was very hesita... Read full Story
shemale lover 2012-04-13 2,600 anal sex Cumshot oral sex
100%
Emily's Punishment
Today I am wearing a white long-sleeved satin blouse, a dark blue knee-length skirt, sheer black stockings and dark blue court shoes with 3" heels. My long, dark hair cascades over my shoulders and down my back. My make-up is perfect and I must admit that I feel fantastic. There is a knock a... Read full Story
shemale lover 2012-04-13 2,566 Stockings Cumshot oral sex
100%
Engagement Sex
I've been with my girlfriend for over a year now and love her so much. She is cute, funny, and really sexy. We have a great time and we love to play around a little sexually, but Melissa is a conservative girl and has told me many times that she won't go all the way until we are engaged. Up until re... Read full Story
shemale lover 2012-04-16 5,621 Cumshot cum swallowing facefucking
100%
First time and what great fun
My name is Jakub, or Jake as my friends call me. At the time this little adventure took place, I was 20 years old and I guess I was a pretty lonely guy. Overall, I am a pretty average dude: 6 feet tall, slim body and average looks, the only thing about me that’s a bit different than most peopl... Read full Story
shemale lover 2012-04-16 3,908 anal sex Cumshot oral sex doggy position
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 9,188 Stockings Cumshot oral sex crossdressing
100%
A Night of Makeup, Cock and Cum
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further,... Read full Story
shemale lover 2012-04-18 4,631 Cumshot jerking off domination Sex Toys cum swallowing
100%
First Time Out
I am a 21 year old straight male and have had fantacies about wearing womens clothing. I have never acted on them and surpressed my desires to dress as a woman. One day I was one the internet and came across a website with crossdressres on it and my desires came back. Well as I kept looking throu... Read full Story
shemale lover 2012-04-19 4,199 anal Cumshot blonde oral crossdressing forced sex
66%
A Night Out To Remember Part 2
Decisions... decisions... we all make decisions everyday and most of them are simple easy decisions. Some may take hours, some take seconds and some are made before we even know it. Some decisions carefully planned and some have planning at all. Some decisions are between several choices and some ar... Read full Story
shemale lover 2012-04-20 2,817 anal sex Cumshot Sex Toys
66%
The teenage slut
Hey folks Sandy here once again. I know every time you see me I go up one grade level but this is one tale I felt I should tell you. Let me start at the beginning after me and Bella fucked each other. Well were still together. Laughing, eating together, just having fun basically. We still fuck in th... Read full Story
shemale lover 2012-04-25 3,549 Teen (18+) Cumshot oral sex cum swallowing
100%
Being Curious Has Big Rewards
I was brought up believing that men were not supposed to have sex together. The thought of this taboo type of sex was always made me curious. When I was 18 or 19, I visited an adult book store, just because I was horny and wanted to get a magazine that showed people getting fucked so I would have... Read full Story
shemale lover 2012-04-26 5,710 first time Cumshot oral sex cum swallowing
40%
Alabama Nan: On The Road
On the way home from work, I thought about the stuff Karen and I had packed. I wanted to be sure I had packed everything I needed for the week long stay. By the time I reached my apartment, I was certain that I had everything. I opened the door and yelled "Get our bags Karen. It's time to go.&q... Read full Story
shemale lover 2012-04-27 2,974 Cumshot oral sex deepthroating
71%
Trans secretary
"Monica Barnes smoothed her skirt before entering the office of her boss, Cord Drake, the CEO of the company his father had founded thirty eight years ago! Like every other morning for the past two years, she brought along his coffee, her memo pad, and of course his copy of the morning paper! &... Read full Story
shemale lover 2012-04-30 4,112 anal sex Cumshot Big Cock oral sex
100%
Dirty Tranny Bitch
I was feeling really horny, massive nervous anticipation. I was all dressed up, looking for my first taste of cock. My name's Nikki, I was aged about 25 or 26 at the time, only 2/3 years ago, but I was fed up being the `closet' tranny tart, I wanted to try out some cock; in short, I wanted dirty ... Read full Story
shemale lover 2012-05-01 3,477 Stockings anal sex Cumshot oral sex finger fucking
60%
The Clinic
I got out of my cab and looked up at the Clinic. It was a small, nondescript hospital. I was still pretty nervous about this treatment since I wasn't even sure of the details. But it was either this or go under the knife. This problem had to be dealt with. I picked up my bag and went into the lobby.... Read full Story
shemale lover 2012-05-02 5,768 Cumshot Big Cock jerking off oral sex cum swallowing
100%
The Poker Game
I'm 21 and i'd always considered myself totally straight until towards finishing school. I started having more fantasies about cocks. I would not find myself attracted to guys but while watching porn i would always love seeing the cock as well as the girl, sometimes wishing i was the girl sucking it... Read full Story
shemale lover 2012-05-04 3,082 anal Cumshot Blowjob wanking crossdressing
88%
Pulled Over
She stammered as she answered him " Y..y..yes Officer." She wenton in her soft cultured voice"It's just that i'm going to be late to work again and my boss isso strict." She looked up to seethe the cop staring at her long legs and shifted uncomfortably. "Step out of the c... Read full Story
shemale lover 2012-05-08 2,447 hardcore Cumshot cum swallowing facefucking
83%
The Hermaphrodite
Being a true hermaphrodite had its drawbacks, but Nicole had resigned to herself early I life that while she would not be able to marry and have children, she could partake of sexual pleasures that ordinary men and women could only dream of!!! She had a close circle of friends who knew of her condit... Read full Story
shemale lover 2012-05-08 3,246 Group Sex Cumshot jerking oral sex
100%
Fuck Me
My life had become pretty boring and my sex life non-existent. The women in my life had all proven themselves to be untrustworthy, transparent and superficial. I was taking a break from the world. I just wanted to sit at my bar stool, get drunk and smoke my Cohiba until I could drink and smoke no mo... Read full Story
shemale lover 2012-05-08 4,263 first time Cumshot oral sex cum swallowing
100%
A life Changing Experience
My sophomore year I began dating this girl named Jan. Jan was blonde, slender, and absolutely gorgeous. She lived in this two bedroom apartment with her roommate Samantha. Sam, as she liked to be called, was a redhead, with dark green eyes and a nice chest. While not as beautiful as Jan she was stil... Read full Story
shemale lover 2012-05-09 3,610 Cumshot oral sex cum swallowing assfucking
100%
Threeway Heaven
Times were tough and I took a job as a bouncer in clubs on weekends. It was a pretty boring job most nights, and frustrating having to deal with drunks all the time, so my boss sent me out to a gay club for a change of pace. Also, I was one of his few workers who wasn't homophobic, and therefore les... Read full Story
shemale lover 2012-05-10 3,159 Group Sex Cumshot sucking fingering
100%
What A Night....
I was just finishing my first sip of the Gin and Tonic when I heard "is this stool taken?" I turned to see the pretty brunette and said "Now it is." She sat down and crossed her legs. She was wearing black hose and a knee length leather skirt with a slit that went a... Read full Story
shemale lover 2012-05-11 2,889 anal sex Cumshot oral sex cum swallowing 69 position
66%
The Making of A Sissy Part 2
As Bella blossomed physically, Jane ensured the girls took control of her; she was made to know her place amongst females and was still subjected to their choosing her outfits. Bella was habitually made to pose before a full length mirror as Jane and the girls scrutinised her feminine shape; the gir... Read full Story
shemale lover 2012-05-16 4,155 Cumshot Fetish spanking sissy
100%
My second time with Jake
The week after my first experience with Jake was amazing. I had finally sucked a real cock and I wanted to again. All that week Jake kept texting me pictures of his hard cock. I couldn’t believe that he was into a gurl like me. On Thursday of the week he texted me another pic of his cock and t... Read full Story
shemale lover 2012-05-16 2,211 anal sex Cumshot transvestite
40%
Becoming wife of competitor feminized by secretary
I am Siddharth Mittal, running my own Company with USD 100 Million of Business. Everything is going on well and I am excelling in my business. I have a secretary named Sonia. She is a smart and beautiful girl with 36-32-36 size. She knows how to get her work done. She wears simple clothes and is dec... Read full Story
shemale lover 2012-05-17 5,650 anal sex Cumshot Big Cock feminization
100%
My First Cock
I always knew I really was meant to be a girl. For a while I thought I was simply gay, but I loved wearing thongs and bras. I loved masturbating while pretending my asshole was a vagina. I never made it a secret. I'm very flamboyant and girly. I still managed to have lots of friends in high school. ... Read full Story
shemale lover 2012-05-19 3,959 anal Cumshot Creampie fingering oral sex crossdressing rimjob
100%
Summer Woods CD
School was just out. My mother and father worked and my sister was older than me and slept most of the summer it seemed. She would get up late and i spent many summer days dressing in her panties and bras, experimenting with her makeup and acting the slut. I was settling into the summertime vacation... Read full Story
shemale lover 2012-05-19 3,242 Cumshot Fetish domination oral sex cum swallowing crossdressing
100%
Awakened by Candy
It was a Saturday and I was just strolling down the High Street, going nowhere in particular, when I noticed a commotion down a side alley. A largish male was pushing two girls around; they both looked pretty distressed. I grabbed the bloke as he slammed one of the girls into a door, and he went ars... Read full Story
shemale lover 2012-05-19 3,212 anal sex Cumshot Masturbation fingering ass licking
100%
Humiliation
My ex-wife and I still get along okay for the most part. She was enthusiastic about feminizing me. Occasionally she would get enough of it and then just go overboard to shut me up for a while. One such incident stands out. After a particularly nasty week at work, I came home Friday evening lookin... Read full Story
shemale lover 2012-05-21 4,374 anal sex Cumshot Fetish domination oral sex feminization
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 7,282 first time hardcore anal sex Cumshot oral sex crossdressing
100%
Dogging tv slut
It was dark enough now I thought. It was about eight o'clock on a warm spring evening and I was ready. I had started getting ready about three hours earlier. I'd showered, cleaned all those special parts, applied my make-up heavily and dressed. I was wearing a skimpy flower print top over a black si... Read full Story
shemale lover 2012-05-22 6,136 anal sex Cumshot oral sex
71%
The Superbowl
I was very surprised when my brother-in-law Tom invited me to watch the super bowl with some of his friends. The only reason he would “invite” me over was to be his little sex sissy, since he had enough pictures of me dressed as a girl sucking and being fucked by him I had no choice but ... Read full Story
shemale lover 2012-05-23 3,274 Stockings anal sex Cumshot Fetish deepthroating sissy
85%
The Making of A Sissy Part 4
After an exhausting evening Bella was made to wait at the door and humbly kiss the guests as they left; some of the males groping her pretty arse as they departed. She was glad of the alcohol she had been treated to as this masked from her the ugliness of some of the brutes she had been forced to en... Read full Story
shemale lover 2012-05-24 3,409 Group Sex Cumshot Masturbation little cock sissy