Sort by
Relevancy

Free Stories

88%
Stepdaughter's Transexual Surprise Part 2
As I ended the first chapter of my love story, my Stepdaughter Dawn and I were returning from loading a Ryder truck with her possessions. We were to spend the night at home, then continue on to her new place in the morning. We had stopped on the way and enjoyed committing acts of sin by Dawn seducin... Read full Story
shemale lover 2011-12-04 6,889 anal cum facefucking jacking off
80%
Mandy Awakens Dave's Desires
We had been flirting across the bar for several weeks at this point. She was just so easy to talk to. Although she wasn't stunningly beautiful, she was quite attractive. Mandy is about 5'2" or so, 110 pounds. She has a light complexion to go with her strawberry blond hair, which she wear... Read full Story
shemale lover 2012-01-10 4,774 anal sex cum 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 2,904 Big Tits Cumshot oral fingering cum swallowing
0%
The Day After
I explained in my previous story, which to really understand me you really have to read My life as a girl besides I am picking up where I left off but if you don't want to take the time to read it, I am what they call an intersexual. A term you should look up or go back to the other article to under... Read full Story
shemale lover 2012-05-04 3,100 Cumshot fingering oral sex cum swallowing
50%
Fantasy Oral Sex with TS Lisa Lawer
This is a pure work of fiction and has nothing truth in it. Only truth stated here is that I am very fond of shemales and addicted to Shemale photos and movies. One particular Shemale whom I love very much is Lisa Lawer, she is from Brazil. I have been a big collector of her photos and movies. I am ... Read full Story
shemale lover 2012-06-28 3,150 oral fingering doggy style cum swallowing pornstar rimjob
100%
A Valentines with a Bang...x
Time had seemingly flown by since meeting the man I was to fall head over heels for on a drunken night in the town centre, the type of guy you would never expect to be dating a transvestite but here I was waking by his side as I had done for the past 6 months or so since we moved in together after m... Read full Story
shemale lover 2012-07-16 3,084 anal sex cum oral sex
100%
Finishing School for Shemales Chapter 2
Davina hurried down the hallway, her books clasped in front of her heavy breasts to stop them jiggling as she ran. It had been almost two weeks since she had truly given herself to Mistress K in the beautiful, imposing headmistresses study, drinking the transgendered woman's seed from another T-g... Read full Story
shemale lover 2012-08-09 6,167 cum fingering little cock
100%
Brad and Tina
It started a year ago; I would get on the AOL chat rooms in hopes of meeting local dominant men. I was seeing a guy named Dan from time to time, just a fuck, nothing serious. Mistress Olivia was an incredible woman and the Domme I was currently serving. She satisfied most of my cravings to be ... Read full Story
shemale lover 2012-08-20 2,300 Cumshot sucking orgasm cum swallowing
50%
For The Sensual
For the sensual, description is everything. The collar. The collar is custom-made; one of two; her request. This particular one matches the corset. The corset—the "bustier." The collar. Literally, no choker here. She is disciplined. Her collars merely evoke ownership. She belongs. Sh... Read full Story
shemale lover 2012-11-14 3,060 anal kissing facefucking
81%
My stepmother has a surprise for me
My name is Robert, I'm 18, skinny and not too tall. I've never had much luck with girls, in fact I never dated one and I used to spent my days playing games on my computer and watching porn. Shemale porn. Dominant shemales fucking men. I wish i could be one of those men on the videos, that turned me... Read full Story
shemale lover 2013-04-08 233,772 suck Big Cock jerking big boobs cum swallowing
97%
My First Girly Cock
It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. ... Read full Story
shemale lover 2013-07-22 10,215 transsexual oral sex ass fingering kissing
81%
My 1st time with a man while dressed and 1st anal
My 1st time with a man while dressed and 1st anal The following story is true. I have been dressing in my wife's sexy clothes at home off and on for a while because I love the feel of hose and panties. My wife and I are swingers, actually we do mostly cuckold swinging but I am free to be with... Read full Story
gennipher 2017-04-11 17,953 first time interracial sex crossdressing black cock cd bbc
100%
A man & Two Hung Shemales meet in Art Gallery o
I spent a week of absolute extreme erotic ecstasy with Stan. I used his throat and ass multiple times a day. He also fucked and fisted my ass as well. It is a week of total decadence debauchery and depravity. In the late afternoon, Stan and I decide to visit a local art exhibit so we can get out ... Read full Story
darrell 2024-02-02 4,301 anal Cumshot Big Cock Frottage deepthroat shemale + shemale swallow cum
100%
Who actually likes English class?
I was sitting in yet another boring as hell English class. Seriously, why do I need to read Chaucer? Is that necessary for anything I will do in my life? As much as I try to convince myself the answer to those questions are yes, I still can't get interested in what he talked about in 1400 a.d. Ho... Read full Story
shemale lover 2011-08-12 7,359 Cumshot deepthroating cum swallowing
75%
Pleasure in the Park
I'd ridden that ride a thousand times.... But I just kept getting back into that huge queue line. I was at the local theme park riding the newest addition to the ragtag assembly of attractions, the Master Exploder. It was the craziest coaster I'd ever dared step my foot into. Everyone else loved ... Read full Story
shemale lover 2011-10-26 3,155 first time Stockings cum
80%
A Fairy Tale Part 1
=-=-Chapter One-=-= "Heather?" My boyfriend was knocking on the bathroom door. "What's wrong, are you okay? Heather?" "Yeah..." I swallowed thickly and that was a mistake. I threw up some more, kneeling on the floor, feeling like I was dying. "Heather?&q... Read full Story
shemale lover 2011-12-06 11,192 Bareback cum ass fucking slave
100%
TG - My new love
The neon light at the Thirsty Hole was like a beacon that grabbed my attention. I heard rumors around town that the Thirsty Hole was a hangout for shemales. Tonight I was cruising bars and decided to see what a shemale actually looked like. Now I'm a straight guy. Never really had even consi... Read full Story
shemale lover 2011-12-25 5,140 suck cum missionary style
100%
Back to School
It all started the day John got a letter in the mail; it was an invitation to his school reunion back home. John was proud of what he had achieved in his life; he had a good job and a house. The only secret John had was that he was a closet cross dresser; he loved to feel feminine from time to time.... Read full Story
shemale lover 2012-02-09 3,760 Shemale Fucks Guy orgy cum swallowing
100%
Bend That Gender
Shannon's Shocking Discovery Shannon leaned against Marilyn. She was definitely light-headed from her last drink. Marilyn's hand resting on her left hip pulled her closer, a move at once comforting and unsettling. She slid her arm around her new friend's waist, resting her head on the silk covere... Read full Story
shemale lover 2012-04-27 6,755 orgasm oral sex cum swallowing
100%
Danielle Works a Saturday
It had been a few months since his wife left him. Well "ex-wife" as the divorce had been recently finalized. It was her choice; she walked out on *him*. She said she got tired of "Danielle", even though she was entirely responsible for Danielle's "birth" to begin with. ... Read full Story
shemale lover 2012-06-18 5,457 anal sex Creampie oral sex cum swallowing
69%
Addicted to Candy
Almost two long weeks had passed since my first meeting with my new slave Candy. Our first encounter was special and my sexy new sub had not left my mind since he walked out of my door. His juicy ass and hard thick cock have filled my thoughts each day since. I had found myself wildly attracted to C... Read full Story
shemale lover 2012-08-12 3,421 anal sex Fetish cum domination Sex Toys cd
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 6,959 Cumshot ass fucking oral sex cum swallowing
100%
Brian and Bree, and Mitch Chapter 1
"Hey, so I'm going to be at Sarah's all night," Mitch said as he was walking out of the door, "Brian, it's Friday night. Get out and do something this time." "Man, I had class all day, it's been a long week. I think I'm just going to call it an early night," Brian re... Read full Story
shemale lover 2012-09-20 2,555 Fetish cum oral crossdressing
60%
Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
shemale lover 2012-09-28 6,366 Cumshot Fetish oral sex cum swallowing
100%
Whitney's Way
My arms were stretched over my head as I finished hanging the last sheet of drywall. Another step closer to the end of the two year process of renovating our first house, it was hard to conceal my sense of pride at turning a worthless wreck into the nicest place on the block. But as soon as I heard ... Read full Story
shemale lover 2012-11-18 8,343 Cumshot oral sex kissing
100%
Westward bound cum slut Chapter 2
Again I'm on the big bird headed out west for another fling. This time is going to be way different though, the players have increased, not to mention both sexes. The tale unwinds in the same fashion as the last trip out this way, the plane flight was long and boring, and being very nervous didn'... Read full Story
shemale lover 2012-12-16 3,404 anal Group Sex sucking Creampie cum domination
80%
Too Much Hospitality
Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned t-shirt and some ... Read full Story
ASSEaster5678 2018-09-17 8,486 anal Blowjob transsexual oral sex cum swallowing romance transgendered Consensual Sex Older Female / Males
62%
Man Is Humiliated By Escort
I am a very adventurous, open minded married guy. I am 6'2", 150lbs and I have a 5" cock. My wife (Mary) is great but she is very straight laced and doesn't like to have sex but twice a year so I decided to look elsewhere to fulfill a few fantasies. I am sure my size and stamina have a lot... Read full Story
shemale lover 2011-09-30 6,923 sucking Big Cock cum domination
85%
The Terrace View Apartments Part 4
I woke up on the third day of my new life, sore all over from having slept the night in my car. Sore, but quite satisfied. After all, I’d been treated to a nighttime tour of Houston’s most erotic sights and capped off the evening with a backseat blowjob from a somewhat masculine, but adm... Read full Story
shemale lover 2011-11-18 3,214 Masturbation cum crossdressing
71%
Glory Hole Girlfriend
My boyfriend likes to take me to the local adult bookstore, into the back where the video arcade is. There's always a lot of men there, strangers that we don't know, and I feel funny when they look at me. They wonder why a pretty young woman would be back there. It smells too. A rich sweaty sc... Read full Story
shemale lover 2011-12-18 7,113 Creampie ass fucking mouth fuck
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 5,818 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 8,592 cum oral domination
100%
The Bounty Hunter - Working With A Partner
My boss, Carl Bronson, was pleased with the results of my first case, and gave me more jobs over the next few months. In each, I learned from my mistakes and was able to apprehend my target. Even better, I was finally earning some good money and doing something that was worthwhile and, more importan... Read full Story
shemale lover 2012-01-29 4,224 sucking Creampie cum fucking
100%
Becoming Elizabeth Chapter 1
My name is Jack and I'm 32, and this is the story of how I was transformed into a pretty, cock-hungry slut named Elizabeth by my wife. I'm married to Debby, who is 44. Big age difference, huh? Well, it suits us just fine. How we met is a long convoluted story, but suffice to say that we were both... Read full Story
shemale lover 2012-03-11 3,180 cum fuck
100%
Digging for Home
Never Make the Last Out at Third After some minutes, Charlie broke the embrace. Backing away a step, she steered her moist brown eyes into Frank's damp grey ones. "What now?" The man tilted his head to one side and shrugged. "I'm not sure. It hasn't been a day yet since you went... Read full Story
shemale lover 2012-08-25 4,508 sucking cum facefucking
75%
X is for Xenia
My best girly-friend Yolanda gushed as she looked across the bar. "Hey, isn't that James? He looks really hot tonight, wow. It's a pity he's married." "Bitch!" I said jokingly and grinned at her. Him. Her. Whatever. I strained my neck to where 'she' was pointing and t... Read full Story
shemale lover 2012-09-22 5,453 cum oral sex facefucking
40%
First Sexual Crossdress Experience
How my secretary found out I'm a bi TV and how me and my TV friend educate her into some of the more zany aspects of TV sex. *** As I laid back against the wall of the toilet with my nylon-clad thighs spread wide and my erect cock jutting up lewdly from between them, the wooden door in front o... Read full Story
shemale lover 2012-09-27 5,412 first time Fetish cum oral crossdressing nylon
100%
Five Into Three Does Not Go
Kristina It is waspish in the late evening out in the open in Portsmouth Harbour as we step out of the vehicle and walk over to the private section of the docks, the sign says Ceres St docks. Dark has long since fallen but lights, white, yellow and orange light up the skies. The feeling is one of... Read full Story
shemale lover 2012-11-07 4,477 cum oral sex Sex Toys
100%
Francis Meets a Black Stud Part 5
I finally came upon a plan that I thought would make everyone happy. I would keep on playing this game with my man. I figured that as long as I was dressed like a girl, it didn't matter who he showed those videos too. I mean no one would know it was me and after all, he would be finish his vacation ... Read full Story
shemale lover 2012-11-20 2,801 cum oral sex Interracial
100%
When Curiosity Fills
I sat in alone in my office at 11:00 p.m. on a Thursday night in April, preparing an important motion in a multi-million dollar malpractice suit. After editing the final draft I sat back and took a deep breath. I was exhausted, and, oddly enough, pretty horny. The wife was out of town and somehow I ... Read full Story
shemale lover 2012-12-08 8,493 anal shemales cum
100%
Ken and Ayala Part 3 Cleansing
I'm glad we ended up at her place and not mine the night before. It's amazing how much cleaner women's apartments always were compared to mine. Especially their bathrooms. Her bathroom was your typical girl's bathroom. There was a host of styling and makeup equipment arranged on the bathroom coun... Read full Story
shemale lover 2011-11-10 3,104 Cumshot transsexual cum swallowing mouth fucking
33%
Fun with Stephanie-Gurl at the Park!!!
After weeks of chatting online I was able to convince Stephanie to meet me but she had one condition it has to be in public place. Now I am not one to hook up in public but I was dying to meet Stephanie and have a little fun. I knew of a park that was nearby that we could meet at late at night and s... Read full Story
shemale lover 2012-02-14 3,091 anal sex sucking cum
100%
Barbie Jo Adventures Part 3
Saturday Afternoon The sound is ringing in my ears as I drag myself out of a deep sleep. I look over at my clock and realize it's not the right time for my alarm. As I come more to life, I pick up my phone. "Hey gorgeous, how you feeling?" Booms a voice through the receiver, making my h... Read full Story
shemale lover 2012-02-18 2,907 anal sex cum jerking off
66%
Trannies in Space
There was no spaceport on Jansen's Planet. There had been, but whatever calamity had befallen the world generations ago had also destroyed its port. It was one of so many planets out in the Barrens that had fallen on hard times. So Dekker set down the Barnabas in a clearing in the forest, a remna... Read full Story
ASSEaster5678 2019-01-25 11,838 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
80%
Vicky Part 1
"Dear Sir, We recognize you as a person of discerning taste. We would therefore would like to invite you to a display we believe you would find most enjoyable." What followed was an address and a date, one week away. My name and address were correct, but I didn't have a clue what they w... Read full Story
shemale lover 2011-11-14 4,392 sucking cum fingering
100%
Birth of a New Sissy Part 3 Completion
I suppose at some level I knew it would happen. Or at least I should have. After nearly a month of servicing Jeff's cock and fucking myself silly on my dildo lover things took a turn. I came home from work a little early on a day Laura was off as well. When I got home she was out, but as soon ... Read full Story
shemale lover 2011-11-17 4,964 cum domination crossdressing
100%
Bookstore Bound
My Master, ever the gentleman, held the car door open for me. I smiled at him as I turned to get out of the car. I made sure to spread my legs in a very unladylike manner, giving him a good peek up my short dress. He simply shook his head and took my arm. We made our way over to the entrance to the ... Read full Story
shemale lover 2012-08-02 5,198 cum oral sex cum swallowing face fucking
76%
She didn't see it coming
I had seen her at a stop light while driving around looking for a spot to eat. She drove a red Pontiac Sunfire, the convertible kind that no self-respecting man would be caught dead in. She was gorgeous, at least from what I saw from my elevated platform of the SUV I was driving. She was petite, ... Read full Story
shemale lover 2013-07-17 4,955 hardcore oral sex big boobs kissing shemale sex
88%
Purple Kiss, part 1
It happened during a week long trip for work. By the third night in a strange city I had grown tired of the hotel bar and broke away from my work colleagues for change of scenery. I told my coworkers that I was going to bed then quickly made my escape. The night was warm so I decided to take my o... Read full Story
Transadmirer 2016-01-02 9,862 Creampie Shemale Fucks Guy Fetish cum domination gangbang sex
46%
My first time and loved it
My name is jay i have been attracted to shemales for a very long time i have always fantasizec of being with one but never happened.i dont know where to go to meet them and im real shy and quiet at first it sort of sucks trying to take to a beautiful woman never know what to say.so i decided to join... Read full Story
Hbjay 2012-08-14 3,840 first time anal sex shemale
64%
She Male 3gp Option On The Lost Phone Gave Me A Threesome
I was in the park just walking around and trying to clear my mind. I was stressed out last few days and I needed something that will relax me. I set on the bench and started thinking about my problems. Two girls passed right next to me and one of them was looking for something in her purse. When ... Read full Story
shemale lover 2016-02-10 5,428 asshole sucking cum swallowing
67%
Librarian with a Cock
I would go to the library on Tuesday's mainly because I was attracted to the librarian. I never really slept with women but for some reason she really turned me on. I guess it was her age, but I love older men and women (sometimes.) A few weeks ago I struck up a conversation and found out her name w... Read full Story
shemale lover 2015-01-21 7,880 ass suck Big Cock
88%
Steamy date with a TS
Last year I had a great experience with a TS escort and I saw she was in town again, I texted her to meet for dinner and to my surprise she agreed. I met her at the restaurant and we had a nice time together, she´s very friendly and incredibly attractive. She wore a red summer dress with high hee... Read full Story
Gracemel121 2018-08-27 9,624 Amateur Shemale Fucks Guy domination Ass to Mouth
88%
My very first experience with my classmate
He was amused by the sight...of me in lingerie..standing on the porch,it was obvious he was in a shock (or state of extacy?) and couldn't take his sparkling blue eyes off my firm body inside the dress...he closed the door behind,like he was worrying if someone could see us ..I don't know why but i f... Read full Story
shemale lover 2012-10-01 3,812 anal first time Creampie
90%
Wedding Night
Animated conversation, lots of affection and laughter – he was chatting to some of the guests at the reception, just waiting for her to get changed before they left their party. He stood to move to another table and as he turned he saw her walk in the door...tall, elegant, beautiful, curvy...a... Read full Story
shemale lover 2014-03-05 6,723 sucking cum ample breasts
96%
My First Time
Hello, I've read a few stories on here some good most bad. I figured I would throw my own experience into the mix and try to bring something fresh to the table. I feel like you can tell most of these are fake, so here is a TRUE story about my first time with a trans girl. Bac... Read full Story
CiCi Kewt 2015-11-25 10,151 first time tranny ass ass fucking teasing teen TS (18+)
100%
2 Girls Out for a Night on the Town
Some of my best friends are transvestites. I met them at a nightclub in L.A. It was pretty famous back in the day. They had a drag and dinner show. Some very talented people worked there. Some actually lived their lives as women, but a lot didn't. I used to hang around with Daniel. He was a very ... Read full Story
shemale lover 2011-08-14 2,555 Blowjob cumming cum swallowing
88%
He or she? It did not matter to me!
I was sitting in my small apartment watching TV and having a few pipes when I heard a ruckus in the hallway. It was my room mate Joel and some of his friends retuning from the pub. When they knocked on the door I answered and there he was with some girls he knew but who were all strangers to me. As ... Read full Story
shemale lover 2012-10-24 2,609 sucking shemale kissing
50%
a diary piece - my next date
A diary piece - my next date I hadn't forgotten how to please a man and I had decided to be a little whore for him. Yes I enjoyed it very much and wanted to be fucked again the next day. When I start having sex I want it all the time. HiltonP had said he wanted a date again on 21st and 28th ... Read full Story
amberdoll 2020-09-16 2,457 Stockings Small Tits Crossdresser Amateur Bareback blonde Lingerie Homemade
66%
My Shemale Cams Extravaganza With The Boys
It was a beautiful late night and I decided to take a stroll home after work. Home was literally about 10 minutes away and I loved the feeling of the late night breeze in my hair. The day was long and daunting. All I could think about was the shemale cams videos I viewed while at work. While most... Read full Story
shemale lover 2011-08-11 2,760 anal sex Creampie shemale
81%
1st sexual experience with shemale
For a long time me and my girlfriend had fantasized about a threesome with a shemale. We even brought in her didlo for fun one time and i found myself very excited by it. After that, thats all i thought and fantasized about. Soon it was to a point that I wanted to experience a sheamale alone. My ... Read full Story
shemale lover 2012-04-01 2,700 fingering oral sex cum swallowing 69 position
100%
First sexual experience with shemale
For a long time me and my girlfriend had fantasized about a threesome with a shemale. We even brought in her didlo for fun one time and i found myself very excited by it. After that, thats all i thought and fantasized about. Soon it was to a point that I wanted to experience a sheamale alone. My ... Read full Story
shemale lover 2012-04-09 3,889 first time big dick oral sex cum swallowing 69 position
93%
My lesbian shemale adventure
My name's Kimmi and I used to be a stripper. I'm a genetic girl, and I always had a wild streak. Guys liked me 'cause of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts. I danced at a place on Sunset Blvd in Hollywood (this is a true story, so I won't use the... Read full Story
shemale lover 2013-07-20 3,706 Cumshot Shemale and Girl big boobs handjob kissing
75%
Amanda at Transcend in Sydney
I just love the tgirls in Australia, at least the ones I know, they are all unique in their own way and very very sexy... Amanda at Transcend is one of my favourites...this is a story about a visit with Amanda last year... I had not seen her in a while but as I was in Sydney for work I decided to pa... Read full Story
xanykeyx 2015-08-19 7,822 sucking fucking tgirl
100%
Seven Minutes in Heaven
This is purely a work of fiction about two 18/19 year olds... It is the summer before our first year of college and we are home alone at his house. My mom works from home, but his place will be empty until his sister gets home from her summer internship. We have been playing truth or dare since... Read full Story
shemale lover 2011-09-20 2,905 first time shemales taboo
92%
The clerk needed a ride
It was a Friday night, and was out with some friends heading to the bars when we stopped at a convenience store for some snacks, and condoms etc. This was my second year of college and these guys had turned into friends that I hung out with almost every weekend. This night I noticed this stunning cl... Read full Story
shemale lover 2011-11-28 2,714 anal shemales taboo
100%
Falling For My Roommate Chapter 2
Naturally, the thing I dreaded the most was the end of the semester, when the two of us would eventually go home and not see each other for a solid month. Thanksgiving break wouldn't be so bad, since that's only a week, but nonetheless it weighed on my mind as the weeks went by. About a week before ... Read full Story
shemale lover 2012-05-23 2,289 fingering facial oral sex
88%
Crossdressing with my moms friend
Mom opened my bedroom door. she stood there in the doorway and stared at me obviously repulsed. after 10 or so seconds she closed the door and walked away. i was mortified. i was kneeling on my bed, with her clothing catalogue open at the lingerie section laying on the bed before me, hard cock in h... Read full Story
shemale lover 2012-06-12 11,419 Stockings Fetish cum crossdressing
87%
My first time
Ok so it was my first time with a crossdresser She picked me up we drove back to hers I was so nerves but excited. We sat down for a smoke and she asked are you never a I said yes so we started kissing and you pulled my dick out I reached down and felt her warm " clit " as she called an... Read full Story
Bigdickmitch12345 2015-05-27 4,860 first time tranny cum cd piss
60%
A Raging Inferno In Phoenix
Relaxing house style music played in the background as I prepared dinner. I wasn't a world renowned chef, but I did know my way around a kitchen. Currently, I had the penne pasta boiling, the chocolate cake baking, the freshly made salad mixed, the white wine chilling, and the well-seasoned marinara... Read full Story
ASSEaster5678 2018-07-10 5,182 Amateur Ladyboy
80%
TG Girlfriend moves in (part 2)
My wife Lydia and I have been married about 9 months, we have a very close TG friend, Joanne, that lives next door and every once in a while, we get together, and all go out and enjoy. We have had sex together, and when Lydia is away Joanne, and I are together at every opportunity. Joanne and I work... Read full Story
Jon Paul 2022-01-21 3,264 Big Tits Cumshot Bareback Creampie threesome Blowjob Shemale and Girl Guy Fucks Shemale
93%
Ann Part 2
The next work day, that evening as I walk up to my townhouse, Ann is sitting on the porch and tells me, “Since you didn’t call I thought I’d come by, I was in the area anyway.” Even though I’d been with her the night before, I have to laugh and Ann asks, “So wh... Read full Story
shemale lover 2014-10-31 4,646 licking sucking swallowing
66%
Electric Shock
I'm glad you enjoyed my story. I have been dressing for many years, and it's only lately that I thought I'd share some of my experiences with other cd's I am NOT convincing; all the stories in Nifty seem to be by gorgeous she-males who cannot be distinguished from the real thing. Much as I woul... Read full Story
shemale lover 2011-08-26 2,499 shemales anal sex Big Tits
60%
Quick Fix
My anticipation couldn't be expressed in words. It had been a while since I'd had a visitor to my apartment. The last experience had ended quite well, with the bed sheets being more than a little tussled up. I was preparing myself with an erotic movie. The sex scenes always turned me on, my fu... Read full Story
shemale lover 2011-08-31 2,304 asshole cum oral
83%
With an 'E' Chapter 2
Waking the following morning, feeling somehow fulfilled. Then, as I came to, I remembered the night. With my frilly shortie nightie disgustingly clinging to my body, back and front, came the realization "I was no longer a virgin!" And -- it felt great. Sometime in the night, Bobbey had ... Read full Story
shemale lover 2012-10-10 2,338 sucking Creampie kissing
72%
Mistress Carol transforms me into a cum slut
I sat on my car and put on my heels, smoothed down my mini skirt and checked my hair growing out nicely and currently in a blonde bob. I was breathing fast and felt my small, c size, breasts move up and down. My nipples were erect and sensitive the piercings quivered slightly in my halter top. Decid... Read full Story
shemale lover 2013-05-17 15,426 Stockings Cumshot dildo fingering domination swallowing
95%
Best session with a T Girl
I like T-Girls. Recently had a chance to go to Costa Rica for work. While I was there I decided to see what Costa Rica had to offer in this department. There is quite a good amount of girls to select from. I started texting this Tgirl and we set a time. I got ready and headed over. It was a Hotel th... Read full Story
horny.hiker 2019-04-30 14,546 Stockings Masturbation Creampie Shemale Fucks Guy Lingerie rimming Ass to Mouth escort ts no lube anal fuck just saliva
33%
Black Book Diary Entry: Barbara
I met Barbara Online on one of those dating sites, Cupid or something. I was drawn to her by her correspondence. She was one of the few women who was skilled enough with the English language to keep me interested and it always excited me when I saw I had an e-mail from her. I had no idea what she... Read full Story
shemale lover 2012-06-25 2,724 transsexual post-op
71%
Xdressing school fucked by black teacher
This is a kinky sexual fantasy about my university teacher .Well it all started the first day my new teacher walked in the door .Six foot, very good looking black man .He was 15 years older than me very smooth with the girls.I just turned 21 and am three years into my transformation from male to fem... Read full Story
shemale lover 2012-08-16 4,048 anal sex cum swallowing black cock teacher
50%
First Night Out
Okay. Last night was weird. It was Halloween night at Spiders, as you all know. And those that went also know that I went with Shel, in a dress… First she waxed me, around dinnertime, and that stung like hell. But I should be hairless for a while. Then she chose the clothes for me. I chose... Read full Story
shemale lover 2012-09-26 2,677 cum Sex Toys condom sex