Sort by
Relevancy

Free Stories

96%
First Time
At this point in my life I have been dressing as a girl on and off for about 5 years. It wasn't just dressing I was into however, I have been fantasizing about a man using me as I tried to present myself. I was a virgin at 18 both with girls and with men, eventually the urge to change this was ... Read full Story
Kels725 2015-05-01 6,517 anal Crossdresser Cumshot suck oral sex
100%
Born to suck
I’m a straight guy who watches to much porn and when I hit my thirty’s regular porn was getting boring. while searching the web I stumbled across some tranny porn, now I always loved blowjob porn it was my favourite but now watching a big dicked tranny getting her cock sucked is my favourite and I ... Read full Story
Beesknees 2018-03-02 6,452 Blowjob blowing
100%
My Afternoon With Venus - Part I
It was a stunningly bright and clear Saturday morning when I left my house to head out and run some errands. Nothing big, just little odds-and-ends that had been building up that I needed to deal with someday and it seemed like this was as good a day as any ... little did I know how good the day wou... Read full Story
funpics 2018-03-23 13,122 Amateur Shemale Fucks Guy Asian Guy Fucks Shemale Homemade
100%
The Day I Went SheCock Crazy
I summed up courage to meet up with my old shemale flame Fransicca (she is a Malaysian but living in indonesia) ... messaged her, she sounded excited and asked if i minded her friend joining us. 'Why not' i said. It was settled. we booked a villa for the next day. I checked in early. cleaned up ... Read full Story
Sara Banks 2021-04-26 6,577 Group Sex Cumshot Outdoor Bareback Shemale Fucks Guy Fetish Blowjob blonde Big Cock Asian Ladyboy gangbang
100%
My first TS girlfriend
This story took place back in 2014 around November when Craigslist was still there, I was looking for a Ts , then found out Diana she had the middle-east style, black hair , beautiful young face with light makeup on , didn't live far away where I used to live, we communicated went to see her In fro... Read full Story
Tslover8814 2021-11-02 5,820 shemale
100%
Casino Girl
I had been working as a casino dealer for several years and would occasionally meet some very attractive women and chat. Asian women have always been attractive to me, whether the exotic appearance or maybe because my Mom was Pacific Islander, and a lot of people thought I was Asian. Mia was a bit... Read full Story
Jon Paul 2022-01-03 2,921 Stockings Cumshot Bareback Blowjob Asian Ladyboy Guy Fucks Shemale
100%
Santa Likes Shemales Femboys
Did you know Santa Clause is real....and he likes shemales femboys??!I It happened last Christmas Eve. I fell asleep watching the snow fall just outside my window. I was comfy under my layers of warm blankets I clutched tightly, in the black lace panties and red lingerie night dress or nighty I wear... Read full Story
Chrissy Tunnell 2022-12-01 3,644 Small Tits Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
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 6,709 tranny asshole Blowjob
94%
Shock and Awe
My name is Frank and I’m a decent looking Irishman in my mid 40’s. Every now and then my work takes me to London for a few days and I like to let my hair down if I can. I try and find a hotel in the Earls Court area so if the mood takes me I can visit one of the many hookers that has apa... Read full Story
shemale lover 2014-05-15 6,402 shemale caressing
82%
Tranny Gas Station Attendant
This happened about ten years ago and I thought I'd share it with you all for your enjoyment and mine! Like I've said before, although I'm bi-sexual, I don't walk around checking out other guys, nor do I like to be intimate with one. Sure, some might consider taking a cock in the mouth or ass intima... Read full Story
shemale lover 2014-06-29 7,844 Stockings shemale cumming
78%
Wild halloween night
First sorry everyone it’s been a several month since I been here was busy with my life. Anyway Halloween comes once a year and we all wear custom and I know personally lots of guys like to wear female custom. I am cross-dress and love Halloween, this Halloween was wild first ever wild Hallow... Read full Story
shemale lover 2014-09-21 5,082 shemales sucking interracial sex
96%
A slave for three beautiful shemales
Here's another great story that was submitted by one of our readers. Enjoy reading. I used to be a bouncer at a night club and one day after my shift a very foxy black busty babe approached me just outside the club. She was wearing hot pink track pants and itty bitty tube top that was some how ho... Read full Story
shemale lover 2015-05-25 7,656 anal cum dildo
93%
The Hot Girl at the Bar
My girlfriend and I broke up the week before, so I was pretty depressed. The guys at work decided to take me out to the bar after work to get wasted cause that’s what we do. So we all packed into the truck and headed to the bar. When we got there we were the first ones in that night so we sa... Read full Story
shemale lover 2015-10-01 10,350 anal suck Creampie
97%
The Best of Both Worlds
“Promise not to fall in love while you’re away?” Lana asked as she wrapped her arms around me. “I’ve told you several times already,” I snapped at her. I had begun to get more than frustrated with her. “This is just a business trip and nothing more, besid... Read full Story
shemale lover 2015-10-11 8,542 Cumshot shemale oral
50%
Out of Town Meeting
Dinner was seamless, the food, the music, the wine, the company. Tony’s out of town business meetings were usually painful, in that he hated living out of a suitcase and eating alone in overpriced restaurants. This trip, he was enjoying every second of it. He’d met up with Chantal, a wom... Read full Story
shemale lover 2011-08-14 3,568 shemales hardcore bdsm
100%
Amy Finally Lives Out Her Fantasies Part 3
Amazing the things one finds when on their significant other's computer. Benjamin -- or should I call you "Kyle"? -- you really should be more careful with hidden files, cookies and predictable passwords. You, along with anyone who reads this story (including you Dave), are reading t... Read full Story
shemale lover 2011-09-15 2,550 asshole orgasm ass fucking
50%
Clinton
"How many inches?" she asked. "Twelve," he said. "Really?" "Really." "If you're lying, you're just wasting your time." And mine, she thought. "I'm not." "Okay, then. It's a date." Tiffany hoped the jerk was te... Read full Story
shemale lover 2011-09-19 10,682 Big Cock cunt anus
100%
Helping a Friend Part 2
I had seen Anna at work for the past two weeks…not a word of what happened at her house, when I fixed her sink. What a great night that was……………the night I found out she was a shemale! I fantasized about Anna all the time, yet nothing from her. It was our s... Read full Story
shemale lover 2011-10-02 2,130 anal shemales gay male
100%
Pay the Genie Part 2
Scott leaned back on his couch and enjoyed the magical efforts of his new best friend, Ura the ebon genie goddess. His jaw ached slightly from paying for the oral loving he was then receiving, but as always it was worth it. It had been a few days since he found the magical pocketwatch that contained... Read full Story
shemale lover 2011-10-12 3,669 asshole shemale oral sex
83%
Mall She-Curiousity
I was ushered into the security office where I was greeted by a tall, dark-haired woman. She was dressed in a violet silk blouse with the top two buttons undone. I could see the tops of what looked like very nice breasts. She also had on a short, black skirt with a slit on the side, dark pantyhose, ... Read full Story
shemale lover 2011-10-15 3,440 Big Cock transsexual oral sex pantyhose
72%
She fucked me so hard...
I was 22 at the time and really horny! I hadn't cum for a whole week... and I was saving it for something special. I was desperate to meet with a Crossdresser, was watching porn videos of big cocks deepthroating and anal fucking, but my favourites were Big cock shemales. Nothing would turn me on mor... Read full Story
shemale lover 2011-10-16 7,388 first time cum oral sex
75%
Encyclopedia Erotica By The Fan
It was a normal-looking enough place. A small town in California. Looking at it, no one would ever guess it sat on the hellmouth. The Mouth of Hell. A portal to a multitude of dimensions filled with horrors and wonders. Many things came to the Hellmouth, drawn by its power. Vampires. Demons. Mon... Read full Story
shemale lover 2011-10-19 4,410 asshole orgy Sex Toys
50%
The Chronicles of Drodge Mallea
Drodge awoke feeling fuzzy headed and stiff. Actually, "awoke" wasn't quite right -- "came to was more like it. She sat up in the lavishly furnished boudoir, stretching her athletic 6-foot frame as she did. Running a hand though her short, thick copper locks, she slipped out of the... Read full Story
shemale lover 2011-10-24 3,027 Cumshot shemale Big Cock
85%
The New Hire
Norman Bancroft wasn't exactly crazy about the job. For one thing, the pay sucked, and there was zero chance for promotions. In addition, fairly long periods of boredom were relieved-if one could call driving several hundred miles per day for several days in a row relief-by trips from one of the rai... Read full Story
shemale lover 2011-10-27 4,322 anal hardcore oral
100%
Sweet Sherri
"The fuck you want," the girl hissed through her teeth. Well, it's hard to say. For one, this was the one night of the week at the particular club that was tranny night. Unless the lucky woman was either a straight freak or had been exposed to the scene, there weren't too many people wa... Read full Story
shemale lover 2011-10-31 5,550 Big Tits transsexual big ass
100%
Old Man’s Folly
I was in the City to speak at a class on Business. I am in my 70′s but still very active and love to travel. I lost my wife of 51 years two years ago after a long and wonderful marriage. We had a very active life, extremely active in the sexual area. So with nothing else to do I make appearanc... Read full Story
shemale lover 2011-11-11 3,519 shemale oral nipples
100%
Don't Go Into The Woods Part 3 The Arrival
Holding the door open for the men I thought this must be the big fat old beer belly man convention. I had learned before to only address them as Sir. Dick had both trained and spanked “thank you Sir,” into me many times over the past months. My pink lipstick smiling lips uttered &ldqu... Read full Story
shemale lover 2011-11-12 3,455 asshole orgasm spanking
75%
Experimenting with Cock
I was 22 and at the time did not have a girlfriend. I had a habit of jerking off at least once a day if not more. Starting masturbation at an early age made me bored by "normal" porn star videos. Leading me to amateur porn. Soon that became boring and I was experimenting with everything. O... Read full Story
shemale lover 2011-12-01 4,795 gay male oral
33%
Growing up CD
Peter, Max and I played together like that for the rest of the weekend. We must have sucked each other's cocks at least 10 times over the three days. Peter and I were both physically drained. Max just seemed to be insatiable for our bodies. He didn't want us to go. He kept on saying how much he ... Read full Story
shemale lover 2011-12-04 4,202 sucking Fetish
66%
Candy Pink Part 2
Chapter 4 My parents had a letter shortly after from the headmaster Mr. James Allen. I was to head out to CA before the start of winter term to get settled into the dorms and go through orientation. The letter said I should be there no later than December 1st and that they would arrange for me to... Read full Story
shemale lover 2011-12-08 4,435 taboo Fetish crossdressing
50%
Chinese Extremes Part 6
If Lien had expected that life as one of Master's special slaves would be easier she was sadly mistaken. As one his chosen few she was expected to perform much, much better to all other slaves. This meant a much harder schedule than all the others had. When Lien had been a house-slave she had never ... Read full Story
shemale lover 2012-01-17 4,390 torture extreme bondage and discipline
50%
The Visit
A visit to a hooker, where I describe my bisexual experiences *** It was a weekday, I had bummed off work and had made my way to Ipswich for a visit to Rona, my favorite hooker. She was a lovely woman in her forties, with a fantastic figure, not slim but not fat and with huge tits. She... Read full Story
shemale lover 2012-01-26 8,311 Group Sex licking sucking pissing fucking
100%
TS Prostitute Urge
After college I began to explore the world. To that point I was the average male that happened to get a lot of tail. My sexual exploits with women were something I was proud of and always gave me a sense of being a real man. After years of watching straight porn and imagining myself in every possibl... Read full Story
shemale lover 2012-01-27 3,581 Group Sex sucking cum
94%
Flying High
The plane landed as scheduled. Luckily it had been a very smooth flight. I made my way through the busy airport. While I was waiting for my luggage my eyes went everywhere looking for beautiful girls. I saw my luggage come around and went for it. At the same time a voluptuous brunette reached for th... Read full Story
shemale lover 2012-02-06 4,197 anal sex Shemale Fucks Guy cum
90%
Roxy
I’ve been the president of my goys school PTA for the last two years and really enjoy doing it, so when the national conference came around, I went with my husband’s blessings. It was a four day conference in Atlanta, Georgia and as I had no one to room with, I was assigned a roommate. I... Read full Story
shemale lover 2012-04-10 4,915 Big Cock orgasm fingering oral sex
100%
Enchantment of the Shadow Realm
It was a enchanting night. The moon was full. The street light reveled an other worldly stream of fog through what I could see of the dark forest. Unfortunately I was having a hard time appreciating all this beauty. I was stranded. I had missed the bus and had no way of getting back to my hotel. I h... Read full Story
shemale lover 2012-04-14 3,992 Group Sex Cumshot Big Cock facefucking
100%
The Club
Pretty soon everyone was naked and in their places and ready to go. "Okay ladies, I'd like you to meet tonight's very special guest, may I present to you, Susi!!!" Missy swung open the door to the adjoining room, and much to the stunned delight of everyone there an incredibly beautiful Asi... Read full Story
shemale lover 2012-05-01 3,947 Group Sex shemale orgasm fingering Sex Toys
58%
My real story
I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him. It had all started two weeks earlier when I had posted an ad on Craigslist. Up until this particular posting I had always been pretty bland..."Willi... Read full Story
shemale lover 2012-06-10 6,307 hardcore Cumshot bdsm oral sex
83%
Surprise pick up
This is how I lost my virgin ass. I got off work one day and on the way home I figure I'll stop by the adult book store to try see some peak show. The place was unusually packed. I usually go there an play with my dick. So the place packed so I leave when I leave I notice two girls walk in acr... Read full Story
shemale lover 2012-07-02 4,671 anal sex Creampie shemale jerking oral sex
100%
Blushing Bride Chapter 4
Chapter Four: The Hen Party I've already told you all about the night a couple of days before my wedding, the night of my stag party, the night where I got to live out all my fantasies and play the blushing bride, dressing in my soon to be wife Gina's gorgeous white wedding dress and lingerie and... Read full Story
shemale lover 2012-07-21 3,925 big dick shemale oral sex crossdressing
100%
Fender Bender
It was the first week of June and school was out for the summer, I was 18 and had just finished my Senior year. One night while we were eating dinner, My Mom and Step dad informed me that they were going away for a week. When they got married they did not go on a honeymoon so they wanted to take one... Read full Story
shemale lover 2012-07-26 8,383 Teen (18+) Fetish crossdressing
100%
Quickie at the Mall Food Court
I was in the food court at the mall just a few blocks from my office. The mall wasn't doing very well since a new, bigger mall and a series of big box stores had been opened at the next exit, and half the stores were closed. The food court itself had lost two more restaurants, and there was a pretty... Read full Story
shemale lover 2012-09-04 4,412 Cumshot Masturbation Big Cock Guy Fucks Shemale condom sex
50%
Alabama Nan in Atlanta: Round 1
It had been three years since I had last seen my family for the holidays. I don't go see them often because none of them understand, except for my older sister Karen. This year I got brave again and decided to go. Knowing how much coming home bothered me, Karen was coming up to Atlanta from Mobile t... Read full Story
shemale lover 2012-09-20 2,686 Cumshot sucking fingering
66%
Alabama Nan: BBW Time
I wanted Betty to know what true pleasure was. To know that "big" girls like us deserve to enjoy another person sexually. She gingerly followed me into my apartment as I turned on the lights. I knew Betty had no idea what was about to happen, but even though I kept telling her I wasn't you... Read full Story
shemale lover 2012-09-20 3,633 shemale cum fingering oral sex
75%
Meeting Grey DeLisle
It had been many months since I had interviewed and then fucked voice actress Tara Strong, and jipping into her panties wasn't as satisfactory as it used to be. Then I found out that there was convention happening in the next town, so I headed down one day. Free entry. While I was there, I enj... Read full Story
shemale lover 2012-09-27 2,543 sucking celebrities cum
83%
Discovering Amber
I have always enjoyed women's lingerie. From looking at catalogs to seeing girlfriends wearing it I have loved the look and feel of sexy, silky lingerie but for me it has always gone deeper. At 18 I tried on my first set of panties, oh my God that was wonderful! It was all downhill from there. Event... Read full Story
shemale lover 2012-09-28 6,186 Cumshot Fetish Lingerie oral sex
100%
Flight of Fancy
Boarding the plane I take my seat and cannot help noticing the beautiful young woman sitting next to me. She introduces herself as Mary Jane and I take her hand in mine feeling the warmth and softness of her skin. We chat and get to know each other as the plane takes off for the overnight flight. So... Read full Story
shemale lover 2012-11-10 3,081 Cumshot shemale oral sex wanking
100%
Angel Chapter 3
On Monday morning, Angel Jones reported for her first day of work at the main office of the big London Bank. As she sat on a chair in the anteroom of the personnel office, she thought about what she would be doing there. It was almost a certainty that nobody in the bank knew she was a T-girl, becaus... Read full Story
shemale lover 2012-12-01 4,882 Cumshot sucking jerking
90%
The Perfect Choice
Andrew had moved in with Hannah a few short months ago and so far everything was going just the way she wanted. She was an endless tease; wearing short skirts and dresses when they were out during the day or tiny shorts and vest tops when they were at home together. She did everything she could to t... Read full Story
shemale lover 2013-01-10 6,522 hardcore Shemale Fucks Guy Blowjob ass fucking domination
100%
Boi Toy
They met me off the train late in the afternoon. Their welcome was warm and friendly. I was exhausted from travelling and spent the evening in wonder as we first had drinks with friends of theirs at one home then all went out to eat at a restaurant, then back to another friends home for more drinks.... Read full Story
shemale lover 2013-01-29 5,993 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
French Frolic
Where to begin? It is never easy to know where to start with a confession. The easiest place to start is at La Rue - a tiny little dive of a club just a couple of blocks from my hotel in Paris. I had only been in Paris a couple of hours. I was extremely jet lagged but only had a few days to make the... Read full Story
shemale lover 2013-02-21 5,677 Cumshot sucking Blowjob facial domination
100%
A "Girl" for Kelly
Kelly was sort of a loner throughout her life. She had very few friends throughout high school and college, and if she weren't around them, she would spend her time alone. Her love life was just the same. She did have a few boyfriends, and only ever managed to get one to have sex with her. It wasn't... Read full Story
shemale lover 2013-03-27 3,837 hardcore sucking Big Cock Shemale and Girl big boobs
100%
CD And Trucker
At least four things went through my mind the moment I heard Hank ask me to go along with him. - One my wife was gone for at least 2 weeks so that was no problem. - Two, with wireless connection and my laptop I could take my job on the road. - Three, I had hardly any clothes in my bag that I was ... Read full Story
shemale lover 2013-04-30 9,596 Cumshot fingering domination spanking cd
100%
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 2013-07-20 3,591 Cumshot oral sex swallowing kissing shemale sex
100%
First Time Sex With Tranny
Wow - if you have ever wondered what it would be like to be with a TS girl, this would be a great place to start. Just got this from a “friend” of mine who wanted to write about his first TSgirl experience. Can’t say for sure if it’s 100% true, but who cares? I do know that they were together so ... Read full Story
sach 2015-11-16 7,840 first time tranny suck stroking mutual sex
77%
Sweet Tranny Face sitting heaven
My stories are my experiences and memories I like to look back at from time to time.I have had some real to honest God sent blind tranny dates giving me some of my best and happiest moments in my life. As I recall this one time coming across this beautiful nubian goddesses personal ad on Craigs... Read full Story
Ur Papi Chulo 2016-01-22 5,290 shemale ass fucking stroking ts facesitting