Sort by
Relevancy

Free Stories

100%
A night to remember
Josie wasn't a girl a man would turn his head for if he saw her on the streets. She was a small, petite girl, her breasts barely an B cup. She was wearing her light brown hair in an inconspicuous short cut and the thick glasses she needed for being able to see anything in her surrounding, didn'... Read full Story
shemale lover 2011-12-11 5,437 first time tg
85%
The Greatest Lie Part 14
For me, my hometown, L.A., is not the sexy, sweaty night clubs of West Hollywood nor the porn scene of the North Valley. Though I feel more at home there, that side of L.A. is not my home but rather the world into which my transsexual destiny exiled me. Home is the leafy, moneyed boulevards and s... Read full Story
shemale lover 2012-01-20 6,263 cum transsexual fantastic
80%
First Time With a Teacher
Jake an average senior boy got C's in most of his classes but he was failing his Creative Writing class. One day he came into class about 10 minutes late and when the teacher, Ms. Wess, asked him why he was late he responded with 'Sorry Ms. Wess, my mom was being a bitch and made me clean the dishes... Read full Story
shemale lover 2012-01-27 3,944 sucking Creampie cum fucking
100%
Shemale Seduction - The Surrender
I cannot remember what drove me to it. Cruising bars for sex had become a habit. Success can do that to you, but even steady success make you yearn for something different. I looked at her from across the bar and acknowledged her stare. She definitely looked hot and hungry, with eyes that seemed to ... Read full Story
shemale lover 2012-02-03 4,964 anal cum fingering
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 3,187 anal sex cum jerking off
100%
Carla Chapter 4
After the shower I staggered to my feet and went into the bedroom and lay down. Carla walked in and kissed me heavily on the lips. "I'm sorry baby, but I need to go to work." I was disappointed. I nervously asked if we could meet again and she laughed, "I am so into you, of c... Read full Story
shemale lover 2012-03-07 3,600 anal sex sucking cum fingering
50%
A Harmless Fantasy?
I lie in bed at night, trying to get to sleep, but my mind wanders. I think of all sorts of things, and eventually my mind heads off into a land of fantasy. In fact, it is one fantasy in particular, and it's one that I have been having ever more frequently over the last couple of years. Each time it... Read full Story
shemale lover 2012-03-09 3,281 Blowjob cum fantasy sissy
100%
A Neighborly Gesture
I spun about in front of the full-length mirror, happily admiring my "new look." An entire week with my wife out of town, I mused happily. This morning's inspection of her lingerie drawers had yielded a treasure trove of dainty feminine items. Fortunately she's a big enough for me to get i... Read full Story
shemale lover 2012-03-29 4,311 Fetish Lingerie crossdressing
81%
A New Beginning
It's not easy to accept the fact that I ruined my own marriage. A lot of guys ruin their marriage by cheating on their wives with some piece of ass that wasn't worth it in the first place. Not me, I ruined it by becoming one of those pieces of ass. From my earliest memories I knew I was supposed ... Read full Story
shemale lover 2012-03-29 3,675 fingering Sex Toys mouth fuck
75%
Amy & Hope
My name is Amy but my real name Anthony and I turned 21 and started my first step on becoming a woman I decided to get some breasts for my birthday since I'm becoming a woman so after the surgery I felt more like a woman I was 5'9 weight120 and had long brown hair and some perfect size tits they was... Read full Story
shemale lover 2012-04-25 3,649 Big Tits cum transformation oral sex vaginal sex
100%
The Boy is A Girl Now
When I turned 16, I decided to go to a gay bar to see what the deal was. I had not been with anyone ever but I was curious and very much feminine. I stole my older brothers ID and caught the Bus to go to the Ballgame, so I told my mom. Then I wound up at the gay bar just as they opened that night at... Read full Story
shemale lover 2012-05-09 3,903 anal Group Sex sucking rimjob
100%
Surprise!
Here I was, on a Sunday night, going in the club to have some fun. After few hours of dancing and drinking, one pretty girl came and asked me to dance with her. Looking at her I saw that she`s not a "grenade" so I was thinking maybe I will have some fun tonight so we started dancing. Afte... Read full Story
shemale lover 2012-06-27 4,282 first time Cumshot Blowjob shemale tiny cock
100%
My TV Sex Adventures Blow Job Slut
“Suck me you fucking whore!” The guy saying that was filling my mouth with his hot nine inches of thick Latino lusciousness. I met the guy whose name still escaped me only minutes earlier in a drag bar in a southwest city. He had been nice enough and he was good looking and fit. More im... Read full Story
shemale lover 2012-07-06 2,538 Stockings Cumshot Blowjob
87%
David Invites JoJo Over
Although I fucked Del that night, for the first time in our marriage I was thinking of someone else. I just couldn't erase the image of our sexy neighbor lying bound and helpless on our bed wearing the very same peignoir set that Del wore when I took her virginity on our wedding night. As I lie awak... Read full Story
shemale lover 2012-07-27 3,652 Cumshot Lingerie oral sex
100%
The Only One
After talking to her online for several hours she invited me over to her house. I got dressed, jump in the car and drove over. I must have been overly excited because my cock was raging hard the entire drive over there. The house was gorgeous, and huge. I thought to myself that this house had to ha... Read full Story
okctshunter 2012-08-18 6,211 Bareback threesome Big Cock
100%
After Gym Class Chapter 3
Sara jumped out of bed, and stood at the side of it, looking down at me. I lay back, still enjoying the afterglow. With my fingers, I absently rubbed circles of her silky cum where it had landed on my breasts and belly, enjoying the feel of it on my skin. I glanced up at her, and we both smiled. She... Read full Story
shemale lover 2012-08-23 4,481 Cumshot blonde jerking off small cock
100%
Porshe's Escapade Chapter 1
Hi, it's Porsche back again and rather disappointed. I thought I would get a much better response to my first story "Interactive Crossdresser...Dare Me" but i didn't. I was kind of reluctant to put myself out there since i have never dressed in public or in front of anyone else but my Aust... Read full Story
shemale lover 2012-09-03 2,075 Cumshot Blowjob Big Cock cum swallowing
100%
Roberta, Molly and Ed
Friday "Commander Cromartie?" Lt. Commander Edward Cromartie, USN, turned toward the voice that had spoken his name. He saw two female naval officers, a tall willowy light-skin Black woman, and a short Asian one. The Black one was wearing the uniform of a full commander, the Asian of... Read full Story
shemale lover 2012-09-04 5,626 Cumshot threesome Blowjob Big Cock condom sex
100%
Porshe's Escapade Chapter 3
Hi all it's Porsche finally back and able to tell you about another escapade. My male half has been so busy lately with work and vacation etc. that Porsche just hasn't had time to play. So for my first free day in a long time I decided to be Porsche all day long. I got out of bed and droppe... Read full Story
shemale lover 2012-09-05 3,307 Crossdresser Blowjob Sex Toys double penetration
100%
Olivia and Katie
After our first meeting me and Olivia became fast friends. We would go shopping, do lunch, check out a movie, pretty much the stuff that girlfriends do. It was lots of fun and most of the time we did these activities dressed up all cute or sexy. Well there was one thing that has eluded me and Olivia... Read full Story
shemale lover 2012-09-06 2,408 Stockings Blowjob jerking cum swallowing
76%
My Wife's Secret Fantasy Chapter 1
PART ONE: REALIZATION The old saying "you never really ever know some one" is quite true when it comes to my wife Debbie. Debbie has always seemed to come up with new surprises to keep our marriage stimulated and adventuresome. As I've recently found out though she seems to have been ke... Read full Story
shemale lover 2012-09-09 10,148 Crossdresser Cumshot Masturbation Lingerie heels
50%
Al Fresco: An Erotic Sci Fi Tale
"Thank goodness for modern science," Ali said as she smoothed her tight black skirt across her shapely hips. The tall brunette turned this way and that in front of her mirror, admiring her taut, toned, and trim figure. Her hands moved up from her hips to cup the twin handfuls at her chest,... Read full Story
shemale lover 2012-09-19 7,412 Cumshot ass fucking oral sex cum swallowing
87%
Working with Trista
Day 1: I had just started my new job; only a month in and so far it was ok. I was laid off months earlier and forced to start working in a temp firm. The hours were all right, the pay was reasonable, and I couldn't complain about the commute. I was told this position could potentially turn into a... Read full Story
shemale lover 2012-09-23 6,628 Blowjob cum massage
100%
Screwed
Randi's excitement grew as she walked outside to her car. She'd been preparing for this all day and dreaming it up for weeks. She began the day by showering and shaving her legs, followed by putting on a nice red nail polish on her fingers and toes. She went to her dresser and picked out a black ... Read full Story
shemale lover 2012-09-24 3,380 Cumshot suck domination cum swallowing
100%
Joe gets to the bottom of things
She kept it tucked away, uncomfortable, squeezed between her legs held in place by the tight rubbery panties that really weren't her style, but they punctuated the "surprise". Joe was aroused by her femininity, as she slipped off the spaghetti straps of her little white dress revealing the... Read full Story
keeponst 2012-10-08 3,091 sucking Ladyboy virgin
100%
I Really Don't Know Chapter 1
My girlfriend of 5 years, the woman I love dearly, it's like she's a different person now. Well ... she sort of is. This all started about a week ago, she happened across an ancient artifact. And somehow, against all reality, it had a genie in it – a magical creature whose purpose is to grant ... Read full Story
shemale lover 2013-01-09 3,860 Cumshot sucking Blowjob oral sex big boobs
94%
Taken Chapter 1
Georgia pulled her Mercedes out of the gas station in Albuquerque back onto interstate 40 heading east. It was a long drive ahead to Chicago. She hated traveling alone, that was for sure, but the move to the office back east made it necessary. It was either drive there or sell her Mercedes and buy a... Read full Story
shemale lover 2013-01-18 7,466 Cumshot Big Cock ass licking big boobs ass fingering
93%
New School, New Life
Part of my father's job is on-campus recruiting, so when it was time for him to spend a week at the university where I was enrolled for the following fall, we decided that I should go with him and familiarize myself with the campus. We left on a Friday morning to ensure I'd have a full week on ca... Read full Story
shemale lover 2013-02-06 8,975 Teen (18+) Crossdresser Cumshot sucking ass fucking
88%
Ivana Pushing Sissy's Limits
"You look ravishing," my wife Ivana said as I stood before her in a short red velvet dress with white tights and black Blahnik mary janes heels. She walked over to put a hair band in my long black hair. It was down to my shoulders now, flat-ironed straight. We stood together in front of... Read full Story
shemale lover 2013-03-19 6,916 Crossdresser Cumshot sucking Creampie ass fucking
100%
Pleasant final
About a month ago I was away at a course. I noticed a guy across the room named Devin who was well dressed and had very feminine features. I sat with him at lunch because I had a feeling that he was a cross dresser or at least gay. Now I've been bi curious for a long time and have had close encounte... Read full Story
shemale lover 2013-04-26 4,158 Cumshot suck Blowjob oral stroking
76%
Sissy Ghetto bitch part 1
-The Guys 4 ghetto guys was inside a porn site looking at random sissy babe pictures when they accidently found a picture of someone they know. Like every album they clicked it that specific one with a tranny dressed so girly with mouth open. The guys had such a stone hard erection by watching al... Read full Story
shemale lover 2013-06-01 6,406 suck Big Cock cum jerking gangbang doggy style Interracial cd
66%
Franks Friend
Frank is a buddy of mine. We grew up and went to college together. While we were in college Frank and I went on a road trip from Lubbock to Dallas. We got to Dallas went to a few strip clubs and then finally found ourselves on Harry Hines Blvd. It was about 1 in the morning we were both horny and a ... Read full Story
shemale lover 2013-06-05 5,059 Cumshot suck threesome ass licking Guy Fucks Shemale fishnet
86%
Never Wanted To Be Your Girlfriend Ch. 03
Derrick really took advantage of having me captive that first weekend. He spent the entire time making me watch porn videos, and then had me recreate the scenes with him. He said, that he needed his girlfriend to be fully versed in all the ways he liked to be pleased. His appetite for sex was unreal... Read full Story
shemale lover 2014-07-21 6,000 Cumshot suck Blowjob facial oral sex
100%
Business and Pleasure: Seduced CD Pt. 2
I breathed in his musky scent while I squeezed and pulled his ample ass cheeks. I could smell that uniquBusiness and Pleasure: Seduced CD Pt. 2e man scent coming from between his legsBusiness and Pleasure: Seduced CD Pt. 2,Business and Pleasure: Seduced CD Pt. 2 sweat, moisture, precum, cologne all ... Read full Story
shemale lover 2014-07-29 4,553 anal Cumshot Lingerie swallowing cd
100%
Daddys Bride-to-be
Daddy rings my doorbell. I was waiting impatiently for him, dressed appropriately...today is a special day...today I promise daddy to marry his cock. I am dressed in a silky white wedding dress. Very short and tight, with shiny beads and pearls, along with a veil covering my face, and long white ... Read full Story
lea1234 2014-10-07 6,021 Stockings Cumshot suck cd
90%
Sissy story and 1st meet humiliation
I recently met up with someone to be a sissy slut for them and wanted to share what happened on my first meet. This is the genuine true story. I use the username indoblu on websites, but my sissy name is Holly so I'll refer to myself from now on as such. I'll mention my history as a sissy before tal... Read full Story
shemale lover 2014-11-19 26,015 ass Fetish domination cd sissy
93%
My Life as a Shemale Part1
In this story, many will find what happened to me socially unacceptable. But since this has happened to me, I get to tell it and if you like, listen. I was very young when I found myself on the streets and it seems long ago that some things I do not remember but its the important stuff that I do.... Read full Story
shemale lover 2015-02-19 5,268 tranny Stockings shemale Lingerie underwear
86%
James's Cum Slut
I had decided to spend the first week of my summer holidays after my AS levels at my friends house down in Hampshire. Both being borders at school we caught the train down to his house after term had finished. The house was a nice county retreat with a medium sized pool and a tennis court set in the... Read full Story
ATC97 2015-04-15 5,527 Crossdresser Blowjob oral bikini riding cd
97%
FAGGOT COMES OUT TO HIS WIFE!
I was married for 3 years before I finally got caught. It happened when my Filipina wife went through my notebooks and found all the gay fantasies I had been writing about. The story she found was one I had just written. It was about a young guy who applies for a modeling job at a gay magazine calle... Read full Story
Kevyn-JeanneHarris 2015-12-25 9,488 homosexual sissy sexd
52%
My neighbor
Peter invited me up to his place to show me the lady I saw through my window. She was a beauty with very sexy lingerie and silk stockings. Her tits were large And I could see them under her transparent top. It didn't take long before I realized she was Peter, only beautiful and sexy. Sit and... Read full Story
warmcream 2016-04-05 5,670 Big Cock cock sucking crossdressing cum sucking ass sucking
90%
Lost Island
Bright light hit my eyes when I opened them after a long time. My mouth was full of sand, my toung dry and the taste of salt overwhelmed me. I was stranded. My boat sank in a terrible storm and my body was washed on this lonely beach of a tropical island. The sea was calm and there were almost no w... Read full Story
xgandalf 2016-05-04 6,577 sucking gangbang domination ass fuking Shemale on Guy
67%
My first time with a shemale
This first time I saw a she-male in my live was in Germany Hamburg at the Reeperbahn. I was in a tranny show where I realised I got horney seeing those women do there acts. After there show I went to talk to the ladies. Nothing went feather then some kisses and that there dicks are full operational.... Read full Story
shmlover832220 2017-08-28 13,577 suck Blowjob shemale oral sex cum in mouth
78%
My Futanari Dreamgirl
My Futanari Dreamgirl I opened the door and there it was, just swinging between her legs. Big and veiny with a bright pink head. My roommate Jesse didn't notice me walk into the bathroom. She had just stepped out of the shower and was toweling off her hair. Her eyes were covered by the towel... Read full Story
Jade Dixxon 2017-10-23 20,562 tranny Cumshot Blowjob Guy Fucks Shemale Futanari
60%
Sucking mature huge cock stepdad
When mom passed my stepdad KEN was alone for 3 yrs he made comments like you need tighter shorts your hair smells pretty one day as I was Su king my friends 5 inch cock as he surf cum on my face KEN walked in my room then told my friend to leave I started to cry and he said it was ok he new i was a ... Read full Story
Cumsuckinfool11 2018-04-11 7,931 Crossdresser Blowjob Ass to Mouth cum in mouth Big cock dad
85%
A Fantasy for the future
I walk up to you from behind. Just as you sense my presence, you hear my husky voice whisper in your ear, "Do not turn around, or all this will stop". A shiver of excitement goes through you. I start to stroke the back of your neck, first with my fingertips, then with the ends of my beau... Read full Story
thesofa 2018-05-02 4,453 Bareback
100%
Fooled Into Love by a Beautiful Transexual
A fictional, steamy love story about a Man’s first experience with a Shemale... a real take charge kinda girl! Maria Lopez was an absolutely stunning 23 yr old Puerto Rican Goddess. I remember the first time I laid eyes on her, bent over inside her hatchback Toyota, pulling out a hanging fern pla... Read full Story
Oobatz 2018-07-24 12,911 Small Tits Amateur Cumshot Bareback Shemale Fucks Guy Big Cock domination cum in mouth
100%
When Fantasy Comes True
I have always had this fantasy to be the object of lust for two trannies. But never till date did I think I had it in me to fulfill the fantasy or be ever so lucky. I had one night been invited over by a trans friend for a few drinks. I went over with a bottle of vodka and a few beers. When I re... Read full Story
Sara Banks 2018-09-10 7,950 threesome trans sissy cum in mouth shemale fucks man double blowjob golden shower
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 8,903 anal Blowjob transsexual oral sex cum swallowing romance transgendered Consensual Sex Older Female / Males
86%
My adventure at the adult bookstore
I was horny as fuck the other afternoon. I had some time to kill so I hit squirt.org and fetlife seeing if there were any dudes needing a free blo-n-go. Nobody took me up. Sad face. I drove to the local adult book store that has video booths. I was sitting in the parking lot watching people go in... Read full Story
shedawg 2019-04-15 6,548 Amateur Outdoor Blowjob cum in mouth
100%
The Girl Next Door Ch. 03 by derezzed ©
Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Alexis's arm casu... Read full Story
StevelovesTgirls 2019-06-11 18,919 Amateur Shemale Fucks Guy Fetish threesome Blowjob domination Guy Fucks Shemale Ass to Mouth shemale + shemale
100%
Decisions, decisions.
So if you have read my stuff I’ve posted before I was with a tranny named Nicole for awhile but she left for work last year so after she left I actually started dating normal again went back to girls but never forgot her. I’ve hid the dildo and all my secrets from my current girlfriend for almost a ... Read full Story
Duke04 2019-07-25 8,097 Shemale Fucks Guy Fetish Blowjob Big Cock cum in mouth
86%
Alex’s Bottom Slut
So when I was younger, I worked at a pizza place as a delivery guy. It was a pretty boring job for the most part but that all changed one night. I got a delivery to just outside of our range but decided to take it anyways because we were slow. When I got there a very tall and muscular black woman in... Read full Story
Jsmithsub 2019-11-18 57,423 Group Sex Cumshot Shemale Fucks Guy Blowjob Big Cock Ebony gangbang domination Interracial Ass to Mouth cum in mouth
100%
Sissy Slut Reunion
Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... Read full Story
Regina10 2020-09-14 4,464 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
84%
SUMMER VACATION by Spanky de Bautumn
In our house, it was a well-known secret that my mother kept her change in the top drawer of her dresser. The same drawer she kept her slips, chemises, panties, and all other satin, nylon, or lacy ladies undergarments. During the summer, my brother and I would run to that wondrous drawer when... Read full Story
SpankydeBautumn 2021-01-22 12,924 Small Tits Crossdresser Cumshot Masturbation Fetish Blowjob Lingerie Shemale and Girl cum in mouth
100%
DOM of a MTF dream
I had a dream the other night. I was getting out of work, and was walking home. I walked by a bar with only a couple people inside. It looked nice and quiet where I could have a drink and unwind. I walked in and ordered a mixed drink. Half way through it I saw a young girl looking my way. I c... Read full Story
77James 2021-10-07 3,179 Blowjob cum in mouth
100%
The Golf Bet
A couple of years ago I joined a new golf course, I wasn't the best golfer but very keen, I would be at the practice area almost everyday for at least an hour. Over this time I got to know a number of members and it was a good way of meeting people to play with. Over that year I met a number of new... Read full Story
chris1989r 2022-01-03 5,017 Amateur Cumshot Shemale Fucks Guy Guy Fucks Shemale cum in mouth