Sort by
Relevancy

Free Stories

100%
Buying Heels
I have to know what it feels like to wear heels. I have the house to myself tonight and I'm going to play. I already have panties but want to buy some new ones. My wife bought me a black, frilly thong which I wore for her when we went out one night; I also have a cheap, supermarket pair of sheer ... Read full Story
shemale lover 2012-09-30 4,973 Stockings Cumshot oral sex crossdressing
78%
A Little Girl Forever
Since I was a little girl I dressed in my sister's clothes, she knew it and she kept clothes for me and sometimes she bought clothes thinking about me. She was my accomplice and still is. When I was alone I dressed totally as a woman and I felt totally satisfied and realized as such, this included m... Read full Story
Mabel Cecilia 2019-05-06 8,320 Small Tits Crossdresser Amateur Cumshot Latina Masturbation Creampie Blowjob blonde Lingerie Shemale and Girl Guy Fucks Shemale Sex Toys Mature self sucking Solo Shemale cum in mouth double anal shemale + shemale
90%
Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... Read full Story
shemale lover 2012-03-01 14,209 first time sucking fuck domination
80%
Office Policy
“Ok ladies and gentleman, please put your hands together for the beautiful and talented Erika!” the DJ’s voice rang out over the thumping alternative beat as the object of my lust strutted to the stage. Erika’s saucy red curls bounced on her head and on her soft porcelain whi... Read full Story
shemale lover 2012-08-30 8,813 anal ass sucking threesome tits fingering sex blondie
100%
Gay friend of my brothers
As I mentioned in previous stories, my brothers met Adrian at university, he was studying nursing, he was in the same year as my brother and they were studying one or another subject together, Adrian has brown skin, green eyes, his short Chinese hair He has a slim body, he was 1.69 tall, his nose is... Read full Story
lkusex 2021-03-08 5,528 Amateur Guy Fucks Shemale
0%
The Greatest Lie Part 19
The booked me as Alex Rios and handed me an orange jump suit and slip-on boots. I changed in a tiny curtained alcove and relinquished my clothes, shoes and purse, and became Inmate 265743. The booking clerk ignored my pleading eyes, so I begged. "You can't put me into a male population. I... Read full Story
shemale lover 2012-01-21 4,991 hardcore femdom erotic encounters
40%
Dating all whole my life
Julia and Ilya, together 10 years It was more than 10 years and 2 children ago. In December 2005, we agreed to meet at the gate of my office after a working day. I did not go out godlessly for a long time (40 minutes from the appointed time), but he still waited. I hope he does not regret it ... Read full Story
PornoDating 2019-08-15 4,245 Crossdresser Amateur Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock Asian gangbang domination Guy Fucks Shemale Interracial sex Mature Futanari Frottage Compilation Ass to Mouth Cartoon cum in mouth double anal dating life in Mars? life
100%
A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
shemale lover 2011-12-06 6,948 Creampie Big Cock ass fucking
96%
Making A Man Out Of Tommy
I have two good friends, Brad and Matt who are actually my fuck buddies. Both of them travel for work, so they tend to be gone a couple of months at a time. I have a key to their apartment, so I can let myself in for sex when they are home and to bring in the mail when they are not. I also get to us... Read full Story
pennypenny 2018-08-31 10,135 Teen (18+) Crossdresser Amateur Masturbation Bareback Creampie Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Jo, Shemale Goddess! Part 1
Jo plumped the cushion and carefully positioned it until it was precisely at the right angle. Nothing less than perfection would do. Ricki, her friend of twelve years was coming to stay overnight and she would notice if the tiniest thing was out of place. An impatient knock on the door signalled ... Read full Story
shemale lover 2011-09-04 5,680 anal sex sucking shemale
92%
Southern Hospitality Ch. 04
XtinaSmith2017 Ash awoke feeling cold, he pursed his lips a little and shivered, curling up a little tighter, nude as he was, the action brought little relief from the cool air. He let out a soft murr of discomfort as his mind shook off the cobwebs of lingering dreams, he could see light throug... Read full Story
Gwapo67 2022-05-16 6,999 Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Mature 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 4,422 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Nunca se Olvida
He tenido la oportunidad de tener sexo con varios hombres, algunos mayores que yo y otros muy chicos, no me fijo en estereotipos o personalidad, solo me gusta disfrutar del sexo..... Pero siempre hay uno que te deja enamorado, Daniel su nombre una persona que conocí por medio de un chat. No pas... Read full Story
Carla Travesti 2020-10-05 3,413 Small Tits Crossdresser Amateur Latina Bareback Fetish Ebony Lingerie Interracial
66%
A different couple
I am Hans, as I already mentioned in my previous story, I am a mature guy (47 years old) who came to the Island of Tenerife more than two decades ago. I am a drinker, a womanizer and a gambler. In these more than 20 years I have seen them in all colors. I have made a lot of money and lost as much, I... Read full Story
lkusex 2021-03-08 5,881 Amateur Big Tits domination
100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 5,405 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
50%
Feriengruss 18.07.24
Um ähnliches, wie im folgenden Bericht, mit mir zu erleben, ist es notwendig, dass man sich sehr gut kennt. Alle Handlungen sind miteinander abgesprochen und es ist beidseitig ein tiefes Vertrauen vorhanden. Nicht nur, dass mir nichts passiert, auch dass ich meine Grenzen während des Spiels klar kom... Read full Story
Cheryl_F 2024-09-03 230 anal Small Tits Amateur Cumshot Bareback Creampie Fetish blonde Big Cock Ladyboy Shemale and Girl Sex Toys small cock
87%
Headmistress' Favorite Sport Part 3
There was no more time for Denise and Susanna to get over their chemically induced bout of incestuous activity as Denise was being sent to school. This was of course part of the plan. Slaves should always feel guilty about something and once their slave training was over, neither would be able to ma... Read full Story
shemale lover 2011-12-12 6,433 toys bondage and discipline chastity belt
80%
Debbie Part 7
As Debbie was led into Dr. Jacobsen's office, she saw that Mistress was already there waiting for her. "Your property Miss Chamberlain", the doctor proclaimed, indicating Debbie. Debbie's heart began to flutter with love and submissive fantasies as she saw Mistress. Mistress was dressed in... Read full Story
shemale lover 2011-12-23 9,800 transgender toys bondage and discipline heavy
100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 9,402 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
100%
The Experience of a Lifetime
My divorce was hitting me really hard. My wife outgrew our relationship and started living her own life and I had a front row seat to everything. My heart and life was upside down. I didn’t go out anymore. Friends and family both told me it was time to get my life back on track and start living ... Read full Story
therefill05 2020-11-30 20,550 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob blonde Big Cock Ebony Uniform domination cum in mouth
100%
The game show,
One day i was looking through a number of competitions and trying to find a way to make some easy quick money. A number of applications were sent, mostly for junk i didn't need or for competitions I knew I had no chance of winning. For example, the types you get $30,000 for answering the easiest que... Read full Story
chris1989r 2022-01-24 5,067 Bareback Shemale Fucks Guy Ebony gangbang Guy Fucks Shemale shemale + shemale
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 3,858 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
85%
Becoming Zoe
My soon to be wife Annie had taken a job out of town and I only saw her every two weeks or so. I was so missing her. She and I had become long distance lovers. She was scheduled for a flight home on Friday night. I was going to pick up her son Zakk from his dorm and the two of us were going to p... Read full Story
Zöe from Kingston 2018-08-09 9,432 Stockings Teen (18+) Crossdresser Cumshot Bareback Blowjob blonde Big Cock Lingerie Mature cum in mouth
100%
College project surprise
So this story happened while I was still in college and remains without doubt, the craziest, most exciting experience of my life. So I the story begins one day when I walking to class. I went to a big university so my walk was quite long, and the first 1/3 was just through off our campus housin... Read full Story
Jsmithsub 2020-09-16 21,567 Group Sex Bareback Shemale Fucks Guy Fetish threesome Big Cock Ebony domination Ass to Mouth cum in mouth
80%
The Grass Ain't Always Greener...
Lawn care takes an unexpected voyeurism and exhibitionism masturbation detour I cut grass, mow lawns, manicure shrubs, trim bushes, and plant trees. Right handed and always trimming from the right side, I've never been a switch hitter when using my hedge trimmer, if you know what I mean. Always ... Read full Story
shemale lover 2013-01-16 5,229 Masturbation Blowjob blonde jerking big boobs
50%
EROTIC FANTASY PART 1.
The Secret Manor of Lusting Intersexual Ts.Ladys as they enforce males into there training house all too become wimpering shemale sexslaves! I met a Lady once at Bar too which she was very sexy Lady as we had some fun now n then as too get too know each other I slowly tranformed myself into her E... Read full Story
Isabella Coupe 2024-09-25 1,342 Amateur Fetish Uniform domination
89%
The Magic of my first Blac Coc
Wow! This was my first real experience with Black Cock. it was right after my divorce. I was in my late twenties. I ran my ads as a crossdresser on a few dating sites and on Craigslist. I received a message on my AFF site from a member whose profile name was BBCRicky. My interest was immediately... Read full Story
Tvtrinity 2021-04-07 21,990 Stockings Amateur Bareback Lingerie Interracial transgender sissy bbc сrossdresser tvtrinity
78%
Cara's First Time
Cara's First Time This little true story is about the first time I was with a man and a night that I will never forget. My name is Cara. Well that's my girly name, I'm a cross-dresser. I've loved dressing up in women's clothes since I was young when I used to dress up in... Read full Story
Emma W 2017-07-05 30,402 Crossdresser Amateur Bareback
87%
Southern Hospitality Ch. 03
XtinaSmith2017 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 ... Read full Story
Gwapo67 2022-05-16 5,016 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
My Gloryhole Daddy
I had been working the gloryhole at the strip club for almost a month. Mostly it was jerking off pathetic dicks with a fleshlight while fake moaning and scrolling my phone. But every now and then I'd get a text from my favorite john saying he'd be stopping by. His cock was so beautiful! A solid 8 in... Read full Story
KaceyKlarissa 2024-09-11 2,062 anal Crossdresser Bareback Creampie Blowjob blonde Big Cock domination Guy Fucks Shemale sissy femboy Ass to Mouth
87%
smoking
Greg decided to go straight. I had to find a new place to live. A nice man, Pete, who I knew from the YMCA, offered me a place in his basement. He was going to rent it out. It was nice, full kitchen, bedroom, laundry room, living room and another space for anything I would need. His rent was che... Read full Story
cd4fun715 2019-01-08 3,035 Amateur
100%
The Dating Game
This happened a few years ago when i had just been accepted into Edinburgh University to undertake my Masters. As all students do, I went to the tourist spots with an eye on the other tourists and potential bars to frequent. Having come prepared with an arsenal of dating apps downloaded I was all s... Read full Story
chris1989r 2021-08-11 6,910 Amateur Bareback Big Cock domination Ass to Mouth cum in mouth
87%
THE ATTIC NOVEMBER 7
THE ATTIC NOVEMBER 7 – PART 1 THE JOURNEY AND GETTING READY. Susan had not had the opportunity to make the journey to the Attic dolled up to the nines so she made do with just wearing her black and pink lingerie under the hideous drab stuff (yuck). Having arrived early and parked up, she relaxed ... Read full Story
sexysusang 2018-03-09 6,156 Amateur Group Sex Bareback Blowjob Guy Fucks Shemale cum in mouth
66%
a day in the life of Amber SissyZofen 264
And the days had passed one after the other and now it was the day of my date. He sent me a txt at 8.30 on Saturday morning to say he was coming And you remember he was leaving his phone at home in case his wife called You know I had sent him my address, parking advice and left the gate ajar. ... Read full Story
amberdoll 2020-09-15 2,923 Stockings Small Tits Crossdresser Amateur Masturbation Bareback Creampie blonde Lingerie Homemade cum in mouth
50%
Baby Face Jack's Biggest Fight
The referee held his gloved hand high in the air. The crowd was hushed as the ring announcer spoke, "Ladies and Gentlemen, the winner of this World Featherweight Championship Boxing Match to unify the title, by technical knockout, and still undefeated; Baby-face Jack Mc Coy." The crowd scr... Read full Story
shemale lover 2012-02-08 7,346 fuck oral
66%
Would You
'Would you...?' 'Look the part to play the part....' 1 5' 4...dreaded, and to be dreaded....bookish, be-spectacled—damn near owlish....so much so that you might miss the way her tits spoke to you no matter how much she attempted to 'silence' them ....that you might miss the way her sk... Read full Story
shemale lover 2012-09-23 6,801 sucking cum massage
0%
Lady Denisa's Gang Banged
The young black youth aged eighteen was lying on the bed while I mounted him for the third time that day. I used his cock and muscular body shamefully to bring myself off with no thought for his pleasure. Kenny was my toy boy, an aircraftsman from the base my husband commanded when he wasn't away on... Read full Story
shemale lover 2011-11-22 4,639 shemale oral orgasm
50%
Giving Away Virginia Holton
Today would have to wait, thought Marla Holton as she hurriedly gathered her bag and notebook in preparation for a no-holds-barred departure from her office at Prism Design. As general manager she had the privilege of arriving and leaving at will, though no one could ever fault her for not putting i... Read full Story
shemale lover 2011-10-08 4,761 shemale cum ass fucking
83%
Teacher Student Confidentiality
It was raining cats and dogs outside as Ms. Catherine Walker (Cat by her friends) graded her Accelerated Integrated Geometry test scores. Her was long and flowing and her sweater was purposely pulled low to embarrass the male teachers with her cleavage. Her cock twitched as she shifted her leg to a ... Read full Story
shemale lover 2012-02-11 14,310 anal Blowjob black fiction
50%
A Perfect Life
The reasons I am not writing this myself. I have finally convinced someone to do it for me. She promised to post it on the Internet, but only as fiction. I suppose it is a bit unbelievable. It all started with the best of intentions. I had married my love while we were still in college. She... Read full Story
shemale lover 2012-05-05 12,852 transgender
100%
Witch Chronicles
I have been asked to write down my perception of the events of the war. After what's just happened, I thought it best to wait and rest before writing things out, but the big wigs want me to get it all down while it's still fresh, so don't expect this to be an extremely military report. I... Read full Story
shemale lover 2012-01-01 6,051 Masturbation orgasm fantasy tg
93%
Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
shemale lover 2015-05-01 15,563 first time ass Cumshot suck cd sissy make up
50%
Liberty meeting, chapter1
On a beautiful summer day, my phone rings. It's Steve, the boss of a transvestite company who calls me. - Hello Sandra, I have four new friends waiting for you at the club. - Thanks for thinking of me, I'll be right there, I said, hanging up. I am happy with his call because I always meet ... Read full Story
sandratvtg 2024-06-20 2,696 Stockings Shemale Fucks Guy Fetish Lingerie shemale + shemale
100%
Amanda and Me Chapter 2
I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. ... Read full Story
shemale lover 2012-10-21 8,916 anal Cumshot shemale oral