Sort by
Date Added

Free Stories

100%
Sweet Encore
I was alone tonight and feeling just a bit paranoid as I listened to the soft music. The soothing sounds put me in a seductive mood, but It seemed that all my lovers were too busy for me, or they had other plans. Uncle Barney and my detective were probably home being dutiful husbands. Bo was under h... Read full Story
Regina10 2024-05-09 990 Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass Ass to Mouth
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 1,627 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
100%
Regina's scary, and sexy Blind Date
I had just finished doing my makeup, finally deciding which blush to use, and I thought I had some time for my meditation. However, Mr. Cobb was early. The gold minidress I wore showed enough legs, ass and tits to make any man horny, and the strappy tanned five-inch sandals, made me feel majestic ... Read full Story
Regina10 2024-03-18 3,103 anal Crossdresser Bareback Creampie Fetish Blowjob Ebony Guy Fucks Shemale big ass sissy Ass to Mouth cum in mouth
100%
Walked naked at night.
It was a hot and humid night in Missisippi. I live near a nice park and golf course so i sometimes walk through there at night. Usually im alone but sometime there is people. I usually bring a small skirt that has my cute little ass and my big cock hanging out the front and a lace bra. I like to fee... Read full Story
Tslover66420 2024-03-01 3,883 public sissy crossdress
100%
Branching Off
Branching Off A colleague at work surprised me by handing me an invitation to his wedding. I was surprised because we seldom spoke to one another and had only socialized once when we were all given tickets to a New Orleans Breakers pro football game in the Superdome because our hastily drawn up ... Read full Story
DRILLMASTER 2023-11-18 6,191 sissy
50%
Towel Boi: You're Hired
Kasey Stevens woke up in his new studio apartment. The five-foot-nine, blue-eyed sissy with ash brown hair yawned and stretched before heading into the bathroom. He showered, taking good care to lather his rosy skin with strawberry scented body wash. He shaved his legs and rinsed off. Then, he appli... Read full Story
Faggyboi and Puzziboi 2023-11-14 5,570 anal Small Tits Crossdresser Amateur Bareback Blowjob Guy Fucks Shemale Interracial small cock big ass femboy
95%
Am I now a genuine Sissy Slut?
I started Crossdressing when I was about 16 years old, the usual story , mother and sisters panties from out of their drawers when I was home alone. As I got older and married I stopped Crossdressing and consentrated on being the family man. As the years rolled by and the kids grew up and left hom... Read full Story
Sissy Kirsty 2023-10-27 13,186 anal sissy stranger
100%
MARDI GRAS MADNESS
MARDI GRAS MADNESS The New Orleans Mardi Gras Season has always been a favorite time of the year for me. I love the beautiful floats, the marching band competition, the marching and dancing clubs, and of course the “throws” tossed to the crowds. I have gotten to the point where I seldom view par... Read full Story
DRILLMASTER 2023-10-26 4,751 sissy
0%
Brother of the Bride
“What in the ‘Get Out’ hell is going on here,” quizzed the warm, brownish-red woman with the Bantu knots as soon as they were safe inside the gold 1970 Deuce and a Quarter. “I don’t even know,” chuckled the driver as he jerked his head to get his short dreadlocks out of his line of sight. “Wel... Read full Story
Faggyboi and Puzziboi 2023-07-15 4,981 anal Crossdresser Guy Fucks Shemale Interracial sissy femboy faggot sissy crossdresser BB jack of spades bblbuttcd bbl
95%
My best friend turned trans.....so I fucked him - Part 1
Theres a bit of history to this one so strap in! I started hanging out with this group of kids in my area when I was 12 years old, we did all the typical stuff you can imagine young kids getting up to (played football, chased girls etc...) over the years I became really good friends with one of the ... Read full Story
iconicirish 2023-05-11 8,416 Stockings Amateur cock Masturbation sucking Blowjob Big Cock Lingerie Latex transgender sissy
50%
MON NEVEU GOUJON ⚧️ ⚧️
"Daadddd, est-ce qu'on doit vraiment faire ça ?" ma fille pleurnichait. "Je suis aussi mécontent que toi, Tracy, mais je ne pouvais pas dire non. Tu es stagiaire dans leur magazine l'été prochain, tu te souviens ? Un bon tour en mérite un autre." Elle m'a juste fait la moue. Tracy est une étud... Read full Story
Femboy 2021 2023-04-16 939 Teen (18+) Blowjob Big Cock domination sissy sissification cum in mouth sexe anal féminisation Sissy
0%
FACTEURS INFLUENTS ! ⚧️ 💞 ⚧️
Ma femme, Jill, était à Denver pendant douze jours pour assister à un séminaire médical pour les chirurgiens plasticiens et ne devait pas revenir avant quelques jours. En raison de son travail, elle assiste à plusieurs séminaires, à l'intérieur et à l'extérieur de l'État, parfois un jour ou plusieur... Read full Story
Femboy 2021 2023-04-02 1,011 Stockings Blowjob Big Cock Lingerie Sex Toys cum in mouth sextape sissified femination forcé maitresse épouse pris en vetements de femme sexanal
50%
DE BRO À SISSY ⚧️ ⚧️
Mon ami Magnus et moi nous sommes connus presque toute notre vie. Nous nous sommes rencontrés en pré-maternelle, quand nous vivions à un pâté de maisons et demi l'un de l'autre. Nos familles étaient proches et nous avons grandi côte à côte. Nous nous connaissions depuis si longtemps; nous nous appel... Read full Story
Femboy 2021 2023-03-26 769 Blowjob Big Cock domination Sex Toys feminisation bbc cum in mouth bdsm scene soumission cocu poule mouillé femme chaude
50%
"SISSIFIED": 12 JOURS DE SISSY-MAS
JOUR 1: mardi 25 C'était le matin de Noël quand j'ai entendu frapper à ma porte, ce qui était, bien sûr, très étrange à dix heures du matin. À midi, j'allais chez ma famille pour Noël, et j'avais rarement des visiteurs inattendus. Toujours dans ma robe, je me dirigeai vers la porte et fus s... Read full Story
Femboy 2021 2023-01-20 1,110 Stockings Crossdresser Amateur Fetish Blowjob Big Cock Lingerie domination Sex Toys cum in mouth
92%
Shy boy to bimbo sissy
it's all started when my older brother showed me a shemale masturbating video when I was 15. after I saw it I was instantly attracted to trans girls than cis girls. I was a very shy pale feminine looking boy.high school wasn't great, boys used to bully me. I am too shy to talk to the girls... Read full Story
drleena 2022-12-08 12,558 shemale submissive cross dressing chastity prostitue real story
100%
Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
darrell 2022-01-03 4,048 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 4,772 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
100%
Lara : το πρώτο μου γαμήσι στον δρόμo
[1[1[1[ Αυτό που περιγράφεται παρακάτω είναι ένα μικρό, μα πολύ μικρό μέρος από μιά ιστορία που διήρκεσε μία ολόκληρη εβδομάδα. Ελπίζω να βρω τον χρόνο να την γράψω και να την αναρτήσω ολόκληρη, στο εγγύς μέλλον. Δημόσια γαμιώμουν πάντα, απ’ την πρώτη φορά που έφαγα πούτσο μέχρι τώρα, αυτή όμως ήτα... Read full Story
hotmatureLara 2021-10-14 1,169 sissy slut anal fuck sissy whore sissy fucked public fuck street fuck
81%
A pervy uncle invited me to his house at 10 PM..!
It's been 8-10 years now, I had this amazing experience. I was standing at the bus stop in my area/street(my daily routine), one uncle was watching me but I ignored eye contact as I feel awkward the way he was looking at me because I act straight in public and I felt that he's seen my girly ... Read full Story
Cindy Sky 2021-07-20 6,929 Teen (18+) Small Tits Amateur Cumshot Outdoor Bareback Creampie Fetish Blowjob Asian Ladyboy Mature
75%
Sissify Your Boyfriend Manual - transation
original= manual-sissificar-a-tu-novio-4979 Used google translate, found some pronoun/object/context issues, and I believe ladybug = ladyboy Sissify Your Boyfriend Manual MANUAL FOR WIFE/GIRLFRIEND TO SISSIFY YOUR MAN, DISCOVER HIS SUBMISSIVE SIDE AND TURN HIM INTO ?HORNAND? AN... Read full Story
shelli_k18 2021-04-20 8,087 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
87%
Body Anatomy Transition
I discovered I like to be penetrate in April of 2016 (according to my buying history, first anal massager), that was I read an article about sex toys review from a male perspective where pocket pussy, prostate massager and butt plug are reviewed together. I decided I also give anal a try, after that... Read full Story
NBClitorissa 2021-03-16 3,800 sissy sissification MtF transition transitioning
94%
Sissy Slut: Gang Favored
I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... Read full Story
Regina10 2021-03-02 7,193 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
100%
TO BE OR NOT TO BE - PART 7
TO BE OR NOT TO BE - PART 7 by Spanky de Bautumn Part 6. Sunny, Mel, and Shari had a heart to heart and Mark took Sunny for a night on the town. I woke up next to Mark, he looked so peaceful sleeping. Was I dreaming? Did I fall asleep and dream that Mark said he was going to take me shopping... Read full Story
SpankydeBautumn 2021-03-01 2,335 Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,359 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial 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 12,405 Small Tits Crossdresser Cumshot Masturbation Fetish Blowjob Lingerie Shemale and Girl cum in mouth
100%
Slut /W Bad Boy
I was excited as always because I was about to go out in public and hopefully I will meet some horny man with some money and get laid. Now, to make sure that I am a picture of femininity, I double checked my makeup in several mirrors from many angles. My lips were perfect and I made sure my cheeks b... Read full Story
Regina10 2020-12-04 6,815 Stockings Crossdresser Big Tits Cumshot Bareback Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale pov Ass to Mouth
87%
My first bi encounter
As a young catholic boy I always prayed I would have a women’s body. I would wear my sister’s clothes and masturbate in my bedroom. I have been a closet cross-dresser for a long time. In my early twenties I rented my own apartment. I would buy from Fredericks of Hollywood catalogue for my outfits, ... Read full Story
Palba 2020-11-12 6,388 Amateur Bareback Creampie Ass to Mouth guy fucks shemales
88%
A hole new world unfolding before my eyes.
When i was still a little boy, i was always surrounded by women, i was raised mostly by them, so i always was in touch with that feminine side of mine. In addition my sexual desires and cravings developed actually kinda fast. I remember loving the feeling of watching my mom's wardrobe specially her ... Read full Story
stranger696 2020-11-06 4,098 Crossdresser solo Cumshot Fetish Ladyboy Lingerie Frist time Closeted
93%
Virgin Slut Cravings.
There have been so many times that I have had to hide how I felt because I lived my life denying who I was. I was a closet queen who was pretending to be normal. Some might have guessed my secret if they were observant. I didn't do things that other boys my age did. I love hanging out at home like a... Read full Story
Regina10 2020-09-29 8,144 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
88%
Daddy Not Dad
I discovered my bisexual inclinations fairly early in life, so by the time I was 19, I had done nearly everything you could do with any combination of genders and numbers. I'm a regular guy on the outside, but in private I am comfortable in both the masculine and the ultra-feminine role. I could pas... Read full Story
Faye Gella 2019-11-04 12,178 crossdressing gangbang sex Stepfather
92%
My Neighbor
When I got divorced and was finally living alone I had many fun times getting fucked all I could by both men and women. I was always dressed when home and loved to stay that way all weekend long and would just put on some pants over my outfit to go shopping sometimes with a coat or shirt over my ope... Read full Story
crossdresser55 2019-10-29 16,274 Stockings Crossdresser
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 11,541 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
78%
Becoming a Sissy - My aunt my Mistress II
There i was on the lobby block, dressed up as a whore with my pants down and my ass plugged, next to me was my aunt, laughing of my boner, my mind went blank for a second not knowing if all this is real but i was interrupted from trance when my aunt shacked me and said that we need to go. I pulled m... Read full Story
sissy emma 2018-08-13 14,869 Crossdresser humiliation slave.faggot mistress orders sissy mistresses
95%
Ginger's First Gangbang
I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... Read full Story
Ginger__57 2018-03-26 8,338 Stockings gangbang redhead domination Guy Fucks Shemale Ass to Mouth cum in mouth
68%
Mary Ann and the Tim the Ranch Hand
A few months after my girlfriend moved away suddenly to her grandparents home across the country,( I learned a few years ago she got pregnant) I was riding around on my bike in the street when my neighbor Mary Ann called me over. She was 18, I was still 12 at the time and very horny since my girlfri... Read full Story
Julliana 2017-01-13 7,198 anal pussy Blowjob cum oral sex kiss sissy Love young faggot
97%
FEM FIRM 4-POP SECRET
Fem Firm 4: Pop Secret by: B-Man View Story Details Rating: XXXAdd Review Added: 11/20/2016 Complete:no Synopsis: Ruby learns a family secret which will change her life forever. Categories:Bimbo Workplace Situations Keywords:Long Finger Na... Read full Story
bennyx709 2016-11-22 9,752 anal sex cocksucking workplace situations
77%
How I Became the Sissy Slut
It all started when I was about 11. I was a very petite and short and had long straight brown hair with whispy bangs as a child. I was often mistaken for a girl. I have a sister who was 6 years older than me about my size she used to dress pretty sexy with the tight jeans and the skin tight sailor b... Read full Story
Tvtrinity 2016-08-29 71,258 Teen (18+) Crossdresser transgender sissy slut.trinity
90%
DISCOVERING BLACK COCK
To the greater Boston general public it was simply a small little known quite private night club located in the back part of Roxbury called The Black Rooster Bar. While in local Gay Community circles, insiders called this private by membership only pub, THE BLACK COCK CASTLE! When first learning... Read full Story
CD DIXIE IN NH 2016-05-10 9,983 Big Cock cumming sperm ebony cock
59%
NORTH HOLLYWOOD GAY BATHHOUSE
Hi so the first time i went to a bathhouse was when i was 18 , i was dating a 44yr old dominate top tranny (Tina) who had the biggest uncut latino thick cock, her cock was the one that made me not only give up on girls but she turned my body and mind into a complete bottom sissy , my butt became her... Read full Story
daddyssissyla 2016-02-22 12,774 anal submissive sissy bbc doggy styду
80%
JUERA MARICON
My name is Keven Jeanne and, Yes, I am a Sissy! When I was 13 I put on my mom's panties and some of her lipstick when she was at work. I had longish blonde hair and I ruffled it up - kind of teased it up - and when I looked in her dresser mirror, I almost ejaculated. Because what I saw looking ... Read full Story
Kevyn-JeanneHarris 2015-12-25 6,119 blonde shemale submissive cocksucking
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 14,933 first time ass Cumshot suck cd sissy make up
92%
The Curse (Sissy Story) by sdvine
I wasn't really having a good time that night at the bar. Truth be told, I had been practically dragged out in the first place by my best friend Joe, who told me he was tired of me "sitting on (my) ass" every night "finding new ways to be boring." Quite frankly, if this is what qualified as being no... Read full Story
shemale lover 2015-02-27 6,730 ass Cumshot sucking cd sissy
33%
Sleazy Walking
I was bored one night, and began to email wanted ads on craigslist to see who was hosting in my area. I lived in spokane, wa at the time in the east central area, sorta behind the fred meyer. This night was boring, my friends had left a while ago with their girl friends, jealousy began to set in. I ... Read full Story
Ville Lohner 2014-05-15 2,722 Stockings Crossdresser Amateur suck Lingerie
36%
The Surprise Visit
I had been chatting for some time online with a guy who said he liked crossdressers and loved getting his cock sucked. we chatted numerous nights, roleplayed online. i guess, i don't remember, but i guess i gave him my address. but i worked long changing hours. one thursdau night about 2 am i was co... Read full Story
bigtranslover 2013-12-17 4,551 first time shemales hardcore
84%
Young sissy goes for a little shopping... caught
May be first a little introduction? My name is Sylvia and I love women's clothes! I like panties, stockings but most of all, I adore high heels! just love them! That feeling when it becomes higher and I feel so sexy and feminine! And you know what? I'm a total slut, I love to be humiliated,... Read full Story
shemale lover 2013-08-14 17,352 Stockings suck oral Lingerie public cd
100%
Finding master
It had been my dream all along to be someone’s sissy slave. To be able to please them time and time again. I met my master in a gay club that had cross dressing night. I was of course dressed in a dress with stocking and stilettos. Master was in leather pants and a tight tee shirt with his mus... Read full Story
shemale lover 2013-07-16 3,511 Crossdresser Fetish domination cd sissy
93%
Miss Bernie
My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... Read full Story
shemale lover 2013-02-22 13,778 hardcore sucking ass fucking Guy Fucks Shemale
100%
Sissy Crissi Chapter 1
Chapter 1 -- One Dreamy Night Like most Friday nights, my roommate Erika would be gone tonight. She and her new boyfriend, Leroy, were taking off for a private weekend. Erika and I had met about two years prior, when we were introduced by a mutual friend. Being fresh off a divorce, I was in need ... Read full Story
shemale lover 2013-01-30 7,676 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 16,994 Crossdresser sucking Big Cock ass licking big boobs
100%
Proud To Be A Sissy Chapter 4
As usual, Mr. Clark was sitting in his recliner when I went into his house. "Good morning daddy," I beamed kneeling before him. "Morning," he grumbled but smiled and said, "more like afternoon." But you do look sweet." "Thank you daddy," I rep... Read full Story
shemale lover 2012-12-24 7,938 Cumshot sucking Big Cock gangbang bukkake
100%
Proud To Be A Sissy Chapter 3
I woke Monday morning actually looking forward to what the day may hold and feeling good about myself. I felt like I was a different person and as I thought about it realized that in a few ways I was. I laid in bed thinking I did have a little better understanding of my sexuality now that was so con... Read full Story
shemale lover 2012-12-23 7,144 Crossdresser sucking Big Cock Lingerie ass fucking
65%
Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
shemale lover 2012-12-19 10,350 Masturbation Blowjob blonde ass fucking big boobs
100%
G Is for Gemma
Stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! *** It all really started on a Monday. One bright sunny Monday, early summer, an unusually warm day for June in England. And it really was stupid thing to do... Read full Story
shemale lover 2012-12-15 4,538 anal Cumshot cock sucking club
66%
Free Shoes
"Lift your leg up on the sink and pull your panties down again. I like to watch you submit," the voice behind me commands. I didn't intend to go this far. It was supposed to be harmless fun. But as my throbbing cockhead rests against the cold of this stranger's bathroom sink and I can see ... Read full Story
shemale lover 2012-11-28 4,038 Crossdresser Fetish heels
100%
Which Are You?
Which are you? A, B or C? A) You treat me well. You insist that I look stunningly pretty 24/7. You insist I always wear make-up, care for my hair and nails. You pay for me to go to a beautician once a week. You buy me sexy lingerie. You get angry if I wear slacks or jeans. You prefer dresses in p... Read full Story
shemale lover 2012-11-22 2,846 Fetish Lingerie sissy
100%
Dress Up
I don't know how to explain it. I am not gay although I may be passive bi. I have had sex with men, but not a lot and I have always been the one receiving, you know once a friend showed me a pack of pictures of his wife from fully dressed in conservative suit to complete nude with some action photos... Read full Story
shemale lover 2012-11-17 4,311 Fetish cum oral sex Sex Toys cum swallowing