Sort by
Relevancy

Free Stories

95%
An itch that finally got scratched
Hey all! New to the site, but have been a major fan of TS/CD etc since I was a teen. I remember always fantasizing about what it would be like if I was to ever get an opportunity to make the fantasy a reality. Well, I finally got that chance and took full advantage of the situation and I wanted ... Read full Story
sizeman 2013-04-10 8,175 Shemale Fucks Guy doggy style Guy Fucks Shemale cum swallowing riding cock
88%
Me being a pet
As you all know i am a bitch of my mistress "sissychick". This incident happen recently during my training of being a little slut. So i was sitting right next to my mistress bed, like a loyal dog, still having anal plug inside my ass and my dog collar. It was the mark of me being my mistr... Read full Story
shemale lover 2013-05-07 5,034 sex toy anal sex Shemale Fucks Guy domination cum swallowing
100%
Traci the Maid
Traci had gotten a job as a maid in a rich man's house. She looked just like any blond 26-year old woman - long legs, slender waist and high size C breasts. She had a heart-shaped face and giggled at all the right times. Only Traci had a secret that nobody at her knew job knew about - she had a 6&qu... Read full Story
shemale lover 2013-07-19 5,353 Stockings Cumshot blonde Uniform Guy Fucks Shemale
50%
The party
So , we where on our way to the party that Monica had arrange for me , the party was in a motel suite on the hills , we drove for half hour , at the reception we where told to enter , some body where already there awaiting for us , we park the car and Leo indicate to go up the stairs , the place was... Read full Story
Suellen blonde 2014-09-02 3,791 Group Sex Fetish shemale orgy crossdressing
85%
THE WEATHERGIRL BY B-MAN
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2015-07-29 7,496 Crossdresser hardcore ass fucking cd
95%
FEM FIRM: Character Intro & Part 1
Coxson & Dicster is a law firm made up of nothing but she males They are: Debra Coxson- 37 Debra has been a lawyer for 12 years and started the firm with her college roommate Angela Dicster 5 years ago. She's a leggy ash blond with 38D tits a great ass and a 9 inch cock. She loves to ... Read full Story
bennyx709 2016-11-14 6,986 Cumshot suck oral cumming cock sucking transsexuals
87%
Fem Firm 3: The Return Of Frankie
PART 1 THE VISITOR Over the next couple of months, it was pretty much business as usual at the Firm. You know, depositions, court filings, motions, hot sloppy blow jobs and ass destroying anal sex (Thanks Angela!).Not to mention Friday Fuckfests. But since I started working here everyone se... Read full Story
bennyx709 2016-11-14 12,284 anal sex ass fucking oral sex cock sucking thick cock
83%
She came inside of me
In my city there are several transsexual brothers where there are usually a good amount of attractive girls working. It had been quite a while since I've visited one but on a hot sunday night I decided to pay one of them a visit. Even though I had been here before I was nervous, the place is... Read full Story
Gracemel121 2017-07-18 17,808 Amateur Shemale Fucks Guy
95%
My First Time
I used to be a normal straight guy, or at least, so I thought. That was until I began exploring trans porn, I was so turned on by it, but thought it was wrong, I tried to fight it, but soon enough trans porn became the only porn I could get off to. I didn't know what to do with this obsession, ... Read full Story
handsome man 2018-06-07 21,996 Crossdresser Amateur Shemale Fucks Guy Sex Toys Homemade cum in mouth
93%
My First Time Made Me A Slut
A true story of my first time. And why I so need a daddy now. The first time I went out dressed. I went to a bookstore in east Portland. As I got out of my car feeling the breeze up under my very short silky skirt, trying to pull it down as cars were wizzing by. I walked or should I say wobbled the... Read full Story
Teddie 2018-09-12 12,486 first time Stockings Crossdresser Bareback Blowjob blonde Big Cock gangbang domination Guy Fucks Shemale slut cum in mouth
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 9,089 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
66%
Oh Samantha
Meeting Samantha for the very first time at the busy theatre restaurant was the best thing that could ever happen to me. She was performing with about 20 other ladies or sort of ladies, I found out later that they were hot shemales, transsexuals and even a few transvestites. Their performanc... Read full Story
iluvgurls 2018-11-12 4,485 Cumshot Shemale Fucks Guy Blowjob Lingerie
90%
It been extremely too long
For me, the ultimate feeling of femininity happens when a man is inside me, and It had been far too long. Over the last few years, my wife had effectively shut down my indulgence in the hobby of crossdressing in public - mainly at bars frequented by the transgendered and their admirers. She only sus... Read full Story
ASSEaster5678 2019-01-09 5,334 Shemale Fucks Guy Guy Fucks Shemale
100%
Foot fetish with a twist
I immigrated to the Green Bay area after I graduated College with a BA in Finance. A discipline that keeps you to yourself and you spend your day crunching numbers and write reports. I’m a very feminine woman, I love wearing lingerie and nylons, any type of nylons (pantyhose, thigh high, etc.) Aft... Read full Story
Stephanie_logan 2019-06-28 5,037 Stockings Lingerie Guy Fucks Shemale
83%
Milking Time Jordan's Arrival
These stories involves a group of shemales who live on an island that exists in our world, but they chose to remain mostly isolated. That's part of the reason I also call them amazons. The shemales in my stories have genitalia that start at John Holmes' size, and then get much bigger. (This is a... Read full Story
gman57 2019-09-25 10,598 Big Tits Big Cock shemale + shemale
40%
vince
been gang banget by a group of bikers on my way to vegas..it was like 2.15 am when i pulled of the 15fwy to take a piss because it was hot and i was driving naked got out it was a dirt road and i walked to the bushes and started pissing when all of a sudden a bunch of bikers were rite at my truck i... Read full Story
ima satisfer 2020-06-03 4,147 Group Sex Outdoor Bareback Blowjob Big Cock gangbang Interracial Sex Toys cum in mouth vegas gang bang
100%
Estelle
Estelle sat before her dressing table, putting the finishing touches to her makeup. She had prepared herself as well as she was able, as her lover tonight was her benefactor – as the kept “whore” of Marcus Smith she owed her whole self to him and indeed, she loved him, but more than that, she loved ... Read full Story
kathysmokes1 2020-08-13 4,349 Stockings Crossdresser Bareback Fetish Big Cock Lingerie
100%
My wonderful life with Pat : The tattoo
Few hours later Marie and Pat arrived, Marie ordered me to stand-up and kiss me hardly with her tongue rolling in my mouth. She say me goodbye and thank you so much for dinner and the marvelous night, Pat is really lucky with you. I was so surprised i reply by a shy thank you. After Marie has le... Read full Story
jperrot 2020-09-18 4,515 Amateur Outdoor Shemale Fucks Guy domination Ass to Mouth cum in mouth
100%
Sissie Slut's Windows of Womanhood
I flash back to my first time with a grownup adult at the tender age of16 . I was so nervous now that we were here in the motel room. I was nervous for so many reasons. I lied to my family and told them I was staying at a friend’s house. Instead, I'm here with Mr. Joey in a motel room and he was my... Read full Story
Regina10 2021-02-22 6,650 Crossdresser Bareback Creampie Fetish Blowjob blonde Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
Horny Writing A Strange Habit
I enjoy watching videos which I can Vicariously live. This is nothing more than my horny hobby, an amalgamation of various thoughts. My form of hands free edging. Spell checked only, "No I haven't proof read a first draft, not trying to publish masterful works here." Hope to hear from those w... Read full Story
Araina 2021-03-08 2,734 Crossdresser Amateur Big Tits Cumshot Bareback Fetish Blowjob Big Cock Guy Fucks Shemale Frottage Homemade Ass to Mouth cum in mouth
100%
The Fabulous Alessia Travestita
Alessia is a real transexual. Several of her porn videos are on this site. She collaborated with me in this story. Alessia is a natural blonde haired, brown eyed, mature fifty -five year old Transsexual woman from England. She is tall, very fit, stands 5'11," 36B-26-30 and a slender 133... Read full Story
darrell 2021-12-14 4,323 Crossdresser Blowjob blonde Big Cock domination Mature cum in mouth
91%
Aby my trans daughter
I am 50 and great shemale fan. I met Aby through PlanetRomio during covid lockdown. I was alone at home that time and i was searching for some good trans or shemale. So Aby so my profile and sent me message. I immediately replied. we exchanged our contacts and then shifted our chat to Whatsapp. ... Read full Story
Stud4Shemale 2022-01-03 4,289 Crossdresser Cumshot Bareback Shemale Fucks Guy Blowjob Big Cock Asian Guy Fucks Shemale cum in mouth
88%
Alex and Jon
Alex was not beautiful, but had a sexy attractiveness that most could not help but take a second look. This was the case with Jon as he searched adult Friend-Finder ads for someone that would satisfy his desires and dreams of a companion. Alex, a transgendered Filipina girl, had the bronze skin colo... Read full Story
Jon Paul 2022-09-21 5,290 Group Sex Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale cum in mouth
80%
Outdoor Tranny Sluts Lust
I wake up really early one morning with my cock throbbing hard under the sheets. I got a white camisole on. Out of bed i go with a desire to vouyer and masturbate somewhere around my home. I'm home alone so i head out to my garden with my cock bouncing up, down & dripping cum. It's about 5am... Read full Story
Tracy Bel 2023-02-14 5,501 Crossdresser Outdoor Fetish Homemade cum in mouth shemale + shemale
100%
Oneness with the bodies
many years went into just fantasizing being with shemales. I was getting hornier day by day to try it out. But being in a relationship there was hardly any room or time for it. I once experienced it in bangkok and confirmed that I really can do it and actually love it. One day suddenly it was br... Read full Story
zyankhaan786 2023-05-30 6,435 Group Sex Bareback Shemale Fucks Guy Big Cock domination big ass cum in mouth double anal
100%
Cross dressing Aunt
CD Aunt Well, my uncle was a crossdresser, but the group is Aunt CD, so it is all kind of confusing. Back in the mid 80's I was fresh out of high school and was offered to spend the Summer with my uncle in TX, he was only 10 years older than I and was offering to let me stay with him so I could work... Read full Story
PARUSHFAN 2023-06-14 6,563 anal Crossdresser Amateur Creampie Blowjob sissy cum in mouth
100%
About Jack and Diane
Thanksgiving was over the college kids are returning to school and Las Vegas has slowed down from the busy restaurants and overcrowded casinos. It’s the best time of year to see a nice show for less. Jack’s friends had all taken off with families and he had time to think about how lonely he really w... Read full Story
Jon Paul 2023-12-20 6,768 anal Cumshot Bareback Fetish threesome Lingerie Guy Fucks Shemale small cock shemale fucks shemale cum in mouth shemale + shemale
100%
A new start in life
“In life, finding a voice is speaking and living the truth. Each of you is an original. Each of you has a distinctive voice. When you find it, your story will be told. You will be heard.” John, living outside Boston, being your average accountant working with Gillette, had gone through a messy di... Read full Story
Jon Paul 2024-05-09 2,901 anal Amateur Shemale Fucks Guy Big Cock Guy Fucks Shemale small cock big ass
100%
Becoming a Chrissy - Chapter 1
I always knew I was a little sissy slut. When I was ten, I took a pair of my mommy’s panties to try on. It was a hot pink G-string that my petite mother must have worn when she was ready to get fucked by my daddy. It was just the right size to cover my prepubescent clitty and also stretch through my... Read full Story
mindlessrobot45 2024-05-13 3,256 Crossdresser Blowjob blonde femboy cum in mouth
50%
The first requirement of a deal with Dominatrix Persephone.e
There was a number of requirements before I even consider'd fucking that sissy ass, firstly, I expected dedication to be shown and to prove that the sissy could obey my orders, after a trial period, then I consider to force my big dick down the throat of the that sissy, and then fuck brutally and ex... Read full Story
Dominatrix Persephone 2024-06-21 1,260 anal solo Cumshot Masturbation Shemale Fucks Guy Big Cock Shemale and Girl domination Mature sissy shemale fucks shemale teen (18+)
50%
Two cocks and a pussy
I'm alone in my apartment and super horny, so I decide to have some kinky alone fun time. I strip and shave my body. I'm smooth now. I put on a sexy thong and bra. Next I put on a garter belt and super sexy thigh highs. Next I put on a super short and sexy skirt, lastly I put on a lace blouse. Next ... Read full Story
spreadforalldik 2024-07-09 679 anal Crossdresser Group Sex Cumshot Bareback Fetish Blowjob cum Lingerie pantyhose crossdressing Ass to Mouth cum in mouth
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 7,833 Stockings shemale cumming
100%
The Naked Day Wedding
I'd looked forward to this day with a feeling of excitement and also a certain amount of trepidation. Now the moment had arrived and it was all happening. I looked at my gorgeous bride Tina as we signed the register of marriage in the towns' registry office. Outside, I could hear the bustling ... Read full Story
shemale lover 2011-11-24 3,085 anal shemale strapon
100%
My surprise Part 2
I managed to force myself free. I slammed my back against the cubicle door and I looked into her eyes. She was beautiful, amazing eyes, great face, nice pair of tits and a great body. She stood up, pulled her tights thong and skirt up and calmly walked by me touching my crotch and winking at the sam... Read full Story
shemale lover 2012-02-21 2,215 hardcore oral sex Guy Fucks Shemale
100%
A Day Driving in the Country
Day off, out for a drive. What a predicament, standing on the side of the road next to my open car door with my hands straight up in the air; looking down the barrel of a Highway Patrolman's handgun. I'm about to pee my pants, that is what little bit of pants I have on. The Highway Patrolman is d... Read full Story
shemale lover 2012-02-26 4,229 Fetish Blowjob crossdressing
100%
A Little Payback
Of course we'd all heard about it, how couldn't we? Apparently the drug had been invented originally for couples who were into the whole dominance/submission thing. Women who had more submissive boyfriends could make them look more like they felt on the inside or something like that, anyways that's ... Read full Story
shemale lover 2012-03-17 3,490 Fetish jerking feminization
100%
Trannies Feminize Dandy Boy
"Yea I thought the singing was OK but I don't really go for that style too much" "And the girls?" Brian prompted me. "Oh come on Brian leave him alone we all know he's not really interested in girls." "Give him a chance, people can change! Perhaps Carl's... Read full Story
shemale lover 2012-05-01 4,274 Group Sex Fetish ass fucking oral sex feminization
100%
Betrayed Chapter 1
She's having an affair. I couldn't ignore it any longer; the evidence was right there on my monitor that Wednesday afternoon. I had felt so... tawdry – a word I had thought I would never use – hiring the detective to follow her, follow up on my suspicions. It was as though I was betrayin... Read full Story
shemale lover 2012-05-28 6,396 anal sex Cumshot shemale oral sex cum swallowing
100%
My shemale GF Part 4
I am now pretty much living at Christys place along with Ashley. So Ive reverted back to my 13 year old self of having wet dreams, and its really annoying especially waking up with a puddle in the bed. Chrisy went shopping, while i was just chilling and smoking weed with Ashley. Christy walks in and... Read full Story
shemale lover 2012-07-19 2,679 shemale cum oral sex handjob
100%
Discovering Amber Chapter 3
There have been very few times in my life I have been terrified and today was definitely the tops on that list. Ms drove us to the mall and as I watched she walked around the front of the car and opened the door for me. I looked up to see her hand extended toward me. "Practice getting out li... Read full Story
shemale lover 2012-09-28 4,109 sucking Fetish domination Sex Toys
90%
Collette's Property
I've been Collette's lover for four years now and this gorgeous, incredibly kinky woman still continues to amaze me. Our sex life would be unimaginable to most people, even those who live lives embracing BDSM and other fetishes, and it's Collette who makes it happen. Of course everything is a trade ... Read full Story
shemale lover 2012-12-19 7,987 anal Crossdresser Blowjob domination ass fingering
100%
I FIND MY ROAD IN SYGKROY
My name is Anastasia, although the real name is Nick. As you can see I'm a decent boy day, a normal relationship with girl (not so normal, but that another story!), Sociableness and not effeminate at work and generally to the outside world. But when you go home and my girl is missing, I beco... Read full Story
ANASTASIS CD CRETA 2014-12-03 3,897 first time Creampie Blowjob ass fucking 69 cd
100%
My Life as a Shemale Part3
The next year would become the strangest and the most turbulent of my life, I will have to write more chapters just to get it all in. What came next was my transformation, even though it was becoming more clear to Tim, Sam and I that I was transgender from the onset. Sam came and saw me more ofte... Read full Story
shemale lover 2015-02-19 2,736 tranny Cumshot shemale ass fucking sperm
91%
My Life as a Shemale Part6
It was the night before my first day of school, I was excited. Sam was over and we were chatting away, she was really becoming a good friend. I told her about what had happened with Mike the week before and she listened to the whole story. She asked me how I had felt about it and I kind of laughed, ... Read full Story
shemale lover 2015-02-25 3,079 anal ass sex toy shemale anus
92%
A Shemale and Her Unexpected Friend and Me
There I was on the boardwalk waiting for texts back from trannies from craigslist. As I sat staring at the ocean, I yearned for some sexy shemales to get back to me. I started walking around the boardwalk more, anxiously, desperately. All the sudden, a beautiful older woman was walking by with her d... Read full Story
tysonsbakery 2015-11-16 6,843 tranny ass shemale domination double anal
88%
First Time Outdoor Festival Fantasy
Fantasy Setting: Summer time in the mountains of Colorado the perfect bluebird weekend we all dream of. The day before an underground rave in the mountains all my friends bail on the show and was now left with either not going or going solo. Well I deiced what the hell and I'll go solo an... Read full Story
xaviergc8 2016-10-26 9,573 anal first time shemale gangbang bondage outdoors fuck toy
73%
Nancy the hot and sexy TS in Pattaya
Hi this is Ris, this is my third story. Well Last year I went to Thailand on lone trip. I went directly to pattaya and had rest and went to Walking Street in the evening. Was visiting many nude bars, ts Bars, dance bars. but while walking on the street one particular girl catch my attention. s... Read full Story
Stud4Shemale 2017-05-22 9,467 Big Tits Cumshot Shemale Fucks Guy Ladyboy Guy Fucks Shemale cum in mouth
80%
Blowing Strangers
I was headed back into town from a couple weeks on the road and decided to stop for the night at a particular hotel, because it a had a small bar attached. After getting a room, I went upstairs to change. As usual, my outfit was right on the border of sexy and slutty. The five inch heels might have ... Read full Story
pennypenny 2017-07-05 7,823 Crossdresser Blowjob Guy Fucks Shemale cum in mouth
100%
one of those stories i wish i was in.
Tim stepped into his new college dorm room and breathed in the possibilities. The sun illuminated the simple tile floor and the simple room furnishings. Freshly cleaned desks and wardrobes neatly lined the walls. The beds had thin blue mats and pencil graffiti etched into the legs. He noticed that t... Read full Story
TylerTheLovely 2018-03-02 6,434 Shemale Fucks Guy
95%
What Lies Beneath (Part 1)
A RENDEZVOUS WITH SUZY – What Lies Beneath (Part 1) It had been a busy last day of the week in the office and I had started something that needed a little more time to complete. The office was quiet with most people having already left. It was a great opportunity to finish with no interruptions or ... Read full Story
The Adventures of Mia & Seth 2020-11-03 14,869 Group Sex Shemale Fucks Guy bdsm Interracial Sex Toys foursome
100%
Shawshank affair
Courtrooms can be a scary place. They smell like older leather, the wood paneling has been polished with oil and each sound penetrates your body like a loud smack from a cap pistol, which echoes in the forest, especially the gavel smacking on a block from the Judge. I felt strongly that I would be f... Read full Story
Jon Paul 2018-08-20 6,592 Stockings Crossdresser Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
66%
The Audition
New York City wasn't a bad palce to be back then. I was a student working at an office job and doing what I enjoyed. That was being a musician. Lots of weekend and night gigs at cocktail parties, lounges and so on. There were a few pianists I worked for as standing time-keeper ( bass play... Read full Story
iluvgurls 2018-11-12 5,657 Stockings Cumshot Fetish Blowjob blonde Lingerie Guy Fucks Shemale cum in mouth
100%
Chinese Apple Turnover
I crashed harder than anytime ever in my life and my dreams were fucking vivid. I dreamt of being fucked. And of sucking huge cock and getting face fucked so hard that I was cock drunk and high from holding my breath so much. But so really horny from him doing that, so into that cock. Of Jax f... Read full Story
ASSEaster5678 2019-01-09 6,567 anal sex Shemale Fucks Guy Asian Guy Fucks Shemale
40%
Kiara's Xtra large treat
I have developed an interest in t girls with the XXL tag, black and Latino girls especially seem gifted in that department, so when I seen this horney bunny on an escort page I knew I'd have to check her stats. A dark Latino Kiara boasted an impressive ten inches, I pondered on my way to meet her... Read full Story
Kinky Dee 2019-05-27 3,568 Small Tits Big Cock Lingerie domination Guy Fucks Shemale Interracial
96%
the park
I was having lots of fun at the park like always dressed like a sissy and taking cocks deep in my ass and mouth like always. It was late and I was getting ready to head home when I saw something walking towards me. I could not make it out at first but finally saw a very pretty girl about 25 with lon... Read full Story
crossdresser55 2019-09-06 7,046 Crossdresser Shemale Fucks Guy
92%
The trip
I was at work and they decided that some of us had to go to Florida to work on some problems so I was picked. I went home and packed and made sure to pack some of my sissy outfits also because I would be in a hotel for 7 days and have the room to myself it was perfect. The next morning me and the ot... Read full Story
crossdresser55 2019-09-18 12,238 Stockings Crossdresser Shemale Fucks Guy Fetish Sex Toys