Sort by
Relevancy

Free Stories

93%
Sissy Maddie's New Apartment Gangbang
I’d just moved into the big city. Me on my own in a cheap apartment block. The flat was nothing special by any means, and the room next to mine seemed to be noisy with parties. But I was glad to be on my own. I had almost finished unpacking my belongings when I came across my stash of female clothi... Read full Story
sissymaddiex 2020-09-25 10,328 Crossdresser Amateur Group Sex Cumshot Bareback Creampie Blowjob gangbang Lingerie Homemade sissy cum in mouth double anal
100%
TO BE OR NOT TO BE – PART 6
TO BE OR NOT TO BE – PART 6 by Spanky de Bautumn Part 5. Sunny and Antonio got frisky at the bar, Sunny moved in with Mel and Shari, and opening night was a success The only other dress that I brought was one that I hoped I would get a chance to wear but didn't think I would. It was a black ... Read full Story
SpankydeBautumn 2021-02-26 2,679 Crossdresser Cumshot Masturbation Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
think about cock all the time
i find myself looking at chicks with dicks all the time. i love them. they turn me on so much. i cant stop thinking about being with one and im going to be with one very soon. i cant wait to swallow all of her shaft. every inch of it. and when she starts to cum i will suck it in deeper. fuck that tu... Read full Story
jenny green 2022-01-05 2,776 Crossdresser Cumshot Bareback Blowjob Big Cock Mature cum in mouth shemale + shemale
83%
How i became a sissy/my first blowjob
I'm a 17 year old sissy now but i started crossdressing 4 years ago when i was 13 :).This is the story. One day my parents went to our lake house for the weekend with my s****r but i was feeling sick so they left me with my grandparents. They were taking care of me for a day or two and i got better ... Read full Story
shemale lover 2013-08-09 54,159 Teen (18+) Crossdresser suck oral cum swallowing cd
69%
Sissy School
I arrived at the school at 8AM for the start of my new life. The school had promised a lot when I saw their website but I wasn’t quite sure what I was in for. I had arrived dressed in male clothes with none of my belongings as I had been instructed to on the website. I walked through the gates into ... Read full Story
Sissysophie780 2019-07-04 19,497 humiliation schoolgirl sissy slut punishment School uniform
82%
How I knew
Like a lot of you we all have our stories and how we arrived at being our unique selves. I was lucky to have girl cousins that saw me as one of them at a very early age and introduced me to my girly side! Sleepovers were great, I would end up wearing their pjs/nighties etc and never once thought i... Read full Story
Veronica Trapani 2019-12-06 7,060 Teen (18+) Amateur Cumshot Homemade cum in mouth
77%
Best friend
Looking back, it seems my early teens were really a time for me sexually. Puberty had set in hard and fast and I was sexually charged. I was constantly touching myself and fantasizing about every sexual explicit act I could think of at the time. Lucky for me I had my best friend Jason. We wer... Read full Story
Veronica Trapani 2020-03-09 6,472 Teen (18+) Amateur Outdoor Blowjob Homemade cum in mouth
80%
Spankys mother cloths torn off on stage reveal she has cockoc
Erotic website remake of the little Rascals short film remake of Beginners Luck. The audience is laughing hysterically at Spanky attempts to open his stuck helmet. Spankys mother, a blonde beauty peeks out at the audience from the stage wing, as the crowd’s loud laughter, nervously biting her finge... Read full Story
kucksissylicktoman 2020-06-16 5,439 Big Tits Cumshot Masturbation Fetish Blowjob blonde Big Cock gangbang Lingerie Guy Fucks Shemale cum in mouth shemale + shemale
81%
First time with ladyboy / bottom
Hi everyone! now it is my turn to share my experience in Thailand. We were on a Christmas vacation on an island, and I didn’t even know ladyboy existed then. At a Christmas beach party I chatted and danced with a woman and we ended up in my bungalow. We kissed a lot and I knew that now I was g... Read full Story
FoxyLover'ts 2020-10-06 16,568 Cumshot Blowjob Big Cock domination Interracial Homemade cum in mouth ladyboy ts thailand ladyboy shemale fuck guys virgin ass bottom boy bottom virgin
100%
From accidental trans porn addiction to a cum filled booty
One night when I was around 30 or so I was watching some porn, nothing unusual for a guy like me, aka a sex addict. Sex addiction is great if you’re Tiger Woods and swimming in poon, but for guys like me - regular, awkward, slightly handsome in a very boyish way, weirdos — it’s not that fun. We... Read full Story
CDJaneBooty 2022-04-01 10,534 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
100%
He Could Have R*ped Me!
This guy was so big, taller than me and I'm 6 feet, and bigger, not fat, just right for his big size, and I am so skinny, except for my tummy, that he could have pinned me down and forced himself onto and into me against my will, and no matter how much I'd struggle with him and fight back, he could ... Read full Story
Chrissy Tunnell 2022-02-02 3,037 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 4,341 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
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 5,784 Crossdresser Outdoor Fetish Homemade cum in mouth shemale + shemale
100%
Fucked by Dany Suad and sucked her off
I'm just back from Glasgow and finally had the chance to make an appointment with Dany Suad. I always found her wide hips, voluptuous thighs, her hot ass in combination with the strong cock extremely attractive. Her face is also very pretty. I booked an hour with a cumshot. She was wearing sexy unde... Read full Story
Bigpruegel69 2024-02-23 7,582 Amateur Cumshot Masturbation Creampie Shemale Fucks Guy Blowjob cum in mouth
82%
My first blowjob
I met a shemale online called melisa and we had been talking over msn for afew days, mainly having saucy chats about sex and getting off. She asked me to meet her on the coming weekend which excited me as i was a virgin to cock. We arranged to meet in a bar that was a stone's throw away from my f... Read full Story
shemale lover 2012-06-06 13,808 first time Cumshot Blowjob shemale cum swallowing
100%
David to Dee
"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... Read full Story
shemale lover 2012-07-29 12,831 Cumshot Masturbation oral sex
100%
Young Sissy Chapter 1
I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... Read full Story
shemale lover 2013-01-04 10,439 sucking Fetish Uniform domination big boobs
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 8,140 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
90%
Shemale Charlotte caught wanking in the bath
Charlotte is a very small 18 year old, very skinny, only just 5 foot but has an amazing pair of breasts which stretching the skin makes them show veins all over. Her pale skin showing the veins even more. Charlotte is also a shemale, her small size and large breasts she also has a very large 8inch (... Read full Story
shemale lover 2013-06-18 7,166 Amateur Cumshot Masturbation jerking Shemale and Girl
72%
A sexy shemale from India
hi im Ris Indian origin and stay at pune and im crazy shemale lover and i was searching for some shemale in Pune city. while brousing on facebook, I came across this shemale kainat. i interacted and made arrangement, and went to meet her. The room was quite dark and as i went through the bright... Read full Story
Stud4Shemale 2014-01-27 4,611 Cumshot suck Blowjob shemale oral 69
78%
Getting dressed one second, cum dripping from my thong the next.
So, I was going to write a cute little story of how excited I was to see my friend tonight. We hung out last week and didn't do much, but cuddle. But, ever since that night I have been craving a hard cock inside me. All I've thought about is sucking his dick until his cum is running down m... Read full Story
Shiloh Patutie 2017-04-29 6,940 Masturbation Guy Fucks Shemale panties Solo Shemale cum in panties
80%
fuck by my best friend's family
= Part 1. Alice's father = My name is Onikky 28-year-old Shemale from ASIAN, this story only shares the first experience of making love. The story begins when I first moved to a big city, looking for a new atmosphere, I don't have a place to live that I know is only my friend's name Alice who ... Read full Story
Onikky 2019-06-25 9,710 Amateur Masturbation Big Cock Asian Ladyboy gangbang Lingerie domination Guy Fucks Shemale Sex Toys Homemade Ass to Mouth cum in mouth
88%
Trip to Portimão
It is about a 3 hour drive depending on traffic to the Tivoli Marina Portimão in the Algarve from where I was staying at the Hotel Mundial. Oliva came to pick me up. She had one of those Toyota SUV things. I put my bag in the car and I noticed Olivia had rather a collection of luggage. I smiled to m... Read full Story
Rusty12 2020-09-18 4,295 Amateur Cumshot Masturbation Shemale Fucks Guy Blowjob domination old-and-young
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 20,543 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob blonde Big Cock Ebony Uniform domination cum in mouth
97%
Shemale fucks guy - My gf fucks my slutty ass.
I have a shemale girlfriend & we both are in a relationship. One day, I decide to give her a visit. I'm 5'7 guy & she's 6 feet. That makes her tall & intimidating & whenever we meet, it's me who become her gf. I visit her, she takes me in. SHe pulls me towards her while giving me a deep kiss. I ... Read full Story
glodobox 2020-12-04 22,926 Amateur Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Homemade cum in mouth
100%
An Orgasmic Uber Ride
"Chris?" the Uber driver asked me after driving up and rolling down his window. "Yes," I replied and then I got into the passenger seat next to him. I usually ride upfront in Uber rides because I get car sick easily in the back. After fastening my seat belt we were off. The guy was older, maybe ... Read full Story
Chrissy Tunnell 2022-02-18 3,718 Crossdresser Amateur Outdoor Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
93%
First Time I tasted Tgirl Sperm
I met a Mexican Trans girl online from Hermosillo and we hit it off and corresponded for a a few months. The vibe was good and ended up deciding that I would help her pay the $140 bucks for her 6-month tourist visa to come up and visit..the process took forever but once she got it, I booked her a pl... Read full Story
AllenB 2022-08-09 9,166 Crossdresser Amateur Cumshot Latina Bareback Creampie Shemale Fucks Guy Fetish Blowjob Interracial Homemade cum in mouth
50%
She also conquered my soul...
Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... Read full Story
hippocampus_171 2022-11-22 4,286 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
100%
My first time
My mother always said she wanted a daughter….my guy name was Adrian, so you could see where she was going with that. I was also a real sissy as a kid, terrible at sports, threw like a girl, did very few real boy things. My best friend and I discovered porn and masturbation together. My mom... Read full Story
shemale lover 2012-10-22 6,443 first time cum oral sex cum swallowing feminization
82%
Dick And Ass
I don't have this kind of sex often, I feel like it's wrong to want this, wrong to crave this so badly. I am by no means a sissy or a gay man. I have a wife a family.... I just need it the domination the surrender of all my will and being, the first thrust that hurts so fucking bad when it... Read full Story
JustaSwitch1 2016-06-15 11,779 Shemale Fucks Guy oral domination bbw
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 22,396 Crossdresser Amateur Shemale Fucks Guy Sex Toys Homemade cum in mouth
100%
Porn Cinemas and GinaG
I really like porn cinemas, there is a certain seediness and sleaziness about them that makes them alluring to me. My problem is that living as I do in the south of the UK, there are no porn cinemas anywhere near me. Fortunately, I travel in my job quite a bit and so can get to cinemas in Birmingham... Read full Story
GinaG 2019-01-08 3,631 Stockings Crossdresser Amateur Cumshot Masturbation Blowjob Lingerie Mature cum in mouth shemale + shemale
100%
Liberty in Lisbon Part 3
After Olivia had so perfectly taken my anal virginity, we laid in bed cuddling, touching, kissing and her cum leaking from me. I had not been so lovingly caressed for such a long time. It was just perfect. She asked me how I was feeling. I think I said before that I don’t do deep and meaningful very... Read full Story
Rusty12 2020-09-16 3,584 Masturbation Shemale Fucks Guy Blowjob old-and-young 69 sucking
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 3,896 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
100%
Maddie and the public bathroom antics
I had put on my lingerie and my dress underneath my manly clothes and was preparing myself to go to a public bathroom. The idea was to enter a cubicle, take off my boring man clothes and sit there looking like a sexy sissy where I could video myself on my smartphone. I needed some hot new pics, so I... Read full Story
sissymaddiex 2023-01-06 4,190 Crossdresser Amateur Cumshot Masturbation Bareback Blowjob Lingerie cum in mouth
100%
Shemale fantasy with female squirting
I just finished my mornig coffee at the breakfast bar in the kitchen when the door beel rung. My wife opened the doo and it was one of her hot friends. She invited her to sit at the bar beside me and serve her a coffee. Right before she gives her the coffe she slips something into the brew. Her ... Read full Story
TRTRAIN 2023-05-21 3,802 anal Stockings Amateur Big Tits Big Cock Lingerie Shemale and Girl pantyhose Mature Homemade Ass to Mouth cum in mouth shemale fucks female
100%
Leticia, a Shemale hooker in Berlin
Last week I was in Berlin again on business and wanted to take a look at what the capital has to offer. My interest immediately fell on Leticia. She answered my phone call right away and answered in English. As we agreed for an hour later. Tariff customary in the industry, 150 for 30 plus 50 for cum... Read full Story
Bigpruegel69 2023-12-12 6,542 Cumshot Creampie Blowjob cum in mouth
100%
My story
Please don't hurt me, I whimpered softly. Oh no my Lil slut, mommy has no intention of hurting you but making your fantasy become real, she said. But your thing, its kinda big. I'm a bit scared, I said. Mmmmmm, don't worry baby. Mommy wants this to be so good that you become my steady, she said... Read full Story
Curious_billy 2024-02-03 6,716 anal Amateur Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Big Cock domination Mature Homemade cum in mouth
100%
A Series of Perverse Dreams, Part 2
Three or four days had passed since my torrid alley way dream. Hannah had recently come over to share a few glasses of wine and a steamy fuck session in the shower. She had definitely embraced the ways of edging I had shown her because when she came in my mouth I could barely contain the massive amo... Read full Story
KaceyKlarissa 2024-02-29 4,867 Crossdresser Big Tits Cumshot Bareback Fetish Blowjob blonde Big Cock big ass Futanari bukkake sissy cum in mouth
100%
TS Lisa from Frankfurt +49151-26928696
Every time I'm in Frankfurt, a visit to Lisa is a must. She has a small apartment near the old opera house. You can always reach her pretty quickly. I call her and she answers straight away. I say hello Lisa, I've been to your place before and she answers in a friendly way, so you know where to go. ... Read full Story
Bigpruegel69 2024-09-07 2,126 Cumshot Creampie Blowjob Asian Ladyboy cum in mouth
100%
In Need of Some Sex
In Need of Some Sex By Sabrina G. Langton *** Author's Note: Hi... Just a teensy tiny story. I'm sure you know what I, um, well we like. Just a little sex in the night to make the heart grow fonder. Just two people meeting for the first time, definitely not the last. A nice intro to a new rel... Read full Story
Brina Giselle 2024-09-18 1,268 Crossdresser Blowjob pantyhose kissing transgender crossdresser with men
86%
Giving shemale a blowjob for the first time
I've been fantasizing about a shemale cock for a long time. Get me right, I am a straight man and all, but somehow the idea of sucking a girl's dick always turned me on. I'm not a big fan of anal sex and I don't think I'd love someone's cock in my ass, I'd rather prefer to give shemale a blowjob. ... Read full Story
shemale lover 2011-07-09 12,317 licking Blowjob shemale
71%
Sissy For My Flatmate
My heart was racing as I gazed up at my flatmate, there was an something of an evil gleam in his eyes as he looked down at me and my mind kept jumping back to the events that lead to this moment. I'm a closet crossdresser, yet now my flatmate (whom I managed to hide my “hobby” from fo... Read full Story
shemale lover 2012-07-25 6,759 Stockings Fetish sissy
93%
Proud To Be A Sissy Chapter 7
"You're being really dirty little sissy slut today," daddy chuckled and asked, "What's gotten into you?" "Making up for the last few days I guess," I giggled hugging him tightly, "and I missed you too." "I missed my little sissy too." He repl... Read full Story
shemale lover 2012-12-24 7,919 Crossdresser Cumshot Blowjob Big Cock ass fucking
100%
Submissive sissy Jennifers first cock
There is a shy knock on your door. You open it, wondering who it can be. A stranger hands you the end of a dog chain, you can see that it leads to a red strap round his neck. "I'm Jennifer, Sir" he whispers, softly & huskily. It becomes clear now - you remember the conversation on the... Read full Story
shemale lover 2013-05-01 6,890 Stockings Blowjob fingering nipples
55%
MY New Experience with Shemale in Pune
I was browsing on Planet Romeo one day and i came across this profile of Nisha shemale in pune. I sent her offline message and second day i got reply that she is available and she charges around 2.5K. then we exchanged contact numbers and i spoke to her and negotiated with her for 2k and she agreed.... Read full Story
Stud4Shemale 2014-09-17 22,105 Cumshot suck Blowjob shemale oral sex 69
72%
Sissy's Cherry Got Popped!
S)heplacement- Definition- Any sissy male that is willing to take the place, or replace any woman who is not properly taking care of their man inside or outside the bedroom... These gu(y)rls will make sure their makeup and lipstick is just right, their lingerie is matching, and that they are always ... Read full Story
Kevyn-JeanneHarris 2015-12-20 9,764 anal sex submissive sissy cross dresser
78%
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 72,348 Teen (18+) Crossdresser transgender sissy slut.trinity
65%
Prostitute Shemale
Im a shemale prostitute,and yesterday one of my customers, booked me as an out call to his hotel, I was dressed super sexy and looked hot, even the taxi driver couldn't take his eyes off me, so I gave him a little show and opened my sexy shaven legs, anyway got to the hotel, went up to my clien... Read full Story
pjboys 2017-04-18 8,453 ass suck Blowjob shemale cumming oral sex
69%
Pune crossdresser Night Girl
Hi friends, I hope you liked my earlier stories. This is my new story about a lady boy / crossdresser / sissy boy. Around 2 years back I came across a profile on Planet Romeo with name Nightgirl. I sent her message that i found her sexy and attracted to her and wanna meet her. I am alway... Read full Story
Stud4Shemale 2017-05-22 7,713 Crossdresser Asian Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
95%
Mai
When I was twelve I met a new classmate named Dave, he and I became great friends hanging out, joining clubs and what ever else high school kids do. His family was from the Phillipines and he and his sister were the first generation born in this country. His sister Mai is the focus of this story. ... Read full Story
Zöe from Kingston 2018-08-09 11,535 Cumshot Bareback Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale Interracial cum in mouth
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 2,914 Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
100%
Deflowering Latina Sissy Destiny
A real life story of my one and only time deflowering someone and being their first real encounter, I was 27 at the time and she was 21. I am absolutely convinced that Trans girls and CDs have a bit of a 6th sense when it comes to perceiving which guys are into them even in a public situation. I ... Read full Story
AllenB 2022-09-07 6,598 first time Big Cock Guy Fucks Shemale Homemade sissy travesti cum in mouth
100%
I fucked my personal trainers ass for the first time
I greeted him on my bed in my sheer black lingerie. I knew he’d be nervous, and truly I was as well. We’d spend so much time in the gym together and I knew he wanted me, but taking that next step was sometimes difficult, especially when our relationship was always professional. Posing for him, I r... Read full Story
Madison Heights 2023-05-18 7,322 anal Shemale Fucks Guy Big Cock Frottage
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 3,542 anal Amateur Shemale Fucks Guy Big Cock Guy Fucks Shemale small cock big ass
100%
A Job in the Theatre Chapter 14
Sarah and Paula shared at drink as they tried to decide what to wear for their date. "Every good outfit starts with lingerie. What do you think of these?" Paula asked holding up a pair of baby blue panties. "Nice. But I really think these will be better" Sarah said holding up ... Read full Story
shemale lover 2012-03-14 2,790 sucking shemale kissing