Sort by
Relevancy

Free Stories

100%
From boy to crossdresser episode 2
940 / 5.000 I had already learned to masturbate, I used to cum several times a day and it continued until I got older. I was still going to school and I was more lustful than before. I remember when we used to go to my aunt's house, my brother and I would sleep next to the cousin, when every... Read full Story
Nickinickharddick13 2024-09-02 2,595 Amateur Big Tits Masturbation Homemade teen (18+)
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 10,930 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 34,987 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
90%
Camming Down the Rabbit Hole Ch. 08
A familiar sensation greeted me as my eyes opened and a yawn escaped my mouth, that oh so delicious feeling of my morning wood straining against my silk night ware. It was becoming an ever occurring pattern that no matter how large the orgasm the night before I would wake with the hardest of cocks, ... Read full Story
Dani_does_Dallas 2021-11-15 4,366 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Uniform Lingerie Homemade self sucking pov cum in mouth
100%
Camming Down the Rabbit Hole Ch. 11
I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hopin... Read full Story
Dani_does_Dallas 2022-04-25 4,702 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth
100%
Part 2..My First time (Cont).
Part 2. I remember asking Andy if being made love to would hurt me, (note I said made love to and not being fucked) and he said it would hurt the first time but after that it should be ok so I asked him to make love to me. He asked me what position I would like and I replied I had no idea as this w... Read full Story
Nicole-Andrea 2022-10-05 4,640 Crossdresser Amateur Bareback Lingerie
60%
Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
shemale lover 2012-09-28 7,006 Cumshot Fetish oral sex cum swallowing
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 9,270 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
90%
A Schoolgirl Fantasy
As I sat on the couch watching some boring show, I was thinking, "Being alone doesn't have good perks. Maybe if I wanted to dream something naughty, it might be cool." So, I closed my eyes, and I dreamed of a very naughty transexual schoolgirl who would do what I needed. All of a sudden, I heard a s... Read full Story
OldHungDude67 2019-03-04 5,963 Amateur Cumshot Blowjob Uniform Guy Fucks Shemale Homemade Ass to Mouth
72%
Wie sich schlagartig mein Sex Leben änderte... Teil 1
ich war nun schon einige Zeit heimlicher Crossdresser. Nie wurde ich von meiner Freundin erwischt, auch wenn es manchmal wirklich knapp war! Ich hatte ein sicheres Versteck für meine schönen Sachen und meine Sextoys und konnte hin und wieder meine geheime Neigung ausleben wenn sie nicht da war.Trotz... Read full Story
Holly Swallow 2019-03-20 8,381 Stockings Small Tits Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob blonde gangbang domination Interracial Sex Toys humiliation Homemade sissy girlfriend chastity cage Ass to Mouth cum in mouth chastity sissy amateur crossdresser fendom
77%
Porn site meeting and fucking ;)
We started talking on a site. I knew you were for real when you sent me a message introducing yourself. We only spoke for 2 days before we decided to meet up and I was excited to play with a real little slut. You told me the only things off limit were anal and scat otherwise i could do what I wanted... Read full Story
BalkanLoco91Ri 2019-08-26 5,494 Teen (18+) Amateur Cumshot Masturbation Bareback Blowjob Big Cock Uniform domination Homemade pov Ass to Mouth cum in mouth
40%
Kitten: A Pantyboy StoryKitten: A Pantyboy Story
It's easy now to look back and play armchair psychiatrist and see where my fetish for school uniforms and cute cotton panties started, but it wasn't until I met MISTRESS that I realized exactly how deep that fetish was ingrained in my mind and soul. Mistress knew I was a pantyboy after the first ... Read full Story
shemale lover 2012-09-10 7,475 Crossdresser fingering Sex Toys handjob 69
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 8,424 anal Crossdresser Blowjob domination ass fingering
100%
Lady In The House Ch. 09
A story by MicheleNylons ( Continued adventures of a cross-dressed prison prostitute. ) I lay there stunned, how had I miscalculated my effect on the Warden? The one man who could guarantee a transfer from this shit-hole; fuck!!!! The cravings of male sexual hunger within the confines of the ... Read full Story
✘Transensual✘ 2019-02-27 6,276 Crossdresser domination Guy Fucks Shemale cum in mouth PRISON FUCKBOY PRISON PUNK prisoner Prison Bitch
41%
My first date with a "shemale"
I met a guy whom i worked with and found out he was bisexual,it didn't bother me nor did i care because i know who i was.I realized he was trying to date me without asking me if i was that way.I flat out turned him down and told him i didn't go that way! I was still young and new to this. I was coo... Read full Story
bmogotti 2020-03-09 13,802 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
100%
SABATO SERA CON PAOLA
L'appuntamento del sabato sera con Paola sta ormai diventando un appuntamento fisso. Ho trascorso la settimana facendo il conto alla rovescia e cercando di immaginare quale sarà il suo regalo che non mi ha mai dato! Sono le 9 di sera, arrivo finalmente a casa sua, il cancello è aperto, la porta è ... Read full Story
Sissy Mari 2021-10-13 1,577 Stockings Crossdresser Amateur Fetish Lingerie domination Homemade shemale + shemale sissy slut sissy crossdresser
100%
Paola mi porta a cena
E' venerdì e mi arriva un messaggio da Paola: "Domani sera vieni prima di cena" Cosa avrà in mente? La sera dopo arrivo a casa sua prima delle sette. Paola mi attende, il viso truccato perfettamente, i lunghi capelli pettinati. Indossa una leggera vestaglia semi trasparente che lascia intravedere i... Read full Story
Sissy Mari 2021-10-25 1,535 Stockings Crossdresser Amateur Masturbation Lingerie Homemade shemale + shemale sissy slut sissy crossdresser
85%
Afternoon Tea on the Lawn
I waited outside the shop for it to open. It was quite chilly and my legs where frozen even though I wore an expensive pair of sheer stockings. The dress wasn't much warmer and I wished I had a full-length coat. Trish, the owner was the first to arrive. 'Hello darling, nice Christmas?' She kne... Read full Story
shemale lover 2012-08-29 4,834 Stockings Lingerie oral sex cum swallowing tiny cock
100%
Josephine's First Day
My life at school was fairly uneventful. I wasn't brilliant academically. I wasn't a talented sportsman, actor or musician. I wasn't one of the popular children. I wasn't in physical fear from bullying, although there was a lot of teasing, name calling and 'jokes' that were funny for everyone else. ... Read full Story
shemale lover 2013-01-04 9,318 Teen (18+) Crossdresser sucking Uniform handjob
100%
la storia di Sara
Erano alcune settimane che ciattavo con Sara, una trans bolognese conosciuta per caso in internet. Di Sara ho visto solo il bel viso molto femminile con lunghi capelli biondi ed il suo meraviglioso seno. Una sera stavamo parlando e lei mi disse " alcuni mesi fa mi sono rifatta il seno, ho conosciut... Read full Story
Sissy Mari 2022-03-22 3,023 Crossdresser Amateur Cumshot cum Ladyboy Lingerie Sex Toys Homemade shemale + shemale sissy crossdresser siisy slut
100%
The Married Man of Summer #1
The Married Man of Summer #1 By Sabrina G. Langton *** Something quick.. something from a nice quiet neighborhood, I hope YOU like it... *Stories from the real world This story is slightly, slightly, very slightly autobiographical. Ha... *** Between the beginning of summer 1987 and th... Read full Story
Brina Giselle 2024-02-03 5,952 Crossdresser transgender blowjobs dress
85%
Boys to girls transformation with a surprise part I
Boys to Girls with surprise For the first time I scheduled an appointment at a studio that will transfer me into a sexy women. I packed my sexiest outfits and high heels and drove to the next city where the studio is. I told everybody I had to go to a business meeting over the weekend. I arrive... Read full Story
TRTRAIN 2024-09-01 2,917 anal Crossdresser Amateur Group Sex Sex Toys Mature Homemade sissy shemale fucks shemale
100%
Sissy For My Flatmate Chapter 2
If you've only just tuned in, here's what's going on in my life. Until recently I was a closet crossdresser trying to keep my hobby from my flatmate. When he caught me in the act, I found out that not only had he known about me for a long time but it was a turn on for him. I agreed to become his sis... Read full Story
shemale lover 2012-08-12 4,067 oral sex cum swallowing sissy
76%
My Wife's Secret Fantasy Chapter 1
PART ONE: REALIZATION The old saying "you never really ever know some one" is quite true when it comes to my wife Debbie. Debbie has always seemed to come up with new surprises to keep our marriage stimulated and adventuresome. As I've recently found out though she seems to have been ke... Read full Story
shemale lover 2012-09-09 10,349 Crossdresser Cumshot Masturbation Lingerie heels
0%
Crossdreaming Thoughts
Last week I crossdressed for a while. Wore tight dark green jeggings, and two different shirts. I was barely able to squeeze these huge fucking J cup tits into a basically skin tight size XS stretchy nylon beige tshirt, and the other was an olive green turtleneck of the same tight fit. Wore both ins... Read full Story
Maika Arreola 2018-03-02 4,800 Crossdresser Amateur Big Tits Big Cock Mature Homemade
100%
SissY Piss faggot Facts Lena Scarlett sissy
Well, hi :) I just want to let you know that I won't post stuff here chronologically as I wanted :) HARD WORK xD Instead I will post all the quick thoughts about me and my sissy faggot experiences, OK? Now, today I just wanted to say that I've just realised that I'm beggining to like stuf... Read full Story
Lena Scarlett 2024-11-06 3,107 Small Tits Crossdresser Fetish Uniform Guy Fucks Shemale Sex Toys sissy piss Solo Shemale Compilation Ass to Mouth teen (18+)
50%
My pink panties
My pink panties .... You pointed to the bed and said to put on the lingerie that you had picked out for me. There on the bed was a pair of pretty pink panties that had a bow on the front, a pink lace bra, a pink lace garter belt and a pair of fully fashioned stockings. What a lovely feeling ... Read full Story
amberdoll 2018-07-09 2,171 Crossdresser Amateur Homemade
60%
My first gurly orgasm
My first gurly orgasm Me being taught to have my first girly orgasm... 'You cute little bitch, Amber, it is time to have your pussy introduced to your first orgasm. You loved my fingers, and this will be better, I promise. It may hurt a little at first, but, let that pass and you will be in ... Read full Story
amberdoll 2018-07-09 2,795 Crossdresser Amateur Homemade
66%
My pink panties
.... You pointed to the bed and said to put on the lingerie that you had picked out for me. There on the bed was a pair of pretty pink panties that had a bow on the front, a pink lace bra, a pink lace garter belt and a pair of fully fashioned stockings. What a lovely feeling rolling the stocking... Read full Story
amberdoll 2018-11-07 3,111 Crossdresser Amateur Homemade
76%
My first girly orgasm
Me being taught to have my first girly orgasm... 'You cute little bitch, Amber, it is time to have your pussy introduced to your first orgasm. You loved my fingers, and this will be better, I promise. It may hurt a little at first, but, let that pass and you will be in girly heaven. I felt s... Read full Story
amberdoll 2018-11-07 4,963 Crossdresser Amateur Homemade
100%
sissygurl
Sissygurl development A true sissy always wants to always look as sexy and desirable as possible and with a body that looks fabulous in your sexy sissy outfits so you will be super motivated to stay sleek and slim. Now let’s talk make-up. Besides the essential stuff to have in your make-up kit... Read full Story
amberdoll 2023-02-16 6,558 Small Tits Crossdresser Amateur Homemade
100%
a day in the life of Amber
Hi daddy, I hadn't paraded for a few days but I did just a minute ago. He just wanted to watch me really take my dress and panties off He didn't ask me to do anything else really I sucked my finger and fondled my tits for him I would have done anything he asked I have become used to that wit... Read full Story
amberdoll 2021-03-18 2,913 Stockings Small Tits Crossdresser Amateur blonde Lingerie Homemade
60%
Dreaming about these Gorgeous woman
I'm always horny 24/7 no matter what I'm doing. I stay horny sometimes I get some play time at the same time I really don't get too much play time. I get a lot of compliments from a lot of beautiful Transgender and CDs and a lot of people think it should be easy for me to get a girl... Read full Story
BigDaddy8inchz 2023-02-10 4,479 Crossdresser Masturbation Bareback Homemade Transgenders fucking shemale
100%
I unlocked my Gooch /Taint pleasure in bed with str8 friend.
So I have this quick story I used to expiremental with a straight friend of mine hes white guy pretty husky body and thick guy with blue eyes. We’re very different but the same on things. A few times when we get drunk we actually and have fun but nothing penetrative. But he does become more… Open Mi... Read full Story
Ezra_Kyle25 2024-09-11 2,747 Crossdresser solo Amateur Cumshot Masturbation Ebony Lingerie domination Guy Fucks Shemale Interracial Homemade sissy femboy
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 17,872 Crossdresser sucking Big Cock ass licking big boobs
94%
My first time crossdressing with a man
It was Christmas night 2016 and I had gone out to the bar with a few friends. Came home a little tipsy and very horny! I rushed to my room, took off all my clothes and put on a very sexy, slutty outfit (black lace thong with matching bra, a blue sweater, black mini-skirt, and black knee high boots) ... Read full Story
Betty D 2021-01-18 9,125 first time Crossdresser Amateur Cumshot Fetish Blowjob Mature Homemade mini skirt small cocks black panties obese