Sort by
Relevancy

Free Stories

90%
First Outdoor Fuck
Sat in my office with nothing to do was making me tired there was no customers to serve which was slowly driving me mad, what was worse was the hot weather outside which always makes me horny, knowing I had all my girly clothes in the boot of my car was making my cock twitch in my cheap nylon work t... Read full Story
shemale lover 2012-12-19 6,195 Crossdresser Outdoor ass fucking pantyhose heels
60%
Fat Indian Crossdresser Slut Gangbang
I am your typical sissy bottom guy who loves mature men. My proportions being large, club me into the BBW category so only the daring types can enslave me. Mature men in the age group 35-60 attract me. Only young guys with very huge dicks are an exception. This is about a naughty adventure of min... Read full Story
shemale lover 2013-03-19 6,118 Crossdresser sucking gangbang ass fucking
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 9,824 Crossdresser Amateur Group Sex Cumshot Bareback Creampie Blowjob gangbang Lingerie Homemade sissy cum in mouth double anal
100%
What a sissy crossdresser really craves and fantasizes about
(This is non-fiction) Lots of attention. To be seen and watched. I want the neighbors to see me as I stroll in my yard wearing white vanity fair panties and bra, heels, with a lacy top and a cute bob wig. With my cock raging hard thru the pretty lacy panties, struggling to be free, bouncing around... Read full Story
kelliecdgirl 2024-05-21 1,404 Crossdresser Cumshot Outdoor Masturbation Lingerie sissy femboy
100%
Lustful Crossdresser by CDlishmis
As I think about the way I feel when I dress in women’s clothes. I become agitated with myself. I can’t stop. I couldn’t stop even if I wanted to, it is an addiction. The physi cal and mental transformation that I go through is ex... Read full Story
cdlishmis 2020-08-31 3,081 Crossdresser Blowjob gangbang Lingerie domination cum in mouth psychological
62%
Crossdressed Lana - Hannover, Germany
Crossdressed Lana - Hannover, Germany Very Sexy & Compliant Sub-Slut Is Searching For Kinky BDSM Live-Dates At Hannover, Germany!!! I Am Bisexual And Want Men, Woman, Couples And Trans For Outdoor, Swingerclub, Porncinema And Public Sex. I Love To Wear Very Hot & Sexy Clothes Like Lingerie, Stoc... Read full Story
Crossdressed Lana 2020-02-06 4,155 Stockings Crossdresser Group Sex Outdoor Bareback Fetish Blowjob gangbang Lingerie domination Latex Sex Toys double anal
100%
Gangbanged at the beach
My BBC friend took me to the beach, where people make sex. We arrived in his van. I was in the back of the van, chained blind folded, with my mouth wide open and a huge horse dildo in my sissy pussy. Suddenly I hear the van door opening. I hear many voices of other men. My BBC friend was telling oth... Read full Story
brunasissyslavedolrj 2022-05-09 4,370 Crossdresser Group Sex Outdoor Fetish Big Cock Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
100%
A Series of Perverse Dreams, Part 1
My relationship with Hannah had always been mutual in the idea that neither one of us was ever truly the dominant one. It was an equal, balanced relationship of mutual fucking and sucking. However, I had REALLY enjoyed being made into a submissive sissy slut by Nikki. Something changed in me after o... Read full Story
KaceyKlarissa 2024-02-24 4,939 anal Small Tits Crossdresser Group Sex Big Tits Outdoor Big Cock gangbang domination sissy femboy Ass to Mouth cum in mouth
75%
The journey down the Rabbit Hole...
Nearly 30 years, living a double life. Sneaking around on two Xwives, several girlfriends, all to play with men.Play,and play and play. Responding to personal adds in the paper at first, then I found the Bath House. Wow, to a closeted homophobic acting oilfield lifestyle kind of guy, who could hide ... Read full Story
badbadboi667 2020-11-24 3,157 Crossdresser Amateur Group Sex Cumshot Outdoor Bareback Blowjob Big Cock gangbang domination Homemade Ass to Mouth
83%
The sissy dreams
Everyday I wake up in a state , halfway between a happy sissy and a closeted white boy. My mind is constantly trapped in that state. Suffering in silence, the people in my life seem to be oblivious to it, I have it well hid. 48 years of fist fights and weed, long hair and leather coats, Oilfield job... Read full Story
badbadboi667 2021-01-04 4,936 Crossdresser Amateur Group Sex Outdoor Bareback Creampie Blowjob Big Cock gangbang domination Homemade Ass to Mouth cum in mouth
50%
Meine sexy set card
Name: gaggedthonglover Geschlecht: männlich Haarfarbe: braun Haarlänge: lang Größe: 187 cm Gewicht: 81 kg Bist Du dominant: nein Bist Du sadistisch: nein Bist Du devot: ja, zu 100 % Bist Du masochistisch: nein Bist du rasiert: nein Bist du tätowiert: Ja Rauchst du: Nein Welche ist... Read full Story
gaggedthonglover 2024-01-11 501 Crossdresser Amateur
100%
Crossdressing at CCBC in Palm Springs
I recently stayed at CCBC in Palm Springs. For those of you who are not aware of it, it is the largest gay resort in Palm Springs area. The resort has about 30 rooms, lockers, a pool, steam room and indoor and outdoor play areas all on a one acre outdoor enclave. I arrived there on a Tuesday and dre... Read full Story
Rocky8844 2024-05-27 1,744 Crossdresser Group Sex Blowjob Lingerie pantyhose cum in mouth
66%
More from my closet....
......being single is so better to play my games, no wives to take up my day, no one to lie to anymore about where I went... I had a layover for 3days in Vancouver last fall, three days all to myself, with the aid of google maps I found the local steambath for men. Steamworks it was called, set... Read full Story
badbadboi667 2020-12-03 3,162 Amateur Group Sex Outdoor Bareback Fetish gangbang domination Ass to Mouth amature
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 4,506 Bareback Shemale Fucks Guy Ebony gangbang Guy Fucks Shemale shemale + shemale
100%
HELPLESS TO MY CRAVING FOR BLACK COCK
This is a totally true account of my addiction to meth and its hand in turning me into the he[pless sissy I've become to my weakness for BBC. My name as a regular male is Richie Budd. But by reading this you'll soon realize that nothing is normal. Not only was I Richard Budd. I spent an equal, if ... Read full Story
Tvtrinity 2021-04-07 9,661 Crossdresser Amateur Group Sex gangbang Interracial transgender sissy bbc Black Owned owned white boy pimped force feminised BNWO
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 7,148 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
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 4,966 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
42%
sexy jane story
I love the idea being a crossdresser wearing women outfit bars in panties n sexy outfit not just for the sex I love sex being on my knees sucking cocks in getting fuck by a big cock see win I was very young I had sex with 3 guys one day they ask me will I suck there cocks in I sand yes we want insid... Read full Story
45sexyjane 2019-05-27 4,095 Small Tits Crossdresser Amateur Big Tits Masturbation Blowjob blonde Big Cock gangbang Lingerie Sex Toys shemale + shemale sexy crossdresser
100%
Quick trip to the park
Monday Morning again, I hate Mondays, why can’t the week start on Tuesday! Thought Justina ,while she stood semi naked in the kitchen drinking her coffee with a semi. I finished my coffee and made my way to my bedroom to get dressed. As I entered my bedroom i spotted my new dress i’d bought on S... Read full Story
Samantha Jewels 2022-01-12 2,233 Crossdresser Amateur Cumshot Outdoor Blowjob Mature crossdressing Ass to Mouth cum in mouth crossdresser amateur
50%
Hello!^^
Ciao! this story was created with the help of google translator, so do not judge strictly. I'm trying. I try every day to be better and more confident, but for now I'm still afraid. it seems to me that I can disappoint or not live up to expectations that they will ridicule and mock me, I’m afraid th... Read full Story
kateleto 2023-06-12 3,720 tranny Crossdresser Amateur Outdoor Fetish Homemade sissy femboy Traps story russian cd read
100%
I Missed Myself
As soon as Dr. Griffin returned to the examination room, I knew that the news wasn’t good. I could tell by the way he avoided my eyes as he studied his clipboard and fidgeted with his pen that something was wrong, terribly wrong with me. The ache in my groin that I had been ignori... Read full Story
shemale lover 2013-03-20 7,876 Crossdresser Lingerie pantyhose cd softcore
71%
A Meeting at a rest stop in Alabama
Typically my wife comes with me when I visit my grandmother in Smyrna GA. Last Friday she didn't want to come with me. Perfect. I stopped at the last rest stop just before the Alabama Georgia line and took my bag of clothes with me to the bathroom. I opened the door and then walked into a st... Read full Story
Rocky Wachenheim 2014-09-02 4,850 Crossdresser Outdoor ass fucking doggy style piss
66%
Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
Go Balls Deep or Go Home 2018-08-06 31,143 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
94%
Crossing lines
It had always been a fantasy of mine. I have very feminine features and long natural straight brown hair. Which recently I had shortened to chin length. I have been dressing in womens clothing now for many months and had decided that this was the night in which I get made up totally and head ou... Read full Story
Zöe from Kingston 2019-02-04 10,971 Stockings Crossdresser Cumshot Outdoor Bareback Shemale Fucks Guy Blowjob Big Cock Ebony Guy Fucks Shemale Interracial
100%
Karen, My School Teacher Part 5
The Bus Station By FoxyHosed I looked around, but no one was there. It was dark and pretty cold night outside. I felt the air blowing around and up my pantyhose encased legs and ass. Mmmm nice. I started walking to the bus stop a few blocks further down from the school. I felt very attractive g... Read full Story
FoxyHosed 2021-03-15 6,930 Crossdresser Cumshot Outdoor Masturbation Fetish Blowjob pantyhose legs pantyhose cd
100%
badbadboi's walk in the park
...My boi hole was freshly washed, shaved and lubed with a lovely hot shower, my wand is perfect for cleaning my pussy, flushing it clean very time, I luv to let the water spray my hole driving deep enough to tickle the bottom of my prostate. My cock cage locked in place, my white crotchless panties... Read full Story
badbadboi667 2021-04-06 3,534 Crossdresser Amateur Group Sex Outdoor Bareback Creampie Blowjob Interracial Homemade Ass to Mouth cum in mouth
100%
Stepping Out
All through the next week we searched through almost all the online dating sites and it was the same as before. Some wanted just me or just Deena, but not the both of us together. One good result was that I found a trans gender support group and they were going to meet on the next Tuesday which was ... Read full Story
Setinkhan 2021-06-02 2,985 Crossdresser Fetish Big Cock Interracial cum in mouth shemale + shemale
100%
K*dnapped & R*ped
"You're nothing but a tease, a flirt, you just like to play around and lead guys on," someone messaged me on the swinger site I'm on called AdultFriendFinder. "No," I replied, "I have actually hooked up with guys I met here, I am just very busy." And that is the truth. I work a full-time job and ... Read full Story
Chrissy Tunnell 2022-02-02 3,374 Crossdresser Amateur Outdoor Bareback Fetish Ladyboy domination Guy Fucks Shemale Homemade
100%
Camming Down the Rabbit Hole Ch. 12
We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... Read full Story
Dani_does_Dallas 2022-05-09 5,135 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
0%
Cruising for Cock!
Cruising for Cock. Not my Story But very hot for you all. A few years back now I took a drive to a dogging & cruising hot spot in the Haldon Hill Forest on the A38 in sunny Devon. I'd been once b4 with a trucker who picked me up hitchhiking. (That's another story) WOW his cock was huge 8.5" @ lea... Read full Story
Streethawk75 2023-04-18 4,128 Stockings Crossdresser Amateur Cumshot Outdoor Masturbation
100%
Caught Spying 👀
Caught spying to 1st time sucking. A few years back now I took a drive to a dogging & cruising hot spot in the Haldon Hill Forest on the A38 in sunny Devon. I'd been once b4 with a trucker who picked me up hitchhiking. (That's another story WOW his cock was huge 8.5" @ least. matched his muscular a... Read full Story
Streethawk75 2023-04-18 5,037 Crossdresser Outdoor Masturbation Shemale Fucks Guy Blowjob Big Cock
81%
My first time with a guy
MY FIRST TIME WITH A GUY Another true story it’s kind of long but I think you will enjoy it I lived west of Lake Worth Florida. At that time we were surrounded by 1500 Acres of woods. There were 10 of us and we all had dirt bikes and would go out riding all the time.. On Saturdays we had a game ... Read full Story
Stephanie101 2024-04-26 2,893 anal Crossdresser Outdoor Blowjob cum in mouth teen (18+)
75%
My Buddy the Crossdreser
I hadn't seen my buddy in a while. I called him up and he was game. We usually fuck outside his front door, I get to his new house and the flood lights come on. I'm thinking what is he planning. I stay in the car and he come by and says he's getting in. he tells me to drive up the road. we got to t... Read full Story
horny.hiker 2019-03-04 4,094 Crossdresser Bareback Big Cock Ass to Mouth outdoor sex breeding swallow cum
91%
My Seductive Secret (True Story)
During my childhood, me and my brother used to play with two other boys who were our neighbors every weekend. One day we decided to wrestle, and I took on the youngest one, (he was about 2 years younger than me, like my brother) and we wrestled in the shed while my bro and his bro (who was my age) w... Read full Story
Chickzdigmeyup 2019-06-18 13,923 Stockings Teen (18+) Small Tits Crossdresser Cumshot Outdoor Masturbation Bareback Fetish Blowjob Big Cock Lingerie domination Sex Toys Homemade cum in mouth
100%
First time doing that!!
So I love to dress like a girl and have done since I was about 15, but being married and all it’s a bit hard to do it very often,. I’m a local tradesman so am out all day in my van and have a good knowledge of the area I live in, or so I thought. About 2 miles from my house is a crushing site tha... Read full Story
Samantha Jewels 2022-01-03 2,460 Crossdresser Outdoor Creampie Blowjob Big Cock Mature Ass to Mouth 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 3,381 Crossdresser Amateur Outdoor Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
100%
Surprise Ending (Part One)
My wife is the picture of professionalism from 8 to 5, but after hours she is a sexual dynamo who loves men and women. Throughout our relationship she has introduced several of her gal pals into our bedroom, hot tub, shower, etc...you get the idea. Anyway, two weeks ago she let me know that one o... Read full Story
Chantel13 2022-08-23 5,321 Crossdresser Amateur Group Sex Outdoor Bareback Shemale Fucks Guy threesome Big Cock Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Been a while and oops!!
Hi been a while since I let you know what’s going on with me. Well after spending the last couple of months getting on with stuff and trying to behave ( boring) I finally snapped and needed to go to the woods for some well deserved dick!! I got myself dressed up as normal, g string , stockings, ski... Read full Story
Samantha Jewels 2022-12-10 3,298 Crossdresser Outdoor Bareback cum in mouth
100%
Glory Hole Memories
The Glory Hole Fun Begins Locking the car I look towards the building. The entrance is open, but from my position it isn’t possible to see inside, the bright sunshine making the entrance look black. My heels click on the tarmac as I approach, my legs beginning to tremble with fear and excitement.... Read full Story
Sexy Michelle 2024-03-13 3,784 Stockings Crossdresser Outdoor Blowjob Big Cock Lingerie
100%
Beginnings
I always knew I was a bit different though due to social stigma I didn't fully accept it till later in life. I wish I knew then what I know now and had embraced it sooner. Puberty hit and gynecomastia (formation of women's breasts) hit harder (36C). I was teased, groped constantly and was even force... Read full Story
CD_Danielle_Doggy 2024-03-26 3,069 Crossdresser Outdoor cum in mouth
100%
Carla goes out
As a cross dresser who loves to dress as a dirty slutty girl I was sat at home thinking about what it would feel like to go out dreesed in public. I had often thought about it but never had the courage to do so. I was so fucking horny and wished I had a reason to go out and do something rather than... Read full Story
Carla Kitten 2018-01-16 8,120 Crossdresser Amateur gangbang Homemade
80%
A New Spin On Role Playing Games
A New Spin on Role Playing Games By: Shawna Summers shawnavinylltv@gmail.com I've always been something of a geek. I love sci-fi and fantasy books and movies; I can recite countless bits of useless trivia back to you about all kinds of movies. So, it was no real surprise that I took to rol... Read full Story
shawnavinyltv 2018-06-14 10,604 Crossdresser anal sex Blowjob gangbang Lingerie bondage
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 12,324 first time Stockings Crossdresser Bareback Blowjob blonde Big Cock gangbang domination Guy Fucks Shemale slut cum in mouth
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 8,549 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
92%
Showing my femininity
When I was still little guy, my stepfather always told me I wasn't a real boy, but I was his little girl. One day, he was drinking beer with his friends, so he grabbed me by the arm, pulled my shorts down and showed off my teeny cock to them. I remember that all of them laughed at me. They made fun ... Read full Story
Shemale Dill 2020-04-27 7,842 Crossdresser Amateur Group Sex Blowjob Big Cock gangbang Lingerie
94%
James's Cum Slut Part 4; Back to Boarding School
It was back to school time and I was back in the boarding house with James. We hadn’t seen each other all summer and were eager to relight the fire. But it was going to be hard. While we shared a dorm together, it would be hard maintaining the privacy. We had both packed items from my secondary ward... Read full Story
ATC97 2015-10-08 6,840 Crossdresser teen cd (18+) cum slut latex ts gangbang sex
100%
Vanessa gets more than she bargained for!
Vanessa had it all planned out meticulously. She had taken the day off and planned on doing a bit of last minute shopping before checking into the hotel in the early afternoon. She eventually decided on buying a massive dildo to get her ready for the party. This would give her plenty of time to take... Read full Story
Vanessa Luv 2020-05-15 7,729 Stockings Crossdresser Group Sex Big Cock gangbang Lingerie Interracial cum in mouth double anal
100%
my journey down the rabbit hole
The bathhouse was busy tonite, there were at least 20 or more men there when I got in , I paid for my room and walked in past the heavy buzzer controlled black steel door, it slammed tight behind me. casting a cool draft of air that trailed down the small of my back and fluttered over my enama clean... Read full Story
badbadboi667 2020-12-23 5,843 Crossdresser Amateur Group Sex gangbang Interracial Ass to Mouth
100%
Becoming a Chrissy - Chapter 2
I had always felt like I had a hot body for a girl. I was naturally blonde and smooth; I guess I had been blessed by my parents’ Scandinavian genetics. My pubes were always just a small fuzz—easy to shave and keep a clean bikini line. Same thing with my armpit hair. And my ass? Completely smooth and... Read full Story
mindlessrobot45 2024-05-13 1,889 Crossdresser gangbang Shemale and Girl cum in mouth shemale fucks female teen (18+)
45%
Threesome with random muslim men from Dubai -
As you all know, most of the meetings with my clients happen in good 3-star or 4-star hotels. Clients normally visit my hotel room and have fun. This exciting session happened during my stay in a 3-star hotel room in Bangalore on March 1st and 2nd. I had bookings for both the days and was prepare... Read full Story
Manusha Tranny 2021-10-14 8,903 Crossdresser Cumshot Outdoor threesome Blowjob Big Cock Asian Ladyboy gangbang domination Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Steve
So on AFF, I used to be gold but guys will just hit you up, sooo I got hit up by an 8in boy. Wasn't sure I'd want to prep up an 8 so I didn't get all ripped up, but nice profile and a fucks a fuck sometimes. What to wear to get cum in tonight? Still pretty warm, I'll go mini with tighter leotard (mo... Read full Story
smtmsbrianne 2020-09-16 3,418 Crossdresser Amateur Group Sex Cumshot Outdoor Bareback Creampie Big Cock gangbang redhead Guy Fucks Shemale Ass to Mouth cum in 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 2,470 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale