Sort by
Relevancy

Free Stories

100%
Crossdresser gets dick for first time
I was so tired of just watching porn. So tired of the sissy hypno threads that made me crave men, crave cock, crave being weak, crave being the bitch...only to cum and do nothing about it. But the desire to transition from fantasy to reality was growing stronger and stronger. I decided it was ti... Read full Story
Sissy Ava 2022-10-11 7,856 Stockings Crossdresser Amateur Bareback Big Cock 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 3,362 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
100%
Linda and Cum on Heels
I was told by a cute guy today they would love to cum in a pair of my strappy heels............this was my answer to him. (I hope you enjoy what happened in what could have been unfortunate circumstances) Actually a person did. I had picked him up from the Lincoln University area and we went off ... Read full Story
Linda Tiffany Vista 2024-05-07 2,168 Stockings Crossdresser Amateur Blowjob blonde
100%
Ill take all the cum I can get
I'm so horny today. I need some dick bad. So I dress up, I put on a sexy push up bra, a slutty lace top, a naughty little g string, and lacy thigh highs with a garter belt. Before getting dressed I showered and gave myself an enema. After I showered, I used some fds so I smelled sooo good after ... Read full Story
spreadforalldik 2024-07-09 1,155 anal Crossdresser Group Sex Cumshot Creampie Blowjob ass fucking Ass to Mouth cum in mouth spitroast
100%
A Night to Remember
About six years ago just before Christmas I went to a transvestite bar in the centre Manchester after I had finished my act at a private party on the outskirts of the city. I was dressed in my sexiest outfit mini dress, suspenders, sheer stockings and 4-inch Fuck me hard stilettos, and my favourite ... Read full Story
shemale lover 2011-10-23 3,770 anal shemales bdsm cum
88%
Audry: My Guide to a New World
For a long time, I've known I liked guys. Well, to be more accurate, I like cocks. Guys, I really don't find sexy. Women, I find sexy. A good set of breasts or a nice round ass with a little waist and big round hips will make me hard in an instant. When I look at a guy, I don't get turned on, but sh... Read full Story
shemale lover 2011-12-29 5,017 Creampie Shemale Fucks Guy huge breasts
100%
Olderman and mature crossdresser Part 2
We left the park and drove to his house which was very nice.I knew he was wealth when he picked up due to his car was new jag. He fixed me drink and we sat on his couch and kissed and made out an heavy petting.He kissed my neck driveing me nuts as he did I rubbed his cock thru his pants which was ha... Read full Story
shemale lover 2012-05-26 3,984 Crossdresser anal sex Cumshot oral sex Mature cum swallowing
100%
Westward bound cum slut Chapter 2
Again I'm on the big bird headed out west for another fling. This time is going to be way different though, the players have increased, not to mention both sexes. The tale unwinds in the same fashion as the last trip out this way, the plane flight was long and boring, and being very nervous didn'... Read full Story
shemale lover 2012-12-16 3,584 anal Group Sex sucking Creampie cum domination
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 6,223 Crossdresser sucking gangbang ass fucking
84%
Shool teen crossdresser first time sex
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest f... Read full Story
shemale lover 2014-11-21 18,761 first time suck fingering Lingerie ass fucking cd
81%
Crossdresser for first time
Hello, first of all excuse my spelling, my first lenguage is not English. I have been a CD since I was 15 years old. I used to wear my sisters dirty clothes in the bathroom. I perfect remember when I cum for first time as a CD using a pair of panties and bra back day. I always check out underware... Read full Story
M_10 2015-02-17 5,054 Crossdresser Cumshot facial doggy style cd
100%
Liberty in Lisbon Part 2
So here I was walking down the Av da Liberdade feeling very pleased with myself. I had just thoroughly enjoyed an experience I thought would only ever be in my dreams and, the best part, there was more to come [cum]. In fact I found myself humming the 59th Street Bridge Song. Life I love you feeling... Read full Story
Rusty12 2019-07-31 4,936 Amateur Masturbation Bareback Creampie Shemale Fucks Guy cumming
87%
Chance Encounter 4/7
With her feet still pointed she starts slowly spreading and rubbing her cream over her nipples while i’m thrusting my cock in and out of her sweet hole. Her hole felt so beautiful! In and out I thrusted until I pulled out. I grabbed her hands, lifted her a little and pulled her towards me as I stood... Read full Story
Katlick 2019-10-30 5,088 Bareback Creampie Big Cock cum in mouth
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 10,024 Crossdresser Amateur Group Sex Cumshot Bareback Creampie Blowjob gangbang Lingerie Homemade sissy cum in mouth double anal
66%
Sex in the kitchen with my hubby's friend - a cop
Ever since my wedding last year, I enjoy a great time with my hubby who loves me so much and takes care of me so much. Since he is married and having another family, he doesn’t stay with me all the time, but comes and stays at least 2 or 3 days in a month and we literally celebrate those nights wit... Read full Story
Manusha Tranny 2021-10-14 5,246 Small Tits Crossdresser Amateur Cumshot Outdoor Blowjob Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
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 10,065 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
100%
From a 50's virgin to a Mature good for all
***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... Read full Story
hippocampus_171 2023-01-11 4,361 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
100%
I Love To Love You
I Love To Love You Baby By Sabrina G. Langton Author's note: I have published this story on two other sites. I always said it was slightly aurobiographical, but reading it back it is a pretty accurate account of my summer of '88. There are only 3 things that I changed. 2 are itsy bitsy tiny deta... Read full Story
Brina Giselle 2023-09-24 5,022 anal Crossdresser Blowjob kissing transgender virgin romantic earrings
100%
Kate Berges the Shemale who fucked first in my ass
I was with her last week. She was in a duo. So I went there and rang the bell. Recognized me right away and gave me a deep kiss. I then asked her if she was available in the duo and her colleague a.) cums properly and if she would also fuck each other, which she confirmed. She then went out and c... Read full Story
Bigpruegel69 2023-12-17 6,822 Cumshot Creampie threesome Blowjob cum in mouth shemale + shemale
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 6,281 anal Amateur Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Big Cock domination Mature Homemade cum in mouth
100%
Dogging in the Park
The last two nights have been great fun in our local park. There is a parking lot where guys gather after dark and I was one of them. Both nights I was dressed up as a slutty CD with a black bra, fake silicone tits, black pantyhose and a short miniskirt. First Night: After waiting about an hour a... Read full Story
Rocky8844 2024-04-02 3,927 Crossdresser Outdoor Blowjob
100%
Sex With Not Just 1, But 3 Females
When I was 18 years old, I was still occasionally going to the Highbridge toilets in Lincoln on a Saturday and getting paid for having sex with guys be it sucking cocks or being sucked off, dirty chats, wanking them off or giving or taking anally. I never turned down any form of payment, money or... Read full Story
Linda Tiffany Vista 2024-05-07 2,248 Stockings Crossdresser Amateur Lingerie cum in mouth teen (18+)
100%
In My Place
I looked disbelievingly at the clothing on the bed before me. They were all mine; all of them. How did she know? How did she find them? I just could not believe what was happening to me. I could not do this. It was not what I had ever wanted, despite what she appeared to think. And him....... I h... Read full Story
Loveto 2011-10-12 4,002 cum transsexuals crossdressers
61%
Car Broke Down
A Fantasy: Car Broke Down My car was running hot so I pulled into a driveway so that it would cool down. I got out and raised the hood and added some water. I then got back inside and smoked a cigarette and sipped on a beer that I had. I listened to the radio and glanced out the window and... Read full Story
iluvgurls 2018-11-14 7,350 Small Tits Creampie Blowjob Lingerie 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 3,408 Stockings Crossdresser Amateur Cumshot Masturbation Blowjob Lingerie Mature cum in mouth 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 9,886 Crossdresser Amateur Group Sex gangbang Interracial transgender sissy bbc Black Owned owned white boy pimped force feminised BNWO
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 3,652 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie 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 2,616 Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
75%
A Tuesday To Remember
A Tuesday To Remember It was much like any Tuesday for the last year, except when I came in my wife, Deena met me at the door coming from the garage. She grabbed my arm and started leading me into the living room as she said, “You better say yes, yes to everything.” I had no idea what she was tal... Read full Story
Setinkhan 2021-04-15 6,145 Small Tits Crossdresser Interracial
100%
TG affair in Bimini
The day was rainy and weather was dreary, not much to do and have the day off. I fly a charter plane that takes people to and from the Bahamas from Ft Lauderdale. My girlfriend Jan and I only stay together a few days a week, she is in Real Estate and with my schedule we have not been together in t... Read full Story
Jon Paul 2021-04-19 3,319 Teen (18+) Bareback Creampie Blowjob Guy Fucks 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 5,176 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
100%
bi to sissy caught and turned
It was during a Wednesday nite supper this past April when Penny my wife of seven years, suddenly looked me straight in the eyes while calling me a GAY COCKSUCKER ! Instantly while I swallowed hard and quickly looked away from her, my worse dreaded fears in life had somehow just become reality! So ... Read full Story
redthongthong 2022-08-02 8,922 Crossdresser bisexual sissy crossdresser forced feminization CAUGHT!
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 5,514 Crossdresser Outdoor Fetish Homemade cum in mouth shemale + shemale
100%
Linda and Cum on Heels
I was told by a cute guy today they would love to cum in a pair of my strappy heels............this was my answer to him. (I hope you enjoy what happened in what could have been unfortunate circumstances) Actually a person did. I had picked him up from the Lincoln University area and we went off ... Read full Story
Linda Tiffany Vista 2024-05-07 2,376 Stockings Crossdresser Amateur blonde Lingerie cum in mouth
93%
The Hot Girl at the Bar
My girlfriend and I broke up the week before, so I was pretty depressed. The guys at work decided to take me out to the bar after work to get wasted cause that’s what we do. So we all packed into the truck and headed to the bar. When we got there we were the first ones in that night so we sa... Read full Story
shemale lover 2015-10-01 10,356 anal suck Creampie
100%
Back to School
It all started the day John got a letter in the mail; it was an invitation to his school reunion back home. John was proud of what he had achieved in his life; he had a good job and a house. The only secret John had was that he was a closet cross dresser; he loved to feel feminine from time to time.... Read full Story
shemale lover 2012-02-09 3,929 Shemale Fucks Guy orgy cum swallowing
75%
My shemale GF Part 2
So today she, her name is Christy, she wanted to do something kinky, very kinky I said that's fine. We cleaned up, she went into her closet, which was filled with dildos, butt plugs, sexy clothing, fleshlights, cock rings, paddles, lube, videos, magazines, bdsm things, and a fuck machine. She came o... Read full Story
shemale lover 2012-07-04 3,635 anal sex Creampie shemale Latex rimjob
66%
An Ass to Die For
It's a very strange thing. We all have our personal quirks. The things that make us unique and stand out from the crowd. I've just never met anyone besides me who has mine before, and to tell you the truth I'm not sure if it's a gift or a curse. You see, I have a girl's ass and not just any old girl... Read full Story
shemale lover 2012-11-13 4,093 big dick sucking porn
100%
Ana in Action
I had fantasized about him for months. I just wanted to know what it was luck to have him pulsing inside me, to feel his body pressed against mine in sheer lust. I just had no idea that it would actually come about and that my wife would be the hook up. You see, Jim has been one of my wife's drinkin... Read full Story
shemale lover 2012-11-23 3,024 threesome cum fuck oral
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 7,359 Crossdresser sucking Big Cock Lingerie ass fucking
100%
Caught In Your Wife's Panties
DRESSED IN YOUR WIFE'S PANTIES I called on a girlfriend of mine the other day and you'll never guess what. I'd gone upstairs to use the bathroom, and I noticed her bedroom door was ajar and, me being a nosy fucking bitch, glanced in. What did I see? I saw her kinky husband pulling on a pair ... Read full Story
shemale lover 2013-01-17 8,364 Crossdresser Cumshot sucking Big Cock Lingerie
88%
Tgirl trained to be the town whore to serve ALL Black men
A few years back I spent time on and off with several shall we say more dominating types of gentlemen One of them, who for this I shall call Leroy, just loved when we got together to make me totally helpless. It was our 6th or 7th meeting. Leroy and i had been chatting on Yahoo and when he f... Read full Story
__tiffanylondontv__ 2014-09-30 6,084 suck shemale ass fucking Interracial big cocks
100%
Threesome goes clubbing
Ft. Lauderdale is probably the most LGBT friendly city on the east coast. So many nice restaurants and clubs that welcome all and have many LGBT employees as well. Lydia and I have been married several months, we had met Joanne an absolute amazing transgender girl during a weekend trip to the Baha... Read full Story
Jon Paul 2021-07-08 5,268 Big Tits Cumshot Bareback Creampie threesome Guy Fucks Shemale cum in mouth
87%
Maria's Fifteen Loads
I had always wanted to try Gokkun, all that cum seeing it in video's being drank down in big gulps always got me so horny and hard. As you see this girl likes her cum mmmm. So on a site that shall remain nameless those of you who have met me here and that other site will know shhh. I arranged wi... Read full Story
Sissy Fag Maria Clayton 2021-12-16 3,737 Crossdresser Blowjob Big Cock Lingerie cum in mouth drinking cum Swallowing Cum
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 3,521 Crossdresser Amateur Outdoor Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
100%
Got my ass pounded in Miami by a tranny escort
Got my ass pounded in Miami by a beautiful tranny escort with a 10 inch thick cock. Years ago I was in Miami for a business trip. Four days just me in my hotel room. I decided to treat myself to some of the X rated channels that my hotel provided. As usual I went straight to the tranny porn.... Read full Story
My Shemale Attraction 2023-01-03 6,787 Amateur Big Tits Masturbation Creampie Shemale Fucks Guy Blowjob
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 3,113 Crossdresser Group Sex Blowjob Lingerie pantyhose cum in mouth
100%
A Job in the Theatre Chapter 7
The next day Paula woke late in the day. She lay in bed feeling the glow from her bottom. It was totally erotic and the most satisfying sexual experiences she had ever had. The more she thought about it the hornier she became. She grabbed her cock immediately focused on how much smaller it was th... Read full Story
shemale lover 2012-03-13 2,689 Stockings cum oral sex
90%
Adventures in Babysitting
When I was 14, me and my BFF, Ashley, started our very own babysitting service. She made an announcement during church and we immediately started getting phone calls. One day, Ashley said, "Come here...U gotta check this out." And she pulled out a handful of 20's. "Damn, where'd yo... Read full Story
shemale lover 2012-08-14 6,111 Crossdresser cum fingering oral sex
96%
How I began my crossdresser transformation
Here are the usual disclaimers this story is for adults only if you are viewing this and are not 18 years of age or older please close this page immediately. There is no crossdressing in the story but this is how I began my transformation from regular boy into cock sucking teenage crossdresser.... Read full Story
srlvictoria 2013-04-10 12,050 anal Crossdresser oral handjob sissy
77%
This that go Bump in the Night
It was the ideal time. My wife was away for the weekend and a long weekend at that. So on the way home from work, I stocked up. Some pantyhose, lips gloss, stockings and fake nails. I raced home, turned off the phone and ran a warm bath. Soon I was soaking in the bath with candles and light music. A... Read full Story
shemale lover 2013-03-28 9,261 Crossdresser hardcore sucking ass fucking domination
100%
Crossdresser 1st time!
Hi, im new to this. this happened about 3 years ago now. I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from th... Read full Story
shemale lover 2013-05-30 7,882 Outdoor Big Cock fingering ass licking virgin public cd piss
100%
Jennifer's first taste of cum
This is another in a long of line of true stories about my crossdressing experiences. This encounter happened back in the 90s. It was Saturday night and I was on the road to the Queen Mary in Studio City. For those of you who were into the scene back then, you know what a happening place the Mary... Read full Story
JenniferJones 2019-01-22 8,619 Crossdresser Amateur Blowjob cum in mouth
83%
Janine awaits
My story is not typical. Sure, it mirrors many of the others you’ve read except for one aspect, that is my age. I recently celebrated my sixtieth birthday. Yep, the big 60. And not that I am trying to brag but I am one of the sexiest bitches around. As recently as five years ago I looked like any ot... Read full Story
bunny cat 2019-02-04 3,816 Crossdresser Masturbation Blowjob Lingerie Mature cum in mouth
100%
Business trip
Craig and I were salesmen for the same company and on a trip together to woo new clients. The last thing I expected was that we would woo each other. It had been a long day and we went to our rooms to relax and unwind. After I had my room service and wanted to go over the proposals I realized Crai... Read full Story
Zöe from Kingston 2019-10-07 7,279 Crossdresser anal sex Cumshot Blowjob Lingerie cum in mouth
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 2,338 Crossdresser Amateur Cumshot Outdoor Blowjob Mature crossdressing Ass to Mouth cum in mouth crossdresser amateur