Sort by
Relevancy

Free Stories

87%
Beginning of my Bi Life
Well It's all Started When I Was at 13 or may be 14 years old. I began to watch porn and reading porn comics and began to masturbate. I wasn't getting much privacy at my home so I was staying at my school even after my classes was over and when everyone was busy at after school Sport hours I masturb... Read full Story
Trapbomb1 2021-05-25 4,440 sucking Blowjob cum bisexual cd sissy femboy bi trap
90%
On the Run
“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... Read full Story
shemale lover 2012-09-01 11,306 Crossdresser Cumshot Blowjob jerking pantyhose
100%
Fucked By BBC pt 2
It has been 3 weeks since I became a bbc cocksucker, since then I have learned to enjoy the taste and the feeling of a cock in my mouth. I have also learned the guys name on the 2nd day of being used by the guy, his name is Darren. One day while I was at Darren's giving him a blowjob he tells me ... Read full Story
kinkyguy18 2023-11-03 6,686 Group Sex Bareback Creampie Blowjob Interracial sissy 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 3,355 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
50%
Tea-Girl's Repeat Performance
It was the last night before my girlfriend was due back from the Hen Night she was on, and I had already washed her clothes from my previous day's fun with the electricity meter reader, during which I made a mess of her satin thongs, pantyhose and white body-tight top. I wanted to relax, with a bott... Read full Story
shemale lover 2012-09-01 3,641 Cumshot Masturbation Blowjob fuck pantyhose
100%
First Time Being a Woman
My heels clicked on the concrete path as I made my way toward the secluded toilet block in the southern parklands. Tonight would be my first experience being with a man whilst I would be dressed as a woman. I had been dressing now for some time and had fantasised about what it would be like. I didn'... Read full Story
shemale lover 2012-10-08 4,663 first time Creampie Fetish crossdressing
92%
Lady In The House Chapter. 01
A story by MicheleNylons ( Man in jail is transformed to prison slut.) How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild... Read full Story
✘Transensual✘ 2019-01-11 9,442 Crossdresser Bareback Creampie Fetish blonde Big Cock Lingerie domination Guy Fucks Shemale transvestite slut PRISON FUCKBOY prison sex Prison Bitch
100%
Theatre Part 2
The man I had been stoking removed my hand from his cock, taking over. He grabbed my head with his other hand, pulling me close in to his cock. His cock was bouncing off my face as he pumped away. A short stream that rolled down my chin was just the start. His cock spewed load after load like a ... Read full Story
LongLegBlonde 2012-11-16 4,505 Bareback Creampie shemale domination Interracial cuckold
92%
MY TS FOXXY & VENUS LUX FANTASY
Alyssa Gomez and Venus Lux were visiting Newark, NJ and decided to have lunch in the restaurant that I work in. It was a rainy day. The seductive pair were returning back to their suite in the Courtyard Marriott, but not before grabbing a bite to eat. Alyssa and Venus sat the bar and ordered a coupl... Read full Story
I_GO_3WAYZ 2021-03-02 11,278 Latina Creampie Shemale Fucks Guy threesome Blowjob Ass to Mouth cum in mouth double anal
72%
ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn
Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... Read full Story
SpankydeBautumn 2021-01-29 11,377 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
100%
The Next Level
Nitromethane It's been a couple of weeks now since I sucked my last shemale cock and swallowed her load, and with enough distractions, it hasn't been too difficult keeping myself preoccupied and my mind off of satiating my new fixation. Still though, I do have my moments when I sit back and imagi... Read full Story
Gwapo67 2022-02-01 5,777 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock gangbang domination cum in mouth
100%
How I was accustomed to a penis
Как меня приучили к члену Часть 1 Раз в несколько лет мы ездим на родину к отцу повидать родню. Отец заезжает к брату к матери, сестре, старым друзьям, везде изрядно выпивает, и мы едем домой. Только раньше я был маленьким, а сейчас мне 19 лет, и я мог выпить со всеми за столом. Приехали к брату,... Read full Story
Sara 69 2022-04-25 3,850 Group Sex Creampie threesome Blowjob Big Cock gangbang Homemade cum in mouth
100%
My New Outfit
My sister knows that I have been dressing in girls clothes for four years now ever since she caught me in her black string bikinis and white patterned tights when I was 14. Needless to say, I freaked out but she was completely cool with it. Ever since, we go shopping for new clothes together wheneve... Read full Story
shemale lover 2011-10-26 3,224 anal Creampie crossdressing
100%
Office Casual
"Good morning Ms. Anderson," Karen said as her boss walked past her desk station and into her office. "Good morning Karen," Ms. Anderson said, not even stopping to make eye contact, "I'm going to be very busy today, so I'll need you to let me know if you get any mail fo... Read full Story
shemale lover 2012-08-30 3,848 brunette cock Masturbation Blowjob shemale big
76%
Sissy Ghetto bitch part 1
-The Guys 4 ghetto guys was inside a porn site looking at random sissy babe pictures when they accidently found a picture of someone they know. Like every album they clicked it that specific one with a tranny dressed so girly with mouth open. The guys had such a stone hard erection by watching al... Read full Story
shemale lover 2013-06-01 6,159 suck Big Cock cum jerking gangbang doggy style Interracial cd
100%
Best Fuck of My Life
This is a 100% true story of the best fuck of my life. It happened almost 2 years ago. I had gotten back into dressing after a very long time. I work very hard at being as passable as possible and it really seemed to work on this particular night. Here's the story. I got all dolled up in one o... Read full Story
JenniferJones 2019-01-21 11,224 Crossdresser Amateur Bareback Creampie 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 7,789 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
94%
Sissy Slut: Gang Favored
I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... Read full Story
Regina10 2021-03-02 7,505 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
100%
Bimini (part2)
Emily was introduced to me by my friend Jan at a night club. ‘Em’ is a 19 y/o t-girl and absolutely adorable figure and very sexy legs. Well after leaving me at the club with Emily, I had invited her to fly to Bimini the next day for a long weekend . If you read part 1 you will know. Waking up... Read full Story
Jon Paul 2021-04-19 3,529 Bareback Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale cum in mouth
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 2,795 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
100%
Sally's First
My heart was racing a mile a minute as my hand reached for the door knob to open a whole new world to me. Although I had been dressing for about 15 years, at 23 I still hadn't been outside or let anyone in on my secret. The last 3 years had been hell for me as I had started to play with dildo's a... Read full Story
shemale lover 2012-08-29 4,663 big dick Cumshot pantyhose cock sucking
100%
Downsizing
Being frail and weak is a gift that not many men see the beauty of. Most consider it a punishment or something of that nature. There is another gift that many men don't see. That gift is affirmative action. Most other people lose the chance at some excellent jobs because of their race, creed, sex, e... Read full Story
shemale lover 2012-11-10 3,750 Cumshot sucking Blowjob
100%
Emily's First Daddy
This is a story how a curious male can become a sissy slut seemingly overnight. So I was in an online adult chat just talking with random people and happened to mentioned where I live. Then all of sudden, I got a message from a man calling himself bear daddy. He introduced himself and said he was ... Read full Story
User Removed 2019-10-21 8,971 Crossdresser Amateur Creampie Homemade cum in mouth webcams
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 5,020 anal Crossdresser Blowjob kissing transgender virgin romantic earrings
75%
TV-TV
My girlfriend Gloria and I had just moved into an apartment together, having gone out for six months or so, before making the committment. We moved in furniture from each of our apartments, after deciding what would go best in the new place. With the exception of a television, we really had eve... Read full Story
shemale lover 2011-12-16 6,699 Blowjob transformation tg
100%
Beryl's birthday suit
I tried on my sister's panties when I was 12. They looked so cute, so sexy.. I couldn't help myself. I tucked my dick between my legs and pulled them over my hips, delicately positioning them just like a girl. They felt yummy! When I saw the shiny, lacy pink briefs in the mirror - snug, flat pu... Read full Story
Beryl 2023-12-12 7,195 first time Stockings Crossdresser Bareback Blowjob Big Cock Lingerie redhead sissy cum in mouth
100%
Connie at an Adult Bookstore
Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * Let me start by i... Read full Story
shemale lover 2011-09-30 4,289 Cumshot Blowjob crossdressing
100%
Quick Fix
My anticipation couldn't be expressed in words. It had been a while since I'd had a visitor to my apartment. The last experience had ended quite well, with the bed sheets being more than a little tussled up. I was preparing myself with an erotic movie. The sex scenes always turned me on, my ... Read full Story
shemale lover 2012-08-30 2,710 anal sex Cumshot Blowjob jerking Sex Toys
100%
A Natural Sissy Part 2
The Party Just before we reached the entrance, which was manned by a doorman, I said, "Now remember, Stacy, you just do what I tell you, and everything will be fine." "Ok... okay." His nervousness was showing, but that was to be expected. He had no idea what was going to me... Read full Story
shemale lover 2012-03-24 4,272 anal sex Creampie oral sex sissy
95%
My introduction to tits & cock
I was just 18 and working maintenance at the Florida condo complex always curious and super horny. It was a Friday and I was sent to 2032 to do a minor repair, I knocked but nobody was home so I used my master key and entered. The condo was very clean but right on the coffee table where some porn ma... Read full Story
In Need Of Some Huge Black Cock 2019-04-23 9,935 Amateur gangbang Interracial
100%
Gemini Sluts and Gang
My good friend Renee and I had set up a double date gang bang for tonight now that she was finally out of the closet and ready. She has decided that life is too short to remain in the closet and miss out on all the fun. Renee and I have so much in common. Besides loving sex, we both have a fetish f... Read full Story
Regina10 2021-04-09 4,476 Group Sex Big Tits Cumshot Bareback Fetish Blowjob blonde gangbang Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
84%
She never saw it coming
When I was 19/20 I used to frequent LGBT bars roughly twice every month. Most nights not much would happen but I found myself going to the trans nights more often. Until I eventually had some experience with trans girls. It was mostly fairly soft fun. Me getting oral and occasionally topping th... Read full Story
chris1989r 2022-02-01 5,146 shemale gangbang facial
100%
Gangbanged By 3 trannys
Gangbanged By 3 trannys This is a story about the night I was Gangbanged by 3 trannys. I was at a Transgender after hours clubs that was filled with hot ass Tgirls. This tall white gorgeous woman was eyeing me the moment I walked in. She was wearing this fitting blue dress that showed off ... Read full Story
My Shemale Attraction 2022-12-11 8,497 Group Sex Shemale Fucks Guy threesome Blowjob gangbang Ass to Mouth cum in mouth
86%
My First Ladyboy
I was working in Bangkok a couple of years ago. As was the normal practice all the guys would finish work on a Friday afternoon and head to the local bar for a couple of beers.. This particular Friday we were in the usual place chatting and having a nice relaxing time......when she walked in....t... Read full Story
shemale lover 2015-05-23 8,541 anal Blowjob Asian
100%
I am a Shemales' Bottom Slut Part 2
I have been with Nancy and I have moved in and quit my job and I run around her house naked 24/7 so she can take me whenever she wants and I love her cock. She has taken pics of me naked with her cum inside my ass and posted them on the web. Nancy said," We are going to have a party to... Read full Story
shemale lover 2011-10-04 3,931 Creampie cum oral
100%
How i became a girl
Hi my name is Mandy and this is my story..in parts. I started dressing when i was in my early teens. At first it was just panties, maybe pantyhose and masturbating with my friend B, but it soon became wearing skirts and heels, little tube tops and sexy dresses, then it was makeup and wigs, and soon ... Read full Story
shemale lover 2011-10-22 3,434 Masturbation Creampie crossdressing 69 pose
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 4,247 Fetish Blowjob crossdressing
100%
First time out of the closet
I had always been more than a little interested in the world of cross dresser and she males. Since I was a teenager I had experimented with cross dressing. Usually just small stuff. As the years progressed whenever I was out of town on a business trip I would sometimes dress up in my hotel room. I a... Read full Story
shemale lover 2012-04-19 3,310 anal Creampie oral crossdressing glory hole
100%
A Turkish Delight
My export business was beginning to take off as I was now on my second over sea's trip. I was doing business with the Turkish government and I also saw it as an opportunity to explore more my fascination of cross-dressing. I would be visiting a country where I was not know and I would blend in with ... Read full Story
shemale lover 2012-07-15 3,002 Creampie oral facial domination crossdressing
100%
Fender Bender Chapter 4
My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I had just turned 18. It was Tuesday evening and I had stayed home alone all day. I had a lot to think about. I was relaxing and listening to some music on the stereo. Mom had just ... Read full Story
shemale lover 2012-07-26 3,174 anal Creampie oral sissy
100%
Fender Bender Chapter 7
The main Characters are as followed: My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I turned 18 a few months ago. Gary is almost 6', 185 pounds. He has short blonde hair and dark blue eyes. He has a nice tasty 7 1/2 inch cock... Read full Story
shemale lover 2012-07-27 3,133 Creampie ass fucking domination oral sex sissy
85%
Whatever Your Heart Desires Part 2
I would love to say I had The Grand Plan: How To Transform Your Husband Into A Ravishing Fem-Toy, A To Z. The fact was, I didn't have a clue. It wasn't a topic normally covered by the Multiple Listing Service. I really didn't think the community library was going to be much help, either. I couldn't ... Read full Story
shemale lover 2012-12-09 3,747 Creampie fuck fondling kissing
65%
Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
shemale lover 2012-12-19 10,594 Masturbation Blowjob blonde ass fucking big boobs
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 8,617 Crossdresser Amateur Blowjob cum in mouth
83%
Epic weekend with stepbrother
Ok so me and step brother both graduated and where ready to celebrate we decided we are going to Vegas. We where both virgins so we couldn’t think of a better place to loose it. How where supposed to loose it was supposed to be a much different story. His was supposed to be like any young handsome ... Read full Story
Wet boy kitty 2021-01-29 4,442 Small Tits Crossdresser Amateur Masturbation Bareback Creampie blonde Lingerie cum in mouth
100%
The Interview
The Interview By Sabrina G. Langton *** 'A crossdresser goes on an interview in lots of pink, of course she gets the job' 'Author's note, just a quick little story with some really graphic sex, and a little tiny moral. I hope YOU like it.' *** "Okay, sit, sit, let's get started. S... Read full Story
Brina Giselle 2023-12-04 6,577 anal Crossdresser Blowjob heels cum in mouth pink dress
100%
Ladies who Lunch - At the Gloryhole
Ladies who Lunch - At the Gloryhole By Sabrina G. Langton *** Author's Note: Hi, just a quick little story to make us all wet and squishy. Three mature crosssdressers have a little more excitement than they are used to after lunch. I hope YOU like it... *** The Boynton Tavern So w... Read full Story
Brina Giselle 2024-01-06 5,257 Crossdresser Blowjob transgender mature crossdresser gloryholes
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 3,072 Crossdresser Group Sex Blowjob Lingerie pantyhose cum in mouth
81%
Brenda & Bry
I like to write stories that involve kids having sex. And one of my favorite subjects is kids having incestuous sex. One story, about a brother and sister, attracted the attention of a 15-year-old boy when I uploaded it to the adult BBS that I regularly called in Reston. It seems that one of the ... Read full Story
ColonelSaint 2012-03-19 8,144 femboy dildo fucking
88%
My first time as a Femboy CD pt 2
David ordered me to dance for him and I hurriedly got off the floor and walked over to the radio and turned it on. I changed the station from an alternative rock station to a top 40 one, which was better for dancing. After I selected the station I moved to the center of the room and started to dan... Read full Story
Nicole_femboyCD 2014-12-03 21,065 anal Crossdresser Cumshot Blowjob rimming cd
50%
Minha primeira experiencia CD REAL [PORTUGUESE]
Não é uma ficção, essa é a minha história de verdade. Primeiramente, como toda história desse tipo, vou me descrever. Sou branquinha, 1,73 de altura, 60kg, magrelinha, meu corpo e rosto são um pouco femininos mas não tenho atitudes afeminadas, sou mais andrógeno do que femboy, olhos e cabelos casta... Read full Story
Nyxie 2020-05-04 1,850 Crossdresser Amateur Latina Masturbation Bareback Blowjob Lingerie
50%
Minha segunda experiência como CD [PORTUGUESE]
Olá, antes de mais nada quero avisar que minhas histórias são verdadeiras e que eu me descrevi na minha primeira história, por isso não o farei novamente. Minha segunda experiência aconteceu 6 meses depois da primeira, não disse qual idade eu tinha na época, então vou dizer agora, nessa história ... Read full Story
Nyxie 2020-05-04 1,463 Stockings Teen (18+) Crossdresser Amateur Cumshot Latina Masturbation Blowjob Lingerie cum in mouth
100%
How I Became Chrissy the Caged Sissy
I am a sissy, or femboy, or tgurl, or shemale? Well either way I like wearing female clothes and being treated like a girl, especially in the bedroom, and now I also like being locked up in a chastity cage that I wear 24/7 now. This is the story of how I became a caged sissy: "Put it on and ... Read full Story
Chrissy Tunnell 2022-01-27 4,172 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
100%
How I Became His Office Fucktoy
Until this job ended last year, every day at my lunch break I would service one of my many Daddies in his office in the building where I worked. He'd always slip me a few bucks, a $20 or even $50 afterwards, not as a payment for sex, but as a "tip" "for all the hard work you do here," he says. I wor... Read full Story
Chrissy Tunnell 2022-02-18 3,747 Crossdresser Amateur Fetish Blowjob Ladyboy domination Guy Fucks Shemale Mature cum in mouth
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 3,621 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
100%
AUTOBIOGRAPHIE D'UNE ESCLAVE SISSY ⚧️ ⚧️
Avec un soupir, je me suis effondré dans mon canapé et j'ai ouvert une bière. J'ai fermé les yeux et j'ai écouté, le silence et le bourdonnement lointain d'une autoroute étaient la seule chose que j'ai entendue. J'ai ouvert les yeux et j'ai regardé autour de moi et je n'ai vu personne. Il a commencé... Read full Story
Femboy 2021 2023-03-27 812 Blowjob bdsm humiliation anal fucking cum in mouth esclave poule mouillé cage de chateté male soumis