Sort by
Relevancy

Free Stories

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 4,362 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
100%
Camming down the rabbit hole Ch6
In the morning I decided to give the running a miss and do a long session with the DVD, my legs had become a little sore and tight so some extra stretches and yoga would really help. I once again surprised myself with how much more flexible I had become, the plug still in my ass giving me occasional... Read full Story
Dani_does_Dallas 2021-10-11 4,898 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade pov cum in mouth webcams
100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 5,069 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
92%
Southern Hospitality Ch. 04
XtinaSmith2017 Ash awoke feeling cold, he pursed his lips a little and shivered, curling up a little tighter, nude as he was, the action brought little relief from the cool air. He let out a soft murr of discomfort as his mind shook off the cobwebs of lingering dreams, he could see light throug... Read full Story
Gwapo67 2022-05-16 6,739 Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Mature cum in mouth
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 7,285 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%
Taking Ricky's Cherry
My work has me traveling all over the US and if you have read any of my previous stuff then you might have figured out that I have a major cougar streak. I just love being the first T gurl to a sexually inexperienced young guy. I was bored and horny in the hotel room, so I logged into a gay dating s... Read full Story
pennypenny 2019-06-11 8,426 Stockings Teen (18+) Crossdresser Cumshot Bareback Creampie Fetish Blowjob redhead Guy Fucks Shemale Mature Ass to Mouth 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 4,045 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
72%
DENISE IN BLACK FF NYLONS AND HEELS
I have a passion for corsets and black fully fashioned seamed nylons, which I like to wear with tight revealing tops and miniskirts or very clingy dresses. I always wear multi strap 10 or 14 suspenders with a tight lacing corset that reduces my waist and gives a sexy outline to my shape. My favou... Read full Story
DENISEFFNYLONS 2018-04-03 8,098 Stockings Fetish threesome gangbang Lingerie Mature cum in mouth
100%
Camming Down the Rabbit Hole Ch. 10
As the sun beamed in through a gap in the curtains my now familiar morning wood strained at the silk of my nightwear. How was it that no matter how hard I came the night before it would wake up eager and ready to go. As had become customary my mind would be filled with the events of the previous nig... Read full Story
Dani_does_Dallas 2022-04-12 3,491 Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking cum in mouth webcams
87%
A Virgin Crossdresser
I was newly turned 18 never even kissed a girl let alone had sex. I had been crossdressing for about a year and had stumbled upon a site called tvchix which where I spent my nights in chat looking and getting an insight into what this world could offer. Bit of background I had named my alter eg... Read full Story
Jessicaxx91 2020-02-06 11,951 Crossdresser Amateur Fetish Lingerie Guy Fucks Shemale cum in mouth
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 11,381 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
100%
Camming Down the Rabbit Hole Ch. 07
Opening my eyes I struggled a little as the residual cum on my face from last night’s show hadn’t been fully wiped off, I felt the dry and crusty leftovers crinkle on my skin, but couldn’t help but smile to myself as I remembered how it had got there. The intensity of that orgasm had been on another... Read full Story
Dani_does_Dallas 2021-10-22 6,335 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade self sucking pov cum in mouth
100%
delicious virile male flesh
Tasted delicious virile male flesh… The breeze caressed my swollen nipples giving me pleasant shivers. The two glasses of Riesling had also contributed to my excitement. My crotch was burning as if the disappearing sun had blown all its thermal energy into me. Under my fine lace panties, purple o... Read full Story
hippocampus_171 2023-04-23 5,009 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminisation cum in mouth gaycd virile
78%
A Little Girl Forever
Since I was a little girl I dressed in my sister's clothes, she knew it and she kept clothes for me and sometimes she bought clothes thinking about me. She was my accomplice and still is. When I was alone I dressed totally as a woman and I felt totally satisfied and realized as such, this included m... Read full Story
Mabel Cecilia 2019-05-06 8,043 Small Tits Crossdresser Amateur Cumshot Latina Masturbation Creampie Blowjob blonde Lingerie Shemale and Girl Guy Fucks Shemale Sex Toys Mature self sucking Solo Shemale cum in mouth double anal shemale + shemale
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 7,208 first time Stockings Crossdresser Bareback Blowjob Big Cock Lingerie redhead sissy cum in mouth
80%
my new life with my sister-in-law
Yesterday, I went to visit my brother's newly-divorced ex-sister-in-law in her brand-new apartment. It was meant to be a friendly visit and an opportunity to discuss her new start in life. To describe her to you, she's a slightly chubby woman in her forties, blonde hair, blue eyes, very charming wit... Read full Story
DicksFly 2024-02-06 6,731 Amateur Fetish Blowjob blonde Lingerie Sex Toys Mature big ass Homemade
100%
Horny Writing A Strange Habit
I enjoy watching videos which I can Vicariously live. This is nothing more than my horny hobby, an amalgamation of various thoughts. My form of hands free edging. Spell checked only, "No I haven't proof read a first draft, not trying to publish masterful works here." Hope to hear from those w... Read full Story
Araina 2021-03-08 2,745 Crossdresser Amateur Big Tits Cumshot Bareback Fetish Blowjob Big Cock Guy Fucks Shemale Frottage Homemade Ass to Mouth cum in mouth
100%
Weekend Fantasy
have so many fantasies....the one that gets me lately, is having access to a house out in the middle of nowhere, for a week or weekend, where i can dress up, all day. No one knows of my lustful secret....so the idea of being able to stay this way without thought, gets me so hard and such in the moo... Read full Story
martley 2020-07-20 5,083 solo Amateur Group Sex Masturbation Big Cock Lingerie domination Sex Toys Homemade self sucking cum in mouth double anal shemale + shemale
100%
Discovering Amber Chapter 3
There have been very few times in my life I have been terrified and today was definitely the tops on that list. Ms drove us to the mall and as I watched she walked around the front of the car and opened the door for me. I looked up to see her hand extended toward me. "Practice getting out li... Read full Story
shemale lover 2012-09-28 4,136 sucking Fetish domination Sex Toys
100%
Daddies New Girlfriend
Doug suspected his 19 year-old son Jerry was stealing money. Doug worked far too much trying to provide for his son to supervise him properly but drew the line at theft. So he decided to set up a web-cam behind the mirror in his bedroom, he'd used the very same 2 way mirror to film his dead wife Cyn... Read full Story
shemale lover 2012-03-09 12,203 sucking Fetish crossdressing
100%
Sissy Slut Reunion
Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... Read full Story
Regina10 2020-09-14 4,185 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Camming Down the Rabbit Hole Ch. 09
As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night ... Read full Story
Dani_does_Dallas 2022-03-22 3,460 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
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 3,912 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Uniform Lingerie Homemade self sucking pov 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 3,623 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
100%
Sissie Slut's Windows of Womanhood
I flash back to my first time with a grownup adult at the tender age of16 . I was so nervous now that we were here in the motel room. I was nervous for so many reasons. I lied to my family and told them I was staying at a friend’s house. Instead, I'm here with Mr. Joey in a motel room and he was my... Read full Story
Regina10 2021-02-22 6,669 Crossdresser Bareback Creampie Fetish Blowjob blonde Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth double anal
84%
SUMMER VACATION by Spanky de Bautumn
In our house, it was a well-known secret that my mother kept her change in the top drawer of her dresser. The same drawer she kept her slips, chemises, panties, and all other satin, nylon, or lacy ladies undergarments. During the summer, my brother and I would run to that wondrous drawer when... Read full Story
SpankydeBautumn 2021-01-22 12,665 Small Tits Crossdresser Cumshot Masturbation Fetish Blowjob Lingerie Shemale and Girl cum in mouth
33%
A Certain Perception
Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... Read full Story
shemale lover 2012-02-23 8,251 Fetish transformation dildo
100%
Birthday Present
Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all about the exchange and nothing else was said about my birthday. The day arrive... Read full Story
shemale lover 2012-06-16 14,166 Cumshot Fetish orgasm oral sex
83%
Elaine & Me
- Chapter One – Our First Meeting - I had two weeks to go before the final degree exams and I was working hard. Perhaps too hard, because I desperately needed a break from the hours and hours of revision. It felt like I just couldn't take in any more detail about Quantum Mechanics or Solid ... Read full Story
shemale lover 2012-03-31 11,407 sucking Fetish transsexual
100%
A Game within a Game Part 1
Epilogue Rob came home from work. His wife Jenny was waiting for him. In her hands she held a letter. Jenny said: "We received this letter today. It is sad news from Marion S. We have met her and her husband John a few times - do you remember? John has had a car accident while driving fas... Read full Story
shemale lover 2012-03-05 14,224 Fetish bdsm crossdressing bisexual
71%
Birthday Present Part 1
Birthday Present or (I've Looked at Love from Both Sides Now) Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all abo... Read full Story
shemale lover 2013-01-18 11,338 hardcore sucking Blowjob Lingerie ass fucking
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,481 Big Tits Cumshot Masturbation Uniform Frottage
100%
A busy Friday night
I had been looking forward to this weekend for a month. My wife was going to visit some friends in NYC, and I was staying home, by myself. Yup, just me and all of my favorite things, like stockings and panties, and sexy little outfits. The torture was finally over, and the Friday she was to leave, a... Read full Story
shemale lover 2012-02-28 3,867 anal gay male Fetish
100%
Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
shemale lover 2012-11-27 11,013 Fetish crossdressing feminization
50%
Sissies Training Part 2
I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by ... Read full Story
shemale lover 2011-09-17 6,569 shemales Fetish bdsm
97%
Stepdaughter's Transexual Surprise
I've been through two marriages in the past. My first wife died at an early age of 29 from a massive heart attack and my second marriage was a nightmare from hell, that I'm now free of. When I met Jeanie, I knew I had to take it slow and easy. Jeanie was a very nice lady in her early 40's. I myse... Read full Story
shemale lover 2011-12-04 13,585 anal Fetish transexual
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 17,321 Crossdresser sucking Big Cock ass licking big boobs
66%
Trannies in Space
There was no spaceport on Jansen's Planet. There had been, but whatever calamity had befallen the world generations ago had also destroyed its port. It was one of so many planets out in the Barrens that had fallen on hard times. So Dekker set down the Barnabas in a clearing in the forest, a remna... Read full Story
ASSEaster5678 2019-01-25 12,201 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
50%
Hard Decisions by Elaine © 2020
Hard Decisions by Elaine © 2020 No one in this story is based on anyone alive or dead. It is a work of fiction and should not be read by minors. I appreciate the kind efforts of many of my friends who cast a welcoming glance over the initial writings. I owe you all a big debt of thanks. Prolog... Read full Story
Elainetguk 2023-09-06 4,838 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
100%
A Dream Comes True
I was sitting in my home... if you could call it that. It was an apartment in a complex that looked so run-down it wasn't funny... and it drove away most of those who wanted to rent there. The only reason I stayed there was because it was the perfect cover for what I did. Anyways, I was readin... Read full Story
shemale lover 2012-02-29 3,541 Fetish cum fingering oral sex crossdressing
100%
Anastasia's Life
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember, not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barb... Read full Story
shemale lover 2012-11-26 7,206 Fetish cock sucking crossdressing
100%
Blushing Bride Chapter 5
Chapter Five: The Wedding Night I guess it's natural to be full of nerves and second thoughts on your wedding day but I'm not sure how many grooms have the sort of thoughts that I was having on the morning of my wedding. It wasn't that I wasn't very much in love with Gina, my beautiful fiancee, m... Read full Story
shemale lover 2012-07-21 4,741 Fetish oral sex crossdressing
100%
Am I Who I Think I Am? Chapter 2
Well,I can't lay here all day and dream! I feel so good, so loved, so ravished. My smile is touching the pillow on both sides! I'm laying here daydreaming about my deflowering this morning. Inside me lives my lover's DNA, looking for a life to create. (Nice try little spermies, but you won't find it... Read full Story
shemale lover 2012-10-19 3,532 Cumshot sucking Fetish
73%
Nightclub Cum Slut
After splitting with my first boyfriend I went through a period of time I call my slut phase. I explored my sexuality in a massive way and did as much cock ass and pussy as I could. I thought that after I had been in a few relationships that my slut phase was over. I still had the odd one night stan... Read full Story
shemale lover 2013-01-10 7,209 Cumshot sucking ass fucking Guy Fucks Shemale ass fingering
100%
The Conference Part 2
I was in an excited mood all day after the previous evenings surprise and events, and was anticipating another evening of fun. At last the time to meet in the bar came and I arrived to find Cleo in there with girl. I went over and said "Hi" and sat down. She introduced me to her friend ... Read full Story
shemale lover 2011-12-24 3,854 Fetish crossdressing erotic encounters
100%
Becoming a Cock Worshipper
I first realized I was bi the summer after high school. Up until then I had only been really interested in girls. Like any high school guy I watched a lot of porn and soon realized that I really liked really nasty deep throat blow job scenes. I especially enjoyed watching a girl choke and gag and... Read full Story
shemale lover 2012-02-29 3,868 Fetish crossdressing
100%
Sissy Femboy Chrissy in Drag 2: At the Apartment
This is Part 2 to the article I wrote called "Sissy Femboy Chrissy in Drag at the Club." In that story I explained how I am 41 but look, feel and sound younger, that I shave myself smooth and like dressing in gurly panties and other female clothes to be a sissy femboy for older guys. A guy I met on ... Read full Story
Chrissy Tunnell 2022-02-03 3,618 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
33%
Growing up CD
Peter, Max and I played together like that for the rest of the weekend. We must have sucked each other's cocks at least 10 times over the three days. Peter and I were both physically drained. Max just seemed to be insatiable for our bodies. He didn't want us to go. He kept on saying how much he ... Read full Story
shemale lover 2011-12-04 4,210 sucking Fetish
100%
Been Caught Cheating Chapter 3
I awoke in pain. I had slept bound all night. And it also seemed that I had been hit with something to wake me up. Angela was standing over me with one hand on her hip and the other holding my bounds that I slept in. She was already dressed and ready to go. I looked around to make sure we were alone... Read full Story
shemale lover 2012-04-23 4,127 Fetish domination crossdressing
100%
Bike Shed Rendezvous
Chapter 1 A meeting you can't refuse The sun is shining brightly, but the ground is still damp from the morning's rain and the air is very cold. It's lunch time and you quickly walk across the College car park to the sports pavilion. Becky your sweet heart has told you to meet her and she's been ... Read full Story
shemale lover 2012-06-11 3,205 Fetish oral sex crossdressing sissy
82%
Bikini Boy
I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage... Read full Story
shemale lover 2012-06-12 15,467 Cumshot Fetish oral sex crossdressing
84%
The Making of Erica - Sperm Loving Crossdresser
Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I have only sucked cocks, but over a hundred at my las... Read full Story
shemale lover 2015-09-03 16,618 shemales Masturbation Fetish
90%
The Conference
It had been a long day at the conference. During my evening meal in the hotel restaurant with some colleagues I noticed a stunning looking woman across the room. We met eyes on several occasions and acknowledged each other with a warm smile. She stood up to leave the restaurant and I was able ... Read full Story
shemale lover 2011-12-24 5,603 Fetish crossdressing erotic encounters
36%
A First Time for Hannah
At age 24 and after years of dressing in private, I finally decided I needed to get out. I had been scouring online personals for some time but never got further than exchanging a few emails and trading pics. I had been in touch with other CDs from all over the country and had even considered travel... Read full Story
shemale lover 2012-03-01 2,832 first time Fetish crossdressing
85%
A Summer Storm
The storm had caught us completely by surprise; we hadn't noticed the darkening clouds on the distant horizon as we lay in the late afternoon sun, talking about how our lives had changed since we last saw each other, nearly eight years ago. We had been best mates since primary school, doing everythi... Read full Story
shemale lover 2012-07-05 8,435 Cumshot Fetish oral sex cum swallowing
100%
Fender Bender Chapter 2
The bright sun shining through the window woke me up, for a moment I was confused and disoriented. Then it all came back to me. I had sex with Mark and Susan James last night and I was still wearing a pink baby doll nighty and matching panties she had given me to put on before we went to bed. I w... Read full Story
shemale lover 2012-07-26 4,356 Teen (18+) Fetish crossdressing