Sort by
Relevancy

Free Stories

100%
Slut /W Bad Boy
I was excited as always because I was about to go out in public and hopefully I will meet some horny man with some money and get laid. Now, to make sure that I am a picture of femininity, I double checked my makeup in several mirrors from many angles. My lips were perfect and I made sure my cheeks b... Read full Story
Regina10 2020-12-04 7,119 Stockings Crossdresser Big Tits Cumshot Bareback Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale pov Ass to Mouth
88%
Girl from Uncle
Tonight, I have to tell it all. It’s no secret that my uncle and I had a very special bond he had been eyeing me with those adventurous eyes from the time that I was 14 years old. And frankly I enjoy his ogling. I could feel my nipples get so hard when he looked through me with those alert and spark... Read full Story
Regina10 2024-02-14 5,284 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy 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 4,088 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
100%
Why I’m a Cock Whore!
Hello Love, The summer before my freshman year in high school. I found a VHS porno video right next to a dumpster behind our local video store. Brought it home. Couldn’t watch it until my family left to use the VHS player. It turned out to be a she male porno at first I felt weird but after watch... Read full Story
Samantha Cummins 2023-04-18 6,224 anal Stockings Cumshot Creampie Lingerie femboy 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 10,157 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
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 7,322 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
80%
intimate Cousins
My favorite cousin and first lover, Billy, was just released from prison and I was anxious to see him. I am ecstatic that he is out, and I am thinking about all the past fun we had as I prepare to revisit those good times. Tommy knows all about my relationship with Billy and he understands my need t... Read full Story
Regina10 2022-05-13 6,119 Stockings Crossdresser Cumshot Masturbation Bareback Blowjob Big Cock Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth double anal
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 11,928 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
91%
Hot Slutty Sissy
Hello, It’s me, and. I am about to make a big decision and right now I am dedicated to my fantasy. I got a call today from one of my ex boyfriends. I got so horny when I heard his voice that my nipples turn to steel. My titties seem to respond to the sound of his vibrating baritone. I couldn’t refu... Read full Story
Regina10 2020-08-14 6,835 Crossdresser Cumshot Bareback Fetish Blowjob blonde Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
100%
Mi primo y yo (2da parte (historia con mi vecino))
Bueno ahora toca el turno a la historia que les prometí con mi vecino. Recuerdo bien que todo comenzo un dia que mi primo y yo estábamos solos en mi casa como de costumbre por uno de los tantos viajes de mi familia, ese día me arregle super linda para mi hombre pues había comprado un conjunto de ... Read full Story
Janin 2019-12-27 3,358 Amateur Fetish Blowjob Lingerie Sex Toys Ass to Mouth
100%
Sweet Encore
I was alone tonight and feeling just a bit paranoid as I listened to the soft music. The soothing sounds put me in a seductive mood, but It seemed that all my lovers were too busy for me, or they had other plans. Uncle Barney and my detective were probably home being dutiful husbands. Bo was under h... Read full Story
Regina10 2024-05-09 3,322 Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass Ass to Mouth
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 14,133 Stockings Teen (18+) Small Tits Crossdresser Cumshot Outdoor Masturbation Bareback Fetish Blowjob Big Cock Lingerie domination Sex Toys Homemade cum in mouth
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 8,467 Stockings Teen (18+) Crossdresser Cumshot Bareback Creampie Fetish Blowjob redhead Guy Fucks Shemale Mature Ass to Mouth cum in mouth
100%
A Night to Remember
I have always had a strong fetish for stockings, garters, sheer panties, heels and other sexy lingerie. I've always required my women to dress this way for me. Even when I walk through the lingerie section in a department store or Fredrick's and I can't help but want to look at the panties and stock... Read full Story
shemale lover 2012-04-26 4,167 anal Fetish oral fingering domination Sex Toys
85%
My First Filling
It was my 18th birthday and my friends were getting on my back about still being a virgin. They’d pick on me about having not had sex with a gir yet, but they didn’t know that I fantasied about something other than a girl, I lusted and craved myself a trans partner. All the fun of a girl but with a ... Read full Story
JessicaEdwards 2018-05-04 21,454 Stockings blonde Big Cock Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Becoming Marie
I'd had always liked dressing in women's undies from an early age. It was usually my older sister's panties and skirts whenever possible. When I finally left home at eighteen and moved into an apartment in the town center, it really took off. I had had a few encounters with a few guys, mainly glory ... Read full Story
shemale lover 2012-03-22 3,542 anal sex sucking Fetish wanking crossdressing
100%
Regina and Tommy
I was getting fucked hard and aggressively by a certified bad boy named Tommy. I've never been the kind of girl who liked bad boys until I met Tommy. Tommy like doing all kinds of wild crazy things to me and I was under a spell and couldn’t object. Tommy was like the asspussy whisperer and he gave m... Read full Story
Regina10 2022-03-02 3,024 Stockings Big Tits Cumshot Bareback Creampie Fetish Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
50%
SOUS LA DIRECTION DE MAMAN
Jaime n'avait jamais eu beaucoup de chance avec les filles du lycée. C'était venu et reparti, et maintenant il en profitait un l'été dernier avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un crétin ou un crétin, c'est juste que la vie et la... Read full Story
Femboy 2021 2023-01-26 1,517 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
50%
My friend Barbara,
My friend Barbara, I look forward to welcoming Barbara. She is a lovely brunette with blue eyes who likes to make love without taboos. She knows how to bring our fantasies to life by imagining exciting role-playing games. - You're going to fall in love when you discover my underwear, she assur... Read full Story
sandratvtg 2024-07-04 1,345 Stockings Bareback Fetish transsexual Lingerie Sex Toys travesti Vintage rosebud plug gonflable gode xxl
100%
The formidable weapon of women
five ears of marriage, my desire for my wife having greatly diminished, she decided to take control of my sexuality. A female association transformed her in a few months into a perfect dominatrix both physically and cerebrally. Every night before bed, she approaches me, dressed in a latex comb... Read full Story
sandratvtg 2024-06-19 1,789 anal Lingerie femdom submissive femboy huge toys
100%
My addiction to anal orgasm,
My addiction to anal orgasm, I love feeling the sensual contact of my corset and my nightie on my skin. In front of the wall mirror in my bedroom, I take suggestive poses to arouse my desire during my lingerie fittings. Feeling vaguely like a woman, I lower my last barrier of chastity by sl... Read full Story
sandratvtg 2024-07-02 1,461 anal solo Fetish Lingerie femboy chastity cage rosebud GodeXXL
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 8,279 Fetish transformation dildo
100%
Tight Spot
XtinaSmith2017 Cody bit his lip as he looked over towards the shop, a little anxious about their planned endeavor but not wanting to come off as uncool to his friends, "Are you sure this is a good idea?" he asked. His friends grinned and laughed, playfully nudging him as they made their way ... Read full Story
Gwapo67 2022-07-22 5,922 Big Tits Bareback Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Lingerie domination cum in mouth
100%
How I sucked my first shemale cock
It was the beginning of the year 2023, in January, three days after New Year's Eve. I was driving home in the morning from a party 100 miles away from my hometown. On the highway, after going half the distance, I received a notification from my dating app, and I was like, "Oh, a new match", I'll che... Read full Story
cock&heels69 2023-05-25 8,803 Stockings cock Masturbation sucking Blowjob shemale orgasm oral sex porn high heels cum shot first experience
100%
Natacha's dungeon,
Natacha's dungeon, For a long time, I have loved wearing lingerie because it always gives me so much excitement to contemplate myself as a woman in front of my mirror. I learned a long time ago to memorize feminine gestures and attitudes while perched on my pumps. I also know how to put on ma... Read full Story
sandratvtg 2024-06-24 1,803 anal Stockings Shemale Fucks Guy Fetish Lingerie domination Sex Toys femboy chastity cage plug urétral
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 11,038 Fetish crossdressing feminization
84%
Lesser of Two Evils
My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... Read full Story
shemale lover 2013-03-27 22,826 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
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 3,665 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
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 3,530 Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking 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 5,129 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
50%
Liberty meeting , Chapter2
When she strums again on her keyboard, I feel that it sinks imperceptibly but inexorably into me. - Relax my darling, Mirella told me, masturbating me with an expert hand. At the start, I have rather pleasant sensations. Being completely submissive to this machine without being able to stop... Read full Story
sandratvtg 2024-06-20 1,563 anal Stockings Shemale Fucks Guy Lingerie domination Sex Toys femboy
66%
Candy Pink Part 2
Chapter 4 My parents had a letter shortly after from the headmaster Mr. James Allen. I was to head out to CA before the start of winter term to get settled into the dorms and go through orientation. The letter said I should be there no later than December 1st and that they would arrange for me to... Read full Story
shemale lover 2011-12-08 4,472 taboo Fetish crossdressing
100%
Two CD's the first time we meet.....
We are meeting for the first time since talking online. I want to dress for you gurl, I want to feel as you do, I want to be your slut, your slave of desire. My panties are a sheer white, my hard cock can be seen ever so pressing against them, I rub myself for you as you watch, drooling now. Hand... Read full Story
kelliecdgirl 2024-04-10 3,964 Stockings Crossdresser Cumshot Masturbation Fetish blonde Big Cock Lingerie pantyhose Frottage sissy femboy shemale + shemale
95%
My best friend turned trans.....so I fucked him - Part 1
Theres a bit of history to this one so strap in! I started hanging out with this group of kids in my area when I was 12 years old, we did all the typical stuff you can imagine young kids getting up to (played football, chased girls etc...) over the years I became really good friends with one of the ... Read full Story
iconicirish 2023-05-11 9,028 Stockings Amateur cock Masturbation sucking Blowjob Big Cock Lingerie Latex transgender sissy
83%
the start of what to cum
I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often mo... Read full Story
oliviabecket23 2023-07-04 6,809 Crossdresser Lingerie domination Sex Toys femboy forced webcams
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 7,283 first time Stockings Crossdresser Bareback Blowjob Big Cock Lingerie redhead sissy cum in mouth