Sort by
Relevancy

Free Stories

80%
Amber
The summer after high school I moved into this cheap hotel downtown. I'd been working in the mailroom for a large company, and really needed to get my own place, but I didn't have much money. I also wanted to have more time to play dress up. It was an old building that had seen better days. I ha... Read full Story
ambersissy 2021-04-23 5,139 Crossdresser Amateur Big Cock Guy Fucks Shemale Interracial cum in mouth
100%
Jesse in a dress
Jesse sat primly, as been instructed, gracefully crossing his smooth, shapely young legs reveling in the sensation of the light-taupe silk stockings, sending yet even more flurries of butterflies through his tender tummy. He gently draped the flaring of the soft pastel-yellow floral summer dress ... Read full Story
ALEXEAMES 2024-01-13 3,988 Stockings Crossdresser Amateur Lingerie Homemade sissy femboy
100%
sex-agenarian's onanic lust
An onanic lust of a sex-agenarian that I am; I'M IN BIG HEAT; it's the season of bodily reunions in nature... I'm like an elephant(e) waiting to be satisfied. My cloaca is starting to titillate at the mere sight (look hah!) of a guy's swollen crotch on the street... I activated all my sensors to sa... Read full Story
hippocampus_171 2024-03-09 2,323 anal solo Amateur Masturbation Creampie Sex Toys Mature small cock
100%
Rebound!
It’d been a while since I’d last been out and had some fun. My relationship with James had broken down, and I had decided to move on. I went back to the string of websites and apps that I had previously used and had a look around for a few casual encounters. Soon enough I found someone, they hadn’t ... Read full Story
ATC97 2016-04-05 3,947 anal Teen (18+) Small Tits deepthroating cd bj
92%
A Hidden Surprise
Winter term at uni means thicker clothes which enabled me to hide some surprises under my clothes. The thicker blouses and tights would conceal anything from a thin g-string or a heavy lace pair of panties. And, me being me, I took this change of wardrobe to my full advantage. I’d been Matt’s fuck b... Read full Story
ATC97 2016-12-20 13,709 anal Teen (18+) Crossdresser Big Cock doggy style
92%
A Sissys new start
I only ever told my father one lie. That was about the boots. I was about to turn 18, jobless, directionless and pretty screwed up to be honest. There had been rows, fights, shouting matches and long frustated silences about what i was doing with my life, but i had formulated a plan. Kind of. Tw... Read full Story
SissyDani31 2018-10-04 5,370 Teen (18+) Crossdresser Amateur
90%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 12,961 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
100%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 4,752 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
54%
The day i bought my fleshlight and it was better then i expected
We have all been there, you want something bigger and better than just jerking off, not sex but something that you can enjoy solo. We have all seen that famous American Pie scene where Jim decides the apple pie will feel amazing to fuck and proceeds to shove his dick into it and if I really think ab... Read full Story
BalkanLoco91Ri 2019-08-07 4,323 Teen (18+) solo Amateur Cumshot Masturbation Creampie Big Cock Lingerie Sex Toys Homemade
100%
First fuck in public ;)
You’re only wearing a coat, I find a place where, I can kiss you then slide my hand between the flaps of your coat. I expose your breasts and slide my hand down across your tummy down to your pussy. My fingers start to explore your soft bush, working there way to your soft pink lips surrounding your... Read full Story
BalkanLoco91Ri 2019-08-26 3,561 Stockings Teen (18+) Amateur Big Tits Cumshot Outdoor Masturbation Bareback Creampie Blowjob Big Cock Uniform domination Homemade pov cum in mouth
77%
Porn site meeting and fucking ;)
We started talking on a site. I knew you were for real when you sent me a message introducing yourself. We only spoke for 2 days before we decided to meet up and I was excited to play with a real little slut. You told me the only things off limit were anal and scat otherwise i could do what I wanted... Read full Story
BalkanLoco91Ri 2019-08-26 4,677 Teen (18+) Amateur Cumshot Masturbation Bareback Blowjob Big Cock Uniform domination Homemade pov Ass to Mouth cum in mouth
100%
Edging lessons for Hannah
Hannah and I began spending our weekends together. She didn't have a job and I was always free those days so every Friday or Saturday night became sleep over night where we could be two 18 year old sissies, doing each others makeup, playing dress up and sharing our deepest desires. Now that our rela... Read full Story
KaceyKlarissa 2024-01-25 2,941 Crossdresser Amateur Cumshot Masturbation Fetish Big Cock kissing Homemade sissy romantic cum swap edging teen (18+)
50%
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 2024-05-07 306 Stockings Crossdresser Amateur Lingerie cum in mouth teen (18+)
96%
Making A Man Out Of Tommy
I have two good friends, Brad and Matt who are actually my fuck buddies. Both of them travel for work, so they tend to be gone a couple of months at a time. I have a key to their apartment, so I can let myself in for sex when they are home and to bring in the mail when they are not. I also get to us... Read full Story
pennypenny 2018-08-31 9,622 Teen (18+) Crossdresser Amateur Masturbation Bareback Creampie Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
88%
Who's She?
School had been a bore for Tony. He was a bright lad and didn't have to work too hard to get through classes unnoticed by the teachers and class mates. He had plenty of friends but no one close. He didn't excel in sports or academically. He had picked up a few good exam results but had decided that ... Read full Story
Vinny_A 2019-07-08 11,398 Teen (18+) Crossdresser Amateur Big Tits Bareback Blowjob Lingerie
100%
Booty call :)
Your cock pounds my ass harder, my cheeks rippling with every deep thrust you give. The sounds of our moans and your balls slapping as you fuck me hard is suddenly broken by the ringing of your phone........... And you wake up. It's 2:30am and I've just finished work. As arranged, I'm giving... Read full Story
BalkanLoco91Ri 2019-08-26 4,880 Teen (18+) Amateur Cumshot Masturbation Bareback Creampie Blowjob Big Cock domination Sex Toys Homemade pov Ass to Mouth cum in mouth
100%
How my date went
There I was on TV with the sound up jus barely enough for my date and I to hear. We had gotten past the introductions at the bar we had jus left & now it seems as if those 4 shots of tequila jus wasn't enough for me to overcome how scared I was. But Alma, my date had run into Nervous Nellies like m... Read full Story
Curious_billy 2022-10-21 5,297 Teen (18+) Amateur Cumshot Masturbation Blowjob Big Cock Lingerie Homemade pov cum in mouth webcams
92%
My story
"You're gonna make me suck that, aren't you?", I asked her. " Yes" she said. "But you're going to suck it because you want to". " I doubt that", I said. "We'll see", she said with a smile. "You're gonna cum in my mouth, aren't you?", I asked? "Yes baby, Mommy is gonna feed you her sweet nectar... Read full Story
Curious_billy 2022-12-01 6,472 Teen (18+) Cumshot Bareback Shemale Fucks Guy Big Cock domination Homemade cum in mouth
100%
Becoming Kacey
I indulged my crossdressing opportunities as often as I could, but as time went on, the chances grew further and further apart. Although I couldn't play dress up in my alone time, the fantasies never seemed to cease. When I entered high school, I dated girls and enjoyed the young passions that teena... Read full Story
KaceyKlarissa 2024-01-16 3,436 first time Crossdresser Amateur Homemade sissy femboy shemale + shemale romantic teen (18+)
89%
The Magic of my first Blac Coc
Wow! This was my first real experience with Black Cock. it was right after my divorce. I was in my late twenties. I ran my ads as a crossdresser on a few dating sites and on Craigslist. I received a message on my AFF site from a member whose profile name was BBCRicky. My interest was immediately... Read full Story
Tvtrinity 2021-04-07 21,340 Stockings Amateur Bareback Lingerie Interracial transgender sissy bbc сrossdresser tvtrinity
95%
"University" Friend
University “Friend” Finally I had earned a little more freedom. I was off out of my sleepy village and at university. I had a small flat in an apartment block all to myself in a nice enough part of town. I unpacked my clothes and settled down for my first quiet night in, but as I put a few of my ... Read full Story
ATC97 2016-06-21 11,445 anal Teen (18+) Crossdresser Lingerie cd
86%
Hitchhiker's Delight
Hitchhiker's Delight Last week I was driving down the east coast heading towards the Gold Coast when I spotted a gorgeous looking hitchhiker. She was wearing a very short skirt that showed off her slender tanned legs very nicely and with the way her large breasts were only just contained in he... Read full Story
iluvgurls 2017-05-15 15,119 Amateur suck oral sex hard dick outdoors
100%
Amy and the Straight Jocks PT1
Only a couple close friends knew for sure and most others knew it as just a rumor. Amy dressed and lived life as a girl like she had since the start of high school when she moved from a new town. The jocks would laugh and whisper to each other when she walked by debating if the rumors were true. Co... Read full Story
DADDY4sluts 2022-08-09 3,660 Teen (18+) Cumshot Bareback Creampie Blowjob Guy Fucks Shemale cum in mouth
100%
Alexis
When I hear both of my parents starting to snore in the room below me, I quietly get out of bed and sneak over to my dresser. I dig past the piles of underwear in the top drawer until I find what I am looking for. I pull out the black silk g-string and slide it up my shaved legs, tucking my tiny coc... Read full Story
shemale lover 2012-10-06 4,160 oral facial cum swallowing jacking off
100%
Pretty Woman
Tyler was as nervous as anyone could be. Hazel eyes darted for the door as silky black stockings slid up smooth white legs to meet garter straps attached near lacy white panties. Next came the bra, straps catching on skin slightly sticky with perspiration. Heart pounding as the black pencil skirt gl... Read full Story
shemale lover 2012-12-22 8,501 Stockings Teen (18+) Crossdresser sucking heels
90%
Shemale Charlotte caught wanking in the bath
Charlotte is a very small 18 year old, very skinny, only just 5 foot but has an amazing pair of breasts which stretching the skin makes them show veins all over. Her pale skin showing the veins even more. Charlotte is also a shemale, her small size and large breasts she also has a very large 8inch (... Read full Story
shemale lover 2013-06-18 6,787 Amateur Cumshot Masturbation jerking Shemale and Girl
93%
Lakeside Awakening
If anyone had told the way I'd meet my soul mate a few years ago, I never would have believed it. It was my senior year of high school and I had recently gotten out of yet another bad relationship with a girl. Lina had been a pretty, chubby blonde with a nice personality but a nasty temper. We ... Read full Story
AlliV 2014-09-02 6,458 tranny ass Teen (18+) Big Cock jerking
100%
Sissy Slut and Stepdads part 2
My mother kicked Frankie out and swore that he was the last loser she would ever date. She believed that we were still having sex, and she was right. Pure raw animal lust drove us, and It was even better when we sneaked and got. That nervous adrenaline mixed with my passion and made me super horny a... Read full Story
Regina10 2021-02-15 3,852 Teen (18+) Crossdresser Big Tits Cumshot Masturbation Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Homemade Ass to Mouth
96%
Ladyboy surprise in Bankgkok
A few years ago I went to Thailand for the first time, my first stop was the bustling city of Bangkok. I had heard stories about the nightlife, the girls and the tourists. The country had never appealed to me that much but through a twist of fate I ended up visiting the city of sin for a couple of d... Read full Story
Gracemel121 2021-03-25 11,522 Amateur Shemale Fucks Guy Big Cock Asian Ladyboy cum in mouth
100%
After Gym Class Chapter 01
I was tired. It was the last period of the day, so at least the day would be over soon. I didn't sleep very well last night, still thinking about that jerk Josh and what he had said. "I really want someone who is more open to doing different things sexually," he had said. What the fuc... Read full Story
alwaysupforu2004 2014-09-17 6,407 Teen (18+) Cumshot suck shemale stroking
87%
Dani & Paulie - 1
It was two years since Carl had taken me in the cellar of that bar. Paulie and I had moved to a large apartment courtesy of an unexpected inheritance from his father. I should really say "her" father, we had started using feminine pro-nouns for each other somewhere along the line, no one could reme... Read full Story
SissyDani31 2018-10-08 3,814 Crossdresser Amateur
94%
SISSY RULES!!!
There are a few things a sissy must understand in order to attract, and then keep, her man. Let’s look at them, these Sissy Rules. (✿◠‿◠) 1. Men are superior to you. This is rule number one for good reason: it is a simple statement of fact. It is so important that many questions that a potent... Read full Story
KittyHot 2021-06-18 7,794 Crossdresser Amateur Fetish submissive feminization sissy submission femboy hypno beta obedient
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 3,094 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
100%
Biggest cum load I ever did see.
You know those porn movies where they fake a guy shooting about a pint of cum? There's obviously a tiny hose of some sort taped to the side of his cock that you can't see and it pumps out vast amounts of whitish fluid and it's all a bit silly, though quite cool. And you know it can't be real because... Read full Story
kiwicd 2022-04-27 3,137 Crossdresser Amateur Cumshot
100%
mushrooms in all shapes and forms
Mushroom season is open! Yummy! I love mushrooms, in all shapes and forms. We were about fifteen mushroom lovers who only get together to pick mushrooms, without any other friendly gatherings! For this last outing of the season, our splendid instructor was accompanied by her cousin, who was sup... Read full Story
hippocampus_171 2023-11-24 6,008 Small Tits Amateur Cumshot Mature small cock big ass bisexual cum in mouth bald men glabrous
100%
Second meet
So I arranged for this guy to come round, was a good few month after my first time so my ass was tight again. I was in the usual, fishnet suspenders, heels, skirt, bra and ladies bikini bottoms, as I had no girly ones which were clean. I answered the door to him and led him upstairs, same routine, t... Read full Story
mikey1993 2016-04-05 2,905 anal Crossdresser Amateur sissy
55%
story of Jojo
Some find it confusing of who i am or what i am, including me. i found some kind of definition: femboy A young boy who presents extensive feminine mannerisms and actions often blurring the line between a boy and a girl. Can be confused with a cross dresser, but it usually refers to boys at v... Read full Story
jojo58654 2017-09-12 10,279 Amateur transvestite strapon cd femboy
73%
Tabitha at 19
Tabitha’s home from her freshman year of college. She’s gone off to California to a screamingly liberal school and I’m sure she’s been making new friends, learning new things, opening her horizons and fucking safely. After I popped her cherry and we had a very discreet summer of me teaching her a lo... Read full Story
Giantsquid 2017-05-16 6,468 Small Tits Amateur Cumshot Blowjob Guy Fucks Shemale cum in mouth
50%
Domination of Bjarne
Dear Diary. At the behalf of my lover Bjarne alias Cigar54, I will ease the curtain of my bodouir and invite the curious reader inside to a little piquant seance that we had together during his recent visit over here. Bjarnes visites always begins with kissing deeply, while my hands find the way to... Read full Story
Louice 2018-03-02 3,055 Amateur Shemale Fucks Guy domination Ass to Mouth
81%
My wonderful life with Patl : The dinner
Hello All, Since Pat told me to serve her fully naked i was/i am really keen to back home and to make her happy. One day she told me, I hate to see you so hairy, I would like you will be fully shaved. I will be very happy to have your cock, balls and ass smooth as a baby skin. I will shav... Read full Story
jperrot 2020-07-21 3,718 Amateur Shemale Fucks Guy Big Cock domination slave guy
100%
Camming down the rabbit hole Ch5
I was jolted out of my sleep by the phone on my bedside table vibrating, bleary eyed I picked it up and saw a message from the couriers that a package would be delivered today around 4pm. The realisation that this was the package I had been waiting for and I could finally wear something else in my s... Read full Story
Dani_does_Dallas 2021-09-29 4,713 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade cum in mouth webcams
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 4,750 anal Amateur Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Big Cock domination Mature Homemade cum in mouth
100%
Working the Glory Hole
After so many nights of torrid fantasies plaguing my sleep, I took a long look at myself in the mirror. I had been slowly embracing my femininity over the past few months. My hair had grown past my shoulders, I was shaving my entire body on the regular, and I would wear panties under my guy clothes ... Read full Story
KaceyKlarissa 2024-04-15 2,379 Crossdresser Amateur Cumshot Masturbation Blowjob facial glory hole whore sissy cum in mouth sissy slut
84%
The One That Got Away
I was out on a Friday night seriously just looking for a couple beers and a burger. I had a lot of work to do around the yard and house on Saturday and was having some guests for brunch on Sunday. Full weekend, tired from the week. I went downtown to a new gastro pub I’d seen reviewed in the local p... Read full Story
Giantsquid 2017-05-15 5,510 Amateur Bareback Lingerie guy on shemale
100%
My Afternoon With Venus - Part II
My mind was still spinning from the out of this world cock sucking I'd just experienced at the expert lips of my exotic little doll as she led me by the hand into her bedroom. Her pink summer dress was draped down onto her waist so now it was only just covering her cute little derriere. As I wa... Read full Story
funpics 2018-03-23 13,050 Amateur Shemale Fucks Guy Asian Ladyboy Guy Fucks Shemale Homemade
83%
Las Vegas Swingers
It had been over 6 months since I seriously dated someone, and I was getting depressed and in a rut. I had directed my attention to my work and it kept me from feeling sad about my loss of someone I almost married. I had met a transsexual girl that absolutely adored, but she was tragically killed. (... Read full Story
Jon Paul 2018-06-11 9,980 Amateur Guy Fucks Shemale Mature Ass to Mouth cum in mouth double anal shemale + shemale
100%
The Mocha Club... A Wife's Awakening
Fran had spent a restless evening in her hotel room, flicking through the channels on the television, finishing the large glass of red that room service had brought her and writing up the actions from the client meeting earlier that day. Now she was bored. It didn't help that the hotel her manager h... Read full Story
ASSEaster5678 2018-07-09 8,805 Amateur
25%
Fantastic threesome w/ Miranda Pinocchio & Danielle Albuquerque
Today taken by the craving for something really big I call Miranda who answers me immediately and despite the language barriers and her way of speaking not always understandable we agree for 70 and a quiet thing. I sling in Naples, central area, the usual low in the alleys between via Marina and the... Read full Story
RonWisley 2020-05-04 4,435 Amateur Cumshot Shemale Fucks Guy threesome Blowjob Big Cock
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 3,609 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Uniform Lingerie Homemade self sucking pov cum in mouth
100%
The formidable weapon of women,
The formidable weapon of women, After five years 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, sh... Read full Story
sandratvtg 2022-09-20 4,632 Stockings Amateur Blowjob Lingerie domination Sex Toys
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 6,024 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade self sucking pov cum in mouth
50%
Giving Away Virginia Holton
Today would have to wait, thought Marla Holton as she hurriedly gathered her bag and notebook in preparation for a no-holds-barred departure from her office at Prism Design. As general manager she had the privilege of arriving and leaving at will, though no one could ever fault her for not putting i... Read full Story
shemale lover 2011-10-08 4,382 shemale cum ass fucking
95%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 30,453 strapon porn
90%
Panty Town
Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... Read full Story
shemale lover 2012-01-29 18,998 Big Tits sucking ass licking fucking
100%
Chapter 1 - My Cuckold Life
I have a small penis. In fact, I have a very small penis. I’ve been in permanent chastity for over 7 years. My wife and her lovers call it my “caged clitty” and that’s about right as far as it being a useful penis. I suppose I should start at the beginning. I’ve never been much of a man. I’m ... Read full Story
Sissy Annabelle 2022-08-23 5,717 Crossdresser Interracial sissy chastity Cuckold Husband
76%
Nylon teasers
They came into the video store where I worked as a clerk. Almost every day. Teasers. Both of them. What made it both great and terrible for me was that it fed my deepest fetish -- stockings -- as it denied me any fulfillment other than frequent and frantic "self-gratification."... Read full Story
shemale lover 2012-01-30 9,655 Stockings Big Tits fucking foot fetish