Sort by
Relevancy

Free Stories

94%
My first incredible CD experience
Following my experience with Gloria I hooked up with some other shemales. The experiences were good, but nothing worth writing about...that is until I met Andrea. While on one of my typical business trips I visited a local drag club a few towns over. It was a very clean place and since it was a Frid... Read full Story
Joe Francis 2018-06-18 9,455 Crossdresser Amateur Blowjob redhead 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 4,527 Small Tits Crossdresser Amateur Masturbation Bareback Creampie blonde Lingerie cum in mouth
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 7,429 first time Stockings Crossdresser Bareback Blowjob Big Cock Lingerie redhead sissy cum in mouth
100%
Being taught a lesson .......... I think!
How did I end up on my back in my own bed, legs straight up with my ankles over her shoulders, ready to have my ass fucked from a lost bet? A bet that Alma clearly cheated at as we discover. I was off to Thailand for a 16 week course in Thai massage at a school recommended highly by a friend I ha... Read full Story
Curious_billy 2023-11-12 8,460 anal Amateur Group Sex Bareback Creampie Shemale Fucks Guy threesome Big Cock domination Homemade Vintage cum in mouth
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 11,434 Crossdresser Cumshot Blowjob jerking pantyhose
52%
Gozei até cair
A aproximadamente a 15 anos, senti um desejo enorme de ter uma relação com uma pessoa do mesmo sexo que eu, comecei a sonhar sendo possuída e me transformando em esposinha de um lindo homem. Um dia no trabalho eu conheci um rapaz chamado Roberto, um moreno com o corpo bem definido muito lindo , gos... Read full Story
fefecdzinha safada 2017-06-26 2,388 Bareback Fetish crossdressing Ass to Mouth amateurs 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 11,796 Teen (18+) Crossdresser Amateur Big Tits Bareback Blowjob Lingerie
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 5,018 Teen (18+) Amateur Cumshot Masturbation Bareback Blowjob Big Cock Uniform domination Homemade pov Ass to Mouth cum in mouth
100%
Karen, My School Teacher Part 4
Meeting my other teacher By FoxyHosed Next morning as I woke up, I jumped in my clothes and got myself a coffee, and went to school. I got in 15 minutes early because I didn't want to run into Karen. As I entered the door to the school, I saw some of my classmates. I thought the coast was clea... Read full Story
FoxyHosed 2021-02-17 7,911 Crossdresser Cumshot Masturbation Fetish Blowjob Big Cock redhead pantyhose feet toes legs cock ass pantyhose legs
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 11,361 Crossdresser Amateur Bareback Creampie Ass to Mouth
100%
Steve
So on AFF, I used to be gold but guys will just hit you up, sooo I got hit up by an 8in boy. Wasn't sure I'd want to prep up an 8 so I didn't get all ripped up, but nice profile and a fucks a fuck sometimes. What to wear to get cum in tonight? Still pretty warm, I'll go mini with tighter leotard (mo... Read full Story
smtmsbrianne 2020-09-16 3,667 Crossdresser Amateur Group Sex Cumshot Outdoor Bareback Creampie Big Cock gangbang redhead Guy Fucks Shemale Ass to Mouth 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 11,512 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
50%
SUBMISSA, ADESTRADA E BEM ALIMENTADA POR UM MACHO DOTADO parte 2
SUBMISSA, ADESTRADA E BEM ALIMENTADA POR UM MACHO DOTADO (parte 2) Como eu falei, depois de ter minha boquinha judiada e meu cuzinho maltratado por um dotado, com pauzão grosso e pesado que gozou tanto na minha garganta que tive que ir engolindo pra não vazar nada pelos cantinhos da minha boca...... Read full Story
Anymelzinhacd 2023-07-04 824 anal Crossdresser Amateur Cumshot Blowjob Big Cock Lingerie domination sissy femboy Ass to Mouth cum in mouth
50%
Rassemblement d'alumni pas comme les autres;
Un rassemblement d'alumni pas comme les autres; 'Mer/Sable/Soleil' et pourquoi pas 'Sex' dans un club de vancance; nous nous sommes rassemblés pour fêter les 40 ans de notre 1ère rencontre en fac. La seule règle était de venir sans compagne pour revivre nos jours de 'frosh'. avec les ca... Read full Story
hippocampus_171 2024-06-13 205 anal Amateur Masturbation Sex Toys Mature small cock big ass Ass to Mouth cum in mouth
50%
Rassemblement d'alumni pas comme les autres; 2/2
... J'ai ouvert les yeux, dessoûlé de l'alcool et mais aussi de mes sensations de luxure. Simo était déjà parti. Je devais me préparer pour la fête, et ce, en homme!!! MAIS, la salope que je suis, pour rendre mes seins plus proéminents sous mon débardeur pourpre foncé, j'ai serré un sangle transpa... Read full Story
hippocampus_171 2024-06-17 203 anal Amateur Cumshot Creampie Blowjob Sex Toys Mature small cock Ass to Mouth cum in mouth
100%
Just Another Sunday Funday
So I just got back from one of my favorite days: Sunday. Most people hate it because it's the day people go to church. But that's exactly why I like it. You see, every Sunday, one of my oldest and dearest lovers invites me to his home while his wife is at church. He also invites several of his frien... Read full Story
shemale lover 2013-04-19 5,124 Stockings Cumshot gangbang cum swallowing rimming
80%
Ein Traum von einem perfekten Cruising-Erlebnis
Die meisten Elemente habe ich bereits beim Cruisen erlebt. Aber die Kombination aus all dem mal un einer Begegnung wäre traumhaft. Ich stehe im Duplexx in einer der Kabinen. Wie üblich trage ich nur BH, Höschen, Hemdchen, enges Top und Halsband. Meine Brüste kommen gut sichtbar zwischen BH und T... Read full Story
Jasmin_P 2021-03-02 3,399 Amateur Group Sex Bareback Creampie threesome gangbang Lingerie Guy Fucks Shemale Ass to Mouth piss drinking cum in mouth
100%
The Beach
Summer on Long Island is the beach season. For those true sun worshipers there was no place better than the south shore, particularly the area by the Fire Island lighthouse. To add to the fun of the area is the fact that there is a section of National Seashore right by the lighthouse and this meant ... Read full Story
lkusex 2021-05-27 3,664 Amateur Blowjob Big Cock Homemade Vintage
100%
Shemale Porn
Nowadays, I masturbate exclusively to shemale porn. Like most guys, I started out reading, then watching, straight pornography. Sure, there was the titillation of happening across a cross-dressing tale in the glossy flesh mags, but they were for a ‘straight’ readership, and didn’t quite scratch that... Read full Story
Daddybear71 2023-05-24 7,733 Crossdresser Amateur Masturbation
100%
Sarah fucking in vienna
Sarah in Wien , sie nennt mir ein mir bekanntes Hotel in der Innenstadt, sowie eine feste Uhrzeit! Überpünktlich bin ich Vorort , komplett glatt , unter der Anzugshose einen schwarzen engen Nylon Slip , sneaker weißes Kurzarm Hemd, guter Duft , klopfe ich etwas nervös an der Zimmertür! Von innen k... Read full Story
Sarah Diener 2023-08-30 1,958 anal Crossdresser Amateur Cumshot Bareback Creampie Blowjob blonde Lingerie Guy Fucks Shemale sissy Ass to Mouth cum in mouth
100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 9,253 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
60%
The Creators: Book One by
Chapter One: The Life Giver BRANDON My twin sister is dead, but she’s not gone. Death is a tragedy in the remote village of Towerhead, but it’s not a rarity. Farming accidents, disease, famine, natural disasters, you name it, it kills people in Towerhead. So, six years ago, when the oxen-pul... Read full Story
sagga 2018-09-18 30,504 Teen (18+)
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 4,161 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
100%
The Mind Flip
IT was a weekend like any other, in the city in the north of England. Rain poured in sheets down the basement windows of the flat I shared with my friend Joe, breaking up the shapes of the buildings on the opposite side of the road like a kaleidoscope, and I sat indoors, slouched in front of the com... Read full Story
shemale lover 2013-01-17 5,466 hardcore Blowjob Big Cock Lingerie ass fucking
90%
When the swimming pool becomes a "hot tub"!
I decided to try and get a bit more adventurous with my act, and one day plucked up the courage to go swimming as my alter ego. I went through my usual habits of cleaning up and slipped on a tight one piece red swim suit. I filled it out with a little padding in the lining and covered it over with a... Read full Story
ATC97 2016-05-04 4,856 anal Amateur cd small dick teen TS (18+)
90%
Oh What A Night
Oh What A Night! As the old 4 Season's song stated, oh what a night. Having been a crossdresser on and off my entire life, I have done the old collect and purge routine too many times. After putting Jennifer away several years and relationships ago, the old urges returned recently. Having lost ... Read full Story
JenniferJones 2019-01-21 4,803 Crossdresser Amateur Outdoor cum in mouth
100%
Tom Didn't Get A Choice
Tom Didn’t Get A Choice This was Tom and I’s first date. We had met online, so he already knew that I was a very femme sissy crossdresser. Tom eventually asked me on a date. I happily said yes, knowing that I turned him on a great deal. On the evening of our date I wore a black dress that wa... Read full Story
pennypenny 2019-02-18 6,329 Crossdresser Cumshot Bareback Creampie Blowjob redhead Guy Fucks Shemale cum in mouth
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 5,391 Teen (18+) Amateur Cumshot Masturbation Bareback Creampie Blowjob Big Cock domination Sex Toys Homemade pov Ass to Mouth cum in mouth
81%
How I knew
Like a lot of you we all have our stories and how we arrived at being our unique selves. I was lucky to have girl cousins that saw me as one of them at a very early age and introduced me to my girly side! Sleepovers were great, I would end up wearing their pjs/nighties etc and never once thought i... Read full Story
Veronica Trapani 2019-12-06 6,950 Teen (18+) Amateur Cumshot Homemade cum in mouth
96%
It All Started
IT ALL STARTED a fanticy by CDlishmis It all started when I was just a little guy, my older sisters and their friends used to dress me up as their real life Barbie doll. I at the time saw nothing wrong with it. (I still don`t.) ... Read full Story
cdlishmis 2020-01-07 10,077 Crossdresser Amateur Blowjob Lingerie CAUGHT!
100%
The Game 2
That next morning again Ada and I went down for breakfast and the table was smaller, It wasn't as grand as it had once been and to every guy at the table was now at least two girls. We had our normal breakfast and for once there seemed to be a little more chat between everyone, I think after bei... Read full Story
chris1989r 2022-01-24 4,578 Amateur Cumshot Bareback Shemale Fucks Guy Blowjob blonde Big Cock Asian domination Guy Fucks Shemale Ass to Mouth cum in mouth shemale + shemale
88%
Surprise Ending (Part Two)
My curiosity, unconscious urges, and my horniness pushed me into action. I gently cradled Karla's balls in my left hand while my right hand settled on her taut ass. I caressed both and then let my left hand move on to her now blood engorged shecock. I am a pretty big dude, but I could hardly get ... Read full Story
Chantel13 2022-08-23 4,539 Crossdresser Amateur Group Sex Outdoor Big Cock Shemale and Girl redhead cum in mouth
100%
Mommy, can I be your fuck-toy?
I saw my step-mom taking a shower by accident or so I thought. It was not until I saw her pretty big she-cock jus hanging there between her sexy well defined legs. It was even hard & it was already as big as my cock when its hard. It looked so big that it was a bit scary yet some muscle in my anus s... Read full Story
Curious_billy 2022-11-22 7,369 Amateur Cumshot Masturbation Bareback Shemale Fucks Guy Blowjob Big Cock Lingerie Mature Homemade Ass to Mouth cum in mouth seduction
50%
Herbert BBC
Because I adore the way Herbert fucks I think of him often, and tonight would be no exception. He used to come for six hours every Friday and Saturday night. For over a year, something always seemed to keep him too busy to return for a visit. I decided to send him an E-Mail; it was only one word “to... Read full Story
PetiteSlutKimberley 2023-03-29 4,524 Bareback cd bbc breeding creampied
100%
Wife got suspicious...
Wife got suspicious... I ended up having a relationship with a married man I'll call Tom. I didn't know he was married until he told me we had to stop kind of like dating because his wife was getting suspicious. We met online, he was a guy who liked crossdressers like me. He was pretty cute... Read full Story
Kellygirl81 2024-06-18 2,660 Stockings Crossdresser Cumshot Lingerie Frottage cum in mounth
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 2,123 Stockings Bareback Fetish transsexual Lingerie Sex Toys travesti Vintage rosebud plug gonflable gode xxl
91%
Birth of a New Sissy Part 1 Encounter
I met Jeff one day at the nearby tennis courts. I could never have imagined what the result of that meeting would be. I suppose I should tell you a bit about me. I'm a happily married 34 year old. About average in most respects. A little spare tire trying to form around the middle but in decent ... Read full Story
shemale lover 2011-11-17 5,396 cum Sex Toys crossdressing
80%
A Fairy Tale Part 1
=-=-Chapter One-=-= "Heather?" My boyfriend was knocking on the bathroom door. "What's wrong, are you okay? Heather?" "Yeah..." I swallowed thickly and that was a mistake. I threw up some more, kneeling on the floor, feeling like I was dying. "Heather?&q... Read full Story
shemale lover 2011-12-06 11,642 Bareback cum ass fucking slave
100%
A life Changing Experience
My sophomore year I began dating this girl named Jan. Jan was blonde, slender, and absolutely gorgeous. She lived in this two bedroom apartment with her roommate Samantha. Sam, as she liked to be called, was a redhead, with dark green eyes and a nice chest. While not as beautiful as Jan she was stil... Read full Story
shemale lover 2012-05-09 3,737 Cumshot oral sex cum swallowing assfucking
93%
Sissy schoolgirl and her black daddy
I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning... It was summer time. As always I spent m... Read full Story
shemale lover 2013-06-22 39,920 Teen (18+) Bareback Creampie Lingerie ass fucking Interracial cd
92%
A very special lady
I knocked at the door, unsure of what to expect. Living in a big city for the last year, where I didn't really know anybody, had certainly put a crimp in my sex life. Where I used to live, in a much smaller town, during my high school years, I'd been able to get my dick into many tight, warm and wil... Read full Story
shemale lover 2013-07-18 6,165 Stockings anal sex Shemale Fucks Guy ass licking ass fingering
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 34,195 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
100%
Exposure, Disclosure
The Greatest Liar, Exposure, Disclosure © Alexandra Rios 2019 Author’s Note: This is a continuation of the narrative which commenced with “My Awkward Phase”, which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. Natives s... Read full Story
the greatest liar 2019-06-18 7,789 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
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 3,645 Bareback Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale cum in mouth
94%
Southern Hospitality Ch. 01
XtinaSmith2017 Ash gawped at his mother, incredulous as to what she had just said. He understood the basic premise of what had happened, but the reasoning she must have had absolutely baffled him. "Why?! Why would you do that?!" He pleaded, voice light and desperate. She shrugged, looking acr... Read full Story
Gwapo67 2022-05-16 7,267 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature
91%
Southern Hospitality Ch. 02
XtinaSmith2017 Laura felt herself lifted lazily from the arms of sleep, her body relaxed and floating on a small cloud of pleasure, her mind filled with images, sensations, not pulled from whatever dream she had just been having but instead, memories, memories from the night before. Memories of... Read full Story
Gwapo67 2022-05-16 4,757 Bareback Creampie Shemale Fucks Guy Big Cock Mature
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 3,969 Teen (18+) Cumshot Bareback Creampie Blowjob Guy Fucks Shemale cum in mouth
83%
Nervous Young Man II
I had been up all night the night before on dating sites and apps with the usual result; many guys promise to meet then flake out at the last minute. The most disappointing was the young Latin whose virginity I had stolen weeks several weeks earlier. I dragged through the day going through the motio... Read full Story
PetiteSlutKimberley 2023-04-07 4,838 bareback anal sex cd slut creampied
100%
Escorted
Hello! Would it be possible to have you send an escort over? A beautiful escort. Not a plain looking woman but someone special, ok? .... Ok, got it. Thanks. I opened my door to a very very sexy woman. Dressed in a tight short dress that hugged her hips and accented her nice size titties. A very bea... Read full Story
Curious_billy 2024-03-13 6,088 anal Amateur Bareback Creampie Shemale Fucks Guy Blowjob Homemade
100%
Sex With Not Just 1, But 3 Females
When I was 18 years old, I was still occasionally going to the Highbridge toilets in Lincoln on a Saturday and getting paid for having sex with guys be it sucking cocks or being sucked off, dirty chats, wanking them off or giving or taking anally. I never turned down any form of payment, money or... Read full Story
Linda Tiffany Vista 2024-05-07 2,388 Stockings Crossdresser Amateur Lingerie cum in mouth teen (18+)
100%
She Lied ......... Part 2
Looking back on that dat & being honest wit myself, I probably made sure I didn't swallow every drop. I think I wanted to finally lose my virginity. I wanted to be the bitch. I wanted to feel like the woman. I wanted to REALLY feel her she-cock expand deep inside me and feel the warmth of her nectar... Read full Story
Curious_billy 2024-07-06 2,800 Amateur Bareback Creampie Shemale Fucks Guy Big Cock cum in mouth seduction Sweet talk Virgin asspussy
100%
My Noisy Upstairs Neighbors Part 3: Making Porn
In Part 2, I recounted how Paul, my commanding upstairs neighbor, coerced me into making porn with him and his younger roommate. Now, I'm excited to share the first video we created together. At 12:45 PM on Saturday, I nervously approached Paul's door. After knocking, Paul opened it with a smile ... Read full Story
Chrissy Tunnell 2024-07-16 2,413 Crossdresser Amateur Group Sex Bareback Fetish Blowjob Ladyboy gangbang Lingerie domination Guy Fucks Shemale sissy femboy
93%
The Babysitter Chapter Two
Over the next few weeks, I could hardly think of anything but the idea of wearing girly clothes and how sexy it would feel. Every house I babysat at now, I would not just go through the underwear, I would dress up in it. I began to build up quite a collection of soiled panties stolen from the women ... Read full Story
shemale lover 2016-03-06 17,594 tranny Teen (18+) jerking off
100%
A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
shemale lover 2011-12-06 6,837 Creampie Big Cock ass fucking
100%
The best sex I will ever have!
I only have this to say about dating a T Girl! i have been in a long distance relationship with an Asian T girl from Toronto. I have been seeing her and dating her steady since then! I love her to DEATH! She is the most sensual and sexual person I have ever known! The first time we met...she gave... Read full Story
shemale lover 2012-02-02 3,583 Creampie Blowjob cum Asian
100%
Best trip to the mountains
I was driving out to the hills for some solo camping. I was alone since all of my friends had quit on me at the last minute, but i figured i'd just enjoy nature while i had the chance. I was almost through with the four hour drive, and noticed fewer and fewer cars as i got closer to the site. Onc... Read full Story
shemale lover 2012-03-04 3,969 anal shemales Group Sex oral