Sort by
Relevancy

Free Stories

100%
My First Blowjob
Fuck! I'm so jealous! Back in my teens I could self suck! I'd lock myself in the bathroom, lay on my back and bring my legs over top. I was able to not only get the head of my.cock in my mouth, but half of my length as well. The first time I nutted in my own mouth, I wasn't prepared for the big lo... Read full Story
Hardrock51Fifty 2024-03-26 4,020 solo Cumshot Blowjob self sucking cum in mouth teen (18+)
94%
My first blowjob from a hot transexual next door
In my neighborhood there's a transexual friend of my mom, she owns a salon, and it was frequent for me to wait for my mom to get her hair done, while i just looked at her discretly, she was around mid thirties, with a very hot body and beautiful blonde hair, it was a common sight to watch her walk o... Read full Story
AhYesReapers 2023-03-30 6,828 first time Blowjob blonde swallow milf cum in mouth
100%
Becoming addicted to her she-cock
"I'm going to make you a very happy woman tonight when I slowly but firmly slide my long, thick, hard she-cock all the way up your tight virgin ass tonight baby" Alma whispered in my ear as we left the bar I had ?mistakenly? stumbled into. I shuddered with both fear & a bit excitement. I don't why ... Read full Story
Curious_billy 2023-05-07 7,227 Teen (18+) Amateur Cumshot Asian Ladyboy domination Homemade cum in mouth
50%
Larissa blond blown in Frankfurt
Very friendly already on the phone. She was very chatty. Asked when I wanted to come and I said at 12:00. I meant if she squirts and she answered yes, but costs 50 € extra. She then said that at 12:00 maybe her landlord will come, the bed would be broken. If he hadn't been there by then, we would ha... Read full Story
Bigpruegel69 2023-12-17 5,079 Cumshot Masturbation Creampie Blowjob cum in mouth
97%
Shemale fucks guy - My gf fucks my slutty ass.
I have a shemale girlfriend & we both are in a relationship. One day, I decide to give her a visit. I'm 5'7 guy & she's 6 feet. That makes her tall & intimidating & whenever we meet, it's me who become her gf. I visit her, she takes me in. SHe pulls me towards her while giving me a deep kiss. I ... Read full Story
glodobox 2020-12-04 22,052 Amateur Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Homemade cum in mouth
100%
TO BE OR NOT TO BE – PART 3
TO BE OR NOT TO BE – PART 3 by Spanky de Bautumn Part 2. At the hotel in New York City, Sunny meets the bellhop, Antonio, and they go out for a drink when he gets off of work. The call came at exactly seven. I had woke up about five minutes before and was watching Antonio sleep. All of the oth... Read full Story
SpankydeBautumn 2021-02-23 2,450 Small Tits Crossdresser Amateur Cumshot Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
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 4,943 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
100%
HypnoSissy Partie 2
DEVENIR CUM SLUT Une fois habillé et James parti, Rose demanda: "Vous êtes-vous amusé?" Je hochai la tête. "Oui, bien que je me sente un peu gay." Rose secoua la tête. "Brian," gay "est juste un mot, comme" lesbienne ", ou" faggot "ou" gouine ". J'ai mangé la chatte et demandé aux filles... Read full Story
Femboy 2021 2023-01-24 3,877 Stockings Teen (18+) Crossdresser Fetish Blowjob Big Cock Lingerie domination cum in mouth
100%
A Fantasy - Part 2
Paula begins to grown, ohhing and ahhing. I suck hard and swirl my tongue around on the head of her cock. Sharon has pushed her dildo all the way into my ass and begins to pump my ass with a slow, steady rhythm. Paula holds my head in place and begins to thrust her cock into my mouth harder. "I'm go... Read full Story
swollenrooster 2023-09-20 4,963 Group Sex Cumshot Shemale Fucks Guy Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
83%
How i became a sissy/my first blowjob
I'm a 17 year old sissy now but i started crossdressing 4 years ago when i was 13 :).This is the story. One day my parents went to our lake house for the weekend with my s****r but i was feeling sick so they left me with my grandparents. They were taking care of me for a day or two and i got better ... Read full Story
shemale lover 2013-08-09 53,369 Teen (18+) Crossdresser suck oral cum swallowing cd
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 3,773 Stockings Teen (18+) Amateur Big Tits Cumshot Outdoor Masturbation Bareback Creampie Blowjob Big Cock Uniform domination Homemade pov 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 6,757 Teen (18+) Amateur Cumshot Homemade cum in mouth
82%
Best friend
Looking back, it seems my early teens were really a time for me sexually. Puberty had set in hard and fast and I was sexually charged. I was constantly touching myself and fantasizing about every sexual explicit act I could think of at the time. Lucky for me I had my best friend Jason. We wer... Read full Story
Veronica Trapani 2020-03-09 6,181 Teen (18+) Amateur Outdoor Blowjob Homemade cum in mouth
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 3,825 Teen (18+) Cumshot Bareback Creampie Blowjob Guy Fucks Shemale cum in mouth
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 1,694 anal Crossdresser Amateur Cumshot Bareback Creampie Blowjob blonde Lingerie Guy Fucks Shemale sissy Ass to Mouth cum in mouth
100%
First Cross-dressings Loosing Anal Virginity
It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... Read full Story
Trapbomb1 2022-07-29 6,667 Teen (18+) Crossdresser Bareback Creampie Blowjob Big Cock virgin virginity sissy cum in mouth double anal sissy slut virgin ass
100%
Dressed in holiday style Part 2
I was up by 1 p.m., showered, changed into some fresh panties and donned some hated boy clothes to hit the streets. I stopped by a local coffee shop (not the national chain-brand type) and over a mocha latte the barrista was kind enough to give me a few pointers about where she thought the best holi... Read full Story
shemale lover 2011-11-20 2,025 anal Stockings cum
65%
Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
shemale lover 2012-12-19 10,517 Masturbation Blowjob blonde ass fucking big boobs
100%
I fucked my personal trainers ass for the first time
I greeted him on my bed in my sheer black lingerie. I knew he’d be nervous, and truly I was as well. We’d spend so much time in the gym together and I knew he wanted me, but taking that next step was sometimes difficult, especially when our relationship was always professional. Posing for him, I r... Read full Story
Madison Heights 2023-05-18 6,885 anal Shemale Fucks Guy Big Cock Frottage
100%
A man & Two Hung Shemales meet in Art Gallery o
I spent a week of absolute extreme erotic ecstasy with Stan. I used his throat and ass multiple times a day. He also fucked and fisted my ass as well. It is a week of total decadence debauchery and depravity. In the late afternoon, Stan and I decide to visit a local art exhibit so we can get out ... Read full Story
darrell 2024-02-02 5,123 anal Cumshot Big Cock Frottage deepthroat shemale + shemale swallow cum
86%
Giving shemale a blowjob for the first time
I've been fantasizing about a shemale cock for a long time. Get me right, I am a straight man and all, but somehow the idea of sucking a girl's dick always turned me on. I'm not a big fan of anal sex and I don't think I'd love someone's cock in my ass, I'd rather prefer to give shemale a blowjob. ... Read full Story
shemale lover 2011-07-09 11,946 licking Blowjob shemale
96%
How I Really Got My BA In College
I was living in an off-campus apartment building two months into my first semester of a two year BA program. I lived on the 22nd floor and my three friends Ray,Jim and Dan lived together on the 13th. As it was Friday night I threw a couple loads of laundry into the wash and went downstairs to cadge ... Read full Story
shemale lover 2013-02-12 6,191 Cumshot sucking Blowjob ass fucking swallowing
100%
TG affair in Bimini
The day was rainy and weather was dreary, not much to do and have the day off. I fly a charter plane that takes people to and from the Bahamas from Ft Lauderdale. My girlfriend Jan and I only stay together a few days a week, she is in Real Estate and with my schedule we have not been together in t... Read full Story
Jon Paul 2021-04-19 3,261 Teen (18+) Bareback Creampie Blowjob Guy Fucks Shemale
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 3,441 Creampie Blowjob cum Asian
33%
My new Experience with Amy Cute Shemale in Pune
Hi friends i am back with new story. I am mad shemale lover. and keep on finding new shemales for me. This time i got new website to search for shemale www.massagerepublic.com I saw an advertisement of Amy and i liked her. called her and fixed appointment. went to her hotel, which was ok ok ... Read full Story
Stud4Shemale 2021-02-20 6,061 Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale shemale fucks man man-fucking-shemale Indian Shemale Pune
100%
Linda and Cum on Heels
I was told by a cute guy today they would love to cum in a pair of my strappy heels............this was my answer to him. (I hope you enjoy what happened in what could have been unfortunate circumstances) Actually a person did. I had picked him up from the Lincoln University area and we went off ... Read full Story
Linda Tiffany Vista 2024-05-07 1,813 Stockings Crossdresser Amateur Blowjob blonde
66%
I've never wanted to have someone inside me this bad
I've never been so anxious to get something deep inside me as I have this babes hard cock. All I've thought about all day is how much I want to rip his clothes off and shove his dick in my mouth until his cum drips down my throat. I've already fingered myself twice thinking about it. ... Read full Story
Shiloh Patutie 2017-04-29 4,541 anal Blowjob cum in mouth cum in ass
66%
Sex in the kitchen with my hubby's friend - a cop
Ever since my wedding last year, I enjoy a great time with my hubby who loves me so much and takes care of me so much. Since he is married and having another family, he doesn’t stay with me all the time, but comes and stays at least 2 or 3 days in a month and we literally celebrate those nights wit... Read full Story
Manusha Tranny 2021-10-14 5,125 Small Tits Crossdresser Amateur Cumshot Outdoor Blowjob Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
84%
Shool teen crossdresser first time sex
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest f... Read full Story
shemale lover 2014-11-21 18,522 first time suck fingering Lingerie ass fucking cd
100%
Born to suck
I’m a straight guy who watches to much porn and when I hit my thirty’s regular porn was getting boring. while searching the web I stumbled across some tranny porn, now I always loved blowjob porn it was my favourite but now watching a big dicked tranny getting her cock sucked is my favourite and I ... Read full Story
Beesknees 2018-03-02 6,384 Blowjob blowing
69%
Catching Up with A Former T-Gurlfriend
I was jogging one Saturday morning at well known West L A park. I was jogging kind of fast almost sprinting when I came up on woman jogging slower than me. I almost ran into her as I was running. She moved out of my way I slowed down and apologized for being rude. That's when I realized she was a fo... Read full Story
Brett1 2018-08-06 4,311 Latina Shemale Fucks Guy Blowjob cum in mouth
81%
First time with ladyboy / bottom
Hi everyone! now it is my turn to share my experience in Thailand. We were on a Christmas vacation on an island, and I didn’t even know ladyboy existed then. At a Christmas beach party I chatted and danced with a woman and we ended up in my bungalow. We kissed a lot and I knew that now I was g... Read full Story
FoxyLover'ts 2020-10-06 16,043 Cumshot Blowjob Big Cock domination Interracial Homemade cum in mouth ladyboy ts thailand ladyboy shemale fuck guys virgin ass bottom boy bottom virgin
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 4,284 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
100%
Cum is a Cross-Dresser New Drink
Nikki looked up at me with her big, brown eyes as her head bobbed on my cock. Nothing was quite so sweet as one of her blow jobs. She had this way of dragging her tongue along the underside of my cock that made me want to cum in seconds. I always tried to hold it, but Nikki wouldn't let me. When she... Read full Story
ASSEaster5678 2018-09-14 6,496 Crossdresser Cumshot Ladyboy cum in mouth
100%
TO BE OR NOT TO BE – PART 6
TO BE OR NOT TO BE – PART 6 by Spanky de Bautumn Part 5. Sunny and Antonio got frisky at the bar, Sunny moved in with Mel and Shari, and opening night was a success The only other dress that I brought was one that I hoped I would get a chance to wear but didn't think I would. It was a black ... Read full Story
SpankydeBautumn 2021-02-26 2,354 Stockings Small Tits Crossdresser Cumshot Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
TO BE OR NOT TO BE – PART 6
TO BE OR NOT TO BE – PART 6 by Spanky de Bautumn Part 5. Sunny and Antonio got frisky at the bar, Sunny moved in with Mel and Shari, and opening night was a success The only other dress that I brought was one that I hoped I would get a chance to wear but didn't think I would. It was a black ... Read full Story
SpankydeBautumn 2021-02-26 2,382 Crossdresser Cumshot Masturbation Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
Kate Berges the Shemale who fucked first in my ass
I was with her last week. She was in a duo. So I went there and rang the bell. Recognized me right away and gave me a deep kiss. I then asked her if she was available in the duo and her colleague a.) cums properly and if she would also fuck each other, which she confirmed. She then went out and c... Read full Story
Bigpruegel69 2023-12-17 6,670 Cumshot Creampie threesome Blowjob cum in mouth shemale + shemale
100%
Crossdressing at CCBC in Palm Springs
I recently stayed at CCBC in Palm Springs. For those of you who are not aware of it, it is the largest gay resort in Palm Springs area. The resort has about 30 rooms, lockers, a pool, steam room and indoor and outdoor play areas all on a one acre outdoor enclave. I arrived there on a Tuesday and dre... Read full Story
Rocky8844 2024-05-27 2,426 Crossdresser Group Sex Blowjob Lingerie pantyhose cum in mouth
86%
Never Wanted To Be Your Girlfriend Ch. 03
Derrick really took advantage of having me captive that first weekend. He spent the entire time making me watch porn videos, and then had me recreate the scenes with him. He said, that he needed his girlfriend to be fully versed in all the ways he liked to be pleased. His appetite for sex was unreal... Read full Story
shemale lover 2014-07-21 5,767 Cumshot suck Blowjob facial oral sex
87%
My way to shemale sex
It all started with porn. 10 years ago, i was watching porn on my bed, jerking off watching a girl sucking a big cock. I looked at my cock and started wondering what that beautiful peace of meat tasted like. After a few moments of hesitation, my curiosity took over and i put my back against the wall... Read full Story
andre_xp_8 2018-07-24 13,665 anal Blowjob shemale first time
90%
Long weekend at work
So I am the low man on the scale at work. My job is with the City I work in dispatch and am one of the people responsible for getting road crews, hydro and sewer crews out to fix problems wherever they occur. My boss is a very attractive woman named Jamie. She stands about 152 centimeters and dar... Read full Story
Zöe from Kingston 2018-08-09 5,926 Cumshot Bareback Shemale Fucks Guy Blowjob cum in mouth
61%
Car Broke Down
A Fantasy: Car Broke Down My car was running hot so I pulled into a driveway so that it would cool down. I got out and raised the hood and added some water. I then got back inside and smoked a cigarette and sipped on a beer that I had. I listened to the radio and glanced out the window and... Read full Story
iluvgurls 2018-11-14 7,266 Small Tits Creampie Blowjob Lingerie cum in mouth
83%
Janine awaits
My story is not typical. Sure, it mirrors many of the others you’ve read except for one aspect, that is my age. I recently celebrated my sixtieth birthday. Yep, the big 60. And not that I am trying to brag but I am one of the sexiest bitches around. As recently as five years ago I looked like any ot... Read full Story
bunny cat 2019-02-04 3,744 Crossdresser Masturbation Blowjob Lingerie Mature cum in mouth
100%
Lustful Crossdresser by CDlishmis
As I think about the way I feel when I dress in women’s clothes. I become agitated with myself. I can’t stop. I couldn’t stop even if I wanted to, it is an addiction. The physi cal and mental transformation that I go through is ex... Read full Story
cdlishmis 2020-08-31 3,113 Crossdresser Blowjob gangbang Lingerie domination cum in mouth psychological
100%
Liberty in Lisbon Part 3
After Olivia had so perfectly taken my anal virginity, we laid in bed cuddling, touching, kissing and her cum leaking from me. I had not been so lovingly caressed for such a long time. It was just perfect. She asked me how I was feeling. I think I said before that I don’t do deep and meaningful very... Read full Story
Rusty12 2020-09-16 3,297 Masturbation Shemale Fucks Guy Blowjob old-and-young 69 sucking
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 5,058 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
50%
I'M A DIRTY WHORE EXPOSED TO PUBLIC HUMILIATION
There are people on porn sites who hunt down people like me and make me a world famous whore. They download all my photos that I publish. Sometimes they add descriptions to photos. They share my photos on all known porn sites, forums, chat rooms. More and more people have my photos. Some people edit... Read full Story
QUEEN HARLOT 2022-02-14 3,003 Big Tits Cumshot Blowjob public humiliation cum in mouth double anal whores humiliated whorehouse degrading degraded public humiliation
100%
I met a guy in the nightclub and I didn't tell him I was Trans
I’d worn an absolutely killer dress just to make sure I got what I was looking for that night. Dancing under the lights I could feel eyes all over me, and as the evening progressed men became bolder and bolder about approaching. This one was athletic, sexy and had all the right dance moves, at least... Read full Story
Madison Heights 2023-03-25 6,597 Cumshot Outdoor Blowjob Big Cock cum in mouth club outfit Surprise Cock Partying surprised
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 6,105 anal Amateur Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Big Cock domination Mature Homemade cum in mouth
100%
Taken and in Public Part 3
I tried to go to sleep but was just so horny; I wanted to dress up again; I wanted to go out; I wanted to be fucked! All these emotions were running thru my head and I just lay there. My mom told me she would be starting the 7pm to 7am shift at the hospital for some time and thought I should get... Read full Story
shemale lover 2012-01-14 2,854 Fetish crossdressing ass fuck
100%
A Night of Makeup, Cock and Cum
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further,... Read full Story
shemale lover 2012-04-18 4,682 Cumshot jerking off domination Sex Toys cum swallowing
100%
Double penetration in Vegas
On a trip to Los Vegas for my Birthday we had a great time. Same old shit, we won and lost, saw all the sites and a few shows. The last night we were there however we were BORED…. That being said and knowing US, We took a stroll around the hotel. Maxx was checking out all the hot women in the... Read full Story
shemale lover 2012-05-31 4,761 anal sex Blowjob transsexual orgasm
80%
Three In A Day
Clara felf especially slutty today. She briefly gazed at her long legs shimmered in the smooth, silky black stockings, and black patent leather pumps as she pressed the gas pedal of her car. Her olive skin and black wig were set off by the brightest shade of red lipstick she could find. Driving d... Read full Story
iluvgurls 2018-11-12 4,524 Small Tits Crossdresser Group Sex Cumshot Blowjob cum in mouth
100%
Business trip
Craig and I were salesmen for the same company and on a trip together to woo new clients. The last thing I expected was that we would woo each other. It had been a long day and we went to our rooms to relax and unwind. After I had my room service and wanted to go over the proposals I realized Crai... Read full Story
Zöe from Kingston 2019-10-07 7,216 Crossdresser anal sex Cumshot Blowjob Lingerie cum in mouth
100%
TO BE OR NOT TO BE – FINAL ACT
TO BE OR NOT TO BE – FINAL ACT by Spanky de Bautumn Part 7. Sunny spent the night with Antonio and the next day they went to Mel and Shari’s for some fun. Antonio had school, so he was up and out early on Tuesday. Mel was in the shower and I was laying in bed, my mind wandering and not real... Read full Story
SpankydeBautumn 2021-03-02 2,451 Small Tits Crossdresser Cumshot Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
DOM of a MTF dream
I had a dream the other night. I was getting out of work, and was walking home. I walked by a bar with only a couple people inside. It looked nice and quiet where I could have a drink and unwind. I walked in and ordered a mixed drink. Half way through it I saw a young girl looking my way. I c... Read full Story
77James 2021-10-07 2,725 Blowjob cum in mouth