Sort by
Relevancy

Free Stories

85%
Gilding the Lilly
It was a dark and stormy night. Oh, wait, I was taught NEVER to begin a story like that. (Snoopy can get away with it, but he does all his writing with a typewriter balanced on his doghouse). OK, getting back to important things. It was actually early Autumn out in the Desert, cool weather was s... Read full Story
CharlotteSlut 2018-03-02 6,010 Group Sex Shemale Fucks Guy gangbang Shemale and Girl shemale + shemale
95%
Ginger's First Gangbang
I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... Read full Story
Ginger__57 2018-03-26 8,634 Stockings gangbang redhead domination Guy Fucks Shemale Ass to Mouth cum in mouth
77%
Chicago TG Romance (part 3)
It is Sunday morning, just barely dawn and I have just spent the weekend with the most amazing girl. You know when everything clicks and it seems that at first you have met the person you want to spend time with and share with. Beth was standing at the glass windows full length and the sun was just ... Read full Story
Jon Paul 2018-06-04 4,274 Cumshot Asian Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
87%
TO BE OR NOT TO BE – PART 1
TO BE OR NOT TO BE – PART 1 by Spanky de Bautumn This is a story about how taking a play to New York City changed people's lives. A transgender coming of age story. I was born Harold Stanley Dayes, not a great name for a kid growing up. I know my parents loved me, but Harold was my mom's dad a... Read full Story
SpankydeBautumn 2021-02-22 3,856 Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob Ladyboy Lingerie Shemale and Girl cum in mouth
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 5,400 Crossdresser Amateur Big Cock Guy Fucks Shemale Interracial cum in mouth
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 5,853 Big Tits Bareback Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Lingerie domination cum in mouth
93%
Homework
Daniel was a 15 year old teenager, like any boy his age, he was full of hormones and sexual fantasies for every pretty girl that passed in front of him. In the last weeks of the school year, the history teacher had a child and was absent from school, being replaced by teacher Marlene, a trans woman.... Read full Story
haroldãosanguebom 2024-01-09 7,103 Shemale Fucks Guy Big Cock Mature
94%
New Girl in Town
Margo sat next to me in the coffee shop late that Saturday afternoon. His real name was Mark, but he was one of the loveliest Drag Queens in New York City. I had been dressing secretly at home in my mother’s and sister’s clothes for just over three years, but at 18 years old, I had never... Read full Story
shemale lover 2019-06-04 10,054 anal shemale oral sex
88%
A Walk In The Park
Each day I spend my lunch down at the park in town. It is down by the lake. I sit and eat my lunch and watch the people walk by. I watch them and they watch me. Then when I’m done I go for a long walk. Each day that I go I start my walk about the same time. At 12:30 pm I start my walk. I like ... Read full Story
shemale lover 2012-07-20 4,755 Cumshot shemale oral jacking off
100%
My weekend with Kelly part 9
My weekend with Kelly part 9 6/12/2013 I rolled off of Kelly, pulling her on top of me.She placed her head on my chest as my hands went down to her sweet tight ass. We layed like this for so long we actually fell asleep for about an hour or so. I was awakened to my cock being sucked... Read full Story
Biguynoc 2014-07-08 3,693 anal Creampie shemale ass fucking ass licking
90%
My Night with Luisa Tavares revisited
I've made some adjustments to this story and will be writing a sequel. Hotspur I flew to Goiânia just to be with Luisa Tavares. She greeted me at the door to her apartment in a bathrobe. She had just taken a shower and invited me to do the same. When I returned from the shower, I found her sitti... Read full Story
hotspur 2020-01-10 11,321 Shemale Fucks Guy Blowjob Big Cock domination Ass to Mouth
100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 4,081 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
50%
Spy Girl
Vicki stood in the dark doorway as she watched her mark, Ivan Patrinkov, approach up the empty street. There was no way he would be able to see her where she stood in the shadows. She wore a skin tight leather jumpsuit with black low-heel boots. She would have preferred to have on a pair of stiletto... Read full Story
shemale lover 2011-11-09 4,719 anal sex shemale Frottage
100%
A Job in the Theatre Chapter 19
"Be a dear and get that bag from the car," Paula winked. "Sure," Billy said stuffing his erection back inside his leather pants. He stood, and for just a moment, was right next to Gary, almost touching. Gary could feel the heat waffling off of Billy. He looked so obscene with ... Read full Story
shemale lover 2012-03-15 3,040 anal sex shemale stroking shaving
100%
Cathy's Friend, Transsexual Mary
I have told you about my daughter Cathy. She is a stripper at a nude club. She has sucked me and I have got to fuck her in her ass. All this in front of her friend Bill and Mary. Bill is Bi, like me and Mary is a transsexual. I'm also a cross dresser. Just two weeks ago I found out that my daught... Read full Story
shemale lover 2012-06-05 3,941 anal sex shemale facefucking jacking off
90%
How I became a cute femboy CD part 4
My legs finally started to work again and I turned and was about to walk to my bedroom when Kevin’s voice stopped me. “Come on, Natalie, you know you want to. You have been crushing on David ever since he moved here.” “You’re an asshole, Kevin. You know that. You are a total asshole! I tho... Read full Story
Cute_Femboy 2016-04-05 12,452 first time cumming crossdressing cd sissy cumshot in mouth
50%
La pistola NEGRA del Tío, entre Las Bragas de Mi Tía LA PUTONA
Aaayyy.. Yo sabía que la Tía había sido Flor de PUTONA.. pero, jamás me imaginé que me iba a tocar a mí 'hacerme cargo de sus cosas'.. su 'herencia'.. la casa ya vieja, por reordenar destinar y.. LAS COSAS que una descubre ya con los años! Todo estaba igual, pero HORRIBLEMENTE ARRUINADO.. más, e... Read full Story
Ari Riè 2021-06-03 2,120 Teen (18+) Small Tits Crossdresser Latina Bareback Shemale Fucks Guy Fetish blonde Big Cock Uniform Lingerie domination Premium HD
91%
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 19,388 Big Tits sucking ass licking fucking
80%
How it started
What got me started off watching shemale porn was actually meeting a very beautiful shemale at a beach party. I already knew she was a guy but she was so beautiful. So at one point I asked her if she wanted to go for a walk and after a few minutes and let her know that I was down. Her response was ... Read full Story
PNPFUCKBOY 2019-02-12 11,874 Teen (18+) Small Tits Crossdresser Amateur Big Tits Outdoor Latina Bareback blonde Big Cock Ladyboy domination Guy Fucks Shemale Interracial Sex Toys Mature Homemade Ass to Mouth
20%
The Greatest Liar, Deal With The Devil
The Greatest Liar, Trans Erotica With a Purpose By Alexandra Rios, © 2019 The Lost Chapter, Deal With The Devil This is a work of fiction. All characters (including the narrator), products, places, events and incidents are either the products of the author’s imagination or used in a fictit... Read full Story
the greatest liar 2019-08-07 3,227 Bareback Creampie gangbang Guy Fucks Shemale double anal
100%
Jo, Shemale Goddess! Part 1
Jo plumped the cushion and carefully positioned it until it was precisely at the right angle. Nothing less than perfection would do. Ricki, her friend of twelve years was coming to stay overnight and she would notice if the tiniest thing was out of place. An impatient knock on the door signalled ... Read full Story
shemale lover 2011-09-04 5,469 anal sex sucking shemale
60%
Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
shemale lover 2012-09-28 6,581 Cumshot Fetish oral sex cum swallowing
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 8,693 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
42%
Piknik az erdőben
Egy szép nyári madácsicsergős reggel úgy döntöttem, hogy elmegyek túrázni a közelben levő erdőkbe. Reggel miután bepakoltam egy pár dolgot a hátizsákomba neki indultam az erdőnek. Szerencsére elég nyugodt kis erdő volt tisztásokkal bozótosokkal tarkítva. Nagyon megnyugtató kikapcsolódásnak néztem el... Read full Story
luckyboy007 2019-12-30 3,676 Teen (18+) Outdoor Bareback Shemale Fucks Guy Guy Fucks Shemale cum in mouth
100%
mein erstes mal
Nur ein paar Häuser weiter wohnte Bernhard, 56 Jahre alt, hatte einen kleinen Bauch, sonst aber sehr gepflegt. Seit 3 Jahren war er geschieden und lebte nun alleine. Schon seit einiger Zeit besuchte ich ihn regelmäßig, um in seinem Pool zu schwimmen, um ihm manchmal im Garten auszuhelfen oder einfac... Read full Story
trans_sabine 2022-10-03 3,314 first time Stockings Teen (18+) Small Tits Crossdresser Amateur Bareback Creampie Lingerie Guy Fucks Shemale schwanzmädchen
50%
SECRETS ET ABANDON ⚧️ ⚧️
Aller dans une nouvelle école pour ma dernière année de lycée était plutôt nul. C'était toute la tribulation de changer d'école, ce qui n'était jamais génial dans le meilleur des cas, plus le fait de savoir que tous les amis ou connaissances que je pourrais me faire iraient tous dans des... Read full Story
Femboy 2021 2023-03-20 749 Teen (18+) Crossdresser Shemale Fucks Guy Blowjob Guy Fucks Shemale 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 4,596 shemale cum ass fucking
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 11,861 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
66%
Samantha sissy TGTF
Theme and genre of the story: The genre is about gender bender, futanari, gay, physical transformations of the body, magic and biology, the kink in particular that must excite in the story is the perversion of the transformation of the body and mind through a magical element that manipulates biol... Read full Story
Samantha sissy world 2022-09-20 4,645 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
50%
PRIS
"Merci d'avoir fait ça, Alex," dit Mr Stevens en me serrant la main. "Au revoir Mr et Mme Stevens !" J'ai crié depuis la porte d'entrée alors que mes voisins me faisaient signe avant de monter dans leur voiture. Ils fêtaient leur anniversaire avec une soirée et je m'étais porté volontaire pour ga... Read full Story
Femboy 2021 2023-01-27 926 Stockings Teen (18+) Crossdresser Fetish Big Cock Lingerie domination Guy Fucks Shemale cum in mouth
50%
L'ACCORD DE LA VIERGE ⚧️ ⚧️
"Ah putain !" Chris crie alors que sa tête est poussée vers l'avant puis se brise contre son siège de voiture. Pendant un bref instant, sa vision est floue. Se ressaisissant, il regarde autour de lui et ne voit aucune vitre ou quoi que ce soit de endommagé à l'intérieur de sa voiture... Read full Story
Femboy 2021 2023-03-19 697 Teen (18+) Crossdresser Fetish domination Guy Fucks Shemale cum in mouth
50%
ÉTÉ ⚧️ ⚧️
Je ne me souviens pas exactement où ma fascination pour les choses féminines a commencé. Mon premier souvenir remonte à l'âge de six ans environ, lorsque je portais une des robes de ma sœur. Mes parents - qui étaient tous deux des conservateurs de la vieille école et des chrétiens - m'ont at... Read full Story
Femboy 2021 2023-03-23 368 Teen (18+) Crossdresser Fetish Guy Fucks Shemale cum in mouth chantage
50%
VENGEANCE NOIRE ⚧️ ⚧️
Vivre près de la périphérie de la ville peut être une chose fastidieuse, surtout lorsque vous avez été retenu au travail au centre-ville pendant plusieurs heures après votre horaire. Et surtout quand il fait nuit et que les bus ne vont plus jusqu'à votre quartier. Et surtout lorsque vous prenez ... Read full Story
Femboy 2021 2023-03-24 1,165 Teen (18+) Shemale Fucks Guy Fetish Futanari femboy cum in mouth
50%
EXPULSÉ ⚧️ ⚧️
Quand mon père est parti dans un accès de colère, ma mère s'en est pris à moi. Elle a ensuite rebondi d'une relation malheureuse à une relation plus malheureuse en me blâmant toujours pour son incapacité à garder un homme. La plupart des hommes étaient des creeps et même moi je savais qu'... Read full Story
Femboy 2021 2023-03-24 665 Teen (18+) domination Guy Fucks Shemale cum in mouth humiliations cage chastity feminisation forcé
50%
Eric...a
There was no doubt that this was going to be my last baseball game in organized ball. I knew that after high school I would not get a chance to play anywhere else, save for the drunken beer league down the line. I was an average player who played for a small school. I played second base. We were los... Read full Story
shemale lover 2012-04-18 5,795 first time anal sex jerking off crossdressing
87%
Alex
I'm a straight guy! a few years ago, I stubble the cross shemale p***. now I must say, it felt weird, I mean being used to watching females doing p*** on my life. but I have to admit, these shemales that I was watching were passable, and most of all looked very f*******. shemale p*** made my di... Read full Story
Mike212 2018-05-28 6,659 Teen (18+) Small Tits Amateur Blowjob Ladyboy Guy Fucks Shemale
86%
Miko and Mali; Thailand's finest teen sisters
Last August my friends and I went on a “lads holiday” to the beautiful country of Thailand. We had booked a fortnight, which was to consist of five nights in a city hotel in Bangkok, and the remainder in a stunning 5* resort in Phuket. It was my first time in the country, my friends hav... Read full Story
shemale lover 2014-06-25 8,211 shemales taboo lesbian sex
50%
The Chronicles of Drodge Mallea
Drodge awoke feeling fuzzy headed and stiff. Actually, "awoke" wasn't quite right -- "came to was more like it. She sat up in the lavishly furnished boudoir, stretching her athletic 6-foot frame as she did. Running a hand though her short, thick copper locks, she slipped out of the... Read full Story
shemale lover 2011-10-24 3,024 Cumshot shemale Big Cock
0%
Lady Denisa's Gang Banged
The young black youth aged eighteen was lying on the bed while I mounted him for the third time that day. I used his cock and muscular body shamefully to bring myself off with no thought for his pleasure. Kenny was my toy boy, an aircraftsman from the base my husband commanded when he wasn't away on... Read full Story
shemale lover 2011-11-22 4,449 shemale oral orgasm
83%
Teacher Student Confidentiality
It was raining cats and dogs outside as Ms. Catherine Walker (Cat by her friends) graded her Accelerated Integrated Geometry test scores. Her was long and flowing and her sweater was purposely pulled low to embarrass the male teachers with her cleavage. Her cock twitched as she shifted her leg to a ... Read full Story
shemale lover 2012-02-11 14,000 anal Blowjob black fiction
100%
Clara Bow's Academy for Ladies
Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his an... Read full Story
shemale lover 2013-03-27 5,032 Teen (18+) Small Tits shemale public softcore
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 4,898 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 5,040 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 4,705 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
100%
The Trip Part 3
I soaked in the tub for close to an hour, thinking about my predicament, it was only the second day of the trip, I figured if I was going to get through the week then I just had to resign myself and do whatever Joe asked of me, sex is just sex, I reasoned, it doesn’t matter who or how many peo... Read full Story
shemale lover 2012-05-20 3,633 anal sex Cumshot oral sex
88%
A Schoolgirl Story
Jason Sheen was eighteen when he moved to River Falls with his mother. Ever since he was a small child Jason had lived with just his mother, Felicity, and he could no longer remember anything about the father who had abandoned the two of them when Jason was just three years old. Fortunately, Felicit... Read full Story
shemale lover 2012-06-05 14,934 cum oral jerking off crossdressing
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 22,781 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
44%
A Lover Wet Dream
I fantasized about my tranny girlfriend fucking me the other night. I dreamt that she told me to be wearing my blue teddy, earring I got me for for birthday, thigh-high white stockings, and black heels. I came home all sweaty and dirty from a long day’s work, and told her to get me a beer from t... Read full Story
ASSEaster5678 2018-05-02 3,114 Bareback Uniform Guy Fucks Shemale deep penetration dreaming
80%
Too Much Hospitality
Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned t-shirt and some ... Read full Story
ASSEaster5678 2018-09-17 8,683 anal Blowjob transsexual oral sex cum swallowing romance transgendered Consensual Sex Older Female / Males
90%
Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
Regina10 2020-11-30 9,241 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
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 7,066 Stockings Crossdresser Big Tits Cumshot Bareback Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale pov Ass to Mouth
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 4,105 Teen (18+) Crossdresser Big Tits Cumshot Masturbation Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Homemade Ass to Mouth
95%
First time
Hi, my name is Sandra. In fact, I'm not exactly a girl, but a CD. Even as a child, I felt different and I used every opportunity when I was left alone in the apartment to dress up, to put on women's clothes, to put on make-up. In time, I started watching porn, as did all my friends. But, unlike them... Read full Story
cd Sandra 2021-10-13 5,702 Stockings Teen (18+) Small Tits Crossdresser blonde Guy Fucks Shemale
100%
Uncle sweet Lover
Uncle Barney called me this morning and wanted me to keep my evening free. He wanted to meet me at the motel with a surprise for me. I was so excited and could hardly wait. I had to decide on something to wear, but when I thought about it, I realized that I wanted to wear something special. He would... Read full Story
Regina10 2024-02-19 4,770 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
73%
Shemale Masturbation Tube Just For Me
I was just coming back from the gym - damn, lights on the parking lot were flickering again - when I heard this noise. I ran and saw a shady looking guy pointing a knife at a woman trying to unlock her car. "Hey", I yelled, "I'm calling the cops and a dozen big dudes are going to be h... Read full Story
shemale lover 2016-02-24 5,813 sucking cum nipples
66%
Buffy the Shemale Vampire Slayer Part 4
Damn! Wherever Willow was, she wasn't home. The witch still hadn't returned to her motel room. At least, this time, Buffy hadn't had to rely on Sunnydale's public transportation system. Xander had given her a ride across town. He'd offered to wait, to make sure that Willow was back, but Buffy, wa... Read full Story
shemale lover 2011-08-19 3,816 shemale orgasm nipples