Sort by
Relevancy

Free Stories

100%
Marathon im Cruisingworld Kirchberg
Ich wurde um 11 Uhr bei mir zuhause von meiner Begleitung abgeholt, gemeinsam fuhren wir ins Cruisingworld nach Kirchberg. Angekommen, wurden wir sogleich nett begrüsst, danach ging es in die Garderobe und gleich ins Spiegelzimmer. Wir starteten den Tag zärtlich mit Küssen und Streicheln. Ich wurd... Read full Story
Cheryl_F 2024-09-02 633 anal Amateur Group Sex Cumshot Bareback Creampie Blowjob Big Cock Ladyboy gangbang domination Guy Fucks Shemale cum in mouth
100%
Ein etwas anderes Grillfest 31.07.24
Am 31.07. wollten wir eigentlich ein geiles Grillfest in der Ruine Anwil feiern. Leider machte Petrus kurzfristig nicht mit, so dass wir bei Andrea Obdach fanden. Nach und nach fanden alle Gäst:innen bei Andrea ein. Andrea begutachtete, als gute Gastgeber:in, die mitgebrachten Würste, während der G... Read full Story
Cheryl_F 2024-09-02 644 anal Group Sex Cumshot Bareback Creampie Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale Ass to Mouth shemale fucks shemale cum in mouth
100%
How My Wife Became a Swinger
Hello, my name is Jackson, Jack for short, and I'd like to tell you about my wife and I and how we became swingers. I've changed the names of people and places to preserve privacy. Just so you know this does involve male on male sex and inter course with a transsexual. So let me begin. For the fi... Read full Story
Loveto 2011-10-12 9,256 anal bisexual gay strap-on
50%
How My Wife Became a Swinger
Hello, my name is Jackson, Jack for short, and I'd like to tell you about my wife and I and how we became swingers. I've changed the names of people and places to preserve privacy. Just so you know this does involve male on male sex and inter course with a transsexual. So let me begin. For the fi... Read full Story
shemale lover 2011-11-13 5,724 Group Sex Cumshot sucking doggy style
100%
A Holiday Job Part 2
“Anne” was stunned by Nico’s offer. When Paul had discovered that his sister had left taking the wrong suitcase, the idea of becoming her for a week had been very appealing. The job in the bar, the innocent flirtation with Jorge the cute waiter over lunch had all been very enjoyabl... Read full Story
shemale lover 2012-03-10 2,782 anal sex Creampie fingering crossdressing
90%
A Good Fit
I didn’t want to be there. Trying on clothes in a department store doesn’t rate high on my list of entertaining activities but I needed a few more sport coats so I bit the bullet and went to the upscale store at the mall. At least I had the freedom to go on a Monday afternoon when there ... Read full Story
shemale lover 2012-04-10 4,446 anal sex Group Sex facefucking
100%
Neighborhood Restaurant Surprise - Kimi
I - The Meeting In the neighborhood restaurant I frequented weeknights after work, I had developed a friendly relationship with several of the college kids who worked as servers. Always having been attracted to the most feminine and petite of girls, dark, almond shaped eyes being a super plus, I ... Read full Story
shemale lover 2012-04-11 5,643 anal sex Cumshot fingering oral sex small breasts
100%
Fantasies Fulfilled
I enjoy crossdressing and do so when ever I can. About the only time I dress as a man is to go to work. I have been doing this since I was eleven years old. I love to have sex with a man as if I was a woman and really think I should have been born a girl. I think like a girl and naturally act like a... Read full Story
shemale lover 2012-05-26 4,837 anal sex Creampie Blowjob crossdressing
75%
Lady In The House Ch. 13
A story by MicheleNylons ( Transvestite prison prostitute gets a visit from the Warden. ) I awoke in my cell the next morning unaware of the terrible fate that had befallen my sister Angie. I knew that Steve had sent his henchman Danny to do something to her in retribution for my recalcitrance bu... Read full Story
✘Transensual✘ 2019-02-27 5,788 Crossdresser domination PRISON FUCKBOY PRISON PUNK prisoner prison sex Prison Bitch
75%
Honeymoon Suite 2
Jason is on the phone with room service, while I am about to change out of my wedding gown. I had just got married, and I was now the blushing bride. Yes I got married. I was nervous now and my pussy was burning, because of the crazy bet we had made about not having sex a week before the wedding. We... Read full Story
Regina10 2021-02-22 4,134 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
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 5,557 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
85%
A Girl Called Eddie
Carrie had always treated me like her little sister, even though we were only third cousins. Though she was only two years older than I was and not of exceptional physical stature, I had allowed her to dominate me for as long as I could remember. Not that she was exceptionally cruel or abusive in an... Read full Story
shemale lover 2011-08-14 5,941 anal sex asshole Lingerie
100%
Angel & Victoria
Angel was a beautiful young girl living with two of her best friends, Monica and Amanda. All were transsexual, and the three shared everything together, from clothes, their sexy intimates, lovers, and each other's bodies. Angel was the youngest, at 23, a Japanese anime lover and the most... Read full Story
shemale lover 2011-09-23 6,690 anal Creampie Big Cock oral
33%
Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
shemale lover 2011-10-01 9,472 Stockings sucking domination
82%
My Sex Fantasy
I want to be raped. I need a forceful guy to fuck me when I’m completely unable to stop him. I’m a crossdresser who is an anal virgin, and for years I’ve wanted to lose it, but never had the courage. I’ve dressed and cammed and come so close to being fucked, but always wussed... Read full Story
shemale lover 2011-11-11 19,380 humiliation fantasies
100%
Slutty Sissy's 2 Loves
Tonight was young and I was already hot and bothered, my ass-pussy was on fire, and I could hardly wait for Bob and John to come over. I had invited them over to fulfill those erotic dreams I am constantly having about the two of them using me like a tool, and I wanted that so bad. I fantasized abou... Read full Story
Regina10 2020-11-23 5,489 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
87%
Body Anatomy Transition
I discovered I like to be penetrate in April of 2016 (according to my buying history, first anal massager), that was I read an article about sex toys review from a male perspective where pocket pussy, prostate massager and butt plug are reviewed together. I decided I also give anal a try, after that... Read full Story
NBClitorissa 2021-03-16 4,847 sissy sissification MtF transition transitioning
69%
From Mob to Shemale
Two years ago, I was a member of the Ciccio family in Chicago. I wasn't very high up in the organization, because I wasn't Italian. I had made my way up through the ranks, however, and was making a pretty good living. I had everything I wanted, got all the girls I wanted, and did just about ... Read full Story
shemale lover 2011-10-29 11,002 orgasm facial oral sex
100%
Becoming Marie Chapter 2
After my encounter with Kevin at his office I knew that I wanted more. I had my own place and had started to build up a nice collection of lingerie which I would often wear while wanking to my slowly built up collection of porn. This was before the age of internet so it was sometimes hard to get por... Read full Story
shemale lover 2012-03-22 3,600 anal sex Creampie cum oral Lingerie
100%
Explore the Inner Woman In You
I fancied the arse off a girl at school called Sharon. The problem was most of my year did. She was beautiful with long blonde hair, willowy legs, a butt to die for and stunning pert tits. She was way out of my league but quite amazingly we did get on and began to make slow but steady headway. My di... Read full Story
shemale lover 2012-05-06 3,812 first time anal sex Creampie crossdressing
100%
Shemale snapped
Camilla took a few steps out the door of her balcony to get a feel for the temperature. Thankfully it was cool out. It had been a hot day, which meant a cool night was welcomed. She closed the door and pulled out a pair of gold hoop earrings. She was suffering from a mild case of the jitters. The... Read full Story
shemale lover 2012-06-21 6,735 anal sex Creampie shemale Big Cock
90%
My very first experience with my classmate
He was amused by the sight...of me in lingerie..standing on the porch,it was obvious he was in a shock (or state of extacy?) and couldn't take his sparkling blue eyes off my firm body inside the dress...he closed the door behind,like he was worrying if someone could see us ..I don't know why but i f... Read full Story
shemale lover 2012-10-01 4,305 anal first time Creampie
100%
Wife Converts Husband Chapter 3
After about a month of being dressed up and acting as a female, trying out all the different outfits we had purchased and Shelley feeding her strap on cock to my willing mouth and ass every chance she got. My ass and mouth was now well and truly broken in. Shelley came home one arvo with a flyer ... Read full Story
shemale lover 2012-10-18 6,003 anal sex sucking cum swallowing
100%
CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
Chrissy Tunnell 2022-03-04 4,179 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
Meeting Amanda Ch. 2 - The Next Day
After a hot evening together, the story continues https://www.ashemaletube.com/story/meeting-amanda-6595/ ------------------------------------------------------------------------------------------------------------- “I could really use a shower,” Amanda said while she... Read full Story
rforasht 2022-09-07 4,771 Masturbation Shemale and Girl redhead Guy Fucks Shemale cum eating anal creampie couple & shemale
50%
Two cocks and a pussy
I'm alone in my apartment and super horny, so I decide to have some kinky alone fun time. I strip and shave my body. I'm smooth now. I put on a sexy thong and bra. Next I put on a garter belt and super sexy thigh highs. Next I put on a super short and sexy skirt, lastly I put on a lace blouse. Next ... Read full Story
spreadforalldik 2024-07-09 3,426 anal Crossdresser Group Sex Cumshot Bareback Fetish Blowjob cum Lingerie pantyhose crossdressing Ass to Mouth cum in mouth
100%
The Wonderful Adventures of Miss K
Miss K sat near her bedroom window in her pink silk robe, staring off into the late morning skyline in the distance while she held a cup of hot chocolate in one hand and ran the other through her waist length bleached blonde permed hair. The indirect sunlight lent the dark chocolate skin on her sili... Read full Story
shemale lover 2011-12-03 6,409 anal oral fingering long dick
85%
Becoming My Roomate's Wife
Him becoming my master started a year ago when we moved in as roommates – we are both in our mid 20's and had relationships break up at the same time (we were sharing apartments with our girl friends at the time). We have known each other for more than a decade and have no secrets from each ot... Read full Story
shemale lover 2012-04-01 9,373 Crossdresser anal sex domination oral sex
100%
A Sissy's New Daddy
Walking in the door the Friday after my eighteenth birthday, everything seemed great. My parents had gone out of town for the weekend and I was for the first time a truly free man. My older brother had decided not to come home for Labor Day holiday which I was kind of bummed about, we didn't get alo... Read full Story
shemale lover 2012-06-16 11,254 anal sex cum oral sex crossdressing
100%
An Unwelcome Visit
It had been over a year since I had split from my boyfriend, Rick. We had a terrible row in which he had accused me of seeing another man. He walked out, never to return. I had tried to give up wearing girls' clothes afterwards in an effort to become a 'normal' person and to try to blot out some bad... Read full Story
shemale lover 2012-11-23 4,079 anal Creampie fingering oral sex stroking
80%
Crossdresser Lovemaking
Oh Daddy, I'm your little princess! Your wife is out taking your kids to a sleep-over at a friend's house across town and we're in your bedroom. I long for you to see me with bursting lust, and I take off my coat to reveal myself wearing a white tutu with bra, panties, stockings and h... Read full Story
CD Lilee 2014-05-20 7,253 Crossdresser anal sex sucking Creampie Lingerie cd
94%
My first Shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe that started my intere... Read full Story
SachinJoy 2018-10-04 33,410 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy cum in mouth
50%
Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
Alicexiao 2023-01-06 5,045 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
85%
Chastity and its effects
I actually thought of writing this for some time now, this quasi-scientific testimonial and reflection about chastity. Now, I finally had some time to reflect, gather and compare info and experimentation from personal experience about the topic. More specifically, the effects it has on the mind and ... Read full Story
DoraTV 2023-02-09 6,923 Crossdresser anal play chastity sissygasm Sissyfication story chastity orgasm
100%
A Win-Win
A Win-Win By Sabrina G. Langton *** Author's Note: Hi, just a quick, crazy story about a wife actively participating in her CrossDresser husbands sex life. Just a bit of fluff, hope YOU like it.) *** We were laying in bed, sex was done, my wife could now relax for the rest of the month ... Read full Story
Brina Giselle 2024-03-31 4,928 anal Stockings Crossdresser Blowjob pantyhose kissing salon
90%
A Sissy Surprise
I got home early from my night out with the girls. Jeff wasn't in the living room watching tv so I figured he was in the bedroom jerking off so he wouldn't have to bother me with a request for sex when I was toasted. I decided to surprise him and slowly made my way up the stairs. I walked into th... Read full Story
shemale lover 2012-06-15 6,397 Fetish oral sex crossdressing
72%
Transsexual Dream - I’m Her Slut
Transsexual Dream - I’m her slut! For the slut that I am, I felt so exposed… I was bent over the desk in a little storeroom at my office with my ass cheeks spread wide in a hope to stretch my virgin ass hole. I wanted to please my hot babe… my babe who has a dick that she had just surprised me ... Read full Story
iluvgurls 2018-11-14 5,580 Cumshot Creampie Shemale Fucks Guy Lingerie
100%
Why I’m a Cock Whore!
Hello Love, The summer before my freshman year in high school. I found a VHS porno video right next to a dumpster behind our local video store. Brought it home. Couldn’t watch it until my family left to use the VHS player. It turned out to be a she male porno at first I felt weird but after watch... Read full Story
Samantha Cummins 2023-04-18 6,820 anal Stockings Cumshot Creampie Lingerie femboy Ass to Mouth cum in mouth
100%
Sweet Encore
I was alone tonight and feeling just a bit paranoid as I listened to the soft music. The soothing sounds put me in a seductive mood, but It seemed that all my lovers were too busy for me, or they had other plans. Uncle Barney and my detective were probably home being dutiful husbands. Bo was under h... Read full Story
Regina10 2024-05-09 3,918 Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass Ass to Mouth
100%
My milking sessions,
My milking sessions. Spending the day at home, I sit in front of my dressing table to put on my makeup and adjust my wig. It's always with the same excitement that I put on my underwear: corset, nightie, slit panties, stockings and stiletto heels. I also enjoy placing my silicone breasts in m... Read full Story
sandratvtg 2024-06-26 3,363 Stockings Fetish Lingerie femdom chastity cage corset gode stockings sex Soumis
100%
My first pre-op story
I started becoming interested in transsexuals a couple years ago, when I ran across some websites where I found some crossdressers attractive. I was 19 at the time. This led me to picking up Transformation magazine, a magazine more for the TG community, but they featured some really got centerfolds ... Read full Story
shemale lover 2015-06-03 11,282 anal Asian domination
100%
With an 'E'
This story could come under a range of headings, Mature, Couplings, or Transgender. But, I guess, Transgender is best, as I have enjoyed the luxury of satin against my body for some time now. Having Lived alone for the last few years, soft, swirly clothing and satin panties keep me constantly ... Read full Story
shemale lover 2012-10-10 3,140 anal cum oral
100%
Sissy Crissi Chapter 1
Chapter 1 -- One Dreamy Night Like most Friday nights, my roommate Erika would be gone tonight. She and her new boyfriend, Leroy, were taking off for a private weekend. Erika and I had met about two years prior, when we were introduced by a mutual friend. Being fresh off a divorce, I was in need ... Read full Story
shemale lover 2013-01-30 8,445 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
50%
A Murder Misstery
When I rolled out of bed that fateful morning, I had no way of knowing that it would be my last day as Matt McCoy. After showering and dressing quickly (how I long for those days!) I bolted out the door for my train, looking forward to another manic day on the floor. Although I was one of the younge... Read full Story
shemale lover 2012-03-20 5,455 Fetish crossdressing feminization
75%
Sissify Your Boyfriend Manual - transation
original= manual-sissificar-a-tu-novio-4979 Used google translate, found some pronoun/object/context issues, and I believe ladybug = ladyboy Sissify Your Boyfriend Manual MANUAL FOR WIFE/GIRLFRIEND TO SISSIFY YOUR MAN, DISCOVER HIS SUBMISSIVE SIDE AND TURN HIM INTO ?HORNAND? AN... Read full Story
shelli_k18 2021-04-20 9,458 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
50%
The Greatest Lie Part 17
They say that life is about making choices. But we humans don't get to choose the two most important factors in our lives. We don't get to choose our genes, so I got stuck with XY chromosomes. And we don't get to choose our natal families, so I got stuck with my mother and father. My father, Edua... Read full Story
shemale lover 2012-01-20 4,910 erotic encounters fantastic consensual
100%
The Mole
Police work is a paramilitary occupation. Uniforms, rank, weapons, discipline…It can be exciting and interesting for some and boring for others. Some officers seem to find lots of action during their career (or maybe it finds them) while others never use their sidearm except for target practi... Read full Story
shemale lover 2012-01-26 7,037 brunette Crossdresser Fetish
100%
Changling
‘My goodness!’ she exclaimed, ‘It appears that you've had an accident, youngster. You'd better come home with me so that we can make you presentable. It's quite safe, 'cos I live in the big house in the woods on the other side of the hill behind the toilets. Come along, now,’... Read full Story
shemale lover 2012-02-02 9,180 shemales Masturbation Big Cock
85%
True story, TS 3-way
This is a true story. It was a typical night in Pattaya Thailand and I'm still recovering from the 25 hour flight from Tennessee to Bangkok that I flew just days before. After a few days in BKK, I arrange for a hotel car to me to Pattaya, a seedy explosion of lights, blaring music and drunken ... Read full Story
Thailover 2014-03-11 10,231 Cumshot threesome jerking ass fucking facial stroking
100%
Eve Quest Part 2
Chapter 6 I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed s... Read full Story
shemale lover 2012-04-21 4,757 bdsm domination transvestite
100%
Seven Lessons Part 1
Bryan was king of the road warriors. Speeding around the country in his sleek, powerful Mercedes selling whatever his latest job demanded. He was damn good at it too, always raked in huge amounts of commission until some faggotty client bitched about a one-sided deal he had put together and then it ... Read full Story
shemale lover 2011-11-30 3,429 Cumshot shemale oral
75%
Old Folks Part 2
It had been eleven months since that day when I arrived at Honey and Frank's house. It was about 1am at night as I stood in a quiet street waiting for Frank to pick me up. I had just finished with my last client for the night a good blowjob with him ending up cumming on my face. I was touching up my... Read full Story
shemale lover 2012-01-10 7,336 transsexuals erotica romance crossdressers
90%
Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... Read full Story
shemale lover 2012-03-01 14,603 first time sucking fuck domination
100%
A Game within a Game Part 1
Epilogue Rob came home from work. His wife Jenny was waiting for him. In her hands she held a letter. Jenny said: "We received this letter today. It is sad news from Marion S. We have met her and her husband John a few times - do you remember? John has had a car accident while driving fas... Read full Story
shemale lover 2012-03-05 14,904 Fetish bdsm crossdressing bisexual
50%
The Invitation Part 4
The light was gently filtering in through the curtains as Jack slowly drifted towards consciousness. For a moment or two of his half awake and half asleep state he was confused - something didn't quite feel right. He stirred in semi consciousness and his eyes shot open at the unfamiliar sensatio... Read full Story
shemale lover 2011-10-01 4,460 shemales Fetish orgasm
50%
The Greatest Lie Part 11
"En Francais", they say "plus ca change, plus c'est la meme chose:" the more things change, the more they stay the same. When Tran and I got back to Minneapolis from our trip to Thailand for our sex change operations, it was every bit as dark, frigid and depressing as it had been... Read full Story
shemale lover 2012-01-20 5,615 cum transformation erotic encounters