Sort by
Relevancy

Free Stories

90%
In Hose and Heels for Daddy
It was shortly after my 14th birthday when I made the decision to seduce my Daddy. I mean, all of my girlfriends were having naked fun with their daddies. I didn't wanna be left out ;-) After all, me and my BFF, Ashley, had been getting naked and having fun with her daddy for 2 whole years now...and... Read full Story
shemale lover 2012-09-30 7,600 Fetish jerking crossdressing
100%
Amanda and Me Chapter 2
I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. ... Read full Story
shemale lover 2012-10-21 8,904 anal Cumshot shemale oral
87%
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 2013-07-19 4,850 Crossdresser Cumshot sucking domination spanking
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 9,386 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
100%
Masturbation fantasies 2: Looking for Amanda
Previously: William, a young lawyer who has no luck with women, decide he needs some relief from a live girl. Scared of going with a prostitute, he decides to try out a peep show first. Without knowing that the stripper he chose is kind of special, he ends up in a show with a shemale called Amanda w... Read full Story
ThatEroticWriter 2019-07-24 9,100 Big Tits Cumshot Masturbation threesome Frottage
77%
Slut indiscretion
At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... Read full Story
Regina10 2020-09-16 5,631 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth
100%
Cheating Sissy Wife chapter2
My sweetheart Keith is back from his road trip and we were about to make up for lost time. He didn’t even want me to fix dinner. Instead he said that we would order pizza later. Meanwhile we started making out right there on the couch. We were both horny and anxious to get next to each other. I felt... Read full Story
Regina10 2020-10-26 5,029 Crossdresser Big Tits Cumshot Bareback Creampie Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth
100%
sex-agenarian's onanic lust
An onanic lust of a sex-agenarian that I am; I'M IN BIG HEAT; it's the season of bodily reunions in nature... I'm like an elephant(e) waiting to be satisfied. My cloaca is starting to titillate at the mere sight (look hah!) of a guy's swollen crotch on the street... I activated all my sensors to sa... Read full Story
hippocampus_171 2024-03-09 4,513 anal solo Amateur Masturbation Creampie Sex Toys Mature small cock
66%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2011-11-14 7,006 Big Cock Ebony transsexual
100%
Amy The Tranny Part 1
I met Amy at an adult theatre in town. She was dressed to nines in a mini skirt, tight halter top, and pumps leading up a pair of fishnet clad legs. I invited her into a private booth and once inside, went over her price for some adult fun. She told me I couldn't fuck her as she was on her per... Read full Story
shemale lover 2011-12-14 4,967 shemales hardcore anal sex Big Cock
100%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2012-05-07 5,099 shemale Big Cock oral sex cum licking
80%
Daniel, Dani, Dana Part 2
Looking in the mirror as I drove the highway, the new me felt and I thought looked great. A new hair color with the old one the trim, my face looked smaller and even more feminine. I never had this freedom at home and hated the idea of going back there. Final exams were all that was left to shed the... Read full Story
shemale lover 2012-06-08 3,864 anal sex Cumshot Fetish crossdressing
100%
A Shell of A Man
Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money... but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty w... Read full Story
shemale lover 2012-06-11 9,703 Cumshot Fetish sissy
50%
Chrissie and Julian
One of my oldest and wealthiest clients is a foreign born gentleman I'll refer to as Julian. I don't see Julian as often as some of my other clients but always look forward to a session with him. I think the reason I so enjoy my time with Julian is because I never know what to expect from him. Whe... Read full Story
shemale lover 2012-06-27 2,404 anal Stockings hardcore Cumshot oral
100%
Brad and Tina
It started a year ago; I would get on the AOL chat rooms in hopes of meeting local dominant men. I was seeing a guy named Dan from time to time, just a fuck, nothing serious. Mistress Olivia was an incredible woman and the Domme I was currently serving. She satisfied most of my cravings to be ... Read full Story
shemale lover 2012-08-20 2,551 Cumshot sucking orgasm cum swallowing
100%
One Night of Lust
Hi, my name is Kelly and I've been a tranny for 3 years now. I'm 22 and just got a stunning boob job, 34C. After three and a half years of taking female hormones, I can turn the heads of any and all straight men on the street. I am also a cage dancer at an erotic club in Atlanta for people of all wa... Read full Story
shemale lover 2012-09-02 3,491 Stockings Big Cock ass licking Interracial heels
100%
Transsexual Sisters Chapter 6
Part 6: A Party to Remember MICHELLE AND NICOLE MAKE A CAREER CHOICE After their tormentors were jailed, Michelle and Nicole felt relieved and happy for the first time in weeks. Whether from curiosity, respect or sympathy for their ordeal they became very popular around the USC campus. They we... Read full Story
shemale lover 2012-09-08 4,296 Cumshot sucking threesome Shemale and Girl deep throat
76%
My Wife's Secret Fantasy Chapter 1
PART ONE: REALIZATION The old saying "you never really ever know some one" is quite true when it comes to my wife Debbie. Debbie has always seemed to come up with new surprises to keep our marriage stimulated and adventuresome. As I've recently found out though she seems to have been ke... Read full Story
shemale lover 2012-09-09 10,091 Crossdresser Cumshot Masturbation Lingerie heels
100%
Caught
Hiya my name is Kara Harris, my parents were really expecting another girl and had put the name on the birth certificate before I was born; I'm nineteen years old and stand at 5 foot 5 inches tall. I have never really looked like a boy with my curly back-length brown hair and my large almond-shap... Read full Story
shemale lover 2012-10-05 4,834 Cumshot sucking Sex Toys
100%
Francis Meets a Black Stud Part 5
I finally came upon a plan that I thought would make everyone happy. I would keep on playing this game with my man. I figured that as long as I was dressed like a girl, it didn't matter who he showed those videos too. I mean no one would know it was me and after all, he would be finish his vacation ... Read full Story
shemale lover 2012-11-20 3,054 cum oral sex Interracial
88%
Tgirl trained to be the town whore to serve ALL Black men
A few years back I spent time on and off with several shall we say more dominating types of gentlemen One of them, who for this I shall call Leroy, just loved when we got together to make me totally helpless. It was our 6th or 7th meeting. Leroy and i had been chatting on Yahoo and when he f... Read full Story
__tiffanylondontv__ 2014-09-30 6,265 suck shemale ass fucking Interracial big cocks
100%
The Story of Stephanie (Chapter 10)
A year had passed since my night with Alan. I'd taken a back seat from the dressing. Only now and again was I getting the urge. I was trying to live a normal, single mans life. Going out with friends, going on dates etc. I had one or two girlfriends in that time. One in particular, who I regretted n... Read full Story
Stephanie Wild 2024-07-14 3,031 anal Stockings Crossdresser Amateur Blowjob Big Cock Lingerie Guy Fucks Shemale
100%
Sex In Stilettos
Standing before the full-length bedroom mirror, I treated my reflection to an almost unjustly critical appraisal. My indecently short black leather dress clung for dear life to my every curve and went perfectly with my high heels, whorish fishnets and black leather jacket. It was the sixth outfit I ... Read full Story
shemale lover 2011-08-13 4,627 Cumshot tattoo cum swallowing
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 15,158 cum oral jerking off crossdressing
100%
Head Cheerleader Mikki
At 18 i was your average kid in high school. Decent grades played sports. I was on the volleyball and swim teams. I was about 5'7" 145 lbs and in good shape. My girlfriend was 19 and used to be the head cheerleader at our school. She was gorgeous. Her names Donna and she was a freak when it ca... Read full Story
shemale lover 2012-06-08 3,681 Cumshot oral sex Sex Toys crossdressing
58%
My real story
I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him. It had all started two weeks earlier when I had posted an ad on Craigslist. Up until this particular posting I had always been pretty bland..."Willi... Read full Story
shemale lover 2012-06-10 6,518 hardcore Cumshot bdsm oral sex
100%
Head cheerleader Mikki
At 16 i was your average kid in high school. Decent grades played sports. I was on the volleyball and swim teams. I was about 5'7" 130 lbs and in good shape. My girlfriend  was 19 and used to be the head cheerleader at our school. She was gorgeous. Her names Donna and she was a freak when ... Read full Story
Mikki A. 2012-06-18 4,309 anal Cumshot oral Sex Toys cd
100%
A Whole New Me Chapter 2
I had just finished cleaning up in the bathroom. A spontaneous encounter with my best friend whilst wearing my girlfriend's thong had left me a bit of a mess and as for the thong... well I guess I'd need to find something new. Fully cleaned up, I ran naked into our bedroom and started looking thr... Read full Story
shemale lover 2012-07-25 2,749 Cumshot oral deepthroating
100%
Thai Ladyboy goddes in Tokyo and a cheap love hotel
This is a real account of my meeting last week with a beautiful Thai ladyboy working at a flashy show at a night club in Tokyo. Written as a not to her. Hope you like it. You sexy ladyboy goddess, I must say you have the most beautiful body. When we first started drinking wine and talking ... Read full Story
lblover77 2012-10-09 10,051 anal Ladyboy oral
66%
Anal Queen
Amanda fell to her knees in the darkened theater and slowly unzipped my pants. My cock throbbed. As she pulled down my underwear, I felt my manhood spring forth. Amanda took the whole sausage into her warm, soft mouth. I could barely see her face in the darkness, but I could feel her between my l... Read full Story
shemale lover 2012-11-24 6,373 tranny anal sex Cumshot cum swallowing
100%
Fucked in the Park
I was feeling really horny, massive nervous anticipation. I was all dressed up, looking for another big cock. I'd done myself up pretty well, great make-up, hair looking good, scarlet blouse (it was warm enough not to need a jacket), black skirt finishing about 3" above the knee, matching bl... Read full Story
shemale lover 2012-12-04 3,687 Cumshot fingering oral sex
92%
A Surprise Relationship
This is a fictional story, although it is based on people I did know. "Tony" and his twin sister "Kim" are based on a set of twins I knew, who were almost identical. I did have a relationship with "Kim" for almost two years, however, the relationship with "Tony&quo... Read full Story
shemale lover 2013-01-29 5,478 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Daddys Bride-to-be
Daddy rings my doorbell. I was waiting impatiently for him, dressed appropriately...today is a special day...today I promise daddy to marry his cock. I am dressed in a silky white wedding dress. Very short and tight, with shiny beads and pearls, along with a veil covering my face, and long white ... Read full Story
lea1234 2014-10-07 5,976 Stockings Cumshot suck cd
80%
Owned sissy girl
I met the mature dominant couple that I now call Mummy & Daddy on the internet. Their ad said they were looking for a full-time live-in mature sissy plaything. After we made contact they invited me to their house. I was instructed to bring any sissy clothes with me and to refrain from orgasm for... Read full Story
Andrellina 2015-09-23 29,413 anal ass rimming cd sissy
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 3,559 Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass Ass to Mouth
100%
Mel - Sexy Olderman
Mel is 66 years old and is in my musical orchestra. he is handsome with a great personality. he is married but his wife is ailing ,so i dont think he gets much action!he is a horn player an i in the percussion section.mel an i joke a welot an he sometimes jokingly says i have a nice ass! he has beco... Read full Story
shemale lover 2011-10-25 2,841 Cumshot Big Cock oral
100%
Betrayed Chapter 1
She's having an affair. I couldn't ignore it any longer; the evidence was right there on my monitor that Wednesday afternoon. I had felt so... tawdry – a word I had thought I would never use – hiring the detective to follow her, follow up on my suspicions. It was as though I was betrayin... Read full Story
shemale lover 2012-05-28 6,669 anal sex Cumshot shemale oral sex cum swallowing
55%
Dawn's Diary Chapter 3
Back at home it took nearly a week before I was able to sit comfortably after my encounter with Sam and her huge dildo. My thoughts constantly drifted back to her. I continued to keep my body cleanly shaven and regularly wore the outfit that I had worn that evening with Sam around the house. I bough... Read full Story
shemale lover 2012-07-31 3,258 Crossdresser Cumshot oral sex
100%
Fifties Housewife After the Party
I had not fallen asleep after Darren had, exhausted, after the party and the incredible lovemaking we had shared. I just couldn't come down from the high and emotions of the whole direction we had taken. I was lying spooned against him, his warm cock nestled warmly against my ass. My nightgown seeme... Read full Story
shemale lover 2012-08-03 3,678 anal sex Cumshot spanking
90%
Professor to Sissy Slut
I had just turned thirty-four and I was miserable. My wife of twelve years had left me for another man and was living with him. We were not yet in the process of filing for divorce and I was hoping she would have a change of heart. I was still in love with her but I understood why she had left. We h... Read full Story
shemale lover 2012-09-04 5,095 Stockings Cumshot Blowjob fingering ass licking
100%
Voodoo
I was walking though a neighborhood, looking for a house to brake into, I came up on to this house it was small, I think about a three bed roomed house, I walked up the path, then I walk around it to find a open window or door and I found an open window leading into the cellar. Yeah, I am Alex Ha... Read full Story
shemale lover 2012-09-09 4,098 Cumshot Blowjob Big Cock Ebony domination
40%
First Sexual Crossdress Experience
How my secretary found out I'm a bi TV and how me and my TV friend educate her into some of the more zany aspects of TV sex. *** As I laid back against the wall of the toilet with my nylon-clad thighs spread wide and my erect cock jutting up lewdly from between them, the wooden door in front o... Read full Story
shemale lover 2012-09-27 5,812 first time Fetish cum oral crossdressing nylon
100%
Wife Converts Husband Chapter 4
Seeing as how Shelley is the money maker in our household, it is my job to keep the house clean, so every morning I get up and make her breakfast while she gets ready for work and since my feminisation, my wife has made me dress up as a sexy French maid while I do the housework. Shelley bought me... Read full Story
shemale lover 2012-10-18 4,346 anal Cumshot oral
100%
How I Became Vanessa Chapter 1
PART I: I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husba... Read full Story
shemale lover 2012-10-31 3,980 anal Cumshot Masturbation Sex Toys
100%
FMDM Inc - Jerry's Story
"I just want him to get what he needs without destroying my family or our marriage," said Mrs. Farrett quietly. She was sitting in a corporate office speaking to Amber Giles, a woman half her age and twice her breast size. Approaching this mysterious FMDM, Inc. had been her last resort to ... Read full Story
shemale lover 2012-11-14 3,701 Cumshot oral sex swallowing
100%
Dress and Drive
I am twenty four years old and have been cross dressing for years now. I started when I was young and when my sister was not at home. Since then I have moved into a house of my own and I have built up a pretty large collection of clothes, shoes, make-up, and a few different pairs of fake breast. I d... Read full Story
shemale lover 2012-11-16 3,756 anal sex Cumshot fingering oral sex
96%
New Job, New Life as as Sissy Slut Chapter 2
I was left lying on the floor, my face completely covered in cum. I was wearing lingerie and a dog collar and I had just been fucked long and hard by my "boss." My virginity had been forcefully taken. The thing is that I loved it. I loved being manhandled by this muscular man and I really ... Read full Story
shemale lover 2012-12-23 7,605 Cumshot Uniform Lingerie ass fucking domination
100%
Christy's Fantasy Come True Chapter 6
The alarm went off and Christy rolled over and hit the off button. The clock face was starting back at her flashing 8:00. Since it was Friday she had slept in a bit. Jim had gotten up early and left for work after spending the night. They had gotten into a minor argument last night but came to a... Read full Story
shemale lover 2013-01-30 5,302 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
88%
How I became a Transexual
I was driving a different way home after work and noticed a kind of sleazy looking sex shop. Not really wanting to go home yet, I decided to stop, it had been awhile since I'd had sex and was horny. I went in and was browsing around the movies section when I noticed there were doors in the back. I w... Read full Story
shemale lover 2013-07-19 6,563 Cumshot Masturbation transsexual oral sex ass fingering
93%
CD Jinn College Experience
So being a secretive cross dresser is very difficult to do with roommates. I only dress when I know that no one will be around for hours I check class schedules and ask what everyone is doing all the time so I know when my chances to dress are. I was planning on dressing over the weekend. It was p... Read full Story
Jinn.V23 2014-03-27 6,166 Crossdresser Cumshot ass fucking domination cd
84%
First Time Crossdressing with a mate part 1
It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I dressed up like a slut for the first time, I couldn't stop thinking about meeting another crossdresser for some horny mutual fun. I had been faithful to my ... Read full Story
shemale lover 2014-07-21 6,286 Cumshot suck wanking swallowing 69 cd
88%
In my bedroom...
Daddy walks in to my room and lays down in bed, right behind me. He starts caressing my stocking covered legs…daddy likes it when I lay in bed in my sexy lingerie. I’m wearing a white garter belt, white stockings and silky white panties. Daddy caresses my sissy bum as he starts kissing my neck and m... Read full Story
lea1234 2014-10-07 5,766 Cumshot suck ass fucking 69 cd
85%
Father In Law Shemale Adventure
My wife's parents were visiting LA from back east. We live in a small one-bedroom apartment in the valley. She wanted them to stay with us but we didn't have room. They got a room in West Hollywood. My wife and her mom had gone shopping for the day. I was supposed to be at work but at the last momen... Read full Story
shemale lover 2011-08-26 6,002 Cumshot asshole fingering
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 6,936 Creampie Big Cock ass fucking
100%
Threeway Heaven
Times were tough and I took a job as a bouncer in clubs on weekends. It was a pretty boring job most nights, and frustrating having to deal with drunks all the time, so my boss sent me out to a gay club for a change of pace. Also, I was one of his few workers who wasn't homophobic, and therefore les... Read full Story
shemale lover 2012-05-10 3,352 Group Sex Cumshot sucking fingering
100%
Caught and Used Chapter 2
In my last story, I was discovered by wife's friends, Mandy and Michael. If you didn't catch the last adventure; they caught me dressed up in my wife's lingerie, fucking myself with a dildo. Mandy took advantage of this opportunity, and catered to Jim's fantasy while her husband Michael watched. ... Read full Story
shemale lover 2012-06-09 4,319 Cumshot domination oral sex handjob