Sort by
Relevancy

Free Stories

100%
Amie's Games
I met Amie at Black Angus where I worked bussing tables at 18. She was 24 and beautiful with a slim sexy body, long straight black hair and a look that oozed sex appeal. She dressed to show it all off, whether in jeans or short skirts. I was still a virgin and hopelessly shy with girls, I was out of... Read full Story
shemale lover 2012-10-29 3,890 Cumshot orgasm caressing kissing
100%
Becoming Aphrodite
My wife and I have been married for 10 years. She is a beautiful brunette of 5'8" and 120 pounds. With her long hair and her cute and innocent face, she looks a lot like the porn star Cheyenne Silver. I would dare to say she's even prettier: her extraordinary green eyes are totally unforgettabl... Read full Story
shemale lover 2012-11-01 3,979 Group Sex cum oral sex cum swapping
100%
The dream
I just finished my shower and stepped in to my bedroom wearing nothing but my boxers. I felt something behind me and turned to find a red headed goddess walking in to my bedroom. I’d never seen this beauty before and had no idea who she was, but she slowly walked toward me, wearing this black ... Read full Story
shemale lover 2012-11-06 3,445 shemale oral sex jacking off
40%
Who Changed More?
"Of course we shouldn't have tried the magic mushrooms, but please stop complaining, my dear husband. The magic mushrooms changed me too. In fact, Pat, I think they changed me more than they changed you." "Are you nuts, Carol? Completely nuts? They changed me into a girl, for gosh ... Read full Story
shemale lover 2012-11-16 2,564 blonde big boobs tit licking
100%
Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
shemale lover 2012-11-27 10,821 Fetish crossdressing feminization
100%
When Curiosity Fills
I sat in alone in my office at 11:00 p.m. on a Thursday night in April, preparing an important motion in a multi-million dollar malpractice suit. After editing the final draft I sat back and took a deep breath. I was exhausted, and, oddly enough, pretty horny. The wife was out of town and somehow I ... Read full Story
shemale lover 2012-12-08 8,523 anal shemales cum
100%
Fun With Kelly
As soon as they’d said “hi” to each other, he told Kelly that he had plans for her that day. He didn’t wait for her to say no, or say I’d rather do something else, or say anything at all, for that matter. He just told her he wanted to take her shopping, and she didn&rsq... Read full Story
shemale lover 2012-12-13 3,314 Fetish orgasm Lingerie
100%
Westward bound cum slut Chapter 2
Again I'm on the big bird headed out west for another fling. This time is going to be way different though, the players have increased, not to mention both sexes. The tale unwinds in the same fashion as the last trip out this way, the plane flight was long and boring, and being very nervous didn'... Read full Story
shemale lover 2012-12-16 3,440 anal Group Sex sucking Creampie cum domination
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 10,400 Masturbation Blowjob blonde ass fucking big boobs
90%
Hermophroditie
Ι am a pure blood. I know many of you have seen Hermophrodites on television, some may actually know one, but I am different. It all started centuries ago in ancient Greece when the gods ruled… My grandmother was a beautiful woman. She was petite with a nice curvaceous body, the desir... Read full Story
shemale lover 2013-07-16 3,795 tranny shemale sex bisexual party
88%
Oh My, You Have a Cock...
It was a regular Friday night no different from others I'd experienced before. I was lonely having broken up with my girlfriend earlier that week. What a bitch! I needed to find me a sweet woman capable of matching my libido. My last lady was all about the lights off, missionary position sex, come t... Read full Story
shemale lover 2013-08-09 32,547 anal sex Cumshot Shemale Fucks Guy redhead
89%
Fulfilling fantasies
What seems like a long time ago in my early teenage years, I found myself being somewhat addicted to watching porn. Every opportunity I got I was at the computer watching porn of all different flavours, and for a while I found myself really enjoying lesbian porn. So one day as I was watching a video... Read full Story
curiosity12 2015-06-30 7,212 anal first time tranny Cumshot Shemale Fucks Guy
96%
My First Sex with Tgirl
This is story about me......Hope you all enjoy it I was 19 years old and itching to have sex like every normal teenager. Years of jerking off to porn had only expanded my imagination and made me want to fuck a girl even more. I was turned on by just about anything and everything except gay porn. Ev... Read full Story
sach 2016-02-16 13,301 first time tranny ass fucking guy on shemale mutual suck
87%
Chance Encounter 4/7
With her feet still pointed she starts slowly spreading and rubbing her cream over her nipples while i’m thrusting my cock in and out of her sweet hole. Her hole felt so beautiful! In and out I thrusted until I pulled out. I grabbed her hands, lifted her a little and pulled her towards me as I stood... Read full Story
Katlick 2019-10-30 4,950 Bareback Creampie Big Cock cum in mouth
50%
My Shemale Sex Adventures
Fresh meat Kevin Judd submits to hot top Korra Del Rio in this sexy Valentines Day special. Sensual domination is Goddess Korra's forte and oh boy does she deliver once she gets her hands on this new submissive slut Kevin. Decked out in seductive, strappy black lingerie, thigh high stockings and hee... Read full Story
KendraK 2020-06-16 3,935 Shemale Fucks Guy
100%
Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
darrell 2022-01-03 4,112 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
100%
Shemale is the creature
Hi I am guy who adopted and raised by shemale was yoga instructor by day at night as a erotic dancer she raised me love and breastfeeding me with her juice from her beautiful dick she taught me everything she was my goddess and I am horniest boy who being naked most of the time mom and me was gangba... Read full Story
Batang 2022-01-17 1,434 Art of heaven and earth
93%
Southern Hospitality Ch. 01
XtinaSmith2017 Ash gawped at his mother, incredulous as to what she had just said. He understood the basic premise of what had happened, but the reasoning she must have had absolutely baffled him. "Why?! Why would you do that?!" He pleaded, voice light and desperate. She shrugged, looking acr... Read full Story
Gwapo67 2022-05-16 6,853 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature
100%
Alessia and the Twins
Alessia and the Twins When the politician David Smallwood awoke that morning his thoughts immediately turned to Alessia, and he started to daydream about her, as he was wont to do now. He had several meetings scheduled for that day, including a rally promoting restrictions on gay and trans-gender... Read full Story
Alessia Travestita 2023-07-21 5,009 Crossdresser Blowjob Big Cock Shemale and Girl shemale fucks female
100%
Wild after-hours for a working... effeminate crossdresser
Left work after-hours, cross-dressed underneath w light lingerie & lots of colored little tattoos I draw myself over my hairless body. After drinking lots of spirits on my way home, arrived at my neighborhood park late at night & felt like wishing to be ..... badly abused! I got rid of the... Read full Story
Alexia Pikara 2011-09-07 4,031 Outdoor Bareback double penetration
66%
Outdoor Pleasures
Every evening of our holiday we would all dress up and head to the nightclub, the glamorous entertainment was for the young and old and it was great to hear the oldies applauding alongside the young ones… One night when we headed to the nightclub there was a sign announcing the entertainme... Read full Story
shemale lover 2011-08-13 2,846 anal sex asshole cum
50%
Puzzle
Women. There's no figuring them. They're a puzzle, one of life's mysteries, and that's a fact. Who knows what goes on in their brains, or whether they even have brains? I mean, what rational creature would get excited over Valentine's Day? Could any holiday be more obtuse? Like your bitch, mine's... Read full Story
shemale lover 2011-09-05 2,934 Big Tits asshole scrotum
77%
The Terrace View Apartments Part 5
I woke sometime during the night and found myself gagged, blindfolded and tied up, spread-eagle across a large outdoor bench. The night breeze brought goose bumps to my already spent flesh, and I moaned into my gag in pain as I tried to adjust my body to a more comfortable position. Comfort was n... Read full Story
shemale lover 2011-11-18 3,871 cum domination crossdressing
0%
How I Learned To Love Drag Part 6
May lived in one of those high-rise apartments in Vancouver's West End. When I drove up in my new silver Toyota Celica, she was waiting at the front door. She wore a summery brilliant white cotton dress and sandals. It was appropriate for the hot humid weather. As was our usual custom, we h... Read full Story
shemale lover 2011-12-30 2,323 crossdressing erotic encounters erotic
50%
How I Learned To Love Drag Part 10
As I stood on the first tee of the Royal Vancouver Golf Club, I must admit that Lotus Land sure had a lot going for it. On one side of me was a breathtaking view of the Pacific Ocean. In front of me was one of North America's finest golf courses. And in the distance was the snow-capped peak of majes... Read full Story
shemale lover 2011-12-31 2,297 hardcore erotic encounters fantastic
25%
As Mistress Commands
I remember the first time I was exposed to this world. I was 20, and in my 2nd year of college, majoring in aviation technology. I had been studying my brains out for a paper when I decided to take a break and have some good naughty fun online. I took out the notebook and was goofing off in the chat... Read full Story
shemale lover 2012-01-04 5,871 bdsm cum oral humiliation
100%
Siisy Bride gets what she deserves
I had Ben on a contact site and we live surprisingly close together in Manchester. Ben is a 6’2” black man who has a large sex drive and likes women and girly trannys. I am a slim white guy who likes to dress like a smart woman, not a slut. I haven’t worn a wig for over 6 years ... Read full Story
shemale lover 2012-01-05 4,348 shemales interracial sex bdsm
0%
Let's do it together
I sit here with my dick in hand! All three of my girl friends and my two boy friends are out of town attending to their WORK and leaving this important stuff to me. I shall carry on alone until they return. I am looking at some pictures of a group of people fucking another group of people. Some are... Read full Story
shemale lover 2012-01-24 3,444 Group Sex Outdoor dildo bondage
50%
The Visit
A visit to a hooker, where I describe my bisexual experiences *** It was a weekday, I had bummed off work and had made my way to Ipswich for a visit to Rona, my favorite hooker. She was a lovely woman in her forties, with a fantastic figure, not slim but not fat and with huge tits. She... Read full Story
shemale lover 2012-01-26 8,094 Group Sex licking sucking pissing fucking
100%
The Problem Of Penile Presentation
There is a great bias, in erotica, pornography, glamour photography, and visual art in general in favor of female nudes, and many women are, indeed, beautiful. However, for visual art (drawings, paintings, sculptures, photographs) created for heterosexual women, bisexuals, and male homosexual viewer... Read full Story
shemale lover 2012-01-29 3,326 sucking Big Cock balls
100%
1st Transsexual Affair
Paul's cock was hard as a rock and with a penchant for sleeping in the nude, its fat length pressed against luxurious satin sheets. The dream of searching for a urinal or bathroom now became reality. He stretched, groaned and yawned his way off the comfortable bed and padded across the room. The mar... Read full Story
shemale lover 2012-02-04 4,103 cum fuck oral
33%
A Certain Perception
Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... Read full Story
shemale lover 2012-02-23 8,052 Fetish transformation dildo
80%
A Drive in the Country
It had been a rare hot dry day and the evening promised to be hot as well. Toni the lovely CD I have met down here in Wales arrived as arranged just before dusk in his car to collect me and take me somewhere secluded he had found for some outdoor fun. We drove about a mile before Toni pulled over... Read full Story
shemale lover 2012-02-29 3,666 Stockings Blowjob huge cock wanking cd
100%
Turning my neighbour on in pantyhose Part 2
So.....there I was. Lucy...dressed up to the nines, crossed legged on the window sill. The guy next door, rock hard, almost licking his lips! I was sooooo turned on. I knew I looked fab today! Big headed? Sometimes you just know dont you? You are about to get to know me better.... Was it wrong to... Read full Story
shemale lover 2012-03-16 2,799 Fetish huge dick
50%
A Murder Misstery Finis
For those who came in late, Matt McCoy -- now Madeline Moreau -- is on the run for a crime he did not commit, and a murder which she did....as the saga concludes, Maddy vows to end her life on the lam. "Jacques, when I saw Dr. Villiers, the name I gave him was Madison Monroe. Do you think w... Read full Story
shemale lover 2012-03-22 2,932 Fetish crossdressing
100%
The best of two Worlds Part 3
Ever since I got married my sex life has become great. My French wife Jacqui is absolutely stunning. She is in her late thirties, blond with a slim body to die for. Her only complaint is her breasts size. I can’t find anything wrong with them, but then again women know better. She is highly se... Read full Story
shemale lover 2012-04-26 2,585 Outdoor oral huge tits
100%
The best of two Worlds Part 4
After our adventure on the beach Jacqui had a moral and physical hangover for a few days. She would do things to me that went beyond my expectation. She was absolutely fascinated with my cock, giving me head jobs the moment I walked in to the door. Upon my arrival home I would find her half naked, h... Read full Story
shemale lover 2012-04-26 2,490 anal sex Group Sex Blowjob orgasm
50%
My Clipped Cock
Technically, right now I am an "It." A few weeks ago I was a "He." In another few weeks I will be a "She." The adventure is a celebration for me. I am doing everything right, and sensually documenting and sharing the adventure with my very-supportive and very-erotic fri... Read full Story
shemale lover 2012-04-27 4,527 transformation 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 6,138 hardcore Cumshot bdsm oral sex
42%
Becoming Alanna Part 1
My name is Alanna Monroe and i am currently a college bound 17 year old senior at St. Anne's school for girls in Middletown Conn. I was once Alex Monroe, but after one fateful day four years ago, I became Alanna. Being a proper “lady”, i have all of the assets of my classmates...well tha... Read full Story
shemale lover 2012-07-12 4,695 shemales Ladyboy
100%
Body Image
"Sit down Mona. We have to talk." He had heard those two tiny sentences more than a few times in the last several weeks. Every time he did he felt a strange queasiness in the pit of his stomach. Yet no matter how hard he tried, he could not refuse. He walked over to the couch across fro... Read full Story
shemale lover 2012-07-23 7,086 Fetish domination submissive
100%
Afternoon Delight Chapter 2
The week was very busy getting ready for the party. All of Auntie's staff was invited, plus several students and professors that I didn't know. Well, this presented me with a small problem: Not all of them knew I was transsexual. I asked Auntie if I could wear a wrap skirt in order not to freak anyb... Read full Story
shemale lover 2012-08-26 2,512 Creampie Blowjob kissing cum swapping
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 5,444 first time Fetish cum oral crossdressing nylon
100%
Working for a Living Chapter 6
I slid out of the old Ford truck driver's side door. Surprisingly, my legs felt a bit shaky as my feet hit the concrete driveway of the Malibu mansion. I nervously straightened my cut-off shorts as I walked around the truck. She was waiting by the tailgate with a big smile on her face. "Wow Jai... Read full Story
shemale lover 2012-10-05 3,445 Group Sex Creampie threesome
100%
Dream Bride Tranny
My niece Avril and I rushed along the ground floor corridor of the hotel and made sure none of our relatives were watching us as we disappeared into the room. Inside, we were met by Miss Anne of the Kinky Brides Group, who immediately ordered Avril to strip me naked. "Please, not today,&q... Read full Story
shemale lover 2012-11-13 5,432 anal cum oral Lingerie
100%
An Ever Changing Story
Caught Out and Permanently Punished I was wearing a ultra short black leather mini skirt, a tight leopard print low cut top, which revealed my cleavage entrapped by my pink lacy bra (with matching panties). The straps of my 6 inch leopard stiletto heels were securely padlocked around my ankles. R... Read full Story
shemale lover 2012-11-15 3,999 sucking Blowjob swallowing
87%
Both Sides Of The Coin
Jessica and I were back at the scene of the crime, so to speak. Her work friend, Mike, hosted a costume party every year on the Saturday night 8 days before the Super Bowl, "Because there's never anything else going on that weekend." Last year, that tagline on the invite offered suffic... Read full Story
shemale lover 2013-01-28 5,376 Cumshot Outdoor sucking Blowjob deeptroat
100%
I Missed Myself
As soon as Dr. Griffin returned to the examination room, I knew that the news wasn’t good. I could tell by the way he avoided my eyes as he studied his clipboard and fidgeted with his pen that something was wrong, terribly wrong with me. The ache in my groin that I had been ignori... Read full Story
shemale lover 2013-03-20 7,843 Crossdresser Lingerie pantyhose cd softcore
90%
The Meadow Snare
Trapped 1 "W-what do you mean?" I stammered, knowing full well what Jason had meant. "You really think we'd invite you up here to toast to your change?" He scoffed, and my stomach sank as I realised how careless I had been. I really should have known. I looked for an ... Read full Story
shemale lover 2013-03-20 5,971 Outdoor transformation Lingerie softcore humilation
100%
Summer sun
Evening sunshine is lovely. For a start I can wear less, no coat, no warm clothes, in fact a skimpy skirt and strappy top that covers not much more than the tops of my hold ups and my bra. I like to walk in countryside and feel the warm breeze gently ruffle my clothes and visit those areas where you... Read full Story
shemale lover 2013-05-22 4,088 suck Outdoor wanking stroking public
100%
Crossdresser 1st time!
Hi, im new to this. this happened about 3 years ago now. I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from th... Read full Story
shemale lover 2013-05-30 7,658 Outdoor Big Cock fingering ass licking virgin public cd piss
85%
Shemale Public Bondage Fantasy
It was a chilly evening, I had arranged to meet him in the city centre. I was wearing a rather skimpy black dress, black lingerie and red high heels. It was my first time dressed in public like this. He was an average looking man, he shook my hand and kissed my cheek, and asked if I was ready. I aff... Read full Story
shemale lover 2013-06-22 4,750 Cumshot Outdoor shemale Lingerie ass fucking domination public
92%
Loaning me out to strangers
My wife and her friend Tina were going shopping in Kansas City for the week end. I knew this meant that I would be with Phillip. Tina's husband and the man I can't stay away from his cock. This meant I would be dressing up like a slut and servicing Phillips cock the whole time our wives were in KC. ... Read full Story
shemale lover 2013-12-03 4,583 Cumshot suck Outdoor oral domination cd
100%
Oh The Joy! Part II (revised)
Oh The Joy! - PART II I returned to the cubicle to get some wipes and clean myself up. Touching up my make-up I ran through in my head what had happened and I smiled inwardly. What else may lay ahead for the rest of the day? After what had been done to me earlier would be hard to beat, that’s for s... Read full Story
Sexy Michelle 2014-05-01 4,511 sex toy Cumshot suck oral public cd
71%
A Meeting at a rest stop in Alabama
Typically my wife comes with me when I visit my grandmother in Smyrna GA. Last Friday she didn't want to come with me. Perfect. I stopped at the last rest stop just before the Alabama Georgia line and took my bag of clothes with me to the bathroom. I opened the door and then walked into a st... Read full Story
Rocky Wachenheim 2014-09-02 4,811 Crossdresser Outdoor ass fucking doggy style piss
90%
Riverbank Tranny Fucktoy
Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river. It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site. I had been chattin... Read full Story
shemale lover 2014-12-03 4,585 tranny hardcore suck Big Cock cum ass fucking deep throat