Sort by
Relevancy

Free Stories

0%
Thai Holiday
On Friday afternoon I had the car go around to collect Krissy at her office, then my wife, Mei, from home, and then me at my office. The girls were both wearing light, summer dresses and looked beautiful! Unfortunately as I was coming from the office I was wearing a Suit (But as usual with Black Lac... Read full Story
shemale lover 2012-02-05 3,568 Group Sex cum fuck oral
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 14,565 Fetish bdsm crossdressing bisexual
50%
A Perfect Life
The reasons I am not writing this myself. I have finally convinced someone to do it for me. She promised to post it on the Internet, but only as fiction. I suppose it is a bit unbelievable. It all started with the best of intentions. I had married my love while we were still in college. She... Read full Story
shemale lover 2012-05-05 12,921 transgender
33%
Click, click, click....
Click, click, click…the sound of high heels contacting a hard surface has always attracted and aroused me. Whether it’s on tile floors in a hallway, the concrete of a parking ramp or the asphalt of a mall lot, I turn in anticipation to drink in some pleasing eye candy. How short will th... Read full Story
shemale lover 2012-06-09 5,646 anal Cumshot oral deepthroating
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 5,147 Stockings Cumshot Blowjob fingering ass licking
66%
Am I Still A Virgin??
I'm a middle-aged, married, bisexual, semi-passable CD (I hate the words 'non-passable'). I've dressed for a few years, but for a multitude of reasons have never had anal sex. I saw an ad in Craigslist (CL) that seemed perfect for me. It ran in their Casual Encounters "m4t" section (T mean... Read full Story
shemale lover 2012-10-18 5,370 Cumshot sucking Lingerie cd
100%
Double Wedding
I was about to marry my childhood sweetheart Paula Rother. I loved her and she loved me but it hadn't been straightforward. After school she went to Manchester University while I went to work at a local accountants as a lowly paid junior clerk. She said we where inseparable but during the two years ... Read full Story
shemale lover 2012-11-08 7,517 Cumshot dildo Sex Toys
100%
Downsizing Chapter 3
Work was going quite well. The company started to grow again, and some new personnel had been hired. Even unknown to me, there had been a couple of males hired in the last few months. Ms. Stanton had informed them when she got to the dress code that the makeup was a requirement, and that the one mal... Read full Story
shemale lover 2012-11-10 3,229 anal sex Cumshot Creampie oral sex
85%
THE WEATHERGIRL BY B-MAN
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2015-07-29 7,930 Crossdresser hardcore ass fucking cd
100%
I Knew Her Secret
I had a serious crush on the postal lady, I would wait on her until I saw that she was coming and then I would either make up some reason to go outside and exchange words with her or I would watch naked from inside of my house. I know it sounds perverted but I just couldn’t get enough of her. ... Read full Story
shemale lover 2011-09-20 6,735 Cumshot asshole fingering
100%
My First Time Out Part 3
Angelo was still working on Shayna's blonde wig. He fussed with it, combed it, and teased it. Angelo knew a romantic style was very important to Sir Dominique. Shayna was escorted to a tremendous makeup table. Saki placed a headband on her that stretched her scalp and raised her non-existent eyeb... Read full Story
shemale lover 2011-10-18 4,563 blonde shemale massage
100%
The Naked Day Wedding
I'd looked forward to this day with a feeling of excitement and also a certain amount of trepidation. Now the moment had arrived and it was all happening. I looked at my gorgeous bride Tina as we signed the register of marriage in the towns' registry office. Outside, I could hear the bustling ... Read full Story
shemale lover 2011-11-24 3,281 anal shemale strapon
100%
Gratitude from client
It’s been 3 years since I got my first experience. I mean sexual intercourse with someone who determined my further life. I still remember my first time with a shemale. She was a tall slim sexy legged blonde that once came into the office of our company. I knew she was an assistant of one of o... Read full Story
shemale lover 2011-12-05 2,430 oral ass fucking
100%
Being Twins
I knew something wasn't quite right but I couldn't be sure. My life for the past 10 years with my wife Jane was great. My name is Richard. Jane was 5'8", 120 pounds, lean trim body, 38D breasts, beautiful blonde hair and stunning features. I was 5'9", 148 pounds, and little chest or body h... Read full Story
shemale lover 2011-12-19 5,674 hardcore erotic encounters fantastic
100%
The Greatest Lie Part 4
Don’t get me wrong, I don’t hate being around people. Actually, I hate being alone: it brings out the weird self-critic inside me. But god, do I hate crowds. Fall registration brought mobs to the campus. The half-empty dormitory that I had shared with a few Asian engineering students was... Read full Story
shemale lover 2012-01-19 4,899 taboo femdom crossdressing
100%
The Greatest Lie Part 12
My Own Worst Enemy Let’s face facts. The so-called the "War On Drugs," "Just Say No," and all the other anti-drug campaigns are complete failures because they ignore reality: getting high is fun. College students drink and take drugs to break a boring routine; the poo... Read full Story
shemale lover 2012-01-20 4,482 hardcore crossdressing fantastic bondage and discipline
50%
The Greatest Lie Part 15
I think that if you could get honest answers, a lot of heterosexual guys would probably admit to having had at least a passing desire to be a girl. If they were honest, they would probably admit they thought of it "when I first noticed a girl's breasts" or "when I first felt a girl or... Read full Story
shemale lover 2012-01-20 6,521 anal hardcore erotic encounters fantastic
50%
Baby Face Jack's Biggest Fight
The referee held his gloved hand high in the air. The crowd was hushed as the ring announcer spoke, "Ladies and Gentlemen, the winner of this World Featherweight Championship Boxing Match to unify the title, by technical knockout, and still undefeated; Baby-face Jack Mc Coy." The crowd scr... Read full Story
shemale lover 2012-02-08 7,399 fuck oral
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 4,555 bdsm domination transvestite
60%
A Revenge Fuck Part 3
Chase gripped my ass-cheeks and plied them apart, shoving his cock up, balls deep into me. My legs, stuck up into the air and folded back, my knees bouncing there even with my head as he fucked me there in his car. We faced each other, panting and kissing, hot breath and saliva mixing. His ruddy coc... Read full Story
shemale lover 2012-06-03 4,177 anal Cumshot shemale oral
100%
Jesse's Dream Job - The First Day
Jesse didn't want to be late on his first day so he got to the office about 20 minutes early. He was looking sharp in a black suit pinstriped in light blue. The shirt matched the pinstripes and the tie was made up of reds, purples and a little of the light blue to bring it all together. Jesse had ne... Read full Story
shemale lover 2012-12-20 9,815 hardcore Cumshot Shemale Fucks Guy ass fucking handjob
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 23,107 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
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 5,190 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
82%
Fetish Club With Shemales
The smell of rubber and latex and the combination of the strobe lighting was overpowering, the techno sound of the club just added to the already intoxicated atmosphere of the place. The club was a frenzy of half naked, latexed, rubberised bodies covered in sweat dancing to the frenzied sound of tec... Read full Story
tgirlloverme 2014-02-19 9,729 Ebony orgy
95%
The club
The smell of rubber and latex and the combination of the strobe lighting was overpowering, the techno sound of the club just added to the already intoxicated atmosphere of the place. The club was a frenzy of half naked, latexed, rubberised bodies covered in sweat dancing to the frenzied sound of tec... Read full Story
shemale lover 2014-10-15 6,531 sucking facial deep throat
100%
Just One of Those Days Part 2
Hello again. My name is Amanda, though sometimes I use the shortened version Mandy, when the mood suits me. I'm 33 and have stayed single for three years, since I discovered that Richard, my boyfriend, was not only cheating on me with dozens of women, some my so called friends but was al... Read full Story
shemale lover 2011-12-09 3,432 cum massage shemale sex
100%
Witch Chronicles
I have been asked to write down my perception of the events of the war. After what's just happened, I thought it best to wait and rest before writing things out, but the big wigs want me to get it all down while it's still fresh, so don't expect this to be an extremely military report. I... Read full Story
shemale lover 2012-01-01 6,094 Masturbation orgasm fantasy tg
75%
Blue collar Master, white collar slave Part 2
About an hour later I was once again naked except for my chastity pouch and my stilettos and once again I was screaming and crying, my body covered with angry red welts from Master Darren's whip. On my knees crying and begging I held his cock in my hands, trying to give the best handjob ... Read full Story
shemale lover 2012-01-13 11,678 torture extreme fiction bondage and discipline
100%
The Greatest Lie Part 3
My weekend escapade with my first real lover, Jake, convinced me that I was destined to live as a girl, despite having been born a boy. Unfortunately, it was my male persona to whom the University of Minnesota had extended admission and a scholarship, and I wasn’t quite sure how they would rea... Read full Story
shemale lover 2012-01-19 4,531 hardcore crossdressing erotic encounters
100%
The Greatest Lie Part 9
Two hours after saying goodbye to Rick and Randy, Tran and I left Minneapolis and boarded a plane to LA. I fell asleep at take off, and woke as the plane began its descent. Tran was staring out the window at the city’s lights spread in an endless shimmering galaxy below. "Wow, I love LA a... Read full Story
shemale lover 2012-01-19 4,070 hardcore erotic encounters fantastic
0%
A Night to Remember
PREFACE I kept my female alter ego (Nicole) a closely guarded secret from my wife for over 15 years of our marriage. I've always enjoyed exploring my feminine side from a more realistic sense -- most cross dressers I met try to wear skimpy outfits and stockings that only a handful of genetic wome... Read full Story
shemale lover 2012-04-28 3,592 anal sex cum nylons
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 2,438 anal Stockings hardcore Cumshot oral
66%
A hard fuck fantasy
I want my man to fuck me. I’ve met him a month ago on the internet, on a transexual dating site. I am a 22 year old transvestite who’s discovered crossdressing at 18 with my ex-girlfriend - or rather in the back of my ex-girlfriend. I started wearing her underwears she had left at my pl... Read full Story
artemisia 2012-07-03 3,236 oral jizz transvestite
25%
A Strange Romance
Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to ... Read full Story
shemale lover 2012-07-05 7,138 Creampie Fetish crossdressing virginity
100%
Boss Lady
Ross looked at the torn-out magazine page tacked onto the wall of his cubicle. In the picture, a man lounged in a reclining with a drink in his hand. A bikini-clad woman, who looked a little like Carmen Electra, leaned against a palm tree and gazed blissfully at the man. The headline across the top ... Read full Story
shemale lover 2012-08-09 5,203 Fetish transvestite crossdressing
100%
Defend Each Other
San Francisco International Airport, San Francisco Ca. Main Terminal area 12:35 a.m. 16 September. Alex sat in the quiet airport terminal, fixing her lipstick in a small compact and checking her make-up, waiting for John to arrive from Japan. John had gone to Japan to convince his investor in ... Read full Story
shemale lover 2012-08-10 3,765 anal Cumshot shemale oral
85%
Where No Man Has Gone Before
I write this with the faint hope that some day, some way, I can send it to the men of Earth. (Maybe via the Internet?) It's been over a year now since that night... I had been driving later that night than usual for me. You see I'm just a single, middle-aged guy who's good at fixing stuff. I had ... Read full Story
shemale lover 2012-11-23 4,776 sucking cum oral
100%
Angel Chapter 3
On Monday morning, Angel Jones reported for her first day of work at the main office of the big London Bank. As she sat on a chair in the anteroom of the personnel office, she thought about what she would be doing there. It was almost a certainty that nobody in the bank knew she was a T-girl, becaus... Read full Story
shemale lover 2012-12-01 5,100 Cumshot sucking jerking
84%
The Making of Erica - Sperm Loving Crossdresser
Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I have only sucked cocks, but over a hundred at my las... Read full Story
shemale lover 2015-09-03 16,886 shemales Masturbation Fetish
0%
Shemale
My whole world changed when Brant came into the scene. I was all set to take over from father in the Jann Troika, something I’d been trained for since birth, and doing anything else just never entered my mind. Then I met Brant Tor, a Killian soldier. I’d met Killians before, and like ... Read full Story
shemale lover 2011-09-22 5,191 shemales taboo humiliation
31%
Headmistress' Favorite Sport
When Susanna lost her second job only two days after losing her first; she had no choice but to accept her sister's kind invitation. Susanna had been loath to do so because of two things. Firstly there was pride. Although she had accepted Rachel's offer of help with paying for the children's school,... Read full Story
shemale lover 2011-12-12 7,173 torture toys bondage and discipline
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 8,530 Fetish transformation dildo
100%
Angel Chapter 10
The sex on Friday night and Saturday with Bob Marley Cliff was the best Angel had experienced up until that date, but it was only one of many fabulous carnal adventures in her life. Because of her beauty, her sexual prowess and her reputation as a woman who was free and open with her charms, she had... Read full Story
shemale lover 2012-12-02 4,073 Cumshot sucking fingering handjob
85%
My dream pt 2
A few hours later I woke up and realized that I had fallen asleep. Sydney must have also fallen asleep as she was still in my arms. I tried to get up with out waking Sydney but that wasn't possible. She woke up and quickly put on her nightie so she could walk me to the door. When we entered ... Read full Story
Sydney Sun Min 2017-12-26 18,365 Shemale Fucks Guy
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 6,278 Group Sex Shemale Fucks Guy gangbang Shemale and Girl shemale + shemale
100%
A Couple of Couples
My wife and I were having a couple over who had gotten married a few months earlier. She was a tall blonde and he was a stud, weight trainer kind of guy. My wife had always had the hots for her and since she hadn't tried another woman yet and I had known her for years, I got that ball rolling. When ... Read full Story
smtmsbrianne 2020-08-16 6,609 Bareback crossdressing blowjobs Swallowing Cum
75%
A Tuesday To Remember
A Tuesday To Remember It was much like any Tuesday for the last year, except when I came in my wife, Deena met me at the door coming from the garage. She grabbed my arm and started leading me into the living room as she said, “You better say yes, yes to everything.” I had no idea what she was tal... Read full Story
Setinkhan 2021-04-15 6,374 Small Tits Crossdresser Interracial
100%
Ladies who Lunch - At the Gloryhole
Ladies who Lunch - At the Gloryhole By Sabrina G. Langton *** Author's Note: Hi, just a quick little story to make us all wet and squishy. Three mature crosssdressers have a little more excitement than they are used to after lunch. I hope YOU like it... *** The Boynton Tavern So w... Read full Story
Brina Giselle 2024-01-06 5,746 Crossdresser Blowjob transgender mature crossdresser gloryholes
50%
Blue collar Master, white collar slave
I sit on the couch in my owner's house, dressed every bit the slave I am. My body from the tips of my toes to my eyelashes is completely and permanently hairless, smooth, soft and beautifully tanned. My upper body is clad in a thin, soft and pink rubber T-shirt and my ass is clad in a pa... Read full Story
shemale lover 2012-01-12 9,904 torture extreme fiction bondage and discipline
100%
Sissy Training
This is a true story, looking back it is hard to believe it actually happened, but it did. I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We&r... Read full Story
shemale lover 2012-03-12 8,415 Group Sex Fetish bdsm
80%
Debbie Part 7
As Debbie was led into Dr. Jacobsen's office, she saw that Mistress was already there waiting for her. "Your property Miss Chamberlain", the doctor proclaimed, indicating Debbie. Debbie's heart began to flutter with love and submissive fantasies as she saw Mistress. Mistress was dressed in... Read full Story
shemale lover 2011-12-23 9,872 transgender toys bondage and discipline heavy
50%
Old Folks
I had been cross-dressing for some years, but I had never been with another man. I had been talking on a gay chat site for some months when I found someone who I got on with well. We exchanged photos I was happy with his and he was happy with mine. Deciding to get together, we arranged a date and ti... Read full Story
shemale lover 2012-01-10 8,260 transsexuals romance crossdressers
100%
Daddies New Girlfriend
Doug suspected his 19 year-old son Jerry was stealing money. Doug worked far too much trying to provide for his son to supervise him properly but drew the line at theft. So he decided to set up a web-cam behind the mirror in his bedroom, he'd used the very same 2 way mirror to film his dead wife Cyn... Read full Story
shemale lover 2012-03-09 12,496 sucking Fetish crossdressing
100%
Angel Chapter 8
When Angel Jones woke up on Friday morning, her long blonde hair was tousled across her pretty face and her ruffled teddy was twisted around her breasts. She brushed her hair back, adjusted the nightie and smiled at her need to do so. Although the long hair and frilly garment were sometimes nuisance... Read full Story
shemale lover 2012-12-01 4,012 Cumshot sucking tit licking
94%
The Babysitter's Secret
The story that I am about to tell you took place on a day that started out very ordinary, but would end up as the least ordinary day of my life. Until that particular Winter day, I thought I knew who I was. I was Peter Fuller -- respected educator, devoted husband, loving father. I had never cheated... Read full Story
shemale lover 2011-10-24 21,444 Blowjob perky tits handjob titfuck
93%
The Babysitter's Secret Part 2
Two months had passed since Jenny and I had first made love on that fateful, snowy night. At least once a week, occasionally many more, Jenny and I had found time to be alone and indulge in our secret affair. I had never believed any sexual experience could be greater than our first time together bu... Read full Story
shemale lover 2011-10-24 6,972 Stockings shemale oral sex bisexual