Sort by
Relevancy

Free Stories

100%
My First Time Out Part 2
It was Saturday morning at eight o’clock when Shayna was rudely awakened by the telephone in the room. “Hello,” she said in a raspy voice. “Good morning, this is the Bell Desk downstairs,” stated the Bell Captain. “Yes, responded Shayna?” “... Read full Story
shemale lover 2011-10-17 2,719 Cumshot shemale jerking
100%
David to Dee
"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... Read full Story
shemale lover 2012-07-29 12,465 Cumshot Masturbation oral sex
100%
Transsexual Mistress
I had heard some intersting comments about this S and M club and so I decided to go by and check it out. I walked in about 9pm and things were just starting to get warmed up. I sat down with a beer and looked up at the main stage where a gorgeous raven haired dominatrix with an enormous set of ti... Read full Story
shemale lover 2012-09-08 4,583 Cumshot Blowjob domination ass fuck
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 11,787 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
100%
My Fantasy Story
My first time, Sissy Cuckold for BBC After ten years of marriage, my wife and I wanted more. First we went to some strip clubs together. One night one of the girls my wife liked told us about a swingers club. So we gave it a try. Best decision we'd ever made. We went, at first just wallflowers, ... Read full Story
Mikky666 2020-10-09 9,749 blonde Big Cock Interracial Ass to Mouth
100%
Reshooting the Scene, Chapter 1
I have been a porn aficionado since I was a teenager. My first dabblings were with Hustler magazine and a *very* hardcore mini-novel called “Her Busted Asshole,” which told the raunchy story of Ginny Cummings’ sexual coming of age. In addition to the very graphic story, it had full color glossy p... Read full Story
Lovelace 2021-06-07 4,480 Bareback threesome Blowjob blonde Big Cock Sex Toys Ass to Mouth
100%
Big Dick Alessia Visits Dallas
Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... Read full Story
darrell 2022-04-20 4,282 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
100%
Daddys Little Slut
I have been living with my dad for the last year after my mum who is Indian, found out that I was doing lots of drugs, and that I was bi and also a cross dresser. We never talked about it as for me, the cross dressing was on and off and usually when i was high. When i turned 25, I tried meth, and fo... Read full Story
aishacox 2023-01-31 5,243 Crossdresser Cumshot Fetish Blowjob Latex
47%
Dr. Visit.
I turned 50 and the Dr. called and said I needed to make an appointment for my birthday physical. Well my birthday fell on a Friday and my appointment was the doctors last one of the day. I was sitting in the waiting room and saw all the employees left the office. I asked the last one exiting if I ... Read full Story
shemale lover 2012-05-22 3,806 anal sex Cumshot Creampie oral sex doctor
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 32,708 anal sex Cumshot Shemale Fucks Guy redhead
83%
My Life as a Shemale Part9
It is now almost a year later and I am a year older, my hormone treatment has been going on for some time. The short version of the past few months seems some of the most poignant in my life but not conducive to this readership. My skin was getting softer, my body hair lighter and most important to ... Read full Story
shemale lover 2015-02-27 3,517 tranny Cumshot Masturbation anus
95%
Late night park visit
It was 11pm on a Friday night, I was driving my car back from a failed meetup with a guy I met online a couple of days prior. I thought it was going to be an amazing night, so I spent close to two hours getting my makeup and hair sorted to look pretty for him when we met. I was wearing a short black... Read full Story
Natalie Bishop 2018-10-08 7,104 Amateur Cumshot Bareback Creampie Big Cock Ladyboy domination Guy Fucks Shemale public Park
50%
Freak House Superstar Come Fest
Kiki and Ty Blaze were doing their thing. They were living on their love and passion, literally. The couple had taken their love, passion and desire to please one another and turned it into their livelihood. They had become stars in the world of underground porn. Their production studio, Nasty Nigga... Read full Story
shemale lover 2012-02-01 6,276 anal shemales Group Sex
60%
The Clinic
I got out of my cab and looked up at the Clinic. It was a small, nondescript hospital. I was still pretty nervous about this treatment since I wasn't even sure of the details. But it was either this or go under the knife. This problem had to be dealt with. I picked up my bag and went into the lobby.... Read full Story
shemale lover 2012-05-02 5,829 Cumshot Big Cock jerking off oral sex cum swallowing
100%
Sandy comes to visit me
If you have read any of my prior stories, you know that while I was born as a boy, I more closely resembled my mother and my older sisters. I was the only boy in our family, and from a young age realized that I was destined to live as a girl. It started early in life, with me sneaking into my sister... Read full Story
shemale lover 2012-06-09 2,929 anal sex Cumshot Creampie
100%
At Jake's Cabin
Jake and I had been secretly seeing each other for about a year. We took every chance we could get to go and fuck. Jake’s famly had a cabin on a private pond in northern Minnesota. He had asked me to go up there with him for spring break. He told the fam that it was a guy’s weekend to fi... Read full Story
shemale lover 2012-08-17 3,095 anal Cumshot Creampie threesome oral
100%
Angel Chapter 5
On Monday morning, Angel Jones woke up smiling and with a feeling of well-being. She was still feeling the effects of the great sex that she enjoyed Friday night and Saturday morning, and the plaudits of the people at the Friday dance at the Gay, Lesbian, Bisexual and Transgendered Association. She ... Read full Story
shemale lover 2012-12-01 4,398 Cumshot sucking fingering
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 3,733 Cumshot sucking tit licking
85%
BANGING AROUND BANGKOK
BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... Read full Story
bkkldby 2019-06-17 14,034 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
100%
TG Neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
Jon Paul 2022-04-22 6,480 Big Tits Cumshot Latina Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale
100%
Lola Chapter 4
We sat at the table. I had made the effort to cook a small three-course French-inspired dinner. I was in love, but Lola’s mind seemed elsewhere. - How nice… She was chewing absent-mindedly. - I have to ask you something. - Shoot baby. Ask away! Lola looked deep into my eyes: - Could you ima... Read full Story
BellaBeau 2023-10-30 5,602 anal Cumshot Latina Bareback Creampie Shemale Fucks Guy Frottage Homemade Lola
100%
Lola Chapter 5
Lola chapter 5 Summer vacation was coming to an end. Most of the time we had been to ourselves, mostly at home but also a couple of shorter trips. Beer tasting in Stockholm's archipelago, a trip to the west coast, overnight stays in hotels, everywhere we were received like any other couple. A fam... Read full Story
BellaBeau 2023-10-30 5,681 anal Cumshot Latina Bareback Creampie threesome Shemale and Girl Lola
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 8,939 Stockings sucking domination
100%
A New Experience
I had been sat in the hotel lobby for a couple of hours, bored, just watching people come and go. I hated these business trips. There I was in a strange city, knowing nobody, hanging around waiting for business meetings. Out of all the people I had seen there were such a variety of people. Pensioner... Read full Story
shemale lover 2012-04-01 2,522 Cumshot Creampie Big Cock
75%
From manager to sub sissy
Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved t... Read full Story
shemale lover 2012-09-12 10,066 Cumshot Fetish bdsm sissy
100%
Lola Chapter 2
Lola Chapter 2: A couple? It wasn't as if we were together. We had jerked off together once, and of course we slept in separate rooms, but I slept restlessly that night. Dreamed something scary that I couldn't remember in the morning. I didn't have work scheduled that day so I took it easy. When ... Read full Story
BellaBeau 2023-10-05 5,322 anal Cumshot Creampie Guy Fucks Shemale Homemade latina Tgirl
100%
Every Year
Imagine me. A slim eighteen year old boy, dressed. I mean Dressed. Dressed up that is, in my sister's clothes. I felt good, very good. In fact I felt incredible. I had done this several times before when my parents had been away but never to this extent. They were away for two nights, visiting Uncle... Read full Story
shemale lover 2012-04-22 5,463 Cumshot oral sex deepthroating crossdressing
100%
Betrayed Chapter 4
I really wasn't surprised when Dianna directed me into the parking lot at Ringers. It was only a few blocks across town from my new home; a five-minute drive, if the traffic wasn't killing at the time. Consciously, it had not been a factor in my decision to take the new place. Sub-consciously... wel... Read full Story
shemale lover 2012-05-29 5,014 Cumshot orgasm condom sex
100%
Fifi La Femme: A Pansy at Last Chapter 2
Coming Out Telling our wives wasn't easy especially for me who had seduced Shirley's gorgeous hetero husband by dressing up in my wife Doreen's lingerie and make-up and offering him full homo sex as a limp wristed effeminate lady-man. It was my first experience as a queer and when Frank asked me ... Read full Story
shemale lover 2012-07-29 4,679 Cumshot oral sex sissy
100%
Fifties Housewife
I walked in Timeless Fashions to see if anything new had arrived. Sheila smiled and said, "I have some new things I think you'll love." She waved me to follow her behind the counter and into the back of the store. Sheila has known me for a few years now. I fumbled into her store trying ... Read full Story
shemale lover 2012-08-03 3,696 anal Cumshot Creampie orgasm
100%
Emergence of Josette
It was a few years ago when I admitted to my wife that I love dressing in women's clothing. It was after she found a stash of some of my panties. They weren't her size, so it was an immediate red flag for her. She didn't immediately believe me. So I gave her an impromptu fashion show. She seemed unc... Read full Story
shemale lover 2013-01-22 4,761 hardcore Cumshot threesome ass fucking Sex Toys
100%
A Night on the Town: Part 3
I woke up like I do most mornings, naked, in Gina's arms, her breasts pressed into my back, her semi-erect cock pressed between my ass. I laid there, thinking about the night before, smiling. Soon, I needed to go to the restroom, and gently rose, making sure I didn't wake her. I wandered out of my r... Read full Story
shemale lover 2013-05-31 3,433 Cumshot suck Creampie threesome ass fucking
100%
Regina and Tommy
I was getting fucked hard and aggressively by a certified bad boy named Tommy. I've never been the kind of girl who liked bad boys until I met Tommy. Tommy like doing all kinds of wild crazy things to me and I was under a spell and couldn’t object. Tommy was like the asspussy whisperer and he gave m... Read full Story
Regina10 2022-03-02 2,924 Stockings Big Tits Cumshot Bareback Creampie Fetish Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
100%
I got anal creampied at the beach!
As soon as we got onto shore, I knew it was the perfect place. The hot sun was beating down on us and my body was tense with anticipation. Finally, we were going to be alone out in the wilderness with nobody around and could enjoy each other thoroughly. My hunky date and his monster cock were going ... Read full Story
Madison Heights 2022-12-01 4,686 Cumshot Outdoor Creampie Fetish Blowjob Big Cock Ebony Guy Fucks Shemale public bbc massive
100%
HE DIDN'T KNOW I WAS TRANS...
I'd worn an absolutely killer dress just to make sure I got what I was looking for that night. Dancing under the lights I could feel eyes all over me, and as the evening progressed men became bolder and bolder about approaching. This one was athletic, sexy and had all the right dance moves, at least... Read full Story
mika96 2023-05-11 6,541 anal Amateur Bareback Creampie Blowjob femboy Ass to Mouth
90%
A Sissy (S)exercise Fantasy
I stopped going to the gym about six months ago, when money got tight and I had to find ways to reduce my expenses. I usually don't get to the gym much in the spring or summer months anyway, so it was an easy expense to cut. I hate going into the office all sweaty, so I avoid working out in the morn... Read full Story
shemale lover 2012-06-14 9,259 Cumshot Fetish domination oral sex sissy
80%
Perfect First Date
i would make dinner for us at my house and we would relax get to know each other better and wed eventually end up sucking each other till ever ounce of fluid in ur bodies was drained, intertwined your cock deep in my throut,as i slowly work my tongue around your cock, you begin to breath harder and ... Read full Story
Tsunami777 2013-04-09 3,860 anal sex Cumshot Creampie Shemale Fucks Guy facial
100%
The four of us
Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... Read full Story
Jon Paul 2021-08-02 4,130 Group Sex Big Tits Cumshot Bareback Creampie Blowjob Big Cock Guy Fucks Shemale Ass to Mouth
80%
Bitch Maker Chapter 2
I woke up feeling pretty good. A new place and an unexpected blowjob had fallen into my lap last night. As such I regarded the maid outfit laid out on my dresser in good humor. Sam was a very silly woman after all. Yawning and stretching I stepped into the hall, hearing movement in the kitchen. I... Read full Story
shemale lover 2012-06-24 4,598 hardcore anal sex Cumshot sucking Creampie
100%
Transsexual Sisters Chapter 2
MICHELLE AND NICOLE TRANNY SISTERS Part 2: Living with lesbians During freshen orientation the girls kindly declined approaches from many men and some women. They needed to find their bearings and were not ready to reveal any hidden secrets yet. They first needed a place to stay and searched t... Read full Story
shemale lover 2012-09-07 4,030 Cumshot Creampie Blowjob Big Cock tits licking
71%
Angel Takes on Two Men
On the Friday after her experiences with Augustus and Peter, Angel attended the meeting of the Gay, Lesbian, Bisexual and Transgendered Association, and found Gus and Kenny both in attendance. After the meeting, which was rather ordinary, they joined her, either of them giving the other rather stran... Read full Story
shemale lover 2012-12-07 4,188 tranny Cumshot oral sex squirting
91%
The Dinner Party
The clock above the kitchen sink read 7:48 when I heard the metallic snap of Aya's key unlocking the front door. I opened the oven door and was rewarded with a blast of steam that smelled like a lazy August afternoon, all rich garden spices and earthy head. Inside was a boxy cookie sheet covered in ... Read full Story
shemale lover 2013-01-11 5,319 hardcore Cumshot sucking Creampie ass fucking
100%
Ravaged by Daddy
For anyone who loves wearing high heels and dressing up to get ravaged by your hungry Daddy. I imagine you laying on your side as I run my strong hands up and down your smooth, soft legs and across your feet. I slowly slide them upwards until I'm caressing and squeezing your thighs. You watch me ... Read full Story
TheWinkster 2023-08-29 5,050 anal Cumshot Bareback Creampie Guy Fucks Shemale
100%
Serving Waitress
This is the first “didi” story I ever wrote. It’s my deepest (and darkest?) fantasy. It probably needs to be rewritten at some stage because I think it’s been written too much by my male brain and not enough by my female side. The story begins….. My wife, Susan, ... Read full Story
shemale lover 2012-08-28 4,745 anal sex Cumshot Creampie oral sex
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 2,997 anal sex Cumshot Creampie oral sex
88%
Ivana Pushing Sissy's Limits
"You look ravishing," my wife Ivana said as I stood before her in a short red velvet dress with white tights and black Blahnik mary janes heels. She walked over to put a hair band in my long black hair. It was down to my shoulders now, flat-ironed straight. We stood together in front of... Read full Story
shemale lover 2013-03-19 6,629 Crossdresser Cumshot sucking Creampie ass fucking
100%
Best night ever
Well the beginning of the story is i meet this absolutely drop dead gorgeous women at an alternative bar, she invites me back to her dorm for some fun little did i know what i was walking into. we get to her dorm room, the whole way here we could not keep our hands off each other, we finally unlock ... Read full Story
Tsunami777 2013-04-09 7,234 Group Sex Cumshot Creampie Big Cock
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 4,830 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
91%
Southern Hospitality Ch. 02
XtinaSmith2017 Laura felt herself lifted lazily from the arms of sleep, her body relaxed and floating on a small cloud of pleasure, her mind filled with images, sensations, not pulled from whatever dream she had just been having but instead, memories, memories from the night before. Memories of... Read full Story
Gwapo67 2022-05-16 4,557 Bareback Creampie Shemale Fucks Guy Big Cock Mature
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 12,505 transgender
100%
Discovering Amber Chapter 3
There have been very few times in my life I have been terrified and today was definitely the tops on that list. Ms drove us to the mall and as I watched she walked around the front of the car and opened the door for me. I looked up to see her hand extended toward me. "Practice getting out li... Read full Story
shemale lover 2012-09-28 4,067 sucking Fetish domination Sex Toys
75%
Debbie Part 1
He had gotten a job with a large company doing odd jobs, mostly filing papers and bringing out mail. It wasn't much, but it was enough to pay for a small one-room apartment on the seedier side of town. Since he was still very shy from his experiences in high school he hadn't made any friends yet, bu... Read full Story
shemale lover 2011-12-22 9,261 transgender toys bondage and discipline heavy
50%
Liberty meeting, chapter1
On a beautiful summer day, my phone rings. It's Steve, the boss of a transvestite company who calls me. - Hello Sandra, I have four new friends waiting for you at the club. - Thanks for thinking of me, I'll be right there, I said, hanging up. I am happy with his call because I always meet ... Read full Story
sandratvtg 2024-06-20 739 Stockings Shemale Fucks Guy Fetish Lingerie shemale + shemale
96%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 30,836 strapon porn
100%
Job Opportunity
So. A bit about me. I'm 5'4", 139 lbs, long brown hair and deep brown eyes. 5.5 cock, cute 'bubblebutt'. I had been looking for a job for a long while with no luck, and REALLY needed the money bad. I finally got a call from the female owner of a coffee shop I had applied to. I had actually fill... Read full Story
shemale lover 2011-10-22 5,326 anal shemales hardcore
75%
Barbie Jo Adventures Part 2
Friday Night After work I picked up the pictures and went home to get ready. I got the call from Wanda this afternoon at work. She first apologized for kicking me out of her house last Saturday night, Halloween, without letting me clean the cum off my face. Knowing that I would have had to walk h... Read full Story
shemale lover 2012-02-17 4,329 Fetish crossdressing fantasy