Sort by
Relevancy

Free Stories

66%
Discovering Mistress Sarah's World Part 9
Part 9 -- The Final Part Chapter 23 Leaving Work Josie's last week at work and concluding week of his normal life went quick. At work he spent time getting things in order for the next unlucky person to take over his job. Mentally he was already checked out of work. All he cared about was gett... Read full Story
shemale lover 2012-10-04 3,973 Fetish ass licking domination
100%
Don/Dawn of the Dead Chapter 2
I really like these white thigh highs I have on today. Coupled with the tall red pumps, the plaid little school girl skirt and the rest of it... I look hot. As I stand and shop, I stop to raise one leg and rub it long and slow against the other one, feeling the wonderful fabrics slide together acros... Read full Story
shemale lover 2012-10-25 2,060 fingering jizz handjob
100%
Five Into Three Does Not Go
Kristina It is waspish in the late evening out in the open in Portsmouth Harbour as we step out of the vehicle and walk over to the private section of the docks, the sign says Ceres St docks. Dark has long since fallen but lights, white, yellow and orange light up the skies. The feeling is one of... Read full Story
shemale lover 2012-11-07 4,674 cum oral sex Sex Toys
96%
New Job, New Life as as Sissy Slut
I was nearing my thirtieth birthday and times were getting tough financially. I had gotten laid off from my job and was collecting unemployment and doing some part-time work helping out friends with odd jobs. One of them suggested that I look into cleaning houses. I've always been very neat and peop... Read full Story
shemale lover 2012-12-23 9,567 sucking Uniform domination swallowing spanking
100%
Allison the pool slut part 1
Allison had now had her fair share of whore experience. The teen boyslut had fallen in love with big cocks, anal creampies, facials, swallowing, and the rest of the nasty fun she had while becoming a sissy whore for her black neighbor and his dark dicked friends. Little did she know she was going to... Read full Story
shemale lover 2013-06-05 7,769 Teen (18+) Cumshot Big Cock ass fucking Interracial cd
84%
Young sissy goes for a little shopping... caught
May be first a little introduction? My name is Sylvia and I love women's clothes! I like panties, stockings but most of all, I adore high heels! just love them! That feeling when it becomes higher and I feel so sexy and feminine! And you know what? I'm a total slut, I love to be humiliated,... Read full Story
shemale lover 2013-08-14 17,571 Stockings suck oral Lingerie public cd
45%
Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
ProstateMilker 2015-05-01 13,818 Masturbation cum orgasm cumshots prostate
60%
My Fantasy Came True
Hello all I'm a trap or a CD or a Sissy anything you can call me.I can be your trap or Sissy. Here is my first BBC Gangbang. When I got my fantasy fuck.I'm a Sissy Bitch of my friend.He make my fantasy came true.So here's the story. Last week I got my First BBC Gangbang.It's... Read full Story
TrapBomb 2016-09-26 9,040 Big Cock gangbang deep throat double anal trap c
68%
Mary Ann and the Tim the Ranch Hand
A few months after my girlfriend moved away suddenly to her grandparents home across the country,( I learned a few years ago she got pregnant) I was riding around on my bike in the street when my neighbor Mary Ann called me over. She was 18, I was still 12 at the time and very horny since my girlfri... Read full Story
Julliana 2017-01-13 7,426 anal pussy Blowjob cum oral sex kiss sissy Love young faggot
100%
My Friend From School "Elevated"
One night, I got on all fours and spread my ass for my best friend (we were "elevated" at the time lol). He got up, I got on my knees. I rubbed his dick over his boxers "You like my hot ass huh?" "Fuck yeah I do." I pulled his boxers off and let his dick tap my face. "Omg **** I've wanted your coc... Read full Story
gibsonjohn575 2022-04-14 3,121 friend
79%
My Shemale Stepmother Part 1
My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was re... Read full Story
shemale lover 2011-09-01 18,934 tranny Big Cock jerking off
50%
Debbie Part 6
Debbie was awakened by someone holding a hand over her nose and mouth, so that she couldn't breathe. She struggled, weakly tossing her head before opening her eyes. She looked straight into the eyes of Dr. Jacobsen, smiling evilly down at her. He continued to hold her head so that she couldn't breat... Read full Story
shemale lover 2011-12-23 4,410 transgender toys bondage and discipline heavy
100%
Permanent Stay in Mastersville Part 4
My training was now reaching full speed and I was handling the maid's duties in the house, while at the same time spending a lot of time with sex training. Diane, on the other hand, was clearly reaching the end of her stay with Mistress. It was quit clear that a buyer would soon be found for her and... Read full Story
shemale lover 2012-01-08 4,518 toys bondage and discipline heavy reluctant
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 12,199 sucking Fetish crossdressing
100%
A New Life Part 3
I have now lived with Mistress Sara and Master Tom for over two years. They are great Masters to serve. We have interacted with other "families" and I have found them less then satisfactory compared to my own. Mistress Sara is a lovely woman, beyond words lovely. She is extremely strict an... Read full Story
shemale lover 2012-04-13 3,742 cum domination fisting rimjob
68%
How I became a sissy
So it all started from answering a random craigslist posting that didn't even have a picture. I was off work and horny so I was cruising the ads and I came across a Cross dressing married dom and his wife looking for a sub. I was no stranger to the lifestyle and it intrigued me so I began to write a... Read full Story
shemale lover 2012-07-30 7,148 Creampie oral domination Sex Toys
57%
DADDY and SIR: my craving for older men....
"I would love to be fucked by an older man. my tight little ass needs a cock from an aggressive, top daddy. I love to dress sexy for my daddy and will do most anything to please. Just one condition: you have to cum on my face. I am a slim, 28 year old slut with a tight little ass and an addicti... Read full Story
shemale lover 2012-10-28 4,367 anal Group Sex Cumshot oral
92%
The first sex! A dream for a little sissy slut!
We decided to meet at your place, I enter quickly and immediately go into the bathroom to get ready for our spicy evening. I'm already shaved and wearing stockings, leopard print panties matching bra. In the rush I'm doing makeup, I get dressed in little black dress, barely covering my bum! I put a ... Read full Story
shemale lover 2013-08-09 5,597 Stockings hardcore Cumshot Lingerie domination spanking
95%
CD Jinn Changing Relationship
So one of my roommates, his girlfriend, and I have had some intense sexual experiences together which I have written about before. And these intense sexual experiences have changed the way I act around that one roommate. I hate when he sees me as a normal male. I try to look as cute as possible wi... Read full Story
Jinn.V23 2014-04-29 5,799 Stockings suck Lingerie ass fucking cd
100%
yes, Mother give it to me
"Do your fucking job right, Henry! Jesus Christ, what are you, five years old? If I ever have to call you in here again, you're done! You hear me? You'll never work in this business again! Now get the hell out of my office." Mona could feel every set of eyes on the floor anxiously awaiting the pi... Read full Story
ASSEaster5678 2018-11-28 12,775 Guy Fucks Shemale
100%
And Life Goes On Part 2
So here I sit in my sexy black Miniskirt. The red silk blouse I am wearing shows off my ample sized breasts. Underneath I am wearing a red Satin corset which reduces my waist to a waspy 26 inches. I have on a pair of black satin panties with a matching black lacy bra. The red nylons I am wearing acc... Read full Story
shemale lover 2012-01-10 3,985 Big Tits Fetish feminization
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 30,973 strapon porn
87%
The Hotel Part 1
I knew when this started it would be like nothing I had ever done before. I drove up to the hotel early friday morning. I was checking in for seven days. Seven Days of non stop pounding of my asshole, Strapons, Crossdressing, fucked fem, huge dildos, and giant buttplugs are just a few of my fetishe... Read full Story
shemale lover 2012-02-11 6,070 Fetish cum domination Sex Toys
71%
The Superbowl
I was very surprised when my brother-in-law Tom invited me to watch the super bowl with some of his friends. The only reason he would “invite” me over was to be his little sex sissy, since he had enough pictures of me dressed as a girl sucking and being fucked by him I had no choice but ... Read full Story
shemale lover 2012-05-23 3,392 Stockings anal sex Cumshot Fetish deepthroating sissy
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 5,293 anal Cumshot oral deepthroating
88%
Feminized By My Mother
Hello. My name is Dan. I'm doing okay, you? I see. Well if you are going to be listening to my thoughts please keep the volume down, I am trying to think. Some things are going on that have got me very mixed up and I have to concentrate. Like most overly complicated things in life, a woman is inv... Read full Story
shemale lover 2012-07-24 67,330 Fetish shemale oral feminization
100%
Fender Bender Chapter 8
My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I turned 18 a few months ago. The last two weeks of summer vacation was a wild time for me, I knew that things would settle down once school started. Gary, my best friend for years,... Read full Story
shemale lover 2012-07-27 3,057 Fetish cum oral cum swallowing sissy
100%
After Church
I was just horny. All of the time. I just wanted to fuck someone in the worst way. 18 years old, never had a date. Too skinny, too weird. I wore my hair long, not a very hairy body, not very athletic. Just a skinny kid who didn't get any attention. Lot of church girls in the bible belt but they were... Read full Story
shemale lover 2012-08-19 6,039 Teen (18+) Fetish oral sex crossdressing
84%
Alex to Alice Chapter 1
Everything had started off simple enough for Alex. He had met Elena at a bookstore while he was researching for a college paper. She was quite the vision at 29. She stood a respectable 5' 8" with a voluptuous body. While slightly plump, she maintained her hourglass figure and filled out quite n... Read full Story
shemale lover 2012-09-25 4,663 Cumshot domination oral sex
100%
Francis Meets a Black Stud Part 2
The first story was easy and this one went by pretty well. If you have any thoughts or suggestions for where Francis should go in installment #3 email me. I will respond to your email and sometimes I will send out previews of what I am working on if you treat me right. Thanks. As I was walking to... Read full Story
shemale lover 2012-11-20 3,788 Stockings cum Ebony oral
81%
My stepmother has a surprise for me
My name is Robert, I'm 18, skinny and not too tall. I've never had much luck with girls, in fact I never dated one and I used to spent my days playing games on my computer and watching porn. Shemale porn. Dominant shemales fucking men. I wish i could be one of those men on the videos, that turned me... Read full Story
shemale lover 2013-04-08 234,686 suck Big Cock jerking big boobs cum swallowing
76%
Nylon teasers
They came into the video store where I worked as a clerk. Almost every day. Teasers. Both of them. What made it both great and terrible for me was that it fed my deepest fetish -- stockings -- as it denied me any fulfillment other than frequent and frantic "self-gratification."... Read full Story
shemale lover 2012-01-30 9,934 Stockings Big Tits fucking foot fetish
100%
Dear Karen Chapter 6
07.13.09 Dear Karen, Well, I have had quite a surprise. I came home at lunchtime recently and found BJ had a visitor. I walked into the bedroom and there was BJ and Frank. BJ was only wearing a bra and panties along with stockings held up by a garter belt. He was on his knees beside the bed an... Read full Story
shemale lover 2012-08-06 2,572 oral sex Sex Toys facefucking
50%
Discovering Mistress Sarah's World Part 5
Chapter 13 Sinking Deeper Into The Feminine World *** Prologue - Joe has made a trip down south to visit for the first time, his online Mistress. Over the past few years she has slowly feminized him with the help of Miss May. Upon his arrival at Mistress Sarah's house, she puts his feminization i... Read full Story
shemale lover 2012-10-03 3,715 Group Sex oral fingering domination
83%
He NEEDED me!
I had gotten dolled up nice and slutty looking in my motel room, and had been internet chatting for a couple of hours, so I was feeling very sexy. All dressed up and nowhere to go in a small southern town. I peeked out my window and could see that the place looked pretty dead. No lights were on in t... Read full Story
shemale lover 2014-09-01 3,668 shemales gay male voyeur
50%
The Greatest Lie Part 1
The greatest lie that they tell you is that what happens in high school doesn't really matter: that life begins in college. I pretended to agree, though I never believed it. For as you will see, I am the world's greatest liar. "Take Sadie Hawkins Day, for example," I said to my buddy Qu... Read full Story
shemale lover 2012-01-18 6,952 taboo hardcore crossdressing
100%
Brazilian Discovery Chapter 3
Chapter 03: Partying in Copacabana On the Ipanema beach, Barbara and Joan were joined by Tereza and Consuela. The beach was less crowded than the Copacabana one. Tereza pulled down her shorts and her T-shirt to appear in a quite hot red bikini, an uplift bra that was supported only by a band arou... Read full Story
shemale lover 2012-08-25 3,613 Group Sex Cumshot oral sex Sex Toys
100%
Discovering Mistress Sarah's World Part 6
Chapter 15 Joe's first 'female' public appearance as Josie was approaching fast. He was nervous about it. Fortunately Mistress Sarah had kept him busy most of the day so his mind was distracted. Shortly after his mind blowing masturbation session with her in the morning, she left to run errands a... Read full Story
shemale lover 2012-10-03 4,213 first time domination Sex Toys
70%
Play Day for Sara
It doesn’t happen often, but an opportunity opened up for me recently to take a day off to get a hotel room, get dressed, and entertain men. So I took it. When I discovered I would have this day to myself the previous week, I ran the following ad on craigslist: “Get ready boys – t4m super horny... Read full Story
saralovescd 2017-05-02 6,432 anal sex oral sex crossdressing Craigslist hotel room tag team
90%
What Just Happened? Chapter 4
Chapter 04 -- I am no longer in control I looked at Beth and so did the pizza guy. The delivery guy started a discussion by saying, I do not want to offend you girls, but you are both very attractive and I see one of you has panties on because I can see them. So the other panties on the floor mus... Read full Story
shemale lover 2012-12-16 3,724 Cumshot sucking Fetish deepthroating kissing cd
88%
Glory Hole Orgy
Driving down the street I spied my destination. A big yellow building with “Adult XXX” written on the marquee in front was on my right. I turn into the parking lot and drove to the back behind the building and park in the darkest spot I could find. Another crossdresser had told me that t... Read full Story
shemale lover 2011-11-20 5,089 shemales cum orgy glory hole
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 7,419 Fetish jerking crossdressing
71%
My black lover
After one year as a sissy whore and secret wife to my turkish Pascha, I felt the desire to look for a black man. I looked for ads online and put ads online myself. One day I saw an ad from a young black man looking for a crossdresser and wrote him an email. I actually thought I would never hear from... Read full Story
shemale lover 2012-10-31 3,239 anal Cumshot
87%
My black lover
After one year as a sissy whore and secret wife to my turkish Pascha, I felt the desire to look for a black man. I looked for ads online and put ads online myself. One day I saw an ad from a young black man looking for a crossdresser and wrote him an email. I actually thought I would never hear from... Read full Story
shemale lover 2013-06-26 3,639 anal sex Cumshot suck doggy style condom sex cd
75%
A Game within a Game Part 5
Another session - or not. The next morning Rob was the first to get out of bed. He took a hot shower and then dressed. Both Cathy and Helena were still sleeping. Their orgasms had taken a lot of energy. Rob went downstairs, filled two cups with coffee and brought them to Helena and Cathy. &... Read full Story
shemale lover 2012-03-06 4,578 Fetish bdsm fuck Sex Toys
83%
Story for adults Part 1
This story is strictly for adults. If you are minor or if you are offended by stories with a sexual content, don't read any further. Chapter 1 Pete thought he was a very lucky guy. In his early twenties he was quite rich, having inherited a fortune from his late parents. Because of his relative w... Read full Story
shemale lover 2011-12-20 6,098 bondage and discipline heavy feet reluctant
81%
Made me a slut
I spent my time online since I was 18 watching tranny porn and crossdresser porn I really enjoy a mix of both especially with a big black cock in between I found a movie with a ebony tranny with a big cock and a white sissy gurl with a nice sized cock also... They got dolled up together and all of a... Read full Story
shemale lover 2012-01-05 6,900 shemales Group Sex interracial sex
80%
Becoming Alanna Part 2
Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... Read full Story
shemale lover 2012-07-12 3,889 sucking Fetish Ladyboy rimjob
100%
Jasmine cuckolds me
Hello, my name is Tim. I am a 30 year-old married man. I have been married for five years to my wife Danielle. She is an absolute beauty of a woman. I remember when we were married, I felt like I was the luckiest man in the world. Since I am no hunk myself, standing at just five foot six and extreme... Read full Story
shemale lover 2012-09-27 5,993 Fetish cum lesbian sex
100%
Anastasia's Life
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, Barb... Read full Story
shemale lover 2012-11-26 7,202 Fetish cock sucking crossdressing
100%
First Time Dressed… at an Electronica Concert
I had been dressing as a girl to get off for some time now. For some reason there is nothing that turns me on more than a tight little cotton thong stretched across the bud of my asshole, holding my tiny little boy toy down where it should be. Over the years I’ve slipped into my mom and sister... Read full Story
shemale lover 2011-10-21 3,386 anal first time shemales Creampie fingering
50%
Growing up CD Part 2
After we left Max, Peter and I fought over who would get to take the magazine home. We decided to tear out some pages so we could have some each. We agreed to catch up the next day and go to his house as his parent were going away for the week. That night after dinner I told mum (dad had left ... Read full Story
shemale lover 2011-12-10 3,753 cum glory hole cd
71%
Headmistress' Favorite Sport Part 2
Over the next week the twins trained him further. He was taught how to apply make-up and how to behave in a properly feminine and submissive manner and they trained his movements to be properly feminine. So as not to wear the skin of his ass, the twins introduced a new punishment tool for these trai... Read full Story
shemale lover 2011-12-12 4,902 torture toys bondage and discipline heavy
50%
Chinese Extremes Part 5
One morning Lien was one of three sissy-slaves were cleaning the slave toilets. The two others were using their tongues to clean the floor meticulously. Meanwhile Lien was using her tongue to clean the toilets. She was carefully licking the funnel leading down into the mouth of castrated toilet-slav... Read full Story
shemale lover 2012-01-17 4,180 torture extreme bondage and discipline
80%
Caitlin and Mistress Vicky
*Clack* *Clack* *Clack* The sound of my heels on the kitchen tile was distracting me right when I needed to focus. My wife, or Mistress Vicky as I'm to call her from now on, had left me quite a bit of chores to do today. I had just finished dusting and was getting ready to polish the kitchen floo... Read full Story
shemale lover 2012-03-01 4,473 Fetish domination feminisation
100%
Moon Probed at Hen Party Part 1
Honestly I had no idea all these things were going to happen to me. Perhaps I was just innocent but maybe when you read on you will be forming your own opinion about that. I guess it was something I couldn't talk about at school, it's just that I get aroused by my own body. I was kind of aware th... Read full Story
shemale lover 2012-05-23 3,512 hardcore anal sex long dick