Sort by
Relevancy

Free Stories

50%
Headmistress' Favorite Sport Part 8
For Denise her life as a fully trained slave began with a stay at Mistress Rachel's house before joining the twins' household. Since it was their idea to turn her into the sissy she now was, it was agreed that she would be their slave. But as the twins were moving out of Mistress Rachel's house and ... Read full Story
shemale lover 2011-12-13 5,697 torture toys bondage and discipline chastity belt
85%
Dominance Reversal Chapter 2
10:30 AM I can't help but think how I could possibly get out of this. Here I am sitting on the edge of my bed with a large assortment of overly sexy clothing that I would never agree to wear in a million years. I hold up the black, skimpy panties and my cock begins to stir from within its steel c... Read full Story
shemale lover 2012-10-21 5,686 Fetish handjob chastity belt
0%
Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
Alicexiao 2023-01-06 3,984 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
87%
Headmistress' Favorite Sport Part 3
There was no more time for Denise and Susanna to get over their chemically induced bout of incestuous activity as Denise was being sent to school. This was of course part of the plan. Slaves should always feel guilty about something and once their slave training was over, neither would be able to ma... Read full Story
shemale lover 2011-12-12 6,077 toys bondage and discipline chastity belt
83%
Headmistress' Favorite Sport Part 5
A new part of the first year slaves training was introduced as part of the plan to make them hopelessly addicted to sex. Every evening when they finished class they would be escorted to a room covered in rubber on the inside. The sissies were ordered inside unbound and unescorted, dressed only in th... Read full Story
shemale lover 2011-12-12 6,025 torture toys bondage and discipline chastity belt
100%
Headmistress' Favorite Sport Part 10
When Denise came to she was lying in bed. She had been washed and she could no longer feel the annoying diaper rash. In fact she felt fine, clean and well rested. On her feet were what turned out to be black Oxfords with seven-inch heels. Her ankles were in steel cuffs and connected by a eight-inch ... Read full Story
shemale lover 2011-12-13 4,462 torture toys bondage and discipline chastity belt
88%
Dominance Reversal
5:00 AM Cindy was lying in bed next to me. Man does she have an amazing body. It's a shame that she's totally shy and doesn't really appreciate what she has. Once we got married, I talked her into getting breast implants. She had pretty nice tits, but B cup is just too small for me. I like my wom... Read full Story
shemale lover 2012-10-19 6,403 erection chastity cage
100%
Headmistress' Favorite Sport Part 4
Over the next weeks Denise and the others settled into the routine, accepting their new life. Cindy did, as Mistress Hoffmeyer had predicted, break very easily and now she had been remolded as the slave-sissy her master wanted her to be, docile and obedient. Others needed more effort and others less... Read full Story
shemale lover 2011-12-12 7,341 torture toys bondage and discipline chastity belt
100%
Headmistress' Favorite Sport Part 6
At Mistress Rachel and Master Tony's house Denise was pushed into the role of maid along side her mother, Susanna. Susanna had been reshaped exactly as Mistress Rachel wanted it. She was now a devoted little nymphomaniac slave who loved her mistress and master and who would do anything for them. Lik... Read full Story
shemale lover 2011-12-13 4,431 torture toys bondage and discipline chastity belt
0%
Headmistress' Favorite Sport Part 7
At the academy Denise and the others immediately resumed their old routines. The training for the second year slaves had started a few weeks before the new batch of sissies arrived at the academy. Not many new elements were introduced in the training as the second year was mostly about perfecting th... Read full Story
shemale lover 2011-12-13 4,432 torture toys bondage and discipline chastity belt
0%
Headmistress' Favorite Sport Part 9
When Denise returned from the academy all this was taking place without her knowing about it. She started her new life as a maid in Mistress Rachel and Master Tony's house alongside her mother, Susanna. Susanna had in the meantime developed into a complete slave, craving punishment and humiliatio... Read full Story
shemale lover 2011-12-13 5,376 torture toys bondage and discipline chastity belt
90%
Collette's Property
I've been Collette's lover for four years now and this gorgeous, incredibly kinky woman still continues to amaze me. Our sex life would be unimaginable to most people, even those who live lives embracing BDSM and other fetishes, and it's Collette who makes it happen. Of course everything is a trade ... Read full Story
shemale lover 2012-12-19 7,727 anal Crossdresser Blowjob domination ass fingering
66%
Fourth Slave
I had been to this particular establishment before. I knew very well what they did and the women here were nearly all abducted. I knew that. What had brought me here today or rather on this night, was the loss of my slave. I had sold her when I got bored with her. I had a particular taste in women t... Read full Story
shemale lover 2012-11-19 7,810 Stockings Fetish domination
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 4,295 Fetish domination feminisation
76%
A little favour
Day 1 – Friday My neighbor Kathleen called me up one Friday evening and asked me if I could come over to her apartment and help her with something. She lives in the apartment next to mine, so I went over there. She was sitting at the kitchen table talking to a girlfriend. They were finishin... Read full Story
shemale lover 2014-03-01 15,101 shemales Fetish bdsm
100%
Claudia Coming out adventure part 1
*Author's Note: This story starts off being told in First person and after awhile the story shifts to third person* Hello everyone, my name is Claudia I am a Cross dresser who one day hopes to be transgendered, although I do not want the surgery, I am looking to eventually live my life full... Read full Story
MissClaudia 2015-01-04 5,714 tranny Stockings suck Creampie ass fucking doggy style Latex
100%
Whoring for freedom
It is four o'clock on a Friday afternoon and I have been driving for almost two hours on my way to a cabin in the middle of nowhere. According to the instructions my Mistress gave me, I still have about an hour to go. I have the air conditioner on because it is a very hot day and I have to make sure... Read full Story
shemale lover 2012-11-07 3,943 Cumshot teasing sucking off
50%
Bewitched, Bothered And Bewildered Part 3
RULES OF THE GAME Where Vivian's mother lays out exactly what she expects from her son if he wants to keep her onside and help him to achieve his dream. Vivian went into the bedroom with a towel wrapped around his waist. He was whistling, there was a spring in his step. "You've been ag... Read full Story
shemale lover 2011-10-15 3,144 Fetish transsexual feminization
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 4,714 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
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 9,281 transgender toys bondage and discipline heavy
71%
Sissy For My Flatmate
My heart was racing as I gazed up at my flatmate, there was an something of an evil gleam in his eyes as he looked down at me and my mind kept jumping back to the events that lead to this moment. I'm a closet crossdresser, yet now my flatmate (whom I managed to hide my “hobby” from fo... Read full Story
shemale lover 2012-07-25 6,340 Stockings Fetish sissy
0%
P.A. for a Day
The gates swung closed behind Charles as he slowly drove his car up the sweeping driveway. Even though he was looking forward to the erotic delights which were in store for him that day, the cares of the world seemed to weigh heavily on his shoulders. As he drove up to the garage he mused about t... Read full Story
shemale lover 2012-09-05 5,666 Crossdresser Masturbation Latex Sex Toys heels
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 3,928 sucking Blowjob swallowing
100%
Fun With Friends Chapter 4
As I stepped into the shower the warm water hit my body and felt great. I relaxed my ass and let Greg's cum stream down my leg. I could not believe that in the last couple of hours I had been shown to one of my best friends as a cross-dressing slut and had now taken his cum in both my ass and mo... Read full Story
shemale lover 2012-12-12 3,318 anal Creampie Latex
100%
Chapter 1 - My Cuckold Life
I have a small penis. In fact, I have a very small penis. I’ve been in permanent chastity for over 7 years. My wife and her lovers call it my “caged clitty” and that’s about right as far as it being a useful penis. I suppose I should start at the beginning. I’ve never been much of a man. I’m ... Read full Story
Sissy Annabelle 2022-08-23 5,739 Crossdresser Interracial sissy chastity Cuckold Husband
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 3,949 torture extreme bondage and discipline
50%
Devastating and dominating
Tracy drove the black SUV with her friend Miss K in the passenger side, both of them struggling not to be bored to sleep with the monotonous countryside I-64, the scenery broken up only by the occasional road sign or truck stop. The Madonna CD thumping in the stereo helped matters though, the t... Read full Story
shemale lover 2012-01-29 4,815 Masturbation sucking Creampie Latex fucking
100%
Sissy For My Flatmate Chapter 2
If you've only just tuned in, here's what's going on in my life. Until recently I was a closet crossdresser trying to keep my hobby from my flatmate. When he caught me in the act, I found out that not only had he known about me for a long time but it was a turn on for him. I agreed to become his sis... Read full Story
shemale lover 2012-08-12 3,560 oral sex cum swallowing sissy
77%
Allie's Encounter on Craigslist
Let me start off by saying this is a 100% true story. I know there's some that will try and pretend to be real but are in fact not. There's no real way for me to prove it, but nonetheless I just wanted to share my experience. About a week ago I posted an ad on craigslist "19 y/o Asian CD loo... Read full Story
shemale lover 2012-10-16 4,705 Fetish Sex Toys crossdressing
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 4,698 shemales taboo humiliation
88%
My wonderful life with Pat : Domi and Morgan
second part of the tattoo ..... I was nervous to be tied and at her mercy.Morgan put on a mask to make me blind and she tightened the ties to keep me from moving. Then with a very soft voice Morgan sussed me, don’t be afraid, i will make this day an unforgettable one. You will have a such intens... Read full Story
jperrot 2021-04-09 2,944 Amateur Outdoor Masturbation Bareback Shemale Fucks Guy threesome Blowjob domination Ass to Mouth cum in mouth
66%
My girlish desires
My girlish desires, I am happy to spend my weekend at home to live my life as a woman. I apply a depilatory cream to my body, which I leave to act for a few minutes before going in the shower. I take this opportunity to do an enema to avoid unpleasant surprises during my girl games. Then, using ... Read full Story
sandratvtg 2023-01-19 3,698 Stockings solo Cumshot Creampie Fetish Big Cock Lingerie Sex Toys
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 4,950 Crossdresser Cumshot Fetish Blowjob Latex
66%
A Perfect Cuckoldress Wife
My wife rose slowly, before lowering herself down his length again. Her head tipped back, she squeezed her breasts, playfully teasing her own nipples. Her eyes opened, lustfully admiring the chiseled ebony body of her lover. Balanced skillfully on her stockinged toes, she began picking up the tempo ... Read full Story
shemale lover 2012-04-30 4,894 Cumshot Creampie Fetish crossdressing
100%
Demoted Chapter 2
The next morning I was awoken by the sun rising and I just laid there comfortably in Kevin's arms. I thought about all the events of yesterday and last night. I was smiling to myself as I felt him move his head and kiss my neck and say, good morning beautiful. I said good morning sexy in reply and h... Read full Story
shemale lover 2012-08-13 2,790 Cumshot Creampie oral sex handjob
100%
The Meeting
He could not believe that he was finally going to see her after all these years. Since his divorce, she had been all he could think of. He fantasized every day how it would be to see her again, make love to her again, and now the day had finally arrived. He could barely sit still. He had decided... Read full Story
shemale lover 2012-12-21 5,483 Crossdresser hardcore Cumshot Lingerie Latex
100%
Darling Nikki
Chapter 1 - The Setup "I'm going to catch him!" Samantha thought to herself as she looked at her disheveled panty drawer. She now had proof that her roommate, Nick, had been wearing her clothes, but had to catch him in the act. She did a search online for ideas on how to catch him. She ... Read full Story
shemale lover 2012-07-15 7,155 Cumshot oral sex Latex sissy
100%
My wonderful life with Pat : The tattoo
Few hours later Marie and Pat arrived, Marie ordered me to stand-up and kiss me hardly with her tongue rolling in my mouth. She say me goodbye and thank you so much for dinner and the marvelous night, Pat is really lucky with you. I was so surprised i reply by a shy thank you. After Marie has le... Read full Story
jperrot 2020-09-18 4,285 Amateur Outdoor Shemale Fucks Guy domination Ass to Mouth cum in mouth
75%
My shemale GF Part 2
So today she, her name is Christy, she wanted to do something kinky, very kinky I said that's fine. We cleaned up, she went into her closet, which was filled with dildos, butt plugs, sexy clothing, fleshlights, cock rings, paddles, lube, videos, magazines, bdsm things, and a fuck machine. She came o... Read full Story
shemale lover 2012-07-04 3,429 anal sex Creampie shemale Latex rimjob
71%
Francis to Frances
It was never my intention to go to live with Aunt Matilda and Aunt May, in New York state five hundred miles east of Arlsberg but when I was offered a place at Uni a short bus ride from their place that Dad suggested I should see if I could stay with them. Dad always referred to them as Aunt Mati... Read full Story
shemale lover 2012-11-21 4,606 Creampie Fetish transformation
75%
Just another Saturday appointment at my Hair Salon
After I applied my makeup and jewelry, the young salon clerk helped me slip into a skin-tight black latex catsuit, with a crotch zipper from front to back. The 2 beauticians then used shiny duct tape to secure my wrists to the salon chair arm rests. They then spread, elevated, and taped my ankles to... Read full Story
PurpleFlower9222 2020-12-16 4,649 Amateur Creampie Fetish salon Colored hair bondage fuck
50%
SISSY AWAKENING ⚧️ ⚧️
"Hey bébé, quand est-ce que tu rentres à la maison?" le message texte bourdonnait doucement. Sortant discrètement le téléphone de ma poche, je tape "Même heure que d'habitude, juste après 5 heures, pourquoi... quoi de neuf ?" C'est mon amante Sarah, ma meilleure amie et une femme que je connai... Read full Story
Femboy 2021 2023-03-25 818 Stockings Blowjob Uniform Lingerie Sex Toys gloryhole cum in mouth cage chastity feminisation forcé maitresse épouse sexe anal
50%
TRANSFORMATION DU SOUS-SOL DE ZOEY ⚧️ ⚧️
Jack a terminé son entraînement du matin en s'étirant. La sueur dégoulinait de ses muscles maigres alors que le chaud soleil matinal frappait la peau nue de sa poitrine. Il se pencha pour ramasser sa bouteille d'eau, reconnaissant pour une brise fraîche soudaine alors qu'il remontait la courte allée... Read full Story
Femboy 2021 2023-04-10 501 anal sex humiliation feminization humilation cage chastity poule mouillé Maitress esclavage gode ceinture
88%
Feminized by My Girlfriend
About 6 months ago I joined a gym because I have never had a very masculine body and now that I just turned 21 it was time to finally get off my butt and try to build some muscle. That is where I met my girl friend Brook who stands 5' 9", has a fantastic body and a gorgeous face. She looks like... Read full Story
shemale lover 2012-07-14 16,233 Fetish oral Sex Toys feminization
58%
Married guy wants a shemale to fuck his wife
I'm a married guy and I've had this fantasy of a shemale fucking my wife for quite some time! She is a very attractive lady. She has been hesitant in the past to try new, kinky things, however, lately, she has begun to get into what initially was my self-imposed chastity. However, she quickly shoots... Read full Story
shemale lover 2015-08-25 8,001 sucking Creampie pussy
100%
The Sin of Lust
"Forgive me, Father, for I have sinned." Father Jeremiah looked up from his paperwork to see Sarah standing in the doorway of his office. He cocked a brow at her, then returned to writing his next sermon. "I'm sorry, I can't help you," he said, without looking back up, "i... Read full Story
shemale lover 2012-04-08 2,539 anal sex Creampie oral sex rimjob
60%
Cassandra Chapter 2
The days and weeks seemed to fly by. My new position at Barnes and Bidwell was a dream come true. It provided me with a cute income to cover my personal expenses (Melissa took care of most everything), exactly fit my bubbly, flirtatious personality, and offered me unlimited opportunity to meet - and... Read full Story
shemale lover 2012-03-28 3,398 Group Sex Fetish Latex
100%
Darla's Video Delight
The day had gone well so far with my girlfriend of the time having just left the night before, going out of state for two weeks visiting relatives. It was Saturday so I didn’t have to work, I had completed my chores... shopping, cleaning the apartment and doing laundry and had spent the aftern... Read full Story
shemale lover 2012-07-14 2,985 Fetish cum oral Latex
66%
Forced to be Feminine
Chapter one Tuesday J was up early, I could hear him moving around obviously looking for his case, he certainly wouldn't find it as I has managed whilst his attention was diverted to drop it off the side of the boat, it meant the only clothes he had were the ones he stood up in plus a couple o... Read full Story
shemale lover 2012-11-17 13,737 Fetish feminization submission
96%
The Magic of the Lamp
"Are you serious? I'll give you $20 bucks for that thing!" said Tommy. Tommy couldn't believe how lucky he had just gotten. Thrift shops were notorious here for ripping people off, but this store seemed to be giving him a pretty good deal! "Yessir. We have had that little lamp f... Read full Story
shemale lover 2013-03-05 8,390 sucking Blowjob domination big boobs ass fingering
95%
My best friend turned trans.....so I fucked him - Part 1
Theres a bit of history to this one so strap in! I started hanging out with this group of kids in my area when I was 12 years old, we did all the typical stuff you can imagine young kids getting up to (played football, chased girls etc...) over the years I became really good friends with one of the ... Read full Story
iconicirish 2023-05-11 8,356 Stockings Amateur cock Masturbation sucking Blowjob Big Cock Lingerie Latex transgender sissy
100%
Additional Thoughts on Sodomy
Although, in the world (or worlds?) of pornography and erotica, it is politically incorrect, perhaps, to suggest that the body, whether male or female, is not built for anal intercourse, the fact is that anyone who has participated in this act (especially on the receiving end) or who has enjoyed wat... Read full Story
shemale lover 2011-10-05 3,773 Creampie sperm anus
100%
First Time
I'm not really sure how I ended up where I am. However, the events below are true and only the names have been changed. It happed to me over 15 years ago and my life has never been the same. It was my freshman year of college, being 35 in the middle of a mean divorce I decided to sell my condo an... Read full Story
shemale lover 2012-09-28 4,054 anal Creampie oral sex crossdressing rimjob
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 11,507 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
92%
MY TS FOXXY & VENUS LUX FANTASY
Alyssa Gomez and Venus Lux were visiting Newark, NJ and decided to have lunch in the restaurant that I work in. It was a rainy day. The seductive pair were returning back to their suite in the Courtyard Marriott, but not before grabbing a bite to eat. Alyssa and Venus sat the bar and ordered a coupl... Read full Story
I_GO_3WAYZ 2021-03-02 10,914 Latina Creampie Shemale Fucks Guy threesome Blowjob Ass to Mouth cum in mouth double anal
100%
Intense
Holding to my word, I didn't let the incident with Billy and his friends scare me away from Bailey; I kept seeing her, even after the beating I took. To be honest, I'm not sure if he was trying to lay low or what, but Billy seemed to keep his distance from me for a while...thankfully. Bailey and ... Read full Story
Verpa 2019-10-21 10,507 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Big Cock cum in mouth