Sort by
Relevancy

Free Stories

71%
A SISSY'S DESTINY
Gayness courses through your body. Your sissy cock soft but tingling in your gloopy sheer g-string, Toes slipping in their stockings pinched just right in high heels. Running your tongue over lips painted and glossy. Here you are. This is what you gave up your life for. This is why you gradually cut... Read full Story
MissDeeLiscios 2015-04-15 5,116 Crossdresser Lingerie cd sissy high heels precum
61%
YOUR SISSY DESTINY
YOUR SISSY DESTINY Gayness courses through your body. Your sissy cock soft but tingling in your gloopy sheer g-string, Toes slipping in their stockings pinched just right in high heels. Running your tongue over lips painted and glossy. Here you are. This is what you gave up your life for. This is... Read full Story
MissDeeLiscios 2015-05-27 5,769 Stockings cd sissy high heels precum
70%
Becoming a Sissy - My aunt my Mistress
For more than 6 months i’ve got this fetish, whenever my mom is out i crossdress with her clothes. It all started with porn, and slowly i got courage and from a pair of panties i ended up full crossdressed, with the make up made. Everything changed on this day, when i decided to crossdress even ... Read full Story
sissy emma 2017-10-05 73,961 Stockings Crossdresser domination cd sissy high heels
93%
Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
shemale lover 2015-05-01 14,975 first time ass Cumshot suck cd sissy make up
77%
Caucasian Sissy
When I go to the adult bookstore I always try to go to the ones in the worst neighborhoods. Most of the places I go are in the ghettos. The nastier the place is the better I like it, cause I know most of the men I'll have sex with will be either black or latino. Being white, I know how much rea... Read full Story
Kevyn-JeanneHarris 2015-12-25 6,916 suck interracial sex oral sex sissy
72%
Black Man's White Sissy
I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my ... Read full Story
shemale lover 2012-07-03 9,245 Cumshot oral sex sissy
90%
Sissy story and 1st meet humiliation
I recently met up with someone to be a sissy slut for them and wanted to share what happened on my first meet. This is the genuine true story. I use the username indoblu on websites, but my sissy name is Holly so I'll refer to myself from now on as such. I'll mention my history as a sissy before tal... Read full Story
shemale lover 2014-11-19 25,336 ass Fetish domination cd sissy
80%
Owned sissy girl
I met the mature dominant couple that I now call Mummy & Daddy on the internet. Their ad said they were looking for a full-time live-in mature sissy plaything. After we made contact they invited me to their house. I was instructed to bring any sissy clothes with me and to refrain from orgasm for... Read full Story
Andrina62 2015-09-23 28,756 anal ass rimming cd sissy
60%
A Sissy Boy is Made
By any measuring stick Greg Martin was a wimp, and a very submissive wimp at that. His wife of 14 years, Jaclyn, had discovered this even before the two of them were married. Actually, Jaclyn wouldn't have taken a second look at Greg, as most women didn't, had it not been for his submissive nature. ... Read full Story
shemale lover 2012-06-15 8,244 Cumshot oral sex sissy
66%
A Sissy's Wish List
Boys, boys, boys. First off, let me tell you that I have a butt plug shoved so deep in my little tranny pussy right now. That might help to explain how depraved I might sound. I really need some cock in my ass right now! I am sitting here stroking my tiny little tranny clit right now thinking of how... Read full Story
shemale lover 2012-06-19 4,282 transformation submissive sissy
72%
Sissy's Cherry Got Popped!
S)heplacement- Definition- Any sissy male that is willing to take the place, or replace any woman who is not properly taking care of their man inside or outside the bedroom... These gu(y)rls will make sure their makeup and lipstick is just right, their lingerie is matching, and that they are always ... Read full Story
Kevyn-JeanneHarris 2015-12-20 9,327 anal sex submissive sissy cross dresser
88%
A Natural Sissy Part 5
Stacy's Interlude "Hi, guys. I'm Stacy, and I guess you know I'm a sissy from what Gail has been writing about me. I don't mind being called a sissy, because that's exactly what I am, and we should all be proud of what we are, shouldn't we? Gail told me that I needed to write this chapter, a... Read full Story
shemale lover 2012-03-24 3,169 Lingerie crossdressing sissy heels wig
100%
A Natural Sissy Part 7
Stacy has a bad? morning The next morning I slept in a bit. Stacy woke me by climbing onto the bed and spreading my legs as was the method prescribed for such times. Stacy was a world-class pussy eater, and I guess I have his sisters to thank for that. When my orgasm came I opened my eyes to see ... Read full Story
shemale lover 2012-03-24 3,165 Fetish Lingerie sissy
100%
A Natural Sissy Part 8
Just as Stacy came back upstairs and told me the recreation room was ready for his tattoo application, the doorbell rang. "That's fine, Stacy. And just in the nick of time. That must be Heather at the door. Go let her in, please." Stacy looked at me like he could stab me in the chest wi... Read full Story
shemale lover 2012-03-25 3,066 cum fingering sissy
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 6,388 Stockings Fetish sissy
92%
Caught in High Heels
I couldn't believe the feeling as I slipped the pantyhose on over my legs. This was an absolute dream come true and I was living it right now. My friend Julie had gone out for the night with her 15yo daughter and she'd given me the spare keys to her house. She'd had a tradesman doing some work an... Read full Story
shemale lover 2012-10-12 5,631 Cumshot Fetish crossdressing
77%
How I Became the Sissy Slut
It all started when I was about 11. I was a very petite and short and had long straight brown hair with whispy bangs as a child. I was often mistaken for a girl. I have a sister who was 6 years older than me about my size she used to dress pretty sexy with the tight jeans and the skin tight sailor b... Read full Story
Tvtrinity 2016-08-29 71,352 Teen (18+) Crossdresser transgender sissy slut.trinity
78%
My Journey and The Pleasure of Fucking a TG/CD/Sissy
I used to think I was crazy. Maybe a part of me thinks I still am. Whatever the case, I'm not going to stop, and I'm going to continue what I'm doing for a very long time. Why? Because it feels so damn good. As I sat there while my latest little Sissy slut was servicing my thick an... Read full Story
JOAT 2018-04-12 12,400 tranny transexual crossdressers sissy t-girl T-Girls sluts
95%
Am I now a genuine Sissy Slut?
I started Crossdressing when I was about 16 years old, the usual story , mother and sisters panties from out of their drawers when I was home alone. As I got older and married I stopped Crossdressing and consentrated on being the family man. As the years rolled by and the kids grew up and left hom... Read full Story
Sissy Kirsty 2023-10-27 13,250 anal sissy stranger
75%
Sissify Your Boyfriend Manual - transation
original= manual-sissificar-a-tu-novio-4979 Used google translate, found some pronoun/object/context issues, and I believe ladybug = ladyboy Sissify Your Boyfriend Manual MANUAL FOR WIFE/GIRLFRIEND TO SISSIFY YOUR MAN, DISCOVER HIS SUBMISSIVE SIDE AND TURN HIM INTO ?HORNAND? AN... Read full Story
shelli_k18 2021-04-20 8,120 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
87%
A Picture Perfect Sissy
"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted wh... Read full Story
shemale lover 2012-05-27 10,464 Stockings anal sex Fetish Interracial sissy
100%
Sabbatical or Continuous Gang Bang? Chapter 2
I awoke several hours later still laying on top of Rick his arms holding me tight to him. His cock had gone flaccid as we slept and slipped out of me. I felt like I had run a marathon and my ass pussy felt like it had a marathon run through it. I slipped out of Ricks arms onto the bed and went into ... Read full Story
shemale lover 2012-08-28 3,665 anal Crossdresser Fetish Interracial
92%
Sissy schoolgirl and her black daddy
I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning... It was summer time. As always I spent m... Read full Story
shemale lover 2013-06-22 39,344 Teen (18+) Bareback Creampie Lingerie ass fucking Interracial cd
100%
Siisy Bride gets what she deserves
I had Ben on a contact site and we live surprisingly close together in Manchester. Ben is a 6’2” black man who has a large sex drive and likes women and girly trannys. I am a slim white guy who likes to dress like a smart woman, not a slut. I haven’t worn a wig for over 6 years ... Read full Story
shemale lover 2012-01-05 4,333 shemales interracial sex bdsm
50%
DATES NUITS
My wife, Denise, and I have been happily married for over 10 years. Over the years, we have enjoyed a vibrant and adventurous sex life. As we've grown in our marriage, we have become very open and honest about our sexual fantasies and desires. Through the years, we have come to realize that my w... Read full Story
Femboy 2021 2023-02-07 1,113 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial Sex Toys cum in mouth
66%
Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
Go Balls Deep or Go Home 2018-08-06 31,045 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
50%
LE PROGRAMME D'ÉCHANGE SISSY ⚧️ ⚧️
Kristy a travaillé pour Le Matriarcat. Cela semblait plus officiel que ça ne l'était vraiment. Comme si c'était un "Nouvel Ordre Mondial". C'était en fait un club dirigé par des femmes spécialisées dans certains services que les hommes paient grassement. Cela pourrait être appelé prostitution selon ... Read full Story
Femboy 2021 2023-03-25 980 Teen (18+) Cumshot Big Cock gangbang Interracial Sex Toys gloryhole cum in mouth femination forcé poule mouillé Maitress bdsm poule mouillé
83%
PF's Black Romp and JoyceLynn's Awakenin
When my wife and I first met, our sex life was fantastic! She was a very sexual lady and always made herself available. She usually wore stockings and garter belt or thigh highs, high heel sandals, and something that was sexy and suggestive. We made love and had sex in every room of the house, inclu... Read full Story
shemale lover 2012-05-17 4,162 Fetish Interracial Sex Toys
71%
TGirl Initiation by 3 BIG BLACK 12
In my teen years I was often told that I was quite feminine.The high school punks always told me that I filled out the back of my jeans in a girly way. After taking a shower one day I did notice that they were right, I had a nice white bubble butt. Not to mention that my lips were also quite girly. ... Read full Story
TgirlJill4BBC 2013-06-04 8,854 Stockings Cumshot suck Big Cock Lingerie Interracial Latex
100%
SOUMISSION BBC DE SISSY
« Tyler ! Arrêtez-vous – vous regardez à nouveau, et il l'a remarqué ! » La voix de Jack chuchota d'une voix rauque à l'oreille de Tyler alors que l'eau chaude de la douche tambourinait dans son dos. Il ne restait plus que les trois sous la douche maintenant. L'entraînement de basket-ball était t... Read full Story
Femboy 2021 2023-01-24 1,212 Stockings Teen (18+) Crossdresser Fetish Blowjob Big Cock Lingerie domination Guy Fucks Shemale Interracial cum in mouth
100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 3,871 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
100%
WHITE DOM EST DEVENU SISSY POUR LA BBC ⚧️ ⚧️
Je venais d'avoir 23 ans et je profitais de mon été. J'ai récemment déménagé en Floride pour mon premier emploi après l'université. Je viens du Midwest, vous pouvez donc imaginer à quel point j'étais excité par le changement de décor. Je suis assez grand, un bon mélange entre musclé et tonique, une ... Read full Story
Femboy 2021 2023-04-11 927 Blowjob Big Cock Lingerie Interracial Sex Toys sissy sissification hypno sissy slut cage de chateté sexe anal féminisation Sissy traitement hormo
100%
BBC DOMINATION SISSY BLANC
Mon nom est Tim. Je suis un homme blanc de 23 ans. Il y a environ 6 mois, j'ai déménagé à Los Angeles pour essayer de devenir acteur, mais comme vous vous en doutez, je n'ai pas eu beaucoup de chance dans ce département. C'était début novembre, quand je suis allé dans le bureau de mon... Read full Story
Femboy 2021 2023-02-04 952 Stockings Big Cock Lingerie domination Guy Fucks Shemale Interracial Sex Toys
83%
How Kevin Became Finesse
Monica went out with JJ! He was a black buff guy who taught karate where she took the kids. He drove a yellow corvette and liked to wear shirts with the sleeves cut off - to show off his big tattooed arms! All the young blonde girls were on his jock, but he had the eyes for Monica. She kept protesti... Read full Story
Kevyn-JeanneHarris 2015-12-20 4,328 sissy cross dresser cuckold
72%
Wie sich schlagartig mein Sex Leben änderte... Teil 1
ich war nun schon einige Zeit heimlicher Crossdresser. Nie wurde ich von meiner Freundin erwischt, auch wenn es manchmal wirklich knapp war! Ich hatte ein sicheres Versteck für meine schönen Sachen und meine Sextoys und konnte hin und wieder meine geheime Neigung ausleben wenn sie nicht da war.Trotz... Read full Story
Holly Swallow 2019-03-20 7,551 Stockings Small Tits Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob blonde gangbang domination Interracial Sex Toys humiliation Homemade sissy girlfriend chastity cage Ass to Mouth cum in mouth chastity sissy amateur crossdresser fendom
100%
The New Nii
The bedroom door opened and the two lovers walked down the hall into the living room side by side. Deena was wearing her nightshirt that she wore a lot, and Jeffery was nude, and he picked up his clothes that I had put on the chair and began to get dressed. “Jeffery is going to go and get dinner an... Read full Story
Setinkhan 2021-05-28 5,346 Crossdresser Fetish threesome Big Cock Shemale and Girl domination Interracial Sex Toys
50%
L'INVESTISSEMENT SISSY ⚧️ ⚧️
La fin d'une autre longue journée. Près de 19h00 et Colin Spencer travaillait toujours dans son box, presque terminé avec le dernier des papiers que l'un des associés principaux de la société d'investissement dans laquelle il avait effectué un stage depuis près d'un an maintenant l&#... Read full Story
Femboy 2021 2023-03-21 682 Stockings Lingerie domination Guy Fucks Shemale Interracial Sex Toys cum in mouth
100%
High Rise Heaven
I was deleting responses to an ad I posted several days earlier because my availability to host had ended. I checked each reply to see if there were gems I would want to keep. One reply stood out as unique. It was from a handsome black man with an offer to host me regularly; the name he gave was Pik... Read full Story
PetiteSlutKimberley 2023-04-04 4,609 Creampie interracial sex bareback anal sex seduction cd slut
100%
A Shell of A Man
Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money... but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty w... Read full Story
shemale lover 2012-06-11 9,244 Cumshot Fetish sissy
100%
A Very Hard Working Girl
I jump around a lot when I tell my story. I don't always tell it in the order that it happened. But I do tell my story accurately. It's all me. I write from experience, love to share the dirty little kinky things I do. There is no moral to the story, no ending. I just like to write about the things ... Read full Story
shemale lover 2012-07-17 4,638 Fetish oral sex sissy
100%
Ride of My Life
As a student at college I wanted a bicycle for Christmas. I hadn't past my driving test and even if I had, I couldn't afford to run one with my Saturday job wages. My parents didn't have much money so I didn't ask for an expensive model by name, anything would do. I didn't think they could go far wr... Read full Story
shemale lover 2012-09-04 7,004 Crossdresser Big Tits Blowjob Big Cock heels
60%
Teasing BIG BLACK COCKS at truck stops
I'm a white blonde bubble butt Tgirl living in Las Vegas and sometimes I go out and cruise the truck stops on I15 down south to I10. I do it at night and sometimes for a whole weekend in my mini van which has darkened windows. I love to get out of my mini van and walk around the back parking row at ... Read full Story
TgirlJill4BBC 2013-06-03 7,730 Stockings blonde Big Cock cum Lingerie Interracial Latex
85%
A Sissy's New Daddy Chapter 2
I hope you enjoy this second installment of 'A Sissy's New Daddy'. I worked hard on it and hope that it brings all of you the same pleasure reading it that it has brought me writing it. There are some extreme moments in this chapter but also some very tender ones. There was a line in the first piece... Read full Story
shemale lover 2012-06-16 12,581 Creampie oral sissy
89%
Tgirl BBC slut Jill ravaged by 3 BB12"Cs at BBC nightclub
I'm a white whore blonde bubble butt Tgirl BBC fuck slut living in Las Vegas. I love it here because we get many big black studs who cum here to be serviced. I dance at a private unadvertized no-name shemale club off the strip which caters to big black studs only. I love the thrill of being on ... Read full Story
TgirlSlut4BBC 2015-02-15 16,462 tranny ass Big Cock gangbang high heels bbc
100%
PantyBoy Gets A Reaming
I love to get really in touch with my feminine side. I get so turned on when I watch a man look my body up and down while I'm wearing some really sexy lingerie. I feel so naughty and slutty, knowing that I am going to let him do anything and everything he wants to me!! I was chatting in a room on on... Read full Story
shemale lover 2012-03-14 2,812 gay male interracial sex Fetish
100%
Who's The Sissy Now?
Like many people, I was bullied in school. I was small, slender and effeminate and, as a result, was often called gay, queer, fag and sissy by school bullies. The fact that what they said was sort of true just made it closer to the bone and more painful to hear. Like many teenage boys, I was going t... Read full Story
shemale lover 2012-11-14 6,820 shemale facial oral sex
100%
A New Way Of Life
This story begins as many do. I stared to dress at an early age in my mom's things. Then I started to buy my own things as I got older; panties, bras and high heels. I was always small for my age taking after my mom, she was a small woman with a nice figure and so was I. I was only 5'4 and 110lb, bl... Read full Story
shemale lover 2012-04-16 3,861 Fetish crossdressing sissy
100%
One experience with two black men
Hello again this is EvA…I am a 40 year old tranny. I do not consider myself a cross dresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine lady boy. I have been taking also hormones for 4 years, on and off and I already saw many changes&h... Read full Story
shemale lover 2013-05-16 4,296 Stockings anal sex suck threesome Interracial cum swallowing
80%
Me and 2 black men
Hello again this is EvA…I am a 40 year old tranny. I do not consider my self a crossdresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine ladyboy. I have been taking also hormones for 4 years, on and off and I already saw many changes&he... Read full Story
shemale lover 2013-06-22 5,400 Cumshot suck Ladyboy Guy Fucks Shemale Interracial swallowing
100%
My TV Sex Adventures Hot time in the Gurl&#
After sucking off the custodian of the offices next door I went back to the club. I was seriously disappointed. I loved how big and hard his dick was and I really wanted a serious cock like his to fuck. I got back into the club with only a knowing grin and a chuckle from the guy at the door. He was... Read full Story
shemale lover 2012-07-05 3,703 Group Sex Cumshot sucking Interracial
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 4,582 Cumshot oral sex sissy
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 9,932 Cumshot Fetish bdsm sissy
100%
Which Are You?
Which are you? A, B or C? A) You treat me well. You insist that I look stunningly pretty 24/7. You insist I always wear make-up, care for my hair and nails. You pay for me to go to a beautician once a week. You buy me sexy lingerie. You get angry if I wear slacks or jeans. You prefer dresses in p... Read full Story
shemale lover 2012-11-22 2,855 Fetish Lingerie sissy
66%
Free Shoes
"Lift your leg up on the sink and pull your panties down again. I like to watch you submit," the voice behind me commands. I didn't intend to go this far. It was supposed to be harmless fun. But as my throbbing cockhead rests against the cold of this stranger's bathroom sink and I can see ... Read full Story
shemale lover 2012-11-28 4,060 Crossdresser Fetish heels
56%
First black T-girl
I've been wondering what to write about lately. I've received a request to write about me and my sister, but that is a road I might have trouble going down. Today I was thinking about my bi-sexual stripper girlfriend from the past, who loved bringing home other strippers (mostly lesbians) for some h... Read full Story
bigtranslover 2014-01-01 6,873 first time shemales interracial sex
100%
Bike Shed Rendezvous
Chapter 1 A meeting you can't refuse The sun is shining brightly, but the ground is still damp from the morning's rain and the air is very cold. It's lunch time and you quickly walk across the College car park to the sports pavilion. Becky your sweet heart has told you to meet her and she's been ... Read full Story
shemale lover 2012-06-11 3,048 Fetish oral sex crossdressing sissy