Sort by
Relevancy

Free Stories

100%
Sissy Boy’s Secret Desire || Part 6
The room was heavy with the scent of sweat and submission, his body still trembling in the aftermath of what felt like total surrender. She lay beside him now, her presence looming, both comforting and intimidating. He had given her everything—his control, his dignity—and yet, there was an odd sense... Read full Story
shemale_club 2024-10-04 1,631 Stockings Small Tits Crossdresser Masturbation Fetish domination Sex Toys small cock sissy femboy hentai teen (18+)
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 3,652 Fetish Lingerie sissy
100%
Proud To Be A Sissy Chapter 4
As usual, Mr. Clark was sitting in his recliner when I went into his house. "Good morning daddy," I beamed kneeling before him. "Morning," he grumbled but smiled and said, "more like afternoon." But you do look sweet." "Thank you daddy," I rep... Read full Story
shemale lover 2012-12-24 8,585 Cumshot sucking Big Cock gangbang bukkake
100%
Proud To Be A Sissy Chapter 5
I awoke in almost total darkness, only a soft glow came into the hall from the kitchen. At first wondering where I was, my bed at home wasn't as soft as where someone, probably my new daddy had carried me after falling asleep on the floor. I shivered in delight remembering how my daddy had shared me... Read full Story
shemale lover 2012-12-24 6,651 Cumshot sucking Lingerie ass fucking cd
93%
Proud To Be A Sissy Chapter 7
"You're being really dirty little sissy slut today," daddy chuckled and asked, "What's gotten into you?" "Making up for the last few days I guess," I giggled hugging him tightly, "and I missed you too." "I missed my little sissy too." He repl... Read full Story
shemale lover 2012-12-24 8,262 Crossdresser Cumshot Blowjob Big Cock ass fucking
95%
Proud To Be A Sissy Chapter 8
I woke up to hear daddy lightly snoring and in my sleep I had draped a leg over him so that my body was almost covering him. I giggled to myself realizing that even in my sleep the sissy slut in me reached to grasp his flaccid penis. Then I curled closer up against daddy and contemplated about how m... Read full Story
shemale lover 2012-12-24 9,717 Teen (18+) Crossdresser Uniform Lingerie domination
100%
Alone at home
Living with my religious parents didn't provide many opportunities to spend time alone to enjoy myself. Only openings I found where, when showering, and occasionally when my parents travel, though that was not very often. I shared my room with my lil siblings, and since they were young and curious, ... Read full Story
Sara M. 2024-01-16 7,059 solo Lingerie small cock Homemade sissy femboy
100%
Caught outside in lingerie. Truth and Fantasy
There's a wood near my house. The path up to it is quite steep so it isn't used very much. I had gone up there early one morning last summer to take some photos and video clips. I have a camera on a tripod and use a self timer to take the photos. I have a long trench coat that I wear if I need to co... Read full Story
EmmaHuntcock 2024-09-23 2,712 Amateur Outdoor Lingerie sissy
75%
A Natural Sissy Part 6
Stacy Finds Joy With Joy I had told Stacy to write about how he came to be a sissy, even before I set it in concrete. But I need him up here in the bedroom now for another round of sissy humiliation. I've been entertaining Amanda and Joel, or Joy, I guess I should say. They just moved in next doo... Read full Story
shemale lover 2012-03-24 3,538 cum facefucking sissy
100%
Proud To Be A Sissy Chapter 3
I woke Monday morning actually looking forward to what the day may hold and feeling good about myself. I felt like I was a different person and as I thought about it realized that in a few ways I was. I laid in bed thinking I did have a little better understanding of my sexuality now that was so con... Read full Story
shemale lover 2012-12-23 7,769 Crossdresser sucking Big Cock Lingerie ass fucking
100%
TO BE OR NOT TO BE – FINAL ACT
TO BE OR NOT TO BE – FINAL ACT by Spanky de Bautumn Part 7. Sunny spent the night with Antonio and the next day they went to Mel and Shari’s for some fun. Antonio had school, so he was up and out early on Tuesday. Mel was in the shower and I was laying in bed, my mind wandering and not real... Read full Story
SpankydeBautumn 2021-03-02 3,040 Small Tits Crossdresser Cumshot Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
My wife doesn't believe I'm a sissy maid
It was our normal evening routing. My wife had gone to bed to watch some of her TV programs and I was left downstairs to watch my TV programs. As usual, I was soon logged onto FetLife, chatting with my sissy sisters and a few select men. I am a closeted crossdress, well a closeted sissy crossdres... Read full Story
DeniceD1975 2024-10-23 1,887 Stockings Crossdresser Cumshot Blowjob Uniform Lingerie sissy cum in mouth
100%
Sissy Slut and Stepdads part 2
My mother kicked Frankie out and swore that he was the last loser she would ever date. She believed that we were still having sex, and she was right. Pure raw animal lust drove us, and It was even better when we sneaked and got. That nervous adrenaline mixed with my passion and made me super horny a... Read full Story
Regina10 2021-02-15 4,609 Teen (18+) Crossdresser Big Tits Cumshot Masturbation Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Homemade Ass to Mouth
94%
dominated by parent's friend
I was 18 & around at a friend of my dad's house sitting for him when he arrived home earlier than expected. He told me he would drop me home until I mentioned that nobody was there until a few hours later so I'd have to stay there. A smirk came over his face at the mention of that & he quickly sugge... Read full Story
sissychloe 2017-01-13 16,320 Crossdresser domination cd sissy submission sissyboi
0%
Charlie and the Chocolate Factory
One of the real joys of the holiday season is how the kink community comes together to celebrate. It seems that everyone is allowed to let their hair down that much more, to party like pagans, and to lose him or herself to pure hedonistic pleasure. This holiday season, the Houston kink community... Read full Story
shemale lover 2011-09-27 4,190 asshole cum Lingerie strapon
100%
Slutty Sissy's 2 Loves
Tonight was young and I was already hot and bothered, my ass-pussy was on fire, and I could hardly wait for Bob and John to come over. I had invited them over to fulfill those erotic dreams I am constantly having about the two of them using me like a tool, and I wanted that so bad. I fantasized abou... Read full Story
Regina10 2020-11-23 5,461 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
100%
Slut /W Bad Boy
I was excited as always because I was about to go out in public and hopefully I will meet some horny man with some money and get laid. Now, to make sure that I am a picture of femininity, I double checked my makeup in several mirrors from many angles. My lips were perfect and I made sure my cheeks b... Read full Story
Regina10 2020-12-04 7,538 Stockings Crossdresser Big Tits Cumshot Bareback Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale pov Ass to Mouth
100%
Cheating Sissy Wife chapter2
My sweetheart Keith is back from his road trip and we were about to make up for lost time. He didn’t even want me to fix dinner. Instead he said that we would order pizza later. Meanwhile we started making out right there on the couch. We were both horny and anxious to get next to each other. I felt... Read full Story
Regina10 2020-10-26 5,288 Crossdresser Big Tits Cumshot Bareback Creampie Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth
50%
Being Shemale
Every night I wear make up and dress up in a sexy lingerie. I stand in my balcony late night trying to lure men and women driving on the road. Last night a truck driver stopped near my house to inspect his vehicle. During his inspection he suddenly saw a long legged booty women in the balcony inf... Read full Story
babydriver 2024-06-04 4,270 Stockings Crossdresser solo Outdoor Ebony Asian Ladyboy Lingerie big ass sissy femboy
90%
DISCOVERING BLACK COCK
To the greater Boston general public it was simply a small little known quite private night club located in the back part of Roxbury called The Black Rooster Bar. While in local Gay Community circles, insiders called this private by membership only pub, THE BLACK COCK CASTLE! When first learning... Read full Story
CD DIXIE IN NH 2016-05-10 10,703 Big Cock cumming sperm ebony cock
93%
Virgin Slut Cravings.
There have been so many times that I have had to hide how I felt because I lived my life denying who I was. I was a closet queen who was pretending to be normal. Some might have guessed my secret if they were observant. I didn't do things that other boys my age did. I love hanging out at home like a... Read full Story
Regina10 2020-09-29 9,240 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
100%
Camming down the rabbit hole Ch4
It was the morning after the night before, and as I stretched under the bedsheets, a smile spread across my face. Remembering last night’s events, I felt myself stir a little and pressure from the panties I had on adding to the arousal. It has been a while since I had morning wood after a big show, ... Read full Story
Dani_does_Dallas 2021-09-06 4,356 Crossdresser solo Amateur Cumshot Lingerie Sex Toys Homemade pov webcams
80%
Samantha sissy TGTF
Theme and genre of the story: The genre is about gender bender, futanari, gay, physical transformations of the body, magic and biology, the kink in particular that must excite in the story is the perversion of the transformation of the body and mind through a magical element that manipulates biol... Read full Story
Samantha sissy world 2022-09-20 5,427 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
50%
The Slave and the Sissy Part 5
Ella took the chain from their collars when they reported to her, together for the first time, in the morning. Pepper’s eyes were exceptionally bright this morning, and slave looked full of vigour and ready to carry out any command that befell him without the slightest hesitation. Pepper gripp... Read full Story
shemale lover 2012-08-13 4,155 anal sex little cock sissy
100%
COMMENT NATHAN EST DEVENU NATALIE ⚧️ ⚧️
Je m'appelle Natalie mais ce n'est pas le nom avec lequel je suis née; c'est plutôt le nom que ma femme m'a donné quand elle a fait de moi sa "sœur" et sa poule mouillée cocu peu de temps après notre mariage. Mon vrai nom est Nathan mais c'est un nom que je préférerais ne plus jamais utiliser parce ... Read full Story
Femboy 2021 2023-04-23 2,291 Teen (18+) Blowjob Lingerie Sex Toys small cock sissy cum in mouth sissify poule mouillée et fille premiere foi
85%
Cheating Sissy Wife
My name is Ginger and my main stud is Keith, a truck driver, who is only in town once a week. We have and ongoing role-playing fantasy that we carried out whenever he was in town. I am his dutiful ideal housewife who is perfect in every way. My talents excel in both the kitchen and the bedroom. I fi... Read full Story
Regina10 2020-07-27 8,081 Crossdresser Bareback Big Cock Ebony Ladyboy Lingerie Ass to Mouth cum in mouth double anal
91%
Hot Slutty Sissy
Hello, It’s me, and. I am about to make a big decision and right now I am dedicated to my fantasy. I got a call today from one of my ex boyfriends. I got so horny when I heard his voice that my nipples turn to steel. My titties seem to respond to the sound of his vibrating baritone. I couldn’t refu... Read full Story
Regina10 2020-08-14 7,233 Crossdresser Cumshot Bareback Fetish Blowjob blonde Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
94%
SISSY RULES!!!
There are a few things a sissy must understand in order to attract, and then keep, her man. Let’s look at them, these Sissy Rules. (✿◠‿◠) 1. Men are superior to you. This is rule number one for good reason: it is a simple statement of fact. It is so important that many questions that a potent... Read full Story
KittyHot 2021-06-18 9,171 Crossdresser Amateur Fetish submissive feminization sissy submission femboy hypno beta obedient
100%
Sissy Slut Reunion
Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... Read full Story
Regina10 2020-09-14 4,656 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
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 26,304 ass Fetish domination cd sissy
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 13,365 Creampie oral 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 3,331 Fetish Lingerie sissy
50%
eromène contre vieille pétasse
Une eromène baise une vieille pétasse Lorsque je levai la tête pour découvrir à qui appartenaient ces mains de mannequin qui me servaient, j'ai été surpris de tomber sur un girly-boy. "Autre chose" sourit-t-il/elle en traînant ses longs doigts vernis incolores sur la nappe. Je n'ai pas pu m'... Read full Story
hippocampus_171 2024-11-09 232 anal Small Tits Amateur Creampie Sex Toys Mature small cock big ass sissy femboy Ass to Mouth cum in mouth teen (18+)
100%
How a Transexual escort showed me how to bottom!!
I was now in my early 40's. I have had many experiences thus far with women, men, transexuals, and crossdressers. The majority of these encounters that involved cocks were mostly oral. I did however have a few experiences being topped. The first was unbearable yet I could not withstand the pain(... Read full Story
likesboth 2024-12-24 1,860 Amateur Cumshot Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Ebony Sex Toys femboy
71%
A Natural Sissy
Stacy is a natural sissy. I knew it the first time I laid eyes on him when he came to visit at my request on an Internet forum. After 3 months of Internet chat, I was ready to implement my plan. I knew he had money. He inherited most of it from his parents when they died in horrible automobile accid... Read full Story
shemale lover 2012-03-23 5,500 Fetish orgasm oral sex sissy heels
66%
Discovering Mistress Sarah's World Part 2
Chapter 4 : Introducing Miss May! Miss May's arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, "ki... Read full Story
shemale lover 2012-10-03 6,185 cum domination Sex Toys sissy
96%
New Job, New Life as as Sissy Slut Chapter 2
I was left lying on the floor, my face completely covered in cum. I was wearing lingerie and a dog collar and I had just been fucked long and hard by my "boss." My virginity had been forcefully taken. The thing is that I loved it. I loved being manhandled by this muscular man and I really ... Read full Story
shemale lover 2012-12-23 7,796 Cumshot Uniform Lingerie ass fucking domination
50%
Sissy Acceptance *
La primera vez que vi porno interracial algo recorrió mi interior de una manera que nunca antes había experimentado, era como un hormigueo que pasaba por todo mi cuerpo….. hasta llegar a mi ano. No sé que fue lo que me motivo más si la insaciable obsesión por probar una verga negra, ó el hecho de... Read full Story
Sissycrick 2023-05-04 1,826 anal Small Tits Crossdresser Amateur Latina Bareback Blowjob Big Cock Lingerie Interracial sissy femboy e
100%
Mein erster Blowjob
Nun hat es endlich mal geklappt. Ich schrieb längere Zeit mit einer anderen Sissy und lernten uns immer besser kennen. Nach mehreren vergeblichen Versuchen sich mal live zu treffen, hat es dann endlich geklappt. Wir trafen uns auf einem Parkplatz. Ich hatte bereits einen heißen String, Strapse und e... Read full Story
Maja 2023-07-04 1,955 Stockings Small Tits Crossdresser Amateur Outdoor Blowjob Big Cock Lingerie Homemade sissy
100%
Beryl's birthday suit
I tried on my sister's panties when I was 12. They looked so cute, so sexy.. I couldn't help myself. I tucked my dick between my legs and pulled them over my hips, delicately positioning them just like a girl. They felt yummy! When I saw the shiny, lacy pink briefs in the mirror - snug, flat pu... Read full Story
Beryl 2023-12-12 8,120 first time Stockings Crossdresser Bareback Blowjob Big Cock Lingerie redhead sissy cum in mouth
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 19,752 tranny Big Cock jerking off
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 18,173 Stockings suck oral Lingerie public cd
80%
A New Spin On Role Playing Games
A New Spin on Role Playing Games By: Shawna Summers shawnavinylltv@gmail.com I've always been something of a geek. I love sci-fi and fantasy books and movies; I can recite countless bits of useless trivia back to you about all kinds of movies. So, it was no real surprise that I took to rol... Read full Story
shawnavinyltv 2018-06-14 11,181 Crossdresser anal sex Blowjob gangbang Lingerie bondage
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 35,005 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
66%
TO BE OR NOT TO BE – PART 5
TO BE OR NOT TO BE – PART 5 by Spanky de Bautumn Part 4. Sunny made a life changing decision and in the process becomes better acquainted with Mark. On Monday, I met Mel and Shari at the theater at ten to run lines. I was confident that I knew my part for the first act. My concern was with m... Read full Story
SpankydeBautumn 2021-02-24 2,611 Crossdresser Cumshot Masturbation Blowjob Big Cock Lingerie Interracial
89%
How I Became a Girl
My name is now Stephanie, once it was Stephen. I would like to relate how I was turned into a girl (really a transvestite slave) by the beautiful young lady who has become my mistress. I have always felt that I should have been born a female. I definitely have female traits. I have a very feminine... Read full Story
shemale lover 2018-12-30 14,214 Masturbation pussy little cock
100%
Birth of a New Sissy Part 3 Completion
I suppose at some level I knew it would happen. Or at least I should have. After nearly a month of servicing Jeff's cock and fucking myself silly on my dildo lover things took a turn. I came home from work a little early on a day Laura was off as well. When I got home she was out, but as soon ... Read full Story
shemale lover 2011-11-17 5,545 cum domination crossdressing
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 3,592 cum fingering sissy
94%
The Accidental Sissy
My girlfriend and I live in an apartment in small town in Texas. She a good looking 31 year old babe with a great body and sex drive to match. My girlfriend, Suzy is full figured but not fat, just a big girl and I love every inch of her. Me, I'm 6', 185, starting to put on a little of that middl... Read full Story
shemale lover 2013-01-04 10,668 Crossdresser Cumshot Masturbation jerking Lingerie
93%
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 40,588 Teen (18+) Bareback Creampie Lingerie ass fucking Interracial cd
100%
bi to sissy caught and turned
It was during a Wednesday nite supper this past April when Penny my wife of seven years, suddenly looked me straight in the eyes while calling me a GAY COCKSUCKER ! Instantly while I swallowed hard and quickly looked away from her, my worse dreaded fears in life had somehow just become reality! So ... Read full Story
redthongthong 2022-08-02 9,808 Crossdresser bisexual sissy crossdresser forced feminization CAUGHT!
100%
Dating my Sissy-sister (English)
You are wearing women's stockings and a thigh-high transparent top, the thin shoulder straps of which leave your arms and shoulders elegantly exposed! You're the real lil bunny to me in that girl outfit of yours... How about, should I teach the little one about the naughty girl? You're giggling a... Read full Story
LulaSissy 2024-09-24 3,424 anal Stockings Crossdresser Cumshot Bareback Fetish Big Cock Ladyboy Lingerie femboy shemale fucks shemale cum in mouth shemale fucks female fucking sissy
91%
Birth of a New Sissy Part 1 Encounter
I met Jeff one day at the nearby tennis courts. I could never have imagined what the result of that meeting would be. I suppose I should tell you a bit about me. I'm a happily married 34 year old. About average in most respects. A little spare tire trying to form around the middle but in decent ... Read full Story
shemale lover 2011-11-17 5,710 cum Sex Toys crossdressing
100%
My Sissy Fantasy Part 2
I lie still not daring to move, holding onto the arm he has round me, slowly trying you control my breathing and my excitement. Crazy thoughts run through my head and I think I’m not gonna sleep tonight, but then before I can realise how tired I am, I drift off to sleep. I wake the next morni... Read full Story
shemale lover 2012-03-27 3,271 fingering little cock 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 9,992 anal sex submissive sissy cross dresser
100%
TO BE OR NOT TO BE - PART 7
TO BE OR NOT TO BE - PART 7 by Spanky de Bautumn Part 6. Sunny, Mel, and Shari had a heart to heart and Mark took Sunny for a night on the town. I woke up next to Mark, he looked so peaceful sleeping. Was I dreaming? Did I fall asleep and dream that Mark said he was going to take me shopping... Read full Story
SpankydeBautumn 2021-03-01 3,232 Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth