Sort by
Relevancy

Free Stories

100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 14,124 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
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 12,035 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
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 34,187 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
42%
sexy jane story
I love the idea being a crossdresser wearing women outfit bars in panties n sexy outfit not just for the sex I love sex being on my knees sucking cocks in getting fuck by a big cock see win I was very young I had sex with 3 guys one day they ask me will I suck there cocks in I sand yes we want insid... Read full Story
45sexyjane 2019-05-27 4,310 Small Tits Crossdresser Amateur Big Tits Masturbation Blowjob blonde Big Cock gangbang Lingerie Sex Toys shemale + shemale sexy crossdresser
90%
Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
Regina10 2020-11-30 9,411 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
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 7,937 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%
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 5,115 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
100%
The Big Tiddy Goth Girl
Hannah and I went to the pool in my apartment complex. This was my first time dressed as female in public and I was loving my new, feminine tan lines. To keep a long story short, while tanning we were perv'd on and approached by a guy calling himself Mark. He was desperate for our attention and fumb... Read full Story
KaceyKlarissa 2024-02-23 5,026 Crossdresser Big Tits Cumshot Masturbation threesome Big Cock Shemale and Girl small cock big ass sissy femboy cum on tits goth
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 10,328 Big Cock cumming sperm ebony cock
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 4,842 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
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 4,921 Crossdresser Big Tits Cumshot Bareback Creampie Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth
66%
Cock Sucking Jail Whore
I've always known that I was not meant to be a guy. Being sexual curious I would look at porn mags like any one does. At first it was just magazines with pictures of naked woment. It was when I ran across my first Hustler magazine that my life was changed forever. Seeing pictures of studly guys with... Read full Story
shemale lover 2011-09-17 4,528 Cumshot asshole oral sex
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 4,319 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Big Dick Alessia Visits Dallas
Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... Read full Story
darrell 2022-04-20 4,522 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
100%
Camming Down the Rabbit Hole Ch. 09
As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night ... Read full Story
Dani_does_Dallas 2022-03-22 3,599 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
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 5,749 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
100%
Fender Bender Chapter 9
My name is Robert, I have been cross dressing since I was 14. I turned 18 last summer and this story takes place during my senior year in High School. I am 5'9" 160 pounds, blonde hair and blue eyes. When I am dressed I call myself Vicki. __________ I had met Julie at a recent party. Well... Read full Story
shemale lover 2012-07-27 3,503 Group Sex Cumshot Sex Toys
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 9,153 Crossdresser bisexual sissy crossdresser forced feminization CAUGHT!
50%
My Parisian escapades,
My Parisian escapades, During my many business trips to Paris, I never miss going to see my friend. Sabrina is a Cuban transsexual that I have known for several months. With her, I can let go with complete confidence and live my fantasies. I am one of his friends and lovers who give him the ... Read full Story
sandratvtg 2024-06-25 2,374 anal Stockings Shemale Fucks Guy Fetish Lingerie Sex Toys sissy wig gode pumps rosebud silicone breast split panties
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 5,790 cum domination Sex Toys sissy
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 1,297 Teen (18+) Cumshot Big Cock gangbang Interracial Sex Toys gloryhole cum in mouth femination forcé poule mouillé Maitress bdsm poule mouillé
66%
Elizabeth: Beginnings of a Sissy
I had a pretty good system going. My 18 year old sister would stay up to watch Sex And The City reruns with me (well she watched, and I smoked weed), and during the first ad breaks, would run downstairs and get changed for bed. During the next ads, I would go to the bathroom, and on my way, raid her... Read full Story
shemale lover 2012-04-02 4,765 first time Fetish Blowjob facial Sex Toys sissy
100%
A New Life Part 2
The next few days I spent packing and repacking. I would need to watch what I packed as I was taking a plain to meet Sara and Tom. Most if not all my toys would either need to be mailed or stay behind. I had packed five suit cases all of them filled with female clothing and shoes. My carry on was pa... Read full Story
shemale lover 2012-04-13 3,194 Cumshot Sex Toys cum swallowing sissy
50%
"SISSIFIED": 12 JOURS DE SISSY-MAS
JOUR 1: mardi 25 C'était le matin de Noël quand j'ai entendu frapper à ma porte, ce qui était, bien sûr, très étrange à dix heures du matin. À midi, j'allais chez ma famille pour Noël, et j'avais rarement des visiteurs inattendus. Toujours dans ma robe, je me dirigeai vers la porte et fus s... Read full Story
Femboy 2021 2023-01-20 1,436 Stockings Crossdresser Amateur Fetish Blowjob Big Cock Lingerie domination Sex Toys cum in mouth
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 1,475 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial Sex Toys cum in mouth
75%
Dottie's Back Chapter 4
Waking up on the single bed in the spare room was not the best way I could imagine to begin a day. Dragging myself from underneath the covers, I made my way to the bathroom and stepped into the shower. The previous night's events were still fresh in mind: Stacy having slept with another man and then... Read full Story
shemale lover 2012-11-02 3,632 Cumshot dildo Sex Toys
100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 9,249 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
100%
Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
darrell 2022-01-03 4,526 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
100%
Meeting Amanda
I’m a happily married man. My wife Tess and I have been together since we were teenagers. We were each other’s first real lovers and being in our mid-thirties by now, we still madly in love with each other. Tess and I always are very honest and open to each other. Both in normal life and sexual... Read full Story
rforasht 2022-07-20 7,616 Big Tits Cumshot Shemale Fucks Guy threesome blonde Big Cock Lingerie Shemale and Girl redhead Homemade Shemale fucks couple
100%
A Toy Party Story
Toy Party Story Recently I met with a person whose sole desire was to be fully dressed and transformed for me. We spent quite a bit of time on the phone discussing why feminization was such a powerful fantasy for him. He explained that he felt so vulnerable and powerless as a woman and that it... Read full Story
shemale lover 2012-07-09 4,509 Big Cock oral sex feminization
100%
Feminized by My Girlfriend Chapter 2
I followed Brook and Linda out of the spa onto the sidewalk and I looked around for the limo but it was no where to be found. As the girls started walking down the street and talking to each other, I asked where the limo was. Neither of them responded and just kept walking. I followed behind as clos... Read full Story
shemale lover 2012-07-14 13,817 Fetish oral Sex Toys feminization
0%
A Working Sissy Girl
I look up at my boots. Cute! Received delivery just day before yesterday, my boy friend hasn't even seen them yet. He'll like them, know he will. 3" spike heel ankle boots, very shiny patent leather, I look up at the one on my right foot. I run my hand down the thigh-high lace top seamed nylon ... Read full Story
shemale lover 2012-07-29 3,890 Cumshot oral sex sissy
100%
Discovering Mistress Sarah's World Part 4
Chapter 11 Discovering the Girl in Him For the first time since he arrived at Mistress Sarah's house, Josie was left alone in silence. His cock was still throbbing from all the attention from the girls. It continued to throb as he thought about his exciting assignments for the night. He picked up... Read full Story
shemale lover 2012-10-03 4,438 domination Sex Toys feminization
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 7,410 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys 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 10,908 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Big Cock cum in mouth
77%
Slut indiscretion
At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... Read full Story
Regina10 2020-09-16 5,553 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth