Sort by
Relevancy

Free Stories

100%
Party Surprise - First sex as a Crossdresser
This is a work of Fantasy. I hope you enjoy. Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly s... Read full Story
shemale lover 2012-05-21 8,359 first time hardcore anal sex Cumshot oral sex crossdressing
100%
Pleasantly Surprised
It was Friday night and Robert was sitting at home alone. His roommates were both out on dates, and his girlfriend, correct that ex-girlfriend, had moved all of her things out three weeks ago. It had been one of the dullest months in his adult life; four weeks of sitting in front of the television, ... Read full Story
shemale lover 2012-08-31 6,709 Big Tits Cumshot sucking threesome blondie
57%
Futa's Are Real
I am writing this letter as my account of truth in the legend of Futa girls. Now I should write a little about me first. I am 26 now but when it started I was twenty-two. A college jock and loved women. I would go to all the parties and college bars and hang outs. I was good looking guy 6'3, 276lbs.... Read full Story
shemale lover 2012-12-14 5,756 Big Tits Cumshot sucking jerking
100%
SissY Piss faggot Facts Lena Scarlett sissy
Well, hi :) I just want to let you know that I won't post stuff here chronologically as I wanted :) HARD WORK xD Instead I will post all the quick thoughts about me and my sissy faggot experiences, OK? Now, today I just wanted to say that I've just realised that I'm beggining to like stuf... Read full Story
Lena Scarlett 2024-11-06 3,123 Small Tits Crossdresser Fetish Uniform Guy Fucks Shemale Sex Toys sissy piss Solo Shemale Compilation Ass to Mouth teen (18+)
100%
Fooled Into Love by a Beautiful Transexual
A fictional, steamy love story about a Man’s first experience with a Shemale... a real take charge kinda girl! Maria Lopez was an absolutely stunning 23 yr old Puerto Rican Goddess. I remember the first time I laid eyes on her, bent over inside her hatchback Toyota, pulling out a hanging fern pla... Read full Story
Oobatz 2018-07-24 13,091 Small Tits Amateur Cumshot Bareback Shemale Fucks Guy Big Cock domination cum in mouth
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 7,792 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
84%
Emily's welcome
Since embracing the feminine me I’ve been on a bit of a shopping spree, it’s tough to be a gurl who hasn’t had anything really nice to wear for so long. In particular I love to buy pretty panties which keep my clitty nicely in place, but also rub up against my pussy as I walk – with nobody any the ... Read full Story
EmilyTG 2019-07-04 6,125 Crossdresser Group Sex Cumshot threesome Blowjob
92%
My Neighbor
When I got divorced and was finally living alone I had many fun times getting fucked all I could by both men and women. I was always dressed when home and loved to stay that way all weekend long and would just put on some pants over my outfit to go shopping sometimes with a coat or shirt over my ope... Read full Story
crossdresser55 2019-10-29 17,183 Stockings Crossdresser
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 11,254 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Big Cock cum in mouth
80%
One night Transtand ;)
One Night Transtand By BalkanMan990 Published on Lush Stories on 05 Oct 2019 I had no idea she was a trans.. I didn't stop kissing or fondling her when I found out. I went out for a drink at one of the many bars at Croatia,where my girlfriend Sabina and I were staying.Sabina and I had been drin... Read full Story
BalkanLoco91Ri 2019-10-24 9,475 Small Tits Amateur Cumshot Masturbation Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale Homemade pov cum in mouth
93%
Sissy Experience - Episode 1: The Beginning
Hello All, Hope you’re all doing well!! This story narrates the beginning of my crossdressing and sissy adventures. Before I begin I’ll tell you somethings about my family. We are a family of four consisting of me, mom, dad and an elder sister. I am currently 20 years old and in college. My da... Read full Story
brownsissyboi 2020-05-15 8,637 Teen (18+) Crossdresser solo Amateur Cumshot Masturbation Fetish Asian Lingerie Homemade
100%
The Experience of a Lifetime
My divorce was hitting me really hard. My wife outgrew our relationship and started living her own life and I had a front row seat to everything. My heart and life was upside down. I didn’t go out anymore. Friends and family both told me it was time to get my life back on track and start living ... Read full Story
therefill05 2020-11-30 20,913 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob blonde Big Cock Ebony Uniform domination cum in mouth
100%
Seduced At The Gloryhole
I love to write Erotica. For story requests please send me a private message or email noirenoire10@gmail.com Enjoy! Golden blonde hair that rested just past her shoulder, piercing blue eyes, full luscious red lips with colorful sleeves of tatoo’d arms. Wow, she was immaculate. She locked ey... Read full Story
therefill05 2020-12-10 10,018 Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale Interracial cum in mouth
80%
TG Girlfriend moves in (part 2)
My wife Lydia and I have been married about 9 months, we have a very close TG friend, Joanne, that lives next door and every once in a while, we get together, and all go out and enjoy. We have had sex together, and when Lydia is away Joanne, and I are together at every opportunity. Joanne and I work... Read full Story
Jon Paul 2022-01-21 3,874 Big Tits Cumshot Bareback Creampie threesome Blowjob Shemale and Girl Guy Fucks Shemale
100%
Camming Down the Rabbit Hole Ch. 10
As the sun beamed in through a gap in the curtains my now familiar morning wood strained at the silk of my nightwear. How was it that no matter how hard I came the night before it would wake up eager and ready to go. As had become customary my mind would be filled with the events of the previous nig... Read full Story
Dani_does_Dallas 2022-04-12 3,989 Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking cum in mouth webcams
100%
She lied ........ Part 1
I had walked into this bar on Castro St. in San Francisco, not realizing that it was a place for transsexuals. I chatted up with this super sexy bartender dressed in all lime green. We made small talk & she invited me up to her place after work. Being that she lived only 4 blocks away & it was a... Read full Story
Curious_billy 2023-04-14 7,175 Amateur Big Tits Cumshot Blowjob Big Cock domination Homemade
100%
mushrooms in all shapes and forms
Mushroom season is open! Yummy! I love mushrooms, in all shapes and forms. We were about fifteen mushroom lovers who only get together to pick mushrooms, without any other friendly gatherings! For this last outing of the season, our splendid instructor was accompanied by her cousin, who was sup... Read full Story
hippocampus_171 2023-11-24 7,187 Small Tits Amateur Cumshot Mature small cock big ass bisexual cum in mouth bald men glabrous
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 4,051 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
100%
Sweet Encore
I was alone tonight and feeling just a bit paranoid as I listened to the soft music. The soothing sounds put me in a seductive mood, but It seemed that all my lovers were too busy for me, or they had other plans. Uncle Barney and my detective were probably home being dutiful husbands. Bo was under h... Read full Story
Regina10 2024-05-09 3,865 Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass Ass to Mouth
100%
Shemale On Webcam Made Me Cum
It wasn't enough for me - regular porn, regular girls... I felt like I was losing it, not having the only thing I really desired: a shemale. But I was new in that world, not knowing where to go, where to look, so I decided it was better to see shemale on webcam first. I searched the internet and ... Read full Story
shemale lover 2015-12-31 4,363 Big Tits Cumshot shemale
100%
Charisma Part 2
After fondling her breasts and her cock and balls for several more minutes while she probed Tiffany's mouth with her tongue, Charisma allowed her guest to get undressed while she removed her own clothes. The seamstress was a beautiful woman, for a genetic female, but, of course, she was nowhere n... Read full Story
shemale lover 2011-09-03 3,419 anal Big Tits Cumshot
100%
Out Shopping with Lisa
Ever since the day she caught me wanking, dressed in her bra and panties, my partner Lisa had made the rules that allowed me to wear female underwear - always when we go out together, sometimes when I go out on my own, and always when I go to the pub with my mates, (in case I fancy my chances with a... Read full Story
shemale lover 2012-08-31 3,350 Stockings Crossdresser Big Tits Big Cock fuck
72%
ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn
Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... Read full Story
SpankydeBautumn 2021-01-29 11,907 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
100%
a day in the life of Amber
Hi daddy, I hadn't paraded for a few days but I did just a minute ago. He just wanted to watch me really take my dress and panties off He didn't ask me to do anything else really I sucked my finger and fondled my tits for him I would have done anything he asked I have become used to that wit... Read full Story
amberdoll 2021-03-18 2,920 Stockings Small Tits Crossdresser Amateur blonde Lingerie Homemade
100%
TG Neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
Jon Paul 2022-04-22 7,165 Big Tits Cumshot Latina Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale
100%
Erotic Dreams come true.
You start having intense erotic dreams — and the faces you see is one you don’t recognize but that feels familiar. Mandy was that girl that Chad had been dreaming of, the kind where to see her made a rush go through you like a hot flash. Chad had just broken off a relationship, and his sister war... Read full Story
Jon Paul 2023-05-26 5,329 anal Stockings Big Tits Cumshot Bareback Fetish Blowjob Guy Fucks Shemale small cock
93%
Birthday Surprise
I decided to treat myself. It was my birthday. Unfortunately, I was stuck on the road traveling for business again. I am, Dan, 45, married, relatively attractive white male. Strong arms, slim waist, rugby player type. Neatly trimmed full beard, 5'9, and 190 pounds. I returned to my hotel after th... Read full Story
shemale lover 2011-10-13 6,108 Big Tits Cumshot oral sex rimming
73%
Tabitha at 19
Tabitha’s home from her freshman year of college. She’s gone off to California to a screamingly liberal school and I’m sure she’s been making new friends, learning new things, opening her horizons and fucking safely. After I popped her cherry and we had a very discreet summer of me teaching her a lo... Read full Story
Giantsquid 2017-05-16 7,067 Small Tits Amateur Cumshot Blowjob Guy Fucks Shemale cum in mouth
100%
Seattle Weekend Part 2
I awakened to the smell of coffee and this beautiful silhouette of a girl standing at the window watching sunrise. I could see through her lingerie the beautiful breast and nipples, and the silhouette of her TG butt which was so sexy looking I was getting hard. I joined Gwen at the window wrapping m... Read full Story
Jon Paul 2018-08-13 7,164 Big Tits Cumshot Bareback Ladyboy Guy Fucks Shemale cum in mouth
38%
Am I gay?
Please help me. I'm confused and unsure if I am gay. I feel so ashamed of myself. I don't want to be gay but I was molested by my neighbors at 6 years old and from then on I would wear my mom's panties or sniff my sisters while masturbating. Cumming would always make me feel guilty for what I have d... Read full Story
Chinaysissyslut 2020-02-24 6,747 Stockings Teen (18+) Small Tits Crossdresser solo Amateur Masturbation Asian Ladyboy Lingerie Homemade webcams
0%
girls need a daddy
Friday July 18 Hello daddy, I have arranged to meet a man next week and we are in 'phone contact. He is coming to visit me and I just need to tell him whether Wednesday or Thursday. I haven't done this yet as once done is done .... I know he wants to take photos of me but I don't know if ... Read full Story
amberdoll 2020-07-22 3,533 Stockings Small Tits Crossdresser Amateur blonde Lingerie Homemade
66%
a day in the life of Amber SissyZofen 264
And the days had passed one after the other and now it was the day of my date. He sent me a txt at 8.30 on Saturday morning to say he was coming And you remember he was leaving his phone at home in case his wife called You know I had sent him my address, parking advice and left the gate ajar. ... Read full Story
amberdoll 2020-09-15 3,113 Stockings Small Tits Crossdresser Amateur Masturbation Bareback Creampie blonde Lingerie Homemade cum in mouth
100%
Nunca se Olvida
He tenido la oportunidad de tener sexo con varios hombres, algunos mayores que yo y otros muy chicos, no me fijo en estereotipos o personalidad, solo me gusta disfrutar del sexo..... Pero siempre hay uno que te deja enamorado, Daniel su nombre una persona que conocí por medio de un chat. No pas... Read full Story
Carla Travesti 2020-10-05 3,654 Small Tits Crossdresser Amateur Latina Bareback Fetish Ebony Lingerie Interracial
100%
TO BE OR NOT TO BE - PART 4
TO BE OR NOT TO BE - PART 4 by Spanky de Bautumn Part 3. Everybody was working hard for opening night when tragedy strikes and Sunny has to make a decision. Walking back to the hotel, I was lost in thought. I was excited but at the same time scared to death, confused and clear of mind, think... Read full Story
SpankydeBautumn 2021-02-23 2,914 Small Tits Crossdresser Outdoor Fetish Lingerie Mature pov
100%
Threesome goes clubbing
Ft. Lauderdale is probably the most LGBT friendly city on the east coast. So many nice restaurants and clubs that welcome all and have many LGBT employees as well. Lydia and I have been married several months, we had met Joanne an absolute amazing transgender girl during a weekend trip to the Baha... Read full Story
Jon Paul 2021-07-08 5,667 Big Tits Cumshot Bareback Creampie threesome Guy Fucks Shemale cum in mouth
100%
The four of us
Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... Read full Story
Jon Paul 2021-08-02 4,721 Group Sex Big Tits Cumshot Bareback Creampie Blowjob Big Cock Guy Fucks Shemale Ass to Mouth
100%
My story; don’t know which one... English version (1)
I notice that the're not many french language readers so have I decided to publish an English version End of the 80s; a tough time for a young reporter travelling thousands of km's for a crumb of titbit. A new event and more pressure every day for me. Seeing me in this floundering state during a ... Read full Story
hippocampus_171 2022-07-21 4,121 Small Tits Crossdresser Amateur Bareback domination Sex Toys Mature Homemade
100%
First Cross-dressings Loosing Anal Virginity
It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... Read full Story
Trapbomb1 2022-07-29 7,370 Teen (18+) Crossdresser Bareback Creampie Blowjob Big Cock virgin virginity sissy cum in mouth double anal sissy slut virgin ass
81%
The Date
When I left you I had just had my first sexual experience as a girl. I had met Dirk in a neighborhood bar and ended up in his hotel room. After a wonderful night of fantastic sex, I woke, we made love one more time, and then I had to leave for school, as I am a junior at the University. I left Di... Read full Story
shemale lover 2012-06-03 4,427 Small Tits Cumshot blonde oral sex
100%
Big Surpise In Small Package
It was a Friday night and I was extremely horny and just my luck my girlfriend was out of town, but I wasn't horny for her I was craving cock. I knew I was bi for a long time and loved to have a nice hard cock to play with every once in awhile. So I decide to call my girlfriend to tell her I was goi... Read full Story
shemale lover 2012-06-11 4,637 anal Group Sex Cumshot Blowjob
91%
First Encounter
I always has a fascination for transsexuals. I remember my freshman year of college, I don't remember how I stumbled upon it, but I was the most aroused I have ever been as I watched the beautiful Mia Isabella stroke her hard cock. Something about a feminine being, with large breast, voluptuo... Read full Story
Drewbee 2014-11-07 9,283 first time Big Tits Cumshot Masturbation shemale
73%
Nancy the hot and sexy TS in Pattaya
Hi this is Ris, this is my third story. Well Last year I went to Thailand on lone trip. I went directly to pattaya and had rest and went to Walking Street in the evening. Was visiting many nude bars, ts Bars, dance bars. but while walking on the street one particular girl catch my attention. s... Read full Story
Stud4Shemale 2017-05-22 10,111 Big Tits Cumshot Shemale Fucks Guy Ladyboy Guy Fucks Shemale cum in mouth
88%
Seattle Weekend
Saturday morning and such a beautiful day nice and cool morning I went for a run. I consider myself in fairly good shape for my age but I try and make it to the top of a hill in our neighborhood. I get winded fairly quickly. Coming down the hill I ran into a nice looking athletic girl, maybe 38 year... Read full Story
Jon Paul 2018-08-09 10,516 Big Tits Cumshot Bareback Creampie Blowjob Ladyboy Guy Fucks Shemale cum in mouth
100%
Frühes Erlebnis im Kino 1
Freitags ging ich immer in ein kleines Kino in der Gegend, das es heute leider nicht mehr gibt. Freitags, weil da in einem kleinen Raum Transpornos gezeigt wurden. Immer häufiger traf ich da einen Mann, der meist in einem anderen Raum war. Dort sah ich ihn häufig wichsen. Eines Freitags ging ich wie... Read full Story
owltranslover 2022-04-20 2,177 Small Tits Cumshot Masturbation threesome Blowjob cum in mouth
100%
Winsome Morgan pt. 2
I was so taken by her, and having so much fun toying with this cute little weenie that I didn’t notice that poor Morgan was getting weak in the knees. Just when I realised that she was trembling she said, “Stacey, I need to sit down.” “Of course my dear.” I gently guided her over to the edge of t... Read full Story
lissomlover 2022-08-09 3,249 Small Tits Cumshot Masturbation Sex Toys skinny flat chested tgirl flat thin delicate frail
100%
First Time I Experienced Eating a Tgirl Out
So this is likely going to seem tabboo for some and if this is not your thing, I respect that but everyone is different. Eating pussy came natural to me like it does for most guys once they start having sex with girls. Other than one time 69ing with a female and having what I would call "incidental ... Read full Story
AllenB 2022-10-21 5,666 Amateur Big Tits Cumshot Latina Creampie Fetish Blowjob rimming Homemade cum in mouth latina ts
100%
My Favorite Trans Model Turned Me in to Her Slut
A couple months ago I was on a trip out in Las Vegas for work. We had some down time after dinner and I was pretty tired of socializing, so I went back to my hotel room to relax. I found myself pretty bored and horny, so I started watching porn and jerking off. I’m married to a beautiful woman, and ... Read full Story
strongjohn518 2024-12-02 2,672 anal Cumshot Bareback Blowjob facial domination virgin rimjob Ass to Mouth gape gaping Hookup topping
100%
A Schoolgirl Story Chapter 2
I must apologise for the amount of time that it has taken for the second chapter of this story to come out. I have to admit that I had kind of abandoned it, but all your lovely feedback comments made me decide that I couldn't leave this one hanging. So thank you to everyone who wanted more of Wendy,... Read full Story
shemale lover 2012-06-05 9,030 Group Sex Cumshot oral sex assfucking
100%
Brazilian Discovery Chapter 1
Joan arrives in Brazil The plot from Susan and John series : Mr Gupta, the wealthy businessman had built his empire from scrap, starting from a small greengrocer shop in B'ham. He had slowly bought similar shops throughout England, federating them in a company that was powerful enough to build it... Read full Story
shemale lover 2012-08-24 5,768 Cumshot fingering Sex Toys feminization
100%
Brazilian Discovery Chapter 2
Chapter 02: First days in Brazil The tub was so large that it could have been a small swimming pool. Joan plunged into the water and started to lick Barbara's pussy underwater. When he rubbed the tip of his nose against Barbara's clit, she mightily climaxed several times in a row! Sometimes, inst... Read full Story
shemale lover 2012-08-25 4,071 Group Sex Cumshot oral sex rimjob
100%
Karen, My School Teacher Part 3
Regret... Hmm Maybe Not. By FoxyHosed My excuse for a cock got hard again. My horniness got the better off me. I went to lock the front door. I took my shoes, pants and sweater off. I stood in the hallway only in pantyhose and t-shirt. ‘Don't do this. Walk away from this now. But you go to boa... Read full Story
FoxyHosed 2021-02-05 9,220 Crossdresser Cumshot Fetish Blowjob pantyhose pantyhose anal crossdresser guy fucks crossdresser
50%
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 4,979 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
60%
Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
shemale lover 2012-09-28 7,012 Cumshot Fetish oral sex cum swallowing
100%
Retail Therapy
It began, as many of these stories do, with a pair of panties. I love lingerie as much as the next girl, but never overly indulge, as money was a little tight. My new husband Alexander and I had finally settled into our post-college lives and were reasonably well off, but had a plan to pay off colle... Read full Story
shemale lover 2012-08-31 4,164 Crossdresser Cumshot Blowjob jerking Lingerie
100%
Paola, una nuova amica
Ho conosciuto Paola sulla chat di questo sito, dopo alcune sere passate a chattare assieme ci siamo accorte che abitavamo nella stessa città. Decidiamo di incontrarci, Paola mi aspetta a casa sua. La sera dopo mi reco da lei, mi aspetta, profumatissima, indossa una lunga vestaglia bianca, i lunghi ... Read full Story
Sissy Mari 2022-03-14 2,208 Crossdresser Amateur Big Tits Cumshot Lingerie shemale + shemale sissy slut sissy crossdresser sissy amateur crossdresser
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 5,967 Crossdresser Cumshot Fetish Blowjob Latex