Sort by
Relevancy

Free Stories

66%
First time
I once met a sexy tranny when i was out walking and she enticed me along a forest path and into some bushes where she began to slowly undress me. I was wearing very soft satin and lacey lingerie underneath my normal clothes, she knelt down in front of me and slowly took my soft satin cock into her m... Read full Story
shemale lover 2011-11-07 2,360 Creampie Lingerie transvestite
50%
ROBE MAGIQUE ⚧️ ⚧️
💞 GRACE 💞 Nous étions des fous d'informatique. Quatre d'entre nous dans la même année à l'école. Tous les garçons, bien sûr. Naturellement, nous nous sommes appelés les Quatre Mousquetaires (bien que personne d'autre ne l'ait fait, et nous n'avons jamais tout à f... Read full Story
Femboy 2021 2023-03-22 453 Stockings Crossdresser Creampie Lingerie domination Sex Toys
80%
Crossdresser Lovemaking
Oh Daddy, I'm your little princess! Your wife is out taking your kids to a sleep-over at a friend's house across town and we're in your bedroom. I long for you to see me with bursting lust, and I take off my coat to reveal myself wearing a white tutu with bra, panties, stockings and h... Read full Story
CD Lilee 2014-05-20 6,651 Crossdresser anal sex sucking Creampie Lingerie cd
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 2,452 Small Tits Crossdresser Cumshot Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
Sissy Femboy Chrissy in Drag 2: At the Apartment
This is Part 2 to the article I wrote called "Sissy Femboy Chrissy in Drag at the Club." In that story I explained how I am 41 but look, feel and sound younger, that I shave myself smooth and like dressing in gurly panties and other female clothes to be a sissy femboy for older guys. A guy I met on ... Read full Story
Chrissy Tunnell 2022-02-03 3,543 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
mein erstes mal
Nur ein paar Häuser weiter wohnte Bernhard, 56 Jahre alt, hatte einen kleinen Bauch, sonst aber sehr gepflegt. Seit 3 Jahren war er geschieden und lebte nun alleine. Schon seit einiger Zeit besuchte ich ihn regelmäßig, um in seinem Pool zu schwimmen, um ihm manchmal im Garten auszuhelfen oder einfac... Read full Story
trans_sabine 2022-10-03 3,217 first time Stockings Teen (18+) Small Tits Crossdresser Amateur Bareback Creampie Lingerie Guy Fucks Shemale schwanzmädchen
100%
Why I’m a Cock Whore!
Hello Love, The summer before my freshman year in high school. I found a VHS porno video right next to a dumpster behind our local video store. Brought it home. Couldn’t watch it until my family left to use the VHS player. It turned out to be a she male porno at first I felt weird but after watch... Read full Story
Samantha Cummins 2023-04-18 6,061 anal Stockings Cumshot Creampie Lingerie femboy Ass to Mouth cum in mouth
100%
Danielle Works a Saturday
It had been a few months since his wife left him. Well "ex-wife" as the divorce had been recently finalized. It was her choice; she walked out on *him*. She said she got tired of "Danielle", even though she was entirely responsible for Danielle's "birth" to begin with. ... Read full Story
shemale lover 2012-06-18 5,585 anal sex Creampie oral sex cum swallowing
50%
Transgender Art
Artists whose work includes transgender, transvestite, or transsexual themes are rare. In other articles, discuss the work of Christopher Leach ("Christopher Leach") and Kimberly Wilder ("Kimberly Wilder: An Assessment"), whose respective styles, if not subject matter, are vastly... Read full Story
shemale lover 2011-09-17 4,453 transsexual transvestite transgender
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 33,609 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
66%
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 4,520 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
81%
Forced Entry
Danny sat at the bar of the Holiday Inn nursing his fourth double scotch, espousing to the man beside him the reasons why his company was the best designer and distributor of accounting software in the world. Danny was a large man in his forties and was running to fat. He was dressed in a travel-... Read full Story
shemale lover 2012-11-16 15,703 Big Cock oral transvestite forced sex
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 1,283 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial Sex Toys cum in mouth
50%
She also conquered my soul...
Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... Read full Story
hippocampus_171 2022-11-22 3,970 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
100%
Planet Of Men
At 1600 Eastern Standard Time (EST) on September 27 in the year 2020 AD the UN announced that General Atomics Corporation (GAC) had saved the world. After years of panic in every country that the world was doomed due to the effects of global warming, GAC announced that, with funding provided by the ... Read full Story
shemale lover 2012-05-04 4,052 first time Stockings facial oral sex transvestite
50%
DEVENIR CASSIE
L'argent était difficile à trouver dans notre foyer. Être l'aînée de quatre enfants et ma mère étant une mère célibataire mettent nos ressources à rude épreuve. Nous avons rarement eu de l'argent supplémentaire dans notre famille à dépenser pour des choses comme manger au restaurant ou aller au ciné... Read full Story
Femboy 2021 2023-01-20 1,427 Stockings Crossdresser Amateur Cumshot Fetish Blowjob Big Cock Lingerie domination
75%
Lady In The House Ch. 13
A story by MicheleNylons ( Transvestite prison prostitute gets a visit from the Warden. ) I awoke in my cell the next morning unaware of the terrible fate that had befallen my sister Angie. I knew that Steve had sent his henchman Danny to do something to her in retribution for my recalcitrance bu... Read full Story
✘Transensual✘ 2019-02-27 5,333 Crossdresser domination PRISON FUCKBOY PRISON PUNK prisoner prison sex Prison Bitch
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 11,785 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
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 8,866 Small Tits Amateur Cumshot Masturbation Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale Homemade pov cum in mouth
92%
Lady In The House Chapter. 01
A story by MicheleNylons ( Man in jail is transformed to prison slut.) How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild... Read full Story
✘Transensual✘ 2019-01-11 9,391 Crossdresser Bareback Creampie Fetish blonde Big Cock Lingerie domination Guy Fucks Shemale transvestite slut PRISON FUCKBOY prison sex Prison Bitch
100%
The Mole
Police work is a paramilitary occupation. Uniforms, rank, weapons, discipline…It can be exciting and interesting for some and boring for others. Some officers seem to find lots of action during their career (or maybe it finds them) while others never use their sidearm except for target practi... Read full Story
shemale lover 2012-01-26 6,454 brunette Crossdresser Fetish
100%
T Is for Teresa
Transgender-themed stories which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! It was when I was still living at home, or at least staying there in the college holidays, that Mum came home and found me and Jack Horton lying on the living room ... Read full Story
shemale lover 2012-08-28 6,213 Crossdresser Cumshot Fetish Blowjob
90%
On the Run
“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... Read full Story
shemale lover 2012-09-01 11,225 Crossdresser Cumshot Blowjob jerking pantyhose
100%
Lady In The House Ch. 08
A story by MicheleNylons (Crossdresser must comply with jailhouse heavy.) "You!!!" Eddie screamed through the bars, then laughed. "Well done girls, quite a show, I really enjoyed that; and so did Michele obviously," he said snickering and pointing at the tent in the front of my skirt caused by... Read full Story
✘Transensual✘ 2019-02-25 5,679 Crossdresser domination PRISON PUNK prison sex Prison Bitch
100%
Regina's scary, and sexy Blind Date
I had just finished doing my makeup, finally deciding which blush to use, and I thought I had some time for my meditation. However, Mr. Cobb was early. The gold minidress I wore showed enough legs, ass and tits to make any man horny, and the strappy tanned five-inch sandals, made me feel majestic ... Read full Story
Regina10 2024-03-18 4,489 anal Crossdresser Bareback Creampie Fetish Blowjob Ebony Guy Fucks Shemale big ass sissy Ass to Mouth cum in mouth
71%
Me and a transvestite man
This isn't a 'story' at all, in the sense that it really happened. I just thought I'd share my experience with you; perhaps you'd care to comment if you enjoyed it, found it sexy, or want to know more. There isn't a 'transvestite' niche on xHamster, so this is filed rather awkwardly under 'Shemal... Read full Story
shemale lover 2011-08-12 3,534 first time shemales gay male
67%
Asian Crossdresser - How My Crossdressing Journey Began
My name is Patrick (Pat) Young and I was in Hong Kong. It all started when I was 5 years old. I was an innocent and naive boy, who had no idea the difference between boys and girls. I thought the differences were that girls had long hair and they wore skirts. When girls grew up, women were sh... Read full Story
pat1young 2015-12-08 11,848 solo masturbating crossdressing high heels Asian TS
100%
Lady In The House Ch. 05
A story by MicheleNylons (Crossdressed prisoner is forced into prostitution.) From Part IV Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread th... Read full Story
✘Transensual✘ 2019-02-25 4,458 Crossdresser domination PRISON prison sex
100%
On Strike!
I got the idea while listening to the news on the radio, during another grinding commute home from the big city. It seemed a couple in Florida had gotten so sick and tired of their spoiled, neglectful children that they were camping outside their house in beach chairs, refusing to go back to being p... Read full Story
shemale lover 2012-09-02 4,027 Stockings Crossdresser Lingerie pantyhose
100%
Lady In The House Ch. 04
A story by MicheleNylons ( Prisoner's transformation continues.) From Part III Steve's orgasm started to subside and he continued to rub his cock all over my face. He smeared his spend all over me, it combined with my lipstick and makeup to make a hot sticky film that covered my face. Steve ... Read full Story
✘Transensual✘ 2019-02-25 3,867 Crossdresser prison sex Prison Bitch
100%
Lady In The House Ch. 07
A story by MicheleNylons (Carmel and Charlotte want theirs.) From Part VI "You look gorgeous Michele," Carmel whispers through the bars. I wondered if she had read my mind when I was standing in front of the mirror admiring myself. "Well, I have to say you girls are looking something spe... Read full Story
✘Transensual✘ 2019-02-25 3,315 Crossdresser domination prisoner shemale lesbians Prison Bitch
100%
Lady In The House Ch. 09
A story by MicheleNylons ( Continued adventures of a cross-dressed prison prostitute. ) I lay there stunned, how had I miscalculated my effect on the Warden? The one man who could guarantee a transfer from this shit-hole; fuck!!!! The cravings of male sexual hunger within the confines of the ... Read full Story
✘Transensual✘ 2019-02-27 5,754 Crossdresser domination Guy Fucks Shemale cum in mouth PRISON FUCKBOY PRISON PUNK prisoner Prison Bitch
85%
Whores and Pimps - Part I
Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm h... Read full Story
shemale lover 2012-05-13 7,944 Stockings Crossdresser Cumshot Fetish oral sex pantyhose
25%
A Strange Romance
Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to ... Read full Story
shemale lover 2012-07-05 6,827 Creampie Fetish crossdressing virginity
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 5,657 Crossdresser hardcore Cumshot Lingerie Latex
100%
I Missed Myself
As soon as Dr. Griffin returned to the examination room, I knew that the news wasn’t good. I could tell by the way he avoided my eyes as he studied his clipboard and fidgeted with his pen that something was wrong, terribly wrong with me. The ache in my groin that I had been ignori... Read full Story
shemale lover 2013-03-20 7,957 Crossdresser Lingerie pantyhose cd softcore
100%
Estelle
Estelle sat before her dressing table, putting the finishing touches to her makeup. She had prepared herself as well as she was able, as her lover tonight was her benefactor – as the kept “whore” of Marcus Smith she owed her whole self to him and indeed, she loved him, but more than that, she loved ... Read full Story
kathysmokes1 2020-08-13 4,298 Stockings Crossdresser Bareback Fetish Big Cock Lingerie
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 4,830 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 8,606 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
100%
Emily's First Daddy
This is a story how a curious male can become a sissy slut seemingly overnight. So I was in an online adult chat just talking with random people and happened to mentioned where I live. Then all of sudden, I got a message from a man calling himself bear daddy. He introduced himself and said he was ... Read full Story
User Removed 2019-10-21 8,884 Crossdresser Amateur Creampie Homemade cum in mouth webcams
100%
An Unwelcome Visit
It had been over a year since I had split from my boyfriend, Rick. We had a terrible row in which he had accused me of seeing another man. He walked out, never to return. I had tried to give up wearing girls' clothes afterwards in an effort to become a 'normal' person and to try to blot out some bad... Read full Story
shemale lover 2012-11-23 3,648 anal Creampie fingering oral sex stroking
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 17,232 Crossdresser sucking Big Cock ass licking big boobs
100%
A Very Happy Holiday To Me
I don't know if it was a dream or just something that happened but it was Christmas and I felt sore and achy all over but with a wonderful feeling none the less. I am a crossdresser who is trying now to discover and explore his female personality and can now happily tell of who I was in the past,... Read full Story
shemale lover 2012-04-03 2,920 Creampie oral sex cum swallowing crossdressing
90%
My True-Love Story
My name is Kim Young. I'm a happy and healthy nineteen this year. This is my very first story (but not my first "submission!") My story begins five years ago, when our neighbors moved in next door. I'll always remember that sunny April afternoon in Omaha, when they climbed out of their ... Read full Story
shemale lover 2012-09-10 5,725 Crossdresser Blowjob pissing Lingerie handjob
76%
How You Became a CD Slut
It started with your mother’s pantyhose. There was something about them that fascinated you. You were inexplicably drawn to them. You touched the delicate fibres and already your young cock stirred. As you excitedly pulled them on, your erection was now becoming painful. You loved how they enveloped... Read full Story
Daddybear71 2023-03-27 8,056 Stockings Crossdresser Masturbation Lingerie
100%
Junior's Department
Junior’s Department The long-haired young male browsing alone in the ladies’ junior’s department caught his eye and he stopped walking to the store exit. He stepped behind a display rack across the aisle, then watched him approach a mirror and scan the area before holding the skirt and blouse up ... Read full Story
AuthorJordanSkythe 2022-01-20 2,667 first time Stockings Crossdresser romance femboi
100%
Fateful Jessica
Fate knocked at the door, I answered it like some automaton and through the frosted glass panel a long-haired figure foreshadowed coming events. Opening the door, my face cracked a smile when I saw it was my cousin Jessica, who lived nearby. "Hi! Come in!", and I stood back to let her p... Read full Story
shemale lover 2012-07-03 2,643 Crossdresser Fetish transvestite
66%
Emily's day out - the fantasy continues
I woke up to the sound of soft moans from the next-door bedroom, two beautiful gurls asleep on the bed next to me, their arms draped over my body. It took a few seconds to remember where I was and what had happened, but the stickiness in my pussy and on my clitty quickly reminded me that I had been... Read full Story
EmilyTG 2019-07-10 5,694 Crossdresser Cumshot Bareback cum in mouth
88%
Becoming Lisa
From when I was as young as 9, smooth and long blonde hair, I was always dressing in my older sister's panties and bra, panty hose. My breasts were kinda girlish and i had long nipples that would get hard when I played with them. I was older now, but still only had a small 4 inch cock when it was ha... Read full Story
shemale lover 2013-08-09 12,984 Crossdresser Masturbation Fetish Lingerie kissing
76%
Woman of my dreams is making me the woman of my dreams (pt 1)
I met Amber one day while I was out at the beach. She was so far out of my league – a 5’4” slender and toned stance and exquisitely tanned body with a bikini that left very little to the imagination. She was unbelievably hot, so it was no surprise that I was tongue tied when she walked past me and s... Read full Story
jenrip 2021-03-29 7,532 Stockings panties crossdresser lingerie woman on shemale
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 4,716 Crossdresser Big Tits Cumshot Bareback Creampie Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth
50%
MARIAGE CLASSÉ ADULTE ⚧️ ⚧️
1. 'Alan à Alisha...' La salle de bain était embuée et le miroir s'embuait alors que je me dirigeais vers la baignoire. Là, dans toute sa gloire, était assise ma magnifique épouse Liz qui occupait déjà un coin de la baignoire, seul le haut de son torse était visible avec toute la mousse qui l'ent... Read full Story
Femboy 2021 2023-02-21 742 Crossdresser Cumshot Fetish Blowjob Big Cock gangbang Lingerie Guy Fucks Shemale Interracial
50%
DU VILAIN PETIT CANARD À LA PRINCESSE SISSY ⚧️ ⚧️
Être un mec très petit 1 mettre 60 avec une petite carrure a été un handicap majeur dans ma quête de compagnie féminine. Avoir un micro pénis était le clou de mon cercueil. Tout au long de ma jeunesse, j'ai été ignoré ou rejeté par les filles. J'ai eu ma première petite amie à l'unive... Read full Story
Femboy 2021 2023-03-23 816 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial cum in mouth shemale + shemale
78%
A Little Girl Forever
Since I was a little girl I dressed in my sister's clothes, she knew it and she kept clothes for me and sometimes she bought clothes thinking about me. She was my accomplice and still is. When I was alone I dressed totally as a woman and I felt totally satisfied and realized as such, this included m... Read full Story
Mabel Cecilia 2019-05-06 7,957 Small Tits Crossdresser Amateur Cumshot Latina Masturbation Creampie Blowjob blonde Lingerie Shemale and Girl Guy Fucks Shemale Sex Toys Mature self sucking Solo Shemale cum in mouth double anal shemale + shemale
75%
Honeymoon Suite 2
Jason is on the phone with room service, while I am about to change out of my wedding gown. I had just got married, and I was now the blushing bride. Yes I got married. I was nervous now and my pussy was burning, because of the crazy bet we had made about not having sex a week before the wedding. We... Read full Story
Regina10 2021-02-22 3,590 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
100%
TO BE OR NOT TO BE – PART 6
TO BE OR NOT TO BE – PART 6 by Spanky de Bautumn Part 5. Sunny and Antonio got frisky at the bar, Sunny moved in with Mel and Shari, and opening night was a success The only other dress that I brought was one that I hoped I would get a chance to wear but didn't think I would. It was a black ... Read full Story
SpankydeBautumn 2021-02-26 2,356 Stockings Small Tits Crossdresser Cumshot Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth