Sort by
Relevancy

Free Stories

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 35,048 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
100%
la storia di Sara
Erano alcune settimane che ciattavo con Sara, una trans bolognese conosciuta per caso in internet. Di Sara ho visto solo il bel viso molto femminile con lunghi capelli biondi ed il suo meraviglioso seno. Una sera stavamo parlando e lei mi disse " alcuni mesi fa mi sono rifatta il seno, ho conosciut... Read full Story
Sissy Mari 2022-03-22 3,066 Crossdresser Amateur Cumshot cum Ladyboy Lingerie Sex Toys Homemade shemale + shemale sissy crossdresser siisy slut
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 5,472 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
100%
Mi primera experiencia anal
Les voy a contar una historia muy excitante de mi vida Soy un chico muy curioso desde temprana edad, desde que tenía 9 años jugaba con mis primos a las escondidas por las noches o a las carreras y bueno ya saben cómo todo niño siempre busca conocer y saber cosas y sentir cosas, pues un día Estaba j... Read full Story
Bigdick1689 2024-10-03 888 anal Amateur Cumshot Big Cock Homemade pov
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 14,669 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
100%
How I Became Chrissy the Caged Sissy
I am a sissy, or femboy, or tgurl, or shemale? Well either way I like wearing female clothes and being treated like a girl, especially in the bedroom, and now I also like being locked up in a chastity cage that I wear 24/7 now. This is the story of how I became a caged sissy: "Put it on and ... Read full Story
Chrissy Tunnell 2022-01-27 4,764 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
100%
Bi-Night 18.09.24
Wieder war die Bi-Night im Cruisingworld Volketswil angesagt. Da Fimia und Andrea in Mykonos im Urlaub sind, habe ich mich allein auf den Weg gemacht und bin so gegen 16 Uhr eingetroffen. Eine nette Begrüssung am Clubeingang und schon ging es in die Garderobe. In der Garderobe sprach mich auch glei... Read full Story
Cheryl_F 2024-09-02 692 anal Amateur Creampie Fetish Blowjob Ladyboy gangbang Shemale and Girl sissy pov shemale fucks shemale shemale + shemale shemale fucks female
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 5,475 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
80%
Outdoor Tranny Sluts Lust
I wake up really early one morning with my cock throbbing hard under the sheets. I got a white camisole on. Out of bed i go with a desire to vouyer and masturbate somewhere around my home. I'm home alone so i head out to my garden with my cock bouncing up, down & dripping cum. It's about 5am... Read full Story
Tracy Bel 2023-02-14 6,055 Crossdresser Outdoor Fetish Homemade cum in mouth shemale + shemale
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 2,924 Small Tits Crossdresser Outdoor Fetish Lingerie Mature pov
100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 4,585 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
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 8,657 Teen (18+) Crossdresser solo Amateur Cumshot Masturbation Fetish Asian Lingerie Homemade
100%
My Fantasie: I am a sissy slutty stripper
My favorite fantasie: I am myself but with a feminine body, but with my cock and with real breasts and a pussie, dressed in heels with lacy anklets, white hose and garter belt, white high-cut lacy panties, white lacy bra with nipples exposed, pageboy short blonde haircut, rhinestone necklace/br... Read full Story
kelliecdgirl 2024-06-27 4,735 Stockings Crossdresser solo Cumshot Ladyboy Lingerie sissy
85%
The sissy dreams
Everyday I wake up in a state , halfway between a happy sissy and a closeted white boy. My mind is constantly trapped in that state. Suffering in silence, the people in my life seem to be oblivious to it, I have it well hid. 48 years of fist fights and weed, long hair and leather coats, Oilfield job... Read full Story
badbadboi667 2021-01-04 6,082 Crossdresser Amateur Group Sex Outdoor Bareback Creampie Blowjob Big Cock gangbang domination Homemade Ass to Mouth cum in mouth
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 1,986 Stockings Small Tits Crossdresser Amateur Outdoor Blowjob Big Cock Lingerie Homemade sissy
100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 5,772 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
93%
Sissy Maddie's New Apartment Gangbang
I’d just moved into the big city. Me on my own in a cheap apartment block. The flat was nothing special by any means, and the room next to mine seemed to be noisy with parties. But I was glad to be on my own. I had almost finished unpacking my belongings when I came across my stash of female clothi... Read full Story
sissymaddiex 2020-09-25 10,758 Crossdresser Amateur Group Sex Cumshot Bareback Creampie Blowjob gangbang Lingerie Homemade sissy cum in mouth double anal
100%
What a sissy crossdresser really craves and fantasizes about
(This is non-fiction) Lots of attention. To be seen and watched. I want the neighbors to see me as I stroll in my yard wearing white vanity fair panties and bra, heels, with a lacy top and a cute bob wig. With my cock raging hard thru the pretty lacy panties, struggling to be free, bouncing around... Read full Story
kelliecdgirl 2024-05-21 4,188 Crossdresser Cumshot Outdoor Masturbation Lingerie sissy femboy
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 3,470 anal Stockings Crossdresser Cumshot Bareback Fetish Big Cock Ladyboy Lingerie femboy shemale fucks shemale cum in mouth shemale fucks female fucking sissy
85%
Sissy and Horses
The scariest and best day in my sissy life, was when I was put in a box, tied up, an anal plug in my mouth and a huge bbc dildo in my ass. I was put in the box by my BBC master, who promised me a day of surprises.... I stayed in the box for some hours, my ass hurts of the giant bbc dildo, my mouth ... Read full Story
brunasissyslavedolrj 2024-09-06 3,302 anal Crossdresser Amateur Cumshot Latina Fetish Ladyboy gangbang domination Interracial femboy Ass to Mouth double anal
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 4,682 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Feriengruss 16.07.24
Heute habe ich endlich jemanden gefunden, der mir einen langersehnten Wunsch erfüllen wollte. Ich wollte, nackig unter dem Mantel und nur bekleidet mit eingeschnürten Titten, durch die Stadt geführt werden, während ich gefilmt wurde. Wir machten ab, als es in Weinfelden gerade einzudunkeln begann. B... Read full Story
Cheryl_F 2024-09-03 850 anal Amateur Cumshot Outdoor Bareback Fetish blonde Big Cock Ladyboy domination Guy Fucks Shemale Homemade pov
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 9,501 Small Tits Amateur Cumshot Masturbation Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale Homemade pov cum in mouth
100%
Feriengruss 20.07.24
Erneut ging es Outdoor, dieses Mal aber an die Thur zum FKK Baden. Nicht am bekannten Platz in Bischofszell, sondern an meinen geheimen Platz, zwischen Kradolf und Bischofszell, unterhalb von Halden. Ich habe erneut mit 5 verschiedenen Herren abgemacht, die mir in gut geplantem, zeitlichem Abstand... Read full Story
Cheryl_F 2024-09-03 588 anal Small Tits Amateur Cumshot Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy pov Ass to Mouth
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 5,009 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
100%
Lettera a Cristina (bocca di rosa)
Beh, e' bene che tu lo sappia. Ero io quel 40enne che hai incontrato in metro'. Avevo, per la precisione, 39 anni e 10 mesi. E, ti sbagli, non stavo scrivendo proprio a nessuno, cercavo solo l'applicazione della telecamera per riprenderti con un filmino o scattarti delle foto per averti anche dopo... Read full Story
Sexbit 2023-08-22 1,132 tranny Cumshot Outdoor Blowjob Ladyboy femboy Vintage cum in mouth teen (18+)
50%
A Shock at the Adult Theatre
I am very often thursdays in the adult theatre, because stylde crossdresser have free entrance at this day. I used to go there by public transportations, because I have no car. In the rear area of the shop we are able to change our clothes and to style up and storing our bags in a locker. About a... Read full Story
SilkeTrav 2020-01-20 8,686 Crossdresser Amateur Outdoor Masturbation Lingerie Homemade
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 5,317 Crossdresser Big Tits Cumshot Bareback Creampie Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth
100%
Parcheggio Tir (ITA)
10/7/2016 Era una domenica sera,ed avendo poi il lunedi' libero,avevo deciso di farmi un'uscita serale,a caccia di cazzi che vogliano divertirsi. Cosi' mi ritrovo alle dieci e mezza di sera apoggiata al cofano della mia auto,a fumarmi una sigaretta annoiata. Il parcheggio di cami... Read full Story
JennySissyTG 2017-05-15 3,233 Crossdresser Outdoor threesome
100%
Ho incontrato una Dea
Era una tiepida sera di primavera, erano da poco passate le 8 di sera ed io avevo già cenato, era tutto il giorno che mi sentivo eccitata e la voglia aumentava dentro di me, volevo divertirmi un po' con i miei giocattoli anali, però era troppo presto, la serata era troppo bella ed invitante per rima... Read full Story
Sissy Mari 2022-03-17 2,859 tranny Stockings Crossdresser Amateur Cumshot Creampie blonde Lingerie Homemade shemale + shemale sexy shemale sexy tranny
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 2,235 Crossdresser Amateur Big Tits Cumshot Lingerie shemale + shemale sissy slut sissy crossdresser sissy amateur crossdresser
100%
im a chronic masturbating sissy slut
i know this is disgusting and really fucked up but i love touching myself more than having sex ive gotten worse as i get older i know how destructive masturbating for hours everyday is i hardly ever leave home or talk to friends or family. i stay dressed 24/7 i even fall asleep dressed as a ch... Read full Story
paul greenwell sissy 2024-10-18 1,217 Crossdresser solo Amateur Big Tits Cumshot Fetish Homemade sissy femboy
100%
Trans sucht Daddy
( Anonymität Diskretion ) Schreibe eher über mich Geschichte meine Sex Lebenslauf !!! kommt Später Da ich ja aus Erfahrung weiß da viele Herren auf Anonymität angewiesen sind und wert darauf legen dürfen mich sehr gerne was mir auch sehr Gefällt mit Maske im Hotelzimmer + Ferienwohnung besuche... Read full Story
Tranny ( Für den ) Herrn 2022-08-24 2,539 tranny crossdressing transgender tv crosssdresser cd solo daddy sissy crossdresser daddy fucks sissy grandpa DWT TV Transe BI
50%
SOUS LA DIRECTION DE MAMAN
Jaime n'avait jamais eu beaucoup de chance avec les filles du lycée. C'était venu et reparti, et maintenant il en profitait un l'été dernier avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un crétin ou un crétin, c'est juste que la vie et la... Read full Story
Femboy 2021 2023-01-26 2,019 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
50%
SOUS LA DIRECTION DE MAMAN ⚧️ ⚧️
Jaime n'avait jamais eu beaucoup de chance avec les filles au lycée. C'était venu et reparti, et maintenant il profitait d'un dernier été avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un salaud ou un douchebag, c... Read full Story
Femboy 2021 2023-03-18 1,553 Teen (18+) Crossdresser Cumshot domination Sex Toys cum in mouth
66%
Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
Go Balls Deep or Go Home 2018-08-06 32,093 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth