Sort by
Relevancy

Free Stories

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 10,798 Crossdresser Amateur Group Sex Cumshot Bareback Creampie Blowjob gangbang Lingerie Homemade sissy cum in mouth double anal
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 4,604 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
88%
Ivana Pushing Sissy's Limits
"You look ravishing," my wife Ivana said as I stood before her in a short red velvet dress with white tights and black Blahnik mary janes heels. She walked over to put a hair band in my long black hair. It was down to my shoulders now, flat-ironed straight. We stood together in front of... Read full Story
shemale lover 2013-03-19 7,121 Crossdresser Cumshot sucking Creampie ass fucking
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 4,703 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
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 35,104 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
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 5,517 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
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 1,691 Stockings Small Tits Crossdresser Masturbation Fetish domination Sex Toys small cock sissy femboy hentai teen (18+)
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 1,786 Teen (18+) Cumshot Big Cock gangbang Interracial Sex Toys gloryhole cum in mouth femination forcé poule mouillé Maitress bdsm poule mouillé
85%
The Making of A Sissy Part 4
After an exhausting evening Bella was made to wait at the door and humbly kiss the guests as they left; some of the males groping her pretty arse as they departed. She was glad of the alcohol she had been treated to as this masked from her the ugliness of some of the brutes she had been forced to en... Read full Story
shemale lover 2012-05-24 4,050 Group Sex Cumshot Masturbation little cock sissy
100%
Sissy Crissi Chapter 1
Chapter 1 -- One Dreamy Night Like most Friday nights, my roommate Erika would be gone tonight. She and her new boyfriend, Leroy, were taking off for a private weekend. Erika and I had met about two years prior, when we were introduced by a mutual friend. Being fresh off a divorce, I was in need ... Read full Story
shemale lover 2013-01-30 8,445 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
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 4,655 Teen (18+) Crossdresser Big Tits Cumshot Masturbation Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Homemade Ass to Mouth
50%
Comment sissy apprend à aimer le goût du sperme
La plupart des poules mouillées veulent entretenir une bite et apprendre à la prendre dans leur précieuse petite chatte de poule mouillée. Ils ont aussi besoin de goûter, voire de manger, le sperme. Bien sûr, comme toute autre chose dans la vie, cela nécessite une formation. Manger du sperme conc... Read full Story
Femboy 2021 2023-01-12 1,081 Crossdresser Amateur Cumshot Creampie Fetish Blowjob Big Cock cum in mouth
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 14,688 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
100%
Regina and Tommy
I was getting fucked hard and aggressively by a certified bad boy named Tommy. I've never been the kind of girl who liked bad boys until I met Tommy. Tommy like doing all kinds of wild crazy things to me and I was under a spell and couldn’t object. Tommy was like the asspussy whisperer and he gave m... Read full Story
Regina10 2022-03-02 3,463 Stockings Big Tits Cumshot Bareback Creampie Fetish Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
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 10,717 Crossdresser Cumshot Masturbation jerking Lingerie
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 8,676 Teen (18+) Crossdresser solo Amateur Cumshot Masturbation Fetish Asian Lingerie Homemade
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 3,079 Small Tits Crossdresser Cumshot Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
From accidental trans porn addiction to a cum filled booty
One night when I was around 30 or so I was watching some porn, nothing unusual for a guy like me, aka a sex addict. Sex addiction is great if you’re Tiger Woods and swimming in poon, but for guys like me - regular, awkward, slightly handsome in a very boyish way, weirdos — it’s not that fun. We... Read full Story
CDJaneBooty 2022-04-01 11,019 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
100%
Surprise Ending (Part Three)
I rolled my dick around her hole to spread the precum off it and lubricate it. The feeling was sensational and I couldn't spend much time easing my way in --I shoved right in the the hilt in one steady push. Karla practically jumped off the couch and screamed. I thought maybe I had hurt her (I am... Read full Story
Chantel13 2022-08-23 4,809 Crossdresser Amateur Group Sex Cumshot Outdoor Creampie Shemale Fucks Guy Big Cock Shemale and Girl redhead Guy Fucks Shemale Ass to Mouth
100%
Sarah fucking in vienna
Sarah in Wien , sie nennt mir ein mir bekanntes Hotel in der Innenstadt, sowie eine feste Uhrzeit! Überpünktlich bin ich Vorort , komplett glatt , unter der Anzugshose einen schwarzen engen Nylon Slip , sneaker weißes Kurzarm Hemd, guter Duft , klopfe ich etwas nervös an der Zimmertür! Von innen k... Read full Story
Sarah Diener 2023-08-30 2,440 anal Crossdresser Amateur Cumshot Bareback Creampie Blowjob blonde Lingerie Guy Fucks Shemale sissy Ass to Mouth cum in mouth
100%
Britney Story
Yeah, for those of you that have already read it, this is just my "Oops, I Did It With Britney" story that has previously appeared in four separate parts in the "celebrities" section, but I've put it on here for a couple of reasons. For one thing, I've noticed that the stories in... Read full Story
shemale lover 2012-09-25 9,555 Cumshot sucking Creampie shemale
100%
Tom Didn't Get A Choice
Tom Didn’t Get A Choice This was Tom and I’s first date. We had met online, so he already knew that I was a very femme sissy crossdresser. Tom eventually asked me on a date. I happily said yes, knowing that I turned him on a great deal. On the evening of our date I wore a black dress that wa... Read full Story
pennypenny 2019-02-18 6,679 Crossdresser Cumshot Bareback Creampie Blowjob redhead Guy Fucks Shemale cum in mouth
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 9,293 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
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 5,335 Crossdresser Big Tits Cumshot Bareback Creampie Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth
100%
Regina’s Double threat.
Hello guys, I recently ran into a former hater who was no longer the hater I had met years earlier. In fact, he had only treated me so horribly because of his own inner dark desires. When we met a few years ago at one of the clubs, he had been very abusive to me. He went out of his way to say hurtfu... Read full Story
Regina10 2022-02-08 3,536 Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock redhead Guy Fucks Shemale Ass to Mouth double anal
100%
Ravaged by Daddy
For anyone who loves wearing high heels and dressing up to get ravaged by your hungry Daddy. I imagine you laying on your side as I run my strong hands up and down your smooth, soft legs and across your feet. I slowly slide them upwards until I'm caressing and squeezing your thighs. You watch me ... Read full Story
TheWinkster 2023-08-29 5,857 anal Cumshot Bareback Creampie Guy Fucks Shemale
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 12,589 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
87%
Beginning of my Bi Life
Well It's all Started When I Was at 13 or may be 14 years old. I began to watch porn and reading porn comics and began to masturbate. I wasn't getting much privacy at my home so I was staying at my school even after my classes was over and when everyone was busy at after school Sport hours I masturb... Read full Story
Trapbomb1 2021-05-25 4,937 sucking Blowjob cum bisexual cd sissy femboy bi trap
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 9,528 Small Tits Amateur Cumshot Masturbation Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale Homemade pov cum in mouth
40%
Dating all whole my life
Julia and Ilya, together 10 years It was more than 10 years and 2 children ago. In December 2005, we agreed to meet at the gate of my office after a working day. I did not go out godlessly for a long time (40 minutes from the appointed time), but he still waited. I hope he does not regret it ... Read full Story
PornoDating 2019-08-15 4,543 Crossdresser Amateur Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock Asian gangbang domination Guy Fucks Shemale Interracial sex Mature Futanari Frottage Compilation Ass to Mouth Cartoon cum in mouth double anal dating life in Mars? life
50%
C'EST LA PATRONNE ⚧️ ⚧️
Le rêve est mort. L'écriture était ma passion, mais cela n'a jamais servi à rien. La réalité a une mauvaise façon de vous rattraper, déchiquetant vos désirs dans son sillage. Ce cycle d'épargne et de vie de ces économies s'est progressivement révélé intenable et maintenant, à vingt-cinq ans, j'ai... Read full Story
Femboy 2021 2023-03-30 1,914 Big Tits Cumshot Creampie Blowjob Big Cock domination cum in mouth analsex femme plus âgée Futanari futa sur femme
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 2,041 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 1,566 Teen (18+) Crossdresser Cumshot domination Sex Toys cum in mouth
50%
Sissygasm : Comment jouir de l’anal uniquement
Vous voulez avoir un orgasme époustouflant en vous faisant baiser dans le cul en moins de 2 minutes ? Je le fais tout le temps, et vous pouvez le faire aussi. Ce n’est pas un mythe, et ce n’est pas seulement quelque chose que seules « certaines » personnes peuvent faire. Tout le monde peut apprendre... Read full Story
Femboy 2021 2025-01-07 70 anal Cumshot Creampie Fetish Sex Toys sissy teen (18+)
65%
Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
shemale lover 2012-12-19 11,131 Masturbation Blowjob blonde ass fucking big boobs
100%
LE CONTRAT DE MARGOT
Madame Margot Elizabeth Stott était l'objet de mes désirs, des désirs très secrets ; désire que je n'aie jamais eu l'intention de la laisser - ou qui que ce soit d'autre - le découvrir. Mme Margot Elizabeth Stott avait, au moment où je l'ai connue pour la première fois, environ 45 ans, peut-être ... Read full Story
Femboy 2021 2023-02-16 1,639 Stockings Crossdresser Cumshot Fetish Lingerie domination Sex Toys cum in mouth