Sort by
Relevancy

Free Stories

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 4,676 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + 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 12,218 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
50%
JOLI GARÇON À SISSY GIRL ⚧️ ⚧️
J'ai rencontré ma femme Tara pour la première fois lors d'une soirée de réveillon. Je portais de l'eye-liner et mes cheveux étaient relativement longs. Elle m'appelait "joli garçon" pendant que nous dansions. Elle était très sexy avec un petit corps, de longs cheveux noirs et... Read full Story
Femboy 2021 2023-03-20 976 Stockings Lingerie Shemale and Girl domination Guy Fucks Shemale Interracial cum in mouth
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 11,686 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
50%
Closet Sissy Son fait en fille
Pourquoi étais-je à quatre pattes avec la bite de mon père dans le cul et la chatte de ma sœur dans mon visage? Je ne savais pas que ma mère était au courant de mon secret. Elle savait que je portais sa lingerie et celle de ma sœur. Cela a commencé lorsqu'un jour j'étais seul à la maison et que j... Read full Story
Femboy 2021 2023-01-24 1,021 Stockings Teen (18+) Crossdresser Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys 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 14,325 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
50%
Ma femme et maintenant elle va me transformer en Sissy
Karen et moi sommes mariés depuis 28 ans. Nous avons eu nos hauts et nos bas, mais nous sommes restés fidèles et avons produit deux excellents sexe en conséquence. J'ai toujours été secrètement bi. J'ai été pris au piège de quelques accessions, mais j'ai résisté aux tempêtes et j'ai visité des relat... Read full Story
Femboy 2021 2023-01-24 1,185 Stockings Crossdresser Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys
100%
Alessia and the Twins
Alessia and the Twins When the politician David Smallwood awoke that morning his thoughts immediately turned to Alessia, and he started to daydream about her, as he was wont to do now. He had several meetings scheduled for that day, including a rally promoting restrictions on gay and trans-gender... Read full Story
Alessia Travestita 2023-07-21 5,620 Crossdresser Blowjob Big Cock Shemale and Girl shemale fucks female
50%
SISSY AWAKENING
- Trou de gloire du sex-shop - "Hey bébé, quand est-ce que tu rentres à la maison?" le message texte bourdonnait doucement. Sortant discrètement le téléphone de ma poche, je tape "Même heure que d'habitude, juste après 5 heures, pourquoi... quoi de neuf ?" C'est mon amante Sarah, ma meilleu... Read full Story
Femboy 2021 2023-02-17 1,547 Stockings Crossdresser Outdoor Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
100%
Becoming a Chrissy - Chapter 2
I had always felt like I had a hot body for a girl. I was naturally blonde and smooth; I guess I had been blessed by my parents’ Scandinavian genetics. My pubes were always just a small fuzz—easy to shave and keep a clean bikini line. Same thing with my armpit hair. And my ass? Completely smooth and... Read full Story
mindlessrobot45 2024-05-13 4,179 Crossdresser gangbang Shemale and Girl cum in mouth shemale fucks female teen (18+)
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 8,331 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
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 4,360 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
100%
Camming Down the Rabbit Hole Ch. 12
We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... Read full Story
Dani_does_Dallas 2022-05-09 5,614 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
100%
Meeting Amanda Ch. 2 - The Next Day
After a hot evening together, the story continues https://www.ashemaletube.com/story/meeting-amanda-6595/ ------------------------------------------------------------------------------------------------------------- “I could really use a shower,” Amanda said while she... Read full Story
rforasht 2022-09-07 4,537 Masturbation Shemale and Girl redhead Guy Fucks Shemale cum eating anal creampie couple & shemale
94%
The Double Sex For Sissy
Jeff Malville awoke slowly, moaning softly. He almost forgot where he was in that moment where sleep and being awake clashed. However, after that split second, it all came rushing back and he moaned in delight. He was a captive on the Double D Ranch, and even though he was considered an employee... Read full Story
shemale lover 2013-04-10 7,880 Creampie threesome blonde redhead domination double penetration
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 7,803 Big Tits Cumshot Shemale Fucks Guy threesome blonde Big Cock Lingerie Shemale and Girl redhead Homemade Shemale fucks couple
88%
Girl from Uncle
Tonight, I have to tell it all. It’s no secret that my uncle and I had a very special bond he had been eyeing me with those adventurous eyes from the time that I was 14 years old. And frankly I enjoy his ogling. I could feel my nipples get so hard when he looked through me with those alert and spark... Read full Story
Regina10 2024-02-14 5,607 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
85%
Gilding the Lilly
It was a dark and stormy night. Oh, wait, I was taught NEVER to begin a story like that. (Snoopy can get away with it, but he does all his writing with a typewriter balanced on his doghouse). OK, getting back to important things. It was actually early Autumn out in the Desert, cool weather was s... Read full Story
CharlotteSlut 2018-03-02 6,247 Group Sex Shemale Fucks Guy gangbang Shemale and Girl shemale + shemale
50%
The first requirement of a deal with Dominatrix Persephone.e
There was a number of requirements before I even consider'd fucking that sissy ass, firstly, I expected dedication to be shown and to prove that the sissy could obey my orders, after a trial period, then I consider to force my big dick down the throat of the that sissy, and then fuck brutally and ex... Read full Story
Dominatrix Persephone 2024-06-21 3,002 anal solo Cumshot Masturbation Shemale Fucks Guy Big Cock Shemale and Girl domination Mature sissy shemale fucks shemale teen (18+)
100%
Vegas Honeymoon to Remember
I had dated my wife (Carmen) for about 6 months before we decided to Marry. One evening we were soaking in the Jacuzzi together and drinking wine. She always wants to try different things, which makes our sex life wonderful. Carmen asked me if I ever had any fantasies. I said I guess like most me... Read full Story
Jon Paul 2018-05-30 20,703 Group Sex Cumshot Bareback threesome Ladyboy Shemale and Girl
100%
Camming Down the Rabbit Hole Ch. 11
I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hopin... Read full Story
Dani_does_Dallas 2022-04-25 4,492 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth
84%
SUMMER VACATION by Spanky de Bautumn
In our house, it was a well-known secret that my mother kept her change in the top drawer of her dresser. The same drawer she kept her slips, chemises, panties, and all other satin, nylon, or lacy ladies undergarments. During the summer, my brother and I would run to that wondrous drawer when... Read full Story
SpankydeBautumn 2021-01-22 12,898 Small Tits Crossdresser Cumshot Masturbation Fetish Blowjob Lingerie Shemale and Girl cum in mouth
100%
Shopping plus extras!!!
Hi, so as you can probably imagine I buy a lot of underwear and have a few favourite places to shop. My favourite by far is Ann Summers. The range is great and the staff are so helpful . Anyway back to the story. So I decided to go get some new underwear to see in the new year, I got myself up and d... Read full Story
Samantha Jewels 2023-01-06 4,613 Crossdresser Amateur Cumshot Fetish threesome Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Ass to Mouth cum in mouth
83%
Fantasy dream
So i had this dream and it gave me such a raging boner i felt i had to write it down. Im at a party, everyone is wasted and having a great time. I had been dancing and flirting with some blonde chick who kept mentioning her friend and wondering where she had gone. Eventually we found her and went... Read full Story
Wanksalo 2019-04-15 4,275 Cumshot Blowjob blonde Shemale and Girl
100%
Antiques
My name is Siska and I have a life (TG) partner named Toni. I’m in my 60’s and Toni in her 40’s. We have a small investment firm (just the 2 of us) and do well over all. As part of the business my beautiful Toni, does the traveling when needed. A few years back, Toni inherited a house in an old so... Read full Story
Karlold 2019-08-26 4,581 Shemale and Girl domination Mature
66%
A Girl's Best Friend
The party was in full swing when Ryanna and her friends arrived. Of course, they were an hour late, since Glenys had gotten lost on the way. The house was out in the back woods; the owners didn't exactly go out of their way to make it easy to find. Their fellow townspeople probably would have frowne... Read full Story
shemale lover 2012-03-06 5,683 Crossdresser Shemale and Girl oral sex condom sex
100%
Towel Boi: You're Hired
Kasey Stevens woke up in his new studio apartment. The five-foot-nine, blue-eyed sissy with ash brown hair yawned and stretched before heading into the bathroom. He showered, taking good care to lather his rosy skin with strawberry scented body wash. He shaved his legs and rinsed off. Then, he appli... Read full Story
Faggyboi and Puzziboi 2023-11-14 6,372 anal Small Tits Crossdresser Amateur Bareback Blowjob Guy Fucks Shemale Interracial small cock big ass femboy
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 1,734 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
100%
DÉBUTS INNOCENTS
"Avez-vous pris votre vitamine, ma chère ?" Ellen a appelé de la salle de bain. Je me frottai le sommeil des yeux et ramassai le flacon de pilule, roulant un gros comprimé dans ma paume. "Ma pilule de cheval ? Je le fais maintenant." "Avez-vous déjà remarqué une différence ?" "Non. Les vitamines ... Read full Story
Femboy 2021 2023-01-26 1,318 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale
50%
LE PATRON DE MA MÈRE
Comme tous les seniors de 18 ans, je vivais vite et chassais le cul. Ma vie avait été une ligne forte entre ce que mon esprit pensait que je devais faire et ce que ma bite voulait que je fasse. C'est pourquoi je suis chez la fille la plus salope de l'école. Elle suce ma bite comme si c'était un Toot... Read full Story
Femboy 2021 2023-02-17 1,126 Teen (18+) Crossdresser Shemale Fucks Guy Fetish Blowjob Big Cock Shemale and Girl domination cum in mouth
50%
LA VENGEANCE D'UNE SOEUR ⚧️ ⚧️
"Maman, maman," cria Michael. "Aide-moi!" Mary tourna la tête vers les cris de son fils pour ensuite entendre Melissa crier: "Sortez d'ici, espèce de pervers!" Mary se précipita dans le couloir jusqu'à la chambre de sa fille où elle trouva Michael passant devant elle, suivi de près par une bro... Read full Story
Femboy 2021 2023-03-26 1,310 Stockings Big Cock Lingerie Shemale and Girl Guy Fucks Shemale Sex Toys strapon feminisation du fils SOEUR ET MERE DOMINANTE FILLE ET MERE LESBIENNE
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 5,003 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
92%
Shy boy to bimbo sissy
it's all started when my older brother showed me a shemale masturbating video when I was 15. after I saw it I was instantly attracted to trans girls than cis girls. I was a very shy pale feminine looking boy.high school wasn't great, boys used to bully me. I am too shy to talk to the girls... Read full Story
drleena 2022-12-08 13,135 shemale submissive cross dressing chastity prostitue real story
50%
A LA DÉCOUVERTE DE L'AMBRE ⚧️
J'ai toujours aimé la lingerie féminine. De regarder des catalogues à voir des copines le porter, j'ai adoré le look et la sensation de la lingerie sexy et soyeuse, mais pour moi, cela a toujours été plus profond. À 18 ans, j'ai essayé ma première paire de culottes, oh mon Dieu, c'était merveilleux ... Read full Story
Femboy 2021 2023-02-17 1,249 Stockings Crossdresser Cumshot Bareback Fetish Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale 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 9,374 Crossdresser bisexual sissy crossdresser forced feminization CAUGHT!
50%
Kendra est née
La tête de Kelli a tournoyé alors qu'elle cherchait à comprendre les événements des deux dernières semaines. À peine 15 jours plus tôt, sa mère en phase terminale avait obtenu son diplôme de la School of Nursing de l'Université de Washington. Après des semaines de fatigue et de délabrement, sa mère ... Read full Story
Femboy 2021 2023-01-20 809 Stockings Teen (18+) Crossdresser Blowjob Big Cock Lingerie Shemale and Girl domination