Sort by
Relevancy

Free Stories

100%
Fuck Friends Forever
"Flip over..." Those two words come as a surprise, filling my mind with expectations. I find it interesting that Brian wants to switch from doggie style to a more traditional sex position, a romantic one at that. Hopefully, he won't be turned off if he sees my cock while we're having sex. I hope... Read full Story
ASSEaster5678 2019-01-09 8,941 Bareback Shemale Fucks Guy Big Cock Guy Fucks Shemale
100%
Deflowering Latina Sissy Destiny
A real life story of my one and only time deflowering someone and being their first real encounter, I was 27 at the time and she was 21. I am absolutely convinced that Trans girls and CDs have a bit of a 6th sense when it comes to perceiving which guys are into them even in a public situation. I ... Read full Story
AllenB 2022-09-07 6,523 first time Big Cock Guy Fucks Shemale Homemade sissy travesti cum in mouth
100%
Horny Writing A Strange Habit
I enjoy watching videos which I can Vicariously live. This is nothing more than my horny hobby, an amalgamation of various thoughts. My form of hands free edging. Spell checked only, "No I haven't proof read a first draft, not trying to publish masterful works here." Hope to hear from those w... Read full Story
Araina 2021-03-08 2,847 Crossdresser Amateur Big Tits Cumshot Bareback Fetish Blowjob Big Cock Guy Fucks Shemale Frottage Homemade Ass to Mouth cum in mouth
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 3,435 Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass Ass to Mouth
54%
Experience with Shemale Kadambari in Pune
PS: this is a genuine experience. Hey, I am back with another story. Let me introduce myself. I am ordinary guy who like to score shemale from Pune. I have already posted one experience with arzoo. So yes let's start, I had a normal chat with Kadambari on what's app discussing the rates. So she a... Read full Story
spidymoto 2020-03-24 6,606 Cumshot Blowjob shemale Big Cock Guy Fucks Shemale indian Indian Shemale Pune Pune Shemale
100%
Crossdresser gets dick for first time
I was so tired of just watching porn. So tired of the sissy hypno threads that made me crave men, crave cock, crave being weak, crave being the bitch...only to cum and do nothing about it. But the desire to transition from fantasy to reality was growing stronger and stronger. I decided it was ti... Read full Story
Sissy Ava 2022-10-11 8,049 Stockings Crossdresser Amateur Bareback Big Cock Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Alessia and I shock our guest!
Alessia was sat on the couch and I was sitting on the soft fur rug between her legs. We were relaxing and recovering watching an old movie. My ass was still feeling hot and wet after Alessia had earlier fucked me hard and long and I had returned the favour to her. But that is another dream! So back... Read full Story
Alessia Travestita 2023-01-12 4,644 Crossdresser Blowjob blonde Big Cock Guy Fucks Shemale Mature cum in mouth
100%
Philippines Vacation with a Dominant Big Cock Ladyboy
I am still in a state of unbelievable joy that I was lucky enough to experience this but I 100% did and I can’t stop thinking about it as I thought things like this only happen in porn or fantasies. Buckle up because this is a wild one and happened in Manila May 2024. I had the opportunity to vi... Read full Story
AllenB 2024-07-14 5,314 Bareback Creampie Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale cum in mouth domination act filipina ts filipina ladyboy
100%
The Story of Stephanie (Chapter 9)
After that encounter with Alicia, I kept a low profile. I was paranoid incase her husband was coming after me. But, one thing I did know, was that I didn't want to get into anything that complicated again. I also knew that Stephanie was ready for some more fun with a man. I'd lived out a fantasy wit... Read full Story
Stephanie Wild 2024-07-14 2,068 anal Crossdresser Amateur Blowjob Big Cock Guy Fucks Shemale
56%
Big cock shemale from Pune, India
I just saw her profile on Planet Romeo, her name is ID is Kaynat / Muskan. I saw her photos and got attracted to her. I am always a big fan and lover of Shemales or TS. I called her and fixed appointment by negotiating with her for 2500 INR. I went to meet her, she stays in a condominium in ... Read full Story
Stud4Shemale 2017-05-22 96,235 Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Catching up with the biggest cock
I have recently written with an account from my diary about the biggest cock that I’ve ever seen and someone saw the experience and wanted to know more as I had said that I met him a few times. So, I can bring that right up to date now because I have recently been to see him again. But let me go bac... Read full Story
lkusex 2021-06-03 11,027 Masturbation Big Cock Ladyboy domination self sucking Ass to Mouth Vintage
91%
Banana Fetish
I was 27 and single and enjoying being free sort of the ‘sworn to fun loyal to non’ stage in young adulthood. I lived alone in a 1-bedroom apartment and loved working on my motorcycle which I kept in my living room. Most Friday nights for me were jamming out to music, enjoying a few beers and tinker... Read full Story
AllenB 2023-02-16 10,098 Latina Fetish Big Cock Guy Fucks Shemale Interracial rimming Homemade Ass to Mouth Banana ass eating
100%
Fuck Room
I'll be honest with anyone reading this. I have been very slutty since I began putting a lot more time into my dressing up and going out. I met plenty of guys off of Grndr and Tinder, and some very hot experiences took place on some of those..."dates". I actually liked the feeling of being used. Kno... Read full Story
Sissy Ava 2022-10-24 4,595 Stockings Crossdresser Blowjob Big Cock Guy Fucks Shemale Interracial public sex
100%
Incubator
For lack of a better term, I will call him my Lover. I call him Grae, which sounds like "gray" if you are doing a rather poor impersonation of a Scotsman. Not that I have anything against the Scots; that's just as close as I have been able to come to pronouncing his real name. You would think that s... Read full Story
ASSEaster5678 2019-04-23 4,716 Big Tits Bareback Shemale Fucks Guy Big Cock Guy Fucks Shemale monster
100%
Train adventure
A new story from me and be patient with my english ;). You can read my other stories here: https://www.ashemaletube.com/profiles/176291/stories/ It's late in the evening, I'm standing at the train station and like every Sunday I take the last train back to t... Read full Story
Marten1201 2023-03-21 5,737 Cumshot Shemale Fucks Guy Blowjob Big Cock Guy Fucks Shemale Ass to Mouth cum in mouth
94%
My Romantic One Night Stand with a Beautiful T-girl.
My Romantic One Night Stand with a Beautiful T-girl. A friend of mine landed a gig DJing at the well known dance club in West Village of New York City. She invited me to check it out. Why not, I had no plans that weekend and she can put me on the VIP guest list. Which means I don’t have to wai... Read full Story
My Shemale Attraction 2019-06-11 7,836 Big Cock Guy Fucks Shemale cum swallowing Love blowjobs cum in mouth My Romantic One Night Stand with a Beautiful T-girl.
92%
The Girl Next Door Ch. 02 by derezzed ©
Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the sunlight that h... Read full Story
StevelovesTgirls 2019-06-11 12,688 Amateur Big Tits Blowjob Big Cock 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 12,073 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%
LE KID GYNÉCOMASTIE ⚧️ ⚧️
Dans la cuisine de la maison de son petit ami, Crystal fait un dernier effort, appelant sa belle-mère, le Dr Burns, à l'aide : "Crystal, tu es en train de dire que tous les médicaments que j'ai prescrits à Nick depuis un an et demi n'ont eu aucun effet sur lui, n'ont eu aucun effet positif sur lu... Read full Story
Femboy 2021 2023-03-26 719 Big Cock Guy Fucks Shemale Interracial feminization sissificatio poule mouillé
50%
💕 TEMPÊTE DE NEIGE DU VENDREDI SOIR ⚧️
Il était tard, près de minuit un vendredi soir glacial, au milieu de février, lorsque je me suis retrouvé au volant d'une tempête de neige absolument aveuglante. Après avoir écouté les bulletins météo à la radio toute la journée, j'étais certain que je pouvais battre la tempête à la maison. Ils avai... Read full Story
Femboy 2021 2023-02-17 588 Crossdresser Fetish Blowjob Big Cock Guy Fucks Shemale 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 14,147 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
25%
CDSissy1 Training Regiment
New regimen for sissy Just wanted to say that lately I have a lot more time and freedom so I can play more....for the moment I have placed myself on a strict routine. I have to fuck my 8" dildo ON MY FUCKING MACHINE I figured that is a pretty good set up for an aspiring BBC slut.. It is important b... Read full Story
CDSissy1 2019-01-28 3,570 Stockings Small Tits Bareback Fetish blonde Big Cock Guy Fucks Shemale Interracial
50%
Fluffy Takes a Walk
It neared dusk at ValueStar Motor Lodge which sat smack dab in the middle of the hood. Inside of Room Twelve, an average height, chubby, brown-skinned femboy repeated the douche. He let out the stream of lukewarm water and turned around to study the toilet as the hip hop music blared in the backgrou... Read full Story
Faggyboi and Puzziboi 2023-04-09 5,392 Crossdresser Big Tits Guy Fucks Shemale big ass sissy femboy BB fagg faggyboi puzziboi
80%
In The Club Part 2
Continuing the story from part 1 After tongue studding deans hard fat knob for a minute my heart was jumping i was just thinking how amazing it must feel in my bottom , i asked him do you fancy coming back to my motel room across the road @ he said yes , i told him the room number @ said i will le... Read full Story
sara gabo 2020-09-16 2,016 Bareback Big Cock Guy Fucks Shemale Club Girl
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 4,272 Teen (18+) Crossdresser Big Tits Cumshot Masturbation Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Homemade Ass to Mouth
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 8,066 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
69%
Pune crossdresser Night Girl
Hi friends, I hope you liked my earlier stories. This is my new story about a lady boy / crossdresser / sissy boy. Around 2 years back I came across a profile on Planet Romeo with name Nightgirl. I sent her message that i found her sexy and attracted to her and wanna meet her. I am alway... Read full Story
Stud4Shemale 2017-05-22 7,626 Crossdresser Asian Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
90%
Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
Regina10 2020-11-30 9,435 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
100%
TO BE OR NOT TO BE - PART 7
TO BE OR NOT TO BE - PART 7 by Spanky de Bautumn Part 6. Sunny, Mel, and Shari had a heart to heart and Mark took Sunny for a night on the town. I woke up next to Mark, he looked so peaceful sleeping. Was I dreaming? Did I fall asleep and dream that Mark said he was going to take me shopping... Read full Story
SpankydeBautumn 2021-03-01 2,800 Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
100%
My Gloryhole Daddy
I had been working the gloryhole at the strip club for almost a month. Mostly it was jerking off pathetic dicks with a fleshlight while fake moaning and scrolling my phone. But every now and then I'd get a text from my favorite john saying he'd be stopping by. His cock was so beautiful! A solid 8 in... Read full Story
KaceyKlarissa 2024-09-11 791 anal Crossdresser Bareback Creampie Blowjob blonde Big Cock domination Guy Fucks Shemale sissy femboy Ass to Mouth
96%
Riding Home With Strangers
The music was running, the booze was flowing through my veins and I was not ready to leave just yet. My ride had to leave early, because my driver's hours were up, and I didn't want to force him. I didn't think I would be having so much fun before I came here. I met a group down here who li... Read full Story
shemale lover 2013-01-30 9,098 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Castro - shemale goddes
Nobody would have believed the scene was true, her slender, smooth and tanned legs crossed in such a deliberately provocative way as to reveal a glimpse of crisp white panties. Her tightly fitting, classically styled little black dress cut to ensure firm large breasts were displayed to maximum effec... Read full Story
Law12 2018-03-04 5,174 Masturbation Bareback Creampie Ass to Mouth cum in mouth Supernatural
33%
My new Experience with Amy Cute Shemale in Pune
Hi friends i am back with new story. I am mad shemale lover. and keep on finding new shemales for me. This time i got new website to search for shemale www.massagerepublic.com I saw an advertisement of Amy and i liked her. called her and fixed appointment. went to her hotel, which was ok ok ... Read full Story
Stud4Shemale 2021-02-20 6,363 Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale shemale fucks man man-fucking-shemale Indian Shemale Pune
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,792 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
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 4,540 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
100%
A new start in life
“In life, finding a voice is speaking and living the truth. Each of you is an original. Each of you has a distinctive voice. When you find it, your story will be told. You will be heard.” John, living outside Boston, being your average accountant working with Gillette, had gone through a messy di... Read full Story
Jon Paul 2024-05-09 3,362 anal Amateur Shemale Fucks Guy Big Cock Guy Fucks Shemale small cock big ass