Sort by
Relevancy

Free Stories

88%
MY FIRST SEX WITH SHEMALE
This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous durin... Read full Story
shemale lover 2013-12-01 40,060 first time anal sex suck Shemale Fucks Guy Guy Fucks Shemale
66%
Sex in the kitchen with my hubby's friend - a cop
Ever since my wedding last year, I enjoy a great time with my hubby who loves me so much and takes care of me so much. Since he is married and having another family, he doesn’t stay with me all the time, but comes and stays at least 2 or 3 days in a month and we literally celebrate those nights wit... Read full Story
Manusha Tranny 2021-10-14 5,233 Small Tits Crossdresser Amateur Cumshot Outdoor Blowjob Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth 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 13,886 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
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 4,898 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
100%
The Game 2
That next morning again Ada and I went down for breakfast and the table was smaller, It wasn't as grand as it had once been and to every guy at the table was now at least two girls. We had our normal breakfast and for once there seemed to be a little more chat between everyone, I think after bei... Read full Story
chris1989r 2022-01-24 4,437 Amateur Cumshot Bareback Shemale Fucks Guy Blowjob blonde Big Cock Asian domination Guy Fucks Shemale Ass to Mouth cum in mouth shemale + shemale
100%
TO BE OR NOT TO BE – PART 3
TO BE OR NOT TO BE – PART 3 by Spanky de Bautumn Part 2. At the hotel in New York City, Sunny meets the bellhop, Antonio, and they go out for a drink when he gets off of work. The call came at exactly seven. I had woke up about five minutes before and was watching Antonio sleep. All of the oth... Read full Story
SpankydeBautumn 2021-02-23 2,520 Small Tits Crossdresser Amateur Cumshot Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
Amy and the Straight Jocks PT1
Only a couple close friends knew for sure and most others knew it as just a rumor. Amy dressed and lived life as a girl like she had since the start of high school when she moved from a new town. The jocks would laugh and whisper to each other when she walked by debating if the rumors were true. Co... Read full Story
DADDY4sluts 2022-08-09 3,878 Teen (18+) Cumshot Bareback Creampie Blowjob Guy Fucks Shemale cum in mouth
0%
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 4,353 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
100%
Taking Ricky's Cherry
My work has me traveling all over the US and if you have read any of my previous stuff then you might have figured out that I have a major cougar streak. I just love being the first T gurl to a sexually inexperienced young guy. I was bored and horny in the hotel room, so I logged into a gay dating s... Read full Story
pennypenny 2019-06-11 8,417 Stockings Teen (18+) Crossdresser Cumshot Bareback Creampie Fetish Blowjob redhead Guy Fucks Shemale Mature Ass to Mouth cum in mouth
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 3,643 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial 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 2,446 Stockings Small Tits Crossdresser Cumshot Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
50%
HOSPITALITÉ DU SUD
Ash regarda sa mère, incrédule quant à ce qu'elle venait de dire. Il comprenait la prémisse de base de ce qui s'était passé, mais le raisonnement qu'elle avait dû le déconcerter. "Pourquoi ?! Pourquoi ferais-tu ça ?!" Il a plaidé, la voix légère et désespérée. Elle haussa l... Read full Story
Femboy 2021 2023-02-05 1,141 Stockings Crossdresser Shemale Fucks Guy Big Cock Lingerie Guy Fucks Shemale
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 2,444 Crossdresser Cumshot Masturbation Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
94%
Sissy Slut: Gang Favored
I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... Read full Story
Regina10 2021-03-02 7,497 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
95%
First time
Hi, my name is Sandra. In fact, I'm not exactly a girl, but a CD. Even as a child, I felt different and I used every opportunity when I was left alone in the apartment to dress up, to put on women's clothes, to put on make-up. In time, I started watching porn, as did all my friends. But, unlike them... Read full Story
cd Sandra 2021-10-13 5,702 Stockings Teen (18+) Small Tits Crossdresser blonde Guy Fucks Shemale
50%
PRIS
"Merci d'avoir fait ça, Alex," dit Mr Stevens en me serrant la main. "Au revoir Mr et Mme Stevens !" J'ai crié depuis la porte d'entrée alors que mes voisins me faisaient signe avant de monter dans leur voiture. Ils fêtaient leur anniversaire avec une soirée et je m'étais porté volontaire pour ga... Read full Story
Femboy 2021 2023-01-27 926 Stockings Teen (18+) Crossdresser Fetish Big Cock Lingerie domination Guy Fucks Shemale cum in mouth
80%
Wrong Vampire
I consider myself a fairly tolerant person. I judge each person on their merits, not their skin color, gender or even sexual orientation. I'm even in favor of the Vampire Rights Amendment, but I must admit, unlike other groups people discriminate against, they make me uneasy. They claim that all the... Read full Story
ASSEaster5678 2019-04-23 6,548 Cumshot Shemale Fucks Guy Guy Fucks Shemale cum in mouth vampire
80%
Group Sex
Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... Read full Story
Jon Paul 2021-04-19 3,188 Group Sex Cumshot Bareback Creampie Shemale and Girl Guy Fucks Shemale 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 4,345 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
100%
Mongoose Hunting and the Dark Car
After my first sexual experience with a trans girl in school (Check out Biology of Music), it was a long time before anything else got me that horny again. Which is obviously understandable given how ridiculous that whole event was. This time instead of a trans girl cumming hot jizz into my mouth af... Read full Story
terrifictim 2023-03-30 5,559 Teen (18+) Cumshot Bareback Creampie Guy Fucks Shemale rimming rimjob Ass to Mouth cum in mouth Surprise secret bathroom sex Daddy daughter risky public
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 4,705 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
100%
About Jack and Diane
Thanksgiving was over the college kids are returning to school and Las Vegas has slowed down from the busy restaurants and overcrowded casinos. It’s the best time of year to see a nice show for less. Jack’s friends had all taken off with families and he had time to think about how lonely he really w... Read full Story
Jon Paul 2023-12-20 6,795 anal Cumshot Bareback Fetish threesome Lingerie Guy Fucks Shemale small cock shemale fucks shemale cum in mouth shemale + shemale
100%
Male or Shemale, Still a Slut
Part 1 My name is Brandon. I'm 18 (still in high school), 5'5", white with black hair, and rather feminine. I'm really slim with barely any body hair. All this has combined so that I'm not so popular with the ladies, which sucks cause I am one horny son of a bitch. Luckily, I'm rather fond ... Read full Story
shemale lover 2012-12-20 9,311 Cumshot sucking blonde ass fucking Guy Fucks Shemale
84%
Lesser of Two Evils
My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... Read full Story
shemale lover 2013-03-27 22,781 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
96%
A Night of Lust
I was out at a night club with a few friends, and we were there for for a while before I noticed this sexy, rather short girl across from me at the bar looking over. I could tell, even from this distance that there was something special about her, I wasn’t sure what that was quite yet though. The mo... Read full Story
JessicaEdwards 2018-08-07 18,258 Stockings Amateur Cumshot Masturbation Bareback Creampie Shemale Fucks Guy Blowjob blonde Big Cock Lingerie deepthroating Guy Fucks Shemale cum swallowing deep throat deep penetration cum swapping pov Ass to Mouth cum in mouth anal fuck sloppy virgin ass
100%
Shawshank affair
Courtrooms can be a scary place. They smell like older leather, the wood paneling has been polished with oil and each sound penetrates your body like a loud smack from a cap pistol, which echoes in the forest, especially the gavel smacking on a block from the Judge. I felt strongly that I would be f... Read full Story
Jon Paul 2018-08-20 6,601 Stockings Crossdresser Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
66%
Trannies in Space
There was no spaceport on Jansen's Planet. There had been, but whatever calamity had befallen the world generations ago had also destroyed its port. It was one of so many planets out in the Barrens that had fallen on hard times. So Dekker set down the Barnabas in a clearing in the forest, a remna... Read full Story
ASSEaster5678 2019-01-25 12,187 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
100%
From a 50's virgin to a Mature good for all
***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... Read full Story
hippocampus_171 2023-01-11 4,353 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
100%
Erotic Dreams come true.
You start having intense erotic dreams — and the faces you see is one you don’t recognize but that feels familiar. Mandy was that girl that Chad had been dreaming of, the kind where to see her made a rush go through you like a hot flash. Chad had just broken off a relationship, and his sister war... Read full Story
Jon Paul 2023-05-26 4,881 anal Stockings Big Tits Cumshot Bareback Fetish Blowjob Guy Fucks Shemale small cock
75%
Backsliding: Tim's Story
Every man has a weakness, but not everyman knows what that weakness is until it is too late. The story I'm about to tell is something I'm not entirely proud of. My name is Tim. I'm a 22-year-old college student at California State University. I'm almost at the end of my senior year studying to be... Read full Story
shemale lover 2012-02-09 4,946 sucking fingering Guy Fucks Shemale
100%
Boi Toy
They met me off the train late in the afternoon. Their welcome was warm and friendly. I was exhausted from travelling and spent the evening in wonder as we first had drinks with friends of theirs at one home then all went out to eat at a restaurant, then back to another friends home for more drinks.... Read full Story
shemale lover 2013-01-29 5,993 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
92%
A Surprise Relationship
This is a fictional story, although it is based on people I did know. "Tony" and his twin sister "Kim" are based on a set of twins I knew, who were almost identical. I did have a relationship with "Kim" for almost two years, however, the relationship with "Tony&quo... Read full Story
shemale lover 2013-01-29 5,318 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
95%
Ginger's First Gangbang
I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... Read full Story
Ginger__57 2018-03-26 8,634 Stockings gangbang redhead domination Guy Fucks Shemale Ass to Mouth cum in mouth
95%
Mai
When I was twelve I met a new classmate named Dave, he and I became great friends hanging out, joining clubs and what ever else high school kids do. His family was from the Phillipines and he and his sister were the first generation born in this country. His sister Mai is the focus of this story. ... Read full Story
Zöe from Kingston 2018-08-09 11,342 Cumshot Bareback Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale Interracial cum in mouth
95%
Halloween Night Again
Last October my girlfriend Kelly and I were drinking wine and playing cribbage on a cold, rainy night. After dating her for six months we usually stayed in on weekends. I consider myself very lucky to be dating her. She is an incredibly beautiful brunette and has a perfect 36C-24-26 figure on her 5'... Read full Story
ASSEaster5678 2018-10-29 13,126 Shemale Fucks Guy Guy Fucks Shemale Halloween
80%
How it started
What got me started off watching shemale porn was actually meeting a very beautiful shemale at a beach party. I already knew she was a guy but she was so beautiful. So at one point I asked her if she wanted to go for a walk and after a few minutes and let her know that I was down. Her response was ... Read full Story
PNPFUCKBOY 2019-02-12 11,874 Teen (18+) Small Tits Crossdresser Amateur Big Tits Outdoor Latina Bareback blonde Big Cock Ladyboy domination Guy Fucks Shemale Interracial Sex Toys Mature Homemade Ass to Mouth
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 4,106 Teen (18+) Crossdresser Big Tits Cumshot Masturbation Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Homemade Ass to Mouth
100%
Bangkok Night with Thai Ladyboy Dancer
I was visiting Thailand back in the 90s and was blown away by the “Potpourri” of sites, sounds, and smells (not all of them good) of this city. Beautiful women were at every corner and very friendly to foreigners. I went out with a group of guys on the town after dark to check out the go-go bar scen... Read full Story
AllenB 2022-04-20 5,843 Shemale Fucks Guy Asian Guy Fucks Shemale rimming bottom ladyboys cum in mouth top Versatile
100%
FILLE DE RÊVE ⚧️ ⚧️
« Alors, à quoi ressemblerait ta petite amie parfaite ? » « Toi », pensa Steph, regardant dans les yeux noisette avec des reflets dorés à l'intérieur. Il lui fallut quelques secondes pour se rendre compte qu'il devait répondre avec sa bouche. « Oh, euh… quelqu'un d'attentionné je suppose ? ... Read full Story
Femboy 2021 2023-02-17 985 Stockings Crossdresser Cumshot Fetish Blowjob Big Cock gangbang Lingerie domination Guy Fucks Shemale Interracial Sex Toys cum in mouth
75%
Aunt trip
In 2013, after almost three years of service in Afghanistan, George Madsen, a gay Royal Navy communications petty officer, retired. His experience in the distant deserts had left an indelible mark, the memories of friends lost and challenges faced still burned vividly in his mind. Coming home was n... Read full Story
Rebba 2024-04-25 3,225 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
73%
Nightclub Cum Slut
After splitting with my first boyfriend I went through a period of time I call my slut phase. I explored my sexuality in a massive way and did as much cock ass and pussy as I could. I thought that after I had been in a few relationships that my slut phase was over. I still had the odd one night stan... Read full Story
shemale lover 2013-01-10 7,201 Cumshot sucking ass fucking Guy Fucks Shemale ass fingering
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 8,992 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
93%
Miss Bernie
My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... Read full Story
shemale lover 2013-02-22 14,088 hardcore sucking ass fucking Guy Fucks Shemale
93%
My First Time Made Me A Slut
A true story of my first time. And why I so need a daddy now. The first time I went out dressed. I went to a bookstore in east Portland. As I got out of my car feeling the breeze up under my very short silky skirt, trying to pull it down as cars were wizzing by. I walked or should I say wobbled the... Read full Story
Teddie 2018-09-12 12,501 first time Stockings Crossdresser Bareback Blowjob blonde Big Cock gangbang domination Guy Fucks Shemale slut cum in mouth
95%
Late night park visit
It was 11pm on a Friday night, I was driving my car back from a failed meetup with a guy I met online a couple of days prior. I thought it was going to be an amazing night, so I spent close to two hours getting my makeup and hair sorted to look pretty for him when we met. I was wearing a short black... Read full Story
Natalie Bishop 2018-10-08 7,190 Amateur Cumshot Bareback Creampie Big Cock Ladyboy domination Guy Fucks Shemale public Park
94%
Crossing lines
It had always been a fantasy of mine. I have very feminine features and long natural straight brown hair. Which recently I had shortened to chin length. I have been dressing in womens clothing now for many months and had decided that this was the night in which I get made up totally and head ou... Read full Story
Zöe from Kingston 2019-02-04 11,100 Stockings Crossdresser Cumshot Outdoor Bareback Shemale Fucks Guy Blowjob Big Cock Ebony Guy Fucks Shemale Interracial
50%
I and the old man's story 后面中文
I am from Chongqing, a boy who loves his father. When I was young, my neighbor aunt always said I looked like my sister, like a beautiful girl. At that time, my family was relatively poor. My Sister, my parents, and my family of four lived in public rental housing of less than 30 square meters. Star... Read full Story
Oldslut Sissy 2024-04-15 8,957 Crossdresser Amateur Masturbation Asian Ladyboy Guy Fucks Shemale Mature small cock Homemade sissy chinese teen (18+)
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 4,302 Masturbation Shemale and Girl redhead Guy Fucks Shemale cum eating anal creampie couple & shemale
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 7,934 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Christy's Fantasy Come True Chapter 6
The alarm went off and Christy rolled over and hit the off button. The clock face was starting back at her flashing 8:00. Since it was Friday she had slept in a bit. Jim had gotten up early and left for work after spending the night. They had gotten into a minor argument last night but came to a... Read full Story
shemale lover 2013-01-30 5,117 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
96%
Making A Man Out Of Tommy
I have two good friends, Brad and Matt who are actually my fuck buddies. Both of them travel for work, so they tend to be gone a couple of months at a time. I have a key to their apartment, so I can let myself in for sex when they are home and to bring in the mail when they are not. I also get to us... Read full Story
pennypenny 2018-08-31 9,899 Teen (18+) Crossdresser Amateur Masturbation Bareback Creampie Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
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 11,861 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%
Getting Fucked by Sasquatch
Bill was about to show up, I had known him from a chat room for years now. I was in his town for work and we had set up this date so we could finally meet each other. I heard a hard knock at the door and when I swung it open, I just stood there in awe. It wasn’t the big beard or really long hair tha... Read full Story
pennypenny 2020-08-21 5,982 Crossdresser Bareback Creampie Fetish Blowjob Big Cock redhead domination Guy Fucks Shemale pov Ass to Mouth 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 8,473 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
100%
Slut /W Bad Boy
I was excited as always because I was about to go out in public and hopefully I will meet some horny man with some money and get laid. Now, to make sure that I am a picture of femininity, I double checked my makeup in several mirrors from many angles. My lips were perfect and I made sure my cheeks b... Read full Story
Regina10 2020-12-04 7,066 Stockings Crossdresser Big Tits Cumshot Bareback Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale pov Ass to Mouth
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 3,655 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth