Sort by
Relevancy

Free Stories

100%
Alessia Travestita Hung Mature Blonde British Porn Star
Alessia Travestita Hung Mature Blonde British Porn Star If you like Transexuals, big cocks, bondage, domination, deep throat, fisting, spit roast, 69, ass fucking, cum swallowing and big loads this story is for you. If not don’t bother reading. If you like my story please leave comments and ... Read full Story
darrell 2022-01-03 4,637 Group Sex Cumshot Bareback Shemale Fucks Guy Blowjob Big Cock gangbang domination Sex Toys Mature cum in mouth shemale + shemale
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 4,338 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
100%
Hung Shemale has Motorcycle Trouble near Vegas
I drive down a deserted two- lane highway outside of Las Vegas, Nevada. It is August and the temperature is well over 100 degrees. In the distance, I see a tall beautiful mature creature that walks alongside the road. As I pull over, I am stunned by her powerful physique. She sports an incredibly ti... Read full Story
darrell 2024-02-02 5,430 Shemale Fucks Guy Blowjob blonde Big Cock Mature deepthroat cum in mouth toe sucking Fisting Anal
50%
Spy Girl
Vicki stood in the dark doorway as she watched her mark, Ivan Patrinkov, approach up the empty street. There was no way he would be able to see her where she stood in the shadows. She wore a skin tight leather jumpsuit with black low-heel boots. She would have preferred to have on a pair of stiletto... Read full Story
shemale lover 2011-11-09 4,714 anal sex shemale Frottage
88%
Shemale Ride Along (Part 3)
It was the last day of classes. All of the finals were finished, and everyone was celebrating. My finals had been particularly rough. It was the last semester of my freshman year and I didn't study as much as I should have. The problem was that I lived next door to a girl that I had been having... Read full Story
qtball 2016-09-26 21,450 anal tranny Blowjob Big Cock bj Ass to Mouth
87%
My way to shemale sex
It all started with porn. 10 years ago, i was watching porn on my bed, jerking off watching a girl sucking a big cock. I looked at my cock and started wondering what that beautiful peace of meat tasted like. After a few moments of hesitation, my curiosity took over and i put my back against the wall... Read full Story
andre_xp_8 2018-07-24 13,728 anal Blowjob shemale first time
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 13,873 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
94%
Shemale Ride Along Part 1
I'm going go ahead and get this out of the way. During my freshman year of college, I was confused about my sexuality. It sounds strange saying this right after calling myself confused, but I loved girls. I really did. I loved all of their shapes and curves. I loved tits, pussy and ass. Now... Read full Story
qtball 2016-08-29 12,457 anal tranny Blowjob Big Cock bj asstomouth
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 33,790 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
100%
A man & Two Hung Shemales meet in Art Gallery o
I spent a week of absolute extreme erotic ecstasy with Stan. I used his throat and ass multiple times a day. He also fucked and fisted my ass as well. It is a week of total decadence debauchery and depravity. In the late afternoon, Stan and I decide to visit a local art exhibit so we can get out ... Read full Story
darrell 2024-02-02 5,247 anal Cumshot Big Cock Frottage deepthroat shemale + shemale swallow cum
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 2,737 Crossdresser Amateur Big Tits Cumshot Bareback Fetish Blowjob Big Cock Guy Fucks Shemale Frottage Homemade Ass to Mouth cum in mouth
100%
The Big Mature Shemale Next Door
The Big Mature Shemale Next Door SugarandSalt "Please can I just wear my old swimming trunks?" Warren begged. "No!" his mom yelled back from the other room. "Barbara purchased that for you. It was expensive so you better remember to thank her." Warren looked at himself in the full length mir... Read full Story
Gwapo67 2022-05-03 7,931 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
The Seductive Seed of a Tranny MILF
The Seductive Seed of a Tranny MILF SugarandSalt Jackson got home and immediately curled up in bed. He didn't want to move for the rest of the weekend. He'd finally worked up the courage to ask a co-worker out at work. She politely rejected the invitation. Then later on in the day, Jackson spo... Read full Story
Gwapo67 2022-05-03 7,785 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 17,299 Crossdresser sucking Big Cock ass licking big boobs
100%
Threesome fun
We had invited friend over who has big cock --he arrived and we sat around for awhile talking about sexual encounters of the past --I'm a bi part time shemale cross dresser who is very kinky --anyway it got around to looking around the house and as it happened we stopped in the bedroom , and all o... Read full Story
goodgurl34 2019-01-08 4,413 Stockings Crossdresser Amateur Big Tits threesome Blowjob Big Cock Lingerie domination Guy Fucks Shemale Mature Homemade threesome sex
100%
Buffy the Shemale Vampire Slayer Part 3
Buffy couldn't stop smiling. It felt great to have left Spike on his knees, clutching his balls in pain after she'd sucked his cock and swallowed his load of icy vampire's semen. Sex was about power, not love, and nothing made a girl feel more powerful than reducing a man-or, in Spike's case, a u... Read full Story
shemale lover 2011-08-19 5,931 hardcore celebrities shemale
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 7,489 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
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 4,341 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
100%
MILF Alessia Travestita finds a bottom boy pt 2
Several days ago, Alessia a beautiful Transsexual with a huge cock seduced Stan on their cruise ship. He willingly and enthusiastically sucked her cock and gave her his ass. She brutally throat fucked his mouth before pounding his ass. They spent over two hours together until they were interrupted b... Read full Story
darrell 2023-08-13 6,001 anal Shemale Fucks Guy Fetish Blowjob blonde Big Cock domination Mature deep throat cum in mouth sandals toe sucking
97%
How I Met Alyssa
I groaned as the sun was shining onto my face. I turned around so I could get some more sleep, but I saw it was 9:22 am and I decided it was time to get up. I got out of bed and went to the bathroom of my little apartment to freshen up a bit. I looked at myself in the mirror and saw a 20 year o... Read full Story
shemale lover 2013-02-12 14,160 hardcore sucking Big Cock ass fucking big boobs
88%
Very Impatient on a sex fanstay
Are you ready for this Mish?" "Not really but it's too late to back out now." I stood in a dark alley before a metal door shaking with both anxiety and the cold, waiting for the door slot to open and for the night to begin. I wouldn't admit it to my friend Simone but secretly I hoped we would ... Read full Story
ASSEaster5678 2018-07-10 10,758 Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale Mature
100%
Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
darrell 2022-01-03 4,334 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
100%
Beryl's birthday suit
I tried on my sister's panties when I was 12. They looked so cute, so sexy.. I couldn't help myself. I tucked my dick between my legs and pulled them over my hips, delicately positioning them just like a girl. They felt yummy! When I saw the shiny, lacy pink briefs in the mirror - snug, flat pu... Read full Story
Beryl 2023-12-12 7,162 first time Stockings Crossdresser Bareback Blowjob Big Cock Lingerie redhead sissy cum in mouth
100%
Buffy the Shemale Vampire Slayer Part 5
By the time that Buffy arrived at Rupert Giles' apartment, the former librarian, her ex-Watcher, had just finished reading a new volume of what Edgar Allan Poe, in The Raven, had referred to as a "curious and quaint volume of forgotten lore." He'd just settled the large, leather-bound volu... Read full Story
shemale lover 2011-08-19 3,675 hardcore celebrities shemale
75%
Picture Perfect
“What do you mean, you won’t? Carlos demanded, squinting into the sun. “Just what I said, I replied. Carlos was a gorgeous guy, with dark, wavy hair; a deep, tropical tan; even teeth, as white Chicklets; broad shoulders; a deep chest; a flat, firm belly; strong arms and legs;... Read full Story
shemale lover 2011-10-27 2,855 hardcore shemale Big Cock
90%
Shemale Surprise!!
I'm a country boy. About a year ago I left my small town and moved to the city so I could attend university. Initially, I had nowhere to stay so I was going to move into my cousin Mike's flat for a few days with him and his room mate, Sandy till I found somewhere of my own. Mike and Sandy worked tog... Read full Story
shemale lover 2012-04-12 4,318 anal cum oral huge cock dp
87%
Shemale First Time
First time Sex with a shemale. Intro. I have read several stories of first time sex with Transexuals and none relate to my experience. So for those who are truly curious about how to go about it and what it is like this is my tale. I have always been a straight guy as far as I know. Married... Read full Story
shemale lover 2011-08-24 9,236 first time asshole shemale
40%
Monsters that crave sex
There wans was a mad docter named hojo who studded how monsters get there mana back when it is used up or even if they even run out like humons do wan day he was working on some experaments to make humens be able to have ever lasting mana with out rest or food so they would never run out and need to... Read full Story
shemale lover 2012-03-04 2,511 hardcore Fetish shemale oral sex
100%
A "Girl" for Kelly
Kelly was sort of a loner throughout her life. She had very few friends throughout high school and college, and if she weren't around them, she would spend her time alone. Her love life was just the same. She did have a few boyfriends, and only ever managed to get one to have sex with her. It wasn't... Read full Story
shemale lover 2013-03-27 3,832 hardcore sucking Big Cock Shemale and Girl big boobs
100%
Chinese Apple Turnover
I crashed harder than anytime ever in my life and my dreams were fucking vivid. I dreamt of being fucked. And of sucking huge cock and getting face fucked so hard that I was cock drunk and high from holding my breath so much. But so really horny from him doing that, so into that cock. Of Jax f... Read full Story
ASSEaster5678 2019-01-09 6,569 anal sex Shemale Fucks Guy Asian 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 5,228 Small Tits Crossdresser Amateur Cumshot Outdoor Blowjob Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
40%
See Me At Shemale Cam Tube
I was dressing when I heard a new e-mail arriving. "You're hot as hell on Shemale Cam Tube", he wrote, "Wanna meet me 4 lunch? Promise to be a gentleman!" It was cute, especially coming from such a skinny guy. I'm a big girl - over six feet, with strong legs and huge breasts whic... Read full Story
shemale lover 2011-08-09 6,427 asshole Blowjob shemale
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 4,171 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth 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 2023-01-24 968 Stockings Crossdresser Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys
93%
MILF Alessia Travestita finds a bottom boy
I was several days into a cruise to New Zealand and Australia with my wife. This morning my wife went on an excursion that I had no interest in, so I had the cabin to myself. I hadn't had any sex with my wife in the last 3 days due to the activities such as the various jaunts to Auckland and the sur... Read full Story
darrell 2023-08-13 6,154 anal Cumshot Shemale Fucks Guy Fetish blonde Big Cock domination Mature deep throat cum in mouth sandals
77%
Shemale Sex Stories Tell The Truth
You couldn’t help it but to notice when the tall blond came to the party. She was steaming hot, and all the guys turned their heads while all the girls glanced in envy. She was dressed a bit slutty and didn’t seem to mind the looks or the attention. Soon enough, she approached me and tol... Read full Story
shemale lover 2016-02-18 14,060 anal sex oral sex tgirl
100%
A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
shemale lover 2011-12-06 6,733 Creampie Big Cock ass fucking
93%
SHEMALE SEX IS THE BEST
I had been in sex with gays for 1 year, but had always been intrigued by those hot looking chicks who packed more than a pussy between their legs. I had no idea where to find one in Kanpur I was definitely bi-sexual, still seeing whores, and still going to gloryholes for my cocksucking needs. I w... Read full Story
shemale lover 2014-03-07 4,716 tranny Big Cock ass licking doggy style big boobs rimming
42%
sexy jane story
I love the idea being a crossdresser wearing women outfit bars in panties n sexy outfit not just for the sex I love sex being on my knees sucking cocks in getting fuck by a big cock see win I was very young I had sex with 3 guys one day they ask me will I suck there cocks in I sand yes we want insid... Read full Story
45sexyjane 2019-05-27 4,208 Small Tits Crossdresser Amateur Big Tits Masturbation Blowjob blonde Big Cock gangbang Lingerie Sex Toys shemale + shemale sexy crossdresser
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 12,538 Amateur Big Tits Blowjob Big Cock Guy Fucks Shemale
100%
A Job in the Theatre Chapter 19
"Be a dear and get that bag from the car," Paula winked. "Sure," Billy said stuffing his erection back inside his leather pants. He stood, and for just a moment, was right next to Gary, almost touching. Gary could feel the heat waffling off of Billy. He looked so obscene with ... Read full Story
shemale lover 2012-03-15 3,040 anal sex shemale stroking shaving
100%
The Experience of a Lifetime
My divorce was hitting me really hard. My wife outgrew our relationship and started living her own life and I had a front row seat to everything. My heart and life was upside down. I didn’t go out anymore. Friends and family both told me it was time to get my life back on track and start living ... Read full Story
therefill05 2020-11-30 20,082 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob blonde Big Cock Ebony Uniform domination 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 9,237 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 3,334 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
84%
Fucked by a Shemale
My names - and I would like to tell you about a very sexual experience I had recently. First I would like to tell you I’m 30 years old and never had a gay experience, until now. It was a Saturday night, me and my brother were round the local town, after a few too many beers my brother met a bi... Read full Story
shemale lover 2011-08-18 169,242 first time shemale cum
87%
They Were Right
They were my friends, but I'd had sex with both of them. Not at the same time, but I had dated the one for a month and just started dating the other. So, although the thought had never crossed my mind before, I found myself dressed up as a girl for Halloween. After we had partied at a few clubs and ... Read full Story
shemale lover 2011-12-29 5,809 shemale Big Cock porn
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 4,936 sucking fingering Guy Fucks Shemale
96%
My First Sex with Tgirl
This is story about me......Hope you all enjoy it I was 19 years old and itching to have sex like every normal teenager. Years of jerking off to porn had only expanded my imagination and made me want to fuck a girl even more. I was turned on by just about anything and everything except gay porn. Ev... Read full Story
sach 2016-02-16 13,507 first time tranny ass fucking guy on shemale mutual suck
77%
Slut indiscretion
At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... Read full Story
Regina10 2020-09-16 5,437 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth
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 7,421 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 5,189 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
100%
Regina's Vagina dreams
I think I wanted to be a female from birth. I once looked through a girlie magazine out of curiosity. I had impossible dreams and I longed to trade genitalia with them. I have always fantasized about my Vagina when I was younger. It was during those times that I would drift into my own private world... Read full Story
Regina10 2024-03-01 5,377 anal Big Tits Bareback Creampie Blowjob Big Cock Ebony gangbang Guy Fucks Shemale big ass cum in mouth double anal
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 2,957 Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass Ass to Mouth
100%
A Dickgirl Part 2
Ginny was mortified. For the first time in her life she hated her body. Why the fuck did she have so little self-control? Why couldn't she hold her body back? Why couldn't she be like normal girls? She cried all the way home, her tears drenching her shirt. She stopped by the time she got home, bu... Read full Story
shemale lover 2012-02-27 6,663 Cumshot sucking Big Cock Shemale and Girl
87%
THE ATTIC NOVEMBER 7
THE ATTIC NOVEMBER 7 – PART 1 THE JOURNEY AND GETTING READY. Susan had not had the opportunity to make the journey to the Attic dolled up to the nines so she made do with just wearing her black and pink lingerie under the hideous drab stuff (yuck). Having arrived early and parked up, she relaxed ... Read full Story
sexysusang 2018-03-09 5,927 Amateur Group Sex Bareback Blowjob Guy Fucks Shemale 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 31,345 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth