Sort by
Relevancy

Free Stories

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 12,692 Amateur Big Tits Blowjob Big Cock Guy Fucks 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 4,544 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
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 14,154 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
100%
Casino Girl
I had been working as a casino dealer for several years and would occasionally meet some very attractive women and chat. Asian women have always been attractive to me, whether the exotic appearance or maybe because my Mom was Pacific Islander, and a lot of people thought I was Asian. Mia was a bit... Read full Story
Jon Paul 2022-01-03 3,059 Stockings Cumshot Bareback Blowjob Asian Ladyboy Guy Fucks Shemale
71%
TGirl Initiation by 3 BIG BLACK 12
In my teen years I was often told that I was quite feminine.The high school punks always told me that I filled out the back of my jeans in a girly way. After taking a shower one day I did notice that they were right, I had a nice white bubble butt. Not to mention that my lips were also quite girly. ... Read full Story
TgirlJill4BBC 2013-06-04 9,210 Stockings Cumshot suck Big Cock Lingerie Interracial Latex
100%
SheMale Pussy and Cock
I once had a friend who always said "never fuck anything you can't bench-press". He was right, the biggest benefit of having sex with someone smaller and lighter than you is you can lift them easily ! On a recent trip to Thailand I couldn't take my eye's off a stunning, short, tiny but ... Read full Story
shemale lover 2012-01-24 4,344 anal shemales gay male
100%
KING OF TRANNY CHASERS ENTRY 2
LAST YEAR TO CELEBRATE MY BIRTHDAY I DECIDED TO FULFILL ONE OF MY SEXUAL FANTASITES. I HAD BEEN WITH 2 CIS WOMEN SEVERAL TIMES BUT NEVER HAD I BEEN WITH 2 TRANNIES. MY BIRTHDAY WAS ON A FRIDAY SO I SPENT THAT DAY AND THE NEXT CELEBRATING WITH MY FAMILY AND GINA..THAT SUNDAY I SET UP AND PLANNE... Read full Story
Ghostface drillah 2024-07-04 2,532 anal Amateur Group Sex Big Tits Cumshot Shemale Fucks Guy Fetish Big Cock Guy Fucks Shemale big ass Homemade Ass to Mouth shemale fucks shemale
88%
Tipping Point -- Chapter 1: Blow by Blow
Chapter 1: Blow by Blow October 12th Thursday evening. Tick, tick tick... the minutes pass by while Nick lies on his back, staring at the white ceiling fan that hovers above. He raises his head, bats his eye lashes, and yawns. His long, wavy, auburn hair falls down his back with small curls. ... Read full Story
Danielle Pillory 2015-11-24 5,491 anal shemale domination spanking submission
100%
Uncle sweet Lover
Uncle Barney called me this morning and wanted me to keep my evening free. He wanted to meet me at the motel with a surprise for me. I was so excited and could hardly wait. I had to decide on something to wear, but when I thought about it, I realized that I wanted to wear something special. He would... Read full Story
Regina10 2024-02-19 4,988 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
80%
Bisexual Black Man's Paradise
The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... Read full Story
shemale lover 2012-06-24 5,537 big dick tranny anal sex Cumshot orgy facial oral sex
92%
T-Girl Meets T-Girl
It was a silent car ride home. He looked at her, she looked out the window. She looked at him, his eyes were on the road. Neither of them broke the silence. It stayed that way until he parked in her mom's driveway. The soft-spoken young man told his girlfriend, "Goodnight Ashley. I'll call y... Read full Story
shemale lover 2012-08-29 6,294 anal sex Cumshot shemale and shemale domination blondie
100%
delicious virile male flesh
Tasted delicious virile male flesh… The breeze caressed my swollen nipples giving me pleasant shivers. The two glasses of Riesling had also contributed to my excitement. My crotch was burning as if the disappearing sun had blown all its thermal energy into me. Under my fine lace panties, purple o... Read full Story
hippocampus_171 2023-04-23 5,150 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminisation cum in mouth gaycd virile
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 5,457 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
100%
The Big Tiddy Goth Girl
Hannah and I went to the pool in my apartment complex. This was my first time dressed as female in public and I was loving my new, feminine tan lines. To keep a long story short, while tanning we were perv'd on and approached by a guy calling himself Mark. He was desperate for our attention and fumb... Read full Story
KaceyKlarissa 2024-02-23 5,062 Crossdresser Big Tits Cumshot Masturbation threesome Big Cock Shemale and Girl small cock big ass sissy femboy cum on tits goth
94%
New Girl in Town
Margo sat next to me in the coffee shop late that Saturday afternoon. His real name was Mark, but he was one of the loveliest Drag Queens in New York City. I had been dressing secretly at home in my mother’s and sister’s clothes for just over three years, but at 18 years old, I had never... Read full Story
shemale lover 2019-06-04 10,180 anal shemale oral sex
100%
The Naked Day Wedding
I'd looked forward to this day with a feeling of excitement and also a certain amount of trepidation. Now the moment had arrived and it was all happening. I looked at my gorgeous bride Tina as we signed the register of marriage in the towns' registry office. Outside, I could hear the bustling ... Read full Story
shemale lover 2011-11-24 3,185 anal shemale strapon
100%
His Perfect Shemale Partner Part 2
Quite a few things have changed since the last chapter. OK maybe not that many, I am still lusting after Sally's body needing to have my dick in her and feel her in me, but we are a lot closer now as we are living together. Sally has gone to her 1st choice University and I decided I would rather get... Read full Story
shemale lover 2011-08-28 4,958 Blowjob shemale cum
100%
Bagging a Bitch with Balls
Watching porn has given me a lot of ideas concerning what to do in bed--and elsewhere. Some of the guys and sluts in X-rated videos do it outdoors--in the woods, a park, poolside, or in a parked car. Some chicks flash their dicks--yeah, I watch shemale movies sometimes, too--in public places, and so... Read full Story
shemale lover 2011-09-27 5,564 transsexual ass fucking tit fucking
100%
The Girl Next Door Ch. 02
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 s... Read full Story
Gwapo67 2022-05-13 5,435 Bareback Creampie Guy Fucks Shemale cum in mouth
86%
Sexy shemale 69
I was out at a casino in Reno after work. It was about 10pm and I was unwinding having a beer playing some video poker and watching ESPN. I saw a beautiful dark hair lady at the end of the bar so I decied to move closer. Once I got down there we chat a bit. Her name was Kim. She had some nice B-cups... Read full Story
shemale lover 2013-06-18 4,453 anal Cumshot suck shemale oral fingering cum swallowing
80%
Buffy the Shemale Vampire Slayer Part 13
Buffy's cock slipped out of Baubo's mouth, and she licked the smooth skin of the stiff, elongated shaft with her tongue. Baubo had no hands, but, even so, she was a superb cock sucker. More than once, she brought the Slayer to the brink of orgasm, then backed off, letting Buffy's sexual passion abat... Read full Story
shemale lover 2011-08-23 3,867 Masturbation pussy shemale
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 21,636 anal tranny Blowjob Big Cock bj Ass to Mouth
100%
Big Surpise In Small Package
It was a Friday night and I was extremely horny and just my luck my girlfriend was out of town, but I wasn't horny for her I was craving cock. I knew I was bi for a long time and loved to have a nice hard cock to play with every once in awhile. So I decide to call my girlfriend to tell her I was goi... Read full Story
shemale lover 2012-06-11 4,405 anal Group Sex Cumshot Blowjob
33%
My shemale GF Part 3
Christy and I are on the couch, we had just woke up, I have a butt plug in and slept with it in cause she was going to fuck me today. She has a Pink G-string on and a Pink bra with her G-string pushed to the side for her cock. Me I'm wearing Metal Mulisha boxers and a Tyler, the creator T-shirt on, ... Read full Story
shemale lover 2012-07-09 3,630 anal shemale cum jerking oral
100%
Totally dominated
I was out walking one night, a walk i used to make with my girlfriend. We had just broken up a few days ago. I don't know why I was walking here again, the memories weren't good ones. She had cheated on me with my best friend. Anyways, I was walking this familiar path through the city streets when I... Read full Story
shemale lover 2012-10-27 5,802 anal Group Sex Cumshot Creampie Big Cock oral
88%
A girl from the bar!
This guy picks up a chick in the bar and takes her to a private room, the only thing on his mind is to fuck her, but there’s a surprise that the chick has prepared for him! When I stepped down to the hotel’s bar I didn’t even notice that girl at once. I sat my ass down on the so... Read full Story
shemale lover 2014-04-23 7,147 shemale ass fucking facial
100%
Sweet Sherri
"The fuck you want," the girl hissed through her teeth. Well, it's hard to say. For one, this was the one night of the week at the particular club that was tranny night. Unless the lucky woman was either a straight freak or had been exposed to the scene, there weren't too many people wa... Read full Story
shemale lover 2011-10-31 5,681 Big Tits transsexual big ass
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 12,640 anal tranny Blowjob Big Cock bj asstomouth
100%
An Empty Hole
"its not working out im breaking up w/ u" The last text he got from his girlfriend that Friday was heavy. It sank, like the hull of a battered battleship, drifting towards the bottomless, cold abyss of his heart. The teen took it hard, harder than most. His emotions flared, rapidly resp... Read full Story
shemale lover 2012-11-13 5,589 tranny Cumshot oral
85%
Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
metamafia 2012-12-21 119,257 hardcore Cumshot sucking bdsm domination
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 4,613 Amateur Cumshot Bareback Shemale Fucks Guy Blowjob blonde Big Cock Asian domination Guy Fucks Shemale Ass to Mouth cum in mouth shemale + shemale
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 4,871 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
50%
I kneel in front of Dominatrix Persephone
Fan Mail. I kneel in front of Persephone.. She looks amazing in Her latex catsuit, but there is something else eye catching. Chance, Persephone huge hó rse c... It looks intimidating in picture, but just think how it must look when it is right in front of your face!! Holding it in my sissy hands, i... Read full Story
Dominatrix Persephone 2024-06-18 3,977 anal Stockings Cumshot Shemale Fucks Guy Fetish Big Cock redhead domination Interracial Mature Homemade sissy femboy teen (18+)
57%
Transsexual Actresses Part 1
The adult entertainment market includes thousands of videos and DVD's featuring transsexual actresses. Some of the more popular of these celebrities have their own web pages. Brief profiles of some of these actresses, including a list of their films, appears after the initial list. Adriana Ventur... Read full Story
shemale lover 2011-09-08 9,407 shemale transsexual porn star
100%
Don't Avoid Daddy
It feels like I haven't been used in ages. I'm too much of a scared sissy. I find guys from all over, talk, email, text sometimes. But when it really comes down to it I get too scared. I've been with this guy before, his cock is soda can thick and he's really rough. The day after my first encounter ... Read full Story
shemale lover 2012-10-23 5,943 Cumshot oral sex deepthroating
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 8,257 Teen (18+) Crossdresser solo Amateur Cumshot Masturbation Fetish Asian Lingerie Homemade
96%
Fucking A Cute Asian CD
I've always wanted to fuck a cute young tranny. I love their femininity - those gorgeous gurl bodies and the way they are into the lifestyle. Such a turn-on. I pulled my cock out of my boy Kevin the other night and the two of us collapsed in a heap, satisfied with what we'd just done. As we lay in... Read full Story
shemale lover 2014-01-29 9,178 Cumshot suck Asian jerking oral fingering
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 4,908 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
94%
My first Shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe that started my intere... Read full Story
SachinJoy 2018-10-04 32,858 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy cum in mouth
100%
Primo appuntamento con Sabrina
Non ho mai incontrato un trans prima di ieri pomeriggio. Mi sono piaciute sempre le femmine ma quando ho visto il profilo di Sabrina su aShemale tube non ho saputo resistere. Quel viso di donna mi attira. E, a dire il vero, mi attirano i suoi video. Così spontanei e naturali. Lei, da sola, che si fa... Read full Story
LoveTSworld 2020-05-05 1,479 Teen (18+) Crossdresser Amateur Cumshot Big Cock domination spanking Homemade balls stretch slut whore ass fingers
100%
Becoming Kacey
I indulged my crossdressing opportunities as often as I could, but as time went on, the chances grew further and further apart. Although I couldn't play dress up in my alone time, the fantasies never seemed to cease. When I entered high school, I dated girls and enjoyed the young passions that teena... Read full Story
KaceyKlarissa 2024-01-16 4,250 first time Crossdresser Amateur Homemade sissy femboy shemale + shemale romantic teen (18+)
71%
My Asian fetish
I have a ongoing fetish and desire to dominate and have as my wife a petite asian sub t girl. I meet her online and fly her here and in the car she reaches over and pulls out my stiff cock. She coooes as she strokes my shaft and tells me how it is just the right size and thickness. She sucks me slow... Read full Story
shemale lover 2012-08-25 3,862 anal sex Cumshot Fetish Asian oral sex
92%
My Brother's Panties
My brother and I are twins, fraternal not identical. Throughout our lives, no one ever confused us, and furthermore, no one ever thought we were siblings. Growing up I would often get the question, "Kevin, why do you hang out with Jamie so much?" People were always surprised when they lear... Read full Story
shemale lover 2013-01-12 13,860 solo sucking jerking Sex Toys swallowing
95%
My first shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe t... Read full Story
shemale lover 2013-07-21 11,885 anal sex ass licking oral sex kissing transexual
90%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 13,578 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
100%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 5,282 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
0%
Brother of the Bride
“What in the ‘Get Out’ hell is going on here,” quizzed the warm, brownish-red woman with the Bantu knots as soon as they were safe inside the gold 1970 Deuce and a Quarter. “I don’t even know,” chuckled the driver as he jerked his head to get his short dreadlocks out of his line of sight. “Wel... Read full Story
Faggyboi and Puzziboi 2023-07-15 5,385 anal Crossdresser Guy Fucks Shemale Interracial sissy femboy faggot sissy crossdresser BB jack of spades bblbuttcd bbl
50%
Tony's 1st Shemale date
The internet was responsible for Tony finding the best sex he had ever had in and considering he was living in Gosport, Hampshire thought he'd never find his dream shemale date and was able to develop an online friendship with an insatiable, sexy shemale. He had begun an affair with Joslyn about si... Read full Story
shemale lover 2012-04-30 3,262 anal sex Cumshot jacking off
100%
David to Dee
"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... Read full Story
shemale lover 2012-07-29 12,724 Cumshot Masturbation oral sex
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 10,747 Masturbation Blowjob blonde ass fucking big boobs
80%
The Farm
“See you Sunday, baby,” said Marcus Jenkins to his wife, Tasha. “Alright! Have a good day at work,” the wireless phone company retail store manager smiled. “Love you, Kobe! Love you, Tiara,” the wastewater plant operator said to his offspring. “Love you, too, daddy,” the youngsters rang out in un... Read full Story
Faggyboi and Puzziboi 2021-12-08 5,749 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
100%
First Encounter (Mexican Travesti)
I grew up near the U.S.-Mexico border and am ½ Mexican Hispanic and ½ Anglo (white). I visited Nogales Senora on the Mexican side on and off during my teen years. As a young adult, I was fearless and sometimes went across alone to visit the strip clubs, get a cheap lunch, or look for Mexican sweetie... Read full Story
AllenB 2022-09-07 7,034 anal sex Shemale Fucks Guy Blowjob mexicana cum in ass first time with a tranny
100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 5,275 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
100%
Dating my Sissy-sister (English)
You are wearing women's stockings and a thigh-high transparent top, the thin shoulder straps of which leave your arms and shoulders elegantly exposed! You're the real lil bunny to me in that girl outfit of yours... How about, should I teach the little one about the naughty girl? I throw you squir... Read full Story
LulaSissy 2024-07-10 1,157 anal Stockings Crossdresser Cumshot Bareback Fetish Big Cock Ladyboy Lingerie femboy shemale fucks shemale cum in mouth shemale fucks female
50%
Giving Away Virginia Holton
Today would have to wait, thought Marla Holton as she hurriedly gathered her bag and notebook in preparation for a no-holds-barred departure from her office at Prism Design. As general manager she had the privilege of arriving and leaving at will, though no one could ever fault her for not putting i... Read full Story
shemale lover 2011-10-08 4,686 shemale cum ass fucking
50%
Freak House Superstar Come Fest
Kiki and Ty Blaze were doing their thing. They were living on their love and passion, literally. The couple had taken their love, passion and desire to please one another and turned it into their livelihood. They had become stars in the world of underground porn. Their production studio, Nasty Nigga... Read full Story
shemale lover 2012-02-01 6,457 anal shemales Group Sex