Sort by
Relevancy

Free Stories

50%
Domination of Bjarne
Dear Diary. At the behalf of my lover Bjarne alias Cigar54, I will ease the curtain of my bodouir and invite the curious reader inside to a little piquant seance that we had together during his recent visit over here. Bjarnes visites always begins with kissing deeply, while my hands find the way to... Read full Story
Louice 2018-03-02 3,322 Amateur Shemale Fucks Guy domination Ass to Mouth
100%
My Afternoon With Venus - Part I
It was a stunningly bright and clear Saturday morning when I left my house to head out and run some errands. Nothing big, just little odds-and-ends that had been building up that I needed to deal with someday and it seemed like this was as good a day as any ... little did I know how good the day wou... Read full Story
funpics 2018-03-23 13,113 Amateur Shemale Fucks Guy Asian Guy Fucks Shemale Homemade
92%
Caught in the act...
One summer, my cousin Nancy came to stay with us for a while, as her parents had gone away on a cruise trip. At 18 years old, she was a couple of years older than me and in the full bloom of her young womanhood, so to speak. She knew it, too, and it was obvious that she had no problem at all in pull... Read full Story
caroletv31 2018-04-23 18,932 Stockings Fetish Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
82%
Halloween Double Cross
It all started off so innocently... My wife Jo, tall, slim, blonde, aged 40 with 34DD tits and the sexiest big ass imaginable, works as a doctor. Her hours are long and arduous. She often comes home completely worn out. Only during the holidays does she tend to recover her sparkle. She is gorgeou... Read full Story
ASSEaster5678 2018-10-29 11,287 Shemale Fucks Guy sissy Halloween
100%
yes, Mother give it to me
"Do your fucking job right, Henry! Jesus Christ, what are you, five years old? If I ever have to call you in here again, you're done! You hear me? You'll never work in this business again! Now get the hell out of my office." Mona could feel every set of eyes on the floor anxiously awaiting the pi... Read full Story
ASSEaster5678 2018-11-28 12,760 Guy Fucks Shemale
100%
My lusty landlord
Gopal Reddy has been my landlord for about 7 years now. I rented his flat back in 2015 at Whitefield, Bangalore and have been staying there with my mom. Gopal Reddy and his wife Manjula are from Anantapur, Andhra Pradesh and they keep visiting us whenever they come down to Bangalore. Both of them... Read full Story
Manusha Tranny 2022-12-12 4,314 Crossdresser Amateur Bareback Homemade Ass to Mouth cum in mouth
50%
KING OF TRANNY CHASERS ENTRY 1
IT WAS AROUND 1AM AND MY GIRL FRIEND GINA AND I ARE GOING AT IT.HER NAKED BODY WAS HANGING OFF THE BED IN DOGGY.HER BIG CARAMEL ASS CHEEKS JIGGLED AS A POUNDED FROM BEHIND. SHE WAS SCREAMING "YES BABY" AND MOANING NON STOP..AS BEAUTIFUL AS SHE LOOKED AND HOW AMAZING HER BACK SHOTS WERE LOOKING..W... Read full Story
Ghostface drillah 2024-07-02 805 Amateur Big Tits Masturbation Big Cock Ebony Guy Fucks Shemale big ass Homemade Ass to Mouth cum in 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 8,989 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
91%
MY FIRST TIME WITH A SHEMALE
I`ve always had this fantasy about being with a shemale,i guess something about a chick wit a dick and tits always turned me on,i`ve always been curious about wat it`s like to be fucked by one.Well last weekend was a weekend i`m gonna remember for the rest of my life bc that was the weekend i decide... Read full Story
shemale lover 2013-06-21 15,025 tranny Cumshot Shemale Fucks Guy Big Cock fingering swallowing
78%
Once wasn't enough!- my 2nd shemale exp
So after my first experience I got really into the porn I bought movies magezines got on websites just couldn't get enough. But watching it wasn't enough I had the real thing once and wanted it again. It had been almost a year now and only one person knew about what I had done that one fat... Read full Story
Duke04 2017-04-01 10,430 anal sex Shemale Fucks Guy ass fucking Shemale on Guy
87%
First time in Key West
I've always been fascinated by shemales.  Aside from having an overall appreciation for how the male member in general functions and, when properly stimulated, pulses and pumps...cum spewing from the tip.  I've watched any number of webcam shows where guys jerk off.  And yeah, I've wa... Read full Story
peepholeman 2018-01-04 28,198 Amateur Latina Bareback Blowjob Ass to Mouth cum in mouth
88%
LONDON CINEMA LIAISON
When I lived in London back in the 80s and 90s, I would often sneak off to a porn cinema with stockings, suspenders and knickers under my suit. My wife didn’t much like sex, so this was a release for me to get away from home and have some sexy fun. Once I had found a suitable seat I would ease down ... Read full Story
GinaG 2018-12-14 7,093 Stockings Blowjob blonde Lingerie Guy Fucks Shemale Mature Ass to Mouth
25%
Fantastic threesome w/ Miranda Pinocchio & Danielle Albuquerque
Today taken by the craving for something really big I call Miranda who answers me immediately and despite the language barriers and her way of speaking not always understandable we agree for 70 and a quiet thing. I sling in Naples, central area, the usual low in the alleys between via Marina and the... Read full Story
RonWisley 2020-05-04 4,677 Amateur Cumshot Shemale Fucks Guy threesome Blowjob Big Cock
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 4,047 first time Crossdresser Amateur Homemade sissy femboy shemale + shemale romantic teen (18+)
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 4,832 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 5,441 transsexual ass fucking tit fucking
0%
Mike and Chris Together
Mike's sex life had taken a definite series of turns for the worse. When he called one of his favorite partners, Stella, she apologized for not returning his earlier calls, and told him she had been very busy lately. "I'm really sorry, Mike. I've had some great times with you, and I will alw... Read full Story
shemale lover 2012-02-07 5,177 anal sex Creampie Shemale Fucks Guy Guy Fucks Shemale
100%
Crossdresser Caught in Act
I do not consider myself gay, nor do I think I am bisexual, but I do enjoy a nice big cock. I am not attracted to men at all and under normal circumstances find any and all homosexual activities quite disgusting, until I get really horny that is. When I get all hot and hard, I can't help but want a ... Read full Story
shemale lover 2012-03-31 5,654 Masturbation Sex Toys crossdressing vibrator
98%
Fantasy cums true
I was on a business trip staying in a nice Hotel. After a business meeting in my room I called down for room service. The maid came up a few minutes later and I let her in. She was stunning, 5' tall with black hair and the bluest eyes I have ever seen. Under her uniform you could tell she was very w... Read full Story
shemale lover 2013-07-11 8,508 anal sex Cumshot suck Creampie Shemale Fucks Guy fingering
93%
Loving TS Sex
living in a medium size city 30 years ago, it was necessary to stay into the closet. That way of live is really still the reason why I never outed myself, even after years living in different bigger cities and several countries. I had acquired a taste for transsexuals, considering them the best o... Read full Story
shemale lover 2013-12-08 4,850 tranny sucking Shemale Fucks Guy ass fucking condom sex
77%
Chicago TG Romance (part 3)
It is Sunday morning, just barely dawn and I have just spent the weekend with the most amazing girl. You know when everything clicks and it seems that at first you have met the person you want to spend time with and share with. Beth was standing at the glass windows full length and the sun was just ... Read full Story
Jon Paul 2018-06-04 4,273 Cumshot Asian Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
83%
Las Vegas Swingers
It had been over 6 months since I seriously dated someone, and I was getting depressed and in a rut. I had directed my attention to my work and it kept me from feeling sad about my loss of someone I almost married. I had met a transsexual girl that absolutely adored, but she was tragically killed. (... Read full Story
Jon Paul 2018-06-11 10,240 Amateur Guy Fucks Shemale Mature Ass to Mouth cum in mouth double anal shemale + shemale
92%
MY TS FOXXY & VENUS LUX FANTASY
Alyssa Gomez and Venus Lux were visiting Newark, NJ and decided to have lunch in the restaurant that I work in. It was a rainy day. The seductive pair were returning back to their suite in the Courtyard Marriott, but not before grabbing a bite to eat. Alyssa and Venus sat the bar and ordered a coupl... Read full Story
I_GO_3WAYZ 2021-03-02 11,261 Latina Creampie Shemale Fucks Guy threesome Blowjob Ass to Mouth cum in mouth double anal
100%
My first time having sex with a Tranny
I have been obsessed with Trannies for as long as I can remember. There is something about a gorgeous feminine woman with a big thick cock that drives me crazy! I turns me on so much that I kept pushing myself further with my love for Trans women. I bought sexy dresses, underwear and heels to wear s... Read full Story
Joe22lovests 2021-09-15 11,841 first time Shemale Fucks Guy Blowjob Big Cock
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
100%
Got my ass pounded in Miami by a tranny escort
Got my ass pounded in Miami by a beautiful tranny escort with a 10 inch thick cock. Years ago I was in Miami for a business trip. Four days just me in my hotel room. I decided to treat myself to some of the X rated channels that my hotel provided. As usual I went straight to the tranny porn.... Read full Story
My Shemale Attraction 2023-01-03 6,767 Amateur Big Tits Masturbation Creampie Shemale Fucks Guy Blowjob
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
100%
Jo, Shemale Goddess! Part 1
Jo plumped the cushion and carefully positioned it until it was precisely at the right angle. Nothing less than perfection would do. Ricki, her friend of twelve years was coming to stay overnight and she would notice if the tiniest thing was out of place. An impatient knock on the door signalled ... Read full Story
shemale lover 2011-09-04 5,459 anal sex sucking shemale
90%
My Night with Luisa Tavares revisited
I've made some adjustments to this story and will be writing a sequel. Hotspur I flew to Goiânia just to be with Luisa Tavares. She greeted me at the door to her apartment in a bathrobe. She had just taken a shower and invited me to do the same. When I returned from the shower, I found her sitti... Read full Story
hotspur 2020-01-10 11,315 Shemale Fucks Guy Blowjob Big Cock domination Ass to Mouth
93%
Homework
Daniel was a 15 year old teenager, like any boy his age, he was full of hormones and sexual fantasies for every pretty girl that passed in front of him. In the last weeks of the school year, the history teacher had a child and was absent from school, being replaced by teacher Marlene, a trans woman.... Read full Story
haroldãosanguebom 2024-01-09 7,084 Shemale Fucks Guy Big Cock Mature
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 5,144 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
80%
A Fairy Tale Part 1
=-=-Chapter One-=-= "Heather?" My boyfriend was knocking on the bathroom door. "What's wrong, are you okay? Heather?" "Yeah..." I swallowed thickly and that was a mistake. I threw up some more, kneeling on the floor, feeling like I was dying. "Heather?&q... Read full Story
shemale lover 2011-12-06 11,475 Bareback cum ass fucking slave
83%
the start of what to cum
I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often mo... Read full Story
oliviabecket23 2023-07-04 6,739 Crossdresser Lingerie domination Sex Toys femboy forced webcams
40%
First Sexual Crossdress Experience
How my secretary found out I'm a bi TV and how me and my TV friend educate her into some of the more zany aspects of TV sex. *** As I laid back against the wall of the toilet with my nylon-clad thighs spread wide and my erect cock jutting up lewdly from between them, the wooden door in front o... Read full Story
shemale lover 2012-09-27 5,581 first time Fetish cum oral crossdressing nylon
100%
Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
shemale lover 2012-11-27 11,000 Fetish crossdressing feminization
100%
Camming down the rabbit hole Ch1
Back in January 2020 I guess I was lucky, I did have a regular job although the pay was miserable and I did have my own place. On my wage all I could afford was a miserable bedsit in a neglected part of town, but on the upside I didn’t have to flat share and it worked well enough for me. The west... Read full Story
Dani_does_Dallas 2021-08-11 5,395 Crossdresser solo Amateur Masturbation Lingerie Homemade webcams