Sort by
Relevancy

Free Stories

77%
Anything to make a sale
“David, you are not the right sales person for this account. I know the CEO of Cybertix very well, he’s been a client of mine for years, and he won’t relate to you.” I was sitting in the office of Victoria, my boss. There was a big sale opportunity at Cybertix and I badly ... Read full Story
shemale lover 2012-09-17 4,941 first time Cumshot Lingerie domination oral sex cum eating
100%
First Time as a Cum Slut Chapter 2
The next day I was very excited and nervous. I put on black stockings, black lacy panties, matching bra, padded it out, and put on a pale blue top with a short flared pleated grey skirt. As I walked along to the spot, I had butterflies in my stomach and nearly turned to go back home, but he appea... Read full Story
shemale lover 2012-10-05 3,102 anal cum oral crossdressing
100%
Proud To Be A Sissy Chapter 3
I woke Monday morning actually looking forward to what the day may hold and feeling good about myself. I felt like I was a different person and as I thought about it realized that in a few ways I was. I laid in bed thinking I did have a little better understanding of my sexuality now that was so con... Read full Story
shemale lover 2012-12-23 7,505 Crossdresser sucking Big Cock Lingerie ass fucking
94%
A Thrilla in Manila
I finally got my wish. For the last twenty years or so ,I've had a secret desire for lady-boys. For the past few years, all of my masturbation fantasies have involved lady-boys. The fantasies involve sucking their cocks or having them enter me anally. Over the past several months, I had been e-mail ... Read full Story
shemale lover 2013-02-21 5,264 Cumshot sucking facial big boobs swallowing
60%
Ass Whore Laurie, Double Penetrated
Ok, its Friday evening. My C List ad is finally published, "Ass Whore 4 MMM Tops" and waiting....waiting for some horney guys eager to pump up a hot sissy cock whore and willing to be in a group! Lot's of responses (my pics never fail!) but only singles looking for a one on one. So, I... Read full Story
Chasis88 2014-03-27 4,196 Crossdresser hardcore Big Cock ass fucking dp
100%
I FIND MY ROAD IN SYGKROY
My name is Anastasia, although the real name is Nick. As you can see I'm a decent boy day, a normal relationship with girl (not so normal, but that another story!), Sociableness and not effeminate at work and generally to the outside world. But when you go home and my girl is missing, I beco... Read full Story
ANASTASIS CD CRETA 2014-12-03 4,059 first time Creampie Blowjob ass fucking 69 cd
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 19,210 Stockings Fetish Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
90%
Long weekend at work
So I am the low man on the scale at work. My job is with the City I work in dispatch and am one of the people responsible for getting road crews, hydro and sewer crews out to fix problems wherever they occur. My boss is a very attractive woman named Jamie. She stands about 152 centimeters and dar... Read full Story
Zöe from Kingston 2018-08-09 6,111 Cumshot Bareback Shemale Fucks Guy Blowjob cum in mouth
80%
Three In A Day
Clara felf especially slutty today. She briefly gazed at her long legs shimmered in the smooth, silky black stockings, and black patent leather pumps as she pressed the gas pedal of her car. Her olive skin and black wig were set off by the brightest shade of red lipstick she could find. Driving d... Read full Story
iluvgurls 2018-11-12 4,771 Small Tits Crossdresser Group Sex Cumshot Blowjob cum in mouth
83%
Janine awaits
My story is not typical. Sure, it mirrors many of the others you’ve read except for one aspect, that is my age. I recently celebrated my sixtieth birthday. Yep, the big 60. And not that I am trying to brag but I am one of the sexiest bitches around. As recently as five years ago I looked like any ot... Read full Story
bunny cat 2019-02-04 3,956 Crossdresser Masturbation Blowjob Lingerie Mature 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 6,756 Cumshot Shemale Fucks Guy Guy Fucks Shemale cum in mouth vampire
95%
Best session with a T Girl
I like T-Girls. Recently had a chance to go to Costa Rica for work. While I was there I decided to see what Costa Rica had to offer in this department. There is quite a good amount of girls to select from. I started texting this Tgirl and we set a time. I got ready and headed over. It was a Hotel th... Read full Story
horny.hiker 2019-04-30 14,967 Stockings Masturbation Creampie Shemale Fucks Guy Lingerie rimming Ass to Mouth escort ts no lube anal fuck just saliva
80%
TG Girlfriend moves in (part 2)
My wife Lydia and I have been married about 9 months, we have a very close TG friend, Joanne, that lives next door and every once in a while, we get together, and all go out and enjoy. We have had sex together, and when Lydia is away Joanne, and I are together at every opportunity. Joanne and I work... Read full Story
Jon Paul 2022-01-21 3,612 Big Tits Cumshot Bareback Creampie threesome Blowjob Shemale and Girl Guy Fucks Shemale
100%
My Love Letter To Joanna Jet
I await my goddess on my knees, my heart pounding in my chest as I hear the sound of your footsteps outside my door. You knock and I spring to my feet, opening the door. You enter, pushing me aside and closing the door behind you. You are radiant, tall and curvy, with long black hair, smooth cara... Read full Story
TgirlLover4Life18 2022-04-12 2,497 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy blonde Big Cock Lingerie Mature Ass to Mouth
100%
I fucked the hotel handy man and he had a monster cock
I was on vacation in a new town and decided to stay at this new hotel. I heard it was the best and the location was close to some sites I wanted to explore. I enjoyed my stay there, especially one evening when my air conditioner stopped working, and the hotel guy came to fix it. He looked so hot tha... Read full Story
Madison Heights 2023-09-05 7,079 anal ass Big Tits Cumshot Bareback Creampie Fetish Uniform piss Ass to Mouth cum in mouth monster cock watersports
100%
Crossdressing at CCBC in Palm Springs
I recently stayed at CCBC in Palm Springs. For those of you who are not aware of it, it is the largest gay resort in Palm Springs area. The resort has about 30 rooms, lockers, a pool, steam room and indoor and outdoor play areas all on a one acre outdoor enclave. I arrived there on a Tuesday and dre... Read full Story
Rocky8844 2024-05-27 4,123 Crossdresser Group Sex Blowjob Lingerie pantyhose cum in mouth
50%
My Descent
This is the first time I've told my story publicly. I wrote this maybe 3 years ago, and have shared it with one person. I used to cross dress in my hotel room while away on business trips. I'm a fat bald 46 year-old who looks ridiculous dressed up in ladies underwear. When you're obsessed, tho... Read full Story
shemale lover 2011-11-05 3,386 anal first time cum oral
80%
A Drive in the Country
It had been a rare hot dry day and the evening promised to be hot as well. Toni the lovely CD I have met down here in Wales arrived as arranged just before dusk in his car to collect me and take me somewhere secluded he had found for some outdoor fun. We drove about a mile before Toni pulled over... Read full Story
shemale lover 2012-02-29 4,088 Stockings Blowjob huge cock wanking cd
100%
A Job in the Theatre Chapter 7
The next day Paula woke late in the day. She lay in bed feeling the glow from her bottom. It was totally erotic and the most satisfying sexual experiences she had ever had. The more she thought about it the hornier she became. She grabbed her cock immediately focused on how much smaller it was th... Read full Story
shemale lover 2012-03-13 2,792 Stockings cum oral sex
100%
A Night of Makeup, Cock and Cum
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further,... Read full Story
shemale lover 2012-04-18 4,897 Cumshot jerking off domination Sex Toys cum swallowing
100%
A Tale of Cum and Passion
It was an anonymous meeting, set up through a popular Internet site. The profile specified I was looking for a transsexual or a transgender woman with nice legs and feet. Basically I was looking for a chick with a cock to satisfy my fetishes for legs, stockings, feet, cock, and cum. Victoria walk... Read full Story
shemale lover 2012-07-06 4,208 anal sex Cumshot shemale oral sex
100%
Ana in Action
I had fantasized about him for months. I just wanted to know what it was luck to have him pulsing inside me, to feel his body pressed against mine in sheer lust. I just had no idea that it would actually come about and that my wife would be the hook up. You see, Jim has been one of my wife's drinkin... Read full Story
shemale lover 2012-11-23 3,143 threesome cum fuck oral
88%
Sucking My first cock
It all started earlier this week, I had begun to watch a lot of sissy hypnosis videos and training videos, mainly ones from Polish Mistress. Every time I watch these videos, I usually would just end up masturbating or going on Cam/Phone with someone. But, after watching a 35 minute faggot hypnosi... Read full Story
shemale lover 2012-12-17 16,653 first time cum oral swallowing
87%
Encounter with a dominant shemale
One night I was feeling really horny. I just came back from the gym and I wanted to release and relax. I then began my search for some fun on the personal ads section. I have always been into shemales especially verse aggressive ones. I found this one particular post about Asian bottoms. I was c... Read full Story
SecretAznMan 2013-06-28 48,377 Cumshot Shemale Fucks Guy Big Cock Lingerie ass fucking ass licking big boobs
86%
My TS experience in India, Pune
Im 6 ft tall fair with handsome looks and regular exercise keeps me fit and healthy. Im also blessed with quite big and thick cock with indian standards. Im total shemale fan and I watch shemale porn crazily every day. I was in search of TS or Shemale in pune since long then one day I was searchin... Read full Story
daynightfun7 2013-07-10 13,401 suck shemale fingering ass fucking Guy Fucks Shemale condom sex
94%
In Love with a Shemale
I was out one night in a busy club and I couldn't help to notice this one girl staring at me constantly. She was incredible wearing a tight little skirt showing off her long legs with an amazing smile and a very cute face. I planned my move and went to the bar when she did and she started talki... Read full Story
curiousshemalelover 2014-11-29 10,495 tranny suck Shemale Fucks Guy ass fucking domination oral sex
56%
Big cock shemale from Pune, India
I just saw her profile on Planet Romeo, her name is ID is Kaynat / Muskan. I saw her photos and got attracted to her. I am always a big fan and lover of Shemales or TS. I called her and fixed appointment by negotiating with her for 2500 INR. I went to meet her, she stays in a condominium in ... Read full Story
Stud4Shemale 2017-05-22 96,405 Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
60%
Sucking mature huge cock stepdad
When mom passed my stepdad KEN was alone for 3 yrs he made comments like you need tighter shorts your hair smells pretty one day as I was Su king my friends 5 inch cock as he surf cum on my face KEN walked in my room then told my friend to leave I started to cry and he said it was ok he new i was a ... Read full Story
Cumsuckinfool11 2018-04-11 7,855 Crossdresser Blowjob Ass to Mouth cum in mouth Big cock dad
100%
Jennifer's first taste of cum
This is another in a long of line of true stories about my crossdressing experiences. This encounter happened back in the 90s. It was Saturday night and I was on the road to the Queen Mary in Studio City. For those of you who were into the scene back then, you know what a happening place the Mary... Read full Story
JenniferJones 2019-01-22 8,847 Crossdresser Amateur Blowjob cum in mouth
88%
Tommy Tries to Make It Up
Tommy Tries to Make It Up I have written about Tommy before. He was the eighteen year old neighbor that always stared at me checking me out, basically eye fucking me and that made me so hot and horny I eventually took his virginity and trained up on being a great lover. Well he had moved out... Read full Story
pennypenny 2019-04-30 6,379 Crossdresser Group Sex Bareback Creampie threesome Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth
92%
Del's 1st sissy
Sometimes an occasion just pops right up for me to satisfy my sissy side. My wife had decided to take the kids on a mini weekend vaca up the coast. I had a lot of daytime work to do, but I remembered her friends Del and Ceci were around. Del is so horny all of the time, he's a bit of a perv, but I f... Read full Story
smtmsbrianne 2020-09-01 5,567 Crossdresser Cumshot Blowjob Ass to Mouth cum in mouth
97%
Shemale fucks guy - My gf fucks my slutty ass.
I have a shemale girlfriend & we both are in a relationship. One day, I decide to give her a visit. I'm 5'7 guy & she's 6 feet. That makes her tall & intimidating & whenever we meet, it's me who become her gf. I visit her, she takes me in. SHe pulls me towards her while giving me a deep kiss. I ... Read full Story
glodobox 2020-12-04 22,839 Amateur Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Homemade cum in mouth
100%
Why I’m a Cock Whore!
Hello Love, The summer before my freshman year in high school. I found a VHS porno video right next to a dumpster behind our local video store. Brought it home. Couldn’t watch it until my family left to use the VHS player. It turned out to be a she male porno at first I felt weird but after watch... Read full Story
Samantha Cummins 2023-04-18 6,398 anal Stockings Cumshot Creampie Lingerie femboy Ass to Mouth cum in mouth
100%
Philippines Vacation with a Dominant Big Cock Ladyboy
I am still in a state of unbelievable joy that I was lucky enough to experience this but I 100% did and I can’t stop thinking about it as I thought things like this only happen in porn or fantasies. Buckle up because this is a wild one and happened in Manila May 2024. I had the opportunity to vi... Read full Story
AllenB 2024-07-14 6,134 Bareback Creampie Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale cum in mouth domination act filipina ts filipina ladyboy
87%
Big Booty Black Boy Gets cheated on
I have been secretly bi throughout my life. But nobody has known. I have had several girlfriends and all. One physical trait that I developed at the age of 18 was a big booty. It grew so much that I couldn't hide it much. One time I went to the gym with tight clothes and my curves were obvious. A lo... Read full Story
Flatch 2015-10-29 7,661 tranny ass Ebony
100%
Taken and in Public Part 3
I tried to go to sleep but was just so horny; I wanted to dress up again; I wanted to go out; I wanted to be fucked! All these emotions were running thru my head and I just lay there. My mom told me she would be starting the 7pm to 7am shift at the hospital for some time and thought I should get... Read full Story
shemale lover 2012-01-14 3,031 Fetish crossdressing ass fuck
85%
TV Cum Slut
As we sit on the couch watching Shemale porn, my friend Bob turns and asks. "Do you still wanna be my buttslut?" "Yeah, Hell Yeah! We've been talking about it for a long time." He smiles "Did you bring some stuff to get dressed up? You keep talking about it, and I'... Read full Story
shemale lover 2012-01-27 4,891 sucking cum domination crossdressing
50%
She-Male Pimp Daddy
I’ve been working the streets for a long time and I know all the ends and outs of the flesh market. I have six she-males that work for me and I get 50% of everything they make plus all the sex I want, any time I want it. I make them work seven days a week rain or shine. I buy their clothes ... Read full Story
shemale lover 2012-02-05 2,738 asshole Big Cock cum
100%
Back to School
It all started the day John got a letter in the mail; it was an invitation to his school reunion back home. John was proud of what he had achieved in his life; he had a good job and a house. The only secret John had was that he was a closet cross dresser; he loved to feel feminine from time to time.... Read full Story
shemale lover 2012-02-09 4,065 Shemale Fucks Guy orgy cum swallowing
100%
A Job in the Theatre Chapter 6
Paula fell back against the couch and closed her eyes. What a marvelous experience it had been! She absolutely loved to suck cock! She loved everything about it. She loved the taste of cum too. She couldn't wait to do it again. She could feel the dried sperm caught in her hair and knew there was ... Read full Story
shemale lover 2012-03-12 3,174 Stockings anal sex oral deepthroating
66%
She-Male Pimp Daddy
I’ve been working the streets for a long time and I know all the ends and outs of the flesh market. I have six she-males that work for me and I get 50% of everything they make plus all the sex I want, any time I want it. I make them work seven days a week rain or shine. I buy their clothes ... Read full Story
shemale lover 2012-03-23 3,629 anal blonde cum Asian Sex Toys
75%
The Succubus with a Cock
His cock felt so good between my lips. I savored every inch with such great passion he moaned and fucked my head farther down his shaft. I gagged many times but I was getting better at deepthroating. His balls were coated with my saliva, and soon the couch we were sitting on became wet to. I really ... Read full Story
shemale lover 2012-05-18 8,154 hardcore anal sex Cumshot cum swallowing
71%
Stephon fucks Sora and her sexy tranny ass
Ya know what fuck it since my last story wasn't good apparently imma just cut the bull and tell the whole story now shit. So my dick is in her ass and im in heaven, like on some cloud nine shit.the head board is knocking she screamming, im not sure how loud though cause im pretty focused.And like... Read full Story
shemale lover 2012-05-25 3,324 anal sex orgasm ass licking oral sex
100%
Bday wish cum true
It was my thirtieth birthday and my wife Alisha had a surprise planned for me, it was one surprise that I will never forget. I found myself on a plane going to Amsterdam, Alisha had planned a dirty weekend for us and what better way than to spend it in Amsterdam. We did the usual, walked round the r... Read full Story
shemale lover 2012-08-14 4,841 Masturbation cum domination oral sex
66%
An Ass to Die For
It's a very strange thing. We all have our personal quirks. The things that make us unique and stand out from the crowd. I've just never met anyone besides me who has mine before, and to tell you the truth I'm not sure if it's a gift or a curse. You see, I have a girl's ass and not just any old girl... Read full Story
shemale lover 2012-11-13 4,215 big dick sucking porn
100%
Proud To Be A Sissy Chapter 5
I awoke in almost total darkness, only a soft glow came into the hall from the kitchen. At first wondering where I was, my bed at home wasn't as soft as where someone, probably my new daddy had carried me after falling asleep on the floor. I shivered in delight remembering how my daddy had shared me... Read full Story
shemale lover 2012-12-24 6,407 Cumshot sucking Lingerie ass fucking cd
92%
Proud To Be A Sissy Chapter 6
It was still early and I wanted to enjoy the feeling of being dressed in my shear hose and garter belt, tiny g-string panties and matching bra and the form fitting shiny black mini dress that barely covered my stocking tops for as long as possible. So I spent some time doing some domestic chores and... Read full Story
shemale lover 2012-12-24 6,447 sucking domination ass fingering deep throat cd
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 7,366 Cumshot sucking ass fucking Guy Fucks Shemale ass fingering
76%
Sissy Ghetto bitch part 1
-The Guys 4 ghetto guys was inside a porn site looking at random sissy babe pictures when they accidently found a picture of someone they know. Like every album they clicked it that specific one with a tranny dressed so girly with mouth open. The guys had such a stone hard erection by watching al... Read full Story
shemale lover 2013-06-01 6,333 suck Big Cock cum jerking gangbang doggy style Interracial cd
100%
My adventures with a TV
I recently had a fantastic time with a beautiful crossdressing friend of mine. Before our date, I had no idea that he was. I did know that he was gay and that him and I were going to get together for some fun... Wow! I didn't know how much fun I was going to have with "her." It had been... Read full Story
shemale lover 2013-05-31 3,719 Stockings Crossdresser sucking Blowjob cum ass fucking
90%
She-Male Pimp Daddy
I’ve been working the streets for a long time and I know all the ends and outs of the flesh market. I have six she-males that work for me and I get 50% of everything they make plus all the sex I want, any time I want it. I make them work seven days a week rain or shine. I buy their clothes an... Read full Story
shemale lover 2013-07-18 5,082 anal sex Cumshot big boobs strapon shemale sex
88%
In my bedroom...
Daddy walks in to my room and lays down in bed, right behind me. He starts caressing my stocking covered legs…daddy likes it when I lay in bed in my sexy lingerie. I’m wearing a white garter belt, white stockings and silky white panties. Daddy caresses my sissy bum as he starts kissing my neck and m... Read full Story
lea1234 2014-10-07 5,738 Cumshot suck ass fucking 69 cd
78%
Bikini contest
I was at this beach bar in Mt Pleasant SC. There was a bikini contest that day. As I attended, the contest started. I was 23yrs old and the thought never crossed my mind about a tranny. However this was supposed to be all girls. Nobody, including me suspected this girl that won the contest was a tr... Read full Story
jim3801 2017-08-09 19,355 Small Tits Ebony Lingerie Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
86%
My adventure at the adult bookstore
I was horny as fuck the other afternoon. I had some time to kill so I hit squirt.org and fetlife seeing if there were any dudes needing a free blo-n-go. Nobody took me up. Sad face. I drove to the local adult book store that has video booths. I was sitting in the parking lot watching people go in... Read full Story
shedawg 2019-04-15 6,479 Amateur Outdoor Blowjob cum in mouth
83%
The sissy dreams
Everyday I wake up in a state , halfway between a happy sissy and a closeted white boy. My mind is constantly trapped in that state. Suffering in silence, the people in my life seem to be oblivious to it, I have it well hid. 48 years of fist fights and weed, long hair and leather coats, Oilfield job... Read full Story
badbadboi667 2021-01-04 5,553 Crossdresser Amateur Group Sex Outdoor Bareback Creampie Blowjob Big Cock gangbang domination Homemade Ass to Mouth cum in mouth
100%
Quick trip to the park
Monday Morning again, I hate Mondays, why can’t the week start on Tuesday! Thought Justina ,while she stood semi naked in the kitchen drinking her coffee with a semi. I finished my coffee and made my way to my bedroom to get dressed. As I entered my bedroom i spotted my new dress i’d bought on S... Read full Story
Samantha Jewels 2022-01-12 2,545 Crossdresser Amateur Cumshot Outdoor Blowjob Mature crossdressing Ass to Mouth cum in mouth crossdresser amateur