Sort by
Relevancy

Free Stories

100%
Head Cheerleader Mikki Part 3 Michael is Back
To understand this story you must read the previous chapters. It's Sunday morning and I'm just waking up. I'm in bed alone. As I get up I see myself in the mirror. Still dressed in powder blue lingerie and a blonde wig. I wonder where the girls are. I leave the guest room and go into mine. I stri... Read full Story
shemale lover 2012-06-14 2,747 anal sex Cumshot Fetish
100%
Bringing Daddy's Work Home
"Whew! I can't believe this shit." Marilyn Walker, recent high school graduate, stared into the reflection in the bathroom mirror and breathed deeply, thinking to herself about her latest situation. Here, she was standing in the bathroom of the office of some city bureaucrat whose name ... Read full Story
shemale lover 2012-09-25 7,000 Cumshot transsexual oral sex
100%
Working My Way Through College Chapter 2
Saturday morning, I awoke wearing the same panties and baby doll nightie I wore to bed. If I hadn't, I might not have believed what had happened Friday night. It felt pretty good to walk around like that, so I went to the kitchen, and made some coffee. As it percolated, and as I drank it, I couldn't... Read full Story
shemale lover 2012-09-30 3,102 anal sex Cumshot crossdressing
100%
The Blood Pact Chapter 4
I finished that single mug faster than I would have liked. However, with the room so warm and the ale so cold, I just couldn't help myself. With head thrown back, I drained the last gulp and slammed the mug down on the table with a movement that was perhaps a little too masculine for my outward appe... Read full Story
shemale lover 2013-01-30 3,975 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
68%
I meet my new Mistress for the first time
I was feeling excited about and looking forward to Friday night. The reason for this was that I intended to dress up as my alter ego, Tania Harvey, and to go for a night out to a club nearby that is popular with TG’s, TV’s and other like minded people. I took a lot of care and attention over the way... Read full Story
Tania Harvey 2017-06-26 8,135 Amateur gangbang 3some shemale on shemale dominating
100%
Stepping Out
All through the next week we searched through almost all the online dating sites and it was the same as before. Some wanted just me or just Deena, but not the both of us together. One good result was that I found a trans gender support group and they were going to meet on the next Tuesday which was ... Read full Story
Setinkhan 2021-06-02 3,088 Crossdresser Fetish Big Cock Interracial cum in mouth shemale + shemale
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 6,012 anal Shemale Fucks Guy Fetish Blowjob blonde Big Cock domination Mature deep throat cum in mouth sandals toe sucking
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 3,347 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
100%
My Noisy Upstairs Neighbors
So... I just moved into my new apartment a few weeks ago, and ever since then all day every day I have been hearing loud noises from my upstairs neighbors. Not just normal walking-around noise, but loud and heavy bangs, crashes, and poundings against the floor, my ceiling. Not only was the sound ann... Read full Story
Chrissy Tunnell 2024-07-15 1,187 Crossdresser Bareback Fetish Blowjob Ladyboy gangbang domination Guy Fucks Shemale sissy double anal
100%
First Cock Came From Old Friend
It was Saturday and I had nothing to do so I decided to go for a drive. I got into my car and headed out of the city in no particular direction. After driving for a while I realized I was close to Jim's house. We have been great friends for years but have not seen each other for a long time. I decid... Read full Story
shemale lover 2011-10-03 4,810 asshole oral sex teasing
75%
Bambii's New World
My mind was racing the whole time. I couldn't believe where I ended up. But the sensations were running through my body. A 9-inch cock was ramming my boy pussy as hard as it could. Another cock, at least 10 inches, was being forced down my throat as his hands wrapped around my head, forcing me to... Read full Story
shemale lover 2011-10-05 5,163 shemales Blowjob cum
100%
Additional Thoughts on Sodomy
Although, in the world (or worlds?) of pornography and erotica, it is politically incorrect, perhaps, to suggest that the body, whether male or female, is not built for anal intercourse, the fact is that anyone who has participated in this act (especially on the receiving end) or who has enjoyed wat... Read full Story
shemale lover 2011-10-05 3,999 Creampie sperm anus
100%
High Rent Tranny Whore
It's morning already and I wish I could just sleep but Maria has a client coming in at 10:00AM and Jasmine is here already to wake me up. Jas is great and has a huge cup of French Vanilla Coffee for me. "Wake up Barbie, Maria will need the lounge to dress and get ready for her session".... Read full Story
shemale lover 2011-12-03 3,150 taboo Fetish crossdressing
100%
Enchantment of the Shadow Realm
It was a enchanting night. The moon was full. The street light reveled an other worldly stream of fog through what I could see of the dark forest. Unfortunately I was having a hard time appreciating all this beauty. I was stranded. I had missed the bus and had no way of getting back to my hotel. I h... Read full Story
shemale lover 2012-04-14 3,992 Group Sex Cumshot Big Cock facefucking
100%
Thursday night at the Gloryhole
So I went out to meet some friends on thursday, after a day of drinks we split or seperate ways. I started walking towards union square with the intent of grabbing a few drinks then heading home. As I got there I saw the bars were crowded so I started walking farther into the tenderloin not really w... Read full Story
shemale lover 2012-06-19 3,217 Cumshot shemale oral sex
87%
Feminized By My Mother Chapter 2
My mom was staying in as were Jen's parents so we parked on a dark road and made out while I fingered her. Her panties were absolutely drenched when I was finished, and she rubbed her hand inside them and used her pussy juice to jerk me off, I spurted all over my pants and she laughed. "I ho... Read full Story
shemale lover 2012-07-24 13,168 sucking Fetish fucking sissy
83%
Discovering Amber
I have always enjoyed women's lingerie. From looking at catalogs to seeing girlfriends wearing it I have loved the look and feel of sexy, silky lingerie but for me it has always gone deeper. At 18 I tried on my first set of panties, oh my God that was wonderful! It was all downhill from there. Event... Read full Story
shemale lover 2012-09-28 6,186 Cumshot Fetish Lingerie oral sex
100%
French Frolic
Where to begin? It is never easy to know where to start with a confession. The easiest place to start is at La Rue - a tiny little dive of a club just a couple of blocks from my hotel in Paris. I had only been in Paris a couple of hours. I was extremely jet lagged but only had a few days to make the... Read full Story
shemale lover 2013-02-21 5,672 Cumshot sucking Blowjob facial domination
87%
Alex
I'm a straight guy! a few years ago, I stubble the cross shemale p***. now I must say, it felt weird, I mean being used to watching females doing p*** on my life. but I have to admit, these shemales that I was watching were passable, and most of all looked very f*******. shemale p*** made my di... Read full Story
Mike212 2018-05-28 6,659 Teen (18+) Small Tits Amateur Blowjob Ladyboy Guy Fucks Shemale
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%
The Day I Went SheCock Crazy
I summed up courage to meet up with my old shemale flame Fransicca (she is a Malaysian but living in indonesia) ... messaged her, she sounded excited and asked if i minded her friend joining us. 'Why not' i said. It was settled. we booked a villa for the next day. I checked in early. cleaned up ... Read full Story
Sara Banks 2021-04-26 6,577 Group Sex Cumshot Outdoor Bareback Shemale Fucks Guy Fetish Blowjob blonde Big Cock Asian Ladyboy gangbang
100%
TG Neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
Jon Paul 2022-04-22 6,557 Big Tits Cumshot Latina Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 3,615 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
100%
Escorted
Hello! Would it be possible to have you send an escort over? A beautiful escort. Not a plain looking woman but someone special, ok? .... Ok, got it. Thanks. I opened my door to a very very sexy woman. Dressed in a tight short dress that hugged her hips and accented her nice size titties. A very bea... Read full Story
Curious_billy 2024-03-13 5,767 anal Amateur Bareback Creampie Shemale Fucks Guy Blowjob Homemade
72%
Got dominated by 2 shemales on the last day in Thailand
I took a trip to Thailand when i was 25. I told my friends I wanted to go alone so I could clear my head. The real reason was that I wanted so see some shemales. When I first arrived I spent a day looking at every club I could find in search of a good Shemale. It was nearly a week and I couldn't ... Read full Story
shemale lover 2015-08-05 12,246 Asian ass licking domination
100%
The Hottest Shag With Naughty Sheena!
I was home one night, feeling kind of down and lonely and that is why I started browsing the dating sites. I wasn't really serious about it, I just needed something to occupy my mind. I came across of free shemale chat and thought to myself that it might be fun. I started chatting with a really stun... Read full Story
shemale lover 2015-12-25 6,640 big dick Cumshot asshole
80%
Caught Watching Free Mobile Shemales
I was watching Free Mobile Shemales on my phone browser during my lunch break when the phone rang. Annoyed by the fact that someone is interrupting my free time, I answered angrily "Yes, who is it?". "Wrong number", said a female voice, "Sorry to interrupt you lunch!", ... Read full Story
shemale lover 2016-05-20 9,367 anal sex Cumshot asshole
80%
Leila
I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most. It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before. I'd stayed over at a friend's house and af... Read full Story
shemale lover 2011-09-27 3,595 sucking shemale stroking
100%
Connie at an Adult Bookstore Part 2
Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * In the previous c... Read full Story
shemale lover 2011-09-30 8,586 Big Tits Blowjob deepthroating
66%
The wonderful adventures of miss K: Down by the river...
Miss K and Tracy walked through the park by the Gateway Arch, content to spend a nice spring day enjoying the outdoors instead of another piece of flesh. Tracy had one a pair of short, tight daisy dukes with a light pink crop top that showed off her tight stomach and nice legs. Miss K herself... Read full Story
shemale lover 2011-12-01 4,214 shemale oral ass licking nipples
100%
Just One of Those Days Part 2
Hello again. My name is Amanda, though sometimes I use the shortened version Mandy, when the mood suits me. I'm 33 and have stayed single for three years, since I discovered that Richard, my boyfriend, was not only cheating on me with dozens of women, some my so called friends but was al... Read full Story
shemale lover 2011-12-09 3,238 cum massage shemale sex
50%
I am Baaack! Part 4
It was 2:00pm, exactly five weeks after The Meeting. Jessica stood fidgeting behind the Vaingirls cash register. Things had returned to seeming normalcy after The Meeting, but all the secondary participants in Rose's plan knew it was like the Phony War of 1939/40, and that things were being done beh... Read full Story
shemale lover 2011-12-15 2,575 crossdressing erotic encounters fantastic
100%
Tony to Tanya Part 2
Tony woke up on Saturday morning feeling excited without knowing exactly why. He tried to sit up, but his left arm was pinned down by Sarah's body. This was normal for a Saturday morning, since she tended to sleep at Tony's house on Fridays. The reason he was excited suddenly hit him. On Tuesday,... Read full Story
shemale lover 2011-12-19 3,152 sucking transsexual cum swallowing
100%
A Maid Family Part 2
Sitting up with a start I felt the cold wet cloth that someone had put onto my brow fall into my lap, and then shortly after that I felt it slide in between my crotch and then onto the seat of the leather sofa where as luck would have it the damn thing then wedged up against me, and after a few ... Read full Story
shemale lover 2012-01-02 3,696 shemale femdom tg
100%
Mieke and Ellen
It was early morning when I first met Ellen and Mieke. I was walking the dogs and they were out too with their dog. The first thing I noticed was that both of them were gorgeous. The second thing was dissapointment as I saw that Mieke was way too young for me. I'm 27 and she looked as though she... Read full Story
shemale lover 2012-01-22 3,160 Cumshot shemale oral
85%
First Time with she-male
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny. S... Read full Story
shemale lover 2012-04-29 4,683 first time Cumshot shemale small cock
100%
Birthyday Party Chapter 2
It was now about 11 pm and Sue and I have been at it for the past 3 hours. Sue had me get up and go into the bathroom. As I stood in the shower I thought of what we did. Sue knew how to pull the right strings on me or in me. And she knew what pleased me. I washed all over. I had no idea of what was ... Read full Story
shemale lover 2012-06-24 2,241 anal sex Cumshot shemale fingering oral sex
93%
First time
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny... Read full Story
shemale lover 2013-07-20 4,969 first time Cumshot oral sex Guy Fucks Shemale kissing
73%
Nancy the hot and sexy TS in Pattaya
Hi this is Ris, this is my third story. Well Last year I went to Thailand on lone trip. I went directly to pattaya and had rest and went to Walking Street in the evening. Was visiting many nude bars, ts Bars, dance bars. but while walking on the street one particular girl catch my attention. s... Read full Story
Stud4Shemale 2017-05-22 9,482 Big Tits Cumshot Shemale Fucks Guy Ladyboy Guy Fucks Shemale cum in mouth
88%
Seattle Weekend
Saturday morning and such a beautiful day nice and cool morning I went for a run. I consider myself in fairly good shape for my age but I try and make it to the top of a hill in our neighborhood. I get winded fairly quickly. Coming down the hill I ran into a nice looking athletic girl, maybe 38 year... Read full Story
Jon Paul 2018-08-09 10,078 Big Tits Cumshot Bareback Creampie Blowjob Ladyboy Guy Fucks Shemale cum in mouth
66%
Oh Samantha
Meeting Samantha for the very first time at the busy theatre restaurant was the best thing that could ever happen to me. She was performing with about 20 other ladies or sort of ladies, I found out later that they were hot shemales, transsexuals and even a few transvestites. Their performanc... Read full Story
iluvgurls 2018-11-12 4,493 Cumshot Shemale Fucks Guy Blowjob Lingerie
100%
MY FIRST TS EXPERIENCE
I was traveling for work across the country. It was a long day. I arrived at the hotel, checked in, went up to my room and took a shower. I was hungry so I went to the restaurant in the hotel and wound up at the bar where they served food. I was alone so I sat at the bar at the only available sea... Read full Story
nico19878 2021-10-01 6,186 Amateur Blowjob Guy Fucks Shemale
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
88%
Alex and Jon
Alex was not beautiful, but had a sexy attractiveness that most could not help but take a second look. This was the case with Jon as he searched adult Friend-Finder ads for someone that would satisfy his desires and dreams of a companion. Alex, a transgendered Filipina girl, had the bronze skin colo... Read full Story
Jon Paul 2022-09-21 5,307 Group Sex Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale cum in mouth
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
16%
Current Fantasy
I really wanna get fucked for the first time and my dream way of doing it, always wanted to do a porn. The dream is that I go there and get done up in such a way, I am unrecognizable, just looking the best. Have a tranny come in and do my make up, the way she likes it and gives me a preview of what ... Read full Story
martley 2023-06-30 5,260 anal Amateur Group Sex Cumshot Fetish Big Cock Lingerie big ass Homemade femboy shemale fucks shemale cum in mouth
50%
A Fantasy - Part 3
Sharon put her cell phone back into her purse, turned to Paula and I and said "I'll be right back, with the Chinese food!", gave us a wink and took out her wallet, grabbed some money and then went off to get our dinner. Paula was sitting on the floor, she leaned back on her left elbow and started... Read full Story
swollenrooster 2023-09-20 5,287 Group Sex Cumshot Shemale Fucks Guy Fetish gangbang Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
94%
Foursome with two ladyboys
It's been quite some time since I posted a new shemale story here. Hope all of You who have experience with shemales will finally have some courage to write about it and share it with us. Let this sizzling story by Tommy be an inspiration to You. Who wouldn't want to be in his place in this crazy fo... Read full Story
shemale lover 2015-03-15 6,715 Group Sex Blowjob cumshots
68%
Extra credit for me
After failing my mid-term exam my day was ruined. I headed back to the dorm crying. Through lunch my friend consoled me and suggested I make an appointment with my professor for extra credit. I called the office of Dr. Writt and was told to show up at 2:00 sharp. At 2:00 I knocked on the office d... Read full Story
shemale lover 2015-06-27 6,543 tranny Cumshot threesome
100%
Charisma Part 2
After fondling her breasts and her cock and balls for several more minutes while she probed Tiffany's mouth with her tongue, Charisma allowed her guest to get undressed while she removed her own clothes. The seamstress was a beautiful woman, for a genetic female, but, of course, she was nowhere n... Read full Story
shemale lover 2011-09-03 3,045 anal Big Tits Cumshot
33%
Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
shemale lover 2011-10-01 8,999 Stockings sucking domination
50%
The Zodiac Coins: Libra
2400 YEARS AGO... He was a humble shepherd. It was night and the flocks were sleeping. As he gazed at the stars, he saw a shooting star. He knew it was a portent of some kind, but was not mystic enough to know what. A little while later he saw another shooting star and guessed that wha... Read full Story
shemale lover 2011-10-18 4,661 Group Sex Masturbation shemale oral
81%
Rebecca's Secret
-1- The hour was growing late as I looked around the cozy living room. Six of my friends were sitting in various places, in various positions, all watching some late night horror movie on the television. There was a feeling of general contentment. We had arrived at the house several hours earlier... Read full Story
shemale lover 2011-10-19 5,240 Cumshot shemale oral sex
50%
Film At Eleven
I'm a shemale. I'm also an exhibitionist. And a news hound. These interests, as I've learned, don't always go together--or maybe they do. Let me explain. Since becoming a woman in every detail but my genitals (which remain, as they always shall, defiantly masculine), I've delighted in "accid... Read full Story
shemale lover 2011-10-29 3,311 Cumshot Masturbation exhibitionist
100%
Permanent Stay in Mastersville Part 2
I had some time to think about this as she dragged me out the front door and threw me into the backseat of her car, shut the door and left me there as she went back into the house. I sat there in the car thinking about what would happen to me, if Mistress had really meant what she had said about tur... Read full Story
shemale lover 2012-01-08 4,371 toys bondage and discipline heavy reluctant
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 6,669 Cumshot sucking Big Cock Shemale and Girl