Free Shemale Stories

Afternoon Delight Chapter 3

When we got to the cottage, the girls stripped me of my jewelry and took theirs off and poured me into the shower. They washed the cum off of me and got me hard again. Damn, Ally and Carmen were all over my cock, giving me a work out. Needless to say, I came a few more times, and we got into the hot... read more

shemale lover August 27, 2012 100%

Woman Cross Dresses for Power & Sex

Tucked in the far corner of a dark, dancehall parking lot, Sarah, also known as Robert, was having sex in a car with Joseph, also known as Josephine. Having sex in a car was no big deal. A lot of couples have sex in cars. Yet, if a passerby could see through the steamy windows, a sight to behold, ev... read more

shemale lover October 9, 2012 100%

Leila My Hermaphrodite Lover

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 after a ni... read more

shemale lover December 17, 2012 100%

New Job, New Life as as Sissy Slut

I was nearing my thirtieth birthday and times were getting tough financially. I had gotten laid off from my job and was collecting unemployment and doing some part-time work helping out friends with odd jobs. One of them suggested that I look into cleaning houses. I've always been very neat and peop... read more

shemale lover December 23, 2012 96%

Training of stacy

Before reading this story please be aware that that some people would label this work as obscene and pornographic in nature. It contains several themes including transgendered, homosexual and lesbian issues in addition to graphic sexual descriptions. To make the action flow more freely and the st... read more

shemale lover April 7, 2014 87%

Ad trap

I saw their ad at the site: “Couple looking for a bisexual guy.” I decided to call them I knew I had to hurry, there were always many people ready to try, I wanted to be the first. When I dialed the number I heard a nice voice, it was a man, he sounded like a beefy man. He turned out to ... read more

shemale lover May 19, 2014 59%

Jenna & Stephen Part 1

Jenna and I have been friends for nearly 15 years. We dated ever so briefly about 12 years ago, but nothing more than kissing and heavy petting occurred before she decided it wasn't going to work out. At the time I was heart-broken, but looking back now, I realize she was correct that we weren't rig... read more

shemale lover September 1, 2011 85%

My First Time Out Part 4

It was Sunday morning at eight o’clock when the phone rang. Shayna’s eyes felt like they were glued shut but managed to answer the phone on the third ring. “Morning,” said Shayna as she was still half-asleep. “Good morning Shayna. This is the Bell Captain calling.... read more

shemale lover October 18, 2011 50%

Tina's Secret

My name is Jordan Conrad. Those of you who read my "Rebecca's Secret" series probably remember me. If you've never read them, I guess I should give you a quick summary, so you're not in the dark about what's been going on in the past few months of my life. Bear with me during the slo... read more

shemale lover November 2, 2011 100%

Vegas Baby: Swinging for the Fences

"Hello," Miss K said as she answered the phone. "Where are ya? You're gonna be here in 5? Alright. You got the address for IHOP, right? OK, See ya in a bit. Bye." "So is this girlfriend of yours on her way?" Jennifer chimed in. "I mean if she doesn't exist, this... read more

shemale lover November 15, 2011 73%

Ticket To Paradise

Oh, no! Toni Matthews thought as she saw the red, blue, and amber emergency lights flashing in her rear-view mirror and heard the shrill siren of the police car shrieking like a banshee. She was being pulled over by a California Highway Patrol officer. She’d been speeding, she knew, but maybe,... read more

shemale lover December 19, 2011 100%

Debbie Part 8

Moira sat in her booth at the entrance to the subway station and saw people pass by. She sat there every day selling tickets, and although several thousand people passed her during a shift, she could now recognize many of the regulars and she even knew when to expect them. It was now almost 9 o'cloc... read more

shemale lover December 23, 2011 100%

Going Up

Siren was perturbed at herself. After months of fruitless effort, she'd managed, at last, to land an audition for her first speaking part in a major motion picture. The scene in which she'd appear, if she was selected, required nudity-and full-frontal nudity, at that-but it might, at long last, b... read more

shemale lover January 1, 2012 66%

Blue collar Master, white collar slave

I sit on the couch in my owner's house, dressed every bit the slave I am. My body from the tips of my toes to my eyelashes is completely and permanently hairless, smooth, soft and beautifully tanned. My upper body is clad in a thin, soft and pink rubber T-shirt and my ass is clad in a pa... read more

shemale lover January 12, 2012 50%

Chinese Extremes Part 2

When he woke up, it was like waking from a very vivid dream. Oddly enough he quickly accepted that it had not been a dream, but he did find the determination that had been missing the day before. It may have been a longtime sexual fantasy of his to be feminized against his will, but in the real worl... read more

shemale lover January 17, 2012 80%

The Trip Part 2

I awoke suddenly feeling dazed and with my head pounding. "Kara, baby...you okay?" asked Chris Chris roused from his slumber and reached for me. I was sitting up, breathing hard. "It was nothing. Just a dream, I guess."

 "Okay. If you say so." He rolled ove... read more

shemale lover May 20, 2012 100%

A Ski Bunny is Born Chapter 4

Our next port of call was Copenhagen (Denmark!). We left London early one wet afternoon and flew across to Denmark's capital, which was also wet! The flight was relatively short and when we arrived we caught a taxi to our city center hotel. We had 5 full days here and were intending to enjoy each on... read more

shemale lover June 22, 2012 71%

Your Waitresses

You begin your evening by taking a long luxurious bubble bath followed by taking the time to apply your makeup at a beautiful white makeup table and mirror from the 1920's. You then slide a sheer pair of black stockings up each leg and attach them to your black and red lace garter belt. You then run... read more

shemale lover August 10, 2012 66%

Digging for Home

Never Make the Last Out at Third After some minutes, Charlie broke the embrace. Backing away a step, she steered her moist brown eyes into Frank's damp grey ones. "What now?" The man tilted his head to one side and shrugged. "I'm not sure. It hasn't been a day yet since you went... read more

shemale lover August 25, 2012 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 more

shemale lover September 30, 2012 100%