Free Shemale Stories

Summer School

Dan woke to the sound of birds softly chirping outside his apartment window. Excited, he sat up realizing that he now finally had the apartment to himself the entire summer. He could do what he wanted and wear what he wanted. No longer did he have to keep many of his "pretty things"... read more

shemale lover January 30, 2012 100%

Danielle's First Time

Danielle was born in the winter to 1976, but she was born a male by the name of Daniel. Daniel looked like a normal male child aside from liking girly things. Whenever Daniel would play dress-up he'd always dress in his mother's or his aunt's clothes and his parents thought that was cute until Danie... read more

shemale lover February 3, 2012 100%

Shemale Seduction - The Surrender

I cannot remember what drove me to it. Cruising bars for sex had become a habit. Success can do that to you, but even steady success make you yearn for something different. I looked at her from across the bar and acknowledged her stare. She definitely looked hot and hungry, with eyes that seemed to ... read more

shemale lover February 3, 2012 100%

Worthy

I knelt down in front of her, nude, my hard cock head bouncing up and down with my breathing. I was so excited, I could barely control myself. Her panties were black rubber and kept her well in place but, I knew the secret treasure they held and wanted it so badly. I clasped my hands behind me and w... read more

shemale lover February 3, 2012 80%

A Change Of Luck Part 2

I froze when I heard the voice, because I knew who it belonged to. "Well, well, well...what have we here? I never thought I would get to see this - my roommate sucking off a girls cock!" I turned around, Lena's cum still splattered on my face, and looked at Gina. I was plastered with... read more

shemale lover February 18, 2012 100%

Heart Shaped Ass

I couldn't believe my luck. Just came home from a long day at work and wanted nothing more than to unwind. Alone. Get my thoughts together, shower, and have a nap. I then noticed my trash bin was getting full and said "Fuck it!". Might as well take it down now and be done with it. After to... read more

RazedGlory68 February 24, 2012 100%

Baroque Buggery

All through college, Jim Benson had earned a reputation for being a little... eccentric. More than a little eccentric, actually. He had an unusual sense of humor, strange taste in fashion, and probably the worst luck of any human being on the face of the earth. Nonetheless, with his good look and ch... read more

shemale lover February 25, 2012 0%

A Dare Gone Right

'Well, Paul, if you're not man enough, just say so!' 'Come on, that's not fair, Isabel. I've never dared you to do anything this risky,' I replied. 'Oh yeah? Walking around the mall in a pink latex micro-skirt and no panties wasn't risky? My balls were swinging around for all to see!' 'Yeah... read more

shemale lover February 26, 2012 100%

Becoming a Cock Worshipper Chapter 2

After sucking Ray he let me use his shower to clean up. He led me upstairs to a rather luxurious master bath, with an enormous marble tub, with expensive looking twin shower heads. Before showering I paused to admire myself in the mirror: I was stunned by my appearance, my lipstick and eyeshadow wer... read more

shemale lover February 29, 2012 100%

Caitlin and Mistress Vicky Chapter 2

I hummed softly as I put the finishing touches on the salmon. Teriyaki salmon was my wife's favorite dish and it filled me with pride to know that I was making her happy. My mouth watered slightly as I arranged the tray. (I would only be having a salad myself, as I had to maintain my figure.) Tak... read more

shemale lover March 1, 2012 50%

Carly is My Xmas Surprise

I’d been living in my building for a couple of years now. I was one of the few who owned an apartment there, so there were plenty of people renting who came and went. Mostly the building was filled with couples. I was enjoying the single life still. Let me tell you a little about me before we ... read more

shemale lover March 8, 2012 100%

Cast a Sexy Spell

I love my body. From my long red hair that drapes over my shoulders to my firm breasts to my slender arms, legs to my round ass. Most of all I love my cock. Yes, I have a cock. It swings between my legs at around 5 inches when not in use and stands proudly at eight and a half when hard. And when I'm... read more

shemale lover March 28, 2012 100%

Becoming Missy

It all started back in 1973 in Seattle, Washington. I was 21, living on the south side with a couple of buddies while we were all stationed at area military bases. One Friday night we had a party at our apt. I was standing outside by my car smoking a joint when this guy pulls up in his pick-up. &quo... read more

shemale lover March 31, 2012 83%

A Pleasant Surprise

I really do enjoy my swing life style. Here is an example of one of those times. My lady has this friend, "G" and I wasn't to keen on her. But thank god she lives 4 hours away. I usually bail out on my lady's visits and she is cool with it. But then once my lady begged me to go with her ... read more

shemale lover April 2, 2012 66%

Fulfilling A Girl's Male Fantasy

"Get undressed," the pretty brunette told me, and I obeyed. She was called Jennifer, we'd met the night before at the rock nightclub, and I'd thought that she looked gorgeous in her goth make up so she invited me back to her place. It turned out that she was eighteen and still living at ho... read more

shemale lover April 4, 2012 100%

Fulfilling A Girl's Male Fantasy Part 2

Since our first meeting had gone so well, Jennifer and I started going out together. Other than the fact that in the bedroom I was the "man" only about half the time, it was a fairly normal relationship, apart from possibly being even more open with each other about our desires. One day a ... read more

shemale lover April 4, 2012 100%

Where Am I??

I was at the bar on a Saturday night drinking as usual. I was scoping out the girls and hoping I could find something to spend the night with. I found absolutely nothing. I continued to drink and drink and drink until I blacked out for the most part and cant really tell u anything after that. When I... read more

shemale lover April 13, 2012 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 more

shemale lover April 14, 2012 100%

A Real Fantasy

It was a boring Wednesday evening. I was away from home on business. With nobody to talk to and nothing good on the TV I decided to go for a walk. I walked for a few blocks and noticed the neighborhood was changing from hotels and bars to strip clubs and adult bookstores. I had never been to a strip... read more

shemale lover May 28, 2012 100%

Hermaphrodite gang bang park

INTERSEX GANG BANG THIS STORY IS 80% TRUE. I DID NOT CHANGE VERY MUCH OF IT I'm intersex. The medical term used to be “Hermaphrodite.” They even distinguished a “True Hermaphrodite” from “Pseudo Hermaphrodite.” A “True Hermaphrodite has an &ldquo... read more

shemale lover June 7, 2012 100%