Free Shemale Stories

Cross-dresser Drinks Cum

Nikki looked up at me with her big, brown eyes as her head bobbed on my cock. Nothing was quite so sweet as one of her blow jobs. She had this way of dragging her tongue along the underside of my cock that made me want to cum in seconds. I always tried to hold it, but Nikki wouldn't let me. When she... read more

shemale lover March 29, 2012 100%

Eve Quest Part 2

Chapter 6 I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed s... read more

shemale lover April 21, 2012 100%

The teenage slut

Hey folks Sandy here once again. I know every time you see me I go up one grade level but this is one tale I felt I should tell you. Let me start at the beginning after me and Bella fucked each other. Well were still together. Laughing, eating together, just having fun basically. We still fuck in th... read more

shemale lover April 25, 2012 66%

The Boutique

Sharon had been working in the little boutique, called The Fabric of Temptation (a name that Sharon secretly thought was just a little corny), for almost four weeks now. She'd applied for a number of jobs for the summer vacation, wanting to make some more money than the allowance her parents gave he... read more

shemale lover May 13, 2012 100%

Mom's girlfriend has a fat cock

When I was a teenager, my mother got remarried...to a woman. At first it was odd, because their roles in the relationship were so clear. My mother was the "bottom", and Jamie was the "top". They're great to each other, and I have grown to love Jamie unconditionally. I'm eigh... read more

TripFontaine May 14, 2012 88%

Daniel, Dani, Dana

After an hour of some hot steamy role playing online I got up from my computer. This newest and best chat friend ever was helping me enjoy this private time more than ever. My feminine alter ego seemed to flourish and delight when I spent time with him in chat. Wearing a little more risque under thi... read more

shemale lover June 8, 2012 60%

Bikini Boy

I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage... read more

shemale lover June 12, 2012 82%

A Sissy's New Daddy

Walking in the door the Friday after my eighteenth birthday, everything seemed great. My parents had gone out of town for the weekend and I was for the first time a truly free man. My older brother had decided not to come home for Labor Day holiday which I was kind of bummed about, we didn't get alo... read more

shemale lover June 16, 2012 100%

Bitch Maker Chapter 3

"Alex bring me some juice." Sammie said, rolling over in bed and hugging her pillow. "Yes mistress!" I replied, with enthusiasm. I crawled out of bed and walked down the hall, on the way past Tim's room I looked in on him. He lay there silent, his cock trapped in it's new c... read more

shemale lover June 24, 2012 75%

Becoming Alanna Part 1

My name is Alanna Monroe and i am currently a college bound 17 year old senior at St. Anne's school for girls in Middletown Conn. I was once Alex Monroe, but after one fateful day four years ago, I became Alanna. Being a proper “lady”, i have all of the assets of my classmates...well tha... read more

shemale lover July 12, 2012 42%

Becoming Alanna Part 2

Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... read more

shemale lover July 12, 2012 80%

Feminized by My Girlfriend Chapter 2

I followed Brook and Linda out of the spa onto the sidewalk and I looked around for the limo but it was no where to be found. As the girls started walking down the street and talking to each other, I asked where the limo was. Neither of them responded and just kept walking. I followed behind as clos... read more

shemale lover July 14, 2012 100%

I punished him..Really

I Was 18,When i bought my first thong.I was excited to Wear it and roam in house,Feeling so sexy about my looks.Just had a quick bath and my thong was ready to kiss my ass hole.I lifed my leg to put in and raised the thong uptil thighs,it became very tight and i made it till my hips hardly.For my ha... read more

shemale lover July 19, 2012 50%

A Visit To an Adult Store

I remember how jealous my older sister always got when I was little and my mother would brush my straight, thick blond hair. "You should have been a girl, Robin," Sis would say, shaking her frizzy, dirty-blond locks. It bothered me because I was not a girl. I was a boy. Mom would sig... read more

shemale lover July 19, 2012 100%

Fender Bender Chapter 2

The bright sun shining through the window woke me up, for a moment I was confused and disoriented. Then it all came back to me. I had sex with Mark and Susan James last night and I was still wearing a pink baby doll nighty and matching panties she had given me to put on before we went to bed. I w... read more

shemale lover July 26, 2012 100%

After Church

I was just horny. All of the time. I just wanted to fuck someone in the worst way. 18 years old, never had a date. Too skinny, too weird. I wore my hair long, not a very hairy body, not very athletic. Just a skinny kid who didn't get any attention. Lot of church girls in the bible belt but they were... read more

shemale lover August 19, 2012 100%

Fantastic Weekend - First Touch

It finally worked! After a year of posting ads on Craigslist, and what I'd decided was my last attempt, I got results. It was short and to the point, "Panty Sub Seeks Oral Top." As is normally the case, I got a lot of one-line responses and picture requests, but buried in there were two gu... read more

shemale lover August 31, 2012 100%

On the Run

“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... read more

shemale lover September 1, 2012 90%

School's Out

Steve asked me if I'd like to come to our school reunion. We were both twenty and being schoolmates seemed a long time ago. I agreed before he told me it was fancy dress. 'Your girlfriend, Sally's ok about this?' I ask dubiously. I knew Sally well, not that we got on particularly and she was ph... read more

shemale lover September 3, 2012 100%

Working for a Living Chapter 6

I slid out of the old Ford truck driver's side door. Surprisingly, my legs felt a bit shaky as my feet hit the concrete driveway of the Malibu mansion. I nervously straightened my cut-off shorts as I walked around the truck. She was waiting by the tailgate with a big smile on her face. "Wow Jai... read more

shemale lover October 5, 2012 100%