Sex Stories - Shemale - PAGE 18

Reunion

The reunion was in full swing, as I took in the sight of fellow classmates from my graduating class. Skyline High School was the pride of Salt Lake City, Utah; Go Eagles! Ten years wasn't a long time, but it was a good chance to get reacquainted with some of my old friends. To be honest, I was a little bit of a dick back then. The crowd I sort of ran with, like to harass some of the other kids. We were jocks, without a clue of the effect we had on others. Today it would be called bullying. Back then it was entertainment. I didn't really get into it like others did, but I didn't try and stop it either. I didn't want to rock the boat, but sometimes the others got a little carried away. It was stupid, but many of the guys were good at stupid. The war in Iraq ... Read More»

Cum drenched afternoon

I was anticipating Marla's return from her work related trip out of town for a week. She was due to arrive around four in the afternoon. I wanted to make sure I was ready, so I spent the day preparing myself. I took a long hot bubble bath and made sure I was completely shaved. I sprayed on body spray and applied my make up and fixed my hair. Next I picked out my outfit, tonight would be my catholic school girl uniform. It starts with my white satin crochless panties with rows of little pink ruffles on the back. Marla always likes it when we have our love sessions in panties, and the crochless ones gives her easy access to my love tunnel. Next came the silk stockings, the white button down shirt, my blue plad short skirt that barely covers my ass, then black ... Read More»

A good friend

I have a friend whos name is Novak.We have known each other since we were little kids.We have always done everything together and have no secrets.But he didnt know that i liked to wear womens clothes.He has blue eyes,is very handsome and is very developed and he also plays football.Since we were really good friends i saw his dick several times and it was nice and big. Sometimes i dreamed i sucked it and that he came on my face. One day we came to my place after a night out in town and he was drunk,so i decided to try to seduce him. He sat on the sofa in the leaving room while i was changing into my girl clothes. When i came out he was watching some porn on the tv. "May i do that."i said.He looked at me"Is that you"he asked me."yes its me dear, and i want you ... Read More»

How I got started dressing

I was a sophomore in high school and like any teenage boy I was extremely horny. I masturbated atleast once a day usually 2 or even 3 times because I had so much time on my hands. I started off watching plain straight porn but I watched so much of it daily that I started to get bored of it. I just used sites like google or yahoo to find videos by typing in whatever I was into that day. It started out with just words like "blonde getting fucked" or "girlfriend giving blowjob." Once I started to get bored my words started to get more descriptive "Slut takes huge cock in ass."I was skimming through videos until I found a thumbnail that caught my interest. The thumbnail was of a girl that was tied up with her ass in the air just asking to get fucked. Of course I ... Read More»

Woody and the Tranny

When Woody entered the lounge he had to wait a few seconds for his eyes to adjust then scanned the room. As his eyes roamed the people inside they locked on one person at the end of the piano bar, she was a vision of beauty. She smiled back as their eyes met and he slowly approached the vacant stool beside her. He smiled at himself as his mind referred to the beauty as she or her, it was a gay bar so there was little doubt the she was a he, a transgender, but then that was fine with Woody, he loved making love with other men. "Do you mind?" He said as he nodded towards the stool. "Be my guest." She said. (There I go again) He thought. "May I buy you a drink?" "Thank you, I'd like that." "Bar tender... two of the same please." The ... Read More»

First time I wore girls clothes

When I was ten years old I had a operation on my penis to widen the tube because it was slowly closing and giving me an infection, The doctor cot off the foreskin and widened the tube and sent me home. My Mother thought it was best that I sleep in her bed with her so she could monitor my health and insert the thermometer to keep it widened, she had me wear one of her flimsy night gowns that she wore. This went on for 4 weeks and I grew to like so I asked If I could dress like a girl she told me yes as long as it was only when I was at home,My mother was a prostitute as was my Grandma and Aunts. We lived in a 1800's former mansion so seeing women in various forms of undressing or completely nude was normal. I got turned on watching my Mom but nothing happened ... Read More»

Joe Surrenders

My new partner is not really a girl's idea of a "ladies man." Nevertheless I have known Joe for a long time and when he asked me out I jumped at the chance. I had no illusions about Joe but one asset he does have is a decent bank account! His parents had died and left him with a nice house. He does have a regular job but I also knew that he was comfortably off with an inheritance. Joe is just 28 and I am 33. As far as I know Joe had never had a regular girlfriend. He was far too shy and reserved. My former husband was a womaniser with equipment to match and he was forever seducing a female. Any female, young or old, it didn't matter to him. I finally told him what I thought of him and he kicked me out. Call me cynical but don't get me wrong. I quite like ... Read More»

The first sex! A dream for a little sissy slut!

We decided to meet at your place, I enter quickly and immediately go into the bathroom to get ready for our spicy evening. I'm already shaved and wearing stockings, leopard print panties matching bra. In the rush I'm doing makeup, I get dressed in little black dress, barely covering my bum! I put a 15 cm high heel and at the end I put the blonde wig! One last look in the mirror and I open the door and doing the first step forward. I see you sitting on the couch already naked. I feel your eyes all over my body, you're telling me to turn around a few times and then come on all fours to you. I'm starting to rotate, bend over a litlle so you could have a closer look at me, I kneel and begin to slowly go on all fours to you and whole time looking in your eyes! You ... Read More»

Intervention

My fiancée's girlfriends were becoming a little apprehensive about the changes Angel was exhibiting since we had started dating. They had noticed her attire had become much more suggestive, and her make up more severe. There were other changes too. She was now sporting a tattoo on her right shoulder, an angel/mermaid holding a heart with my name on it. She also had taken up, smoking pot on a regular basis, joined an S & M Club, took stripping lessons and often attended risqué plays and performances. For a formerly demure, Christian lady, this change in behavior was a bit shocking to the friends she had grown up with and had been fellow members of the Bluebirds, International Order of Rainbow for Girls. They were afraid she had fallen under the spell ... Read More»

Franks Friend

Franks Friend Frank is a buddy of mine. We grew up and went to college together. While we were in college Frank and I went on a road trip from Lubbock to Dallas. We got to Dallas went to a few strip clubs and then finally found ourselves on Harry Hines Blvd. It was about 1 in the morning we were both horny and a little d***k. Frank pulls up to this leggy blonde in a short skirt and fishnet hose and asks how much. She told us she would do us for free for a ride home. We said fuck yes. Frank had me drive to her house while he had her in his lap, kissing and groping her. We got to her house and went in. Soon all three of us were on the couch. We could play with her tits, her ass but she would not let us near her pussy. Finally Frank and I were naked with hard ... Read More»

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 wanted me to pop, she'd plunge her head all the way down my pole. Less than three minutes into the BJ, my cock disappeared into her face. I shot my load. Nikki froze while I unloaded. She couldn't say a word, but the bemused look in her eyes told me she was loving every second of it. I must've dropped a gallon of cum into her gullet. But Nikki was so good that not a single drop spilled out of her mouth. After squeezing out the last shot, I leaned back in the ... Read More»

My Girlfriend Has A Dick. A walk on the wild side

Sometimes you never know that you're looking for something until you find it, or rather it finds you. Two and a half months ago things were pretty normal for my wife Molly and me. We've been married for two years and things are still good between us so the last thing I was expecting was to find myself with a piece on the side when she went out of town. At 28 I was still a bit of a horn ball and will do just about anyone or anything. That Saturday with Molly gone I decided that the action in Lakewood was a bit stale, so I was off to Denver. After some driving around, I spotted a bar called Charlie's. It looked interesting enough so I found a parking spot and headed inside. At first I didn't realize that anything was out of the ordinary about Charlie's until I ... Read More»

My night with my Black Master

I posted on this site i would like to be a blackmans sissy,i did get a response from a guy who said he was looking for a white sissy to use i told him i was 55 and never done this before but i would love to be his sissy for a night,we arranged to meet at a holiday inn on the M6, we meet in the bar he was 6 foot 6 and very big build i am only 5 foot 6 and small build i felt a bit scared, once we were alone i would have no chance of stopping him from doing as he wanted to me i said that to him but he just looked at me, he told me to go to the room get dressed in what he had told me to bring and to be kneeling on the floor by the door knees wided apart with my hands on my head and wait for him .i went to the room shaking in side with fear as i went to the room. He ... Read More»

Cheri

My name is Cheri, I live my life in lace and satin. I have always loved the way those materials feel against my soft skin. I have shoulder length red hair and bright green eyes. My friends used to call me Charles but about 12 years ago i had this epiphany that i felt out of place as a man and one night while I was out at a club with some friends, I realized that being a woman felt... I don't know, right, to me I guess. It's been a long road but I'm so much happier now. The first time anyone ever found out I had a dick after that was about 10 years ago. I went to a new doctor for some antibiotics for some throat thing that had been bothering me for a couple weeks. I guess maybe the doctor had talked about me or something, I'm not really sure, but the next ... Read More»

Meet up of a life time with a tranny

So one day a couple of months ago, I needed some BC powder, Chapstick and something to drink. I walked in and headed to the headache isle. As I walked back I noticed there was a really hot looking Latina girl in the same isle. As I walked by she looked up and smiled at me. I said hello and walked on by. I got to the medicine and she was still there but had her back to me. She was wearing tight blue jeans and a black tank top with sexy heels. While she had her back turned I took the opportunity and looked at her butt. Man it was nice. She turned and caught me looking and I went the other way down the isle. I got my things and went to the register. She was there checking out. After a couple of minutes I noticed that she was having trouble with her debit card. She ... Read More»