Sex Stories - Shemale - PAGE 20

Marceyah and My Wifes Favorite Things

There are two things my wife Cindy and I absolutely get off on when we're really horny. The first thing is I love to suck cock and she loves to watch. The more the other guy and I are into it the better. The second thing we love is, after I'm done with the other guy and he's completely spent, I spend the rest of the night hammering her pussy from every position. She has one requirement that I love, whenever I cum it has to be inside her vagina, always, during these sessions. There are other times when she likes me to squirt on her tits, ass, and even in her pubic hair. But on these nights, it's always inside her. Before Cindy and I got married I'd met someone through a dating site. S/he was a very pretty pre-op shemale named Marceyah, or Marci for short. At ... Read More»

1 st time

I was a student, I had a nice girl. I went out for a night on my own in Amsterdam. In a bar at de Nieuwmarkt I noticed a black woman on the bar and sat next to her. During the conversation I noticed there was something about her, and I knew what. Which set me on fire. I had sucked a friend's cock twice, liked it, but realized then there was something missing: the upper part was all hard and hairy. The woman next to me was really chatting me up drinking white wine. Dressed in een loose flowery shirt, short white skirt started stroking my leg. My hand went slowly undr her skirt and soon I felt something that I expected there. I was hitting the ceiling! She lived closeby she whispered and we went outside. In her apartment we went straight to her bedroom where I ... Read More»

A girl called Eddie

Carrie had always treated me like her little sister, even though we were only third cousins. Though she was only two years older than I was and not of exceptional physical stature, I had allowed her to dominate me for as long as I could remember. Not that she was exceptionally cruel or abusive in any way. It was just that she seemed to realize I was different, long before I myself knew. I could never remember her treating me like a boy. By the time I reached my teens, I was wearing her clothes at any available opportunity, with her permission and no small measure of encouragement. In our secret world, we talked about boys, makeup and fashion, just like two real girls. Naturally, our unusual relationship eventually turned fully intimate, but Carrie only ever ... Read More»

A Close Encounter

Another great tape and another great yank of the crank. Yea, she-males were pretty hot, Tom thought as he hit the eject bottom on the tape deck, but where on earth would he really find one? He had little doubt that if he did find a place where they hung out that there would be more than a few with a serious case of ugly. The chances of finding one like the ones in the video taped he had just been watching was pretty slim. But, he knew if he never went looking, he would never find one. He knew they preferred to be called transsexuals and not she-males as they regarded she-male as a rather derogatory term; the term "tranny" seemed to be okay with them. Getting into the sack with one was a fantasy of his. It wasn't that he didn't like women, he just liked ... Read More»

Caught by my cousin

I'll never forget the first time I tried my mothers pantyhose and high heels on. I slid a pair of tan nylons on and became instantly erect She had these gorgeous two tone brown heels that i'll never forget. They were made with perforated leather. A thing of beauty really. My legs were thin supple and toned so I looked great in them. I remember having the most incredible orgasm that day. The first of many in heels. One day at school they had an auction to raise money for the the seniors grad trip. They had the boys and girls behind a chalkboard. And as I think about it now I am thinking it was maybe a little inappropriate. They had them roll up their pants or they had shorts on. Their legs were smooth so I'm assuming the boys shaved prior to this. Baby oil covered ... Read More»

Josephine's First Evening Out

After the wonderful experience of spending a day at school dressed as a girl I didn't get a chance to repeat the experience. I wanted to, very much, but the following week the examinations started and it was important for me to do well as I was going onto college. Miss Stone and Mr. Graham told me that was no way I could do my exams as Josephine, as it would cause too many problems, so reluctantly I had to accept my school days as Josephine were over. However they were as determined as I was that the end of my time at school was not to be the end of Josephine. One evening they took me to their house. I wondered what was going to happen, feeling an odd mixture of worry and excitement at being alone with them, but this visit was all about preparation. Miss ... Read More»

My weekend with Kelly part 6

Kelly started to rock back and forth on my cock faster and faster. I could feel my cum starting to boil in my balls.We were both moaning in deep pleasure.When I felt I was at the nut busting point, my hands gripped her waist, I told her I was about to cum seconds before I erupted deep inside of her. Kelly's cock erupted as I was exploding deep inside of her. Her cum flying up into the air, landing on my face, into my open mouth.Her cock twitched and shot her load for 5-6 large spurts.Kelly collapsed onto my chest, her cum now on both of us.She looked up at me, smiled and said "That's what I've been wanting for a long time, I knew you would enjoy fucking my sweet, tight little ass. I looked down at her and said "I've actually wanted to fuck ... Read More»

Lovely Jade

My first marriage ended in divorce almost 15 years ago. Me and the first ex just couldn't get things right - we were young, stupid, and hot-headed. I packed my bags and headed for Miami, where my buddy had started a boat-building business. My wife and my 4 year-old son, Jim Jr., stayed in San Francisco. Time passed. I kept in touch with Little Jim. Christmas presents every year. A trip to Florida every year for him. Phone calls. And, oh yeah, child support every month. Jim grew to be a big guy like me - tall, heftily-built, reasonably good-looking. There was some concern among my wife, myself, and her second husband when Little Jim didn't seem interested in girls. But, then, he went to college and suddenly it seemed like he was bringing a new girl home very ... Read More»

CD And Trucker

At least four things went through my mind the moment I heard Hank ask me to go along with him. - One my wife was gone for at least 2 weeks so that was no problem. - Two, with wireless connection and my laptop I could take my job on the road. - Three, I had hardly any clothes in my bag that I was carrying. All the clothes in the bag were girl clothes; my boy clothes were in the back seat of my car. - Four, my ass (oops, my pussy) was on fire and now stinging a bit from Hank's big cock taking my virginity just moments earlier. Who's Hank you ask...he's the trucker that just asked me, a somewhat passable CD, to go along with him on a 'road trip'. Spinning around to talk to him while thinking about those four situations, I turned right into him. "I ... Read More»

Crossdressed cocks

I was looking forward to the fun I could have in my own place. I spent some time on the male chat line looking for someone to play with. he to liked to dress but like me was not at all passable . when he showed up at my place he hade on black thigh highs open toe heels and a corset ,he was taller then me and of average build . it was the bulge in his panties i was interested in. I was dressed in pink thigh highs red strappy heels pink panties and a light purple chemise with a pink bra under it. we sat on the couch watching some porn he took out his semi erect cock and told me he wanted to see me on my knees , i got down on all fours with my ass in the air he stood over me running his hand s over my ass massaging my cheeks making me squirm as he rubbed my ... Read More»

The Training of Julie

The story of the successul aiteration of a good looking youn man into a stunning, talented, ultra feminine boy/girl John was about to learn obedience in the strietbatt sense of the word. his whole life style was about to be changed, The rather alightly built, pretty boy of 17 was to become Julie, a boy/girl, changed mentally and physically to perform as a girl, It all started when he was approached one day by a rather captivating young lady who having Introduced herself quickly won him over to her confidence. They subsequently had several dates and wasn\'t he falling in love with Carol? One day Carol said they had been invited to a costume party and all boys were to come dressed as girls! "It would be so much fun to dress you up, please do it." In the end ... Read More»

Jo and I

It was a typical Saturday morning. I was at the grocery store doing my weekly food shopping. As I was perusing through the vegetable section my eyes caught sight of a a very attractive woman. She had long dark brown hair, pretty face and a nice body. I worked my way over to her and checked her left hand for any signs of a wedding ring. She had none. I made some remarks about the slim pickings the supermarket had. She and I quickly engaged in conversation about cooking etc. We walked around the store side by side picking our own groceries an just having a good time. It was time to check out. I introduced myself and she told me her name was Joann, Jo for short. We exchanged phone numbers and over the next several weeks had lunch a few times. After just a couple ... Read More»

My lesbian shemale adventure

My name's Kimmi and I used to be a stripper. I'm a genetic girl, and I always had a wild streak. Guys liked me 'cause of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts. I danced at a place on Sunset Blvd in Hollywood (this is a true story, so I won't use the name). On the outside, it was a dive, but inside it was pretty nice. The stage was gorgeous, had a generous runway, and beautiful lights. I loved dancing there, and I loved working with all the fun people - especially the D.J. I also made friends with the boyfriends of one of the other strippers. The three of us used to hang out - and that's where this story starts. I had worked a day shift - I got off at about 5 and wanted to go do something. My two buddies, Niles ... Read More»

Isabelle

After my divorce and moving back to the city into a little two room apartment on the third floor of a remodelled office building. It was smaller then the house I was still paying for but at least it was on a front corner so I could watch the world go by. Within a month I had gotten real tired of nuked food and found a small diner about a block away. It was cheap, but the food was good and the helpings always just enough to be satisfying. All in all it had a nice comfy home like atmosphere with friendly waitresses. For the most part the girls where just teenagers, working part-time while going to school. Isabelle was the exception. She seemed to be around my age, early thirties, long blonde hair always tied back and a thin but well proportioned figure. I ... Read More»

Engagement Sex

I've been with my girlfriend for over a year now and love her so much. She is cute, funny, and really sexy. We have a great time and we love to play around a little sexually, but Melissa is a conservative girl and has told me many times that she won't go all the way until we are engaged. Up until recently, I had only seen her naked breasts. God! does she have wonderful breasts. Melissa is about 5 foot 8, 130 pounds, and has size C cup breasts. They are implants, but you can hardly tell, and they feel so nice. She said she was born flat-chested and got her implants to make her look as sexy as she felt. I can't blame her, and I'm not sorry I get to be the one to play with them occasionally. Once in a while she lets me suck on her nipples, which drives her wild! ... Read More»