Shemale Stories

[a9127]

The inspiration for this comes from something I read on the Internet... now that guy could write!

"I got fucked by a shemale for the first time. Her name is Kylie. I like girls with muscle. So I let Kylie fuck me all night long.

She is the only one that fucked me till now. And my ass is very sore.

She does drugs and it effects me and my dick stays limp. She sometimes doesn't even touch my dick while fucking.

She is almost 5'5 and weights 130 pounds. But she lifts me and fucks me. And it is amazing. She lift me in cradle and front carry.

She loves that she is stronger and had way bigger dick than me."

(Personally I consider this to be my finest work yet. Much better than those silly fantasy stories I've posted... Why would I want to wake up in 1978 in a gorgeous, sexy, blonde transwoman's bed anyway? )

[a9127]

As a “30 something” virgin. I have always found it hard to meet women. Especially since I am barely 5’6”, fat, and have a micropenis. When I was a kid I was small and weak and never allowed to play with the “big kids.” When I tried out for football in 6th grade coach told me to get the fuck out of his office.

I have been with prostitutes but even they couldn’t do much with my little “stub.” One tried her best to get me off but ended up laughing so hard I just got dressed and walked out.

Earlier this year I started going to “tranny bars” downtown. It’s really hot to see a woman with a big dick. Last week one of the dancers took me home with her (I can’t afford a car) after she said I was cute. When we got back to her place we both got drunk and started fooling around. Soon she had her cock out. It must have been at least 12”! I got down on my knees and started sucking. At first, I was kind of embarrassed. I had never sucked a cock before. But she said “You're doing great baby.” Just before she came, she stopped, turned me around and fucked me in the ass. It hurt at first but she was very gentle and soon I was rubbing my tiny cock. Pretty soon we both came.

Afterwards she showed me her wardrobe and told me I’d never be able to fuck a woman “with that little thing” but I could make a great “sissy slave” if I lost some weight. So she started taking me to the gym with her. She’s a personal trainer. Soon I was able to fit into some of her outfits. We spend the weekends together at her place where she lets me dress up like a slut then service her. Sometimes she ties me up, uses the whip on my ass, and makes me call her “mistress” as she fucks me. Only after she comes does she let me rub my little “clit” to orgasm.

[a9127]

OMG. Fuck me. I had forgotten all about this post.

Where DO i get these ideas from?

[a9127]

During my Sophomore year of college I developed a friendship with a guy who was very feminine looking and acting. He was from California (the Los Angeles area), had shoulder length blonde hair, shaved his legs and body, and typically wore shorts and cropped t-shirts around the dorm. His name was Jordan. He was a Chemistry Major and very smart. We would often stay up late in his room eating pizza, drinking, watching TV, and talking about stuff well into the night. Many of the other guys in our dorm thought he was gay and talked about him behind his back calling him names and making fun of him.

If you have checked out some of my other posts or WordPress site, you know that my first girlfriend was transgender. Stephanie and I met when we were both 12 and she was still known to me as “Stephen.” Before we started high-school she began her transition and we dated exclusively through our Senior year. She is the first girl I was ever really in love with and the person I first had sex with. Sadly, after we graduated, we broke up. My family moved to Indiana from Michigan and I ended up going to college at Purdue University where I also played football. (Yeah, I know, everyone thinks I played at U of M. Makes sense. I had been to many games in the “Big House” as a kid and have met Tom Brady and Charles Woodson. My entire family graduated from there except for my Dad who graduated from Michigan State. I had a full-ride scholarship to “State” and had to “start over” when we moved.)

Anyway, at a Mid-Western school like Purdue, Jordan was sort of an “outcast” and although at the time I had a cis girlfriend, I used to look after him to make sure he wasn’t bullied. I remembered what Stephanie had to put up with. At 19, I was listed at 6’5” 264 lbs. and alternated between defensive end and middle linebacker. I could also bench over 500. Yes. Really. Must have been from all the “vitamin supplements” I took of course.

Jordan in some ways reminded me of Stephanie early in our relationship. But really nothing ever happened between us. Until late in the Spring semester. During Finals Week, through one of Jordan’s other friends, I got word that several guys in the dorm were planning to dress him like a girl, beat him up, and throw him in the Wabash river (a common hazing and bullying practice). Late that night I went to “visit” them down at the other end of the floor. I banged on the door and told them to let me in. They were of course all smoking weed and high or drunk.

There were five of them. I told them what I had heard and that Jordan was my friend. I said if they had any problems with that we could settle it right now. Of course they didn’t and I said “good decision.” Before I left I told them if anything ever happened to Jordan I would fuck them up. There wasn’t much they could do. Besides the only guys around bigger than me were some of our “O Linemen” (all well over 300 pounds) who were also my teammates. Chances were good they would back me up if anyone gave me any shit.

A few days later, Jordan and I were hanging out, watching TV, and sharing a bottle of Jack. He was wearing a bathrobe and I had on only my black Nike spandex “training shorts.” Finally Jordan turned to me and said “I heard about what happened, Andy. Thanks.” I said “No problem.”

Getting up and then kneeling in front of me Jordan took off his bathrobe. Underneath he was wearing a red satin bra and panties. Very hot. Looking up at me but not saying anything he proceeded to take my hardening cock out of my shorts and suck it. I didn’t stop him. Laying back on the bed I let him continue until I came in his mouth. It was great. Then it was my turn. I removed his bra and licked and bit his nipples gently. I started to stroke his cock ever so slowly. Stopping me, he got two pairs of handcuffs out of a drawer and let me cuff his wrists to the supports of his bed. We kissed and made out while I continued to stroke him. Finally I knelt in front of him and sucked him off swallowing all his cum.

Releasing him from the cuffs we laid down together on the lower bunk. His roommate had gone home for the weekend and so we watched TV for a while then dozed off.

He would transfer to UCLA the next year. That was the only time we ever did anything and of course I never told my girlfriend about it. She and I would continue to date for a while then I met a graduate Nursing student several years older than me down at Indiana University. She and I dated that summer. Later that Fall we were married. She is my "ex" that I have mentioned in other posts on here before.

[a9127]

Rome 79 AD. During the Feast of Jupiter I at last won my freedom in the arena. So many years have gone by, I cannot count the number of men I have killed, it must be in the hundreds. Before I was captured and enslaved by the evil leaders of the coup against the government, I was General of the Legions of the North. Trained in all methods of combat, and veteran of countless battles, I was selected to be a gladiator, determined to win back my freedom and return to an ordinary life. I was declared a “Hero of Rome” by the true Emperor and my citizenship was returned to me.

To make up for my loss, I was presented with a huge villa made of beautiful marble, with lush gardens, a courtyard, gymnasium, and indoor waterfall. I was paid all back wages from the military, plus a pension totaling many millions. This made me one of the richest men in Rome and because of my vast knowledge of military and political affairs and loyalty to Rome, the Emperor has made me his personal counsel and bodyguard on special occasions.

But that’s not the best part. Knowing my desire for beautiful young feminine males, I have been given a harem of the finest slaves from around the empire all between the ages of 18-25. They are primarily servants but at any time when the mood strikes, they are there exclusively for my pleasure. They have been trained well in the art of love and knowing my interests, are all submissive. I treat them with love and respect and never abuse them. They have luxurious accommodations and are free to go anywhere on the grounds of my estate. I don’t imprison them or keep them in chains (unless of course we’re fooling around ).

One slave in particular is my favorite. He was born in the North and is about 19 or 20. A beautiful boy, you would at first think he was genetically female until you saw his cock. Before he was captured, he had extensive education and is well read and literate. We have much in common. He was also raised to be a warrior and is fit and muscular. Unfortunately, his army was ambushed by our legions and he was taken prisoner. Given his beauty he was not killed but instead taken to Rome and trained to be a slave. Fortunately for him, I won my freedom before he was assigned to a Master and personally selected him as my own.

How to describe him? Tall, long blonde hair, pretty face, blue eyes, freckles, slender but fit hairless body, fantastic legs and ass, fair skinned but lightly tanned (he loves to sunbathe nude in my private courtyard), and beautiful 7” cock. Around my villa he usually wears a very short robe or sarong made of the finest silk or just goes naked. His given name was “Eric” but he prefers to be called “Erica.”

Never married previously, I consider him my wife and he sleeps in my bed with me every night. We frequently enjoy long “sessions” in my dungeon. He loves to have me torment his cock endlessly and then fuck him while he is tied to the rack or some other device. We also make love every night in my bed. He is very strong and likes to “ride” me while I play with his tits and cock. We often spend our days together and enjoy discussing art, literature, philosophy, and history. We also practice martial arts and sword fighting. The loser always must suck off the winner.

Occasionally we travel throughout the empire. My friend, the true Emperor, has issued orders that we are to be given safe passage anywhere. Anyone violating these orders would be crucified. Yes, I am in love with Erica. We have made arrangements that if anything were to happen to me, he will automatically be made a Citizen of Rome and given my entire Estate as well as any of my slaves he desires. But for now our life is wonderful. I can’t imagine anything better.

Copyright © 2019 AMS

[a9127]

It was the middle of July in Michigan. Stephanie and I had been together for more than five years. Our relationship had grown from the “friendship” stage (the big kid and his cute little “guy” friend) to genuinely falling in love. It was wonderful, and we were practically inseparable. Everyone by now knew she was my girlfriend and her mom especially, was very supportive during her transition. She had been seeing a doctor as well. I went with her sometimes. Even though we loved each other I still had a lot to learn. But this week she had gone with her parents to visit relatives in California.

We used to play around a lot in my room when my parents were gone and often had contests to see who could make the other go the longest without cumming. Usually I won. Her small cock was the perfect size and so cute. I could go to work on her all day. I knew just where and how to suck, lick and stroke to drive her wild and also when to back off. I could keep her on edge for hours. She used to scream and swear and plead for me to let her come. Finally when it seemed she was at the breaking point, I used long and steady strokes until she had the most intense orgasm. Of course she was really good at getting me off too. Although she never really had an interest in fucking me in the ass. It didn’t matter. And she could be almost as wicked in her torments…

What she really liked more than anything however, was for me to fuck her. She was able to cum from the pressure on her prostate (sometimes I would also jack her off while I was inside of her and sometimes we used to rub our cocks together) but we almost always did it with me on top. She told me that made her feel more “feminine” because it was like what she had seen in movies and imagined other girls doing it that way. The first time we ever had sex I was on top. She said she liked to feel my strong body and larger cock inside her. Afterward we used to lie close and talk about our future. We always kissed and cuddled and she would giggle.

So, there I was sitting by myself daydreaming. I hadn’t realized it, but all the time I had been thinking about Stephanie I had been playing with my cock which was now very hard. Also I needed to cum badly. I was wearing very short shorts and a tshirt. My parents had gotten me an old recliner when we moved in and it had a very wide seat with wooden supports for the arms. Perfect to tie someone up.

Stephanie sometimes liked for me to tie her to the chair and suck her off. God knows what she was thinking about but I noticed that she was almost in “another place” and her orgasms were super intense. I would jack off and usually we came at the same time. I used a quick release knot on her wrists so she could escape and afterward I just laid there, my head resting on the chair between her legs, while she held me and stroked my hair.

I got to thinking… What if I tied myself up and slowly edged myself to orgasm? Could I stand it? Could I really do it? And for how long? Of course I’d have to leave my arms and hands free so I could go to work. All the rope was in the garage and I dared not go out there like this. So I thought quickly and grabbed a couple of neckties and belts from my closet. I tied my thighs and ankles to the chair legs spreading them very wide.

Taking a bottle of Hawaiian Tropic suntan oil, I poured it on my hands and began to slowly stroke and tease my sensitive cock. I wanted to just grab it and jack off quickly but I decided it would be more satisfying to take my time. To make it more interesting I imagined I had been kidnapped and was being “tortured” by a beautiful woman. One of my “celebrity crushes”? Maybe an older Stephanie? That did it. The “scene” was set.

I tried different things. Starting with slow long strokes. Rubbing the head like I was “polishing” it. Running my fingers around the glans. Playing with my pee hole. Everything felt great. And even better none of it was enough to make me come. I also played with my balls squeezing them and gently massaging my nipples which were very hard. I wondered if it was possible to come just from having your nipples played with? I had read about that but figured it was just a story. I also had seen porn pictures of people being “tortured” with electricity. I wished I could try it but thought it might be dangerous. Besides I didn’t have the right equipment for it. Once, I tried touching my cockhead with a 9 volt battery but it wasn’t sexy. It just hurt like hell then burned… So I decided to save “electrical play” for when Steph and I knew what we were doing. We’d have to read up on it.

This “self-torture” went on for a while. Good thing I locked the door to my room. My parents were still up. Just in case, I also had wedged a chair under the doorknob. The possibility of getting “caught” added to the excitement—but I would have had a hell of a lot of explaining to do…

I’m not sure how much time actually passed. But I was getting to the point where I couldn’t stand it anymore. I wondered what would happen if I really was at the mercy of someone and she wouldn’t stop? Could you really be kept on edge like that for hours? Would you go crazy? Would you eventually cum?

My left hand began to make regular strokes up and down my cock. The feelings of torment turned into the familiar feeling of a building orgasm. I could feel it surge through my entire body. It was as intense or maybe even more intense than sex with Stephanie. I maintained a slow and “machine like” pace although I so wanted to cum quickly.

My patience paid off. Without warning, my cock began to pulse and I shot the biggest load all over everything. The chair, the floor, me… everything. Some even landed on my bookshelf and TV. I didn’t care it felt awesome. Exhausted, I collapsed back against the chair and just laid there. I don’t know why but I couldn’t resist licking my fingers to taste it.

Carefully, I cleaned up the mess. I made sure I got it all then put everything away. Then I turned off the lights and went to bed. All I could think about was how much fun we were gonna have when Stephanie got back from vacation.

Copyright © 2019 AMS

(Moderators: Most of this story is true. Any sexual activity described of course took place during our Senior Year of High-School and we were both “18.”)

[Boner]

Wow! Hot story!

Reminded me of this sexy pic...