Thread: Shemale Stories
View Single Post
  #245  
Old 05-16-2019
a9127 a9127 is offline
Senior Ladyboy Lover
 
Join Date: Jun 2013
Posts: 3,111
a9127 has much to be proud ofa9127 has much to be proud ofa9127 has much to be proud ofa9127 has much to be proud ofa9127 has much to be proud ofa9127 has much to be proud ofa9127 has much to be proud ofa9127 has much to be proud ofa9127 has much to be proud of
Default A Solo Experience?

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.”)

Last edited by a9127; 05-16-2019 at 09:25 PM.
Reply With Quote