My Story by Destiny1961 – Non-Fiction

Writer: Destiny1961

Subject: My Story

Link: Email LS666 / 01.02.2022

Author’s Notes: This one is where it all began and felt the urge to tell my story. Not sure what to call it and may repeat some things in past stories but here goes.

My Story

I am a very small young man, while of age still have a younger mentality and a bit naive. Have always had an above average IQ and went to Catholic school so kind of the good boy. But inside have had dirty thoughts and even played around with my own cousin who showed me my first sex. Was always the one who was scared and when meeting with the neighborhood whore could only ask why. The only thing she said was everyone has there place, why not enjoy it. You know the way Catholic girls were perceived. 

I am older and finally made friends with the bad boys as am consider the shy smart guy. Again small in build and not endowed so wasn’t a ladies man. Found myself trying things like drinking and even smoked pot with those friends and started having sex thoughts. I had a friend named John, he was about five foot, six inches and maybe one hundred and eighty pounds, kind of chunky.

I am about five foot, and lucky if I weigh one hundred pounds, with my long hair looking like a girl. It is a usual day where instead of using my mind for good was finding ways to not go to school when I met up with John at his school. Something took over and we decided to cop but there was something at work here maybe I did not understand. We decide to go to a park in the winter and there on a pond was a nerf football.

He reaches to grab it and falls in and is soaked. What to do? He lived close so we went to his place, but he had to put his two dogs in a separate room as they were nasty. We went into his room and he got changed. He suggested raiding his moms liquor and so we did and started to talk about sex.

We were sitting on the bed when I felt something but never understood as he leaned me back and slid on top of me fully clothed. He was horny and I always wanted to make my partner happy, wait, my partner? He laid and started to rub against me, but I felt strange, as if I was the female in it. He said not to worry, no one would find out. We rubbed until we made a mess in our pants and he could change. I felt the mess and as I cleaned it had a weird feeling about it. We went our separate ways.

It was less then a week later when we went to his place again and he asked if I was okay about what happened and if I liked it. I could not tell him I felt like not only a sissy but his hooker. He asked if I wanted to do it again, this time I suggested naked so did not have the mess in my pants. I got naked and laid down, almost like a compliant sub as he took off his pants.

It was weird, but the sight of his cock got to me and the feel of it rubbing against me like it owned me, oh my. What was in my head. He got excited and pushed hard til we came and then rubbed against the mess and it felt wild. He got up for a towel and I ran my finger in it and tasted it. Then I felt a weird tingle below that stuck with me. I think he even mentioned something about my size being feminine.

Two weeks later and haven’t been able to stop thinking about it, and even praying to figure out what was up. But kept thinking about the things my cousin and the whore said about the feel of a cock inside. So we end up at his place again and as we start talking about it I mention real sex and he tells me he will not be penetrated. I joked about his dogs and he said that he could and let the other eat me up and laughed. That was when I offered to bottom out of nowhere.

He asked me if I seriously wanted to let him fuck me and the sound got me. He gave me a few ways to back out as I got naked and was feeling this weird hooker vibe. He told me he had no lube and could only offer using soap. It was my duty and said okay. I laid on my belly as I felt him soap my ass and then press the head of his cock against my hole then go into me. I jumped as it caught me off guard and he pulled out and said he would stop but I needed it for some reason. He went back in slowly more and more and in and out until I was moaning almost like a bitch in heat.

He got excited as he ended up fully on top of me and started to pound into me. At one point I could hear him pant as he slapped off my ass and was shoving deeper and deeper. He lost track of who I was and took me like a little bitch and I was getting excited. It went from pain to a feeling of enjoyment to be taken as he shoved. I was hoping and it happened as he shoved deep a few times and paused in between.

I knew he was close, but would he, or not. Then he shoved deep and I felt that door open as you shot deep inside me as he quivered and then lay on top of me spent. After a few minutes I sighed and he realized where he was and got up quickly and said he was sorry but did not realize who was under him and that he could not hold it and came in me. He told me I had a nice ass and went for a towel. I reached around and slid a finger into my open and sticky hole a d it felt like I had a pussy. Who was I and who was in my head I thought, but wanted more. But that’s okay, this was just a one time, right?

We lost touch and a couple of years went by as I thought about that moment and even other things. I was drinking and horny and decided to walk it off when came across friends who were picking up old men and robbing them. They told me I should do it, as the old men would pick them up to have them suck them and pay them. It was easy, get the money first and then hop from the car and told me to try it. I had them watch as I got into a car with an older man, but asked him to go a certain distance.

I told him what was going on as he rubbed my leg and thanked me. He gave me a kiss which stunned me and said he wanted to thank me. I figured why not, though did not understand as knew of men picking up girls and paying them, but for the guy to do the sucking. I remember a few times walking back from the bar, my skinny body with long hair and guys asking me to ride and a couple times I did. They would tell me that I was cute and one even ask if I was a girl.

Then came the night I was heading home and it was a really older man and I knew the guys were close so I talked with him and noticed he had his cock already in his hand. I got in and warned him as we went to a secluded place and talked. He made small talk about me looking like a girl and how men suck better and if I even and so on as he, stroked and leaned over to loosen my pants.

He slid his head down and sucked me and then opened the door and spit and I watched as he stroked. He had a nice size for his age and asked if I wanted and to let it just flow. I licked the head and shaft as he got even harder and took it in my mouth and went up and down.

Something took over as I started to gag myself as he said to relax. He told me I was a natural as he slid a hand down my pants which excited me more. I felt his hand on my head guiding me like a slut as he took my face. He told me he was getting ready and I milked him and he came.

I sat back up as he told me to open the door and spit, but I had swallowed and he told me I must be a sissy. He told me with my talents and my ass I may want to think about it. But who am I and what am I becoming. Who is in control.

It was years later and I was married though it felt like a sham. The internet now out and I needed to try and spice my straight sex life up. I started to watch porn and found myself seeing tranny porn. I saw CDs for the first time really and had these wild thoughts so tried on my wife’s things. I thought back to those times and wondered, but. So I decided to get into a few chat rooms and personals and talk and even bought a couple things and tried on make up. But there were guys out there who wanted what was inside and not to worried about the full looks.

I met a guy who wanted to see how I looked and at the time had long dyed black hair and put it in pigtails. I remember it was the start of looking into dark things as I liked the goth look and was into the undertaker on wrestling. I said that I needed to see something, so invited him over while wife was at work and it was like I wasn’t me. I remember having a drink and talking about possibilities as I dropped to my knees like a call girl. I started to suck him as he grabbed my hair and worked him as he got excited and so did I as if being guided by some sort of spirit of a whore. I remember him grabbing my head and holding it as he exploded in my mouth and said he wanted to fuck me, but I was so good he couldn’t hold out.

I said next time as I was falling into a new identity. We talked about it and next time I met him at his place. We started to usual way and tried to get him in me but I was tight. We ended up with just more swallowing and I remember him telling me he wanted me as his side girl. That when with him would become a girl and live that way. I felt it and was ready to do it. I then had this idea and was unsure how it would work but thought back to the soap.

I met him again and sucked him hard and then went into his bathroom and used a syringe to shoot lube into my hole to make it like a wet pussy. I came back and got into position as he sat and lowered until he popped into me and it was like something popped. I remember him telling me I was his as he kissed my neck and I pounced trying to take him deep as possible like some cum craved whore. I felt I was no longer myself as I rode him til he pulled me down and shot. I think something got in.

It has been years and I have been between light and dark and male and femme and sissy but which path to go? I feel there is one more step to not turning back but who wants to take me there? Is there someone who wants to penetrate and take me and send me off into the abyss?