How I got my start as a tranny (trans-sexual)

TSLindsay's sex story
My first experience that told me being a tranny slut was my calling. I went from a nerdy, skinny redhead boy, to a hot slut bimbo that summer.



My mom and dad divorced when I was 12. I was never too sure why, but it happened about the time my dad got very religious and wanted to become a minister. I used to see my mom on weekends, as my dad had custody, but she moved to the opposite coast when I was 15, so I spent summers there.
The first time I went there, I met a guy next door to her, in his late 20s. I met him because I smelled him smoking pot in the backyard and asked if I could have some. He was a nice guy, and was curious about my mom. Now, guys always like my mom. She was 35 then, but looked younger, was tall with red hair, slender, athletic, big boobs.
One afternoon, I told him about a little discovery I had made I had made. By climbing a tree by our garage, you could get on the roof of the garage and could see directly into my mom's bedroom and bath at night.
That night, I met him, after I had supposedly gone to bed, and went out the bedroom window. We smoked some pot, and climbed on top of the garage. It was not too long until we saw the lights go on in my mom's bedroom. She immediately pulled her t shirt off and she had no bra on, so her boobs were there for us to see. She pulled off her jeans and walked to her bathroom mirror in just her panties. She stood there cleaning her makeup off, her big tits jiggling as she did. My neighbor took his cock out and began to stroke it as he watched her. I was going back and forth from watching my mom, to mostly watching my neighbor. He was a dark skinned Mediterranean type guy and his dick was dark and big. It was standing straight up and he stroked it. My mom eventually took off her panties to take a shower. When she got out, she bent over and we could see her ass and pussy from behind clearly. I heard my neighbor moan and he shot a big load of cum. Soon, my mom turned off the lights and went to bed. We climbed down and went our separate ways.
I talked to him the next afternoon, and he told me he loved watching my mom, and loved her red haired pussy. We agreed to do it again that evening.
That evening was going pretty much the same way, except I also took my dick out and stroked. I was mostly watching him, and we came together. This went on a few times over the next week. One evening, we were really high, and waiting for my mom. He asked me about the fact I always looked at his dick when I stroked. I was kind of embarrassed and did not say anything. He told me it was cool with him. He asked me if I could stroke it for him that night as he watched my mom. I was really nervous, but said sure. My mom came out, and he took his cock out. I sat down on the roof and touched it. It was so much bigger than mine. I began to stroke it and it got hard really quick. My dick was out too and I rubbed it as I stroked him, not even glancing at my mom. I was really turned on and realized that when he came, from the position I was in, I was probably going to get hit by his cum.
Sure enough, he came and it hit my face. Without even thinking about it, I licked some of the cum off my lips. It made me feel very nasty, but good.
The next evening, we started as before, I was stroking his cock, now looking forward to getting sprayed. When my mom got out of her shower to dry off, he put his hands on the back of my head and guided my face to his dick. I knew what he wanted and willing took his cock in my mouth. I could only get the end of it in my mouth, but liked licking it with my tongue as he moaned. I gradually got more of it down my throat, until it was about half way in. I felt his cock throb, and knew he was going to cum. My mouth filled with warm hot cum as he let go in my mouth. I rolled the thick, viscous goo over my tongue and then swallowed it.
After that, when I met him in the afternoon, sometimes I brought some of my moms panties. He liked sniffing them, and I would suck his cock. I got better and better at it with practice.
Then, one weekend, my mom was going to be out of town, and I was going to be alone. I was bummed as I liked our garage meetings. I told him, and he said if I want, I could come over to his place and we would smoke weed and watch porn. I tried to act nonchalant and said that would be cool.
That evening, I prepared a little surprise for him. I went into our attic and sorted through some old clothes of my moms. I also got an old wig she had bought many years ago, after she had cut her hair short and hated it. I put on one of her old bras and took a pair of old stockings of hers, and put rice in them, until they were about the size of her tits. I put them in the bra. It looked pretty good. I put on an old pair of her panties, and put on a pair of her pantyhose. I cut them to resemble stockings with garters. I used her make up, which I confess, I had fooled around with before so knew how to do it. I put on her brightest red lipstick, and pulled one of her old mini dresses over me. I put on the wig and looked in the mirror. It was a little freaky how much I looked like her. I tried her heels, but they would not fit me, so I just put on a pair of sandals.
It was dark out, and I knew no one else could see me if I went to the back door of my neighbor. I knocked on the door, and he looked through the window. I could tell by his initial reaction, that he thought it was my mom at first. He was stunned. He stood there and just said holy shit.
I came in and we went to his living room. He took out a bong and we took a few hits. I told him I was sorry I got lipstick on the bong, but he said that was OK, and that he had plans for lipstick getting on other things as he smiled.
He put in a porn movie on the TV and took off all his clothes. He sat back on the couch, his legs open, his dick standing tall. I got between his legs and began to suck him. I had become very good at it, but this time he blew his load very quickly. I was disappointed that we were finished, but he said give him a little time and he could cum again. We smoked some more, and he could not take his eyes off of me. He told me it was amazing how much I looked like my mom.
He asked if I could do something for him that was a bit kinky. I said, yeah, I guess. He went to his computer and web cammed a friend of his who lived far away. He told me before hand, not to talk, just smile wave, and do what he says.
His friend came on and that chatted. He said to the guy did he remember his neighbor he had talked about, the hot red head. The guy said yeah. He waved me to the camera. I came over and waved and smiled as he told me to.
My neighbor then stood up, exposing his dick. He told me, suck it slut. I began to suck him, on cam, and soon saw his friend had his dick out stroking as he watched. All he could say was oh my god, fuck, I cant believe it. Soon my neighbors cock was really hard again. He told his friend he had to go, and closed the cam. I heard him say wait, don't go as it turned off.
My neighbor laughed and said his friend will be beating off to that for a week.
I sucked him again and soon he was rock hard, but he wanted to wait a little. We smoked a bit more, drank a beer, and turned on a porn video. He was sitting on the couch watching both the porn and me. Maybe because I was pretty high, I decided to dance for him as he sat there wasted with his cock standing straight up. I tried to undulate as hot as I could, I gave him a lap dance, and he grabbed my ass with both hands as I sat facing him on his lap. He pushed me down and guided my face to his dick. I was eagerly licking and sucking his dick now, totally uninhibited. I figured I was going to get a mouth full of hot cum, when he pushed my head off. He stood up, his hard dick standing at attention. He told me to wait a minute and he went into the other room. He came back in a short bit holding something in his right hand, he walked up to me as I was sitting on my knees, and with his left hand he grabbed the back of my head and shoved his cock in my mouth. He was moaning and saying what a hot slut and dirty little whore I was, and I mumbled agreement as my mouth was full of cock. He pushed my head off again and looked at me with I now saw something I figured was lubricant on his right hand. He slathered his cock with the lube and smiled at me, he said, I believe it is about time for you to get fucked.
I was all ready pulling the panties off, and getting on all fours. He hiked my dress up, and I felt his still lubed finger rub around my hole, then he slowly worked the finger in me. He told me to relax, to concentrate on relaxing he muscles in my hole. He soon had two fingers in me, then pulled them out. I felt the head of his cock press against my hole, he pushed gently. I felt my hole stretch then tighten around his head as it popped in. He very gently just popped his head in and out of my hole a few times, with me gradually relaxing until it went in easy. He slowly slid his dick in me stroking a few times at a certain depth, until I was used to it, then a bit deeper. It took a bit, but soon he was all the way in, buried tot he balls, as they say. Now my hole was relaxed, yet I could squeeze when I wanted to. It felt amazing. I liked everything about it, feeling his cock slide in and out, occasionally squeezing it with my hole to his delight, the feel when it was deep in me, so full of throbbing cock. He rubbed my ass. I moaned with his thrusts. He asked if I liked it, and I said yes. He slapped my ass a little and said thats all, you just “like” it? I said no, and he slapped my ass again. He told me to tell him exactly how much I like it. I swallowed and said, I love being fucked, I love your big hard dick fucking my mouth, cumming in my mouth, and even more I love you fucking me like this, fucking me like a slut, I love feeling your cock going in and out of me, your balls bouncing as you fuck me good.
I felt his cock deep in me start squirting cum, he fucked me harder and I could feel the cum dripping from my hole down my legs onto my stockings.
I knew at that moment, this was what I was meant to do, be a tranny slut girl.
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