Raised by Strippers - A Trans Story - Cover

Raised by Strippers - A Trans Story

Copyright© 2021 by Shirley Wanton

Chapter 2: Going Back to School

Erotica Sex Story: Chapter 2: Going Back to School - This is the story of the son of a stripper, raised in the dressing rooms of strip clubs and evolving into the Trans woman she was always meant to be.

Caution: This Erotica Sex Story contains strong sexual content, including Consensual   BiSexual   CrossDressing   TransGender   Fiction   Anal Sex   Exhibitionism   Oral Sex  

Although my stripper family had comforted me and made me feel better about myself and the things I was discovering that I needed in my life, I still had to figure out how to live my life outside of the strip club. For those paying attention, I basically ran screaming from school after accidentally outing myself in front of MANY f my classmates in the high school locker room. The school itself was pretty great about it. My Mother talked with the Principal and explained what was going on in my life and he was very understanding, at least that is what my Mother said. He must have been, because I never heard anything more about leaving school like I did. Well, I didn’t hear anything from any Teachers or Administrators. The other kids, that was a WHOLE different thing.

Walking back into that school was one of the hardest things I ever did. I would say it was an exaggeration that everyone in school heard about what happened and was talking about it, but I am pretty sure, that is exactly what was going on. Even though I still went to school in my boy clothes, I felt like everyone was staring at me. Suddenly, all the confidence I got from my stripper family and my pride in my new found oral skills, went POOF, when I faced the reality of being surrounded by my school peers again.

The confident dancer that wanted the world to watch her was gone in a puff of smoke. In her place was the slightly built, awkward boy, who wanted to melt into the floor, rather than face the judgement of a bunch of high school seniors. Suddenly, the lace thong under my pants, that started my day making me feel so sexy and bold, now only highlighted my vulnerability to this pack of wolves, who seemed ready to rip me to shreds.

It wasn’t all bad. Some people actually approached me and shared words of support. However, it seemed like WAY more of them couldn’t resist sharing their thoughts regarding the kind of guy who wears women’s underwear and what they believed that kind of guy likes to do with other guys. Even many years later, I am not sure how I felt about those judgements. I mean it is hard to counter that, when I had been spending a LOT of time learning the best techniques for sucking cocks.

Luckily, I didn’t have a lot of friends, so I didn’t feel any more alienated than I was before all this started. On the positive side, as time went by, I actually started to have guys catch me when they were not around their friends, etc., and they took great interest in my sexuality. Some even asked if I wanted to meet on the weekend or after school and “talk”, if that would help me. I quickly discovered that “talk” was code for seeing how it would feel getting their cocks sucked by the freak that wears girls’ clothes.

As it turned out, there were a lot more guys in my school who wanted to “talk” than I would have ever dreamed possible. It also turned out that I did a LOT of talking, which is funny because I usually had my mouth full and couldn’t talk if I tried. As it turned out, most of these guys would rather talk to Samantha than Samuel, so Samantha came out to play more and more. In a way, it really helped me make the big emotional jump to finally coming to school as Samantha.

Because I had tied so much of dressing as Samantha with my sexual activities, it was hard to be Samantha in school and not be constantly distracted with my sexual desires and needs. On the plus side, once I embraced Samantha, I became a different person. I now walked the halls like I was walking out on stage. Now, all of the judgmental stares became appreciative cheers of my fans, at least in my head. Samantha became so much more than Samuel could ever be. She was even invited to a party thrown by the popular people, including many of whom were on the football team. I was actually going to a party with the popular crowd. Finally, I was going to be accepted. Or so I thought.

Trevor was a Senior like me, and he was apparently quite talented as a running back. I had absolutely no clue what that even meant really, but he was really hot and I was thrilled that he wanted me to go to the party with him. He told me how cute I was and told me to wear something really sex, so I could really WOW everybody there. After classes ended for the day, I was so excited and giddy, I almost ran to the club, to share my news with my stripper family and solicit their advise on what I should wear.

Most of my club family were overjoyed for me. Of course there are always those who want to crush your joy. Jasmine was one of those people. She was the stereo typical man hating lesbian dancer; and yes, she was one of those that insisted that she is a dancer NOT a stripper. I don’t want to be mean. I know that she had a lot of bad experiences with men. She was shit on by quite a few, and was even married to a guy, who was a HUGE asshole, who regularly beat her and even knocked her out a few times. She earned her right to hate men, I guess. I am just glad that she didn’t see me as a man, and most of the times I felt like she actually liked me.

Well, Jasmine warned me against going. She was sure that those guys were just going to mess with me and humiliate me. She said that guys are assholes and even the ones who want to be accepting and inclusive, will betray me, especially if their friends are around. Naively, I told her, that isn’t the way it is; and that Trevor was DEFINITELY not that way. He seemed like a really nice guy and I feel like he really likes me. Yes, I should have listened to Jasmine.

Instead, I listened to everybody else, who were much more focused on dressing me like I was their personal, life sized Barbie doll. They tried all kinds of sexy outfits on me. Everyone had their own opinion of what I looked best in. The one thing they could all agree on was that my butt looked amazing in thongs. I have to admit, my butt is round and firm with just enough flesh to make it move just right when I walked, and YES, it looked amazing in the thong. The red lace one, that they picked, looked even better. The way the color stood out next to my pale white skin, dividing my round butt cheeks, looked amazing.

Of course, a matching red lace bra was a must. The problem is that the bra was one of Victoria’s, and she is a full 34D. I am very slightly built and all of my bras are A cups. I never experimented with falsies. Fortunately, several of the girls had inserts that they wore when they were going for a fuller, bustier look, when they were dancing. This was not always a good strategy, especially when most dances ended with their bras discarded on the stage. However, some of them were like professional Magicians, and could drop a bra with falsies inside and never miss a beat. I guess turning, bending over, and slapping your ass, has a way of distracting guys. Who knew?

OK, so now the underwear decisions were made. Of course everyone agreed that black stockings and a garter belt completed the erotic look. Now, what to actually wear?

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