Trying To Find Myself

I desperately wanted to find myself and if I was who I was becoming or someone else.

If you have read the previous chapters of this story, you’ll know that my best friend, J, and I had turned harmless teenage boys fooling around into love. Which on the surface seems like the greatest thing in the world, except when you’re a confused teenager struggling to find yourself and figure out who you really are.

Now, in the beginning story I mentioned that there was some shame involved in this saga and this is the part where it comes into play. Sometimes in finding yourself, you find yourself doing things that you’re not proud of.

As I said in previous chapters, as our relationship progressed, our roles became much more defined. J was an alpha male type, all-star high school Quarterback, in very good shape and very popular. Definitely did not come off as homosexual in any way shape or form. Me on the other hand.. well, I was the weird kid in school. A social outcast. I played sports but I was overweight and was never very good at them. Also, I liked to dress up in my mom’s clothes and masturbate, but no one outside J knew that.

I knew that I was attracted to women, and J. I didn’t find myself lusting after other men. Not once did I masturbate to gay porn, and truth be told there wasn’t anything about me that screamed gay either. However, as our relationship evolved, I found myself becoming more and more feminine. More submissive to J, and more confused who I was becoming.

When the two of us were together, things were awesome. We never argued about anything. We never judged each other. And, the more we explored sex together, the better it got. I absolutely loved dressing up in women’s clothes and having sex with J. The build up to it was exciting, while we were having sex it was exhilarating but after I’d go home I’d feel exhausted and unfulfilled. Despite all that, I still found myself growing my hair longer, learning how to apply makeup properly, painting my nails, keeping my body hairless, and acquiring an impressive feminine wardrobe for in and out of the bedroom.

I was 17 now, J was 18 and I had reached a point where I needed answers for the questions in my head. The only problem was, J and I had been doing this is various forms for over 5 years and to our knowledge, no one knew what we were doing. We took every precaution possible to keep our secret. The problem is, if I were going to get the answers I needed, I was going to have to tell someone my secret because I couldn’t figure this one out on my own.

After weighing my options for over a month, I finally decided the only person I could approach with this was my older sister. My sister is 12 years older than I am and if I come off as a sexual freak then she’s some sort of mutant super freak. She’s the kind of girl that has no shame and will tell you everything she’s ever done sexually. To this day, now in her mid 50’s, she still tells me about a party she went to in college and she let 6 guys fuck her and piss all over her. NOT, the kind thing you want to hear from your sister. But I digress…

I went over to her house and laid everything out. I told her everything! And I mean everything! Even the part when I wear our mothers underwear and lingerie and let my black boyfriend fuck me in the ass. That’s a very hard thing to confess to anyone let alone your own sister.

She admitted she had no clue which didn’t surprise me, I barely saw her at this point in my life but it was still comforting to hear.

The advice she gave me wasn’t the advice I wanted to hear but it was the advice I needed to hear, however unsettling it was. She told me that if I wanted to find out if I was gay or just doing this with J because of my feelings towards him, I was going to have to be with a girl and then be with another man. The thought of both of those things scared me and despite disagreeing with her, I knew she was right. I had no interest whatsoever of being with anyone behind J’s back though.

Another month went by before J and I finally had a discussion about this. What started out as pillow talk after an evening of sex turned into me spilling my guts all over the place. At first it was a frantic purge of my feelings but J was able to calm me to a point where we had a civilized conversation about everything. I believe J could tell I needed some time apart and that’s ultimately what happened. We agreed to separate ourselves from each other for some time, and I packed my things and went home.

It took a couple weeks of feeling incredibly sorry for myself and desperately wanting to call J and go running back to him but I kept my head on straight and moved forward.

It only took about a month before I started flirting with a girl I had always kind of liked. She was by no means perfect and part of me felt a bit guilty if I did end up having sex with her and decided I was gay but I had to do what I had to do and I’ll cross that bridge when I get to it.

Her name was Sarah, she was a couple years younger than me and always very nice to me when we’d see each other. I finally got the nerve to ask her out.

“It’s about time. I’ve been waiting forever for you to ask me out.” She answered with a laugh and then hugged me.

About a month after we started dating she handed me a note as we passed each other in the hallway.

“I’m ready.. let’s skip last period and go to your place.”

So.. that’s what we did. I lived just a few blocks from school so even though I had a car now, I still walked to and from school. In the 5 minute walk, her and I held hands and there was tons of nerves. She was a virgin and I had never been with a girl before. We squeezed each others hands so tightly as we walked much faster than our normal pace.

We had sex. It was, as most first timers.. awkward and quick. However! I did get one of the answers I was looking for. I just had sex with a girl and I fucking loved it!

The second half of my dilemma was going to be much more difficult to accomplish. I didn’t know any gay guys. It was the late 90’s and everyone really kept their sexuality secret. Certainly there were guys I thought were, but then you run the risk of them being straight and telling everyone that you’re gay and you tried to fuck them or some stupid ignorant shit teenagers do.

It took me almost 3 months before I devised a possible solution. Now, disclaimer.. this is where the shame comes in. I did what I did and I’m not proud of it even to this day.

Senior year was about to wrap up and I really wanted a solution to this before summer started. Besides, J had been calling me and asking me to come over and hang out or spend the night and with each passing day the offer which was already incredibly enticing, became harder and harder to resist. J was also a good Quarterback and had already committed to a college that was 4 hours away, so I wanted to spend as much of the summer with him if that was a possibility. So I did my last resort.

I skipped school this day. I made up a story about being ill and convinced my mom to let me take a day off even though there was only 2 weeks left. I knew J would be at school and his dad would be at work. His dad’s boyfriend, Mark, however was unemployed and would certainly be home alone. You probably see where this is going…

As I knocked on the door, a lump in my throat formed and a fleet of butterflies fluttered in my stomach.

“Hey V, J is at school. Shouldn’t you be there too?” Mark asked

“Actually, I was wondering if I could talk to you.” I answered

Mark agreed and ushered me inside. Offered me a beverage and we sat on the couch. It took me a minute or two of thinking if this is really how I want to play it out and unable to come up with anything that moment I decided to proceed with the plan.

I made up a story about me being confused about my sexuality. Now I know what you’re thinking. I was confused but I tweaked the story a bit just to not give away any details or suspicions about J. I remember telling myself that this wasn’t going to work and this was a stupid idea. Mark was going to see right through this convoluted scheme.

“So what do you want me to do about it?” Mark asked

That’s it, I knew it. He saw right through me. What I haven’t mentioned is that I’m somewhere on the high functioning end of the autism spectrum and I don’t always notice the signs of what people mean when they say things. Mark didn’t say that in a condescending tone as I thought. He said it in a way a porn star would say it to me. Which I didn’t know until we continued talking.

“Well.. actually.. I was wondering…” I muttered

“You wanna suck this cock?” He asked pulling his erection out of his sweat pants

I was in no way attracted to Mark. He was a tall skinny pasty white guy with gangly arms and a nasally voice. He did have a decent cock though.

“Go on.. it’s not going to suck itself.” He said pulling his pants down to his ankles and kicking them aside.

I was hesitant at first but I did get on my knees in between his legs. I gently grabbed his shaft and licked it a couple times before sliding it in my mouth. It wasn’t terrible but it wasn’t J either. Within seconds I just found myself fantasizing about J. If I was smarter, I would’ve gotten up and left right then and there but I was scared Mark would tell J’s dad, or worse.. J.

A minute or two went by and Mark ejaculated in my mouth without warning. I really wanted to avoid that happening and I was extremely fortunate to have not gotten any disease or STD from him.

“You’re good at that. Why don’t you let me fuck that big ass of yours.” Mark suggested

“No thanks. I know I’m not gay.” I said with a smile and I got up and left.

Mark, to his credit kept his mouth shut about what happened and I made sure to thank him and apologize to him if he felt used in anyway.

“Baby, I got my dick sucked. I ain’t complaining.” Was his response.

As soon as I got to my car and headed home I started coming up with a plan to be with J and give him a night to remember….

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