Friday, August 27, 2010

The High School Years – boys, girls and men

Even though I liked to wear my mother’s clothing I never considered myself anything but straight, during grade school.  I loved how girls smelled, I loved how they looked, I loved the way they felt when I touched them.  I loved girls!!  So the funny thing is I had a homosexual experience before, I lost my virginity to a girl.  I know if you read my previous you are going you had a homosexual experience before you slept with a girl?  There is a surprise.  You had been wearing your mother’s underwear since you were eleven.  Yeah, I know but I was never attracted to boys, so looking back it was a surprise to me.

Now it was not anything special and lots of guys have done the same thing.  My best friend and I were riding our bikes in the woods during the summer before we started high school.  We decided to stop and take a rest, so we get off the path, moved in behind some bushes and put our bikes down, sat down and relaxed.  We started talking about girls, sports, dreams normal guy stuff.  Somehow we got on the topic of pubic hair and he suggested we show each other what we had. 

Now we had seen each other nude before, we were best friends, had stayed over at each other’s homes, and had gone away for weekends together with our parents.  Anyway, we look around pull down our pants and start comparing what we got.  Thinking back he did have a wonderful big dick, but the one thing I did notice right away was that he had no pubic hair.  I on the other hand had quite the little bush growing.  When I teased him about his lack of hair, he just laughed and said the reason he wanted to show me, was that he had shaved it all off.  When I asked him why, he just said because he liked the smooth look.  He then started masturbating and I was mesmerized.  He was so confident standing there jerking off in the woods with his pants around his ankles, so I joined in and we stood there jerking ourselves off until we both came. 

That was my first homosexual experience, beating off in the woods with my best friend.  As I said pretty innocent and I bet you if you ran a poll, most guys will admit to doing that when they were growing up.  Now the interesting thing about this friend is that he ended up being the first person I knew to come out as being gay in high school.  The funny thing was that in the last two years of public school and the first two years of high school, he always had a string of girlfriends.  Girls would not leave him alone.  But when he came back for his third year at high school, he came out to everybody.  We had drifted apart by that time because we were running in different circles, but I felt for him because he was ostracized by just about everybody.  But he stood his ground and made it through high school and then excelled later on in University and then after that went to law school and became a lawyer.

Beside that one experience with my friend at that point in time I only had eyes for girls, girls, and girls.  I will admit I was not much of a lady’s man; I was and still am pretty shy.  But I kept trying and finally landed myself my first real girlfriend in grade 9.  Things moved along quite nicely and during the summer between the first and second year of high school, I lost my virginity to her.  It was nothing spectacular; it was the usual, lots of fumbling around, having trouble putting the condom on, but I was very proud of myself that I lasted more than five seconds.  Lol

We lasted a few more months then broke up during the first semester of our second year.  During this time, I was still wearing my mother’s clothes any chance I got.  But once my girlfriend and I broke up, I decided that I needed a change in my appearance and it was time to get rid of the hair around my penis, and go for the that nice smooth look.  A couple of weeks later my parents went out of town for the weekend, so I was able have the house to myself and the time necessary to complete the task.  I took my mother’s scissors that she kept in the bathroom and trimmed as much hair back as possible.  Still not satisfied, I found my Dad’s electric razor and used the side burn trimmer, to get rid of some more hair; finally I pulled out my mother’s electric razor and finished the deed.  I was bald as an eagle and loving it.  I spent the whole weekend wearing my mother’s sexy panties everywhere I went.  To the mall, to work, I had no pubic hair and nobody knew!!!

On the Sunday before they came home I spent the day doing laundry, and cleaning so that there was no evidence that I had worn my mother’s underwear or shaved myself bare. I was extremely happy.  I knew I could not get away with shaving my legs; or torso because my parents would be able to see it, but my pubic area no one could see.  It was brilliant and fool proof.

And then the girl of my dreams decides that I am not an idiot and she really did want to date me.  Yikes!!!!  Here I am smooth as a baby’s bottom, and a hot girl wants to date me??  I had to go into damage control.  I went on a few dates with her, and no matter how many times she suggested we take it to the next level, I kept demurring and claiming that I wanted to make sure that I really loved her before I had sex with her.  For whatever reason, she bought that, and after 6 weeks, I figured enough hair had grown back that it was safe and lo and behold she did not say anything, but I was extremely nervous the whole time because I thought for sure she would notice that my pubic hair was not very long.
Next big life event of course was turning sixteen and getting my driver’s license.  Now you may be wonder how could the ability to drive have anything to do with this story?  Well two things actually, with the car I was able to venture out dressed “en femme” and being able to drive lead to my first relationship with a man.

I will start with the going out dressed as a female.  Now I will be completely honest I was not able to go out fully dressed up because I did not have any woman’s shoes.  But what I did do was go out in full make-up and, t-shirt and jeans, with a bra and panties on underneath.  I also, used to stuff the bra a little because if you are trying to pull off make-up you better have some cleavage.  Lol

The first time I went out in full make up it was very late at night on a Friday night.  My parents were out of town visiting relatives, I got to stay home because I was working on Saturday.  I had been playing around with some make-up that I had bought for myself (yes, make-up counter ladies are very helpful when you tell them you want to buy your mother some make-up for her birthday lol) and finally got it exactly the way I wanted.  For whatever reason, I just had this urge to go out and show it off.  So I hopped in my mother’s car and went for a drive.  After a few minutes, I got really scared, you know all those things start growing through your mind, like what happens if somebody sees me, what happens if I get in an accident, what happens if a police officer pulls me over for a traffic violation.  I quickly lost my nerve and headed home vowing never to do that again.

The thing is of course was that I was hooked.  There was a real thrill to going out in full make-up, wearing a bra and panties under my t-shirt and jeans and not getting caught.  So each time thereafter, whenever my parents went out of town, I would venture out and go a little further and stay out a little longer.  The other thing I decided was to get drive out of the town where I lived, therefore decreasing the chance of running into anybody I knew.  After a while I even got up enough nerve to stop into convenience stores to buy a can of pop.  I never said a word when I would go into the store, always made sure I was the only one in the store and I never got caught. 

To be continued….

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