New Blog: My Life as a Sissy Wife

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Monday, December 5, 2011

Did you have a crush on a boy during high school?

I looked through my collection of sexy men pics looking for the photo at right and I think it is pretty close for what I need for this post.

Anyway, starting in 7th grade when I was 13 and all through junior and senior high school, I had a very deep crush on a boy who looked like the hunk at right.

He was very popular and always was a class officer or head of some club and he was captain of the tennis team and I believe he was so good that he may have won the state championship.

He was in my exact same grade and we had many classes together. So I got to really like him and I have to say that I was really in love with him! And despite the fact that he was popular and I was not and he was so outgoing and I was shy and he was the big sports star and I was a sissy, he was always quite nice to me.

And that last fact may have made me hurt even more than if he was mean to me like some of the other boys. The fact that he was so nice to me made me love him even more and it really really hurt to know that we could never be together -- he liked girls. It hurt doubly when I would see him with the prettiest and most popular girls in school because I envied them so much and I knew that the only way I could ever have him was to be one of those pretty girls, which, of course, I was not.

Now, why would I search for a picture of a gorgeous naked hunk to illustrate this post? I had to see this boy for six years in the shower and locker room after phys ed classes in junior and senior high school. And he looked like the hunk above. He was built like him and he had a big gorgeous cock like that that I would keep trying to get a look at with being too obvious and getting caught at it.

I just wanted to hold him and kiss him and caress him all over and suck on his cock -- which I had already been doing with some other boys, by the way, as I have written about previously. But while I loved playing around with my sissy friend Timmy and those other boys, he was the one I really wanted to be with.

I don't know if he ever knew about what Timmy and I were doing with the other boys, but I would have to assume that he did because you know how rumors fly around a school. But he was always my good friend anyway. How I wish I would have had the opportunity to pleasure him like Timmy and I were doing to some of the other boys.

I don't think I ever saw him after high school. He went to college and then law school as far as I know. But I am still thinking about him.

So my question is: Did you have a crush on a boy during your school days? How did you deal with it? Were you fortunate enough to follow through on it or did it remain just a hard-to-live-with crush like mine?

* Please take part in the poll on this subject!


Cashcooper said...

What a stud. love to suck his cock and swallow his hot cum!!!

polly said...

I had minor crushes on several boys, Stevie, but the pic here does remind me of one in particular. We were about 15, and he had a fight in the school yard with another boy. Everyone crowded round chanting, and he was winning easily. At one point, he ripped off his shirt, got down on his knees, and offered the other boy a "fair chance". I remember being transfixed by the site of his muscular torso - and realised for the first time probably, just how girly a real man could make me feel. It all felt SO basic and natural.

I never dared approach him - he had lovely girlfriends etc - but I often used to "conjure him up" in my head. Usually with me in a school pleated skirt behind the pavillion.

Sorry you never got your hunk, Stevie!

Lovely post as usual. x

Billie said...

I'm very well aware of how rumors can fly at school, in my case they especially did! I was a queer boy and didn't look anything like the very pretty girls despite being overcome by the exact same full feelings of one while seeing a boy in the showers! My face actually got hot a few times!

My good friend was named Neil and we did "girly" things for other boys and just imagined the hunks.

That actually helped me become the MTF I am today.

Nice story!

jellybean said...

I don't believe that I was considered a queer boy, but was the boy never picked on a team, because I never really wanted to play. There was one boy who was a fox and I have NEVER admitted this but I have always been sure that I would have loved to kiss, hug and suck his dick if it had ever been possible. I was always to afraid to try anything. Queers could really get beat up quite often.

jellybean said...

P.S. But the more I look at this VERY pretty boy and of course, very prettily I think that I would need alot of instruction, but this guy could probably teach me every thing I nee AND MORE. He does seem that he is so near perfect....WOW

Stevie Stevens said...

Can you just imagine what I went through trying to hide my desire for this boy that I had a crush on! Can anyone else relate to that?

Throughout your life as a sissy T-girl, what derogatory name have you been called the most?

Why do your wear bras? Or not?

Ever pilfer panties from a girl's drawer, clothesline or laundry, etc?,

How do you wear your pantyhose?

As a young sissy, did you look at naked men in locker rooms?

Did you ever raid a clothesline for bras or panties?

Do you hate getting erections?

Do you want to have your penis removed?

Do you take female hormones to be more girlie?

What is your mental state as a T-girl who wishes they were a girl?

Do you tuck away your sissy clitty to pretend you are a girl?

Do you wear a bra on a daily basis?

As a t-girl, what do you shave? (Pick closest choice)

What is your favorite lingerie?

You have always wanted one, but what would you call it?

Did you have a crush on a boy when you were in high school?

When you see a gorgeous girl, do you want to:

At this exact second, what are you wearing?

Do you use feminine protection?

Who was the first female you envied and wanted to be like?

Growing up, did you place dress-up with a sissy friend?

Did you play with dolls like Barbie and Tammy as a young sissy?