Friday, June 8, 2012

Sissy Marries Cheerleader

When I was a high school freshman, there was this girl.  She was one of the Varsity cheerleader co-captains.  She was also a senior.  But more importantly, she was a cheerleader.  And I had a major crush on her.

As you can imagine, with her being a senior, and one of the head cheerleaders, and me being a freshman, the chances were that I had no chance with her.  And you'd be correct.  I didn't.  She didn't even know I existed - literally.  I am 100% certain of that statement.  But, that she didn't know I existed, and that I would never get up the nerve to do or say anything to cause her to notice me, didn't stop me from fantasizing about her endlessly, and doing everything in my power to be near her and her orbit.  I went to all of our school's football and basketball games - home and away - always sitting in the bleachers near the middle of the cheer line, where she and her pretty co-captain were situated.  I followed her wherever a Varsity team went my freshman year.  I didn't have a girlfriend my own age.  Shoot!  I was too afraid to approach any girl - much less this senior cheerleader.  And I never did.  She graduated, and I transferred from that high school the next year, without ever even speaking to her.  She was, as we've heard it said, the most popular girl in school.

So, now we go back to where I left off at my last post.  My first wife left me for another man, or, as I've acknowledged, a man.  We had to go through the required legal separation before we could get divorced.  We had no children, and I saw no reason to battle her, since she had her mind made up, so I simply watched her walk away into the arms of this man she'd found who could satisfy her.   I didn't date during my separation.  At all.  No one.  I was pretty despondent over losing my wife, especially knowing deep down inside why it happened.  Friends were trying to set me up like crazy.  I was viewed as a very eligible bachelor.  I was a successful and respected attorney.  I was (am) a pretty good looking guy.  But I resisted my friends' efforts to get me to go on dates. 

If it hasn't yet, this is where my story gets interesting.  There was this girl friend of mine who kept telling me that she had a woman I had to meet.  That we were perfect for each other!  This woman had recently been divorced by her jerk husband who'd left her for another woman, leaving her with two young children.  I resisted my friend's effort to set us up for two reasons.  One, I simply wasn't ready.  And two, I wasn't sure I wanted to get involved with a divorced woman with children.  But my friend was patient.  She told me to let her know when I was ready.  I let it go at that.  

The week after my divorce became final, I attended a Friday night after work function at a downtown Happy Hour and bumped into a guy who had been a juror on a big (by "big," I mean "huge") case I'd just won.  He and his wife approached me and he began telling me how cool the trial was, and how impressed all of the jurors were with how I controlled the courtroom.  Yeah!  That was nice to hear.  While he and I talked, his wife was checking me out.  She managed to find out that I wasn't married.  Women and their guile!  I envy it.

As we were about to say our goodbyes, she asked me if I had plans for dinner.  I'm not stupid.  I could tell she wasn't just randomly asking me to join them.  So I asked her why she asked.  She told me they had a friend who she'd like to introduce to me.  Again, I'm not stupid.   I had no idea what this woman looked like.  I wasn't accepting efforts to set me up with girls I knew were pretty.  I sure wasn't going to randomly agree to go to dinner with someone I'd never seen.  So I'm giving this juror's wife a non-committal response when guess who walks up?  I hope someone guessed it.  It was my cheerleader.  I didn't hesitate.  I turned to the juror's wife and said, and this is a verbatim quote, "Absolutely!  I'd love to join you guys for dinner."  I didn't want there to be any chance for them to back off.  

Somehow, at dinner, I got around to telling my cheerleader about my high school crush on her.  She confirmed for me that she didn't remember me at all.  Like I said.  

She seemed hesitant at first, but I could tell she liked me.  It's amazing how those three years that separated us in high school seemed like a generation of difference, but at our current age, it seemed like only weeks apart.  To shorten the story some, I'll simply say we began dating.  I liked her kids.  And they liked me.  We began seeing each other nearly every day.  

Soon, we reached the moment.  The moment when we were going to spend the night together.  I was so scared.  I really liked her.  I thought we were falling in love.  We were falling in love.  But would I be able to perform?  I knew she could.  She had been pregnant twice.  But I never had done it.  At my age, that was something no woman would understand.  Despite my fear of failure, I knew that I had to at least try, and fail, or our future would never be.  

So, one night, I let the kissing and petting go further.  That almost sounds funny - doesn't it?   For the guy to be the one who let sex escalate, rather than the other way around.  Her kids were spending the night with her parents, so she took me to her bed.  I could tell she wanted it, and was tired of me delaying making my move.  The first thing I did was something I knew that I could do.  Something I was good at.  I went down on her.  And she liked it.  A lot!  She let me know how much she liked it too.  I licked and sucked and ate her for at least an hour.  Finally, she couldn't stand it any longer.  I was amazed at how hyped she was.  I'd never seen a woman respond this way, because I was completely inexperienced.  I'd certainly never made a woman react to me like that.  

She was totally in charge as she pulled me on top of her and directed my penis toward her pussy.  I can still remember the moment vividly - I was so afraid that, once again, I would fail to perform, and then, before I realized what was happening, I was inside of her soft, wet pussy, and she was begging me to fuck her.  To fuck her!  To fuck her!  I couldn't believe it!  I was fucking her!  I was fucking her!   I was fucking a woman!  It was unbelievable, to be nearly twenty-eight years old, and fucking a woman for the first time in my life.  And she enjoyed it too.  No.  She loved it.  I pleased her.

We fucked all night long that first night.  As soon as I could get it up again, I fucked her.  And we began fucking like that nearly every night.  She'd been hurt so badly by her jerk ex-husband who, by the way, was the starting quarterback for our high school.  I'm not making this up.  I know it wouldn't have happened if I looked like a sissy on the outside.  But I didn't.  I'm a good looking man. And I was with the head cheerleader who'd married the quarterback, and I was pleasing the hell out of her.  

Again, to shorten the story some, we were married within six months of meeting.  At that point in my life, wearing women's underwear was the furthest thing from my mind.  All I knew was that I could have sexual intercourse with a woman.  As you can imagine, I worshiped her - the woman who helped me fuck a woman.  And so, we moved on with our wonderful life.  It was only later in our marriage that my "urges" bubbled back to the surface. And I don't think anything could have prevented them from escaping.

We're still married.   But a lot has happened since we met and married.  More on that in a post in the near future.  Oh - one more thing.  The woman my girl friend told me I had to meet?  Because we were perfect for each other?  It was my cheerleader.  Pretty cool - huh?


  1. Very cool! And congratulations.

    Finding a partner is difficult enough, but then finding one that accepts, or even supports, is phenomenal.

    I've been blessed to have spent time with 3 women who accepted, and particpated, in my love of dressing. But while my first wife accepts, I must everyday deal with the gap left by her not wanting to participate.

    I wish you all the best.



    1. Dear Marilyn,

      That's great for you. I hope my journey continue to grow and improve.



  2. Leeanne- OMG!! I LOVE this post!! I didn't see how it came together at first.. We all have those girls from HS we adored. And after what you went through. I almost cried, hun, when I read the part of her teaching you to Fuck her-- and you succeeded!!! :)
    Know what you mean about being nervous about being set up on dates before I was married. Maybe it's because we're girls, lol... but I think it's because maybe we're more sensitive, and don't want to hurt someone's feelings if they aren't attractive enough for us?
    Happy hug, Sara

    1. Dear Sara,

      It is, without a doubt, one of the best parts about my life that she and I ended up together. I wonder if I would have ever been comfortable, if even able, to make love to a woman if it were not for her. And to know that even today, she is the only one for me, despite having been married for several years before her. Thanks for your thoughts. You seem so nice.



  3. well i'm glad it all worked out for you leeanne, this time around and i'm quite sure you'll know that any women will tell you, if a guy can't use his tognue, then the womens lost half the battle

  4. Sounds like it was fate, if you believe in that, which I do.