Sissy Makes Life With Cheerleader

My Beautiful Cheerleader

I left off my account of my personal sissy journey of self-realization with my marriage to my high school cheerleader crush.  I think it is important to clarify that, while the events and activities of my life that have led me to where I am today were occurring, the concept of "being a sissy," that I now understand, wasn't even a thought process for me.  I saw myself as a man.  Even though I loved all of my girly dress-up opportunities, I never thought, "Gee!  I should have been born a girl!", or, "I wish I could have a sex change and become a girl!". Nope!  I was simply a guy who liked wearing women's lingerie. 

But there was more, and I did struggle with it.  That I was never able to have sexual intercourse until I met my cheerleader, was a problem that I was completely aware was a problem.  And part of the problem was I could never admit the problem.  And, moreover, I had to lie about it to make sure no one ever knew the truth.  Even my cheerleader didn't know, when we married, what she'd done for me that first time we made love.  As far as she knew, I was a typical man who enjoyed sex.  But, what she did do for me, was to make it possible for me to stop obsessing about it.  Because, with her, it was no problem.  And given my track record, I was so thankful for her being that woman who helped me "solve my problem," even if she was unaware that she'd done so, that I was like a puppy dog who would follow her anywhere after that.  And, she did love my "special talent" quite a bit.  Even now, we each realize that my "special talent" lies in what I do with my mouth, as opposed to what a woman needs a man for.

So, after I married my cheerleader, we settled into our life.  She was my savior, and in many ways, I was hers as well.  Remember, her crap ex-husband ran out on her, leaving her with two children to raise.  I stepped in, and if I say so myself, did a good job.  We built a very happy and good life together.  Our sex life was amazing.  And, it stayed hot for a long time.  Because I was so hyped from finally being able to fuck, I initiated a lot of that.  And she was up for it also.  Only in time did my draw to lingerie return to me.  My cheerleader was throwing away some old clothes one time, and I was carrying it to Goodwill.  I noticed a few bras, bodybriefers, and nylon nightgowns in the bag. I don't really remember what caused me to do it, but I pulled them out and kept them. I took them home and hid them in my closet, and so began a part of my marriage when I hid something from my cheerleader.  I would never have thought she'd accept that.  While she was really a hot lover, and loved sex, her thoughts and view of the world made me think anything out of the mainstream would be considered "sick.". And I didn't want to risk anything, even with her.  Maybe, especially with her.

For a good while after finding her lingerie in the Goodwill bag, when I could, I began dressing in her things.  It was about then that the Internet was really taking off, and my curiosity led me to discover crossdressers. I was amazed to find how many beautiful "girls" there were.  I began to wonder if I could pull it off.  I had to know.  I researched and researched.  Soon, I had a plan for how I'd give it a shot.  I couldn't risk delivery of women's clothing or a wig to my house, so I knew I'd have to buy what I needed from a store.  I couldn't do that in my hometown.  Too many people knew me.  So, I planned it for a conference I had to attend alone out of town.  I researched stores in the city of the conference and planned out every detail.  I was, as you might imagine, scared to death when I went shopping for my clothes, makeup and wig, but I was determined.  Confident that no one knew me, I was prepared for whatever store clerks might think of me.  I didn't care.  They'd never see me again the moment I walked out of their store.  All I knew was that I had to try.  And I did.  And it was amazing.  I'm pretty sure I looked like crap.  But I didn't care.  I was dressed up like a woman.  Fully.  Completely.

When I returned home from my conference, I hid all of my woman stuff in the garage where no one would find it.  The lesson I learned from my mother many years before - that men who dressed like women were perverted sex freaks - had stuck.  I could not let my cheerleader know.

This went on for a while.  I began wanting my cheerleader to be involved, but could never get up the nerve to tell her.  Instead, I began leading our sex life into more variety.  A little, especially from her standpoint, more kinky. For example, I got her to agree to try out a dildo.  She liked it.  She was uncomfortable at first, but she liked it.  When I saw how she liked it, I pushed the envelope.  I got a big one - shaped like a cock.  She really liked it.  I began inserting fantasy into our sex.  I'd lick her while I used the dildo on her.  I'd talk about her getting fucked with a big cock while I licked her.  She would never talk like that, but she liked it.  A lot.  I could tell.  She was hooked.

 

  Then, one night while we were making love, I got up the nerve, and told her I thought it would be fun if I wore a pair of panties.  She froze up immediately.  I'd gone too far.  She did not react as I'd hoped.  The subject was dropped.  I apologized profusely for suggesting it.  But then about a week later, when I got home from work, without a word spoken, she handed me a present.  When I opened it, she was watching my reaction closely.  My cheerleader had bought me a pair of panties.  She told me she'd decided if it was something I wanted to try, she was willing to let me.  But, the lie was still there.  She was "letting me try it out.". The truth was, I was simply drawing her in to something I had already tried out.  I was beyond "trying it out.". But, with her, it was a step forward.  She may not have known the entire story then, but she knew her husband wanted to wear panties.  

The Actual Panties My Wife Bought For Me

We made the first time we made love with me wearing my new panties an event.  Our children stayed at their grandparents' house.  We built a fire, and we put a sleeping bag on the floor.  I got inside wearing the panties, and brought the big, fat, dildo cock.  My cheerleader was great.  I think she really suspected even then that my desire to wear panties had not just "materialized" out of the blue.  She made it easy for me.  We had an amazing night of sex.  I licked and sucked her for hours, finishing with a great fucking with the dildo, and then me.  She always wanted to end with me inside of her because she said she loved feeling my hot sperm fill her pussy.  She still loves that.

We went on like that for a while.  She was tolerant of me wearing the panties.  A few months after that, I asked her if she would mind if I wore a nightgown.  I could tell this was going a bit too far for her.  I must have caused her suspicions to rise.  She saw my desire as a problem, as I realize many women who find out their husbands like wearing women's lingerie must feel.

She began checking behind me on the Internet, and hit jackpot.  Not only did she find the many cross dressing sites I visited, but she found a chat room where I went to play out my feminine fantasy.  I even had posted a few photos of me, and that really freaked her out.  She eventually confronted me.  I thought she was gone.  But instead, she arranged a long weekend away - just the two of us - to talk it out.  I was scared to death, but I was afraid she was going to leave me too.  And I loved her.  I love her.  I decided I had to, as we say in the law, tell the truth, the whole truth, and nothing but the truth.  And I did.  We went for a long walk one of the days we were away, and I told her everything, from the beginning to the end, including that she was the first and only woman I'd ever made love with.

She was definitely stunned by all that I revealed.  I think what confused her the most was that there was no way - no way- for anyone to have ever guessed that I might be a man who'd wear women's underwear.  That I was a sissy.  But, even then, the "sissy" word did not come up.  I didn't realize it, intellectually anyway, even then.  On the other hand, she was deeply touched by my honesty (finally), and concerned that I'd lived with this truth about myself for so long without ever being able to share it.

Well, I wish I could tell you that my cheerleader reached a moment of acceptance and that everything was hunky dory after that.  But that isn't what happened.  Instead, we lived with the knowledge of the "truth" for a while, with no reactions taking place.  We simply went on with our lives.  I continued to sneak wearing lingerie, with her permission - just not in her face.  And I had to promise no more photos on the Internet.

We moved on.  We continued having great sex, including the use of my cheerleader's new best friends, the big dildos.  Every now and then, she'd invite me to dress up for bed. And I'd joyfully accept.  I think even she realized that, on those nights, I enjoyed it more.  And she even did too.  There was a slow erosion of resistance going on.

And we went on like that for a while.  Until our last child went away to college.  And then, something happened.  And the next time I write about my journey to being a sissy,  I'll tell about it.