Ashamed by Anonymous

This is a real confession.  This is the first time I have ever shared it.  Nobody in my RL knows this, and I still feel ashamed of it.

 I moved to the South of England when I was 16 in a heart-wrenching period of my life, and settled in a town called Horsham.  I attended an all boys school, and made a few new friends, though my northern accent caused more conflict than anything else there.  In short, I was isolated and alone.  Until Stephen invited me around to his to hang out.

Stephan and I were friends, though I didn't really have much in common with him.  He was fat, smelly and liked football.  I was short, slim and preferred rugby.  We had to find something to talk about... And thats where his girlfriend came into play.

Meeting at his house, I met Laura for the first time.  I am not a confident person, but she was really pretty.  She was perhaps two years older than me.  She was a woman, really, and I felt like a spotty kid.  Instantly, I fancied her.  We three were alone in the house (Stephen's parents worked shifts or something I think.  I never met them).  So, being alone, and teenaged, we got some larger out and began drinking and talking.

As I said already, I was small... and it didn't take much for me to feel the warm glow of the beginnings of being drunk.  We started talking about what each of us were going to be, and me, slightly inebriated, mentioned being a lawyer.  This led to talk of wigs, and that led to makeup... and that led to Laura suggesting she gave me a makeover.

I should have said no.

But I didn't.  It sounded fun.

For the longest time, I have always fantasied about being female.  The idea of a makeover made me squirm.  It sounded forbidden, taboo, and yet at the same time, so right.  I should have said no.

But I said yes.

Stephen thought this was hilarious, and found his mum's makeup.  Laura sat, straddled, on my lap and began to apply foundation, blusher, eye-liner and lipstick...  And I loved it.  I found her hips over mine and, being a teenager, had no control.  I think all boys of that age think with their balls.  I know I was.  Laura could have done anything to me then, if she simply remained on my lap, like my girlfriend.

"There now... a proper little sissy" Laura said at last, when she was done.  I remember I felt really same-faced at that, but elated too.  Although it was obviously over, I didn't want it to be.  I was embarrassed, but it was fun too.  Her next words made me stir even more.   "We should dress you up!"

In no time at all, I was handed a dress of Stephen's mother's.  Her shoes wouldn't fit me, but in the end, I had on some tights, a pair of (I am afraid to say) granny pants, and a white dress that was impossible to zip up behind me.  Thankfully, Laura helped me out there.

That isn't the confession though.  That just sets the context for what came next.  Something I have never done since.

Returning to the room, I say Laura and Stephen kissing, and instantly felt in the wrong place.  Obviously Laura saw this and waved me closer, guided me by my hands...

...and sat me on Stephan's lap.

She told me to kiss him.  I did.  His tongue invaded my mouth and I let him.  I closed my eyes, imagined I was a girl... And kissed back.   I felt Laura stroking my back, encouraging me.  The kissing ended a little while later... And Stephen unzipped his fly.   I looked at him and watched as Laura took him out of his pants and stroked him.  She was looking at me, and gestured me closer....

God knows why i got closer.  I think I was caught up in the moment, perhaps in the fantasy of being female, or simple because a pretty girl was asking me to...

I stroked him.  Other than my own, his is the only other cock I ever touched.  He was hard, and kinda crooked.

"Kiss it..." Laura told me.

I am ashamed to say that I did that.  I kissed the head of his cut cock, It was weird.  I didn't really like it.  But Laura kept telling me I was a good girl... her hand was on my head, gently pushing me down on him...

I didn't last long.  I couldn't stand it.  I pulled away and ran into the toilet.  I didn't emerge for half an hour, ashamed... Laura wasn't there when I emerged, but Stephen was.  I phoned home for my mom to pick me up.

I never saw Laura again.  And shortly afterwards, my family moved back up north.  I left the past there...