Sissy Steve and Me


Introduction:  Steve and I have been friends since 2nd grade.   You could say we literally grew up together.  As little boys we liked all the usual things, baseball, cars and trucks, fishing, and later ‘girls’.  When girls entered the scene things began to change.  Everything about girls was a mystery to us.  We had no idea what was under their dress.  Everything about them was a secret to be kept from boys.  Particularly their bra’s, panties, slips and petticoats, these things were all girl, and were all alien to boys.  Oh well, this is where our story starts.

Chapter 01:  Discovering girls and their ‘stuff’

Since both Steve and I had access to sisters, he had an older sister, Karen, whose clothes would fit him, and I had a younger sister, Judy, which was no help, too small.  But my mom was a small woman and her dresses would do perfectly.  So here sat Steve and I on a rainy spring day, wondering what we should do.  No one was home on this Saturday, everyone was out shopping, so we could get into mischief without worry of getting into trouble.  Pondering our options, which were limited primarily to games, so we decided to try something new.  “Let’s play dress up” Steve offered, that’s new alright and I readily agreed.

OK Stephaney, let’s get some dresses from moms room. She has kept all her old dresses and dolls for Judy.  Then we can play girly stuff.  Oh by the way Brian where did Stephaney come from?  I just thought it fit you Steve (giggle).  Well then what’s your girlie name Brian?  How about Barbara, or better yet, Brenda.  That’s it, come on Brenda, you need a dress (tee-hee).  So do you Stephaney, I piped in (with lots of giggles).  Picking out dresses was real fun.  Seems like mom had saved them all (they were almost new).  It was hard for two little boys to pick two out.  Finally, they decided on two full skirted day dresses, one ‘hot’ pink and the other pale blue.  Guess who got the pink dress, ‘me’.

Sliding into them was easy.  But the back zipper was another story, our arms just wouldn’t bent that way (we would find it easier in the near future).  Zipping up each other’s dress we stood back and admired what a pretty little girls we had become. The dresses we had picked were little girl dresses with short skirts, and bending over wasn’t an option.  You could see our underpants.  So we vowed to be ‘lady like’ when in a dress.  Giggling, we started to look through moms doll collection.  Wow she has a lot of dolls, all types, Bridal dolls, Ballerina dolls, Formal and play dolls, and she had a huge doll house.  We had a hard time picking some out.  But finally we found two that we liked, a formal for me, and a Ballerina for Stephaney.

We played with our (her) dolls for some time, dressing and undressing them when Stephaney realized we hadn’t put on and girlie underwear.  OMG that’s right I exclaimed, but looking at the night stand clock I realized we didn’t have time today.  Mom was due home at any time and if she caught us like this we’d get a beating for sure.  So we picked up everything and put the dolls back in the Doll House, exactly where we found them (but we couldn’t stop giggling like little girls).  Next we hung our dresses on hangers, carefully smoothing them out, and placed them on the closet rack, all the while we talked and planned out next adventure in ‘girlie world’.  The next time we would do it right, panties, bra and a stiff crinoline petticoat (giggle).  But Brenda, there’s no girlie shoes in here, where will we get them?  Maybe from Karen, or my mom, or we’ll have to get them somewhere else Stephaney.

We were deep in ‘fantasy land’ when mom and my little sister got home. ‘Brian, Steve, where are you?’ mom shouted up the stairs.  Up here mom, we’ll be right down (giggling softly so she wouldn’t hear).

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