Adventures at the Mall

By Kozmik Alaska

Unsure of where to spend my Saturday night, I decided to visit the shopping
mail in a nearby town.  I dressed stylishly, donning a pair of black trousers,
a white shirt, red tie, and stepped into a pair of penny loafers.  Underneath,
I wore a white athletic shirt, white Fruit of the Loom briefs, and black socks.

I had splashed on some Brut after-shave and trimmed my fingernails short. This
was, incidentally, my first time in public dressed as a guy. At the time, I
was an eighteen-year-old female, a senior in high school.  I'd been
cross-dressing in secret, borrowing my younger brother's clothes whenever I
could.  My parents were gone for the weekend and my brother was away, so this
was the perfect opportunity to go out dressed as "Steve" (my alter ego).

As I drove to the mall, seeing my handsome face in the mirror and feeling the
masculine clothes against my body was making my jockey shorts wet.  With my
short unisex hairstyle I looked very much like a boy.  My brother was on the
small side so we were about the same size, therefore his clothes fit me pretty
well.  I looked and felt quite handsome.

I picked a mall in another city so there wouldn't be much possibility of
anyone recognizing me.  As I walked through the mall, no one seemed to notice
that I wasn't really a boy. Some girls even flirted with me, which excited me
greatly. I even began to feel like a boy!

While there, I purchased some after-shave and cologne in a fragrance I liked.
I then went to a sporting goods store and picked out a few jockstraps for
myself.  Later, I went another department store to pick out some shirts and
ties.

While I was looking at some ties, someone whispered, "Stephanie?"

I turned around, and standing there was Jim, a boy from my school.

He said, "I can't believe that's really you dressed as a boy.  You look great."

He told me not to worry - he wouldn't tell anyone about me.  Then he said it
turned him on to see me dressed that way.

We both picked out matching striped Y-front jockey shorts, and then he
followed me back to my house.  There, we stripped, put on our jockey shorts,
and made love for hours.  He told me she had dreamed of making it with me ever
since he saw dressed in my running silks on the girl's track team. I told him
that I, too, wanted to screw while dressed in a pair of sexy jockey shorts.
The cotton of the briefs felt so good on my clit, as we rubbed our crotches
together. Our kisses were incredible. 

Jim and I began dating right after that, and even went out cruising for
chicks together several times as two guys.  He made me wear jockey shorts on
each date, and suggested that I stop shaving my legs.  He even bought me a
fake moustache.

A couple years later, Jim and I were married.  Underneath our wedding garb,
we wore Bike jockstraps. On our honeymoon night we reaffirmed our vows with
me in a tuxedo that matched Jim's.  Since we've been married, we both sleep in
just tee-shirt and jockey shorts.  I don't shave my legs or underarms, and
wear Fruit of Loom guy's briefs daily. Needless to say, our sex life is
fantastic!