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My name is Jimmy James. When I started high school, my parents shipped me out to boarding school to teach me discipline. They were mad because I had always been a disappointment to them. I wasn’t terribly manly and I liked to dress in girls clothes. The more often they caught me dressed like a girl, the madder they got.

The final straw was when they found me in the pool house wearing my
sluttiest outfit. It wasn’t so much what I was wearing that bothered them
tho. What bothered them was that I was on my back with my legs spread.
While my friend Bob was laying on top of me, fucking the ever loving shit
out of me. It was quite a shock for all of us.

So off I went.

The place sounded horrible. It stressed regimented schedules and family.
The housing was set up to be two person cabins to promote self reliance,
blah blah blah. It wasn’t so bad as I thought tho. I ended up being
quartered with the perfect room mate. His name was Mike, but everybody
called him Mickey.

I found out he was the perfect room mate about six weeks into the first
semester. I was s’posed to go home for the weekend, but missed my train.
When I got back to the cabin, there was Mickey wearing the sluttiest
little school girl outfit I had ever seen. Black high heels, thigh high
white stockings, tiny white thong, ultra short plaid skirt, thick black
belt, see thru white top, stick on D-cup breast forms, no bra and long
black wig….

He was fucking HOT!!

I could only hope that I looked that good when I dressed up. Everybody
always teased him about having a big ass, but dressed like this, IT WAS
PERFECT!!! The whole thing just screamed ‘slutty little sex kitten’. I
was sure he liked getting fucked as much as I did.

As I stared at him, I could feel my cock getting hard. That’s when it
dawned on me that I should have a little fun. We were both still staring
at each other in shock. He quickly began to scramble to cover himself.

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