Prep school boy experiences different perspective during a club initiation
where he and some friends pose as girls at a local YMCA Dance during the
1960's when sex, class and racial barriers were rigid!

Gyrl in the Red Dress!
Illustrated cd interracial gay stories
TJ Ryder

gay teen cd tgyrl ladyboy Blackbulls/shemale romance
http://sissytrain.com/Fpage/fpage.html
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When I was a junior attending a boys prep school in the
Northeast I did the dressing in drag initiation as entrance
requirements for a stupid clicquey club like many kids do.

Since our school didn't have girls we did this at a teen dance at an
big inner-city YMCA, and the rules were I had to get a
minimum of three dances from strangers witnessed by club members.

I went with three other 'boys' wearing my older sister's red
miniskirt and tank top and mom helped me with lip gloss and eyeliner.
My hair was long enough anyway, no beard line at all,
(never had one), and being only 5'5" and slender I realized listening
to the jealous remarks from other guy/gyrls in the van that
they were envious of me! They didn't want me hanging around them
at the dance to get all the dances!

It wasn't until we walked into the dance and I saw myself in the
glass doors with the other three 'gyrls' what they mean't! By then the
big question the other guys were concerned about was what they
would do if a 'negroe' asked them to dance. We were in an
inner city Y after all! One kid, Travis, was from the south and
also on the tennis team and the next best-looking gyrl compared
to me and he declared he would never accept a dance with a
black guy.

I didn't even know any negroes hardly so I didn't have much
opinion, but I did feel it would be rude to refuse a dance.
I'd been to dances and my sister taught me to dance pretty well.
Franklin was the club prez making sure we didn't cheat, and
the fact is he drove the van and I wasn't leaving until all the boys
got dances, and he told me regretfully I had to stand on the
other side of the huge room which was a basketball court
along with Travis so we didn't spoil the other guys' chances.

Because the Y had monitors making sure no heavy making out took
place they played mostly fast songs until the last half an hour
so there wouldn't be too much grinding or groping.

My first experience was a shock. I just stood there,
not looking boys in the eye because that made them shy away
I thought, just standing there neutral, chatting with Travis,
but this one white boy made two passes and I was smiling
at him ready to say yes when he chose Travis!
Something he never let me forget, that he got first pick!
I knew by the way my face was hot I was blushing!
I was passed over and I looked at myself in the glass
doors and wondered why!

I had competition, more girls than boys as usual at these
dances, and I realized all I could do was just stand around like an
idiot. Yeah, I don't run the risk of asking someone and being
rejected, but at the same time I could spend the whole night
just standing there. Better to at least have some other 'gyrls' to
chat with, but then I remembered being on the other side and shying
away from girls giggling in a group, thinking they
weren't really available.

I did get asked toward the end of the dance by a shy boy and we
hung out for a bit. He wanted to do another but the rules
were that didn't count, had to be three different boys but I
knew I got credit for that one seeing Franklin checking me off
on his little pad, so I begged off saying I had
to get something to drink.

The next one was easier, all I had to do was arch my padded
bra out and smile neutrally as he pretended to casually walk by.
Check off # 2! Snagged him with my phoney tits!

When I returned to my wallflower location Travis was there with a
superior smile holding three fingers up!

"So your'e set then!" He laughed. Once again he was one up.

"That last one asked me for my phone number and he goes to
Classical and I beat his ass last month in straight sets!"

That was still another one he had on me getting the first phone
number request.

I hadn't even considered meeting people I already knew. I got asked
for a dance soon after that and that settled it up for me and Travis.
We couldn't leave because Franklin drove us and the other two hadn't
scored anything yet and we knew that Leon, our varsity wrestler,
would have trouble. He wouldn't shave his big arms and legs like we told
him and he had such a deep voice he decided just to smile. I thought that
made him look a little crazy!

I knew when the first slow dance began I was going to get hit on.
Several boys were circling, one I had danced with already.
This was getting weird! I had never even got to second base
with a girl! And Travis and I were talking like the girls around
us by then, even talking to them, and they all accepted us as girls,
another weird thing. When a cute brunette asked me if I went to
St Catherine's, I said no, we were from out of town.
At first I felt kind of strange but it was like being in a secret club.
Now in front of the other girls Travis and I were having fun
mimicking them.

"What about him? What do you think?"

"You can have him, he's like 15!"

"I think he likes you!" he teased!

"Oh fuck!"

"Uh oh, left flank!" I warned Travis. Two big black boys from
Central High wearing varsity football t-shirts were grinning at us.
The white girls around us started giggling and shying away except
for a bold one who smiled at them.

"I don't think so!" Travis said as he looked away. I saw they
were still coming over and making eye contact so I took his hand.

"Theyr'e going to do it and you cannot leave me on my own!"
I told him.

Travis looked at me, "I don't even know how to follow! What hand
do I put up?"

I looked at him then, I realized I didn't remember either, but it
was too late, because two towering, muscled-up black guys, probably
seniors, were right there with big smiles.

"Hey ladies, like to dance?" They had stood in front of the 'girl'
they had already chosen like boys do, and the speaker was in front of
me and there was a little pause all around us as everyone watched and
listened.

I was not doing this by myself so I took Travis by the elbow and
pulled him forward with me,

"Sure, " I said with a smile, swallowing because I was so nervous.

Travis hesitated for a bit, but nodded and smiled and we went out
onto the floor and I started a little at a big hand on my hip, and
the hand question was settled by the way their big hands moved
and soon I had one arm over a brawny shoulder and one in a
big hand, and was closer to a black person than I had ever been,
and his hand was close to my butt! I knew my face was hot so I
just peered over at other people but he was quiet as we danced
and then asked me my name. Aw shit, I had never even thought of
having a girl's name. I settled on Terry cuz that was my name.
Where did I go to school? After a bit I looked over at Travis whose
face was red and biting his lip as his partner talked. After that
we were back doing the wallflower bit and I looked at his expression.
Neither boy asked us for a second dance. I just looked at Travis.

"What is it?" he asked.

"Nothing, I didn't say anything!" Changing the subject I looked
across the room and said we had to give Gus and Leon a little help
or wer'e going to be here all night! Franklin had already given up
on them and he and the other club members were dancing with
girls.

"How do we do that," he laughed,
"they actually make uglier girls!"

I was always a hustler. "We charge them ten bucks a dance
and give five to boys saying theyr'e our sisters!"

"No," he smiled, "wer'e much too popular for that. We keep the ten
and tell boys we'll dance with them after they ask those
guys first!"

"I like the way you think!" I went across the room to make
the proposal and while Leon groused at it, they were secretly
relieved.

That still took a while and even when Leon finally got his
three, Franklin was having so much fun pitching a blonde that he
said we were staying to the end. So we took several more dances because
it was boring just standing around and at the end of the night
they played more slow ones to wind things down and I was dancing
with a big Italian hood trying to grind as I kept pushing him back
and then I see Travis dancing with that first black jock and
he had his head on his shoulder and the boy was actually cupping his
butt a little in his miniskirt. Damn! After the dance they
went off laughing to the refreshment area, which was just a weak
punch and some cookies on a couple of cafeteria tables.

Half an hour later they were dancing again, and then it was time
and monitors stated turning up the lights, the band said good night
and Franklin came by with the other two asking where Travis was.
I was still trying to shake my Italian suitor and was grateful now,
and finally Travis came over, and we were outside getting into the van,
but Leon was impatient to take off his wig and we drove back
laughing and exchanging stories; except for Travis, who just
sat there looking out the window with a pensive expression and just
occasionally nodding and giving a little smile of acknowledgment.

The next day Travis dropped a bombshell on me during tennis practice
when he remarked that the second time he danced with that black guy,
he knew what we were and wanted to know if I was interested in double
dating!

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While a stand alone story, it has been included in an Omega Fraternity
series at Sissytrain.com/ starring the same characters in Have Dress/Will Travel!