Halloween Surprise, Pt 1

It’s been a while since this happened but I remember it like it was yesterday.

I had just turned 17a few days before my favorite holiday. I’m a good looking guy, 5’6” maybe 140 lbs. Not the biggest guy in HS but not the smallest either. I have what I call camouflage colored eyes. Sometimes their brown, others green depending on what I’m wearing. I have a nice slim toned body from track and always loved being outdoors.

Yep, Halloween was right around the corner. Trying to come up with a good costume was always a tough thing to do. I needed help coming up with a good idea or two, asking my friends and family, easily discarding their ideas of zombies, bums or a football player… I asked a few teachers at school. My English teacher, Mrs. Roberts laughingly suggested I dress up as a cheerleader. It’d be different but I don’t see myself doing it for obvious reasons. But after telling my girlfriend, she was all over it and decided to make this her thing to do! I couldn’t argue with her as excited as she was so I went with it. We had plans to go to her older sister’s Halloween party at her Dorm upstate so no one would know me and it was all for fun anyway.

So the morning of the party came. Sherry, my girlfriend, brought the costume over along with hers. She told me last minute she was going as a Vampiress. I couldn’t wait to see her in her costume. We fooled around a little then about 2 we got down to business of getting dressed up. She had me shave my legs and the little bit of hair on my arms and face, armpits came next, which I argued about but eventually lost. Oh well, get into character right?

Once all that was done, it was time to get dressed. First, satin panties, then cheerleader knickers, short white and blue skirt. Bra and some silicone breast forms. Well, the forms kept moving around so Sherry decided to glue them in place. After that was done, the bra went back on, followed by the tightest sweater I ever wore. I have somewhat short hair, so she pinned a black wig on my head.