Long Time Friends First Time Lovers

Young man finds herself with the help of a close friend.

I had always had difficulty connecting with anyone or attracting women. Being six foot five, one hundred and forty pounds and being eighteen during my senior year of high school, my appeal to women wasn't very high. I was never the wrestler or jock material and coming from a small town in South Dakota. If you weren't athletic you wouldn't get the ladies. So being the loaner I was and had a lot of free time on my hands and developed a liking to women's clothes. I had acquired quite a collection that I would often wear under my normal school clothes. Bras, panties, and pantyhose or thigh highs the more feminine the better loving the way they felt against my smooth shaved skin, what little hair I had. There were many times at school when I thought I would get found out and I‘m rather sure I would get my ass kicked badly if anyone did. But family being family I couldn't keep a secret hidden for long considering my collection took up almost my entire bottom dresser drawer.

Being that I didn't have anyone in my life to go out with romantically. I spent a lot of my time with my best friend, Doug. We would go to movies, hang out playing PlayStation, or go to the bar and shoot a couple games of pool. Many times we spent almost all night at his house. But Doug always talked softly around my dad my father would say Doug was gay all the time to me. So they didn't get along very much.

One day Doug had mentioned to me that his mom and his big sister were going to be gone for the weekend. They were going to some big flea market with his grandmother and aunt. He asked if I would like to come over and stay the night. I jumped at the chance to get out of my house. So I packed up some overnight clothes, and some sexy stockings and bra and panties with a nice black slip, and a pair of ankle strapped pumps. Doug didn’t know about my dressing but I so had the urge to get dressed up.