Never Quite Right
I wouldn't call this a story per se. More a history of my cross dressing and experiences related to it whether it was just dressing up or sexual as well. How bout if we go all the way back? If I'm going to do this, might as well do it right.
I remember as far back as twelve or thirteen discovering the pleasures of satin panties. My mom wasn't much into cotton I guess and wow how exciting for me.
I was putting my dirty clothes into the hamper and there they were, laying on top. They were a pretty peach color and shiny as well. I was curious, so I felt them. Man did they feel good. Immediately, I wondered how they would feel on my cock. Everyone was home so obviously this wasn't a good time; I hatched a plan.
The first day that I knew my sister had an extracurricular event planned, I hurried home from school. Before changing from my school clothes into a pair of shorts and tee shirt, I stripped all the way down. My heart must have been slamming in my chest. I reached around in the hamper until I could feel what I wanted. My boner was aching.
In my hands was a lovely pair of baby blue panties with lace trim. I rubbed them on my hairless chest and stomach. I had thought about laying on my bed and experimenting with them, but didn't make it. I had such an overwhelming desire to masturbate, I laid down on the floor in the hallway outside my bedroom.
I started by just teasing my prick with them; holding them in both hands, stretching them out a little and lightly waving them over my penises shaft and head. That made it stand right up!! I noticed that my testicles were rolling around, up and down.
I took the panties, putting my hand inside and began massaging my balls. I did this until I could no longer bear it and began stroking my cock with them in earnest. Full fledged jacking off until I finally exploded. Didn't have any Kleenex or toilet paper either, so I scooped my cum into my fingers and swallowed it. Learned I like something else that afternoon as well!!
White pairs, beige.....chocolate brown, peach...the baby blue ones, black......Used them all. Even began sliding them on as well.....being careful to not leave any tell-tale stains on them. Oh how I enjoyed those afternoons and occasional nights when my parents stayed out late. I played with them in bed in the darkness, making sure not to fall asleep with them.
Time to move forward a few years. I've graduated from high school and still masturbating as much as possible (no girlfriend), quite often with my mom's panties. My sister is on her second or third boyfriend and sometimes I have the house to myself for weekends. Parents up north, my sister away as well.
Over the years, she hasn't had much in the way of panties. Plain old cotton.Guess she was trying to look like the good girl. With everyone gone for the weekend though, I decide to rummage through her drawers more thoroughly. Surely she must have something to tempt her boyfriends with.
My search was rewarded with an incredible prize!! Hidden deep in her drawer was a sweet little sea-foam green teddy. I had searched early so most of the night I could hardly wait to turn out the lights and call it a day. Soon after dinner, I read a little, watched some TV with a beer and decided it was time. Heck....I don't think the sun was going to be down for about another hour when I decided to get in bed!!
This time was going to be different though; I wasn't just going to be stroking myself with this teddy. I was going to wear it for the whole night. I decided that I wouldn't jerk off right away, I wanted to savor the delicious feeling as I fell off to sleep.
Once again in my life, my heart was pounding like a trip-hammer due to lingerie. I put on the teddy, adjusted the straps and snapped the crotch; it sure was tight. For kicks, I got out of bed and went into the bathroom looking at myself in the full length mirror. What a turn on.
Coupled with the mugginess of the summer night and my arousal, it was hard drifting into a slumber. I did eventually though. It was such a sinfully sweet sensation to wake up throughout the night and one last time before sunup the following morning.
Upon waking up in the morning, I unsnapped the crotch and freed my penis. It was painfully hard and throbbing. I pulled the teddy up to my chest and began masturbating slowly until climax, once again swallowing my seed as I usually did when masturbating.
After I got out of bed, I took my sisters teddy to the basement and washed it in the basin and then dried it on delicate. The sweat stains were worse than my precum while I slept. When I was sure it was totally clean, I put it back in my sisters dresser the way I found it.
Oh that night was magic and I never heard anything from my sister either!!!