A cute blue silk pj set started it all
It started with my sisters pajamas when I was 13 years old. They were light blue silk with lace and I just had try them on after feeling them on my c***. The camisole had a thin strap and the shorts had wide loose leg. The affect was immediate every time I wore them, instant hard-on. I can still get hard just thinking about it. I would also sneak a pair of her panties to j******* into. But I missed wearing these PJs after she left for college. My mother’s panties weren’t as nice, but it was all had until I met my first real girlfriend.
I never really had the final growth spurt that my dad wished for and when I left for college i was only 5’ 8” and 150lbs, all the men his side of the family were 6’ or taller. I was kinda shot, not too short, but short enough to make it more difficult in attracting girls in high school. I did manage to have a steady girlfriend who informed me one night after drinking too much that I had cute little b**** and my d*** was small than she was used to so I could I please pound her harder.
I stole a few pair of panties and even took a pair of her panties when I left college, a pair of red silk and lace thongs, they fit me almost perfect and I was thankful for the first time for having a smaller package, I wore and jacked off in them so many times I lost count.
A few years later I figured out I could by my own panties, always posing as a caring and thoughtful boyfriend. After college and living on my own, my courage grew and I began experimenting with stockings, pantyhose, bras and bralettes, camisoles and so many styles of panties. It was paradise.
It all ended when one of my girlfriends found, what I thought was my well hidden collection and freaked out. I swore that a previous girlfriend must have left them and I had no idea they were even there. She told me later that evening she thought something was off when I kept buying her things from Victoria’s Secret and that she also suspected that I might be gay when I licked my c** from her face. She also was certain that I had used her d****, which I adamantly denied. It was much bigger than me and I never could comfortably enjoy it in my ass.
Since that incident, I kept only few pieces when dating for fear of getting caught again. In between girlfriends my collection would grow and I would try few new pieces and even tried to crossdress, but I didn’t have the figure to pass. I did however find enough pieces to fit and flattered me, that I could go out in public dressed completely in women’s clothing including shoes, albeit flats or sandals and only a few women seemed to notice.
This went on for a few years until a cute gay man noticed and followed me the restroom at the mall. Once the room had cleared he told me I was cute and kinda sexy. He offered me a b******* right there in the bathroom, he pushed me into the handicap stall, pulled down my Gap boyfriend jeans and my Victoria’s Secret satin panties and sucked me to completion. Honestly it didn’t take long, I was so turned on. He didn’t stop when I came and sucked me the point I was too sensitive and begged him to stop. He stood with a grin on his face and leaned into kiss me, I had never kissed a boy before and was nervous and excited. When he stuck his tongue in my mouth it was followed with something thick and a little salty - it was my c**! I didn’t know what to do and swallowed it. He said thank you and left. I think I would have tried to return the favor if he would have stayed.
I then met my wife, she was smaller than me at 5’ 3” which made me feel strong and manly, she was only a cup and think that helped us with my smaller package. She was for more sexually curious than any other woman I had been with and had me try so many things for the first time. I fell for her hard and almost shared my secret with her more than once. As you may have guessed, I would sneak my wife’s panties from time to time, they were too small to be comfortable, but they worked to fulfill my secret needs and I’m sure she caught me once, but never said a word.
We have two beautiful kids, our son graduated college this year and received a permanent position with the company at which he interned. My daughter is the most independent of our family, tall at 5’ 9”, very athletic and was always more of tomboy. She started as a freshman on a volleyball scholarship at a college out of state this year. Not sure if I like it or not, her being so far away. Despite having boyfriends, I would not be surprised if she came out as gay, but who knows about these things anymore and she is at the age of finding herself. I suspect why she chose a school so far away, makes experimenting easier when no one back home is there to judge you.
So last weekend My wife went on her annual girls trip and I was left alone in the house with no projects, plans and or kids at home for the first time. I was curious and after trying on most of what my daughter left, I can fit into almost everything but the bodycon dresses I never liked my her wearing and a few tops. She also hid, poorly I might add, a small, but still a bit larger than me lifelike d**** and harness, it had veins and noticeable head. After becoming drunk on the experience, I slowly managed to get relaxed enough to fit it in my ass and be comfortable, albeit filling full if you know what I mean. I decided to strap it on a gigantic bear her boyfriend gave two years ago. I was able to ride him a little and wished he could mount me. When I did c**, I was dressed in a yellow satin nightie with homer in my ass, and I came so hard so much more than I ever have before.
I’m torn about telling my wife what I have kept secret all these years. But I want to share this with her and I want her to use the strap on d**** on me.