First Ever Pantyhose Sex

My first time having pantyhose sex with another person was in college. I had been wearing pantyhose and pleasuring myself for years, but this would be the first time anyone else had seen me wearing them.

My GF and I had been dating a while and we decided to go to the beach for a bit of intimacy. It was night time and very foggy, so you could hardly see a thing. We had been out to dinner, and had a bit to drink. My GF was wearing a dress with pantyhose and high heels. This was the early 80s and women wore pantyhose quite often.

We grabbed some blankets and found a fairly secluded place on the beach. We laid out some blankets on the sand, laid down and pulled more blankets over us. We began kissing and fondling one another. Slowly, we began to take off each others clothes. At some point during all of this, I asked her if I could try on her pantyhose. My GF at the time was a fun loving girl, and said, "Sure!" She handed me her nylons and I began to roll them up and slide them on. I got them on quickly, and that should have been a clue to her that I had done this before, but she didn't seem to take notice. Once I got them on, she giggled and said, "Let me see!" So, I stood up and she got see me and my legs all clad in her nylons. She laughed and said, "Turn around, I want to see your butt!" I twirled, and gave her a good look at everything. She giggled some more and seemed to think it was fun.

Of course, I was hard as a rock, which was another clue I had done this before. Still, we had been making out, getting naked, so being hard was not unexpected.

I climbed back under the blankets and resumed our kissing and fondling. Of course, the pantyhose stayed on, and my GF did not ask me to remove them. At the point in which we were both ready to screw each other, I simply got on top of her, lower the pantyhose down enough to take out my ****, and then slid it inside her. We ****** for like a minute and then I blew my load. It was a bit embarrassing as I typically lasted quite a bit longer - but having sex with the pantyhose still one me was just a little too arousing.

Our relationship went on for many months and we had pantyhose sex several times after that night on the beach.
BizSuitStacy BizSuitStacy
56-60, T
1 Response May 18, 2012

I remember my first pantyhose sex. My girlfriend (now wife) was a little weird about it, but after a while, she grew to enjoy it as much as I do.

I find it interesting how some women grow to really enjoy it. They feel a little weird about it at first, primarily because they have been raised that way. No one grows up thinking about how great it would be to have a relationship with a crossdresser. Yet, so many women admit it later that having sex with their significant other while he is dressed up can be mind blowing.

Very true. Now she almost insists I put on something silky for sex. Had I been asked 17 years ago if I thought my girlfriend would accept my wearing, I would have said no, but now my relationship with her is incredible...both in & out of the bedroom...she has no problem with me wearing hose or panties out under my clothes even if somebody else may see...