Okay gals, here's a true story.
I'm BI so I date women regularly. The women I date are a product of my searches of a couple of singles websites.
Up until recently, I have been dressing at night and then finding friends here to help me explore my femm side. That has been real exciting for me ( as well as for some of my sissy friends on-line- you know who you are...) anyway, recently I met a woman online that is about my age. We chatted for hours over the past weeks. This morning a longtime dream of mine came true. This woman kept asking to meet me and would not take no for an answer. So I finally gave in and agreed to meet for lunch. Before I left, she said that one of the things she wanted to help me with was to "help me explore my feminine side." So I was curious if not a bit naive. Just as a back-up, I carry an emergency overnight bag in the trunk of my car. It has what I call- a change of sex kit in it. Everything I would need for that special someone.
We met, had lunch. During lunch I noticed she had on a fairly short leather skirt and black nylons and a pair of black boots. I always notice what women are wearing. She had on a pearl-white silk top with a thick black belt. She asked me if I had plans for the afternoon and I said nothing that couldn't be broken. She asked me to follow her back to her condo which was only about 2 miles from the restaurant on a secluded avenue.
It was about 2 PM when we got there. She had a beautifully decorated living room, kitchen and then came the bedroom. She was sure to point out the over-sized closet. Went inside she asked me if I saw anything in there I liked. I said, I thought she had fine tastes in clothes. She then came over to me and began caressing me around the shoulders and chest. I was immediately turned on and my clit responded to her hips as she pressed against my southern region. We began kissing, softly at first and then more deeply, more passionately.
She then asked me if I was "open-minded" and I said what do you mean? She said she couldn't help but notice how my face lit up when I examined her wardrobe. I then told her I enjoyed dressing occasionally ( lying of course about the frequency). She asked me what I like to wear. I said it depended on my mood. She then grabbed my clit and started rubbing me. I said I'm in the mood. I forgot all about my overnight bag as her stuff made mine pale in comparison. She asked me if I was a sissy, and I said yes. She said she wanted to realized one of her fantasies and make love to a man dressed as a woman. I said I would very much like that. She asked me what dress size I wore and as it turned out she had several dresses in her closet my size. I pick a few out and while I was doing that, the went for the undergarments.
She was also the same bra size I regularly wore when I dressed (40C). She gathered up a black push up bra, corset, garter belt and some very nice black laced panties. She also had some open-toes black heels which were one size smaller, but I made them fit. Before we dressed. we each stripped each other naked. We took a shower together and while in the shower, she shaved my legs. She applied some very sweet smelling after-shower cologne on my butt, legs, chest and neck. She also supplied me with cosmetics which she put on me. While she applied the make-up I glue on some french-tip nails- my favorite. It was almost like we were lost sisters re-united. When the make-up was completed, she put an Eva wig on me which complemented my skin tone and head shape. I applied the lipstick as I knew how to do that. I then found the black lingerie on the bed she had laid out for me.
While I got the under garments on. she finished her makeup. Then I helped her dress in her white crotchless boy-shorts, bra and white nylons. She looked fabulous. We both then helped each other put on our outfits. I chose a black woven skirt and a silk red top with a ruffled frill around the chest. I had a natural cleavage and the push up bra just made my breast appear two sizes larger. She opted for a blue one piece dress with a white belt.
By the time we were done dressing, it was after 4PM. Over the next hour, we had a lot of fun, we mutually masturbated, then she sucked my clit and then we went into the 69 position. Then I fucked her in the ass and she returned the favor with the strap-on she kept hidden in her night stand.
I'm still flush with excitement over the experience. I will have pleasant dreams tonight!