Memorable Experience

One of my first memorable experiences crossdressing was before I was married and seeing a women older than I was.
One evening we were watching X and R rated movies. One of them had a scene where a man was stretched out on the bed next to a women wearing lingerie, nylons and high heels. Lou turned to me and asked “would you do that if I asked you to?” Try to look surprised I said “I guess but on one condition you have to wear matching.” She knew I had a high heel fetish but had no idea that I had already crossed the boundaries of cross dressing. I did not try to pass I just loved the feel of lingerie, nylons and of course high heels. After the movie she asked me my shoe size and brought out a tape and took my measurements writing them down. Sitting back down she asked another surprising question. “What do you know about **** rings? They eluded to them in one of my magazines but gave no details.” I explained to her why and how they where used and that I had several. “I will wear one the next time you suck me or I **** you.” This became the norm when we had sex. She took pleasure putting it on me.
As the days went by I gave no more thought to our discussion about cross dressing, *** to find out she had not, in fact her mind and imagination went into overdrive. One afternoon when I arrived she said “I have a surprise.” There laid out on the couch matching lingerie, nylons and black leather thigh high boots with a 5” spike heel. She said I know the heels are outrageously high but what the hell! “That’s alright you will be on your knees or back anyway.” I replied. We both undressed, she then placed the beloved **** ring on me. We then dressed each other in the lingerie and nylons. As she placed the boots on my feet she kissed and licked the toe of one of the as it were a ****. She then slid the spike heel in and out of her lips and mouth as if it were a ****. Doing the same to the other she grabbed the heel and brought the toe to her **** and ***** alternating between the two. She closed her eyes lick her lips and begin to **** the boot!
Many memorable and enjoyable encounters were had while we were attired this way. One of her favorite scenes was for me to sit on a chair my ringed **** across my high heeled boot while she crawled across the room to suck my **** before I ****** her
wellheeled2 wellheeled2
51-55, M
1 Response Sep 20, 2012

ooh my wonderful read