My Friend Kay

Although I started pleasuring myself with kid gloves and satin when I was 13 years old, I did not completely cross dress until I was in my late thirties. At that time I was living with the sexiest, horniest female that I have ever known. Her name was Kay and I met her when I was working as a car salesman. I had just sold her a new car and was telling her that it was my birthday and that I thought that the girlfriend that I was living with at the time had forgotten about it. One thing turned to another and after about an hour or so of flirting we made a date for that evening. Needless to say it was a most memorable birthday.

Shortly thereafter, we moved in together and worked at remodeling this old house at those times when we were not having sex. She was insatiable which was great for me. I confessed my fetish for ladies kid leather gloves and satin and she thought that it would add excitement to our lovemaking. Anything that would add excitement to our lovemaking was great with her. She had me wear the gloves and massage her tits and her pussy and agreed that the gloves did indeed heighten her orgasms if that was possible. We went shopping and she bought a whole collection of leather gloves and satin lingerie. Looking back, I honestly believe that I created another glove fetishist

One night we got into sharing our deepest and most private fantasies and I poured my soul to her on how I really wished I had been born a woman and would love to dress up as a woman and go out in public to see how it felt...She said that her fantasy was to have a "threesome" with her girlfriend Vonna and a stud. She confessed that she and Vonna did have lesbian sex occasionally and that they were both bi and highly sexed . It was no surprise then when she said she would help me to realize my fantasy. We went shopping and bought everything that I had dreamed of wearing as a woman from bras and panties to a corset and lacy thighhighs to satin slips and camisoles and pencil skirts, boots and a walking coat to wear with my elbow length black kid gloves. The night came and I got all dressed being very careful not to cum on any of my precious new things. She did a masterful job of applying my makeup and found a short dark wig for me. When I looked at myself in the mirror I could not believe the transformation. From that point on, I was hooked. I had never felt so sexy or sensual in my life. So this is how women feel, I thought to myself.

She asked me if I still wanted to go out of the house dressed as a woman and I quickly agreed. We headed for the Mall at Tyson's Corner and parked just outside of Macy. We parked as close as we could because it was still a challenge for me to walk in high heels even though I had been practicing at home. We went to the sportswear department and checked out some leather skirts. Finding one in my size, we took it into the changing room for me to try it on. I must have looked pretty good as a woman because nobody batted an eyelash. Of course I just had to have it. We went to the ladies room and I removed my pencil skirt and put on my new leather skirt. Afterwards, we went out for a drive and she could not keep her hands off of my leather skirt and red satin blouse and she kept stroking my leather skirt covered thighs wanting to hold my gloved hand. She admitted that my being dressed up as a woman was making her very horny. Finally, she worked her hand up under my skirt and wriggled my panties off enough to allow my hard cock to spring out and she started to give me a hand job as we were driving. I protested (mildly) that this was very dangerous ( if you ever read the book (Thinner) by Stephen King) so she directed me to an empty parking lot where I parked the car while she gave me the most fantastic blowjob of my life

She cleaned up the cum and straightened out my skirt and asked me if I would do her a favor. She reminded me of her fantasy as she called her girlfriend to see if she was home. I found out later that the two of them had had an affair on and off for many years. Her friend answered the phone and she invited her to come over to our house but she had to bring a satin nightgown and the longest pair of kid leather gloves that she had and that she had a surprise for her. She hung up the phone and we hurried home to change.

She arrived wearing her trademark long leather coat over a black satin nightgown and black knee high boots and long almost up to the shoulder black kid gloves. She was wondering what was going on and asked where I was. She said that I was in the bathroom changing and that she was also getting into her satin nightgown and putting on her kid gloves. By that time I came out in a red satin nightgown and black elbow length black kid gloves as well, Kay had already changed into a beautiful light blue satin nightgown and a pair of elbow length white kid gloves.

Kay introduced me as her "new" friend Sylvia who was going to pleasure both of them ."She loves satin and kid gloves and eating pussy and sucking tits. and have "lesbian" fun", said Kay. Vonna walked up to me and gave me a warm hug and a long wet kiss with her tongue down my throat, She said, "Wow" don't you ever look sexy" "I think that a good time will be had this evening".

We poured ourselves a glass of wine and Kay explained to Vonna about our little fantasy swap. Vonna could not get over the transformation and what a remarkable job Kay had done with my makeup and hair and clothes. Then Vonna asked Kay if I knew about their little adventures and also what was the deal with the kid gloves. Kay just said that it was one of my fetishes and that it had become one of hers too and she should not say anything until she tried it.. With that, Kay gently put her gloved hand on Vonna's face and gently kissed her. Vonna took Kay's gloved fingers and slid them down into her nightgown to massage her tits. Before I knew it the two of them were putting on a lesbian love and sex show like I had never seen before. At one point, Kay's head was buried in Vonna's pussy and Vonna had her gloved hands on the cheeks of her ass and hollering, " Oh Yes, I love the gloves, I love the gloves", as she pushed her mound to meet Kay's eager mouth.

By this time, Kay called out to me asking me if I wanted to get in on this and I eagerly went down kissing and licking her already moist pussy. I was caught up in an avalanche of orgasms all of us holding each other with our gloved hands. After a while, Vonna disengaged and took my swollen cock in her mouth and began a slow rhythmic sucking. I was trying my best not to cum, but I exploded in her mouth, and she kissed me with a mouth full of cum and then kissed Kay with cum on her lips.

We rested a while and had some more wine. The girls wanted to know if I could fuck both of them and I replied that I would give it my best. They had me lie down on my back and Kay let Vonna kneel over me to mount my cock and she kneeled facing Vonna which meant that she was siting on my face and I had my leather clad arms around both of them and sliding my gloved fingers to play with their tits. The girls took turns riding me this way and kept having orgasm after orgasm. Kay finally took pity of me and took my cock which was all wet with pussy juices in her mouth and gave me her trademark slow rythmic blowjob, and we all kissed each other sharing all our cum and wetness.

This orgy went on all night and became a weekly event for a couple of months. I would look forward to these evenings getting all made up and dressed up.

Alas all good things must come to an end and I suffered a heart attack but survived after open heart surgery.