Remembering Louise

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Cross-dressing in Leather.
1.6k words
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The only times in my life that I can say that I have ever felt free and happy were those few years between marriages when I was living single and had my own apartment. Those were the days when I felt like a complete person. Although I could not live 24/7 as a woman because of my job requirements, I still managed to live most of my social life and most of my personal life dressed up and "en femme". Still I felt very heterosexual and loved women. I never had any desire for gay encounters, although I did meet a few "cross-dressers" that I felt I could have become intimate with under the right circumstances, but mainly it was still a case of "cherchez la femme".

I was in my early forties at the time. Essentially, I became a cougar in reverse. Instead of hunting younger men, I was on the prowl for older, sexy women.

The best places that I found to meet older women was in "country" type bars and lounges. These older gals all loved to dance as I did. For me, my clue as to whether or not we could be compatible was if they wore leather skirts or pants and or either leather boots. If they wore satin blouses and satin dresses, I would add even more points.

Now women know that they look sexy in leather and they also are hornier in leather. Don't let them lie to you about that. The same applies to satin blouses and skirts and dresses. Chances are that if a woman thinks she looks sexy, she will act that way too. . . and that is how I chose my dancing partners.

If nothing else happened, at least I would have the chance to get to feel some great satin and boobs and some fantastic leather covered asses. Even if nothing developed , I would at least have the chance to enjoy the company of some great women.

Of course, one thing that seemed to turn on these older gals is if they knew you had your own apartment . That seemed to be the "clincher". Not too many older gals live alone. They either live with their children or are taking care of grandkids or just plain cheating on their husbands. Talking them into coming home with me was never much of a challenge.

When we left the bar at closing time, I would check what kind of coat my date was wearing. If she was wearing a leather coat that would be more points. If she pulled out a pair of leather gloves that would be more bonus points. Most times my "date" would have come to the club with other girl friends and so I could get to drive her to my apartment.

One gal in particular will always have a place in my heart. Her name was Louise. Oh, how she loved to dance. Not only was she a looker. . .petite with long brown hair, great complexion, and a fantastic smile to go with a great personality.

She must have lived in that black lambskin leather skirt. Lord only knows how she ever kept that skirt clean, but it always looked brand new. I asked her outright a couple of times how she did it but she always laughed and said it was her secret.

She had a great collection of satin blouses; some shells, and some with long sleeves. I soon found out that when she wore the shells, she would also be wearing her long black leather gloves, and a three quarter sleeved lambskin leather coat and her designer boots. Came to find out that she worked at one of the best departments stores in the city.

Right from the beginning, I felt that I could be honest and open with her. We never did play any of the silly games that so many singles and divorcees play. I knew she was going to find out sooner or later that I was a cross-dresser but I did not want to lose her.

I would always play her compliments on the way she looked and on her clothes. I told her that if I was a woman, I would want to dress just like her. She thought that that was the greatest compliment. We teased each other a little and she wondered what I would look like in women's clothes. She thought that I was more aware about women's things which was something she liked about me. I was busting in my jeans to tell her that I was a cross-dresser, but I knew she would find out when she came to my apartment.

Now I kept a fairly clean apartment which was definitely feminine in its decor. I always had fashion magazines laying around and the ironing board open with some lingerie draped over it and a lot of photos of myself "en femme" and other cross-dresser friends.

The first time that she agreed to come and see my apartment, she had come to the club with two other ladies, so she had already planned to come to my apartment with me that night if I asked her.

I knew during the first dance that she was ready for romance. The band played all our favorite songs and we kissed all through the slow dances. After a couple of drinks, I asked her if she was ready to see my apartment. She nodded yes, and we left early.

I especially enjoyed watching her put on her lipstick and her long black leather gloves and that fantastic leather coat. I took her hand in mine as we walked quietly across the parking lot, the only sound was the tap tap of the heels of her leather boots.

When we got to my apartment, we took our coats off but she kept her long black leather gloves on. I opened a bottle of Chardonnay which had been chilling and poured each of us a glass. She really had me wondering why she kept her gloves on. Had she found out about my fetish somehow?

I put some romantic country music on and we came together with our glasses of wine and slow danced in the kitchen. I loved holding her gloved hand and kissing her fingertips. I told her that I thought that the gloves were a wonderful and exciting touch and asked her if and how she knew that I had a fetish for ladies' leather gloves.

She gently caressed my cheek and told me I really was never that subtle about it and of how she noticed the effect that her gloves had on me. She also confessed and said that she had made inquiries about me. I asked her who it was that knew me and that I had a leather glove fetish.

She laughed and said that her aunt Alice had told her about this cross-dresser that she had known years ago and that he was one of her best customers when she sold ladies gloves and from the sound of it, might be me. Her aunt also confessed that she had a torrid affair going on for a couple of months even though I was much younger than her. She added that she had taught me everything about how to please a woman.

The next day her aunt came into the department store where she worked and presented Louise a picture of me all dressed in a formal blue satin evening gown with long white kid gloves and a blond wig. She had also managed to sneak a picture of me in male clothing. Her aunt also told her that if she did not make out with me to please give her my phone number.

She told me that she had known for a short while but was waiting for me to tell her. She also said she had no plans for going home that evening and she would love to see me in women's clothes. I thought that I had died and gone to heaven. I brought her into the bedroom and showed her all my closets and drawers and all the female apparel that I had.

I suggested that she might want to get comfortable and offered her a choice of satin night gowns. She accepted the offer and while she was rummaging through my closet, I headed to the bathroom to shave and put on my makeup, my breastforms and my bra, my brown wig and a black satin night gown with a pair of opera length kid gloves.

When I emerged from the bathroom she was sitting in the living room, glancing at the pics of my cross-dresser friends and of me. She had chosen the light blue satin night gown and had kept on her black leather gloves also. She had freshened her makeup and put on some new red lipstick. She had refilled our glasses of wine and she made a toast to dear old aunt Alice, "I hope that aunt Alice taught you well because I am so horny and so much in need. . . I hope you treat me nice" With that we embraced and I went to my knees and buried my face between her legs.

We had a torrid sexual relationship for three months. I am sure she must have been reporting to dear aunt Alice regularly because she always wanted to take pictures of me. . .either that or she was planning to blackmail me. . .no, she wouldn't do that. In any event, I had a cardiac episode and I had to give up the apartment and lost my job and wound up living in my parent's basement.

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AnonymousAnonymousover 5 years ago
Worth reading to very end

Damn that ending smashed it!

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