1. A Crossdressing Story


    Date: 11/4/2018, Categories: Anal, First Time, Author: oldguy1951, Source: xHamster

    ***A crossdressing story*** (All characters are fictitious...maybe…!) I had been dressing for a number of months when this adventure occurred. While I felt that I was learning the basics of makeup and dressing, I needed some expert advice and so I placed an AD in a local TV/TS newspaper for an understanding woman to help me with my feminine side. Little did I know what an erotic journey this would take me on! I got a number of good responses, but the best came from a woman named Debbi. Her husband travelled a lot and so she had a good deal of privacy in her home and she confided that she had done this with a friend who was also a TV. Her letter had a photo showing her to be a cute brunette, with a nice firm figure and tastes in clothing that stopped just short of looking slutty. I was trying to get the semi-slut look down myself and being a brunette, I figured she could really help transform me. Besides, she had made it very clear she was interested in &#034playing around&#034 with her pupil. I called her and we arranged to have me come over after her husband had left on one of his trips. I looked forward to that day very much and it soon arrived. I drove over to her house dressed, because we did not want her neighbours to &#034get the wrong idea&#034 with her husband gone and all. She greeted me at the door and said, &#034Not a bad attempt, but we have a lot of work ahead of us.&#034 I was grateful for the attention and had to admit it was true or else I would not have ...
    visited. For her part, she was dressed in spandex bikers pants, a t-shirt and bare- footed. She explained that we would start dressing together, from the ground up. We spent the next couple of days going over the basics of makeup, hair, even how to walk. She was an excellent teacher and her price was easy to meet. She wanted me to have sex with her as her lesbian lover and I had no problem with that. We would get completely dressed and then sit together as though we had just met at a bar. I would walk into the room and approach her, trying to pick her up. &#034Hi, I couldn't help but notice you were alone here, mind if I join you?&#034 I would say. She would make small talk and flirt and finally I suggest that we go back to my place for a drink. She always wanted to protest that she was not interested in anything sexual. Part of the fantasy was that she was to be seduced into lesbian sex by me. After a couple of times we had our routine down. Everything was going fine until the day before her husband was to return. We had entered the bed room and I began by sitting too close to her, making her aware of my body against hers. She blushed and tried to move away and I slowly slid my hand up her thigh, playing with her inner thighs by lightly stroking there. She gasped and I moved my other hand up to her breasts. Through her blouse I was able to stroke her breasts gently. I brought my mouth over to her ear and started to lick her ear and the nape of her neck. She always had to protest, ...
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