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 "playing around" 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 "get the wrong idea" with her husband gone and all. She greeted me at the door and said, "Not a bad attempt, but we have a lot of work ahead of us." I was grateful for the attention and had to admit it was true or else I would not have ...