Starting out

I was only just 18 and was working for a small company. They needed someone to sit in the office on Sunday awaiting a delivery. The other person who was working was a lady called Fran, who was in her 50s and the mother of a girl I had known at school a few months earlier. We were both sitting drinking tea and listening to some inanities on the radio. The programme ended and another one started about crossdressers and their sexuality. I was listening while trying to pretend I was uninterested, when Fran quietly said "You know my husband, Bill, was a crossdresser. I helped him with buying all his clothes." (I was aware he had died some years before.) We continued drinking our tea and for some inexplicable reason I blurted out that I was a part time cd as well. Fran looked at me and said "Why not come over to my house and you can look through Bill's wardrobe to see if you would like any of it?" I agreed like a shot and then panicked to myself. "Dont worry" said Fran " My daughter is away and I will keep this our secret" A few hours later Fran had laid out Bill's stuff. He was into the prim and proper look and his clothes did not suit or fit me but I was grateful for the Janet Reger underwear set, corset and false silicon breasts. There were two dark brown wigs (one short and one long) and I have kept the colour to this day. Fran was keen for me to take more and I chose the tartiest of the outfits which was a mid thigh length rara skirt and a sparkly top. "What is your girly name" she asked. "Nikki" I said "Please just put the clothes on for me" she asked "I would like to see them one last time" I did as she requested, dreading that she would want more but that was not the case. "Now Nikki, I have a friend who I expect would like to meet you. I can assure you he will be as gentle as you want. Bill and I loved fucking with him. Are you happy if I give him your telephone number?" I said that I was and we parted. About a week later the phone rang and it was her friend wanting to see me. I gathered my tarty stuff together and went to his house. I was greated by his wife who explained that she would not be involved but said I was to change and wait in the bathroom. I was trembling with fear as while I was not a virgin I had never actually been with a man. I remember I was wearing the long wig and a tight black top with a red satin miniskirt. Roy came into the bathroom and made some nice remarks about how I looked and then called his wife who came in, made some helpful suggestions on how to improve my makeup and then she left. Roy stood behind me and ground his very firm cock againt my bum. He stroked my thighs and worked his fingers up under my skirt but avoided my tool. His fingers eased under the edges of my panties and then lifted my skirt up. "Come with me Nikki" he said leaving the bathroom We went into the bedroom and I sat down on the bed. He stood in front of me and I pulled out his cock which I remember as being quite thick but of what I would now call average size. I gave him the first blowjob I had done until he pulled out of me asking if I wanted to be fucked. I could not speak I was so nervous but just nodded. Roy got me bending over the bed and I felt his fingers lubricate me. Then I felt the head of his cock against my ring. I was very tight and he asked if I was an anal virgin which I admitted I was. At last the head pushed in and it was so sore. "Slowly" I begge "Slower please" and he was as gentle as he could be. After a few strokes, the pain receded and a filled fealing overtook me. He was thrusting from behind and I started to rock against them driving him deeper and deeper. "Oh you are so tight" he cried out as I felt him slump against me. He pulled out and his prick was covered in spunk and I could feel it dripping out of my bottom. (this was pre safe sex days!) I had never tasted another man's spunk before and I tentatively and then more eagerly swallowed his cock. He started licking my arse and so "cleaned" me out. I thanked him and we agreed on another meet in a weeks time.

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