I had my first time when I was a young boy of 15. It was an older woman in the neighborhood, I worked at her place a lot, managed her pool and could swim whenever I wanted. She had let me see her topless in her swimming suit bottoms or in her panties many times through the years. She talked me into changing in her bedroom once and walked in on me naked. I tried to cover up and she said not to. She demanded that I hold my hands at my side. She stripped and I once again saw her shapely body, flat tummy, and her B cups. "I was born a man, and still have the ability to properly thank any man properly" she said. This was said with my 8 inches growing hard in her hands. She pulled off her panties, and I saw brown hair on her 58 year old "pussy" but I didn't see a cock. She knelt down in front of me and opened her beautiful mouth and started sucking me. I came in about 5 minutes, almost collapsing on the floor. She laid me on the bed and started feeding me her nipples and her lips while I was lying there. Then I put my hand between her legs, and she told me I didn't have to touch it, but I did. It was small, probably 2" at most, with tiny little balls and sack.


I got aroused again, and at full hardness, she pulled me on top of her and spread her legs, moved up her hips and inserted me into her ass. It was my first time having sex and I was fucking a tranny in her asshole. She whispered that no one knew about her, that I was the only one, and no one would ever know. She told me to just relax and enjoy being with her and in her. In about 15 to 20 minutes I was ramming in and out of her fast and shot my load in her. It was a terrific relief.


I fucked her a lot, for several years actually. I tell people who ask about my first sex that was an ongoing relationship with a much older woman in her late 50s who relieved me of my virginity. I never tell them, not even my girlfriend that my first sex was in a tranny, not a real woman. To me, she was and still is a real woman.