Back when I was 15 I was working for an older woman on our block. She had no husband and was a friend of my moms. I spent a lot of time with her helping work around her yard and house. She was 44 years old, 5ft. 9in, weighed about 135lbs. I remember that she looked very pretty, and I liked her body. I got to see more and more of it, sneaking peeks at her through her partially opened bedroom door when she'd come out of the shower and change. She had small B cups for tits, reddish nipples that weren't too big. Everyone once in a while I'd sneak a peek at her black haired bush. We'd spend a lot of time in her pool her in a 2 piece, and me in my underwear. Eventually she told me I could go commando in the pool. She had a large privacy fence so I thought it might be a way to see her naked more and did it. She eventually took off her top and we would touch each other some times. She never let me touch her pussy, I told her I hadn't had sex and really wanted her to teach me.

The day came and she sat me down in the kitchen having just come in from the pool. I was naked and hard, she was topless. "I would really want you to fuck me David" she said, "But you wouldn't want to, because it wouldn't be the way you think" she added. Not knowing what she was talking about and being puzzled I didn't know what to say. Then she said "You will probably not want to come by anymore after this, but if you still want to, you can have as much sex as you ever want, anytime you want it. . . but you must promise, even if you run out of here, you won't tell anyone what you are about to see". I promised and she further made me promise to sit there for at least 5 minutes and talk to her after she took off her bottoms.

Her legs together, she pulled down her swimming bottoms and I could see her black hair on her bush and I was getting even harder. She turned around and showed me the most beautiful butt ever. Spreading her cheeks with both hands she said "This and my mouth and my boobs are all yours, and you never have to even touch me in front". I still didn't know what she meant. "I was born a boy, like you, only I felt and looked like a girl". Her beautiful bush was right at me then she spread her legs and out popped a little cock. It was only about 2 or 3 inches at most with a tiny little sack. When she had it pulled up between her legs, it really looked like a pussy. "Stay for the 5 minutes please, I'll do anything and answer anything you want" she said.

I stayed. I asked her a few questions, then asked her if she meant that I could have sex with her. The reply was yes. To me she was a woman, she'd been on hormones for many years, her small b cup tits were all natural, she had a very womanly figure, feminine voice. We went to her bedroom, she sucked me till I blew in her mouth swallowing it all. "You taste great" she told me. She kept playing with my cock and I never went fully soft, and when I was hard again, she lubed herself and me, and laid on her back and I got between her legs, which she wrapped around my back and fucked her. I fucked her several times a day, staying overnight to help her "work" as much as possible. My mom thought it was great I helped her so much. One day she went with my mom, my sisters, and me to the pool. I thought it was all up when they went to the changing room but they all came out without a care. She later told me, it's just like when she used to let me peek at her in her bedroom, when she's tucked in, no one can tell.

She was my sole source of sexual relief for almost 3 years. I finally got a date with this slutty fat girl when I was almost 18 and got my first piece of actual pussy. She was so damn used up and loose it was OK but slightly disappointing. When I wanted to stick it up her ass she thought I was nuts. I eventually popped her butthole without her consent. After than I thought that she wouldn't go out with me, but for some reason she thought we were boyfriend/girlfriend just because she'd never had a cock up her ass before. I finally got rid of her and a good thing too. The next poor bastard to fuck the slut was a dweeb who didn't stand a chance at getting a girl, and he dumped in her and knocked her up (On purpose on her part she told me). After that I still fucked the older GURL, and eventually got real girls my age or a bit older to let me fuck them too. I fucked her up until I got married. I wanted to fuck her some more but she wouldn't do it. I was off the market.