| This is a real relief to get off my chest even though it may seem a bit silly, but even now as a married adult I’m a bit ashamed that I lost my virginity to an older woman. We were highschool kids becoming sexually active. I had my eye on a few girls at school, but mostly I kept to my books and got rid of my sexual frustration my jacking off at night. I’d stolen some Penthouse mags from my uncle and would cum in my sheets before going to sleep. One day, in the middle of school I suddenly remembered it was the day the cleaning lady came and if she made my bed, she’d find a magazine under the pillow. I freaked out and skipped out of school to try and beat her to it. When I came in the house, she was vacuuming the livingroom and I made up an excuse about feeling sick and ran to my room. Too late. The room was clean, the bed was made, and the magazine was neatly placed on my side table. I was humiliated. Our cleaning lady was a divorced 30 year old who was extremely attractive, but still looked old to me as I was still a few months shy of being 17. I think I had thought of her as attractive, but never thought about her sexually. She was an adult and as such could scold me and “tell my parents.” I just didn’t know what to do. I went to put the magazine away and began thinking of excuses or about just playing dumb when Mary came into the room. She laughed and put me at ease and promised she wouldn’t tell my parents. Then she gave me a lecture about how masturbating was fine, but shouldn’t replace the real thing and why didn’t I fuck some of my girlfriends. I told her I was too shy and didn’t think the girls would want to. She told me I was wrong and that if I’d had sisters I would know that girls want sex too. Then she told me that she also wanted sex and that she also liked masturbating but that the real thing was better for a healthy mind and body. Then, before I really knew what was going on she said she thought I needed some sex lessons and began sucking my dick. I came in her mouth and she swallowed everything. I thought that was it, but then she told me to get undressed and we both got naked. She told me it was my turn to service her, and then taught me how to lick a woman’s cunt. She was gentle and warm but as she came close to orgasm she became leud and forcfull. She jammed my head into her pussy till I thought I would suffocate and then started cursing, yelling “fuck,fuck,fuck” while she came. It’s funny now, but at the time I didn’t know what was going on. When she came down, she told me that that was foreplay and now I had to learn to fuck. She got me hard again with her hands and mouth and then lay me down on my back, she rode me for a while and then showed me how to take her missionary style and then doggie style. She said I had a nice dick and that all the girls would like me. She gave me five more “lessons” over the rest of that year, but when Summer came she told me I had to get a girlfriend my age. I had actually had some “luck” with one of the girls in class, but she freaked out when I went down on her and tried to lick her pussy. I told Mary and she told me than some girls think it’s dirty and not to get discouraged, that it was important. Sure enough, during the summer that girl’s best friend told me that she’d heard I was willing to give head and we started a “normal” sexual relationship. Still though, I remember Mary giving me my first blowjob and first fuck as if it were yesterday. I think I’m lucky to have had it so good the first time, but still feel funny telling anyone about it, and admitting I was too shy to begin with girls my age |
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