I had known Mary for almost 5 years, as she had worked for a place I also worked when she was 15. At the time I didn't notice her much, as she was a very tiny and young looking girl, about 4 foot 10 and 90 pounds, almost looking like a little boy with no hips and a pretty flat chest. She was also very quiet and shy, and being both home schooled and a Southern Baptist, I assumed she was pretty meek and mild.
The first clue that I was wrong was when she, at 17, showed up at work one day and told us that she was pregnant with her boyfriend. They quickly got married, and she left work to get a better job and had the baby. She'd still come by though, but after having gotten married, she was much more outgoing than she had been before, and over the next year became somewhat flirty. Having a child had also made a difference in her body... for the first time she had hips and breasts, and had suddenly become a petite yooung woman with a smoking hot body, still only about 95 pounds. With an almost 30 year age difference, I passed it off as nothing that was anything more than innocent flirtation however.
More time and a second baby, and I began to see her more. She'd drop by the shop and talk to me about things, which weren't going well. Difficult children and an abusive husband left her wondering what to do, and she didn't have enough confidence in her abilities to move out. Then he made that decision for her, and took a girlfriend, telling her that he intended to seek a divorce.
One Summer day she came by the shop and confided in me that she didn't even have enough money to buy groceries for the week. I gave her $120, and she asked how she could pay me back. I planned on working all weekend, and needed help, so I offered her the chance to work it off. She showed up that Sunday afternoon, and it was a fun day, getting stuff done and talking. It also got flirty. Very flirty.
When she commented that her back was sore from carrying kids around and that she hadn't had a decent backrub in ages, I took the bait and offered one. She promptly came over, sat down on the floor facing away from me, and peeled of her shirt, now wearing just shorts, a bra, and flip flops. Within 10 minutes, she remarked that the bra strap was in the way, and peeled that off as well.
In just a few seconds we were kissing, and as I began to rub my hands across her tiny little dark brown nipples, she started moaning and shaking. I'd been with a girl once before who could have an orgasm from just stimulating her breasts, but nothing like this... she was almost screaming and shaking it was so wild, and it seemed to go on as long as I let it. Opening her shorts and rubbing down inside of her panties found no hair; a nicely shaved little pussy! Sliding my finger into the slit revealed a very wet clit, and her noise intensified. After a while she seemed almost exhausted, and I simply held her and kissed her while she laid in my arms, eyes closed and silent.
Exhaustion or not, I was rock hard and hurting, so I finally reached down and began to pull her pants off, as she kicked off her flip flops and helped. Next came her panties, and I finally got to see her totally naked. Two children had had it's effect, as her small breasts sagged slightly, and she had very light stretch marks, but my pervy side was rewarded with a yooung woman who looked much younger than her 20 years.
I helped her back down onto the floor, where i went down on her, and she resumed her thrashing about and screaming. I don;t even know how many orgasms she had, it just seemed like one long orgasm. She later told me she'd been this way as long as she could remember, even as a child masturbating. By this time I was teasing her a little bit, askign her if she needed to be fucked, and she was groaning and pleading yes. Then came the surprise... I had been fingering her, and pulled the finger out and ran it across her little asshole. She screamed again, this time at the top of her lungs. I assumed that wasn't a good sign, but she quickly told me that she loved to be touched there more than anywhere else and to please not stop.
But I did stop. I needed to fuck her really badly, so I picked her up and laid her on the desk, pulling her ass toward me until it was at the edge. Then I dropped my pants, and began to rub the head of my cock against her opening. She told me that having had children had left her loose, and that she needed me to enter her as hard as I possibly could. I complied, and the sight of her eyes rolling up in her head as I thrust my entire length into her as hard as I could was a sight I'll never forget. She did her now normal screaming long orgasm, and when I warned her that I was about to come, she scooted back off of my cock, sat up, and bent over going down on me and swallowed it all. My God what a sexy sight and feel. She then kissed me deeply, and the taste of the two of us together in her mouth was wonderful.
We laid back down on the floor, and she crawled on top of me and slept for a little while. WHen she woke up, she went back down on me, and I got hard again, something that I hadn't done that quickly in many years. I asked her if she also enjoyed anal, and she told me she had never done it, that she didn;t trust her husband to be careful. I told her I knew how to do it without hurting her, and that if she ever wanted to try, I'd be happy to oblige.
She mounted me and rode me on the floor, scrubbing her clit against me with the motion. Then she stopped, looked at me, and said the sentence which will probably always be the wildest thing I've ever heard. "I want you to fuck my ass." Back up on the edge of the desk we went, and I stood with my cock against her ass, explaining to her how to push with her asshole as if she was going to the bathroom so as to open her ass and make my entry easier. I lubed both her ass and my cock up with the only thing available, hand cream, and began the slow process of pushing, then relaxing, and pushing again, each time getting just a bit of the head farther in.
Finally the head was in, and I just held it there, nto moving. She had her eyes shut and looked like she was in pain, but when I asked, she insisted that she was okay. I began to push and pull, very slowly, just a quarter of an inch or so at first, but within 5 minutes I had my entire cock sliding all the way in and out, even if still very slowly. She looked like she was hating it, with her eyes clentched, her face frowning, and her head rocking back and forth, so it came as no surprise when she reached down with her hand and seemed to stop me while moaning my name twice. I asked if she wanted me to stop, and was shocked when, her eyes still clentched shut, she said "no, I need you to fuck my ass really hard."
I did, and didn't last long before filling her tiny little ass with my sperm.
Afterward, I helped clean her up, and she went on her way smiling. it was to be the first of many times with her, and while I'll tell some of the other wild stories later, there was never anything quite as shocking, wild, or fun as the first time.