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Enjoying a BBW

The first time I masturbated with a woman is still a memorable experience for me. It had been quite a long time since I had sex with a woman, and I was really feeling the need. Even masturbating didn't seem to help the way it usually did, and I was feeling very unsatisfied even after just having an orgasm. But finally I hooked up with a woman named Trudy through an online personal ad.

Trudy was babysitting the night when I first called her, but she said come on over. I guess she was in her late thirties and what they call a BBW (big beautiful woman) and a little on the tough side, but I still found myself looking at her and thinking, 'Yum!' I don't know why, but I seemed to always attract women of this sort, you know, the kind that love motor racing, hard rock, and riding on the back of motorbikes. Whilst some of them can be pretty tough, but they are invariably kind to me and really know how to please, so I've come to appreciate them since meeting Trudy.

We hung around and behaved ourselves until 11:00pm, when the kid's mom came home, after which it was off to my place. I lit candles and created a romantic atmosphere, and within minutes we were making out on the living room floor. She was a good kisser and knew how to use her tongue, so I had a hard-on in no time. Raising myself up on my elbows, I gazed down into her eyes, trying to judge whether to take this further. There was a definite 'yes' there, so I slid my hands under her t-shirt. She didn't need any further encouragement to take her shirt and bra off, and in no time I was kissing her breasts and sucking her nipples. So we both enjoyed that for a while, and our clothes seemed to just disappear of their own accord. I was just beginning to wonder if I would get my dick jacked when, as if reading my thoughts, she touched me down there. Jackoffs are great especially when the girl is really enjoying herself. Trudy was really going to town and I was really getting off on it, but she didn't quite have the knack, so my cock began to get a little soft. Girls, if you're reading this, you have to mix things up a bit, you know, alternate between fast and slow, etc. But I wasn't worried, because we had all night and I knew she would get it right. But in the meantime, I decided to finger her. With my fingers, within ten minutes or so, I brought her to an incredible orgasm. By this time, I really wanted to cum bad, and after letting her rest for a few minutes, led her to the bedroom.

I would have liked to have had intercourse with her, but I wasn't quite sure it was a good idea on only our first encounter, so I thought I would do something a bit dirty. I asked Trudy to get on her knees, and she looked expectantly up at me while I masturbated, waiting for me to squirt. This image is so powerful that I still get off on it to this day, several years later. I've found that relatively few girls (ok, none since Trudy) like to have me cum on their face, but Trudy seemed to like it and even expect it, so this image is really burned into my mind. Sometimes I wonder what happened to Trudy, as her cell phone number no longer works. Maybe she moved away, or got a new cell phone number, or maybe both. But perhaps she'll read this story and remember me with a smile.


Posted on: 2018-09-04 12:00:01 | Author: