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Chapter 2 by mattpantyhose mattpantyhose

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Eve and Tom end their relationship

My relationship with Tom could not last forever. We were both aware of it, even though we had never really talked about that issue. The large age gap and the fact that the relationship was based solely on sex caused it to run on borrowed time. But we genuinely enjoyed it while it lasted. I was having a blast with my second youth and Tom had an experienced girlfriend with a high libido. He rejuvenated me and I was his sexual teacher; temporarily it was a perfect match.

The reason for our break-up was trivial. Tom had recently turned nineteen, soon he would finish high school and continue his education at a university; that meant moving to a different city. And a relationship based on sex could not work remotely. While Tom was still here we enjoyed our very active sex-life while it lasted. We agreed to remain friends with benefits and would certainly have sex whenever he returned to the city. But before he moved out we wanted to end this period in our lives with a bang. A gangbang.

Tom had a small group of trusted friends and suggested that he wanted to share me with them. I had already sucked the cocks of some of his friends in a club. Plus I told him about everything that had happened at a bachelorette party which I had attended. There, among other things, I got fucked by a few well-endowed strippers. [The whole story can be found in “Successful Businesswoman 5”]. So obviously I agreed to all of his ideas.

One of the starting rules was no orgasms throughout the whole week before the ‘party’, only anal sex and edging. I knew that I would be as horny as hell and I loved it. Tom and I established a general plan for the evening, it included mostly the limits of how far the boys could go with me. I was generally open to most not-necessarily-completely-normal sexual activities, but we did not want anyone to be uncomfortable. Tom assured me that all his ideas were within the limits, but did not tell me all of them. It was fine with me, because I wanted to be surprised.

When the big Saturday finally came I was grateful that I would finally get my pussy fucked. Not that I was fed up with anal sex, I still loved it. I simply craved ‘regular’ intercourse and, crucially, an orgasm. My ass was not getting any rest yet though. Throughout the whole event I would be wearing an anal plug. It was not the smallest one either, but a moderately thick toy. More importantly the plug had a built-in vibrator which could be remotely controlled.

My ‘official’ role during the evening would be to serve drinks and snacks. There was an actual football game on the TV and the boys were supposedly genuinely interested in its result. I had an appropriate costume for the occasion - a naughty maid. It consisted of the customary black and white dress, which was tiny and seemed to be made almost entirely of frills and lace. It had a generous cleavage and barely covered my nipples. My legs were covered with black fishnet stockings and I wore fancy pumps on fifteen centimetre tall heels; they would have been not only too tall for an actual maid, but also way too expensive. A tiny lace thong completed my outfit. I was not wearing a bra, so my huge breasts bounced with every step.

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