My wife Tabitha and I are big fans of the site. It has opened up some new possibilities for our sex life and we have become a bit more adventurous. I've wanted to see her with another man but that is way beyond what she is ready for.
So we compromised.
While having sex I asked her how far she could go and she got all excited at the plans we decided to make. Basically we wanted to find another guy to masturbate in front of her. She would stay dressed sitting in a comfy chair, but he would come in, talk a bit, then take as long as he needed to start and take it out and start stroking. I would watch from the bed.
We immediately placed an ad online and had a few good replies. She choose one who answered our messages well and who was polite. She didn't want it at home so we rented a motel room and waited. At 7:30 we heard a knock and it was him. He was very nice and after an hour of talking and getting comfortable it just sort of started.
He took a bit of time to get hard understandibly since everyone was just watching him. Then he got into it and Tabitha was breathing heavier. After 5 more minutes she pulled her tits out to give him a good visual which made him go faster. I didn't expect that and it was not part of the plan but was turned on badly.
Once she started pinching her nipples he lost it and came all over the floor.
He left just after and we went into bed to talk about it. I felt her pussy which was hot and soaked. She said it was s shame he didn't cum all over her tits. It wasn't what we agreed upon but maybe next time. We had great sex and then fell asleep, exhausted.
WE may do this again or we may do something different. Who know, for now we'd like to submit our dare and see what happens.
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The MILFs are single, married but looking, or in open relationships and most have busy lives being moms and working. So discretion is preferred and they are usually quick to act without much in the way of gamesmanship.