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I (18F) let a regular at the restaurant I serve at (56M) to pretty much be him and his old friends (55M) play thing for the weekend so I could see Alan Jackson
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So here's some context. My regular (lets call him Doug) and I had already hooked up a few times up to this point. He is the first and only man so far that I had been with thats significantly older than me. I spent a weekend out of town with him and we spent most of it in and out of the bedroom doing the deed in one shape or form. I loved it pretty much being his toy whenever and wherever he want, whether it be in the room, on the car ride or on a hiking trail. Other than great sex, a nice penis his gentle but strong personality it sweetens the deal even more that he helped cover pretty much all my bills for that month.

So this last weekend Doug took me to Salt Lake City to see one of my favorite artist Alan Jackson. He flew us out in first class, we stayed downtown in a really nice hotel called the Grand America. We got a suite there looking at the beautiful mountains. We had discussed a third person in the past but never made plans, low and behold when we get to the hotel and are settling in his friend he'd mentioned that we'd see (lets call him Greg) shows up with and overnight bag. He once floated the idea of Greg, him and I having a threescore in Utah but I didn't give it much thought.

It didn't take long for us being in the suite (along with a few drinks) for me to be on my knees in front of my new friend after Doug had done everything short of ordering me to do it (which I happily would have if he did 🥵). I was happily surprised to discover Greg had just as nice of a package as Doug. I went down on him until he finished on my face apparently it was a fantasy of his and his "ex-wife" (he said they are practically divorced but are keeping up "appearances") never let him finish there. Of course my desire to please really set the mood for the rest of the weekend (thank you daddy issues).

Greg took us to members only club that night where they didn't ID. We had a nice dinner and some drinks. We messed around some more in the locker room (since the club has a gym) Doug had a turn in there with me later on before the night ended as well (back to back cream pies make it a bad day to wear a dress with no panties🤪) The next day we hung out around the city and the hotel (fooling around throughout it of course) and then went to the concert. It was amazing and I had a great time. That night after getting home the guys told me that they wanted to have me together as if it was a secret. I'll must say it was magical having two older experienced guys devour me. Greg asked me to call him G-pa which drove crazy 😝. The next day after another go at it with Greg he had to get going apparently he had church and I found out he's a mormon (insane). Doug and I then got breakfast and headed back to the airport where he sent me on a flight back to AZ.

All in all it was an amazing experience I really love being with older men. Doesn't hurt that Greg sent me a generous venmoeither not that I did it for those reasons.

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4 days ago