I'd been having trouble with guys for a while. I know I'm decent looking -- your basic tall blonde -- but I tend to come off as too serious and maybe even intimidating. One guy I asked -- the husband of a good friend -- said I just looked unavailable. Plus I've been working far too hard at the engineering firm and not been taking care of my appearance or paying much attention to guys.
For the express purpose of getting some outrageously casual sex, I took two weeks off, got a facial, full body wax, etc. and flew down to Florida. Figured being away from home I could just go into a bar and pick up a different guy every night.
Well it didn't work out like that. There was a lot of competition --tall blondes all over. Plus I think I may just come off as too serious or whatever. I got approached by a few losers -- I mean real losers. I wasn't feeling that choosy, but ...
But I did meet two guys in a beach bar and flirted a bit. They didn't seem that interested, but I ran into them the next day at the beach and then again that night in the hotel bar. These guys seemed nice enough, and certainly honest! They were both married, waiting for their wives to return from a cruise, but also sort of looking for adventure. I told them that maybe they should each go trolling alone and take off their wedding rings.
Eventually they implied -- in a sort of joking way - that if I wanted to spend the night with one of them, I could choose, and the other would just fend for himself with no hard feelings. I know this sounds like a really lame proposition, but - I don't know -- I really liked it. It was so straight forward, just an offer of non-binding sex, and I liked these guys. How would I choose? It just made sense to offer to spend the night with both. Still I could hardly believe it when I heard myself saying it. They had 2 nights before the wives' arrival, so we planned 2 nights and a day together.
Before my pre-date shower, I went to a drug store and got a dozen condoms, a couple of different lubricants, and a some enemas. I kind of like the fullness of a finger in my anus when I'm getting a cock rammed into my pussy. Plus I'd heard about - and always wanted to try - a cock in both orifices at the same time. This seemed like the time, if ever.
So as you can see I was planning on a little orgy, fucking two guys at once, but as I was about to find out, they saw it as two separate dates.
My dates had rooms across from each other on the same floor as mine in another wing, and we agreed to meet in one of their suites. At this point I wanted to dispense with all the businesslike dealing and shake them up a bit, so I gave into my exhibitionist tendencies and walked completely naked from my room to theirs a little before they were expecting me.
I knew I would probably be seen, and I wasn't disappointed. About halfway at the end of my wing near the elevator I encountered a young couple. She giggled -- he stared. Not far from my dates' rooms I encountered two middle-age men and stopped to chat and be ogled. Why was I naked? Just for fun. I was stuck in the hall a bit longer trying to find my dates, since I was early, and they were in a different room than I'd expected.
My dates (Let's call them by their hair colors -- Red and Blonde) were surprised to see how quickly I had gotten down to business, and said that Red was preparing to "receive" me in his room across the hall first.
I sat down in the middle of a small couch in the living room of Blonde's suite and said let's warm up with a drink. As they got drinks from the bar, I relaxed back into the couch leaving my open a bit, so they could see my waxed pussy crack. I asked them to sit on either side of me, and I suggested watching some light porn on the hotel's network.
The couch was not really wide enough to be comfortable for three, so I was soon sitting on their laps -- one then the other and eventually spreading across both. I began to realize that they had not planned it this way -- they thought I'd spend the first night with Red and the second with Blonde. Nonetheless, I was still planning on my orgy and double fuck and figured I could slowly push the situation in that direction.
Naked, lying across the laps of two fully dressed attractive guys watching various sex acts on the screen, nature began to take its course. My two dates didn't take long to begin massaging my body, especially my breasts, long thighs and rapidly moistening pussy. Soon they were taking turns massaging my clitoris and pussy lips and slipping their fingers into my vagina. Both had stayed completely dressed, making me feel so totally exposed, lying wiggling around and moaning on top of them, as a strong orgasm shook my whole naked body.