Usually, I-75 from Fort Lauderdale to Naples isn't a very exciting ride. But as my car sped along, passing Florida State Road 19 at around 75 mph, I was pretty fired up. Yeah, I noticed the hundred or so gators sunning themselves on the embankment that lines the interstate; that was different. However, the hormones that were coursing through me this day didn't have anything to do with being excited over cars, or mileage, or gators. The drive itself was a nuisance.
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I knew before it was over that I had to write this story, to cement the memory in my mind. To somehow make this surreal experience that once resided only in my darkest fantasies even more real. This was a once in a lifetime experience that's simply too good to let fade with time. So here's my story...
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Even today anal is still a bit of a taboo, more with the older generations then the younger but most girls will simply say "No" to anal and that'll be that, which is a great shame as I think anal is probably the pinnacle of all sexual acts and a sign that a couple love each other enough to do it correctly.
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All he could think about was her ass. She was a beautiful woman, inside and out, and her pussy had provided him more pleasure than most men could only dream about in a lifetime. But he couldn't stop thinking about her asshole, that sweetly puckered opening, so tightly closed, so vulnerable. What was wrong with him?
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It started off as a stupid joke, one of those things sororities want entering freshmen to do during rush week. All the older sisters in the house I was most interested in voted that all the new freshman pledges would have to try anal sex before the end of the semester. If we wanted to join up, we'd have to take it up -- up the ass, that is.
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I vividly remember touching myself in the shower. I was making sure I washed well because I have always been a bit of a clean freak, and as I rubbed my hands through my pussy lips I got that feeling, that "oh my god what was that feeling." Needless to say, like most all girls I began constantly touching myself in the shower, using the hot water and the shower head to send me to climax after climax! Months later, again in the shower I ran my finger a little harder than normal across my tight little asshole.
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I sat at the kitchen table and stared into my coffee like it was an oracle that could tell me what to do next. I honestly had never even considered this possibility. Not that I felt bad about that. Who could possibly have expected this?
When Cathy appeared in that doorway, I thought I was going to die. My first thought had been that she was catching me in the act of cheating on her.
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"Uncle Joe, please! I'm serious, OK? You have to stop sleeping with my friends!"
Lilly, my niece, was livid. I'm not exactly sure how she found out, but then I hadn't exactly been going to great lengths to hide it either. Emily and Laura were both consenting adults. Sure, I was twice their age. But it was they who had come to me.
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Becca got her studio ready for her first customer after checking to make sure that Dean was also getting prepared.
This was the first time she'd be trying something so new and different... and although she wasn't totally comfortable with all of it she definitely wasn't going to back down now. Her good friend Chelsea had some fantasies that she shared with Becca one drunken evening - specifically about being spanked by a large and dominating man (something she'd never done before) and then having him take her anally (something else that would be a first as she was a virgin there still.).
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I was around thirty-eight at the time. I'd been off work for a few weeks after I'd broken my arm on the boats...at least that's what I'd told the doctor. Once I got the sling off, he told me to do some light exercise to help fix the break, and he suggested I go to the Y in town and do a couple of lengths of the pool a day. I'm a big guy anyway, and I've never had much need of exercise, but it certainly sounded like a change from looking for jobs and watching the tube all day.
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