A bachelorette party goes in a wild direction.
Enjoy..
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It’s been just over 36 hours, just a day and a half, and I still can’t believe that it happened. It’s so wild, so inconceivable. And if I can’t believe it happened, no one else is going to either. But what I can do, what I need to do for my own sanity, is put it all down on paper, while it’s still fresh in my mind. So here goes…
I guess I should start with a little background. I’m 26 years old and engaged to be married. I’ve been with my fiancee, Rachel, since our junior year of college, over six years now. We were both scholarship athletes at UCLA. I was on the swim team; she was a soccer player. I saw her from across the room at a party, with her long curly brown hair and her infectious smile, and I was immediately smitten. I’ve basically been in love with her since that moment.
Flash forward six years. We live together in L. A. and have been engaged for a while now. The wedding is in three weeks, near her parents house in the Napa Valley. But the thing that’s been on both of our minds for the last few weeks — and now will be for the rest of time — is her bachelorette party.
Rachel has a ton of friends; she’s funny and engaging, the kind of person that everyone considers a friend even if they’ve only met her a few times. Deciding which of her countless friends to invite to the wedding was a really difficult process. But for her bachelorette party, she only wanted her three closest friends, Maya, Nicole, and Syd (short for Sydney), all of whom she’d met her freshman year at UCLA. The plan was to have a girls night out in Las Vegas.
The problem was that her friends — at least Nicole and Syd — had been pushing her to do something risque, like hire a stripper or worse, which Rachel didn’t really want to do. This had been an ongoing theme in their friendship over the years. Both Nicole and Syd had high “body counts” so speak; they’d been with a lot of different guys over the years. But Rachel has only been with two: her first boyfriend, who she’d dated for three years, and me. Nicole and Syd had told Rachel a number of times that she was too young to get married, that she hadn’t had enough experience with men and that she’d eventually come to regret not having done more before settling down. In their minds, this bachelorette party represented a last opportunity for Rachel to do something wild.
The pressure had gotten to a point where Rachel was genuinely bothered by it and had contemplated calling off the party altogether. What she’d tried to explain to them, countless times over the years, was that her sex life was really good, that monogamy didn’t mean that she was a prude or didn’t enjoy sex. And that was all true. Rachel and I have always had a really satisfying sex life. We enjoy it, we have it frequently, and we both do our part to try to keep it fun and interesting. But all of this fell on deaf ears with Nicole and Syd, who were convinced Rachel would come to regret her limited experience with men.
That’s when Rachel came up with the idea. At first it was just a joke, a crazy idea that we laughed about together in bed. But the more she talked about it — and the more Nicole and Syd pushed her — the more it crystallized into an actual thing, something that she genuinely wanted us to do. As wild as it sounds, here’s what she proposed.
She wanted me, wearing a mask, to pretend to be a hired male stripper. She noted, flatteringly, that I was in really good shape and had a really big cock. I believe her exact words were: “I bet you’re more impressive to look at than anyone we could hire.” While I wasn’t certain about that, it is true that I still have a competitive swimmer’s physique as well as the good fortune of being pretty well-endowed.
The idea was that if I posed as the stripper, disguised in a mask, she could touch me, flirt with me, push the envelope a little bit in a way that satisfied Nicole and Syd but which she would never feel comfortable doing with some random, creepy, probably STD-carrying stripper or escort. I understood her thought process, to a point, but I still couldn’t believe she was serious. “You’d really be okay with your closest friends staring at my penis, up close?” I asked her incredulously.
“They won’t know it’s your penis,” she responded immediately, “and I’m pretty sure they’ll be impressed.” She smiled mischievously as she said the last part and reached out with her hand, gently placing it between my legs. We were sitting next to each other on the couch, watching TV. I felt my cock begin to stir as soon as she made contact. “You’d do that for me, wouldn’t you?” she continued, giving me her puppy dog eyes as she stroked my cock through my pajama pants.
“So I’d have to drive out to Vegas by myself,” I asked, finding it harder to concentrate, “get myself my own room and wait for the right time to come over to your room in disguise?”
“Yep, pretty much” she answered, as she reached down and pulled down my pajama bottoms, exposing my now solid erection.
“And then I would just strip down for you girls, dance around and show you my cock, and then just go back to my room by myself for the rest of the night?”
“Well,” she answered slowly. She was now leaning into me, staring up at me with her beautiful green eyes as she stroked my cock with her right hand. “I was thinking that, maybe, at some point in the night, I might sneak out and visit this hardworking stripper in his room and, you know, reward him for all of his efforts.” And with that she flashed that mischievous smile again and slowly lowered her head down onto my cock.
By the time she was done, I’d had an amazing orgasm and knew that it was too late to back out. Unless she had a change of heart, we were going to actually go through with this crazy plan of hers.
DOUBTS AND CONCERNS
As the party night approached, my apprehension grew, but Rachel seemed to grow even more committed to the plan. She had apparently told Syd and Nicole that she’d be willing to hire a stripper, but only if they let her take care of it. She told them that she’d only feel comfortable if she did the vetting. I think they were just happy they were getting their way, so they didn’t push back. But because of that, Rachel had absolutely no interest in backing down. For obvious reasons, she hadn’t actually booked anyone or done any research at all, and she clearly did not want to deal with the fallout from Nicole and Syd if the night arrived and there was no stripper to be found.
So whenever I attempted to voice my doubts or concerns, Rachel was either dismissive or quick to come up with a solution. For example, at one point I warned her that if she was expecting me to have a huge erection during the stripshow, she’d probably be disappointed. I was so nervous about the whole thing that I didn’t see how I could possibly manage that. A week later she handed me a one-dose pack of Viagra. She had made a quick two-day trip to visit her parents to take care of some wedding preparations and had apparently raided her dad’s medicine cabinet while she was there. “That should solve any performance anxiety,” she told me, very matter-of-factly.
The other issue I kept bringing up was about the mask. To her credit, she had managed to find one that was relatively lightweight but fit snuggly and did a pretty good job of rendering me unrecognizable. It was a Guy Fawkes mask, like the one from the movie ‘V for Vendetta’, all white with a big smile, curly mustache and thin goatee. My concern was less about them recognizing me through the mask and more about how to explain why I was wearing a mask at all. I hadn’t spent a lot of time around male strippers, but I was pretty sure that they didn’t normally wear masks. To address this, Rachel had come up with a pretty elaborate backstory.
She was going to tell her friends that the company she hired me from requires all of its performers to wear masks at all times, that it’s a way of shielding them from being recognized or photographed and thereby allows the company to employ people who might not otherwise be willing to do this kind of work, in particular aspiring actors and other show performers who need the money but don’t want it to be known that they’re strippers. It was at least a superficially plausible explanation, assuming her friends didn’t try to dig past the surface or google anything.
Even with the mask on, though, I was worried that her friends might recognize me from my body alone. Luckily I didn’t have any tattoos or obvious identifying marks, but they’d all seen me in a swimsuit before, either at the beach or at a swim meet. Rachel was dismissive of this concern too. “You have a generic athletic build, Jason. I don’t mean that as any kind of insult. You’re gorgeous and very fit. But in Southern California? In Las Vegas? There’s no shortage of guys with bodies just like yours. There are entire gyms full of guys with your exact body.”
And so on and so forth. There was no way I was going to talk her out of it.