If any of you happen to be a comedian and you get offered a corporate gig on a cruise, seriously consider taking it!
Okay, I know most of you who read this won’t be a comedian, so let me explain. Big corporations often do a yearly retreat for their executives across the country, and it’s common for them to hire a comedian to come in and do a standup set. They are the worst kind of gigs in my opinion, because most of the audience are the overworked, overstressed kind of people who don’t care about comedy and don’t even try to laugh. Most of the time they’re a bunch of rich assholes, and I don’t know why they keep thinking it’s a good idea to bring in a comedian to try to lighten up their mood. The gigs pay massive bucks, more than what I make from ten normal gigs on the road. Even so, I normally turn them down.
This one gig was on a cruise though—that meant five days of commitment for only two shows, for the top notch executives of a high profile insurance company. It sounded awful. I definitely didn’t want to be trapped on a cruise ship with these people if one of the shows did poorly, but I figured I could make something out of it—maybe the other passengers besides all the corporate executives would be fun, right? And most importantly I really needed the money.
First thing I noticed when I got there: these people were freakin loaded. I thought it would be a normal cruise with a few rooms reserved for 30 people in the business. No! These guys rented out the whole entire ship for some 30 executives and their wives and families. The ship was so under booked that it felt totally empty throughout the day when they were in meetings. And the ship they had rented was luxurious all around. I would hang out at the pool or bar and chat with bartenders or read in my room—not too bad for a free vacation.
Second thing I noticed: a few of them liked to put it back. By day this was a corporate retreat; by night it was a booze cruise, still with boring work talk all through the evening.
I was set to go on the first night, and the was crowd fine, except for a couple of men in suits who must have gone through hell in their meetings—now they wanted to make the skinny, nerdy comedian on stage their personal punching bags. They heckled the shit out of me after every other joke, and no one in the audience wanted to say anything. I assumed they were a couple of the big heads. What always pisses me off the most about hecklers is they think they’re adding something fresh and spontaneous to the show, when really what they’re doing is hogging attention and being terrible at it. Normally I rip into hecklers and eventually get them to shut up, but I didn’t know how important these guys were. I’ve heard horror stories of comedians overstepping very thin lines at corporate gigs and not getting paid because they “violated the contract.” So I tried my best to go on.
But this one guy up front was the king of assholes. I got into this bit about the clothes I wear, and he tried to add to it and make fun of my clothes. He literally got out of his chair and poured beer on my shoes, saying all along a bunch of crap like, “I’m gonna send you some shoes a real man wears after this. Don’t worry, you’ll thank me later!” He looked like a 40-year-old model, slicked back hair, shiny watch, strong cologne, and an obvious trophy wife latched onto his table. She looked like a model too, with long black hair, expensive dress, expensive earrings.
When the set was over I tried as best I could to put him out of my mind. I ordered two drinks from the bar and planned to take them down to my room. Then his wife came up to me and apologized for his behavior. To my surprise, she was actually a nice person. She looked to be the same age as me, early 30s. When I thought about it, she was laughing at my jokes and not at her husband when he was heckling me. We had a moment to chat at the bar. She told me her name was Chelsea, apologized again for her husband, and asked if I was doing another show.
I told her I had one scheduled on Thursday but that I might try to get out of it.
“No way!” She said. “Are you going to tell different jokes?”
“I will if I do the show.”
She told me she wanted to hear more of my material, and that she’d try to encourage her husband not to come. Also, all the meetings and talks were apparently running late and some of the top executives, her husband included, might be working during the show.
That’s right. Mr. Asshole would be working during my comedy show, the one his wife so thoroughly enjoyed…
In my dreams, right?
At least it was fun to think about.
Fast forward to Thursday. I talked with the company’s event manager and, to my surprise, managed to successfully get my set cancelled that night and just take half pay. A couple of hours later, while I was killing the afternoon at the bar, Mr. Asshole stops by and makes some snarky remark to me about how maybe I’ll be allowed to come back next year if I get a little funnier, and he patted me on the back as he headed off to his next event. This fucking guy.
And about half an hour after that, Chelsea strolled in with three of her girlfriends. Through talking with her more I finally had to admit to myself that she was much nicer than her fashionable appearance might make her seem to most people. She was quite a laid back person, and she must actually enjoy comedy, because when I told her that I had cancelled my show that night she practically begged me to go on. If I thought she was flirting with me the night before, I was starting to become sure of it now. And there were people around who probably knew her husband. They were at the tables across the room and not paying any attention to us, but still her carelessness was starting to turn me on! I was still certain that she was just messing with me out of boredom from days on the cruise ship—and hopefully her boredom of having a dull husband—but hell I was bored as hell too, so I went with it.
So I contacted the event manager and got set to do the show again. I put on my nicest shirt, a tie, cologne—I went the whole nine yards to get ready for this night.
It went much better. The audience was really small, like 15 people, mostly bored wives, so it was hard to get laughter rolling, but I didn’t care. The hecklers were gone, either continuing their meetings with Japan, or brooding in the cigar room—I couldn’t care less where the hell they were. As long as Mr. Asshole was out of the room, this game was on. Chelsea was sitting at the front table, and the eye contact between us was damn near constant. She and her friends were pounding round after round, and as the show went on I felt like I was giving a private show for the four of them.
Afterwards I joined their table to get a drink of my own. After about 20 minutes, I noticed her exchange a few subtle glances with her friends, and next thing I know they’re making up excuses to go back to their rooms and pass out for the night. This put my senses on high alert. The conversation got heated. A couple of times she complained about her husband any chance she could, about how he works too much and doesn’t even realize when she’s in a bad mood, or he doesn’t care. It was at that moment a little voice started bubbling up in my head that was asking: Is this actually about to happen between us?
And another voice saying: No way. Something this awesome doesn’t happen to a guy like me.
“To make things worse,” she said, breaking me away from my thoughts. “I accidentally under-packed for this. I didn’t bring enough panties.” And she leaned forward, whispering, “I’m not wearing any right now.”
“You didn’t pack enough panties?”
“Well I had enough, but then I soiled the pair I was wearing this afternoon… got myself a little too hot thinking about this comedian I was excited about bumping into.” And she winked at me.
I shit you not, fellas, she said this to me in a completely serious manner—and that’s when the blood drained from my head. She was wearing a plain cotton dress, and I wanted to get under it any way that I could. I went to the bar to get us another round of drinks, and when I turned around she was standing right behind me. She told me to follow her, and she led me to an upper level to the bar, a small room that no one else was in. We sat close to each other on a long leather couch, with a window above the pool area. Next thing I know, she’s leaning into me, feeling on my crotch area while talking about how much my jokes had made her laugh, even hours after the set was over.
It had been quiet downstairs all night long, and the upstairs room seemed to be a complete secret to almost all the other attendants at the retreat. Still I was hesitant for a while, but after I finished my drink I ceased to care and went for it. In fact, a little part of me was hoping her husband would walk in on us and see me feeling up his wife. We made out heavily, and after that it was like I had given her full permission to go crazy. She slipped off the couch and pulled my cock out of my pants and sucked me off! I was in the middle of the Caribbean, drinking scotch that was at least 50 dollars a bottle and getting sucked off by the most beautiful woman who’s ever put her mouth on my penis. This was the high life.
I could have cum in her mouth right there, after only one minute, but I slowed her down. She stood up, she pushed me down along the couch and laid on top of me. We made out again, with my dick still hanging out of my pants, and I never lost a bit of my erection. She proved to be amazing at giving a hand job too. Finally I couldn’t resist any longer and I retrieved my emergency condom from my wallet, which until that time had only helped me out once in life, years ago. I held it up in front of her, and for a second I felt the same as my first time stepping up to an open mic, so afraid of the reaction. But her eyes lit up. She grinned, biting her lip with some sort of devilish stare, and snatched the condom out of my hand. She slipped it on with expertise and lifted up her dress so far up that I could see her bra. Indeed, she was pantyless.
We started fucking, and my pants were around my ankles by that point. If we had heard someone rushing up the steps at that point, we would have been caught for sure, but it was too hot to stop. A moment later her phone started vibrating in her purse, which almost gave me a heart attack, then she started laughing. We sped up to a super fast pace. This woman could fuck,
and she was loving it. She damn near ripped a hole in my shirt from her tight grip, doing whatever she could to keep from screaming out. She started breathing super heavily and let out a squeal, which I assumed was her having an orgasm, and that put me over the edge. I had one of the longest, most intense orgasms of my life!
And without a doubt, it’s one of my best memories related to any standup gig I’ve ever had.
After the act was done, she took a minute to freshen up in the bathroom, gave me a kiss on the cheek, and told me good luck on the road. She went down the stairs, and I didn’t even get a chance to chat with her for the rest of the trip. I still don’t know what to say about that one. I’m pretty sure the booking agent and most of the crowd like me though, so maybe next year I’ll see her again.
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