The Work Trip Pt. 01: Night Out

There were six of us sent to the Montreal office of our company for some training on a new software platform. The details of our job or of the new platform are not interesting -- not to me, anyway. I was competent enough and engaged enough in my work that I was a viable choice for the trip, but for my part my interest began and ended with a free trip to a new city, and a change of pace for awhile. The trip was to be for a month.

I will say that I work for a marketing company which is made up mostly of women. So it wasn't a huge shock when the six people chosen were myself and five women.

They put us up in an airbnb - they wanted us hanging out with each other, sharing ideas, making sure each one of us were coming along with the new platform. We were each going to be in charge of passing on this new information to our coworkers back home, so it was important that we all kept up.

The first weekend was fairly uneventful. We arrived Saturday afternoon and chose our rooms -- there were only two bedrooms, which was a bit of a shock since the place was advertised as comfortably sleeping six. Gloria (the manager) had to share a queen in the master bedroom with Bethany; Frida, Leslie and Kendra had to go all in one room -- Kendra in a twin by herself and Leslie and Frida in bunks -- and I was given the pullout couch in the living room. Not having even a bedroom for a month would be a trial, but I couldn't see any other way around it. I stowed my stuff in the closet and tried not to appear too put out.

When we were settled in Gloria pulled out a bottle of wine and proposed a toast.

"I just wanted to say to all of you, thank you," she said, holding the glass of red aloft. "I know a month is a long time to be away from your personal lives, and we very much appreciate the sacrifice."

"Cheers," we all said, clinking our glasses and sipping. It was slightly awkward. Leslie and Kendra were close already, but most of us didn't know each other that well. Bethany was on Gloria's team, but Bethany was a very quiet person, and I didn't get the feeling they'd grown terribly close in the office. The group was gathered in terms of who was competent enough to learn and re-teach the new platform, and willing enough to spend a month in a new city (read: single).

Gloria suggested we stay in that first weekend, get some pizza and some drinks, and try to get to know each other a little better.

It was extremely casual, with everyone in sweatpants or yoga pants, myself in my red plaid pajama pants that I never actually wore to bed -- they were my guest-ready comfy pants -- and a t-shirt.

I felt a bit like an intruder, an outsider sneaking in to a girls' night. I was painfully conscious of the fact that one wayward comment from my lips could turn this whole trip very uncomfortable -- not that I was particularly prone to sexual harassment, but we were having drinks and the conversation did turn personal. And, after all, these were colleagues.

It was kept pretty tame, but I did learn a few things to my surprise: Gloria, at thirty-five the oldest of the bunch, had been married once, very briefly, and incidentally had not been with a man in almost a year; Frida was named after Frida Kahlo, who she was evidently distantly related to (that was the juiciest item Frida divulged, but she smiled knowingly at every sexual tidbit that escaped the rest of us); Bethany, the quiet one, apparently owned a set up fuzzy pink handcuffs which she had made not infrequent use of (she wouldn't say whether she'd brought them to Montreal or not); Leslie admitted to having a decent-sized porn collection; and Kendra had had a particularly adventurous relationship once where she'd fooled around in a number of public places -- we didn't learn any specifics. For my part, the group managed to needle out of me that I had a daily (often multiple times) masturbation habit, which they all seemed to think was hilarious.

Some of the initial awkwardness aside, that night seemed to help us loosen up, and the first week went by smoothly. (Though, since I mentioned the habit I so ruefully revealed to the group, it bears mentioning that I was not able to find time or sufficient privacy to indulge that first week. I thought about it in the shower a couple times, but chickened out.)

Friday came along, and we were all looking forward to going out, having some drinks, seeing what this city had to offer. We went home a little early from the office -- it was a slow day, and I think Gloria was antsy to get a drink -- and got ourselves ready. This took me about five minutes, since all I did was change into a slightly nicer shirt (from a polo to a button-down) and jeans.

The ladies came out one by one, and though I felt consciously creepy in noticing, each one surprised me by how sexy they made themselves.

Bethany was first. She was short, not overweight but not what you'd call skinny either. She had straightened her dark hair and applied a bit more makeup, and wore a navy-blue dress (with what I later learned was called a Peter Pan collar) that fit her form closer than what she usually wore, and showcased a very large pair of breasts that I somehow hadn't noticed before. Before I could stop myself, my first thought when she emerged was to picture her stalking around swinging a pair of fuzzy pink handcuffs, deciding what to chain me to.

Bethany sat down on the couch opposite me and smiled shyly. I wanted to tell her she looked nice, but didn't know what kind of boundaries that might be crossing. So I just smiled back.

Kendra came out next, saving me and Bethany from our awkward silence. Where Bethany was cute, Kendra was intimidatingly sexy. She wore dark purple eyeshadow that perfectly complemented her deep brown skin, and a bright red dress that hugged her like a second skin, wrapping around every beautiful curve. She, too, had very large breasts, though I can't say I'd never noticed these. Her body never seemed to stop curving, from her big beautiful tits to her big beautiful ass, her smooth brown legs rippling out from where the dress ended about a foot above her knee. She wore black high heels that seemed to make everything tighter.

The effect Kendra had on me was immediate, and uncomfortable. I had to shift in my seat and cross my legs, trying to distract my mind and stall the stirring in my jeans. She smiled knowingly at me and sat down next to Bethany, clutching her little black purse in her hands.

Gloria was a bit more modestly dressed, but still looked nice. She wore red too, a loose-fitting dress that was cinched in the middle with a brown belt. Her eyes went to Kendra as if ashamed to be wearing the same color as someone who wore it so sexy. Gloria looked sexy too, for her part, though not quite as dramatically so. She had a nice body in her own right, though perhaps a bit softer in the middle, with a more modest pair of breasts.

Leslie and Frida came out together, laughing quietly. Leslie was tall, blonde, skinny everywhere. She had kind of a trendy-punkrock style typically, and tonight she wore a black lacey dress, long and tight, with her arms bare to display her many tattoos. Frida was quite a bit shorter and quite a bit wider -- she was perhaps slightly overweight, but she carried it well. She wore a yellow, loose-fitting dress that hung low to present her large dark cleavage. The dress looked very flimsy, and her boobs bounced with every step, looking one tremor away from bounding free. I tried very hard not to look at them, but they had a hypnotic effect on me.

I looked around, feeling both lucky and a little intimidated to be heading out with such a group of beautiful women. I was trying very hard not to think too sexually of them, both to control the ever-present stirring in my pants and to keep things professional. But they were making it hard, so to speak.

I decided a communal compliment would be appropriate.

"You all look great," I said as I stood up, trying not to look at any one of them in particular, but my eyes kept roving between Frida's and Kendra's chests.

They all smiled and murmured thanks, and Kendra gave me a knowing smile and her eyes crept downward to see if I'd kept my stirring under control. I had, to some extent, though the bulge in my jeans may have been slightly swollen. Her look certainly didn't help.

We had dinner at a casual place one of the guys from the office had suggested, but the main order of the evening was drinks. I was a little surprised at how driven everyone was to get after it, but from the moment we stepped into the restaurant it was evident we were here to party. Kendra ordered a round of shots, Gloria made sure the drinks kept coming, and everyone was on board.

I stuck to beer, punctuated by the occasional shot, and the ladies mostly drank wine, though Kendra gravitated toward Jack and gingers.

After the third round at the second bar, we were all in various states of drunkenness, and no one seemed to have any inclination of slowing down. The bartender seemed entertained by us, and kept drifting to our side of the bar when her demand slowed.

She was a big woman wearing a black tanktop that barely contained her breasts (seemed to be the theme of the evening, which I did not fail to notice), and had in the course of the last hour or so become our unofficial Montreal tour guide.

"But if you want to get real weird," she was saying, after rattling off a few bar options, "there's a club a couple blocks away that does bottle service for a decent price."

She kind of half-winked when she said "club," which I found curious, and apparently Leslie did too.

"What kind of 'club' is this?" she said, giving the same sort of half-wink.

The bartender looked from Leslie to me and smiled broadly.

"Well," she said, "I'll just say that this guy who's been staring at my tits all night will be right at home there."

I blushed, stuttered an attempt at denial, but my eyes went right back to her tits. She smiled at me.

Everyone else laughed, Frida loudest of all, who had evidently noticed my eyes wandering to her chest as well.

"So like a titty-bar?" Gloria said. I could see her blushing a little too, but to my surprise she sounded excited.

The bartender just winked again, and made her way to the other end of the bar to take an order.

I laughed and finished my beer, assuming that was the end of it. Of course this group of women didn't want to go to a club like that. A fun thought, something we'd joke about later, but not a viable option for the night, right?

"So," Kendra said, "we goin?"

She looked around. I said nothing. It wouldn't be my idea, if it turned out to be a disaster.

"I'm down," said Leslie.

Bethany shrugged, looking at each of us in turn. It wasn't a refusal.

"Are we serious?" said Gloria. More shrugs all around. "Fuck it, if no one objects, why not?"

I couldn't believe it. I still didn't say a word, assuming someone would speak up. I looked at Bethany, Frida, but they were both smiling. This was happening.

Being in strip clubs has always been a slightly unpleasant experience for me. Don't get me wrong, I very much enjoy seeing women take their clothes off. But when they do it for money, to satisfy the lewd drunken whims of a bunch of drooling men, it just makes me feel a little skeezy. The places tend to stink of desperation, and I find the stink clings to me, and try as I might to be above it all I know I'm not. I'm another drunk pervert desperate for a bare ass to sit on my lap.

But going with a group of women is an entirely different experience. Somehow I felt in on the joke, like I was an honorary member of the club coming in through the back door. Standing apart from the regulars, observing. There in company with the women who worked there, not as some outsider waving money demanding to be pleased.

Gloria asked for a table with a bottle and we were led upstairs, to a little alcove that could be separated by the rest of the room by a curtain. There was a small table we all gathered around -- I found myself sitting in the middle, as if I were a guest of honor. They brought us a bottle of booze, but I ordered a beer -- I'm not a big liquor drinker, and I was now particularly afraid of reaching a point of drunkenness where I might do something I regretted later.

The evening changed dramatically once we were settled in, and the drinks kept flowing. Where before the conversation was loose but generally restrained (at least to an R-rating), now it was no holds barred. Everything that had come out the following weekend was back on the table, subject to increased scrutiny.

"So Bethany," Leslie said. "Tell us about these handcuffs."

Bethany giggled and blushed a little.

"What do you want to know?"

"Like what do you use them for?"

Bethany stole a glance at me.

"I like to get a guy down to just his underwear, and cuff him to the bedpost, so he can't control what happens. And then I strip for him, and rub my hair and my tits all over his body while I pull his underwear off..."

"Jesus..." I said, not intentionally audible. The stirring in my pants become quite a bit more insistent, and I shifted in my seat trying to adjust. I caught Gloria's eye as I did so, and she raised an amused eyebrow.

"So by this time he's hard, yeah?" Frida said. I blushed and Gloria laughed, and Bethany shot another glance at me before nodding.

"Oh yeah," Bethany said. "It drives 'em nuts. Sometimes I can get 'em to cum without even touching their dicks."

I believed it. Just her talking about it about had me ready to shoot, and I was fully hard, trying to keep hidden under the table as best I could.

"What about you, Sam?" Kendra asked, looking at me. "Would that do it for you?"

"Looks like it from here," Leslie said, her eye trained on my crotch. I could tell from where she was sitting to my right my hard-on was clearly visible, drawing a thick line down the left leg of my jeans.

Frida, to my left, burst out laughing when she looked down. I blushed furiously, but there was nothing I could do to hide it short of covering it with my hands, and the sudden attention to it only made it strain more.

"Is he hard?" Bethany said, stretching her neck to try to see over the table.

"Oh yeah," Frida said.

"I guess you haven't been keeping up with your daily routine," Kendra said. "Your dick feels neglected."

"Pity I can't see it from here," Gloria said, with a wry smile. She was sitting across from me.

"Unless he stands up," Bethany said, her face bright red. Kendra passed her a look of amused shock.

"Stand up," Leslie said in a chanting cadence, pumping her fists together. "Stand up, stand up."

Gloria joined in, then Bethany, then all five women were chanting for me to stand up and display the bulge in my pants. I couldn't believe it. This night just kept surprising me.

I was embarrassed, and felt like I was failing some test, violating some rule, but I was also incredibly turned on. So I stood up,

And five sets of eyes snapped to my crotch, where my cock shoved against the leg of my jeans with all its might, drawing a clearly-defined shaft and a round bulge outward where the head was.

"Damn," said Kendra.

"Amen," said Gloria.

As I stood on display a woman came around wearing barely anything. She had red hair, huge tits squeezed into a tiny bra, a slight softness in her belly decorated with a butterfly tattoo, and a tiny g-string.

Her eyes joined the others on my crotch for a moment before I sat back down, further embarrassed.

She smiled. "Who got this big boy all riled up?" she said.

Leslie pointed at Bethany, who smiled and blushed.

The woman pulled the table out and sat on Bethany's lap.

"Don't you know that's my job?" she said. "Did he tip you?"

"Just through the jeans," Frida said, and ran her fingers lightly over the bulge in my pans. If I hadn't been as drunk as I was I probably would have cum right then. As it was I just jumped in shock. That got a laugh from everyone.

"He's jumpy," the woman giggled, rising from Bethany's lap and coming to stand over me. "Should we give him a little dance?"

That got enthusiastic yeses all around, and the woman strutted over and pulled the curtain shut, cutting our little alcove off from the rest of the bar.

"Who's got money?" she said. I assumed that's where it would stop, but every woman present reached into her purse and laid cash on the table. It looked like about $200, at least. More surprises.

The woman looked at the money and smiled, and said, "Well that should about do it."

Then she climbed onto my lap and whispered in my ear, "I'm Jasmine, baby. You want me to take care of you?" She ran her hand over the bulge in my jeans, sending shudders through my body. I just nodded, and she smiled.

She sat on my lap facing the curtain, and grinded her ass into my crotch, her hands rubbing her own tits until somehow they came away with her bra, which she tossed at Bethany.

"You can touch, baby," Jasmine whispered.

I ran my hands up her sides, grabbed her tits, filled my hands with them.

"Mmm, that's good, baby," she said. "What's your name?"

It barely registered that I was meant to speak, so it came as a relief when Leslie answered for me.

"This is our friend Sam," she said.

"Nice to meet you, Sam," Jasmine said, squeezing my cock through my jeans. "Take my thong off, Sam."

I ran my hands further down her sides, pushing her panties down, sliding them down her legs. I heard an "Oh yeah" from Kendra, and an "Amen" from Gloria.

Jasmine turned around, ran her hands down my chest, and with one incredibly deft motion unclasped my belt and whisked it out my jeans, letting it fall to the floor. How far was this going?

As if in answer, she pulled my shirt down over my crotch and undid my jeans, pulling my fly down. I sighed in relief as my cock was given a little more room to breathe. Then she grabbed hold of my boxers and pulled my shorts and jeans down together, leaving my shirt draped tented over my cock, pointing at the ceiling.

"Holy shit," Frida said.

Jasmine smiled, pulling off my shoes and socks and taking my pants completely off. My heart was racing, I was breathing heavily. I couldn't believe where this seemed to be going. I felt so exposed, with just thin layers of shirt covering my hard cock, every eye glued to it.

Jasmine stood over me and slowly pulled my shirt open, button by slow button, soon leaving my with just my white t-shirt sitting on my cock, not reaching my balls.

"You ladies want to help with his shirt?" Jasmine said.

There was no hesitation. Leslie on my right and Frida on my left each grabbed their side of my t-shirt and lifted. I raised my arms in automatic compliance, and then I was sitting totally exposed, with six sets of eyes trained on my cock, hard and red and pulsing, glistening with precum. I don't think I've ever felt so naked, or ever been so hard. My cock looked angry and, I was pleased to observe, huge.

"Fuck," Kendra said.

"Amen," said Gloria.

Jasmine smiled. "Nice cock," she said.

I just moaned. I'd never been so turned on. I felt like the slightest breath on my cock would make me explode.

But I managed not to cum when Jasmine climbed back on my lap and wrapped her hand around my cock. She started stroking, slowly, gently, her fingertips tracing patterns on my cock. I could feel the heat coming off every woman as they leaned in, watching.

Jasmine kissed my neck, my chest, still stroking as her lips made their way down my body. Finally she kissed the head of my cock and took it in her mouth, sliding her lips all the way down until she swallowed every inch.

"Jesus," Bethany said.

"Girl's got talent," said Kendra.

I just moaned as Jasmine slurped her way up and down, her wet lips sliding all the way to the tip and all the way back down to the base, my cock slipping silently into her throat.