Unexpected Anal Office Tryst Ch. 06

The following morning, I ate breakfast alone. Whether she was exhausted from last night's festivities, or if she just didn't want to talk about it, I can't say for sure. Kathryn arrived at the hotel lobby in time to grab a scone and coffee and consume it on our five-minute walk to the convention center. The few words we exchanged that morning were focused on sales strategies, and once we hit the floor, we didn't see each other until the end of the day.

It wasn't until we were back at the hotel bar, nursing the obligatory celebratory cocktail, that we were able to discuss what had happened.

"Do you want to talk about it?" I asked.

"I suppose it's best that we do."

"I had a good time. Did you?"

"Well, yeah...in one respect," she said, hinting at something deeper.

"Go on..."

"Well, I mean, physically I undeniably enjoyed myself. It was super intense, and I'm not going to deny a sense of accomplishment for having done it...especially the finale."

"Yeah, that was unexpected. At least, it was for me. I'm not sure how much you two had planned before I got there."

"No, it was a surprise for me, too. If she had told me beforehand, I probably would have insisted that she give up the idea. But that's not the issue. As great as the action was, I was overcome with melancholy after you left. There were so many times when Amber and I were younger that I passed on opportunities like that, and now I wonder whether I should have had more fun when given the chance."

I nodded in understanding.

"You know, I often find myself wondering whether I should have done things differently. And I always ask myself whether I would risk trading what I have now for whatever would have transpired had I walked a different path in life. And the answer is always no. I would bet the same is true for you. You have a great job, make a ton of money, just got married to a good guy..." I paused there. It felt fucked up for me to include him in this.

"I know, and you're right. But I think I probably could have had one or two flings and still be in the same position I am today."

"Not for nothing, Kathryn, but I'd posit that you're living the most extreme version of having your cake and eating it too. What we're doing is so risky, and so fun, and yet we've been able to maintain our married lives as well."

She smiled even as she sipped her martini. "Yeah, you're right again. I suppose I should just allow myself to enjoy the now and not worry about what could have been. Anyway, do you want me to leave before Jenny arrives?"

"I was wondering that myself. It would probably be the cleanest way to prevent any uncomfortable circumstances. But it wouldn't be weird for two coworkers to be sharing a cocktail after a long day. I don't think she'll suspect anything."

"I was thinking the same thing. Good. Because I didn't want to have to chug this heavy pour the bartender served me."

We chatted for a few more minutes, before I saw Jenny enter the bar. She looked stunning, adorned in a little black dress that stopped just above her knees, and a relatively low cut that showed off several inches of cleavage. Her blond hair cascaded over her left should and down towards her breasts, ending near a pendant necklace I had purchased for her on our tenth anniversary. Black three-inch heels completed the look.

She found me through the crowd and smiled broadly, clearly excited to see me. As she moved serpentine through the tables, it seemed like every guy in the bar followed her with their eyes. Kathryn noticed I was staring past her, and turned to see Jenny making her way to us. I felt Kathryn slink as she saw Jenny approach. You know how sexy I think Kathryn is, but in her pant suit, she was no match for Jenny's coquettish appearance.

Jenny skipped past Kathryn like she wasn't even there and kissed me flush on the lips.

"Hi babe!" she giddily greeted me.

"Hi, honey!" I tried to match her enthusiasm. I took her hand and turned her back towards Kathryn.

"Honey, this is my friend and coworker, Kathryn. We've been kicking ass the last couple days."

"Hi Kathryn, it's so nice to meet you! I hope I'm not disrupting your work routine by being here."

"It's nice to meet you, too, Jenny. I've heard a lot about you. And no, you're not interrupting anything. Would you like a drink?"

"Actually, I'm famished. Do you think we could grab a table, babe?" Jenny replied, shifting her attention from Kathryn to me.

"Uh, yeah, if there's a free one in here. Looks like half the convention came here to put a load on. Or, we could go somewhere else?"

Jenny scanned the room and found a two-top near the corner. "Got one," she said. "Kathryn, it was so nice to meet you. I promise, he's all yours tomorrow."

Kathryn bid Jenny goodbye with a wave and a smile, and Jenny took my hand and led me to the only free table in the room.

"She seems nice!" Jenny said. "I don't remember you mentioning a Kathryn at work."

"Truth is, we almost never work together. We just happened to get randomly assigned to the same work trip. But it's been nice getting to know her. She just got married last month," I offered, intending to allay any suspicion.

"That's no surprise. She's absolutely adorable."

"Yeah," I said, noticing a well-dressed man occupy the seat I had just abandoned.

"Looks like you're not the only one who thinks so."

Jenny turned over her shoulder to understand what I meant. The guy was trying to chat up Kathryn, but she wasn't reciprocating.

"I'm sure she gets a lot of attention," Jenny said.

"Well, not nearly as much as you. Especially in that dress, babe. Are you kidding? Could you feel the heat as every man stared lasers at you as you crossed the room? You make me feel like the luckiest guy in here!"

"Aww, you're sweet. It's been a while since I was able to dress like this. You know I did it mostly for you, even if I must admit that it did feel good to receive that attention."

The waiter took our order. Jenny had a salad and ordered a boulevardier. I ordered steak frites and a Lagavulin neat. As we ate, I attempted to pry some information out of Jenny.

"So what did you have in mind for tonight?"

"Oh, I didn't have anything specific in mind. Just thought it would be nice to have a night alone. No chance of the kids interfering. No need to drive home. Have a couple cocktails, get a little wild..."

"I mean, you know that sounds great to me. It's the 'get a little wild' that I was most curious about."

"Like I said: no specific ideas. Get a little tipsy, let's see what happens."

"OK, I can be down for that."

As Jenny lowered her head for another bite of Caesar, my eyes drifted beyond her to Kathryn. The guy who had occupied my seat was still there, unable to take a hint. Jenny caught my stare and for a minute I thought I was in trouble. She turned to see what I was looking at, and noticed Kathryn was dealing with a slightly inebriated suitor.

"Do you want to go over there and shoo that guy away?" Jenny asked me.

Yes.

"No, Kathryn can take care of herself."

"That guy looks awfully persistent. She's clearly annoyed. Maybe I should go over and rescue her."

Absolutely not!

"Yeah, that might be a good idea. If you're comfortable doing so."

Jenny, always one to make sure everyone was happy, immediately rose and made her way to Kathryn. Kathryn hadn't seen her coming, and startled a bit when Jenny tapped her on the shoulder. When Kathryn turned, Jenny gave her a big hug, as if they were old friends. They guy who had been hitting on Kathryn was disappointed to lose her attention, but his pain was softened as he caught a healthy glimpse of Jenny's cleavage.

I saw Jenny encouraging Kathryn away from her stool. No. What was she doing? Kathryn seemed unsure, too, and was as hesitant to go with Jenny as she was to talk to the obnoxious patron from whom she was being rescued. Then, to my horror, I saw Jenny grab Kathryn's hand and lead her back to our table. With Jenny ahead of her, Kathryn looked at me with wide eyes and a shrug, indicating that she was basically being dragged here.

Jenny pulled a chair from a neighboring table and squeezed Kathryn between us at the table built for two. Her ample cleavage jiggled a bit as she plopped back down in her chair.

"That guy was the worst!" she said.

"Thanks for the save, Jenny. But really, I didn't need rescuing. I don't want to intrude on your night. Henry said he was really looking forward to a night away from the kids."

Jenny looked at me with wide, almost tear eyes. "Really, he said that?"

No, I didn't.

"Yes, I did. Sorry, I hope you don't mind that I mentioned it to Kathryn."

"It was probably all my yapping about being a newlywed, Jenny."

"Of course I don't mind! It's not like it's some secret why a wife would be spending a night with her husband away from their kids."

Jenny took a first sip of her second boulevardier, and waited for the waiter to leave before continuing.

"Besides," she said, "I hope he is excited. I said we might get a little bit wild tonight."

I, mid-sip, nearly sneezed my Scotch through my nose. Kathryn, though, seemed to appreciate Jenny's loose tongue.

"Oh really?" she pried. "Care to elaborate?"

Jenny chuckled, then turned to me. "I like her," she said.

Me, too.

Jenny had the flush cheeks that always arrive after her second quick drink. "You're falling behind," she said to both of us.

I flagged the waiter and ordered a third round of drinks. As we waited for him to return, the conversation hit a bit of a lull, with Jenny and Kathryn discussing their jobs. What the fuck was happening? How did we get here?

A part of me was glad they were hitting it off. If our affair ever came to light, maybe Jenny would understand why I might have been enamored with her. No, that's fucking stupid. Doesn't matter how charming she is, Jenny would be fucking pissed. If Kathryn and I had planned to eat with Jenny, we could have game-planned and been on the same page. Now, I didn't know what she was thinking. For all she knew, I encouraged Jenny to have Kathryn sit with us.

Christ, now they were giggling like they'd known each other for years. Jenny even put her hand on Kathryn's wrist, and Kathryn seemed totally at ease with it.

The waiter returned with our drinks. Jenny's licked her lips as her third boulevardier was placed before her. Kathryn took her third martini from the waiter's hand and sipped it before setting it on the table. I, needing to slow down a bit, opted for a gin and tonic.

The ladies seemed to be feeling better than I was. After starting in on their drinks, Kathryn lowered her voice to make sure other tables couldn't hear us.

"So, seriously, Jen...what do you mean by 'wild?'"

Jenny blushed. "Seriously, you and my husband! We can't just let things happen and see where we end up?"

She hiccupped, a historic indicator that she was starting to feel a little loopy.

"Sorry, I didn't mean to pry. I just thought that maybe you had an idea that I could take home to the hubby."

Jenny shrugged her shoulders. "No, it's not a problem. I don't have anything specific planned. I just thought I could come down here, get a little loopy, and get uninhibited with my husband. Who knows? Maybe we end up trying something we've never done before."

There was a pregnant pause, begging for someone to say something. The conversation could have gone in any direction at that point. Kathryn could have bowed out and excused herself. Any one of us could have cracked a joke and changed the subject. I could have forced a change of subject by pointing out how uncomfortable this was making me.

But Kathryn took things in a different direction.

"You mean, like...anal?"

It was a record scratch moment. The music switched between songs. Every other conversation in the entire room hit a pause at the exact same time. It felt like all eyes were on our table, including mine. I couldn't bring myself to stare up from my plate.

After a few seconds, the next song started playing, and Jenny and Kathryn erupted in laughter.

I noticed the men at the tables nearest to us lean their ears closer as Jenny responded.

"Well, no, not specifically. But also not...necessarily...not...?"

Kathryn gasped in mock shock. "Jenny!"

Now, no doubt, all the men within earshot were fantasizing about bending my wife over the table, flipping her skirt up and fucking her ass.

"Wait!" Kathryn nearly yelled, clearly feeling the effects of all that gin. She grabbed

Jenny's wrist, which was perched on the table, then lowered her voice to continue.

"Is that why you invited me over here?"

Jenny laughed again, but I felt like I was visibly shaking. My worlds were colliding, and Kathryn was encouraging it. What happened to rule number one? Was she doing this because she thought it was my idea? Was she just completely blitzed and not thinking clearly?

"Kathryn, you're too much!" There was another brief pause as they both laughed.

"Besides," Jenny continued, "I was hoping to do something I've never done before."

Kathryn gasped again. "Ohh. Emm. Gee! Jenny, you?"

Jesus Christ, this was spinning out of control.

"I mean, I went to college after all. Didn't we all experiment a little in college?"

This was not a revelation to me. I was aware that Jenny had hooked up with a couple girls in college, including once in front of a bunch of randy frat bros. But to my knowledge, this was the first time she'd talked about it since then.

"Well, Jenny, I have to be honest. Every time you open your mouth I learn another reason why Henry loves you so much."

She looked over to me and winked, then returned her attention to Jenny.

"You know, I've barely worked with your husband at all, but I've gotten to know him pretty well on this trip. And to be honest, I was thinking that he must be married to a very lucky woman. But now, it's clear that he's the lucky one."

Jenny looked over to me and smiled. "I think we both feel pretty lucky."

"As it should be," I answered.

Jenny maintained our eye lock as she moved her hand on top of Kathryn's.

"I suppose," she paused, "that this would classify as 'pretty wild.'"

Kathryn remained mute, seeming to want to hear my opinion before responding.

"Whoa," I said. "Don't get me wrong: that's every guy's dream. But I don't think that's a good idea."

"Why not?" Jenny asked. "I think she's beautiful. Don't you agree?"

Kathryn flipped her hair over her right shoulder and turned to her left to face me. Her eyebrows were raised as if to say, "well, don't you?"

"I...yes...of course I do. But we work together. You're not worried about us seeing each other all the time after this?"

Jenny shrugged. "Not really. You both said that you barely ever see each other at work. And besides, I trust you."

I looked over to Kathryn, pleading with her to back out. This was going too far. But perhaps my intoxicated pleading looked like hope, because Kathryn was squarely on Jenny's side.

"I'm down. I don't know what my husband would think, but I'll trust you both to keep this between us."

Fuck me.

The expression in Jenny's eyes was one of hope. I believe that she didn't come here with a plan, but three potent cocktails in, this seems to be exactly what she needed.

An experience that reminded her of her youth, of a simpler time before kids when we were more free-spirited. A time before I was checking my phone every five minutes, and when we could just up and drive three states away if we wanted to.

"Tell you what," I said. "I feel like I'm negotiating against myself here. I'm going to take myself out of the equation. I'll go pay the bill, then head up to my room. You stay for another round, and decide if this is really something you want to do. If you both come to my door in half an hour, I'll consider that consent from all parties. Deal?"

Kathryn gave a salute. "Aye aye, captain!" she said, mocking the severity of my speech. Jenny yelped at her response. She reacted as if it was the funniest thing she'd ever heard. She clenched Kathryn's hand tighter as they both laughed.

Seriously. What the fuck?

I told the waiter to bill my room, then headed towards the elevators. I was a little dizzy from the three drinks, and the reflective walls did little for my balance. But I managed to make it to my room in one piece. I cracked the window as far as it would go, hoping the fresh air would bring me back to the present. Then I countered that by pouring myself a bit more Scotch. I removed my jacket and tie and tossed them on the desk.

Sitting in the lounge chair by the bed, I reflected on where I was. I decided that I had actually made a pretty good call, leaving it up to the two of them to determine next steps. If Jenny came back to the room, I'd fuck her senseless before she even took her dress off, and I'd be more than happy with that. If they both came back, it was their choice to do so. The only issue there was if Kathryn and I showed a bit too much compatibility. But at this point, I'm not sure Jenny would even recognize it. She was three sheets to the wind.

As with last night, I heard Kathryn's door open and close, but there was no knock on my door. This confused me further. Did they both go into her room? If so, why? Did they decide not to do it? Did Kathryn come up ahead of Jenny while Jenny finished her drink? I was tempted to repeat last night's spy method, but my glass was still half full of Lagavulin, and you don't waste good Scotch. If they were both next door, they were being awfully silent.

A few minutes later, the door opened again, and that was followed by a knocking on my door. I took a deep breath, finished off the dram, and opened the door. Jenny was standing there alone, with an urgent look on her face.

"Honey, something's wrong!"

"What is it?" I said, suddenly in a panic.

"The babysitter abandoned the kids. They just called to say that she left and they're home alone!"

Of all the possible scenarios.

"Wait a minute. I thought your sister was watching them tonight?"

"She was going to, but had to back out last minute. I found a girl on Craigslist who lived in the neighborhood and had a lot of recommendations. I'm so sorry. I really didn't want to miss out on tonight."

"Well," I said, calming down a bit. "I suppose they'll be OK by themselves for a couple hours. Are you going to catch the next train home."

"No," Jenny said, her demeanor shifting. "I actually tracked down the sitter."

"Oh, well where is she?"

Jenny reached to the left beyond the doorframe.

"She's right here," she said, pulling Kathryn into view.

"Wha-?" I said as confusion reigned. Then, it hit me like a ton of bricks. Roleplaying. I couldn't believe Jenny would resort to pretending our kids were in peril in order to make it seem so real. Kathryn was wearing a tight pair of jean shorts and a spaghetti strap tank top that revealed a bit of her abdomen. I guess this is what they were doing next door, trying to make her look like a babysitter.

I stepped backwards, suggesting that whatever happened next probably shouldn't happen in the hall. They both entered, and Kathryn put her hand on my chest.

"I'm really sorry," she said in a pouty voice, trying to sound like a ditzy teenager. "But I saw that picture in the living room of you and your wife at the beach, and I really needed to know if you had a trunk beneath your trunks."

Jenny cackled, clearly enjoying the charade.

At this point, what was I supposed to do? Kathryn was into it. My wife wanted me to enjoy it. They had been allowed plenty of opportunities to back out or change their mind. And yet here they were: my wife encouraging Kathryn to fuck me. I allowed myself to join in.

"There's only one way to find out," I said, removing my belt.