Unexpected Anal Office Tryst Ch. 03

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In the early afternoon on the following Monday, Kathryn and I were strolling through Central Park together. The autumn weather was cooperating, maintaining a refreshing fifty-five degrees. The leaves were changing color, adding complexity to their sylvan hue against the blue-gray sky. It was a perfect day, but I had a difficult time focusing on any of that.

Kathryn had popped into my office shortly after I arrived that day. Keeping things quick, she asked that I meet her at the southwest entrance to the park at 12:30pm. Knowing that obeying her every command had resulted in the two best sexual experiences of my life, I was happy to oblige her, whatever the reason.

As it turns out, she hadn’t planned another tryst. This rendezvous was strictly for the purpose of laying out the ground rules, upon which we had to agree before taking anything further. In typical Kathryn fashion, she laid out the subject matter bluntly and irrefutably.

“I came up with six rules, Henry, and I think that if we abide by them, we’ll be able to continue meeting.”

“I’m all ears,” I said, though I wasn’t. Knowing what lay beneath her tight pants and blazer made it difficult for me to concentrate. We were close enough that our arms occasionally grazed against each other, but carrying on with a professional demeanor in the hopes of subduing speculation.

“First, and by far the most important, we don’t do anything for or with each other that would endanger the foundations we’ve built at home. We don’t meet in lieu of a date night with your wife or an anniversary with my husband. You don’t skip one of your kids’ soccer games to come fuck me senseless. Our homes take absolute priority. Do you agree?”

“Yes, that’s exactly right. That’s what I said on Friday, too. I don’t want to risk what I have there, even if it means never hooking up with you again.”

“Well, I’m hoping we see each other a lot. That’s what these rules are for.”

“What’s the second rule?”

“I don’t think you’ll object to number two, but here goes. As much as I loved what occurred on Friday, moving forward, my pussy is off limits. Back to our original deal of anal only. I have a stigma about it. I want Jeremy to have exclusivity on my pussy moving forward. It just feels right. We can continue our affair, but only butt stuff. Is that a problem?”

I allowed space for a pregnant pause to consider what had just been asked of me. I can only move forward with this beautiful side action if I limit myself to her asshole? How did I get so lucky?

“I understand and respect that, but can I just clarify what that means? When you say your pussy is off limits, does that include oral? What about fingering?

Kathryn lowered her head as her cheeks began to redden. I had given her the first oral orgasm of her life just a couple days ago, and I had only done it because her fiancé never went down on her. Did she really want to give up on that experience for the rest of her life, with some halfwit who didn’t know what he was missing?

“I hadn’t considered that. Let’s say no penetration. So you can rub, and you can lick, but no penetrating me with your fingers or your cock.”

I loved the way she spoke so mater-of-factly about this.

“I can live with that.”

“On second thought,” she added, “Let’s agree that if I want to make an exception to that rule on the fly, that’s within my right. I can’t lie. Overcome with lust, I let you violate our agreement on Friday, and it was the most powerful orgasm I’d ever experienced. Let’s agree that it’s a rule, but never say never. OK?”

“OK by me. I’m just happy to serve.”

“Yeah, I bet. OK, rule number three. We can’t continue to meet every Friday. Our cadence needs to be sporadic and random. I’m worried that if you and I are always the last two out on Fridays, it will arouse suspicion. We need to find other ways to sneak around.”

“Makes sense. Like what?” I asked.

“Well, there’s a thousand hotels in this city. We’re both well-enough positioned in life that we can easily afford one night’s stay, even if we just use it for the afternoon. Or, and this is a long shot, if there’s an evening where we both find ourselves free, we could use a hotel for that, too. We pay cash so there’s no evidence on credit card bills or bank statements.”

“OK, but are you saying the office is out of play moving forward, or that we need to mix it up? Because I don’t think we should rule out another office session if we both feel that it’s safe.”

“I agree. I just don’t want to make it a habit. Even if the chances of getting caught are smaller than one percent, the more we risk it, the more likely a bad outcome.”

“Heard. So how do we decide when and where?”

“Great segue. On to rule number four. We communicate only through this app called Incognito. sıhhiye escort It is basically a text message program, but everything you send is automatically deleted ten seconds after it’s opened. It also disables screen capturing, so there’s no way that any of our communications will be intercepted. And hell, it allows me to perhaps send an occasional naughty pic.”

“Seems you’ve thought of everything,” I said.

“Thanks. Once you download it, I’ll send you a message to confirm that it’s working.”

I was already opening my phone to find the app, and ten seconds later it was being installed.

“Also, we both travel for work every couple months, but in eight years, we’ve only been on 2-3 trips together. We should lobby our bosses to send us on the same trips. Maybe we end up making a really great team, and they start scheduling us to travel together all the time. Can you imagine? 2-3 nights in another city. No interruptions? Think of how easy it would be to cast our inhibitions to the side and get freaky. Hell, we could even visit a sex shop together, pick out some toys for the night.”

“Ha, you’ve considered many more possibilities than I have,” I replied. “Probably because I’m a guy, I’ve only thought about what’s happened so far, and how to replicate that. Yes, a couple days alone would be amazing. You might have just opened Pandora’s Box.”

Kathryn smiled and blushed. She managed to constantly shift between demure and dominant. She knew what she wanted and was confident in pursuing it, but also embarrassed by achieving it. It was one of the reasons I was infatuated with her.

“I believe you said there were five rules. What’s left?” I asked.

“The fifth rule is that if we are ever going to run in violation of any of the rules above, we need to mutually agree to it. No surprising each other. Spontaneity can be nice in a romantic relationship, but when hiding an affair, we need to be diligent and respectful.”

“I agree, but honestly I’m surprised you felt the need to outline that. You know I would never do anything to compromise this.”

“I know that, Henry.” She paused, appearing suddenly shy. “I actually made that rule for me. I have an idea I want to run by you.”

“Uh, yeah. Go ahead.”

“I have this friend, Amber. We’ve known each other since we were kids. She grew up in the house next door, we went to the same high school. We separated for college but always stayed in touch. We were like yin and yang: polar opposites, but always in harmony with each other.”

She paused again, in a manner reminiscent of before she took her shirt off in front of me two weeks ago. She continued after taking a long breath.

“We were polar opposites in every way, including sexually. She was always promiscuous…I’d guess she’s had at least twenty partners, and has always been pretty open to experimentation. You know I’ve always had a reserved sex life, until you. Anyway, at my bachelorette party over the weekend, we both got pretty drunk, and one thing led to another. She started her friendly ribbing of my non-existent sexual history. She mocked that I’d spend the rest of my life with some milquetoast, generic, dad-bod kind of guy. I wasn’t mad, because she wouldn’t say something like that maliciously, but suddenly, the secrecy of our affair felt more like a burden.”

“You didn’t tell her about us, did you?” I asked, nervous for the first time.

“No. But I was probably one cocktail away from confessing. I just wanted to shut her up, you know? Let her know that I can be wild and naughty if I want to.”

“So how does this play in to rule number five?”

“Well, I tried to vaguely fight back by talking about how satisfied my partners were. I said that I had so few because they each fought so hard to keep me. She took it well, and we kept jostling around the issue. At some point, one of us opined — and I honestly don’t remember who — which of us could give a better blow job.”

At these words, my cock started to stiffen. I bent my knees to provide a bit more space in my pants, but I had a feeling I was going to need to sit on a park bench soon.

“Two weeks ago, I would have said she would be the blow job queen between us, but after what we did in the conference room, I think I might be able to take her. I mean, not every woman can deep throat, but I did after just a couple minutes of your persuasion.”

“Do you mind if we sit down here, Kathryn? You’re getting me a little excited, and I don’t want to startle any of the innocent pedestrians walking our way.”

Without awaiting her reply, I sat on a nearby bench, crossed my legs, and held my hands over my crotch in as natural a way as possible.

“You men and your uncontrollable urges.” She rolled her eyes and sat next to me.

“Please. You’re going to tell me you’re not a little wet from all this sex talk?” I prodded.

“Maybe a little. But listen, I haven’t got to the point yet. Amber and I are very close. I honestly think I could tell her about tandoğan escort us, and she’d be proud of me. And she’d never do anything to harm my upcoming marriage.”

“That’s fine, but why risk it? What do we have to gain by her finding out? You can’t just keep it a secret?”

“Well, my idea is that I invite her to join in.”

My eyes nearly popped out of my head.

“I mean, how could either of us claim to give the best head unless we give it to the same guy? She’d be down to participate. Of that, I’m certain. I’d get to prove that I can out-sex her, at least in one category. And you’d get a double blow job. I mean, is that not a win-win-win?”

“I, uh…yeah, I guess,” I stuttered incoherently. “Seems like we might be going a little fast, but I do trust you. If you think she’ll keep quiet, I suppose I’m in for that.”

Kathryn, feeling empowered by the effect her words were having on me, glanced knowingly down to my trousers.

“Having trouble concentrating with that bulge in your pants?”

I chuckled. “Yeah a bit. See what you do to me, Kathryn?”

“Stay here,” she said.

Kathryn sauntered about fifty feet away. At first, I thought she was just going to abandon me like this. Instead, she found a coin-operated newspaper dispenser, entered the necessary payment and return with today’s New York Times.

Sitting next to me once again, she opened the cover page and handed it to me.

“Here, hold this,” she said. “This will cover you up better than whatever you’re doing with your hands right now.”

“Always thinking, Kathryn. Thank you.”

“You’re welcome. Now, just relax and let me know if you see anyone coming.”

I startled as Kathryn slipped her right hand into my lap, finding and grinding on my erection.

“Wha…” was all I could get out before I thought to look around. We were in a relatively isolated are of the park, near Gapstow Bridge, on a bench about 15 feet back from the path. We’d only passed a couple people during our stroll, and since sitting down maybe two or three more had passed by. Still, given her insistence on being discrete, this seemed like a pretty big leap.

“Just relax,” she said, sensing my concern. “Nobody can approach us from behind; just keep your eyes forward. I’m being subtle enough that no one would suspect a thing from a distance. If someone comes close along the path, I’ll withdraw.”

“Fuck, Kathryn, it feels so good,” I groaned. Holding up the paper proved to be a bit of a challenge with the magic she was working.

Having stroked me to full staff, she clasped onto my cock and made long strokes up and down the shaft.

“Where do you want me to cum?” I asked. “If you put your head in my lap, you’ll definitely draw more attention.”

She laughed. “Oh, no, that would be too big of a risk for sure. I’m just going to pump that cum into your pants. How does that sound?”

“But I have to return to work after this. How can I explain the stain? Or the smell?”

Kathryn removed her hand. “Are you asking me to stop?”

My cock twitched in disappointment, aching for her touch again.

“Oh, damn you, you tease. No, keep going. I’ll figure it out.”

Kathryn looked straight into my eyes as she brought her hand back to her cock. In that moment, she could have asked me for literally anything and I would have acquiesced. But as much control as she had over me in that moment, I loved that she had chosen to be this naughty little mix with nobody except for me. Even her future husband didn’t know this side of her.

Kathryn alternated between an aggressive tug and a cooling, tingling gesture with the tips of her nails. She danced across my entire lengthy agilely, teasing my head and rubbing my balls. Her movements had caused the tip of my cock to extend up beyond the waistband of my boxers, pressing frustratingly against the bottom of my belt.

I bit my lower lip and kept my eyes on the path, looking for anyone who appeared suspicious of us. Fortunately, nobody appeared to notice us at all, let alone our public ribaldry.

“Are you almost there, baby?” she asked in a tone that was entirely un-Kathryn. She sounded more like a porn star than the conservative officemate I’d known for the last eight years. “Are you ready to cum for me?”

“God, yes. I’m so close. Please don’t stop.”

She held her wrist still just above my cock, then tantalizingly traced each of her five fingernails over my underside, coaxing the cum higher. For someone who was historically shy, she was unnaturally good at this.

She giggled. “Why would I stop? Do you know how much fun it is for me to have this effect on you? Which method will get you off sooner? The squeezing, the rubbing or the tracing?”

“Oh..the rubbing, please. Gently close your hand around it and piston up and down. I’ll…” I caught my breath. “I’ll be done in no time.”

The corner of Kathryn’s mouth curled up into a wicked smile. She had me exactly where she wanted me. But she was kind tunalı escort about it, too. She followed my exact instructions, gripping my cock and pumping with alacrity. Within seconds, I erupted.

I hung my head and gripped at the newspaper, crinkling it into an illegible mess as cum started to spew into my pants. With that first shot, Kathryn sat back against the bench and eased her grip, slowing her tempo as she did. I sat back, too, letting it happen. There was no preventing a messy situation at this point, so I resigned myself to enjoy it while I could.

Kathryn removed her hand after I started to go soft, and I focused my efforts on normalizing my breath. My boxers felt warm and wet, but as yet there was no visible stain on the outside of my pants. Still, I needed to find a way to change before it dried and grafted the fabric to my skin. I considered myself lucky that whatever shot north landed on my belly, and not outside of my shirt.

“That was amazing. You continue to surprise me, Kathryn.”

“I continue to surprise myself. This one wasn’t planned, but all that talk had me nice and horny, and I really wanted to do something naughty for you.”

“Well, thank you. I don’t think anyone noticed. You should head back to the office. There’s a Target just outside of the park. I’m going to need to buy a change of underwear there before I come back.”

Kathryn blushed. “I’m sorry. I wasn’t thinking that far ahead when I started.”

“Don’t be sorry. It’s worth any embarrassment I might experience. Besides, there’s always a few weirdos in that location, so I probably won’t be the focus of any attention. Should be able to sneak in and out relatively easily. Changing in the office is going to be the real challenge.”


One of the things I love most about living in New York is how easy it is to blend into the masses. I’ve seen so much crazy shit that I don’t even tell my wife about half of it anymore. Hell, I’ve seen guys getting a hummer in the park, and I just kept walking like it was totally normal. When you’re the person being exposed, it seems like a much bigger deal than the witness considers it.

So as I walked to the Target with my pants full of cum, I kept my eyes on others on the sidewalk. If any of them noticed, they didn’t let on. After all, this is New York. A man with a stain on his pants isn’t going to crack the top twenty list of strangest things you’ve seen today, even if you correctly surmise what that stain is.

Even in the Target, nobody seemed to know or care. I bought my Hanes and a packet of hygienic wipes and headed back to the office. In the atrium and the elevator, I held the Target bag over the fading stain, as I was more likely to run into someone I knew here. But the gods of mercy were on my side. Straight out the elevator to the bathroom, which was empty, and into the stall to change.

Fortunately, the ejaculate had yet to dry, so it peeled easily off my cock. Still, it was smeared all around, tucking into the folds of my scrotum and splattered down to my knees. But before I started to clean, I removed my phone and snapped a picture.

From there, it was relatively easy to clean up. The wipes proved more than sufficient, and the underwear felt like freshly laundered sheets compared to the dankness that had developed.

I disposed of the boxers and wipes in the bottom of the trash can, covering it with copious amounts of paper towels just in case. Then, I turned my attention to the small stain on my pants. The only thing embarrassing about it was the location, just to the right of the zipper. Even if my coworkers wouldn’t assume it was cum, the implication was still there. The best thing to do was make it more obvious, I thought. If I acted weird about it, it might get people talking.

I wet a paper towel and started rubbing at it. It made for quite the scene as my boss walked in with me vigorously rubbing my dick.

“Ha, first time drinking coffee there, rookie?” he chided. But I mentally thanked him for giving me an easy excuse.

“Uh, yeah. Probably a sign that I should just stick to my morning cup,” I answered.

“Well, at least it didn’t land in an embarrassing location or anything.”

“Haha. Well, good luck with that,” he said, stepping into a stall.

A short walk down the hall and I was back at my desk. As soon as I was situated, I opened the Incognito app and sent Kathryn a message.

“Testing, testing, 1,2,3…”

Immediately I received a reply.

“Roger that. Are you safe and sound in your office?”

“I am. See what you do to me?” I sent, along with the picture I had taken in the bathroom.

She replied with the blushing emoji, and the face-in-hands emoji.

“I’m so sorry! But I couldn’t contain myself. You’re too sexy. And besides, I promise I’ll make up for it soon.”

“I know you will.”

“Lost in all the excitement this afternoon, I forgot to tell you that I’m taking the rest of the week off to prepare for the wedding on Sunday. I’ll be running errands in town all week, so it would be easy to get a hotel room and spend a lunch break together.

One last fuck before I’m married?”

For someone who was preaching caution, she sure was putting the foot on the accelerator. But an opportunity like this was almost impossible to pass up, especially with her saying she’ll “make up for” what happened in the park.

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