Unexpected Anal Office Tryst Ch. 03

"Wednesday would be best."

"Perfect. I'll message you that morning."

"Can't wait."

I sent the last message, and then confirmed that all prior messages were already deleted. The app worked like a charm.

.....

On Wednesday morning, I made love to my wife. We weren't normally a morning sex couple, but I was already excited about that afternoon, and Jenny was more than receptive to my advances. It was spontaneous and passionate, with my thrusts being a bit more emphatic than normal. At one point, I almost yelled Kathryn's name, but fortunately only "kah—" came out, and it sounded more like a spasm than anything else.

With Jenny's head on my chest, post-coital, she asked what came over me. I told her that I had woken a bit before her, and the way the sunlight had illuminated her face that morning, I was overcome by how beautiful she was. The truth was that I was envisioning fucking a tight little asshole over my lunch break. The sensations of it clasping to my erection and sucking the cum out of my balls were still fresh in my memory, and I was ready for more. But Jenny seemed convinced, given how she squeezed me tighter.

The fringe benefit of morning sex was that I would hopefully last a little longer with Kathryn. Though with the way she pressed my buttons, there was no guarantee that I wouldn't be shooting my load up her ass or down her throat in a few short minutes.

At 11am, a message came through the Incognito app.

"La Quinta Inn on 71st St. I'll be ready at 12:30p."

"I'll be there. Not sure how much time we'll have, so you should probably be naked when I arrive."

A minute later, an image came through. It was a shot over her shoulder and down her back. The curve and crack of her ass were just starting to come into view before the frame cut it out.

"I'm already naked. Just preparing myself for your huge cock. Don't be late."

For the next 70 minutes, I was able to perform only the most perfunctory of tasks.

Anything that required critical thinking or analysis would have to wait until Kathryn's lithe body wasn't front of mind.

At 12:10pm, I began the 12-block trek to La Quinta. NY streets are much closer together than the avenues, and can usually be walked in under a minute each. Sure enough, I was at the hotel by 12:20pm. I reached for my phone to ask what room number, but Kathryn had already sent it.

"Room 513."

Three minutes later I was at the door. Early, but she wouldn't mind a few extra minutes to play, right?

I knocked on the door, and Kathryn answered it immediately. She was wearing only a plush robe.

"You're early," she said, not at all upset.

"I couldn't wait."

"How long do you have, do you think?"

"I have a meeting at 2pm. Should be back at the office by 1:30p, so maybe 50 minutes?"

At that, Kathryn grabbed my hand and pulled me inside. "50 minutes. We shouldn't waste a single one."

She grabbed for my belt and started freeing it from its buckle. I whipped off my jacket and tie and got to work on my shirt buttons. Kathryn pulled the belt from the loops and tossed it behind her, then attacked the zipper and button of my slacks. Once she felt she could do it without looking, she turned her head up to me and pressed her lips against mine.

I finagled my shirt off, and broke our kiss only to lift my undershirt over my head. Kathryn had pooled my pants and underwear around my ankles and was now stroking my cock to attention. I grabbed the back of her neck and held her tight to my lips as our tongues began to wrestle. Meanwhile, I stepped on the heels of my shoes to pull my feet free, then kicked everything off to the side.

Kathryn now stepped back to take in my body.

"You know, it's kind of unfair that we've already had three sessions and this is the first time I've seen you naked," she teased.

"You were on my like a rabid animal. Didn't even give me the chance to take my pants off."

"Well, I'm glad I've seen it now. You have an amazing form," she said, moving in to run her hands over my chest and midsection.

"But like I said, no time to waste. And I owe you for what happened in the park."

Kathryn undid the belt of her robe and let it fall off her shoulders. Her perfect body revealed itself to me once more, and each time it was as stunning and inspiring as the first. I reached out to cup her breasts, but she pushed me back on the bed.

"I want to practice, just in case we ever invite Amber to join us."

At that, she dropped to her knees and took my cock in her left hand. She enveloped my head with her mouth, and then started pumping slowly with her hand as her tongue tickled my hole.

"Fuck yes, you're off to a good start, baby," I said.

She cooed sexily, though it was muted with her lips closed around my dick. She started lowering her head deeper onto me, taking in several inches until it hit the back of her throat. It caused her to gag for a bit, but she handled it like a pro. She opened her mouth and allowed some of the saliva to spill onto my shaft, which made her hand feel all the better.

Kathryn then removed her mouth and knelt lower, licking up the bottom of my erection. She covered the entire length a couple times, then sunk down to my balls.

In my entire life, I never had a girl suck one of my testicles into her mouth. Never even thought to ask, honestly. But now that Kathryn was doing it, I wasn't sure I'd be able to cope without it. She held a ball on her tongue, then wiggled it around, feeling every crevice in my scrotum as she did. She then repeated the process with the other ball. Soon, I was fully taut, with hardly any wrinkles left to explore.

"Fuck, baby. Where'd you learn to do that?"

She let my scrotum fall out of her mouth with a plop.

"I watched a couple videos on PornHub. And I'm just getting started."

She managed to dip even lower, exploring the short patch of skin between my balls and my asshole, before running her tongue lower and into the crack of my ass.

"Whoa!" I said, startled and unsure if that was something I wanted. But Kathryn was persistent. She pushed my right leg up so that the foot was sitting on the bed, then pulled my right check open a bit to gain better access to my ass. As she did, she started pumping my dick with her left hand again. My ass clenched as Kathryn lapped at my sphincter. That motion caused everything to feel tighter, and amplified the sensitivity of my cock.

I laid flat on my back, allowing myself to relax and give into this new experience. Kathryn was making mewing sounds as she lapped away, and her pace on my dick was accelerating.

It was amazing. Not just the physical sensation of having a seemingly sweet and innocent officemate lap at my asshole while she gave me a hand job. But also the mental sensation of knowing that some poor sap was about to marry this woman. That in three days, he was going to raise her veil, revealing her sweet face, and kiss her innocent lips, proclaiming his love for all eternity. And now, that sweet face, those innocent lips, were buried in my ass, searching my darkest area for a source of pleasure as her forehead pressed against my balls.

It was good, but given that I'd already cum that morning, if she were to get me off right now, I definitely wouldn't be able to muster another round before returning to work. I sat up and grabbed Kathryn's hair, pulling out from between my legs. She looked up to me, her face smeared with her own saliva and perspiration. Probably some of my own as well.

"Did you not enjoy that?" she asked, seeming genuinely concerned that I may not have.

"On the contrary, that was fucking amazing. Never had a woman do that before. But I don't want to blow my load too early. We still have forty minutes or so."

"I don't imagine you'd still be willing to kiss me after that?" she asked coyly.

I hadn't considered it, and the idea initially repulsed me, but I quickly got over it. If she was willing to do such a dirty act for me, shouldn't I reciprocate? I pulled her up to me, both of us standing, and locked lips again. It wasn't as bad I was expecting. It was musky, but not overly pungent, and if anything it just heightened the taboo nature of what we were doing. My cock managed to get harder.

I sat back on the bed with Kathryn standing naked before me. I pulled her close and closed my lips around her left nipple. My arms enveloped her waist and pulled her flush against my midsection. My right hand drifted a bit lower to cup her ass, giving it a hard squeeze before spanking it forcefully. She yelped in surprise.

"You've been a bad girl, Kathryn," I said before spanking her other cheek. "You've been very bad, and I love it!" I spanked her left cheek again. With each spank, he pelvis ground into my ribs. She bit her lips, the pleasure apparent on her face.

Without a word of warning, I broke off the kiss and threw her face down on the bed. I was ready to get her butt in my hands and my pulsating shaft deep in her asshole. She giggled, but bade me wait. It was then that I noticed something rubbery and black peeking out of her ass.

"I told you I was preparing myself for you. Not only did I give myself an enema, but I managed to work this beauty up there."

She turned onto her side and grabbed the base before slowly pulling out what looked to be around a six inch dildo, black and incredibly lifelike. It glistened from whatever liquid had remained from her enema, but otherwise ran clean. Then, continuing to shock me, she slid it right into her pussy. Her back arched and her left knee bent slightly as she accommodated its girth. A satisfied and exceptionally naughty grin took form as she began to slowly work the fake cock in and out.

"I don't want you to get too used to the feeling of my asshole, baby. I thought maybe you could fuck it while I fuck my pussy. What do you think?"

Without a word, I jumped on the bed, much to her amusement. She literally laughed out loud, freeing herself of any inhibition. I think she was still coming to terms with how sexual she could be, and was allowing herself to not feel guilty about it. I, too, had begun to care less about having an affair. A beautiful woman offering her puckered asshole to you while she DPs herself has that effect on a guy.

She was still on her right side, so I straddled her right leg and bent her left knee up towards her chest. This position exposed everything to me. Her pussy was oozing, and her juices were slick on the thick rubber cock pistoning in and out of her. Her asshole was noticeably gaping, but still smaller than the circumference of my dick. I grabbed her left cheek with one hand and pulled it open, and took aim with my right hand wrapped around the base of my cock.

I slid in easily at first, my head popping past her sphincter more smoothly than the previous two times. But once inside, she felt tighter than I remembered. I could feel the weight and veins of the dildo, sliding against me as she pumped away. It seemed to surprise us both.

"Oh fuck!" we each yelled in unison, before pausing to laugh at the situation.

Nobody who knew us would ever imagine either of us in this situation, especially with each other. But here we were, two respected, upstanding members of society, engaged in the raunchiest of sex.

"Hold still. Let me get a bit deeper, then you can start pumping again," I advised.

Kathryn obeyed, holding the dildo so just the head lay inside her pussy. That freed up some space, and I took advantage by forcing the rest of my length up her quivering anal chute. Kathryn turned her head down and bit the bedsheet, emitting a guttural moan as I bottomed out in her.

Meanwhile, the head of her dildo was pressing against the base of my cock, having the same effect as a cock ring.

"OK," I said. "Try to push your dildo back inside."

Continuing to bite the bedsheet, Kathryn pushed the dildo deeper. Fuck, what an amazing sensation that was. The heat of her body combined with the saliva she had slathered all over me to create a hot and humid atmosphere inside her ass, and the dildo was stroking against the sensitive glans just below my head. I forced myself to resume my motion, moving slowly in and out of her as she continued to do the same to herself.

"Are you OK?" I asked, worried that it might be too much for her.

"Fuck yes," she answered breathlessly. "I'm about to explode."

That encouraged me to give her a bit more effort. I started pumping faster.

"Do it, Kathryn. Squirt all over these sheets for me. Fuck your hips against me like we'll never be in this room again, and you can be whoever you want to be."

She groaned again -- through a lascivious smile -- and began rocking back to meet my thrusts, all while continuing to fuck her own pussy. Her nipples were hard and protruding noticeably from her breasts. I grabbed her left one, and pinched it gently.

With my right hand, I grabbed her shoulder for leverage, and started thrusting as hard as I could manage.

Kathryn's left leg started shaking uncontrollably, the back of her thigh connecting with the front of mine as her orgasm became inevitable. Finally, she pushed the dildo all the way in to the base, and her body was racked with an apoplectic fit.

"OH MY GOOOODDDD!" she screamed, surely alerting the neighboring rooms to our salacious activity.

She rolled onto her stomach as her body reacted to the orgasm. I could feel her liquids splashing against my thigh and dampening the mattress below us. As she turned, her butt pulled away and my cock slipped out. Though I was tempted to follow her movement and reenter her, I took a moment to appreciate the sight before me.

Her adorably toned butt, the one I had fantasized about long before we ever got together, was perched upward and presenting itself to me. Her asshole was open wide, missing my presence. Beneath that, her pussy clung tight to the dildo, but it was now shimmering with her juices, which cascaded down her nimble fingers, still securing the fake cock in place. A couple of her fingers traced the folds of her pussy in post-climactic bliss. I did my best to commit this view to my memory bank.

Then, not wanting to lose a single minute, I mounted her again. As she was now lying face down and flat on the bed, I straddled both legs this time, letting my erection sit on her ass for a second.

"Ready for more?" I asked.

"Abso-fucking-lutely."

I aimed down at her open hole and plunged all the way in. Her dildo was still lodged on the other side, but I was prepared for what to expect now. I went from zero to sixty in one second, unable to temper my lust. Her tight ring clung to every centimeter of my length. It was at once agonizing and euphoric. Euphoric for obvious reasons, but agonizing in how quickly it was going to make me cum.

Kathryn was no longer moving the dildo, but was stroking her clit with her fingers, edging herself towards another climax.

I collapsed on top of her, using my elbows to support my weight as I slid my hands under her. My stomach pressed flush against her back. My left hand cupped her right breast, with her left breast pinned against my forearm. My right hand grabbed her throat firmly, but not hard enough to prevent her from breathing or speaking. I kept pumping away at her ass, albeit with narrower thrusts given my new position.

I lowered my lips to her ear and whispered, "I'm going to cum. Where do you want it?"

"Yeah, baby. Give it to me. Deep in my dirty little asshole, baby. I'm going to cum, too."

That was all I needed. I clenched my ass and burrowed as deep as I could go. Cum shot out of my balls like a geyser, shooting so hard and so deep that I couldn't even feel it after it drained from me. I held her tighter as her sphincter pulsated against my base, coaxing any remaining jism into her anal passage. At the same time, she continued to stroke her clit until she exploded in her second orgasm of the afternoon.

I held her like that for several minutes, neither of us saying anything. We were happy. It felt organic, not at all true to the sinful nature of our behavior. After my cock softened, I pulled out and helped her up towards the pillows. She laid on me in a similar fashion to how my wife had that morning.

"I don't know how long we'll be able to keep this going, Kathryn, but I want you to know I think you're amazing."

She nuzzled her face into my chest hair.

"Me too. I was so nervous about making the first move, but you've proven my intuition to be correct. This is beyond what I had hoped for. It's blossomed into so much more. And I agree: I don't know how long we can make it last, but I'm so grateful for what we have done so far."

I held her tightly, enjoying the feel of her skin against mine. Her leg repeatedly brushed up and down against mine. I could feel some her heat and her moisture against my thigh. Her nipples, still rock hard, pressed against my rib cage. Her silky hair draped peacefully on my shoulder. It was getting harder to reconcile just how wrong this all was.

"I hate to say this, but this might be our last time together for nearly a month. I won't have any time before my wedding on Sunday, then we're going on a two-week honeymoon. When I get back, I'll definitely have work to catch up. Not sure I'll be able to sneak out."

I had anticipated this news.

"Honestly, maybe that's a good thing. I'll miss you, don't get me wrong. But we've met three times in the last five days. Maybe some time apart will heighten our anticipation of the next time."

"Good. I was worried you'd be upset."

"Kathryn, how could I be upset at you? We agreed that nothing would get in the way of our home life. I'm happy for you and Jeremy."

I felt the weight of her head grow as she pressed into me a bit harder.

"You should head back, but before you do. The company just posted a four-day trip to Philly next month. It's a sales conference. We should both lobby out bosses to send us. I don't think there will be a lot of people clamoring for it, because Philly is only an hour from here, and most prefer to spend the company dime traveling to places they can't go on the weekend. I've already put in the request. If we get to go together, imagine how much fun we could have."

"Consider it done," I said. "I love Philly. We could go to South Street and visit a couple of the adult shops, pick up some new toys for our next adventure?"

Kathryn's hand dug into my ribs as I suggested it. "I like the way you're thinking," she said.

"Do you want me to pony up for my half of this room?" I asked.

"No, you can get the next one. Now get out of here. You should probably towel off before you get dressed. And take a mint from my purse for the walk back."

I kissed her one more time before arising, and did exactly as she suggested. It would be nearly three weeks before I saw her again.