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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. 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 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 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.
“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.