Unexpected Anal Office Tryst Ch. 06

Kathryn gave me her patented grin and lowered herself to her knees. We were still just inside the door, my back up against the wall, with Jenny standing behind Kathryn in the doorframe to the restroom. Kathryn easily slid my slacks and boxers to the ground, freeing my semi-firm cock.

"Holy shit," she continued in her ditzy teenage voice, pretending that this was the first time she'd seen it. "This is way bigger than the boys at school."

At that, she wrapped her fingers around the base and took the head into her mouth. Now Jenny approached started kissing me hard. She was standing off to the side to allow Kathryn her space, and her breasts nearly spilled out of the top of her dress as they mashed against my ribs.

"Is this what you want?" I asked as quietly as possible.

Jenny bit her lip and nodded excitedly. "Are you OK?"

"I'm more than OK, so long as you're comfortable."

"I'm more than comfortable. I didn't have anything planned, but this is beyond my wildest dreams."

At that, Kathryn grabbed her hand and tugged insistently, encouraging Jenny to kneel next to her. Jenny raised her eyes at me as she lowered herself, as if to say,

"Here goes!"

Kathryn popped my cock out of her mouth and steered it towards Jenny. I suppose now would be a good time to mention that Jenny almost never goes down on me anymore. After the birth of each of our kids, she was exhausted all the time, and it felt awfully selfish of me to ask for head. Even after we found our stride as parents, it felt weird to expect her to blow me after a long day of dealing with the kids. Let's just say, it's been a while.

But it had also been a while since Jenny had consumed four cocktails in one night, and she was showing signs of complete inhibition. With Kathryn's hand at the base of my cock, pointing it directly at Jenny's face, Jenny opened her mouth and took the head inside without hesitation. I'd forgotten how good her mouth felt. Her soft tongue was plump against the underside, and her cavernous mouth felt almost unnaturally wet. Perhaps it was the head start Kathryn had provided.

Given that we'd gone this far, I allowed myself to get into the roleplaying aspect.

"You're both going to have to suck a lot harder than that if you expect my forgiveness. What kind of mother trusts her kids to a Craigslist babysitter? And what kind of babysitter abandons her charge?"

They both groaned, enjoying the fact that I was getting more into it. Kathryn lowered herself to my scrotum and sucked the left testicle into her mouth. I put a hand on each head and pulled them in tighter. They, as though it had been coordinated, each wrapped an arm around my leg, pressing themselves closer as we formed an entanglement of human mass.

Jenny was now more than halfway down my cock, which to my recollection hadn't happened since our honeymoon. I was at the back of her mouth, but wasn't yet prepared to try to force myself into her throat. I was still uncertain of what lines I could cross tonight.

Kathryn had her neck craned so that she could suckle my balls and still look me in the eyes. When I met her gaze, she winked at me. Even with her mouth full of scrotum, I could see the hints of a smile. God, she was amazing.

Jenny had worked me to full staff, and removed her heard to catch her breath. I pulled Kathryn away as well, and admired the sight of both of them kneeling in front of me. Their lips were glistening with saliva and sweat. Their cleavage sparkled with perspiration. Their chests heaved as they refilled their lungs.

"Get undressed. Both of you," I said as I started unbuttoning my shirt. "And decide between yourselves who is going to get punished first."

I kicked off my shoes and stepped out of my slacks, then walked over to the bed to watch them obey. It was still shocking to me how quickly they had taken to each other. Of course, the fact that Jenny had no idea that Kathryn and I had been fucking for the last two months had something to do with it. But even still, they'd only met an hour ago, and now Jenny was holding up her hair so that Kathryn could lower the zipper on her dress.

Once it was down, Jenny seductively lowered the straps of her dress and let it fall to the ground. She was wearing a lacy, black bra-and-panty set; one that I'd told her repeatedly was my favorite. She looked sexy as hell, but it was still a relatively modest look compared to what I'd seen from Kathryn recently.

Jenny and I both watched as Kathryn raised her tight top over her head and dropped it next to her. She, as I'm sure Jenny already knew given that they pre-gamed next door, was not wearing a bra. Somehow in the rapid fire onslaught of surprises I'd missed this fact. Kathryn then turned away from us to peel her tight jean shorts off, exposing a thong that seemed to match the lingerie she was wearing last night.

Neither of them moved to remove any more clothing, and I wasn't going to push it yet. I sat back on the bed, slowly attending to my erection with my left hand.

"Who's first?" I asked.

Kathryn turned to Jenny and said, "I should go first. It's my fault we're both here. I shouldn't have left the kids."

"How do you want to be punished?" Jenny asked, unable to mask her excitement, or her curiosity. I still had trouble believing how genuinely into this she was.

"I think it's only fitting that daddy gets to fuck my ass."

Here, Jenny turned to me, her mouth agape. "I don't think daddy has ever done that!" she said after a few seconds. Little did she know.

I stared back at Kathryn. "Assume the position."

She strode over to the bed in a style that was both confident and demure. I rose to make space for her, and she climbed up on it, positioning herself on all fours facing away from me. Jenny, continuing to surprise me, followed her to the bed and stood next to me. As Kathryn waited, Jenny kissed me aggressively, her tongue delving deeper than I could ever recall. As we kissed, she put her hand on Kathryn's lower back.

"Spread your legs for daddy," she said while staring penetratingly into my eyes.

Kathryn moaned and spread her knees further apart. Here, Jenny grabbed the waistline of Kathryn's thong and started pulling it down. With Kathryn's thighs spread wide, the material stretched until it lodged a few inches above the knees.

Jenny whispered to me. "Enjoying yourself?"

It wasn't a question. She knew I was. She just wanted affirmation.

I nodded.

Jenny turned back to Kathryn and spanked her left cheek hard enough to leave an imprint for a second. Kathryn yelped in surprise, but immediately returned to her prostrate position.

"Ask daddy for your punishment, you little slut!" she barked.

Kathryn groaned again, clearly into it. She wiggled her ass at us and said, "Daddy, please punish me. I've been so bad. Please punish be by fucking my ass."

Jenny looked at me again with an eye gesture that said, 'what are you waiting for.'

I gripped my cock and aimed it at Kathryn's tight hole. As much as I'd fucked it recently, this experience was entirely new. It was like I was experiencing it for the first time again; though I knew I'd fit a little bit easier after all the exercise her hole had received recently.

With a grunt, I pushed the head through her sphincter, which stretched to accommodate me with relative ease. Kathryn and Jenny both gasped: Kathryn at the sensation, Jenny at the sight. Stepping a bit closer, I eased another couple inches in, and both women purred. Not wanting to ignore my wife in all this, I wrapped my left arm around her and turned to kiss her as I kept delving deeper.

Jenny was ravenous. She ran her hands over my body so furiously that she almost pulled me out of Kathryn. And Kathryn was trying to make me cum in record time with her dirty talk.

"Yeah...YEAH...fuck my ass, daddy....I've been such a bad girl...give me that cock, daddy..."

I'd never been one to enjoy being called 'daddy' in the bedroom, but Kathryn's tone was perfect for it. It felt like my cock managed to get even stiffer inside her, encouraged by her roleplay.

After a minute or so, I realized that I wasn't giving Kathryn the proper fucking she deserved. It was impossible with Jenny twisting my body towards her. So I broke off the kiss and grabbed Kathryn's waist with both hands. I motioned for Jenny to go around the other side of the bed.

"You're doing a fine job apologizing to me, but what about to my wife? You abandoned her kids, too."

Jenny stared at me in shock, her mouth somewhere between smiling and agape. But I could tell she was into it. She climbed up on a pillow, her panty-clad pussy just a few inches from Kathryn's face.

"Yes...I'm...sorry, miss... Let me...make it right," Kathryn squeaked out between by thrusts.

Jenny, for once this evening, was at a loss for words. I could see her thinking of a way to put it dirtily, but she couldn't bring herself to say it. She simply slid forward and pulled her panties to the side, granting Kathryn access. As if we had choreographed it, I used this opportunity to bottom out in Kathryn's ass, rocking her forward into my wife's juicing pussy.

Kathryn's body felt as incredible as ever. Her ass cheeks pressed tightly against my lower abdomen, her anal tunnel clasping tightly to my pulsing cock, my balls nuzzled humidly against her dripping cunt. Her calves, clenching against the outsides of my legs, were trembling in a way that I'd come to learn meant that she was cumming.

As her lips made first contact with Jenny's pussy, Jenny's eyes rolled into the back of her head. It was a reaction more animalistic than she'd ever had with me. At first, I took it personally, but quickly rationalized it was the four cocktails and the incredibly naughty nature of what we were doing that caused her to react that way.

Convinced now that all three of us were one hundred percent on board, comfortable and turned on by what was happening, I fully gave myself to the experience. I spanked Kathryn's ass and criticized her for being such a bad babysitter, an action that elicited a deep moan that was muffled by my wife's cunt. Those vibrations seemed to work wonders for her, as Jenny let out a squeal and grabbed the back of Kathryn's head, holding her tighter.

For several minutes, it went on like this. I got more aggressive with my thrusting, but Kathryn never stopped licking my wife. If anything, she licked faster and plunged deeper. Jenny was writhing on the pillow, clearly on the verge of climax. She humped her hips up towards Kathryn's mouth as we used her like a sex doll.

I could make out Jenny's labia parting around Kathryn's lips as she explored her depths. As far as I knew, this was Kathryn's first time eating out a woman, but she sure wasn't being shy about it. She seemed intoxicated not just from the gin, but from the scent of Jenny's womanhood. Her nostrils were flush with pubes, but he still inhaled deeply to take it all in.

The room was filled with the sounds of sex. My thighs slapping against Kathryn's, her ass getting spanked, the wet, sloppy sound of cunnilingus, and impassioned moans and whines from all three of us. But before any of us came, Kathryn backed away from Jenny.

"Daddy, you said you were going to punish both of us. I think your wife is getting off easy."

I came to rest with my cock at full hilt inside her ass and looked at Jenny with an eyebrow raised.

"Well, honey? She's not wrong."

Jenny was flustered from being so close to cumming. Red in the face and hair plastered to her forehead, she said, "I...I don't have a specific punishment in mind."

"I think he should fuck your ass, too, babe. We're equally to blame here," Kathryn said.

Jenny looked like she was actually considering it, but objected at first.

"Oh...I...I...don't think I could do...that..." It sounded like she was actually worried about offending Kathryn for having just taken it up the ass, and it was ironically adorable that she was thinking of her.

"Daddy," Kathryn started, "Give me that Scotch, please. Jenny, roll over onto your stomach real quick."

Having no idea what she had in mind, I reluctantly backed out and retrieved the remnants of my drink. A few dwindling ice cubes rattled as I brought her the glass.

By the time I returned, the women had rearranged. Kathryn had move back to allow Jenny more space, and Jenny had turned onto her stomach, her ass directly in Kathryn's vicinity.

"I've never tried this before, so let me know if it's uncomfortable. Might be a little bit weird at first, OK?"

Jenny nodded in response.

Kathryn then gently opened Jenny's ass and started tonguing her asshole. Jenny had appeared tense until that moment, probably thinking that Kathryn was going to start with a finger. But the tongue eased her concerns and she gave into it immediately. I stood off to the side and watched them in awe. I couldn't believe that it had come to this, and that everyone was so willing; that, if anything, it was all Jenny's idea!

Jenny was moaning as if she was getting a massage. Occasionally, her legs would spasm when Kathryn flicked one particular spot or another, but undeniable pleasure had appeared on her face.

It was at this point that Kathryn picked things up a bit. She removed an ice cube from the Scotch and, positioning it at her finger tips, brought it to Jenny's sphincter. Jenny gasped at the unexpectedly firm, cold intrusion, which contrasted so starkly from Jenny's tongue. But once she realized it was ice, she settled back down.

Kathryn rubbed the ice around the perimeter of Jenny's tight hole, teasing it open and numbing it. She alternated between that technique and using her tongue, lapping at the peaty smokiness that enhanced Jenny's musk.

"She's super wet, daddy. And not just from the ice cube," Kathryn said as she turned to wink at me. I was stroking my cock to keep it primed, not that the scene alone wasn't stimulating enough.

"Is that true, baby? You like what she's doing to your ass?"

Jenny couldn't verbalize a response, but nodded eagerly as she pushed her ass back towards the sensations. Believing her to be ready, Kathryn then slipped the rest of the ice cube inside Jenny's ass. By that point, it had melted to about half the width of my pinky, so it slipped in easily. Jenny barely reacted.

Kathryn grabbed a second cube and repeated the process. The room smelled of Scotch, or maybe that was just from my hyper concentration on the scene in front of me. Jenny had her head resting on her forearms, as if she was completely at ease with this entry-level penetration.

This time, when Jenny worked the second cube inside her, she followed it with her forefinger, pushing it several inches deeper. Here, too, Jenny didn't react too much. The ice had numbed her to the point that she was ready for something bigger. And I was happy to oblige.

Kathryn stood up and moved to the other side of the bed, standing in front of Jenny. I disturbed Jenny's peacefulness by pulled her back so that her ass was closer to the edge of the bed. As I eyed my new target, Kathryn climbed in front of her and spread her legs.

"Come on, baby. Time to return the favor."

Without awaiting affirmation, Kathryn slid forward and planted her pussy on Jenny's lips. At the same time, I started easing my cock into my wife's ass. Not once, in our entire dating or married history, had I ever asked for this. She had never offered, either. We were completely content with vaginal intercourse. But now that I was on the cusp, there was nothing I wanted more.

As my head snuck past her sphincter, I experienced a completely new sensation. The melted ice had pooled just beneath the surface, and as my cock plunged into it, the water displaced and enrobed my cock. It was frigid but stimulating. It took me a few seconds to realize that Jenny hadn't even reacted to the penetration. She was devouring Kathryn's pussy like she hadn't eaten in weeks and was sustaining only on her sweet nectar. It wasn't until I was a few inches deep that I felt any resistance from her ass.

Kathryn repeated Jenny's gesture for earlier, cupping the back of her head and holding her flush. She and I exchanged a glance, and she smiled with a shrug, as if to say "I didn't plan this, but I sure am enjoying it!" I shrugged back, still stunned at how the evening was turning out.

When I bottomed out in Jenny, I felt the familiar sucking sensation, and it caused me to lurch forward. I planted my hands on either side of her, propping myself up on the mattress as I continued to pump in and out. Jenny was making muted meows as she broke two sexual barriers at once. At least, to my knowledge she'd never gone so far to give oral to any of those sorority gals. At this point, I was starting to wonder.

"Fuck, I'm gonna cum," I grunted, unable to hold out any longer. You'd think I'd have built up more stamina over the last couple days, but each ensuing day resulted in a more erotically charged scenario. Never in a million years would I have imagined fucking my wife's ass while she ate out my side lover, with all parties not only consenting but eagerly encouraging each other.

"I'm coming, too!" Kathryn yelled. Her chest was heaving rapidly Jenny brought her to orgasm.

Not wanting my wife to be left out, I worked my left hand beneath her and started frigging her clit. Stiff and slathered in her own juices, it responded immediately, bringing Jenny over the edge.

Within 15 seconds of Kathryn's cum, Jenny and I followed suit. I emptied myself deep inside her, relishing the feeling of her tight tunnel squeezing out every last drop. Reluctantly, I backed out and lay on my back. Jenny, too, turned onto her back and scooched between Kathryn and me. Unprompted, Jenny started giggling uncontrollably. It proved to be contagious, as Kathryn matched her. I chuckled a few times, too, but quickly nodded off to sleep. The alcohol, exertion and mental strain had proved too much for my feeble brain.

.....

I awoke to the incredible sensation of a wet mouth slathering my cock. It had been ages since Jenny had woken me up this way. It was surprising not because it's always surprising, but because she was doing it the morning after my cock had been in her ass. And to the best of my memory, I hadn't washed yet.

"Hey there, sleepy head," she said as she continued to stroke my cock with her hand. "I have to head out in half an hour, but I wanted to milk this for all its worth.

She kissed the tip of my head, then added, "No pun intended."

I groaned and gently rocked my hips up to meet her mouth. Excited to have turned me on, she went deeper and deeper. It turned out to be the best blow job she'd ever given me, and I finished shortly after waking.

Jenny crawled up and laid her head on my chest. "Are you OK?" she asked.

"I mean, I'm still processing, but yeah, I think I'm OK. No question last night was incredible. Did you have fun?"

"We went a lot farther than I had anticipated, but yes. I absolutely loved it. Honestly, it was just what I needed."

"Well, if you're OK, than I'm definitely OK."

"Are you concerned about going back to worth with Kathryn? I know you don't see each other that much, but it's inevitable that you would run into each other at some point."

"No, I don't think so. After all, she's married, too. She's not going to tell anyone. And as much as I'd love to shout it from the rooftops, neither am I." This was the same logic Kathryn had offered that first night in the conference room.

Jenny kissed my chest. "OK, I should get dressed and to the train station."

"I'm going to jump in the shower. See you tonight?"

"I can't wait."

.....

As with yesterday morning, Jenny was late to breakfast, and ended up eating a scone on the walk to the convention center. The final day of the show ended at 1pm, but we had both already exceeded sales expectations, so we weren't likely to stay that long. It was more obligatory that we show up for a few hours to schmooze. It wasn't until we were on the train home that we had a moment to talk.