Unexpected Anal Office Tryst Ch. 05

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The first day of the convention proved to be a rollicking success. Kathryn and I split up to hit as many customers as possible and ended up generating enough sales that…you know, never mind. You’re not here to read about our sales strategies.

By late afternoon as day one was winding down, I started to get butterflies in my stomach. Being the referee in a blow job competition had been lingering in the back of my mind all day, but with it just hours away, it had forced its way to the front. My illicit liaisons with Kathryn had been so entrenched in my way of life that I was no longer worried about getting caught. I was worried about performing. What if Amber and Kathryn combined to be an intimidating duo, and I shrunk in the spotlight?

Oddly, I felt pressure to perform not just for myself, but for Kathryn. This seemed to mean a lot to her. It was a way to prove herself to her friend. I didn’t want Amber to think Kathryn’s super naughty affair was with some lame, limp dick chump. I wanted Amber to know that Kathryn had been one-upping her with a bonafide cocksman, capable of bringing even the most experienced woman to her knees in orgasmic bliss.

When Kathryn and I met at the elevators, I sensed she was experiencing similar trepidation. Alone on our ride to the 17th floor, she grabbed my arm with her trembling hand. Her head was tilted towards the floor but in my direction, and she spoke in a hushed tone.

“I’m nervous,” she said. I watched her in the reflective metallic sheen that covered the elevator doors.

“Me too. But are you nervous, or are you scared?”

Her head fell sweetly against my shoulder.

“How do you distinguish those in a moment like this?” she asked.

“Nervous as in you’re nervous that you won’t perform, or that you’ll be intimidated and chicken out. In that sense, I’m nervous. Scared is: you’re scared that by letting Amber into our liaison, she might out you to Jeremy.”

She seemed to perk up at that suggestion. “Oh, no, I’m not scared, then. Amber is 100% trustworthy. But I’m definitely nervous the way you defined it. I feel like this is my opportunity to impress a friend; to convince her that I’m not some sexual noob…that I don’t take myself so seriously all the time. But she’s so open about her sexuality, I’m worried I’ll relapse to the woman I was before we got together. I don’t know why.”

It was endearing to see Kathryn like this. I almost forgot about her timid side, which hadn’t been apparent since our very first tryst in the conference room two months ago. Since then, she’d been take-charge, get-what-I-want Kathryn.

The doors opened and we walked to our adjacent rooms.

“Look,” I said as we got to her door. “I’m the one who should be nervous. Do you have any idea how hard it will be for me to ‘perform’ for two beautiful women? You’ve definitely helped improve my performance, but this is a tall task. I’m putting pressure on myself to perform, because I want Amber to be jealous of the man you’ve been fucking.”

Kathryn let out a muffled laugh. “You’re sweet,” she said, smiling.

“It sounds like Amber is more experienced than either of us, but she also sounds loving and trustworthy. If I can’t perform, or if she wins, or whatever happens, it’s not like she’s going to belittle us, right? She’ll probably help us, the way you describe her.”

“That’s true.”

“And besides, no matter what happens, I’m going to say you were better.”

Kathryn laughed again. “Thanks, but I don’t think we’ll have to take your word for it. There are more obvious ways to determine who gets you off better.”

It was my turn to laugh.

“Ha, you’re probably right. Well listen: she’ll be here in about an hour, right? I’m going to shower and brace myself mentally for anything that might come up tonight. You should get ready, too. After she arrives, talk with her about boundaries. If anything doesn’t seem right to you, just tell her I bailed, and you two can go have some drinks together. Otherwise, I’ll be ready whenever you beckon.”

Kathryn stood on her toes to kiss me flush on the lips.

“Thank you. I feel very safe with you, and that gives me more confidence. I feel better about tonight already. Thank you for reminding me what a good man you are. I guess, more than anything, I’m worried you’ll want Amber more than me after tonight.”

At that, I let out an uproarious yawp. “That, Kathryn, is not possible. Are you kidding? I love what we have because we share it exclusively with each other. We’ll just be two more people Amber has slept with.” I lowered my voice as I offered more detail. “But you and I are each other’s one and only affair. Each other’s one and only anal. Amber means nothing to me beyond the fact that she means something to you, and I promise that will be the fact after tonight.”

Kathryn smiled in a way that reminded me of all the things I love about her. I seem to have said the right things.

“Thank you, Henry. I’m confident again. Go get ready. I’m going to suck your brains out in an hour.”

We went to pendik escort bayan our separate rooms, and I immediately stripped down for a shower. As the hot water cascaded over the back of my head and steam enveloped me, it dawned on me that I hadn’t considered all the possible hiccups tonight. Not only could I potentially underperform, but I could perform too quickly. What if I was so overcome by the sight of two beautiful women servicing my cock that I came in 5 minutes? That would certainly put a damper on things.

Wanting to prevent that possibility, I rubbed one out right there in the shower. I envisioned Kathryn’s eyes looking up at mine as she wrapped her lips around my scrotum. As she flicked her tongue around my balls, Amber bobbed her head up and down my iron erection. I realized in that moment that I had no idea what Amber looked like. Kathryn hadn’t shown me a picture, nor had she described her. In my head, it was a faceless mouth moving back and forth, occasionally obstructing my view of Kathryn. Then, as I got close to cumming, I put my hands on the backs of each of their hands and pulled them closer, allowing me to deposit my load right down Amber’s throat.

I shot my sperm onto the glass wall of the shower, then directed the showerhead towards it to wash it away. I still had plenty of time to recuperate, but I’ll have cum recently enough that I won’t blow my load five minutes after dropping my pants. I toweled off and wrapped myself in the provided robe before pouring myself a Scotch.

I sat on the couch and stared at the serene Philadelphia skyline, with City Hall’s clock tower front and center. It was a pleasing view, and one that enabled me to mediate a bit. I wanted to think about tomorrow night, when a whole new pressure situation would arise. Jenny was coming to let loose, whatever she meant by that. I needed to perform there, too. But I needed to take things one night at a time. Kathryn and Amber would demand my attention soon enough.

A knocking at Kathryn’s room disrupted my serenity. I could barely make out Kathryn’s footsteps as she made her way to the door, but the sound of the door unlocking and swinging open was much more obvious. There was a brief pause where I heard nothing, followed by a jovial shriek that can only be described as two best friends preparing for a wild night.

When the door closed, I could only hear excited murmurs, but couldn’t distinguish any language clearly. I downed my Scotch and used the glass as an amplifier, placing it against the wall with my ear snug against the other end. The rudimentary solution proved to be rather effective, but I could still only make out bits of conversation.

“Girl, I’ve been wanting to do this with you for, like, forever!”

“You look nervous. Are you sure you want to do this?”

“What did you bring all this for? It’s just blow jobs.”

“Sometimes BJs lead to more. And I might only have one chance at this, so I want to be prepared!”

“You’re crazy!”

“I love you so much. I just want this to be fun for everyone.”

After a moment where it sounded like their conversation died off, I received a message on my phone from Kathryn. She said to come over in ten minutes. I heard what seemed to be like more prodding from Amber, and then they shuffled out of the room adjacent to mine.

The following ten minutes were the most anxious of my life. I stroked my cock a bit to bring it back to life, wanting to make sure that it was ready to go. Once it was firmly halfway, I rewrapped the robe and headed next door.

Kathryn answered the door in her customary fashion: adorned in her fluffy white robe, and with a piercing, suggestive stare. I was anxious to see what Amber looked like, but I didn’t want to disrespect Kathryn by looking beyond her, so I kept my eyes locked on hers.

“Come in,” she said, opening the door further and stepping aside. As I moved past her, I smelled a hint of tequila on her breath. A then saw the half-consumed bottle on the drawer, with two glasses still partially full.

I stepped further inside, and Kathryn took my hand to guide me towards the main room. Amber’s feet came into view first, with her right leg crossed over her left. Two more steps and I could take her in completely. She had many striking features, but what captivated me most was her hair, which matched her name. It contrasted smartly with the light blue lingerie she was wearing. A cup-less bra framed her breasts, which were noticeably larger than Kathryn’s, and the matching garter belt perfectly accentuated her slim waist. She was leaning back with her hands braced on the bed behind her. By the pillows, there was a large purse that I presumed to be hers.

She and Kathryn were a study in contrasts. Where Kathryn had a tight yoga body, Amber had a bit more weight on her, but it sat on her in all the right places. Whereas Kathryn — even at 38 — had a girl-next-door cuteness, Amber was a voluptuous sex goddess. Kathryn: demure. Amber: oozing sexuality.

“You must be Henry,” she said.

“And you maltepe escort must be Amber.”

She turned to Kathryn. “Well done, honey. He’s very handsome!”

I heard a gentle thud and turned to realize that it was Kathryn’s robe hitting the floor. She was wearing the same set of lingerie, but in green.

“I told you,” she replied, approaching me and reaching for the belt of my robe.

“And Kathryn’s told me a lot about you,” I said to Amber.

Amber bobbed her right foot up and down, still swinging over her left leg. “I assume, as always, she demonstrated her penchant for hyperbole.”

“I can’t say for sure, but it was all flattering. You two clearly have a very special bond.”

“Be that as it may, I think Kathryn’s imagination sometimes gets the best of her when it comes to my sexual past. For instance, after she explained her — your — unique, anal-only arrangement, she was surprised to learn that I’ve never taken it up the butt.”

“To be honest, given what she’s said about you, I am a bit surprised by that, too.”

“That’s what I thought,” Amber went on. “The idea never appealed to me, and honestly, a few guys asked, but they were more than happy to get with the rest of this,” she said as she gestured to her entire form.

“That said,” she continued, “Based on what Kathryn has told me about it — or at least, how you do it, – I’m a bit more curious now.”

Kathryn took over the conversation from here. “We decided to up the ante a bit. If I win the competition, you get to take Amber’s anal virginity. But if she wins, I have to do whatever she says for the rest of the night.”


“I can get on board with that,” I said. “It’s a bit awkward to talk about it so bluntly, but you both just go down on me and I say who gives better head?”

Amber scoffed.

“Ha. I love Kathryn, but I don’t trust her that much!” She arose and ventured to the purse behind her. Reaching in, she pulled out a few items, laying them out on the bed for dramatic effect. A Hitachi Magic Wand, two pairs of leather cuffs, a strap-on dildo, and finally, a blindfold.

“There’s no way for me to know if you two are in cahoots, so I thought long and hard about how we could do this fairly. Kathryn agreed to this before you arrived, but I think you’ll like it, too.”

As she spoke, she locked herself into the cuffs. She then approached me and held them up to me for inspection.

“Look,” she said, pulling at the clasp between them. “With just a little force, they snap apart, so it’s nothing you can’t escape if you ever want to.” She pulled hard and her wrists easily separated.

She continued. “You sit on the chair, and we cuff each of your wrists to the arm rests. Then, we blindfold you so you can’t know for sure who is blowing you. Kathryn and I take turns, one minute at a time. Whoever gets you to blow, wins.”

I looked at Kathryn for reassurance. This isn’t exactly how I envisioned it, nor was it the double blow job I had been fantasizing about since agreeing to this. But it did still sound fun. And the cuffs were easily escapable, should things get weird. Kathryn smiled and nodded.

“It will be OK,” she said.

Not waiting for my confirmation, she pulled open my robe to expose my naked form.

“Wow!” Amber said when she saw my dick. “Again, Kathryn: nice job. It’s not even erect and I’m already impressed you could fit that up you butthole.”

We both blushed at that.

I was transfixed as these two, beautiful, lingerie-clad women each took a shoulder and pushed me down into the desk chair and cuffed me to the armrests. Before blindfolding me, Amber made one final adjustment. She pulled Kathryn’s hair back and tied it into a ponytail, before repeating the process on herself. It was awe-inspiring watching her breasts jut out and jiggle as she reached behind her head to finagle her hair. She was the classic depiction of beauty, here to suck my cock.

“Don’t want our hair giving us away,” she said by way of explanation. It was true, her hair was probably eight or nine inches longer than Kathryn’s and I probably would have felt the difference on my thighs.

“Ready, baby?” Kathryn said as she approached with the blindfold.

“Ready as I’ll ever be.”

A second later, all was black. I heard some scuffling, and tried to envision Amber and Kathryn deciding who would go first. I then sensed one of them approach and kneel before me, a touch of skin against my inner knee being the first contact.

And then it began.

A lush, warm tongue pressed against the top of my cock head, which, being semi erect, was still drooping towards the floor. My whole body flinched as my dick sprung to attention. In an instant I was a bit harder and pointing up slightly, and whoever was before me took the entire head into her mouth.

It felt unfamiliar, both in technique and form. This tongue was fuller and wetter than what I had experienced recently with Kathryn, so I made a mental note that Amber was going first. Thing was: I didn’t know who I kartal escort wanted to win. Would it be fun to take Amber’s virgin asshole? Sure. But there was a part of me that wanted to keep the anal fucking to just me and Kathryn, each other’s one-and-only anal. At the same time, it would be exciting to see Kathryn serve as Amber’s sexual slave for the night. But I also wanted Kathryn to win for her own self confidence.

Caught up in the mental maelstrom, I decided both options had pros and cons, and I should just allow myself to enjoy the moment. Most guys would kill to be in my spot. Last thing I wanted to do was ruin it for myself.

As I was lost in thought, the first minute elapsed and Amber (I think) dislodged from my still-hardening cock. It proved to be a good idea that I had masturbated before coming over here, otherwise I wouldn’t have lasted too long. Now, it was going to take the women at least a turn each to get me fully hard.

Or so I thought.

The next mouth closed around me and I immediately recognized the sensations. Kathryn flicked her tongue against the underside of my head in a similar manner to how she had done the previous day, as if to provide a hint that she was now before me. Then, to drill the point home, she lowered my cock so it was parallel to the floor and slid it all the way to the back of her mouth. I felt her try to force it into her throat, and her gagging ministrations triggered something in my psyche that got me instantly hard.

Following a quick moment where she repositioned herself, she pushed forward and overcame the tight barrier. Her throat clamped down tightly around me, her lips murmuring against my base. Fuck, she was good at this!

But as soon as she got into a rhythm, she had to back away, leaving my cock twitching with excitement and bobbing in the cool, conditioned air.

Amber, I was now certain, replaced her and upped the ante. Using only her mouth, she lifted my cock and slid her face below it to suckle my scrotum. She nuzzled it lovingly, sucking it into her mouth and dancing her tongue between them. But she clearly didn’t want to spend too much time down there, as it would take longer to get me off that way. So halfway through her turn, my balls fell out of her mouth with a plop and she returned to my shaft, which was now fully erect and ready to blow.

She worked harder this time, moving halfway down before returning to the head, and repeating this as quickly as she could. While Kathryn’s deep throat was tighter and more mentally stimulating, it’s hard to compete with the effect of focusing on the head, and Amber certainly knew how to do that.

I was probably a good 15-20 strokes away from blowing, but time ran out and Amber obediently backed away. If Kathryn had been faster about replacing Amber, she probably could have maintained the momentum and finished me off. Unfortunately for her, it took a bit too long, and she needed to build it back up.

Her dainty mouth fluttered over my cock, quickly bringing me to the cusp. It seemed that she was now trying to replicate Amber’s technique, having seen the effect it had on me. But Amber was more skilled at this method, and while I certainly found it enjoyable, she was unable to get me off before her minute was up. She was close, though, and for the first time since I was blindfolded, I made a sound.

“Uuuugghhhhh,” I groaned in frustration as Kathryn dislodged. She was mere second away from winning, and I was craving release.

Amber eagerly replaced Kathryn and took me into her mouth. Unlike the last transition, she didn’t waste any time and quickly had me on edge. Amber seemed to sense it, too, because she actually paused for a minute to gloat.

“Sorry, baby,” she said. “I think I won this round.”

She returned her attention to my head and sucked hard. I felt drool sliding down my shaft towards my balls, then dripping off onto the floor. I felt her silky soft lips working wonders on the top of my cock. There was no preventing it. My arms strained as far as the cuffs would allow them and I slid forward in my seat as my orgasm hit.

Amber made a giddy victory sound as the first shot landed on her tongue. She continued sucking hard until I had completely drained myself inside of her. I slumped forward, breathing heavily as my cock fell out of her mouth. Amber giggled again, unmuffled this time, and I could hear her elaborately smacking her lips, indicating how tasty she thought my cum was.

I knew Amber had won, but I feigned ignorance. “Before you tell me who won, I just want to say that it was incredibly close. Whoever went right before this would have won if she had five more seconds. And the same is true for the round before that.”

In a flash, my blindfold was removed and my eyes blinked rapidly as the light flooded them. Amber was standing there with her hips cocked, and a finger still in her mouth from scooping up cum.

“That’s sweet, babe. But it looks like you won’t be fucking my ass tonight.”

I looked behind her to Kathryn, who was standing there with a look of fake anger on her face. Almost the McKayla Maroney “not amused” face, but with a hint of smile creeping up the sides of her lips. I was relieved that she wasn’t too devastated by the loss. Amber rose from her knees and sexily strode over to her.

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