Unexpected Anal Office Tryst

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 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 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.”

Whoa.

“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 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.
“Sorry, babe. I know this meant a lot to you. But for what it’s worth, I think you’re the real winner here.”

Kathryn scoffed.

“No, seriously. This was such a hot idea, and it was all your idea! And for fucks sake, I never thought I’d see you deep throat a guy. If you were trying to prove yourself to me, consider yourself proven. I’m seriously impressed.”

Kathryn jokingly pushed her away. “Whatever, I still wanted to win. I really wanted to see you get fucked raw by my man.”

Amber tossed her hair over her shoulder and looked towards me. “Oh, I suspect I’m still going to get fucked raw. Just not in my ass. And not before I spend a little time with you first.”

Amber slipped the blindfold over Kathryn’s eyes and returned for my cuffs.

“Hands behind your back, babe,” she said to Kathryn before locking her wrists above her butt. Amber then escorted Kathryn closer to me, so that our knees were only about a foot apart. She stood behind Kathryn and held her tightly, her hands gliding sensuously over Kathryn’s tight abdomen and perky breasts. Amber planted a deep, lasting kiss on the nape of Kathryn’s neck before baring her teeth and giving her a gentle nibble.

Kathryn gasped. “Be careful,” she said. “Don’t leave anything lasting. I’ll be seeing Jeremy in two days.”

“Oooh,” Amber purred. “If only he could see you now.”

Kathryn flushed at this comment, but her hips still rocked forward as Amber’s touch ventured further south. Her fingers dipped below the hem line of Kathryn’s garter belt, then tickled their way through her small patch of pubic hair. I could make out the glimmer of Kathryn’s juices as they twinkled in the dim light. She was clearly wet and ready to go, and Amber was playing her like a fiddle.

Amber traversed the final inch before finding Kathryn’s pussy lips, and she supplely pulled them apart. Kathryn gasped again, knowing that she was exposed to me in a way I’d not yet seen before.

If it weren’t for Amber’s left arm wrapped around Kathryn’s torso, Kathryn would undoubtedly have tipped over. Off balance in the blindfold, delirious from her friend’s finger play, and ashamed of her infidelity, Kathryn was already on wobbly legs before Amber started stroking her clit. But now Amber was sliding up and down Kathryn’s slit, paying special attention to the nub at the top, and Kathryn was going weak in the knees.

“Hold still, babe,” Amber whispered in her ear with her eyes locked on mine. “We’re just getting started.”

Amber steadied Kathryn, then left her alone for a minute. From the bed, she grabbed the Hitachi and switched it on to its lowest setting. Then, bracing Kathryn with her left arm again, she placed the bulb of the wand just south of Kathryn’s bellybutton. Kathryn jumped again, her thighs pinching forward, her soaking cunt thrusting out towards me unwittingly.

“Have you ever used one of these before, babe?”

Kathryn could only shake her head in reply.

“Before the night is over, you’ll be buying one on the internet. Once you’ve used this, your fingers will never live up to it.”

She circled the wand closer to Kathryn’s pussy but intentionally avoided it, heightening her anticipation. The wand drifted below its eventual target, tracing Kathryn’s inner thighs. But as it neared contact with her outer lips, Amber jumped it back up to her pubes. Kathryn groaned in frustration, wanting this release badly.

“Please,” she whispered.

“Please what?” Amber asked, teasingly.

“Please touch my pussy. I want to feel it. I need to cum.”

Amber lowered the want to her clit and continued purring in her ear.

“That’s a good girl. The more obedient you are, the more you’ll enjoy this. I promise you. With respect to your side piece over there, I’m going to make sure you have the best cum of your life tonight.”

Kathryn swirled her hips in short but emphatic thrusts, pushing hard against the wand’s round head. She was smiling and squirming in Amber’s grasp.

“You know, Kath, for all these years, I thought you were looking on me with pity for hooking up with so many different guys. I never really imagined you would want to hook up with me yourself.”

Kathryn’s mouth hung open a bit, surprised at this revelation.

“It wasn’t pity, Amber…” a particularly effective pulse of the wand caused a shuttering breath… “it was envy.”

Now it was Amber’s turn to be surprised. “Well, that is a shame. What fun we could have had if we had just been a bit more honest with each other.”

Amber sunk lower, steering the wand between Kathryn’s blooming lips, and Kathryn clamped her legs tight around it. At that, Amber turned off the wand and removed it.

“Wha-” Kathryn got out, demonstrably shocked and disappointed.

“Spread your legs, honey. This isn’t just about you. We’re putting on a show for Henry, too. I want him to see what he’s missing.”

On shaky legs, Kathryn spread her legs about a foot apart.

“Wider,” Amber said.

Kathryn huffed and slid her right leg further to the right, until her feet were beyond shoulder length apart. As an immediate reward, Amber activated the wand and brought it back to her clit. Kathryn moaned in appreciation.

“Henry, I just have to know,” Amber said. “Does it pain you to not get to fuck this gorgeous, tight, wet pussy?” She delved deeper, causing Kathryn’s outer lips to envelope the head of the wand. “Look how delicious it is, Henry. Don’t you wish you could just bury your cock in here and feel its carnal heat polishing your knob? Wouldn’t you want to feel it suck the cum out of your balls?”

Kathryn went weak in the knees, to the point that she would have fallen if Amber weren’t bracing her. She was clearly enjoying the effects of both the wand and the dirty talk. I wanted to tell Amber that I’d experienced Kathryn’s pussy, and that it was as good as she described, but I didn’t want to betray our secret. I also didn’t want to pressure Kathryn into breaking one of our rules.

“To be honest, I’m quite content with her ass,” I said truthfully.

“Really? It’s that good?” Amber replied. “Let’s find out.”

To Kathryn’s great disappointment, Amber removed the wand and tossed it — still vibrating — on the bed. She moved Kathryn to the corner of the mattress and bent her over it, so that her legs were on either side of the corner, forcing them wider apart. With her hands still cuffed behind her back, Kathryn’s chest fell flat on the comforter, her head turned towards the ominous, vibrating Hitachi just inches from her face. Her legs, though spread, were perfectly straight, which allowed for a couple inches of separation between her throbbing pussy and the mattress.

Amber walked past her to retrieve the wand, tracing a fingernail over Kathryn’s ass as she did so.

“I won’t lie, Henry. I certainly see the attraction…especially from this angle,” she said.

Kathryn’s butt cheeks clenched a little as Amber picked up the wand. Amber noticed it, and shared a glance with me in amusement. “My, she is eager.”

Amber sat next to Kathryn on the bed, facing me. My view was of Amber’s luscious body, framed by her frilly lingerie but leaving nothing to the imagination. Next to her, Kathryn’s taut ass was exposed and prime for attention, while her pussy — oozing juices onto her inner thigh — gaped below it. I thought back to the number of times I admired her butt in a pair of tight slacks over the last eight years, and how lucky I was to have such a remarkable view before me now. Amber looped her right arm over Kathryn’s lower back, snaking her hand towards Kathryn’s pussy from below. With her left hand, she turned the wand up a notch and brought it directly to Kathryn’s puckered asshole.

“Ooooohhhh, fuuuuck!” Kathryn screamed, turning her face into the mattress to muffle herself.

I was enraptured by the scene before me. The Hitachi vibrated hard against Kathryn’s sphincter, which in turn caused a ripple of excitement through the rest of her ass. She was shaking uncontrollably against its power, and against the assault of Amber’s right hand. Amber’s fingers were spreading Kathryn’s cunt wide open, providing me with a view unlike anything I’d seen in person before. Kathryn was fully exposed and dripping wet, as evidenced by the glistening, pumping fingers penetrating her.

Amber turned the wand up to level three, then tactfully passed it down to her right hand, between Kathryn’s legs. After a moment of repositioning, she had the head of the wand on the mattress below Kathryn, who in turn bent her knees to press flush against it once more.

“Good girl,” Amber said as Kathryn humped furiously against the magical source of pleasure.

Amber moved her left hand up to Kathryn’s ass and pulled her right cheek to the side, exposing her winking hole to us both.

“I’m going to be honest, babe, I’ve never done this before. Let me know if I’m not doing it right.”

And with no more forewarning, Amber slid her pointer finger up Kathryn’s asshole to the first knuckle.

“Hhuuuhhhhffff,” Kathryn grunted at the intrusion, but did not offer a rebuttal.

“Holy shit,” Amber said. “It just sucked me right in!”

I was certainly familiar with that sensation. But Amber’s recognition of it stirred my cock back to life. As Amber worked more of her finger into Kathryn’s backside, my cock got harder and harder. Kathryn’s legs went from trembling to convulsing. Her knees bent, and her feet lifted off the floor as Amber’s masterful, orgasmic touch brought her closer to climax. She was squealing into the mattress as if it were the only sound she knew how to make.

With a final push, Amber worked her entire finger into Kathryn’s hole, and that’s what ultimately did it. Kathryn’s squealing stopped, and for a brief moment I was concerned that the wind had been knocked from her. Everything was dead silent, save for vibrator and Kathryn’s thighs sliding over the comforter. Her arms strained against the cuffs until the safety gave way, allowing her wrists freedom. She clasped the sheets tightly as the final few waves of pleasure rocked over her, her mouth turned to the side and hanging open in a silent scream.

Mercifully, Amber removed the wand and switched it off. Only now could Kathryn’s calves, still trembling, lower themselves to the floor. Amber removed her finger and stood, leaving Kathryn a motionless, sweaty heap pressed heavily into the mattress.

“Holy fuck!” Amber said. “That looked like a better cum than I’ve ever experienced!”

Kathryn seemed like she was trying to reply, but had forgotten how to speak. I rose from my chair so that I could see her face more clearly. There was a stain below her, possibly from drool. Her look was half dead-to-the-world, half cloud nine.

“Kathryn? Are you with us?” I asked.

Her eyes shifted up to meet mine, but her head didn’t move with them. Slowly, the rest of her features started to catch up. Her mouth closed and formed her classic, post-orgasmic smile. Her eyelids blinked a couple times. She relaxed her death grip on the sheets, and turned onto her back.

“Fuck, Amber. Fuck.” She clearly had a lot on her mind, and lacked the mental capacity to articulate it at the moment.

“I think she liked it,” Amber said.

“It’s safe to say she did,” I replied. “Almost too much. I thought she might have passed out!”

“Fuck, cumming so hard that I pass out remains an unattained life goal,” Amber laughed.

There was a moment of uncertainty when I thought the night’s festivities might have just concluded. The one thing convincing me otherwise was the presence of the strap-on still lying on the pillow above Kathryn.

“Do you have specific plans for that?” I asked Amber, gesturing towards it with my eyebrows.

“Oh yeah. Just waiting for this one to come to.”

Kathryn finally mustered the energy to sit up. She was positively glowing, from her forehead to her inner thighs, radiant from perspiration and her undeniable excitement.

“That was pretty amazing, babe. I don’t even know what to say.”

Amber lifted her face with a couple fingers under her chin.

“You don’t have to say anything, doll. You just need to keep doing what I say. Now, from what I understand, Henry here thought he was coming over to get sucked off by both of us at once. Let’s give him what he wants.”

Amber pulled my hand so that I was standing in between them, Kathryn sitting on the bed behind me, and Amber on her knees in front of me. I was semi-firm at this point, and Amber easily took in most of my length on the first go.

Kathryn stood and moved to come around next to Amber, but Amber stopped her.

“No, babe. Let’s give him something else. I want you to kneel behind him.”

Kathryn looked at me for approval, but who was I to protest? She had ventured back there with her tongue only once, and it felt pretty great. But I’m sure it would feel better with another mouth wrapped around my cock. Unless she was bitterly opposed, I was happy to experience this. I shrugged, indicating I was OK, and she simply responded, “OK, big boy.”

Kathryn knelt behind me and put her hands on both cheeks, pulling me apart. I was particularly happy that I had showered just before arriving, though I was sure I’d worked up a bit of sweat with all the activity so far. But if there was anything unappealing about it, Kathryn was undeterred. She dove right in and started tonguing my tight ring.

Amber, meanwhile, was bottoming out on my ever-hardening dick. I could feel the tip of my cock seeking entrance to her throat, and once I gained the inch or two I still had to grow, I would surely get there.

The sensations on both sides of me had me swaying back and forth, going up on my toes every time Kathryn prodded further. I had nothing to grab onto to keep my balance except for the women serving me, so that’s what I used. I placed a hand on the back of Amber’s head, then reached behind me to do the same with Kathryn. It was inadvertent, but I pulled them both tighter against me, causing some muffled responses, but no physical rebuttals.

After about a half minute with their mouths tightly pressed against — or wrapped around — me, Amber put her hands flat on my stomach and tried to push off. I immediately relented, not wanting to kill the mood, and Amber dislodged.

“You’re too big to pin me there, big man. I can’t breathe around your giant fucking slab.”

She was serious but lighthearted about it.

“Sorry, you two are just two effective. I was losing my balance.”

Amber rose to her feet. “Well, I’m sorry we were giving you too much pleasure! Here, let’s make it a little easier for you.”

She pushed me back on the bed, and Kathryn rose to stand next to her.

“Why don’t you ride him, babe. I really want to see how your tight little hole swallows that enormous fuck stick.”

“I thought you’d never ask,” Kathryn replied playfully. She practically jumped onto the bed, her legs landing on either side of mine. “I know it’s only been a day, but I’ve really missed this guy,” she said, referring more to my cock than to me.

She shifted her weight forward to make space, then, with a tight grip on my erection, positioned it at the entrance to her ass. The fingering Amber had given her earlier proved to be enough of a warmup. She easily eased herself down, lodging the first couple inches in place before there was even a modicum of resistance. I opened my mouth to grunt, but Kathryn was quicker, muffling my mouth with her own. What we were doing, without any room for argument, was wrong. We were both cheating on our spouses, and were doing so with the utmost pleasure and with no thought for the sins we were committing. Perhaps what pushed those sins out of mind was that there was, undoubtedly, love between us. Or at least some form of love. Perhaps it was infatuation. We were each other’s secret; each other’s vessel and source of the raunchiest sexual acts we’d ever committed.

Sharing that secret with a trustworthy friend only amplified those feelings. It was simultaneously risky and secure. Amber wasn’t going to betray us. Kathryn rode me fervently, working another centimeter up her ass every few seconds, while our lips kissed, licked and nibbled at each other like we were the other’s favorite meal.

Amber took a few playful whacks at Kathryn’s ass as it bounced on me, and that snapped Kathryn out of her kissing mood.

“Oh, you bitch!” she said, without a whiff of resentment.

“Oh, you deserve it, bitch!” Amber said. “Holding out on me all this time? Do you know how hot you look right now? We could have taken our town over if we had joined forces.”

She swatted her ass a couple more times. “Are you going to get it all in there, babe?”

I couldn’t be sure, but it felt like Kathryn still had about three or four inches to go before bottoming out. At Amber’s question, she paused. Closing her eyes, she seemed to be focusing her energy on something, but I wasn’t sure what. I was about to ask if she was OK, but then she set to action. In one determined motion, she sat all the way down on me, her butt coming to rest on my inner thighs. She took the rest of my cock straight up her anal chute, to the astonishment and cheer of Amber behind her.

“Holy fuck, babe! You’re a wonder!”

Kathryn had a proud grin on her face as she wiggled her butt at Amber. She was as tight as a condom, but infinitely more pleasurable. With subtle movements, she flexed her hips so that she could stimulate me more. She was only moving about an inch up and down, but that was enough. If I hadn’t already cum twice in the last hour, I undoubtedly would have erupted by now.

I closed my eyes and tilted my head back, savoring the sensation. Kathryn’s hands were on my chest, her pussy was teasing itself on my close-cut pubic hair, and her ass was squeezing me for all it was worth.

“It’s not too late to change your mind, babe,” she said to Amber. “I’m sure he’d fuck your ass if you let him. Best to learn with someone who knows how to do it.”

Amber chuckled. “I admit, you do make it look tempting, but I think I’m going to save my ass for my one, special guy. And while Henry performs like he could have been that guy, he’s your guy.”

As she spoke, I could hear her voice moving to the other side of the bed. When I opened my eyes to see what she was doing, I found her picking the strap-on off the pillow.

“Besides,” she said as she slid it up her legs. “I’ve got more fun planned for tonight.”

She moved back down to the foot of the bed. “Mmm,” she said as she admired Kathryn’s ass. “You know, my original plan was for you to ride him while I rode his face. I haven’t cum yet tonight, and I was really looking forward to testing Henry’s oral skills. You’ve said they’re excellent. But I didn’t want to break up your kissing. It looked so passionate and intense. I nearly got off just from seeing that. But it’s time for the grand finale now. I think we’ll all cum with what I have in mind.”

Amber instructed Kathryn to dismount and for us to lie in a spooning position. Once there, she ordered me to enter her ass again, which of course I was happy to do. Kathryn took me easily, her anal passage having loosened just a bit in the last ten minutes. I slowly moved in and out of her, which proved to be a bit of a workout for my abdomen. But it was easily the most motivating exercise of my life.

Amber then lay on the other side of Kathryn, facing her and cupping her cheeks. She moved in and locked lips, and Kathryn replied in kind. There seemed to be as much energy and passion in their kiss as there was in ours, and for a moment I was envious. I thrust a little harder to remind Kathryn that I was there, and the gesture broke their kiss for a moment.

“Oh, babe, he’s turned on by us kissing,” said Kathryn. “I just felt him swell up even more. It feels amazing.”

“Oh really, Henry? Does it turn you on to see two women kissing? How about this?”
She lowered her head to take Kathryn’s left nipple in her mouth. Kathryn gasped and immediately put a hand behind Amber’s head to hold her close. “Yes, baby,” she said.

I then felt a hand between Kathryn’s legs, and knew that Amber was stroking her pussy. The occasional fingertip grazed against the base of my cock as it slid in and out of Kathryn’s ass. Kathryn was clearly responding well to the overstimulation. She wasn’t only moving in rhythm with my cock, but with Amber’s nimble gestures towards her pussy and nipple.

Amber decided to test the waters a bit more, slowly inserting a finger into Kathryn’s clasping cunt.

“Mmmmmmph,” Kathryn emitted, welcoming the intrusion. She opened herself up further, turning her left leg akimbo and bending the knee so she could plant her foot on the mattress. Amber read her response perfectly, and pushed further by adding a second finger in short order.

Kathryn wasn’t the only one enjoying the sensation. I could feel the knuckles of both fingers sliding against the bottom of my cock from inside of Kathryn. It was surreal, but the effect was undeniable.

“Oh, fuck,” I grunted. “That feels fucking amazing!”

“We’re just getting started,” Amber said.

She removed her fingers and repositioned herself to be level with Kathryn again.

“Amber, please, go slow,” Kathryn said, her first sign of any trepidation that evening. “I don’t know if I can take both at once.”

“Don’t worry, sweetie. I wouldn’t hurt you.”

I knew exactly what was happening even though I couldn’t see clearly. I felt the head of Amber’s strap on fumbling around the entrance to Kathryn’s pussy, and I held still to give her an easier target. It was going to be incredibly tight, but Amber was insistent. The plastic head pushed forward at first, pressing somewhat painfully against the base of my cock even as it was lodged inside Kathryn. But once it popped in, it shifted north and ran parallel to my shaft.

“JESUS CHRIST!!!” Kathryn blasphemed.

“Holy fuck!” I yelled again.

Amber’s one movement had caused sensations unfamiliar to both of us. She clearly had only worked a couple inches inside, and then paused to allow us both time to grow accustomed to it.

Paradoxically, she contrasted this most extreme sexual act with a sweet, romantic gesture. She returned to Kathryn’s lips and they started making out again. In this moment, I felt like a human butt plug, there as a prop for two passionate lesbians. Not that I minded; it was quite the sight to behold. But it did feel like Kathryn had forgotten about me for a minute.

Without breaking their kiss, Amber shifted her hips forward and started working more of her cock into Kathryn’s ambrosial passage. Kathryn tensed with each passing inch, and she let out an increasingly high-pitched squeak the higher Amber went.

I, on the other hand, got deeper in my grunts as the ribbed rubber rod slid smoothly against my cock, separated only by a thin membrane inside Kathryn. At once, all the novelty of ass-fucking that had worn off over the course of our repeated trysts came flooding back. This was new territory for both Kathryn and me — and perhaps, also, for Amber — and that certain arousal that comes only with the taboo washed over us simultaneously.

Amber broke the kiss to scooch herself a bit closer. She then studied Kathryn’s strained and euphoric face as she pushed the last of her dildo inside. Kathryn sunk her head into Amber’s shoulder, biting her there as she neared orgasm.

“Yes!” Amber responded to the bite, clearly turned on by the impact she was having on Kathryn. Her eyes went wide and locked with mine. She was fiery, almost frightening in her glare. I soon realized this was how she looked as she approached her most raucous orgasms. She pulled Kathryn’s left leg around her so that it was hooking her own leg in place.

There was now no space between us. My belly pressed tight against Kathryn’s back, Kathryn’s and Amber’s bellies squished against each other. Their breasts mashed together, poking each other with erect nipples. Their lips locked again, their hands anxiously exploring each other’s faces and bodies.

The tight space did not allow much room for thrusting, but we didn’t need it. In all my life, I never imagined I would have been brought to orgasm by a dildo. But in all my life, I’d never imagined that a dildo would be pressed against the bottom of my cock inside a woman. The ridges of the pink cock stimulated my every inch. Combined with the heat and liquidity inside Kathryn, it proved to be too powerful for me.

“Fuck, I’m coming!” I shouted.

Kathryn and Amber both immediately replied, “ME TOOOO!!!!”

I reached past Kathryn to grab Amber’s back and pull her closer. My right arm, pinned underneath Kathryn’s neck, grasped for Amber’s shoulder. In our tight cocoon, we came simultaneously. My third orgasm of the night was powerful, even if the cum exploding from my cock was thinner than the previous two loads.

And distinct from my own pulsations, I could feel Kathryn’s loins contracting in orgasmic bliss. From the look on Amber’s face, her cum was equally powerful, her strap on having manipulated her clitoris in just the right way.

With each of us spent, we lay in that pile for who knows how long. Our arms were heavy and draped over each other, our legs slumped and interlaced. The arms we were lying on fell asleep at some point, which triggered us to move around and shake it off.

Amber gingerly pulled out of Kathryn, who seemed to deflate a bit without the two pillars inside of her anymore. We all rolled onto our backs, with Kathryn still between Amber and me.

“That was fucking amazing,” Kathryn said. “I’m so glad we did this.”

“Me too,” I said. “Amber, Kathryn needed to talk me into this, as I didn’t want to share our secret. But in this moment, it’s hard to say that it wasn’t worth the risk.”

Amber chuckled. “Henry, neither of you has to worry. Are you kidding? I would never betray this one. She’s my BFF, and I only feel that more powerfully now. I know Kathryn thinks I’m sometimes too easy to bed, but I can honestly say that was the most meaningful sex of my life.”

Kathryn turned to look at her. “Aww, really?”

Amber shrugged and nodded her head, locking eyes with Kathryn again.

I could tell they were sharing a moment, and thought that it might be a good time to excuse myself.

“I think I should get going,” I said. “Long day tomorrow and all.”

“It was nice to meet you, Henry. Thanks for tonight. Hope we can do it again sometime,” Amber offered.

I smiled and nodded. Slipping my robe back on, I nearly said, “see you tomorrow” to Kathryn. But that might have betrayed the white lie we were keeping from Amber, that Kathryn and I were coworkers.

I settled on “see you later,” then left for my room. As I closed the door behind me, I heard the sounds of lips smacking, and knew they were kissing again. I wondered how much longer they would go on without me.

Settling into my own bed, I was relieved to have survived the night with all parties happy. Now, for a good night’s sleep so I would have the energy to navigate tomorrow’s challenge: the arrival of my wife.