Chapter 3

For the next couple weeks it became a delightfully familiar thing, Emily sleeping with me. She moved in.

During those two weeks we made arrangements for us leaving, since the class would be in Denver. Not sure if it would be permanent, Emily treated it like it was, although she had little that would change. Mostly she had a roommate, a gay young man, a fellow genius, who couldn’t afford their nice apartment in the upper eastside without her help.

I decided to kill two birds with one stone. A former student of mine from my first class who would sometimes substitute for me when I needed him, to whom I managed to break through his nerd shell, revealing a casual and cool guy that everyone seemed to like, agreed to take over the program. Since he was as good at recruiting as I was, having pulled together small groups of fellow nerds to establish successful computer based companies, then moving on, profiting from the sales but also making sure the companies sustained under a new boss, his third time just completed, he might even keep the program going if I permanently left him to it. He was also gay and never found any lasting relationship.

So I did some matchmaking, inviting Emily’s roommate and the man taking over for me on a double date.

“It has to be the Bistro!” Emily insisted. “We can flirt with Ariana, put sex in the air.”

It turned out not to be necessary. Emily’s roommate had a crush on the new man in charge, the man had thought the roommate cute if a bit too young. No longer. Once the roommate got over the stutters, they connected, forgetting about any company sharing their table.

Not surprising, Ariana joined us that night, and since we arranged it at dinner, Emily decided to stop at a sex shop.

“Oh my,” Ariana reacted to the purchase.

“You were worried Joe would be too big,” Emily explained.

The surprise came later. When Ariana buzzed, I let her know via the intercom the door would be unlocked, and, with the drapes closed, I returned to Emily, to whom I’d been feasting on while she sat in the armchair to a couple big climaxes, and she lay, front down, awaiting my cock.

I loved gazing at her when we made love, often just sitting with her straddling my lap, rocking gently for many minutes until we both finally needed more and I’d lift her and settle her onto her back still inside her and we’d go at it wildly, fucking more than making love. It usually happened after she sucked me off, changing places because I’d knelt like her between thighs lapping until she came, and after clearing her pallet with a close by drink, wine usually, she’d return to my flaccid penis and get me hard again before straddling until we changed to me above her fucking her hard and fast through at least one of her orgasms, and sometimes two, greeted by mine.

That said, having her amazing ass in front of me while I fucked her was definitely a close second in preference. Seeing me thrusting into Emily, hands grasping those wonderful cheeks, Ariana immediately stripped and moved her naked pussy for Emily to suck. “I washed at work,” Ariana let us know.

It may not have been Emily’s best cunnilingus what with a couple more orgasms distracting her, but somehow she managed to get Ariana off for the last one, possibly because of Ariana’s horniness or because she happened to latch onto Ariana’s clit, buzzing it with her moan, for the second cum, and I happened to join them as well.

Only then did we three naked people move things to the bedroom where the surprise awaited. A dildo significantly shorter and slimmer than my cock, and a harness to place it in.

Emily and I focused on our horny waitress, and since Emily got to taste her pretty quim first, I got the honors while Emily kissed her and eventually moved to suckling her nipples.

“Fuck me Joe!” Ariana moaned, edging close to climax.

“Ride me?” I asked.

“Okay.”

Emily handed her the condom to roll on, and once covered Ariana slowly descended. Then it got to the point when my glans tapped her cervix.

“Wait,” she said, lifting off my cock. “I want you fully inside me. I want you to fuck my ass Joe.”

“Me too,” Emily grinned. “Joe’s been craving to fuck my tight little butt.”

“Let me make you cum first,” I offered Ariana.

“Okay.”

“I’m going to get prepped,” Emily said.

“You sure?” I asked.

“Make love to her Joe.”

Which I did, stroking into Ariana slowly, missionary style, her legs high to gain distance so my cock didn’t go too deep, kissing her, tongues dancing together, before slurping at her nipples. “Rub yourself,” I told her, my thrusts quickening when she obeyed. Not long after I sawed into her orgasming cunt, helping sustain it.

“There’s an enema with your name on it,” said Emily when Ariana’s climax subsided.

“Okay,” Ariana responded.

“We’ll wait,” I said.

“You don’t have to.”

“But we want to,” Emily smiled.

“Okay.”

I pulled my erection from Ariana’s pussy and she slid off the bed, both Emily and I watching her firm round butt sway, tighten and loosen while she exited the bedroom.

We didn’t completely wait. Emily straddled my face and removed the condom to suck my cock. But neither of us worked aggressively, more sustaining a plateau.

After at least ten minutes, Ariana returned. I decided to go on attack, and Emily did like her audience. Ariana watched me bring Emily to orgasm, but also figured out the harness and attaching the dildo to it. After applying the KY as if masturbating, she moved behind Emily, kneeling at the head of the bed. I guided the fake cock into Emily’s pussy.

“I wish I could feel it,” said Ariana.

“Me too,” Emily agreed.

“Stroke her high,” I instructed.

“Could you bring the KY to me and stand in front of me?” Ariana asked.

I handed her the lube and stood where she wanted me. She brought my cock to her mouth and sucked. Squeezing out a dollop of KY, she coated her pointing and middle fingers with it and pushed them into Emily’s anus.

“Yes!” Emily exclaimed.

I watched Ariana’s fingers widen that smallest of holes.

“Squeeze some in my hand,” she said, bringing me the tube.

I did, and she stopped sucking, fisting me instead, slicking up my cock.

“Can you turn around underneath her?” I asked

“Okay.”

The two managed to shift down the bed a little while Ariana slipped underneath Emily. The faux cock came out and I guided it back in when Ariana took her position.

“Tell me if it hurts,” I asked Emily.

“Do it,” Emily insisted.

So I pushed through her sphincter, tight squeeze, but she must have relaxed because it was easier than I imagined. “Keep going,” Emily moaned.

God it was tight, but I managed to ease in. I noticed Ariana rubbing Emily’s clit while lifting into her and pulling her down, which affected my strokes, making them longer while I gradually went deeper. I also felt the dildo rubbing my already well stimulated cock.

“Oh fuck, so fucking much,” Emily growled, but not in the least like she wanted me to stop.

When I finally immersed myself fully in her bowels, pressing into her but not withdrawing, she murmured, “That it?”

“Yes.”

“Then fuck me, Joe.”

When I withdrew, her incredible ass, the one I was plunging deep inside, began moving. She began taking control of the double fucking. Ariana stayed with the pattern from below, creating greater impact when the two pelvises met. I on the other hand worked at a slightly slower pace, complicating the friction and the filling of her holes, and even when Emily sped up and I did too, I kept it a little slower. It was a weird kind of steady, but a steady that worked.

“Oh fuck. Oh fuck. Oh fuck,” Emily kept repeating at the pace that she bounced, which continued to speed up until it stopped and she stiffened and I sank deep, feeling the pulses of her pussy and the flutter of her sphincter pulled the cum right out of me surging into her bowels.

“God Joe so hot,” she growled, apparently feeling those spurts.

We showered before the next round, somehow all three of us fitting in the tub along with the dildo.

Once back in bed, Ariana said, “I want to taste you, Emily.” So they formed a sixty-nine, Ariana on top, and while they got each other off, I slicked up my cock and Ariana’s anus. “Do it Joe,” Ariana murmured, post orgasm. “Fuck my ass with that fucking monster cock.”

I moved behind her at the head of the bed. Emily reached for my cock and placed it at the small round opening, made bigger by my fingers but not all that much. Relaxed when I pushed past Ariana’s sphincter, it tightened immediately, and a sort of “woosh” sound came out of her mouth. While I waited for her to relax, Emily aided the effort by pushing three fingers into her and sucking her clit. A deep moan and a quivering sphincter followed with the relaxing needed and I pushed deeper.

Several careful thrusts later and I was fully in, no barriers to worry about, just friction which, though her moans and growls and her comments about being so fucking full told of the intense effect, she not only handled, but seemed to enjoy it, helped by her other hole being filled by all four fingers of Emily and Emily’s mouth continuing to work her clit. Neither Emily nor I fucked her fast, both keeping a steady, moderate speed, though like I did with Emily before, we kept a different pace, causing Ariana to be entirely full in both orifices sometimes, and nearly empty at others, but mostly somewhere in-between.

It didn’t last all that long, the intensity of it made for a powerful orgasm, but also the tightness for me finished me off not long after. Whether the throbs expanding her sphincter or the heat of the semen spurted into her bowels or both, but, post orgasm, Ariana definitely reacted. “God,” she growled, and she trembled both inside and out, achieving a second orgasm or her first reasserted itself. Whichever it was, it became too much, and she moved away from both Emily’s hand, Emily had already eased off the clit sucking, and from my cock, sliding out still mostly hard, the last of the spurts continuing, the first against her obscenely open asshole and the rest on her lower back, that bit of dimple from where her ass cheeks formed.

“I got some Epsom salts for the bath and some soothing cream for after,” Emily informed her.

“Sounds good,” Ariana barely replied.

“I’ll take care of it,” Emily volunteered, sliding from beneath our lover. “You guys cuddle.”

I moved down the bed so my head neared the foot of it and pulled a lank Ariana atop me. “You okay?” I asked.

She smiled and nodded, her face glowing with a blush, and she gently kissed me. Several kisses later, with her body, other than her head lifting to meet my mouth, relaxing more and more, Emily let us know, “Bath’s ready.”

Both had my big cock inside their too small butthole, so both needed the soothing bath. I sat on the covered toilet seat after cleaning my penis at the sink and watched the ladies clean and caress each other.

“You’re staying,” Emily said at one point.

“Okay,” Ariana smiled.

It was Friday. I think she planned to stay, but being invited was nicer.

We cuddled and slept after the bath and the applying of cream, and in the morning we made love, had a lovely breakfast and made love again before Ariana felt she needed to leave. We offered to accompany her to her apartment near Columbia and she accepted and we enjoyed the subway ride there. After each of us kissed her and promised a last date the night before we left, “Maybe without the anal,” Ariana suggested, to which Emily replied, “We’ll see,” Emily and I decided to stroll down Manhattan, eventually entering Central Park for much of it. It was a sweet day strolling with my love, the weather cooperating with a bit of Indian summer.

With Emily’s needs resolved with getting her roommate taken care of, probably with him moving into the fancy Park Avenue apartment of his new boyfriend, I still had things to handle. Mostly hurrying things along which meant taking more concentrated amount of meetings than I’d been accustomed, hooking up clients with students or ex-students, but also advancing and completing some advisory work I’d taken on significantly ahead of schedule, surprising and pleasing my clients.