Chapter 7

In the hour before Shelly arrived, I got a good amount of weed and various smoking implements ready. I remembered her preference for marijuana over cocaine. I also prepared an anal training station in the bedroom. I laid out three butt plugs, in order from small to large, along with Lelo lube, which I had found was ideal in keeping maximum lubrication without getting too messy. I also took out some cocaine and a medicine plunger, in case Shelly wanted to numb herself for the main event. I didn't know if Shelly had ever tried anal sex before, so I wanted to be prepared for the full range of possibilities.

I popped a bottle of Pinot Noir and sat down on the couch to await Shelly's arrival. My thoughts drifted to how things with Kat and Jess had evolved so quickly in the past couple weeks. They weren't kidding when they had made the decision to maximize hedonism. The tattoos, maybe more than anything else, indicated how serious they were about this. But also about us. A permanent mark, a constant and enduring reminder of our infinite commitment to each other. And their lives as escorts.

Escorts. I swirled and sipped the wine and considered this. These were two women I loved deeply. We had cultivated something honest and enduring, I firmly believed that. It was unique. It was debauched. It was ours. And it worked. Would it continue to work? Kat and Jess showed an undeniable zeal for this new, amped up lifestyle. I was fully on-board with it, but there were doubts that lurked in my mind. Doubts about safety, mostly. I knew Jess had cultivated a high-end clientele for her agency and a level of information-sharing that created a kind of mutual destruction scenario for the clients and escorts if they went beyond the rules. Still, prostitution came with inherent risks. Physical ones. Health ones. Legal ones. Nevertheless, those potentialities lurked in my mind shrouded in fog. The thrill of it, in part driven by those risks, made it even more delicious.

But one thing didn't sit right with me. The girls dictated the fun. Everything happening so far was on their terms. It wasn't their fault. I had been passive so far. I started wondering how I'd fill the time while they were out whoring around town. It wasn't something I had considered. The rapid change that came to our lives hadn't afforded me the time to prepare for it fully. As I did, however, it dawned on me how much freedom their work would give me. If they were out fucking for money? I could be left to my own devices. For the better part of five years, I had been singularly devoted to -- and fulfilled by -- my dual relationships with Kat and Jess.

Now, though, if I wanted to remain true to the "maximum hedonism" mantra we had instituted? Then I would need to find something for myself. I wasn't quite sure how to initiate it. Being the screener for Jess's whores was a good start, of course. Shelly would be a lot of fun to sample again. Part of me wanted something of my own. Maybe we would need more games, to raise the stakes by playing off one another. But maybe I'd also need to channel my old playboy bachelor self. With more money than I had ever dreamed of having, it could be delicious to see how much power it afforded me when it came to attracting the fairer sex. I immediately found myself drawn to the idea of discovering what women would do for a taste of this level of wealth. It settled in on me, and while I may have believed I didn't know how I would fill my alone time, subconsciously I knew it would be in pursuit of leveraging my money and lifestyle to get as much pussy as possible.

I was pouring a third glass of wine for myself, my thoughts already drifting into what avenues would be the best for finding new women to fuck, when the doorbell rang. It was Shelly, and she was right on time.

She stood nervously at the front door as I approached, tugging down the short, tight tube top dress she wore. The royal blue color flattered her gray eyes, which sparkled as I let her inside.

"Hey, stranger," I said and gave her a hug. "It's so great to see you."

"Hi, John," Shelly said. "You're right. It's been too long."

I guided her inside and to the great room sofas, noticing she walked a bit unsteadily in her tall heels. Her perfume was thick and cloying. Her luxurious brown hair teased like she was a pageant contestant. I detected a faint whiff of spearmint and wondered if she was chewing gum to hide her pre-game drinking.

"I have to say, this is a really pleasant surprise," I said.

She took out her gum and folded it into a tissue. "Jess said it was time my menu expanded," she said. Her voice was definitely unsteady.

"Don't worry about business," I said. "You're here as a friend."

Shelly laughed. "A friend with very specific tasks to accomplish," she said. I saw her eyes glance over the weed on the coffee table.

"Why don't we smoke, and you can tell me about it," I suggested.

"I would love that," she said.

I let Shelly take the lead. We went outside, and she packed a bong with bud. A few rips in, and she opened up.

"Football season is coming up," she said. "Johnny Burris made it clear to Jess that he wants me at all the post-game parties."

I nodded. This wasn't new information to me.

"And?" I said.

"He made it clear that anal needs to be on the menu," she said. "And Jess said so, too."

"So you're going to be my new trainee?" I said.

"All the girls say you're the best," Shelly said with a smile.

"You seem nervous," I said. "If you don't want to do it, it makes me less comfortable with it."

She smiled and took another bong rip. "You're too nice," she said as she exhaled a cloud of smoke. "A real gentleman."

I wasn't sure how to respond to that.

"Don't get me wrong," she continued. "I want to. I want the money that comes with it. I love the money. Jesus. But, like, does this make sense? I want to enjoy the things I have to do to get the money. I get it. It's a requirement. But I'm not the kind of person who can just put on a fake smile and say, okay, fuck my ass."

I laughed. "I get it," I said. "I totally get it. Have you tried it before?"

"Once," she said. "It hurt so bad I made him pull out as soon as he put it in."

"And when was that?" I asked.

"Years ago," she said. "In college with my boyfriend."

"Let me guess," I said. "No lube, and he didn't prepare you. Anal sex is not like regular sex."

Her bloodshot eyes lit up. "No! No lube!" she said. "Do you need it?"

"Oh, sweetie," I said, finally putting a hand on her thigh. "Let's start with a blank slate and pretend you never even tried that. Unless you've got an anatomy that simply won't accommodate anal? There's no reason it should hurt. It might be uncomfortable at times, but it shouldn't hurt if it's done right."

"For real?" she said.

The weed had kicked in, triggering my aggression when I was stoned. "For real," I repeated. "Do you want to find out?"

"Honestly, I do," she said. "I really think I want to find out."

Shelly was different from the other girls in Jess's agency. She gave off a more wholesome, innocent vibe. She wasn't as brazen and overt in her pursuit of lust. I think she liked being arm candy more than anything else, and she excelled at that. Her body was flawless, like a fitness model who retained all the curves of the sexiest cheerleader.

As it turned out, she also was an excellent student. It served as a timely reminder about what a powerful motivator money was when it came to some women, their bodies, and the access to those bodies certain financial incentives might give me.

We started with a lengthy oral session. I ate her out and mixed in an increasing amount of rimming her sweet ass. I was mesmerized by her supple skin and complete lack of tan lines. Shelly loved when I licked her asshole, and she pushed my head roughly between her cheeks as I tongued on it. When my face was dripping with her juices, and she seemed at ease with two fingers probing her ass, I decided it was time for toys.

I prepared her with some of the Lelo anal lubricant and took a slight risk. I skipped the smallest plug, which was smaller than the two fingers I had used on her already, and went straight for the medium. I instructed Shelly to do the same breathing regimen I had taught Rita in her first anal session. I ate her pussy some more while I worked the medium plug in and out of her ass. She was tight but showed no signs of discomfort. When she had her third orgasm of the night, I decided it was time for her to graduate to the largest and, finally, her ultimate test.

There was always something magnetically attractive to me about the mystery, trepidation, and anxiety in girls experiencing good anal sex for the first time. Accessing that forbidden hole never got old. Training a girl like Shelly to be paid to have her ass fucked? There was something primal inside of me that craved it and sought it out.

When it was time to use to the largest butt plug, I moved from between her legs to making out. I sucked Shelly's improbably pert, perfect natural tits on the way. Her lips were like pillows, since she had recently gotten fresh filler injections. It was the only enhancement she allowed herself. Her long eyelashes brushed against my eyelids while we made out. I maneuvered the plug into position by feel, spreading her phenomenally firm ass cheeks with one hand while gliding it past her sphincter until it nestled all the way inside. The whole time, I never took my lips off hers, our tongues dancing urgently.

Shelly pulled back and said, "Is it supposed to feel this good?" A wicked smile cracked across her face.

"If it's done right, it can," I said, returning the smile.

"Jess says guys pay a lot more for anal," Shelly said.

"At least a few hundred bucks," I said. "It's definitely worth a premium."

"Then I need to get good at it," she said.

"Are you ready to try it?" I asked.

"There's no reason to wait, is there?" she responded.

"Do you want some coke to help numb you up?" I asked.

"Like a booty bump?" she said. I nodded, and she said, "Yeah. I think that's a good idea."

I patted myself on the back for having the plunger prepared already and directed Shelly to get on her hands and knees. I injected the cocaine-and-water solution up her butt and, while we waited for it to fully take effect, had her suck my cock to get me ready.

It took almost no time for me to become fully erect. Shelly pulled her mouth off and said, "You know, when I first started sucking a lot of dick in college, I thought it was gross and weird. But guys liked it so much, I kept doing it and got good at it. And now it makes me so wet. I figure butt stuff is no different."

I positioned myself behind her and retorted, "Let's find out."

I coated my cock in lube, then pushed some inside her asshole with my fingers.

"God, it feels so different after the coke," she said. "It really did make me super numb. I'm flying right now!"

The lube and ample foreplay had done its job. My cock slipped past Shelly's sphincter easily, and she was adept at keeping up with my breathing instructions. The weed and coke seemed to make her very relaxed, and the large amount of lube made my cock fully penetrate her ass faster than I normally would have. Yet she didn't seem to mind in the least.

"How does it feel?" I asked.

"Different but good," she said.

I took that as my cue to fuck her ass. It was tight, and through the wine and weed, it took concentration to make sure my cock didn't just pop out of her tight hole during my strokes. Shelly got used to the anal penetration, and she started bucking her hips back into me. From her grunts and moans, I sensed she was enjoying it, so I increased the intensity. I grabbed her thick hair and tugged, eliciting a yelp from her but also forcing her ass deeper onto my cock.

"Do you like it up your ass, slut?" I growled.

"Fuck, I love it," she said. "I don't know if it's the coke, but it feels so fucking good."

"Imagine how much better it'll feel when you're getting paid for it," I said.

I used Shelly's hair to pull her back almost upright, grinding my cock into her asshole, then let go of my grip on her locks. I moved my hand to her throat and squeezed. She squealed delightedly, so I began aggressive upward thrusts into her while I gradually cut off more air flow. In only a couple minutes, Shelly burst into an incandescent orgasm that might have curled paint off the walls of the bedroom. She was furiously frigging her clit, and her ass gripped me so tightly, I had to stop thrusting in and out of her. It simply was too difficult and tight. But her climax carried on.

"Oh my fuck!" she said through heavy breaths. "What did you do to me? I've never. I've never cum like that before. Jesus. Fuck me. You fucker. What was that?"

"That was the moment you became an ass slut," I said, grinning.

"I want your cum," she said. There was an urgency in her voice that I didn't expect. "Put it up my ass. God, you have made me an ass slut. I'm going to cum again!"

Shelly's body seized up and shook, but this time her orgasm wasn't as intense, and the friction of my strokes in her anus created a superlative feeling that pushed me to the brink. I tweaked her nipples, which were like small walnuts and severely hard. I thought about how this would be the first load of cum Shelly had ever taken in her ass, and that gave me a joy that triggered my geyser of pleasure. We toppled over onto the bed, my cock embedded in her ass and twitching. A cooling sheen of sweat covered our naked bodies.