The Christmas in July Luau

"Well, I heard that the girls who work here are... like, escorts."

She looked me up and down some more.

"Tell me, Colleen honey, and be honest—how old was the oldest person you've had sex with?"

Was she just toying with me? I needed some clarifying statements here.

"Um, 25," I lied, "but I almost had sex with a man in his 40s. I mean, I wanted to."

"You'll be having sex with men, and couples—if you're interested—who are almost all between the ages of 40 and 65. Have you seen a man that old, naked?"

Holy shit. Holy fucking shit. It was real. It was so, so real. My pussy was dripping, and my mouth went bone dry. My heart was galloping. I was going to fucking do this.

"I mean, not up close in real life, but I've seen older men in porn."

She took a breath.

"So, those men are usually in great shape, I'm sure. These men are in... well, alright shape. We do have certain... standards, I think, but they're not going to look like that. I just want you to understand what you're thinking about getting yourself into, sweetie."

"I wanna do it," I said. "I think... I've wanted to do it for a long time."

I breathed out and she looked deep into my eyes, then spoke.

"You... want to fuck for us... for money."

"I want to fuck for you, for money. I really really want to, yeah. Yeah."

I closed my eyes and calmed my nerves, then opened them again.

"Yes," I said.

She shook my hand.

"Colleen, baby, welcome to D&V," she said.

I was on my way. I was on my fucking way, and it was real. Oh god it was real.

"Can I ask what that—um, what D&V—stands for?"

She laughed.

"Well, our clients joke about what it stands for, and we laugh about that and embrace it, but it really stands for Danielle and Vincent. Vincent is my husband."

"I can't wait to start," I said.

I signed a few employment things for the ice cream shop part, and we began the whole long process.

I did everything they asked of me. I got a physical, I was tested for every STD under the sun, I got some blood work done, and my background check came back sparkling clean.

First, I learned how to work the shop. I obsessed over it and became a virtuoso ice cream slinger in mere days—I wanted to get to the other stuff, and I hated waiting for it. I had waited for the next part for almost two years. The other girls were so nice showing me the ropes, as nice as they could be in broken English, and three of them were absolutely hilarious. Those crazy girls. I owe so much to all of them, and they don't even know it.

By the first week of June, I was finally taught how to do the other job. My 'trainer' was Vincent, the owner, and the training ground was their palatial beachfront condo. The same house where, in a little over a month, my life would completely change.

Vincent was 53, but he looked younger. Both of the owners were in pretty good shape. Their deeply tanned beach skin was just a pinch saggy and old, they were fit and lean, and Danielle's tits were actually still pretty perky from what I could tell—I never did get to see her naked. They seemed to bounce like normal tits, I seem to remember, so I don't think they were fake.

My trainer was as hot as a 53-year-old could be. I wanted to do it—I wanted to be trained and fuck him and other older men. The idea was beyond thrilling to me, and had built up in my head and my body for a year and a half at that point. However, in all honesty, yes, it did take some effort to get over how old his naked body looked compared to the young guys with perfect skin and tight bodies that I had been with up to that point. It's hard when you're a teenager, but I have a lot of resolve. Whatever it took, I cleared the first hurdle that night.

Vincent kept his body hair entirely shaved off, so that made it a little easier on me. That night he must have just gotten waxed, or something, because there was no stubble and not a single hair except the short hair on his head.

His definite physical saving grace was his objectively gorgeous cock. At that point I had only seen three cocks in real life, but untold hundreds in porn. I have been able to judge a cock with fairly accurate criterion for some time now. His cock was the kind you want to get all wet and take pictures of in studio lighting, then stuff in your mouth for a few hours and just suckle on it. This thing was a thick, juicy, circumcised cock with heavy-looking balls and a smooth, purple head. It looked just as beautiful flaccid as it did hard.

Somehow I don't remember so much about that night. Vincent was really a total stranger to me before I showed up—he hadn't been in the shop much that week. Actually? I never thought about this before—maybe that was intentional on his part, right? Wow. Huh.

My body was overdosing on adrenaline, and we had a few glasses of wine first. He asked me about my life and told me how he had met Danielle and some other stuff, and I just do not remember those details. I got a little tipsy. I remember him sitting in only plain green shorts with one leg over the other on a wide couch, with the dark ocean behind him through a massive window. I remember standing in front of him there and pulling my slutty romper off with nothing on underneath. I remember being startlingly wet standing in front of him naked.

I vividly remember that he just looked at me, really looked at my body, just sitting there. He took his time appreciating what he was about to get to have for the night, with an expression you might see on someone's face at an art museum. He signaled for me to turn around with a lazy rotating finger while his hand rested on his knee. That ultimate patience, maybe that's what got me hooked on older men.

Vincent and I did everything that night, and thankfully we took a lot of breaks. Danielle stayed somewhere else, and I spent the entire night with him. We would fuck, fall asleep, wake up, fuck, fall asleep, wake up, and repeat, until around noon the next day. I rode him, and he showed me how to make it look even hotter. He fucked me and coached me in making noises. He gave constructive feedback and never once made me feel stupid. I was respected and valued. He taught me how to give amazing head by tenderly touching a man's balls and by getting as much 'throat slime' out onto the cock as you can, and he showed me how to deepthroat by demonstrating it on a thick dildo with his own mouth and fucking throat. That, ladies and gentlemen, is a teacher.

He painstakingly broke down for me how to properly clean myself to prepare for anal sex, which is something I just do every day now. He got me to eat his very clean asshole, then patiently, carefully opened up my own fucking asshole with his dick and a ton of lube, thank God. I had messed around with my fingers, but I had never been fucked in the ass before, and I fell in love with everything about it right away. He showed me positions that I had never even seen in porn, and I guess selfishly just did so many brain melting things to my body that no boy had ever fucking done.

I don't know how many times I came that night—after the initial anxiety I came a lot—but I know for a fact that he came inside of me at least three times, if you can catch my drift.

We have unprotected sex with all of our clients, and they're encouraged to cum inside of us. They're all relentlessly screened and tested, and Danielle and Vincent pay for our sex-related health needs. Shit, listen to me talking like I still work for them. That's a little tragic.

I had an IUD put in the week after my training, and I took birth control just like all of the other girls. I love cum, so I loved that they wanted us to be able to take it wherever clients wanted to give it to us. I love the feeling of a cock suddenly pulsing with an orgasm and squirting cum into me. Christ, I fucking love that. I'll swallow, no problem—hey, give me my daily dickmilk and I will drink it all down and lick the thing clean, sir—but what I really want, what I need and must have as often as I can, is for that cum to rocket unfathomably deep into my immaculate lower body holes as men who have doctorates in the science of fucking rock my frail girly skeleton loose from the splintering cartilage and fraying muscle fibers with thundering, pulverizing cock slams you can record on distant seismographs. Do you know what I fucking mean? Do you understand what the fuck it is that I'm fucking talking about here?

'You think it's a game? You think it's a fuck-ing GAAAME?'

Whoa. Fuck. Yeaaap—gonna need a shower. Once you bust out my man DMX, y'all know y'all done dirted up some shit.

I have to be true to who I was back then, though. That little Colleen Shakespeare crap I just regailed your asses with about the seismograph? That's me talking—23-year-old me, here and now, after a few solid years of that good good beducation to perhaps coin a phrase. I didn't understand myself and my sexual needs like that after just one night with Vincent, and hell, I hadn't even met that second client yet. Oh, you'll read about that one.

I remember Vincent kept calling me a 'natural,' and I remember when he began 'teaching' me the basics of dirty talk. That's what I remember most, because I got to be creative, and it turned out I already had that merit badge. Fuck that—turns out I was a fully tenured professor in that field boys and girls and all precious children in between the two. Naw, I taught him, motherfuckers.

I came howling to life in that house, and the nastiest toxic shit I had ever heard just spewed out of my mind across my twisting tongue through my flapping born-again-slut lips into a torrent of noxious sludge flow from half a decade of watching the most perverted pornography I could find and from my own once-dormant and now blinding verbal brilliance. That was sort of better than all the sex we had—finding out I had that kind of disgusting filth inside of me, and discovering that I could wield it nude and snarling and hissing with no fear at all before this presumptuous man-person I hadn't known until like 3 or 4 hours ago.

Like a warrior. Like a legend. Like a goddamn poet.

Like a woman.

With legs spread wide for all to see and with one beautiful hand gripping my knock-you-on-your-ass perfect teenage pussy I drew that hot fucking flaming laser dragon-blasted heavy metal shit right out of my fated ancient stone on my own chosen high hill and thrust it up into the fucking Moon and out over sleeping Cape May, New Jersey and out over Mahwah and out over my awkward young years and out over the deep red water and out over the land and the sky and the creatures and out over the whole empire of femininity. My empire. My realm. My fucking birthright. It was empowering, sisters and sisters and sisters across the planet. I was proud of me.

Rrrrrrrrrrrrrrrrggggghh!

Vincent was disappointed for my sake, but completely understanding, when I told him that I had no interest at all in fucking another girl. I understood that this would hinder my rates—Danielle had broken those down to me already—but back then, and to this day, I only want to fuck men. He explained that I would definitely have threesomes with other girls, but they would always make sure I was never asked to fuck them or even touch them. I said I'd think about kissing another girl, but he waved his hand. No, I'd have to keep it black and white. They espoused hard boundaries for their beloved girls.

Vincent and Danielle were unlike the 'pimps' you have always pictured. They cared for all of us like we were top employees at an investment firm, like we were highly talented resources they needed to protect and serve. They treated us like people, they respected our rare collective disposition, and they loved us. I'm too old now to work for them—they cut you off at 22 as a rule—and I miss it so much.

Sigh.

Before I left, after a hearty lunch Vincent whipped up, he surprised me with a thumb drive. On it was the recording of our entire night, with the sleeping parts automatically cut out. Apparently, their house was covered in high-quality secret cameras. There was audio. Their, like, house 'system' had synthesized one single flowing video with changing angles and changing room cameras, based entirely on an array of motion sensors. God bless Vincent, he really tried to explain it to me. How much fucking money does that kind of technology cost? You've got me, dude, I just work here.

I watched almost the entire thing that night. It was like some kind of artsy professional pornography video starring me. I still break it out once in a while. Haha, in that video, at one point I'm kneeling on the couch buck naked with my tight, fat ass sticking out, facing the back cushions and that big ocean view window, and I'm looking back at him as he walks towards the couch to fuck me. I wag my ass at him with nanny-nanny-boo-boo attitude as he saunters forward, and I look like a little shit-eating demon. I glare straight into his face and with venomous glee speak to him the following unladylike remarks:

"I fucking dare you to get me pregnant, you old fucking slut. Look, whatever your fucking name is—Vance or Varn or whatever?—is that sloppy fucking cock gonna get in here one of these days? Will you just hurry the fuck up and do my little teenage shit already? My fucking tits are going out of style. I'm supposed to have more cum in me by now and I have to get home for fucking dinner soon.'

My fucking tits are going out of style. My tits. You just have to laugh. The whole composition was definitely something I couldn't have said to him at the ice cream shop. Well, scratch that, that's not true. He loved my mouth. I love my mouth. I was born for this, that's stone cold apparent in the video.

He promised me—and I fully believe him—that I had the only copy. It was for me, for further study, if I wanted. It was for the betterment of my new profession. He shook my hand and told me he would never, ever do this again with me. That was just their rules—they are such good people. Well, to us, I mean. You'll see what that's about.

As I was leaving, he turned me around and gave me one final piece of advice. A little speech.

"This is going to sound mean, Colleen, but you need to hear it—I think you'll understand what I mean."

He made sure I was looking him in the eyes, and he spoke to me.

"Under no circumstances should you ever tell any client that your mother died when you were young. You told us, that's fine, we aren't clients, but don't tell them. That's something that an older gentleman, perhaps a lonely older gentleman, might find themselves latching onto for whatever reason, and you risk these clients becoming uncomfortably attached to you. Just, believe me, it's for your own benefit. Don't do it. Easy as that."

"What if they—"

"They're not allowed to ask about your family. Trust me, they usually don't want to know about your family. They want to have fun."

I followed his advice to the letter, and it never steered me wrong.

Two nights later, I had my first client. I remember exactly what I wore that night. I wore a red and purple plaid flannel shirt—unbuttoned and with the sleeves rolled up—over a black spaghetti strap loose-fitting crop top, high-waist jean shorts, and low-top black Converse All-Stars with white socks. I hadn't exactly premeditated 'my thing,' but what 'my thing' became was dressing like what I was—a slightly introverted, 19-year-old engineering student between my freshman and sophomore years of college. The Ukrainian girls all dressed like fashion models—and, well, prostitutes—for their clients. I wanted to feel comfortable that first time, and it just stuck.

My first client was Jules, and Jules and I to this day are pretty close, as close as a young prostitute and her 57-year-old client can get. Jules is a widower, and he's not in the greatest of shape. He has something of a belly, his hair is kind of thin, and although he gets his back hair shaved it's still clear that he has it. He does have strong arms, strong legs, a mesmerizing soft voice and a big dick, so it's not a total chore. That first night, he couldn't have made my first 'assignment' any better. We just talked, we drank wine, we laughed a lot (he's funny), and we showed each other some of our favorite music. He paid for me to just hang out with him until something maybe happened, and that's not so typical.

Finally, I just stood up and shed my clothes for him. Here I was. I was now about to truly become a prostitute. I swear I almost came just stripping, and I know for a fact that I could not drink enough water that night—my mouth was the absolute driest it has ever been. I was shaking, more than with Vincent.

Jules was so sweet. He asked me to come sit on his lap, and we kissed for a while. He's a decent kisser, he knows how to respond. Then, he held my hand and led me up the steps to his giant bedroom, which was nearly pitch black—I didn't really see his full naked body until a few encounters later. He undressed, laid on the bed, and I slowly brought myself up over him on my knees.

With Jules, I do most of the work. That's how he likes it. I was nervous at first, but after I sat on his face and he ate my pussy for a little bit, I let myself go. I gave Jules a fucking show that night, and we had sex for maybe 20 minutes. When he came inside me, the floodgates burst. I immediately had my first staggering orgasm as a prostitute.

We weren't really supposed to spend the night with men unless they paid a lot extra, but Jules invited me to sleep in a guest room (he snores) and I just did. I stayed up late, drank some of his wine out on his deck next to the ocean in some sweatpants and a hoodie he had laying around, listened to the waves, and dealt with all of my complicated thoughts. I remember thinking about my family, and some friends back home, and trying to figure out where this was fucking going, you know? Much later, I went to sleep to the sound of waves gently crashing. In the morning, like he always does now, Jules made the shit out of some eggs Benedict, and we talked and laughed until I left.

The next client two nights later was... rough. This was Keith, a muscular, alright-looking 44-year-old attorney who lives and works in Texas in the fall, winter, and spring, but who I think grew up on the east coast, maybe Boston. Keith is into edging, Keith is into pain, Keith is into restraints, and Keith is into getting his goddamn money's worth. Every cent.

He. Is. A. Jackhammer.

There was no chit-chat with Keith. I was living teenage girl-meat that he had paid $5,000 for—$1,000 an hour—and we stopped once for about 20 minutes during the five hours until his fucking timer went off. I might have had an easier time completing one of those ultramarathons.

I was excited to meet my second client after my wonderful night with Jules. The new client's place was close by—five or so blocks away—so I walked over under a glorious clear night sky, whistling. He had booked five whole hours, and after Jules I assumed a chunk of that would be a nice dinner, music, conversation, hell I don't know—billiards? Boy. Whoa.

I walked merrily down the lane to his place wearing a heather gray Gap sweatshirt, purple panties, and tight jeans with white Pam Beesly-style Keds. I had put my hair in cute pigtails with little bows at the top for goodness' sake. I rang the client's doorbell. He opened the door a few seconds later. I smiled big like the stupid kid I was and stepped into the gauntlet.

"Hi Keith, I'm Colleen. We'll be, like, working together tonight."

I stuck my hand out to shake his hand, but that didn't happen. Without so much as a hello, as soon as his front door shut behind me Keith mechanically cut my clothes off with giant scissors like I was an Amazon package and we got to work. He left my Keds alone, and they stayed on my feet all night. Unlike my night with Jules, it actually was work. That night with Keith was hard, backbreaking labor.