My boss Peter and I met one of our customers at a bar at the Seasons. Peter seemed to have a thing for that particular hotel. I wasn’t certain why I was there, since I had little to do with customer relations. But I was interviewing for an opening in my department and it turned out the gentleman had a relative he hoped to recommend. We discussed all that and ate a light supper before he made an exit. “Whew, that was a trifle awkward,” Peter said, “Let’s sit at the bar. I need a real drink.” I understood what he actually needed was to talk about his girlfriend – well, former girlfriend now. The bartender looked familiar for some reason but I’m not terribly good at recognizing faces. Peter, however, greeted him by name and I realized the guy had worked at the company reception I’d attended at this hotel. Todd was his name.
The air conditioning was up higher than I was used to, which, I soon noticed, made my nipples stand rigid. They must certainly be showing through my scoop top. Fortunately, I was also wearing a short open jacket that I could pull closer to hide them. Peter sometimes devoured me with his eyes but was just as likely to be oblivious. Tonight, I was glad to see, he paid no attention. The bartender, on the other hand, kept angling for a better view. I was nursing my first drink but Peter was finishing his second and ordering a third. It was looking like this could be a longish therapy session. While the drink was being mixed, he sloped off to the men’s room. Todd set the drink down at our place and leaned toward me, “You’re Mindi, right?”
I was trying to recall if Peter had called me by name. “Yes, that’s right.”
“I thought so. Derick used to come in here. He mentioned you.” I must have gone pale because he hurriedly tried to reassure me, “No, not like that. No offense intended. Just how happy he was with you.” He glanced around for anyone who might be close enough to overhear. “I make a lot of contacts here. High rollers looking for…introductions. If you want, I can direct some of them your way.”
Oh wonderful, this jerk wants to be my pimp! Okay, it is true that guy Derick did pay me for sex – twice. But the first time he left it for me without a clue on my part. The second time was a little different. But, still. Peter returned at that moment, saving me from having to reply. I took a moment to scan the room and wonder how many of the more glamorous patrons were professional escorts. I had one more drink with my maudlin boss and left for home.
_
Denise and I intermittently watched a streaming movie and hashed over Peter’s girlfriend woes. Generally, we felt sorry for him. I also told her about Todd’s business proposal.
“You’re shitting me!” She made me repeat every detail of what he’d said, then sat pensively for several minutes. “I have a better idea. I came across something the other day on the internet. So, um…it’s a kind of dating app/site. It has thousands of members all over. Men join and request the kind of date they want. But they give a donation to their date…
“It’s an escort site? They book escorts there? That’s what it is, isn’t it?”
“No, it’s not like an agency or anything. Men who want a hookup for a particular period of time go there to find willing partners and women go to do the same – except they get paid. There’s the money part, but that’s…I mean, we all get something from men we date. Dinner or drinks or gifts. What’s the difference? This eliminates most of the surprises because we’d know what was happening before the date. And, besides, neither one of us is interested in a relationship with them as we sleep with.”
We looked closely at the site and discussed the possibilities and potential problems. I saw that Denise was hot to try it and I couldn’t deny that having things agreed to beforehand was alluring.
In the end, we went through the signup process. One of the best features was that women members could view the men’s profiles but the men could not look at theirs or contact them unless that woman responded to their date requests. So if I responded to a request, the guy could view me and, if he liked what he saw and read, we could chat about details.
Both of us browsed the site for a couple of days before we took the plunge and responded. We intentionally accepted dates for the same evening and in locations within easy walking distance. The fellow I accepted was older, well late-forties, but trim and good-looking, in a distinguished gentlemanly way. He was in town from Chicago.
The night of our rendezvous, Denise was like a nervous cat and I admit to a case of butterflies. Both of us had gone with out-of-town business types to avoid, we hoped, any later complications. I met my guy at a venerable but very upscale hotel – well, in the restaurant. I wondered if this kind of top-shelf venue was usual for paid dates. But at least the man was instantly recognizable when I entered, so his profile photo was accurate. He guided me to a select table in a small window alcove, with far more crystal and silver than anyone could truly need. Still, he was accomplished in putting his companions at ease. The conversation was light and effortless, even for me. He was involved in some sort of finance that I didn’t profess to understand. I kept my own work and personal details suitably vague and he didn’t press me.
The dinner was remarkably fine. We had moved beyond dessert to after-dinner drinks. I stole a glance at his watch and was a bit shocked to see we’d already been there for over an hour. It never occurred to me the preliminaries would take this long. I…of course, I’d not thought completely through any of that. But it was expected that he’d pay for time, not just sex. We’d agreed on a two-hour range. After another half hour, I was starting to wonder. Then he said, “This has been an absolute pleasure. I’m afraid I have a very early flight. May I call you a cab or…”
“Oh, thank you, no. I have transportation.” It occurred to me, for the first time, I hadn’t gotten my gift up front. Well, okay…the site has verified credit card info on each man as a backup. The men know that if they stiff a date, the site will charge it to their card. While these thoughts raced through my head, the gentleman discretely withdrew a slim blue envelope from his jacket pocket and placed it on the table near my empty glass. I rather self-consciously thanked him for the lovely evening and walked out with him, stopping at the ladies' room on the way. With my lips and makeup restored, I peeked into the envelope. There were ten hundred-dollar bills. Wow, that was easy!
Denise was waiting at the cozy lounge where we’d agreed to meet. She looked like she’d had a far more strenuous night than I had. “I can say this for my date, he had plenty of stamina. What a workout! How was yours?” I told her about it. We agreed that, all things considered, it had gone pretty well.
Of course, it was a pleasant enough evening, and very lucrative, but not exactly what I’d been anticipating. I wasn’t lusting for sex but… well, you know. So Tuesday found me checking the date requests on my personal tablet at work. I soon came across a likely candidate. Mid-thirties, shortish blond hair and a surfer tan. That’s not really my type – if there is such a thing – but he was cute and had a nice build. He wanted, as far as I could tell, a quickie. I could deal with that this evening, I thought. A concise chat later, we were on.
I rushed home, showered and changed into a cocktail dress and stiletto heels. We arranged to meet in yet another hotel. After a brief introduction and a fast drink, we retired to his room. He wasn’t big on foreplay at all, but he did sport a very impressive hard-on. I was soon on all fours, with him plowing me from behind. It wasn’t exactly romantic sex but he filled me nicely and I loved the way his hands moved over my body as he did it. A change of positions and I was on my back with my legs draped over his shoulders, his cock moving rhythmically in and out. He shifted me to my side and fucked that way for several more minutes, before flipping me on my back again. Now, he was absolutely driving into me, causing the bed, and me, to bounce like a trampoline. Just as I thought I’d have to ask him to ease up, I felt the strong pulses of cum deep inside.
_
That weekend I was alone, Denise having arranged a tryst with an old boyfriend. Saturday afternoon, against my better judgement, I was perusing the site. The urge to continue with these dates, for some reason, was very strong. I went ahead and set one up for fairly early in the evening. I met the man in a trendy gastropub near Society Hill. We had a cocktail – he had three, while I nursed the first – and ate light fare. It was agreed we’d go to his apartment, which was just a short walk. He was confident at the pub but not in bed. He lasted maybe eight minutes once we got down to it.
After he cooled off, I tried to stroke him back to hardness. After all, he was paying for an hour. It took forever to finally get him off. All in all, rather disappointing. It was only 9 PM, so I sat in a Starbucks and checked who was up on the site. I was looking for someone who could be ready to go in an hour, or thereabouts. It was Saturday night so there were a lot of choices. I eventually accepted a very athletic guy with sort of dark hair and a rather imposing body. I used the restroom to freshen up and drove to our hotel meet. It was not one of the five-star places but still fine.
I was a little taken aback when I saw the guy in person. He was at least 6’5 and well over two-hundred, well-muscled pounds. He looked like he could play for the Eagles. I’m 5’3 and 110 lbs, so I was wondering how we would actually do it! He stripped me out of my dress and undies, then asked me to display myself in the usual porn model way. He was very curious about my clit hood piercing.
We moved to the bed where he began fairly gently, changing positions often. By the third change, he was getting far rougher. I asked him to go easier and he did for a while. But soon, I was being tossed around like a rag doll. He didn’t actually hurt me but it was not the treatment I was accustomed to. It’s crazy but, in a total surprise to me, I found it a bit exciting. Soon he was literally pile-driving me, forcing the air from my lungs with every lunge.
He jerked me from the bed onto my knees and fired a long, warm stream of semen across my face. Some of it went in my eye, forcing me to blink, but I was still able to sense there was another person in the room now.
Before I could clear my vision, a second hard dick was pushing against my lips. At first, I tried to avoid him, but finally welcomed him into my mouth. The scene became surreal. I alternated their cocks, sucking one then the other, just as I’d seen it done in sex videos. They picked me up and dumped me onto the bed. It seemed impossible but I was almost certain there was a third man standing on the other side of the bed. It didn’t fully register because I was immediately covered by a massive body. There was a switching of places more than once. I was sure now – three of them! And they each fucked me… repeatedly.
I was getting worn out, sore and bruised. Now, I was on my side with one of them facing me and forcing himself into my pussy. I was vaguely aware of another lying behind me. Then, in one movement, a penis was jammed hard into my anus. I let out a short but sharp scream. I tried to speak, but no words came. There was only something between a gasp and a hoarse shout. But I caught my breath... and could have shouted in protest, demanding they stop. They might have done.
But I didn’t do that. I wouldn't have had the courage to ask for this but I did want it. It was immensely exhilarating. Almost intoxicating. They took turns double-penetrating me. I don’t know how many times or for how long.
I must have dropped off after they finished. When I came around, there was no one in the room. After a few minutes, I was able to sit up and eventually start for the bathroom. I could see in the large wall mirror that I looked as disheveled as I felt. My face was heavily streaked with eye makeup, tears and cum. My hair was matted with wet semen, the skin on my body was mottled and red. There were traces of blood around both pussy and anus – not actual bleeding, but some blood. My piercing was also red and swollen. The sex was a little rough, but I'd also had a series of small but increasingly intense orgasms. I wasn't complaining.
I shakily continued toward the bathroom. I wanted to take a shower but couldn’t muster the energy. The best thing to do was to lie down and rest some more. When I woke, it was 2 AM. At this point, I figured the room was paid for and those guys weren’t coming back. So I showered and climbed into bed, stripping off the soaked and stained duvet first.
I was about to turn out the light when I saw my bag was sitting open on a side table. Oh no! But when I examined it, I found it stuffed with cash.
