by Thomas Henry
About two and a half hours later, the SL cruised past me. I was still in the driver’s seat, so I was able to follow with no problem.
My whole body relaxed when the SL turned onto Sally’s street. Apparently, Karen had just been the dapper man’s dinner date. Maybe he really was gay, too.
But the SL didn’t stop at the Oasis. It didn’t even slow down. It just cruised to the end of the street and turned onto Kalanianaole Highway. My body tensed again. Where was he taking Karen?
The SL made a left on Laukahi and headed up Waialae Iki. My stomach knotted. There was nothing up there but private homes. No night spots. No entertainment. Only private homes. And I could think of only one reason for the dapper man to be taking Karen to his home.
About half way up the ridge, the SL turned onto a side street. I was reluctant to turn right behind it because I thought that would make it obvious I was following. So, I cruised past the street, but as soon as I was out of sight, I made a U-turn. I pulled over to the curb and forced myself to count to fifteen before I rolled down to the corner and made the turn.
Halfway up the side street, I could see a garage door eclipsing the interior light of a garage. Surely that was where the SL had gone.
I pulled over to the curb and killed my lights. I left the windows up and the engine running as I waited for half an hour. Then I cruised down the street and parked across from the house. I lowered the window on the other side of the van and killed the engine.
Window coverings kept me from seeing into the house, but they did emit a faint glow from what I assumed to be the living room. In the quiet of the night, I thought I could hear hints of romantic music.
I’d guess it was about half an hour before another light came on farther back along the house. And then the living room light went off. My stomach lurched and my balls tightened. I was pretty sure he had taken her to his bedroom.
So how long would it take? Would it be slam-bam-thankyou-ma’am? Or would he take his time and enjoy her for a couple of hours?
The hours ticked by very slowly. One, two, three, four… Apparently, Karen was staying all night. I considered going back to my place to get some rest, but I just couldn’t leave.
About 3 am, a set of headlights appeared at the corner behind me. They came up the street a short way and then went off. A few seconds later, the Cadillac glided to a stop across the street from me.
It sat there with the engine idling and the lights off. After a few minutes, I saw movement at the front door of the house. Karen stepped out and walked gingerly toward the Cadillac. Her stockings were gone, and she was carrying her stilettos. Her hair was a mess.
Karen got into the back seat of the Cadillac. With its headlights still off, it rolled further up the street, made a U-turn, and came back past me. It stopped at the corner. Its lights came on as it turned down Laukahi.
I had no doubt the Cadillac was taking Karen back to the Oasis. I didn’t see any point in following, so I headed out to my place in Halawa.
* * * *
I was jolted into consciousness by my ringing cellphone. Who would be calling me so early on a Sunday? Karen maybe? My heart skipped a beat as I opened my eyes and looked for my phone.
I had been sleeping on my arm, and my hand was numb. I tried to pick up the phone, but my fingers couldn’t grip it, and it fell to the floor. By the time I managed to pick it up, it had stopped ringing. My heart sank. What if I had missed Karen?
I checked the caller ID. It had been Sally…or her number, anyway. My pulse quickened. Was something wrong? Had something happened to Karen? I tried not to imagine the lurid possibilities as I touched the screen to return Sally’s call.
“Hey, Lover-Boy!”
“Hey...what’s up?”
“You sound sleepy. Rough night?”
The cheerfulness of Sally’s voice was both annoying and reassuring. She wouldn’t have been so cheerful if she was calling with bad news about Karen.
“Uh… Yeah, I guess you could say that.”
“Must be hard to get any sleep in that van.”
I was nonplussed. How did Sally know about the van?
“Look,” Sally continued. “You can’t keep following Karen everywhere she goes. Sooner or later, one of my clients is going to take notice of your van, and that’s going to be a big problem. You know how I am about confidentiality.”
“How did you know it was me?”
“My driver ran your plates.”
I didn’t bother to ask how it was she had a driver who could do that. Sally obviously was well-connected.
“Does Karen know?”
“Not unless she figured it out on her own. We didn’t tell her. You know how I am about confidentiality.”
“Yeah…”
“So I take it she hasn’t called you.”
“No. That’s why I’ve been watching for her. I was hoping to talk to her in person, but I haven’t gotten a chance yet.”
“Yeah. But you know my clients expect the utmost in discretion. Can I trust you not to approach Karen if she’s with one of them?”
“Of course. I don’t want to make a scene. I’m just concerned about her. She’s acting very strangely.”
“You jealous?”
I took a deep breath. “Of course. But that’s nothing new. That seems to be integral to our relationship.”
“Uh-huh. You two do have an interesting relationship.”
Neither of us said anything for a while. I had the feeling Sally had more to say, so I just waited for her to say it.
Finally, she asked, “Are you sure I can trust you not to interfere with what Karen is doing for me?”
“Sure. Well, assuming she’s doing it voluntarily.”
Sally chuckled. “Oh, don’t worry. No one is coercing her or trying to keep her away from you. I actually did tell her you wanted her to call, so if she hasn’t, that’s her decision. I had nothing to do with it.”
“Okay,” I said. “I’ll behave. I’ll wait until Karen is ready to talk to me.”
Sally was silent for a minute. “Well, maybe I can help. Remember Lita?”
“Who?”
“Lita…that little college girl who had you stepping on your tongue at my club.”
This was the first time I had heard her name, but I remembered her well. Lita was the little hapa “cheerleader” with the great ass and tiny tits who had taken on three guys at one time as some kind of sorority initiation rite. My balls tingled as I visualized her puffy nipples and hairless pussy.
“Oh yeah, I remember. But I didn’t know her name was Lita.”
“Yeah, short for Lolita, actually.”
“You’re kidding.”
“Well, that’s not her real name, of course. But we gave her that nickname because of her tiny tits and bald pussy.”
“Yeah, I get that. So what about her?”
“Well…do you know what the ‘girlfriend experience’ is?”
“More or less. That’s when a hooker behaves in the more personal and intimate way a girlfriend would…although I understand there are differences of opinion about exactly what all that entails.”
“Oooh! ‘Hooker’ is such an ugly word. But…basically, you’re right about what the girlfriend experience is. So, Lita is trying to qualify to join a very exclusive sorority that specializes in providing the girlfriend experience to carefully screened men who can afford to hire the best in female companionship. Demand for this level of service far outstrips supply, so it’s a lucrative business. Sorority membership is very rewarding for a college girl with tuition to pay and the right perspective. And our little Lolita has the right perspective. She’s determined to become a full member of the sorority as a means of paying her way through college and law school.”
“Okay. So what does that have to do with me?”
“Well, to become a full sorority member, Lita still needs to pass her final exam, and I thought you might help with that.”
“I see. So you’re trying to distract me f
rom focusing on Karen?”
“Not so much. Actually, I’m trying to get you into physical proximity to Karen without interfering with what she is doing.”
“Oh? How does fixing me up with Lita help with that?”
I heard Sally take a deep breath. “Okay, here it is…I have some male clients coming to the Oasis from the Mainland and Asia for a little three-night rest-and-relaxation holiday. It’s an all-inclusive package I offer from time to time. Accommodations…gourmet food…liquor and wine…and top-shelf girlfriends to take care of all their needs for female companionship.”
I was surprised. I had heard of sex vacation resorts in such places as the Dominican Republic and Margarita Island, but I had never heard of one in Hawaii. Maybe that’s because prostitution is legal in those other places, but quite illegal here.
“So…how does this involve me?”
“Well, I thought you could join in with the group of clients, and I would set you up with Lita as your girlfriend. As you saw that night at my club, that little girl can fuck with the best of them, but to become a full member of the sorority, she still needs to demonstrate that she can provide a credible ‘girlfriend experience.’ So I thought I’d let you evaluate her performance as a sort of final exam for her.”
My balls tightened and my cock swelled a bit as I visualized Lita in my bed. “I see. So…how do you define the ‘girlfriend experience?’ What sort of stuff is she expected to do?”
“Everything a real girlfriend would do. Companionship…romance…kissing…cuddling…every kind of sex…you name it.”
“Every kind of sex?”
“Sure. Oral…anal…threesomes...whatever you want…whenever you want…as much as you want. Everybody’s carefully screened, and the girls are all on birth control, so it’s all bareback, of course. That’s why my clients are willing to pay my prices.”
“Sounds more like everything a real girlfriend wouldn’t do.”
Sally chuckled. “You mean everything a wife wouldn’t do.”
“Yeah, I suppose.” I had an uneasy feeling. “So how is being fixed up with Lita going to get me closer to Karen?”
“Well… Karen is going to be in the lineup.”
“Lineup?” My apprehension grew.
“Yes. On the first evening, a group of the sorority girls will mingle with the clients for a couple of hours, pretty much like the mating dance you saw that night at my club. That way, the men can decide which girl or girls they want as their girlfriends during their vacation. Most of the men will want a different girl each night. Some may want more than one girl at a time.”
My stomach knotted. “How does this involve Karen? She’s not in the sorority.”
“No, not technically. I guess you could say we’re making her an honorary member.”
“You’re turning Karen into a hooker?”
“No! I mean, it’s not like she’s going to be walking the streets in Waikiki. Think of her as a courtesan. She’s just going to be providing the girlfriend experience to nice, well-to-do men who place a very high value on her services.”
“And she understands you’re prostituting her and she’s okay with it?”
“Everything is on the up-and-up. I’m not some sleazy human-trafficker, you know. Karen’s involvement is purely voluntary on her part. I’m just in the business of matching up consenting adults who wish to engage in a value-for-value exchange.”
“So you’re actually going to make her some strange guy’s paid sex slave?”
“Well, technically, she has to be chosen. But I expect that most of the men will want her, so yes, I expect her to be someone’s paid girlfriend. Actually…she most likely will be the girlfriend of a different man each night.”
My mind was spinning and my stomach was doing flip-flops. I was struggling to make sense of what Karen was doing. “What makes you think Karen is capable of performing to your standards?” I asked.
“Are you kidding? You saw her with the bulls at my place last month. She could be a porn star.”
“Yeah, but she was drunk and drugged that night. And what about the ‘girlfriend experience’ part? How do you know she’s capable of providing that?”
“Oh, she aced her final exam last night. The man she went out with is one of my top local clients. He said she was the best he ever had. In fact, he wants to set up a regular thing with her.”
My stomach churned at the thought that Karen might become some guy’s paid lover. But that would be a problem for another day. Right now, I needed to focus on this sex-vacation thing.
“So, if you think all the men will want her, how do you determine who gets her?” I asked.
“Well, it’s kind of complicated, but it’s similar to cumulative voting in an election, only with dollars instead of votes. As part of the package he purchases, each man has so many virtual dollars to spend on girlfriends for the duration of his vacation. The more he spends to get the girl he wants on any one day will reduce the amount he has available to spend on other days. So, whoever bids the most for Karen on any given day will get her for that day, but it’s unlikely that any one man will get her for more than one day.”
“What if there’s a tie?”
“Oh, let’s just say I flip a coin.”
“I see. So how are you’re going to set me up with Lita? Rig the bids?”
“Exactly…but in your case, you won’t be bidding anyway. I’m not charging you, so you won’t have any dollars to bid with.”
“So that means I can’t bid on Karen…”
“Nope. I’m reserving her for the paying customers. You get Lita for all three nights. I want you to give her an extensive and extended try-out. Really challenge her skills and commitment. But…even though you can’t have her, Karen will be nearby, and you’ll be able to see her in action some of the time…if that’s what you want.”
As always, I was conflicted. The idea of Karen selling herself to strange men was repugnant, but the idea of a bunch of men bidding big bucks for her was a real turn-on. My stomach was roiling, but my balls were aching with need. There really was no question that I would accept Sally’s offer.
“So,” Sally said. “You in?”
“I’m in. But I have a question. Are you going to tell Karen I’ll be there?”
“You know how I am about confidentiality.”
So Karen was in for a surprise. I had no problem with that, but I wondered how Karen would react when she saw me there.
“Okay,” Sally continued. “The other men will be arriving on various flights tomorrow, so we will wait to have the lineup of girls until after everyone is here. I imagine that will be about six, so I’d suggest you arrive at least by five so you can settle into your room ahead of the lineup.” She paused for a few seconds. “Meanwhile, get some rest and don’t come spying on Karen tonight. Okay?”
“Okay.”
“Oh! One more thing…”
“What’s that?”
“You owe me, Lover-Boy…big time.”
I didn’t know when or where Sally intended to collect, but I feared I knew how the horny transsexual wanted to be paid. My butt clenched.
* * * *
It was almost five on Monday evening when I called Sally’s number from my car as I cruised down the street toward the Oasis. She had sent me a text earlier telling me to call her when I was nearly there.
Sally’s phone rang several times and went to voice mail just as I got to her house. I was momentarily annoyed that she hadn’t answered, and I was about to leave a voice mail when one of her security guys stepped out onto the sidewalk and pointed toward the four-car garage. One of the doors was going up.
As I pulled into the garage next to Sally’s Cadillac, I mused that it was a good thing I had decided to bring the Merc. The van would have been too tall to fit through the door.
As the door closed behind me, I popped the trunk lid and got out of my car. I was pulling my bag out of the trunk when Sally appeared sans her outrageous wig and makeup. Notwit
hstanding the vaguely masculine aura of her broad shoulders and narrow hips, she was quite lovely in a silky robe that telegraphed her big nipples enticingly.
“Hey, Lover-Boy!”
“Hey.”
It was obvious that Sally intended to give me a hug, so I dropped my bag as I closed the trunk lid. She paused a couple of steps away from me and spun around once. “Like my new robe?” She posed with one hand on her hip and the other hand on the loose end of the knotted belt.
“It’s quite lovely.”
Sally winked. “You should see what’s underneath.” She tugged at the belt end, and the knot disappeared. For a moment, the robe remained closed. But when she took the last two steps toward me, it billowed open. The fact that she was buck-naked under the robe barely had time to register in my brain before she wrapped her arms around me and drew me into a bear-hug. She gave me a three-Mississippi kiss on the lips. I was thankful she wasn’t wearing that garish red lipstick she often wore.
Sally pressed her huge tits against my chest and rubbed her groin against mine. She wasn’t fully erect, but she was getting there. Truth be told, I was swelling a bit myself.
“Too bad you need to save all your juices for Lita,” she whispered in my ear. “Otherwise, I’d drag you into the bushes and drain your balls right now.”
I tried to disavow the swelling of my cock as I raised my eyebrows to feign innocence. I made a show of looking around the garage. “I don’t see any bushes.”
“They’re metaphorical, silly,” Sally said. She cupped my balls and gave me a more lingering kiss. Then she took a deep breath and stepped back. She shook her head as she re-tied her robe. “One of these days Lover-Boy…one of these days soon.”
My butt clenched for the second time in as many days. I picked up my bag.
Sally took me by the hand and led me into the house, through the kitchen, and out across the central courtyard. Caterers were putting out food for a buffet and setting up a bar. I didn’t see Karen or any of the other sorority girls, nor did I see any of the other male guests. All but one of the bedroom doors that opened onto the courtyard were closed.
