Virgin Gigolo Ch. 09

~

Melissa had always, to date, been perfect in vetting customers. There was always that is there something fishy? about this booking, question. Is there something fishy about this contact? Melissa had said that any of her girls could walk away from any arrangement with no questions asked, but what about me? There had never been any thoughts like that with any of my direct customers; they had always been referred to me, by someone who had been referred to me, by someone whom I knew or had dealings with.

There was something niggling in the back of my mind on this one. It was another phony police gig. Robin and I had been requested for a standing 69 for what was supposedly a retirement party. I can't say what it was that caused me to question. Perhaps the location? An office building rather than a hotel room? Perhaps that it wasn't a bachelor or bachelorette party, or a frat party, or someplace where young horny guys or girls were going to be there?

We parked in the parking garage below the building, Robin and I getting out and walking toward the elevators, when I saw someone's head move in a car situated where whoever it was could see us as we walked by. I still didn't think anything of it, until I glanced at the front window of that car and saw two men pretending to be talking and not really paying attention to us. Behind the steering wheel in the driver's seat was Joe. The last time I'd seen Joe he'd nodded and lifted a hand to wave goodbye to me as he was boning some chick doggy style while his wife was asking me if I'd like to stay around for a blowjob. I'd never seen him clothed; when we'd met originally, he'd been wearing only a mesh sack around his cock and balls, and his wife hadn't really been wearing much besides a bold gold necklace that broadcast: Cocksucker.

I wasn't at first sure it was him, but his head moved slightly back and forth, one half of a "no" shake of his head and, in that instant, it all clicked, and I was sure. For some reason I refrained from nodding my head in acknowledgement, as the other man in the front seat was pretending not to be watching, instead continued walking beside Robin toward the bank of elevators as if I really hadn't seen him. As we got on, I turned back, seeing Joe and whoever he was with just getting out of their car, but also seeing four other men getting out of two other cars and following us toward the elevators. I reached over and pushed the button for the 14th floor as we'd been instructed, and then pushed the button for the 2nd floor.

"What's on the 2nd floor?" Robin questioned.

"The exit. We're leaving."

"What? Why?"

"Something not right," I answered, taking her arm and guiding her off at the 2nd floor. I explained that I'd recognized the man I knew as Joe while pushing the down call button on the elevator panel. Almost instantly another elevator door opened, and we stepped back on. I told her that I knew he'd recognized me, and I'd interpreted his subtle shake of the head as a warning. In the parking garage, the men I'd seen had all disappeared, presumably into other elevators going up.

There was a parking lot across the street which I pulled into. I immediately called Melissa, told her what I'd seen and that my spidey-sense had told me to bail out. I told her about seeing Joe, about his warning, and she said she'd call me right back. Ten minutes later she called back, confirming that Jean told her that Joe was an undercover cop, and that if he'd seen and given a warning -- it was probably legitimate. We never did hear what exactly they were there for as it never hit the news, but just as Melissa finished telling me this, several cop cars pulled up in front of the building and Joe, along with his teammates, came out the front doors with several people wearing handcuffs. I couldn't help but wonder if the "retirement party" was actually an undercover sting operation for prostitution. Technically we'd only agreed to perform a sex act between two consenting adults, but we all knew that was just quibbling, as we also knew that for an additional price...

~

I guess it was bound to happen. I don't know how many times, maybe half a dozen where I'd picked Robin up, we'd worked a gig, gone back and had a late meal, when I broke my one margarita limit, and we ordered a second. And we ordered a third. When we got up to leave, I knew there was no way I was OK to drive, it was all I could do to walk. "I better call an Uber," I said when we got back to my car, "there's no way I'm driving anywhere."

"No, you can just stay with me and go home in the morning."

"Are you sure?"

"Danny, you are still a dweeb. Yes, I'm sure."

"I uhm... I uh... have you got a couch?" She did, or rather they did, as I hadn't realized until she said, "You don't want to sleep there, Savanna gets up a lot earlier than I do, at least when she's home."

"Savanna?" I said, suddenly remembering this was a two-bedroom apartment and she had a roommate. I'd never seen Savanna there.

"Savanna. You know, your occasional fuck buddy? She's my roommate."

I could have slept in my boxers, except that I was going commando. I usually wore underwear when I was visiting my clients, but on our fake police gigs, since I went commando in the outfit, I'd taken to just leaving my place the same way. Now, mostly drunk, all I could do was either sleep in my clothes or get naked.

I got naked.

Robin went in and took a shower first. "Your turn. I left you a towel on the counter," she said as she came out with a towel wrapped around herself. I went in and showered, returning the same way she had -- with the towel wrapped around my waist. Robin was already in bed, sheet up to her neck, but her arms were on top and her shoulders were bare. I dropped the towel just before I slid under the sheets on my side of the bed.

I'd been occasionally having sex with Robin on our gigs. Sometimes it was with Savanna, and even occasionally with Melissa. But I'd also been regularly having sex with Mary and all the others, literally dozens, of women. I'd gotten where Paul was sucking my cock every time I visited Lindsey, sometimes sucking me off, usually just sucking me hard so I could do Lindsey again. But yet, it felt really strange being naked, in bed, with Robin. I was even fucking Robin's mother's ass every couple of weeks, but still -- something about this felt funny. And then I realized what it was. "You know, I've only ever slept in the same bed with a woman once before."

"Really? You've never had an overnight gig?"

"Just one, but it wasn't intended. We fell asleep. You?"

"Usually twice a week."

"Here?"

"No. Usually hotels, sometimes at their homes. Nobody comes here, nobody knows where I live."

"Except me. And Savanna." I thought about it for a moment. "Does Melissa know where you live?"

I felt the bed shake with her head bobbing before she said, "Yeah. You don't know?"

"Know what?"

"Melissa and Savanna? They um..."

It clicked. "Ah, I knew they both liked women, I didn't put that together."

"When we were talking in the office, and she said she didn't want any real names?"

"Yeah?"

"She knew your real name before she ever talked to you. But if you never say, it's plausible deniability."

"She is pretty thorough."

"Danny?"

"Yeah?" I answered, sensing a question coming at me.

"I was reading about porn stars and how they often date... each other..."

"OK..." I wasn't sure what she was getting at.

"After a day of having sex in front of the camera, do you know what most of them do... at the end of their date?" Her hand reached over under the sheets and found mine. I squeezed her fingers in return.

"No. What do they do?"

Pulling against my hand she rolled over towards me, her naked body landing across my shoulder. In the dark I could see her face above me, her eyes open. "They have sex."

I stared into her eyes for a moment before I raised my opposite hand to Robin's back, slid it up to her head, and pulled her mouth down to mine.

Our kiss was tender, passionate, slow, and long. My hands weren't even stroking her body, she wasn't stroking mine. At first it was all about the kiss. The longer we kissed the harder I was growing without otherwise even touching her body. Not that I didn't; soon enough we were wrestling together, caressing, stroking, pleasuring each other, but this was no show, no sex exhibition for others to watch. This was totally different -- this was sex for us. This was mutual pleasuring because we wanted to -- not because we were getting paid for it.

We broke the kiss, and I rolled toward her, pushed her over onto her back, and let my hands caress her body. Her nipples were hard once again, her pussy wet and hot. I hadn't even thought about a condom, but she had, she already had it palmed, and I had to wonder if this was a seduction, and if so -- who was seducing whom? When she unrolled the condom onto me and I slipped my dick inside her, she wrapped her legs over mine and welcomed me home. Despite not going down on her, or even sucking her nipples, she came before I did. For the first time I realized that I had just had sex, and it had been something more than just sex.

~

"Did you ever do anyone that you knew?"

I'd awoken and had just been lying there with a throbbing head. It was past dawn, the room lit by the light seeping around the window blinds. It had only been three margaritas, but that was more than I'd ever had before, and I realized that perhaps I was a little hung over. Certainly, I was a little dehydrated. I rolled my head toward Robin after she asked the question, finding her lying on her side facing me with her eyes open.

"You mean as a customer? Yes, of course." That I'd never done anyone, except for her, who wasn't a customer I didn't say.

"Who?"

"Well, Mary Wilson obviously."

"I wonder if I'll like sex the way she does when I'm that old."

"I'd almost guarantee it." She scooted over closer to me, I raised my arm and she snuggled against me. "I don't think we ever really get tired of sex, but maybe just don't desire it as much as when we're our age."

"Thank you," Robin whispered, her fingers stroking through the hair on my chest.

"For what?"

"That was really nice. Not having to get up and go home. Not pretending I really care about someone who's paying to stick their cock in me." I didn't say anything. "Danny?" she said a few moments later.

"Yeah?"

"I never disliked you."

"I always liked you too," I answered. We just lay there for a bit without saying anything.

"What about you? Have any of your customers been anyone that you knew?" For the first time I wondered if she'd been fucking anyone that I knew, and realized her question to me had probably had the same reasoning.

"Yeah. Several. My old high school friend, Chloe Kai? I don't know if you knew her. Cute little Chinese gal?" I remembered her and said so. "Her mom and dad are divorced, her dad goes back and forth to Hong Kong all the time, and every time he comes to town, he books me for the night. He's always got a business meeting and takes me along. He introduces me as his girlfriend, and then likes to fuck all night long."

"Does Chloe know?"

"No."

"Anyone else?" She hadn't continued immediately, and I sensed there were more answers to my original question.

"Yeah."

"Who?" She didn't say anything for a moment.

"I shouldn't tell you."

"But you're going to..." I prodded.

"Do you remember Mr. Blankenship?" I knew the name, but it took a second before I remembered why.

"The junior high school Principal?"

"Yep. That's him. I've seen him two years in a row."

"Wow. I don't think I've even heard that name since I left Middle School. Two years?" I asked. "Why two years?"

"His wife booked me and gave me to him for a birthday present."

"Oh my God. Really?"

"Really. He wanted to do anal sex and she didn't, so she bought me for the night, and I took care of him."

"Oh." I thought back with my tryst with Robin's mother, Martha. "Do you like that?"

"It's OK. I like it in front better than in back. What about you? You ever do anal sex?" I'm sure my heartrate went berserk while I contemplated the answer.

"Yes."

"Really? With anyone that I know?" Now my heart was practically beating out of my chest. Do I lie? Do I tell her? I decided to keep it simple.

"Yes." I didn't say which question I was answering yes to.

"Really! With someone I know?" I could tell she was curious who it was, but I merely affirmed that it was someone that she did know while also affirming that the yes applied to both questions.

"I don't think you really want to know," I said when she pushed again for an answer.

"I told you, you need to tell me." She giggled, "Who do I know that has a butt kink?" I looked over at her, knowing I shouldn't tell her, but on the other hand she'd told me. I opened my mouth, started to speak, and closed it again. "You can't tell her. I'm not sure you'd want to anyway."

"Who?" she pushed again, "tell me."

I finally relented. "Your mother."

Robin's mouth fell open and she pulled away from my shoulder, saying nothing for a moment.

"My mother?" she asked, obviously aghast at the revelation. She looked away into the distance, and then her eyes focused back on me. "You've been... butt fucking my mother?"

"Every few weeks. About once a month."

"Does dad know?"

"Pretty sure he doesn't. Your mom said he never liked anal and won't do it."

"How long?"

"Just a couple of hours."

"No. I meant how long have you been doing her?"

"The week after Helen's sex toy party. She got the number from Helen and called."

"That was just before my divorce was final." I could see her eyes, but she wasn't focused on me, but rather focused in her mind. "Where? Do you do her at home?"

"No. We meet at the Crowne Plaza downtown. She said it's near her work."

"Amazing. I never would have thought it of her."

"I've done a lot of people I never would have thought would be paying for sex."

"Who else might I know?" I thought about it for a moment.

"Do you remember the high school librarian, Ms. Silver?"

"Maryann Silver? You're doing her? Wow. She was at Helen's party, too. Her and Ms. G. I could never remember her name, really pretty woman, Ganglion or Ganglish... something like that."

"Gangwitch. Sally Gangwitch."

"Yeah, that's it. I never had her. Did you?"

"Yeah. Had her for Senior English."

"Hmm," she said, "My boyfriend Adam? The one with the big dick? He had the hots for her."

"A lot of the guys thought she was pretty hot."

"Did you?" I thought about what to say for a moment.

"Yeah. I did. I used to think she had bedroom eyes. She always had a look like she would love to spend the afternoon in bed with me."

"Adam flashed her."

"What? In school?" Her nod confirmed the answer to my question. "How do you know? Did he tell you?"

"He was bragging to his buddies, after they took that picture for the school annual of the two of us. He didn't know I could hear. He was telling them how he'd gone commando while wearing shorts and let if flop down the leg of his shorts, and that even though she didn't say anything, he knew she'd seen him."

"She never said anything about that to me."

"What? When?"

"When I spent the night with her." I ended up telling all about being with Maryann, how she'd called Sally Gangwitch while I'd been in her, actually fucking, and how Sally had hired me. It had been late, I'd fallen asleep and spent the night, and that both of them had said they occasionally had fantasies about doing some of their students.

"Wow. You fucked a teacher."

"Not when she was my teacher. And technically it was two teachers if you count Maryann."

"Mr. Matson was the one that always made me hot."

"Mr. Matson? Who was he?"

"He was the volleyball coach. The one that had the affair with the women's basketball coach?"

I shook my head. "I must not have ever heard about that. Who was she?"

"She?" She laughed, "No, not she. He. It turned out they were both gay. But my God, was he a hottie. They transferred the women's coach to another school when they became a thing, but I think they're living together. I'd have done him in a heartbeat." I didn't respond, I didn't have anything to say. "So, my mom likes it up the ass?"

"She likes sex."

"Regular sex too?"

"Regular sex too," I affirmed. I lay there for another moment or two before rolling over and getting out of bed. I asked Robin if she had any aspirin or ibuprofen, and she said in the medicine cabinet. I walked to the bathroom naked, took a pee, found the aspirin and washed it down with a full glass of water. I walked back into the bedroom and found Robin still lying on her side. I slipped back under the sheet and turned toward her.

"I can't believe you've been fucking my mother."

"She said she wondered what you would think if you found out she'd gotten me while you and your girlfriend hadn't."

"My girlfriend?"

"At Helen's? The one that was a cheerleader with you?"

"Lori. Yeah, she thought you were a hottie too. She's got a boyfriend now." I didn't say anything, but saw her shaking her head back and forth. "I can't believe you're fucking my mother."

"She won't believe it when I tell her I'm fucking her daughter."

"What? she said, at first shocked, and then realized I was joking. "You bastard! You wouldn't dare."

I laughed.

~

"Brent, I've got a divorce party next week," Melissa said over the phone, "they're asking about a standing 69 and probably a fuck for the divorcee. Are you in?" She gave the date, and that far in advance, I knew, without looking, it wasn't a problem but double checked my calendar anyway.

Melissa went in first when we got there, telling me to stay outside until she texted me. She wasn't sure who all would be there, so as usual, I wore my mask for the group setting. Some of the women didn't know that Melissa was part of the entertainment, but the hostess of the party did.

It was only a couple of minutes before I got her text to come on in. Along with the hostess we'd come up with a barely plausible scenario of my 'forcing' my way into the room, with Melissa 'greeting' me and telling me that I wasn't welcome, 'this was a women's party.' She met me at the door, and when I tried to step in, she put her hands up and immediately my Velcro attached shirt 'ripped' leaving me shirtless. Of course, I pulled on her clothes, our fake fight leaving me in just my tight underwear in no time. I ignored the other women in the room, pulled Melissa to me and slipped my hands under her bra and onto her breasts. I forced her clothes off, just as she'd "ripped" my shirt and pants off, to the cheering and clapping of the women who now were all sure this was all part of the act.

I hadn't been hard when we started, but Melissa's hand on my cock stroked me harder, and when she dropped to her knees to suck me in, all the watchers were cheering. As we'd planned, no sooner had she gotten me hard than I reached down and flipped her over into a standing 69. She sucked my cock and I licked her pussy, turning in different directions so everyone could see that I really was doing her, and then flipped her back over. Now naked, with a hard-on, I stepped up to the new divorcee who was sitting in a straight-back chair and straddled her legs to sit in her lap. She looked down to my erection pointing up at her, and I could sense that she was reluctant to touch it. "It's there for you," I leaned forward and whispered into her ear, "whatever you want." I saw her lick her lips and then leaned forward toward me. Sliding back and standing, my cock ended up right at face level and there was no more hesitation. To the cheers and claps of her girlfriends, she took me in her mouth, her hand wrapping around my shaft. Leaning back and putting my hands on my butt to display my cock to the room, I just glanced around, seeing that everyone was avidly watching. One woman had her hand over her mouth, blushing, but most everyone else was clapping and urging my divorcee on.