Virgin Gigolo Ch. 08

"Do we need to do a strip search?" Robin, or rather, Tiffany, asked right on cue. I reached back to pull my shirt free, easily pulling the Velcro loose and slipping it off.

"Absolutely," I said, slipping a hand into Melissa's blouse and onto her bare boob. "She might have a weapon. I found bullets," I said as I rolled her nipples with my fingers.

"I think she's drunk. We'd better administer a breathalyzer." Tiffany directed, stepping up behind me and, two-handed, pulled the sides of my pants, which immediately pulled loose and fell, leaving me naked, although I wasn't yet erect. I caught the heels of the shoes and they came free easily before I stepped around Melissa, and said, "All right, young lady. You're going to need to blow into the breathalyzer or we're taking you in." I heard the tearing Velcro on Tiffany's uniform, and looked over to see her now in just panties and her black half-cup bra, her tits on display.

"Just a minute, Officer..." Tiffany stopped. "What's your last name? I can't call you Officer Brent."

"Huh. Yeah, you're right. How about... Barnes? Brent Barnes? What about you?"

"Tiffany... Roberts. Like Julia Roberts," she giggled, "as long as we're being actors!" Melissa didn't say anything. "Ok, back at it. Just a minute, Officer Barnes, it looks like we need to recharge the breathalyzer." Stepping up to me, she dropped to her knees and momentarily took me into her mouth.

My mind was screaming. How many times over the years had I imagined Robin sucking my cock? Too many to remember, but not once had it ever been like this. "This is too weird," she said, pulling away. "Too sterile."

"Well, what do you suggest?" Melissa asked, "He really should be hard before he offers it to me to suck."

"Well, what do you think of a standing 69 like he did with Savanna?"

"You know about that?" I asked, surprised that she did.

"She told me. Said it was actually pretty fun."

"You've never done it, have you?" Melissa asked. She shook her head no. "I think it sounds like a great idea. You'll have to shed your panties, but you're virtually naked anyway. Take 'em off, and let's try it. Brent -- are you game?"

I nodded, and Melissa directed Tiffany how to approach me, where to put her hands, and where for me to put my hands, and we tried the lift and flip. I almost lost her the first time, but it was practically effortless by the third time. "Ok, let's try it again," Melissa said, "from the start. Clothes back on. Outside, bang on the door and let's get it right."

Tiffany and I had pulled our clothes back on when Melissa said, "Hey guys, are we forgetting something?" Turning, she pulled her arms a little sideways showing she was still handcuffed.

"Ah... minor detail, minor detail," I laughed, reaching over, and flicking the catch on the artificial cuffs. She pulled them free and I put them back in the holster, and we did it again.

Everything went flawlessly. I handcuffed, "Betsy", fondled her from behind, stripped my shirt and pants off, while Tiffany did the same, and then when I stepped around and she said we needed to 'recharge the breathalyzer.' She stepped up and grabbed me while I grabbed her, flipped her upside down, and this time -- she really did suck my cock while I ate my dream girl's pussy. I rapidly rose to the stimulation. When I relaxed my grip, Tiffany did also, and I easily flipped her back over.

"Ok, Betsy," Tiffany said, taking my cock in hand as I stepped toward Melissa again, "Be a good girl and blow into the breathalyzer."

Not unexpectedly, Melissa took me in her mouth, but just for a moment. "My God, he's got a nice cock, doesn't he?" she said when she pulled away. "Ok, what did you think? It was a bit rough the first time, but you two will do well together."

~

For the "real" Betsy, she may have been slightly inebriated, but she wasn't all that drunk, laughing and stopping me when I initially tried to expose her breasts, but not stopping my hands at all when I slipped them into her blouse and fondled and twiddled her nipples, eventually letting me pop her breasts free.

Betsy was very much like any of the other MILF's that I'd been servicing. She wasn't the smoking hot raving beauty like Robin or Savanna, or even Melissa for that matter, but not ugly by any means either. She was a bit overweight, not obesely fat, but a lot of her weight was carried in her D-cup breasts.

Tiffany did a great job of working the others (four women and three men), accusing them of hiding weapons or being drunk, fondling both the men and the women, eliciting many laughs, and I suppose many fondles of herself in return. When I finally got naked to "make" Betsy blow into the "breathalyzer," Tiffany and I easily slipped into the standing 69 until I was erect. Everyone thought that was hot, and after Betsy sucked my cock to "prove" she wasn't drunk, three of the other women took a short turn also, drawing laughs from everyone. All of the men backed away from that, which didn't hurt my feelings in the least. When I made my way around the room and back to Betsy she didn't hesitate to take me in her mouth again, and then almost immediately pulled away, grabbed me by the cock, and drug me into the bedroom to the hoots and applause of her friends with a "Fuck her good!" call from one of them, eliciting laughter from the others. She stripped off her pants and laid back on the bed, and when I stepped forward, naked and cock hard, she shook her head no and said "Uh-Uh. Tongue first."

As Melissa predicted, Betsy was a well-satisfied customer by the time we left.

That was the first time that Robin and I performed together. The word apparently got around that our standing 69 performance was hot, as we performed it several times upon request over the next few months.

~

Robin and I had met at Melissa's to go to our police gig, which became the norm whenever we worked together. Driving together, to wherever we had to go, gave us time to talk and connect. "You fucked her?" Robin asked as we were heading back to Melissa's, acknowledging that I'd gone into the bedroom with Betsy, but whether I had actually fucked her or not wasn't necessarily a known fact.

"Yeah."

"I guess it's no different than me with my customers." I shrugged my shoulders. "How many women have you made love to?"

"Made love to?" I repeated, in my mind immediately translating to the difference that Mary had taught me. "None. I've never made love with anyone, I've never had a lover, but I've had sex with... wow, I don't know... I guess, more than 30?" I mentally flashed through name after name, every name leading to another.

"Really?" she asked, is that all? Why do you say that it's not making love when you have sex with someone?"

"That came from Mary. When I said to Mary that she was my first lover, she corrected me, saying that having sex and making love are two different things. She said that when you're in love with someone, sex accents your love and makes it better, but if you're not in love, it's just sex. It kind of made sense, even though I didn't know the difference, but I've always just kind of used that definition in my mind."

She was quiet for a moment. "You've really never had a girlfriend?" I shook my head no. "I've thought I was in love three different times. My first boyfriend in high school was David, and then there was Adam. Everybody thought that Adam and I were going to be a forever thing, but he was just eye candy, but OMG... he had the biggest cock I've ever had." She giggled, "Kind of spoiled me for anybody else." I laughed.

"What's so funny?"

"That's what your mother said."

"What? My mother? When?"

"When I overheard her telling my mom that she'd caught you two fucking in the living room. She said something like 'you were a really lucky girl' and she hoped he didn't make you think every man was going to be like that."

"He may have had a big cock, but he was a lousy fuck. I don't think he ever gave me an orgasm that way." She giggled. "I think he was the definition of premature ejaculation."

"And of course, I made the mistake of marrying Dennis," she continued. "It's funny, when I look back on it now, I wasn't in love with any of them. I thought I really liked them and thought it was love, but you know, I was probably closer to actually being in love with David than with any of them, and I realized early on that I was just infatuated with him. When I think about it like that, with your definition, in hindsight, I guess I'd have to say I've never made love with anyone either."

"How many have you had sex with?"

She looked thoughtful for a moment before answering. "Including blowjobs?"

"I guess," I answered, not having considered that before. "Do you consider that having sex?"

"I don't know. I did a lot of dating once I turned 18; sucked a lot of cocks. We didn't consider that having sex at the time, it was just foreplay, but I'd say it was now."

"Not many of my... clients... don't want to suck me at least a little. Do all women like sucking cock?"

"Oh yeah, I think most do. Didn't you ever hear my nickname?" I shook my head no. "The girls on the cheer squad called me BJ. I dated a lot, but wouldn't have sex with them. David and Adam were the only two that I ever fucked, but I almost always gave a blowjob at the end of a date if I'd had a good time, and I did a lot of dating. Sometimes it was just a hand job, but I've always loved sucking cock."

"Wow."

"Yeah, so I guess that was sex, of a sort. But I didn't start fucking for money until after Dennis and I split."

"Escorting?"

"Yeah. Businessmen will pay big bucks to have a pretty girl on their arm at some business meeting and most don't even think twice about paying lots extra to take me to bed."

"How often does that happen?"

"A lot," she paused. "I, um, usually have a date anywhere from 3 to 5 times a week. I never do Sundays, that's my homework day, and I try not to on Saturdays. I've got one guy who comes into town the first Tuesday of every month. He takes me with him to his business dinner meeting, I'm his eye candy, and then I spend the night with him."

"I play with Mary almost every Saturday morning, and sometimes someone else on Saturday evenings, but most of my trysts are during the weekdays."

"Lonely housewives?"

"Some. More divorcees and widows than just lonely housewives." I pulled up into the parking garage. "Where's your car?"

She directed me to where she was parked, and we got out to go upstairs to change back into our street clothes. I offered to take both uniforms back to Marty and she agreed, handing hers to me. I saw her glance back over her shoulder toward me as she drove away, and I walked toward the elevators.

~

Fake Police strip and sex parties were quite popular, but it seemed that bachelorette parties were the ones that requested two of us as 'police' the most -- and almost always they wanted a standing 69 exhibition. Sometimes it was with a 'fuck the bride' party, but often, rather than fuck the bride, watching us have sex was requested. I don't know as we ever had a Fake Police request for a bachelor party, but multiple times for someone's work-related party.

Robin and I definitely had a certain 'chemistry' together and when the word got around, we were probably the most popular request. We would go through our "arrest" routine, gradually stripping, followed by the 'blow into the breathalyzer' gag, and then if the bride didn't want to, or we knew she wasn't going to beforehand, or if it had been requested, Robin and I would put on a fuck exhibition. The breathalyzer routine always started slow, until one of the ladies finally succumbed and took me in her mouth, and then more often than not -- most of the women in the room wanted a taste of me.

After a while, just walking into the room, I could tell which woman was going to do it first. I'd approach others; they would giggle and beg off, and then when I got to whomever I'd identified as the most open, with just a little bit of extra banter she'd lean forward and take me in her mouth. Many of the girls would fondle my cock or butt as I worked my way by the first time; many would grab my ass and hold me while they took me into their mouths. More than one did a deep throat, probably "proving" to her friends that she could. After that, another round of the room would get many of the women who had passed the first time to also "blow into the breathalyzer."

The first time Robin and I fucked for a show, she pushed me down onto a straight-backed chair, straddled me, slipped a condom on, and then slipped me inside her. We did it cowgirl, and then she pulled off and did reverse cowgirl, which made it easy for me to fondle her breasts, and as we got close I reached down and fondled her clit, until she came before I did.

"Why'd you do that?" she asked later as we were on our way back to our car.

"Do what?" I asked, puzzled at her question.

"When I did you..." I could feel her looking over at me, "You reached down and fingered me until I came first."

"Yeah, I always try to make my lady cum first." I glanced over at her, feeling her looking at me. "Why?"

"Not many men do that. I would bet the times that I've cum first I could count on one hand. Hmmm." I glanced over again; she was shaking her head thoughtfully. "When I was married to the dick, a lot of times he wouldn't even realize I hadn't cum unless I told him he needed to keep going. Once he'd cum, it's like he assumed I already had."

"Again, that's because of Mary. She always said that, if I took care of my girl, that my girl would take care of me, and if she didn't cum before I did, I was doing something wrong."

I kept glancing sideways toward her, but she didn't say anything more until I pulled up by her car. "Thank you."

I didn't have to ask "Thank you" for what.

~

It was an afternoon Frat Party, at a University in another town, with easily a hundred people there, both men and women. Melissa worked a lot of Frat Parties herself, admitting it could be difficult for those of us attending the University if we were recognized by classmates. Whenever I worked a party where people might know me, I always wore my mask.

It was originally supposed to be Savanna and me but late in the week Savanna came down sick and Robin agreed to go instead. Frat parties were always difficult for the girls, especially if it was only Frat brothers there. Somehow the frat brothers always thought that because they had paid for the girls to be there, the girls would fuck everyone, and it should be included in the fee they'd already paid. Melissa always made sure that when one of the girls went to a frat party either a coworker went along, or a bouncer/bodyguard, and frat parties always paid more because of this.

In typical frat boy fashion, the guys at this party seemed to not understand that Tiffany and I were there to entertain, but then they showed us the back room where Tiffany could fuck anyone that wanted and they wanted to get her first before the party officially started. She said it didn't work that way, but when they started getting aggressive, I had to step up and get between her and the guys. "Listen guys, that's not the way this works. We're here for an exhibition, and if that helps you get lucky with some of your guests while we're here, fine, but Tiffany isn't part of the package. Back off, or we're out that door, and what you've paid already will go with us."

I couldn't believe that I'd stepped up and confronted these guys. These were the same type of guys that had intimidated me in high school, except that now I was as big as they were. There was one that didn't want to back off and I thought it was going to be real trouble when he said "Fuck, we paid for a sure thing to be here," but another brother stepped up with a "Dude, back off. He's right, we paid for them to give a show, not to fuck everyone." That's all it took and an hour later, with everyone watching, I walked through the crowd holding Robin upside down while I licked her pussy and she sucked on my dick. We moved back to the front of the room where a mattress was set out, sort of as a stage, and once again I lay on my back while Robin rode me to orgasm."

I heard a woman's voice say, "Fuck, she really came! Let's go to your room because I want to do that with you."

~

"Thank you," Robin said as we were headed back later that evening.

"For what?"

"Helping to defuse that... situation." I nodded. "You know Savanna probably would have?"

"Fucked the frat boys?"

"Yeah. She likes doing groups. Not me."

"But you've done threesomes?"

"Yeah, but that's about my limit. Threesomes are really one-on-one with rotating partners. Even then, there are times when it's the two of them and you just get to watch." I thought back on my times with Paul and Lindsey, and for the most part, she was right. Lindsey and Paul, Lindsey and me, and even lying there with Lindsey watching Paul suck me hard, she was watching while the only interaction was between Paul and my dick.

"Even when you're with two guys?"

"Yeah, not always though. Two guys always want to spitroast me, have me suck and fuck at the same time. I like that, but even then, invariably the guys will get off on fucking me but then they usually end up with each other, too. When that happens, I'm the third wheel."

"Really?" I asked, having not experienced that directly, I wasn't quite able to decipher the interaction. "Just right in the middle, they start in on each other?"

"Most of the time they talk about how hot it is to be seeing the other fuck me, but usually after they've cum the first time, one will go down on the other to "get him hard" so he can do me again. Sometimes they openly admit to being bi, but sometimes I don't think they've yet admitted it to themselves." I nodded.

"Hey Danny, are you going home?" I glanced at the clock on the dash, seeing 1 am before answering.

"Yeah, why?"

"Wanna get something to eat? I'm hungry. I didn't have anything to eat before our gig."

"Now? Where?"

"There's a 24-hour Mexican joint near my place. They've got killer Margarita's."

"Yeah, but I can't legally drink just yet."

"Oh my God, Danny. You're in college, you fuck for a living, and you haven't got an ID that says you're old enough to drink? Oh my God," she repeated shaking her head and laughing. "Don't worry about it, I know the people, they won't give us a hard time."

It wasn't far to her place, and it became our little ritual on the occasions that we worked together. I'd swing by, pick her up, we'd go to our gig, and we'd go back to her place and walk to the Mexican joint. I never asked to go into her apartment and she never offered.

She was right; they didn't check our IDs, but that first time -- one margarita was more than enough. I'd had a beer a few times in my life, but never had anything harder. I had never been drunk before and could tell the margarita had really affected me. I finished it but followed up with a coke, and by the time we sat and talked for an hour and walked back to where my car was, I was feeling OK again. With Robin's apartment door visible from the street, I just sat and watched until she got the door open before I drove away.

~

"Is this Brent's, uh... Yard and..."

"You've got it," I answered, interrupting the stuttering question. "May I help you?"

"I'm, uh, wondering if I can get an appointment." I'd double-checked the caller id -- nobody I'd ever talked to before, or at least I didn't have their phone number in my addresses.

I asked enough questions to ascertain that she knew the "Yard Service" was a façade that explained an income and something I could report to the IRS that wouldn't draw too many questions, but pleasuring older women with my cock or tongue was my specialty. "Maryann Silver," she told me when I asked for a first name, but I told her I didn't keep last names, that way I never had to confess something that I didn't know. I added her first name to my address book.