Virgin Gigolo Ch. 07

Going to college I found my GPA climbing. What had previously been a marginal passing history, was now much more than that. I'd like to say it was because I was no longer chasing girls and spending time drinking with the guys, but really it was that my evenings were booked, and I had to actually get up and do homework or it wouldn't get done. It's funny how paying attention during class and then reiterating on my own every morning what had been taught - exactly as every counselor and professor had ever recommended was needed to succeed - actually worked.

My 19th birthday came and went. I had enough regular MILFs and semi-regulars that I was in someone's bed about three nights or afternoons a week, and at least once every Saturday and Sunday. My routine was classes or studying in the morning, followed by studying or classes in the afternoon -- until I departed to my customer du jour.

It was obvious, even before I went to school, that I'd not be able to live at home. Following the advice of Melissa, I got a simple non-descript apartment off-campus. Rather than paying for a dorm or joining a fraternity where I would constantly be distracted by those who were more there to get laid than to go to school and learn, I had the privacy I needed and the ability to come and go at will. Melissa did indeed introduce me to her investment advisors, and suddenly I had money being put away while having more than enough to cover all my expenses. By the time the first semester ended, I had enough money invested and saved to pay for the rest of my education.

Besides regularly servicing Mary and my other MILF's, about every second or third week I'd get a call from Melissa and she'd have a bachelorette party or a sex show for us to do somewhere. Her number, like mine, was always passed around strictly by word of mouth. The bachelor and bachelorette parties were normal and understandable, and occasionally a woman would call for a man which she'd pass on to me, but also occasionally something surprising came up. One such case was a swinger's party where we performed together. Another, also quite memorable, was a 'black tie" event in a neighboring town.

At the first party Melissa told me we had agreed to be the 'warm-up' entertainment. It was at a private home, in a normal residential neighborhood. I'd gotten used to the idea that behind closed doors, though I'd never seen it myself as a kid, people were doing sex, and not necessarily just with spouses. Here it was very much a neighborhood just like I'd grown up in -- with no hint that anything was different.

The home had a large hot tub in back and an enclosed patio or party room, with a bed set up front and center which couldn't be seen from the front door - but as soon as anyone entered and turned out of the entryway -- the entire front and party rooms were visible. Jean and Joe were the hosts, Jean greeted us at the door wearing a white silky robe and explained that she hadn't expected us for probably another 15 minutes or so. Jean said she'd be right back, and Joe came out to greet us, already dressed for the occasion. He was almost nude, just his cock and balls in a see-through mesh cock sack and seconds later, Jean reappeared, having shed the robe, now wearing "barely-there" lingerie, dangling nipple jewelry, and a gold necklace that read "COCKSUCKER."

They showed us to the party room, indicating where we were to position ourselves. Melissa had already told me we were expected to be fucking and sucking each other on the bed as people were arriving, visually breaking the ice for people who already knew what they were there for. They showed us a side room to put our clothes in, and as we were going to be nude, just got naked. Melissa had made the arrangements with Jean and reiterated that we were performing with each other, and if anyone wanted extras, she should tell them that private parties were $500 for one of us, or a thousand for the two of us. They said that everyone had already been told that, and since everyone was chipping in for our fee, that was probably a bit out of most people's price range. Everyone had agreed that watching us fuck was what they wanted, and a vertical 69 had been specifically requested as a great change of pace. When the doorbell rang, just a few minutes later, Melissa and I moved to the provided bed and began playing.

Even though we were both nude, I hadn't even begun to get hard yet. Melissa took care of that, pushing me onto my back and kneeling on the bed beside me so that she could suck my cock. I rapidly stiffened to her mouth music, and when I looked again, half a dozen people were now watching. Most of them came up to the edge of the bed and greeted us, somewhat surprisingly thanking us for being there.

Eventually Jean came over and said everyone had arrived and we should do the promised standing 69 that everyone thought had sounded hot. Looking out into the room, I saw nobody masked or hiding their identity, but I didn't recognize anyone. There were easily twenty-five to thirty people or more. Unlike the last time we'd done a standing 69, where I just stood there, this time I walked around with Melissa locked in place, giving everyone a closeup view of our unusual coupling with her head bobbing on my erection, my face locked in her pussy. When we got back to the bed, I lowered us into a "sitting 69" where I sat on the edge of the bed and held Melissa in place which wasn't nearly the athletic event that a standing 69 was. Eventually Melissa slipped off, I turned her over, she made an overt demonstration of wiping a condom onto my cock, and we began having regular sex - or at least performing different positions. Just like the last time, she pushed me onto my back and climbed on, but unlike where she'd gotten herself off, this time it was just a short display before we moved on. Someone called out, "Do her doggie!" so she rolled up on her hands and knees and I slipped into her from behind. From there we moved on every couple of minutes, sometimes to a request, other times just to change positions.

Virtually everyone paired up as couples and were playing themselves as we were fucking and playing in front. I'd occasionally noticed couples coming in, usually already undressed or dressed for sex, but only when there was something distinctly different did they register as memorable. I had seen one black couple arrive, and now noticed both with a white partner. I'd noticed a very buxom gal with dangling nipple jewelry along with a shorter man who's head barely rose to her breasts -- and now she was fucking a tall, good looking, man while her partner was just watching. All these images were just flashes as we didn't have a lot of time to look at the crowd except when we took a slight break and got drinks ourselves. Even though I'd only seen and specifically noticed a few of the couples arriving, now as I looked around I could tell that most of those that I did remember from earlier were no longer with the person they had arrived with.

At first all I saw was couples, but as I looked around I saw one woman who had a man straddling her while she was sucking his cock, with another man between her legs licking her pussy, and what I assumed was her husband just sitting beside her in a chair, stroking his cock, while watching two men servicing his wife. I realized there were a couple of threesomes, MMF and FFM variety, as well as at least one couple of just two women together. I saw Jean sucking a cock, and a while later saw her sucking the black man with his mate standing next to him and watching.

We were only scheduled until midnight, and as we got ready to leave, Jean came up and thanked us. I asked how long the party was going to go, and she said many would be spending the night, but many also had kids and babysitters they had to get back to so would be leaving fairly soon.

"You're more than welcome to stay and play," Jean offered, "or if you'd like to come back and join our monthly party, you would be more than welcome."

"Thank you for that," I answered, Melissa slipping in next to me and taking my arm, "but most Saturday nights are booked well in advance."

"I understand, but the offer's always open. Think about it, you're both welcome, either alone or together." Reaching up she rested her hand on my arm just after Melissa had pulled away and stepped to the door, "Can I offer you a blow job before you go?" she asked, a smile on her face. "I don't wear this necklace for no reason," she giggled, "I really do like sucking cocks."

"Maybe some other time?" I smiled, "but right now my ride is leaving." Melissa had cracked the door open, obviously waiting for me.

"Of course, next time. A young cock like yours is always welcome." I turned and followed Melissa.

"Well done," Melissa said as we stepped out to the car. "There will always be an offer to join them, or come back on your own, but just remember, this is your business. She already knows you're available for a price."

~

The black-tie affair, a couple of months later, was a little bit different, mostly just in who was there (in that, we never actually found out -- but we had our own suspicions) and in who went with me. The swingers party had been "normal" people; the black-tie affair on the hill were all "pretty people" and, I presumed, wealthy people.

"Are you willing to go with someone else?" Melissa had asked when she called me up to tell me about it. "I've got an appointment that night, but one of the girls said she'd be interested." When I said I would, she said "This will be a bit different. It's a black-tie dinner party and only you and Savanna will be getting naked, at least while you're there. They're all swingers, just like the last party, but they're very secretive about who they are. Your standing 69 is becoming pretty famous, they've asked about that, but other than that it's up to you guys what you do. Are you in?"

"I'm in."

"Ok, good. Can you come over tomorrow so you can meet Savanna? She's never done a standing 69 before."

Up until that point I'd never met even one of Melissa's "girls." I knew that she always said that her girls were high class escorts who liked to be wined and dined and were more than just eye candy on someone's elbow, but I knew most of them also were usually willing to just have sex with a client without the escort duties. Melissa told me the girls were only an "almost" sure thing, in that they always had a veto. If the guy was a jerk, mistreated them, or something "just wasn't right," they could walk away, and she supported that. She said that several times she'd gotten a call complaining that the girl had walked away, and, in every case, the girl's tale had been quite a bit different from that of the complaining party.

When I arrived on Wednesday, Savanna was already there. To say that Savanna was smoking hot would be an understatement. She was absolutely fucking gorgeous, and that I would be having sex with this beauty and getting paid for it, seemed absolutely unbelievable. Savanna was closer to my age than anyone I'd yet been with, and even though this was "business" I felt myself a little intimidated. I knew if I'd tried to talk to this girl, this woman, and tried to ask her for a date, tried to get her to where I could maybe try to seduce her in a normal situation on my own -- I would have been a blithering idiot. As it was, with our relationship to be strictly business, I just nodded and said "Hello."

"Melissa says you're pretty good at a standing 69? That's a bit athletic. I've never done that before," Savanna said without so much as an introductory "hello." The way she spoke, the tone behind the words, said it was a challenge to me. Unspoken was a "Who the fuck do you think you are? Do you think you're good enough for me?" I wasn't sure why but that unspoken challenge was all it took for my intimidation to take a back seat.

I just looked at her for a moment, sizing her up. She was slightly smaller than Melissa and perfectly proportioned, so I knew I'd have no problem handling her. Shapely, athletic, legs disappeared into a skirt several inches above her knees. A sliver of belly showed beneath a blouse that pulled tight against a moderately large bosom. Her face was absolutely barbie-doll perfect, silhouetted by gorgeous, silky, naturally blonde hair. This was a woman who was naturally beautiful, knew she was naturally beautiful, knew that every guy she'd ever met had his tongue hanging out, and consequently she expected those slavering guys to kiss her ass.

I sensed Melissa watching, seeing how I was going to respond, but I didn't break eyes with Savanna to see whether she was or not. What was this start, almost an attack from someone I'd never met? I barely hesitated, reached out my hand in greeting, and said "Pleased to meet you too. I hope your pussy's not as tight as your ass."

I saw it in her eyes that I'd answered perfectly, although I still didn't know why. She took my hand, I shook it, and turned toward the chair, my eyes crossing over Melissa and catching a smirk from her.

"I'm sorry about that," Savanna said, her voice no longer attacking, now apologetic, and then she sighed. "I guess I didn't have to be a bitch. I've been hit on by virtually every man that I've ever met since I was fourteen. You get a bit jaded; when everyone you meet just wants to get into your panties it's hard to tell the nice guys, even though Melissa said you were."

"I thought you two would be perfect together," Melissa interrupted, "and I can see I chose well." Going right into explanations, she said "This one will be a most unusual job." She went on to explain that this was a very exclusive swingers party. The participants were politicians, doctors, lawyers - the elite of society -- and they had all the sexual wants and desires of anyone else, but they had an inordinate need to keep their private lives private.

"It's a very exclusive black-tie affair," she said, "and you have to blend in, at least when you're arriving and departing." She pushed a business card across the desk towards us, which Savanna took, and then thumbed something on her phone. I hadn't even noticed her earpiece, but when she just started talking, I realized what was happening. "Hey Marty, Melissa. I've got a couple I'm sending over to you to dress for the party... Yeah, that party..." she laughed. "Yeah, the usual. Black tie for him, sexy formal... yeah, you know the drill. OK, they'll be there in half an hour."

She looked back at Savanna, who handed the card to me. All it had on it was a name and an address. "Marty's like us, she only works through referrals," Melissa explained. "She'll send me a bill; all you need to do is go to her and get fitted and then go back on Friday to get the clothes and try them on. And then on Saturday, bring them here with you, get dressed here, and I'll have a limousine to pick you up."

She pushed another card to me; it had an address on it. "This is the party location, It's a gated community, you'll need an invitation to get in." I looked at it and passed it to Savanna before Melissa held her hand out to take it back. "Even the exact address is kept discrete," she said as Savanna handed her back the card, "You'll get this back on Saturday," she said as she put the card back. "Bring your clothes up and change here, and then you'll put these masks on," she said indicating two masks sitting on the desk. I'd noticed them before, stacked, but hadn't thought anything of them at the time. "Once you're dressed and masked, the limo will be waiting downstairs in the basement. You will not go outside of this room without the mask on until you get to the party. Going in or coming out, until you're back in this room, keep your masks on. You'll need this invitation," she said, flashing a larger card but not showing it just yet, "just to get onto the grounds once you're inside the gated community. The driver will drop you off, and then he'll come back later when you let him know you're ready."

~

The mansion on the hill was obviously a very expensive place. I'd never even been in a black-tie tuxedo before. Although I'd seen them on TV shows and movies and knew they were considered high-class dress for men, even though, in my opinion, they were somewhat plain. It wasn't until we arrived that it dawned on me that perhaps that was the point, to make the women exotically beautiful by parading them next to a plain black escort.

Savanna was exotically dressed; her own gown was as exceedingly sexy as my tuxedo seemed exceedingly plain. A plunging neckline went nearly to her naval. Her breasts, at least half exposed and almost too large to be braless, swayed pleasantly as she walked. The side was slit clear to her hip, a thong string occasionally letting any casual observer know she wasn't totally nude beneath the dress although the naked back and vee of the dress plunging to her naval made it plain her breasts were unencumbered by a bra.

Even arriving in a limousine we'd been required to present the invitation to get through the community gate. We'd then had to present it again at the gate of the house property, and yet a third time where we had been required to relinquish the actual invitation card at the door. We were greeted by two men in tuxedo's, also wearing masks, as was everyone that we saw. Servers, waiters, bellmen, anyone that we saw also had masks and were mostly totally indescribable.

Other party participants were arriving at the same time we were, one car pulling out just as we pulled in and another arrived right behind us. Even after two gates it seemed strange that we still had to present the invitation at the door, and although I wasn't aware how -- somehow it must have been marked as the man at the door told us the host would be right with us. The previous couple was no longer in the entry when we got inside, and a moment later a man appeared seemingly from nowhere, saying quietly "Savanna, Brent? This way please," and led us down a side corridor. Opening a door at the end of the hall, he waited for us to step in and then followed. "We've heard good things about you two," he said, "I'm sure our audience will be most approving." He closed the door as he stepped in behind us.

"Melissa did quite well with both of you. OK, ground rules. Sorry about requiring a tuxedo and evening dress when you're just going to take them off, but paparazzi and others are always looking for something, and believe me, there are probably already pictures of you arriving. We're quite circumspect about what is seen in public... and what takes place behind closed doors. By wearing masks and dressing as everyone else, they probably won't be able to decipher who you are. But, these people ..." he said, indicating toward a door on the opposite side of the room, "want their privacy and this way you look just like any of the other people arriving. I doubt that anyone will take a mask off while you're here, but if they do and you recognize them... you will never admit you saw them," he said, reiterating the instructions Melissa had given. He paused, looking back and forth between us. "Do you understand?" I nodded; Savanna did the same. "Good. Melissa was highly complimentary of both of you and said you'd have no problem with utter discretion." For the second time tonight, he'd used Melissa's name outright, and I couldn't help but wonder how he knew her.

"This is your room where you will undress and leave your clothes and masks. This is the toilet," he said, stepping to yet another door and pushing it open. "Toilet, bidet, shower if you need. After the dinner entertainment, you two will return here and dress to leave. Once you're dressed and have your masks on, you'll come back out here," he said, indicating the exit, "and mingle with the other guests. Most will be moving into the theatre, to the right, but several couples will not be staying. You can leave along with those that don't stay."