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 other than Mary's about three nights or afternoons a week, and at least once every Saturday and Sunday. My routine during the week was classes or studying in the morning, followed by studying or classes in the afternoon -- until I departed to my customer du jour. I could play with Mary on Saturday mornings, and invariably Saturday customers wanted afternoon or evening trysts so I often got paid twice on Saturdays.
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 advisor, 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 having 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 the 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 whose 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 were 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 slipped in next to me and took 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 swinger's 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?"
