The Prize | THE BOY SERG | Chapter 7

I’ve grown closer and closer to the inner circle of The Collective. Actually, it has happened faster than I expected. I’m still self-conscious at times, but they never fail to make me feel welcome.

I love to play cards, more particularly poker. The first game that I hosted for men from The Collective was just a low key way to return Legrand’s hospitality after he invited me over for dinner. It has turned into a monthly occasion.

The first Saturday afternoon of the month, four or five of the guys came to my place for a cash only, high stakes poker game. We played Seven Card Stud. There are no limits but no IOUs; you bring what you are willing to lose. The guest list varies but this month it was Legrand, his best friend Adam Snow, Dallas Steele, and myself.

Adam had won an online auction bid on two sealed 60 year-old bottles of Glenlivet scotch whiskey. I was deeply honored that he chose to bring one to my party and equally thankful that I had just recently invested in a set of Baccarat whiskey glasses that were worthy of such a treat. Let’s just say that the whiskey was everything you might imagine and we were enjoying it immensely. All of us were more than a little bit tipsy, the game was more suspenseful than usual, and we were getting pretty rowdy.

I’m generally a good poker player and that’s part of the reason I enjoy it. I was down on my luck, though, and not doing as well as usual, then my luck changed. I picked up my cards and there they were, three aces. I asked for cards and got the fourth one. I was ready to play! Unfortunately, Legrand was, too. Adam folded right away, but Legrand and Dallas stayed in.

Dallas is a great guy, but he's a lousy poker player even when he’s sober. He never knows when to quit. Legrand on the other hand, is a very cagey player and totally willing to bluff on a half-way decent hand. I had been dealt trash cards all afternoon and I don’t think he believed I finally had something worth playing. Unfortunately, after a few rounds of bets, my chips were running low and neither man would let me call.

There was only one thing to do. I went all in, putting my boy Serg’s ass on the table with the last of my chips. Since Legrand had the most chips on the table, it was his choice as to whether this bet would be allowed. It wasn’t exactly an IOU, since Serg was right there and ready for collection as soon as the game was over. It wasn’t like Legrand didn’t know exactly what the value of the offer was, so to speak.

Legrand gave me a lopsided grin and said, “add your ass to the pot and it’s a deal,” pushing his chips into the center of the table. Poor Dallas just looked confused, and folded, reaching for the almost empty bottle of whiskey. Adam tipped his glass up to drain the last few precious drops of whiskey onto his tongue and leaned back in his chair slowly looking back and forth at us.

I have to admit, it set me back a moment. Legrand’s dick is huge! On the other hand, my hole twitched at the thought of what it might feel like. It’s not like I haven’t been fucked before. It doesn’t happen often because there are not many men that I will submit to, but Legrand Wolf is Legrand Wolf and, as they say, “In for a penny…”

I giggled, with what turned out to be too much confidence, and said, “Sure!” I proudly laid my four aces on the table. Legrand didn’t even look at them. Holding my eyes locked with his, that odd little grin still twitching on his lips, he laid his cards down one at a time… seven, eight, nine, ten, jack…all hearts. “Fuck!”

Adam let out an amused chuckle and said, “Yep, Eddie, ‘fuck’ indeed! Come on, Dallas, my driver will drop you off at home and you can send your boy back for the Maserati later. These gentlemen have business to settle.”

Dallas was busy cashing out his remaining chips and slurred, “Do you really think I let my boy drive the Maserati?! I do appreciate the lift, though.”

The two men gathered up their things. I started to get up, but Serg was already standing in the foyer holding the men’s jackets and Adam put his hand on my shoulder and said, “No, don’t get up. We know where the door is. Have fun!” The two men stepped out onto my front porch, already making jokes at my expense, although I knew it wouldn’t go any further than the back seat of Adam’s Mercedes town car.

That left me and Legrand sitting at the card table with Serg standing by expectantly. He had been in the room and heard the bet being negotiated. While he’s a boy of impeccable training and would bend over for any man that I ordered him to, I suspected that he was secretly thrilled at the opportunity to be fucked by his old master.

Suddenly, I was actually facing the prospect of Legrand Wolf fucking me and me realizing that I wanted it. Wanted him. I mean, I respect him, of course; admire him, certainly; think he’s handsome, that’s simply an objective fact. I wanted him to fuck me. I wanted him to want to fuck me. Suddenly, I felt incredibly, disturbingly vulnerable.

I stood up and said, “I’m a man of my word. Serg, go make sure the guest room is ready. We’ll be up in a minute.”

We went up to the guest room and Serg crawled in on his knees to meet us like the well trained slave that he is. We slowly undressed him, admiring his beautiful young physique, and then had him undress us. Standing there in our jock straps, with Serg worshiping our bulging packages, Legrand leaned in and we shared another long lingering kiss. Then, Legrand ordered Serg onto the bed and motioned for me to go first.

I fucked Serg for a while and then turned him around for Legrand, who then beckoned me around. I had almost begun to think Legrand wouldn’t fuck me after all but, as I took my boy for the second time, I felt the fat knob of Legrand’s cock pressing between my cheeks and shuddered, realizing that it was time. At first his cock forced my hole so wide that I wasn’t sure if it would go in. It did.

He slowly sunk it into me. As he began to fuck me, I felt my ass transform. It felt right. I realized that I wanted him to fuck me harder but I held my tongue and let him go at his own pace which was very gentle. Just as I was beginning to hunger for his load, getting myself ready for him to plant his seed deep in my guts, he pulled out.

He had me turn over on my back and told Serg to ride me. He pushed my legs back and I thought he was going to finish fucking me. Then I felt his cock against mine. Serg let out a loud groan as Legrand’s cock stretched his hole wider than he thought possible, certainly wider than I would have imagined.

I felt Legrand’s fat, hot, slick rod sliding up into Serg’s, now impossibly tight, velvet hole next to mine. Both of us fucking, and feeling each other fuck, this boy that had belonged to both of us. I had thought that having Legrand fuck me was the closest that we would ever be to each other. This, though, was the most amazingly intimate connection I ever had with another man and my nuts boiled with a mind bending orgasm.