Pool Bet

[This is the second chapter of a story that started with a bet on a game of pool. There's enough background in this installment that it can stand on its own, but you might want to read the previous installment first if you haven't yet. It's my highest-rated submission so far. It's at http://www.literotica.com/s/pool-bet. Either way, I hope you enjoy the new chapter. - TD]

This is awkward.

I was afraid it would be, but Dan had sounded very nonchalant and ordinary when he'd called me over to shoot some pool again, and it was an ordinary invitation. We'd been getting together at his place to shoot pool about once a month for years, and I was grateful the invitations hadn't stopped when my wife and I split up. I hoped I had sounded equally nonchalant on the phone, and I'd picked up some beer on the way over as always.

But now, after a few minutes of small talk about his kids, my divorce proceedings, and work -- both of us studiously avoiding any mention of his wife or the last time we'd been together -- we'd been quiet for a long time. It was unusual; we usually laughed and joked a lot. And it was awkward.

I guess that's understandable, given that the last time I'd been here, we and his adorable wife, Melissa, had all wound up naked together after she proposed a bet on our pool game. I'd won, entitling me to a blowjob from her. Then, to my shock and her delight, she'd persuaded me to pay up as if I'd lost -- by sucking Dan's cock while she watched. Afterward, she thrilled me by sitting on my face until she came twice, then sucking me off twice, the second time while Dan did her from behind. This was the first time Dan and I had seen each other since then, and Melissa wasn't home. And now here we were, shooting pool in silence except for the occasional "Your break" or "Want another beer?".

I knew we had to talk about it, but I couldn't decide what to say. I figured Dan was probably having the same problem, which didn't make deciding what to say any easier.

When our second game ended with no change, Dan tossed the rack on the table to get ready for another, but I said, "I don't know, I'm kinda wiped, maybe I'll get outta here."

"C'mon, man, rack 'em up," he said. "And look, uh, can I ask you something?"

"Sure," I said, racking the balls without looking up.

"So, uh ... how was it?"

"How was what?" I asked, knowing exactly what he was asking about.

"Yeah, right, as if you haven't been trying to figure out how to bring it up all night," he replied.

I looked up and acknowledged it. "You're right. I have."

"So? How was it?"

"Totally worth it," I said.

"Yeah, I could tell you had a good time with Melissa afterward. But that's not what I mean. What was it like?"

"I'm not switching teams, if that's what you mean," I said, probably too defensively. I hadn't quite come to terms with it myself yet.

"That's not what I mean either, and you know it," he said. "Look, I think Melissa would still like to see me do it, and I want to know what you thought about it."

"I don't know, man," I said. "That whole night was hotter than hell for me. I mean, I finally got to see your wife naked, and she's fan-TAS-tic, and then to have her sit on my face and blow me -- I can't really separate, uh, what I did to you from everything else, y'know?"

"OK. It's your break, by the way."

After I broke, he said, "I guess what I really want to know is, would you ever do it again?"

I thought about it a little, then said, "In the right circumstances, yeah."

"And what are those?" he asked.

"A beautiful woman asking me to," I said. "And promising to make it worth it."

"So ... you don't want to do it now," he said, lining up a shot. It wasn't a question.

"No," I answered anyway. "Why, do you want me to?"

"No," he said -- but I thought he sounded a little uncertain about that. He took his shot, then said, "Look, at a certain level, the best blowjob you've ever had was the one you had last, right? So at that level, I guess, yeah, I kinda want you to do it again. But not because it's you, just because it's a blowjob, y'know? But I'm not asking."

"I get it," I said. "And even if you were asking, I'd still say no. I'm gonna have to be horny to do that again, and you just don't do it for me, pal."

"Fair enough," he said, laughing a little. "One more question?"

"Shoot," I said.

"Why were you so good at it?"

"Was I?" I said. I felt oddly proud of this.

"I'm not saying you were the best I've had, but it was way above the middle of the pack."

"I don't know, dude. I just took Melissa's advice and tried to do what I like having done to me."

"Fair enough," he said again. "See the Red Wings game last night?"

And just like that, things went back to normal. We spent the rest of the evening cracking each other up, ranting about the referees or our bosses, whatever. After our fifth game, and my third beer, I said I really did have to call it a night.

Just as I was reaching for the door, Dan said, "So look, if Melissa asks me to do you, would you be cool with that? 'Cause I'm sure she's gonna ask me to, and I might decide to do it."

"Can I call you Emma?" I said.

"OK, asshole, I deserved that," he said.

"Yeah, you did. But yeah, as long as your wife is there and her clothes are on the floor, it's cool." And I left.

A week later, Melissa called. "Hi, stud," she said when I answered.

I chuckled and said, "Hi, gorgeous. How are ya?"

"Horny," she said. "Get over here."

"Is Dan there?" I asked.

"Does it matter?"

"It does to me," I said.

"Interesting," she replied. "Do you want him to be here?"

"What I want is to know it's OK with him."

"Hang on," she said. There was a brief pause, and I heard a few shuffling noises over the line, then Dan's voice: "You heard the lady. Get over here. And we've got plenty of beer already, so you can skip the shopping trip."

"Gimme 20 minutes," I said. I took a fast shower, dressed hurriedly and made the 10-minute drive to their place. Dan answered the door when I rang the bell.

"C'mon in, have a seat," he said. "Melissa's upstairs. Beer?"

"Sure, thanks," I said, relaxing in a comfortable chair. He came back with two bottles, handed me one, and took a swig from the other before sitting down on the couch opposite me. We made small talk for a few minutes, mostly about work, but I could tell he had something else on his mind. It didn't take him long to get to it.

"So look, you remember what you suggested last time, after we were finished?"

"You mean when Melissa asked me if I'd, uh, go down on you again and I suggested she and I could do you together?"

"Yeah," he said. "Obviously you do remember."

"I also remember she said you'd have to do something pretty amazing to deserve that."

"Yeah," he said again. "She told me what that is."

I just waited, looking at him. It was a full minute before he spoke again.

"She wants me to tell you that she's upstairs waiting for you, and that you can do whatever you want with her for an hour while I wait down here," he said.

I would not have guessed that in a hundred tries, and I didn't know quite what to say. The thought of it made me even hornier than I'd been ever since she called, but this would be a big change, and my inner angel and demon started battling it out. I mean, here's my best friend telling me his wife wants to cheat on him. But here's this beautiful, incredibly sexy woman maybe putting her marriage on the line because she wants me? It didn't compute; I'm just not the kind of guy women cheat on their husbands with. So I just said a long, drawn out, "Okaaaaaayyyy ...", and waited again. It was a shorter pause this time.

"I'm not gonna tell you that," he said. "Not quite, anyway. Not whatever you want, 'cause if you hurt her or don't stop when she says no, I'll kill you."

"Dude, I would never hurt her, you know that," I said.

"Yeah, I know that. Had to say it anyway."

He didn't say anything else, so after a while I said, "That's it? That's the only restriction?"

"Yeah," he said.

"Whatever I want? You sure? 'Cause that would mean I'm going to have sex with your wife."

"Kinda figured that," he said with a wry smile.

"And ... you're OK with that?" I asked, still incredulous.

"Honestly? I think it's hot as hell."

"And you want two mouths on you at the same time," I said.

"Yeah. That too," he said, still smiling. "So what are you waiting for?"

I shook my head, still not really believing it. I took a swig from my beer and looked him straight in the eyes for several seconds. Then I shrugged, stood up, and started for the stairs. With one foot on the bottom step, I turned and asked over my shoulder, "You sure?"

"Go," he said.

"OK then. Thanks," I said, and trotted up the stairs. I remembered where their bedroom was from the tour they'd given me when they bought the place a few years ago; the door was shut, so I knocked.

"Come on in," Melissa said.

I opened the door and saw her sitting on the edge of the bed, ankles crossed and knees together; she would've looked demure, except that the dark red silk robe she was wearing exposed the skin between her breasts and on down below her navel, and was so short that it barely reached the bed in back. She smiled beautifully when she saw me.

"I've been waiting for you," she said, standing and walking a few steps toward me. "I just have one question before you do whatever you want to me."

I arched an eyebrow questioningly. She said, "Have you been with anybody besides Nikki since you got married?"

"No," I said truthfully.

"Good," she said. "Then we won't be needing this." She tossed a condom she'd been holding onto the nightstand, then pulled the belt on her robe to undo the knot. The robe fell open, still draped over her breasts but revealing her beautifully groomed landing strip and a glimpse of her protruding lips. "I'm all yours, lover," she said huskily.

I pulled off my shirt and pushed my shoes off with my feet, then closed the gap between us quickly. I took her face in my hands and kissed her tenderly, then let my hands roam down her shoulders and back, sliding down that slippery robe until I felt the naked tops of her thighs below it. I brought my hands back up to cup her ass and pulled her tightly to me as I intensified our kiss to hungry passion. Then I wrapped one arm around her back, bent slightly and slid the other arm behind her knees, and picked her up. Her arms quickly encircled my shoulders as I carried her two steps back to the bed, knelt on it, and laid her down gently. I kissed her some more, leaning on my left arm as my right hand caressed the outside of her thigh, then up her side; the robe slid slowly off her left breast as I moved my hand higher, and I cupped it gently, then traced a spiral in toward her nipple as I moved my kisses to her right cheek, then her ear, and then slowly down her neck and chest. Cupping her breast with my hand again, I flicked her nipple with my tongue, then licked circles around it before finally taking that beautiful mound into my mouth. She moaned softly and put a hand on the back of my head.

After a bit I moved left, licking and kissing as I went and pushing the robe off of her right breast with my chin and cheek while gently rubbing her left nipple, still moist from my mouth, with my fingers. I gave her right breast the same treatment, then started lower, kissing my way down her ribcage and firm, flat stomach.

"You don't have to do that," she said.

Pausing briefly, I said, "I want to. And remember, I get to do whatever I want." I resumed my slow journey southward while I reached down with my right hand and caressed the inside of her left calf, then gently pushed it outward while sliding my hand up to her thigh. I moved over her right leg, and she moved it apart to give me room to settle down comfortably. I thanked her by licking down to the little cup on the inside of her right thigh where it meets her butt, then flicking my tongue across her folds to the same cup on the other side and back up a little ways. Then slowly, I moved my tongue to her clit, licked it gently, then licked straight down, parting her already moist lips with my tongue. When I reached her passage, I stopped being gentle and plunged my tongue into her hole, burying my face in her sweet pussy. She drew a sharp breath, then raised her knees, opening herself more to me and letting me probe deeper with my tongue.

She moaned again and grabbed my hair with both hands, pulling me upward so my tongue was on her clit; then, as her hips began to roll gently, she pressed my head firmly against her. I licked and sucked and twirled and did everything else I could think of with my tongue, lost in delight. I looked up to see that she was holding her head up to watch me; our eyes met, and she bit her lower lip. I pulled my head back against the pressure of her hands so she could see my tongue flicking up and down briefly, then quickly buried my face again. When I switched from circles to short up-down strokes with my tongue, she groaned, dropped her head back to the pillow, and pressed her hips into my face. I kept up the same motion and pace, and just when I thought she was on the edge, I thrust a finger inside her. She gasped, then bore down on my finger. I curled it upwards inside her, feeling for that magic rough patch. I found it, stroked it, thrust harder into her so my knuckles pressed on her lips, pulled back out a little and stroked her g-spot again. Her hips bucked hard, then again, and she screamed as she came hard. I kept licking, going more gently and slowly as her climax ebbed.

When she suddenly and fully relaxed, I moved lower and ran my tongue straight up her slit from bottom to top. This got another moan, and left me with a delicious dollop of her juices on my tongue. I held it in my mouth as I moved up; her lips parted to kiss me, and I let that dollop drain into her mouth as we kissed deeply. After a while she took my face in her hands and moved me up so she could lick more of her juice off my chin, then brought me back to kiss her again. Then I rolled off the bed, stood up, and dropped my jeans and shorts to the floor. My cock had been hard for quite a while already and sprang up as if glad to be free.

I leaned over and kissed her again, then climbed back onto the bed and knelt over her chest. I raised her arms above her head, tugged the robe from underneath her and off, and pinned her wrists with one hand, then used the other to rub the underside of the head of my cock over her lips. She flicked her tongue over my frenulum, sending a shiver of pleasure up my spine. I moved up, letting my cock rub her face as she continued to lick my shaft until my balls reached her mouth. She took one gently into her mouth, closed her lips over it to stretch the skin tight, and licked the bottom of it softly, then swirled her tongue around it. Then she pushed that one out and gave the other one the same treatment.

Then she opened her mouth, and I could feel her jaw working and her head twisting; I knew what she wanted, and I wanted it too. I was still pinning her hands over her head with one hand, so I used the other to guide the other ball into her mouth so she had them both at the same time. She moved her tongue deliciously all over my sack, giving me the thrill of pressure almost, but not quite, to the point where it would hurt. I stayed that way for several minutes, enjoying it immensely. But when she managed to get her tongue out of her mouth to lick my perineum, I told her to open her mouth. She did, and made a disappointed little sound as I raised up out of her mouth -- but then I moved forward just a bit more so my taint was poised over her mouth, and the next sound she made wasn't disappointment. She licked everywhere her tongue could reach, softly, just the way I love it. I stayed that way for several more minutes, then moved slowly downward, dragging first my sack and then my shaft over her tireless tongue. I paused for a bit when my movement brought my frenulum to her tongue, and she kept right on licking it for as long as I left it there.

Then I moved down a bit more, pointed my cock down with my free hand, and lowered myself slowly but relentlessly into her willing mouth and throat. She took all of me and never let her tongue rest, pressing, licking and sucking. I raised up until I was completely out of her mouth, but held my cock pointing down so she could lick the head; then I lowered myself again at the same slow, steady pace and stayed buried in her throat for a while. I repeated that two or three more times, and on the last upstroke I got pretty close to the point of no return, so I moved up so she could lick my balls again for a while. When I was no longer in danger of coming sooner than I wanted to, I pushed fully into her throat again, still moving slowly because I like it that way.

As I felt myself building toward the edge again, several thoughts ran through my mind. "God, I'd love to come in her mouth again" was first, but that was followed by wondering whether I'd ever have the chance to fuck her again. Then I said to myself I could do both; I'd never had trouble getting it up again for a second round, and certainly didn't expect to with such a beautiful woman in such a hot situation. My next thought surprised me: "If I come twice, I won't want to go down on Dan with her." Then I debated with myself briefly about whether my chances for fucking her again were better if I lasted longer while doing it tonight -- which would argue for coming in her mouth first -- or if I went down on Dan with her. I quickly decided that helping her suck off her husband was more likely to earn me a repeat invitation, then told myself that if I did that Melissa would probably make sure I got off a second time tonight anyway, and that clinched it. I pulled slowly out of her mouth again.

Not willing to give up completely on relishing her tongue, though, I positioned my balls for some more licking and sucking, then dragged my cock down slowly over her mouth again. This time I kept moving lower, trailing the tip across her chin, down her neck, between her breasts and down her stomach, and finally letting it slide down her moist folds. I kissed her, then raised my head so I could watch her adorable face as I penetrated her for the first time.

As I pushed the head of my cock into her, her eyes locked on mine and her lips parted. As I pushed inside her at the same slow, relentless pace I'd used on her mouth a few minutes earlier, her back arched and one foot slid up my leg all the way to my ass and clamped me tightly to her. At the same time, she squeezed my cock tightly with her pussy; I stayed there, as deeply into her as I could be, until she relaxed a little. Then I pulled almost all the way out and, remembering a trick I'd read somewhere, gave her nine quick, short thrusts followed by one deep, slow one, and pulled almost all the way out again. Then eight short thrusts and a deep one, then seven, and so on. When I gave her the long thrust after four short ones, she moaned loudly and said, "Oh yeah, fuck me!" She repeated "Fuck me!" with every long thrust after that, and soon I was alternating short and long thrusts to that rhythmic chant.

It wasn't long before her chant changed to "Oh god, oh god, oh god," and as I felt my own release building I said huskily, "Oh yeah, I'm gonna come!" She said, "Do it, baby, come inside me, come with me, baby!" I gave up the short strokes and drove into her fast and hard once, then again, and exploded inside her. Her own orgasm started just after mine, her pussy clenching and unclenching on my throbbing cock as she wrapped me in her arms and legs and tried to pull herself right through me, burying her face in my shoulder and screaming one loud long, "Ohhhhhhhhh!"