The cards were slick and stiff in my fingers. They smelled new. I took a long pull from my sweating bottle of beer, feeling relaxed and happy to have people over. A few days ago I read an article about how American men often don’t have close friendships. They get lonely and the loneliness makes them sick. Well, I was determined to nip that in the bud and that same afternoon, when a few of the guys from work were talking about their weekly poker game, I jumped right in and offered to not only host it, but cater it. I needed an in, and I was willing to bet that food would do it. Well, I can tell you that the bet paid off, and I was feeling luck on my side again right then as I looked at us all seated around the card table in my basement. I might win more than just a few friends tonight.

“Adam, the big blind is you.”

“Huh?” I turned to Rafael, seated to my right.

“The big blind. I just threw down the small blind, now it’s to you.”

“Oh. Yeah of course. My bad.” I hesitated. I looked at my cards.

“A quarter, Adam. Put twenty-five cents into the center of the table.” Zach, who was seated directly across the circular plane of brown vinyl looked at me with concern.

“The fuck?” began Big Tony, “I thought you said you’d played poker before.”

“Totally,” I lied, as I tried to recall what color chip a quarter would be. “I love poker.” I tossed a white plastic disc onto the tabletop with panache.

The camaraderie was intoxicating. Cards were laid upon the table. Bets were made, jokes were followed by laughter. I brought more beers from the mini bar and filled people’s plates with sandwiches. I admit I sometimes didn’t follow exactly what was happening with the game, but I got along pretty well just repeating whatever Rafael had done before me.

Earlier in the evening, my wife Cynthia kissed me on the cheek and told me to have tons of fun. She was off to Jackson Hole to visit an old friend from undergrad, so it was just me and the boys. Yep.

“Adam, it’s your turn. Are you going to fold?”

I looked up to match eyes with Zach, who, once again, was shepherding me through a rough spot in the game.

“Oh yeah – thanks! Sorry.” I looked at my cards. I had two Jacks, and there were two Jacks on the table in that place that they said was fair game. Even I knew that I was going to win this hand. Fortune favored me. I was in the zone.

“I’ll raise.”

“Adam, you’re out of chips.”

“Huh?”

“Dude, you’re done,” said Rafael, with much less patience than Zach. “You’re busted. You can’t play anymore.”

“Hold on Raf,” Big Tony leaned back on his folding chair and his gaze tilted downward to keep eye contact with me. “What if Adam wants to stay in? I mean, surely we can make some kind of… accommodation for him. What do you think Adam? We could find some alternative currency and you could stay in the game.”

I felt grateful that Big Tony was willing to be my advocate. I’d always found him a little narcissistic, but now I can see that I just misread him. I’ll feel bad taking his money when my four Jacks bring it on home. “Yeah,” I nodded. “That’s cool. Thanks Tony.”

“Let’s say…” Tony’s thumbnail picked absent-mindedly at the bits of dried mustard in his cuticles. “Let’s say that I’ll float you the cash if you win - which it sounds like you will – and if you lose, you’ll go upstairs and put on Cynthia’s sluttiest outfit.”

He raised a hand quickly: “Not saying Cynthia’s a slut. Don’t want to cause offense. But the outfit. It’s the outfit that’s from whoretown.”

I was a little baffled by Big Tony’s offer. It sounded juvenile, but it really didn’t matter. He could ask me to go upstairs and grow wings – I still had four Jacks. I was solid.

“You’re on, Tony. That sounds fair.”

Tony beamed. “I like your style, Adam. You’re a competitor.”

Zach’s expression of concern deepened, but I shot him a reassuring grin while the sound of more chips hitting the pile blended into the sound of the music (I’d made a playlist for tonight right after entering the date into my Outlook calendar). I felt like Bad to the Bone by George Thorogood and the Destroyers was an omen. It was a harbinger of my victory.

“If you’re in, you have to raise, Adam.”

“Huh?”

“This is why you can’t play without chips, dude.” Rafael seemed irritated now.

I stammered.

“No, no – it’s cool,” Tony interjected. “We can add to the alternative currency. It’s easy.”

“Thanks Tony.” I beamed.

Big Tony threw down three chips on my behalf. “It looks like you’re going to be pocketing all this anyway,” He sipped slowly from his beer. “But in the off chance you don’t, well then while you’re down here in Cynthia’s getup you can suck my dick.”

I admit I was a little jostled by that last bit. I couldn’t tell whether there was an edge to Tony’s voice, or if he was just thinking hard in order to find a fair unit of exchange. I looked at the pile of chips. I looked at Big Tony. I avoided looking at Zach, who I knew was trying to get my attention. I looked at my cards. Four Jacks.

Poker Night Part Two: Payment

“Now… what’s a straight flush, again?” My frontal lobes felt clouded by beer and by the stress of trying to take in new information while everyone was talking over the top of one another. Rafael was explaining flushes, including some sort of royal variety, and Zach was trying to convince them that this all wasn’t fair for some reason. In the chaos it was becoming clear that I’d miscalculated. I looked at Big Tony.

“Looks like you’re headed to the dressing room, Adam. Tough break.” He punctuated this by looking downward. I’m assuming at his crotch. I was still a little fuzzy on where it all went wrong, but a deal is a deal and I asked the group if they needed anything while I was up.

“You might just bring us all another round when you come back,” Tony suggested. That seemed sensible.

I dug around in Cynthia’s closet. I knew she had a lot of clothes but this was the first time I needed to interact with them in this particular way and I felt overwhelmed by the choices. Slutty, I thought to myself as I dug around in her drawers. I came up with a black lace thong that I really liked on her. I sifted some more and found a pink camisole. Was this a top or was it underwear? Fuck it – if I don’t know, then Tony won’t either. Oh – and these thigh-highs. My Lord, I love when she wears these.

I stripped down and put on the thong. It felt different, for sure. And it was hard to keep my junk contained. This wasn’t built for testicles and no matter what I did one or the other would spill out and just loiter in space. I pulled the stockings on and found them even more challenging. They got hung up on my leg hair and when I was able to roll them all the way I noticed that the seams were all over the place up my calves and hamstrings. It looked ridiculous. I worked furiously to align them.

“Hey Adam!” Big Tony’s voice boomed from downstairs. “Let’s get moving! This cock isn’t going to suck itself!”

Duh, I thought. Tony’s not exactly limber, if you know what I mean. “Hold on,” I said – I’m working on the seams!”

I heard a distant “What the fuck did he say?”

By this time, I’d selected the shortest skirt I could find. Black with a lace pattern overlaying a sort of satin. It was nice. I dug around for makeup in her drawer and I can tell you firsthand that the learning curve on this shit is steep. I don’t know how many times I tried to color within the lines when I was doing my lips, but at least it ended up being good practice for the eyeliner. I really overshot the left eye but I pivoted and did the whole cat-eye thing to them both. To be fair, it wasn’t bad. Eye shadow felt pretty straightforward after that and I found a wig from three Halloweens previous in a plastic storage bin. It looked a little tousled, but way better than my own hair which was desperately in need of a trim.

I gripped two beers in each hand and descended awkwardly down the last few stairs into the basement. Heels turned out to be a challenge, and the "slutty" requirement dictated the tallest pair that Cynthia owned. I felt a little like a newborn giraffe and I was embarrassed when I saw my three friends turn to look at me. It went quiet. They looked me up and down – mostly down and I could see that they noticed I was erect. I’d hoped that they wouldn’t. Something about dressing this way was deeply erotic to me. I felt a kind of exhilaration I’d never imagined and admittedly, it was difficult to hide. Tony seemed speechless, which was new – and disorienting. Finally, Zach came up and took three of the beers out of my cramping fingers.

“Adam,” he whispered, “you look… beautiful. Seriously.”

I looked at him, puzzled; I felt like I could have done so much better. Zach backed up and twisted the caps from the cold bottles, distributing them to the other two men, and then took a long drink from his own, still watching me.

Tony raised one eyebrow and then rotated to face me. Time seemed to slow as he unclasped his belt. It swung free and pulled his trousers wider when he pulled his zipper. Bringing his white and blue striped boxer shorts downward from the waistband, he exposed his hairy half-erect genitals.

I kicked off Cynthia’s heels in order to shorten my travel time and sank to my knees in front of Big Tony. I took his penis in my hand; it was veined, thick and intimidating and although I’d been on the receiving end of this process, I hadn’t exactly taken good notes. He was musky and sweaty but I bent his cock down to the level of my lips and placed them gently over his head.

At that point I felt Tony’s splayed fingers on the back of my head and he pressed me over him. I struggled not to gag as he thrust forward into me with his still-growing erection. I felt overcome by a confusing tangle of sensations and managed to wrestle my skull free from his grip. Spitting and blinking I looked up at him:

“Jesus Christ, Tony! What the fuck?”

“What?” Tony seemed genuinely confused.

“I can’t fucking breathe with your cock in my pharynx! Seriously, there’s no room in there. I can’t get oxygen. I can’t think!”

“What the hell, Adam! That’s how it works – haven’t you ever watched porn? Come on, you can do this. Try it again.”

I steadied myself and returned to Tony’s cock. I licked it along its length and teased his frenulum with the tip of my tongue. I saw the head swell with arousal and at the same time, I felt someone behind me. Two hands lifted my skirt and caressed my ass. My God, the tingles that it sent through me. I raised myself up a little on my haunches in order to expose more of my backside and I went back to sucking Tony with a newfound excitement. Behind me, I felt the soft brushing of a cockhead against my anus. Pliable. Teasing. Hypnotizing. Tony reached down toward my head again and…

“Jesus Christ! What are you doing?” I turned to see Rafael behind me. My senses were overcome by a white-noise wave of pain from my anus.

“What, dude? That’s like…where it goes.”

“It’s agony!” I pleaded. “That can’t be right!”

“He wants you to spit on it, Raf. Try that.” He looked down at me impatiently. “Focus, Adam.”

I took another tentative pull on Tony’s shaft and felt Rafael work a little spit over my asshole. I couldn’t help but clench in fear for the moment when…

“God dammit Rafael! That burns!”

He looked frustrated. “That’s what you do! I’ve seen it in porn all the fucking time. What’s wrong with you?”

I told Rafael I’d go upstairs and find some lube. Spit definitely wasn’t cutting it and there had to be a secret to this kind of thing. This was the point when Zach kneeled down beside me and rested his hand kindly on my shoulder.

“You’re not very good at erotic fiction, are you, Adam?” His irises were nearly as dark as his large pupils. His voice was calming.

“I’m new,” I said quietly.

“I know. It’s OK. Hey man… hey don’t cry - you’ll fuck up your eyeliner.” He brushed some of the wig away from my cheek. “Look, Adam. People are stroking. And they’re busy. Three thousand words isn’t a lot of time and they don’t want to read about you heading back upstairs to dig around in the nightstand for that half-empty bottle of Astroglide.”

His look was tender and sincere. My tension began to subside. “This is a fantasy, Adam. You have to relax a little.”

“But he’s going to lacerate my colon.” I looked back sternly at Rafael.

“No man, it’s OK. I promise. It’s just pretend. Like porn.”

“Wait – porn’s not real?”

He shook his head.

“Someone should tell us that.”

“Yeah – someday. But for now, you’ve got to get this rolling. Just let it happen, all right?”

Zach’s generosity opened my heart. I felt a tremendous wave of relief. “Thank you, Zach,” I kissed him sweetly on his stubbled brown cheek, leaving behind a jagged smear of lipstick.

Poker Night: Jackpot

With a deep breath, I took Tony by the hand and led him toward the couch where I could support my weight on the armrest. Rafael lined himself up behind me. As I took another deep breath, the light of the room seemed to dim and grow warm and Tony’s bulbous cockhead looked more palatable. I looked up and made eye contact the way I’d seen it done and brought his thick shaft into my red-painted lips. He groaned in affirmation and I winked upward at him. Meanwhile, Rafael had spread my ass cheeks and sunk his five and three-quarters inches to the…

“Hey. Excuse me…”

Sorry.

He spread my ass cheeks and sunk his eleven inches right to the hilt in one push. He began to hammer at me, swinging forcefully from the hips. My panties, pulled to the side and straining under the pressure of his grip, could no longer contain my balls, which tumbled violently from each impact. I’d never felt anything like this before and I arched my slender back to give him better passage. Tony had gripped me by the hair and found the wig to be unstable. Adapting, he took control of me by the throat and pushed his turgid penis mercilessly past my hard palate and into the soft, tight tissues beyond. Buoyed by Zach’s pep talk, I paid no mind to my asphyxiation and each time Tony was at maximum depth I extended my tongue to lash away at the looming bulk of his testicles.

“Swallow my cum, you bitch,” was Tony’s cue that he was close. My upturned face was streaked with running mascara and I locked eyes with him until he ejaculated into me. I struggled to keep up as each surge flooded my cheeks and boiled, astringent and bleachy, down my open throat. Tony shuddered and quaked and eventually pulled from my mouth, leaving a long arc of saliva and semen bridging the increasing space between us. As Tony staggered backward to sit down, I felt Rafael grip me by the neck and arch me into an impossible crescent. My asshole was hot and tight around him and as he gasped I felt his slippery cum filling me and traveling in rivulets down my sweat-covered ass and scrotum.

I looked for Zach, who had been watching all of this with his typical endearing concern. I motioned for him to join me and when he had stripped naked, I ushered his athletic tan frame onto the couch above me. I felt the powerful muscles of his ass and ran my fingers playfully through his crack. His cock, pressing against my hips and belly, was so hard that he had to have been aching for touch – desperate for release. Placing both my hands on his face and kissing him deeply, I raised my legs up high, flexing my body to present him with my opened, reddened hole. Within the next heartbeat he had followed my lead and placed the velvety head of his penis against me.

I gasped as he entered. Pleasure radiated through my body and I felt pre-cum stream from the opening of my cock onto Cynthia’s now-rumpled camisole. Zach drove long confident strokes into me, pulling more fluid from me with each pass. I didn’t know what I was feeling – it was all so new. Was I going to piss myself? Cum? Go mad? The sensations felt like they would become too intense to handle. Zach lowered to kiss me and I heard his breathing grow more rapid alongside my own whimpering desperate sounds: sounds I didn’t recognize as my own. Sounds that came from a previously unrecognized part of me. And as Zach gasped in pleasure, grunting animalistically through his orgasm, I was set off as well: a rapture across my whole body that left me shivering uncontrollably.

“God, yes,” I whispered into Zach’s curly black hair. “That was unbelievable.” He held me tightly as the pace of our fucking slowed. Just gentle now. I felt him softening and the sensation was delicious – smooth, slick, languid passage of his penis back and forth into my grateful body. We shared one more kiss and then caught Rafael in our peripheral vision - masturbating just inches from my face. He was up and ready for round two – like they do it in porn.