The Poker Game

Author's Note: Typical conditions apply. This takes place in Fantasyland and is for your reading enjoyment. Things may seem unrealistic at times and may move a little fast, but try to ignore them and let the story take you where you want to go. Have fun!

The Poker Game

My name is Taylor and I'm in the middle of some financial problems. I am a few months late on rent, utilities, and credit cards. I need about $10,000 by the end of the week. Sure I have a job, but not one that's good enough to cover my debts.

My problem is my friends. Well not really, I'm the problem because I try to keep up with them when I know I can't. My three best friends, Brent, Alan, and Will, all have family money. They have never worked a day in their life and spend money like water. I do my best to try to hang and not look like a loser, but the trips and nights out have caught up to me.

Why don't I just borrow from one of them, you ask? It's because I have and haven't done a good job in paying them back. I owe each of them a couple thousand dollars. Luckily for me they've either let it go or forgotten about it. I know that if I ask again it might trigger their memories and I'd rather not have that conversation. I have enough problems.

I heard my phone ring. Oh good, it's not disconnected yet. It was Brent. I answered it.

"Hello," I said, timidly.

"Hey Bud! What's Up?!" He said, loudly.

"Oh nothing much," I replied.

"Free tonight?" He asked.

"I guess so," I said.

"Awesome, you remember my friend JD?" He asked.

"Yeah, I met him a few times. He's the one with more money than all of us combined, right?" I said.

I wasn't kidding. JD was left millions from his Grandmother and hit for a few more on Powerball. He was truly set for life.

"Yep, him. He's hosting poker tonight. Me, Alan, and Will are all going. You in?" He asked.

"I'm a little light right now," I said, a little embarrassed, "How much is the buy-in?"

"It's not too crazy. $2500 with a $2500 re-buy if needed," he said.

"$2500? No way I can swing that. I've gotta come up with $10k by the end of the week," I said.

"Oh man, I'm sorry. I didn't know you were that strapped," he said, "The game won't be the same with out you. Poker with only 4 is kinda lame."

"No I'm sorry. I feel like a gimp that I can't keep up with you guys. You know I love to play poker," I said.

"Yeah and if memory serves you are pretty good at it. Too bad you don't have the $2500, you could try to turn that into the $10k you need," he said.

I knew what I was about to ask was a bad idea, but I took a shot anyway. I had nothing to lose at that point, at least that's what I thought.

"Well um, you could lend it to me and I could pay you back from my winnings," I asked, timidly.

"Oh Man, you know how I am with lending money to friends," he said.

I turned up the heat and said, "Come on, you know I'm good for it. I'll pay you right back at the table. Plus you'll have your 5 for the game."

"Okay, I'll tell you what. I'll lend you the $2500 plus another $2500 for the re-buy. Anything you win over $5000 we split," he said.

I did the quick math in my head: 5 guys, $5000 each is $25,000. If I clear the table, $5000 back to Brent and $20,000 split between us gives me the $10,000 I need. Could it be any more perfect? I was about to find out.

"That would be great," I said, "I really appreciate it."

"No problem. The game is at 8. I'll text you the address," he said.

"Thanks again Buddy. See you soon!" I said.

I pulled up to JD's huge house just before 8pm. The guys were already there and the pizza guy followed me in. As rich as all my friends are they still loved pizza and beer. I gave bro hugs to Brent, Alan, and Will and slapped five with JD. Then Brent pulled me to the side and handed me an envelope with $5000 in cash.

"I expect that back at the end of the night," he said.

"No problem," I said.

We each handed JD $2500 in exchange for chips. Then we grabbed a slice and a bottle of beer and sat down at the table.

The game started out slow with a lot of checking and folding. We were all having fun and it was a nice distraction from my money troubles. Things escalated quickly when Brent, Alan, and Will went all-in on a hand. Alan won the pot and Brent and Will handed JD another $2500 to buy back in.

A few hours had gone by and I was still nursing my original buy-in. I was getting a little impatient until I finally got a pair of Aces. I quickly went all-in when the third Ace hit the table. Brent and JD went all-in too. Of course JD pulled a straight which beat my three of a kind and Brent's two pair. Brent and I bought back in and now there was $22,500 on the table. Only JD hadn't needed to re-buy.

Things slowed down again until it got closer to midnight. I got pocket Aces again and I thought there was no way I could lose twice with a pair of bullets. When the third Ace hit the table I went all-in. Brent, Alan, and Will followed me and JD folded. When the fourth Ace hit the table I had a huge grin on my face. I had $15,000 in front of me and JD had $7500. I had knocked my three friends out.

"Well shit," Alan said, "Looks like you got us all. I'm getting tired, I think I'm gonna head out."

"Yeah, me too," Will said.

"Wanna call it a night?" JD asked me.

I looked at my stack of chips. $15,000 meant $5000 back to Brent and then I had to split the $10,000 leftover with him. That only left me with $5000 my way, not enough to cover my debts.

"I'm cool to keep playing if you want to," I said.

"You two knock yourselves out," Brent said, "I'm gonna head out too. Taylor, do you have that money you owe me?"

I started to count my chips.

"No, no, no, you can't take money off the table!" JD said. "He can pay you tomorrow."

I looked at Brent and shrugged.

"Okay, text me when you wake up," Brent said to me.

JD and I said goodbye to the guys and went back to playing. With the larger stack I was able to control the action. I was slowly building up my lead until I tried to go for the kill. Of course I lost and my lead shrunk a bit. The next time he wasn't so lucky and I had all of the chips on the table in front of me. $22,500 was more than I had seen in my life.

"Looks like you got me," he said. "This was fun tonight."

I did some quick math in my head and realized I only had $8750 coming my way. While I knew I could probably get away with that. the gambler in me made want to keep going.

"Don't you want to re-buy?" I asked.

"That's right," he said, "I only put my original stake into the kitty. Why don't we call it a night anyway."

"You sure? I pressed him, "I'm not tired yet."

"Okay, if you insist," he said.

At the time I didn't know this would be a life changing decision.

With the smaller $2500 stack JD kept going all in and chipping away at my lead. Then a hand came up and I really thought I had him. I just knew I would be going home with the whole pot and bailing myself out. I had a straight and I didn't see any combination of cards that could beat me. He ended up getting the only card that could beat me and caught a full house on the last card. Our chip stacks were now even.

It went all downhill from there and my stack kept getting smaller and smaller. With my last $2000 I went all-in and he knocked me out. After all that time ahead, I totally blew it. Not only did I have my original debt, I owed Brent $5000. I did everything in my power not to cry.

"Good game," he said.

"Yeah, I guess," I said, clearly upset.

Noticing that I was upset, he said, "You okay? It's just money."

"Yeah, to you," I said, "I'm in deep trouble."

"Shit, I didn't know," he said.

Teary eyed I said, "Not only do I have my own debts, I owe Brent $5000 from tonight."

"Oh man, I guess that's why he was trying to take his money on the way out. You know what, if you want I'll let you re-buy and try to win some money back," he said.

"But I don't have anything," I said.

"What if you offer me something in trade for it?" He asked.

"Like what?" I asked.

He thought for a second and said, "Well it does get lonely in this big house and believe it or not finding a girlfriend is hard. Most of them are just money grubbing bitches and I don't like that."

"What are you saying?" I asked, nervously.

"I'll give you $5000 in chips in exchange for a blowjob," he said.

"What?!!! I'm not like that. I didn't think you were either," I said.

"Everyone is a little bi," he said, "Plus don't you really need the money? Five thousand dollars for a blowjob is a great deal. Plus you only owe it to me if you lose your whole stack again. If you win you me owe nothing."

I agreed, having faith in my poker skills. Little did I know he was setting me up for more than that.

"Okay, I'll do it," I said, reluctantly.

He counted out $5000 in chips and slid them over to me.

"Good luck," he said.

"Thanks," I replied.

I won a few hands but I was really getting tired. It was almost 4am and my mind was starting to slip. I was miscalculating the possible cards left in the deck and JD knocked me out for the second time that night.

"Fuck!" I yelled out.

"Yeah that sucks. Sorry about that. I was actually rooting for you," he said.

I wasn't sure if he was patronizing me, but I just said, "Yeah."

"Well speaking of suck, I think you owe me something," he said.

Giving my last ditch effort to get out of it, I said, "You were serious about that?"

"Serious as a heart attack," he said.

"Yeah, I know," I said, tearing up a little.

"Listen, its been awhile and I don't like to jerkoff, so it should be quick," he said.

"Gee thanks," I said.

He stood up and began to walk towards me. He unbuckled his belt as he got closer. Holy shit, he was really gonna make me blow him. I was in a daze and was startled by the sound of his belt hitting the floor with his pants. He was standing in front of me in his boxers and I could make out the impression of his dick. It looked big.

"You've had blowjobs before, right?" He asked me.

"Yeah, a couple from my college girlfriend," I said.

"Just do what she did, I promise it won't hurt and I'll be quick," he said.

"Okay," I said, accepting my defeat.

"Take it out," he said.

I couldn't believe I was doing this. I grabbed the waistband of his boxers and pulled them down. His semi hard dick was staring me right in the face. Not that I was an expert, but he had the biggest dick I had ever seen.

"Holy shit! You're huge!" I said.

"Nice, right?" He said, smiling.

"It wasn't necessarily a compliment," I said.

He laughed and said, "Come on, the faster you get going, the faster you'll be done."

I had no choice at this point. I was sitting in my chair at the poker table and there was a giant penis right in front of my face. I slowly parted my lips and closed them as I reached his head.

"It's okay if you want to kiss it, but it will go much quicker if you just suck it," he said.

I opened my mouth to say, "I wasn't kiss...

He interrupted me and pressed himself inside my open mouth. I guess he thought he was helping, but I gagged and he pulled out.

"I'm sorry," he said, "I thought I would give you a little assistance."

"Just let me go at my own pace please," I said.

"No problem. You're the boss," he said.

"Gee thanks," I said.

"I've already been in your mouth. It should be easy now. How did it taste?" He asked.

"Actually not too bad, it was kinda sweet," I said.

"That was my precum," he said, "Maybe you will enjoy this."

"Not likely," I said, "Anyway, enough talking. Let me do this so I can go home."

"My lips are sealed," he said, "Now open yours!"

I listened and took him inside my mouth again. I slowly moved down his dick and he moaned. When I thought I couldn't take anymore I stopped. I swirled my tongue around and gave him a big suck. I pulled my head back so just the tip was inside and then I plunged back down as far as I could go.

"Oh My God, so good!" He yelled out.

For a second, I smiled, happy that I was making him happy. Then I remembered I had a giant dick in my mouth and wanted it to be over quickly.

I grabbed his hips and started to bob my head. I was sucking him hard and giving him a tongue bath at the same time. I could tell he was going crazy.

"Yeah, suck that cock!" He yelled out.

Encouraged by this I kept going, faster and faster. I felt his dick start to swell and knew what was about to happen. I tried to pull back, but he put his hands on the side of my head. He exploded and came deep in my mouth. Since he was holding me in place I had no choice but to swallow.

When his dick finally stopped pulsing he let go of my ears and he slipped out of my mouth. I immediately grabbed the bottle in front of me and guzzled my now warm beer. I had just given a man a blowjob to completion and swallowed his cum, and my first instinct was to try to wash it away.

JD pulled up his boxers and pants, buckling his belt.

"That was awesome, thanks so much," he said.

"You're welcome, I guess," I said with tears in my eyes again.

"Shit, don't be like that. I was really trying to help you when I made this deal," he said.

Very upset now I said, "I know you were, but now I'm still deep in debt and I just sucked a dick! My landlord is gonna kick me out if I don't pay by the end of the week, they're gonna shut my cell phone, take my car, and on top of it Brent is gonna come looking for his money tomorrow."

"You owe him $5000, right?" He said.

"Yeah," I said.

He walked over to the table with all the money and counted out some.

"I feel bad for you so I'm lending you $6000. Pay Brent and your phone and your car," he said.

"Thanks, but I have no idea how I would pay you back," I said.

"I'll call you tomorrow and we'll figure something out," he said, "I'm too tired to think right now."

"I really appreciate it," I said.

"No, thank you, seriously," he said.

He was thanking me for the blowjob, which I still couldn't believe I did.

All I could think of to say was, "No problem."

"You okay to drive?" He asked.

"Yeah," I replied.

He slapped me five, like we were buddies and I didn't have his sperm swimming in my stomach. I walked to my car and drove home.

On the ride home I couldn't get the blowjob out of my mind. I still couldn't believe I had a dick in my mouth, and not just any dick, a huge one. I started to get hard and was rubbing my crotch with one hand and steering with the other. When I got home I immediately stripped naked and jerked off to the vision of JD cumming down my throat. I immediately felt ashamed, but was too tired to dwell on it. I fell asleep right away.

I was so exhausted that I actually slept well. As I was waking up the events of the previous night flashed through my head. What was wrong with me? I liked pussy, not dick! I never had a thought of being with a man before, yet I blew him and swallowed in exchange for a loan. A loan I had no way of paying back on top of my other financial woes. I guess we would figure that out together when he called me. I decided to clear my mind with a nice hot shower and get moving.

My first stop was to the bank to deposit the $1000. I went online and paid my phone bill and car bill. Then I met Brent at a diner where I gave him his $5000 and we had breakfast. I told him I lost everything else and unfortunately there was nothing left to split. Of course I didn't mention my extracurricular activities. Then he had to go and I went back home.

At about noon my phone rang and it was JD.

"Hey Pal, how are you doing?" He asked.

"Good," I said, "I slept really well."

"Did you take care of everything you needed to this morning?" He asked.

"Yep, thanks. Me and Brent are even and Verizon and Honda can leave me alone for another month," I said.

We were talking like two buddies and like nothing happened last night.

"So I was thinking..." He started.

Here we go, I thought.

"Yeah?" I asked.

"How would you feel about coming over and playing for that $6000 you owe me?" He asked.

"Um, okay, I guess. I don't have any cash left for a buy-in though," I replied.

"That's okay, we can do it in trade like last night," he said.

"Oh," I said.

"I won't make you do anything you don't want to do and it will be the same arrangement: you win, we're even, and you can also win more" he offered.

I paused and thought for a second. His dick had already been in my mouth once. I owed him money, plus I could cover my debts. Then I would find the first girl I could and forget last night ever happened.

I guess I waited too long to answer and he said, "Don't worry, we'll start slow for your buy-in, nothing nearly close to last night."

"Okay, deal," I said.

"What are you doing now?" He asked.

"Nothing," I said.

"Be here in an hour?" He asked.

"Sure," I said.

The hour went by quickly and I found myself parked in front of JD's huge house again. We slapped five again and he led me to the poker table. He had $2000 in chips by each seat on opposite sides of the table.

"I figured we'd start at $2000 with unlimited re-buys. We can stop whenever you want," he said.

"Okay, so what do I have to do for the first buy-in?" I asked.

"Follow me," he said.

He led me to the guest room. Sitting on the bed was a pink and black ball of lace. Upon further inspection I saw a Pink Bra and Panties, a Pink Garter Belt and Black Stockings. Here we go again, I thought.

"You want me to wear that?!" I asked.

"Yeah, in exchange for $2000 credit. Not bad, right?" He said.

I shook my head in defeat and said, "Yeah, I guess."

Wearing lingerie was certainly better than a blowjob! Besides my plan was to bust him out, take my money and go home. If I had to dress up a bit to do it, so what.

"Take your time and I'll be waiting," he said.

He closed the door behind him. I took a look at my outfit for the day. I had seen my girlfriend get dressed so I sort of knew how everything worked. I stripped down and folded my clothes, putting them on the bed. Having blonde hair, my body hair was very light and I had very little of it anyway.

I started with the panties and pulled them up my legs. They were a thong and I wondered how girls walked around with a wedgie all day. As the strap settled in between my cheeks my dick started to stir. The last thing I wanted was to get hard and let JD know I was enjoying this.

I picked up the bra and laid it across my chest. I reached behind me to clasp it, but it wasn't working. Then I remembered seeing women hook it in front and swinging it around. That worked and my slight man boobs settled into the cups. It was a nice feeling and now I was completely hard.

I wrapped the garter belt around my waist and sat on the bed to do the stockings. As I sat down the back of the thong went deeper inside my crack and a small drop of precum appeared on the front. I started to freak out, but I knew I couldn't take much longer to get ready.

I slid the left stocking up my leg and then the right. The nylon felt amazing and didn't help my erection situation. I took me a second to figure out the garter clips, but I got them attached pretty easily.

I stood up in front of the full length mirror and saw my reflection. I looked exactly how you'd think, a guy in lingerie. Seeing my crotch, for first time in my life I was happy I wasn't so well endowed. Sure I was still hard, but it wasn't very noticeable. I figured everything was good enough and it was time to win some money.

I walked back towards the game room and was greeted with a whistle you'd hear at a construction site.

"Wow, you look great!" He said.

"Yeah, right," I said.

"With a little longer hair and some boobs you'd look even better!" He said.

"Whatever you say," I said, "Can we play now?"