A to Z

~Collin~

I have always been a competitive person to my detriment. If one of my friends challenged me to do something nine times out of ten I would do it without a second doubt. Whether it be something as simple as doing a belly dance in the middle of the cafeteria in high school or more wild like giving the bartender a blowjob in the middle of happy hour, I'll do it. I don't even need a reward for completing the dare, once I am challenged it becomes a pride thing.

That's why I am currently making out with a blond hunk in his hotel suite. My back against the front door as we explored each other's bodies. His hands were reaching under my shirt tracing the lines of my abs, while I cupped his ass cheeks through his tight pants. He was moaning into my mouth as we kissed and I could feel his hard-on pushing against my own. All of this was happening while my boyfriend was none the wiser back at our own place, sleep in our bed.

It all started when I met up with my friend, Jacob, earlier tonight. He had come to town to visit family during his vacation and we decided to hang out before he left back for work. He was staying at his favorite hotel downtown during his stay, a hotel that was known for having patrons that fall under the rainbow. That's exactly why Jacob always stayed here when he came to town, it was the easiest place to get a night of fun with no strings attached.

I was at the bar nursing a beer as I saw him bounce from man to man. He was strutting back towards our spot after just talking to a couple of twinks at a corner table, "Looks like I'm gonna have double the fun tonight," he said as he sat down next to me.

"Congratulations," I replied as I took a sip from my beer.

"Jealous Collin?"

"No, just confused on why you chose them. I thought you were over twinks."

"Oh I am, but those two were just so cute. Plus there are two of them, it's been a while since I've had a threesome."

"Why not just convince two other guys to join you."

"Easier said than done my friend, it's hard to tell who would be up for that or not."

"Jacob, we're at Menset hotel, I can assure you with the right words we could have an orgy started in the lobby," I said but he just scoffed, "Unless you think you don't have what it takes to pull someone else."

"Oh trust me, baby, I have what it takes," he said with confidence.

He had every right to do so. Jacob would never have a shortage of men with the way he looks. At 27 years old he stood tall at 6'1" and had a full head of dark black hair and a stubble beard. It was obvious that he worked out from the muscles that bulged under his clothes, every time he moved his arms I swear it seemed like his biceps would rip through. His eyes were a deep ocean blue that you could get lost in and his smile could make your pants drop in less than a minute. He was hot and he knew it. That didn't mean I couldn't make fun of him.

"Sure you do," I laughed.

"Don't get mad just because you don't have game anymore."

"Excuse me, what makes you think I don't have game."

"Please you're only 26 and you've been with what's his name for like 4 years now, you haven't had the time to have game."

"I've been with Finn for 5 years, Jacob. That means nothing though before I met Finn I was pulling more ass than you."

"You mean while you were drunk at frat parties with guys you barely know the name of or remember how they look. They would have slept with anybody Collin that doesn't prove you have any game," Jacob started, "To have game is to be able to go up to a guy. Flirt with him, get him genuinely interested, take him back to bed, and fuck the hell out of him with little to no help from alcohol."

"I don't need help from Alcohol thank you very much. Finn doesn't ever need convincing."

"I'm not talking about from your dumbass boyfriend either. I'm talking about a complete and total stranger. You couldn't do it."

"You'd be surprised what I can do."

"Oh really," he said with a devilish smile.

"Yeah," I said with a similar smile.

"Then prove it," he said.

"What?"

"Prove it, go find a guy and get him to agree to go to bed with you," he said.

"Fine you're on, it shouldn't be that hard to get somebody to agree to that," I said confidently.

"I don't think you get what I'm saying," he said, his smile becoming wider.

"Yes I do, get a guy to agree to go to bed with me," I started.

"Then go to bed with him," he finished.

"Huh?"

"You need to convince a guy to go to bed with you, go to bed, and fuck him, or you know get fucked whichever one you want. That's the only way to really prove that you have game enough to get someone into bed," he said.

"I-I can't do that. What about Finn?"

"What about him? Is he expecting you back soon? Just text him and say you will be a little late."

"No, I can't just go and cheat on him with some stranger. That's wrong, just let me flirt with the guy and let it end there."

"Anybody can flirt, Collin, you're gonna have to do more than that to prove that you really have any game. The only way to do that would be to go through with the whole thing. So either go through with it and prove to me that you really have game or sit back down and let me show you how it is done."

He was taunting me now, not only that but disrespecting me and my capabilities. Yeah, I may have been off the market for a few years but that doesn't mean I can't get a guy. I mean I would say I'm pretty good looking if I say so myself. I was the average height at 5'10 but my muscles were well defined. I was clean shaved with a messy mop of blonde hair. My eyes were a sweet hazelnut and I've always been told I had a handsome smile with deep dimples.

"Does it have to be all the way, what about if we just make out?" I asked.

"All the way," he simply said.

"Okay blowjob?" I asked.

"All the way," he repeated.

Now the thought shouldn't even be crossing my mind. I mean I love my Finn, I want to marry him one day. Sex with him is amazing as well. I can't just let Jacob call me out like this though.

"How will you know I actually did it?"

"Record some of it. I need proof that it is a different guy too, can't be some old video you made with Finn or something."

"You want it tonight?"

"While I'm still in town, yes."

I couldn't believe what I was about to say, "Fine. I'll prove to you that I have game."

Jacob's eyes widened in both surprise and excitement that I actually agreed to do it. He knew once I agreed to a challenge I was serious. He also knew I would not stop till I had it completed.

"Ohh yay, you want me to choose a target. I'll go easy on you."

"No, I'll choose. You, you just wait and see." I said, now determined to complete the challenge.

"Sure Collin, I'll wait and see up in my room. Looks like my guests are ready," He said as his two twinks walked over to us and he gave them a flirtatious look. He winked at me before he got up and led them to the elevator to take up to his room.

I didn't waste any time though. I was already scanning the room for a guy that I would find suitable. If I was going to cheat on Finn for a bet it was going to be with a guy that was worth the effort. I also knew he couldn't be too far out of my league if I wanted it to actually work. I spent about 45 minutes in the bar trying to find guys but every guy I talked to was not interested and quickly walked away.

Finn had texted me twice asking when I would be back home and I ended up saying that I was spending the night to get as much time as possible. All the while I was sure Jacob was having a blast in his room with the two guys he took up. This honestly seemed like a challenge that I would fail at proving Jacob right so I sat at the bar to think about how I can possibly win.

While I was deep in thought the seat beside me was taken by another young man. He had asked for a menu to look over before he ordered. I looked over in curiosity and saw him, he was about my height, average looks but cute in a boyish way. His hair was platinum blonde and his body was nice and lean. His ass just popped off the barstool too, like an extra cushion. This was it, he was attractive and right beside me, he had to be the one. This is gonna be my last try.

With a deep breath, I turned to him, "Hey I'm Collin."

He looked back and smiled, "Adam."

"Are you from around here?"

"No, I'm just here for the weekend. Got a room here because I heard that this hotel is a lot of fun if you know what I mean."

"Oh really?"

"Yeah, but it seems like I picked a bad night. So I was just going to get something to eat before I head to sleep. I have plans with some friends tomorrow I need to get ready for.

"I feel that I've sort of been striking out tonight too. Apparently, I've lost my game according to my friend."

"You're cute, you can't be having that much trouble."

"You'd be surprised," I said looking him up and down. He did the same and there was this look in his eye. Like he wanted me, jackpot!

"Hey since we're both out of luck why don't we spend the night together. We can always head up to your room," I suggested as I placed a hand on his lap.

He smiled and shivered a little to my touch. He put the menu he had down, "I would like that."

With that, we both got up and went to the elevator. He pressed the 7th floor and we stood close together as the elevator went up. His hands grazed against mine and I got all giddy. Was this really about to happen? Was I really going to cheat on Finn for a bet?

The elevator dinged and we got off on his floor. He led me down the hall to his suite door and let me inside. I knew the second I entered the door it would be a done deal, this would happen. I didn't even think though, I just walked inside. Then I was thrown against the closed door and his lips attacked me. At first, I was thrown off by the sudden kisses but I quickly melted into his embrace. His hands trailing my body under my shirt while I cupped his ass. His dick was rock hard against my leg and so was I.

He moved his lips to my neck, licking and sucking on it. I couldn't help but moan his name as I squeezed tighter on his ass. The more pleasure he gave me the more Finn left my mind. He began to lift my shirt up and over my body leaving my chiseled torso vulnerable to the cool air. His lips trailed down my neck to my chest, my stomach, and to my treasure trail. He licked my navel as his fingers undid my belt and pants pulling them and my boxers down in one swoop leaving me fully exposed.

My 8" dick flopped out hard as a rock. I was initially worried I wouldn't be able to be aroused enough for this to work, but that was not a problem. Adam took hold of my dick and looked up at me from the floor. He stuck his tongue out and took a long lick up my shaft, then another and then another. Without warning, he took the whole shaft down to my balls. I was feeling the back of his throat and my knees buckled. This was the first man other than Finn to suck my dick in five years and it was amazing.

I relaxed against the door as Adam went to town on my shaft he bobbed up and down and twisted it with his hands. My own hands instantly went to his head and guided him up and down, sometimes keeping him down longer just to keep that amazing feeling. He did it with no issues, smiling around my dick.

He eventually got up and we resumed our kissing as we walked towards the suite bed. I was taking his clothes off as we did. Feeling his muscles and smooth skin. It was exhilarating. By the time we got to the bed, we were both completely naked. I pushed him down onto the bed and climbed on top of him. As I hovered over his body I looked into his eyes. They were filled with lust and want, and I knew mines were too. I leaned down and kissed him again, our naked bodies fully entwined.

Skin on skin as I ground on him and attacked his lips. This time it was my turn to explore his body with my mouth. I licked his ears and neck, giving him shivers with every breath. I then descended to his nipples. I licked around his right nipple, nibbling at it while I played with the left one with my hand. I got it nice and hard before I switched. All the while Adam was moaning my name under me. I liked down his torso to his achingly hard 6" cock.

I teased the head with my tongue before I slowly engulfed my mouth around it. Adam moaned as I sucked him deep, the first cock other than Finn's that I have sucked in five years. The taste was new, it was different, and I liked it. I couldn't get enough as I sucked him deeper and deeper, ignoring my gag reflex I just needed his dick. I felt his hands grip my head and push me up and down, as he began to fuck my face in pleasure. Drool was falling down my face.

He eventually released my head and I got up back with my face equal to his, "fuck me." he said in a faint whisper.

That made me smile as I let my fingers tease his hole. Now obviously I wasn't prepared for this cause fucking some random guy was not on my to-do list, and even then I haven't used condoms with Finn in nearly two years.

"Do you have lube and condoms?" I asked and he nodded his head. He scooted from under me and went to one of his bags and pulled out both a bottle of lube and condom. He handed it to me while he turned and got on all fours. I licked my lips as I rolled on the condom and applied the lube, I got some more lube on my fingers and began to play with his hole. I could already tell it was going to be tight.

I went slowly with one finger, then two, then added a third. With every movement, with every new finger, he moaned. I was ready, I needed my cock in his asshole now. I was just about to mount him when I remembered that Jacob said he needed evidence to prove that I did this. I would hate to go through all of this and not even get the proof I needed.

"Hey, Adam would you mind if I recorded some of this, for later? I won't get your face in it," he just moaned in pleasure as he nodded his head. I quickly got up over to my forgotten pants and pulled out my phone and opened the camera.

I held it with my left hand as I positioned my cock right at the opening of his asshole, "Are you ready for this Adam?"

He moaned in affirmation but I wanted him to use his words. I needed Jacob to know that this was the real deal, "You need to say it, baby, say it or you won't get it."

"Please, please give me your dick sir," he moaned and with that, I slowly inserted myself into his tight walls. We moaned in unison as my dick slowly inched inside of him until I was bottomed out. I stayed still inside of him for a moment so he could get used to the length before I slowly pulled out till just my head was in there and slowly back in. I held the camera steady as I slowly fucked him, the pleasure overwhelming. Though it was weird wearing a condom again after such a long time of not using them.

Adam started to fuck back on my dick cause my slow pace was not doing it for him. He was bouncing back hard and fast and it was getting to be too much. I dropped the phone on the bed as I grabbed him by the hips and started to really pound into his ass. I was going hard and fast. The sound of skin slapping filled the room along with our moans.

He was reaching back to jerk himself off as I fucked him deeper, "Yes daddy, give it to me," he moaned. I just fucked deeper into him, and the feeling was getting too close.

I moved my hands to his shoulders to get a better angle as my thrusts became more erratic, "Oh Adam I'm about to cum, I'm about to cum."

"Oh yes, me too daddy. Me too," he said as he jerked his cock faster and faster. When he started to cum on the sheets his ass hole began to constrict around me. That made it impossible and with one final thrust I unloaded into the condom as I came like I never have before. My body was sweating and I leaned down to kiss his back.

"Ooh thanks, I needed that," he said with deep breaths. He groaned some when I pulled my dick out of his ass and turned over to his back while I laid beside him.

"That, that was good," was all I could say as my body was out of energy.

"You seemed like you needed that. Has it been a while?" he asked.

"You could say that," I said. The afterglow of sex was beginning to fade as thoughts of Finn began to come back in my mind and guilt started to settle.

"You okay Collin?"

"Yeah, just thinking, and tired. I should head out."

"You sure you don't wanna spend the night, we can always go for another round."

"Actually no, I'm good. Thanks that was really really good," I said as I started to collect my items and put my clothes on.

I gave Adam an awkward kiss goodbye before I left. When I made it to my car I had a tiny panic attack as I drove back home. What if Finn finds out what just happened. How would I explain it to him, would our relationship be over. Would we make it through this? These thoughts raced through my mind all the way home and into my house. I didn't even wait to hop into the shower and wash off what just happened, even with all the negative thoughts I couldn't help but remember how good the experience felt. Good sex is good sex no matter what.

I got out of the shower and quietly snuck into the bedroom I share with Finn. Before I got into bed I went to the video on my phone and sent it off to Jacob with the message I do have game. I tried to get into bed as quietly as possible so as not to disturb him. When I got settled he turned around half awake.

"Hey baby, I thought you were staying over at Jacob's," he said groggily.

"Oh yeah I was but then he found some lads he wanted to take back to his room. I decided to give them some privacy," I said. Finn just nodded his head as he drifted back to sleep. With that, I was in the clear as I cuddled next to my boyfriend and fell asleep, after just having fucked a total stranger in the hotel.

The next morning I woke up alone in bed, not a total surprise seeing how Finn usually worked early hours at his job. I grabbed my phone to see text messages from Jacob.

Jacob: Damn that ass looks hot, sounds like you had fun.

Jacob: You were really going at it man.

Jacob: Didn't know you had this in you.

I just shook my head at his messages when I decided to go ahead and call him. He picked right up with a cheerful scream.

"Damn man I didn't think you would really go through with it, that was fucking hot!"

"You know me when it comes to a challenge. I never disappoint."

"No you do not, are you still with that hot ass?"

"No, I'm home. I came back right after. Finn is at work."

"So how was it man?"

"It was actually pretty good, just felt weird afterward. But the sex was definitely good. Besides, it proves to you that I do have game."

"Well not really."

That made me stop in my tracks, "How is that not really? I fucked the guy, talked him up from the bar."

"Yeah, but that was only one guy, who's to say that it wasn't a fluke. No, you need way more than just one guy to prove you have game."

"How many do I need to prove that 'I have game'?" I asked, now worried about where he was going with this.

"What was that guy's name, Adam?"

"Yeah, why?"

"Adam starts with A. The first letter of the alphabet, if you can get with a guy from every letter of the alphabet successfully then I will say you have true game. No Finn will not count for the letter F, needs to be new people."

"You want me to have sex with 25 more people, I can't do that. One was dangerous enough what if Finn finds out."

"Than make sure he doesn't find out, that shouldn't be too hard for you."

"Jacob..." I trailed off.

"What do you not think you can handle? If you have as much game as you claim that you have then it shouldn't be an issue, unless you want to admit that I was right."

He was taunting me again, and it was getting to me again. I can't do this, I can't continue cheating on Finn for a stupid challenge. I love him and this is unfair to him, it's not worth ruining our relationship. The sex with Adam was fun though and new, and if all the sex is as good as that, maybe. No, the guilt afterward would be too much to bear, but maybe it will fade with time.