A Straight Bet

by Lee Obrien

6 Oct 2022 5264 readers Score 9.6 (122 votes) PDF Mobi ePub Txt


We all arrived at our weekly card game, Brad barely looked at me when he came in. I quickly brought up the football game and how exciting it was, this started Jace telling us how great it was in person. This seemed to put Brad a little more at ease.

We all sat down and started our game, Jace gave me a questioning look, I raised an eyebrow and gave him a slight nod. He motioned toward Bubba, I shook my head, “so Brad, it was nice to get to know your brother this weekend.”

Jace’s eyes opened wide as I nodded in his direction. Brad said, “yeah, he was glad to meet you too, he said he liked having someone help him give me a hard time.”

Bubba laughed, “did they pick on you Brad?”

Brad rolled his eyes. “Yeah, you could say that.”

Harrison changed the subject, Brad relaxed, and the rest of the night was just like all our other nights. I was the last to leave as Jace said, “so Brad, huh?”

I replied, “yep, and his brother too.”

He gasped, “seriously?”

I nodded, “actually, Chad was the one that started everything.”

I walked toward the door, “when I finish with the other two, I will tell you all about it.”

I still wasn’t coming up with a plan to get Bubba alone, then about two weeks after I was the center of a twin sandwich, I was trying to send an email. I knew my 5-year-old laptop was coming to end of its life, when it kept losing my Wi-Fi connection, I was getting frustrated. I knew I was due for a new laptop at work, they have us set up on a rotation, so we all get new ones every three years. They let us buy our old units for a very cheap price, I just needed my old one to last for a few more weeks.

I called my personal IT guy, “hey Harrison, I keep losing my Wi-Fi, can you tell me what I can do to fix it?”

Harrison said, “sure, tell me what it’s doing.”

I read him the error message that appeared when I lost my connection. He gave me instructions over the phone and everything we tried failed. He finally told me it would be easier to work on in person.

Harrison said, “I’m not doing anything this afternoon, if you want to bring it over, I can see if I can get you going.”

I replied, “I would appreciate that, I will be there in a little while.”

As I was putting my laptop into its case, it occurred to me, this may be a perfect time to see if Harrison was open to a little man-to-man fun. Just in case he was, I took a quick shower and since it was Sunday, I just threw on a pair of sweats and a t-shirt, I assumed Harrison would be dressed similarly.

I was of course proven wrong when he answered the door in a nice polo shirt and pressed jeans, he at least wasn’t wearing any shoes. I chuckled to myself when I noticed his socks matched his shirt.

I said, “thanks for helping me out, I really do appreciate this.” I pulled the laptop out and handed it to Harrison.

He looked at it and said, “oh wow, I am not making any promises, it looks like you have gotten the most out of this old thing.”

I sighed, “yeah I know, I have a new one coming in a couple weeks, I just need it to last until then.”

He nodded, “ok, let’s see what we can do.”

I watched over Harrison’s shoulder as typed and clicked all over the screen trying to connect to his wi-fi. He finally got connected and just as quickly lost it.

Harrison ran his fingered through his perfectly combed hair, “I don’t know Adrian, all the quick fixes I know aren’t working.”

He started to bring up a lot of screens and menus I have never seen before and clicking away at the mouse. I stood up and paced a little, looking around the apartment. I was not surprised to see that everything is in its place and neatly organized, there wasn’t a speck of dust anywhere.

Harrison sighed, “I think I may need to call in a backup.” He picked up his phone. “Hey Joe, it’s Harrison, I am working on a buddy’s laptop, I keep getting a kicked off the wi-fi with an error message.” As he read the error message to Joe, I motioned to Harrison that I needed to use the bathroom, he nodded and pointed me in the right direction.

I went onto the bathroom and took a pee, noticing that it was as neat and tidy as the rest of the apartment. His deodorant, shaving cream all lined up on the shelf above the sink, labels all facing the front, I chuckled as I washed my hands and left to rejoin Harrison.

As I walked back into the room, Harrison was staring at the screen, he didn’t notice that I had returned. Once I got closer, I saw what was on the screen, it was a video that I had seen before. It showed a redhead guy getting roughly fucked by a dark-haired jock type. I moved closer, Harrison still not aware that I was in the room.

I said, “that is a great video.”

Harrison nearly jumped out of skin, “oh, I was, it just, fuck you scared the shit out of me.”

I was laughing so hard I couldn’t speak.

He shut the laptop, “shit, it just came up when I got connected and reloaded your last session, I didn’t bring it up, you must have been watching it when your laptop crashed.”

Still laughing, “dude, it’s ok, relax.”

Harrison calmed down, “I needed to reset your IP address, it should be ok now.”

Smiling, I said, “thanks bud, I appreciate the help. You know it’s ok if you liked the video.”

He snorted, “what makes you think I liked it?”

I looked down at his crotch, “that bulge you have in your pants.”

He quickly moved his hands to cover himself. I reached over and opened the laptop, and hit play and looked back to Harrison, his eyes immediately went back to the screen.

I asked, “do you know why I like this video?”

Harrison just shook his head.

I said, “because that redhead getting fucked kind of looks like you.”

He blushed as he went back to watching the video. I walked up behind Harrison as he stared at my laptop, I rested my hands on his shoulders and started to massage him slightly. The hand that he had covered bulge with was now rubbing his hardon through his jeans. I increased the pressure of my massage and leaned down and started to kiss his neck, he leaned his head to the side to give me better access. I moved my hands down to his chest exploring his tight body. I reached up under his chin, turned his head toward me and kissed his lips, Harrison looked at me, then started to kiss back.

I pulled him up out of his chair and we wrapped our arms around each other while our tongues danced in and out of each other’s mouths. Harrison let out a deep moan when I ran my hand across the rock-hard cock trapped in his pants. I fumbled with his belt, then unbuttoned the jeans and pulled the zipper down. I pulled his shirt out of his pants and broke our kiss so that I could pull it over his head. I looked him up and down, having never seen Harrison without his shirt, I was impressed, I smiled and went back in to continue our make out session. Harrison was really starting to get into it and was exploring my body with his hands, he finally worked up the courage to reach down and squeeze my dick.  I opened his pants up to prepare to pull them down, I stepped back and pushed the waist band off his hips, that is when I saw it. I could barely contain my laughter, Harrison’s underwear matched his socks, I mean the same stripped pattern and color exactly. Luckily the large bulge distracted me, and I went back to my task and pulled the underwear down to the floor.

A perfectly shaped 6-inch cock appeared before my face, I smiled and looked at the cock and then up the abs, to the chest and back to the cock. Harrison was completely smooth from his waist up, in fact the only hair on his entire body was a small amount under his arms and the bright orange patch just above his dick. Our eyes met, I grinned and ran my tongue across the head of his dick as Harrison shuddered, I then sucked his entire cock into my mouth. Harrison went weak in the knees and put his hands on my shoulder to steady himself and let out a “holy shit.”

He pushed my head off his dick, “dude, you are going to make me cum.” I stood up and removed my clothes, Harrison gave me the once over and reached out and took my cock in his hand and began to stoke. I returned the favor as we once again were kissing.

He pulled back and whispered, “can I try to suck you?”

I nodded as he went to his knees and said, “I have never done this, tell me if I do anything wrong.”

I said, “just relax and go slow, start by just licking it and then watch your teeth when you suck.”

He took to it like a duck to water, he was a natural and I told him so, I could see the pride in eyes as he looked up at me.

I pulled him up, “let’s go lay on the living room floor so we sixty-nine.” We got into position and went to work on each other, I played with his smooth balls and then worked a finger along the crack of his ass. I was surprised when he lifted his leg a little, I took this as a sign and worked my finger a little deeper until I brushed across his hole. He released my cock and let out a deep groan, I pushed further, and he grabbed his cheek to open his hole even more. My finger broke through the first layer of muscle and Harrison began to squirm.

I asked, “do you like that?”

He breathed, “fuck yes.”

I replaced my finger with my tongue and pushed it in as far as I could, giving his ass a good working over.

Harrison gasped, “oh Jesus Christ, that is incredible, holy shit I want you to fuck me.”

I froze, did he just say he wanted me to fuck him?

He repeated, “please Adrian, please fuck me.”

Thankfully I was a boy scout when I was a kid, and learned to always be prepared, I scrambled to my laptop bag and pulled out the condoms and lube I had packed before I drove to Harrison’s place. I rushed back to Harrison as he was on his hands and knees with his ass in the air. I gave his hole another good licking as I rolled the condom on and lubed up and prepared to send my eager cock to heaven. I was slowly pushing in, when Harrison pushed back quickly, and my nuts were tight against his ass.

I heard him gasp, I stopped and asked, “are you ok.”

Harrison panted, “shit yes, fuck me.”

I picked up speed, his ass was so tight, it felt amazing and from the sounds Harrison was making, I think he was enjoying it too. A few minutes later, he pulled off my dick and flipped over onto his back.

He threw his legs in the air and said, “fuck me, like in the video.”

I was happy to honor his request, I leaned in and kissed him as I pushed my dick back in his hot hole.

We broke our kiss as I started to pick up speed again. He grabbed my hips and pulled me into him deeper, then yelled, “harder, faster.” I pushed in deeper and faster and was looking into Harrison’s eyes as they were rolling back in his head.

He grabbed my hips again, “please Adrian, fuck me harder, pound my ass.”

I said, “ok, you asked for it.”

I let loose, as fast, and as hard as I could, I had him pinned to floor, his cock flopping between our stomachs. Harrison was moaning and groaning, squirming under me. He let out and oh God, as his dick exploded all over both of our chests and stomachs. His spasms pushed me past the point of no return, and I filled the condom with my seed.

I rolled off Harrison as my dick began to soften, we lay there trying to catch our breath, that was the wildest fuck I ever had.

I looked at Harrison, “how was that?”

He took a deep breath, “I have to admit, it was fucking awesome.”

I chuckled, “how long have you wanted to do that?”

He sighed, “I didn’t think that I did. When I saw that video, then you started to touch me, well I guess I just lost all control.”

I said, “well, you are great bottom, just a natural. If you ever want to lose control again, please let me know, I will be happy to help you out.”

Harrison thought a moment, “I am surprised at how much I liked it, and I do have to admit that I have a been a little curious since Bubba was asking you all those questions that night we were playing cards.”

I smiled, “I am always happy to help straight guys try new things.”

We lay there for a few more minutes, my mind went back to when we were undressing, I burst out in laughter.

Harrison sat up and was looking at me, “what the hell are laughing at?”

I sat up too, “where do you find matching underwear and socks?”

He was serious when he answered, “oh, I buy them online, there is website that sells all kinds of matching clothes, they recommend colors and…”

I rolled over laughing again, holding my gut.

He looked confused, “what?”

I said between laughs, “you wear matching socks and underwear.”

by Lee Obrien

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