Married Friend Loses Himself in my Cock
My friend Jake and I were on a quick guy's weekend getaway together. It'd been years since we'd had any real bonding time; his wife and kid obviously took priority, and my job kept me pretty busy. This weekend had been a long time coming, we'd both been looking forward to it for a couple of months. Jake was a long time buddy, we'd met in college, where we spent most of our time together or with his girlfriend (now wife) Lisa. Our shared love of sports led us to a couple days in Vegas where we'd spend time at the bars or sports book, watching anything while drinking and catching up.
We'd always had a competitive relationship, whether it was playing sports together, trivia nights, or who could eat the hottest wings, that competitive spirit was always nearby. It had come out a few times over the weekend, whether it was who'd bet more on the roulette wheel (he would), who would pick more games right over the course of an evening (I would), or who could drink the other one under the table. After a few drinks, Jake asked me about my dating life.
"Eh, it's hit or miss. It's tough out there, lots of girls don't really know what they want." I had had a couple girlfriends over the last 5 years since graduation, but none of them lasted very long, usually because of one specifically large problem, but I wasn't about to get into that with Jake.
"Ah come on, you're a great guy! Look, that chick across the bar, let me go wingman for you." he suggested.
"Nah, that's not why we're here. Don't worry about my love life, things will work out; they always do! And anyway, how are things at home?" I questioned.
"Eh, you know. I love being a husband and dad, but it's exhausting. I have no time for myself, and you can imagine what it does to our sex life!"
"I can safely say I probably shouldn't be imagining your sex life, Jake, especially not after a few beers! Not with my imagination!" I laughed.
"Sicko." he chuckled. "She has the energy for it, it's really my fault. Work all day, handling the kid, I'm just tired! But we still find time occasionally. I honestly don't know why I brought it up. Guess I miss it more than I realized."
"Who can blame you? She was always a firecracker. I always figured she was amazing in bed" I wondered how inappropriate the liquored up Jake would be.
"Best I've had! And the only, as you well know. But seriously, you must be talking to *someone*, right?" he was insistent, so I figured I'd play along.
"Yeah, online dating is different than it used to be. Lots of picture exchanges, a lot less chatting."
"Let me see! Who's been sending you pics? Lord knows I don't get this kind of fun anymore."
"Alright, let's see..."
I showed him a few different girls I'd been chatting with lately. I was careful to only show their pictures, not my own, those apps can be confusing sometimes.
"Dang! Some of them are hot! Good for you!" he complimented me. "Wonder if they'd respond like that to me...I never really got to explore."
"Well, you know, we could make this interesting." I suggested. "I'll send pictures of you to those girls, but you have to send a picture that I take of myself to Lisa. Always wondered what she thought of me."
"Brett, what the hell? No way! That's across the line, she would be shocked!" he exclaimed.
"Well obviously I wouldn't include my face, so she wouldn't know it was me, you could make it some kind of 'get in the mood' game for the future. See who you both find attractive. We used to do that sometimes in college, remember?"
"Yeah, we did." he was considering his options. "Hey, let's make it real interesting. Since we're already gambling this weekend." He had a weird look on his face. "We've known each other forever, and we've never done some things lots of guy friends do. Well...let's have a dick measuring contest. If I win, I'll send pictures to those chicks you're talking with. And if you win, you can send a picture to Lisa."
Now, that one specific big problem that most girls had was...my cock was too big for them. They'd try so hard, but either they couldn't really fit it into their mouth, or I'd bottom out while fucking them, and while I could make it fun for them by being slow and gentle, it was never that fun for me, and eventually I'd lose interest. What that meant now though, was...I knew I would win this bet.
"You're on!"
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We'd finished our drinks and headed up to my room, where a drunk Jake was excited and confident. "What should I send those chicks? Are dick pics still popular? Or would they prefer body shots?"
"Don't count those chickens yet. But yeah, the occasional dick pic is fine if you warn them. We'll see what we do after we find out who wins. How do you want to do this?" I asked.
"Oh, I'm already ready to go, so I'll go first. Here, my phone has a ruler app, so we can make it official."
He must have been really excited for this, because he wasn't lying. He pulled down his jeans and boxer briefs and pulled out his already erect cock. I hadn't been around another dude's cock since the showers in high school, and even back then I wasn't one to look around, so this was new for me.
He seemed very confident, almost cocky. "Didn't expect this, huh? Can't handle the heat? 7 inches, easy. 5 inches around. You can measure if you want. I bet those girls will love seeing a big cock for once, what was the most recent one, Katie?"
I ignored his jabs, knowing what I had in store for him.
"Impressive." I noted. It really wasn't bad, and in my experience, it was still in the top 25-50% I'd seen around the internet. Nothing to be ashamed of. At least, not normally.
His confidence disappeared as I slowly lowered my pants. Still soft, the outline of my cock was obvious against my loose boxers. Clearly almost as long as his, just as thick, and I wasn't close to hard yet.
"Brett, shit. You must be a shower! Doesn't get any bigger than that, right?" he questioned, doubting himself.
"I think you know better than that...just watch."
I lowered my boxers, and slowly started rubbing up and down the slowly growing shaft of my dick. The attention and proximity of another guy was something I'd never experienced before, and knowing I was bigger than him was turning me on in ways I hadn't felt. The confidence, knowing his manhood was nothing compared to what I was about to show him.
Slowly it got bigger, inch by inch.
"Well fuck, you're already bigger than me." he said, knowingly.
