We'd been best friends for almost 10 years. Worked together for about 6 on and off, and we knew each others family's and I loved his wife and puppies almost as much as I loved him.
He's not much to look at, tall and skinny, with a cute face and the ability to grow a 5 o'clock shadow in about 2 hours. His personality is infuriating yet endearing, his sense of humor very similar to mine and an insatiable desire to break the rules (and lie about it). Never big rules but certainly a mischievous streak through him.
I can't lie that I have pretty much wanted him sexually and had a massive crush on him since the first time we hung out but obviously nothing came of that especially since he has always been with his girlfriend come wife and I got to be in their wedding.
We'd been talking about a trip for a while and finally the time comes for us to go on a skiing trip to his family condo in the UP of Michigan. Dates confirmed, time booked off and all was in place. His wife had to change plans and cancel due to a work thing, and my boyfriend couldn't make it either last minute. We packed up the car from work and start on the 6-hour journey north from Chicago. The drive was pretty uneventful, dogs in the back, smoking cigs (our favorite things to do together) and one or 2 stops for piss breaks, snacks and booze for the condo.
We pull in and unpack, turn on the heat, order pizza, and start drinking. He doesn't get very many drinks in before he starts getting woozy and falls asleep on the couch. I let the dogs out, clean up (this always seems to be the trend when we hang out- I clean up and he sleeps), and head to bed leaving him on the couch. Being alone with him makes me so horny, especially when he's wearing sweatpants. I lay down, flip through tumblr and rub one out. I get up to go pee before drifting off to sleep and see he made his way into the bedroom.
We wake up the next morning and get ready for a full day on the slopes. Start with coffee and a few shots and take the dogs on a big long walk. Back in for another shot or two and head out. Have lots of fun, talking about work and laughing and joking the whole time, head to the lodge for lunch and of course a few more shots- why not? We're on a mini vacation! Back to the slopes for a bit and now it's time to go in for the day. We're cold and a bit wet and the buzz has now settled in and we just need to chill.
I go into my room and get changed- I hear him yell something at me and I can't hear it- I ask him to repeat it and he does but I still can't hear him- I head down the hallway past the bathroom and there he is peeing with the door open. I have never seen his dick before, only ever his bulge but never his dick and there it is. I try my best not to stare but this is like 8 years in the making. He's rambling about dinner or something but I literally can't even pay attention cause I'm like looking at his prick like it's the last thing I will ever see before I go blind. I'm not sure what I was expecting but I wasn't disappointed. He was a moderate flaccid size, probably like 3 inches soft, with a defined color difference about halfway down. At this point he notices me looking and asks me why I'm staring. Automatically I go "bro" and respond with a small dick comment or something like that. He shakes and puts it away and we grab another shot and sit down and turn on a movie. We settle in with the pups on the couch and about ½ way through we decided to order take out and keep watching the movie. He places the order while I piss. He shouts for my wallet to pay for the order and run out of the bathroom and hand it over. He points out that I didn't wash my hands.
I said "neither did you before and besides my dick is super clean".
He said his was too and I said it didn't look like it since it was two different colors. He punched me told me to shut up and that it was his circumcision scar and he's really self conscious. I told him not to be as I have an obvious scar and a (very small) mole.
He said "no way! Let me see...". My mouth was instantly dry and I got a little light headed. I'm thinking "what the fuck is happening right now?" But I actually say "I'm not showing you my dick. You can't really see it when it's soft anyway."
Now I know this was a two-fold ploy- he would either drop it and I'd get out of showing him my soft dick (of which I'm not a huge fan due to being a grower and not a shower) or he'll opt for me (or us) to get hard. Neither happened really...he kind of protested and stated I'd seen his soft and I shrugged it off and told him he showed, I didn't ask to see it and then it just got quiet and we kept watching the movie. My mind is reeling- I want to get hard and see each others dicks and maybe even jerk off together- would I be able to suck him even? I'm being mind-fucked right now but he just gets up and gets us another drink. He sits back down next to me and starts talking about his dick again. Super chill, not sexual, just about his size, and it's appearance and it actually gets a bit sincere for a hot minute (which only happens when we're drunk) and we're just sitting here talking about cock. Why not right? I can't help but to get a bit hard, I would say half chub right now but my shorts aren't hiding it but not showing it off either. The doorbell rings, the dogs go crazy as I run for the door to greet the delivery guy and he wrestles the dogs into the bedroom. Half chub on view I come back to the couch and put the food on the coffee table.
Dick is no longer the topic of conversation and we dig in to the food as if we've never eaten before. We drink and eat for a while and then I take the dogs out for a few minutes. I come back in and he's fallen asleep on the couch. Not asleep asleep but just dozing I suppose. I stand and watch him for a minute- He's not always my favorite person drunk but I really do love him- in this fucked up brother kind of love like I just want to take care of him but then also this step-brother kind of love where I wanna suck him.
As I let my mind wander and my hand rub my dick through my shorts for a second, I see his bulge swell just a little. I stop breathing hard like I just got caught and listening for his steady nap breathing and he's not waking up but I am on edge for sure. I watch for just a little longer (without rubbing myself) and sure as shit his dick grows just a little bit more.
I cough a little and he kind of startles awake, nods my direction in thanks for taking his dogs out and gravelly states "what's next? More drinks?" I nod about the drinks but say "maybe you need some alone time- your dick doesn't look like it wanted to nap."
He looks down with little shame and rubs it through his pants. It's so weird- he's not a sexual being to me, he's a target of my sexuality but he isn't sexual to me so this obvious act is odd to me but I'm not gonna lose an opportunity to share something with him (if it goes there). He mumbles something about how his wife doesn't ever blow him and barely has sex (of which I already know from talking to her) and I offer him alone time again. He ignores me as I hand him another glass of bourbon. We clink glasses and I sit down in the chair opposite him. I console him on lack of sex and talk a bit about me and my boyfriend's sex life which also had slowed down recently. He'll talk about it with me but we don't ever talk details. He gets up to piss and I follow just in conversation and he pulls his dick out again.
Perhaps a bit bigger now, I say to him "I almost think you want me to look at your cock". He just looks down at his piece and shrugs
"well you've seen a lot more dicks than mine- other than the color what do you think?"
I stammer out "it's good yeah- I mean from what I can tell it's a decent size that will obviously get bigger and your......well your head it a good size and shape. I mean I'm not expert but yea sure- well done...hahaha."
He smiles and his eyes close drunkenly halfway. He steps out of his sweat pants and just leaves his boxers on and stumbles out into the living room to grab another shot. I ask if he thinks he needs another one, but he ignores me and swigs out of the bottle. Been here before- he reached the apex of his drunk and now he's on the down swing. He'll stumble around for a bit longer and fall asleep in some random spot. At this point it's easier to join him than beat him so I grab my bottle of jack and take a deep swig. We step onto the deck and smoke a cig and go back inside. Well almost like writing a story, he takes another sip, lays on the dog bed and falls asleep. I keep drinking while I clean up dinner stuff and straighten up until I figure it's time for bed. I go and try to wake him but he just grumbles and rolls over. He's basically a bag of bones so I grab him by the arm, pull him up, and drag him into the bedroom. Throw him on the bed and grab the blanket. I happen to notice his dick poking out of his boxers- well this is the end of the line. I'll probably never see it again, so I study it. I don't touch it- that would be weird and creepy but I sure do get close and will it to get hard. It won't but I am rock hard. I just want to jerk off being so close to his crotch, this ethereal thing that I never imagined I would see let alone be in such proximity to kind of smell his musk. My judgement falters- I grab my phone and take a few pics. I scurry off to my room to cum to this real life fantasy happening in front of me. I feel guilty but the power of the cock is much more powerful and I try to last but I can't. My balls are tender from being teased all evening and I let it bust. I wipe off with my undershirt, throw it on the floor, pull my underwear up and pass out.
He comes in the next morning as cheery as can fucking be which is so frustrating because truthfully I feel hungover and shitty, cup of coffee in one hand, a shot in the other and a big grin on his face.
"Ready for another day on the slo....WHOA! Dude I can see your dick and it's hard!"
I look down bleary eyed and my dick that had sneaked out of the fly of boxer briefs and there it was in all its morning glory. He was staring pretty hard at my dick and then says "gross" and looks down as he stepped on my cummy undershirt. I am so mortified- he's now seen my dick and stepped on my cum shirt (of which I unloaded on looking at his dick). "DUDE! Please tell me that isn't your load I just stepped on!" I can't lie as I reached for the shot before the coffee and just shrugged and said sorry as I sat up and covered up my dick. I assess his reaction and notice he's not particularly bothered and also doesn't care about the dick show. I chase the shot with the hot coffee and tell him to get out while I get up and about. "Why does it matter now, I've seen yours and you've seen mine."
I said "it's weird and I didn't see yours hard- get out!"
He walked out and casually said "I'll start laundry if you wanna throw that shirt in...hahaha." "Fuck off!" I retort.
I compose myself, my dick deflated, pants on and an armload of laundry, ski clothes from yesterday, and of course the cum shirt. I dump the laundry into the washing machine and flick it on, fill up my coffee and pad into the bathroom to shower and get ready.
I'm in the shower under the hot water and my brain is so jacked up right now- he's in my head and I don't like that- I've kept my feelings under wraps all this time and it feels weird but exciting that this shit is finally going down but I'm not sure what is actually going down but that doesn't stop me from chubbing up. I'm chillin' under the water and the door opens to the bathroom. He walks in past the shower curtain and pisses while he talks loudly over the water and his stream and asks what I want to do today. I tell him I'm a little sore from all the skiing yesterday and maybe we should hit up the casino first and then do some afternoon slopes. He agrees and walks out of the bathroom. I go into my bedroom and get dressed, come back out for more coffee- and I sneak another shot.
I ask in general "when do you want to leave?" I hear a mumble but nothing I can make out so I asked again. I walk into his bedroom and his dick is standing to attention, with his hand wrapped around it and he's got a shit-eating grin on. "what the fuck are you doing?!" I say to him. He laughs and says he didn't think it fair that he had seen me hard and I hadn't seen him fully hard yet. I call him a weirdo and he says
"I kind of remember you talking about your own dick last night and said you were had a scar and mole- can I see it?"
"What in the actual fuck are you talking about?"
"Come on- we know everything about each other- just let me compare..."
"well...no...well...are you sure?"
"Sure why the hell not?"
I'm so glad I've had 2 shots by now as the dutch courage is kicking in. I'm already so fucking hard but my jeans are restraining it so I tell him I'll be right back and go to my room to shuck my jeans and pretend I had to work on getting hard on there. I walk back in with my boner tucked up underneath my waistband feeling more self-conscious than ever. I see he now has no clothes on at all and his cock standing proudly almost entirely straight and a right angle from his body with the slightest of up-curves (like barely there but still there). Mine on the other hand is straight as an arrow but points upwards. It's only about 5.5" but it's a pretty one. His is about 6.5 and I was right- the head filled out to be a perfect helmet. My mind is blank- all I can think about is dropping to my knees and having him skull-fuck me until he comes down my throat but I shake that vivid image out of my mind and hold my cock out front of me so he can see it. I am so shy and he takes a few steps forward and I take 1 step back. He laughs quietly but takes a bigger step forward and we're almost tip to tip. We stand in silence for like 90 seconds just checking out each others dicks. My mouth is dry as a desert and my breathing is super shallow and he's acting like we're on the deck having a smoke- bizarre behavior for this weird situation. Come to think of it though, his H.S. friends always said that he wanted to be gay but his body would allow it! Anyway- there's been no contact so it's not gay per sé - right? That's what any straight guy might say. He doesn't- he looks me in the eye and taps my dick with his left hand. Not hard, not soft, just kind of a test the waters love tap? I am shook!
"we're pretty similar I guess, except I'm a bit longer but you're a bit thicker and your head is nicer looking than mine." I just stared blankly back at him and nod in agreement.
He looks back down at our pricks and then says "cool- ready for the casino?"
"yea...sure...yea...let's go...do you want a drink?" my mouth and brain work really hard to form this sentence and I kind of zombie walk back out to the kitchen to pound another shot before he even joins me. He appears 1 minute later fully clothed, pulling on his jacket.
20 minutes later we're walking into the casino. We both agree not to spend more than $100, as he blows through his in about 12 minutes, I'm actually on a good streak. He pulls another $100 out of his account and blows that too. In the end, about 2 hours later he's in the hole about $240 and I'm up $120. He's pretty annoyed and I'm ecstatic. We hop back in the shuttle to take us back to the condo.
"is it ski time?" I ask happily, riding my gambling high, and he snaps back
"no, I need a nap."
"Fair enough, I could do that before we go out."
Back home, dogs out, dogs back inside and he's in his room with the door closed. He can be such a sore loser but I'm not phased, I'm used to it by now. I fall asleep for about 45 minutes when I hear the door open. He lays down next to me and I am on high alert- nervous energy in the pit of my stomach wondering what the hell will happen. He apologizes softly for being a dick after the casino and stares up to the ceiling. He's wearing the gray sweatpants again and I can't think of much else. I ask him if he wants to get ready for the slopes and he responds
"yea in a bit"
He's oddly quiet- and a switch flips in my head- he's obviously in here for a reason and maybe he's not sure of the reason but I have an idea that he's just seeing how far he can push me. For being the older, nurturing side of the relationship I can be pretty passive when it comes to him. I'm not sure why or even how I had the balls but I lifted my hand and put it on his crotch. He breathed in sharply and hesitantly but he didn't move. I start to rub, and boldy slide my hand in between his waistband and his hips...no underwear- surprise surprise!
Now I'm the one in control- I take over and sit up and pull his waistband down and under his balls. I hadn't noticed his balls before, but they were hairy, loose but not very big. I look him once more in the face to confirm that this is actually going to happen. I can't necessarily say his look was confirming but it wasn't negating the situation either so I grabbed his hot cock and started to jerk him off. Slow, rhythmically, with a little pressure. He's staring at the ceiling as if he looked down at what was happening something would happen. I leaned in closer to this cock, bringing it close to my lips, and spit on it. I needed that prick in my mouth but it was too fast too soon and I couldn't risk freaking him out and stopping this experience almost a decade in the making. I worked his cock and glancing up to him to see what his face was saying about the situation. Eyes open, ceiling focused he was just breathing deeply. I stepped off the bed and kneeled next to the bed and kept my steady jerking of his cock. He looked at me wondering what I was going to do. I didn't change anything other than my position but this time he continued to look at me. I smiled to him and he returned the smile, hesitantly but still a returned smile.
"Do you like it?" I asked him quietly and kind of breathy- it actually sounded a bit porny coming out of my mouth and that is not me so I cleared my throat and asked again "Is it cool that I'm doing this?" He smiled and whispered a yes. This high school jerk fest was lasting a bit too long for me to be honest as all I wanted was to blow him. I got closer to his cock to spit on it again to lube him up and he thrust his hips up as I approached. He immediately looked away like he was almost embarrassed for it but I loved it. If I was gonna suck him, I wanted to make my fantasy work too so I spit again, settled back to sitting on my feet as if nothing even happened. His eyes found his way back to my face and I looked at him silently telling him what was about to happen. I tugged at his leg closer to me, as if to tell him to turn and he obliged. He's now laying in front of me waistband still under his balls and I'm looking up his body.
I tell him "stand up" and he looks down and does what I ask. He's stood in front of me and I slide his sweatpants down to his ankles, almost straight dick at eye level. I kneel up and I run my tongue around his slit, and suck in his head into my mouth.
He does the typical guy "mmmm" but he has no clue what's about to happen.
I work quickly but thoroughly up and down his shaft and feel his balls with my left hand. That spot right behind his balls and before his ass is a little damp and smells amazing. I inhale his dick, balls deep so my nose is in his bush. He surprises me and grabs the back of my head. Holds me with a little pressure but not enough I couldn't pull off- but I don't want to, not quite yet. With his head in my throat and look up to meet his gaze, and smile with my eyes. I pull back about half way and go back down again but a bit more...slutty...
I slobber on his dick and throat fuck myself with his hot cock. I am in a daze, finally getting this moment and trying to savor every minute. I get the urge to rub his chest and up and down his body but that might make it too real for both of us. This will be the ultimate sexual experience NSA with no feeling, manners, or care. Just sex.
I know that it won't advance any further than this blow job (even though that would be fun) but I honestly love him so much that this was way too close to potentially damaging our relationship as it is so blow and go would have to be the limit.
I grab his hands, and he pulls them away, as if I was going to hold them or something. I sucked his prick back in my mouth, reached for his hands again and placed them either side if my head. The open invitation to fuck my face. He gets the message and starts slowly at first but I close my eyes and concentrate on breathing and he starts thrusting into the back of my throat time after time. His balls are hitting my chin every other time and I'm gagging every once in a while. He's not as big as the boyfriend, but he deserves a gag right?
He starts getting vocal, nothing specific, more like the "fuck" and "oh yea" but that's all the encouragement I need. I pull off his while his prick leaks on my forehead and across my eyes, I'm eating his balls like it's my next meal. He's sensitive but I don't care. I nuzzle into his sack and breathe in his smell. FUCK I am so hard and leaking precum through both layers of my underwear and shorts. If I reach in and pull my dick out will it weird him out? I actually giggle to myself as I gobble on my best friends balls I'm worried about weirding him out.
I pull my shorts and undies to just below my knees and spread my legs to get access to my pole.
I glide right back up to his dick and put it back in my mouth with my tongue doing flips round his head, and start jerking him a little while his head is on my tongue. He gets a bit rougher with my head and thrusts harder into my mouth. He looks down and we make eye contact and he says what every gay boy loves to hear-
"I'm getting close"
At this point I let him figure out what he needs. He pulls out of my mouth and starts jerking off as his cock head rubs on my tongue hanging out of my mouth. He going harder as I rub his balls and press my finger on his taint, lightly but intentionally. He gasps slightly, and rubs harder. I'm getting close too and my head is swimming in euphoria. He chokes out "I'm gonna cum" and looks me dead in the eye- I see his eyes roll back slightly and force his cock into my throat. I feel the first blast of cum shoot down my throat, and I start blasting my load on the floor while I pull out slightly to taste the rest of his on my tongue and pull out a little more so it paints my lips and a little of my cheek. He's shaking and heaving and recovering but I'm not sure I can handle this being over so I keep licking and sucking his dick as it starts to recoil slightly. He looks down at my face, all red and sweaty, with his seed on my lips and a big smile on my face. He says "Thanks bro" rubs his dick on my lips, and steps out of his sweatpants and turns and walks out of the room.
I instantly go into freak out mode that our relationship is over, how am I ever to look at his wife ever again, he probably thinks I took advantage of him. I hear the shower running. I look down at my spent cock and try to wrap my brain around this. I hear a muffled sentence- wipe my face on my undershirt (yes another one to wash) wipe my dick, pull up my shorts and walkout of the room toward the bathroom.
He says it clearer now "are you ready to head out in a few minutes?"
I say back in my chillest voice "yea sure...I just need to wash my face, brush my teeth and throw my ski pants on and I'm good."
"Great!" he says "pour us a drink while I finish up."
I obviously get ready and pour us a drink. He walks out of the bathroom with a towel wrapped around his waste, grabs the drink from my hand, and goes into his room to get ready.
We're on the chair lift heading up the hill, and I haven't really said anything since we left the condo. It's a bit quiet and a tad awkward on the lift- and he turns and looks at me. I see him out the corner of my eye and he says
"ummm...I know that was a big awkward, but I don't want it to be, and I wanted to say thank you again." He leaned in a gave me a quick peck on the cheek. Silence...
And I start laughing so hard- like crying laughing and hes laughing but kind of confused. I can't control it- it's hilarious to me.
I warbled through my laughter "that was the gayest thing you have ever done and that includes sticking your dick in my throat." He stops dead, realizes what I said and punches me and starts laughing. We ski until the lights come on and head back in for a lot more drinks and to enjoy the last 12 hours of our mini-vacation.
Thank you, Johnson.Wank10@gmail.com