Drinking Games - Dirty Bets

Freshman year of high school, my hormones were running my life. Jerking off every single day, sometimes twice or a marathon if my parents were out. At first I thought I had a problem, but talking to my best friend Tim I realized I was fairly normal. 

Tim and I had become really good friends over the summer between junior high and freshman year of high school. My family had moved to the same block Tim lived on so, through proximity we became best friends. We didn’t have much in common, but our interests were not far off. He was an athlete, loved baseball, I was on the swim team so we did train together. It was mostly running.

By the fall, we were best friends. He and I did everything together. Almost every weekend he would spend the night at my place or I would his place. A couple times we jerked off in the same room. It was an under the blankets thing, but it was still so much fun to share that experience with each other. We didn’t do that often, just when sleeping over when we were both really horny...just to get off. It would be weird if we liked doing it together right?

The weekend of Thanksgiving my parents were away, they were driving my older brother Jeremy and his girlfriend back to college and made a weekend of it out of state. So naturally me and Tim planned a three day weekend of being stupid. No sooner did my parents drive away Friday morning, Tim was knocking on my door.

The evening started out like any other. Mostly horror movies, pizza and can after can of Pepsi. Somewhere around 9pm Tim was getting bored of the blood and guts, “not enough tits” he joked. I was amped up from all the caffeine, and needed to blow off some energy before we called it a night.

“I can’t believe your prude parents let that hot girl stay over for Thanksgiving” Tim said.

“Yeah, and they let her sleep in Jeremy’s room too,” I laughed.

“Do you think they were fucking?” Tim asked with a huge grin, and adjusted himself in his basketball shorts.

“I think so, my room shares a wall with them and I either heard them doing it or they were playing tennis at 1 in the morning” I laughed.

“Awesome, tell me you jerked it while listening?” he asked.

I blushed, “well I was jerking off before I noticed the sound, but I just imagined I was fucking her and that did the trick,” I laughed, miming jerking off and having an orgasm.

“Let’s go see if there’s evidence,” he suggested.

My hormones in full swing, any evidence of a hot nude girl having been in the house would give me jerk off material for a week. We went into Jeremy’s room, it was a bit of a mess. We entered like it was a crime scene, at first not touching anything. Then Tim hopped on the bed and started humping the air, moaning and pretending to fuck a girl that wasn’t there. I just laughed at him.

I opened his night stand, there were a couple condoms and some lube.

“Well, they definitely were prepared for sex” I pointed out, holding up the condoms and lube, then set them on the night stand.

“That doesn’t mean anything, could be from when he was living here” Tim suggested.

“True, or maybe he used them to jerk off,” I said.

“I heard about making a fleshlight out of condoms, probably what he did,” Tim joked.

I went over to the clothes basket, there were dirty clothes and I carefully picked through. I saw no evidence of her clothes but I found a pair of his dirty underwear and held them up.

“Here’s some evidence,” I said.

“Of what? You and your brother wear briefs so he’s likely a virgin just like you” Tim laughed.

“Fuck you dude, you’re just jealous because I have a dick that’s big enough to need the support and yours is nonexistent in those ratty old boxers” I jabbed.

“Jokes on you, my Mom got me some new trunks to hold my junk,” he said.

“Your Mommy needs to buy you some balls to put in them” I laughed.

Tim grabbed Jeremy’s briefs from me, “looks like your brother blew his load in these,” he pointed out.

Looking inside there were some white tracks in the package area.

“Nah, that’s just pre-cum, it happens to mine too if I get hard wearing them,” I told him.

“So every five minutes” he jabbed.

Tim tossed the underwear back into the bin and went over to the dresser.

“Oh shit, your brother has one of those old Super Nintendo systems?” he said.

“Yeah, that’s the original, not the emulator” I told him.

He started digging through the top drawer.

“Dude, check it out,” Tim said, holding up what could only be a joint.

“Oh shit” I said, taking it from him. “You think it’s weed?” I asked.

“Only one way to find out,” he said with a mischievous look, and tossed it to me. “Bro, there’s more,” he said, pulling out a bottle of whiskey.

“Oh wow, my parents would kill him for bringing this into the house” I said.

“Well we’re just going to have to dispose of it, you know...to protect Jeremy” Tim laughed.

“Maybe later” I said nervously, never having tried alcohol or weed.

Tim opened the bottle, took a swig and made a disgusted face, then laughed, “good stuff” he could barely say. Then passed it to me. I wanted to try it, and certainly had to now that he tried it. I closed my eyes and took a huge swig.

Coughing, “oh yeah...smooth.” I passed it back to him, feeling it burn all the way into my stomach. He laughed at me.

I went over to the desk, there was a small trash bin between the nightstand and the desk. I looked in, there were some tissues.

“Yo, do you think those are from cleaning up after sex or just...like regular tissues?” I asked, showing Tim the bin.

“Probably tissues from him jerking off, he’s probably in the friend-zone” Tim laughed and took the bin from me.

I lay down on the floor and started looking under the bed.

“Oh shit, dude” Tim said.

I rolled over onto my back to see what he was excited about.

“Gross, is that a used condom?” I asked.

“Fuck yeah it is” Tim said, examining it.

“Don’t touch it dude,” I said, grossed out.

“Why?” he asked.

“I don’t know, because it was on my brother's hard dick” I laughed.

“Yeah, it was also inside her vagina” Tim said, matter of factly.

“Still, that’s Jeremy’s cum inside it,” I said cringing.

“I don’t care, I’ve had my own cum on me so many times, it’s all the same” he laughed.

“But it’s different when it’s your cum” I said, trying to sound cool and not uptight.

“Don’t be such a punk” he said, “this is the closest you’ll ever come to touching a vagina in real life” he held out the used condom for me to take.

I was not comfortable touching it and he could tell so he started waving it around in my personal space.

“Don’t be a baby Noah, just touch it” he said, shaking it around.

“Gross dude, no way,” I said.

“Just touch it,” he said again grinning.

“I’ll touch it if you lick it” I countered.

He laughed, “that’s gross, but I’ll lick it if you put the tip in your mouth” he countered.

“Nasty dude, no way,” I said.

“It would be like you technically ate her out dude” he pointed out.

That didn’t make sense to me, but at the same time it kinda did and my hormones were in overdrive and I took the condom. It was cold and felt weird. It was tied in a knot at the open end, I guess to keep the cum from oozing out into the trash bin. I held it by the rubber band end between the tips of my fingers.

“Do it dude” Tim said in a daring tone.

“I have to put it in my mouth?” I said cringing.

“Yeah, and then I’ll do it too, I’ll put the full length up to the knot in my mouth” he laughed, assuming I’d chicken out.

“Fuck” I said, then quickly put the tip in my mouth and quickly pulled it out. “Ugh, so gross” I almost gagged. It was so cold and felt so weird in my mouth, also something about the latex left a weird taste in my mouth.

Tim busted out laughing, “Holy shit dude, I can’t believe you did that. I really thought you’d be a punk” he continued to laugh.

“Your turn” I said very seriously, holding it out for him to take.

“Ah…”

“Unless you’re a punk” I cut him off, not letting him give me an excuse not to.

“I’m not a punk” he said, taking it from me.

He had it pinched at the rubber band end and held it up above his head so the length pointed down to his mouth. I just stared.

“Oh God, so gross, you gotta do it” I antagonized.

“Just the tip” he said, cringing.

“Nope, I did the tip, you have to go down to the knot” I laughed.

“Fuck, ok” he said.

Closing his eyes, he held his head back, opened his mouth and slowly lowered it in. Once it was down to the knot, he closed his mouth around it, opened his eyes looking right at me and slowly pulled it out until the tip filled with cum popped out of his mouth making a weird squishy noise.

“Ugh...oh God that was weirder than I thought it would be” He started to gag.

I died laughing. “So fucking gross” I continued to laugh at him.

“Bleh, that latex leaves a lingering taste doesn’t it?” he said.

“Yeah, it really does” I laughed.

He went over to the bottle of whiskey and took a swig, wincing he passed it to me. I took a smaller swig, just to wash away that latex flavor. 

“Oh man, that’s possibly a worse taste” I said, shaking my head and capping the bottle.

“Well, I guess it’s safe to say your brother got in that hottie” he laughed.

“Unless he just used the condom to jerk off” I laughed.

Tim laughed, “oh man I hope not, that would mean I basically sucked your brothers dick” he continued to laugh.

I laughed at him and nodded along.

“Don’t laugh, I may have sucked a dick, but you sucked your brother's dick” he laughed.

“Shit, good point, let's assume my brother fucked her then,” I said and took another swig of the whiskey.

Tim took another swig, “agreed.”

I couldn’t help but notice Tim was slightly aroused in his gym shorts. Not hard, but a noticeable bulge. For some reason that made me start to get aroused. I decided it was becasue I hadn’t jerked off yet today and all this talk of sex was getting me going.

“So you jerked off listening to your brother having sex?” he asked, putting the condom on the nightstand.

“I...not exactly” I said, a little embarrassed.

“Yeah you did, perv” he teased.

“Technically I was jerking off already, I just happened to hear some sounds that could’ve been sex and…”

“It made you cum” he laughed, cutting me off.

“Basically,” I admitted.

I took another swig of whiskey.

“Well what did you hear?” he asked.

“I don’t know, I think I heard the bed squeaking” I hopped on the bed, and pretended to hump a girl in a missionary position that didn’t exist.

“I don’t hear any squeaking” he laughed, he took another swig. Then hopped up on the bed behind me.

He pretended to hump me from behind, we both laughed but the bed did make some subtle squeaking noises. So he pushed me down flat and started grinding against me. We were both fully clothed and joking around, but I did feel his bulge rub against my ass and he felt semi-hard at this point. I didn’t say anything to stop it, I wasn’t sure what was happening. There’s no way he didn’t realize I could feel that.

I tried to push him off, but he’s a little bit bigger and stronger than me all the way around. I’m about 5’4” and he’s about 5’8”, I weigh about 120 and he weighs about 140. He has the extra muscle from working out for baseball, whereas I am more lean from swimming. I’m not weak, he’s just stronger. Trying to wrestle him has always been a losing battle for me. I just rolled onto my back so he couldn’t fake hump my ass anymore.

He stopped immediately, but I could see his semi bulging in his shorts. I pretended not to notice. I just laughed at him.

“Do you think he took her from behind or missionary?” Tim asked.

He was basically straddling me at this point, so I thrust my hips up into him, “she’s probably into riding a big dick” I laughed. I thrust a few times into him but wearing briefs my cock and balls didn’t have the swing his had, so I don’t think he felt my junk like I did his when he thrust me from behind.

He laughed, “assuming your brother has a big dick.”

I laughed, “well, mine is huge so he had to get at least a big dick” I joked.

He got off of me, grabbed the whiskey and took a swig. He passed it to me, I took a swig. Something about his mood changed.

“You ever ‘drink and drive’?” he asked.

“What, that’s dumb and no, I have never drank...before this” I laughed.

He laughed, “not like that, it’s where you play Mario Kart and the loser takes a shot after every round.”

“Oh, can’t say that I have.”

“Want to? We have plenty more rounds in this bottle?” he asked, holding up the bottle.

“I’m down, but be prepared to lose,” I suggested.

“You talk a big game Noah, I’ll bet I beat you within the first three rounds.”

“What do you want to bet?” I asked.

“I don’t know something big,” he said.

“Well it can’t be worse than putting that used condom in my mouth” I laughed and cringed at the thought.

“Oh I know”, he walked over to the hamper. He pulled out that pair of underwear with the precum in them. “The loser has to wear these, and only these for the rest of the night” he said very seriously.

“Ah, that's gross, I’m in” I laughed. 

I was starting to feel light headed already. We played a game, I won. He took his shot.

“Fuck, lets go” he said getting amped.

Second game, I won, he took another shot.

“Shit dude, you’re fucking going down,” he said.

Third game was close, neither of us came in first but I barely placed ahead of him in 5th place.

“That doesn’t count,” he said.

“Fuck do you mean it doesn’t count? I beat you,” I told him.

“You just lost better than I did,” he laughed.

“You’re just trying to punk out,” I told him.

“Fuck that, I’m not a punk, you just can’t get away with out some sort of punishment” he said.

“Like what?” I asked.

“Well, I’ll take my punishment, but you should have to take a shot too” he made sense.

I laughed, quickly took the bottle and took a swig. “Ugh...there,” I said tossing him Jeremy’s underwear.

He stood up, twirled the briefs around his finger like a hula hoop and laughed. He turned his back to me, dropped his shorts and boxers revealing his hairless ass. One foot, then the other into the briefs and pulled them up snapping the waistband once they were up. He turned around as if modeling them for me.

I laughed, “shirt too, your rule was the loser had to only wear the underwear.”

He gave me a fake scowl, quickly grabbed his shirt from the back of the neck and pulled it over his head and tossed it at me with a laugh.

“Happy?” he asked, doing a little dance that made his package bounce.

“How’s Jeremy’s crusted undies feel?” I asked as a joke.

“Surprisingly comfortable” he laughed.

I couldn’t help but notice how good he looked in the gray sport briefs. His toned body didn’t have any fat and they really accented his muscled ass and package in a way I never noticed when I saw him in his loose fitting boxers. I’m not sure if it was the underwear or him, but his dick looked big in them, maybe he was getting turned on?

“Next round, if you lose you have to take a shot and strip to your underwear” he said.

“And when I win?” I asked, very cocky.

“I don’t know, if you win I’ll...let you suck my dick” he laughed.

I laughed, “fuck no, but if I win...you have to suck on the knotted end of the condom.”

“Ew, that’s nasty. That end definitely had your brothers dick in it and probably has some of his juices on it,” he said.

“I’d be scared too if I sucked as bad as you,” I told him.

“Ok, fine, I’ll take that dare, but if you lose you have to strip to your underwear and hold the condom in your underwear until I lose a round,” he countered.

“That’s so weird, but you’re going to be sucking latex” I laughed.

“Wait, do we have to come in first or just beat each other?” Tim asked.

“Hmm...I’m going to win either way so I guess it’s up to you.”

“Ok, how about this, if the winner also comes in first place the loser has to do both dares” he laughed.

I laughed, feeling really tipsy but also confident I would win. “You’re on.”

We played the next round, did a random course and my bad luck...it was a course I struggled with. It was a pretty close game. He was doing really well, I had some setbacks but caught up with some red shells. On the last round he was in second and I was in third closing in on the finish line. All of a sudden stupid Princess Peach used a lightning bolt and we all shrank. I got run over, 4th place, 5th place.

“Fuck yes!” he shouted, crossing into first and the finish line in the last millisecond.

“Nooooooo!!!!” I shouted.

“Suck that condom!” he laughed maniacally, handing me the whiskey.

I took my shot like a champ at this point, a slightly bigger shot than I had all night because...fuck I just lost big.

“Where is it?” I asked, definitely feeling on my way to being drunk.

He hopped off the bed, grabbing it from the dresser, walking slowly over to me with a huge grin on his face. I couldn’t help but notice how his package moved in those briefs as he walked, I don’t know why but I thought it was hot. He handed me the condom.

“Fuck, ok, you’re really going to make me do this?” I asked.

“Hell yeah, man up, put it in your mouth” he laughed.

I looked at it, the cum still in the reservoir tip, the knot between my fingers and the open end...still open and looked wet.

Tim just laughed at me, “don’t think about it, just do it!”

“Ugh…” I shook my head.

I closed my eyes and put the open end in my mouth. Instant latex flavor.

“Put your tongue inside” Tim laughed.

I did as he said, I slid my tongue inside where my brothers dick had definitely been about 20 hours ago. It was still a little wet, I started to gag a little and pulled it out of my mouth.

“Thats...ugh...fucking disgusting” I gagged and laughed.

Tim laughed at me, “ugh, you’ve practically sucked your brothers dick.”

“You’re so twisted,” I laughed.

“You’re not done yet, shorts off” he said.

I did a little strip tease, slowly letting the shorts down over my round butt, exposing the package in the front. My shorts hit the ground. I held up the condom from the knot.

“In the front or the back?” I asked.

“Right between the cheeks” he said with a laugh.

I laughed, “You’re so weird.”

I dropped it into the back of my underwear and let the waistband snap shut of my stipped Jockey briefs.

“No no, right between the cheeks, turn around” he said.

I turned my back to him. I felt him grab the waistband of my briefs and stretch it out. He reached into my underwear, brushing my butt and grabbed the condom. Holding it once again by the knot, I felt it lengthwise between my ass cheeks. His hand resting just above my ass where the crack starts sending shivers up my spine and kinda made my dick twitch.

“Clench” he said.

I did and I could feel the cold latex filled with cum between my cheeks. It felt so gross, but at the same time, kinda hot in a weird way.

“There, now sit” he laughed.

I sat back on the end of the bed like before, still clenching. Tim sat back down next to me. I looked over at his bulge, it looked slightly bigger than before. I wanted to see it, just to compare. I slowly looked up his body, impressed by how defined he was for being only 6 months older than me. Eventually making eye contact. I was definitely feeling drunk at this point.

“Let’s go,” I said.

“What are the stakes?” he asked.

“Loser takes a shot” I laughed.

“Obviously. Alright, if I win…” he started to say.

“Nothing gross” I cut him off.

He laughed, “well now it’s gotta be.”

“Ok, let's set the game to hard. The loser has to take a shot, but if the winner makes it into the top 4…”

“He gets to drain the condom onto the loser” he cut me off laughing.

“Oh gross, no fucking way” I practically yelled.

“What’s the matter, you afraid you’re going to lose?” he asked.

“No, I just don’t want to touch that thing” I laughed.

“It’s already being warmed in your ass,” he laughed.

I forgot about it already, I could feel it between my cheeks, now warm and squishy.

“What difference does it make, you cum on yourself every night before bed anyway?” he pointed out.

“Yeah, but it’s my brother's cum” I said with a cringe.

“Would you prefer my cum?” he asked.

I hesitated, “well, at least then it would be fresh.”

He laughed, but I was serious. I didn’t want anyone's cum on me, but if I had to choose, that’s the way to go. I laughed at that thought and looked at his bulge in my brother's briefs.

“You got a better bet?” he asked.

“Ok, but it’s quick and then it gets cleaned up right away, no playing with it or anything weird” I said realizing I basically said what we were doing was somehow normal.

“Totally” he said.

“Alright, let’s go” I said, hitting start on a random course.

This one was a course I was pretty good at, but not set on hard. Tim seemed to be doing better on hard so I had to really focus. It was not a good round, he took a hit in the second lap and then decided to keep me from placing rather than beating me. He managed to put me into 8th place and he barely got 7th place.

I took my shot and made him go again right away, same stakes. I was definitely drunk at this point and I lost the round, I came 7th place and he got 4th...barely.

“Fuck yeah!” he shouted. 

He hopped up and strutted around, I watched his package bouncing around, I really wanted to see it.

“Take your shot and give me the condom,” he said with a laugh.

I took my shot and stood up, pulling my underwear down to reveal my ass and the condom.

“Come and get it” I said in a fake ‘sexy voice’.

He laughed and to my surprise he reached in and grabbed it, pulling it fairly quickly and it snapped out like a rubber band. We both laughed, he definitely touched my ass when grabbing it though...probably accidental.

“Where do you want it?” he asked.

“Nowhere” I quickly fired back. “I don’t care at this point,” I said, praying he didn’t want it on my face or worse in my mouth.

“Ok, lay down, face down,” he said.

I lay face down on the bed, my head by the foot of the bed by my controller facing the TV. I was relieved he wanted me face down, at least this wasn’t going to be gross.

He climbed on the bed, he straddled my legs, I could feel his balls in the briefs resting between my legs. I felt him grab my underwear and start to pull them down.

“What are you doing?” I asked, glancing over my shoulder at him.

“Bro you lost, I’m going to dump it out onto your ass” he laughed maniacally.

“Ew, gross man” I shook my head.

I paused for a second shaking my head, then caved and lifted my hips so he could pull my underwear down. The waistband caught on my dick which got hard the second he started pulling down my Jockey’s. I had never had someone pull down my underwear before, I was rock hard, it made me laugh, the comforter underneath me felt good against my dick. I felt Tim pull my underwear all the way off and he got between my legs spreading them a little with his knees.

He dragged the condom up and down my crack, snickering the entire time. I heard him struggling to get the condom un-knotted.

“Man, your ass warmed this up good” he said with a snicker.

“What can I say, I have a hot ass” I joked.

He spanked my cheek, “it’s nicer than any girl I’ve seen.”

“Yeah, you’ve never seen a girl this naked” I jabbed.

I heard a snap, he broke the condom open.

“Ah, there we go” he said, feeling him lean forward, closer to my ass.

“Ready?” he asked and I felt him fake hump me.

“Ew, I guess” I cringed.

Then I heard him chuckle and he faked an orgasm sound, thrusting his hips into me. His underwear clad dick and balls slapping my bare ass.

“Ungh, ungh...ahhh,” I immediately felt the warm cum splooge onto my ass crack, the condom being squeezed to get every last drop out. Tim was laughing the entire time.

“Ugh, it’s so warm” I said.

“Bro you just got your first hot load” he said, and proceeded to drop the condom on my lower back and spread my cheeks so the cum got to my hole. I felt it drip down to my balls.

“Dude, so gross” I laughed, trying not to move and make it all run down to my balls.

No one had ever played with my ass before, certainly never had anything touch my hole before and this was like a warm lube. My dick twitched and let out another drop of precum.

“Clean it up man,” I told him, trying to sound like I wasn’t for some reason enjoying it.

“Alright, alright, calm down ya baby” he joked.

I felt him wipe it up with a rag, paying extra attention to my hole. He spread my legs a little more and wiped my balls which felt amazing. I felt him pick up the condom and wipe that spot too and then toss the rag into the clothes bin.

“All clean,” he said.

I was afraid to sit up because I was so hard at this point, he would see it for sure and I didn’t want him to think this turned me on. So I just lay there. I looked over my shoulder at him, kneeling between my legs still.

“Where’s my underwear?” I asked.

“Oh…” he giggled. “I ugh, I used them to clean up the cum” he laughed. “The condom is wrapped up in there too” he laughed again.

“Aw man, now I’m going to know my brother's cum was in my underwear every time I wear them” I shook my head.

“It’s not so bad” he grabbed his package and shook it.

I laughed, “Oh, yeah”, I had forgotten he was still wearing my brother's underwear.

“You want to go grab a fresh pair?” he asked.

I couldn’t get up with this hard dick pointing out.

“Fuck it, whatever, let’s just go” I said.

“We only have like, two or three more shots in this bottle,” he said.

“They’re all going to be yours” I said with a new found confidence.

I subtly humped the mattress, slowly grinding my hard dick into the comforter. I stopped when I remembered Tim was sitting between my legs with a clear view of my ass flexing.

“Get your controller,” I said, not looking at him.

He scooted up closer, pressing himself into my ass, pushing my dick further into the mattress felt so good. My hormones were off the charts at this point. I could feel his package through the briefs between my ass cheeks. I didn’t say anything. I know he was just as drunk as I was, if not more, so I don’t think he knew I could feel it.

“What are we playing for?” he asked.

“Well, I’m already naked, and technically you dropped a load in my ass” I laughed.

“Yeah, I did,” he said proudly.

I am pretty sure I felt his dick get hard, it definitely flexed.

“Well when I win, You have to take a shot and get naked for the rest of the game” I said.

“What if I win?” he asked.

“I don’t know, what have you got?” I asked.

“Well it would be awesome if you let me actually rub one out on you” he suggested.

“What do you mean, jerk off on me?” I laughed.

“I mean, let me get off on you, actually cum on you,” he said, half kidding, half serious sounding.

“No way man, that’s so gay” I laughed.

“No, it’s just two friends having fun” he corrected me.

“And one of those friends cums on the other friend” I laughed.

He giggled, “You already let me cum on you once tonight.”

I’m certain he was hard now, I could feel him flex between my cheeks.

“Alright, if you win, if you come in first place you can get off on me however you want,” I said.

I felt him flex again.

“But if I win, in first place, you have to jerk me off,” I told him.

He laughed, “what if neither of us come in first?”

“If I win, but don’t come in first, you still have to take a shot and strip naked,” I told him.

“And if I win, but don’t come in first, you have to take a shot and sit in my naked lap” he laughed.

“So either way you’re getting naked?” I tried to clarify.

Clearly a bit drunk, he started to grind his dick between my cheeks, “I guess so.”

“Then why not just get naked now, and...play high stakes?” I asked not really thinking.

“Good point,” he said.

I felt him stand on the bed, heard him strip the underwear off and they fell on my head. I grabbed them, and looked at them. There was an obvious wet spot where his dick was, this made my dick twitch for some reason and I did a small grind into the mattress. I felt him sit back down on my ass, he was definitely naked. I could feel his balls on the lower part of my butt and his cock clearly wedged between my cheeks.

I pretended not to notice even though all of my senses went into overdrive. I was so horny and feeling pretty drunk, I didn’t care.

“Ok, so If I beat you and place in the top four, you will take a shot and let me jerk off on your hole. If I beat you but don’t place top four, you take a shot and just let me touch the tip to your hole” he said as if that was no big deal.

I just shook my head, “Ok, perv, if I win first place, you take a shot and have to lick my hole for 1 minute. If I win and place top four you have to take a shot and give me head for 1 minute.” I couldn’t help but laugh.

“What? No way that’s not a fair bet,” he protested.

“You haven’t taken first place in...half the bottle” I joked.

“Fuck you dude. When I get first place, you have to let me put it in you,” He said very serious.

“Fine, then if I take first place you have to suck me off until I cum” I laughed.

“But if I beat you and place top four you have to let me jerk off on you,” he said.

“That’s so gay dude” I laughed.

“Nah, it’s just a bet,” he said, somehow making sense.

“Ok fine, but just the tip, you don’t get to fuck me” I laughed.

“I’ll take it,” he said, his dick twitched again.

A bit nervous, I hit start. I was really in my head this round. It didn’t help that I kept feeling his obviously hard dick pulsing between my butt cheeks. After the first lap I got into 4th place, he was in 6th and getting competitive. He kept shifting his weight, leaning his whole body going around turns and it made his dick shift and throb, it was so distracting.

“Fuck I’m close” he said.

In my head I thought dirty, like he was about to cum, but then I realized he was getting closer to 4th place. I was determined to stay ahead of him. Quick thinking I realized I just needed to distract him, so I started flexing my ass as I went around the turns.

“Mmm, I’m close” he said, going into the third lap.

“Bro, get ready to lick my ass because I’m closing in on the…”

He got the lightning bolt and pushed it, everyone but him shrank. He caught up to me and ran me over, I quickly dropped into 7th place. He was in 3rd place, then 2nd place. I clenched my ass really tight, I heard him moan and cross the finish line in 2nd place.

“Damn, that was close” he said gloating.

“Fuck, I can’t believe you got the lightning bolt” I protested.

“Still I won, take your shot,” he handed me the bottle.

I took the shot, “you probably have whiskey dick.”

I knew he was already hard, but I hoped he would take that as an opportunity to not go through with it.

“I’m already getting hard,” he snickered. I felt him start stroking his dick between my ass cheeks, sending shivers up my spine.

“Fine, but you only said jerk off, you didn’t say cum” I laughed, thinking quickly.

“That’s bullshit” he said, humping his hips into my ass.

I felt the entire length of his shaft on that one.

“Sorry dude, but the bet was clear, that’s why I said if I came in first you had to blow me and let me cum in your mouth” I chuckled, feeling like I somehow was the winner for finding that loophole.

“Whatever dude” he said, spreading my cheeks apart to look at my ass.

I felt him stroking his dick. I looked over my shoulder to get my first look at his hard dick. I had seen it soft a couple times changing, but never hard. It was at solid 6”, but looked huge on his body. He had a little patch of hair above his raging hard dick and a dusting of hair on the balls that were tickling my ass as he slowly stroked his dick.

I turned back to face the TV. He spread my cheeks again and started to rub the head of his dick on my hole, it felt slick.

“woh, did you just cum on me?” I asked seriously.

He giggled, “no, that’s precum.”

Somehow that seemed fine, clearly I was drunk. Here I am, a straight boy, with my straight best friend rubbing his precum on my ass hole with his hard dick.

“Oh ok” I said, laying back down.

I felt him flexing his muscles as he jerked off. He shifted a little so he was between my legs, spreading them wider. He teased my hole with his cock with every stroke, it felt really good. I didn’t know my hole could give me pleasure. I accidentally let out a soft moan.

“Man, this probably sounds gay, but I really want to try...putting it in, you know, to know what it feels like” he tried to sound like he was joking.

I was clearly enjoying this gentle teasing, almost like a massage, but I was not going to let him penetrate me.

“It doesn’t sound gay, we’re both straight, it’s just...you know...a hole would feel good no matter who’s it is right?” I tried to make it less weird.

He stopped jerking for a second, rubbed more precum on my hole and smeared it up and down my crack. I felt a little pressure on my hole for a second but then he moved on.

“Obviously it would just be...you know to get off, not sexual like that” he reassured me.

“I don’t think so man, and that wasn’t the bet anyway,” I said, knowing that would be the end of it.

“Yeah, you were going to make me lick your hole, this is kind of like...the same feeling right?”

I laughed, “It doesn’t feel bad, just weird.”

“Yeah, but it’s kinda like we both won,” he laughed.

“Not really, if I won-won I was going to get my first blow job and probably cum in your mouth” I laughed.

“Yeah, and you won’t let me cum on you but you wanted me to swallow your load” he laughed.

He had me there. It was probably the alcohol but his dick was feeling good teasing my hole. This felt so gay though, so weird. I wasn’t going to let him penetrate me, that would be too weird.

“How about we play another round. If I win, you suck me off, if you win…” he cut me off.

“If I win, you let me put it in you?” he asked.

“I don’t know about that, I was going to say you could cum on me” I told him.

I felt him rub his dick across my hole again, putting more pressure on the hole, more precum smearing on my hole. The teasing felt so good, I’m sure it’s just the alcohol talking.

“Tell you what, you get first place, you can…” he pushed directly on my hole, electricity went into me and my brain went into overdrive, I felt a drop of precum come out of my dick onto the bed under me. “...You can push it in,” I said, hesitantly.

He rubbed the head on my hole again, a little more pressure this time, I accidentally let out a low moan. I don’t think he heard it over the music from the Nintendo.

“For how long?” he asked. “I’m not going to let you get me with another loophole” he laughed and tapped my hole with his slick dick a few times.

“Well, you’re not going to come in first, but...if you did, you could put it all the way in for like 5 minutes, but you have to pull out if it hurts and you can’t cum inside me...that’s gross” I chuckled.

“What if I place and beat you?” he asked.

“If I place and beat you, you have to clean the precum off the tip of my dick with your tongue” I laughed.

“Well if I place and beat you, you have to let me put the tip in you” he said very serious.

He long stroked across my hole, I’m pretty sure I heard him spit on his dick. I definitely heard a soft moan as the head caught on my hole without any pressure this time. It was as if my ass was inviting him in for some reason. It sent shivers up my spine. 

I was really nervous and confused as to why I was enjoying this, I’m not gay. I just told myself this is no different than when we goof around wrestling...we’re just drunk and enjoying each other's company.

“Alright, let's go then,” Tim said, pushing start on a random track.

The stakes being so high, I did my best to focus. He had a head start though because he place higher than me in the last round. I felt his dick throb between my cheeks again, it felt so soft and so hard at the same time. So much heat coming off of it.

“Yes, red shell” he said with excitement.

He leaned back a little, his hard dick sliding down my crack as he did. When he went around a turn I felt him lean forward a little and his dick poked hard at my hole.

“Oh shit” I said, it threw off my attention, I fell off the track.

I went from 5th to 8th place waiting on that stupid tow truck guy.

“I’m in 4th, fucker” He practically shouted.

I felt him grind against my hole. I started getting nervous, his dick felt so big sandwiched between my ass cheeks. Second lap, I picked up a red shell. Started catching up, 6th then 5th.

“Where you at?” I asked knowing I was trailing him.

“I’m right here” he said grinding himself into me with a forceful hump.

Again my head started to spin, it felt so good and so wrong at the same time, another drop of my precum squeezed out onto the bed.

“I see you” I fired my red shell.

It knocked him behind me into a fighting position for 5th place with DK in 6th.

“Fuck you dude” he jostled around his dick hit my hole again.

I let out a soft moan and tried to maintain focus.

He picked up a star, speeding up and knocking me and everyone else out a spot. He was now in second place. Third lap, I picked up a lightning bolt and used it right away. I ran over 4th place and 3rd place.

“I’m gaining on you” I yelled.

I was right behind him, he swerved and I hit a banana peel, spinning out into 4th place. We are on our final lap and he used his mushroom to launch him into first and over the finish line.

“Holy shit I just came in first” he gloated as I crossed the finish line barely in 4th.

“Fuuuuck!” I shouted. “Rematch?”

“Take your shot” he said, dropping his controller on the bed.

I took my shot, I felt so nervous, was he actually going to stick his dick in me? He again tapped the head on my hole, teasing it in a way that felt so good.

“How do you want to do this?” he asked.

“I don’t want to do this,” I laughed.

“You’re going to punk out?” he asked.

“No, just...ugh, just do it I guess” I admitted defeat.

“Just let me know if my dick is too big” he said seriously and seemed like a brag.

I felt him spit on his dick and use his precum to lube my hole. It was so gross and at the same time I was so hard. My best friend was about to lose his virginity to me...and I guess I was about to give him mine.

“Ready?” he asked, putting pressure on my hole.

“You only get 5 minutes” I reminded him.

He started to push his tip into my hole, my ass rejected it and clenched tight enough to be a knot.

“Relax dude” he said.

“I’m trying,” I laughed.

He pushed a little harder and the tip popped in, along with searing pain.

“Holy...fuck dude. No way, you gotta pull out” I grunted in pain.

“Hold on man, let me get a little deeper, then I’ll pull out” he said, grunting into my ear.

I grit my teeth and tried to man up. My head was spinning from all the alcohol and nevers, my dick had gone limp quickly. I felt Tim’s hot hard dick pushing a little deeper.

“Oh man, that’s so weird” I said, trying not to sound in pain or pleasure.

“Dude, it feels so good,” Tim said, in pure ecstasy.

He slowly pulled all the way out.

“Are you ok?” he asked.

“Yeah, just felt huge dude” I laughed trying to sound like I didn’t punk out.

“Maybe some more lube?” he suggested.

“Probably.”

He went over to the night stand and pulled out the lube we saw earlier.

“Should we use one of these condoms?” he asked.

“Maybe, if you think it will help it slide in.”

He repositioned himself on top of me. I heard him open the condom, not having ever used a condom before he realized he was trying to put it on backwards.

“Oops” he laughed.

He flipped it over and rolled it down his dick. Not knowing what he was doing, he left no room in the tip and pulled it as tight as he could.

“There we go” he jerked himself a little.

I heard him uncap the lube, he drizzled a little into my crack. Neither of us had used lube before so we didn’t know really what we were doing. He didn’t push any of it into me, just got it on the outside.

He lined his now condom covered dick up with my hole and started to push in. The head popped in quicker and a little less painful this time. I heard the latex stretching and this sound I had never heard before, it was the sound of my hole taking a dick in.

“Oh man” I said, feeling stretched.

He kept pushing in until he was all the way in. I felt so full, less pain than before but certainly a little bit of pain and some good feelings too, mostly felt weird to have Tim put his dick inside me.

“Oh wow, dude, I’m all the way in,” Tim said.

“Yeah, I can feel it” I tried to joke.

“It feels so much better than I thought it would,” he said, making small thrusts.

“It’s so weird man...your dick is inside me.”

“I know, I can’t believe I’m inside you,” he laughed.

Laying completely on top of me, his head next to mine, holding my shoulders he started to pull out most of the way and then pushed back in.

“Oh shit” I said, feeling him hit my prostate.

“Oh yeah, that feels good” he moaned in my ear.

“So weird” I whispered back.

Only a minute or two had gone by at this point, but he was picking up the pace. Not slamming me or really fucking, but pumping his hips in and out of my ass. On the down stroke he would shove hard and grind into me, then pull out an inch or two and right back in.

“Do...you...like it?” he asked as he bottomed out and grinded as deep as my ass would let him.

“It’s so weird” was all I could say.

“Fuck dude, so weird” he whispered back.

It was starting to feel good. On the next down stoke I felt something different, I heard a sort of pop sound.

“Oh man” he laughed.

“What?” I got nervous again.

He reached down, I felt his hand brush my balls as he reached for his dick.

“The condom broke,” he laughed.

“Oh” I said, relieved it wasn’t my ass that broke.

“Do...do you want me to stop?” he asked, while still slowly pushing back in and humping me.

“You only have 5 minutes, you might as well use all 5” I said, feeling him push even deeper than before.

“Man, you feel so good, this is so weird” he said, thrusting deeper and faster but still sensually into me.

“Are you close?” I asked.

When the condom broke his precum added lube inside me, his thrusting felt so much better, no more pain.

“I’m close,” he whispered.

A few more thrusts, some soft moans from both of us. I felt his hot breath on my neck.

“Fuck dude, you feel so good” he said, slightly out of breath.

“I think it’s been 5 minutes,” I said.

“I’m about to cum man,” he said, thrusting harder now.

I let out a louder moan, that thrust felt so good.

“Did you just cum in me?” I asked.

“No, I’m close though,” he said, gripping my shoulders and humping me as hard as he could.

“You’re going to pull out right?” I asked out of breath, trying not to sound like I was enjoying this.

I could feel my dick was hard again, rubbing into the mattress. He felt so good inside me, I was loving this weird new feeling.

“But I want to…” he started to say, “Oh shit…” he spasmed on that thrust.

I felt his dick swell and he slammed into me, I felt his hot cum shooting inside me, lubing my hole.

“Oh fuck man” he whispered into my ear and collapsed his head onto the pillow over my shoulder.

I felt his dick throbbing inside me.

“Did you just cum inside me?” I asked, knowing the answer.

“Sorry man, I...couldn’t stop” he laughed into the pillow.

“So gross dude,” I half heartedly said.

“Oh man, that was amazing,” he said, giving a few more pumps to milk it.

He slowly pulled out and rolled onto his back.

“Did you like it?” he asked.

“That was so weird man,” I said, rolling onto my back.

“Looks like you liked it” he laughed, looking at my hard dick.

I couldn’t deny that, I just shook my head.

“Want me to jerk you off?” he asked, still out of breath.

“Sure,” I said, nervous.

No one had touched my dick other than me in my life. He grabbed it and started going hard and fast, pumping it harder than I had ever jerked myself.

“You should suck it,” I half joked.

He didn’t put up a fight, just leaned in and put it in his mouth, immediately gagging but pushed all 5” into his mouth.

“Oh shit dude, that feels amazing” I said.

He bobbed up and down for about thirty seconds and I could feel my balls tighten and my toes curled.

“Oh man...Oh fuck…” was all I could say to warn him I was going to cum.

My body convulsed, my ass clenched the warm cum he left inside me and I shot the biggest load I’ve ever shot. Giving me the best orgasm I’ve ever had. Filling his mouth with my cum, he gagged, swallowing some of it and spitting some of it.

“Ah, gross,” he said coughing up my cum.

“Oh man, sorry” I laughed.

He continued to cough and try to swallow what was in his mouth.

“Dude…” he laughed.

I got off the bed and reached into the hamper for something to wipe up the cum. I pulled out the briefs Tim had on earlier, Jeremey’s condom fell to the floor while I used them to wipe the cum off my stomach. I handed the underwear to Tim to wipe off with. He pulled the broken condom off his tick, used the cum covered briefs to wipe his dick off.

“Man, these have three guys loads on them” he laughed.

“Just like your mom” I joked.

“Fuck you dude” he laughed, we both laughed at the irony of that statement.

We went into my bedroom, I gave him a pair of my clean underwear and put on a fresh pair myself. We were pretty drunk and very tired at this point so we called it a night and went to sleep.

That was the first time I lost my virginity.