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"Relax buddy, we won't cum in you. Today is all about your pleasure, not ours." That's what they said right before they started tag teaming my asshole with their raw cocks. But I'm getting ahead of myself.

 

When I was 19, my family took a trip to one of those all-inclusive resorts to Cancun. It was over Christmas break, so I guess it was a nice escape from the winter, but the resort wasn't exactly geared for the fun of a 19 year old who wasn't drinking. We had done the side trips to the ruins and shit, but mostly we hung at the resort where I was bored and mostly alone while my parents drank and had fun. One day they opted for the catamaran drunk cruise. I begged them to not make me go. I pulled the "I'm not a child anymore" card and said I would be quite content reading, napping and lounging by the pool. They finally relented, and I was left to my own devices for an entire day. If only they'd been more protective of their horny, gay son.

I hit the pool pretty early with only my book, towel, mirrored shades, and swimsuit. Since I used to be a competitive swimmer I still had my speedo, which is what I decided would make for the best tan lines. I claimed one of the lounge chairs and set in for a nice day of relaxation. And I promptly fell asleep in the warm sun. I awoke some time later hearing hushed voices next to me. It was two, obviously American men whispering in close proximity to me.

Voice 1: Look, the kid totally has a boner!
Voice 2: Shhh! Don't wake him up and embarrass him.
Voice 1: (laughing) Looks like part of him is already awake!

(This is when I realized that I had one of those relaxed, sun-boners and they were talking about me! I was mortified and kept still while desperately trying to will my hardon away, but it wouldn't budge.)

Voice 1: Damn, it just flexed in his suit! Totally hot!
Voice 2: Yeah, the kid has a nice package on him, and a nice little body.
Voice 1: I'm getting hard just looking at the outline of his cock. Oh the things we could do...
Voice 2: Don't even think about it.
Voice 1: Oh, like you aren't thinking about filling that young ass.
Voice 2: Go get us a couple beers and cool off.

I heard Voice 1 guy get up and flip-flop away toward the bar. Hearing them talk about me in a gay way was making my dick so hard that I knew it wasn't going to go away without a serious spank. I made sort of a fakey "I'm snoring and waking myself up" noise and rolled over onto my stomach. I tried to lay there quietly like I was still asleep. And when Voice 1 came back, I did an equally fake slow wake up and roll over, but simultaneously grabbed my towel and covered my still throbbing junk. I sat up and decided to read a bit, thinking this might take my mind off things. No such luck. Especially when I saw the two men attached to the voices. One was mid 40's, salt and pepper hair, rough beard, and a stocky, muscular body covered with a pelt of coarse, curly black hair. The other was blonde, a bit younger (maybe mid 30's), tall, smooth, tanned and toned. Both were exceedingly attractive (the blonde could have been a model) and both were wearing straining speedos that left very little to the imagination. I tried to ignore them, but they could tell I was staring.

Voice 1: Hi there! What are you reading? (it was the blonde)

Oh my god. They were so hot and they were talking to me! I stuttered a bit before telling them that I was reading Humboldt's Gift for my American literature class. I remember this fact purely because I never did finish that damn book and had to cliff note the fucker. This opened the doorway into conversation, through which I learned that they were John (Voice 1) and Vince (Voice 2), a gay couple on vacation. They asked many questions about me, like was I there alone? Was I enjoying my free day? What time would my parents be back? Did I have any plans for the rest of the day? By this time my boner had actually gone down and I was thirsty, so I uncovered myself and stood up to go to the bar to get a coke. My further mortification was imminent.

Vince: Um, you might want to sit back down.
Me: Why?
John: (laughing) Because you left a spot of precum in your speedo the size of a half-dollar!

I looked down, and sure enough my penis had betrayed me yet again. My electric blue speedo had a huge, dark blue spot of wetness centered right at my cock head. I hastily sat down and covered up again, completely and utterly embarrassed.

Vince, however, knew what to do.  "John, go get him a coke would you?"

 

"Sure thing."

 

As John walked off, Vince quietly remarked "Don't be embarrassed. It happens to all of us. And, truth be told, that's a pretty impressive spot. You must be a big leaker. Or just incredibly horny."

 

"Well... um...."

 

"So, are you? A healthy cummer, I mean?"

 

"Isn't that sorta personal?"

 

"Lemme guess. You are stuck here with family and you haven't jacked off in days. And now you are so backed up you were going to fire off a few loads today with your free time. Am I right?"

 

"How'd you know?"

 

Chuckling, Vince replied "We've all been there, guy."

 

"What are you two laughing about?" John asked as returned, coke in hand.

 

Taking the lead, Vince explained "The poor guy hasn't cum in days because he's been cooped up with his parents.  Hence the gigantic wet spot."

John handed me my coke, and a glance passed between he and Vince. I couldn't believe I was having an open conversation about jacking off and precum with two relative strangers, even if they were two, handsome gay men.  Apparently they were of one mind, cause without any further discussion John remarked "You know, we could help you out of your jam. You need to empty yourself out before you make a mess all over this pool deck, and it just so happens that Vince and I like to pleasure guys, such as yourself."

 

"Oh, I don't know... I um...," I stuttered, turning even beet red in embarrassment.

 

"No pressure or anything. It would just be a relaxing, fun time and all about your pleasure. We would make sure you would be empty enough to survive the rest of your stay here with your parents," Vince explained, in a very discrete, man-to-man voice.

 

"Honestly, I'm not sure I should," I responded, honestly more than a little interested.

 

John: What else have you got to do today? I guarantee you'll have a better time than just sitting by the pool kicking yourself for missing a mind-blowing afternoon of sex.
Vince: It's your call, but we're nice guys and I think you would have fun.
Me: .... ok.

We left the pool together and they escorted me up to their hotel room. Now, while I wasn't a virgin (I'd been having oral sex with other boys for a few years now, and I had a fairly regular suck session with a fraternity guy at school) but I'd never done any kind of anal. And definitely had never done a three way. And I'd never had sex with men clearly much older than I was. So you can imagine how very nervous I was. At first we just sat on their bed and they gave me a beer. I drank it fast and relaxed a little. Then they each reached out a hand and started stroking me lightly. Massaging my neck a little. I started to get hard. Both were very patient to start. They gently stripped off my swimsuit and laid me back on the bed. Both of their mouths fell to working on my body-- my neck, my nipples, my stomach, my thighs, my balls. And then I felt the wet heat on my cock. Instantly I was rock hard and straining to hold myself back from the waves of pleasure rocking my body. It was John sucking my cock while Vince sucked and tongued my nipples. He slowly traced his tongue up my neck, to my adam's apple, and then over my chin to my mouth. When Vince's mouth met mine, everything exploded-- including my orgasm. John greedily clamped down on my cock and took every drop. He stayed there until my dick finally stopped squirting like a minute later.

John: Holy FUCK this kid's a cummer! God damn!
Vince: And I think I found his trigger points.
Me: I'm sorry! It's just that when you kissed me I couldn't hold back. You are just so... handsome. And hairy!
Vince: (laughing) Yeah, I do have a bit of fur.
Me: It's hot!
John: I think the kid isn't done yet... he still hasn't gone soft.

After that, John and Vince stripped off their suits... and wow. John was totally clean shaven, which made his cock look exceptionally huge. Judging from the size of mine, I figured he had to be at least 8 inches. And Vince had a dark bush of pubes, big balls and a shorter, but decently thick, uncut cock. And both had these curious tattoos on their hips.

Me: Oooh. You guys have matching tattoos! Looks like a nuclear symbol. Are you guys radioactive or something?
John: (smirking) Something like that.
Me: Well, you both are pretty hot!
Vince: I think we should massage another load or two out of our friend here, John.
Me: Hell yeah! Deal!

We had another couple of beers, and then Vince got the lube out of their travel bag. I was buzzing well at this point and feeling pretty good. Vince got me up on all fours, and then proceded to do something that nobody had done to me up to that point. He ate my ass. And when his tongue hit my pucker, I almost came unglued. This released the last of my inhibitions, and I became an insatiable fuck hole that afternoon. John was kneeling on the bed close to me, and as soon as Vince started rimming me, my mouth latched onto John's cock and I started sucking for all I was worth. I was only able to fit about half his cock in my mouth and I tasted his precum as I worked his salty slit with my tongue.

John: Damn Vince, this kid can SUCK!
Vince: Yeah, but we're here to milk him dry. And I think he needs to be milked from the inside.

And with that, Vince lubed a finger and slid it into my butthole. Electricity jumped through me and I became a sex crazed novice bottom. He fingered my prostate (nobody had ever done that either) and it made me go crazy with desire. I sucked John like a hoover while bucking around on Vince's finger, all the while drooling precum all over the bedspread. Vince worked a couple fingers into me along with more lube... then his fingers left my ass. It felt like someone had shut off my horny switch. But then, I felt Vince's cock head rubbing up against my hole, teasing and pressing against my pucker. And while it was electric, warning bells were going off in my head.

Me: Do you have a condom?
Vince: Yeah, somewhere I think. But how about I just tease your pretty butthole a bit with my cock first?
Me: We really need a condom. And you need to go easy on me-- I've never been fucked.
Vince: Never??
Me: Nope. I've wanted to do it, but it just hasn't ever happened yet.
John: Vince, pass me the poppers. I'll help our little bottom virgin out.
Me: What are poppers? They aren't drugs are they? I don't do drugs.
John: No, you just sniff them and they help you relax. They actually have a medical purpose.
Me: Um....
John: Here, I'll show you. Just take a small sniff like this...

John took a hit, and I could see him go flush a bit and relax. Then he held the bottle under my nose. I debated it for about a second, and then took a hit. The warm rush was incredible. Vince timed my rush with another finger assault which had me begging for more. The damn poppers had made me desperate for cock and had silenced those pesky warning bells.

Me: Oh god. Fuck me!
Vince: You want it?
Me: Yes! I need to feel your cock inside me! Now! Please??

Vince didn't need to be asked twice. John held the little bottle under my nose again, I took a hit. And as I went soaring on a wave of pleasure, Vince entered my ass. While it hurt, it really didn't hurt as much as I thought it would. Sure it burned a little bit, but overall he was able to slide right in and I just felt full. It probably helped that he was uncut and I was an incredibly horny teenager. Vince slow fucked me while I got used to having a cock in my ass, and I went back to working John's big cock with my tongue and throat. The pleasure I was getting from both ends being filled, plus the alcohol, plus the poppers had me rock hard and begging for as much sex as these two men could dish out. Vince eventually sped up his tempo and the sensation his fat cock was giving me was making my head reel. I was tingling everywhere and begging to cum again. I reached back to cup Vince's balls and to feel his cock sliding in and out of my ass. And that's when I noticed he didn't have a condom on.

Me: Where's the condom?
Vince: You told me you wanted cock in you now. I didn't have time to put one on.
Me: But sex without a condom is risky...
Vince: Relax buddy, we won't cum in you. Today is all about your pleasure, not ours.
John: Here, have some more poppers...

Vince continued to fuck me and my protests ebbed as the pleasure increased. John pushed his dick back into my mouth and I let the poppers relax me into the pure ecstasy of man on man on man sex.

Vince: Oh Johnny, you really need to feel this boy's ass. It's so tight and smooth!
John: I can't wait for my turn!
Vince: Well, it's coming soon. I'm about ready to share...
John: Sweet! Here kid, take another hit
Me: Damn this feels so good.
Vince: It's gonna get better in a minute. I'm going to put my cock head right at your prostate and you are going to feel me flex it. Trust me, it will drive you wild with pleasure.
Me: Do it! I wanna feel that!

Vince thrust a few more times in me quickly, then parked his cock a little more than halfway inside me. And then I felt it. His cock head was pressed up inside me, and I could feel throbbing and flexing inside me. The sensation was incredible!

John: You doing it Vince?
Vince: Fuuuck yeah. You feel that, kiddo? Yeah, I'm trying to milk your load out from the inside.
Me: It feels amazing, I don't want it to stop.
Vince: I can do it again later, but now it's John's turn though. And just wait til you feel him inside you!
Me: I don't know... he's so big! I'm not sure I can take it...

Vince pulled out with a wet plop, and shifted around the bed. He suggested that I try riding John's cock to start. That way I could control it better and be more comfortable. Without Vince in me, I felt like my switch had again been turned off and I desperately wanted it back on again. So I agreed. John lay down on the bed- his cock enormous and intimidating. Vince lubed him up and worked a bit more lube up my ass.

Me: Shouldn't we get a condom?
John: Vince didn't have to wear one.
Me: But we have time to get one one now and...
Vince: It's okay kid, just try it for a bit. We can always get one on later. I want John to feel what I got to feel!
Me: Just... don't cum in me. Okay?
John: Wouldn't dream of it.

I straddled John's groin. John held onto the base of his cock while I tried to line up his head with my hole. Vince fed me more poppers, and before I knew it I was sliding down almost the full length of John's big cock. He bottomed out inside me with still about an inch of cock to go. There was a dull pain deep in my abdomen when John's cock head was poking my guts, but the sensation of that much cock sliding inside me and filling my guts sent me over the moon. I think my eyes literally rolled back into my head.

John: Holy fuck! This kid is a natural born bottom!
Vince: What did I tell you?
John: So fuckin' hot and slick! Thanks for lubing it up for me!
Me: Oh my God! You are so fucking BIG!
Vince: Enjoy the ride you two.

I started sliding up and down on John's cock and he let me control the fuck action. Every thrust into me from his cock gave me the sensation like I was stroking my own erect penis. Only I wasn't touching myself. It was like I was jacking off, but no-handed. The pleasure was building, and it sent my body into sort of a fuck frenzy. I was fucking myself down onto John's cock and building my orgasm with every bounce. Vince straddled John's face and fed his soft, uncut cock into John's mouth while John grabbed my hips and helped ram my ass up and down faster on his cock. Vince worked my nipples and then planted another deep, wet, scratchy beard kiss on me. I went into overload.

Me: Oh God! I'm gonna cum!
Vince: Do it, kid!
Me: Dont' stop fucking me-- I'm so close!
John: I wanna feel you cum with my dick jammed in your sweet fuckhole!

Vince grabbed the back of my head and kissed me again hard and with that kiss my first shot arced up between us and spattered all over Vince's hairy chest. As soon as he felt me start to shoot, John grabbed my hips and thrust all the way into my butt, even that last inch that wouldn't go in seemed to find a place inside me. The pain in my guts mixed with my orgasmic pleasure was enough to make me cry out into Vince's mouth. But I couldn't stop cumming. Volley after volley of my spunk coated Vince and dripped down onto John's face. I was spasming like I was having a seizure and Vince eventually just looked on in amazement as John started laughing and licking up the cum gobs that spattered his way.

I kept shuddering and shaking with the post orgasmic shivers. Vince kissed me gently while I was still impaled on John's cock and trying to relax my quivering sphincter. John told me that if I stopped wiggling around so much he could make himself go soft so it would be easier to pull out. A few minutes later and after some deep breathing on my part he was indeed flaccid and I was able to ease myself off of him. Feeling fully satiated, I was going to take my leave but Vince and John convinced me otherwise.

Vince: You are a young stud, and I bet you have another load in you yet.
John: Besides, we haven't cum, have we Vince?
Vince: No we haven't. And there's still a few more things we could do together. Three cocks offer so many options...
John: It would be a shame to waste them.
Me: But I probably should be going...
Vince: Where? You're parents aren't gonna be back for a few hours yet. Might as well spend it fucking.
John: Hasn't it been fun? Haven't you enjoyed yourself? We've sure enjoyed you.

In the end I agreed to stay for another round of sex. We had a few more beers, and they eventually got me hard by tongue-fighting over my cock. This got them hard too and the next thing I knew it was a free for all on their bed. We were all kissing and sucking whatever we could get our mouths on, rubbing on each other, humping, etc. I ended up on top and this time rode Vince's cock (I had decided that I quite liked riding and being in charge) while John stood on the bed so I could suck him. Then John squatted over Vince's face so Vince could tongue his hole while John and I made out. John worked my nips and I begged Vince to do the pulse-trick on my prostate again. After about 15 more minutes of fucking, he grabbed my hips and I felt the magic throbbing inside me again. Each pulse was like an joy buzzer shock inside me- I loved it! Then they both maneuvered me so that I was on my back with my head hanging over the edge of the bed. More poppers and John was fucking me again with his huge cock while Vince stood over my face with his flaccid, wet, uncut penis.

Me: I've never sucked an uncut cock before.
Vince: Well, this is a day full of firsts for you!
John: (giggling) And lasts...
Me: I think I'll remember this day for the rest of my life
Vince: Of that I have no doubt.

John grabbed my ankles and took to fucking my ass hard. And I took Vince into my mouth and let my tongue savor his foreskin. The feeling of the skin was silky, and I could taste a mixture of lube and what I thought was his precum. When I inhaled, I got a full whiff of his musky manscent. It was almost better than the poppers. The rush of blood to my head and the feeling of foreskin in my mouth was dizzying. John flipped me around (all while not pulling out his cock) and got me on all fours. He then suggested to Vince that since this had been a day of firsts, how about they make me Lucky Pierre? Vince agreed and hopped up on the bed in front of me. I had no idea what a "lucky pierre" was, until Vince spit on my cock, and shoved it into his ass. It was so warm and velvety... so unlike anything I had ever experienced. So hot! So much better than a blow job! I was getting my ass fucked by a big cock while simultaneously losing my anal topping virginity inside a hot, furry daddy! It was all too much. I think I lasted all of a minute before I warned them that I was getting close. That's when John reached forward, grabbed Vince's hips and Vince reached back and grabbed mine. I was locked in place between them and stuck in Vince's ass!

Me: I'm gonna cum! I should pull out!!!
Vince: Just cum in me, kid!
John: Do it! He wants you to!
Me: But... but...
Vince: I trust you
John: C'mon kid! Shoot that load! Breed my boyfriend!

John thrust again hard inside me and with that I erupted inside Vince's ass. The wet heat of my orgasm enveloped my cock as I shot my third load of the afternoon into Vince's bare ass, groaning "God DAMN, this feels awesome!"

 

Apparently it was an impressive orgasm because Vince echoed my remarks saying "Holy fuck, I can feel him cumming in me!"

 

In full approval, John answered "So hot!  Take that virgin load!"

After my orgasm finally subsided, John slid out of my ass with ease and I did the same to Vince.  We collapsed in a sweaty heap on their bed.  I awoke about an hour later, with a headache and instant fear. According to the bedside clock, my parents were due back at any time.  I jumped to my feet, pulled-on my speedo, grabbed my stuff and headed out.  I thanked Vince and John for the best sex of my young life and they said it was truly their pleasure.  I made it back to the pool and managed to rinse the sex off about ten minutes before my parents arrived, so they were none the wiser about my afternoon activities.

Several weeks after we got home I got really sick.  My parents figured it was just some bug I picked up while in Mexico.  Six months later at the student health center at college, I found out my parents were right.  It was something I picked up in Mexico.  And I discovered the meaning behind Vince and John's matching tattoos.

  • Like 24
  • Upvote 56
  • Piggy 9
Posted

Ah, innocence lost. And in a really hot, sexy, mind-blowing way. So nice of Vince and John to tutor him so well as they introduced him to complete debauchery. What an awesome souvenir from Mexico.

  • Upvote 1
Posted

I agree...great story and what a great way to bring him into the fold with the best sex of his life. Now it will get even better for him as he shares his gift with others.

Posted

Great story, and good introduction to being pozzed. Reminds me of a similar situation when I was 18 and went on holiday without pasrents for the first time, ,I met this handsome guy at the pool and we eventually went to his room and i had my first experience of bare cock sex, never had 'safe sex' again afterwards

  • Upvote 2

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