OK, go gentle on me, first time sharing a story here :-) t might be a longer read than most stories.
This story that happened a few years ago involves me (M then 26, my best friend (M then 25), and a group of shared friends who became unknowingly part of the story.
I and my best friend go way back, we've been together forever since before high school, and shared all and everything with each other, you know the type.
My best friend is straight as a 2x4 but doesn't shy away from the "best friends with benefits" part if he is single for a long time, as a good friend (and someone that has had a crush on him since forever) I do not mind at all to lend him a hand, or a mouth...
I confessed to him in high school that I've had a crush on him for years, even though I knew he was straight I felt it would only be fair to tell him, at least now he knows why I stare at his boxershorts clad body during sleepovers or freeze when we change into swimming shorts at the pool.
He took it in great spirit, but he did like to "tease" me with it, sending harts, mildly flirting. The "playing" as you will, but as usually happens with straight guys, they get girlfriends...
My best friend was no exception, especially since this is the type of guy that can eat all he wants and stays lean as hell, sporting a nice flat tummy with some nice muscles and a well-defined V shape that leads into his jeans.
I am not that special, just your average young guy, a little less muscle than him and a little taller. Dark hair but still a lean physique. On the dick size we are not far apart, he has a nice 17 cm /6.7-inch cock with a big mushroom head, not too thin either, and I am about the same, but with a nice round head and a little more girth than him, both uncut!
So we've been toying and teasing each other for years, you know. Going on vacation and stealing his boxershorts to force him to go around commando. He unknowingly fed me "candy" that happened to be Kamagra (we did "candy" now and then, but not this kind..) Forcing me to walk around with a semi at PE in high school (yes I was very embarrassed)
To the part of pulling each other's jeans down (he was very fond of the wide low hanging style, so no effort was needed) and sabotaging each other swim suits (i removed the rope on his shorts more than once, and he switched mine out with a white speedo on more than 1 occasion)
Apart from the toying and teasing we also liked to get the other boned up just for fun in the most inconvenient places and situations (usually he started it). Lying underneath a car while working on it and getting the inside of my legs rubbed until I sprouted a nice tent, or rubbing my crotch under the table while having dinner at his house when his mom was off to grab something from the kitchen...
Of course, I retaliated, but I was less gutsy so it had less effect.
There are a lot of stories I can tell about us, but I'll go to one in our 20s to start! If successful I might write up the others.
So fast forward 10 years or so, He's been single for more than a year and it's been a few months since he last unloaded his balls (he's not the one for one-night stands and hookups, too shy with women for that)
We've planned the best buddies' vacation with a few of our best friends, leaving the girlfriends and boyfriends at home, so you can count on silliness and strong drinks!
The resort we were staying at had a humongous pool on site, with waterslides, saunas, wave basins the whole damn lot. It was MASSIVE. We rented a cottage with the 8 of us, most of the guys were straight, 1 was bisexual and I was the only gay guy, but we all knew each other for years so that was no surprise anymore.
We've been close with all of us to the part that nobody would bat an eye to share a 2 person's bed or sit on someone's lap if all chairs or couches were taken, especially if we were a bit on the drunk side.
My best friend and 1 shared a 2-person bed that vacation, since the cottage provided 2x 2-person beds, and 2x 2-person bunks, since some of the guys were a bit short they took the bunks and the rest took the 2-person beds.
We all had a nice evening the night before and it turned out LATE, drunk, headache in the morning, and a lot of Advil to start the day. After breakfast, we agreed to take an off-day to explore the on-site aqua resort so we all went to our rooms to grab our gear before we head out by bike.
I went to our room to grab the backpack and throw in our swimming trunks while my best friend went to the bathroom to shave, I knew he brought 3 swim shorts, 1 with cords and a fly, 1 normal one with an elastic band and a tight one like cycling shorts...
Hmm, tough pick, even though I had a nice breakfast I still was a bit tipsy, and maybe therefore mischievous, so I tossed in the one with the fly, minus the string... I grabbed one of my favorite dark blue Speedo shorts and grabbed some towels and we were good to go.
When everyone was ready we jumped onto the bikes and headed off, at the pool we noticed there were 2 styles of changing rooms, the lockable ones (which were all occupied) and the communal changing rooms. Knowing each other all too well we decided to not wait and just go communal!
After unpacking the bag and undressing my best friend grabbed his shorts and gave me a muffled gnarl when he noticed the strings missing, the other guys soon caught up on what was happening and gave me a sly smile and some nasty (in a fun way) remarks about me being out for his ass, etc.
Before I changed to my speedo I went for a quick piss, returning a minute or 2 later in my boxershorts ready to change, I grabbed my speedo's and found my best friend grinning from ear to ear while discovering that my white string was missing... I guess 2 can play that game, we had a good laugh and went into the pool.
After having gone through several wild waterways, having the occasional bad boy fun of grabbing, wrestling, and groping each other the group decided they wanted to go from the highest slides, my best friend and me exchanged looks and we knew what that meant... we'd lose our pants for sure.
Not wanting to be a party pooper we all tagged along for the ride and Whaddaya know, the first round my best friend came out of the slide, followed by his swim shorts, greeted by our other friends waiting below. They managed to keep their pants even though they went down "bare butt" to go faster, a lovely sight for sure!
The light jumped on green and it was my turn to go down, I tried to hold on to my speedo best I could but by the time I came down and ejected from the shoot, it was down on my ankles, what a surprise!
Though what did worry me was that the slide was wearing down on the seam of my swimsuit, it started to get thin on top and I noticed I could poke my finger through a hole and touch my cherry! I've had this speedo for years by now so guess this will be the last pool visit with this one, good excuse to buy new ones!
After a few more laps of the slide, this time having a little more success to keep our shorts (3 out of 7) we all decided it would be good to relax in one of the jacuzzis they had on the side part.
Great! only 1 issue... the jacuzzi had seats for 6 people... so I and my best friend shared a spot and the bisexual friend shared a spot with his best friend. Since I was the taller one I got to sit on the bench and my best friend would sit on my lap, once everyone was settled we turned on the jets (these were manual, not timers) and took some time to relax.
It was nice feeling the jets, but due to being a bit cramped into it, I managed to have a jet right up my butt, not that I minded. I secretly enjoyed it a little too much, my best friend got lucky that he had one of the floor jets bubbling underneath his balls because he was sitting a bit forward on my lap, The blond Bi guy had the same issue by the look on his face.
Now I couldn't leave an opportunity like this go unused, the jacuzzi was deep, the jets were bubbling ALOT, so who would notice if I would put my hands on my best friend's legs? Nobody right... Indeed, nobody did notice except my best friend.
I got a nudge against my leg when he noticed I moved my hands on his legs, but he couldn't say much about it because others would notice. I left them on his upper legs for a while before taking them up a notch.
We just kept having a nice conversation with the rest, but underneath the foamy bubbles, I slid my right hand further up his leg, discovering a massive tent to my delight, the guy was HARD as a rock, I felt the floor jet and figured he's been hard for a while now because of it.
I slide my left-hand further up and get a more firm nudge against my leg, almost a kick. I let out a Yelp and he takes the opportunity to turn around, look me straight in the eye with a look that says "Don't you dare" and say "What are you doing!?", "Nothing, just bumped my toe sorry..." With a sly face and a grin.
We turn around and continue to talk and laugh with the others, but my right hand has started to massage his dick through his shorts, very very slowly. I know how he likes it, it's been 6 weeks since I last held it in my hands, that was when I offered to give him a blowjob on his sofa in the living room after a few beers, he was high and dry for so long after all... First, he objected, but as soon as I unzipped his jeans and got him hard he caved in...
We continue like this for about 15 minutes or so, by this time I've opened up his velcro fly and moved my right hand inside his shorts, slowly rubbing his hard cock and moving his foreskin up and down agonizingly slow, rubbing his nice mushroom head every once in a while.
At this point, I was rock hard myself, but desperate for a piss and a drink, this was one of those pools where you would have an indoor bar where you could get (non-alcoholic) drinks in certain parts. So I offered to get out and grab drinks for all of us.
My best friend and I traded places and when I got up to exit the jacuzzi there was a very noticeable boner in my speedo, one of the guys made a remark but I quickly clapped back "I have a hard jet up my ass for the last 45 minutes, I'm gay, what did you expect?", we all laughed and I got out to go take a piss and get the drinks.
After 5 minutes I got back with the drinks, I got into the jacuzzi and handed the drinks to everyone, starting with my side of the jacuzzi, when I turned my back towards my best friend to give the drinks to the last 2 I felt him grab my hips and pull me onto his lap, when I landed I gasped let out a hard Yelp and covered my mouth in shock, Everyone asked what was wrong, "Sorry! I whimpered, I bumped my toe again, BADLY"
Of course, that was bullshit, I would not Yelp THAT hard if I only stubbed my toe... no... I got impaled... BY MY BEST FRIEND'S HARD COCK.
The bastard actually left it out and hard from his fly and wanted to get back at me... and now he slid his full length right in one go, god it hurt, I took his dick before, but never without lube...
I just sat still, sipped my drink, and let the pain subside a bit, but after a minute or 2 the pain turned into pleasure, I could feel his mushroom head right against my P-Spot, god it felt so good... I became harder than steel from the feeling.
Luckily the jets were still on, and this pool is rather deep, sitting on his lap my upper chest was still above water, and he was down into the water right up to his neck.
I noticed he started flexing his leg muscles a bit, since I'm sitting on his lap and not touching the ground I have little choice but to endure it, He starts rocking me up and down very slowly, barely noticeable, luckily the jets hide most of the movement but the Bi friend seems to notice what is up (he sits almost straight across of me on another friends lap)
Feeling his hard cock pushing my P-spot surrounded by our friends in a pool is AMAZING! not what I expected from this holiday but I'm not complaining... I slowly slide my hand in my speedo to massage my hard cock when suddenly I feel a foot pressing against my hard cock. I look up and lock eyes with our Bi friend who gives me a wink while starting to rub his foot up and down over my hard cock...
By now due to all the rubbing, my cockhead is sticking out beyond the waistband, I feel his toes wrapping around it. OH MY GOD, I'm getting secretly fucked by my best friend and getting a foot-job by the other, I can't take this very long...
With every rub of his foot and touching my sensitive cockhead my muscles clench and my sphincter starts milking the throbbing monster inside me, I have a hard time suppressing moans but with every slide, I feel my cock getting harder and harder, I'm very close to cumming...
All the clenching of my muscles has left my best friend in a tight spot, I feel his hands clenching my upper legs and pushing me firmly onto his lap, I feel his mushroom head swell against my P-Spot while he unloads a hot load of boycum deep inside me, it's too much for me to take, getting blasted full of cum while getting my cockhead jacked off by a foot.
I stop mid-sentence for a moment while my balls silently unload their load across my friend's foot... I feel them contracting a few times and it takes all I have not to let out an enormous moan. My best friend's semi remains inside me for a while until we decide as a group we've had enough water for today. Everybody starts to get out and our Bi friend helps us out by saying "last out turn off the jets"
This allows me to get up first so my best friend can put his cock back in his shorts before he gets out and turns off the jets.
We go on to shower, towel and change, and get back on the bikes for the cottage, I can feel the cum coming out of my cherry with every peddle stroke on the bike and it makes me horny as fuck...
When we arrive at the cottage everybody dumps their stuff in the rooms, I wished in my best friend's ear that he is an asshole and warn him that I'm not done with him yet, he smiles and replies "I was hoping you weren't"... I guess someone is getting some cum tonight...
I love my best friend, and I love the benefits when he is single! writing this now makes me crave for his cock again... I should give him a call and see what he's up to this weekend
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