Home » Summer trip with brother's friends takes a unpredicted turn...

Summer trip with brother's friends takes a unpredicted turn...

This story is completely true!!! (although names have been changed)

It was during the summer that me and my older brother’s friends went up to visit him in another state. By that time I was 18, but the three guys I went with, my brother Andrew’s friends, were all 20, as was my brother. So the plan was for the four of us to drive up and see him, we’d stay in a hotel while he finished his last week of work before his holidays, then he would come back with us, and all the while we’d be partying and drinking.

By the way, my names Jackson, I’m average height, decent build, not huge, but defined, blonde, blue-eyed and a 7.5 inch cock. I knew I was gay, had known ever since I was 10, and I’d fooled around a couple of times with guys (including Andrew) but ultimately wasn’t that experienced in gay sex. The three guys I was going with were all amazingly hot, especially Michael. He had wavy brown hair, a ripped body, tight ass, and from what he’d said, a 9 inch cock. I’d wanted to have him fuck me for years. The other two were Craig and Tom, who were both still really hot, but Michael was my favourite. Craig had dark brown hair, was really buff, like huge, and had a 10 inch cock, (he was the biggest in the group for cock size, something he constantly bragged about). Tom wasn’t buff, but he was ripped and defined, every part of his six pack was chiselled, and he had a 7 inch cock.

So anyway, the four of us began our trip, and the journey up was uneventful and a bit dull. It wasn’t until we got to the hotel that things began to get interesting.
We were all staying in the same room, and there was a double bed and two singles. Tom and Craig immediately jumped on the single beds, so me and Michael were going to have to share the double. Which neither of us were really worried about, and I was particularly excited about.

The rest of that day was spent unpacking, looking around and wrestling (Craig and Tom didn’t stop for hours). The hotel we were staying at had an indoor pool, a sauna, a gym and two spas. So at the end of the day Michael, Tom and I decided to go to the sauna, Craig was ditching to go fuck some chick he met during the day.

So late that night the three of us grabbed a towel each and made our way up to sauna. We were happy to see that it was empty when we got there.
“Should we strip down naked or just stay in our undies?” tom asked.
“Get naked, as if you go in a sauna wearing anything except a towel.” Michael said.

So we all stripped off completely, I took care to check out Michael’s package, he wasn’t lying, he was definitely 9 inches. At that moment he looked at me strangely, and I quickly averted my gaze, embarrassed.
We all wrapped our towels around us and entered the sauna, which Tom had already turned on so it was really hot already. I sat down in the corner on the bench which ran along the side of the room. Michael sat to my left and Tom to my right.
After about 15 minutes of talking and a large accumulation of sweat on our bodies (Michaels looked amazing), and mainly Michael and Tom talking about chicks they wanna fuck (strangely enough, for his age and high level of attractiveness Michael was a virgin, something Tom frequently bagged him about because that’s the only thing Tom had over Michael), it finally got interesting when tom asked me:

“Hey Jackson, you don’t have to answer if you don’t want, but are you gay?”
“Um...” I didn’t know what to say.
“Yeh he is.” Michael said.
“What? How do you know?” I demanded.
“Andrew told me.”
“What else did he tell you?” I was worried now, what if what we had done was circulating?
“A lot.”
“So have you done anything with a guy?” Tom asked.

At this point I didn’t see any point in lying or pretending I’m straight anymore, so I said “I’ve been fucked once, blown a few guys and gotten a couple of bj’s.”
“Woah, he’s had more action than you Mike!” Tom winked.
“Shutup! Doesn’t count.”
“Pretty sure it does. So Jackson, who do you think’s hotter: me, Craig or Mike?” Tom asked.
After a pause, I said: “Mike.”

“Oh burn! Suck shit Tom!” Mike laughed. Tom actually looked disappointed.
“Well this is boring, so how about we do a bravery test?” Tom said.
A bravery test was like a dare contest, it was to see how far people were willing to go, to prove they were the best in the group, Mike and Andrew invented it when they were at a party with some chicks or something. I was happy to join in.
“Yeh sure!” I said. Mike agreed too.
“Alright, Mike you go first.”
“Okay, Tom: take your towel off and throw it out of the sauna.” Mike said.

So Tom took his towel off and opened the door and threw it out, then sat back down next to me, although his dick was nowhere near as big as Mike’s, I still couldn’t help but feel a tingle in my crotch in desire to have that cock inside me somehow.
It was my turn. “Mike you have to take your towel off and then get a hard on.”
“Don’t get too excited Jackson.” But he took his towel off and threw it outside the room like Tom, and then sat back down next to me and started stroking his cock. He got hard surprisingly fast and the sweat dripping down his body to reach his 9 inch hard uncut cock made me get so horny I got hard too. I tried to position the towel hoping they wouldn’t notice, Tom did.
“Jackson’s loving it!” I covered the rise under the towel, but Tom grabbed my hands and moved them. “It’s okay Jacko, we understand that you’d get aroused near us, like if Mike was a chick right now I’d get hard too, so don’t get embarrassed.” He smiled and I smiled back.

It was Toms turn. “I’m bored of these easy ones, lets get it going, Jackson: suck Mike’s cock.”
“No I can’t do that...” I started, but Mike had got up and was standing in front of me, pushing his rock hard cock in my face.
“Suck it Jackson!! Suck it!”

I grabbed his cock and shoved as much of it in my mouth as I could, taking about three quarters of it. He tasted so good. I grabbed his ass with my hands and squeezed it as I blew him. He started to get excited and grabbed my head and began face fucking me, pushing his cock further and further down my throat. I was gagging on him but he kept going, faster and faster. I could taste his sweet salty precum and moaned as my tongue played with his cock in my mouth. Mike groaned as he fucked my face, I looked at saw Tom’s rock hard cock in his hands out of the corner of my eye. Mike pulled out of me and sat down again, continuing to jack himself.
“Woah, why’d you stop?” Tom asked.
“Didn’t want to cum yet.” Mike smiled. “Okay Jackson, I want you to fuck Tom.”

I looked at Tom and he smiled and got up and bent over so that his arms were resting on the bench and his ass was sticking out. I got up and stood behind him.
“Won’t we need a condom and lube?” I asked.
“Na just fuck him bareback, and just lick him out for lube.”

So i got on my knees and looked at his tight tanned ass, I grabbed his ass and shoved my face into it, my tongue licking every inch of his crack and entering his hole. Then I stood back up and positioned my cock at his ass.
“before you start, I don’t care what he says, fuck him hard and fast from the start, don’t ever go slow.” Mike said.
“But...” I started. “Do it.” Tom said.
So I got ready and shoved my cock in his ass, he was so tight and it felt amazing on my cock. Tom yelled out in pain. But I didn’t wait for him to get used to the feeling, i started fucking him hard and fast. I stroked his back as i fucked him. He groaned and groaned but I kept going faster and faster. Then I saw Mike get up.
“Fuck this game, I can’t just watch this.”

Then i felt his tongue playing with my whole and I almost came then and there. The pleasure was insurmountable. I could feel my dick leaking precum inside Tom’s ass. Then I felt Michael’s cock enter me, and I yelled out in pain. It hurt so much. He was so big. So much bigger than Andrew had been. But he didn’t wait, he was fucking me immediately. I was groaning in pain and pleasure, I grabbed Tom’s head and pulled him up to me and kissed his lips, rubbing my hands down his ripped chest as i did, reaching his cock. I grabbed it in my hand and began stroking it. Michael was pounding my ass harder and harder, he held me on the sides of my ass as he fucked me. I was moving back and forth between them, moving back, further down Mike’s cock, and forward, further into Tom’s tight ass. I was getting close to finishing, and finally thrust all the way into Tom, my entire cock in his ass and exploded inside him. My cum filled his hole and leaked out down his ass, I kept cumming for ages and ages, Michael continued fucking me as I did, egging me on.
“Yeh Jackson, huge motherfucking load, fill that boys ass!”

When I’d finally finished, I pulled out of Tom as Mike continued fucking me, and he turned around and put his cock in my mouth. He was significantly smaller than Mike, but tasted so much better. I went all the way down on his cock straight away, fingering his ass as i did. My fingers came out of his covered in my cum, so i moved them up to Tom and he licked them clean.
“Yeh Tom, swallow his cum, fuck yeah!”
I could soon tell Mike was getting close to cumming.

“Oh god this is so fucking amazing, you can really take a cock Jackson! Oh you’re so tight, oh my fucking god!! Soooo good!!!” Mike moaned. “I’m gonna cum in your mouth Jackson, and you’re gonna swallow all of it!”
“Me too, you can take both our loads!” Tom moaned.

So Michael pulled out of my eyes, and I got on my knees inbetween them. I opened my mouth wide and they both positioned their cocks at the tip of my lips, Mike finished first, his load spraying into my mouth, it was a decent load, and i didn’t swallow immediately, I kept it in there, his white load, as I waited for Tom. Then Tom came, and his load was huge, bigger than mine, he filled my mouth, and it began seeping down my face, i swallowed and opened up again as he continued cumming.
“Oh fuck, oh fuck, oh fuck! This is so fucking good!!! Oh god!!” Tom moaned.
“Yeh, fuck thats hot, you like the taste don’t you Jackson!?”
I nodded.

I swallowed the second mouthful and tom was finally finished. But I grabbed Tom’s cock and pulled it toward my mouth, trying to drain every last drop out of him, he shuddered as I did, but some more cum came out.
“Stop it Jackson, I’ve got nothing left.” Tom said.
Then Mike and Tom pulled me up and Mike kissed me, while Tom licked up the cum that had leaked out of my mouth and swallowed it. Then they sat me down inbetween them and Michael held me, as tom licked my cock clean.
“That was fucking amazing.” Mike said.
“Not bad for your first time hey Mike?” Tom said smiling.
“Not bad at all. But fuck Jackson, you’re a pro.”
“Thanks.” I smiled and kissed him.