First Time with Family Friends

It was Christmas break of James' senior year of high school. Just two months earlier, he had turned 18 and made a pact with himself to finally get laid this year. He knew it was stereotypical, but it needed to happen. And being in the closet certainly didn't help.

James was tall at 6'1'', with dirty blond hair and blue eyes. He was pretty skinny, but not lanky either. Although he had attracted the attention of a couple girls at school, he of course wasn't interested. No one was out in his grade, so finding someone to fuck him would be tough.

For Christmas break, his family was going on a ski trip with two other families, the Smith's and the Jorgenson's. The three families had always been close. The dads all worked together, the moms were friends, and they each had one son. Josh Smith was 22 and a college senior, and Matt Jorgenson was 25 and working in marketing.

James was most excited about this trip because he could spend lots of time with Josh and Matt. The three of them always shared a hotel room, which usually involved Matt buying lots of booze for them and getting drunk together. James had developed a huge crush on both of them in recent years. Josh was a built 5'11'' with short brown hair and a wide, gorgeous smile that lit up the room. Matt was 6'2'', a little chubby, with medium length blonde hair and bright blue eyes. The thought alone of sleeping in the same hotel room as Josh and Matt got James hard. But he had to be careful, as they didn't even know he was gay.

The trip started on a Saturday. Each family packed up their cars and headed off in a caravan towards the ski resort, a five hour drive away. When they finally arrived, they split up into their own hotel rooms, and James got to chat in private with Josh and Matt for the first time this trip.

"Hey little bud, how's senior year of high school treating you?! Getting laid and partying every night?" Matt asked James with a big smile.

"Don't listen to him," said Josh. "You don't need to go as wild as Matt to have a good senior year."

James laughed at their ridiculousness. "Hasn't been too crazy yet, but we'll see about the spring semester."

The three of them began to unpack and catch up on their lives since they last hung out. Both Josh and Matt had new girlfriends, who they described in great detail. Josh kept bragging about his girl's huge tits, which he had recently gotten into fucking. Matt was a bit more reserved about his sex life, choosing a "don't kiss and tell" attitude. But after some persistent nagging from Josh, he started to show some pictures of them together on his phone. As he swiped through an album, he accidentally revealed a picture of the two of them having sex. He quickly flipped his phone over and got bright red.

"Fuck!! Didn't mean to show you guys that one!"

But James and Josh had already taken it in. The picture was a POV, where you could see Matt's dick entering his girlfriend. James was shocked at how big Matt's dick was. He was easily 8", thick and veiny.

"Damn bro," said Josh in shock, "your dick hardly fits in her! I didn't realize you were so hung."

The three of them had never talked so candidly about sex before, but the photo had really broken down that boundary. Matt responded with a little smirk, clearly thinking about sex. Suddenly, he wasn't feeling so shy.

"Yeah man, she's wild in bed. I wouldn't normally be the type of guy to record us having sex, but she always wants to. Says she loves seeing the pictures later and wants me to jack off to them."

Then, Matt really ramped things up. "That's fucking hot, man. I'd jack off to those."

As James looked around, he could see all three of them getting hard. Matt slowly turned back over his phone and pulled up the pictures again. The three of them started discretely rubbing themselves over their pants looking at the picture, but of course, James was focused mostly on Matt's huge dick.

"Don't have any pictures to show us, James?" Josh teased. "It's all good dude, we know you're not quite as experienced yet."

James knew that if they were going to all jack off together, he had to tell them first. "Okay guys, I just have to let you know something before we do...well, anything else. I'm gay."

Josh and Matt immediately looked up at him, a bit surprised.

"Wow man, thanks for telling us. I know I speak for Matt too when I say we're super proud of you and support you."

"Absolutely, this doesn't change anything at all," added Josh.

James was relieved. But of course, all three dudes were still rock hard and staring at some nude pictures on Matt's phones.

"Okay but I'm still horny as fuck," said Matt. "Mind if we still jack off together? I don't even care if James wants to jack off to my dick" he teased.

Clearly Josh agreed, whipping off his shirt and pants in two quick movements. His 7" cock was fully erect, with big balls and short brown pubes that smoothly blended into his trimmed stomach and chest hair. Matt also ripped off his clothes, revealing the same massive dick from the picture. In real life, it looked even bigger, maybe 8.5 or 9 inches total.

James knew it would be weird if he didn't get naked now, so he took off all his clothes and began to stroke his dick. He was around Josh's size at 6.5" inches but not quite as girthy. He couldn't believe his luck. Just twenty minutes into their family vacation and they were already jerking off together.

The three of them sat down next to each other in the hotel bed, facing the TV and jerking off silently. Matt was in the middle, still holding up his phone as they enjoyed the picture of him fucking his girlfriend.

But suddenly, Matt put his phone down. "Wait guys. Since all three of us are clearly horny and one of us is a gay virgin, why not have some real fun?"

Matt and Josh looked over at James, who was taken aback by the suggestion.

"Come on dude," pleaded Josh. He was obviously into the idea. "We'll go slow. Why not have your first time with two guys you trust and know will get you off?"

James didn't need convincing. He was horny as fuck and needed to get laid. So why not by two of his hot older friends at the same time?

"Okay, let's fucking do it," replied James. Josh and Matt geared up immediately. As Matt pulled out some lube from his bag, Josh got on top of James and pulled his legs up over his head. After putting some lube on his finger, he began to massage James' asshole.

"Like that?" He asked James, who nodded back. Josh slowly pushed a finger inside of his hole, stretching it out and preparing him for the main act.

James was ready for more. "I want you to fuck me, Josh." Josh smiled and put some lube on his dick, giving it a few strokes before pushing it up against James. With a few pushes, he entered James completely, taking his virginity.

At first, James only felt pain. His cock went limp as he struggled to enjoy this new sensation. James had never even fingered himself before, so this was uncharted territory for him! But after a few moments, the pain subsided and his cock got hard again.

"You're so fucking tight dude. Feel good?"

"Does now," said James as he started to stroke his cock.

Josh kept thrusting back and forth into James, stretching out his boy pussy and hitting his prostate. He was grunting loudly, sweat rolling down his face and chest. He was leaning directly over James' neck, so close that James could feel his hot breath after every push. James was in heaven.

Matt was kneeling on the bed next to them, stroking his cock at the two of them.

"You're fucking that virgin hole good, dude!"

He slapped Josh on the ass, then grabbed it and held on. Josh obviously loved the feeling of a man playing with his muscular bubble butt. His thrusts got faster and faster.

"I'm gonna fucking cum in your tight hole," Josh screamed as he gave one hard, final pump into James and unloaded. His eyes went fuzzy as he kept shooting deep inside James' ass, unable to speak a word. This sent James over the edge. Without a moment to realize his impending orgasm, he shot the biggest load of his life onto his chest. Six huge wads came out of his dick, rolling off his body and onto the sheets. Josh collapsed on James' chest, the semen sticking to each other's chests.

After a moment, Josh pulled his dick out and let cum loose onto the bedsheets. But the encounter wasn't over, as Matt still needed his turn.

"Can't leave me hanging, bro! Ready for another round?"

James couldn't believe it, but he was. Matt had a much bigger dick than Josh, so he wasn't sure how it would go. Matt flipped James over onto his stomach and assumed the position. He pressed his dick against James and slowly pushed in, carefully but forcefully.

"FUCK!!" James screamed as Matt went fully inside him. Thankfully, Josh had already stretched out his hole and lubed him with cum.

"You'll get used to it in a sec," Matt whispered in his ear.

Matt took a moment to let James get used to his dick, and then began to fuck him. At first, he took long, deep thrusts, almost fully in and out. He was holding James tightly to show him who was in charge. James could feel his dick getting hard again, but he couldn't stroke it because it was pressed into the bed. After a few minutes, his thrusts got faster and harder. His body clapped loudly against James' ass rhythmically.

Josh was also getting hard again, and kneeled next to the other two. When Matt saw him approach, he pulled up Josh onto his knees in a doggy style position, beckoning Josh to get in front of James and have his dick sucked.

James thought this was perfect. Not only was he getting fucked from behind and sucking cock for the first time, he could now stroke his own dick at the same time.

Josh and Matt grinned at each other as they tag-teamed James, timing their thrusts to move inside him in unison.

"First time and you're getting fucked by two dudes at once. You're a little slut, aren't you?" Matt teased James with a smile. Having known each other for so long, the whole situation was a bit weird but comfortable and hot as hell.

Matt was obviously getting ready to cum as his thrusts got quicker and quicker. He grabbed James' dick and started to jerk him off quickly, wanting them to cum together. The feeling of another man jerking him off was too much.

"I'm gonna cum, Matt!!" James shouted as he shot his second load of the day onto the sheets and Matt begin cumming inside James. Watching both his friends explode made Josh cum too, directly into James' mouth. James was full of semen. Matt and Josh's loads in his ass and mouth, and his own all over his body.

The boys caught their breath after a few moments and pulled out, collapsing in a big, sticky heap on the bed. Josh was the first to speak.

"Damn guys, I can't believe we just fucked each other."

"I can't believe I just lost my virginity to you two," said James.

"Well don't think that was just a one-time thing man," replied Matt. "I love fucking girls, but anal is always better. By the time this vacation is over, you're gonna be a pro."