Eli - Euro-trippin

I’ll admit it, I was a judgy bitch. Born in 1981 I grew up knowing you’d have to be an idiot to have sex with another guy without a condom. I knew without a doubt that I was gay when I was 11 years old, watching Home Improvement and I felt something special for Jonathan Taylor Thomas. One thing we all learned in the early 90s was unprotected sex, straight or gay, was going to give you an instant STD, a baby, or death. You couldn’t use a public restroom without seeing ads for STD medicine, or to get tested for HIV. Having that ingrained in my head, I knew you’d have to be a fool, a sucker, something of a criminal to risk unprotected sex. So I was a condom queen from my first time at 15 with a fellow virgin who was happy to wear a condom as long as he got to pop my cherry.

In 1999 I was 18 and going through a rebellious phase. Using my bar mitzvah money to travel through Europe instead of interning at the cancer research facility my father was on the board at, which my parents let me know I was “throwing away an amazing opportunity, just to party in Europe” with my “gentile friends.”

I didn’t care, that summer I was questioning everything I knew and had learned, and traveling only made me question more. I wasn’t even sure I wanted to go to medical school or if that was something my parents had determined for me and brainwashed me into thinking it was something I wanted. Thankfully my best friend Eric, the gentile, had grown up in a very different lifestyle. His parents were loaded in every sense of the world. They had a fuck ton of money and were always under the influence of some kind of party drug and alcohol when I saw them, giving Eric free rein to do whatever he wanted whenever he wanted. He’s what my parents would call, “a bad influence.” They’re not wrong, but he was a ray of sunshine for me. Not romantically. He was somewhat bisexual, so I gave him a few blow jobs over the years, it was never reciprocated, but we both got something out of it.

At this point in our trip, we had done London, Paris, Greece, Rome, Amsterdam, and now we were heading to Berlin on a train. Eric had been going through his hoe phase since we were 15 years old, but I had just started enjoying mine. I had tried a new guy in one way or another in each of our destinations. I was careful though, always using condoms and not letting guys cum in my mouth were some hard-set rules I had. Even in 1999, well before PrEP guys would groan at safe sex, but I didn’t care, I was obviously smarter than they were because I knew better. Yeah, I was judgy.

The train ride from Amsterdam to Berlin took the better part of a day. We managed to make friends with some fellow travelers, two single guys and a guy traveling with his girlfriend. They were a lot of fun and Eric offered them to stay with us in his suit at the Ritz-Carlton. They were pretty stoked because they were looking at a hostel so this was definitely an upgrade.

Claire, the only girl in the group was beautiful and I could tell Eric’s goal was to sleep with her. She made no secret of her attraction to Eric either. I had seen it a thousand times though, Eric is a good-looking twink, with a big dick, but to most women, he’s just a skinny guy with reasonably good looks when they first meet him in the wild. However, when he starts throwing money around, driving fancy cars, suggesting we take his father’s yacht out for a trip, or in this case casually dropping that we’re staying at the Ritz, women give him a hard second look. Claire was no exception.

I wasn’t sure if her boyfriend Carter was too dumb to notice or if he didn’t care. He was one of those pretty boys from Southern California, a bit of a doufus surfer type, but he was very easy on the eyes. Wavey sandy-blonde hair that went almost to his shoulders, light blue eyes, strong jaw, dimples when he smiled, if he was educated I’d be teaming up with Eric to divide and concur, but that wasn’t my thing and I was very over “straight boys.”

David and TJ were also pretty bohemian but David was going to Harvard in the fall and TJ was from Albania originally, speaks five languages, and is the son of a former diplomat for former President Bush, going to Brown in the fall.

The suite had two bedrooms, one for Eric and…whomever he has climb into his bed at night, I was going to offer mine to Claire and Carter so they could have some privacy, but they said they were fine with the pullout couch. Eric had two cots brought in for David and TJ.

We all showered and Eric made reservations for dinner, then we all went out to a dance club near the red light district. I had gotten pretty good at clocking guys that were scoping me out in the new cities, but more so guys that were cruising me. Older guys were less subtle, but I enjoyed watching the closeted guys my age squirm as they let their hormones take over and gave the hints that they would be into doing anything sexual they could with me.

At the club the music was loud, the drinks were flowing, Eric always had a hookup for whatever party drug we wanted, and tonight it was ecstasy.

Out on the dance floor, I was really feeling myself, the music was hitting just right, the warmth in my body was causing me to feel happy feelings about the world and life, and the lasers were keeping me distracted enough not to get lost in my head, the smell of sweat and booze in the club were keeping my blood flowing. Through the slits in my eyes I was enjoying the couples grinding against each other, guys and girls, girls with girls, boys with boys, it was just an uninhibited free-for-all of humans enjoying each other in the most natural and harmonious way.

I danced with Eric in a loving, somewhat romantic way, his scent always turned me on. Claire came up between us and stole his attention. Carter came between Clair and me, so I wrapped my arms around his neck and danced with him. At first, it was to let Eric dance with Claire, but something about the way Carter responded to my touch gave me that same tingly feeling I get when I see a sexy guy cruising me.

Carter was about 6’1 and lean, I am 5’8” so I could wrap my arms around his shoulders pretty easily as his hands went around my waist, pulling me tighter to him. I couldn’t help but feel my dick start to get hard as his bulge started to grind against mine. I let my fingers go into his long hair and massage the back of his head until he leaned in and kissed me. Right there on the dance floor, this Abercrombie model just started to kiss me, grinding our bodies against each other, with his girlfriend behind him feeling up my buddy Eric. This was the most exciting thing I had done and that part of my brain that would’ve normally told me to “stop, he’s straight and dating that cute girl”… didn’t seem to be working, if anything it was encouraging me to push this further because “who cares?”

I let my tongue slide across his sexy lips, and like a secret password his lips opened and we started to explore each other's mouths, moaning and groping at each other. His hands slid off my waist and went into the back of my jeans and boxers, grabbing my bare ass. Fuck, my dick went from stiffening to rock hard instantly. Carter’s hands were big and he completely palmed my ass cheeks with a sensuality I hadn’t experienced before. Slowly cupping, gripping, pulling at my cheeks inside my boxers on the dance floor, I was in heaven and nearly squealed when his index finger slid across my puckered hole.

I broke our kiss and looked into his eyes, they were like saucers and the lasers in the room were reflecting in the glassyness of his eyes giving the illusion of sparks and it made me tingle. I slowly pulled away from him, not breaking eye contact the same way I had cruised other guys. Just like those other guys as soon as I was more than a few feet away from him an invisible tether yanked him to follow. I could see behind him that Eric and Claire were hardcore making out, his hands already up her shirt so I felt encouraged to enjoy whatever was about to happen with Carter.

I pulled him to the far side of the club where it was a little darker, pushing him against the wall I went straight for his lips, giving him a kiss that would hopefully question his sexuality for years to come. I felt his surfer body through his sweaty t-shirt. Then let my hand slip down the front of his jeans to give his bulge a once over, making sure he was as into this as I thought he was, boy oh boy was he.

“Let’s go back to the hotel,” I whispered in his ear.

He grinned and nodded, not hesitating to leave his friends and Claire at this club, clearly only thinking with his dick.

There was a line of taxis waiting outside the club, we hopped in the first one, “The Ritz-Carlton,” I said to the driver before Carter closed the door and slid up next to me.

We tried to keep our hands off each other in the taxi. Even under the influence, we were not dumb to the way Eastern Europeans can be closed-minded.

In the elevator at the hotel, Carter pushed me against the wall and started to kiss my neck, then stuck his tongue in my ear which was a new one for me. Then proceeded to suck on my neck, no doubt giving me a hickey I’d have to care about in the morning, but it all felt too good to stop.

We stumbled into the bedroom, crashing onto the bed in a frenzy of hands roaming each other's bodies, moans of pleasure as we grind our clothed dicks together.

I was on my back with him between my legs, his long hair surrounding our heads as we kissed, my hands moving his shirt up as I felt his defined torso until I was able to pull it off of him. I ran my hands up his chest, feeling his pecs I pushed him off of me and onto his back. I ripped my shirt off, then shimmied out of my jeans, keeping my boxers on as I got between his legs and started to undo his belt.

He leaned up on his elbows to watch as I quickly unbuttoned and unzipped his pants, pulling them and his boxers down as his massive dick popped out. I didn’t realize the bulge I was feeling on the dance floor was his flaccid dick, this was easily 7” and growing harder and longer fast. I had played with a lot of skinny boys and been pleasantly surprised by their size, but this was almost intimidating…and I wanted it.

His pants and underwear falling to the floor he spread his legs and I climbed right into place, letting his dick rub on my face, taking in the musk emanating from his hairy balls, causing me to salivate like Pavlov’s dog hearing a bell. I moaned and slapped his cock on my face a few times, the weight of it felt so good on my skin. Looking up his body my eyes met his, his smile telling me everything I needed to know. I licked the head of the meaty dick and he moaned. The taste of his cock was everything I wanted in that moment, he knew it too. I put the head in my mouth and went straight to the back of my throat, my saliva flowing I was able to quickly get it lubed up enough to slip into my throat and started to choke on it like a man on a mission.

“Oh yeah, that’s it, choke on it,” he groaned his head falling back, his legs spreading wider so he could rock his hips up and get a few more inches into my throat.

I was on a mission, I wanted to make this sexy fucker cum. The taste of his precum was so delicious and intoxicating, I wanted to make him cum in my mouth. I knew it was stupid, but fuck this was all stupid and so hot. I bobbed up and down, getting about 7 of his 9 inches into my throat, but it kept getting thicker as I went down and I just couldn’t get it all.

He kept running his fingers through my hair, rocking his hips up and trying to help me get him all the way in but I just couldn’t get my mouth that wide, boy did I try though.

“Fuck yes...Eli, that feels so good,” he moaned.

I squeezed his balls which pushed another large drop of his sweet precum into my throat, I was like a dog in heat and he was giving me anything I wanted.

He pulled my head off his cock, wiping the spit off my face, “fuck,” he smiled at me, “I want to fuck you,” he grinned.

I smiled, climbed on the bed next to him, and started to kiss him, letting him taste himself on my lips, “just be gentle,” I told him.

“Of course,” he grinned, rolling himself on top of me, his cock immediately sliding between my ass cheeks as he used his legs to spread mine wide and kissed my neck, his hair tickling my shoulders as I arched up on my elbows to give him better access to my neck.

“Mmm, yes Carter,” I groaned feeling his cock slide across my hole which was naturally opening in anticipation of his big cock pushing in.

“Yeah, you want it don’t you,” he sucked on my shoulder blade.

“UmmHmmm,” I moaned out.

“Fuck, yeah, I love fucking a tight ass like yours,” he whispered.

The words ringing in my head, I realized this wasn’t his first time with a guy.

“I have condoms in my bag,” he kissed my neck again, “mmm, and lube,” I groaned.

He nibbled my ear, thrusting his dick between my legs, passed my balls, “why, I don’t have anything,” he said.

“Because I don’t bareback,” I reflexively arched my ass up to get more pleasure from his dry humping.

He pushed himself up onto his knees, spit on my hole, and rubbed his thumb on my pucker, “mmm, I moaned.”

“It feels so much better though,” he tapped the head of his dick on my hole.

I’ve heard this line before, it didn’t work then, and it’s not going to work now, “I’m sure it does, just grab my pants, there’s a condom in the pocket.”

He reached off to the side of the bed pulled my pants from the floor and started digging through the pockets, “Nah, just cash and your ID, no condom,” he said, handing me the pants to check for myself.

Sure enough, no condom in any of the pockets, I rolled off the bed and started pulling things out of my backpack that was in the corner of the room, “ugh, I don’t think I have any, maybe Eric has one in his bag,” I ran out the room.

In the bigger bedroom, Eric had his backpack lying on his bed, the contents pulled out, some cologne, a notebook and pen, some candy, ahh, and an open box of condoms with a single condom still in it.

I ran back to the room where Carter was now lying on the bed, slowly stroking himself, looking sexy as hell in the dim light of the lamp. I held up the condom and grabbed the lube from my backpack. Handing him the condom as I started to lube myself up I watched as the stretched the condom over his big dick.

“I guess Eric has a small dick,” he chuckled because the condom was really tight on him, “I have to wear magnums,” he shrugged, a hint of pride pulling the corner of his mouth into a smile.

“This will work just fine,” I told him, adding lube to his tool quickly so we could get to it.

He got behind me and I assumed the position on all fours. Lining up with my hole he didn’t waste any time and started to push in. “ungh, shit,” I felt that familiar sting of being stretched out. Thank God I was still rolling on the ecstasy and drinks from the club because it quickly dulled the pain and turned it into colors of pleasure.

“Yeah, fuck yeah, so tight,” he growled and gave my ass a light slap.

He kept pushing in slowly until I felt his pubes brushing against my ass. Holding it there so I could adjust, for only a few seconds, then he started to pull back and push in hard, pushing me flat onto the bed, “ungh, fuck Carter, gentle,” I groaned.

He chuckled, “Sorry, it feels so good,” he started humping me. Grinding deep at the end of every thrust. He put his hands on my back and started to slowly build up a rhythm fucking in and out.

“Mmm, fuck that feels good, you’ve got such a big dick man,” I groaned, grinding my dick into the comforter.

He thrust harder and faster for a minute and then suddenly the friction changed and he was gliding inside me, he was warmer inside me, I thought maybe he blew his load already but he started thrusting harder and his dick became more rigid. “Ungh, fuck Carter, you feel so good,” I moaned.

“Your ass feels so good,” he was pounding me now. He lay flat on my back so he could kiss my neck and stick his tongue in my ear again and it sent shivers of pleasure through my body. I couldn’t help but clench down when he did it. “Mmm, yeah Eli, give me this beautiful ass,” he moaned in my ear.

I arched my ass as high as I could to give him a better angle to thrust into me, the root of his dick still stretching my hole, his cock pelting my inner ring deep inside me, sending waves of pleasure up into my gut. “Mmm yeah, that’s the spot,” I groaned feeling his cock slide across my prostate, swelling even more than before. Something about Carter had me going insane from pleasure, his big dick just felt so good, more with every plunge into me. If he keeps this up I’m going to cum into the mattress. I keep rocking my hips with his, getting as much of my prostate beaten by the length and thickness of his cock as I can.

He pulls out and tells me to flip around onto my back, that’s when I notice the condom is only a ring of crumpled latex around the base of his slick shaft. “Shit, the condom broke,” I pointed out.

“Oh fuck, you’re right,” he grinned.

“How long has it been broken?” I asked.

“Fuck, I don’t know,” he shrugged, “It felt good this whole time, could’ve been early on, I don’t remember condoms feeling this good,” he chuckled, pulling the destroyed condom off his dick and tossing it on the mattress.

He started spreading my legs and scooting back up to my ass.

“What are you doing?” I asked.

He stroked his dick up and down my ass crack, catching the head on my hole, “I’m going to fuck you.”

“Not like that, ungh,” I told him, feeling his head center on my well fucked and lubed hole.

“Come on man, what’s the big deal, I’ve basically been fucking you like this the whole time,” he shrugged, “it doesn’t make a difference at this point, and like I said, you’ve got nothing to worry about with me,” he started to push in slowly.

“Ungh…I, wait,” I groaned, trying to think through the pleasure but my brain wouldn’t let me.

He kept pushing until he was all the way in, then leaned in and kissed me, moaning into my mouth, “See, that feels so good doesn’t it?”

Oh man did it feel good, I wrapped my legs around his waist and my arms around his back, “make sure you pull out ok, don’t cum in me,” I whispered.

He nodded, thrusting up into me, “I have good control, trust me,” then thrust again and we both moaned.

He quickly got up to speed, pummeling my hole and it was blowing my mind. I kept rocking my hips up into his lap as he thrust down into me, “mmm, fuck,” I groaned. Reaching down between us I started stroking my dick, the pleasure he was giving me was too much, “oh shit,” I groaned, my ass clenching on his raw cock, each additional thrust beating my prostate and it sent me over the edge, “ungh,” I groaned, feeling my balls unload, my hot cum hitting his washboard abs as I continued taking his dick like a champ all the way through my orgasm. He kissed me hard, his tongue finding mine, I sucked on his tongue and held him tight as the euphoria of it all washed through my body.

He picked up the pace, “I’m close,” he moaned, “want me to be the first?” He looked into my eyes, thrusting hard into my aching hole. I just nodded and watched as he thrust a few more times and his face contorted as I felt his cock swell inside me and then he slammed hard into me as he blew his load inside me. Another thrust pushed it deeper as another shot of hot cum mixed in, lubing my insides, “ungh, shiiit, ungh,” he twitched inside me.

“Oh fuck,” I groaned, my legs still wrapped tight around his waist. As his orgasm subsided he tried to pull out but I just held my legs tight and pulled him back into me. I was going to savor this moment.

He collapsed onto me, smearing my cum between us, and panted in my ear. “Wow, Eli, that was amazing,” he groaned.

I rubbed his sweaty back as I held him, still catching my breath I whispered, “So good,” I shook my head in disbelief that I never experienced this before.

He lifted his head and kissed me gently, letting me know with his lips how much he enjoyed sharing in this moment with me. Then he slowly pulled out and got off the bed, going into the ensuite to shower.

I lay there basking in my new best sexual experience. Wondering how this will change things.

The next morning was awkward. Everyone was hungover. I ordered room service and was standing by the counter drinking coffee, hoping to not be walking funny. Claire and Eric came out of the big bedroom looking like they had been fucking all night, a look of guilt on her face while he looked like he just won an Olympic Medal. Meanwhile, Carter was still asleep, naked, in my bed. I gave Eric a knowing grin, he smiled back raising his eyebrows at me as if to ask “Where’s Carter?” I shrugged, smiled, and nodded to my bedroom.

“Anyone want coffee?” I held up the carafe.

Everyone nodded in unison so I poured a few cups and ate some buttered toast while we all sat in silence.

As it would turn out, Carter and Claire have shared a few men, this was the first time they fooled around without each other, and while it was awkward when he walked out of my room only wearing his boxers, no one seemed to care. He kissed Claire on the cheek and they both acted as though it was no big deal.

We spent a few more days with their group before we moved on to Prague. I gave myself a bit of a reset in Prague, I didn’t have sex at all and then when we moved on from there I told myself that I would be even more strict with condom use after that. Turns out…I was lying to myself. When we made our way to Isreal I met a very sexy Jewish boy my age who claimed to be a virgin and wanted to “try it naturally,” and well…who was I to say no to a fellow Jew?