Xander - Wasting Condoms (Patreon)

Born and raised in NYC I lived and breathed a world of diversity. At least outside of the apartment.

Living in Queens with a single mom, an older brother, and a younger brother, you can imagine everything was tight. The living space was cramped and money didn't fall off the trees either. Oh and as a gay boy with a catholic mom who immigrated from the Dominican Republic, “diversity” was a good thing for skin color but not for sexual identity.

With such tight quarters at home, there was no privacy, at all, so I was only able to jerk off in the school toilets and man was that unsatisfying. So I would go a week, sometimes two weeks between orgasms, then I would be blind with horniness and be able to rub one out in under 5 minutes.

When I found out about Craigslist personals, I went through all of the current posts and over a couple of weeks put up dozens of my own, claiming to be older than I am, and wanting to try gay sex. I would email a few times with people until they realized I wasn't going to go through with it and would stop responding.

Living in New York City it wasn't hard to be a closet gay though. I lost my virginity to a stranger off Craigslist in 2002 when I was 15. He was older, said he was 20 but he looked 30 when I met him. He was still hot though and I was too horny to pass up losing my virginity to a hot guy.

Over the next couple of years, I repeated this process about once every two months. A different guy every time. Always playing safe, almost always bottoming.

When I turned 19 in 2006 I moved in with a couple of friends in a 3-bedroom apartment in a different neighborhood in Queens. Still not out, but I had my own room to jerk off in whenever I wanted and it was easier to sneak out for sex from my apartment than it was from my mom's place.

My roommates were both straight and always teased me for “having no game” even though I am ‘good-looking’ and considerably more articulate than they are. I'm 5' 10”, thin, and I have what my friends jealously call “skinny guy abs.'' It works well with clothes so I can pull off any fashion trend I want. They also joke that since I'm Dominican I have a big dick by default so I'm wasting it by not getting laid all the time. I just laugh it off because they are right, I do have a big dick, but I realized over the last couple of years I'm a total bottom. I enjoy a *good* blow job, but most people don't know how to give good head.

This particular Friday night, I found myself home on my shitty laptop, I posted my usual “19/m/ Queens” ad on Craigslist with a picture I took of myself with my hard dick stretching my boxer briefs and nothing else on, my face cropped out of course. I wrote that I was looking to “meet like-minded guys around my age, must have a picture to meet.”

Before 8 pm I had dozens of responses. The most intriguing was one guy, White/25/M/Hyatt. He wrote that he was in the city for business, looking for NSA head, maybe more.

I wrote him back asking if he had a picture of himself.

The other that looked interesting was “Hispanic/29/M/Queens,” he sent a couple photos, all of which made him look to be in phenomenal shape. He said he is 6’2”, 195, with a 7” uncut dick. He said he was looking to fuck a tight boy ass.

I responded, “I could get down for that. You have to be gentle though, I'm not very experienced.”

I logged off when one of my roommates, Aiden, came home from work. We started smoking weed and catching up. He had plans to go out with coworkers but wanted to pregame at home since he didn't have the money to go all out at the bar. He asked me to go with him to the bar but I told him I already had another thing and wouldn't be back until late, but that I'd text him if mine ended early.

My phone buzzed in my pocket.

I opened my Sidekick and read the email from the guy at the hotel. It was a photo that looked like it was a professional headshot of a cute blonde guy with pretty eyes and a cherub face. “Sorry, I only have this one from my company's website, I don't have nudes if that’s what you’re looking for. You should still come over, no pressure, if you don't like what you see you don't have to come in. It's the Hyatt at Grand Central, 1015 if you're interested. I'm Kyle. Let me know if you're going to come.”

I checked to see if the other guy wrote back, he hadn't. Kyle seemed like a safe and sexy guy though and I wrote him back, “Sounds good, I can be there in an hour.” I told him.

I finished smoking with my roommate then took a quick shower, grabbed a condom out of my drawer just in case, and headed out.

I always get nervous meeting guys like this, but it's good nervous. The weed definitely helps me loosen up. I went up to the tenth floor and found room 1015, knocking quietly and then taking a step back so I could be out of grabbing distance…just in case I needed to run.

Kyle opened the door, wearing a t-shirt and gym shorts, he was definitely freeballing in those shorts because you could see his junk flop back and forth just from opening the door. He looked great, exactly the kind of guy I needed to scratch that itch for me and I’ll be good to go for a month or so. He waved me in and locked the door behind me.

The room was nice, but small. I kicked off my shoes at the door and then sat on the end of the bed.

‘Do you do this often?” He asked.

“No, do you?” I felt my nerves running through my body even though the weed was in full effect.

“Not really, only when on work trips. Want a drink?” He asked.

“Sure, whatever you're having,” I said.

He walked to the desk where he had a paper bag with a bottle of alcohol and a bottle of Coke. Got some ice from the little container and mixed it up in one of the hotel glasses. He handed it to me, “It might be a little strong.”

I took a sip, it was like fire burning down my throat. “It's good,” I lied.

We drank our drinks and talked about his work and how they paid for all of this. He finished his drink pretty quickly so I chugged mine to catch up.

He took my glass and set it with his on the desk, then came back and kissed me awkwardly and aggressively. Then he pushed his shorts down to the floor, his dick flopped around, soft with disproportionately large balls dangling with it. He grabbed the back of my head and pulled me to his crotch.

“Suck me hard Xander,” he groaned.

I was feeling quite buzzed and went with it. I put his dick in my mouth and started giving him my best work. He slowly got hard after a few minutes, but not fully hard.

He pulled his 4.5” cut dick from my mouth, gave me a sloppy kiss, and moaned into my mouth like this was the hottest thing he'd ever experienced.

He broke the kiss, stroking his dick, holding my chin, and looking into my eyes he said, “I don't usually do this, but you're so hot and I really want to fuck you.”

It felt like he was reading a script, but I was horny and figured I'd let him hit it. I smiled at him, playing the game and I moaned, “yeah, ok, do you have condoms and lube?”

“I have lube, but no condoms, I didn't plan to go this far, but you're so hot,” he said, trying to feed me a line I've heard before.

“That's ok, I came prepared,” I pulled the condom from my pocket and handed it to him.

“Oh good,” he feigned elation.

He hopped on the bed, pulling the last of his clothes off, and lay on his back. “The lube is in that bag,” he pointed at his travel kit.

I got out of the bed and grabbed the lube, handing it to him as he rolled the condom down his softening dick. I stripped my clothes off and crawled back into the bed. Not really feeling this guy anymore, he seemed very fake but I still wanted to get some, it had been too long since my last hookup.

He handed me the lube and I applied some to my ass, fingering it into my tight hole.

“Come ride me,” he said, his voice doing that fake ‘overwhelmed with passion’ breathy thing he seemed to think was sexy.

I straddled his waist, my soft dick was bigger than his semi-hard dick and it dangled down onto his stomach as I hovered over him. I reached behind me and lined him up with my ass, he wasn't hard enough to even attempt to push into my hole. I slowly jerked him back to life for a few minutes, getting him hard enough and tried to get him in but I was too tight.

“If you're not feeling it, we don't have to…” I tried to say tactfully.

“I am,” he said with a frustration in his voice, grabbing his dick and quickly stroking himself for a few seconds and then attempting to press the head to my hole.

With a lot of effort on my part his head popped in. It stung a little, but his girth was average at best so the entire 4.5” of his dick slid in with minimal effort on his part.

He immediately started thrusting mechanically up into me at top speed. I watched through blurry eyes as his body flopped around under me like a fish out of water while he moaned and grunted like a dog with a bone.

To say it didn't last long would be an understatement. After about 3 minutes of fast, uncoordinated thrusting, without warning he pushed in hard and blew his load, filling the condom. To his credit, he produced a good sized load and inflated the condom enough inside me that I felt pleasure from that brief second, but his cock deflated instantly and he pulled out quickly. His cock slipping out of the condom as he did, leaving me to pull the condom the rest of the way out of my tight hole.

“Oh man, that felt so good,” he huffed out of breath, chuckling loudly, very impressed with his performance.

I dismounted and did my best to agree with him without sounding sarcastic.

“Mind if I shower real quick?” I asked.

He looked uncomfortable with the idea but allowed me to shower. I just wanted to wash this lack luster experience off so I could meet my roommate out at the bar and not feel needlessly dirty.

When I was done he was already dressed. I quickly dressed and thanked him for inviting me over, telling him I had an early morning and left.

I texted Aiden to find what bar he was at and asked if I could get in with my fake ID. He said I could, and thankfully it wasn't far from the hotel, about 15 blocks, so I walked, texting him to order us some shots.

I was at the bar for about an hour and managed to do two rounds of shots, go out and smoke with Aiden and one of his coworkers, then come back and nursed a beer. By 1 am I was pretty drunk and ready to leave. He was trying to hook up with a woman from his office that showed up late, so I caught his eye and signaled that I was leaving. He gave me a thumbs up and I left.

Waiting on the train back to Queens I noticed I had an email on my phone. It was from the 29 year old and only 10 minutes old.

“I can be as gentle as you need me to be. I would love to stretch that ass out if you're free tonight.”

I felt a rush of excitement, looking at his photos from the previous email I felt my balls begging me to go and get something resembling satisfaction.

I wrote him back, “I'm kinda drunk, hope that doesn't bug you. If you're up for it and want to pleasure my tight ass, send me your address and I'll be there as quickly as the MTA will allow it.”

As soon as my train got above ground and my phone service reconnected, it buzzed. The new email had his address and said, “I'm a little drunk too, but I definitely want to use your hole for pleasure.”

Thankfully I was on the right train already, just needed to get off at a later stop. I messaged him back, “I'll be there in 20 minutes.”

Of course the late night MTA fucked me worse than Hyatt-Kyle and it took me closer to 45 minutes to get there. When he opened the door he was wearing athletic shorts, his boxers sticking out the top line a muffin as if he rushed to put them on, his dick clearly tenting in the front.

“Xander?” He asked.

“Yeah, sorry it took so long,” I looked up his body, it was sexy as hell, every muscle looked finely toned like he had a perfect gym regimen and never had a cheat day. His skin was tanned, a few tattoos on his right shoulder and the beginning of a sleeve down the arm. His skin seemed to be glistening, like he was doing a light work out.

“I thought you bailed, I started jerking off,” he smirked, grabbing the bulge in his shorts, “but I'm glad you're here now.” He motioned for me to come in.

“I'm Mateo by the way,” he smirked.

“Nice to meet you,” I walked into the living room.

The carpet was outdated, the furniture was sparse but seemed like everything was a deliberate choice with a real clean and comfortable vibe.

“Do you smoke?” He pointed to his small glass bong on the table.

I grinned, “set it up,” and sat down on the couch next to him.

We each did a few rips, holy shit that was good weed.

He also had great taste in music, a playlist coming from his laptop of great slow songs someone had remixed to club beats as it thumped through his sound system and we got high as fuck from his weed.

I was feeling relaxed as hell and he slowly pulled my shirt off. He didn't kiss me, but he used his massive hands to hold my head and looked me in the eyes then rest his forehead on mine. We shared a moment, it was very sensual. He took another rip from his bong and did it again, this time he shotgunned it to me, still not kissing me, his lips hovered over mine, taunting me in a way that had my insides heating up as this hit did its job.

He leaned in, kissing my neck, his one hand massaging my head, running his fingers through my short wavey hair, the other hand sliding down my shirtless back, gently massaging every muscle until it reached the waistband of my boxer briefs.

“Mmm,” I felt a guttural moan escape my lips.

He nibbled my ear, then fisting my hair, pulled my head back so my Adams apple was on full display and he licked it and down to my neck to my clavicle and fuck it felt so good. He sucked on the skin, nibbled, and teased it until the pleasure was too intense, he sensed it and moved on. His hand came up my back to hold me as his other pushed me gently onto my back on the couch. I was like putty in his hands.

He kissed the center of my chest, licked one nipple and then nibbled the other with so much pressure I moaned, “Ungh, too hard,” and he moved down, rubbing my abs with his big hands, his fingers tracing each little bump until he got to my waist. Without hesitating he licked my treasure trail from just above my belly button down to the waistband of my underwear and pants. Hooking his hands into the waistband he pulled slowly, but firmly enough to pull my jeans and underwear down together, my hard dick sprang free and he caught it with his warm mouth.

Sucking the tip as he gently and completely removed my pants and underwear. He leaned in, spreading my legs he used his hands to massage my thighs, up to my crotch where his thumbs massaged my taint as he licked one of my balls, then the next, alternating until they each got sucked into his mouth, sucking gently at first and then hard enough my body rocked from the tension.

“Oh fuck,” I groaned, pleasure shooting through my body, my hips rocked up into him instinctively.

He dropped my balls and even though my dick was hard and leaking he ignored it, pushing my legs back with ease, his big tongue went flat and licked up my crack from the back, across my hole and grundle, landing on my ball sack and he sucked each ball into his mouth giving each one equal treatment and the perfect amount of teasing that it borderlines torment.

“Oh God,” I groaned in pleasure.

“Mateo,” he corrected me, and then his tongue made its way back down, lingering in my hole this time, a new torture technique called ‘pleasure’ rocketed through my body.

“Oh fuck, Mateo, that feels so good,” I reached down to massage his head, and his tightly cropped hair tingled on my fingertips. “That's it…mmmm.”

His tongue pushed deeper into me and I managed to spread my legs while keeping them elevated just using my muscles, giving hem all the room he needed to manuever his head to do the magic he was doing to my hole.

“Mmm, oh my G - ahh it feels so good Mateo,” I continued to feel myself open up for him. This was the pleasure I needed to scratch that itch. Mateo worshiped my hole like it was his religion and I was here for it. He kept eating me out until I was leaking so much precum  it was starting to pool in my treasure trail, I scooped it up and used it as lube to start stroking my cock slowly. I had to take it easy or I would bust right away and I wanted this to last.

I rode his tongue and the high from his weed and just enjoyed the waves of pleasure that ran through my body.

When he pulled his tongue from my ass I was feeling so relaxed I just slowly lowered my legs into a frog position, watching him as he slid his shorts off without getting off the couch, his massive dick sprang free. He said 7” but it looked bigger, it was certainly thicker than the pictures made it look. He opened a well worn cigar box on his coffee table, he pulled out a tube of lube and squirt some in his hand, stroking it onto his cock, pulling his forskin back and coating himself. He squirt another dollop on his hand, gently fingering some into my well eaten hole.

“Mmm,” I couldn’t help but enjoy the attention.

He pulled out a bottle of poppers and took a long hit, inhaling deep and then holding it like we did with the bong, then blowing it out, repeating on the other side. Then he passed them to me. I hadn’t actually done poppers before, but I’d seen other guys use them during sex, and something about the combination of the weed in my system, the euporic amount of pleasure still running throug me from his lengthy ass-rimming session, I just wanted to go with the flow. I took the bottle and took a small hit, the rush was there, but nothing to write home about.

He smirked, “you’re going to want to take a real hit,” he said, putting my legs around his waist, lining up his lubed up cock with my hole, he leaned in to me and grabbed the bottle. He held it under my nose, closing one side, “Inhale as long as you can and hold it,” he instructed.

I did as I was told, trying to impress him with my lung capacity but the rush was intense and quick and I felt my body relax and I thought I might pass out for a second but didn’t, “oh wow,” I smiled.

He wiggled his dick on my hole, his precum smearing and adding to all the lube, sending an exhilarating tingle through my body. I held the bottle under my other nostril, closing the first one, “again,” he said in his sexy, husky voice. Again I inhaled deep, the rush hitting harder, my heart beating fast, the room spinning, my lust for him intensified in a way that can’t be measured.

“Fuck,” I breathed out, feeling him push his cock head on my hole.

He capped the poppers, putting the bottle in my hand for me to control. He leaned in over top of me, one hand on the cushion on either side of my head, hen bent his head down and kissed me for the first time tonight. Sparks instantly flew, I moaned into him, his ass rimming skills were amazing, but this was something else. His tongue explored my mouth, my hands wrapped around his muscular back, feeling him flex as he held himself above me, and my legs wrapped tighter around his waist, feeling his cock teasing my hole, I was in heaven.

He reached down with one hand and stroked his dick, not breaking our kiss he lined it up with my hole and started to gently push in, the thanks to the precum pooling at the tip of his dick inside his forskin he was slick and the head popped in with surprising ease. I moaned into his kiss feeling him breech my outer ring without causing me any pain, holy fuck did he feel good. He gently pushed further and sank a couple inches into me, I tried my best to relax but he could tell I was starting to struggle with his girth.

He broke our kiss, licked my lips and whispered, “take two more hits on each side this time,” then he lowered his lips to kiss me and then kissed my chin, my neck and finally straightend up, bringing his hands back to my thighs.

I did as he said, two more on each side and my head was spinning, I felt my body open for him and he felt it to, “that’s it Xander, open up for me,” he slowly pushed forward until the last of his dick sank into me with a groan. “Oh yeah, fuck you’re tight,” he rocked his hips making sure to get as much of him in me as possible.

I felt my asshole stretchign to accomodate his massive tool, “fuck you’re way bigger than seven inches,” I groaned.

He smirked, “your sexy hole wrapped around my dick either way,” he ran his hands up and down my abs like he was pushing out any negative energy.

He just held his dick in me, flexing gently, “are you ready?” he stroked my still-hard dick, rocking his hips ever so slightly back and forth.

I couldn’t get over how good his dick felt inside me, how much I could feel of his heat and the ridges of his veins and even the forskin felt amazing. It was in this state of bliss that it hit me, he hadn’t put on a condom.

He gave a slow half dick pull out and a gently push all the way back in, it felt so good, he slid so easily inside me, “Ungh…mmm, fuck, umm…” I held my hand on his abs to stop him, “did you put on a condom?”

He leaned into me and kissed me, “no,” he rocked his hips again, a little more than half his dick sliding out and back in.

“Ungh…” he hit that spot inside me, “we need to wear a condom, can you put one on?”

He thrust again, most of his dick sliding out and then back in deeper than it had initially, we both moaned, he kissed me, “I don’t have any, don’t usually wear them,” he whispered, then kissed my neck and stroked most of his dick out and then back into me.

“Ungh mmm, fuck, wait,” I thought about it and remembered I wasted the only condom I broght with me on Hyatt-Kyle. “I…I don’t have one,” I admitted.

He stroked his dick out and then grind deep inside me again, “mmm, I am negative, tested recently,” he kissed my neck, “just let me fuck you,” he pulled out and pushed back in to the hilt.

“Mmmm…ungh,” he hit that spot with all his inches, “I don’t…I’ve never…” I tried to form the right words.

“It’s ok, I’ve got you, just enjoy that raw dick sliding in you,” he pushed deep into me.

“Ungh, G- uh Mateo, fuck, we shouldn’t,” I held onto him tight, the pleasure was so intense I couldn’t think.

“That’s it, just take my dick Xander,” he thrust again.

“Mmmm, ok…just, pull out to cum ok?” I pleaded, his dick hitting my spot again.

“I’ll warn you when I’m ready to pop off,” he kissed me again, sticking his tongue down my throat and building up a slow, steady rhythm. Rocking his hips into me, stretching my hole to its limits, I could tell he was holding back, making sure he didn’t hurt me and just enjoying the tightness of my hole around his raw dick.

“Mmm, Mateo, yes, fuck me,” I groaned.

He kissed my neck, his muscular arms wrapped around my back and held onto my shoulders as he started to fuck into me with more power in each thrust. His dick peging my prostate as it slid in and out, it felt so good to feel him inside me. I rocked my hips up to meet his thrusts as he started to really pound my ass, the sound of his hips slapped in time with the beat of the music, it was pure bliss.

Mateo sat up on his knees, putting my legs on his shoulders, and continued his animalistic fucking, taking my ass as his own play toy. He started thrusting at a speed that made me think he was about to cum, but then he stopped and pulled out gently, stroking his dick.

I hit the poppers again and started stroking my dick. I wasn’t going to last long. My legs were still on his shoulders, he teased my hole as he stroked himself, kissing my ankle and gently rubbing my thigh with his free hand. Fuck he was beautiful.

He pushed the head back into me and held it there, I rocked my hips on it, sending myself over the edge. “I’m gonna cum,” I warned him.

He thrust a little deeper into me, slowly sinking the entire rod in as I rocked my hips and impaled myself. I felt my balls tighten and my ass constricting around his cock.

“Fuck, I’m cumming,” I warned, jerking my dick furiously.

He rocked his cock into me, stretching my hole a little more, “yeah, get that nut,” he thrust his hips.

I couldn’t hold back any longer, jerking my cock and flexing my muscles, my cum shot out of my dick and landed several ropes onto my chest and abs, a few smaller ropes landing on my hand and treasure trail, “ungh, fuuuck,” I groaned and spasmed.

He let me ride out my orgasm, and then when he could tell I was done, he gently started to pull his dick out, then right before the tip fell out he pushed right back in.

“Ungh, fuck,” I groaned loudly. “I can’t, I’m too sensitive,” I said.

“Take a few deep hits and let me pop off,” he said in his deep sexy voice, continuing to thrust into me.

It was gentle thrusting, but I was too fucked out to enjoy it. I quickly found the poppers and took several hits, then a couple more for good measure. The waves rushed over my body.

He could tell I was feeling it and he started to fuck me to the tune of his pleasure, short thrusts that went as deep as possible, it was a combination of pain and pleasure and the poppers helped me to focus on the pleasure.

He went for another minute or two, “are you close?” I groaned.

“I’m getting close,” he leaned up into me, my legs falling to his sides as he continued to fuck me gently. He kissed my lips, scooping some of my cum off my chest and putting it in his mouth, licking his lips and swallowing. Then kissed me. I had never tasted myself before, something about his moaning and me tasting myself with his bare cock pistoning deep inside my guts, I was hard again.

His abs stroked my cock with every thrust, his tongue deep inside my mouth, he moaned. “Let me pop inside you,” he licked my lips and looked into my eyes. “I’m so close,” he moaned, rocking his hips faster and more erratic with his rhythm. One, two thruts, he kissed me hard, “I’m gonna pop,” he thrust deep into me, “Ungh, AHHH,” he groweld, pulling me tight to him, his hot cum unloading inside me, “fuuuck,” he thrust agian, coating my insides.

I held him tight, rocking my hips up into him, “mmm fuuuck,” I groaned, feeling his cock swell to an even bigger girth than before, his slick dick sliding in and out as a few more ropes of his nut unloaded into me.

He collapsed on top of me, “oh fuck, Xander,” he breathed heavily on my neck as he caught his breath.

“Oh shit, Mateo, you nut in me,” I tried to crane my neck to look down his body, seeing his muscular ass flexing with my legs wrapped around him. There’s no doubt his entire load is inside me. Yet my hips still instinctively kept flexing, milking his slowly deflating cock.

“Fuck, Xander, you took it like a champ,” he chuckled. “That’s the best ass I’ve had in a long time, I had to pop in you,” he kissed my neck.

I just held him tight, unsure what to do next. He lay on top of me for what felt like a half hour, his dead weight making it hard for me to take a deep breath as I held him.

He eventually pushed himself up off me, my cum sticking to both our torsos as he did. Then he slowly pulled his flaccid cock from my well fucked hole, I felt some of his cum squirt out with him. I slowly closed my legs, those muscles well stretched out left me feeling weird.

“You can shower here, I have extra towels, you can stay the night too…if you want,” he sat back on the couch.

I nodded, pointing toward where I thought the bathroom was, he nodded and smiled at me.

I took a long hot shower, relaxing into the idea that I just let a stranger breed me for the first time in my life. It was a weird feeling, a good weird, hard to wrap your mind around.

I didn’t spend the night, I made up an excuse about roommates being up and expecting me home. I told him we should do it again sometime and took his contact info.

I didn’t contact him though. However, I did run into him about 6 years later at a Pride event in the city, turns out he is a DJ. That’s another story.