Riley - Twas The Night Before Christmas

Christmas Eve 1998 I was sleeping on the couch in my parent's living room. My family was hosting Christmas this year, so every single bedroom was packed, along with the “bonus room” in the basement. I was stuck on the couch.

I was 19, I didn’t go to college, and was still living at home, oh and I’m gay, but the only people who know I’m gay are the guys I’ve had sex with. The extended family showed up a few days ago, so I’ve been without privacy for more than 48 hours and it was severely disrupting my nightly routine of jerking off before bed. As you can imagine, I was horny and going insane. I couldn’t even jerk off in the shower because there wasn’t enough hot water for all the people in the house so my dad, ever the marine, put a ten-minute timer rule on all showers.

With everyone in bed and asleep by 11:00 pm, waiting for Santa to come down the chimney, I decided to sneak onto the computer (which lived in a corner of the dining room) and have some horny chats online before I go to sleep.

I immediately signed into Yahoo Chat, which was kind of the Grindr of its time. With millions of chat rooms, with topics ranging from Politics to gay teens, I was able to find a chat room that was specific to my town in Pennsylvania, not far from Penn State.

“ASL” popped up in a private message.

“19/m/Pine Grove” I sent back

“Really, I’m not far from PG, 22/M here, visiting family for the holiday.”

“I have family here too, it’s fun but also a little frustrating.”

“I know what you mean, I haven’t been able to jerk off in about a week.”

“Wow, I’ve only gone two days, but it feels like a week ha ha ha”

“You ever jerk off with another guy?” he asked more quickly than most guys in the chat rooms that were not gay specific.

“Yes, and you?”

“Yeah, it’s fun,” he said.

I didn’t usually offer up this information, but it was late and the longer I was online the better chances I was going to get caught by someone, “I’ve done more than that too ha ha ha.”

There was a pause, I thought maybe he lost connection (people still used dial-up back in those days), but then he responded. “Oh, yeah me too, what have you done?”

“Everything.”

“Me too ha ha ha.”

This got my pulse racing. “What do you look like?”

“Almost 6’, short brown hair, brown eyes, 160lbs, in pretty good shape, how about you?”

This made my dick twitch, “I’m only 5’6”, 130lbs, I’m pretty thin, sandy blonde hair, dark blue eyes,” I told him.

“You sound hot.”

“Ha ha ha, well, you could come find out, you said I’m not far.”

“Ha ha ha, if I drove to Pine Grove I’d want to see more than your face.” He told me.

“What would you want to see?” I played dumb.

“I wouldn’t mind seeing you in your underwear?”

“Oh yeah?”

“Yeah, boxers or briefs?”

“Briefs, how about you?”

“I also wear briefs ha ha ha”

“Hot, most of my friends switched to boxers,” I told him.

“Mine too, but my dick is too big, I need the support,” he said.

“Ha ha ha, I doubt it’s that big.”

“It’s not that big, it’s 6.5 but it’s thick and since I haven’t been able to jerk off in a few days my balls are huge and hurting ha ha ha.”

“I’m 6” too, average thick I guess, and yeah, I need to jerk off real bad.”

“Would you want to jerk off with me?”

“Yes,” I told him, my heart started beating.

“I could drive over, it’s only about a ten-minute drive,” he suggested.

I started to get really nervous. Could I sneak out on Christmas Eve without any of the 11 people in the house noticing?

“I have a bunch of people in my house, I can’t invite you in,” I told him.

“That’s ok, I know a spot we could go, if you want?”

I listened to the sleeping house, no creeks of people moving, no noise at all, “Yeah ok,” I sent him my address, “Just pull up to the end of the driveway and I’ll be waiting.”

“Ok, MapQuest says it’s a 13-minute drive, so I’ll be there in 15 minutes.”

“Ok, I’m going to log off and put warmer clothes on, I’ll see you in 15 minutes.” I signed off and as quietly as I could started to get ready to leave. I was only wearing my holiday pajama pants, white briefs, and a T-shirt so it wasn’t nearly warm enough for the outdoors. The trouble was all my clothes were either in my bedroom where people were sleeping or in the dirty laundry which is only accessible through the basement where people are sleeping.

I just threw on a heavy winter coat and slipped my sockless feet into some sneakers. As quietly as I could I snuck out of the back of the house because the front door has an automatic light that would certainly wake people up in the house. It was freezing outside, probably 25 degrees Fahrenheit. I tip-toed around to the front of the house, trying not to get any snow into my shoes. Our driveway is long, about 25 yards, and even though it’s paved it had potholes from years of snow removal so you had lots of patches of black ice and had to be careful.

As soon as I got to the end of the driveway it hit me how stupid I was being. It was freezing, it was Christmas Eve, and I could get picked up by a murderer...or worse someone who looks like Santa Clause and then raped. I thought about running up the driveway and leaving this guy high and dry, but then I panicked at the idea that he would show up and honk his horn and out me.

I saw headlights coming up the street slowly, this had to be him. Sure enough, a 1988 Honda hatchback pulled up and the passenger door popped open. Inside was a really cute-looking guy, who looked much younger than 22, but everything else looked as he described. “Get in,” he said with a cute smile.

I took a deep breath and got in the car, closing the door as quietly as I could.

“Hey, I’m Evan,” he held out his hand.

“Oh, I’m Riley,” I shook his hand and couldn’t hold back my smile.

He put the car in gear (it was a stick shift) and slowly drove up the hill.

“Where are we going?” I asked, breaking the 20 seconds of silence.

“Not far from here actually, a friend of mine lives near here and he told me his entire family was going to New York for Christmas, so there’s no one there,” he grinned.

“Oh, ok,” I was getting nervous, the cold night air was sinking through my thin pajama pants so I was shivering.

“You…ok?” he asked.

“Yeah, I…just a little cold out there,” I laughed trying not to seem nervous.

“Well you didn’t put on much for warm clothes,” he put his hand gently on my leg and started to rub my thigh.

I just looked straight ahead. We made a couple of turns and drove for about 10 minutes listening to Christmas Carols on the radio.

On one of the back roads he turned off the headlights and started to drive slowly, turning into a driveway and then putting the car in park without driving up the driveway.

“We can walk up the hill, my car is going to wake the neighborhood if I try to drive up the icy driveway,” he said and laughed.

“Oh, ok, yeah,” I unbuckled.

We started walking up the unplowed driveway, snow immediately getting into my shoes, and of course, halfway up I slipped on some ice and fell flat on my ass.

He just tried to hide a laugh and helped me up, “you ok?”

Brushing snow off my paper-thin pajamas, “Yeah,” I couldn’t help but laugh at the situation.

We got to the top of the driveway and instead of walking to the door, we went around to the back of the garage where a tag-along camper was set on cinderblocks. He pulled the door handle and the door popped open like a time capsule. We went in, it was really dark but he seemed to know the space well and found a light switch that turned on a small dim light above a small stove.

“They keep this plugged in all year because my buddy’s dad comes home drunk and his mom doesn’t let him sleep in the house, so he will sleep out here. We also would come out here in the summer to camp out and smoke weed,” he laughed and started taking off his jacket. He reached over and turned a nob that kicked on a humming electric heater from the 1970’s. “It’ll get it toasty in here pretty quick.

I took off my jacket and my wet shoes.

“Oh no, your pajamas are wet,” he reached over and tugged at my pants.

“Oh yeah, the snow I fell on was really wet,” I shivered.

“Here, take them off, I’ll help you get warm,” he said, giving my pants a gentle tug and then sat on the bed that was probably a couch when folded up. It didn’t have any pillows or blankets but we could certainly jerk off here.

I pulled off my PJ bottoms and put them on the table across from the heater so they could dry or at least warm up while we fooled around.

“Your undies are wet too,” he smiled, pointing at the wet spot on my left ass cheek where you could see my pink skin through the wet material.

I smiled, “you want me to take these off too?”

He quickly nodded yes.

I slowly pulled them down, giving him a dramatic reveal of my dick which wasn’t hard yet but despite being frozen it was quickly getting hard. I put my briefs on the table with my pants to dry. Then quickly hopped on the bed next to him.

He quickly unbuttoned his jeans and pulled them down, his white FTL briefs glowing in the dim light, his dick was clearly hard and snaking up the right side of his underwear. This made my dick go from halfway to full mast instantly. I started stroking my dick. He reached into his briefs and pulled his dick and balls out over the waistband and started stroking with me.

We quietly jerked ourselves off for a minute until he broke the silence, “Can I jerk you off?”

I let go of my dick and nodded yes.

He reached over and started stroking me, his hand was cold on my dick for a second but my balls didn’t care, I was so horny I could scream and cum right there and then.

I lay back on the bed so he had better access, my legs dangling off the edge. He stroked me for a few minutes and then out of nowhere leaned down and put my dick in his mouth. “Mmmm,” I moaned instantly, encouraging him to continue.

His experience sucking dick was pretty low and it showed, but his mouth was really warm, and I was a horny 19-year-old who could cum from fucking a tube of broken glass at this point.

“I’m getting close,” I warned him after only about two minutes of getting my dick sucked. He seemed to double his efforts, I gently rocked my hips up into his mouth, hearing only the slurping sounds his mouth made I gave him one last warning, “Evan…shit I’m cumming,” and shot my load into his mouth, he tried to pull off but half of my load was definitely in his mouth and he used his hand to pump out the other half for a few pumps.

He jumped off the bed and spit what he could of my cum into the sink. “Ugh, I thought I could swallow it but I couldn’t,” he laughed.

“Sorry, I tried to warn you,” I lay there catching my breath as I felt him sit back down on the bed.

“I don’t suppose you’ll suck my dick too?” he asked nicely.

I don’t like sucking dick, especially since I’m not horny now that I just blew my load. I sat up and reached for his dick and started jerking him off, “I don’t really like sucking dick,” I told him in an apologetic voice.

“Oh,” he paused a minute as he enjoyed my handjob a little, “I don’t suppose you’d let me fuck you?” He said with pleading eyes and a huge smile.

I laughed, “You’re not serious?”

“Riley, I’m so horny,” his eyes were desperate.

I didn’t want to but I felt bad, I guess I didn’t really have to do anything but lay there, no chance he was going to last long.

“Ok, but be gentle,” I resigned.

“I will,” he started pulling his shirt off, revealing a very nice body.

“I mean it, it’s been a long time since I last did this,” I started pulling my pajama pants and underwear back off, leaving my shirt on because it was too cold in here.

He pulled a condom out of his pocket and a small jar of Vaseline. I lay flat on my stomach and tried to take some deep breaths and relax. He put a dollop of Vaseline on my hole, smearing it around a little, it was really cold and my hole puckered around his finger that he pushed in, smearing the Vaseline inside and getting me nice and greasy.

I watched over my shoulder as he pulled the condom tight over his dick and then slathered it with more of the Vaseline, then used his briefs to wipe up the excess off his fingers. He climbs onto my legs and starts rubbing the head of his cock between my ass cheeks.

“You ready?” He asks.

“Yeah, ok,” I turn my head towards the faded wood panel wall of the camper.

I haven’t let a guy fuck me in a couple of months and even though I wasn’t horny anymore since Evan just sucked my dick, but feeling the head of his dick rubbing on my hole was still exciting.

It was quiet out here in the camper, the only sound you could hear was Evan slowly stoking his dick with the condom on, that familiar squishy latex sound, and then he found my hole and started to push in. Now you heard me inhale sharp, “ahh…” I exhaled as he sank his entire dick into me without stopping. Then a satisfying grunt from him.

“Mmmm, oh yeah," he moaned. "You ok?” he asked.

“Yeah, just…just give me a second…fuck.”

He lay flat on top of me, holding my hips, and started to kiss the side of my neck, “fuck Riley, your ass feels so good, you like my dick in you?”

I groaned and he started to raise his hips and rock his dick into me, “ungh,” I groaned, his dick felt huge inside me. Thankfully the Vaseline helped him slide easy in and out because he quickly went from gentle to deep thrusting, not hard but he was digging me out. The way he held me tight so he could really shove in and then get a little deeper with each thrust.

“Fuck yeah, oh fuck yeah your ass, oh my God, Riley, I could fuck your ass all day,” he moaned and groaned.

I grit my teeth, “are you close?”

He gave a few more thrusts, “Not yet,” he slowly pulled most of his inches out and then pushed in hard, slamming his hips into my ass cheeks.

“Ahh…shit man, take it easy.”

His hands still on my hips, he grind into me, “Sorry man, fucking been a long time since I fucked a tight ass like this,” he gyrated some more and then started fucking me in a nice rhythm, pulling half his dick out with each thrust.

“Ungh, fuck man, are you almost there?”

“I’m getting closer,” he moved his hands tighter around my waist and was humping me like his own personal sex pillow. “Fuck you feel good.”

I tried to rock my hips a little, hoping to give him a little more pleasure so he would cum quicker as his dick stretched my hole a little more with every thrust. “Ah, fuck Evan,” I groaned.

“Riley, ungh, I’m getting close, I’m getting close,” he mumbled into my ear, his hot breath tickled my skin. His hips pushing his dick deeper into me, “Ungh, fuck, yeah, I’m going to cum, just a little more,” he grinds hard into me, holding my hips tight.

“Ungh, yeah, cum for me,” I moaned, his slick dick was feeling really good now.

“Yeah, you want me to cum?” He kissed my neck, thrusting harder.

“Yeah, fucking cum,” I was starting to really enjoy it now, now I wanted it to last longer.

“Oh fuck yeah, I’m about to cum man, you want it? You want me to shoot my load?” He didn’t let up.

“Fuck yeah,” I spread my legs as wide as I could under him, feeling his dick slide in and out of my hole, every ridge of his dick now sending pleasure through my body.

“Oh fuck, ungh,” he groaned and humped up into me, pulling my hips up into his cock, “ugh, yeah there, ugh, take it…ungh….fuck,” he groaned as he shot his load and twitched inside me.

I couldn’t help but moan from the pleasure, it felt so good as his swollen cock twitched inside me, the new warm feeling was so good and so slick, I just rocked my hips milking his cock.

“Fuck Riley, that felt amazing,” Evan lay lifeless on my back, his sweat getting through my t-shirt I could feel the moisture on my body.

He slowly rolled off of me onto his back. I rolled onto my side, looking at his naked body in the dim light. He was breathing heavily still, I watched as his chest moved up and down, and I looked further down to see his cock now limp but glistening with lubricant and cum.

“Wait, where’s the condom?” I popped up.

He lift his head, lift his cock, the rubber was shredded. “Oh shit,” he popped up and looked at me. “I didn’t realize, I swear.”

I reach back and felt how wet my hole was, “did you cum inside me?” I started to worry.

“Riley, I…it felt so good and you were bucking against me, yeah…I came hard inside you, like a week-long of built-up cum,” he looked like he was trying to hide a smile.

“Fuck man,” I jumped off the bed, grabbing some paper napkins off the counter and trying to wipe the leakage off my crack.

“Dude,” he chuckled, “It’s ok, don’t panic, I get tested regularly and I don’t ever do bareback,” he confessed.

I grabbed my underwear off the table, now warm from the heater, and pulled them on, missing the leg hole at first and nearly falling onto him before steadying myself and pulling them on with a snap of the waistband. I paced the tiny space of the camper looking for something before I realized I was looking for my pajama bottoms, right there on the table. I pulled them on in a huff.

“You ok Riley?” Evan asked with legitimate concern in his tone.

“Yeah,” I huffed, crossing my arms. “I’ve just…I always use condoms, ya know?”

“Yeah, I get it,” he sat up and slowly pulled the remains of the condom off his dick, then used the rest of the napkins to wipe his dick clean.

“Now I have cum…6 inches up inside me, and I just met you, on the internet,” I tried to sound coherent.

He pulled his briefs on, “6 and a half inches inside you, but that’s not your point,” he shrugged, standing and pulled me in for a hug. “Trust me, you’re fine, I don’t have anything, you’re going to go home and take a shower and realize the only thing that happened to you tonight is a new sexual experience that…hopefully felt really good for both of us because fuck it felt good for me.”

His arms around me, his body heat warming me up, I was already starting to relax because he was right, I just had sex, and a guy, a hot guy just unloaded inside me for the first time in my life.

We dressed and he drove me home. I quietly snuck back into the house. I didn’t shower because I didn’t want to wake anyone. I just lay on the couch and passed out. Of course, I was woken up only 3 hours later by my younger cousins letting me know, “Santa Came!” I couldn’t help but laugh, yeah…someone came down my chimney last night.