Wild Nights in Winter Park
Author's note: This is 85% reality. Aside from names, very little was changed to protect identities.
Also, please contribute to keep Nifty running! Otherwise we would be able to share such stories, would we?
Back in the summer of '88, I travelled a lot of the south doing audits for a major retailer. My audit partner & I travelled the southeastern US, about 2 weeks of every month. And a lot of the time, we were paired up for larger engagements so that we could get them done more efficiently.
JC and I were in our 20s at the time, and right out of college. He was 24 and I was 22. I'm taller, and a bit on the slender/wiry side at the time - mainly from biking & swimming. JC was shorter, and a bit of gym rat. He was pretty muscular, and didn't skip leg day, either! Both of us had dark hair, and he was the more social one compared to my somewhat geeky nature.
Company policy at the time was that two travelers of the same sex would share hotel rooms, which was really no big deal. And when we were on the road, we often found things to do after work to have a little fun. Over the couple of years we worked together, we got to be very good friends. He was engaged, and I was living with my GF at the time, but we ended up hanging out after work and on weekends even when we weren't traveling.
Over time, I learned that JC would get a little `friendlier than usual' after a few beers. And that was OK with me, because if I was honest with myself, I was more than a little into him. I'd had a short-lived relationship with a buddy in high school, so wasn't really afraid of the idea - but my GF was tall and hot, so I was doing what I could to play it cool.
This trip, we'd been sent to Winter Park for a week of audit retakes. And as is typical with a retake audit, everyone is on edge from the minute you show up. On that Monday, we'd went from the airport straight to the first retake locations to take care of business, and then grabbed dinner before finally heading to that Holiday Inn, which would be our base of operations for the week.
Needless to say, the day had been stressful. Rough flights, rough audits, arguments/debates with on-site management, and so on. So when we hit the Applebee's for dinner that night, we went heavy on the alcohol and light on the actual food. We drank, blew off steam, bitched about the job, and joked around as usual. Fun times!
Monday night, we got to the Holiday Inn, checked in, and grabbed one last beer in the hotel bar before heading upstairs. Once we got up to the room, we hit our default routine: JC grabbed the bed by the window and cranked down the AC. I grabbed the TV and would spin it to HBO or Cinemax, and then we'd strip down to our boxers and hit the beds. Only this time, when I turned on the TV, it came on to the hotel Pay-Per-View channels!
"All right! Porn!" JC said, and proceeded to strip down to his boxers. "First one to splash the TV screen wins!" And he turned to look at me. OK, then!
"Hey, I'm game if you are" I replied, and proceeded to strip down as well.
"Seriously? Cool!" He seemed pretty excited.
It didn't seem like he was joking around, so when I was down to boxers & socks, I sat down on the foot of his bed with him, so we were both fairly close to the TV. He started the movie, and we were pretty quiet at first, just watching the couple on screen get it on. By the time that the girl on screen started sucking cock, we were both pretty much rock solid, and it didn't take long before JC leaned back, tucked his boxers under his balls, and started stroking himself. And 30 seconds later, I was doing the same!
I'd seem him naked before, but not like this! JC looks almost Greek - very pale with jet black hair, and that includes around his thick 6" cock, which was topped with this massive mushroom-like head - I knew right then that from now on, I was going to be setting up drunk nights as often as I could!
"Oh man, your dick's so big!" He said, once we were both actively stroking.
"It's ok, I guess, but you're thicker!." I'm about 7" with a bit of girth. I was longer, but he was definitely thicker! And although we made a show of watching the porn by commenting on the action, I'm pretty sure we were watching each other more!
By this time, the girl on screen was riding Peter North's cock, and we were both pretty close to the edge. JC's cock was leaking more precum than mine, and I took a big risk.
"Let me help you with that" I said and wrapped my hand around his dick.
"What are you doing?" I felt his dick get thicker as I started stroking him, and ran my thumb around that massive thick helmet ridge and along his piss slit. His cock pulsed again, and I swirled his precum around as I started seriously stroking him.
"Oh Jesus!" He groaned as he started to fight against cumming, but that didn't last! About 4 more strokes, with my thumb running up along his frenulum each time, and he was shooting all over his chest & abs! And to feel that fat cock pulse in my hand with each shot was mind-blowing!
While he was catching his breath, I quickly straddled his leg and grabbed my own cock again. As I started stroking frantically, he tentatively reached up and cupped my balls, and when the tips of his fingers made contact with my taint, I coated his abs with my load!
I collapsed beside him, and as we tried to catch our breath, Peter North was shooting his load, and we joked about being outgunned by him. I got up, grabbed a towel from the bathroom, wiped myself down and tossed it to him. As he wiped himself up, I pulled my boxers back on and sat on the edge of my bed. "Dude, that was awesome"
"Holy shit! When you grabbed my dick I almost came right then! Why did you do that?"
"Seemed like a good idea? Did you like it?" I asked, hoping he wasn't gonna freak out.
"Yeah! But, um, dude are you gay?"
"Now you know better than that!" I laughed. "It was a wild idea, and you're my best friend, so I just went for it."
"OK. Holy shit we came a LOT! I need a shower." And while he went to take a shower, I crawled into my bed and crashed.
Tuesday morning came, and it was as if nothing had happened. The alarm went off, we got up, and went about our routine, loading the audit bags with the folders we'd need for the day, and heading out to get the job done. As was typical, we hit the Hardee's after a night of drinking to get the right amount of greasy breakfast into us, and kept on going. Nothing was said about last night, and I was a little bit afraid to bring it up.
Tuesday & Wednesday's audits went pretty well, and we'd overspent our per diem on Monday, so we spent evenings with cheap takeout and HBO while we prepped for the next day. We'd give each other time to call our girlfriends, and just hung out. But then came Thursday...
Thursday we were just north of Tampa, dealing with the worst retake of the week. The original audit had been bad, and there was seemingly no improvement to be noted! "Deliberate incompetence" wasn't something we were allowed to write down, however. After 10+ hours of dealing with this, we were both stressed beyond belief! And as we were pretty close to the coast, we hit a bar on the beach, ordered dinner, and the happy hour special - half price Long Island Ice Teas. Suddenly the night looked promising!
After dinner and too much booze, we headed back to Winter Park. Yes, it was dumb to drive drunk, and I wouldn't recommend it to anyone, but we survived without incident. We got back to that Holiday Inn, had one last beer at the bar, and staggered up to our room at about 1 am.
Conversation in the elevator ("I still can't believe you gave me a handjob," and "Mr Mighty Penis") led me to believe that we were probably gonna get it on again, so I was trying to remain calm. We got in the room, and I headed straight to the bathroom to pee. And just my luck, when I came out, JC was sprawled out face down on his bed, in just his boxers, snoring. So much for that idea! So I covered him up and crawled into my own bed.
A little while later, I woke up to find JC crawling into bed with me. I rolled onto my back when he started to slide his hand into my boxers, and next thing I know, my cock is in his hand and he's straddling me. It wasn't long after than when I'm tucking my boxers under my balls, and he's got both our cocks in his hand, stroking them together. Holy FUCK that felt so good! So with my right hand I started cupping our balls together, and then suddenly we're actively grinding our hard cocks together!
After all these years, I can still remember how incredible it felt to feel that hot, hard cock dragging down the full length of mine, and then grabbing his ass to pull him back up to the top to do it over again! As we got more into it, I started to bring my left leg up to hook around him - I really wanted to feel that fat cock of his work it's way inside of me by this point! Of course, we were still in our boxers, so that had to change! I pushed back against his chest just enough to break contact and we quickly stripped down to nothing, and got back to it!
I'd never thought it would get to this - cock to cock, grinding against each other until we were both seriously dripping precum everywhere. It was AMAZING! Finally, after we'd kissed a couple of times, he pulled up a bit and said "we gotta stop." and I answered "Like hell!" and rolled over and backed my ass up against his cock and started grinding against it. I wasn't going to pass this opportunity up!
He groaned a bit, and started humping my ass, hardcore! I can still remember the sensation of his fat cock and mushroom head grinding in my ass and sliding over my hole, again and again, until I shifted a bit, reached back, and finally got him to slide into me instead! When that happened he FROZE, with just the tip in me at first, but IT WAS IN!
"Oh fuuuuck" he groaned and then he lost control and started fucking me hardcore, with his hands on my hips pulling me to him as he pretty much nailed my prostate head-on! YES! It hurt at first but not much, thanks to all the booze, and I didn't care because I was pushing back against him with every stroke, and it was just unreal! His cock was incredible, and I could feel his hairy balls brushing against mine as we fucked, and he was pulling almost all the way out on each stroke, so each time I feel him go all the way back in.
I hadn't even had a chance to grab my cock, because we were so into the fuck, when suddenly I was over the edge! I started cumming so hard I thought I would pass out! I practically saturated the sheets and my pillow, and my ass was actively squeezing his cock as he kept fucking me, and that set him off, too! He let out a grunt, and I could feel his cock expand in my ass as he kept fucking, and then he pulled out and his last couple of cumshots splashed my hair and between my shoulders! He collapsed on top of me, kissed the back of my neck, and then we shifted to the side, with him spooning me, and we pretty quickly drifted off.
A little while later I woke up, and it was around 4 AM. We'd shifted in our sleep to where I was spooning him now, and this was great, because my mostly-hard cock was where I'd wanted it for a while now: nestled into his ass, with my head almost touching the back of his balls as we slept. I was suddenly getting harder still, and so I reached forward to grab a feel of his cock, which started firming up in my left hand.
I started to wake him up with a handjob while I very slowly humped his ass. I knew when he was fully awake because that's when he started pushing back against me, and then very quickly shot his load in my hand. He then grabbed my cock and stroked it maybe half a dozen times before I shot off all over his hip. I kissed his shoulder, and pulled him close, and we went back to sleep.
When the alarm went off at 7, JC was a bit weirded out when we woke up practically glued together in my bed! But unlike Tuesday morning, we were kinda forced to at least acknowledge it. In the end, we chalked it up to "too much stress and too many Long Island Iced Teas" and went about our day. After a final round of audits in the morning, we left Florida and went back home to our girlfriends, and we never mentioned this again once we got off the plane. We're still buddies - both in second marriages with adult kids and established careers. But we don't hang out like we used to. And I miss that, with or without the alcohol-driven sex.
JC, if you ever read this, I still get off thinking about this and I hope you do, too. You know how to reach me if you ever want to do it again. Just suggest a weekend camping trip and see what happens! I'll bring a little bourbon, and we'll see what happens!