South by Key West

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Gotta go and my girlfriend's round ass provides relief.
2.7k words
4.4
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Back in the late eighties my girlfriend Chelsea and I spent a summer in Key West. We were both in our early twenties and had really just started seeing one another. She had long wavy honey blond hair with big brown eyes, stood 5' 7" and weighed about 125lbs. I was 6', 180 lbs with wavy brown hair to my shoulders and green eyes. At the time I knew she was really good looking, but looking back now, I think we were both probably pretty alright.

When we met, Chelsea already had plans to stay with a friend in Marathon, Fl. for the summer. The more time we spent together though, the less we wanted to spend the summer apart. We were both going to school in Montreal and it was always so hard to find a job there, so soon enough we were making plans to head south together to give the Keys a try.

We ended up taking the bus to Florida and it was an incredibly long, long, long ride. When we got there we learned that her friend never told the guy she was living with that I would be coming too and he didn't disguise his annoyance at the surprise. It was a rough start and it didn't get any better. Within about forty-eight hours of our arrival it was pretty obvious that things wouldn't work out for us in Marathon.

As charmless as our host was, it quickly became clear that Chelsea's friend was a far greater irritant. Aside from her naked dishonesty, she was one of the most ignorant people that I'd ever met. On top of neglecting to tell her boyfriend that I would be coming, she had also falsely told us that she had jobs lined up for us. Her head was an ark full of bad ideas and mistaken beliefs that she never hesitated to share. For instance she let us know that alcohol was her chief form of birth control. She felt that if her boyfriend drank enough, the booze would work as some sort of general spermicide. The system had failed a few times, but everyone knows that no form of contraception is perfect, right?

Once we announced our plan try our luck down the highway in Key West, our host's attitude turned around. He didn't mind letting us leave most of our luggage at his place for pick up later and he also ended up giving us a ride to Key West. The three of us had breakfast on Duval St and before he headed home he even told us if we couldn't find a place that we were welcome to take a bus back to Marathon.

After we ate Chelsea and I got down to business. While I looked for a job, Chelsea began looking for a place for us to stay. It turned out finding a job was the easier part. Within the hour I was busing at a restaurant, but when we met up at the end of the day Chelsea was frustrated and exhausted. She'd been walking all day and had only found two potential apartments, both seeming to be over our budget. We were a little worried we'd have to head back to Marathon.

As luck would have it though, a guy working at a sidewalk kiosk beside the steps we were sitting on heard our conversation. He had a friend with a place for rent and gave us his number.

The room turned out to be pretty small, but it was right on Duval and close to everything. Most importantly though, at least we could afford it.

The landlord was a Lieutenant in the Coast Guard who was originally from Arkansas. After he left, the girl renting the other room introduced herself to us and told us to be ready, because the landlord hits on all the girls who stay there.

Looking at Chelsea she said, "He can be little creepy, but he's pretty harmless."

True enough, though I never got invited, he was always asking Chelsea if she'd like to come over to his place for a swim. After moving in we also found a couple of naked polaroids of him in our room. We found one of him antediluvian selfies in the drawer of the nightstand and the other was left under our bed.

Not the smoothest of moves, but maybe that's just what Arkansas courtship is about? After all, in a few short years a real smoothie from Little Rock name Bill would emerge onto the world stage and despite possessing a true silver tongue, reportedly still liked to just drop his pants as an opening line.

Key West was a great place to spend the summer. Even though we worked too much and spent most of our wages on our puny room, it was still pretty good. I even worked as an extra on a Goldie Hawn movie while we were down there.

Chelsea heard about the filming and found out where to apply to work as an extra. Since Chelsea worked during the day and I worked evenings, she had me bring over our photographs and fill out the application forms. Chelsea was a huge Goldie Hawn fan, and not without merit, felt she bore a strong resemblance to the actress. So when I got called to be an extra and she didn't, she was a little jealous.

During my day on the set I spent most of my time reading a book while everyone waited for the sun to come out. When the weather finally broke they spent about an hour on the shot that I was in, but it never made it into the movie. Chelsea's jealousy was much reduced when she found out that I never met Goldie and with the extra money that I made we were able to have a rare night out.

We ended up going to eat a touristy place on Duval and we followed diner with drinks on a hotel rooftop patio just down the street. The sunsets in Key West are a thing of beauty and atop the hotel was one of the best vantage points in town.

In addition to the sunset that night there was also a lightning storm flashing in the distance. The night darkened as the storm approached and the light show over the gulf was spectacular. Eventually the wind started to really whip up and when the staff began scrambling to batten down the patio furniture we took it as our cue to move inside. Since the lounge was so full with people coming in from the patio, we decided to finish our beers and just head back to our place.

Waiting for the elevator Chelsea firmly declared, "I want sex when we get home!"

By the time we got to the street it was already pouring rain. We tried to run for it, but we didn't make if far before deciding we were just too drunk to run any further. Besides we were already soaked. The rain was coming down so hard and Key West is so flat, that by the time we got to our apartment even the raised sidewalks were under a few inches of water.

We'd forgotten our keys, so we had to climb up a tree and get in through the patio at the back of our apartment.

The layout of our place was a little weird. Our kitchen led to the bathroom, and the bathroom opened up to the first floor rooftop at the back, which doubled for us as a patio. So the patio access wasn't really ideal or without the occasional interruption. On this night though, entry through the bathroom was perfect for us. Not only could we hang our wet things up on the shower curtain, but after a night out drinking I really needed to piss.

We stumbled inside, completely drenched and making out. I pressed Chelsea up against the wall and we began pulling each other's clothes off as we kissed. As much as I wanted to turn her around and fuck her against the wall, the beer we drank had caught up with me and I desperately needed to pee.

"Hold on Chelsea," I said interrupting things. "I gotta piss first before I bust."

"No problem," Chelsea said, before tuning quickly and giving me a shove away from the toilet. "So do I."

Giggling hysterically Chelsea whipped down her panties and plopped herself down on to the toilet seat before I could get there.

"Hey!" I protested.

"Ladies first, you'll just have to wait your turn," she laughed.

Except for the dress that was bunched around her waist, Chelsea was naked as she sat there tinkling. Wearing a great big grin on her face, she was obviously quite amused to make me suffer.

Dropping my short I stepped in front of Chelsea and threatening leveled my rigid cock at her, "Maybe I'll just go as if you're not even there."

"Don't you dare!" she laughed.

Then dangerously calling my bluff Chelsea took my cock in her mouth while she peed. If I weren't so hard I doubt I could have held it.

I was never so happy to pull my cock from a girl's mouth as I was when Chelsea finally finished peeing. Rushing Chelsea off the seat, I leaned forward bracing myself against the wall with one hand while my other hand tried pushing my cock down toward the bowl. I could barely manage a trickle with my cock bent down like though. After so many beers it was also a bit of challenge to hold my balance in that position too. When I'd slightly relax the angle of my cock I did manage to fire a few uncontrolled bursts, but none that managed to hit the target. I was making a real mess.

Since close proximity wasn't working, I took a couple of steps back to try from three point range. With my back against the wall I let my cock point upward in the hope I could arc a stream into the bowl. I managed to launch a few spurts toward the toilet, but before I could adjust my aim into the bowl the flow always ended. I bet eighty year old men are able to maintain steadier streams.

It was about then that Chelsea chimed in, "Just so you know, you better clean that up after."

"Sssshh!" I said to silence Chelsea's laughter.

It just wasn't working and it was a little uncomfortable. If I weren't afraid of getting hit by lightning I would have gone outside and pissed off the back of the roof. There was one tried and true solution for getting rid of a hard on that came to mind me. I would have to fuck Chelsea first.

I pulled Chelsea over and leaned her up against the wall. Crouching down behind Chelsea's long legs and I began the tasty preparation. I could have licked her sweet pussy longer, but my discomfort only afforded me an abbreviated effort. That's what she gets for laughing at me - less foreplay.

Standing I passed my cock under Chelsea's ass cheeks and easily slide into her welcoming wetness. I found myself fucking Chelsea rather gently though. I realized that every time I drove my cock into Chelsea, that her butt would press into my stomach and squeeze my bladder. It was really unbearable, but it did seem to be creating the pressure on my stomach that could help overcome my hard-on's capacity to staunch my piss.

"Are you alright?" Chelsea asked.

"I'm okay, just give me a second," I said.

An idea began forming in my head. I pulled out from Chelsea and said, "Come on, let's get in the tub."

Tuning on the shower and then sliding up behind Chelsea I pushed my cock back into her silky pussy. As we fucked my thrusts kept compressing my bladder and when I felt I couldn't take it any more I pulled out and tried to piss on Chelsea's ass. Other than a few spastics spurt of piss though, there was no relief. It was torture, but considering the circumstance, it was awfully enjoyable torment.

I kept fucking Chelsea while continuing my futile attempts to piss. Without Chelsea's ass pressing into my stomach though, I was just too hard to pee. That's when another light went off in my head.

I slide back inside Chelsea's pussy and once I was nice and wet with pussy juice I slide back out. I took my dick in my hand and aimed it carefully at Chelsea's tight little asshole. Finding the target I slowly began pushing my cock in. Once I got through her threshold's initial resistance Chelsea began pushing back against my cock.

I fucked Chelsea until I was nice and deep inside her ass and then began just holding her tight against me. My hands felt over her body, feeling handfuls of Chelsea's breasts, roving all over her naked midriff and especially stroking and probing and her wet pussy. Chelsea began rhythmically thrusting her ass back against me and I needed to tell her to stop.

"Why?" she asked.

"Just let me relax inside you for a bit," I said.

I held Chelsea tight against me with her round butt pressing my bladder, closing my eyes I listened to the rain outside. Then finally it started. Deep in Chelsea's ass my cock began shooting out long interrupted streams of piss, slowly at first and then with growing intensity.

As the streams became longer and steadier I asked, "Can you feel that?"

"Yes," Chelsea whispered as she moaned.

"What does it feel like?" I asked.

"I can't believe the way it feels," she said. "It feels so hot inside me Mike."

My piss seemed to go on forever. Not surprising considering all the beer that had been dammed up inside me. I held Chelsea tight throughout until a mighty shiver shook us both.

Breaking out of her reverie Chelsea's asked, "What was that?"

"Don't girls get piss shivers?" I asked.

"I guess, but not like that."

With a real sense of relief I started fucking Chelsea's ass. As I began slowly driving my cock in and out of Chelsea the remaining shots of piss streamed out inside her. By now Chelsea felt like she was melting I my arms. I wasn't just holding her tight against me, I was also holding her up.

"Oh Mike, that feels incredible," she whispered.

The shower was splashing over us, but as I fucked Chelsea I could still feel the hot piss trickling down our legs.

As I picked up pace, I pressed Chelsea against the wall. With her tits pressed flat on the tiles, her back arched pushing her ass out to meet my thrusts. Turning her face toward me Chelsea opened her mouth for a hungry kiss. The way she kissed confirmed that Chelsea might have been enjoying having her ass filled with hot piss even more that I enjoyed doing it.

After fucking Chelsea slowly against the wall for a while I re-positioned her facing the back wall. Using her outstretched arms to brace herself against the wall, Chelsea bent over in front of me to take my cock. Then just as I began ramming back into Chelsea a bright bolt of lightning lit up the night outside and the lights went off in the bathroom.

It was suddenly pitch black and I took a moment to pause. The water was still splashing over us and I could feel the tightness of Chelsea's ass squeezing my cock. The house was quite inside, but outside the wind was whistling and the bright flashes of lighting that momentarily lit up Chelsea's body where followed by thunder that rattled the windows.

As I got used to the darkness I restarted slowly fucking Chelsea's ass. I knew that Chelsea liked to be fucked hard though and I eventually began building up the pace again. The harder I fucked her, the more Chelsea began pushing back against me. Over and over I drove my cock to the hilt, while Chelsea's body shuddered in orgasm. Even as she moaned in pleasure, Chelsea continually demand I fuck her harder.

I pounded Chelsea ass while the thunder rumbled and the lighting illuminated our bodies. Then finally driving deep into Chelsea's ass, the cum surged from my cock. Thrust after thrust I kept surging, adding my sperm to complete the mixture deposited deep inside Chelsea. I held her a tight to me and continued pumping my cock into her until I was completely drained. When my cock softened and slide free, Chelsea turned back around toward me and we kissed in one another's arms.

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3 Comments
dirtywhiteboy67dirtywhiteboy67about 4 years ago
Hot and Nasty

I've done a lot of things, more than most people, but I've never done that.

I'm going to have to try it.

But right now, I'm going to have to jack this thing off.

MrNiceguy777MrNiceguy777over 8 years agoAuthor
Thx!

Thanks Snube. Appreciated.

SnubeSnubeover 8 years ago
Holy mother of gawd and all that is precious

Love this story more than a $100 bill.

I should write my staining story too.

OMG.

AWESOME

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