Making sense of my adventures with women, one disaster at a time.

The Disturbing Yacht Story

Twenty-two miles off the coast of Southern California lays a hidden gem in America: Catalina Island. Technically it’s part of California, but anyone who’s ever experienced it will tell you otherwise. Known for its big city, Avalon, most people overlook the quaint island village of Two Harbors. It has only one restaurant, one bar, and one general store, all of which are run by residents who work for dormitory accommodations. It makes a profit mainly during summer from its campgrounds and visiting yachts. Every June, a group of 20-40 of my college friends will camp there for a weekend of sports, hikes, barbecues, swimming, drinking games, and public debauchery (there is no law in Catalina for drinking in public, which is why I don’t consider it California).

After a couple hours of drinking games, accompanied with a few shots, our group had taken over the bar. The only downfall of Two Harbors is the quality of women. Very rarely will you come across a solid 8 between the ages of 21-35. Because there are so few acceptable targets, girls who are actually 5s seem like 9s—like Double A pitchers at a little league game. If I were an ugly chick, I’d move to a low-populated place like this, snag a guy way hotter than me, get married in a haystack or something, then move back to the mainland and start a family. Beats competing with all the other California bimbos who get spray tans, “mani-pedis,” and dress better than I do.

So as a result of such a poor selection, we are usually stuck going after high school chicks or 45-year-old divorcees—and only after we’re severely drunk. Since I’m not into jail or being chased around by an angry dad with a knife, I stick to the older women.

I recognized her immediately. Her blonde curly hair, giant jugs, and huge dancing smile brought me right back to a year ago when I unknowingly made out with her in the wake of Hilliard’s sexcapade with her in a nearby field—while her husband tried to watch or something. I didn’t get all the details. She had apparently told Hilliard she was in her fifties, which meant she was 59, easily making her the oldest woman anyone I know had ever boned.

I had already struck out with the two lone 20-year-olds at the bar, so I made the pre-walk-of-shame over to the big-breasted grandma. This is what sucks about being a horny bastard like me. Most single guys would look at this geriatric beast, become disgusted, and throw in the hook-up towel. But I’m not like most guys; if there’s any opportunity for island sex with someone remotely attractive, I’ll jump on it like a hobo to a freshly stocked restaurant dumpster.

I approached her on the dance floor. “So do you remember last year when we had sex on the field?” I’m not sure why I took this angle; it was probably my instinct telling me that it gave me the highest chance of success. Deep down I had faith in Hilliard’s sex abilities, and I sensed she wouldn’t be able to discern that I wasn’t Hilliard (we did both have dark hair, how could she tell the difference?).

“Yes. That was you?” she faked.

I smiled. “Yep.”

“Wow. That was a hot night. Do you remember throwing me against the bathroom door and pounding me?”

Uh What? “Yeah, it was so good.”

She looked me up and down. “Dance with me.”

I soon learned that her name was Georgia, and she was there with her husband, but he “didn’t mind.” After five minutes of talking while pathetically dancing to Madonna’s “Like a Prayer,” she led me over to a table where a balding dude with white hair was sitting. “Jerry, this is Dave.” (I thought about telling her my name was Hilliard, but there was no way she’d remember.)

I shook his hand.

Georgia turned to me. “Okay, so we need to drop our friends off at their yacht, then Jerry and I will pick you up. Sound good?”

“Sure. You know where to find me.”

I gave it about a 75% chance she’d return, so I spent whatever time I had left partying with friends and downing two more drinks and a shot. I had to be royally drunk to enjoy what lay ahead. A couple of my friends saw what was developing and didn’t even try to talk me out of it; they knew I was a goner.

Georgia returned half an hour later just as I finished a monster piss. She apparently knew people at the bar and didn’t want anyone to know she was leaving with me, so she told me to follow her out thirty seconds behind her.

When I walked out, I saw her silhouette standing at the base of the dock.

“Hurry up!” she yelled and walked down the dock.

I followed her to a side branch of the dock where all the dinghies were. Sitting in one of them was her husband Jerry.

“Our yacht is in another harbor two miles away. It’s like a 15 minute ride,” she told me.

“Cool. Let’s go.”

Before I continue, let me assess what I was getting myself into, since obviously I didn’t then. I was boarding a fucking dinghy with a 60-year-old lady and her even older husband at one in the morning to go to their yacht, which was God knows where. And I was supposedly going to have sex with this woman with her knowing husband chilling somewhere on the boat. While it’s true I’ve had some very bad luck with hook-ups in my lifetime, I’d be lying if I said that I didn’t know what I was getting myself into. I asked for this.

“Just step right here,” Jerry directed me.

I stupidly almost tumbled into the ocean but smartly fell face first into the dinghy instead, blocking my fall with my forearms like Lieutenant Dan.

“You okay?”

I grunted and sat on the end pad at the nose of the dinghy. “Yeah.”

Georgia got in and sat next to me while Jerry sat in the driver’s chair directly across from us.

Not even a minute out, Georgia started making out with me while Jerry nonchalantly focused on driving (I think). Then Georgia started fiddling with her shirt and bra until her giant fake tits were out in the cold ocean air. I sucked on them immediately. Moments later, with the dinghy bouncing wildly at max speed, she unzipped my shorts and fished my dick out.

It was rather dark, so I couldn’t really make out the expression on Jerry’s face, but I could have sworn he was smiling while his wife bobbed me up. This was already getting too weird, but I let her continue at it because she clearly knew her way around a penis.

When we arrived at their yacht, I realized I had no idea where the fuck we were. Their boat was a solid 500 feet away from land, and way the hell to the left of the actual harbor—where half a dozen yachts sat, none of which had any lights on.

Georgia saw me analyze the situation and explained, “We like to be far from the other boats…so we can make all the noise we want.” I acknowledged her and walked inside.

The hallway was narrow, and every room I peeked into was littered with laundry and crap. “Our room’s at the end of the hall. I’ll be there in a sec.”

I laid in bed for a minute or so in the dark room when Georgia walked in completely naked, crawled onto the bed like a saber tooth tiger, unzipped my pants, and started blowing me again. Jerry, thankfully, was nowhere in sight.

Five minutes into the blowjob, Jerry walked in naked! With Georgia’s ass exposed at the end of the bed, Jerry began to work his dick in. According to my friends, the moment Jerry’s dick touched vagina, it was officially a threesome. Figures that I’ve blown threesomes with two 18-year-old hotties, then another with two horny Aussies, but the one threesome I’m successful at is with a 60-year-old woman and her fucking husband.

I was hard before Jerry walked in, but now I was distracted and losing my wood by the second. Jerry, by the way, was awful at sex. His thrusts were so slow you’d think he was on the moon or something.

After two minutes of threesome hell, Jerry pulled out like a snail and laid down next to us! He lay on his side and propped his head on his hand, like he was posing for Playgirl. I couldn’t do this anymore.

I grabbed my softee dick out of Georgia’s mouth, made it off-limits, then turned my head away from Jerry. “I can’t do this,” I muttered.

Mid-sentence it seemed, Jerry got up and walked out.

“Okay, he’s gone. Now I want you to fuck me,” Georgia demanded.

“Are you kidding me? His dick was just inside you. I can’t do it now.”

She ignored me, got on top, and tried thrusting my dick inside of her. I wiggled away. “No.”

Frustrated, she started blowing me again. My eyes kept venturing toward the door, expecting grimy-ass Jerry to make another entrance. Before long, I was hard again and horny enough. I put on a condom and started plowing.

After a couple minutes of Georgia riding me, I felt a wet sensation at the base of my dick. Had she squirted? She was way too old to muster up such juices; there was no way. To make sure, I started pumping her hard and fast, and sure enough, she gushed a healthy stream onto my stomach. Wow, talk about an outlier. Though it smelled uriney, it was still awesome, so I induced several more gushes until my stomach was drenched in her gross juices.

Suddenly I saw movement near the door. I darted my eyes there to see Jerry’s head duck back behind the wall. What a sicko! Georgia continued to ride me. Then suddenly she yelped.

“What happened?”

“Nothing. I just bumped my head. I’m fine.”

We switched to doggy, thus giving me a better view of the doorway to make sure Jerry wasn’t George McFlying us. Every fifteen seconds or so, I’d glance at the door. On my third perusal, Jerry was back! This time he was stroking his cock! He immediately ducked away, but I know what I saw. I shortened my glance intervals to every ten seconds. And like a hungry pigeon lurking around a barbecue, Jerry was there every time, only to franticly scram the moment I looked back.

After catching him for an eighth time, I was no longer hard. This was too weird. I gave up on sex and lay there in defeat until Georgia decided to finish me off with a blowjob.

As we lay in bed, light from a circle window shined momentarily on Georgia. The entire right side of her face was coated in blood. The blood had streamed down to her tits even. This was bad.

“Holy shit. You’re bleeding,” I told her.

“I know. I bumped my head. Is it bad?”

“Uh. Yeah, go check it out.”

She got up and wobbled to the bathroom. Moments later, I heard her cry out, “Jerry!”

I had the bed to myself for a solid ten minutes, during which time I tried to sleep, but just as I was dozing off, a cleaned-up Georgia crawled back into bed and had this awful piece of news: “Jerry has to sleep with us.”

I was wide-awake again. “What!? Noooo!”

“He has to. Don’t worry. I’ll sleep in the middle.”

Oh My God. A minute later Jerry walked back in, still naked, and slipped under the covers on the other side of Georgia. This was rock bottom. All I wanted to do now was get the HELL out of here. I thought of my options, and seriously considered jumping ship and swimming the 500 feet to shore in my clothes to make the two-mile mountainous hike home in the dark. I could make it.

I didn’t do it. Instead I curled up into the fetal position on my side of the bed and whimpered myself to sleep like a broke bitch.

I woke up a couple times in the middle of the night, remembered where I was, realized I was soberer, and felt a pang of fear. I had to will myself into being drunk again just so I could fall back asleep. Morning eventually came, and I woke to Georgia giving me a handjob. Jerry was still laying next to her. She then tried to blow me, but I pushed her back down. “Not with him right there,” I whispered. Obviously deaf to her ears, a couple minutes later she tried riding me. I pushed her back down.

Suddenly Jerry got out of bed and walked out. Georgia followed him, then walked back in. “Okay, he left. So now we can play.” She got on top of me. With daylight seeping into the room, I noticed a bloodied Band-Aid on her temple.

“I need to get back to my campsite.”

“We’ll take you back, but I want you to fuck me again.”

I had no desire for any sort of sexual activities for at least two weeks after what happened last night, but I suppose I had to pay my dues to get out of there. “Okay, warm me up,” I said, and pointed to my dick. She took the hint and began blowing me. We robotically fucked after that. Not surprisingly, I caught Jerry peeking in three times. I never blew my load.

After taking two minutes to find one of my damn shoes, I got dressed and walked out to the deck. Incredibly, Jerry was fully clothed. He grinned at me as if we were old buddies. “Do you have to get back?”

“Yeah. Got a lot to do today.”

“Where are you staying?”

“The campsites.” I took my phone out.

Then out of nowhere: “Did you get any good pictures?”

What the fuck? I quickly glanced up. “Not really.”

Georgia walked out in an oversized sweatshirt. “Okay, we all set?”

“Yep,” I said immediately.

We all took our same spots in the dinghy—Jerry driving, Georgia and I sitting across from him. With the dinghy bucking boisterously, Georgia began asking all sorts of questions about where I lived, worked, blah blah blah. Unfortunately, they lived like ten minutes away from me, which prompted Georgia to suggest we “do this again sometime.” I falsely agreed with her and changed the subject to her kids, who were apparently older than I am.

In what seemed like seven hours, we finally docked back at Two Harbors. I thanked them for the ride, shook no one’s hand, and power-walked back to the campsite. I needed a shower.

 

On a serious note, this might very well be the most disturbing night of my life, up there with the “It Can Happen to You” night. The decision to get on that dinghy and go through with what I did is not something I’m proud of. Jerry could have held me at gunpoint and told me the only way I was getting off that boat was if I sucked him off…or worse. Or I could have drunkenly gone through with my jump-ship-hike plan, and died of exhaustion somewhere on a mountain. I like to think I’m a man who stays out of shitty situations. But when you reenact fucked up stories from Penthouse Letters, things change.

I still recommend Catalina Island to everyone who hasn’t been, just be careful of those yachts, especially the dark ones in the secret harbors. Bad things happen there.

 

 

  • Drew

    Wow, that was a disturbing story. I would’ve jumped ship a long time ago haha Just glad you made it out alive!

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  • Anonymous

    This is the funniest thing I’ve read for ages. Legend.

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