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Meet a ravishing beauty; take her to my boat.
Chapter 36:

Rachael Helps With Stuff

I woke up to a gentle rain pitter-pattering on the deck of my boat. I crawled out of my bed and stumbled around getting a pot of coffee brewing. Once it was set, I checked the weather app on my phone to assess this rain. The radar showed that the cold front responsible for causing this rain would pass through and be gone by noon.

Rain is a double-edged sword when at anchor. It rinses the salt off the deck and hardware, but it traps you down below unless you’re a masochist who likes to dress in obnoxious, cumbersome foul weather gear to venture out in the dinghy. I decided to hunker down and sort out my current situation.

By now the coffee was ready so I poured a mug and sat at the nav station to ponder. I knew that I’d have to move on soon. This place, with all its benefits, was clearly going to be busted wide open. Much as I was enjoying the liberal, totally open attitudes towards sex, the thought of spending my twilight years in prison was haunting me.

I had to throw a dart at the dartboard to determine just where I’d go. This decision is not one made lightly. Many factors play into the choice: the time of year (think hurricane season), the prevailing weather patterns, the water quality and depth, the availability of supplies and communication. A glib answer I give to people who ask “Where do you go on your boat?” is: “Anywhere there’s 5 feet of water depth.” Yet, in reality, the decision of where to go next can be a bit more complicated.

I was getting stressed about having to leave this paradise coupled with the where to go quandary. So, I punted. I grabbed my porn-exclusive tablet and fired up my bookmarked porn vids. My “go to” vids are the few that have women with no gag reflex, who let their partner fuck their mouth like a pussy. As I watched these angels let big cocks stroke, balls deep, down their throats, I quickly felt my own cum swelling up in my junk. A few more strokes and voila! There it was. My cum juice squirted out and onto my abdomen and I felt that instant gratification.

Now relaxed again, I sipped my coffee and turned my attention back to the issue of my next destination. As I took stock of my situation, I realized that no matter where I was headed, I needed to restock my provisions, especially my booze locker. This, of course, meant going ashore. I checked the weather app again and saw that the rain front was nearly passed. That gave me time to gather myself together to dink into shore when the rain stopped.

As I tied off to the dinghy dock, Randy was standing there waiting to lend a hand. “Howdy, Sailor! Now that the rain has moved on, what brings you to shore? You looking for some more of my nine-inch cock?” “Hey, Randy. Sorry, but I have other things on my mind today. Maybe later on the big cock offer, but thanks. Tell me, Randy. I haven’t seen much of your lovely village except the only bar and grill and Timmy’s liquor store. Where can I get some groceries nearby?” “Oh, there’s a small grocery just around the corner from the movie theatre. But if you want a full-sized grocery store, you’ll have to go to the next town over, about 5 miles away.”

I wandered into town to check out the “mom & pop” grocery. Sure enough, around the corner from the movie theatre was a small grocery store. It was more like a convenience store with very few fresh vegetables and a paltry ***********ion of frozen meats. The shelves of canned goods had a layer of dust on them. It appeared as if the locals came here for just the necessaries: cigarettes, beer and lottery tickets. I decided to grab some lunch at the only pub in town and see if Carla was there with any advice.

The place was packed, so I sidled up to the only open stool at the bar and settled in. Sure enough, Carla was there, running back and forth behind the bar, pouring drafts, serving plates of burgers and fries. “Howdy, Sailor! Haven’t seen you in a few days. What can I getcha?” “Hey, Carla. Just a draft Bud and a fish sandwich, please.” “Fish ain’t no good today. You’d be better off with a burger.” “Got it. Burger it is, then. Thanks.”

As Carla scurried off, I surveyed the crowd for any familiar faces and to check on any rampant sexual activity taking place in such a busy, crowded place. Sure enough, in one booth there was a couple, he in his 40’s, she was older. But she had massive boobs. Like oversized balloons. Seemed obvious that they were implants although hard to tell from a distance without actually feeling them.

She had her shirt pulled up, sans bra, and the guy was fondling and sucking her tits. He was going to town on them, ravishing her nipples and squeezing them hard. He’d suck her entire nipple and areola into his mouth, bite down on the nipple and pull his head away from her chest, pulling her entire boob straight away from her chest. These boobs were massive and he was obviously having fun.

She showed little or no interest as she casually continued to sip her drink. I was hoping against hope that I didn’t run into Carol. My plans for the day did not include her. Fortunately, I didn’t see any familiar faces, although the place was packed.

When Carla delivered my food, I told her that I needed to get groceries and inquired about the best way to get to the store. “Your best bet is to call Rachael. She runs the taxi service in town. We don’t have Uber or Lyft. Here’s her number.” “Thanks, Carla.” Once I had finished my lunch, I rang up Rachael. “Be right over” she said. Within about 5 minutes, up drove a mini-van.

The driver was a dark haired beauty with sparkling, crystal blue eyes. Her hair was nearly jet black and hung to just passed her shoulders, flowing free. She was in her middle 30’s and she sported some eye-catching tits. They were nice sized and were standing up firm.

“Hop in” she said, motioning for me to sit in the front. As I climbed in, she said “To the Kroger’s, right? Isn’t that what you said?” “That’s right. Thanks for showing up so quickly.” “No problem. There’s never much of a wait. My taxi service is a necessity but most things are so nearby, not too many people call. Kroger’s is my biggest moneymaker. I swear, this van can probably drive itself there, it’s been there so often. Every once in a blue moon, I get a call for an airport run. Nearest airport is a 45 minute drive.”

“Well, I really appreciate it. I’m Sailor, by the way. You’re Rachael, right?” “That’s right. Nice to meet you, Sailor. I’m honored to finally meet you. I’ve been hearing lots of talk about you around town.” “It’s all rumor and hearsay, Rachael. Like the internet, you can’t believe everything you read or hear.”

“From what I hear, you’re a real ladies man. You know how to treat a lady and have the skills to back it up. Most of the assholes in town are only interested in getting a blowjob or pounding you into submission for their pleasure. There’s no consideration for the woman.

“Even with the Partnering thing. When a woman makes a request, the guys just give it an amateur, half-ass treatment as though they’re just going through the motions, hoping to get their dick sucked again. They have no finesse.”

“Maybe it’s a good thing that I’ve never participated in the weekly raffle then. I’d hate to either let someone down or get let down, either way.”

“As I’m sure you’ve figured out, the raffle is simply a system to guarantee sex for the participants. The mayor created it some years ago after going ten years without sex with his wife. He didn’t want to cheat on her, so he developed the system we have today. It’s not perfect, but it does provide a legal way for so many folks to enjoy sex.” “Uh … Rachael. I hate to bust your bubble, but the raffle is certainly NOT legal.”

We drove on in silence as Rachael considered the ramifications of my comment. Finally, I broke the silence. “Look. I’m neither endorsing nor criticizing the raffle system. To me, sex between two adults must be, first and foremost, consensual.”

Seeming a bit agitated and on the defensive, Rachael shot back “Well, buying the ticket implies consent. So, there you have it.” “Rachael, the introduction of money into the system makes it illegal. Whether the participants can be seen as consenting or not, it still boils down to money for sex.”

We continued driving in silence as my mind was realizing that I had pissed off this very attractive woman. I figured that I had just eliminated any possibility of being intimate with her, although my desire was strong.

After a few more minutes of total silence, we arrived at the grocery store. Rachael said, somewhat curtly “Do you want me to wait while you shop? I only charge $10 extra for up to an hour’s wait.” “That would be very nice, Rachael. Yes, please wait. And I apologize for pissing you off. That was certainly not my intent.” “Oh, you didn’t piss me off, Sailor. You just got me thinking, that’s all. By the time you get finished with your shopping, I’ll be smiling again.”

As I exited the store, Rachael was standing near the door, ready to help load my bags into her van. As we pulled out of the parking lot she inquired “So, back to town, Sailor?” “Can you drop me at the marina, please? I’d like to get these bags aboard. Especially the booze bottles. I’m gonna need a stiff drink after pissing you off earlier. Again, I’m really sorry about that.”

“Marina it is. And please don’t give it another thought. You didn’t piss me off and I’m not pissed off now, either. You just gave me food for thought, that’s all. While you were shopping, I came to some conclusions. You’re absolutely right about sex between consenting adults. Consent is key. And paying someone for their consent does sound somewhat shady.”

As we drove along, I attempted to lighten the mood by switching the topic of conversation. “So, Rachael. You said that your taxi service isn’t really a full-time gig. Do you do anything else to supplement your income? Or is your husband able to financially support both of you?”

“Not married, Sailor man. Went that route right out of high school. He turned out to be one of the dumbest people I’ve ever met, unable to hold a job. Divorced him, no kids, fortunately. So now I run this taxi service and do odd jobs around town.” “Hmmm … Interesting. What kind of odd jobs if you don’t mind me asking?” “Well, most anything, really. Kind of a mish-mash of stuff. I clean people’s homes, occasionally fill in for Carla at the bar, that sort of stuff. Since I don’t officially participate in the raffle, I have lots of free time on my hands.”

“Wait, what? What do you mean by you don’t “officially” participate in the raffle?” “I don’t buy a ticket. I don’t go to the Friday event at the theatre. But there are a few *********** men in town who specifically request time with me. It’s all about my jet-black hair and my crystal blue eyes. That look just drives them crazy.

“About once a week or so, I’ll get a call from someone who’s Partner has specifically requested me as a surrogate. These guys really get off on looking at me as I give them head or staring intently at me as they fuck me missionary. My look seems to drive them crazy. Sessions usually don’t last very long because they cum almost instantly! Craziest thing I’ve ever seen.”

“I must admit, Rachael, that you took my breath away when I first laid eyes on you. You are very attractive, very desirable.” “Why, thank you, Mr. Sailor. That’s very kind of you to say. As an older guy, you’re not so bad yourself. Your long hair and full beard plus the vibe you radiate all work together very well. Mostly, though, it’s your vibe. It’s very strong, very positive, very appealing. I can see why everyone in town talks so highly of you.”

“That’s nice to hear. But, honestly, it’s just that I’ve discovered that you catch more flies with honey than with vinegar. So, I try to be positive as much as possible.” “Oh, but it’s more than just being positive. You exude a certain confidence and it’s clear that you have much empathy. People are attracted to you because they just feel that you’re going to treat them right, with respect. That you’ll take care of their needs, too.”

By then we had arrived at the marina. “Let me help you carry your bags to your boat.” “That’d be nice, Rachael. Let me get a dock cart.” We loaded my bags into the cart and we settled up the taxi bill. As I started pulling the cart to the dinghy dock, she oddly followed right along. I climbed into the dink and she handed me my bags. When she saw that the job was done and I was about to cast off, she blurted out “Wait, Sailor. Would you mind if I came out to your boat with you. I can help put all this stuff away.”

Seeing a golden opportunity my response was quick, almost too eager quick. “Of course. Climb in.”
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