Chapter 8:
Black Out Sam
I had been on the run, going from port to port, for months now. I was getting tired and needed to find somewhere to land, somewhere to stay for a bit and regroup. I saw a protected harbor on the charts with mooring balls available. Perfect! Made my way there and hooked on a ball at the edge of the mooring field. Dinked in to register, then back to the boat. Feeling a bit stressed, first thing I did was go below, pull out my cock and jack off. My thick creamy cum juice shot like a cannon up my torso, almost reaching my face. "Oh, boy. I needed that" I said to no one.
The next morning, I was eager to explore my new surroundings. Dinked in to shore and found the local watering hole, within a block of the harbor. As I sat at the bar, a sweet, young lovely twat approached. "What'll ya have sailor?" "Burger and a beer. And your number." "I can help with the food & drink but I'm 'off limits'. See the bouncer over there?" I looked and saw a burly, bearded guy, size of a bear, muscles everywhere. "That's my husband and he's very possessive." "Got it. Thanks for the warning." After I finished my meal, she approached with "Anything else, sailor?" "Just my check, and some info. I've been on an extended passage and I'd like someone to come help me clean up my boat. Can you recommend anyone?" "Sure. There's plenty around. Give me a minute and I'll give you some names and numbers."
Her list had 5 names. I called the first one, Samantha, who sounded eager and had reasonable rates. I arranged to meet her at the dinghy dock the following day. Went back to the boat and couldn't wait to get below to masturbate. Pulled out my dick and closed my eyes, fantasizing about fucking the sweet little barmaid. I knew she was a cunt that just couldn't say no. As I stroked my cock, I could feel it fucking all her holes. As I got her on her hands and knees, my strokes quickened as I alternated between fucking her luscious cunt and her tightly puckered asshole. First her twat, then her ass, back to the pussy until my cum shot all over her ass, creamy and thick. I used the cum to fuck her ass some more, then realized that the cum was all over my belly. And I was alone.
Decided to do a 'wake and bake' the next morning. Ate a loaded cookie and washed it down with a cold beer. Dinked in to meet Samantha. Sipped a couple more beers as I waited at the dinghy dock. Soon an early 30's woman approached. "Hi! I'm Sam. You the sailor that needs cleaning?" "Yup. That'd be me." I sized her up and she was, let's say, different. She was seriously overweight, like approaching obese. And her face was not attractive. Maybe a 3 on a 10 scale. Her hair was on the short side, kinda ratty and she had tried to make herself more attractive by coloring it. It was 3 or 4 different colors, roots dark brown, then layers of bleach blonde, blue, red ... you name it. It looked like a flag and was so overdone it looked like straw.
We got to the boat and went below. "So, sailor, what do you want done? Looks like a bachelor pad down here." "Let's start with a good wash down of everything. Just wipe it all down with some cleaner and then we'll see what's needed." "Roger that, captain." I got her some cleaning supplies, grabbed more beer, and went topside. I tried to imagine any sort of sex with such an overweight cunt. She had very large boobs I could fuck. But that's never really turned me on. I like sucking and fondling tits but sliding my dick up and down between them pushed together is kinda boring. I much prefer warm, wet sloppy holes to fuck.
She was busy down below, there were no neighbors visible, I now had a good buzz going on and I had been thinking about sex. My cock was hard and wanted to be serviced. Sitting alone in the cockpit, I pulled him out and started stroking up and down. I closed my eyes and started fantasizing about the next name on the list - Cheryl. As I mentally fucked and sucked Cheryl, my strokes quickened. It didn't take long for me to cum, but it was a feeble load kinda thin and watery. When I opened my eyes - Holy Shit - Sam was in the companionway watching!!! "OH MY GOD! I'm so sorry. I didn't mean for you to see that!" "Well, I finished an area and came up for some fresh air." She flashed an engaging smile from her chubby face. She then disappeared down below.
I sat there wondering what to do next. Finally, I summoned my courage for the awkward encounter and climbed below. Sam was just rinsing out her rags and announced that she was finished for the day. No hint of embarrassment, no judgment, but a hint of anticipation. "Looks better already" I said, a bit embarrassed. "What do I owe you for today?" She said "I'm kinda thirsty. Can I have a beer?" "Of course. Grab me one too."
With cold beer in hand, she said "Sit down and let's talk about my pay." Oh, boy. Here we go. I fuck my hand daily but just couldn't imagine fucking this ugly cow. "I have mirrors in my house. I know that I'm not attractive. I know I'm fat. When I go to the bar not a single guy gives me even a second look. I've gone online but never had a right swipe. Never. So, I do a lot of what you just did. I play with myself till it's sore. I have a drawer full of toys, I use them all." "Listen, Sam. You're a nice girl, very pleasant and all but ...." She cut me off. "I'm not asking you to fuck me. Shit, if I got on top, I'd probably crush you. And you'd need a 12-inch dick to get between my butt cheeks to ass fuck me. I've seen your dick - It's not 12 inches!"
"Well, what do you want then?" "I get by okay with my dildos and vibrators in my pussy and my asshole. Just for reference, my asshole is very, very tight. It would make some guy really happy. But swallowing a dildo just doesn't get me off. I practice with it a lot, I can swallow at least 10 inches, but it's just not the same as a live cock. Could you bring yourself to face fuck me? Can you get passed my looks and my weight and slide your cock down my throat? I'd really like to have a real dick in my mouth. Is that too much to ask?" "You just saw me jack off and shoot my load. If I fuck your mouth, it might take a while. A guy needs to recover you know. You up for that?" "I'm so cock starved; you can pound my throat till tomorrow if you want."
"I just shot my wad so you're gonna have to suck him up a bit." "No problem. Can't wait!" She told me to stand up as she got down on her knees. She fumbled with my belt, eventually succeeding as my pants fell to the floor. She yanked my boxers down revealing my now limp, shriveled dick. "Looks like I've got some work to do" she said as she pulled it into her mouth with her chubby fingers. She started working on it and, honestly, had quite a nice touch. Her warm, wet mouth and her eager tongue soon produced the desired effect. My cock started responding and, as I started pumping it in and out, it was getting hard. She took her mouth off and started jacking me off, occasionally sucking on the tip and swirling her talented tongue on my clit. This worked and soon I was rock hard again.
I told her to lay on the bed on her back with her head hanging off the edge. She eagerly complied, a sparkle of anticipation in her eyes. Standing over her I straddled her head and guided my hard cock down into her waiting mouth. In this position she could just lay there as I did all the work. I began to stroke my cock in and out of her mouth, going deeper all the time. She didn't gag or choke. She seemed to be enjoying having my dick fuck her fat face. I soon leaned over, my arms holding me up, my face over her fat belly and started pumping my cock hard down her throat. She moaned in pleasure and reached up, grabbing my ass to assist in the pounding I was giving her face. I kept on fucking her mouth, knowing that an orgasm was miles away. She kept pulling my ass and hips toward her head, obviously enjoying this.
Then disaster happened. She removed one hand from my ass and spread her legs so that she could rub her clit as I face fucked her. Now, my face was hovering right over her groin as I was bent over holding myself up with my arms, my dick down her throat. When she spread her thighs ... I nearly blacked out. The stench was unbelievable. Each woman has their own pussy smell. They're all different and the vast majority are actually quite nice and erotic, at least to me. (I've heard that every cock and balls have a unique odor but I've only experienced mine. Not bad - at least to me!) But her cunt smell was just God awful. Smelled like something died down there or that she never washed her pussy.
I reared up and pulled my cock out of her mouth. It immediately went soft. "What's wrong? You were doing great! I'm really, really enjoying this and was close to cumming. Why'd you stop?" Not wanting to embarrass her with the truth, I just stammered "It's not working, I'm not anywhere near an orgasm and I'm tuckered out. I’ve gotta stop now." "I can get back on my knees and finish you off if you want." "Honey, you just saw me shoot my load in the cockpit. You got it hard again for a minute. But I'm just spent. See ... even my dick is on break. He's all soft." She got up and wiped the spit and drool from her face. "Well, this sucks. Or not" she said crestfallen. "I was having such a good time having a real cock to swallow. I was really hoping for you to shoot your cum in my mouth." "I'm sorry, Sam. It's not happening today." It was an awkward ride back to shore.
