Chapter 10:
Cheryl Says Yes
In the morning I had my coffee and gave myself a quickie hand job. Then tidied up to meet Cheryl. Dinked in and before I even got tied to the dock, there she was. "I'm Cheryl." "Hi, Cheryl. Climb in." She was pleasant looking, neither stunning nor ugly. Just above average. In fact, everything about her appeared average. Straight brown hair, not quite to her shoulders. Plain face, little or no makeup. Her body had no real shape to it, no curves, no hips, no voluptuous breasts. Just a totally average plain Jane. She stood on the dock, motionless, looking at how to get into the dinghy, unsure of herself. Seeing her hesitancy, I quickly tied off and climbed up to assist. "Here, just hold my hand to steady yourself and step right down in the middle. You can sit on that front seat." She hesitantly complied, kind of awkwardly, but got situated. At the boat it was the same thing in reverse. Hooked to boat, I got out, extended my hand, and showed her where to step.
Once below she just sat down and looked at me, saying nothing. "So, I'd like you to start with the Vee berth. Take everything out, wash it all down and then put everything back, okay?" She gave me a blank stare and said, "What's a Vee berth?" Oh, boy. I had a live wire here. Lights on but nobody home. I decided to just sit and chat for a minute to see what was going on. "So how old are you, Cheryl?" "28." "Do you live alone or at home?" "Yes." "Are you married, single, have a boyfriend?" "Single." "Have you done this before?" "Done what?" "Uh ... Cleaned boats." "I'll do whatever you say." She was obviously not all there mentally so I tested the limits. "Would you kiss me?" "If that's what you want." "Would you strip naked?" "If that's what you want." "Would you have sex with me?" "If that's what you want."
I now had a dilemma on my hands. She obviously wasn't going to be any good at cleaning my boat. I'd have to guide her every move. Yet she'd do anything I told her to. Would it be wrong to take advantage of such a helpless lass? "So, Cheryl, have you ever had sex before?" "Yes." "How many times?" "Oh, lots and lots. All the guys at the bar I work at take me in the back room." "What do they do in there Cheryl?" "They have sex with me." "What kind of sex?" "Oh, everything." "Do they put their penis in your mouth?" "Yes." "Do they put their penis in your vagina?" "Yes." "Do they put their penis in your anus?" "Yes." "How many guys do these things with you every night Cheryl?" "Oh, I don't know. Maybe 8 or 10. Sometimes there's 2 or 3 at one time." "Do you like this Cheryl?" "Oh, yes. It makes me happy to do whatever they tell me."
My dilemma now solved, "Cheryl, I want you to take off all your clothes, please." "OK, but you don't have to say please." She got up and disrobed as did I. I lay on the bed and told her to climb on top. She climbed on top but did it so that she was just lying flat on top of me. I nearly busted out laughing. "No, no Cheryl. Straddle me on your hands and knees." She still had that blank stare, but she got in the right position. "Now what?" she asked. "Reach around and guide my penis into your vagina. Then sit back on it." This she did like she'd done it hundreds of times before. My cock found her pussy and, because she was not lubed up, it had a hard time going in. Finally, after doing some slow, gentle pumping, it found its way in. She just sat there, not moving. "OK Cheryl. Now lean forward and kiss me." Her kissing was passionless, more like just there waiting for me to kiss her. With her leaned forward, I started stroking my cock into and out of her cunt. It finally got moist, so I grabbed her ass cheeks and started fucking her hard. I got a rhythm going and was soon slamming my dick deep into her slit. Over and over, I jammed my dick up her pussy. I paused and reached for the KY, got some on my fingers and lubed her asshole. "Now I want you to guide my penis into your anus Cheryl." "OK. If that's what you want." She reached around and guided my dick expertly to the exact spot. She even held it there as I pushed to get it past the tight entrance. It finally popped in and I started gently fucking her ass, going faster and deeper with each stroke. I held her ass cheeks as I continued to pound her very tight asshole. I kept it up, first slamming it in her, then slow strokes the entire length of my dick, then fast pounding again until I had had my way with her ass.
I told her to lie next to me as I took a break to catch my breath. She just lay there, motionless, not even breathing hard, staring at the ceiling. "Want something to drink?" "Water." I got up and fetched a bottle of water for her and a beer for me. After our refreshments I told her "Now Cheryl, I want you to just lay on your back and put your legs up high in the air. Can you do that for me?" "If that's what you want." "Yes, Cheryl. That's what I want because we're going to do what we just did but with me on top and you on the bottom." "I'm confused." "No worries, Cheryl. Just lay there while I fuck you again." I climbed into position between her thighs and folded her legs back, up by her shoulders. With her folded in half with both her holes easily accessible, I did the same routine. First, I went nuts destroying her cunt. Then repeated it in her asshole. Then back to her twat, alternating between her now gaping holes. Being on top allowed me to pound deeper and harder into her wet holes. Finally, as I was deep in her ass, that feeling welled up in me. I jammed my throbbing cock deep up her ass, held it there and had a mighty orgasm. I shot a big load far up her ass. I knew that my cum would come draining out her ass when I was done. I was like a kid in a candy shop having this submissive fuck toy let me do whatever I wanted. Throughout this fuck session, she had just lay there, never making a sound or offering any body motion. Her expression was blank - it was like fucking a blowup doll. All I had to do was tell her what position and then have my way with her. For as long as I wanted. This sounds like every man's dream. But truth be told, having to direct every single move on her part got tiring. I knew why she was single, and all the guys just had their way with her in the back room at the bar.
I took Cheryl back to shore, gave her a hundred-dollar bill and wished her well. It was barely noon. Back on the boat I revisited the list for the next name: Joan. Rang her up, got VM. Drat. Next name was Patty. Dialed her number and spoke with a sweet, enthusiastic sounding, engaged young voice. Patty asked lots of questions and sounded eager to have me meet her ashore to discuss details. "How 'bout talking over a burger and a beer this evening?" she asked. I jumped at the opportunity.
