Chapter 40
Randy, Timmy And Donna

Rachael’s phone woke us up. I heard her say “I’ll be right there. Don’t worry.” She crawled out of bed and started putting her clothes on. “How about a quickie before I take you to shore? You know, start the day off right.” Her look said it all. “Sorry Sailor. It’s Mrs. Johnson. She’s diabetic and must have her insulin now. Like right now. So drag yourself out of bed and get your mind out of my pussy, at least for now. I need to get to shore pronto.”

With no time for coffee, we climbed in the dinghy and zoomed to shore. Of course, Randy was waiting on the dock when we arrived. “Good morning, lovers! How are you feeling today? Sexy I hope.” Rachael retorted, “Not this morning, Randy, sorry. I’ve got to get to Mrs. Johnson’s in a hurry. She needs insulin, stat. Maybe another time.” Randy turned to look at me with an expectant, imploring expression. “You part of this medical emergency, too, Sailor or can I fix you a cup of coffee?”

Rachael sprinted to her van and peeled out as Randy and I secured the dinghy and went into the office. He poured two mugs of java and we went into the smaller, private office behind the counter. As we sipped our coffee and made small talk, I could clearly see the outline of his massive cock under his shorts. Our talk centered on our various sexual exploits over the years and I could see his cock starting to swell up to full size. Occassionally, he’d reach down and rearrange it as it continued to grow.

Once I saw the small wet spot appear on his shorts, I couldn’t take the tension any longer. I commanded him to pull his shorts off as I dropped to my knees between his legs. I grabbed his big, hard cock and spanked my face with it. I stroked it up and down for a minute, then put my lips on his head. I sucked the few drops of pre-cum and began using my tongue to give him pleasure. I was still kind of new to sucking dick but I had the advantage of knowing what felt good. I practiced different techniques as I gauged his response. The deeper I took it into my mouth, the better response I got. “Oh, yes…hmmm, that’s nice, that’s nice. Keep it up and I might feed you some cum for breakfast.” “That’s the goal, Randy” I said as I continued thrusting my mouth down on his shaft, getting it to the back of my throat.

I was having a bit of trouble getting his hard dick past my deepthroat door. It wasn’t naseau; my throat just didn’t want to cooperate. Somehow Randy sensed this as his cock was just banging on that glorious door wanting to get in. He stood up and, holding my head, started fucking my mouth. This seemed to help as it was now him doing the work. He thrust it in, over and over, continuing to bang against the back of my throat. “Just relax, Sailor. Close your eyes and imagine my cock effortlessly sliding all the way in and out of your mouth. Relax that jaw and my cock will give it all to you. Yes, that’s good, let me fuck your mouth like this. Let loose, Sailor, you’re doing fine. Just let my dick slide all the way down your throat.”

His encouragement allowed me to switch my focus and turn off my worries. I let my muscles loose as he pumped his huge dick in and out of my mouth. He could feel me relax so he jammed his rod hard at the back of my throat and succeeded in getting it all the way in. Holy Shit! Nine inches all the way down my throat, going in and out, balls deep! This felt more natural as I held onto his hips, pulling his long cock deep down my throat. It didn’t take long before he tensed up, pulled his cock out and grabbed ahold of it, stroking it at my face. Thick ribbons of cum came rocketing out of his dick, squirting on my face, in my hair. He stroked it through four or five spasms until he was spent. That’s when I went into action using my tongue and lips to wash his staff. I sucked the last remaining drops of cum juice from him and licked him clean.

“Ooooooo that was nice, Sailor. And look how I decorated your face!” As he said this he tossed me a towel to clean up. Once I got his load of cum wiped off my face, he poured two more mugs of coffee. We sat in the afterglow and talked more sex. He gave me some insight on the locals and who was good at this or that. I realized that I had fucked most of the best in town. But I hadn’t fucked anyone today and I needed some release.

Out of desperation, I reached my hand up my shorts and started stroking my cock, slowly, gently. Soon that magic wet spot appeared and Randy reacted. “Hold on there, Sailor. Let’s get you off right. No need for you to sit there and wank your willie when you’ve got two willing holes right here. What’s your pleasure? My mouth or my ass? Take your pick. Or, shit, have them both, one after the other. Have at it, Sailor.”

I pulled my shorts down and liberated my hard cock, motioning for him to get on his knees between my legs. He nearly jumped at the chance and quickly began giving me head. He was good at it, better than some women I’ve had. He had had lots of practice and worked his mouth on my dick like a pro. I watched his head bobbing up and down, saw my shaft sliding into and back out of his mouth. As I grabbed his head to start pounding his face hard, he brushed my hands away and looked up at me, “Don’t you want my ass, too? Don’t spill your seed in my mouth yet, fuck my ass first.”

Getting arranged with him on his knees on the chair and getting lubed up allowed me to regain my cum schedule. Although still feeling full, I relished the thought of plying his asshole once again. Even though he was the slut for all the guys in town, his asshole was still very tight and made a cock feel welcome.

I placed the head of my dick against his tiny hole and pushed. It was tight, very tight as he was pinching it shut on purpose. After pushing twice, he let loose and it popped right in. I began stroking it in and out, feeling that tight hole squeeze my dick. It was a delightful feeling and I grabbed his hips as I pumped my stiff rod in and out. With my entire cock all the way in his ass, I felt my orgasm coming on. I rammed it in deep, taking short strokes as my cum juice came swelling up. It shot into his rectum in four big spasms. I slid him in and out a few more times, not wanting that delightful feeling to end. When I pulled him out of Randy’s hole, my cum juice began dribbling down, drenching his balls. A wonderful sight!!

Now that we were both satisfied, I had to get on with the business of the day. I needed to visit Timmy to score my weed. Then make some final preparations to cast off. Randy saw that I was ready to leave so he pulled out a joint and we shared it as we sat in silence, etching our tryst into long term memory.

On the walk to town I realized that I was hungry, so before I visited Timmy’s I stopped at the local eatery for some food. I arrived at the pub and took a seat in an empty booth. Shortly, Donna approached. “Howdy, Sailor! What’s shakin’?” “Oh, hey, Donna. Some black coffee would be nice, please.” She scurried off, returning with a mug and a pot of freshly brewed joe.

“What’ll it be today, Sailor? You want any food?” “I’ll just have a grilled cheese sandwich, please.” “No problem. We’ve all been wondering about you. Haven’t seen you in a few days. Hope everything’s alright.” “Yeah, everything’s okay, Donna. I’ve just been preoccupied lately. I have a lot on my mind.” “Well, everyone’s been talking. We all want to know if you’ll be at the raffle tomorrow. There’s even a betting pool. Odds are that you’ll be there. I sure hope so. If you are, it’ll be like winning the lottery for whoever gets partnered with you.”

Holy fuck. This place was insane. And getting crazier by the minute. It only confirmed that I needed to be long gone by the time the raffle started. “Well, Donna. There are no real guaranties in life other than death and taxes. Can’t say whether I’ll be there or not. But my time here has certainly been interesting. Especially my private times with you.” She blushed a bright red, cast her eyes down to her shoes and scooted off to the kitchen.

I was lost in thought reviewing everything I needed to get done before leaving. Soon Donna returned with my sandwich. “Anything else, Sailor?” “That’s it for now, thanks.” I dove into my food as if I hadn’t eaten in weeks. As soon as I was finished, Donna reappeared. “More coffee?” “Sure. By the way, where’s Carla?” “Oh, she had an appointment in the next town over so I’m filling in for her.”

Now that I had a full belly, things were looking brighter. As Donna stood next to the booth, I surveyed her body. She was still a tight little thing, her thin frame and cute ass wrapped in quite revealing clothes. Her top was so tight, it flattened her A cup boobs against her body, making it appear as if she only had nipples and no real tits. Her skimpy shorts appeared molded to her body, almost as if they had been painted on. Her outfit left little to the imagination.

“I’m glad you’re here, Donna. Nothing against Carla, but the sight of you excites me.” She blushed again and shuffled her feet, nervously. She looked at me with her pretty teenage face and muttered “Gosh, really?” “Yes, really. And the memory of that first-rate blowjob on my boat the first time we met only helps. I’ve been fantasizing about that and wondering if I’d ever have the pleasure of your talented mouth on my cock ever again.”

That’s all it took. She slid into the booth next to me and reached for my belt buckle. Within moments, she had freed my half-hard dick from his prison. She stroked it a moment, then bent over and put her lips around his head. Just his head, no more. The feeling of her warm, wet lips on him sent a shiver up my spine.

She started swirling her tongue around it making sucking noises. Then she gently started bobbing her head, taking just a couple of inches in at a time. Her mouth was so soft and warm; it felt sublime. My normal response would be to start fucking her mouth, but that just seemed a bit crass in the moment. She was being so gentle, so affectionate, so focused on the pleasure she was giving me.

This teenager sucking and licking my cock in broad daylight, in a booth, in a very public place was unique. Needless to say, I would live with this memory far into the future. I watched as she continued her ministrations to my swollen dick. She only took about half of it in but she used her tongue expertly. I started to moan as I felt that unmistakable tingling sensation beginning.

I began fucking her mouth, ever so slowly, not ramming it in, just matching her genteel mouth action. It didn’t take much longer before he let go. She kept her lips around his head as I squirted my load into her mouth. There were three spasms and she took it all in. Her lips still around his head, she worked her tongue back and forth along his underside, massaging my clit as she sucked the last of my jism into her mouth.

When she sat back upright, she swallowed it all and licked her lips. “Did that satisfy your fantasy, Sailor?” “That and more” I replied, a very satisfied expression on my face. “Thank you, Donna. Thank you.” “Glad to oblige. Can I get you anything else?” “That’s it for today. Just my check, thanks. Oh! And tell me where the nearest ATM is, please.” “Just around the corner, next to the convenience store.” I made sure to add a $100 tip. It’s only money and a hundred dollars meant much more to Donna than to me.

I visited the ATM and got cash for my purchase from Timmy. When I got to Timmy’s, a few locals were just leaving, bags of booze in their arms. “Greetings, Timmy! We all set?” “Yup. Come on in the back room.” We went through a door into the stock room and Timmy grabbed my half pound. I gave him cash, stowed the weed in my backpack and was ready to turn and leave when he piped up “What, no tip? I mean usually you give a tip to your supplier.”

Caught off guard for a moment, I quickly calculated that I didn’t really have enough cash to make it worth his while. And I had already exhausted my cum quota for hours. “Gee, Timmy. I guess I overlooked that part of the equation. I’m short on cash and, to be totally honest, I’ve already shot my wad several times today. There’s not much left in the bank.” “Well, how ‘bout you let me fuck your ass?”

Seeing an easy, enjoyable way out of my predicament, I instantly dropped my drawers and bent over some nearby boxes. They were at different heights so I got one foot up on a small box to open up the pathway to my asshole. He dropped his drawers and lubed up with spit, covering his shaft and leaving a big dollop right on my puckered hole. He guided his cock there and pushed. With just spit for lube, it didn’t want to enter my hole. I reached around and spread my cheeks, hoping that would help. Sure enough, the head of his dick found it’s way past my tight sphincter muscles. I gasped as it went in but soon my gasps turned to moans of pleasure as he pushed his cock in deeper and deeper.

Timmy took his time fucking my ass. He was obviously in no hurry and just leisurly rocked his dick in and out of my hole. Sometimes he’d ram it all the way in, hold it there for a moment, then withdraw it, only to repeat that motion. Then he’d get back to just leisurly stroking it in and out. It felt good having a cock up my ass, just steadily fucking me slowly. Even though I had shot my wad several times already, my dick swelled up as Timmy enjoyed fucking me. Just the thought of his dick sliding in and out of my tiny hole excited me. I began stroking my own cock as he continued pumping his up my ass.

Just then, the bell on the door tinkled, signalling that someone had entered the store. Timmy called out “Be there in a minute!” That said, he began pounding my ass mercilessly. He held my hips and thrust his rock hard cock in and out fast and deep. He rammed it in furiously, smashing his balls against mine. He was reaming my asshole like a young teenager, just pounding it until his stifled moans signalled his orgasm. He shot his load in my ass and took a few more strokes for good measure. Abruptly, he pulled out and pulled up his shorts. Then disappeared through the stockroom door.

I was panting a bit from that wonderful bout of ass fucking. I regained my composure and pulled my shorts on as I emerged from the stockroom. It was now late afternoon, too late in the day to get to anywhere during daylight. I walked back to the marina, avoided Randy, and drove my dinghy back to my boat.

 

Really hot