365 Days Ch. 05

Cyndi – Day One (Lunch)

I was wondering why I was so tired out.

When Cyndi asked "what do you say we grab some lunch?" I realized that I hadn't had anything to eat or drink all day except the water I'd used to wash down the little blue pill. I hadn't really noticed how hungry I was, but then, my mind had been occupied elsewhere.

And I was so thirsty! I wonder where all my bodily fluid had gone to?

I scrambled around and found both of us some shorts and t-shirts to wear. The shorts kept falling off of Cyndi, so she just went with only a t-shirt. Small as she is, it covered pretty much everything. Mostly. Most of the time. Actually, it was almost more distracting when she wore the t-shirt than having her walking around totally nude. So I left well enough alone, as I liked it that way!

I hadn't really been expecting company, so the pickings were pretty slim in the kitchen. We rummaged in the refrigerator and the cabinets and finally settled on a balanced meal of left-over pizza, some frozen French fries heated up in the microwave, Cheerios with chocolate milk, slightly mushy pears, Power Bars, kosher dill pickles, and frozen juice bars, all washed down with Cokes. I also popped another little blue pill.

We also found some spray whipped cream, for which Cyndi invented a great new serving suggestion involving no dishes, and for which clean-up was the main attraction. I think if they showed this serving suggestion on their label, sales would go up one thousand percent.

After lunch, and especially after Cyndi's whipped-cream dessert idea, we were pretty funky, so we took showers. Well, we took A shower.

Usually, after I shower, I just dry off and get dressed. But Cyndi showed me the advantages of rubbing baby oil all over myself. Which is to say, SHE rubbed baby oil all over me. Then I rubbed baby oil all over HER. Then she rubbed herself all over me, and so on, until we were all hot and sweaty again, and had to take another shower.

We finally did get out of the bathroom, but somehow, we never did get dressed that afternoon. I mentioned to Cyndi that I couldn't remember everything she had taught me that morning, so she suggested a review, which we actually went over a couple of times. As kind of an extra-credit assignment, Cyndi instructed me in the use of The Grand Canyon as yet another place to relieve my erection. I was amazed to find it at once similar, yet quite different from exploring her vagina, and Cyndi seemed to enjoy the novelty of it, as well.

At first when we tried it, I tried to simply push my penis, which was ready to go again and hard as ... I don't know what ... hard as an erect penis, I guess, into little Cyndi's asshole, but all I accomplished was to smash the spongy tip of my cock flat against her and nearly fold the length of it in half. Before I could ask Cyndi if she knew of a better way to go about this, she said, "Oh, sorry Dale, I should have known you'd need some guidance. Don't you have any lube around here?" She looked around, then looked at me, then said, "Of course you don't. Just a sec!"

She hopped up and went into the bathroom and came back with the same bottle of baby oil we'd just been using as an extra-shower inducer. "Here ya go, Dale, just splash a bunch of this around on me, smear some on yourself, and things should go quite a bit easier!"

I got a little diverted here, and was starting to worry out loud about all the various, copious, and not altogether sanitary fluids we had been depositing on my bed. The surface of my sheets was starting to become kind of gamey, and it was becoming harder and harder to find places to play with my new friend that didn't have uncomfortable chilly puddles of one kind or another. Actually, I was more worried about permanently ruining my mattress beyond repair than anything else, even comfort.

"Well, in the first place, Dale, you remember that promise you made me about maybe lowering the bar a little bit on the sanitary issues?"

I acknowledged that I remembered it well, and was trying to be more open-minded. Cyndi said, "Well, honey, you've been doing good, but this concern about laundry would totally qualify as one of those things, not to mention that it's a real mood killer to have a guy stop things in their tracks when I'm trying to teach him how to fuck me in the ass in order to fret about his mattress! You know?"

I told Cyndi that I could see how that would be true, but I had paid two thousand dollars for that mattress and box springs, and as much fun as we were having, I wanted to own this bed for many more years, but not if it was all squishy and smelled all the time like my room smelled at that moment.

"Okay, Dale," Cyndi said, with the kind of frown on her face that I was much more used to seeing on the faces of beautiful women that I usually interacted with. "I'm maybe beginning to see why you don't have a girlfriend." Seeing her look at me that way actually kind of relaxed me a little bit, since I felt that now I was on more familiar ground. Next, she would slap me, storm out, and I would never see her again, if things followed their usual pattern.

But no! Cyndi looked like she was counting to herself for a few seconds, then smiled, but with a lot of teeth and stretched-out lips like maybe she really didn't mean it, and she said, "Here's what we'll do to get us through this. First, give me a few minutes and some new sheets, and I'll re-make the bed for you, okay? I'll put a couple of your big ol' bath towels under the bottom sheet to protect your precious mattress, too! That gonna work for you?" She hit that last "that" pretty hard, and I thought I maybe detected a little bit of sarcasm.

"That would be terrific, Cyndi!," I said, trying to make the interchange as upbeat as possible.

"And you know what else, Mr. Home Beautiful?" Cyndi asked. "I'll even call the service and ask them to include a mattress pad from now on when they bring new linens! How's that?"

"Sounds great!" I said. "And what should I do while you're doing all that?"

"Couldn't you help me ...? No, never mind, I'll tell you what you can do, pal," Cyndi started out, kind of brusquely. Then she paused a little bit, and seemed to be doing that counting-to-herself thing again that she was doing earlier. The she said, very sweetly, "Why don't you go make us some nice big drinks to share for when I'm done, huh? You know, the ALCOHOLIC kind of drinks? And, Dale, would you make mine really strong?"

I did as I had been asked. I found some ginger ale in the cabinet over the refrigerator from last New Year's Day, and most of a bottle of vodka. I got out the two biggest water tumblers I had, put several ice cubes in each, and filled them about half-and-half with ginger ale and vodka. I sipped one, and decided that Cyndi might not think it was strong enough, so I drank about half of it down in one long gulp and filled it back up with vodka. I made a mental note that my right hand was the one holding Cyndi's drink, and found my way back to the bedroom.

Cyndi was just finishing up making the bed, but she still seemed, I don't know, kind of tense. I said, "Thank you SO much, Cyndi, you're just fantastic!" trying to sound like I imagined regular guys would sound when they were trying to make regular girls feel good about them. Cyndi looked at me funny, maybe as if she thought I was being sarcastic myself, and then she saw the drinks I was carrying.

"Well, hell Dale, you don't fuck around when a girl asks you for a big drink, do you? What you got there?"

"All I had was ginger ale and vodka," I said.

"Sounds great," Cyndi said. "Why don't we go out into the living room and just relax a little bit and see if I, mean WE, can't get back into the mood?"

I told her that sounded like a grand plan, so we did. I wasn't certain by the time we sat down on the sofa which drink was Cyndi's, my memory suddenly didn't seem as sharp as it usually was for some reason, so I gave her the one in my left hand. She took a little sip, and said, "Oh, no! That's a bit TOO strong, Dale!" and switched glasses with me before I could say anything.

She took a sip of the other drink and spit it out all over my carpet. "Jesus, Dale!"

What had I done? Cyndi got up, and took her drink into the kitchen. I could hear her pouring most of it down the drain, then I heard her open another can of soda and pour it. When she came back into the living room, her drink didn't really look any different than it had before. She took a sip and said, "There, that's better!"

We sat for quite a while in the living room drinking our drinks while I told Cyndi about my work, and she told me about hers. All in all, I'd say she had the more interesting job. Over the course of maybe half an hour or forty-five minutes, we both had drained our drinks.

I was feeling a little odd. The room still looked slightly blue, but now it was also kind of fuzzy, and maybe rotating very slowly. I felt a battle going on in my crotch between that drink I'd had and the little blue pill over whether I was going to stay alert and hard or get all limp and fall asleep. Luckily, after a while, the room settled down a bit, and the little blue pill apparently won the battle.

Cyndi seemed to have mellowed out considerably, too, and was smiling at me like she meant it when she got up, took my hand, and led me back into the bedroom. She carefully turned down the bedspread, blanket and top sheet, and climbed up onto the bed, indicating that it was time to start classes again.

I climbed up next to her, and she got up onto her hands and knees, put her head down right on the surface of the bed, and handed me the bottle of oil. "Lots, Dale, use lots!" was all she said, then closed her eyes, reached behind herself to spread her cute buns apart, and just waited.

Okay, I told myself, I can do this. I'm a smart guy, I can figure this out.

I opened the spout of the bottle, and just held it over Cyndi's butt crack and squeezed. A steady stream of oil ran down over her, although I missed at first ... my aim seemed to be off a little, and a stream of oil ran down her butt and onto my sheets. I thought about saying something to Cyndi like "I told you so!" but then I thought better of it.

Anyway, I must have poured a quarter of what was left in the bottle into Cyndi's ass crack before she said, "Dale! Dale! That's probably enough, Dale!" I stopped pouring the oil, and Cyndi said, "Now rub it all around back there, Dale, and rub a bunch all over yourself!" I started to massage the oil around onto Cyndi's ass, when she said, "And, you know, Dale, when I say rub some around on yourself, I just mean on your cock!"

"Oh, no, I didn't know. Thanks!" I thought I had everything lubricated up pretty good, but Cyndi said she thought maybe I should try to get some oil actually INTO her asshole, so I poked a finger in there, and tried to guide as much oil in there as I could. Then, as she seemed to be loosening up a little back there, I tried the same thing with two fingers, then three. After about ten minutes of this, she was about as oily as I could ever get her, and she also seemed to be in a much, much better mood. I guess the drinks had taken effect!

"Now, just push it in there, Dale! But, go a little slow, and be careful, okay?" Cyndi said.

I tried again to push my cock into her asshole like I had before, but now that everything was so oily, it was slippery and I had a hard time getting myself centered in on the target. But I kept at it, as Cyndi sighed, and finally, I got the head of my dick seated right in the little pucker of her ass. I pushed, hard, and I thought I was going to rip the head of my cock right in half! When Cyndi had told me to be cautious, I thought she was worried about ME hurting HER, but if this was how it was going to feel, I wasn't sure I really wanted to do this very often!

But, just as I was thinking of giving up entirely, something gave and my cock just sort of slipped in there. Because it was so oily, and I had been pushing so hard, it went in just as far as it was long, and thanks to the little blue pills, it was pretty long. Cyndi gave a yelp, then another sigh, and I felt my dick surrounded by a nice, warm, soft pillowy area deep within her, plus a ring of piano wire or a strong rubber band right at the entry.

As I had when I had my penis embedded in Cyndi's lovely vagina, I felt that same illogical urge to pull myself right back out, then push myself right back in, back out, in, out, and so-on. As I said before, it felt similar, yet different to fucking Cyndi in the more usual place. The constriction around the base of my cock actually felt quite uncomfortable, but in a phenomenon which I have since experienced many times, that very discomfort perversely led a heightening of my overall sexual feelings. Cyndi reported that she had similar feelings, composed of both pain and pleasure at the same time.

Otherwise, it was okay.

While we reached a mutually satisfying orgasm this way (Cyndi screaming out, "Oh you ass-fucking weirdo bastard!" at the critical moment actually helped me achieve my explosion into he anus), all in all, I don't think I'll ever make ass-fucking a big part of my sexual repertoire.

... to be continued in Cyndi – Day One (Dinner and Beyond)!