365 Days Ch. 03byDear_Dora©
Cyndi -- Day One (morning)
Cyndi, as I have already described her, was unforgettable. Although she was my first, and I have since had a busy, busy year, I can yet picture her in my mind's eye, smell her fragrance in my mind's nose, and feel her hot, firm but yielding flesh in my mind's fingers to this very day.
Let me say this about Cyndi: She was totally at ease with our agenda, and totally at ease with the fact that I had no idea whatsoever what to do about it.
Cyndi first sat me down, then pushed me back onto the messy and unmade bed. For an instant, when she was right in front of me and as I was sitting there, I noticed for the first time that Cyndi seemed to have gone prematurely bald. Not on her head, of course, but in another place on which I had always imagined hair might grow. In fact it was a place where I knew hair usually grew on adult women, from long study sessions with reference magazines and on the internet.
Right after pushing me back onto the bed, with my legs still hanging over the side, Cyndi kicked off her shoes and sox, tossed her cute little brown cap across the room, climbed up onto the bed with me, and swung her leg over me, straddling my chest like she was planning on riding me, somehow.
"Now, here's an idea of something we can do while we're waiting for that little pill to take effect," Cyndi said. She moved her legs over my arms and trapped them in the crook of her knees. "Like what you see?" asked Cyndi, but I was unable to really see anything except her naked and bald crotch. Then I realized that that's what she was referring to.
"Oh, uh, yes, I suppose," I stammered, "It looks ... nice!"
"Oh, dear, you are a sad one! The right answer to that question is always 'Oh, YES! You look wonderful ... you're beautiful!' You never say 'it' looks this way or 'they' look that way. It's always 'you,' and it's always 'wonderful,' or 'fantastic,' or 'sexy,' or 'beautiful'! Okay?" instructed Cyndi. "Now, let's try that again!"
"Okay," I said.
"Like what you see?"
I tried to marshal my thoughts to remember what exactly I was supposed to say. "Oh, YES!" I gushed, trying my best to seem enthusiastic, "you look terrific!"
"Better," Cyndi said, "but that little hesitation there makes me think you had to think about it and that maybe you don't really believe you like what you see, but you're just saying that to make me feel good. So let's try it again, okay?"
"Like what you see?"
"Good Lord, yes!" I spit out.
"Much better," said Cyndi. "Now do you know what to do to make me really believe you like what you see?"
"Uh, well, I've read about some things," I said.
"Yeah, that doesn't surprise me," Cyndi said, "I'm sure you've spent quite a bit of time reading and looking at pictures in here."
"But, you know," I said, "I've always been a little concerned. I think you're talking about, uh, well, me licking you?"
"Yeah, hon, that would be it," answered Cyndi.
"Well, Cyndi, uh, don't you pee out of there?"
"Yeah, Dale, I do," said Cyndi. "But you need to get used to the idea that what we're about to do may get a little messy, and you probably will be happier if you just try to lower the bar a little bit about bathroom issues and hygiene hangups! You think you could do that for me? In the interest of learning a new skill? Huh?"
"Well, sure," I said, "I guess. So I should just go ahead and do this? No matter what it tastes like?"
"Yeah, you romantic devil, why don't you just give me a lick? I promise, it won't do you any harm."
I tentatively stuck out my tongue and lightly licked upwards along Cyndi's pouting groove. It wasn't really all that bad.
"Yikes!" cried Cyndi jerking upwards suddenly. Reverting to exclamation-point-talk she said, "Gentle is good, but not so gentle! You just tickle when you do it like that! I won't break ... try it again, but a little more firmly!"
So, I licked upwards again along her groove, pressing my tongue against her a little more firmly, when something happened, and my tongue slid into the groove, where there was a whole different taste and texture.
While Cyndi was saying "There we go!" I was sputtering and spitting, sure I had breached some kind of barrier and gotten a mouthful of some sort of organic, disgusting girl-stuff.
"You are the flatterer! You really know how to make a girl feel special!" said Cyndi with a clearly sarcastic tone. "Am I really that gross to you?"
"Oh, no, Cyndi," I stammered, turning my head to wipe my tongue on her thigh. "I'm sure you're fine! It's just, well, I've never done this before!"
"Really?" Cyndi said, again with her sarcastic tone of voice. "I could never guess! Look, Dale, give this thing a moment's thought, okay? Every girl tastes a little bit different, but this is pretty much what girls taste like, okay? While we're waiting for the little pill to kick in, this is a good way to help the girl, meaning me in this case, get ready for the fun stuff later. Get it?"
"Uh, yeah," I mumbled, "I guess so. But what I read, it sounded, well, more pleasant, more fun, and maybe, um, tastier!"
"Yeah, well, fun is where you find it, big guy. This is one of those things that gets better with experience. If you'll just give it a chance, you might actually get to like it!" said Cyndi. "In the meantime, I can feel from something nudging at my butt that our little blue friend is having an effect!"
Cyndi swung her leg over my torso again, releasing my arms, which had begun to go to sleep. "Here," she said, "scoot yourself all the way up onto the bed."
I swung my legs up off of the floor, and lay back along the length of the bed next to where Cyndi was sitting, instead of cross-ways the way I had been before. I had sprouted a stiff new appendage; it was much bigger than I remembered it ever having been before. The entire room seemed to taking on a slightly blue tinge.
"Well, well, Mr. Dale!" Cyndi said. "Let me give you some show-and-tell oral instructions!" Cyndi pulled back my skin and licked me a bit, then lowered her head and moved her lips and tongue in ways I had never imagined, and I have a pretty good imagination. She didn't seem at all reluctant or hesitant, and it felt just grand. She was at once gentle but insistent.
"See, there's how you do it," Cyndi said, briefly interrupting her demonstration to my dismay. "You need to keep in mind the four basic E's that make for satisfactory foreplay: Enthusiasm, Energy, Endurance, and Exploration. Now, if I promise to keep going with this, do you think you could keep up your end of the deal along those lines, Dale?"
I was very eager for her to proceed, so I was sure my Enthusiasm would be excellent. I had only just got out of bed, and Cyndi had certainly gotten me excited, so my Energy was at an all-time high. The little blue pill seemed to be taking care of Endurance issues, and this whole endeavor was totally an Exploration, at least for me, so I said, "Oh, my, yes!"
Cyndi straddled my chest again, but this time, facing away from me and leaned forward to continue her demonstration project. I followed through on my promise by delving deeper into the mysteries of her groove.
Although what she was doing to me was very distracting, I soon became enthralled by what I found there between her legs. Using my thumbs, I spread her groove open, and you know what I found? Another groove! Only this one was formed by two folds or flaps which pursed out within the enclosure formed by the outer groove. Where they came together at the front, there was some kind of little nubbin; when I licked or nibbled on this nubbin, Cyndi seemed to respond noticeably. Her response didn't seem to be an objection, though, so I continued my Explorations, occasionally getting distracted by whatever it was she was doing to me at the same time.
I attempted to look within this second groove, thinking that perhaps women are like those little Russian nesting dolls, and maybe there would be an infinite number of grooves-within-grooves if I just kept looking. But alas, no; inside this second groove, there was merely some kind of deep recess. This recess was quite soft, spongy to the touch, and moist. As I explored further (mostly by feel now, as it was too deep and dark in there to see clearly, not to mention I was applying my mouth and tongue so I was unable to see much), this channel seemed to be becoming ever more moist, or even, dare I say it, sopping wet, and more than a little slimy.
"Cyndi," I said, taking a breather from my efforts, "are you quite alright? There seems to be quite a leak or something here! Am I doing something wrong?"
"Shut up Dale! Just go back to what you were doing, and keep it up!"
I noticed a sharp decrease in pleasure when she had stopped what she was doing to say this to me, so I assumed she was also feeling the same. I resumed what I had been doing, delving deeper into her recess with my tongue and fingers, while retreating back to her entry from time to time to massage her tender grooves and that curious little nubbin, which seemed to be becoming very sensitive, and was now maybe protruding a bit.
I'm glad Cyndi had mentioned to me the need for me to relax my usual standards of hygiene, as by this point, my entire face was becoming quite covered with the moisture from within her grooves. I could feel some sort of moisture also literally dripping from myself where she was so busy, as well, so I assumed she thought this was normal for these proceedings.
Suddenly, Cyndi started bouncing up and down on my face, simultaneously clamping my cheeks between her thighs and moaning loudly. For such a small person, Cyndi seemed to be quite capable of clamping me firmly in place there between her legs, regardless of any inclinations I may have had toward escape. I intended to inquire whether she was okay, but I found myself unable to disengage from licking at her grooves. Cyndi, however, had quit her own ministrations to me, and was devoting her entire attention to assisting me in my efforts there below her.
Her moaning had gotten quite loud, and soon grew into shouts of apparent joy and/or pain. I was unsure which, as my ears were quite muffled by her thighs and my hearing was further interfered with by her thrashing about upon my head. But I assumed a best case scenario, and continued in my efforts.
After a minute or two of this treatment, Cyndi's knees tightened even further, and I thought my brother may have set this whole charade up as a pretext to further some diabolical plot of his to have a hired assassin crush my skull. But just as I was about to succumb to the combined effects of skull compression and anoxia, Cyndi suddenly stopped moving altogether, and froze in position. Her entire torso throbbed a time or two, at which point, she relaxed her death-grip on my head, and slumped off the top of me, to fall to the my side on the bed, breathing heavily and moaning slightly.
"Cyndi, Cyndi!" I implored. "Are you okay?"
"Uh-huh," she murmured very quietly, completely without exclamation points. "Give me a minute, huh?"
I was able to see that she had apparently been very stressed by this whole encounter, as besides being out of breath, she was covered in perspiration and quite flushed.
On the other hand, other than being soaking wet over my entire head, I by contrast had never felt better. I still noticed a strange sort of blue lighting effect over my entire bedroom, but I couldn't determine where this was coming from.
I also noticed that my rather large protuberance was still in full bloom, and also soaking wet for some reason. I finally realized that Cyndi must have spit all over it for reasons of her own. She was a very strange girl, but I was certainly willing to give her the benefit of the doubt in this area about which I knew so little and she seemed to be so accomplished. While Cyndi continued to recover there beside me, I used a corner of the bed-sheet to mop my face and crotch dry.
"Well, that was fun!" I said to Cyndi, as she seemed to be calming down somewhat. "Now what?"
I had always admired the breasts of woman acquaintances, but sadly, my direct acquaintance with breasts, per se, was pretty superficial. I had noticed, from time to time, that when some women moved about, their breasts followed only reluctantly, resisting their motion by deflecting and distorting in various interesting ways. A few times, my careful observations of these phenomenon were not so well received by the women being observed, if I may say so, for reasons I don't fully understand.
My detailed knowledge of the female human breast was mostly visual, obtained again by way of determined research on the internet and in magazines. Ever the inquisitive student, I have always been curious to learn more about breasts' texture, taste, and odor if any.
Cyndi, lying here on my bed, breathing heavily, did not seem to mind so much my detailed inspection of her breasts. In fact, when I tentatively reached out to touch them again, she smiled and pushed out her chest to assist in my inspection.
I was pleased to discover that breasts, at least Cyndi's breasts (and I knew even then that they might not be representative of all women's breasts) were somehow simultaneously firm yet extremely pliable. Their overall texture was wonderfully soft and they were quite warm.
I knew about nipples, of course, but I was surprised to see that the textured field surrounding the nipple proper was not just sort of the foothills of Mt. Nipple as I had assumed, but rather a sort of terrain all their own, which I later came to understand to be called the areole. This circle of skin around the nipple proper seemed, in fact, to be quite rough, and yet also soft and pliant all at once, covered with what appeared to be tiny proto-nipples.
"You getting' a good look, there, Dale?" Cyndi said, startling me right out of my contemplative inspection. I had leaned in for a closer look, and my nose was nearly touching her sternum.
"Oh, yes!" I barked, pulling back suddenly. "Sorry, your breasts are just so fascinating!"
Cyndi laughed. "Well, your choice of words could be a little more romantic, but you're at least being flattering now! Go ahead, look as much as you want ... I don't mind!"
When I had started looking before, Cyndi had been breathing quite rapidly, and her whole upper torso was flushed. The nipple at the center of each breast at that time stood out quite a bit from the surrounding flesh. But now, after a few minutes respite, her nipples had recoiled or retracted somehow, and were just minor protuberances, no more significant than my own (although nestled on a much nicer background).
I tentatively reached out an index finger and gingerly poked at one of the nipples. Its structure was quite a bit firmer than that of the surrounding breast, and rebounded immediately after each tender poke. I noticed, however, that as I poked a few more times, the nipple began to grow again, as if coming to life.
"Oh, that's interesting!" I remarked.
"You really want to see something interesting," Cyndi said, "lick at one of 'em, or suck on it a little bit!"
Cyndi seemed very orally fixated, but I followed her advice and licked a bit at the other nipple. It had no noticeable taste, except maybe a little oily fragrance, which I assumed to be her perfume or body wash, and maybe a bit of saltiness from perspiration, I guessed. In comparison to the slow emergence of the other nipple under my touch, this one grew much quicker and to a much greater protuberance than the one I had been poking at.
"It's growing," I observed.
"Yeah, Dale," said Cyndi, "that's a good thing!"
I pursed my lips and grabbed this newly-enlarged nipple tightly with my mouth, then began sucking, hard.
"Jesus Dale! Not so hard! You'll give me a hickey right on my boob!" said Cyndi. I could see that intensity control was going to be a learning area for me for a while ... don't lick too softly, but don't suck too hard. Okay, noted.
I spent a bit of time alternating between Cyndi's delightfully soft and supple breasts, sucking (gently!) and licking (vigorously!) one, then the other. I was learning a great deal, supplemented by some additional explorations with my hands on the sides and perimeters. I decided that her breasts felt like nothing less than two sturdy but supple leather bags full of warm milk!
"Yeah, I guess they would feel that way," Cyndi responded when I told her of my analysis. "You know, Dale, I'm not really sure you need to tell me everything you're thinking while we do this, okay?"
"By the way," Cyndi said, "Not that you've asked me, but I like what you're doing there!"
"Oh, good," I said, "I like it too! May I do it some more?"
"Sure, honey. But, I have another idea that you may like even more. Get up on your knees right next to me here," she said as she patted the bed right next to herself.
"Now, try touching all over my boobs with your cock instead of your hands."
My penis was swollen to the largest, stiffest condition I had ever seen it in. It was almost painfully erect. I used it as Cyndi directed, rubbing the tip of it all over her breasts, leaving a trail of sticky fluid all over her chest. It was pleasant, in a different sort of way from using my hands or my mouth, but all in all, if anything, it made my penis even more painfully stiff.
"Look, Cyndi," I said, "this is fun, and thank you. But my penis is actually starting to hurt it's so swollen. Is there anything we could do that might relieve that a little?"
"Oh, Dale, you little rascal!" Cyndi said, although I didn't know what she meant by that. "Sure, there is!"
Cyndi scooted herself to the edge of the bed, and lay back so that her hips were poised right at the side of the mattress. "Now you just hop on out of bed there, and come on around over here, Dale."
I climbed out the other side of the bed, and walked around to the side where Cyndi's legs projected out, then bent at the knees and continued down so that her feet were on the floor, as if she had been sitting on the bed, but fallen backward.
"Now, you just come on in here," Cyndi said. She was propped up on her elbows so she could see what was going on down at the edge of the bed, and she widened the space between her knees and patted her inner thighs. I stepped forward, my foolishly enlarged penis flipping and flopping as if I were a dog wagging his tail.
As I arrived between Cyndi's thighs, she reached down between us. She grabbed my erect shaft, and using it as a sort of handle, pulled me toward her until the tip began to lodge into those folds I'd noticed earlier. Cyndi lifted one foot off of the floor and used it to reach behind me and pull me ever further into those folds.
A strange and pleasant sensation overwhelmed me. Something tight, moist, and warm surrounded my aching penis, making me feel immediate relief, and yet paradoxically making me feel a new sort of urgency.
I pulled my penis back a bit and looked down at it. It was still rudely inflamed, swollen red and purple, but now the first inch or so of it was also slimy with moisture -- I supposed from within Cyndi's folds. I hadn't pulled the tip of my penis all the way out of her; as I withdrew, my cock pulled with it parts of Cyndi's inner layers.
"Interesting," I observed.
"Fuck me," Cyndi said, and I wasn't quite sure if she was making a sarcastic comment about my observation or was making a simple request. The huskiness of her voice and the lack of an exclamation mark suggested the latter.
In any case, I decided that my penis had felt much better when inserted into Cyndi's opening, so I pushed it forward again, embedding it as deeply as I was able.
"Yeah, there you go!" Cyndi remarked.
Oddly, as soon as I had myself fully embedded, I felt an irrational urge to withdraw my penis again, and then, having withdrawn it, I felt an equally strong urge to plunge it back in. Completely illogical, but in each situation, fully embedded or nearly completely withdrawn, my over-riding interest was to immediately be in the other position.