Chapter 79 – Caiden’s Extensive S*xual Education

"Oh, I like the sound of that." Caiden grinned from ear to ear. His excitement for what was to come was a major turn-on for me, but I couldn’t tell if he was excited about the prospect of me teaching him all about how to pleasure a woman or that by the end of it he would be able to make me cum so hard I wouldn’t be able to think straight. Either way, we were both bound for a hell of a lot of fun together.

"There’s no time like the present then, why don’t we get started with your extensive, first-hand sexual education," I chuckled as I repositioned myself on the bed, my legs spread, giving the young man a clear view of my flushed, cum leaking pussy.

As my fingers went down to the lips of my bare pussy, spreading everything wide so that he could see every part of me, it was not lost on me that this was not my first time doing such a thing. During my first day in this world, I also gave Vel a quick bit of a sexual education like this, one that was heavily focused on how to pleasure me. The intimacy and the fact that I couldn’t hide anything when teaching someone like this added a certain something to the act that made it feel very special.

However, Caiden’s sexual education was going to be far more extensive than his cousin's ever was. Unlike Vel, the young man wasn’t a woman and didn’t have a pussy of his own, so he knew even less than she did. Not to mention the fact that, unlike her, he couldn’t learn how to touch a woman by touching himself and seeing what worked and what didn’t. No, in order to gain experience and get better at this, he needed someone to practise with. And as it just so happened to be, he had a very eager volunteer ready to fill that role right in front of him.

"This is my pussy. The outer part that you can see is called the vulva. The lips here are the labia minora, and the outer puffy bits here are my labia major." I started with a brief mention of all the sexual anatomy going on down there. "After that, we have the two most important places: my clit and my vagina. Obviously, the hole leaking your cum is my vagina, as that is where your cock penetrated deep inside me when we were fucking moments ago. The other important place for you to remember is my clit here. That’s the magic button if you really want to get a woman to cum. Oh, and I also guess I should tell you that this little pin-prick-sized hole is my urethral opening, where the pee comes out of, but don’t ever touch it during sex. In fact, just ignore it completely."

To his credit, Caiden attentively nodded along as he paid close attention to everything I said and pointed out, even going as far as taking action on his own to get a closer look, to the point that his head was only a couple of feet from my pussy and getting closer stills. However, at the mention of his cum leaking from my pussy, a look of concern washed over the young man’s face.

That said, he only acted on that concern once I had reached a moment of pause, at which point he spoke up, saying. "Shit, umm…. Eve, I probably should have asked you this before, but have you taken any tea of the nightlilly recently?"

"No, I don’t think I have. I actually don’t know what that is." I responded with a curious look while still remaining in the rather compromised position that I was in. Given what we were doing and talking about, I had my suspicions about what this tea could do, but I didn't express them in the hopes that he would tell me more on his own.

"Oh, that’s not good…" Caiden sighed before going on to explain. "Tea of the nightlilly stops women from being able to get pregnant for around a week after drinking it. However, it doesn’t work retroactively, and it is recommended for women to drink it at least two hours before having sex for its effects to be fully active."

A week is a weird period of time for such a thing to work for. You would think it would either affect the whole reproductive cycle or it would be required to be taken every day like the contraceptive pill back on Earth. Why a week? I mused to myself while the young man continued to talk.

"If you do get pregnant, please know that I will take responsibility and be a father to our child. We don’t have to-"

"Whoa, hold up!" I cut the young man off before he got too serious about this. "I’m not going to get pregnant. I’ve got a trait that stops me from getting pregnant as long as I don’t want to, which, no offence, but I definitely don’t want to have your baby or anyone else’s baby for that matter."

"Oh…" Caiden paused for a moment before letting out a sigh of relief. "Thank the Gods. I’m not ready to have a child either. But if the worse was to happen, I could never neglect my responsibilities… But, wow, that is some trait."

"Yeah, it is rather handy. It also stops me from catching anything, but this is just a distraction. We were in the middle of something." I said, drawing the young man’s attention back to my cum leaking pussy, which I was still spreading wide for his ease of viewing.

"Oh, right. Yes, please continue on." Caiden eagerly focused his attention fully on me and my pussy.

"So, like I said, the clit is the best place to focus on if you really want to make a woman cum…" I went on to explain how I liked having my clit played with by demonstrating the methods for him to see. After that, I guided his hands to my clit and went through those motions first-hand. Eventually, I even stopped guiding him, letting him explore and play with my pussy all on his own. Not just my clit, but the rest of it too.

"Now, one of the most basic but incredibly important principles you want to keep in mind, not just during this kind of activities but any time you are sexually with a woman, is to watch and pay careful attention to your partner’s reactions," I explained as his fingers slid down my slit, across my pussy lips. "It’s simple really, but too many people ignore it in favour of their own pleasure. When a woman moans, generally it means you are doing something right, and when they get all closed off and stiff, then you are probably doing something wrong and should change it up."

"What’s more, if a woman says to do something harder or a little to the right, then do that. Oh, and if she says to keep doing something just like that, then for god's sake, keep doing it just like that. All in all its about being attentive and focusing on your partner more than yourself."

Honestly, the amount of effort I was putting in to teach Caiden how to pleasure a woman wasn’t really necessary. The difference between someone who was bad at sex and someone who was good at sex was relatively small. All it took was for someone to be attentive and focused on their partner, and they were bound to have a good time. That said, I wasn’t just trying to make Caiden good at sex; I wanted him to be great at it. Maybe I was being a little self-interested by teaching him like this, but he sure wasn’t complaining. No, he would get just as much enjoyment out of it as I was going to.

While the gap between good sex and bad sex was relatively small, the gap between great sex and good sex could be vast. great sex wasn’t just a fun time with a nice little orgasm to cap it off. No, it was a mind-blowing experience that left all those involved breathless, exhausted husks of themselves. It was the kind of sex I had been having with Damien and Vel ever since I arrived in this world. And it was the type of experience I hoped to provide to customers when I eventually got to work at the Red Den, provided Sophia thought I was the right fit for her establishment.

After giving Caiden a little time to explore all the nooks and crannies of my pussy for himself, it was time to get back to the lesson at hand. It just so happened that at this point in time, he already had two fingers inside me, so I might as well teach him about a certain spot up in there.

"Okay, so inside the vagina, there is a spot commonly referred to as the g-spot. You should be able to feel it if you curl your fingers slightly. Its texture feels a bit different from the rest of… Oh, yep you found it already. Ah, yeah, keep caressing it like that. Fuck, that feels amazing." My explanation turned into a bit of a moaning session as the young man continued to stimulate my g-spot just as I directed him to. Not to mention, paying great attention to my moans and body language, just as I had initially told him, was a simple but important principle.

Although Caiden’s fingers curled up inside me, hitting all the right places felt so damn good that I continued on nonetheless. "If you can manage to hit a woman’s g-spot with your cock while fucking her, it will do wonders to make her cum, but you should know that doing such a thing is not easily done in all sex positions. It is easier to do in some positions than it is in others. Furthermore, hitting the g-spot and playing with a woman’s clit at the same time is double the stimulation and double the pleasure."

Caiden, the attentive learner that he was, took the hint without a moment of waste. Soon enough, his fingers were stimulating both my clit and g-spot in the ways that were best suited for making me cum. As much as I wanted to continue speaking and guiding the young man through his extensive sexual education, words were beyond me as the pleasure reached a breaking point.

As the sexual bliss of an orgasm coursed through my body, my fingers clenched down on the silky soft sheets under us, while my toes clenched up. Inside me, the tight, wet walls of my pussy spasmed and convulsed around the fingers penetrating deep into my most sensitive of places.

As I came, Caiden's efforts to touch and stimulate me immediately stopped as he instead just sat there, with a look of awe and pride on his face. As the spasming and pleasurable waves of my orgasm faded away, the young man couldn’t help but grin a big smile and ask. "Did I do it? Did I make you cum?"

"Oh, yes you did." I giggle excitedly before pulling myself up and giving him a congratulatory kiss on the lips. However, the kiss was only a short and sweet one, as before too long, I was pulling away and whispering into his ears. "But, don’t think making me orgasm once makes you a master of sex. I still have a lot to show you, and you have a lot to learn."

"And I’m willing to learn." The young man replied, brimming with more confidence than I had ever seen him have before. I had a feeling that after today he would be a changed man.

"Then I think it's time we move onto something a little more direct. I think it's time you fuck me with that big cock of yours again." I purred excitedly as I bent over on the bed, wagging my butt in his direction. "But, this time you will be taking the lead."

Unable to resist such temptations when put directly in front of him, Caiden wasted no time getting into position and sliding his manhood deep into my eager pussy, pushing out any remnants of the load of cum he left in there earlier. Of course, after having an orgasm only seconds ago, my pussy was still quite sensitive and having such a thick cock fill me up caused no small amount of moans to escape my lips.

Continuing his sexual education as he thrust in and out of my tight, little pussy was harder than I imagined, but it was a challenge I was more than willing to undertake. "This position is called doggy style. It's one of the easiest ones to hit a woman’s g-spot that I know of, but that isn’t something that is true for all women. Just like how not all women like to be touched in the same way, different women like being fucked in different ways. And other than getting her to tell you, the only real way of finding out what works and what doesn’t is by experimenting and paying close attention."

"For instance, the way you are hitting deep inside me when you thrust just like that is amazing. However, it would feel even more amazing if you gave me a few spanks on my butt every now and then. Oh, and don’t forget to reach around with one hand and show my clit some attention. You can’t forget the clit."

Just as he said, Caiden was very willing to learn. What’s more, though he was a very quick learner, and before long, his hands were coming down on my butt, spanking me in just the manner I had liked. Spanking wasn’t something I was super into back on Earth, but after that time when Damien spanked me during my sexual training back at the log cabin, I started to really like it. Especially when having either my ass or my pussy fucked.

As much as Caiden was getting the hang of things and driving my pussy wilder and wilder with the pleasures of the flesh, he was still relatively new to sex. As such, his stamina wasn’t what it could have been. To help him in this regard, I offered a handy bit of advice. "If you're getting close to cumming but don’t want to finish yet, change positions. The brief respite can do wonders for lasting longer."

The young man took my advice to heart and immediately acted on it, leading me through a change of positions in the heat of the moment. Given that he was experienced with such things, it was a little awkward and clumsy, but that fact only helped contribute to the moment of respite this change in positions brought about.

Before too long, he was balls deep inside me again, pounding away at my pussy as his fingers danced on my clit. What’s more, we were positioned in the missionary style, which afforded us the ability to kiss each other, something that he immediately took up the opportunity to do, much to his benefit.

Between the way he was fucking my pussy, playing with my clit, and kissing me, it was no surprise that I was getting close to cumming again in only a matter of moments. That said, Caiden was also getting close to cumming again, and it would be a race to see who came first. However, even if he did come before me, I’d just have him finish me off with his fingers after the fact. It would have been a good learning opportunity to teach him that you didn’t always have to get the woman off with penetrative sex.

"Ah, fuck. I’m cumming again." I squealed out in delight as my pleasure surged forth, more certain than ever that I was going to be the first one to cum first

However, that wasn’t the case. Neither of us really came first; instead, we came at the same time, sharing in simultaneous orgasms. Something that was quite rare and also quite powerful. The bliss of having my orgasm course through my body just as the young man’s own orgasm was coursing through his heightened the whole experience. Not only was my pussy quivering and pulsating in joy, but it was being filled to the brim with his hot, white seed.

The only way this could have been better for either of us was if I had used my class skills to boost our sex to the next level, but Caiden wasn’t ready for such things. The only class skill that really being used was tight fit, which was a passive skill, meaning its effects would always be ongoing. I couldn’t choose not to use it even if I wanted to. Although he was quite close. A few more times going at it, and I’m sure he would be able to handle me at my full, while still being able to last long enough to get me off.

As our simultaneous orgasms faded, the two of us fell down on the bed, utterly spent and out of breath. The young man’s cum leaked out of my thoroughly fucked pussy, pooling on the sheets under us and making a mess of things. But neither of us was concerned about that. Instead, we were just content to lie there, side by side, catching our breaths.

The bed was no doubt going to get a whole lot messier as we continued to fuck each other’s brains out. This wasn’t the end of Caiden’s sexual education. No, it was just the beginning. After all, he hasn’t eaten me out or fucked my ass yet, and those were things he was definitely going to have to learn sooner or later.