Jen's Sexual Education Pt. 01

***

As I followed closely behind Josh's car, I wondered just what I expected to happen once we got to his apartment. I thought once I got to know him a bit more, this immature infatuation I had towards him would vanish. But somehow only the opposite had occurred. In our six years of marriage, I had never seriously considered cheating on Nick, but for whatever reason my hormones and my body were in overdrive for Josh.

I continued to reflect on my own emotions. Why was I so attracted to him? Again, physically he was certainly no match for Nick. He was a bit shorter, less muscular, less well groomed, etc. His face was attractive enough, but not necessarily handsome the way my husband's was. It really was just the way he carried himself. That confident control. Plus, the fact that he was treating me like a genuinely normal person and not a sexual object like most men I guess only increased my desire for him.

But would I really go through with it? I used to really get off from seducing quiet, shy, unsuspecting boys back in college, ones that would never approach me on their own. Something about that really did it for me back then, but I genuinely thought that part of my life was over. It was now back with a vengeance. And the way Josh acted towards me, pleasant and cordial, but not infatuated like most guys would make the conquest all the more satisfying.

My body was flushed with excitement from all of these naughty thoughts as we pulled into a couple empty spots on the street in front of his building. Soon he was unlocking the building's front door where he held it open for me and pointed me towards the nearby flight of stairs. As I climbed them in front of him, I wondered if he was checking out my sculpted legs and wide ass under my mid thigh-length skirt. He had to have been, right? No way he could resist.

Once inside his one bedroom apartment, Josh headed to the kitchen area to brew up some coffee while I took a brief look around his dwelling. I was somewhat surprised that it mostly looked to be neat and organized. I had been worried that due to Josh's tendency toward an unkempt personal look that his apartment would be super messy, but it was actually very well put together, and from my view quite clean, especially for a guy living alone.

I made myself comfortable on his oversized couch and after a couple minutes he returned with the hot beverages. He sat down casually, two couch cushions over from me. After determining the drink was a bit too hot, I placed it on an end table and scooted closer to Josh.

"So anyway... you remember what we were chatting about on messenger a couple days ago, right?" I asked.

"Ha, yea, I could not forget that. You were certainly direct in your questioning."

"Well, I read through a lot of info on that website and it got me curious. I might have tried some stuff on Nick later that night."

"Oh, really?" Josh responded turning towards me with more interest.

"Yea I might have put a finger up his ass just to see what happened," I laughed.

"And did he like it?"

"Well, he did not really act like he liked it, but his body sure responded to it." I laughed again. "I am pretty sure I found the right spot too. I knew where to feel for it based on what that website said, and when I pushed ther... let's just say he did not last long."

"Sounds like you found his prostate all right. Where you also touching his dick?"

"Yea, I was sucking him too."

"Well, yea, that is what generally happens when you do those things together." This time he laughed.

"But it didn't seem like he actually liked it that much. Not sure if he thought it made him gay or whatever, but he just described the whole situation as weird, even though he honestly had a pretty big cumshot."

"Haha, that tends to happen as well."

"So do those massagers, like the one device you showed me, do they feel even better than a finger up there?"

"Well, it is a totally different kind of thing. The type of prostate stimulation that you gave him with your finger is more what I would call an 'acute' type of pleasure. You can cum quickly like that, but is honestly not that different than normal pleasure from penile stimulation, just more intense. The type of pleasure that the devices can give starts much, much more subtle, but then can grow into a whole different thing."

"So you're saying I should buy one of those devices for Nick." I laughed more loudly.

"Well, it is not that simple. It honestly takes lots of practice to get anything that feels close to an orgasm with those. You have to have a ton of patience and discipline, but once you get it, I swear it is life changing. The problem is that it is a very personal thing, and takes long hours by yourself, which is not great for sharing it with a partner. Hence one of the reasons I am totally OK not having a sexual partner." He smiled at me.

I was certainly very interested in everything Josh was telling me, but I was having somewhat of a difficult time following all of the logic.

"I think I understand mostly, but I still don't see why you can't get your partner involved. Maybe I could 'help' him practice. That sounds like it could be hot."

"Maybe, but I am not sure that would be much fun for you. A 'session' literally would involve him lying still and experimenting with very tiny muscle movements inside his body. And the most important thing is that you can't touch the penis at all. Like not even a little bit. Guys are so used to getting all of their sexual pleasure through their dicks, that we have to completely ignore that to learn to receive it through other means."

I sat and thought for a second. It was difficult to imagine doing something sexual with any guy and not involving his cock. That seemed so backwards from how sex usually went.

"So you don't even masturbate by stroking anymore?"

"Not really," he responded quickly, shrugging. Back when I was first starting my journey of prostate focused arousal, I would occasionally give in and masturbate normally, but I found that this definitely detracted from my progress. My best sessions were always when I completely ignored my dick. And plus, if you don't ejaculate, then you stay aroused much more and your next session is way more likely to produce an orgasm."

"Wait, you are telling me that you don't ejaculate when you orgasm?"

"Well sometimes some stuff leaks out, but it is not like a traditional ejaculation at all. Honestly a prostate orgasm maybe should not even be called an orgasm... it is nothing like a penile one. One of the benefits of not ejaculating is that you can chain together orgasms or let them build all the way into what they call a super orgasm."

"Yea I did read something about that," I interjected.

He quickly continued. "Haven't you noticed that guys tend to lose all their arousal as soon as they cum?"

"Yea."

"Well, with a prostate orgasm, that does not happen at all. Each one that you have can actually make you hornier."

This was all so backwards from everything I knew about the world. I just sat in deep contemplative thought for what felt like over a minute.

"So anyway," Josh finally continued, "that is why I am OK being asexual. Or at least asexual when it comes to sex with a partner."

My competitive nature suddenly took over. I quickly kicked off my sandals pulling my smooth legs fully onto the couch and slid right next to Josh.

"So you are telling me that if I wanted to fuck right here, right now, you would turn me down?" I boldly rubbed his chest gently with my left hand.

He looked down at my hand and made a funny face, kind of half way in between a smile and a frown. Then he quickly stood up, forcing my hand away from his body. He turned towards me with a caring look on his face.

"Look Jen, you are a gorgeous woman, and I am totally flattered. But like I said, I am in no position to start some shit with Nick. I know you might think he would never find out, but I just can't do that to him. I'm sorry."

"What if I wasn't married?" I protested.

He laughed. "Well, it is always hard to deal in hypotheticals." A cute smile spread across his face.

"Fuck Josh, you are giving me some blue balls." I giggled.

He shook his head, unsure if I was being serious. "I don't think women get those."

I laughed again. "Well I don't know what is wrong with me, but I have been so incredibly horny lately. I'm sorry. I don't know what has gotten in to me." For the first time, I actually felt a pang of remorse. Josh was being so sweet and I was obviously putting him in a very awkward position.

"Hey it's OK," he responded softly. "Like I said, it is kind of cool that you are interested in all of that stuff. I honestly have never talked much about it with a woman. I always assumed that women were not into that at all."

"Well, something about it is very wild to me. And yea, it did make me really horny and really attracted to you at the same time."

"You know, I also got pretty turned on the other night when we were chatting about it on messenger."

"Really?" I responded.

"Yea," he chuckled. "I actually ended up having a really good session after that."

"What did you do?"

"Just used one of my massagers and it went amazingly well. I guess talking to you about it had my body craving it."

"You got off?"

"Ha, that is an understatement. I think I had three super o's. Not even sure how long they lasted, but it was awhile."

"Mmmm," I instinctively moaned at the thought. "And how about our conversation today?... has that made you want to do it again?"

Josh seemed to ponder my question for a moment. "Sure, I guess. Lately, I seem to always be in the mood for it," he reluctantly responded.

"Would you let me watch?" I said looking directly in his eyes.

He looked away shyly. "I... I don't know," he stammered. "Is that something you would actually be into? It might not really do that much for you."

I closed my eyes and imagined seeing Josh writhing before me in orgasm. My body was burning with arousal.

"You really are insatiable today," he laughed again staring at my hand.

Without even realizing it, my hand had somehow made its way between my thighs, up my skirt and was pressing on an increasingly wet spot on the front of my panties. I quickly pulled it away embarrassed.

"Fuck, I am such a slut," I stated, putting my reddening face in my hands.

"Hey, no judgment here," Josh said reassuringly. He walked over and put his hand on my shoulder.

"That is not helping," I laughed, jumping in arousal from his touch.

"Sorry," he responded sheepishly. "Look, if you want to watch me do that, fine. But you have to stay on the other side of the room. No touching me or anything, OK?"

I looked up at him wide eyed and nodded. "Can I touch myself?"

He laughed once more. "Well, it looks like you might not be able to keep yourself from doing that!"

***

We silently made our way into Josh's bedroom. He sat a chair out for me and then walked to the window, closing the thick curtains from each side. They were made from the kind of fabric that blocked out nearly all of the light so the room suddenly became nearly pitch black as my eyes desperately tried to adjust to the dimness. I could barely make out his figure as he moved to his bed where he adjusted the sheets and blankets on top of his mattress. He then reached into his night stand and got out a small cylindrical container and a box. Quickly opening the box, he pulled out an object and sat it down next to the container. Thought I was I squinting through the darkness, I thought I could recognize the object as the massager he had first shown me on that website.

"This is the old reliable one," he stated, turning towards me.

"How many do you have?"

"Six or seven I think. But yea, this one gets the job done pretty much every time. I generally have to get naked for this to work well. Otherwise, clothing is kinda distracting. Is that OK?"

I started to comment that I was not going to be able to see him that well anyway here in the dark, but I thought that maybe that was by design. He did not seem keen on me being able to make out every detail anyway. "You just do whatever works for you," I chuckled back. "Pretend I am not here."

"Well that might be kind of hard, but I will do my best."

With that, Josh quickly pulled his shirt up over his head and let his shorts drop to his feet. He was now standing before me in just his boxer briefs. His pale skin captured a bit more of the soft light in the room and I could also make out a dark patch on his chest. I generally was not a fan of body hair on a guy, but on Josh I thought it suited him well as it likely helped to give his somewhat slight frame a bit more of a masculine look. He was certainly not as well built as my husband, but I think most women would have found his body to be at least somewhat attractive.

Josh put his thumbs at the waistband of his underwear and looked at me once more. "Are you sure you are OK with this?" he asked, earnestly.

I nodded. He sighed heavily and looked down at the floor, almost as if he was dejected. Was he having seconds thoughts? I started to open my mouth to tell him we really did not have to do this if he didn't want to, but then he quickly shrugged as if to say 'what the hell' and then pushed his underwear down letting it fall to the floor with the rest. Just as he fully disrobed, he began to turn back towards the night stand so I did not get the best view of his genitals in the dim light. I did, however, notice a bit of movement as he turned away from me, almost as if something seemed to bounce against the middle of his thigh. Could that have been his penis?, I quickly thought to myself. No, there is no way it would be hanging down that low, it must have been a trick of the light.

Soon Josh was facing away from me doing something at his nightstand. I later realized that he was putting lube from the container onto the massager in preparation for his session. I found myself staring at his cute butt. Again, it seemed to be bit hairier than what I was used to, but it wasn't terrible and was actually shaped quite nicely. Josh then reached behind him and pushed a finger in between his cheeks, obviously rubbing a bit of lube onto his hole. I had never seen a man touch himself in that way and I found it to be incredibly erotic.

After wiping off his hand on a nearby towel, Josh then climbed onto his bed, the lubed massager in hand and proceeded to lie on his back. Before I could get another good look at his package, he reached down and put his hand over his cock and balls then kind of pulled them up, exposing his taint and anus. He moved with an efficiency and confidence of someone who had done this many times before.

Next, Josh moved the massager between his legs and seemed to guide the tip towards his lubed hole. He began to push and within seconds it disappeared into his body. He let out a soft moan as he succumbed to the first feelings of prostate pleasure, then carefully withdrew both of his hands, letting his genitals fall back into their normal resting position. Now seeing his penis well for the first time, I was taken aback by its length. The shaft reached all the way over his balls and the tip easily reached the surface of the bed. I craned my neck forward trying to see better.

Josh now was lying flat on his back with his legs spread, knees bent and his feet planted flat on the bed. His hands were at his side, but soon he began to run them up his body, gently touching his sides and chest. They eventually found their way to his nipples where he began to rub in small circles. Josh moaned again and I noticed his penis twitch slightly.

As silently as I could, I began to scoot my chair across the floor so that I could get a better view of what was happening down below. Soon I was only a couple feet from the foot of the bed and was now positioned directly between his open legs. Now that I could make out more detail, I noticed that Josh appeared to be uncircumcised, yet I could still make out a large bulge in the foreskin near his tip. His head must have been huge. And I again marveled at his overall length even though he remained totally flaccid. I remembered reading quite a bit about how prostate pleasure often did not lead to erections, and it certainly seemed this was the case with Josh. But how large would he be when hard? I delighted in the thought.

Suddenly Josh let out a louder moan and his legs began to twitch and spasm as if he didn't have much control over them. His cock twitched again and I now began to notice a bit of glistening wetness at the tip. My heart began pounding and for the first time since entering his room, I became acutely aware of how aroused my own body was. My clit was burning with desire and pleasure as I squirmed in my chair trying my best not to make a sound.

Josh's own sounds and motions now began to steadily increase. His session had only lasted maybe five minutes at this point, but it sure seemed like he was well on his way to a big climax. I squinted harder as I could now make out a bit of movement behind the tip of Josh's large penis. It seemed that the massager was moving itself in and out of his ass. I knew from reading that it was pelvic floor muscle contractions that were moving the device, but at this point it almost seemed as if it were battery operated and was moving on its own.

As I watched in total fascination, I began to feel a very pleasant pressure on my engorged clit. Without even realizing it, my hand had again made its way inside my panties where it was firmly pressing on my pleasure spot. I could just about cum at any second I thought to myself. This was so fucking hot.

After another minute or so Josh's moaning had turned into full blown groans and he began to lift his butt off the bed. His whole lower body was now thrashing about, his long dick bouncing between his legs and balls. His hands quickly went to his sides where they firmly gripped the sheets, steadying himself so that his convulsions would not throw him of the bed. But his orgasm, or at least I assumed it must have been an orgasm, persisted.

A small moan escaped my lips as my arousal hit a peak and a very satisfying orgasm of my own shot through my body. My vision blurred for a moment and I closed my eyes trying to regain my composure. When I opened them a few seconds later, Josh's state had not changed. He was still shaking and twitching on the bed, moaning wildly. This was some next-level stuff and I began to almost feel a sense of jealousy toward the pleasure that Josh must have been experiencing. His orgasm must have persisted well over a minute at this point.

Finally, Josh let out one final loud groan and his legs seemed to relax, straightening out a bit on the bed. His whole body gradually went limp but his breathing remained fairly heavy for the next couple of minutes. His face now looked more relaxed and I thought I could perceive a subtle smile flash across his lips. I can't even imagine what kind of sexual bliss he was experiencing at that point.

I suddenly had the intense desire to embrace Josh. It wasn't even so much of a sexual thing, but I just wanted to show him gratitude for sharing this super intimate part of his life with me. Without thinking I stood up and moved toward the side of his bed.

Josh opened one eye and looked towards me. I quickly crouched down so that my face was level with his. He turned towards me, still recovering his breathing.

"Hey" he muttered. "Did you like?"

"Oh my God," I whispered. "That was crazy. You are amazing!"

"That was a pretty good one and it happened pretty quick. I think you watching me might have made it even better." He smiled.

"I thought your orgasm was never going to end."

"Yea, that was very nice. Sometimes they are continuous like that. Sometimes it goes up and down more."