Jen's Sexual Education Pt. 01

There on my computer screen was a pic of Josh, he looked maybe mid 20s, with a gorgeous blond girl sitting in his lap. Her arms were draped around his neck and she was kissing his cheek while he smiled for the camera. As I scrolled further I spotted the same girl a couple more times. In each photo they were always very close and it was pretty obvious they were a couple. I continued further and found some of Josh looking even younger. In some of these he was with another very attractive girl. She had dark brown hair and very cute dimples and again it was obvious that they were romantically involved in some capacity.

As I stared at these pretty young women with a young Josh on my screen I was amazed that I actually felt a tinge of jealousy towards these girls. How irrational was that? But the feeling was certainly there. I could not help but feel envy towards the way Josh obviously felt about them. But I hardly even knew Josh. How could I possibly feel like this?

Just then a message popped up at the top of my screen.

"Joshua ***** has accepted your friend request." I about fell out of my chair. With my heart thumping in my chest, I immediately went to send him a DM. Typing my opening message, I felt like a nervous school girl.

"Hiya Josh!. Hope you remember me from the cookout a couple weeks ago."

Seconds later he replied:

"Of course I remember you Jen. Not like you weren't the center of attention all night at that party lol."

"Haha I guess I was," I replied. "Do you remember the conversation we were having?" I continued.

"Um... vaguely. I seem to remember you grilling me about my lack of a sex life ;)."

"The last thing you said was that you were 'asexual.' I just wanted to know what you meant by that." I decided to just be super direct.

"Well... I guess that is not entirely true. I sometimes say that just to shock people!"

"So you are sexual?"

"Well, I sometimes say 'asexual' just to mean that I am not seeking a sexual relationship with another person. Does that makes sense?"

After reading those words I sat and thought for several seconds. I was confused, but still quite curious about his situation. I continued: "It makes sense but I don't really understand I guess. Why don't you want a relationship? Are you not attracted to anyone?"

"Ummmm... It's complicated."

"We don't have to discuss it if it is a sensitive issue for you." I was worried I was offending him.

"No it's OK. You are probably curious because you don't meet too many men like me."

Relieved, I continued my questioning. "Yea, I thought all guys were pretty much horny all the time. You know the thing about you all thinking about sex every 7 seconds lol. You aren't like that?"

"Well, I am not sure it is every 7 secs, but I guess I do think about it pretty often."

"Oh yea? So you do get horny?"

"Yes I do."

"Well now I am even more confused :(." I genuinely was!

"lol sorry."

"So do you just like jerk it all the time or what?"

"Something like that."

"Really? And that is as good as sex with a partner for you?"

There was a pause of over a minute, and I again thought I had maybe offended and annoyed him. But then he finally responded.

"You might not believe this, but it's actually a lot better."

A strange feeling pulsed through my body. Was this guy for real? Those cute girls in his pics must have been terrible in bed I thought. But guys usually did not even care about that. I had had sex with a few where I literally just laid totally still and they had claimed it was the best sex they had ever had. How could they be worse than that? Maybe he never actually had sex with them.

"Have you ever actually had sex?" I pushed on.

"lol yes."

"and... was it not good?"

"I mean, it was OK, but other stuff can be better."

Other stuff?

"Were you attracted to the girls you had sex with? I assume they were girls?"

"Oh yes, believe it or not I had some pretty hot girlfriends back in college. Maybe not as hot as you of course ;)."

"Oh so you do think I am hot?"

"Well of course. I think any straight guy would be attracted to you lol"

I enjoyed the flattery, but I had never been more confounded. "So you are attracted to women and think I'm hot, but you would still rather jerk your cock than fuck me?" I could not believe I actually typed that.

30 seconds passed.

"Is that an offer?"

I laughed to myself. Did I actually break him already?

"You wish ;)," I replied back, hoping he would take it somewhat playfully.

After another lengthy pause, he replied again.

"Well, even if it was, I would have to refuse. I am sure you would be amazing, but you are, you know... married to my boss now (lol) and like I said, masturbation for me is just simply better."

My confusion boiled over again.

"But how do you know?"

He must have been typing quickly because his next response came back quite fast.

"Because the way I am creates certain challenges with normal sex, but I have learned to cope with that by finding new and different ways to experience self-pleasure."

New and different? I was beyond intrigued. And what the fuck was wrong with him that made sex such a challenge? I needed to press him further, if nothing more than for my own sanity.

"OK well now you have to give me some details. What do you mean by 'new and different'?"

"Well, just like how woman have different ways to receive pleasure, men do too. Most think male sexuality begins and ends with the penis. They have no idea what men are actually capable of."

I could not even think of how to respond, but fortunately after a few more seconds he continued.

"Do you know much about prostate stimulation?"

"I know some guys like stuff shoved up their ass if that is what you mean lol."

"Well that is a very un-nuanced way to put it. There is a lot more to it than that. When a guy learns to make the prostate the center of his pleasure (not his penis) a whole other sexual world opens up."

This guy was seriously altering my entire worldview through a simple messenger chat.

"So what exactly do you do?"

"It was honestly a long journey for me, as it is for a lot of guys that discover this kind of thing. About 10 years ago I started experimenting with prostate play. I read a lot about it... there is a ton of info online if you know where to look. Then I bought myself a prostate massager and never looked back ;)."

"Is that like a vibrator?" I asked, my confusion now turning more into pure curiosity.

"They do make those, but I don't think they are very effective honestly. The best prostate massagers are just devices that just go up there and rest against the prostate. Your muscles do the rest."

After a brief pause, the next message he sent contained a link to another website. I cautiously clicked it to see what in the hell he wanted to show me. It took me to what looked like the product page of the 'massager' that he was describing. The device was made entirely of clear plastic and had the most peculiar shape. It was not entirely unlike a dildo, but was different than any I had ever seen. It had a bit of a head on one end (the end that would obviously go inside the man) and then had a series of tapers and bulges up the shaft. At the other end were two small arms extending in opposite directions that curved back towards the head of the device. The end of each was formed into small orbs of plastic. The whole thing had quite the exotic look, almost like a piece of modern art.

"Wow that is pretty wild looking," I responded after studying the page for a minute.

"Yea, you can read about it if you want on that website. But believe me, that thing changed my life completely lol."

I was trying to come up with something witty or flirty to say back to him, but another message suddenly flashed up on the screen.

"Hey, I gotta run for now, but we can chat more later if you want. I actually like that you are interested in all of this. Not many people are. See ya!"

***

For the next solid hour, I explored a great deal of the prostate massager website. It turned out they had a variety of products that were similar to the one he showed me... in fact too many to look through in great detail. I did however find a FAQ and some general guides for using their products that I thought were endlessly fascinating.

I read about how the shape of their devices helped create muscle spasms in the area when they were inserted, so that they kind of moved on their own a bit (or something like that... I was not close to fully understanding this stuff). I learned about how men could achieve orgasms from this, even without any penile stimulation whatsoever. A few places on the website also mentioned a kind of "super orgasm" that could last for several minutes and could be achieved through this kind of stimulation. That sounded so wild!

All of this new information was beginning to become overwhelming. I sat back and tried to relax for a second. Looking down, I noticed that there was a large dark spot at the crotch of my purple leggings. OMG, I was soaked. I did not realize how aroused my body had become. The chat with Josh and all the material I had been reading had left me as horny as I had been in a long time.

I slipped a hand under the waistband and marveled at how wet the soft folds were. I had been getting regular waxings for the past several years, so I was completely bare down there and when I got wet, I got really wet with no hair to soak up the moisture.

Just as my fingers made contact with my swollen clit, I heard our garage door open. Fuck, Nick was home. I had totally forgot that I was going to make us some dinner for when he arrived. I quickly jumped up, closed all the windows on the PC, and scampered off towards the kitchen.

***

"Mmmmmaaaagghh," I moaned loudly as my second orgasm washed over me. I was on top of Nick, riding him enthusiastically while I squeezed my right breast firmly. We had been going at it pretty hard, or at least harder that the usual slow romantic sex that I normally preferred. He probably was wondering what the hell had gotten in to me. I had jumped him the first chance I got after we had eaten dinner. I just had so much residual arousal from my chat and reading session earlier.

As I collapsed forward against my husband, I kissed the side of his face passionately. "Did you cum?" I asked.

"Haha no, I was just trying to make sure you got all the pleasure. Seems like you needed that!" He kissed me back.

My husband had always had great stamina in bed. It was one of his special talents and certainly something that set him apart from pretty much all the other guys I had been with. All of them would have cum in seconds with the way I was riding, but he had lasted for at least a solid 15 minutes, through two of my own climaxes.

"I wanna make you cum. Let me try sucking you." I whispered seductively into his ear.

I rarely made Nick cum from a blowjob. He always said that they felt great, but just that it wasn't quite enough stimulation to put him over the edge. I was surely appreciative of his stamina most of the time, but I did very much love making him ejaculate in my mouth or on my body and I wished it was a bit easier to achieve sometimes.

I quickly slid down my husband's body and took him into my mouth in one motion. Nick had what I would call a very "normal" penis. From my experience, his length, girth, and overall shape was all exactly what you would expect a penis to look like. It was like if you looked up penis in the dictionary, it would have a picture of his as the perfect example. His always felt comfortable inside me and I enjoyed the circumcised look and its entire aesthetic.

Nick moaned softly as I began to bob my head slowly from base to tip, swirling my tongue around the underside as I moved. Suddenly a naughty thought popped into my head. All this info about prostate stimulation had me really wanting to try something. I moved my right hand to his balls and began to gently massage. He moaned again. Then I slid my fingers down and began to work his perineum, feeling his cock swell even harder as I explored the area.

I then pulled my hand back and moved it up to the base of his cock. His whole shaft was covered in a mixture of saliva and my own wetness from earlier. I coated my fingers as best I could, even dipping them into my mouth briefly to make sure they were extra slick.

With the tip of his penis still in my mouth, I then moved my hand back to his perineum and began to search even lower. Soon I found the rough texture of his puckered hole where I began to massage in small circles. He moaned even more loudly.

Next, I began to push my middle finger against his hole much more forcefully. The tip quickly slid in a tiny amount. His body tensed up.

"Jen! What the fuck!" He sounded more surprised than angry.

"Shhhh," I said, after taking his cock out of my mouth momentarily. "Just relax."

He inhaled deeply. "OK, but I am not sure that is helping me," he chuckled.

"Does it hurt?"

"No, just kind of weird. I am not sure I can cum with something in my ass." He laughed again.

We had never done any anal play on him other than just some brief outer stimulation. We had discussed it before, but he had never seemed super interested I was generally OK with that. But at that moment, I just had to doing some exploring.

"Just try to relax more," I reiterated. His ass was clamped down hard on my finger but I soon felt his muscles loosen up a bit. I took this opportunity to push in deeper.

"Oh that is weird," he cried out, tensing up again. His erection had began to wane just a bit as I felt him soften in my mouth. Maybe anal play just really was not for him, but I wanted to explore just a bit more before giving up entirely.

I pushed in another inch or so until my finger was buried just past the second knuckle. Some of the info I read earlier, including a description on where to find the prostate, was still fresh in my mind. I knew to curl my finger up towards his belly and search for a spongy walnut shaped spot. It was difficult to tell exactly what I was feeling, but my finger soon found something that seemed to be a bit firmer than the tissue around it. I gently pressed on it.

Nick suddenly inhaled deeply and his cock swelled back to its max hardness almost instantly. I tasted something a bit sweeter as well in my mouth.

"I uh.... um... ahhh." Nick muttered, not being able to find words as his whole body twitched. I placed my left hand around the base of his cock to steady him as I continued to suck the head and upper shaft.

I then began to move my finger tip against his p-spot, using a gentle curling motion while I worked the shaft in tandem with my mouth and left hand.

After only a few seconds of this, Nick grunted loudly. I at first thought that I had become too vigorous and hurt him so I took my mouth off of his penis and looked up at his face. That turned out to be a bad idea as a blast of cum suddenly hit my chin and lips. I gasped as another one flew up and landed on his chest. I continued to squeeze his base and work his prostate as more and more shot out.

After 6 or 7 spurts, his orgasm subsided. I carefully withdrew my finger and moved to go clean us up. Nick just lie there with a dumfounded look on his face. "That was so strange," he finally said.

"It was good, right?" I asked as I wiped the cum off my chin with a tissue.

"It happened so fast. Where did you learn that?" he inquired slyly.

"Just was reading some stuff online today."

"Well that was certainly something. Not sure I want to do that very often though... kind of makes my ass sore," he chuckled.

I just smiled back at him as I moved to clean the cum off his hairless muscular chest. Obviously there really was something to prostate stimulation. It absolutely made Nick cum much more quickly that a simple blowjob normally would have. But yet, he did not seem to overly enjoy it. Maybe I needed to ask Josh a bit more about the topic.

***

The following day, Nick had a flight to catch to one of his increasingly frequent business trips. I was glad that we had the opportunity to have that amazing sex the night before as I would not see him for the next three days straight. As I drove back from the airport, I reflected on my wild evening and looked forward to learning more about my new found fascination in the coming days.

As soon as I got back home I shot Josh a message.

"Need to chat, have some juicy details to share and maybe more questions. Let me know when you are free! :)"

I got no immediate response but it was the middle of a work day so I decided to be patient.

As I went about my daily business, I periodically checked my phone to see if he received my message. Each time I went to check, I tinge of excitement shot through my body, but alas there was no response. Finally, late in the evening, just when I was about to settle down for bed my phone buzzed.

"Hey there, sorry I have been busy all day. Can chat a bit now if you want, or I am free all day tomorrow."

All day? I thought to myself. Without really thinking, I suddenly found myself typing.

"Do you wanna hang out tomorrow?"

There was a brief pause.

"Um, like with you and Nick?" he responded.

"No, he is out of town."

"Oh yea, I forgot him and Boss left this morning for that conference."

"Just you and me :)" I hoped I was not coming on too strongly.

"Would Nick be OK with that?"

"Oh yea, he does not care who I hang with. We are cool like that!"

"Well, OK, sure we can hang. What time?"

"How about we meet for lunch and then see where it goes from there?"

"Sounds good," he responded.

From there we decided upon one of the hip local restaurants and said our goodbyes. After I shot a separate message to Nick wishing him a goodnight, I drifted off to sleep looking forward to tomorrow a bit more than I probably should have.

***

We both showed up at the restaurant at the same time. I spotted him as soon as he got out of his car. He was dressed similarly to how he had been at the party, not totally disheveled or anything, but certainly not like he made a ton of effort to look good.

I, on the other hand, was wearing a spaghetti strap top that showed both a ton of cleavage as well as side boob with one of my cutest skirts below. I left my hair down this time, cascading all around my bare shoulders and upper back.

"Hi there," Josh greeted me as he walked towards me.

I took a few quick steps towards him and threw my arms around his neck. He hesitantly brought his hands up to my sides lightly returning the embrace. He laughed as I pulled away, seemingly amused at my enthusiasm. I also noticed once again, that he did not even try to steal a glance at my breasts, which had just been pressed firmly against his chest. Josh was certainly a hard nut to crack.

After making our way into the restaurant, we ordered, then had a nice meal with mostly casual conversation (nothing too spicy). We chatted about each other's past and I felt I finally got to know Josh as a person. Throughout our conversation, I kept wanting to bring up my experience with Nick from a couple nights before, but with the way tables were laid out in the restaurant, it would have been impossible to not be overheard.

As we wrapped up the meal, I decided to again be very direct.

"So, you remember I had some juicy details I wanted to share relating to what we chatted about over messenger?"

"OK," he muttered almost as if it was a question.

"But not here. Do you want to hang out at your place?"

He looked at me suspiciously. "You sure Nick would be OK with this?"

"Haha, don't worry about him so much," I assured him, placing my hand on his.

"Well OK, my apartment is just around the corner, if you want to get out of here now."