Jen's Sexual Education Pt. 02

I could not contain my excitement as I drove towards Josh's apartment. It had been a few weeks since we had decided I could give him a prostate massage. We had waited for a date when Nick was going to be on yet another business trip so that there would not be any surprises. In the days leading up to our rendezvous I can't even count how many times I masturbated, having some of my better solo orgasms I can remember.

Nick and I had also had sex nearly every day during that time. Though most of the sessions were still quite hot, none of them had reached the level of excitement that first one back from his previous trip had reached. I had even let him in my ass a couple more times, but he actually seemed to be losing a bit of interest in that area. I figured this was all the more reason to learn how to give him a mind-blowing prostate massage. I desperately wanted to surprise him with my new skills when he returned from his current trip. For that reason, I had avoided doing anything backdoor to him over the last few weeks. Nick even had a birthday coming up in the not too distant future. I was surely going to give him the time of his life on that special day!

Soon I pulled my car onto the familiar street and parked in the closest open spot to Josh's apartment door. I messaged him and he was down in no time to let me in. He was wearing his usual "not trying very hard" get up... a simple white t-shirt and a pair of grey sweatpants. The soft fabric seemed quite thin and there was quite the conspicuous bulge protruding from the front. I wondered briefly if he was going commando under there, a thought that sent a pleasant tingle through my body, hardening my nipples.

Josh gave me half-hearted hug as I strolled in through the doorway. Anyone seeing us there together would have never had any idea what was about to go down. Once inside his place, he offered me a drink and then proceeded to begin laying out a towel on his cushy sofa.

"I thought it would be easier to do this out here," he stated casually, gesturing to the couch.

"Right down to business I see," I remarked, shaking my head.

"Hey you are the one that wanted to do it so much," he replied, smiling back at me.

"Sure, let's do this." I then noticed that he had a few more things laid out on one of his end tables in preparation for our "session." The first obvious thing I noticed was a large bottle of lube, but next to it was the unmistakable shape of a condom wrapper. Upon seeing that, my heart briefly leapt into my throat. Was he expecting us to?... No, that is not like him, I thought to myself.

He must have seen me staring at the condom wide eyed because he quickly spoke up. "No, it's not what you think," he chuckled. I looked back at him, confused. "That is for your fingers... makes is quite a bit easier and less messy in my experience."

"Oh," was all I could say in response. Josh then motioned for me to have a seat on some cushions he had placed on the floor just in front of the couch.

"Are you ready? I think everything is set." I nodded as I made myself comfortable on the cushions. "OK, here we go."

Standing next to me, Josh then pulled down his sweats and my earlier suspicions were immediately confirmed. His oversized manly sex organ swung into view in all its glory. Out in the living room, the lighting was far better than in his bedroom and I was much closer to him than I had been during our last session. So to say I was being treated to quite the visual show would be an understatement.

Josh's uncircumcised cock hung a couple inches past his large balls, which were covered in a thin layer of dark hair. His cock was quite veiny but overall looked soft to the touch. There was not any sign of an erection, but still his size was beyond impressive. The thick shaft and an even thicker head was covered by the supple foreskin in a very inviting way. I had the sudden desire to peel back the skin to see what lie beneath, but I restrained myself. I needed to honor his wishes... no penis touching!

Once his pants were completely removed, Josh turned and sat back against the couch. He spread his legs apart and leaned back, rolling his hips up towards me. He then pointed at the condom and instructed me to open it and roll it over my middle and ring fingers of my right hand. As I opened the wrapper, I noticed that the condom was marked "large." Of course it was, I laughed to myself. I wondered if he bought these purposefully for this session, or if he still had them from a previous time in his life when he was still seeking partnered sex.

Once the condom was fully rolled onto my fingers, Josh had me lube up the outside of the rubber. It was already pre-lubed, but as he explained, you can never have too much when doing this kind of thing. He also had me squirt a tiny bit of lube on his finger and he quickly brought it to his opening, expertly lifting his cock and balls out of the way to find the puckered hole. Once he was pleased with the lube job, he leaned back against the couch again, closed his eyes and seemed to relax a bit.

"Are you ready?" I smiled at him. He opened his eyes, half smiling back.

"Sure... but just like I said, please don't touch my dick. It really takes away from my focus."

"Whatever works for you babe," I responded playfully.

Josh's cock was now kind of draped toward his right hip, the tip pointing up to my left. His balls however had returned to a hanging position and were partially covering his anal opening.

"Do you mind if I...?" I whispered as I gently tried to move them up and out of the way. Josh chuckled and moved a hand to help roll their weight up and to the left. Now unrestricted, my condom covered fingers shot to their target. As I begin to massage around the sensitive opening, Josh made no noticeable reaction. He remained still with that look of relaxed focus on his face.

After a few seconds, I decided it was time to enter, and began applying pressure. I was surprised how easily my fingers parted his opening. As soon as the very tip was in, his muscles seemed to almost draw my fingers in the rest of the way. This was very different than doing it to Nick, but I assumed Josh's years of experience in this realm made his body far more receptive here.

My fingers were now pretty much fully inserted, nearly to my third knuckle, and Josh still had had almost no reaction. His breathing may have been a little deeper now and he certainly was not in any discomfort, but I was not sure if he was getting any pleasure.

"How does that feel," I decided to ask.

He cocked another half smile. "Oh, it's very nice. It has been awhile since doing this with a partner, so I am enjoying myself."

As soon as he said those words, Josh's muscles clamped down hard around my finger. "Whoaaa!!" I yelled out instinctively. "I guess you are enjoying." He laughed back at me.

He then released his grip a bit and I took another few seconds to get used to being inside him. I was eager to see how much pleasure I could give him like this, so I soon began to search for his prostate. I curled my fingers up towards his belly button and very quickly found the firmer, spongy texture. I pressed gently and Josh contracted his muscles again, though not as hard this time.

"Is that the spot?" I asked, hopefully.

"Well, you are touching I guess the back part of my prostate, sure," Josh flatly stated. "That feels nice, but I have found the best sensations are when I can get more on the top side, so you have to reach in a tiny bit further."

I was already buried pretty deep, but I began to push against his hole more firmly now, trying to reach farther. "Is this OK?"

"Yea, you don't have to be that gentle, I am used to it."

I pushed even further in, my two middle fingers now entirely out of view. I continued to curl them up, sliding around his gland. Soon I found the right spot as Josh clamped down even harder around my fingers.

"Ooouuuww!" I cried out.

"Sorry," he responded, releasing his grip.

"It's OK, but fuck you are strong," I marveled. My fingers weren't really in pain or anything, I was just shocked at how hard he could grip. I wondered if my own ass could do that, and if so, is that why some guys really loved anal so much? That would have to feel amazing squeezing their cock, right? It was a sexy thought.

"That's the spot, rub around there a bit." Josh's words brought me back to the present and I happily followed his instructions. The top of his prostate was even spongier feeling as I began to massage in small circles. His breathing was now clearly heavier and he even began to moan slightly with each exhale. Glancing to my left, I also noticed another sign of success, a thick strand of pre was hanging from his tip. In seconds, the flow began to pool on his hip in a very visually exciting way. His dick seemed to remain totally soft, but I could see it kind of quivering a bit, the muscles spasming at the base. I could also feel these spasms inside him, more and more as I rubbed his spot. It was almost like his ass was milking my finger, drawing me further into his body.

Soon Josh's hands shot to his nipples where he began to caress them in small circles. It was almost like he didn't even realize this happened, it was just a sub-conscious instinct. His moaning picked up even more and I felt his entire body begin to rhythmically contract. It was quite apparent he was enjoying my massage immensely, but his eyes remained tightly closed, a look of deep concentration spread across his face. I briefly pondered why he would not want to watch me while I was doing this to him. It seemed pretty much all other guys I had been with would never shut up about how much they liked to watch me give them a blowjob... and while this was not a blowjob of course, it was still an attractive woman pleasuring him. But Josh really was different, and I guess that is what fascinated me about him

Again refocusing myself to the present, I noticed that the pool of Josh's fluid had now begun to spill over the side of his hip and some was getting on the couch. Josh did not seem to mind, notice, or care of course, as his breathing was nearing orgasmic states. He had now transitioned from one small sound on each exhale to longer, continuous moans of ecstasy. The whole sight in front of me was so incredibly sexy and I began to recognize a significant feeling of wetness in my own panties.

Suddenly Josh cried out "I'm cumming!" I immediately became overwhelmed with arousal at the realization he was experiencing an orgasm right here in front of me and my hand shot right to my crotch to give my rock hard clit some needed relief. My eyes darted to his cock to see if anything was going to shoot out, but the strands of pre just kept pouring from the tip. His ass muscles continued to rhythmically clamp down on my fingers and his moaning persisted.

After several seconds, his verbalizations calmed a bit and I began to lessen my motions inside him. "No, keep going," Josh insisted. Apparently the sexy man in front of me was not done. I pushed further inside him, redoubling my efforts on his prostate. A few larger drops of fluid ran from his cock making my mouth water with desire.

My own horniness was on the verge of taking over now as I slipped my left hand under my waistband. I had to feel skin on skin contact to my clit. It had never been harder and I began to rub it furiously. I suddenly became aware that I was also moaning along with Josh, maybe even a bit louder than he was. He apparently noticed this too and smiled back at me although his eyes remained closed. There was no doubt about what I was doing to myself, however.

In seconds, I began to near my own orgasm, and Josh seemed to be gearing up for his second. As my arousal increased, Josh seemed to become overwhelmed and his chest was now heaving up and down. I glanced down and noticed that his cock had suddenly become much fuller. It twitched with each of his heartbeats, also growing longer and moving towards the center of his body. Was he finally becoming erect?

Without thinking, I adjusted my position between his legs, getting a bit more on my knees. This allowed me to spread my legs more, giving me easier access to my own genitals. It also put my head higher and more over top of Josh's body. As his erection reached a near-maximal state, his cock had now lifted off of his belly and bounced tantalizingly below my moist lips. I lowered my head towards the impossibly long shaft, which stretched well past his navel. The lime-sized head was now just peeking out from his veiny foreskin. It was by far the largest cock I had ever seen. Would it even fit in my mouth? Probably not, but I desperately needed it.

I opened my mouth, but something stopped me. I froze, my lips barely an inch above the gorgeous monster. I could feel the heat from it on my face and smell the sweet, salty fragrance of his pre cum, now smeared all around the head. But I did not lower my head any further.

I am not sure if it was just a line I did not want to cross (as far as cheating on my husband), or I was genuinely compelled to respect Josh's wishes, or if it maybe just the eroticism of the whole situation. Maybe crossing that line would eliminate some of the intrigue, some of that burning desire I was experiencing in that moment. Whatever was the reason, I went with it.

My left hand had now moved past my clit and three fingers were inside my dripping vagina. I was not even sure at what point I had pushed them in, but they were making audible wet sounds as I sloshed them about, my palm pressing down on my impossibly hard bud. I was about to cum hard with my face nearly touching Josh's engorged cock.

I looked back at Josh and he was still basking in his own pleasure, eyes shut, concentrating, cumming again? It was hard to tell at this point. I assumed he was just having one long continuous orgasm, in total ecstasy. His arousal was bringing me there as well. Suddenly one hand was not enough for me and my own sexual desire had pushed my needs to the front. I quickly withdrew my fingers and fell back away from him. I carefully removed the condom then grabbed the waistband of my sweats and panties and slid them a few inches down my pale thighs. I just had to have unfettered access to my lady bits, even if just for a second.

I was now leaning back again a coffee table a few feet from the couch as I inserted fingers from my left hand into my dripping pussy and placed my right hand ones on my throbbing clit. I looked back at Josh, expecting him to have come down from his orgasm, but he was still breathing quite hard, his steel hard cock bobbing as he continued to experience multiple dry climaxes. It seems my fingers inside him helped him get to his current state of arousal, but they sure were not necessary for him to stay there.

I began to furiously finger myself while I watched him. The whole scene was way more erotic that I could have ever imagined. Two people about to cum their brains out yet we had barely even touched one another, at least not in the traditional ways. Of course, my body wanted nothing more than to climb on top of him and attempt to shove his large member into my hole. Honestly, I don't even think he could have fit, but I was so aroused I would have done anything for him at that moment.

But on the other hand, knowing that we were going to stay disciplined, keep this as it was, gave me a lot of trust in him and possibly made the situation all the more erotic. It was like a super sexy mind game we were playing with each other. Or at least that is how it was in my head.

After what could have been a few seconds or several minutes, my physical arousal finally reached a peak. A hot tingling sensation tore through my body making every single one of my muscles contract. My vision slightly blurred and I felt flush all over. My heart was about to pound out of my chest. There seemed to be an immense pressure building in the lower part of my gut. My pussy clamped hard... harder than it ever had on my fingers, squeezing them out in a slick pop. Then, to my huge surprise, a torrent of fluid gushed out of my hole and onto the carpet in between my legs. Thinking back, it wasn't like it was a gallon of liquid or anything, but it was enough to make a significant sound as it hit the low-pile fabric. I was mostly surprised at how there wasn't much of a warning. I had squirted several times in my life before, but it had never come out like that... usually more or a drip. This was one single gush of cum.

My squirt seemed to snap Josh out of his orgasm finally as he looked over at me with a kind of "what the hell did you just do?" look. I immediately felt a rush of emotions, ranging from embarrassment to excitement and a bit of post orgasmic bliss as well. "I'm sorry," I mouthed to him as I continued to rub my clit and outerlabia. Everything was just delightfully soaked down there.

Josh then slowly pulled himself off the couch. His still mostly hard cock was sticking out at about a 90 degree angle from his body and swung amusingly as he walked to find some tissues for us to clean up. After wiping himself up a bit, he handed a few to me. I used some on my crotch and legs and some I used to try as best I could to sop up the dampness of the carpet in front of me.

After a couple awkward minutes, I piped up... "So how was that?" I asked, mostly rhetorically.

"Well, not like I can hide this," he said, pointing at his still very hard member.

I laughed. "Yea definitely not. I definitely had to resist grabbing it when it got harder like that. I can't believe you can keep from touching it yourself." I laughed again as I threw away the used tissues.

"Yea, well, it did take a lot of discipline at first, but now I am used to focusing my arousal and deriving my pleasure elsewhere in my body. Usually I don't even get hard during sessions anymore."

"So why did it get hard this time?"

"Well I think maybe you being here caused that, especially when you starting moaning."

"Oh really?" I was intrigued. "It seemed like you were concentrating really hard there most of the time. I did not even know if you were paying attention to me."

"Oh, sorry. I kind of zone out when I do this normally, I guess it is just a habit."

"You mean like a Zen thing or something."

"Ummmm, maybe. Well, nothing that mystic really. You just have to be really aroused to get in the right mindset for this, so I usually fantasize."

"Fantasize about what? A girl with her fingers up your ass?" I teased him.

"Ha, well, yea I guess I have in the past, but I do have a 'go to' one that always does the trick."

"Tell me about it," I pleaded flashing him my wide eyed cute look.

"You might think it a bit strange."

"Well my fingers were just in your ass and I squirted all over your floor, so I think we are past strange."

"Haha, of course," he chuckled. "Do you know what a futa is?"

"That is one of those Anime girls with a huge dick, right?" I had watched a decent amount of porn in my life, more than more girls like to admit, so I knew the adult scene pretty well.

"Well, yea, but I don't necessarily imagine her being anime or anything. Just a sexy woman who happens to have a cock. It doesn't have to be big, just hard. And she is fucking me with it." He smiled at me, waiting to see my reaction.

"Ha I see... well I think that is kinda hot actually. And you were thinking about this when I had my fingers in you?"

"Oh yes, definitely, and you know what was really hot? I was fantasizing about her moaning from fucking me, then realized it was actually you moaning. I think that is what got me really going."

I marveled at how analytical we were being about the highly sexual scene that had just occurred, but I think it honestly helped both of us see the situation less like cheating and more of a "friendly experiment." After chatting a bit more, I apologized again for wetting his carpet (which he totally shrugged off as no big deal) and soon it was time for me to get going.