Jen's Sexual Education Pt. 03

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Jen's sexual explorations reach their inevitable culmination.
10k words
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Part 3 of the 3 part series

Updated 06/14/2023
Created 02/28/2023
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"So what do you want for your birthday?"

I casually dropped the line to Nick as we got ready for the day. It had been a few weeks since I gave my husband his first true prostate massage. It had also been a rare length of time without an out of town trip for him, so we had seen each other a bit more than usual. Yes, there had been several other incredibly wonderful sexual sessions, but nothing like the one where I gave him his first hands free orgasm, and the mind blowing coitus that followed.

Nick looked at me as if he wanted to say something but he remained silent.

"Well, tell me. What do you want?" I repeated.

"I... I am kind of embarrassed to say it."

"Just tell me!" I laughed. Nick was generally not one to get embarrassed about anything, so I was keenly interested in what he was on about.

"Well, do you remember my dirty fantasy? You know, we talked about it when you were... um... giving me that special massage?"

"You mean that prostate massage?" My skin began to tingle, almost as if my body was trying to anticipate where he was going with this.

"Yea. Um... you know how I said I would love to see you with another guy?"

"Yea... and?" My heart was now pounding in my chest. Nick just stared at me without continuing. "And what baby... what do you want?"

"That," he said matter-of-factly. "I want that... to see you with another man. That is my birthday wish."

"Are you serious?"

"Yes. Does that upset you?" Nick asked with a surprising level of confidence.

"No baby, I just..."

"I think you would enjoy it." He was bolder now, more resolved in his request. His managerial qualities were coming out. "And I am pretty sure I can talk Josh into doing it." He grinned slyly.

"Josh? Oh yea, I remember talking about him with you." I again tried to play off my familiarity.

"Yea, and you said you heard he has a big dick, right?"

I just nodded in response.

"And, I know he thinks you are hot. I asked him straight up the other day. He will never come right out and say it, but he gets very nervous and antsy when I talk about you. I can tell what he likes. Plus, I know he is single. I think I am going to ask him over for dinner on my birthday. And maybe you can wear something super sexy. We can have a few drinks. Would you seduce him in front of me?"

I was in shock to say the least and just stared at my husband blankly.

"Well... what do you say? I know I have never asked for anything like this, but I have been out of my mind thinking about it. Would you do this for me?"

I kind of snapped myself out of it and looked directly at Nick. "Sounds like you have it all planned out. What if he does not want to though?"

"Baby, look in the mirror. Do you really think he is going to say no?" Nick laughed.

"Well, OK, you can invite him and we will see what happens."

***

Later that evening I decided to message Josh. We had not seen each other since our last rendevouz at his apartment. And we had only chatted a little online. I did tell him briefly about giving Nick the prostate massage and the amazing fucking afterwards. He was quite impressed I was able to make him cum hands free. But since Nick had been home so much lately, I really had not gotten a chance to chat more with Josh.

But now, here I was in the most awkward situation. My husband was going to ask this other man--one whom he thought I barely knew, but had no idea I had been in a couple very sexual situations with already--to dinner at our house, so I could "seduce" him. I knew Josh and knew that if I did not say anything, he would very likely find some reason to not come to the dinner if invited. He was already very worried about Nick finding out about us, so I was sure he might freak out if Nick really pushed him to come.

Yet at the same time, here was this opportunity. If I could somehow figure out how to walk that fine line, I might be able to have my sexual curiosity with Josh fulfilled beyond what I thought we could ever do, yet without it feeling like I was cheating on my husband. I knew what I had to do. I needed to preemptively warn Josh about Nick's invitation. If he knew that I was OK with him being invited over, maybe he would be more likely to go along.

"Hey there, busy?" I messaged Josh.

After about a minute he responded. "Hey! How's it going?"

"OK, well I will just come right out and say it... Nick is going to invite you over to our house for dinner pretty soon. I know that might be weird for you, but whatever you do, you need to say yes."

"Umm, OK. That might be a pretty awkward situation. You don't think he found out about us do you?"

For a second I actually considered telling Josh that he had actually found out about us (which would have been a lie), but thought that might complicate the situation a bit too much. I decided to keep walking that fine line. "No, we can keep our secret, right? He just wants to get to know you outside of work a bit more."

"But are you going to be there too?"

"Haha, yea. I do live at my house, silly!"

After several more seconds, he finally responded. "Well OK, if I am free, I guess I can. It would be nice to see you again."

I felt a pleasant flutter in my stomach when reading his last sentence. He continued, "we just need to be on our best behavior!"

"We'll see!" I shot back.

***

Josh smiled at me from across the table as Nick continued one of his long rambling stories of his early years at the company. I chewed my food slowly opening my eyes a bit wider as I shared his bewilderment in my husband's sense of duty. Nick just kept rambling right along, totally unaware of our non verbal communication.

Josh had arrived at our house about an hour prior and after a few drinks and casual conversation, we settled down to our somewhat fancy meal that we had delivered from one of the local hip restaurants. We would not have normally catered food for such a small dinner party, but being Nick's birthday and all, we decided to splurge just a bit.

For the occasion, I had put on one of Nick's favorite outfits of mine. A dark blue-green knee-length dress with a deep V cut that went all the way to my sternum, exposing a vast section of my cleavage. The dress had a bit of structure in the front, but without the support of a true bra, my breasts felt quite exposed, especially when moving around. When we had first greeted Josh at the door, I noticed him take the tiniest peek at my chest before he quickly averted his eyes.

After Nick finally wrapped up his latest company story of the evening, he apparently decided to make my outfit the next topic of conversation.

"So what do you think of that dress?" he stated very directly. We both turned to Josh, his face suddenly turning a bit more pink than usual.

"Uhh, yea, it's a good one."

"Certainly shows off the girls, doesn't it?" Nick laughed and I mustered a small chuckle.

"Umm yea," Josh quietly responded.

"Hey man, it is OK to look. I don't mind, really." Josh looked at Nick then back at me. "And you don't mind either, right baby?" Nick continued, turning towards me.

"Hey, I am totally used to it." I said, wondering how best to keep the situation from getting too awkward.

"You want to know something, Josh?" Nick continued. "I um... how do I say this?... It's kind of one of my things... I like when guys look at Jen's tits. It you know... it 'does it for me'."

"I see. They are very nice, I must say," Josh responded, now looking more directly at my cleavage for the first time.

"Do you want to see them a bit more?" Nick smiled slyly looking back at me, encouraging me to play along.

I decided to just be very direct as I was suddenly not in the mood to beat around the bush any longer. I reached across the table and placed my hand on Josh's. "What my husband is trying to say is, it is his birthday and he wants to see you enjoy my boobs."

Josh suddenly had a mixture of fear and confusion on his face.

"Would you do that for me, man?" Nick asked.

"What... what do you want me to do exactly?"

"Ok, picture this..." Nick began to bloviate again. "Jen's dress pulled down, her amazing pair totally free, your cock resting between them, do I need to continue?"

"Are you serious?" Josh inquired, still seemingly quite puzzled. "Have you all done this kind of thing before?"

"No," Nick answered quickly. "It would be our first time. But oh my god I have been fantasizing about seeing Jen tit fuck another guy for so long."

Josh sighed heavily then spoke quickly. "Ok, this might sound weird, but I am actually asexual. I don't think I am the right person for this."

"Asexual?" Nick cried out, dumbfounded?

"I think it means he does not have sex," I tried to clarify.

Josh half way rolled his eyes at me as if to say "no shit."

"You are telling me you are not attracted to Jen?"

"Well, no it's not that exactly. I just don't like to complicate things with sex. I haven't even had sex with anyone in years."

"Well I am not asking you to have sex with her. Just maybe let her tit fuck you, maybe a quick blowjob, you know?" Nick argued.

Josh seemed to ponder Nick's request more seriously for the first time. "And you are sure you want that?"

"Hey it's my birthday dammit. I know what I want." Nick laughed.

"And you are OK with it too?" Josh politely asked, turning towards me.

Once again, I was kind of over the talk and decided action was a much better response to Josh's query. I looked Josh right in the eyes, giving him my most reassuring stare. Without breaking eye contact I reached up and pulled the left shoulder strap of my dress down to the middle of my arm exposing the entire top half of my boob. I soon did the same on the other side. Without the support of either side, the fabric slowly fell away and my large breasts were now fully exposed in the soft light of our dining room.

Josh's eyes widened and I heard my husband draw in an excited breath. I did not look over at him though. I instead maintained direct eye contact with Josh. His eyes quickly darted back and forth between my piercing stare and my bare chest. After letting him enjoy the view for several silent seconds, I slowly slid my chair back and stood up. I carefully walked around the table and grabbed Josh by the hand once again. I squeezed him and pulled slightly, beckoning him to stand and follow me. He quickly obeyed and my husband soon was following us down the hallway.

Once in the more comfortable confines of our bedroom, I pushed Josh back against a soft chair in one corner of the room. I twisted around and unzipped the back of my dress letting it fall to the floor. I was now wearing only a pair of heels and a simple black thong. Nick took a seat on our bed and prepared to watch the show.

I moved back over to Josh and quickly began to unbutton his shirt. As I worked, I could feel his excited breath on my exposed tits. The feeling was enticing and only heightened my anticipation for what was about to happen. My head was spinning as I fumbled with each button, lower and lower on his torso. As I reached for the final button, I leaned over and whispered directly into Josh's ear.

"Hope you don't mind but I'm snapping your streak tonight."

Soon Josh's shirt was crumpled beside us on the floor and he quickly pulled his undershirt off as well. My hands shot to his pants where I slowly unbuckled his belt and undid the button on his trousers. He skillfully lifted his butt off the chair and helped me pull his pants down over his legs. I liked how his abs trembled as he engaged his core. He was certainly nowhere near as cut as my husband, but I had to admit, his thin body was sexy in its own way. Soon I was face to face with a fairly significant bulge protruding from his grey boxer briefs. I placed my hands on the waist band ready to pull them down, but then stopped, looking over at Nick on the bed.

"Are you ready for this baby?" I asked lovingly.

"Oh my yes. Do it please."

I pulled firmly, sliding the fabric over his thin but toned thighs. Josh's giant uncut cock sprang free. It was maybe half hard, but the foreskin still completely covered the bulbous head.

"Fuck dude! You are big." Nick commented. Josh just smiled. I extended my right hand and gently placed it around the soft ball of flesh covering his glans. He looked huge, but felt even bigger in my hand. It was if I was squeezing a firm water balloon. At my touch, his cock immediately began to lengthen. I slowly started to slide the skin down his shaft while I positioned my body between his legs, taking care that Nick had a clear view from the bed.

It was so arousing to feel his massive cock harden in my hands, pulsing with each beat of his heart. Soon the head began to poke out of its veiny sheath. The tip was already glistening with precum and I instinctively lowered my head to lick the slit. It tasted even sweeter than I had expected.

Nick moaned loudly from the bed as he saw my mouth make its first contact with Josh's member. "Do you mind if I...?" I heard him ask. I glanced over to see him sliding out of his own pants and underwear, his already rock hard cock springing free. He also quickly removed his shirt without even a hint of modesty and sat back down on the bed, dick in hand ready to watch the rest of our show.

I laughed at my husband's enthusiasm but soon quickly turned my attention back to the monstrous erection in front of me. Josh's cock was now pointing straight up at the ceiling and it was a sight to behold. His foreskin was still clinging tightly to the engorged head and the shaft had grown so thick I could not even reach my fingers around its circumference. I slowly began to stroke the supple skin, marveling at how it moved against the swollen flesh beneath. Josh breathed in deeply and moaned.

"Fuck you have him so turned on baby," Nick chimed in. "Put it in between your tits!"

I moved my hand to his wide base and firmly gripped the cylinder of flesh. Moving closer, I situated my torso in between Josh's open legs. My breasts were now touching each of his hair covered thighs. Josh moaned softly and I began to slide my body further forward. At the same time I pulled on his shaft, aligning his length with my deep cleavage.

Lowering my body one more inch, the large head finally nestled itself between my soft mounds. I pressed his shaft firmly between them and squeezed my arms together to more fully envelop his hardness. His cock was so long that even with my large tits fully wrapped around it, the top couple inches were still completely exposed.

Looking down it was an incredibly sexy sight from my point of view. Without thinking, I lower my head and took the tip into my mouth. It was not even the entire head, just the tip, but still I had to open my mouth fairly wide to fit any inside. Josh moaned more loudly feeling my soft lips on his sensitive skin. With one hand still gripping the base, I pulled a bit more of his loose skin and the head finally popped free. Taking it out of my mouth I marveled at its perfect mushroom shape. It was almost a shade of purple at this point, the skin tight from being so incredibly engorged.

Josh's breathing picked up as he was obviously incredibly aroused from a woman's first touch of his sex organ in years. I moaned in response and then squeezed my tits even more firmly around his shaft, moving them up an inch or so until his head was directly in between them.

"Oh my God," Josh moaned again. "You have me right on the edge."

Those words were like music to my ears as I adored making love to a cock like this, working it into such an aroused state that it could explode at any moment. And I had never done it to a cock this beautiful, so to say I was thoroughly enjoying myself would be the understatement of the century.

I next went to move my tits back down his lengthy shaft. I wanted to give Josh the best tit fuck he had ever had in his life, but just as I began to move he let out a gasp, almost as if he was in pain. Then a sudden hot blast of liquid hit me squarely in the chin and splattered all over the top part of my boobs. Another stream blasted out from his cock, this one landing right on my collar bone. Quickly more and more hot white cum shot and then oozed from Josh's pulsing member until by breasts were thoroughly covered in his glaze.

As his orgasm subsided, I realized I had totally frozen once he started cumming. I guess I was kind of shocked how easily he came and how much of it there was. I had not even realized what was going on until halfway through. I quickly tried to make up for my lack of action by squeezing the last few drops from his thick shaft. Josh let out a long sigh and relaxed back against the chair.

"Fuck!" was all I heard from the bed as my husband had also gone silent through Josh's orgasm. I looked over at him quickly, cum still running down my neck. His hand was furiously pumping up and down his own cock which was as rock hard as I had ever seen it. I suddenly had the urge to grab it, feel its hardness. I carefully rose to my feet and moved the short distance to where my husband was seated naked on the bed. As I walked towards him, another deliciously naughty though popped into head. Since he enjoyed seeing another cock cum between my tits so much, maybe this would be even more mind blowing for him.

I lowered my body and crawled between Nick's legs. His eyes went wide as I reached for his cock, moving his own hand out of the way. I gripped his shaft, then slid his hardness between my cum covered tits, the thick white glazed serving as the perfect lube. My cleavage fully enveloped Nick's smaller cock and I looked down only to see a huge pool of cum which his dick had pushed up between my breasts.

"Baby, oh my..." was all Nick could say as I began to slide him up and down just as I had done with Josh just 30 seconds prior. But also like Josh, Nick very quickly drew in a quick breath and grunted. I felt him pulse and soon several streams of his own white glaze was shooting from his tip, mixing instantly with Josh's previous emissions.

While Nick's cumshot was not quite as massive as Josh's, it still was considerable and my boobs were now coated with an absolutely ridiculous amount of semen. Nick looked down and must have noticed the same thing as he just started cracking up. I carefully backed away and rose to my feet, turning towards Josh. He also began cracking up. The situation was just so absurd. I had just made two sexy men totally empty their balls onto my body less than a minute apart. I had never felt so powerful, like such a sex goddess, and I was overjoyed at how much pleasure I was able to give in such a short amount of time.

"Hell of a birthday present." Nick finally remarked after the laughter had died down.

"Can't believe you both popped that quickly," I added.

"I was just so fucking turned on. Oh my god dude," Nick responded. "And shit man, how the hell did you cum that much?"

"Well," Josh began to answer. "You probably won't believe this but I hadn't cum in like over a year I think."

"The fuck? Really?" Nick asked.

"Yea, like I told you I am asexual."

"Dude, with a dick like yours you should be getting all kinds of tail."

"I used to when I was younger, but just found other stuff to do I guess. But this was nice. I enjoyed cumming in a more traditional way again. Reminded me of old times."

"More traditional way?.... what the fuck are you talking about dude?"

I rolled my eyes and got up, anticipating exactly where this conversation was headed. I walked over to our night stand where I began using an embarrassing amount of tissues to wipe the cum from between my breasts. As if not even noticing my actions, the boys kept up their conversation.

"Well, several years ago I kind of discovered that I really enjoy prostate play."

"Oh really?" Nick perked up.