So…this story continues several weeks later. After a period of several weeks where we’d sort of kept our distance, purposely or not, things got particularly weird when I joined the gym where Joe worked out.
In my defense, I casually mentioned to Joe that I wanted to start working out again after having a major abdominal surgery back in January of this year, and after being medically cleared to resume physical activity, Joe was anxious for a workout buddy.
Since he was made aware of my chastity cage, and that was no longer a secret, I didn’t feel like I needed to hide it any longer, which opened the door to gym membership. In fact it was Joe who encouraged me to join the same gym nearby where we worked.
Since it had been almost a month since we’d hooked up l honestly put that in the back of my mind as a one off drunken evening, never, ever expecting anything to happen again between us ever again.
I’d been used to one night trysts at this point in my life so I wasn’t too upset about it. I’d been brought up on the idea that you never mix work with romance, I was perfectly alright with keeping our tryst a distant memory. Honestly, I had decided it was for the best that we cool things down given Joe was my boss, and from an ethical perspective, it just was the right thing to do to stop lusting after my boss.
Yeah…well…then we decided to go to the gym together and go for a 30 minute run on the treadmill to ease me back to the gym and that changed everything.
We changed in the locker room, and Jesus Christ Almighty, I snuck side glances at my boss changing into his gym clothes, and the dirtiest thoughts emerged into my mind. I think seeing him in army fatigue boxers and nothing else took me right back to this forbidden place of me lusting after my boss.
I tried to hide my gay instincts and not pay too much attention to my boss changing right across from me, but I have no willpower, and I was remembering what it felt like when Joe bedded me. I knew what he had underneath those boxers, and I wondered if I’d ever get to experience it again.
I dared not linger in that locker room. There was so much eye candy I could have just stayed there all night lusting after some of the hottest naked bodies I’ve seen in a while. I quickly changed into running shorts and tank top carefully as I was not about to expose my cage to a locker room full of virile men. Once I tied my shoes, I went up to the treadmills.
I found two open treadmills towards the end of the row and took one. Joe took the other. For thirty straight minutes we both ran side by side working up a sweat. I tried to stop myself from peaking over, from watching my hot boss grind it out on the machine next to me, but as I said earlier, I have no willpower and every couple of minutes I took a quick glance.
Sweat stains developed all over his shirt which was now clinging to his body. Boy was it a good thing my dick was locked away and secured in a jockstrap because it would have been hard to hide a hardon. I felt my cock tingle, trying to come alive, but little Richie was stifled by its confines. Maybe one of the benefits of chastity is not sporting a woodie at in inopportune times. There’s zero chance of that happening, which for me, was a blessing.
After our thirty minutes of running had completed, I did a shorter cool down than Joe. On my way to the water fountain I got to see that beautiful ass in action. I recalled grabbing onto it when Joe pounded me out over a month ago. The memory was so vivid. The contours and the flexing of his glutes…and my mind drifted away.
“Are you heading for a shower?”, Joe asked, startling me back into the present.
“Oh…ah…yeah. Let’s go.”
I hoped Joe couldn’t read my mind because that would have been terrible.
We headed back into the locker room and stripped off our sweaty clothes. This time I got to see Joe wrapped in a towel, and I didn’t have to hide that I was checking him out because it was all out in the open. Joe did give me a knowing look, fully aware that I was checking him out, not like a usual bro seeing another bro head to the shower, more like a gay guy worshipping a straight guy’s physique, and then a cheeky smirk formed in his face. He knew what was happening, I had no doubt.
I wish I could tell you there were open showers at this gym, but that was not the case. Individual stalls with full doors. We each took one and rinsed off the sweat and afterwards, another look at Joe’s wet and glistening muscled body wrapped in a skimpy towel. While I was soaping up, I pictured Joe soaping himself up just next to me, and that visual made my hole quiver. Not enough to poke a finger inside it, but it did pucker for sure.
We dressed and the show was over. We were both fully clothed now.
“Wanna grab a celebratory drink?”
“What are we celebrating?”, I asked.
“That you ran for thirty minutes for the first time in over two years and didn’t need to stop. That’s pretty good if you ask me.”
“Thanks, yeah, sure, let’s go.”
We headed to our favorite bar and ordered a couple of martinis.
A few sips in and things and the alcohol washed away our inhibitions.
“You were checking me out while we were running. I saw you, Richie.”, he exclaimed, with no attempt to be subtle.
“No I wasn’t. Stop accusing me!”, I was determined not to crack and admit to anything.
“You can deny it all you want but I know what I saw, and then in the locker room you did it again. You’re perving on me.”, and that same knowing look grew on his face again, the one that saw right through me.
There was no point to try to deny it any longer.
“Joe, what do you want me to say, you’re a very attractive guy. I’m gonna look, just deal with it.”
Joe and I took more sips and ordered a second round.
“So you really think I’m hot, huh?”
“Yes, I’ve already told you that.”
“I wish my wife was here, Richie. I miss her. I haven’t had any sex since…”
“Since what, Joe? Since we hooked up?”
“Yeah, that. What about you?”
“Well, not that it’s any of your business but Jace and I hooked up a few times since then.”
“Are you guys dating or something?”
“No, I told you, we’re just fuck buddies and he’s my keyholder. There was a time when I wanted more, but a man like him doesn’t do relationships. I don’t even know why I’ve kept it going so many years.”
“I can tell you why, Richie.”
“Oh yeah, why?”
“Because you like dick, and you love his dick. I think I’ve learned by now that you’re a real slut for dick.”
I was blushing.
“Joe, you’re my boss, I can’t believe you just said that to me. I report you.”
“I’m not wrong, Richie. You obviously like how he dicks you down and that’s why you keep going back for more, and I told you already that outside of work I am not your boss so stop saying that!”
“Ok, ok, you’re not wrong about that. I also think he’s a great guy and I trust him. Hell, the man has been holding the keys to my cage for over four years, so there’s that, too.”
“So when’s the last time you hooked up with him?”
“Joe, why does it matter?”
“Because I want to know. Just tell me. At least one of us is getting laid.”
“Two nights ago I went over to his place.”
“And”
“And what?”
“You went to his place and what happened?”
“I don’t know, we started making out. Jace reached into my pants and squeezed my nuts and…”
“Wait! Squeezed your nuts?”
“Joe, you asked me to tell you what happened and now I’m telling you. Yes, Jace likes to torture my heavy balls. Since I rarely cum they are always full. He gets a kick out of watching me squirm when he does it.”
“I guess if that’s your thing, I’m not judging. So then what happened after that?”
“He sat in his recliner, smoked a little dope while I sucked his cock for a long while until he was ready to take me to his bed. Then he knocked me up a couple of times.”
“A couple of times?”
“Yeah, Jace is always good for a couple of rounds.”
“I guess you don’t have to tell me the details about that. I get the picture. Did you stay over?”
“I did, but I don’t always stay over.”
“It must have been nice to have someone to sleep next to.”
“It was”
“Oh Richie, you’re so lucky,”
“Lucky?”
“Yeah, you gay guys seem to have sex all the time. I feel like I’m missing out.”
“I’m sorry, Joe. I wish it were different for you. You’re in the prime of your life. You should be enjoying it while you can.”
In an effort to console my boss, I placed my hand on his thigh. Damn, it was thick as a tree trunk. Before I could remove it, Joe took a look around us and I guess he thought nobody would notice, he moved my hand over his throbbing crotch.
“Joe, what are you doing?”, I whispered.
“I’m showing you how desperate I am for attention, Richie. You feel that? Listening to you talking about Jace made me fucking hard. Now what am I gonna do?”
“Joe, look around. There are so many women here. I’m sure you can find one to take home tonight if you really wanted to.”
“No, no, I’m still married. I don’t wanna cheat on my wife with another woman.”
“Joe, what are you saying?”
I needed him to say it. I knew where this was going, but I needed him to say it.
“I’m saying I wanna go back to my place. Let’s finish up here and go, ok?”
“Joe, do we really want to do this again? I don’t know. I mean, you’re my boss. This is so wrong. You’re the CEO, what if we get caught?”
“We’re not going to get caught because nobody will see us and nobody will know. We’ve already done it so I don’t see what the big deal is, and I know by the way you were gawking at me earlier, you want it, too. So let’s stop all the bullshit and go!”
Joe was getting bossy and in doing so, I was becoming his little bitch. I’m extremely turned on by power exchange and men telling me what to do.
“Is that an order from my boss?”
“Yes! Stop being such an asshole and let’s go already!”
“Ok ok, fine!”
I went to pee and then I followed Jay back to his place.
Once we entered his apartment, he took me into his bedroom and started stripping.
I just stood there and watched because I wasn’t sure what it was that he wanted exactly and because I was enjoying the show.
By the time he realized I hadn’t taken a stitch of clothing off, he was only wearing those camouflage boxer briefs.
“Aren’t you getting undressed?”
“I can if you want.”
“I don’t see how I can fuck you with your clothes on, so yeah, I do want.”
I shrugged my shoulders and pulled off my clothes. I did have a jock under my pants and didn’t take it off.
“You wear a jockstrap even when you’re not working out?”
“Yeah, I like how it keeps my cage tucked nice and tight.”
Joe walked over and took a feel.
“Yeah, I can see that. That thing isn’t gonna move anywhere, is it.”
“Nope, it’s not going anywhere.”
“Can I try something with you?”
“What is it boss?”
“Don’t call me that in here, ok. I’m not your boss now!”
“Yeah, ok, sorry, Sir!”
Joe rolled his eyes in exasperation.
“Lay down here”
Joe had me laying on my back, head hanging from the bed.
“I saw this on a video once, always wanted to try.”
“A gay one?”
“No! Of course not! I’m not a homo, Richie. I’m just horny and you’re helping me out, ok! That’s all this is!”
“Ok, Sir.”
Joe huffed at “Sir”, but didn’t say not to call him that.
“I know how to keep your mouth busy, open up!”
Joe pushed his hard cock into my open mouth. I tasted his salty precum pass over my tongue. He’d been leaking for sure.
Joe gripped the sides of my head like a basketball and began pumping in and out of my throat. I didn’t gag, but I sure was making a mess of myself, throat goo and juices spilling out everywhere.
“Oh fuck, Richie, this feels so good. Gay guys give the best head. Fuck yeah!”
I thought to myself that Joe thinks that all gay gays good give head, but I know from personal experience, that is hardly true. I’d definitely tell him that later!
Joe’s balls were now smacking my face as his cock fell deeper inside my esophagus. That was the first time I gagged and Joe pulled out.
“Come on, Richie. I know you can take it. Open up, let’s try again. I wanna bottom out in your throat, ok?”
After recovering my breathing I nodded my head in agreement. I wanted to do this for Joe. He deserved to feel good, and was gonna make it happen for him.
With more focus and determination, we succeeded. I had swallowed all of his inches and Joe was all too eager to throat fuck me. I tasted even more precum now, which signaled that Joe was getting close.
He pulled out and I looked up and saw his nice rod throbbing. All the veins were swollen, his foreskin completely rolled back, his cock head an angry shade of red. His balls had tightened and risen, too.
“That was close, Richie. So fucking good, but I still wanna fuck you.”
“I’m glad you liked it, Joe. By the way, not every gay guy can do what I just did.”
“What do you mean?”
“You seem to think that every gay guy is a good cocksucker. That’s not true. I am a great cocksucker and I know that, but not all of us gays can do what I just did. You need to know what I’m giving you isn’t common. That’s all I’m saying.”
“Ok, I stand corrected. Well then, I picked the right gay to play with, didn’t I?”
“Yes, you did.”
“Now let’s see how that ass is tonight.”
“Oh yeah? Is that what you want?”
“Yes, I do. I wanna fuck you on your hands and knees.”
“Do you?”
“Stop asking questions and just do as I say! Cut the bullshit!”
“Yeah, ok, SIR!”, I emphasized.
Joe actually smacked me on the ass after I said it.
“You’re insubordinate you know that! Reach into my nightstand and get me the lube.”
“You just hit me!”
“I know what I did and I’ll do it again if I have to, just get methe lube already!”
Joe had an opened tube of K-Y which no gay man I’ve ever met had in his lube assortment. I grabbed it and passed it back to him while I positioned myself on my hands and knees, just like Joe wanted.
Joe kneeled behind me, first pushing some into my butthole with his finger and then coating his hard cock with it. He threw the tube beside him on the mattress and I braced for that initial insertion.
Joe pressed his dick head up to my assring and gave a shove strong enough to break through.
I gasped and told myself to count to ten to work through the initial discomfort.
“You ready for more cock?”
“Uh-huh”, I said.
My head rested on my right forearm and my eyes were tightly shut. Joe gripped each side of my hips and pressed forward, his cock so slick it wasn’t gradual by any means. From just the tip to his entire cock, a new round of discomfort passed through me.
“Just stay right there a minute, ok?”, I pleaded. I realized that Joe hasn’t had much experience with fucking assholes, so I wasn’t mad at him.
“Yeah, ok. Tell me when you’re good.”
I hesitated a few more seconds until my hole settled down and relaxed.
“Ok, I’m good.”
“You sure?”
“I said I’m good, yes!”
Joe smacked my ass again.
“What was that for?”
“I don’t like it when you raise your voice at me like that. Don’t do it again.”
“Ok, Sir!”
Joe gave me another half-hearted slap and then his hand picked up where it was before resting on my hip along with the other one.
Joe took his hips back and pressed forward again. I felt his hardness claiming more space and depth inside my rectum and with a few more slams of dick we’d hit maximum depth.
“Awwww, Richie this is ass is so good. I can see why Jace likes to fuck it all the time. I would, too, if I could.”
That was not anything I ever expected to hear from Joe while his cock was buried inside me. I chalked it up to the moment and the alcohol. In his right mind, Joe would never say anything like that.
“You like my cock up your ass, Richie? Does it feel good for you, too?”
“Ohh, yes, it does. Keep fucking me! You can go as hard as you want. Don’t hold back.”
Truth is, my hole enjoys a good pound out and if the top hits my p-spot, I’d likely cum, too.
“Really? You want me to go harder?”
“Yes!”
“Be careful what you ask for, Richie.”
I knew Joe was strong, but strength doesn’t always translate to stamina in bed. Joe literally fucked me so hard and for so long that somewhere along the line he knocked the cum right out of my balls! I was defenseless to his insistent cock rubbing against my prostate over and over and over, it was inevitable.
I felt drops of sweat landing on my back as Joe continued to pound away, ignoring my orgasm and solely focused on his own.
“I’m gonna cum soon, Richie. Where do you want it?”
“Put it inside me! Cum up my ass!”
“Yeah, I’m gonna fuckin’ blow my load up your ass now, Richie! Fuckin’ take my cock! “
Joe swatted my ass twice.
“Ohhh fuck yes! I’m fuckin’ cumming! Ohhhh fuuucckkk! Jesus! Ohhh yeah!”
Joes cock shot out like a cannon! I could feel his cock twitching inside me, gushers of jizz flying out of his balls and straight into my rectum.
Joe fell on my back and I fell to my stomach.
Joe’s sweaty body smothered mine. I felt Joe’s heart beating fast and his heavy breathing. The scruff of his beard scratched my shoulder.
Joe didn’t say a word. I just laid there hoping the awkward silence would end, but I wasn’t going to be the one to end it.
Joe eventually rolled off of me and laid next to me on his back, hands clasped behind his head looking like he just conquered the world.
I looked over at him, still on my stomach.
Our eyes met and he said, “Fuck Richie. I needed that. Thank you for being here tonight.”
“You’re welcome”, I said. “Hey, can I get some water?”
“Yeah, bring me some, too.”
Once again my boss was ordering me around. I just peeled myself off the bed and went to grab two glasses of cold water with ice and came back to the bedroom and sat at the edge of the bed next to Joe.
“So…do you want me to go now or…?”
“No, you don’t have to leave. I mean if you want to go I’m not going to stop you but if you want to stay you can.”
Oh shit, more head games.
“Joe, just tell me what you want and I’ll do it, ok. What do you want me to do?”
Joe placed his hand on my thigh and said, “I’d really like if you spent the night here. I don’t want to be alone.”
“Ok, I’ll spend the night. Do you mind if I take a shower though, I feel sticky.”
“Not yet, ok, just come back to bed with me and we’ll take a shower later. I promise.”
I walked around the bed to the other side and I laid on my side, facing away from Joe.
Joe positioned himself behind me. His arm fell over my chest and his pelvis pressed against my ass.
“This feels nice. I miss having someone to sleep next to, Richie.”
I started to feel used. I was a hole for Joe to unload in, and now a human teddy bear to replace his wife. It was obviously he missed her terribly, but this was becoming unhealthy for so many reasons. I won’t lie and say I didn’t enjoy the sex, but other than that what we’re doing wasn’t good for either one of us, personally or professionally.
I don’t know why, but I shifted my body away from Joe.
“What’s wrong?”
“Nothings wrong.”
“Goddamn it, Richie. Just be straight with me. What’s wrong?”
“You’re using me to replace your wife, Joe. You can’t fuck her so you fuck me. You can’t sleep next to her so you ask me to sleep next to you. You’re my boss, Joe, this is all so fucked up.”
What Joe did next surprised me. Joe softly kissed my back and pulled me back to him so I was nestled against his bigger, stronger body.
“Richie, you’re more than just my employee. You’re also more than just a hole to fuck. I’m sorry if I ever made you feel like that. You’re my best friend. I really like you. I feel a connection with you that I never felt with another man.”
Then Joe’s fingers traveled to across my chest and those same fingers latched onto one of my hard wired nipples and gave a little, gentle, twist. He found the very spot that makes me weak in the knees every single time.
“Thank you, Joe. I think I just needed to hear that. I had no idea you felt this way.”
Joe pulled my torso back so now I was facing him as he hovered over me.
His lips found mine and we kissed, no tongues, but it was tender and sweet. I felt his cock hardening against my thigh.
“What’s that?”, I asked.
“What?”
“This.”, I said taking his hardening shaft in the palm of my hand.
“You see what lying here next to you does to me, Richie? It makes me hard.”
“Does that mean you want to go again?”
“Yeah, definitely.”
Joe kissed me again and climbed on top of me. I spread my legs for him as his chest pressed against mine. My hands caressed his back as we now included tongues in our lip lock and I let myself be taken by him. All of the noise in my head dissipated.
Joe felt around the bed for that tube of K-Y and rose to his knees to put some over his cock. My hole was still wet from the first fuck, but more lube is always a good idea when it comes to butt sex.
I pulled my legs back so Joe would have a clear view of my bullseye and this time Joe’s slicked up erection found home base quickly. Joe fell right back on top of me, kissing me as he slowly rocked his hips.
“Ohhh Richie. Mmmmm. This is so nice. I wanna take my time with you. I want it to feel good for you, too, baby.”
My fingernails clawed Joe’s back and I grabbed a handful of ass. I felt Joe claiming me, physically and mentally owning me with every passing moment. My hole was the perfect glove for Joe’s penis. I could feel the heat building inside of me. Joe containing his animal instinct to breed me like a caveman and attempting at something more civil.
I wanted to be ravaged.
“Fuck me, Joe. I know you’re holding back.”
“I don’t wanna cum yet, just let me drive, ok, Richie. I got you.”
Joe kissed me again on the lips and then on my neck, and then he softly bit my earlobe.
I cooed into him, gentle moans signaling my reactions to his ministrations.
I could feel Joe tensing up and his cock growing just slightly more rigid. His breathing became more erratic.
This time my hands grabbed handfuls off juicy ass mounds as I felt Joe ready himself for a second orgasm of the night.
“Yes! Yes! Yes! Fuck me, Joe!”, I pleaded.
Joe was grunting like a savage now. No more holding back.
“Grrrr, fuck Richie. I’m gonna cum again! Ohhhhhh, ohhhhhhh, ohhhhhh my God! Ohhhhhhg fuck! Ohhhhhhh man!”
Joe let himself cum with no inhibitions at all, fully free to express the pleasure of his orgasm while dumping another one of his loads inside me.
Joe was panting and sweating again, this time we were face to face and not chest to back.
Instead of saying anything, Joe kissed me again.
“Ohhh Richie. I…”
Then he cut himself off.
“You what, Joe?”
“I love what we just did. I love having sex with you. This was so hot. You’re so hot.”
In my typical pattern of diffusing uncomfortable moments with humor, I said something really stupid.
“What if the rest of the executive team saw us right now. They would die!”
I didn’t want to admit any feelings so I deflected altogether. Bad move.
Joe rolled off of me so quickly and went straight to the bathroom to wash up.
When he came back to me he said,
“Why’d you say that, Richie? Of all the things you could have said, you said that! I just told you I love having sex with you and that I find you attractive and that’s all you got?”
Joe’s cock was no longer even semi-hard. He was naked, uncut cock dangling loosely as he yelled at me with his usual animation.
“Hey, I’m sorry for what I said. I always say something stupid when things get too emotional. I’ve done that all my life.”
“Yeah, well, it was stupid, but I’m sorry for snapping at you.”
“So…umm”
“Um what? Just say what you want to say Richie. I told you no bullshit!”
“Ok. I really like you, Joe. I like having sex with you, too, and you already know that I think you’re hot.”
“You can’t keep your eyes off of me, especially in the locker room.”
“No, I mean, look at you. Who could not look at you.”
“So did you want to take that shower now?”
“Yeah, I do. Do you want to do it together. There’s room for the both of us.”
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