--------------Chapter 24--------------------
***Normal cautions apply up front. This story contains sexual content including some underage content that may be offensive. If you're offended by man to man sex, BDSM and other similar topics, this isn't the story for you. If you are underage in your area to read this, don't read it. There may be unsafe sex described in this story...be smart in the real world and make good choices.
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***This story is a work of fiction and should not be taken to represent any real people. That being said, there were several "inspirations" for characters but I've tried to keep them different enough to protect the innocent and not so innocent.
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------------From Chapter 23-----------
Once we got home, we all got into the master suite shower together. We spent almost a half hour soaping each other up and groping and fondling each other. Afterward, we all crawled naked into the massive bed and Kyle and Jorge fed me their cocks and fucked me before we all fell asleep in a tangle.
------------Chapter 24---------------
The next morning began, not surprisingly, with more sex. I had the fun of waking each of my masters up by crawling under the covers and sucking their cocks. My efforts were rewarded with their cum.
As Kyle was coming down from his orgasm, Jorge said "I've got to go take a piss" and started to get out of bed.
"May I SIR?" I asked.
"What, take my morning piss?" Jorge said with a surprised look. "Are you sure?"
I answered by crawling between his legs and taking the head of his still semi-hard cock in my mouth.
"You little piggie" Jorge said with a smile as he began to piss in my mouth.
He was right, it was strong but I happily swallowed every drop and made sure to lick the slit and clean the head properly before pulling off.
"Hot" I heard Kyle say.
I immediately jumped back between his legs and took the head of his cock in my mouth. Within a few seconds, he was also feeding me his golden juice.
"Well now that is out of the way, let's get some breakfast" Jorge said.
"Coming right up SIRs" I said, jumping out of bed and heading for the door.
"Josh, hold on a minute. Come back here" Jorge said.
I returned to the bed where these men lay, wondering if I had messed up something.
"We need to discuss if your submission to us is just in the bedroom and playroom or if it's 24x7" Jorge said. "You are not expected to serve us all the time."
"Speak for yourself" Kyle said with a grin. "Nah, he's right Josh. I am enjoying domming you but I also enjoy being your buddy and hanging out."
How had I been so lucky?
"Tell you guys what" I began. "Let me go cook you breakfast as a thank you for arranging that amazing party and for making me feel so good here in this bed. Ok?"
"Ok man" Jorge said.
In the kitchen, I prepared egg white Denver omelettes, fresh fruit and toast for Jorge and Kyle. I wanted to minimize solid food for myself since I was sure there would be some more fucking in my near future so I made myself a protein shake and a cup of coffee. I set out cups by the brewer for Josh and Kyle when they came down. I set the table in the kitchen and texted the men to come down for breakfast.
"Give us 10" Kyle texted back.
Interesting, they don't even need to get dressed. What's taking 10 minutes.
15 minutes later, Kyle and Jorge entered the kitchen. Kyle had a goofy grin on his face and Jorge appeared to be trying to contain something.
"What's the deal?" I asked as I served their plates.
They looked at each other and Jorge said "go ahead Kyle. We should not have secrets."
"Well, uh" Kyle began. "After you left, Jorge and I were laying there checking our phones and talking and I noticed his cock laying against his leg."
"Ok" I said questioningly.
"And, I don't know what came over me, but I reached over and began to stroke it" Kyle said, turning very red in the face.
"Ok" I said questioningly.
"I sucked him off" Kyle blurted out. He seemed scared of my reaction but relieved to have said it.
There was a perceptible pause in the room as the three of us looked at each other. Three naked studs around a breakfast table who were discussing one of us sucking his first cock, at least I assumed it was Kyle's first.
Jorge finally broke the silence. "It was very spontaneous Josh. Neither of us were planning on this happening and I'm, honestly, not sure what it means. Most of that will be determined by Kyle."
Kyle looked like a deer in the headlights.
"So, Kyle, was that your first cock?" I asked.
"Yeah" he said, looking down.
"And did you like it?" I asked.
He looked up and began to grin sheepishly, "yeah."
"And was he any good?" I said, looking at Jorge. "Was he as good as me?" breaking into a grin.
Jorge grinned back.
"I'm not going to cum and tell but let's just say I wasn't disappointed and I would not have known it was his first if he hadn't told me" Jorge said.
We continued to eat our breakfast in an awkward silence.
Kyle finally spoke. "I don't know, right now, what this means. Ever since we started playing together and hanging out together, I've been feeling more drawn towards men. Jorge, hope you don't mind me saying it, but I've been crushing on you since I met you that first night at your diner."
"I'm flattered" Jorge said, smiling.
"And Josh, you turn me on big time but more as a bottom. It doesn't mean I won't flip with you now and then but I think our relationship is as buddies and as sex partners with you serving me."
"Ok" I said. "So what relationship do you think you and Jorge should have?"
"Honestly, I don't know that Jorge wants a relationship with me" Kyle said, looking at Jorge.
"Whoa" Jorge said, putting his hands up. "Let's take this a step at a time. Josh, you know we've never been exclusive and, honestly, an exclusive relationship is not what I'm looking for. That being said" he continued, looking at Kyle "if it's ok with Josh, I'd love to explore some sort of relationship for us. It can be just sex, it can be BDSM, but maybe we just let it evolve to where it goes naturally."
"I'm totally ok with it" I said, smiling.
Kyle let out a breath that it seemed he had been holding while Jorge talked. "Thanks man. Yes, let's just see where it goes."
"Ok, well I need to go get myself ready to pay my amends for my first drink fuck up customer" I said. "Didn't you say first guy would be here at noon?"
"Yeap" Jorge said. "The guy in the football pants."
My cock immediately began to swell.
"Fuuuckk, he was hot" I said.
"Yes he was" Kyle said.
I turned to him with mock surprise.
"Hey" Kyle said. "I like looking at guys as much as anyone."
"Ok boy" Jorge said, assuming a more directive tone towards me. "Downstairs, clean inside and out. After that, come back up and find us."
"Yes SIR" I said, clearing the table and heading downstairs.
As I walked out of the kitchen, I glanced back at Jorge and Kyle. They were both drinking coffee and looking at each other. Interesting turn. I was very happy for both of them.
When I was done with a thorough inside and out clean, I went upstairs and found Kyle and Josh sitting in the living room watching ESPN.
"Ready SIR" I said.
"Ok, let's get you ready" Jorge said.
"Yes SIR" I said.
Jorge lead me back down to the playroom had me lay on the platform in the middle of the room. Over the next 30 minutes, he tied me in an elaborate rope arrangement. My legs were bent and my upper and lower legs each bound together in a frog tie. A rope harness was put over my shoulders and around my waist. Ropes were also tied from the harness between my legs and to the front and back of the shoulders of the harness.
Finally, my arms were tied behind my back in shoulder to wrist restraints so that my arms bent at a right angle at the elbow.
Jorge then brought a hook down from the ceiling and connected it to the harness around my torso and under my legs and began to lift me off the platform. I was suspended in a sitting position with my legs tied up against themselves. It was surprisingly comfortable.
"So, are you sure you're ok with Kyle and me exploring?" Jorge said. "No dom/sub talk. Be honest."
"I'm totally ok with it" I said. "If I've figured nothing else out about our lifestyle, conventional is not part of it! Do what feels right but please be gentle with him, Jorge. I don't think he's quite ready for this level of play."
"Nothing to worry about man. Unless something surprising happens, I don't see this going beyond sucking and maybe fucking any time soon" Jorge said.
"Fucking?" I asked.
"While you were down here getting ready, he and I talked and he wants me to fuck him, so, he's upstairs prepping and, while you serve your man, he and I are going to fuck" Jorge said.
"Wow, moving fast" I said.
"I think this is something that's been building in Kyle for a while. This weekend has just been the opportunity to release it" Jorge said.
"Well, your guy should be here in 15 minutes or so. I'm going to go upstairs and meet him" Jorge said. "Now don't go anywhere."
"Funny" I said.
After Jorge had left, the room got quiet and I had some time to think while hanging in mid-air. About what I was doing, what Kyle and Jorge were doing, about my life in general. Where did I want it to go? What was college going to be like?
After what must have been more like 30 minutes, the door to the room opened and my football pants man stepped in. He was dressed more conventionally today in street clothes. A form fitting t-shirt showed his well developed pecs and tight torso. The ripped jeans were tight in all the right places and he capped it off with a pair of black Chuck Taylor low rise Converse sneakers.
Yummy.
"Jorge tells me I've got you for an hour since he has something else or someone else he's going to be doing" football pants man said. "Before we get started, I'm Eli but you will call me sir"
"Yes SIR" I said.
"You were very impressive last night boy" Eli said as he turned me in mid air and inspected various parts of my body with his hands. "I kept waiting for you to try to stop things but you didn't. Shit, you thanked that one guy for using you as a punching bag."
"I'm here to please men SIR" I said.
"I'm glad to hear that because I plan to be very pleased when I leave. You only got a brief look into my particular kinks last night" Eli said pulling off his t-shirt and making my cock jump.
"When we are done here, you will have a new appreciation of BDSM. I want you to be surprised but just know that I'm not conventional in my tastes. I tend more towards the unusual" as he took off his shoes and socks. He took his socks and stuffed them in my mouth. They smelled and tasted sweaty. My cock lurched again.
Eli left his jeans on and stepped over to the wall of BDSM equipment. The first thing he brought back was a ball crusher. He quickly installed the base behind my cock and balls and brought the hinged top down and used the bolts to begin to close it on my balls.
Once he had it snug but not uncomfortable, he stepped back over to the equipment area. When he returned, he was carrying what looked like a microphone stand except it had a reciprocating saw attached so that the saw end was vertical. At the end of this was a large black dildo, probably at least 10 inches and thick. Eli applied some lube to the dildo, positioned the stand under me and inserted the dildo into my asshole. He adjusted the height of the stand so that the dildo was about two thirds of the way inside me. After plugging the saw in, he returned and set it to a slow in and out pace so that the dildo went completely inside me and pulled about halfway out before returning.
I moaned as the dildo stretched me and rubbed my prostate. My cock was rock hard and dripping.
After tightening the bolts of the ball crusher a few turns, causing me to moan more, Eli stepped over to the equipment and returned with a cane.
"You ever experienced bastinado?" Eli asked.
I shook my head no.
"Know what it is?"
Again, I shook my head no.
"It's caning or whipping of the soles of the feet. It's particularly nasty because you can use a lot of force meaning a lot of pain but not cause injuries" Eli explained as he walked around me lightly slapping the palm of his hand with the cane.
Oh shit.
"Once I'm done with this, we'll move on to some more conventional stuff" Eli said. "But for now, you're in for a treat, well, at least I'm in for a treat."
The pace of the fucksaw was increased some and the ballcrusher was given a few more turns.
Suddenly, my feet felt like they had a line of fire running across them. I screamed into the socks in my mouth.
"That was not even close to what we will get to" Eli said.
Despite how much that statement scared me, my cock seemed to get harder.
For the next twenty minutes or so, Eli administered a severe caning to my feet while periodically changing the pace of the fucksaw and tightening the screws on the ball crusher. My cock remained rock hard and continued to drip pre-cum as I screamed with every crack across my feet.
Somewhere along the way, Eli had removed his pants and was naked, stroking his large cock as he circled me, administering shots to my feet and adjusting the fucksaw and crusher. His cut cock which I guessed to be about 8.5 inches stood up and out from well trimmed hair. His balls hung low and swayed as he walked.
"Here, look at this" Eli said. He was holding up his phone. On the display was a picture of the bottom of my feet. They had red lines across them. As I looked closer, I realized he had done the lines in perfect spacing from my heels to the toes. Each line looked to be the same space from the other lines. While I was aware of how much my feet hurt, I had to be impressed at the precision of his work.
"You should be able to walk when we're done here but you'll remember it for a while" Eli said. "You are an impressive pain slut Josh. Most guys are in tears when I'm done. Not only are you not in tears but you're hard as a rock" and he began stroking my cock.
Looking at his watch Eli said "we've got about 15 minutes left. I didn't get to make you cum last night so I'm looking forward to that and getting a run at your ass before I go."
Eli quickly turned off the fucksaw and removed the stand from under me. He also took the ball crusher off, causing me to groan as the blood returned to my balls.
I felt myself being lowered to the platform again. Eventually I was on my knees, legs still bound in the frogtie and the harness with my arms behind me.
Eli removed the hook from above and positioned me onto my back. He then moved between my legs and slammed his cock into my ass completely. I groaned at the pleasure. Reaching down and grabbing my throbbing cock, Eli set a rapid pace of fucking me ass and stroking my cock. It wasn't long before I felt my orgasm rising.
"Mmm mmm" I tried to yell through the socks in my mouth.
"Oh yeah, cum" Eli said. "I want to see you shoot your load while I fuck your pussy."
That was all it took. I arched my back and yelled into the socks in my mouth as my cock blew shot after shot all over my chest, stomach and a few hit my face.
"Fuck yeah" Eli yelled and began to grunt, obviously pumping a load into my hole.
As we both began to breathe again, Eli reached down and scooped up some of my cum from my abs and licked his fingers. He then pulled the socks from my mouth, scooped up more of my cum and fed it to me. I greedily sucked on his fingers.
"You are one hot little fuck man" Eli said as he extracted himself from my ass and stood up.
I lay on the platform, still tied up, panting.
Eli calmly put his socks back on and put on his pants, shirt and shoes. He then walked over, bent down and gave me a deep kiss. I moaned as his tongue probed my mouth.
"This won't be our last time" Eli said as he stood up and walked out of the playroom.
The afternoon proceeded from there. The other four men who were entitled to time with me only got 30 minutes each. Kyle and Jorge never appeared again but I knew the room had cameras and that they were watching both for my safety and for their pleasure.
The second guy untied me and put me on the bondage table and stretched my arms and legs until I began to moan in pain. He then used a flogger on my abs and chest before climbing up on the table and standing over me while he blew his load on me.
Third guy released me from the bondage table and put me in the sling, cuffing my wrists and ankles. He stretched my ass with several dildos before finishing off by fucking me and cumming in my hole. He shoved a large butt plug in me before he left me in the sling.
Round four featured an older, heavyset guy. He released me from the sling and put me on the platform with my hands tied above my head. He then spent the rest of his time licking all over my body before jacking off his load on my feet and then licking them clean.
When number five walked in the room, I was surprised to see Kyle and Jorge accompanying him.
Number five was about 6'4, looked to be about 55 with a well maintained physique. He was wearing a pair of black leather pants, black work boots and a flannel shirt with the sleeves cut off, showing off large biceps with several tattoos. His head was bald, either naturally or shaved. Sort of reminded me of a BDSM version of Mr. Clean.
"Josh, this is Paul. You will refer to him as Sir or Master Paul" Jorge said. "Paul requested a chance to fist you. I told him you hadn't been fisted before. Good news for you, Paul is a master at fisting and being fisted so he's the right guy to introduce you to it."
My eyes must have given away the nervousness I felt at the prospect of Mr. Clean putting his large hand inside me.
"Relax, Josh. It was going to happen eventually. No better time that now and no better top than Paul" Josh said. "Kyle, get Josh down from here and put him back in the sling."
Kyle stepped up on the platform and released my hands from above. Grabbing my balls, he lead me over to the sling and I got in.
"Restrain his legs and left hand" Jorge instructed. "Use your right hand for these" as he handed me a bottle of poppers with a flip top instead of the normal screw top. Perfect for one-handed operation.
While I was getting set up in the sling, Paul had removed his shirt revealing a leather harness that sat atop a chest covered in hair. He had large pecs with nipples that stood out very distinctly and his torso had a nice V shape that lead down to his pants. He had also removed the front cover of his pants revealing a large semi-hard cock with a metal cockring.
As I watched, Paul put on a pair of long leather gloves that were tight like exam gloves. He brought a stool over to the foot of the sling while Jorge got a small table and set it next to Paul. He then retrieved a large bottle of lube and some towels.
"We're going to start slowly" Paul said in his first words since arriving. "Fisting is not a thing to be rushed. When done right, and I'll do it right, it takes time and small steps of progress. Especially your first time."
"The important thing is to keep eye contact between us" Paul said, looking at me intently. I found myself sinking into his brown eyes. "With that eye contact, I'll be able to gauge how you're doing and either speed up or slow down. And once I'm in, it will further the connection you will experience. These guys" he said referring to Kyle and Jorge "are here watching but this is between you and me, ok?"
"Yes Master Paul" I said.
"Good, now we'll start with removing this plug so I can see what I have to work with" Paul said, pulling the butt plug number three had left in me out of my hole. He removed it slowly and kept his eyes on me the whole time.
My ass felt empty and I envisioned that my asshole was open and puffy from the workouts it had been getting since yesterday.
"Let's clean you up a bit" Paul said. "Kyle, grab me an enema and a bucket."
Kyle retrieved the fresh enema bottle and a bucket.
"I'm going to put this in you" Paul said, referring to the enema bottle "and I want you to clench down and hold it until I tell you to release."
"Yes sir" I said.
I felt the tip of the enema bottle enter me and the cool feeling as the water from the bottle entered my rectum.
"Hold it" Paul said as he removed the empty bottle and handed it to Kyle.
Paul then began to rub my asshole and around my cock and balls. It was a gentle rubbing and we maintained our eye contact the whole time. I felt myself relaxing quite a bit but was careful to keep my asshole tight.
Picking up the bucket and positioning it under my ass, Paul said "Ok, release it and push out".
I did as instructed, relaxing my ass and bearing down. I felt and heard the water splash into the bucket.
"Very nice. Clean other than a fair bit of cum I'd say" Paul said with a grin.
"Josh has had a busy couple days" Jorge said.
Kyle took the bucket from Paul and stepped over to the wet area to empty it and rinse it out.
"Now, let's bring the lights down a little" Paul said. The lights began to lower as Kyle or Jorge adjusted them. Soon, the rest of the room was barely visible outside of the space around the sling. Kyle and Jorge disappeared in the darkness and it was just Paul and me.
Paul continued to massage around my ass, cock and balls. He kneaded the cheeks of my ass and rubbed the upper part of my legs. Again, non-stop eye contact. I felt myself relaxing even more and beginning to feel safe in the hands of this man I'd only met several minutes ago.
Smoothly without breaking eye contact, Paul reached over and picked up the lube bottle and put some on his fingers. I felt him begin to rub the lube around my ass and gently push some inside with a couple fingers. I moaned without thinking.
This continued for a while, Paul adding more lube periodically, increasing the number of fingers he was putting in my at once.
"Take some of those poppers" Paul said quietly. I took two hits in each nostril.
As I felt the poppers kick in, Paul began applying slightly more pressure at my hole. I couldn't tell how many fingers he was using but it felt amazing.
Paul continued to apply pressure. A couple more times he had me take some poppers.
"I think you're ready" Paul said after a while. "Just keep breathing calmly. It's going to feel strange and might be a little painful but that passes, quickly."
At that, Paul put his other hand around my leg to keep me from moving backward and began to bear down on my hole with his hand. I could feel my hole spreading more and more.
"More poppers" Paul directed and I complied.
As I capped the bottle Paul said "Deep breath in" I took a deep breath and held it.
"And let it out" Paul said.
As I released the air in my lungs, Paul pushed and I felt my asshole expand even more. There was pain but nothing major for me. Suddenly, I felt his fingers moving inside my ass. I cried out involuntarily. Not from pain but from pleasure.
"And you've been fisted for the first time" Paul said with a smile. "What do you think."
"Holy shit" I said. "Holy shit!"
Paul chuckled. "Yeap, I think I might have said about the same thing my first time. Now, let's take this ass for a ride and see what it can do."
Paul kept the gentle but persistent pace we had been doing throughout. His free hand continued to massage and rub me all over, even moving up to my abs and chest, tweaking my nipples.
While he was doing this externally, inside me his hand pressed forward. Every once in awhile he would encounter some resistance and coach me through poppers and breathing.
Throughout it all, we maintained eye contact. The connection felt so much deeper than physical. It was like we were reading each other's thoughts.
After a while, I had no idea how much time, Paul began to stop applying forward pressure and began to back out of me.
"Stop, no" I pleaded.
"It's time for a break Josh" Paul said gently. "Don't worry, you'll get more of my fist and perhaps others later."
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