In Deep (Part 4) - Jake

I stared down into the toilet bowl, trying to will my hard on to soften a bit so I could pee. My cock was not cooperating. Finally after channelling my best Homer Simpson, willing myself to think unsexy thoughts, the stream finally broke through.

I washed my hands, getting ready for dinner like SIr had said to. I checked my hair in the mirror and could hear the sound of drawers opening on the tool chest. Then the jangle of metal clinking on metal. When I was first chatting with Sir online, he had shared some pictures of his toy cabinet. He and Matt had a sizeable collection of gear and I was excited to see what he was getting out. I noticed it first in person on my way to use the washroom when I first arrived, and had been hoping for a bit of a tour. I dried off my hands and opened the door, hoping Sir would be still outside looking through the gear.

“Take these out to the main room and wait for me there boy, just trying to find the right set of locks for them” he said, handing me a set of padded leather cuffs with locking buckles.

“Okay” I replied.

“Okay, what boy?” he said, cocking an eyebrow expectantly and staring at me.

“Okay SIR!” I responded, slightly embarrassed.

“That’s better boy, I’ll be over in a second.

–

I walked out into the main living area in the basement, as instructed. Matt was standing with his back to the wall about two feet off the end of the sectional, along a small stretch of empty wall, almost in the corner. His hands were at his sides, staring forward, statuesque. Sir must have woken him up out of trance while I was in the washroom and ordered him to wait there. I wasn’t quite sure what I should be doing, so I held onto the set of cuffs and sat back down.

Matt didn’t move or make any effort to acknowledge I had come back, it was making me feel kind of awkward, but I couldn’t help but steal a closer look at Matt’s package. I wanted to reach out and run my hand over his crotch, get a little feel, but didn’t dare. Sir had mentioned he had rules for sessions, and he was strict about them, like calling him Sir, or Master. But we hadn’t talked about all of them over Grindr, just mentioned in passing, and I didn’t want to risk being caught unknowingly breaking one out of respect, and a bit of fear there might be repercussions later if I did.

“That’s it, good boy,” Sir said as he walked back into the room. I wasn't sure what I'd really done beyond sat back down.

“You’re doing great." He continued. "In a minute, Jake and I are going to put the set of leather cuffs that Jake brought out with him on you. You’re going to stay nice and deep for me, but you’ll still be as responsive and able to move and stand, just as you are right now.”

Turning to me, he said “I’ll be back down in a second, just going to throw the pizzas in, I think I just heard the oven reach temperature”.

“He’s still hypnotised!” I exclaimed “I thought you had just told him to stand there and ignore me until you came out”.

He laughed lightly as he went up the stairs and then said “You almost sound jealous boy. Don't worry, your turn is coming soon”.

–

We ate quickly and then I helped Sir clear the table. Matt wasn’t a ton of help, he moved very deliberately, almost robotic throughout the course of the meal, and Sir had to keep prompting him through the most basic of things.

At one point as we were clearing the dishes, Matt was left seated at the table staring out into the living room. Sir said to me “This is the longest I've kept him under like this and I wasn’t sure exactly how it was going to work. But the effect at the end for him is going to be so awesome if I can pull it off” as he loaded plates into the dishwasher.

“It’s ok for him to be so out of it like that?” I asked “What do you mean by 'the effect’?”

“When we are done here, we’re going to go back downstairs and you and I are going to set up that massage table you probably saw leaning up against the wall. Then I'm going to tie Matt down and bring him back fully out of trance. If I’ve done a good job setting him up, I did some quick work with him while you stepped away to take a piss before dinner, he shouldn't remember much since I put him under on the couch for you. For him it will feel as if no time passed and he’ll wake back up in full bondage.” he paused, and looked over at me, and then said “That sort of trance takes time and practice. Not saying we won't get there if you want it eventually, but you don’t have to worry about ending up like that tonight”.

“I’m feeling pretty comfortable with you guys, if you want to tie me up as well you can” I said. I was breaking my usual rule, no hardcore bondage on the first date, but we’d been talking for a while, and I felt like I could trust them.

“If you want to be a boy, but no pressure here, I’m fine if you want to just try going into trance for me and then having a bit more vanilla fun, ease into things tonight.

“I still want you to try and put me under. I’m even more a believer now than I was earlier” I said, looking back over at Matt, sitting wearing the set of cuffs, his chain collar, and a jock. The quintessential picture of what I’d conjure up in my mind when jacking off to the thought of being a bondage slave. “But I’d be down for some bondage as well. If I’m feeling uncomfortable I’ll just yell something ridiculous, like 'purple pina colada' as a safeword or something”

“Ha, love it, as long as you're feeling good about it all” he said. “Go grab condiments from the table and throw them in the fridge” he said and slapped my ass as I walked away.

–

After Matt was securely, and in my opinion, inescapably strapped down to the table, Sir had me sit down in the chair beside the couch. He brought Matt back out of the trance, and I watched as Matt struggled against the bonds, quickly realising the situation he was in. Trapped. We had taken off Matt’s jock when we had strapped him down, and now his cock, free from the fabric pouch, was at full mast and had a large bead of pre-cum forming. I could tell he was enjoying it, but from his initial struggle, it must have been at least a bit surprising.

Sir talked me through some basic hypnosis 101s, that it all was contingent on me relaxing and just going with the flow. He’d talk me through an induction and help take me down into trance. I might go deep, or I might not, but I’d go into trance either way. Even if I didn’t think I did, it doesn't mean that I can’t be hypnotised and we could always try again. I was assured my mind wouldn’t let me do something that I didn’t want to do, and that he wouldn’t try to push boundaries or manipulate me on any of my limits.

"Are you ready?" he asked.

“Yes Sir” I said. Took a deep breath and I started to let go of any last nerves I was holding onto from the anxiety of first hook up and listened intently to the sound of his voice.