In Deep (Part 3) - Sir

I had been talking to Jake for the better part of two weeks, and was very excited when he finally said he was ready to meet. He seemed very eager, but was somewhat new to kink. I was trying to be realistic, guys were often attracted to the fantasy of it all, often ended up having second thoughts and ended up getting cold feet and ghosting at the last minute. I had tried to check my expectations, and yet here I was standing in line at the cash at the local sex shop, holding a matching large Doc Johnson silicone butt plug to the one in our collection at home, picturing the things I had in store for him if he ended up showing.

The young couple in line in front of me was trying to use a coupon for sort of water based lube and there was much discussion about if it contained a particular ingredient with the sales clerk at cash. The woman had an allergy and they would forgo the 3 dollars off if needed and to the local pharmacy and stick with the brand they normally bought there if it did. It seemed to be the only thing they were buying, and thought about how strange it was to come to sex shop, only to buy lube explicitly because it was on sale. I pegged them as extreme coupon-er's and tuned them out. I didn’t need to hear how this ended, I knew it was going to be a poor life choice and quickly returned to daydreaming. I had Matt and Jake on all fours beside each other in front of me on the couch, their toes curling as my thumbs pushed the base of the plug deeper into their asses My hands were resting flat on the tops of their lower backs with my thumbs continuing to drive them deeper. They both made guttural noises of enjoyment while I was working their holes.

“Next” the clerk called, shattering the image. Jake better not flake out.

–

After having dropped the plug and pack of condoms I had picked up back at home, being sure to take the plug out of the package and put it with the others in the tool cabinet in the basement for quicker use later, I headed out for the park we had agreed to meet at.

As I walked, the late summer sun heated the leather of my biker’s jacket. I used to ride, but had not in years. I had gotten a little older, my biker bear side fading as I grew more into my domineering Sir/Master/Daddy self. There were still elements from my biker days that I held onto, I adored the look of a nice jacket. I pulled out my phone as I walked and flipped through the pictures Jake had sent me, getting turned on again.

The boy was hot. He was shorter than Matt and I, around 5’7” with a slender build, but he had some lean muscle on him as well. A self proclaimed exhibitionist and slut, he loved playing with his ass, often putting on cam shows on Cam4 and other sites. He loved the idea of chastity and what he had seen online on gay twitter about it, and had fantasies of being made to be a sex toy for an older man or group of men to use. Our interests were congruent.

He became intrigued when I had started talking about hypnosis, and we had chatted at length about it. He seemed genuinely interested, but had reservations and I suspected he doubted if it was actually real, but that was not a deal breaker by any stretch. I put my phone in my pocket again as I rounded the corner and took the path along the easement between two houses, a short cut into the park. I looked across the ball diamond to the picnic pavilion and there sat the boy from the photos. Even at this distance I could make out the nervous smile spread across his face when he saw me approaching.

We chatted for a little while, and when he was feeling comfortable we started to walk back to the house.

“Mind if I ask about your and Matt’s relationship? He really doesn’t mind you chatting with other boys?” Jake asked me as we walked.

“Matt is my sub as much as he is my partner. We are committed to each other and love each other an incredible amount, more than words can really describe. Our Dom/sub dynamic exists not just when play, it carries subtly into everyday our everyday life and other elements of our relationship. We usually play with other guys together, neither of us feel that having fun with others guys and the spark and spontaneity that comes with it diminishes any of those feelings." I paused for a minute, looking to gauge his reaction.

“I’m open with the boys I talk to online and in my profiles that Matt is a part of my life, and my goal is always to find someone we get to have fun with, and ideally someone we can maybe share our relationship with. Find someone interested in maybe more than just a one night stand.” Being honest was the right call, but a part of me worried I was oversharing.

“We had a guy, Tanner, who we used to play with frequently, for nearly three years on and off” I continued, “It was a great dynamic and we learned lots about ourselves, about being open and communicating, the pitfalls of emotions like jealousy, and we had crazy amounts of freaky kinky sex” I chuckled.

“That’s awesome to hear,” Jake said. “I was really nervous about the idea of meeting a couple and what Matt was going to think”.

“I told him you might be coming over earlier this afternoon, he was very excited” I said, trying to put him at ease. Besides, Matt wasn’t going to be doing much thinking tonight, and if I had it my way, neither would Jake.

–

Once we got to the house I made introductions and we chatted for a while. Given Jake had his hesitations about hypnosis, I wanted to put on a little bit of a show for him using Matt as my subject.

“Go ahead, tickle him” I said, knowing full well Matt was out like a light, focusing so intently on the sound of my voice, his subconscious successfully suppressing any efforts by his conscious mind to take over, dragging him deeper into relaxation each time, exactly as I’d trained it to. People always think it’s the hypnotist putting their subjects into trance, when in reality it's the subject putting themselves under, the hypnotist just helps them along. Once the subconscious lets the hypnotist in though, that was a different story. For a Dom like me, a boy's mind was stronger than the heaviest restraints, A boys mind would always be one of my favourite toys in my dungeon, leveraging hypnosis or otherwise.

Jake gingerly lifted Matt's leg off the couch and let it fall a few inches back to the couch. I watched as curiosity got the better of him. He smirked while he ran a light finger down Matt’s rib cage, which ordinarily would have usually made Matt flinch, if not outright protest. An involuntary muscle spasm caused a ripple across Matt’s torso as Jake neared the band of Matt’s jock, his finger tracing more slowly around his hip. He switched his attention back to Matt’s right foot, clearly enjoying himself and attacked his sole quickly with five rapidly twisting fingers, his focus turning to Matt’s face which stayed relaxed and slack.

“Damn, that is crazy Sir. Alright, i think I buy it That's so cool. You’re sure you can put me under like that too?” Jake asked, still in disbelief.

“Yes, fairly certain, if you are feeling comfortable enough to relax and are willing to give it a go?

“Ok. Put me under Sir. How does this work?” he said.

“Let’s grab a bite to eat first” I said, resisting the urge to skip the meal entirely and start playing with him. “I’m glad you are curious. I can show you a bit more with Matt, setting up a little more for us to have a good time tonight and then we can really get into it. Go wash up boy”.