How I Found a Keyholder Ch. 08


8.a: serving Tony

It was Wednesday, and I had to head over to Sir’s for my regular inspection. I was expecting something perfunctory, which I was looking forward to for a change as I was eager to head on to my next stop, with visions of that gloryhole in the department store restroom dancing in my head.

But as he gestured at me to wait while he worked on his computer, I was reminded that Sir’s pace and timing were unconcerned with my needs. Surely he knows I have to get done at the department store before work, I thought to myself, then realizing he indeed knew that very well and was surely enjoying watching me squirm with anticipation. So I tried to calm myself and wait patiently.

It felt longer, but he only kept me hanging for ten or fifteen minutes before he turned his attention to me. He had me briefly stand up to examine my cage before signaling for me to return to my knees, then addressed me. “You’re getting used to being seen now, and getting used to being out in the world as a locked sub, which is good. But you need to start accepting even more that this is part of your life, something that people who know you know about you.

“Your friends you were with on the night we met have obviously already found out what you’re up to, so you’re going to spend some more time with them, and get used to the idea of your friends thinking of you as a locked sub.”

“So I reached out to them.” He looked over at his computer screen and clicked to a different tab in his browser. “James and Tony and Edward. They were all enthusiastic about this. So basically, you’re going to serve each of them for a night, in whatever way they want. They’ll be getting in touch with you.”

That hit me as a shock. It was one thing to be carrying on with strangers, but these guys were a part of my life. It definitely felt like a different category. But the misgivings were pushed aside by that other voice in my head. This is what you asked him to do. You agreed that he was the one making decisions. If you only submit to the things you want to do, that’s not submission.

So I sucked it up. “Thank you Sir,” I said.

* * *

I actually got a text from Tony that night at work, when I was mostly de-frazzled from the afternoon’s events at the gloryhole. I don’t know if he’d won a paper-rock-scissors with the other guys or if they figured going with Tony first would be easiest on me. I knew him the least well of the three friends, and he was a pretty quiet, introverted type like me. He also broached the subject like it was my choice to make, and not an order from Sir.

“Hey, do you want to get together to hang out soon? When is good for you?”

He seemed to want this to happen as soon as possible, and I decided there was no reason to stretch out my uneasiness, so I suggested Tuesday night next week. If I was going to be his for the night, might as well do it on the night before my day off.

“Great! Just come by my place when you’re done work.”

Sir must have passed along a green light after my inspection that afternoon, as I also had a text from James that night. “I’m going to the regional ComicCon for the weekend at the end of the month. You should come with me.”

In the context of Sir’s news, I took that as more of an order than an invitation; still, sounded like it could be fun. I knew that James did the circuit of conventions, so he’d know what was interesting there. And at least I had a month’s notice. I wasn’t really planning on taking any time off over the holidays, so I had some days available, and I figured I’d be able to get that weekend off.

* * *

To my surprise I felt a little wobbly when Tuesday came around, mostly because I literally had no idea what to expect. I should be prepared for sex, I figured — that was the implied goal of the whole thing, but I realized I didn’t really have any idea what Tony was into. Although my friends used to try and embarrass me by talking about what I used to think of as “gay stuff”, Tony had kept mostly quiet in those sessions.

So I was definitely feeling unusual as he let me into his condo — awkward, but with the buzz of anticipation I’d been feeling when Sir had sent me out into the unknown.

“Nice to see you,” he said, opening the door with a smile. At least I was being received with friendly enthusiasm. Tony was tall and gangly with short, sandy hair. He did something at the one of the big banks, something vaguely financial that I could never keep straight. It definitely meant he could afford a nice place, in the fortieth floor a new tower with a sweeping view of the city.

“Good news for you,” he said with a smile. “I’m taking you out for dinner!”

That was not the opening I was expecting. “But there’s actually one thing we should take care of first.”

He unzipped his fly. “Would you be okay with giving me a blowjob?”

More out of force of habit than anything, I dropped to my knees and crawled the few steps over to him. His hand was about to reach istanbul travesti into his pants, but I gently pulled it aside and did that for him, fishing out his cock and balls. His cock was exactly the kind that made me drool, his tight foreskin tracing the shape of his cockhead and tapering to a puckered point.

I leaned in and started licking at his balls, which were shaved clean, as I let my hand play with his cock. Then, gripping the top of it, I swept the underside back and forth across my lips a few times, giving it light kisses up one side and down the other. My fingers pinched to retract his foreskin, then pulled it back into place. I repeated that gesture a dozen times, jerking his cockhead, and then squeezed gently. I was rewarded with a drop of clear precome, and I licked at it, then pulling back his foreskin again to lick all around his head. I still wasn’t really sure yet how to “read” a guy to see if he preferred to have his foreskin back or his glans covered, but Tony’s cock was getting hard so things seemed to be going okay like this.

After licking his shaft a little more, I started properly sucking him, moving my hands to his hips and engulfing about half his length and working my head up and down. That brought him to full attention, so I pulled off for a moment and leaned back to admire his cock. He looked to be a solid six inches, and his cock had a subtle downward curve. It looked like it wanted to go right down my throat like that, so I put that to the test, taking in his full length and working my tongue on his shaft while I squished my nose to his belly until I felt my stomach flutter.

Then I pulled back and did my best to deep throat him, feeling his cock pushing in and out of the ring of my throat as I involuntarily made a gek-gek-gek half-choking sound. Again, I could only do that for so long before I had to pull back, spitting a giant wad of saliva along the length of his cock.

“I’m glad I got to do that before dinner,” I said, looking up to look him in the eyes for a few seconds before going back to shallower bobbing with more intense mouth suction.

Tony was definitely responding, and it felt like it wasn’t going to take too long before he’d hit the point of no return. Although usually with Sir I’d never bring my hands back into play without being told to, here I decided the vibe was okay for me to move my left hand over and gently squeeze at his balls as I kept working on his shaft.

That little experimental improvisation paid off a minute later as I felt his balls twitching. I pulled back and just kept my mouth wrapped around his cockhead, tongue working away at his glans. I felt something oozing against my tongue, so I opened my mouth as wide as possible and leaned back, so Tony would be able to watch the rest of his semen surging into my mouth. After a half-dozen spurts his cock was still, so I leaned back until his cock was released, closed my mouth, and gave myself a moment to swirl his come over my tongue. It tasted like butter and vanilla, and it went down with no bitter aftertaste at all.

“Wow,” I said, again making eye contact. “Your come is delicious.”

Without waiting for a response, I leaned back in to lick his cock clean, restoring his foreskin so I didn’t linger too much on an overly-sensitive spot and licking him up and down until he took a half-step back.

“You… you can really suck cock,” he said.

“It’s sort of like I’ve been taking a continuing education course for the past couple months,” I replied.

Tony held his hand out and helped me back to a standing position. There was a mirror over by his entryway, and we both moved over there, examining ourselves. We were neither of us worse for wear, though I did have one wet spot on the right side of my chest, though it looked to be saliva and not semen, so I figured it would dry out okay.

“Shall we?” Tony said, gesturing to the door.

We took a short walk to a French bistro that was in his neighborhood, and right from the start there was a particular aspect to the way Tony was behaving. It took me a while to put my finger on it, as he pulled out my chair and ordered wine for us. He refused the menus and also ordered for us as well (in fairly passable French, even!) and then I put my finger on it. Are we… are we on a date?

Once I had that realization, I could tell from Tony’s behavior and body language that he was definitely acting like he was on a date. On the other hand, I was also having a really nice time. Tony and I had never really hung out on our own before, and when we did hang out, the tempo was usually set by James and Edward. But it turned out we were had more in common than I had realized, and the conversation was actually flowing really naturally.

Without really meaning to, by the time we were done dinner, I realized I was really leaning into my having-a-nice-time-on-a-date routine. Well, I did intend to put out in any case.

When we were done, Tony excused himself to go istanbul travestileri pay the bill, and I took a moment to check my phone. I was surprised to see I had a text from the number that sent me my video instructions reading, “BE READY TO GO BY 6 AM TOMORROW.”

I must have groaned just as Tony got back to the table as he gave me a concerned look. “Everything okay?”

I put my phone down and gave him a smile. “Just work stuff, I can worry about it later.” I hated getting up early under any circumstances, but I resolved not to let that distract me from my night out.

Saying we should walk off the meal a little, Tony took me the long way back to his place, walking around looking at people’s Halloween decorations and then winding through a couple of the parks in his neighborhood. It was actually a pretty nice night for the end of October, and we were still telling each other stories. At some point, we went off the main path, and Tony reached out to offer me a hand when I followed him stepping over a log. Somehow after that, we ended up holding hands as we walked.

And then, after we looked out over the reflection of the city in a little pond, he leaned over and kissed me on the lips.

This wasn’t something I was expecting.

I could say that I felt a moment of discomfort, of something that had violated even the extreme flexibility I’d been experiencing with my heterosexuality over the past couple months. But while I did feel a sort of instinctual twitch of weirdness, it was several items down the agenda of things I was feeling. Though to be honest, more than some sort of new acceptance or anything, my main reaction was one of acquiescence, again remembering that I had accepted that my role was to submit.

But it did feel nice to be kissed.

I kissed back, and it was not unpleasant when we ended up standing there, making out for a few minutes. Tony broke it off and smiled at me. “Thanks,” he said, as we both caught our breath. “I know this isn’t… what you’re really into, but I’m glad you’re okay with this.”

“I’ve been… re-evaluating ‘what I’m into’ quite a lot lately,” I responded. “Right now, I’m pretty willing to try most stuff and see where it falls on the what-I’m-into scale.”

Tony squeezed my hand and led me back down the path as we started heading out of the park. He appeared to be in a bit more of a rush to get home now. “Well, I’m glad it’s okay. I mean… did you ever figure out that I used to have a huge crush on you?”

“I… what? No, to be honest, I never did. Gaydar fail, I guess.”

“Yeah, well, speaking of gaydar fails, I was totally into you when you started hanging out with all of us, but I was sure you were completely straight, despite what James said.”

I was about to ask what it was that James said when we were almost run down by a teen on a bicycle with no lights and no helmet. After that scare, the conversation shifted into other things as we got back to his place.

And when we were back at Tony’s there was suddenly not much conversation. He started kissing me again, and soon enough we were undressing each other, and then we were nude, making out on his sofa. Eager to feel it again, I reached out to grasp his cock when Tony pushed my hand aside and stood up. He gave me a hand to rise as well and he said, “let’s go to my bedroom.”

As I followed him I got to admire his ass, which was tautly curved in a really exciting way. I was eager to touch that too, but as Tony gestured for me to sit beside him on the bed, he diverted me again.

“I want this to stretch out, and to go nice and slow. I’m instituting a rule: each of us has a pair of invisible underwear on, made out of a fabric that you can’t feel anything through. So we’re going to touch each other, but no touching anywhere that’s covered by the underwear.”

This was another new thing. Pretty much one hundred per cent of my time with men had been spent interacting with the parts covered by underwear.

Perhaps noticing my hesitation, Tony gently pushed me back so I was laying on the bed, and his hands started exploring my body — my chin and neck, then my shoulders and arms, then his hands running down my legs to rub my feet. He gestured for me to turn over, and his hands worked their way back up my body, skipping over my butt as he shifted over to lean in a bit more and massage my back and shoulders.

And then I was on my back again, and he was stroking my chest and nipples, a bit more open sensuality in his ministrations. It had been months since I’d been touched like this — months even before Sir had taken over my chastity, and I’d forgotten just how nice it felt to be touched, stroked, caressed. To be able to feel your body relaxing all over, endorphins flowing.

Tony leaned in and kissed my chin and then my neck, and then his lips started making a similar circuit of my body as his hands had done, still skipping over my invisible underwear. After he had kissed and sucked on my toes for travesti istanbul a little while, I felt like it was time for me to get return the favor, so with the same relaxed slowness he’d been showing, I took over and explored his body with hands and then lips.

It had been ages since I’d had a slow, sexy sort of session like this, and perhaps it shouldn’t be so surprising that it just made me feel good all over. Tony was relaxed as well; there was a dreamy look in his eyes as I finished my tour and was licking and sucking on his toes.

It had affected him in another way as well, and I saw he was sporting a nice, rigid hard-on. I wondered if it would be okay to move things along.

I shifted up so I was sitting beside Tony as he continued to lay back, hands behind his head. I put a hand on each of his hips and made a tugging motion.

“What are you doing?” he asked, smiling down at me.

“I’m seeing if these invisible underwear can come off yet.”

He laughed and wiggled his hips. “Yeah, I think it’s time.” Playing along with me, he lifted his butt off the bed, so I shimmied the pretend underwear down his legs and mimed tossing them off to the side.

“Oh, look what was hidden underneath!” I said, as if noticing his cock for the first time. Using as much slowness as we had been maintaining, I let my fingertips move slowly toward his erection, still never quite touching it as I ran my fingernails above his smooth-shaved pubis, then down the crack of his leg, then spending a fair amount of time gently stroking his scrotum. Drops of pre-come oozed down his shaft as his cock twitched, waiting for my touch.

Just as I was about to move forward once more and actually start playing with his dick, Tony shifted. Motioning for me to lay back, we switched positions, and he proceeded to remove my invisible underwear as well, expressing admiration for my locked cock, then gently letting his fingers explore the area around it.

“I didn’t really want to get so sexual right when you got here,” he said as his fingers gently brushed across my balls, causing my cage to jerk. Then he rotated and pulled himself up so he was sitting at the end of the bed, legs dangling over. “But I think it’ll work out now. I almost always bottom, and if I didn’t have that big orgasm earlier on, I wouldn’t be able to fuck you for nearly as long as I want to. I had thought about just jerking off before you came over…”

“Oh hell no! I would have been mad at you if you wasted all that excellent come,” I said.

He laughed again, “well, it worked out. I feel really turned on now, but I feel like it’ll be a slow burner. Here, turn over.”

I flipped over, and following another gesture, I shifted so I was laying face down across his lap. I could feel his cock gently poking against my belly as he started stroking my ass.

Once more with extreme slowness he worked his way inward until finally a finger brushed against my asshole, and I gasped. He licked a finger and slowly began rubbing all around my hole, lightly brushing and caressing my eager entrance. I was in heaven. This was one of my favorite parts of getting fucked, and it never lasted as long as I wanted as guys were getting ready to fuck me. Now, with it stretching out, I could feel my insides glowing as I started to feel a palpable craving to have my hole penetrated.

Reading my reactions, Tony leaned over to his nightstand to grab a bottle of lube, which I soon felt dribbling against my sphincter. His fingers became a little more insistent now, gently pushing inward. My hole offered no resistance and opened itself up to the kind intrusion, and soon, there was a twisting finger moving in and out of my hole.

“Christ, that’s so good. I’d always liked playing with my ass, but when I started locking up, it’s like it made buttplay a hundred times better.”

“Really? Hm…” but instead of pushing his own line of thought further, Tony added a second finger going into my hole, and the pleasure I was feeling increased. I was twisting my hips now, trying to push back to force him to penetrate me further, but he wouldn’t be rushed, and I had to relax and just feel that glow building up inside me. Three fingers felt just as exciting, even more when he really got his wrist twisting back and forth.

“Oh fuck…. I can’t, I can’t wait much more,” he said, giving me a gentle swat that directed me to move off his lap. “I really, really, really have to fuck you now.”

I did a sort of controlled slide off the bed so that I ended on my knees in front of him. His cock was still fully hard, and didn’t need any more attention to make him ready. He leaned back over and grabbed a condom off the nightstand, handing it down to me. “Would you do the honors?” he asked.

I took it from him and tore it open, setting the condom on his tip. “Do you need this moved back?” I asked as I gently touched his foreskin.

“Not this time… it’ll help me last like that.” So I unrolled the condom down his shaft, before leaning back to admire his cock.

“I would… like it very much if you fucked me now.”

He grinned. “Okay.”

I stood up so I could climb onto the bed. I got on my hands and knees, lowering my shoulders and presenting my ass to him.

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