I'll Look After You

By Touchstone
published May 22, 2019
Summary

Darren promised he wouldn’t go too far. Promises are made to be broken.

Author’s Note: Sorry this took too long! For the few who comments on the last chapter suggesting they would have preferred the hypnotist to convince Jack to call him ‘sir’ instead of boy, hopefully this chapter will reveal that there is a little bit of method to my madness.

“Hey, I know we planned to hit the sauna tonight, but something came up. Hope you don’t mind.”

Darren’s ears perked up, the young lawyer looking up from the book he’d been reading laid out as he was on the hotel room balcony clad only in the same black speedos he’d been wearing at the pool earlier. He caught a glimpse of Jack disappearing into the bedroom and got to his feet, wondering where that mixture of curiosity and disappointment had just come from. He could hear the sound of tinkling as he approached the bedroom door, and he realized that the older man was likely peeing in the adjoining bathroom without having bothered to close the door given how engrossed Darren had likely seemed in his book.

Since their encounter in the showers earlier, Darren had spent the rest of the day convincing himself that hypnotizing Jack into letting him suck his cock was as far as things would go. He’d even allowed himself to suggest the two of them spend the rest of the afternoon wandering on their own after the drink they’d had together. The older man had been adorably clueless as to why Darren had a smile on his face like a cat that had been fed cream. Regardless he’d resolved that tonight he’d hypnotize the man one last time (after one last round of looking but no touching in the sauna) to help him get to sleep, and that was it. He’d asked so nicely for it by the pool, after all.

He’d probably have been okay with one last glimpse of the man in his speedos tonight before they left the resort the following day and went on with their respective lives. Of course, hopefully the man would at least be a little less hostile. If he was even a little more accepting of him it would be good enough. Probably.

Common sense told him to stand outside the bedroom altogether until the man was done peeing. Something else made him lean in and peek, catching a glimpse of Jack as he pulled those mouth-watering red speedos back on. His eyes were almost magnetically drawn towards the man’s soft member before it was tucked out of sight.

“Oh hey,” Jack greeted him as he stepped out of the bathroom, before heading straight for his duffel bag. Fishing out a pair of light blue beach shorts followed by a white linen shirt, Jack didn’t notice the crestfallen look on Darren’s face as he started to get dressed. If nothing else, the suggestion that they should be comfortable with one another was still holding as far as Darren was concerned, as he was sure the man would have had a few choice words to say about him standing and watching him get changed had this happened yesterday.

‘Maybe a suggestion for him to send me one selfie per month wearing nothing but that speedo wouldn’t be too out of order..’

“Something wrong, boy?”

Snapped back out of his thoughts, Darren immediately remembered that the other suggestion he’d left was still there too given the way he’d just been addressed. ‘Maybe I could get away with once a week?’ He tried to justify it internally. Maybe if he did that in exchange for getting rid of the suggestion to make Jack call him that? Not that his own treacherous cock seemed to mind, given the way it was twitching. Hiding a boner at work (if not from Jack, at least from the rest of the office) was bound to become tiresome at some point if Jack continued to call him that.

But they weren’t at the office, and Jack was starting to look concerned that he wasn’t answering his question. Looking just as good dressed, Jack walked towards him, looking more than a little apologetic. “I’m sorry about cancelling our plans…” the man muttered while Darren continued trying to find his tongue. Evidently the man had mistaken the disappointment on his face as being due to the last minute cancellation rather than the fact that that delicious, hairy chest was now hidden under a white linen shirt.

“Here…” Darren found himself whispering, unsure of when he had closed the distance between them,. Reaching forward, he unbuttoned the top two buttons of the shirt so he could at least get a decent glimpse of that chest. “It’s much too warm to keep it buttoned all the way up.”

Despite his attitude towards Darren prior to last night, Jack just flashed that handsome smile. “I suppose you’re right,” he agreed, before a brief moment of silence passed between them.

“Oh… you said something came up?” Darren managed to ask when he finally regathered his thoughts.

“Yeah. I bumped into Sarah at the bar after you went up. You know Sarah… she works on our floor.”

Darren could feel himself prickling up internally. “Oh yeah. I know Sarah,” he confirmed, doing his best to keep the venom out of his voice. About ten years younger than Jack, the woman had a certain reputation about the workplace that was enough for Darren to smell an ulterior motive.

‘Because my own intentions have been so pure, after all.’

“She bought me a drink. Turns out she’s leaving her husband too. It was nice to talk to someone who gets it. She suggested we meet for dinner and go check out one of the jacuzzis…” Jack explained, although the guilt was still there on his face.

Of couse she did,’ Darren thought to himself, trying to keep a neutral expression. Jack deserved to have some fun that he would actually remember, he tried to rationalize with himself. “I’ll see you when you get back?” Darren asked hopefully. ‘To undo some of the more overzealous suggestions I made at least. Nothing more.

“Oh… about that…” Jack actually looked like he was about to start blushing. Given how stern he always was at work Darren was almost disturbed as he was awestruck. “I know… I asked… if you could hypnotize me again tonight to help me sleep… but I might be um… late…”

“No problem,” Darren put on his best smile. “I don’t sleep too early either.”

“Actually… I… think there might be a chance I’m spending the night in her room… Wouldn’t… wouldn’t feel right to keep you waiting…” Jack paused, the guilty schoolboy look melting in confusion as he paused. “Wait… I mean. Sorry if that’s too much information, boy. I don’t know why… we barely speak to each other at work, but since we got here I feel like we can tell each other anything. You won’t tell anyone, will you boy?”

“Of course not…” Darren replied, wrestling internally with his desires. It would be so easy. The other suggestions were still in place. Why wouldn’t the trigger to bring him back under instantly?

Jack reached across to squeeze his shoulder. “I’m glad I can trust you, boy. And I’m sorry if I let you down.” Smiling warmly, he slowly let go before he started to walk past Darren.

‘Don’t do it…. Don’t do it…’

“Sleepy daddy!” He almost couldn’t believe that he’d chosen those words in the end, but there they were. And as much as he didn’t want to believe that he’d just used them, it was his voice. And evidently Jack had heard those words too, given the way he had suddenly stopped in his casual walk towards the hotel room door, so close to having had a choice about what he would be ultimately doing tonight. Standing tall where he had frozen, his head was slumped down towards his chest.

Approaching carefully as he’d never tried to use a trigger to bring someone back under before, Darren eventually mustered the courage to press a finger against Jack’s shoulder.

No response.

“Jack? Can you hear me?”

“Yes, boy.”

There was that word again, even if it sounded monotonous in comparison to the man casually using it unthinkingly when awake. Although he wasn’t sure he would ever get used to it, there was certainly no denying how his cock felt about the matter. Now wasn’t the time to deal with that, however.

“When is Sarah expecting to meet you?” Darren asked.

“Fifteen minutes…” came the blank response.

Thinking quickly, Darren reached into one of Jack’s pockets before fishing out his phone. “Jack, you can open your eyes, remaining in this perfectly relaxed state,” he commanded. And although he had asked for it, he still paused when those blue eyes opened to reveal how empty and expressionless they truly were. “N.. now… would you kindly unlock your phone for me?”

“Yes, boy…” Jack answered, doing as instructed before Darren took the phone back. Before he could set about with what he was planning however, curiosity got the better of the younger lawyer again.

“Do you… know the rumors about Sarah?” he asked, hesitating to call off something potentially good for Jack.

“Yes, boy…” Jack replied quietly.

Good, so the man wasn’t being led on hopefully. “Okay, so how did she convince you to meet up with her?” he pressed further.

“She asked if I had any plans tonight. I told her we were going to the sauna. She said I shouldn’t hang out with fags or it would rub off on me.”

The decision to interfere was becoming easier rather than harder. It was still strangely disappointing to hear the slur coming out of Jack’s mouth, however. Although the man had made his opinions about his sexuality known on more than one occasion, he’d always thought that the one saving grace was that he was too dignified to resort to using words like that. It was probably just him repeating her words, he rationalized before inevitably asking, “And… what did you say to that?”

“I said that she shouldn’t use that word, and you weren’t as bad as I thought you were.” Darren found himself feeling pleased about that. It was some progress, at least. However Jack then continued, “She pointed out that I used to hate you and used that word behind your back a lot. She said you were a bad influence on me, and that she had seen us by the pool when you gave me that back rub. She told me I looked good in that speedo, and said she wanted to see it again when I came down to the jacuzzi to meet her.”

Darren bit his lip. So much for Jack being better than that (until today, anyway). But more importantly, he remembered now what he had suggested last night. He had convinced Jack to accept compliments regarding the swimwear he’d been so hesitant to use. Would he have accepted her offer if not for that? Possibly.

The phone vibrated in Darren’s hand.

U ditched him yet?’ flashed across the screen, followed by an emoji of an aubergine.

Ugh.

“Well, fuck you too, Sarah,” Darren seethed, typing back: ‘Actually I’m not feeling up to meeting you tonight, and I don’t appreciate the way you’re talking about our colleague. Please don’t contact me on this number again.’ Blocking her was perhaps overkill, but this was a good thing he was doing. ‘A good thing for Jack, not for me!’

“Jack, I want you to repeat after me. ‘Sarah is no good for me. She is after my money, like my ex-wife was.’” There. He wasn’t generalizing it to all women. Jack could still be as straight as he wanted, just not with her.

“Sarah is no good for me. She is after my money, like my ex-wife was.”

Darren made Jack repeat those sentences a few more times before he considered the matter resolved. A thought suddenly occurred to him, and he asked, “Does she know what room we’re in?”

“No, boy.”

At least that. But if she knew about the sauna would she really question the text message enough to come find him there?

Maybe they could stay here for now. But if they were going to do that…

“Strip for me, Jack. Down to your speedos,” he found himself commanding. If tonight was going to be the last night that he got to enjoy having a muscular, good-looking daddy under his thrall, he might as well enjoy it even if they were going to be staying in the room. He watched as Jack did as he was asked, unbuttoning the rest of the shirt he had just put on a few minutes ago. Darren wondered how much of what he was doing was out of spite for the conversation Jack had had with Sarah, remembering how nice it had felt to hear Jack admit regret for some of his comments at work. Did he mean the comments he was apparently making behind his back as well? Even if Darren had planted that seed himself, it had still been nice to hear. There were other things however, he realized he could make the man say. And by the second, these things were becoming filthier.

Ok, get a hold of yourself,’ Darren tried to think of something else. Only Jack was still there, standing right in front of him wearing nothing but that tight speedo, no signs of life but the slow rising and falling of that firm, inviting chest. And those eyes of course, hazily awaiting instruction.

Ok, just a little bit of fun tonight. But I make him forget in the morning before we check out, and undo whatever suggestions I’ve put in apart from being a bit less homophobic.

“Jack… I want you to listen to me,” Darren commanded, unable to resist reaching forward and fondling Jack’s bulge through the stretched red fabric. “When I command you to awaken, you will forget that you made any plans with Sarah. You ditched her because she was being unfair about me and you couldn’t stand that. And you’ll forget anything she said about you in that speedo. From now on you’ll prefer receiving compliments from men exclusively, do you understand?”

“Yes, boy,” Jack confirmed.

Darren paused to contemplate the gravity of what he had just commanded. ‘Oh yeah. My intentions are so pure.’ Whatever he felt about it however, he still continued. “You won’t even think about your phone for the rest of tonight.”

“Yes, boy.”

“And the first thing you’ll remember… is how good it felt to have me rub your shoulders by the pool. How nice I was to help you put on your suntan lotion on. You’ll notice the towel on the balcony, and offer to return the favour. As far as you remember, you had a nice, quiet drink at the bar before Sarah rudely interrupted, but you came back up because you wanted to see me again. You’re feeling so grateful for my help that anything I suggest you’ll ultimately find yourself doing.”

“Yes, boy.”

Was he risking failing spectacularly by giving so many commands in quick succession after using a trigger he’d never used before? Perhaps. There was only one way to find out, however.

“Good. Now awaken.”

The focus slowly returned to Jack’s eyes. “Oh,” he muttered, just noticing how close Darren was, before his eyes roamed further down to confirm where Darren’s hand still was, lightly palming his bulge. Instead of looking surprised or outraged however, he looked back up at Darren’s face. “I… must have spaced out or something. Sorry I took so long downstairs. I could have stayed down there drinking for another few hours but I…” his voice trailed off slightly, a light grunt escaping him as Darren dared a light squeeze.

“I’m glad you’re wearing this,” Darren found himself blurting out. “It really accentuates your junk.”

The goofy, almost proud grin on that bearded face was one Darren wished he could take a picture of. “Thanks, I wasn’t so sure when I first bought them, but I liked the look of them too. To think I was initially going to come here and leave them in my bag the whole time…” The fact that Jack’s cock even throbbed against his hand made the moment all the more delicious, and Darren found himself wondering why he had regretted planting the idea for the now docile giant to accept and even appreciate being touched.

“A… anyway, I saw you on the balcony when I got in. Looks like there might still be a bit of sun left today before it goes down,” Jack commented.

“Mmhmm…” Darren answered simply, sounding more than a little distracted.

“And… I was thinking that you not only helped me out last night with the hypnosis thing, but the shoulder rub you gave me by the pool was kinda nice too. I always thought that it was only worth going with female masseuses, but I guess a guy would know the best way to do it.”

“Mmhmm…”

“Maybe I could return the favor? We’ll enjoy the sun while it’s still out on the balcony, then hit the sauna like we planned?” If Jack seemed disturbed by Darren’s fondling, he still wasn’t showing it.

“Oh?” Darren smiled, feeling strangely fired up enough to push his luck. “Have you ever offered another man a massage before? Weren’t you teasing me about training to be a masseuse rather than a lawyer?”

Jack chuckled, a sound that Darren was starting to find endearing. “No… I haven’t given another man a massage before, but I’m happy to try what you did or have you give me pointers. It’s the least I can do given how decent you’ve been to me, even with how I can behave at the office sometimes.”

“Well. When you put it that way…” Darren could feel his cock swelling. It took every ounce of willpower he had to remove his hand and turn away from Jack, walking to the balcony with the older man following him closely behind. He passed the older man the bottle of sunscreen before laying down on his front on the hotel towel.

“You wouldn’t mind just putting on another layer would you? It’s a good place to start as any. No need for any squeezing or pressing yet, just rub it in… starting at my shoulder,” he instructed.

“Sure, boy,” Jack replied, starting to get down on his knees beside him.

“Wait, I think you’d be in a better position if you straddle me,” Darren stopped him.

“Oh of course, boy,” Jack replied sheepishly. “As I said, happy for you to give me pointers.”

Darren was grinning to himself as he felt Jack loom over him, before feeling a weight press down on his speedo-clad ass. That felt good on its own, given the pressure exerted indirectly on his cock, but even better was the realization that his ‘casual fondling’ had left Jack noticeably semi-erect, that member pressing between his asscheeks. He heard the squirting sounds from the bottle, and the next thing he knew, two large hands came down, slowly rubbing the lotion into his shoulders.

“Nice… take your time with it… feel your way…” Darren muttered softly, his cock giving a twitch as Jack replied with another soft ‘yes, boy’. Those hands slowly, almost sensuously began working their way lower. “You’re sure this isn’t awkward for you?” Darren dared to ask.

“Why would it? We’re both men after all. Nothing wrong with us touching each other, is there?” Jack replied confidently.

“Mmm… I suppose you’re right,” Darren smiled, loving how well things seemed to be working out. “Oh, you can skip my legs, just keep focusing on my shoulder and back,” he instructed by the time Jack was getting ready to shift positions, all so he could keep that cock right where it was.

To his dismay however, even with Jack following his instructions once the man was beginning to knead and rub his shoulders in earnest, that cock was slowly beginning to soften. “You’re not doing too badly,” he found himself saying, “Hope you’re liking it as much as I am?”

Jack’s chuckling this time didn’t inspire confidence. “Well I’d get it if you’re liking it a bit too much, boy. But I’m straight, remember? Hope it doesn’t offend you. I am just returning the favor…”

‘We’ll see about that.’

“Sleepy daddy.”

The soft sigh came first, although Darren barely had time to register it before he suddenly felt the man collapsing on top of him, his entire weight coming down. Jack’s face landed just on his shoulder beside his face, his limp arms and legs unmoving while his crotch remained right where it was.

“D… damn…” Darren grunted, feeling slightly embarrassed about the position he’d ended up in. “J… Jack… open your eyes and put your hands on the towel beside my head… support your own weight…”

“Yes, boy,” came the unconcerned response, Jack slowly shifting onto all fours so Darren could turn over onto his back. Staring up at those empty blue eyes, Darren reached his hands up, feeling the man’s back and gradually trailing them down towards his ass.

“L… lower yourself for me,” Darren continued, pulling Jack’s hips towards him specifically until he could feel the man’s crotch perfectly aligned with his. “Rest your hips on mine… that’s it…” Darren bit his lip as his cock throbbed, still able to feel Jack’s despite the apparent lack of excitement in the older man.

“Did you feel my cock throb?” he asked.

“Yes, boy.”

“From now on…” Darren whispered, slowly rubbing his own hard cock up and down along the outline of Jack’s bulge. “Whenever you feel another man’s cock throb, it will make yours throb in response.”

“Throb… in response…” Jack echoed softly. Almost as though he was demonstrating it, it did, just as Darren felt his own cock pulse against Jack’s once more.

“The more your cock throbs, the hornier you become…” he continued.

“Hornier…”

“…and the hornier you become, the more you will start to realize that you actually enjoy the idea of making another boy throb for you. Ache for you. Lust for you.”

“Enjoy… throb… ache… lust…”

“Yes… exactly…” Darren grinned lustfully, loving that Jack’s cock was steadily throbbing its way back to full hardness. “You love making good boys throb.”

“I love making good boys throb.”

“And you also love putting them in their place. Reminding them of who’s in charge. You love feeling in charge, don’t you Jack?” he went further.

“Yesssss…” The way the man seemed slightly more enthusiastic to that particular suggestion wasn’t surprising. Jack always did love ordering others around. Only now he was going to channel that love of being in control in a slightly… better direction.

“You love it when boys call you daddy. It tells you that they’re ready to submit. And you oh so love to make boys submit…” He could hear himself say these things, even though he’d never been much for kinks or daddies up until last night (not counting his previous phase before he became a working adult). He could almost feel a part of himself trying to warn that he was playing a dangerous game, but the thrill of having Jack mindlessly soaking up his suggestions was just too intoxicating.

And just the prospect of seeing what the end result would be was too good to pass up.

“Rub yourself against me daddy… make me throb with your cock…” he purred softly.

“Yes, boy.” And although that response was just as monotonous as the others, it took nothing away from the fact that Jack was starting to move his hips, that pulsing daddy cock pressing down so deliciously against his own. Darren squirmed, ground back, moaned. His fingers gripped the towel as he drank in the delicious sight of Jack mindlessly humping against him despite having just reaffirmed his ‘straightness’ minutes ago.

“The more we throb together, the deeper you go…” Darren groaned out.

“More… throb… deeper…”

“Thaaaat’s right… deeper and deeper. Throb for me, daddy…”

“Throb…”

Darren’s toes were beginning to curl. Jack was steadily grinding harder and faster, beads of sweat starting to form on the older man’s forehead. His jaw was starting to fall open, and a single trickle of drool escaped his lips and trickled down his well groomed beard.

“You love making gay boys throb with your daddy dick…” Darren panted out between thrusts.

“I love-

But Jack never completed that sentence. Suddenly those drooping eyelids shot wide open, that rigid cock in that tight red speedo soon spurting out the older man’s load with enough volume that it was seeping through the fabric. Adorably, the man was starting to slump down onto Darren once more, if with less force and suddenness than the first time. “M…making… gay… boys…” the man continued to slur as his cock oozed out the last of his load into his swimwear.

“Shhh… it’s okay… relax… sleeeeep…” Darren cooed softly, wrapping his arms around Jack’s head and caressing his hair. “Sleeep.”

“Shleeep…” Jack agreed weakly before his eyes finally drifted shut.

‘Well,’ Darren thought to himself, still lying beneath the unconscious Jack. ‘So much for drawing that out.’ His cock was still hard, but finishing himself by continuing to grind against the sleeping Jack just didn’t seem good enough anymore.

‘*Fucking Sarah. We could have had a great night in the sauna together and now…’ *

He stopped that thought as he realized that just because Jack was presently asleep, didn’t mean the night was over. The sun was just about to set on the horizon, and they weren’t due to check out until 11am tomorrow, at which point the rest of the company would gather in the foyer for the transport they’d booked to the airport.

And then a thought occurred to him. It was definitely spiteful, but that made it even better.

Somehow managing to crawl out from under the sleeping Jack, he got back on his feet and headed over to the phone in the hotel living room, immediately dialing for the front desk as he got there.

“Hi. I’d like to book one of the jacuzzis out towards the beach for two hours. And uh, we’d like some privacy, so can we get one far away from the others? Could we pay you to cordon off the whole section?”

Luckily, from the response he received, it was not an unusual request. Just expensive.

“Yes, I know the company isn’t covering that. My uh. Roommate is insisting. Yes. Put it on his card. So… 8 o’clock? Perfect.”

Grinning to himself, he returned to find Jack right where he left him, lying on his front in nothing but his cum-filled speedos.

“Can you still hear me, Jack?”

“Yes, boy…”

“When you hear the hotel room door shut, you will awaken. You won’t remember what we’ve done, but you’ll think you were dreaming about it even if you won’t recognize that the boy was me. The fact that you just came in your speedos won’t bother you. You like the way you look and feel in them too much to let it bother you.”

“Yes, boy…”

“You’ll realize that you dreamt of rubbing your cock against another man. Another boy, even. You’ll remember how your ex-wife treated you, the awful rumours about Sarah and the spiteful way she talked about me, and realize that women don’t deserve your cock…”

“Women don’t deserve my cock…” the man parroted. Darren paused. Hadn’t he promised himself he wouldn’t go this far?

I will just change him back before the night is over.’

“All you ever wanted was a boy, a son, and she never gave it to you which is why you’re leaving her. You’ll realize that the next best thing, no, the best thing for you now will be to find a young man you can guide, protect and shape… in return for pleasure…”

“P… pleasure…”

“And as much as you enjoyed dreaming of making a boy throb using your cock… deep down you know that it can feel even better if you could just fuck him or make him swallow your load…”

“Fuck… swallow…”

“Thaaaat’s it. You will forget that we made plans tonight, and even who I am until I remind you in this state. Instead of falling under whenever you hear me say ‘Sleepy daddy’, from now on you will come back to this state when I say the words ‘Throbbing daddy’. Is that clear?”

“Throbbing daddy…”

“That’s right. Because that’s what you are. Or what you want to be,” Darren suggested. “You will realize you’re still horny when you wake up. But because women no longer deserve your cock, you will seek the company of another man. You will put a robe on over your speedo and go down to where the jacuzzis are. There will be a sign suggesting that it’s closed, but you will go in regardless. And when you find me there waiting for you, you will instantly know that I’m just what you were looking for…”

“Looking for…”

“Even if you won’t know me, you’ll approach and join me when I invite you. The moment you sit down and look at me, you will know for certain that you want to try fucking another man. That you want that daddy dick in my mouth or in my hole…”

“Yes, boy…”

Darren wasn’t quite sure who was under whose thrall when he leaned down to lightly peck the man on the cheek. His still hard cock throbbed again in his speedos, and he found himself excitedly running back into the hotel, throwing on whatever would at least be considered decent over his swimwear.

He made sure to slam the door as loudly as he could on his way out, chuckling lecherously as he made a beeline for the elevator.

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