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Secrets (AllThingsCuddly/Gumdrop)

Lifting the bottom of the shirt further, Jeremiah hooked it over the man's head, leaving his chest exposed while keeping the shirt on his arms. Walking away for a moment, he found a couple other items to bring over to the man. He clamped one vibrating slip into Oliver's left nipple, then one onto his right. Finally he pressed against him, grinding again while he activated both vibrators at the same time.

Now his hands began to trace circles and lines over Oliver's bare chest, slowly getting lower and lower. Eventually he got to the pants and undid the button and zipper but left him trapped inside while he pressed his lips to Oliver's neck and began to kiss at his flesh.
 
Oliver looked around as soon as Jeremiah left him, the stimulation was gone and he didn't know what to do with this. Though he soon gasped as something was clamped to his nipples. This was already enough to give him a bit of a tingling sensation but when they were activated and vibrated he gave a moan and a small whimper as the pleasure shot through his body. His body shivered as Jeremiah played with his body, his hips arching into the hands that were simply undoing his pants. He wanted more than to be trapped inside. He gave a whine at the other not pulling him out and giving him more satisfaction but moved his head so the other could kiss his neck more. He tugged at his restraints wanting to pleasure himself but found he couldn't. He groaned a little louder as his body kept being stimulated, just not where he wanted the stimulation.
 
Jeremiah chuckled at the whimper and the way Oliver started to strain against the restraints. With careful movements he lowered the man's pants down and over his hips, dragging his underwear with them. Grabbing a bottle of lube, he poured some on his fingers and began to rub it around the man's hole then pressed his middle finger into his tight hole and pressed it in deep. Wiggling his finger around, he found the spherical bundle of nerves and began to rub at the prostate. "Show me on a scale of one to five... How badly do you want me to take my finger out and slip my dick in?"
 
Oliver helped the best he could in moving his pants off of him, at least over his hips with enough access to get to his ass. He moaned at the fingers inside of him and even if the pants kept him in a certain position with his legs, he was doing his best to press into the finger inside of him. Had Jeremiah asked him before he found that wonderful spot he would have been able to deal for a little longer like this, but when he hit that spot he moaned and opened his hand to show a five nearly immediately. Though, he honestly had no idea which way the scale was going. Which one was super bad? He wanted to be fucked, whether it be by machine or by Jeremiah. Though at the moment, something less silicone and more hot and needy as well was preferred.
 
Jeremiah knew instantly by the noises Oliver was making and the way he was squirming that five was high, that Oliver was desperate for something more than a finger inside of him. "Mmm, only a five?" He asked, intentionally misinterpreting. He pressed a little more firmly on the spot, rubbing at it in slow circles. Then he pulled his finger back before thrusting it back in and rubbing past that sweet spot. His finger pulled back and instead he inserted two fingers and they began to rub and press on those nerves.

As he teased his prostate with one hand, the other hand wrapped around and grasped the man's cock, stroking it slowly at first but picking up the pace with each stroke.
 
Oliver gave a moan in protest when Jeremiah seemed to misinterpret his number, it almost vaguely sounded like Jeremiah's name, but it was hard to tell through that gag. He quickly switched his fingers to a one, hoping the other would change. He continued to groan as the other interested another finger and started to mess with his cock as well. He was gonna come like this if Jeremiah didn't hurry and shove his cock in. Not being able to see anything that Jeremiah was doing was driving him crazy. He could and couldn't tell where his hands were, they felt bigger somehow, like they were completely filling him or surrounding him. He couldn't even imagine how amazing he was going to feel when he had a cock inside him.
 
Jeremiah saw the fingers immediately change but acted like he didn't notice them. Instead he started shaking his hand, pressing his fingers against the other in a quick motion, making it feel like a vibrator. His other hand stroked faster and faster. Then a at once he let got and pulled out simultaneously. Leaving Oliver high and dry was one of his favorite things and watching his cock twitch and dribble precum turned him on a lot. "Mm, you like that?"

He hooked his thumbs through his own briefs and slipped them down and off. He stroked himself for a moment, bringing himself to fully erect, licking his lips while he watched.
 
Oliver let out a gasp as the other pressed him closer and closer to coming. And then nothing, his hips twitched. His brain protesting swearing that Jeremiah said he wasn't going to do this, that today was about coming over and over again, so why was he left like this. His hips pressed forward as his cock leaked almost like it was crying out to be allowed to release. He moaned out, wanting to entice the other to play with him ore and not leave him here like this. He shook his head when he was asked if he liked this, "No!" he said, though it didn't sound like much coming through the gag. He tried to lean forward but once again his restraints were refusing to let him move much of anywhere. He was right there, but because of this wait, it was slowly going down basically ruined, even if he was still rock hard.
 
"Don't worry, I'll make it feel better soon." He spoke into Oliver's ear then reached down to pour some lubricant over his own cock. He brought himself to the man's entrance and pressed against him, feeling his muscles twitching with need. Slowly he began to push in, then pull out, then push in a little deeper, then pull back out again.

In and out he thrusted, soon feeling his entire cock buried deep inside the younger man. He stopped moving, just enjoying the feeling of being buried deep inside such a hot, tight hole. Reaching up, he undid the gag and pulled it away. "Before I let you cum... I want you to tell me something."
 
Oliver nodded, groaning as he was pressed into. God, he felt insanely full and the man wasn't even completely in him yet. As Jeremiah slowly worked his way to be completely inside him his cock twitched and begged for the other to be faster and pound him but nothing, just nice slow thrusts. He could feel his brain short-circuiting a bit at the slowness of it all. As the gag was removed his tongue followed a bit before he slowly pulled it back in, "W-what?" he asked, groaning, "Please Jeremiah, what...I want to come," he moaned. He tried to move on his own and even as he did it wasn't enough, just a little bit here and there since his feet didn't quite reach the floor so he couldn't get any good leverage.
 
Jeremiah knew he had Oliver where he wanted him. The boy was like putty in his hands. He wrapped an arm around him and slowly stroked up and down his cock. "Nothing too difficult..." He said in a low voice, encouraging Oliver to whisper his response as well. "Haru's phone number." He told the other, licking along his neck while he ground his hips just a little against the man. It really wasn't a lot to ask and he was sure even if he had asked for it when the other wasn't bound and desperately waiting to cum, he would have supplied it. It was just more fun making the other divulge something like this while he was so clearly not in the right state of mind for it.
 
Oliver arched into the hand pumping his cock so slowly. He would have looked confused if it weren't for the mask, why did Jeremiah want Haru's phone number? If it had been moments before he probably wouldn't have quickly connected the dots but at that moment, it wasn't making sense. "O-okay," he said, just as quietly. He whispered the number to Jeremiah his voice showing off his confusion. What on Earth was he planning on doing with Haru's number? And why ask for it now of all times? Now was not the time to be making a call- His brain stopped with its trail of questions, "You...you aren't?" he asked, groaning a little as his neck was licked and he was ground into.
 
Jeremiah chuckled at Oliver's realization and confused question. "Oh no, don't worry. I know he's at work. I wouldn't call him now... And make him listen to you moaning with pleasure, begging for more... That would distract him too much... I'm just gonna send him a picture." He said and smiled. When Oliver opened his mouth to protest, he shoved the gag back in and fastened it behind his head. Picking up the pace, he began to thrust harder and fast into the desperate man. At the same time his hand began to stroke faster, quickly urging him to come to completion.
 
"Wait, of -" he groaned against the gag being placed back into his mouth and gasped as the other started to actually fuck him. He arched into each thrust and stroke. It didn't take long for him to come. He moaned loudly as his hips shook a bit as he came. He rode out the orgasm and as he came down from that high he took deep breaths, he struggled a little bit through the gag and the mask, but it still didn't concern him, he still could get decent breaths in and find himself winding down a little bit from coming. He was tight around Jeremiah and he leaned back a bit into Jeremiah as he moved his hips slowly to encourage the man to keep going if he hadn't come.
 
At the feel of Oliver clamping down on him, Jeremiah moaned and thrust harder. "That's right, enjoy that high." He told Oliver and watched him shoot his load hard. When he came down, he was panting heavily but seemed to be able to breathe fine. He slowed his thrusting for a moment but as Oliver began to wiggle, he started to thrust harder again. He could feel himself getting close and groaned, pulling out. "Fuck..." He hissed, wanting nothing more than to shoot his load inside the other but the long-lasting belief in not doing so prevented him. "I bet you'd like to suck my dick right now, wouldn't you?" He asked as he stroked himself, keeping himself on the edge.
 
Oliver gave a gasp groan when Jeremiah went back to thrust hard inside of him. He moaned in a small protest when Jeremiah pulled out of him. He wanted him so badly to come inside again, but this was Jeremiah's hard line and as much as he wanted it he knew also not to cross it. However, he would admit it was hard for him to keep himself from shaking his head when he was asked if he wanted to suck on his dick. He nodded after a moment, unsure if he was going to get to suck on him. Jeremiah seemed to be having fun not listening to him today, at least when he came to pleasure. He started to tongue at the gag though it didn't really show, minus a little bit of drool managing to make it out the sides of his mouth.
 
"I bet you would, wouldn't you?" He made no move to release the gag. Instead he walked around in front of the man and shot his load over Oliver's bare chest, letting out a gutteral moan as he did so. Then he repositioned the fucking machine And turned it on, allowing it to push up into Oliver. He turned it on to about half speed and left the room.
 
Oliver waited for the other to pull off the gag, but nothing, then he felt something hit his chest, he could only come to one conclusion. He gave a slightly unsatisfied moan, at least until the machine entered him. He was already so sensitive because of the sensory deprivation but adding having already come once he became more sensitive. He groaned and arched every now and then trying to get the machine to hit him just right, though he found it nearly impossible with the restraints and the lack of being able to move very well. He heard Jeremiah's footsteps become faint, but he wasn't really sure where he was. It almost left him a bit uneasy but he was sure he wouldn't have gone far. Not to mention Haru had shown him out to use the emergency release if he needed it.

After a few minutes, he was straining against his restraints and groaning loudly as his second orgasm came into play. He felt himself slowly slipping into that high but not nearly as quickly as he had the previous day because of where the machine was set at. However, the moment that his second orgasm was done he was still being used by the machine that showed no signs of slowing down and he was now sensitive because he had come twice and he couldn't see or really hear. His groans were becoming a bit quicker as his body slowly became overloaded with stimuli.
 
Jeremiah didn't go far, just to the guest bedroom to retrieve his cell phone. He got back to the room in time to be standing in the doorframe as the man achieved his second orgasm. Smiling, he snapped a picture of him mid-shoot. The he composed a text message to Haru.

[That's number two. I told him he's not getting out until you get home from work. If he reaches 5 before lunch, I'll commission one of these machines from you to the specifications we spoke about last night and I'll pay you twice the asking price. If he gets 7, I'll pay more. Of course just because he's in there until you get home, doesn't mean I have to let him out when you get here ;)]

He attached the picture then hit send and walked into the room and turned the machine off. "Enjoying yourself?"
 
"Hold on a second," he said to one of his clients when he felt his phone vibrate. He didn't recognize the number, but that wasn't anything new. He opened the text and smirked before writing back.

[Looks like I'm gonna be paid more than double then. Just so you're aware...that dildo is removable...interchangeable with any in the middle drawer, second dresser from the left. Oh, and if you're wanting to get rougher...that stuffs in the closet. Just remember to clean up. Enjoy.]

Oliver groaned in response to the machine being turned off, he nodded and squirmed a bit. Almost as if he was trying to get the machine to continue. His breathing was a little more shallow, but once again he was pretty sure he'd be okay. Though admittedly his judgement was starting to fade quickly.
 
Jeremiah felt his phone vibrate as it chimed again and pulled it out. He chuckled. "Arrogant asshole." He said out loud, though he didn't bother to explain what he was talking about. After a minute he made his was over to the drawer mentioned in the message and pulled out a slightly larger dildo. When he returned to Oliver he slid the current one out of him and detached it, attaching the larger one. After inserting it, he turned the machine on a notch passed the middle.

[Think I should hook him up to an IV to keep him from dehydrating on me? Sounds like he's going to be losing a lot of fluids.]
 
Oliver was still trying to keep himself coherrent so he really hadn't heard the other to question in the first place, not like he could anyway. He gave a small moan as the machine was pulled out of him, only to give a gasp as something larger was pressed into him and then set to pound his ass again. And he was very quickly back to moaning in a broken moan kind of way. He wasn't even sure how long he had been on this thing yet, but given the fact that he wasn't hungry yet, he figured it hadn't been very long.

[I got him to 5 before he needed some water, I'd just be careful with that gag and mask...he starts to breathe less later, from what I remember]

Oliver started to feel the beginnings of that lovely place he had been before, his brain was starting to move over to just simply pleasure as the machine thrust into him over and over again. His head moved a bit slower as he was trying to figure out where Jeremiah was once again.
 
Jeremiah rolled his eyes at the reply. Though he kinda had that coming because of what he asked.

[Don't worry, I'm giving him a break between each one and checking his color. I'm planning on removing one or both items when he gets to yellow. Btw, I found your video camera so you'll get to see every splendid second of his torment. Anyway, I told him I wouldn't call you so that I wouldn't disrupt your work but here I am disrupting it anyway. I'll let you get back to it. Have fun.]

At this point he was only half paying attention to Oliver as he started to search the web on his phone. He found what he was looking for and was about to make a phone call when Oliver came a third time. Smiling, he turned the machine off again. "Give me your color." He said sweetly.
 
Haru quickly read the message his interest peaked a bit at what he read. He hummed and said goodbye to his client before hopping into his car. He sat for a second before smirking.

[Just finished with a client and I've got a long way to drive for the next. Trust me, it's pretty hard to disrupt my work.]

And with that, he drove off.

The closer and closer Oliver got to his third round of coming his moans were turning more into small whines as he chased the orgasm that was right there. As soon as he came again he screamed out. His brain was right there, right on the verge of being where Haru liked him. He turned his head slowly over to the voice and slowly raised two fingers. It wasn't that he wanted to stop or even slow down but it was getting a little hard to breathe with both the mask and the gag on. His breath was shallow and he felt like he couldn't get enough air. Though he had to admit it made coming a whole different experience and though he liked it he was on this side of making sense that he knew he should let Jeremiah know.
 
Jeremiah read the message from Haru and grinned. A long drive huh?

[Long drives can be boring. Would you like to listen to some entertainment while you drive? Of course it might be a little distracting...]

At seeing the two fingers, Jeremiah nodded and pulled the gag from Oliver's mouth. "I'll give you a minute before I start the machine back up. I want to change the dildo again anyway." He explained, allowing Oliver some time to relax. He went to the drawer and picked out the next dildo. This one was like the anal beads that Oliver had teased Jeremiah with, only with stiff connections, allowing them to be rigid yet a little flexible. Each head got a little larger in girth but even the largest one was smaller than even the first dildo Oliver had been riding. The beauty of how these beads connected, however, was they could be shaped however the wielder chose. Jeremiah attached the phallus up to the fucking machine and then slowly slid them into Oliver, twisting the beads as they went in, making it so that each larger ridge of the beads would brush against Oliver's prostate with each thrust. They might be smaller, but this device would certainly be effective, especially once he turned the vibrations and thrusting on.

He waited to do that just yet though, he wanted to wait until he got a reply from Haru.
 
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