Stuart’s body obeyed Jeff before he could even consciously process the command.
He got it. Life had led him to this perfect moment, making all the waiting more than worth it. Better this than some cheap motel room encounter with someone whose name he’d probably never remember.
They were absolutely right.
When Brandon tried to insert a second finger, the burning pinch drew a whine from Stuart. Jeff leaned in and sucked on Stuart’s right nipple, drawing his attention even as Brandon slowed his hand and increased his suction on Stuart’s cock.
Immediately, the burning pinch transformed into aching pleasure, helping him hold back his release. Before long, Brandon was easily finger-fucking his ass with two fingers and nothing but pleasure remained.
Jeff alternated nipples, mouth and fingers, keeping the pleasure charged up and flowing through his system as Brandon started working him up to three fingers.
This time, Brandon went much more slowly, nearly bringing Stuart to the brink of release before moving his hand more, scissoring his fingers, loosening Stuart’s virgin ass. Pulse racing, Stuart both wanted this to never end and wanted Brandon to hurry up and get that cock inside him now!
Only once Brandon was satisfied that Stuart was prepared did he start finger-fucking him again, hard. At the same time he released the pressure on the underside of Stuart’s cock with his other hand, swallowing his cock deep. The hand in Stuart’s ass found his prostate, Brandon’s fingers sliding along it with every thrust.
The orgasm slammed into him, Stuart’s hands jerking against the restraints as the strongest climax he could ever remember experiencing swept through him. Brandon stayed with him, licking and sucking and swallowing, intensifying the sensation until, finally, Brandon’s hands stilled and his mouth was left holding Stuart’s cock, waiting.
Jeff leaned in and kissed him Stuart, tongue fucking his mouth. “Damn, that was hot.”
Brandon finally released Stuart’s cock and withdrew his fingers from Stuart’s ass, leaving him feeling empty. Brandon stripped off the glove and tossed it, inside out, onto the floor.
Then he reached for a condom. “I fully expect that, at some point fairly soon, you’re going to get hard again. The next orgasm, you have to earn it.” He tore the pouch open and slowly rolled the condom down his cock. “I haven’t decided exactly how yet.” He smiled. “I want to keep my options open, boy. But there will likely be begging involved.”
“Yes, Sir!” He was still trying to process the fading echoes of pleasure circling through his nervous system like ripples on a small pond.
Brandon knelt between Stuart’s legs, pushing them farther apart. “Jeff, hold him.”
Jeff sat up and grabbed Stuart’s ankles, pulling his legs back, keeping them wide open.
Leaving his ass exposed, vulnerable.
Brandon smiled down at him. “Good boys beg their Sirs nicely to fuck their ass.”
“Please fuck my ass, Sir!”
He chuckled, fisting his cock and slowly stroking it, making Stuart drool, wanting to taste it, suck it, make him come and swallow every drop.
“I can’t believe I’m going to be the first to fuck this sweet hole.” He drizzled some lube into his palm and slicked it up and down his shaft, over the condom, before wiping his hand on a towel Jeff had grabbed earlier.
“I want you to fuck me, Sir. Please!”
He arched an eyebrow at him. “A lot of times when I fuck you, it’s going to be after I’ve spanked or caned your ass. Nothing I love better than fucking a freshly reddened ass, how hot it literally feels.”
“Yes, Sir!”
“Are you going to be my good boy and follow my rules?”
He eagerly nodded. “Yes, Sir!”
“Including punishment?”
“Anything, Sir. Please!”
He nudged in, the head of his cock pressing against Stuart’s rim.
This was it. This was happening!
Brandon took hold of Stuart’s ankles and slung his legs over his shoulders. “Go down on him. Get him hard again, keep him hard, but don’t let him come, or it’s ten cane strokes for you.”
Jeff grinned at Stuart before leaning in and engulfing his cock with his mouth.
Almost immediately, Stuart felt his cock respond, trying to thicken and harden. Jeff was every bit as good as Brandon, just a different technique.
In his ass, Brandon started gently pressing until the head of his cock popped through the outer ring of muscle. That’s where Brandon paused, watching his face. “That’s it, baby. Focus on my cock. First cock inside you. You’ll never forget your first time, will you?”
“No, Sir.”
Brandon took short, slow thrusts, going a little deeper each time, until his body was pressed against Stuart’s ass. “Look at that. You took every bit of my cock the first try. Such a good boy.” He slowly withdrew until just the head remained inside him, then pressed forward deeply again.
“Once you’re used to me, don’t be surprised if there are times I bend you over and use you, hard, and then send you on your way again to do whatever you were doing.” He smiled. “My personal fuck toy. Make you eager to earn your orgasms. Might be times I let Jeff use you like that, too, if he’s been a good boy. Maybe even at the same time. Fill you up at both ends before we let you come.”
Stuart realized he was nodding, even though he had no conscious notion of doing it. “Yes, Sir!” Nothing was hotter than picturing that scenario, serving this man.
Both of them.
“You are an eager bottom,” Brandon said. Another long, slow thrust that left Stuart moaning. So much better, different than having his fingers in there. “I can’t wait to train you now that we’ve crossed this line. Expect to be wearing a butt plug to work sometimes. I might even have you call me on your lunch break and let you stroke yourself but not come until the next time you’re with me.”
Jeff eased up with his mouth as Stuart’s cock twitched at that mental image. To cede all control like that had been one of his biggest fantasies.
“And I’ll make sure my boy gets to come a lot, don’t worry. Especially at first. I’ll be using orgasms as rewards for you after spankings, so you start getting hard whenever you even think about me taking something to your backside.”
Brandon picked up the pace, slowly fucking him but now in steady thrusts, every stroke going deep before pulling nearly all the way out and plunging in again. It felt amazing, especially combined with the magic Jeff was working with his mouth.
“I think for the next round, I’m going to let Jeff fuck you on your hands and knees while I teach you how to worship my cock.” He smiled down at him. “Would you like that?”
“Yes, Sir, please let me worship your cock.”
“You know exactly the right answers to make me happy, boy. See? You’re a natural.” Brandon didn’t seem to be in a hurry to come, taking his time fucking him. He reached down and stroked Jeff’s hair, grabbing a fistful of it and holding on tightly. “You enjoying my boy’s cock?”
“Yes, Sir,” he mumbled around said cock. The vibrations from his voice reverberated throughout Stuart’s balls.
“I’m trusting you to obey me. You don’t get to make each other come, or make yourselves come, without permission. Understand? He breaks a rule, you’ll get punished for it. You’re more experienced, and you said you wanted to switch and top him sometimes. That comes with responsibilities. You have to take care of him when I’m not around.”
“Yes, Sir,” Jeff moaned around his cock again.
Brandon released Jeff’s hair after ruffling it. “Such a good boy for me. Maybe it is for the best that you two are living together right now. Less chance of you feeling jealous over me that way, if you guys are close. I’m hoping at some point we can talk about you guys moving in with me.”
Brandon dropped his hands to grip the front of Stuart’s thighs. “Okay, buddy. I need to bust this nut.”
Hard, deep thrusts had Stuart moaning wi
th every stroke. Now he really wanted to come again, amazed to be ready so soon after the first time. Brandon’s gaze bored into his, watching him.
“Yeah, baby. You take that…for…me.” He fell still as his eyes closed, Jeff also stopping what he was doing and now holding Stuart’s hard cock in his mouth. Then Brandon reached down and held the condom as he pulled out. “Be right back. Jeff, stay where you are.”
Brandon left the bed and Stuart wished he could reach Jeff’s cock with his mouth.
When Brandon returned a moment later, he sat next to Stuart on his other side, propped against the headboard with a pillow behind him. He leaned in to kiss Stuart before unclipping his wrist cuffs.
“Between my legs, baby. Hands and knees. Jeff, get yourself ready but don’t you fuck him until I say so.”
“Yes, Sir.”
Stuart turned over and stared at Brandon’s cock. Even having just come, it was still large and he couldn’t wait to get his mouth around it.
* * * *
Jeff knew he was damned close to subspace. While he couldn’t wait to fuck Stuart’s ass, he’d be lying if he said he didn’t want someone to fuck him, too. Sure, Brandon had already talked with him privately about this, just between them, that tonight was focused on Stuart and making sure this night was good for him.
He got it.
Didn’t mean he didn’t want to be used hard, too.
After nudging Stuart’s legs wider apart, he rolled a condom onto his shaft, added lube, and got ready.
Brandon was stroking Stuart’s hair and talking him through sucking his cock. It was sexy as hell watching Brandon’s cock disappear into Stuart’s mouth.
Lucky guy.
He consoled himself with the fact that Brandon had agreed to work with him, anal training to make his fantasy of DP come true. Well, to hopefully make it come true. Even if all they did was do it once and he wasn’t fond of it, still worth it.
He stroked Stuart’s back, holding on to his hips, waiting for the signal from Brandon.
Brandon plunged his hands into Stuart’s hair, holding him deep on his cock. “Good boy. It’s going to get really hard and big for you here in a minute. Jeff, get in there but don’t come yet.”
Jeff lined up his cock with Stuart’s well-prepared hole and slowly slid in. The moan Stuart let out around Brandon’s cock made Brandon smile.
“Yeah, buddy. See? I knew that would get me hard again.” He controlled Stuart’s head, slowly fucking his mouth up and down his prick. “Be my good boy. Suck your Sir’s cock.”
Jeff took another long, slow stroke, forcing himself to hold back. After so long, it felt damn good to have his cock in an ass again.
“You want to pound his ass right now, don’t you?” Brandon asked.
“Yes, Sir.”
“Something else you have to look forward to, boy,” Brandon said to Stuart. “Might be nights we tie you up on the bottom and I let Jeff ride your cock while I fuck this hot mouth of yours.”
Another moan from Stuart.
Jeff knew damn well what Brandon was doing and felt his heart sliding closer to love with every word the man said. He was searching for keys to dropping Stuart into subspace without having to lay a hand on him. Brandon already knew one of Jeff’s triggers was biting, that it would put him hard and deep into subspace without any effort at all.
Stuart was new to everything.
And Brandon wanted to make sure he did things right, even if it meant aching balls for both of them in the process.
“How’s his ass feel?”
“Good, Sir,” Jeff said, taking another stroke. “Nice and tight even after you fucked him.”
“Excellent.” Brandon stroked Stuart’s hair. “Okay, Jeff. Go ahead and fuck him. You’ve earned it. You can come.”
Jeff gripped Stuart’s hips and started fucking him. Not as hard as he wished he could, because he didn’t want to hurt him. But he couldn’t hold back, not as good as it felt. He fucked him fast, quick, short strokes that drew gorgeous moans out of Stuart and soon had his own balls tightening and coming and filling the condom as he buried himself in Stuart’s ass one last time.
His eyes fell closed as he savored it, relief, sooo much better than his own hand.
Brandon playfully cleared his throat. “Clean up.”
His eyes popped open. “Yes, Sir.”
“When you get back, get your ass ready.”
“Sir?”
He smiled. “I’m going to let this good boy fuck your ass next.”
Jeff grinned. “Thank you, Sir!”
* * * *
Brandon really wanted to play eenie, meenie and pick one of them to fuck him, but he also knew that could wait.
He wanted their focus on Stuart tonight. When Jeff returned from the bathroom, he quickly lubed himself and it was all Brandon could do to force Stuart off his cock and not shoot down his throat.
“Save some for Jeff, baby,” he hoarsely said. “Get a condom on.” Stuart wobbled a little when he sat up, the sweet subby glaze on his face unmistakably signaling subspace had been reached.
He crooked a finger at Jeff. “Your turn.”
Jeff dove onto his cock, needing no further encouragement or direction. He wasn’t worried about being rougher with him, either.
And Jeff spread his legs wide, ass high in the air for Stuart.
“Go ahead and fuck him,” Brandon said. “Just like we fucked you. Slow at first, until he’s used to you.”
But when Brandon lined up the head of his cock, Jeff rocked back, impaling himself and making Brandon laugh. He held Jeff’s face down deep on his cock for a long moment. “Didn’t tell you to do that boy, but good job, you.” He let Jeff up so he could breathe and went back to his previous rhythm with him. “Don’t come, Jeff. Once the boy comes, he’ll crawl under you and you can fuck his face.”
Jeff moaned around Brandon’s cock, obviously on board with that plan.
Just the fact that Brandon was able to get it up a second time so quickly triggered all his instincts in a good way. Stuart would likely be riding both of them to exhaustion from eagerness and the age difference.
But this felt right.
* * * *
Stuart bit the inside of his lip to keep from coming right then. Jeff’s ass engulfed his cock, eager, squeezing him. As he slowly started fucking him, Jeff picked up the rhythm, meeting him stroke for stroke.
If this was how sexy he’d looked in this same position, he wondered how Jeff had held back as long as he had. This was incredible!
“Go ahead and come, Stuart,” Brandon said. “You don’t have to wait.”
Holding on tightly to Jeff’s hips, he fucked him, pistoning his hips like a jackrabbit and feeling the explosion building in his balls. It didn’t take long at all, seconds for him to feel it erupt and hot cum filled the condom. He’d barely caught his breath when Brandon spoke.
“Get out of there and on your back on the bed, between Jeff’s legs.”
He did, Jeff’s cock stabbing at his mouth before finding his target.
“Okay, Jeff,” Brandon said. “Make me come first, then you can fuck a load into the boy’s mouth. I’m letting you be the first load he gets to swallow, since I got to fuck him first.”
Jeff moaned something unintelligible around Brandon’s cock, but Stuart felt him moving.
He tasted salty pre-cum, licked and sucked but not able to control his movements like he could when on his knees in front of Brandon. So he wrapped his arms around Jeff and held on for the ride.
* * * *
That wasn’t nearly a long or hard enough fucking for Jeff’s tastes, but he knew for tonight it was the best he would get. Even better, he’d get to come twice inside Stuart.
He struggled to hold back as he deep-throated Brandon, using every trick he knew until he felt his cock grow harder, hotter in his mouth.
And then Brandon’s fingers dug into his scalp as he took over and started fucking his mouth.
“Get ready
, boy,” Brandon said. “This one’s for you.” He moaned as he swallowed hot, salty cum, his hips now fucking in time with Brandon’s strokes as he was finally able to let loose and fill Stuart’s mouth.
In another minute or so, they lay sprawled across the bed and each other, catching their breath.
Jeff moved a leg so he wasn’t pinning Stuart down. “Go clean up.”
“Oh, yeah.” Stuart climbed out of bed and disappeared into the bathroom.
Brandon sat up and flipped Jeff onto his back, kissing him hard. “I’m going to plow that sweet ass of yours next time, buddy.”
Jeff melted against him. “Yes, Sir. Please.”
Brandon smiled down at him. “You two are going to keep me on my toes. I can already see it.”
Chapter Fifteen
Over the next month, while the men dated, Brandon kept their sex at the men’s shared house. But both men, sometimes alone and sometimes together, spent plenty of evenings at Brandon’s house with him and Emma, having dinner, working on the house, or just watching TV.
Enough of the living room was finished that Brandon could move his living room furniture out of the garage and into the living room.
Slowly but surely, the house was coming together.
And, slowly but surely, Tracey and Emma were trying to rebuild their relationship. Emma still wouldn’t spend the entire weekend there, but she did spend a couple of Saturday afternoons that gave the men alone time together, and she spent a couple of school nights there.
Brandon let Stuart and Jeff have sex on the condition that Jeff had to spend time wearing increasingly large butt plugs, which Stuart had to help him with.
That was all to help work Jeff up to the goal he wanted to reach of eventually DPing him.
It was in month three of them dating when a tropical system that hadn’t quite developed enough wind to be named moved in and sat on top of the area, thanks to a confluence of several weather fronts. For three days, the area received torrential rain in record levels.
Brandon even had to keep draining water from the pool. Their street flooded at one end, but at least the lot their house sat on was high enough they weren’t worried about the house flooding.