Who: Justin Taylor and Billy Kaplan What: Billy's First Time! When: Backdated: Saturday, November 16th. Evening Where: A Hotel Rating: NC-17 Status: Complete
So far Justin was very much enjoying his surprise weekend getaway with Billy. When Billy had told him to pack a bag he’d assumed they were going somewhere for the weekend, but he certainly hadn’t expected the hotel Billy had brought him to. It was a very nice surprise. So far they’d spent most of their time wandering around the nearby area and were just now coming back to their room from dinner.
It was a beautiful hotel and Billy was humbled by Jillian’s gift, he’d have to take her out for coffee or something. They had been shown to their suite - Billy had never stayed in a suite before - and anything they needed or wanted was available to them. It was incredible to see how the other half lived. Though mostly he was just enjoying Justin’s company.
“It’s been a lovely day” he sighed happily, arm wrapped around Justin’s waist as they walked to their room.
“It really has been,” Justin said, smiling as they reached their room and pulled a keycard out of his pocket, “Now the question remains, what do we do for the rest of the night?” He smirked mischievously as he slid the key card into the lock and turned the handle once he heard the click that signaled that the door was unlocked.
Billy chuckled, “Oh I’m sure we can think of something to keep us busy” he said with a cheeky grin and a light slap to Justin’s ass as they entered the room.
Justin’s brows rose slightly as Billy slapped his ass, but his grin remained in place as he followed the brunette inside, “You’re gonna get. You know that?” He said as he followed. Before closing the door, Justin took the ‘Do Not Disturb’ sign off the inside door handle and placed it on the outside then closed and locked the door before turning to face his boyfriend.
“Gonna get what?” Billy asked trying to look innocent and working mostly if it weren’t for the naughty smile on his face. He moved closer to Justin and placed his hands on his boyfriends waist, thumbs rubbing his sides through his shirt.
Justin grinned as Billy came closer, his own hands moving around to cup the brunette’s ass and squeeze lightly, “This.” As he spoke, he rolled his hips forward against Billy’s. He was already half hard and he wanted nothing more than to finally take that next step with Billy. They’d been working towards it for the last few weeks and he was sure that this was the right time.
“Mmm, I do hope so” Billy replied, leaning up to whisper it into Justin’s ear before he kissed the side of his neck. Moving his own hips closer to let Justin know that he was very much with him in agreeing that now was the time for them.
If it were possible, Justin’s grin widened as he low moan escaped his lips. He hadn’t wanted to rush Billy, seeing as he was a virgin and all, but it appeared that they were in complete agreement that this was the right time and Justin didn’t want to waste any more time. Giving Billy’s ass another squeeze, Justin licked his lips before speaking, wanting his voice to sound as commanding and confident as possible, “Then you should probably get on the bed.” Justin didn’t normally act so commanding in the bedroom or any other time really, but he had a feeling that Billy would go right along with it.
Billy appreciated Justin’s patience but he was definitely ready to take their relationship to the next step. Justin’s feeling was right and Billy moved to follow his command to get onto the bed, his heart rate was already increasing and he was anticipating Justin joining him. He licked his lips as he lay down leaning on his elbows to watch Justin’s movements.
Justin removed his shoes before moving towards the bed to join Billy, crawling along his body till they were face to face, “Are you nervous?” It would be completely logical if he was, after all it was going to be his first time and Justin wanted to know so he could do everything he could to make this experience as good for Billy as possible.
Looking into Justin’s eyes Billy nodded “A little” he admitted, “But excited too. It’s a good feeling, being with you” He smiled as he placed his palm against Justin’s cheek and leaned up to kiss him.
Justin smiled into the kiss as he rolled his hips down against Billy’s. “I’m glad that I get to be your first.” He said as he started kissing along Billy’s jaw and back towards his ear, “Now, what do you say we get rid of some of these clothes?” He smirked as he nipped at Billy’s earlobe.
“I’m glad too” Billy agreed, his hips lifting to meet Justin’s and he smiled as Justin kissed along his jaw. “I think that sounds like a really good idea” he replied with a little squeak at the nip.
Grinning, Justin moved down Billy’s body until he was straddling his boyfriend’s thighs and ran his hands back up his thighs till he reached his hips then proceeded to undo the button and zip of his pants, deliberately brushing his knuckles over his crotch as he did so. It being Billy’s first time, there was a chance that he wouldn’t last long, but Justin was going to drag this out as long as he possibly could. Besides, they were both young, so chances were good that they’d go more than once.
Billy was also determined not to let this happen too quickly, though when it came down to it he’d have very little choice in the matter. Still his hips pushed closer to Justin’s hand when it brushed over his erection. He ran his own hands down his boyfriend’s arms and helped Justin remove his pants. His breathing was irregular and his heart rate erratic.
It was clear just how much Billy wanted this and Justin couldn't help but smirk a little as he hooked his fingers into the waistband of Billy's pants and started pulling them down off his hips and legs. Once the brunette's pants and shoes were off and on the floor, Justin pulled his own shirt off before returning to drape his body over Billy's and kissed him again, slipping a hand under Billy's shirt. He’d probably be embarrassed later about how wanton and obvious he was being but right now all Billy cared about was touching and being touched by Justin. As they kissed Billy ran his hands over Justin’s bare chest, loving having the freedom to do so.
Billy would learn soon enough that Justin could be just as wanton and needy, so there was really no need to be embarrassed over it. “Still too many clothes,” Justin murmured against Billy’s lips as he rolled his hips down hard, his erection almost painful in his jeans. Sitting up and straddling Billy’s hips, Justin pulled his boyfriend up so he was sitting also and pulled Billy’s shirt off, leaving him in only his underwear. “Almost there.”
Billy grinned, “Well, I am, but I think you’re a little behind” he said squeezing Justin’s ass through his jeans before running his hands around the waistband to begin undoing them. He kissed Justin’s chest as he did so, running a tongue over his nipple experimentally watching Justin’s reaction as he did so.
Justin groaned, his fingers curling in Billy’s hair as his body responded to Billy’s tongue, “Shit.” Once his jeans were undone, he pushed Billy back down onto the bed and pushed his jeans and underwear down and off then hooked his fingers into the waistband of the brunette’s underwear and pulled them off to join the rest of their clothes on the floor. “That’s a lot better.” Smirking, he crawled up and pressed a kiss to Billy’s lips as he lowered his hips to meet Billy’s and rolled his hips, a moan escaping his lips as their erections brushed against each other.
Billy decided he wanted to hear Justin moan a lot more after he did so in response to Billy’s tongue, it sounded incredible especially knowing it his actions causing the noises. Billy hummed in agreement once they were both naked and then gasped as their erections touched, thrusting his hips up as he kissed Justin rather desperately.
Justin’s hips rolled down against Billy’s again as the brunette’s came up to meet his. It was clear that Billy wanted this just as much as Justin did. “Did you bring anything?” He asked, pulling back to look down at Billy. Despite not knowing where they had been going, Justin had assumed they were going to a hotel and he’d felt it was the right time so he’d packed condoms and lube just in case it happened, so if Billy hadn’t they would still be prepared.
Blinking through the lust filled haze that was now coating his brain Billy nodded, “In my bag” he said, remembering how red he’d gone when he’d gone to the counter and brought them. He hadn’t really known what to get so had brought quite a wide selection of everything really.
"Well aren't we prepared," Justin smirked and kissed Billy once more before he slid off the bed, naked and hard and went over to Billy's bag, "Fuck, Billy, did you buy out the store?" He teased as he glanced over his shoulder and smirked at Billy again as he grabbed a box of condoms and a tube of lube then got back on the bed, "Ready?"
“Hopeful maybe” Billy said with a grin, watching Justin as he moved over to the bag. He blushed brightly at the teasing, “I wasn’t sure what to get. Have you seen how many different brands and stuff there are?” he asked in his defence but he grinned too. “Ready” he nodded pulling Justin down for another kiss.
Justin nodded, "It's kind of insane how much there is to choose from," He smirked and kissed Billy back, hips rolling down against Billy's. As they kissed, Justin slid his hand down between Billy's legs, fingers skimming his balls and behind, careful to avoid Billy's hole, wanting to see the brunette's reaction before he went any further.
Billy whimpered into Justin’s mouth as he touched behind his balls, hips canting up to encourage Justin’s hand to go further. Yes he was a virgin but he’d seen enough porn and touched himself enough to know what was going to happen. And he wanted it. He didn’t want Justin to think otherwise.
“Fuck….” Justin wanted to hear Billy make that noise again and skimmed his fingers over the sensitive skin behind Billy’s balls once more, pulling back just enough to look down at him, wanting to see his face, wanting to see his reactions. His fingers slid back further, just barely touching his hole before pulling his fingers away and opening the bottle of lube. Justin hadn’t actually had sex since before he’d started dreaming and in his dreams with Brian he was always the bottom so this was a nice change.
More whimpers were pulled from Billy with every stroke of those fingers, his mouth gasping and his eyes blown wide as he looked at Justin. He was painfully hard and really wanted Justin to touch him more, he’d imagined this so many times since meeting his boyfriend. In every imagining Justin was always top, it never occurred to him to think otherwise.
It was clearly evident just how hard Billy was and Justin had to resist the urge to take him into his mouth, because he was pretty sure that Billy wouldn’t last very long if he did that. Instead, he coated two fingers with the lube then gently pushed one of the brunette’s legs back a little to give him easier access. Justin’s own cock throbbed at the sight before him and he bit his bottom lip as he rubbed one of his slip fingers against Billy’s entrance, waiting for the muscle to give enough so he could slide his finger in without hurting him. His finger went in to the first knuckle then he pulled it out slowly before sliding it inside again. “How’s that feel?”
Justin was right Billy wouldn’t last long at all once his cock was touched by mouth or hand. Billy bit his lips as Justin’s lubricated fingers settled against him and one slipped inside. He gasped but gave Justin a lust filled smile, “It feels good. Keep going” he managed pushing down against that finger. It didn’t feel too different to how he’d done it himself in fact it was better as Justin had a much better angle.
Justin watched Billy as he slid his finger in and out; watching his reactions and smirking as Billy pressed down against his finger. When he thought Billy was relaxed enough, he added a second finger and twisted them a bit as they slid inside. Billy felt so good around his fingers and he couldn’t even imagine what he’d feel like around his cock. “You feel so good, Billy.”
Billy’s face was flushed, a combination of excitement and embarrassment as Justin watched him. He’d heard people tended to make some very odd faces during sex and he desperately hoped he wasn’t one of them. He whimpered as both fingers twisted inside him, his breathing was ragged but he smiled at the words, “Your fingers feel amazing” he replied, “I..ah...bet your cock will be even better” he added cheekily, grinning as his cheeks heated.
Justin grinned and leaned over to press a kiss to Billy’s lips as he continued his ministrations. “Just you wait.” He slowly added a third finger, wanting to make sure Billy was ready before he moved on. The last thing he wanted to do was hurt Billy and since the brunette was a virgin, it was bound to hurt either way, but Justin wanted it to ease as much of that inevitable pain as possible. He continued thrusting and twisting his fingers and occasionally spreading them to test Billy’s muscles while at the same time, watching his boyfriend’s reactions closely. If he’d thought Billy was gorgeous before, seeing him like this was just mindblowing.
Once he was satisfied that Billy was stretched enough, Justin slid his fingers out and reached for the condom, “Ready?” He asked, a moan escaping his lips as he rolled the condom down his painfully hard cock and spread a liberal amount of lube over it.
The fingers were uncomfortable to begin with, not painful, just an odd sensation but as Justin twisted them the pleasure spread through his body, causing a flush to spread across his chest and cheeks. He gasped and closed his eyes as his boyfriend played his body like a master musician.
When he asked the question Billy was more than ready, “Please” he nodded, eyes blown wide with lust as he reached out to pull Justin against him.
“Just tell me if it hurts and I’ll back off.” Justin’s heart was pounding against his chest as he moved in to position himself at Billy’s entrance then slowly pressed forward until the head of his cock slid in, “Okay?” He asked, gazing down at Billy, wanting to make sure his boyfriend was alright before he continued.
"Promise" Billy replied, though his words came out somewhat breathily. He felt the pressure as Justin started to enter him, it was different than his fingers but it eased slightly once the head was in. "Okay" he confirmed, reaching up to stroke Justin's cheek. It really meant a lot that he was being so careful.
Justin smiled down at Billy as the younger man stroked his cheek then closed the space between them by capturing Billy's lips with his own, his hips moving slowly as he slid further inside him. The tight heat of Billy's body caused Justin to groan into the kiss and once he was fully seated inside, he stopped, giving Billy a chance to adjust and himself a moment to compose himself so that this didn't end before it began. Billy gasped into Justin’s mouth as he entered him completely. There was pain but it wasn’t anything beyond what he could handle. He appreciated being allowed to get used to the sensation though. Once the pain had settled to a dull aching feeling Billy rolled his hips experimentally, just a little movement but one which caused new, more pleasurable, sensations to zip through his body.
“Fuck...Billy, you feel so good…” Justin groaned, lifting his head to gaze down at his boyfriend, wanting to see his reaction as he, slowly started moving his hips, pulling out halfway before thrusting back in. Justin hadn’t had sex with a virgin in a long time and Billy was so tight that Justin wasn’t sure how long he was actually going to last.
“Oh god, Justin” Billy moaned his hands reflexively clutching his boyfriend. Billy felt incredible, there was still a dull ache but pleasure was definitely overtaking that feeling. Justin felt big and hot inside him and watching him move was amazing.
Grinning, Justin ducked his head to press a kiss to Billy’s throat then nipped lightly as he picked up the pace a bit, hips moving faster as he continued thrusting in and out of Billy’s body. The tightness and heat was overwhelming and his train of thought was beginning to falter as all he could think of was Billy and the noises they were both making.
Billy arched into the touch, exposing his throat more before he captured Justin’s lips with his own once more. They were moving together now and it felt so good that Billy decided to try something he’d seen, carefully he lifted his legs to wrap them around Justin’s waist. The movement caused Justin to enter him at a slightly different angle, going deeper than before and Billy cried out his name breathlessly.
On Justin's next thrust, he groaned, going even deeper, the new angle caused his cock to brush the sensitive bundle of nerves deep inside Billy's body. Feeling his climax start to approach, Justin slid his hand between their bodies, wrapping his fingers around Billy's erection and started stroking in time with his thrusts.
Billy's eyes went wide and his whole body shuddered when Justin brushed that spot inside him. It was like nothing he'd ever felt before and he cried out Justin's name. This turned into a wordless moan as that hand wrapped around his cock, it wouldn't take Billy long with how excited he was.
Justin knew from Billy’s reaction that he’d hit the right spot and he would have grinned, but he was far too focused on getting Billy to reach his climax, wanting to try and get him there first. Billy was making the most erotic noises, in Justin’s opinion, and while he knew what he sounded like when he came it was a sound he would never get tired of hearing and had already decided that he wanted to hear those noises as often as possible. As his climax approached, Justin’s hips stuttered slightly while his hand continued stroking Billy’s, faster.
Billy felt his climax approach and could do nothing but cry out as it rushed through his body before he came all over Justin's hand and his own stomach. His body tensed causing his ass to squeeze around Justin's cock.
As Billy's body tightened around him, Justin moaned, thrusting once then twice more before his orgasm washed over him and he came hard, inside Billy, his face pressed into the crook of the brunette's neck as a string of moans and Billy's name as well as curses slipped past his lips.
Billy wrapped his arms around Justin as little shivers of pleasure continued to slip through his body. He nuzzled into his boyfriends hair as he stroked his back, “That was amazing” he said softly, feeling shattered but incredible.
As Justin, slowly, came down from his orgasm, he collapsed on top of Billy, his head resting on his boyfriend's shoulder as his clean hand stroked his side lightly, "You can say that again." Justin's heart was beating so fast that he wasn't sure it would ever slow down, but it was totally worth it.
They lay there together, hearts beating frantically and breathing slowly returning to normal, and Billy thought it was the most perfect moment ever. If he could freeze time he would right now, but he couldn’t. At least not yet anyway. Instead he held Justin to him and thanked whatever was out there that he’d found such a wonderful boyfriend.