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“Dr. Whitaker, as you know they are doing free STI screenings today, I would recommend taking some time to get tested, the health and wellbeing of our staff is of the utmost importance,” Robby recites that last part from one of Gloria’s emails. The idea of Dennis sleeping with anyone makes him feel repulsed, but it’s not like they were together. He has no right to be jealous, though that’s never stopped him before. Dennis makes a face and turns to the board.
Every few months the hospital had some sort of wellness practice, or whatever the rebranded name was, for employees. Sometimes it was a blood drive other times giving out pedometers to track steps during a shift. One time they held a raffle for staff who completed the planking challenge for a chance to win a new pair of tennis shoes. Anything other than actually making changes to improve the lives of the staff like better pay or benefits.
“I’ve never…” Dennis gestures vaguely, his face bright red. “So I don’t think I really need to test for that,” He clears his throat.
“Any history of oral sex?” Maybe he shouldn’t have asked that, but now his dick was taking the lead instead of his brain.
“Uh no… I haven’t even had my first kiss, I haven’t done anything, Dr. Robby” Robby pauses at that but then resumes typing. “Sorry that was too intimate,”
“No worries, we’re all adults here,” He shrugs but hasn’t looked back at Dennis yet. How the fuck could he? “It’s just important to get screened if you are sexually active,” He finishes his chart and stands up, looking at the board like he doesn’t have it seared into his eyelids after eight hours. All he can think of is Dennis’ confession, all he wants to do is drag him to a bathroom and help himself to the other man.
Robby turned the new information around in his mind, over and over again. Whatever compelled Dennis to confess to him that he had absolutely no experience didn’t matter. What did matter was that it sat heavy in his stomach, threatening to move south. Not now, he thinks, willing himself to think of other things rather than his student taking him as deep as he could. Fuck, knowing he hasn’t even been kissed? That was dangerous fuel he didn’t need added to his already inappropriate attachment to the man. Since he came back for his internship, Robby had been jacking off every fucking night. And every night he imagined it was someone else’s hand on him, someone else moaning, someone else cumming onto his hand. A someone else by the name of Dennis Whitaker.
Later, as he stares at Dennis and Trinity’s retreating figures leaving the ED, he continues to obsess over the information. Completely untouched…how would he react to his first kiss? Would he shake a little, nervous at the anticipation of it? Would he be bold and try his best to kiss like he knew what he was doing? Robby’s thought of those lips against his and around his cock far too many times, but he never considered he would be the first to have Dennis’ lips on him. And that is dangerous, it fuels something in him, a part of him that always leads to making rash decisions, like the one he was about to make.
“Whitaker, can I talk to you for a moment?” He had followed Santos and Dennis without thinking about it. Fuck what was he about to say? Dennis leaves Santos to come back to Robby. When he is close enough that only the two of them can hear, he can’t believe what he’s saying. “If you ever want to practice, let me know,”
“Practice?” Dennis repeats and Robby can see the gears turning in his head. He sucks on his bottom lip and his cheeks get a little pink and yeah there’s no way he’s letting anyone else touch the man. If this strategy doesn’t work he’ll go directly to asking the man out, but if it does work well, some little white lies never hurt, did they? After all, he’d make sure Dennis would never want anyone except for him, so what’s the harm in fudging a little to get his in?
“It’s just a suggestion. I remember how nerve wracking my first time was, there’s a lot of pressure to have it be right,” He has little air quotes around that last part. “Sometimes it’s easier to just get it over with,”
“Okay, I’ll think about it,” Dennis nods but Robby already knows his answer. It might be today or next week, but he knows that blush and knows what will come of it. Fuck maybe he should’ve just asked out Dennis, that would be so much more normal, wouldn’t it? But there was something hot about the idea of actually teaching Dennis how to kiss, how to have sex. Fuck he really needed Dennis to say yes.
“Uh Dr. Robby,” Dennis finds him at his station the next day and he looks up, nodding. He knew what he was coming over for, could tell by the blush that had made its way up his neck. “I’ve been thinking about your… offer. I have a date next Thursday and maybe it would be good to… get it over with,” Robby doesn’t even care that he’s saying it like it’s a chore, his heart is beating double time. Keeping a neutral face, he just nods.
“Great, well do you have an off day between now and then? I’m off on Saturday so Friday could work,”
“Oh I’m off Saturday too,” Meant to be, thinks Robby, hungry at the thought of Dennis spending the night at his. “So it’s a date?”
“It’s a date,” He has to turn away for a moment. Whatever smile he gives probably looks completely ridiculous because of how excited he is. Schooling his features, he turns back to Dennis, who was hopefully none the wiser.
“Should I… just head over with you after work or?”
“That’s probably best,” He’ll need to clean and change his sheets, maybe even get a candle so the atmosphere is right. While he fully intends to ‘practice’ with Dennis, he does want to make it somewhat special. It was his first time and he deserves something more than just a quick fuck on his couch. Dennis departs to check on a patient but his heart is still beating hard.
He has two days to make sure his place is properly cleaned and smelling nice and not looking like a sad, lonely man lives there. That last part might be harder to fix in two days. But he could at least vacuum and maybe even dust so his place doesn’t look as untouched as it is. Truthfully, he doesn’t do much at home, and home is a loose word for the place, he mostly just sleeps, sometimes eats, and showers there. It wasn’t a place he particularly looked forward to going to after each shift. Maybe if he had someone waiting for him or a certain someone coming back with him after a shift, he wouldn’t be so depressed about it. A someone named Dennis Whitaker. Thinking of him riding home with him after every shift makes his already racing heart beat harder. Would they make dinner, tired as they are, together? Would Dennis scold him for his empty fridge and freezer full of frozen meals? What if they started to fall into a sweet, domestic routine together? Grocery shopping, coming up with meal ideas, taste testing each other’s food—
“What’s with you, you look like a school girl thinking about her crush,” Dana’s voice shakes him from his thoughts. He’s suddenly aware of the goofy, probably smitten looking, smile on his face.
“Oh you know me, I’ve got exciting weekend plans, as always,”
“What, you’re going to a mixer for seniors?”
“Very funny,” He huffs out, but doesn’t elaborate as he moves to look at the board. “Status on any openings?”
“Yeah, King’s discharging the lady in West with the UTI after getting some antibiotics, trauma one is moving upstairs, and there’s an open room in South,”
“Perfect, let’s see who else we can get out of here,” He stares at the board, mind still circling back to the fact that Dennis will be in his house in less than 72 hours.
When Dennis enters Robby’s house, he’s not surprised by how… bachelory it feels. There’s very little art or decoration save a few photos here and there, the furniture looks out of date, and he can tell that the couch and TV are probably the most used things in the place. The kitchen looks like it hasn’t been touched in months, maybe years. What the hell does his attending eat? Surely not just frozen meals and takeout? Maybe he’s a sandwich kind of guy.
Dennis did feel a little bad as he stepped inside. Robby had extended him a… strange but kind offer and he was definitely exploiting it for his one sided crush. Truth be told, he had wanted Robby to be his first for a long time. Despite the dates he had gone on, no one ever felt right. They couldn’t compare. Not when he could only think about those large hands under his shirt, around his wrists, between his legs— no one could come close to Robby. So when he had offered to help Dennis out, he had been over the moon but had to make up an excuse to not seem too eager.
Dennis had been trying to figure out how to get Robby interested in him for months. He tried reading older books, watching classic movies, reading the newest research so he could impress Robby. None of it seemed to work. Maybe Trinity was wrong and Robby wasn’t actually bi or gay. Maybe he was just a really caring straight guy. Straight guys sometimes sleep with trans guys, he was well aware of that. But did Robby even know he was trans? He’ll take whatever he can get.
But now he had an opportunity to get him interested. Even if he only ever wanted his body, Dennis needs to find a way to make tonight memorable for Robby. He had been good about his estradiol the past few weeks, which hopefully would prevent any pain from penetration. He had trimmed his pubes very tastefully last night if he said so himself. This morning he had done pushups and stretched throughout the day. Guys were interested in flexibility, right? But he was completely stuck on the sex aspect, or how to be good at that. He didn’t have a dildo to practice with and even with extensive research of how to give a good blow job, he was completely out of luck when it came to making this something Robby would continue to want. He was just trying to be helpful to Dennis, even if it was intimate, it probably didn’t mean anything to someone like Robby.
Dennis was well aware of the gossip about Robby’s previous relationships. It’s not that he slept around but he was… experienced. Beyond just his age, the stories from a nurse who had hooked up with him years ago made it seem like he was genuinely really good at sex. It could just be an exaggeration but Dennis wouldn’t be surprised if those steady hands were as skilled in bed as they are in the ED.
“Whitaker? Did you want anything to drink?”
“Oh, uh water is fine, and you can call me Dennis,” His nerves were scrambling under his skin. Now he was in house. This was real. This was actually happening. Robby nods and disappears to the kitchen, so Dennis wanders to the couch, not sure what exactly they do. Are they just gonna strip and go right to it? Or will Robby kiss him first, taking that first before he takes the other firsts?
Robby sets a glass of water on the coffee table in front of the couch and sits beside Dennis.
“I want you to know that at any point we can stop and be done, okay? This is about you,” Robby is looking at him with such sincerity that it makes Dennis’ stomach warm. Oh he was so fucked. By the end of the night, if not sooner, Robby would realize how in love Dennis is with him. And he would probably laugh and ignore it or worse lecture him about it. So he’s gonna have to try to hide that as long as he possibly can. In response Dennis just nods.
“Thank you, for this,” Robby looks surprised, eyebrows raised. “You’re right that it feels really nerve wracking, just holding on to this for so long,”
“There’s a lot of pressure around sex and intimacy in our culture, at the end of the day it’s really about feeling good and making sure your partner feels good,” Robby’s explanation makes that heat in his stomach travel lower. He was going to make Dennis feel good, that he had no doubt about. What he did doubt was being able to make Robby feel good. “So this date next week, you think you’ll be taking things to the next level?”
“Uh yeah, we’ve gone on a few dates already and it’s been going well,” Lies. He hadn’t dated anyone in months. But this was his only acceptable in to getting access to Robby, in his mind. Otherwise Robby might see him as too eager to sleep with his attending.
“Hm,” Robby looks amused and Dennis wonders if it’s clear that he’s lying. “That’s good, I know the dating world right now is a little difficult,” Okay maybe he believes him.
“What if I can’t make you feel good?”
“You really don’t need to worry about that. Tonight is about you, okay?” God his head was spinning, he thinks he’s already getting wet. Just being this close to Robby outside of work was making him short circuit. He nods and takes a long sip of his water. Robby stares at him the entire time, probably waiting to get this started so he can get it over with sooner.
“Okay, I’m ready,” Robby chuckles at that and slowly moves closer to Dennis. He can feel his face starting to flush at the proximity, able to feel Robby’s warmth inches away. Never before has he needed someone to touch him as much as he needs Robby to touch him.
A hand cradles his face and he relaxes into it, staring at Robby with widened eyes. This was actually happening. The very first kiss of his life and it was going to be the man he was definitely in love with. A thumb brushes his cheek softly and he closes his eyes as he leans in. Robby’s lips find his a moment later, finally kissing him. There’s no doubt Robby can feel how hard his heart is beating, it’s practically in his throat.
It’s better than Dennis has expected, soft and Robby’s lips aren’t as dry as they look. It makes something in his stomach that he’s never felt before turn molten. Robby moves his lips against Dennis’ and it takes a few moments before Dennis realizes he’s supposed to be kissing back. It’s a little clumsy, trying to figure out the rhythm, but once he does, it feels really good. Like insanely good.
“Wow,” Dennis breathes, unable to help himself. “That was…”
“You’re a quick learner, Dennis,” Hearing his first name from Robby’s lips had that molten in his stomach moving south embarrassingly quick. “Do you want to try to take the lead?” He nodded but was unsure. “It’s okay, it doesn’t need to be perfect, it’s only your second kiss sw—Dennis,” He catches himself and Dennis burns even more at that. Was he going to call him a pet name? Oh fuck, he really wasn’t going to seem cool at all tonight.
Leaning back in, Dennis mirrors what Robby had done when he kissed him. Robby kisses back instantly, for a moment there’s a little fumble as Dennis’ brain goes offline before he’s back to kissing Robby again. This time, Dennis moves one of his hands to Robby’s shoulder, holding onto him. As their lips move, it’s becoming easier for Dennis to predict Robby’s movements and match them in reverse. Without thinking, he sucks on Robby’s bottom lip, and the other man makes a small noise in his throat.
They pull apart and Dennis feels absolutely wild. Robby’s eyes are dark as he strokes Dennis’ cheek. Oh fuck, he was definitely wet as hell by now, replaying that sound in his mind and wanting more. He wants to make Robby feel as good as he’s making Dennis feel.
“That was a bit of an advanced move,”
“I’m sorry, I just thought—“
“It’s good Dennis, maybe you’re ready for the next stage,” Robby says but doesn’t explain further, instead he’s kissing Dennis again, this time his lips a little more firm and guiding. Now he sucks on Dennis’ bottom lip and he moans, unable to help himself. It felt incredible. Instead of pulling apart, Robby rubs his tongue against Dennis’ lips. Is he supposed to open them?
Awkwardly opening his mouth, he moans again when Robby rubs his tongue against Dennis’. Shit, that was really incredible. Who knew kissing felt so good? He doesn’t really do much with his tongue. he just sort of rubs it back against Robby’s as best as he can. The hand cradling his face is firmer now, less like support and more like he’s holding Dennis in place.
“Feel good?” Robby asks, barely parting from Dennis, his breathing heavy. Dennis nods, chasing Robby’s lips. This time he presses his tongue against Robby’s lips and is thrilled when he feels his mouth open to him. Now he’s a little unsure but tries to do what Robby did. The way Robby’s tongue responds is absolutely mind blowing, it’s almost like he’s massaging Dennis, applying a little pressure to his tongue. Again, Dennis moans and this time he presses himself into the couch to get some friction. Robby notices the movement and pulls apart. “You’re getting hard?”
“Uh… wet,” Dennis corrects and Robby slowly moves his hand on his face to his crotch. Dennis can’t help it and pushes up then gasps in embarrassment. “I’m sorry that was so—“
“Don’t be sorry, your body just couldn’t help it, hm?” Oh his voice was really doing something to Dennis. He doesn’t know whether it was condescension or not in his voice, whatever it was, it was making Dennis feel like putty in Robby’s hands. Robby takes Dennis’ hand and places it on his own crotch and Dennis gasps again.
“Oh you’re— fuck you’re big,” Dennis can’t help but grip at Robby’s bulge and Robby gives a shuddering breath. He didn’t feel fully hard, which made Dennis’ head spin. How big was he? And would it hurt? No, Robby would make sure it didn’t hurt, he was sure of that.
“Okay, we should probably move to the bedroom,” Robby stands and takes Dennis’ hand with him. Embarrassed, he takes his hand back. Really, he wants to keep feeling Robby and exploring what a cis dick feels like. His own dick was like two inches but he’s been thinking of wrapping his hand around Robby and stroking him for so long, now it’s so close to actually happening.
Dennis follows Robby like he’s leading him to heaven. And in a way, he is. The bedroom is just as bachelor paddish as the rest of the house, only a bed, a night stand, a wardrobe against against the wall, and one framed piece of art on the wall. It smelled nice though, like lavender and eucalyptus. That always made him feel calmer and breathing it in, he did find his heart slowing a little. Just as soon, as Robby waits at the foot of his bed, it skyrockets again.
“C’mere,” Robby’s smiling, something amused with a touch of fondness. It makes Dennis stumble a little, embarrassed by how much that smile impacts him. “Can I put my hands under your shirt?”
“Yes,” Dennis’ quick answer makes the other man laugh a little. Just as soon as Dennis is about to feel embarrassed again, he’s pulled into another kiss. While he’s distracted by their lips and eventually their tongues moving together, he barely registers a hand slipping under his shirt. It’s not until said hand meets his skin that he chokes on his spit. Robby could probably feel his heart stammering at the touch, but he slid the hand up, up, up, from his stomach to his nipples. Taking a bud between two fingers he pinches a little and Dennis pushes himself against Robby, eager for more. “Fuck,” He whispers against Robby’s lips and is brought into a more feverish kiss. It’s sloppy, uncoordinated, as his own hands push up under Robby’s shirt.
Maybe he should have asked but as soon as his hands touch the hairy belly under the shirt, he’s obsessed. Of course Robby would be hairy, he’s probably got a nice happy trail that leads to his dick too. Dennis lets his hands explore as Robby finally goes to push Dennis’ shirt off. Their kiss breaks and Robby is staring down at him with a look he doesn’t fully understand. Did he like this? Just as much as Dennis did? The same way Dennis did?
“Can yours come off too?”
“It can,” Robby strips his shirt and Dennis marvels at him.
“Oh fuck,” He was gorgeous shirtless. He had a bit of a belly that Dennis wants to rub his face against and bite. His nipples are hard and now he wants to feel them, see if it feels as good for Robby as it does for Dennis.
“Sorry I’m not as in shape as I probably should be but—“ Robby sounds insecure, something he rarely ever showed, and Dennis was quick to shut that down.
“No it’s— fuck Robby, you’re hot you’ve got to know that,” Dennis blurts and then freezes. “I mean, you’re an attractive man,” He tries to back track but Robby has a grin spreading across his face.
“Is that so?” He’s pulling Dennis so their chests touch. It makes Dennis squirm, pressing to try to get impossibly closer. He can feel Robby’s dick through his pants and god he needs it inside him.
“Yeah,” Dennis can feel Robby’s pounding heart and a few things start to cross his mind but before he can think too much about it, he’s pulled into a kiss. Again, it’s sloppy, and it makes him pulse around nothing. Now he took a leap and went to take the belt from the other man’s pants. When he gets a moan, he decides that’s a ‘yes please’ and undoes the belt, followed by unbuttoning and unzipping the pants. Robby gracefully steps out of them as he does the same to Dennis.
“Your turn,” Dennis awkwardly strips himself, accidentally pulling his underwear down too. He almost pulls it back up but they’re gonna be fucking anyway, right? He steps out of them and pushes his socks off too. “Let me see,” Robby gently commands, pulling apart so he can stare at Dennis.
Now he feels self conscious as Robby drinks him in. His moles and freckles were scattered around his body, not forming a cohesive pattern at all. He had a bit of a stomach but at least he had his arm muscles. Robby’s gaze stops between his legs, his breathing suddenly heavy.
“May I?” He reaches out and Dennis nods excitedly. The idea of Robby’s hands finally touching him there makes him even wetter than he already is. He doesn’t think he’s ever been this wet in his life. Carefully, Robby strokes his dick, both of them moaning. “You are hard, so fucking hard,” His voice no longer sounds professional or relaxed like it had earlier. It sounds hungry. A finger slips between his thighs and he gasps at the wetness he finds. “And you’re soaking wet,” A finger teases his hole and he whines, unable to help himself.
“I can’t- I can’t help it,” He argues but Robby just keeps his smile plastered on his face.
“It’s good, Dennis. When you’re wet it makes things a lot easier, and it shows your partner how excited you are,” He takes his hand back and steps closer to Dennis, pressing his dick against Dennis’. “Are you excited, Dennis?”
“Yes,” He stares up at Robby who leans back in for a kiss. It’s short and he chases Robby’s lips when he pulls back but the man just tsks.
“You wanna get on the bed b- Dennis?” Again, he swears he was going to use a pet name for him. Dennis wishes he would, wishes he would call him baby or sweetheart while he destroys him. But that hunger Dennis thought he heard must just have been in his mind, clearly Robby is trying to keep this somewhat professional. Even though he’s going to be fucking him soon, hopefully.
Dennis complies, feeling incredibly vulnerable as he lays naked against what he assumes is an expensive comforter. What if he gets his wetness all over it? Would Robby get mad at him? No, surely he wouldn’t, even if it didn’t make him ecstatic, the man was never cruel to Dennis.
Staring at him, Robby pulls his boxers down and Dennis sits up, alarmed. Jesus christ he was massive. Not just in length, he was girthy too. His head was red and dripping pre-cum that Dennis desperately wanted to lick off of him. But suddenly anxiety struck through him. How the hell was that supposed to fit inside of him? Robby seems to take notice of his anxiety.
“We’ll open you up first or if you don’t want to continue we don’t need to,” His voice is soft and caring as he climbs on top of Dennis. The truth is that Dennis needs this. Not just to get his first time ‘over with’ but because he needs Robby inside of him. And as the anxiety subsides, a new excitement builds. The image of Robby’s cock stuffing him full made him clench again, which Robby seems to notice and takes a breath in.
“O-okay,”
“You sure?”
“Yeah, yeah I’m sure, keep going,” He says with more confidence and Robby nods. “You know if you want to stop at any point or if this is uncomfortable for you, we can,”
“Oh trust me, I’m very comfortable,” Now Dennis was questioning things again. Did that mean he was glad to be doing this? Did he actually want Dennis, physically at least? Beyond just being turned on from making out, was there more here? He hopes he’s not reading into things but it felt like maybe… maybe Robby liked him back. Robby leans down to kiss him and Dennis’ anxiety is completely washed away. Their lips move slowly but Dennis’ heart races all the same.
A hand pets down his stomach, fingers circle his clit and play with it, but then they dip lower, until they’re sliding against his lips, playing with the wetness there. Dennis moans, arms wrapping around Robby’s neck as their tongues move languidly against one another. A finger circles his pussy and he spreads his legs, nodding into the kiss, an invitation. Robby takes it.
When his finger starts sinking in, Dennis begins to understand why sex has such a hold on people. Feeling someone else’s finger sink inside him was making him pant and hump upwards. Fuck it felt so much better than his own finger, probably because it was longer and thicker. God just one of Robby’s fingers had him feeling dangerously close to cumming.
“Oh fuck,” Dennis breathes out shakily.
“Okay?”
“More than okay,” He pushes himself against the finger, eyes fluttering closed as he feels the knuckle brushing his lips. Robby pulls out before pushing back in. “Mhm,” Dennis is really trying to be professional, to not ruin this for the sake of their working relationship, and he already feels bad enough for taking advantage of Robby’s offer. Now he felt like a creep, for months he’s been fingering himself imagining this and now he would use this for the rest of his life to get off.
Robby kisses him again, pushing in and out of his sticky cunt, making the lewdest sounds Dennis has ever heard. He never got this wet on his own and it was like a damn faucet the way he was leaking all over Robby’s finger.
“Someone’s really excited,” Robby teases and it make Dennis feel faint. “That’s good, Dennis. Really good that you feel good,” He nods, staring up probably looking like a damn fool. A second finger slowly pushes in and he’s surprised it fits after so little prep with the first one. Now Robby starts scissoring his fingers inside of him and makes a curling motion that has Dennis arching his back.
“Oh!” His voice feels foreign, he’s not even quite sure it was his voice but somehow a voice that still came out of him. Robby halts his movements and stares at him, waiting. “No it was… could you please do that again?” Robby obliges and he arches off the bed again, moaning.
“Hm,” Robby looks pleased with himself as he rubs that spot over and over. Dennis could feel his orgasm approaching but just as quickly, Robby went back to fucking him slowly with his fingers. He did that scissoring motion again, the one that he could feel stretches his walls out. Pulling out, he rubs Dennis’ clit, the wetness making it nice and slippery between his fingers.
“Oh fuck, fuck, I’ll cum,” Robby was massaging him slowly, like they had all the time in the world. His hole clenches around nothing as that warmth in his lower half is threatening to boil over.
“That’s alright, baby,” The pet name is what does him in. He whines as he cums, rocking up into Robby’s fingers that stroke him through it. “There we go, just like that,” It’s more like he’s talking to himself but the fondness and pride in his eyes is clearly for Dennis. Before his pussy stops throbbing, three fingers sink in easily.
“Holy shit,” It’s too much but at the same time not enough. It’s a larger stretch than anything he’s ever had inside of him. Robby is slow again while fingering him and it’s making Dennis lose his mind. “You can- you can go faster,”
“You sure?” Robby pauses and Dennis nods, feeling like he’s touching a live wire, Robby’s fingers shocking him over and over. Obliging him, Robby speeds up and Dennis tries to open his legs even further, needing more. He whines and moans and should be more embarrassed that he’s doing this in his boss’ bed but it just feels too good. He can’t help it. And Robby looks like he’s in a daze, staring at Dennis like he’s committing this to memory.
The moans get louder as Robby gets faster, wrist snapping as his fingers drag against his walls. Dennis could feel his cum coating Robby’s fingers as he fucks info him over and over, not giving Dennis a moment to experience anything other than pleasure. He curls his fingers at that spot again and Dennis can no longer take it.
“Need more,” Dennis pants, eyes feeling a little wet. Fuck he needed to feel Robby inside him as soon as possible.
“Another finger?” Robby’s eyebrows raise a little as he keeps fingering Dennis. He can barely get his words together, can only feel those fingers curling and rubbing against that spot again. He shakes and lifts his hips, eyes fluttering closed before he snaps them open again.
“No, you, need you,” Robby’s fingers still and then slowly pull out. Robby holds his hand in front of him.
“Spit,” Dennis does, watching the liquid in Robby’s palm. It’s joined by Robby spitting into his hand and then stroking himself with the mixture. For a moment, Dennis feels a little dizzy, looking at Robby’s full boner just inches from his pussy. Now that dick is pressing itself between his lips as Robby rocks back and forth, getting himself more wet from Dennis. Staring at the site before him, he feels enraptured.
“Oh fuck, so big,” He says it under his breath but Robby chuckles. Looking up, he sees Robby staring down at him with that hunger again. Oh he is going to ruin me, thinks Dennis as he suddenly feels Robby’s tip pressing against his entrance. He clenches a little, he can’t help it he’s nervous.
“We can stop,” Robby starts and Dennis whines, unclenching. His Magen David swings as he adjusts himself between Dennis.
“No, just nervous, don’t stop,” He sounds absolutely pathetic. Like he’s begging. And Robby doesn’t seem to mind it, instead it seems to egg him on. He slowly starts to push into Dennis.
When his head finally enters Dennis, Dennis makes yet another embarrassing sound, but it feels so good. So much better than his fingers, Dennis is finally being filled by Robby. His head pushes past that spot that makes him wild and he whines, trying to get him to push in faster but Robby keeps his pace.
“Taking me so well, that’s it,” Robby’s voice is soft, like he’s trying not to scare Dennis. Fuck he was so screwed, how the hell is he supposed to have sex with anyone else? He was barely inside him and it felt so good. So much better than Robby’s fingers, which had been miles above his own fingers.
“It’s too big, it won’t fit,” Dennis whines, because he does want it to fit, but he feels like he’s being split open on Robby’s dick. And he was loving every second of it, but there’s no way he’ll be able to sink all the way in. Fuck how was he getting fucked with the biggest possible dick for his first time?
“It’ll fit sweetheart,” Robby consoles him, pushing in inch by inch still. Dennis feels like he’s in heaven already, so full of Robby. God he can’t believe that this is really happening. “There we go, all in,”
“Fuck— you’re so big,” Dennis moans, looking down and he swears he feels him in his stomach. And sure enough, Robby is flush against him, hairs touching Dennis’ pussy. “Fuck,” He covers his face with his hands, it felt so fucking good. How the hell was he supposed to know just being penetrated like this would feel this amazing? It’s almost like he’s high.
“C’mon, let me see that handsome face,”
“It’s embarrassing,” Dennis whines, clenching involuntarily and then gasping at the sensation that follows. It’s like the pleasure is echoing through his body. “Oh god, fuck it’s so good,”
“I haven’t even moved yet,” Robby teases and he looks through his fingers. The man is staring down at him with so much lust that Dennis’ heart skips a few beats. The older man wants him, wants to fuck him, Dennis isn’t just imagining this. So he lowers his hands from his face, despite his face that probably reads like a book, telling Robby how he feels. Which is that he’s head over heels for the man and now can’t imagine kissing anyone else, let alone having anyone else touch him. “There we go,” He sounds pleased with himself and now his expression is wolfish, like he’s going to eat Dennis alive.
“You can move now, I can take it,” In reality he wasn’t sure if he could. What if it hurt? What if Robby fucked him hard like he probably wanted to? What if Dennis couldn’t tell him to stop if he needed to? All his doubts and worries are dismissed the instant Robby pulls out and slowly pushes back in. Oh god he’s soaking wet.
“That okay?”
“More than okay,” Dennis’ voice comes out of him but he can barely register the words. The only thing he’s really thinking about is Robby’s dick slowly filling him over and over again. He can feel his wetness coating Robby and he hopes he likes it because he’s getting wetter with every thrust. “Oh fuck, fuck,”
“Need me to stop?” Robby’s eyebrows knit together and he shakes his head furiously. God, stopping is the last thing he needs.
“No Robby— it feels so fucking good I can’t— it’s too good,” Now his voice shakes a little and Robby keeps his slow pace, making Dennis melt all over him. He felt like his pussy was literally melting all over Robby. If it didn’t feel so amazing maybe he’d have half a mind to ask Robby if it felt nearly as good for him too. “Oh god Robby— fuck that’s— you’re so big,”
“You’ve mentioned that,” There’s a smirk. “You think your date will have a dick this big? You think he’ll be able to fill you up like this?” Robby’s pace is starting to speed up and Dennis whimpers, he thinks he’s touching his cervix. His legs wrap around Robby’s back, heels pressing into his sides. He doesn’t give a damn about the lie he told Robby because now he knows Robby had definitely lied to him about ‘practice’. The man simply wanted Dennis, the same way Dennis wanted Robby.
“Don’t care, just want you,” The admission pleases Robby. A grin, like he has been waiting for that answer the entire time.
“Good, I didn’t plan to share,” That makes his head spin. He was right that this was a set up of sorts but he didn’t care, it turns him on that Robby devised this little plan to fuck him. “Only I get this pussy,” He leans down to kiss Dennis and now he really can’t help himself. Kissing was also really fucking good, he thinks as their lips move against each other. He latches on and is panting into it as Robby keeps fucking into him harder and harder.
“G-god, fuck,” His head is so hazy, he doesn’t know how he’s supposed to focus on anything ever again. “Only you,” Robby grunts and now he must be fucking into Dennis with his full strength because the bed is squeaking and slamming into the wall, his full weight sinking into Dennis over and over and over. There’s these wet sounds that he belatedly realizes is his pussy and if he could be embarrassed would cover his face again. But now as he moans and whines and even whimpers as Robby plows him like he’s been imagining for months, he doesn’t care about the sounds. In fact, the sound of Robby’s balls slapping against him turned him on even more.
A hand pushes between them and starts to touch Dennis and somehow everything feels even better, which he didn’t think was possible. How could sex feel so good? Or was it because it was Robby that it felt so heavenly? Either way, as he’s rubbed he realizes he’s going to cum and tries to hold on, just a little longer, but the combination of Robby’s dick making itself at home in his pussy and his deft fingers working Dennis’ clit, he falls over the edge. Oh god it felt so good to cum with something inside him, spasming around Robby’s hard dick and clenching down on him, like he didn’t want him to pull out. The moan he lets out is so goddamn embarrassing, it’s high pitched and needy, but Robby seems to love it.
“That’s it, let it out, just like that, you’re doing so well,” Robby’s voice is so soft and soothing it has him whining. He needs more, he needs—
“You’re gonna cum in me right?” Dennis slurs as Robby keeps fucking him. But he abruptly stops, pushing all the way in. He’s at Dennis’ cervix, just letting his tip rest against him, letting him feel how full he makes Dennis. It’s enough to bring him back to the edge, despite having just cum. “Oh—please?” He looks up at Robby who is shaking now.
“I’ll cum pretty soon if you keep talking like that,” He squeezes his eyes shut and takes a few steadying breaths. “Fuck, doubt I’d even be able to pull out anyway,” He starts fucking into Dennis again and throws his head back, moaning loudly. “Your fucking cunt, fuck,"
“Yeah?” Dennis felt a sudden surge of pride that Robby was becoming as undone as he was. That he could please Robby. Maybe it was enough that Robby wouldn’t even think of fucking anyone else, not if he had Dennis.
“Can’t get enough,” He pulls Dennis back into a kiss, though it’s broken by Dennis’ incessant moaning. He eats them up and moans back into Dennis’ mouth. It makes him dig his heels deeper into Robby. Then he has a better idea. He drags his fingernails down Robby’s back and the reaction is even better than he could have imagined. “Fuck, Dennis, fuck,” He repeats the motion and Robby slams into him sloppily, his rhythm breaking down. “Gonna fill you up,”
“Please,” Dennis whimpers, needing it more than anything else. Part of him doesn’t want this to end, but another part that is growing wants to see Robby finish inside him. He needs to see him cum, needs to see if he can feel him cum. “Please, cum in me, I need it, daddy,” He tries the name out and it feels good in his mouth.
“Oh fuck— fuck,” Robby suddenly pushes all the way inside him, mouth falling open as he moans. He’s staring down at Dennis, still like he’s hungry but also the pleasure on his face pleases Dennis. It’s like he’s so lost in it, that the only thing he can think of is Dennis. And then he feels a warmth bloom inside him that has him gasping. It felt good. Fuck it felt good to actually feel Robby cumming inside him.
Robby leans down to kiss him, panting into it and moaning and Dennis needs this all of the time. How was he supposed to do anything ever now? Now that he knew this pleasure, how was he supposed to be calm at work, knowing what Robby feels like cumming inside of him? Fuck, he kisses Robby back, rubbing their tongues together. Eventually Robby pulled apart and pulled out. The sudden coldness and emptiness makes Dennis whine, why couldn’t he just stay inside of him?
Robby lays beside him, breathing heavy. Neither talk for a while and Dennis finds himself staring at Robby’s profile. The man has his eyes closed as he catches his breath, his chest hair is matted with sweat and his Magen David clings to it.
“I’m gonna cancel that date,” Dennis stares at Robby’s side profile, which turns to him as soon as he says it. Robby looks content with that, more than content, a little ecstatic. A smile is plastered on his face.
“Good,” Robby pulls him into a kiss. “Be mine instead,”
“Already was,” And now Robby moans a little, pulling Dennis on top of him. They keep kissing and Dennis gets lost in it, feeling himself getting wet again. It’s like Robby intends to ruin him so thoroughly he doesn’t leave this bed again. That sounds like a nice idea. A hand moves to between Dennis’ thighs and he can’t help the whine he lets out and the squirm that accompanies it as Robby’s fingers stroke his lips.
A finger slides in and he pushes back against it. He can feel Robby collecting the cum that had started to dribble out and push it back inside of him. Good, he needed it to stay inside of him. It was what he deserves, he thinks as Robby moves to suck on his tongue. That made him squirm against the finger leisurely fucking him.
“Forgot how strong a libido young people have,” Robby murmurs against his lips and Dennis can’t help but giggle. Normally he didn’t have a high libido and wasn’t really expecting another orgasm but as Robby spread his cum alongside his walls, he was close anyway. The giggle turns into a low moan and his hips rocking back. “There we go baby, just let daddy make you feel good okay?”
“Daddy,” The name once again just feels right in his mouth when he calls Robby it. It wasn’t something he’s thought about but now he can’t stop thinking about it and can’t stop wanting to hear Robby call him his daddy. “Daddy,” He repeats and Robby chuckles.
“Yes baby, what do you need?”
“Another,” He wiggles his hips and his demand is met. A second finger pushes in and then they’re both pushing against that spot again. “Oh god,” He whimpers, pushing back against the fingers for more. If only Robby could fuck him again. Instead those fingers probe at the spot.
“Let’s see if you can cum on daddy’s fingers, okay?” Robby murmurs and he nods, tears starting to well up. It felt so fucking good, even though it almost felt overwhelming. The wet squelches of his pussy echo alongside his moans and Robby looks incredibly pleased with himself. Those fingers fuck back into him and he is feeling breathless, heaving as his over sensitive pussy gets pleasured again. It felt too good, it felt like too much after Robby had just fucked him to heaven, but he needed it. Needed to keep feeling Robby take him apart.
Robby’s back to pushing at that spot and Dennis feels erratic and helpless. He starts humping against the fingers, pressing that spot over and over, he’s basically riding Robby. It felt so fucking good and he’s pulled back into a kiss that makes it even better. God Robby was so incredibly good at this. When he starts rubbing circles around the spot, Dennis can tell he’s close. His hole pulses around Robby’s fingers.
“So close, fuck, Robby,” Dennis buries his face in Robby’s neck and decides to bite. It gets him a moan and a shift of Robby’s hips. He could feel him twitch against him, but he was still soft. Sucking on the spot he moans as he licks off the salty sweat that had gathered on the spot.
“That’s it baby, leave a mark, let everyone know I’m taken,” Dennis whines against the skin and pushes his hips down hard. He’s barreling towards his third orgasm and he wants to cum on those fingers so badly and show Robby that he can follow his commands. “Such a good boy for daddy,” That’s what gets him cumming around those fingers, clenching and spasming, hearing a wet squelch as he can feel wetness and Robby’s cum pushing out of him. Robby’s fingers go to massage his clit through his orgasm and he sobs against his neck. “I’ve got you, I’ve got you,”
“Mmph,” Dennis pushes his ass up as Robby keeps rubbing him, it’s all too much. Robby understands and pulls away but not before he pushes his cum back inside Dennis. Finally he pulls his face from Robby’s neck, connected by a strand of spit from where he had maybe started drooling. Robby doesn’t seem to mind.
“There we are, my handsome boy,” Robby brings his fingers to Dennis’ lips, the ones that had just been inside of him. Without hesitating, Dennis licks them clean, watching Robby’s expression darken. “If I were twenty years younger, I’d be fucking you until the morning,”
“There’s always tomorrow,” Dennis says hopefully. It doesn’t seem like Robby expected him to leave and he really didn’t want to leave.
“I hope you’re amenable to spending your day off in bed?” Robby rubs his ass before squeezing it and Dennis squirms again. How many times did Robby plan to turn him on and make him cum? But then his hands are moving up Dennis’ back, stroking him softly.
“I’m more than amenable, I think there’s a few things I need to be taught,”
“Like what?”
“Blow jobs, riding, I wanna touch you more,” He lists them off and watches as Robby squeezes his eyes shut and breathes in deeply.
“You are going to be such a menace aren’t you?”
“A little,” Dennis can’t help the smile that breaks out and Robby just pulls him back into a kiss.