How could you not be? It’s your first time traveling for business, and though you’ve graduated from your internship, you still don’t feel like you’ve found your footing. To make things worse, you’re going to be traveling with your boss. Mister Robert Clarke is his name, and you’re very worried about disappointing him.
Mister Clarke is a nice, friendly man. That’s why he’s often sent on these business trips; he’s very good at charming potential clients and reeling them in. You hope to learn a lot from him. You want to impress him. Whenever he gives you a compliment, you feel your chest flutter.
The two hour car ride you share with Mister Clarke is a bit awkward, at least from your perspective. You don’t know him very personally, and you’re not quite good at making small talk. It’s alright, though. Mister Clarke fills the empty air with idle questions and chitchat. You like listening to him talk. He’s an Englishman, a transplant from your employer’s UK branch, and both his accent and his voice are rather soothing. He speaks smoothly and evenly, lifting his tone for inflection. It’s almost silly the way he says certain things, but it’s charming. You could listen to him talk for hours.
You almost wish the car ride could’ve been longer, but you’re definitely glad when it’s over and you can stretch your legs. Before retiring to your hotel, Mister Clarke asks if you’d mind having dinner first. He says it’ll be his treat, and you shyly accept his offer. You probably would’ve even if he hadn’t been so generous.
“So,” Mister Clarke begins as he patiently waits for his appetizer. “Do you have any hobbies? Anything you do outside of work?” When your answer doesn’t come quickly, Mister Clarke smiles. “Come on, lad. Don’t be shy. I’m not trying to be nosy, and you’re not being evaluated. I just like to get to know the people I work with.”
You blush and laugh a bit awkwardly. Mister Clarke offers a small chuckle of his own. You think he does it just to help you relax. “Well, sir, I guess I like making art. I like painting, but I’m not that great at it. I’m better at drawing.”
“Oh, really?” Mister Clarke responds, his voice carrying a genuine interest. “You’ve got to show me some of your work, I’d really love to see it.” He says, and you oblige. You take out your phone and begin to show him some of your sketches. You’re surprised when he grins from ear to ear. “These are fantastic, lad! You’ve got a real talent there.” You smile brightly and feel your cheeks heat up.
“Thank you, Mister Clarke.” You reply, feeling a bit giddy that you seem to have impressed him.
“Please, we’re not working. You don’t have to call me ‘sir’ or anything else. Just ‘Robert’ is fine. But please, show me more.” And you do, and he continues to compliment you. You feel like your head might explode. What he says next catches you completely off guard, though.
“Do you think you could draw me sometime? Haha, it’ll be just like that scene in ‘Titanic’.” He laughs, and so do you, but when it clicks in your mind, you blush brightly.
Mister Clarke, Robert, half naked and lounging while you do your best to capture how handsome he is. Oh, what a sight that would be. You want to tell him you’d love to, but there’s no way you could ever get the words out. Thankfully, you don’t have to. Your food arrives and Robert changes the subject. You can’t help but think about that scenario throughout the duration of your meal, and on the car ride to your hotel, where another surprise waits for you.
“Oh, you have to be kidding me! Can’t we even get a cot? I’ll sleep on a bloody cot if I have to.” Robert pleads with the receptionist. Thanks to a booking error, there are no two bed rooms left available. Like a rushed scene from a cliche story, you’re going to have to share a bed with your boss. You feel like you’re going to faint. The feeling lasts until you’re actually in the bedroom with him.
“I’ll sleep in the tub if you want me to, lad. This is, well, I don’t know if it’s against policy but I doubt we’re encouraged to do this. Are you sure you don’t mind?” Robert asks for the third time. You shake your head. You’re once again so anxious you could shout, but you really don’t mind, and you certainly don’t want him sleeping in the tub.
With all the lights off in the little room you’d been abruptly given, you can’t see Robert as he crawls into bed. You can certainly feel him, though. He’s so close that you can feel his warmth against your skin, and you can smell the soap he’d used when he’d showered. You wonder if he’s thinking about the same thing, but you don’t wonder for long. Robert begins to snore, quite loudly, and it almost makes you giggle. You settle in and do your best to sleep.
You manage to drift off after a while, but something wakes you only a few hours later. You feel warmth against your back, and a weight across your waist. It takes you a moment to realize that Robert had wrapped his arm around you. His snoring lets you know it had been a sleeping action, but it doesn’t matter. It still makes your heart flutter. Even with your nervousness, you’re able to fall asleep in Robert’s comforting presence. Only a few more hours later and you’re being woken up to get ready for your meeting.
And of course, you almost blow it. You say something awkward, you embarrass yourself, and your client is clearly put off. Luckily, Robert is there to salvage things. He smooths it over, works his charm, and manages to seal the deal. You feel like an idiot and as you leave, you expect him to turn coldly towards you. You’re sure you’ve disappointed him.
To your relief, though, he doesn’t chew you out. He sympathizes. “It’s alright, lad. Everyone makes mistakes, you just have to learn to recover from them.”
“I don’t know.” You reply. “I’m just not good with people. I don’t even know why they sent me with you.”
“I’ve been in your shoes, lad. Believe me. When I was around your age, I got fired for completely blowing a deal. Sneezing in your client’s face is much worse than saying something silly. Don’t worry about it. Learn from it, but don’t let it drive you nuts.”
Robert makes you feel better. You’re still beating yourself up over your mistake, but you can’t help but giggle at the mental image of him embarrassing himself in such a way. He giggles, too, and he pats your knee. “There’s a good boy. Laughter fixes everything, doesn’t it?” You agree with what he says, but did he have to call you a good boy? It’s got you imagining him in much naughtier ways, and you blush. He doesn’t seem to notice, even if your face burns for the duration of your car ride.
To your surprise, you don’t immediately head back to the hotel. Robert says that he’s going to treat you to dinner again, and then a bit of shopping. You’ve always known him to dress nicely, but you don’t expect him to fill so many shopping bags with clothes. Some are for you, too, and he refuses to let you pay him back. “A man must look his best both when at work, and when at play.” He says. That doesn’t explain why he’s bought you a hoard of new art supplies, and you have to ask. “It’s an early Christmas present.” He says. It’s June, and you remind him of that, but he simply shrugs. “I said it was early, didn’t I?”
When it’s time for bed, you can’t believe the day you’ve had. It started off so miserably with your flub at your work appointment, but ended so wonderfully with Robert and his compassion and generosity. You wonder how you could thank him. You think about it until you fall asleep again, listening to the sound of the older man snoring behind you.
Once again, though, you’re woken up in the middle of the night. Robert’s arm is around you again. You don’t mind, of course, and you’re determined to stay awake for a bit and enjoy it. It’s only moments after that you notice something else. Against the bottom of your pajamas, you feel something stiff. You immediately know what it is, and you can’t help but push back.
Mister Robert Clarke, your direct superior, has his morning wood pressed right against your ass as he holds you close. He’s still snoring, and you can’t stop yourself from pushing back against him. Your head feels light and your cock harden almost immediately. God, this is wonderful. You wonder how long it’s going to last. You need it to last. You’ve never been in this situation before, you’re still a virgin! You know you’re going to be after this, too. Robert is sound asleep but-
And then you notice that at some point, the snoring had stopped. You freeze, stilling your hips as you debate on what to do. Should you immediately stand up? Should you lay still and pretend to be asleep? You can’t come up with an answer, and you don’t have to.
You feel Robert’s hips begin to move the same way yours had. You feel his cock grind against your ass and his grip on your tightens. “Heavens, lad.” He says. “I didn’t know you were such a tease.”
“Mister Clarke, Robert, I -“ you stammer, but he shushes you. His breath hits the spot just behind your ear and you shiver.
“It’s alright, love. You don’t have to say anything. Just let me know you want me to touch you.”
“Yes, please. Yes, sir. Please.” Your mind races, and you feel a chuckle rumble in his chest behind you. Your begging is answered with a hand sliding up your shirt and over your belly, then down again. Robert gives you a few more rubs, making you wait a little bit, before he squeezes your cock through your trousers. Your hips jerk forward into his touch, and he slowly begins to stroke you through the fabric. As he does so, he continues to grind against your ass and he begins to press small kisses to your neck. Your back bends around the curve of his chubby stomach, but it feels wonderful how you fit together like a puzzle piece.
“That’s a good boy.” He whispers into your ear. “Have you done this before?” You shake your head. “That’s alright. I won’t push you. He momentarily moves his hand away from your cock and hooks his thumb into your waistband to tug your pajama bottoms down. Before he can, though, you’re rolling over. You want to face him.
He smiles at you. Unlike the night before, you’d left the window shade open. The late night glow of the city is enough for you to see Robert’s handsome face. You reach to kiss him. When you pull away, he’s still smiling.
“Now that’s what I like to see, taking some initiative.” You blush, and he doesn’t need to see it well to know that you are. He tilts your chin upwards and goes for another kiss. It’s slow and gentle, very patient. You open your mouth after a few moments and he accepts the invitation.
You feel Robert’s tongue against yours and you moan. You want him deeper, and he obliges. He moves his hand from your chin to the back of your neck and holds you still as his mature tongue explores your mouth. It makes you feel desperate and needy in a way you’ve never felt before. When he pulls away to breathe, you ask him to do that again. Again, he obliges. You want him to kiss you like this over and over again, in front of everyone, letting them know that you’re his because at this point, you well and truly are.
But still, you’re unsure of what to do next. You’ve never been one to take charge. Robert knows, and he softly asks “Do you want to touch me?”. You nod your head, then feel his warm hand taking yours. He places it on his chest, and slowly moves it downward.
You can feel his body so well, even through the fabric of his shirt. His chest has been softened by age, his tits sitting somewhere between firm and succulent. You’d squeeze them if you could. You will, you’re determined. Later, though, because right now you’re rubbing his belly. You wouldn’t call Robert a fat man, but his belly does hang over the waistband of his trousers. It feels a little firm as well. You want to kiss it. Again, you’ll have to do that later, as Robert’s hand comes to rest at his crotch. You squeezes your hand around his cock, then places his own onto your hip. He wants you to squeeze it on your own. You’d never be able to say no to that.
You squeeze the older man’s finely aged member through his trousers, and you try to imagine what it must look like. It isn’t massive, only a little thicker and longer than average, but so very hard. Just imagining it isn’t going to be good enough.
“Can I see you?” You ask rather bluntly. It makes Robert laugh, and he nods. You don’t waste any time reaching over to turn the bedside lamp on and as you do, you can hear Robert shedding his shirt.
When you turn back around, your hands move of their own volition.
You place them on his shoulders and slowly bring them down over his chest. He’s a hairy man, not exceptionally so but there’s more than enough to run your hands through. The hair in the center of his chest has gone as gray as his hair, and you follow it down over his stomach. You wonder if it follows all the way down to his cock. As red faced as you are, you can’t just imagine it. You hook your fingers into your boss’s waistband, he lifts his hips, and it only takes a moment for his trousers to hit the floor.
You can’t believe your eyes. Just as you’d pictured, Robert was only slightly bigger and thicker than the average cock. His member curved upwards ever so slightly, and ended with its blunt head covered entirely with foreskin. You should’ve guessed, given that he’s British. You want to touch it so badly, and Robert knows. He reaches out to take your hand again, placing it on his hairy chest and dragging downwards. Your fingers trace through his graying, untrimmed pubic hair before they’re curling around his cock.
“There we are.” He says gently, closing his eyes with a satisfied look on his face. “Do as you want. I’m not going anywhere.” And to make his point, Robert folds his arms behind his head as he relaxes. You watch him and think for a moment that you’d quite like to bury your face in his armpits, but you brush the thought aside. His throbbing cock demands your attention right now, and you’re more than willing to give it.
You stroke him slowly, watching with fascination as his ample foreskin glides over the head of his cock. You trace your thumb around it, marveling at its slick wetness. You want to lean down and repeat the action with your tongue, but you’re not quite sure you’re ready for that. Instead, you just keep stroking him.
Your free hand reaches out down below, cupping his balls. They’re quite big, sprinkled in a layer of fine brownish-grayish hair. You squeeze them, tug them a bit. The actions earn satisfied groans from Robert, and a few words of praise.
“That’s a good boy. Keep it up. You’re making me feel wonderful.”
You smile widely and do as you’re told. As you stroke him, you can’t help but admire his cock. It’s such a perfect, natural thing. His foreskin is magnificent, and you can’t help but stretch it out as you stroke. It makes your cock ache when you see how far it will stretch, and how many fingers you can slip inside it.
Robert notices the way you’re playing with his cock, but he doesn’t say anything. Not for a few moments, anyways. He lets you have your fun for a while before posing the question. “Now, is it my turn to see you?”
Your face flushes again, and you shyly nod your head. He tells you it’s alright if you don’t want to, but you tell him that you do. It’s just that, well, you’ve never done this before. You’re a virgin in every possible way and he’s the first man who wants to undress you. He tells you that it’s an honor to be your first, then, as he begins to remove your shirt. Next comes your trousers, and he tosses them on top of his own before laying back down. Face to face, he kisses you again as he guides your hand back to his cock. His own wraps around yours and he begins to stroke. You follow suit.
“That feels wonderful, lad. You’re doing so well.” He says against your lips. “Thank you, sir.” You reply.
After a few moments, Robert reaches down to brush your hand away from his cock. He isn’t getting close to an orgasm, but he does want to be physically closer. You feel your breath hitch as he rubs his cock against your own. You feel like you’re going to pass out when he wraps his hand around the both of you and he begins to stroke your parallel members.
You moan, you whimper, you make every sweet little noise that you can, and Robert hangs onto every one. Your hands search for something to do before finally settling on running through his chest hair. You trace your thumbs over his nipples and hear him groan. You’d suck on them if what he was doing didn’t feel so fantastic.
You wonder if he’s going to go all the way, to stroke you both to completion, but he lets go before you can get too close. You visibly pout, and it makes him laugh. “Don’t make that face, lad. I believe you’ll like this.”
Before you can ask “like what?” you have your answer. Mister Clarke holds your cock in one hand, and his own in the other. His foreskin is pulled back all the way, and your tips are pressing against each other. To your amazement, his foreskin glides past his head and over yours. It’s malleable enough to completely cover it and then some. God, you really are going to faint. You throb and ache as he begins to stroke.
“Do you know what this is?” He asks. “It’s called ‘docking’. Something you can only do with an uncut man.”
“I only want to do it with you.” You stammer out. It makes him smile so sweetly, and he leans in to kiss you. “If that’s what you want, my dear.” “I want you.” You reply. “Then you’ll have me.” he croons.
It’s barely more than a minute before you start to feel the rising tingle in your cock. You’re going to cum, and it’s certainly going to be a hard one. You whimper and try to warn. “Mister Clarke, I’m going to-“ he shushes you again and just keeps stroking your cock with his foreskin.
Your fingers curl into his chest hair, your eyes squint shut, and you erupt. Your cock spasms hard within the older man’s hand, your cum coating his cock, spilling out onto his hand, and onto the bed sheet. His hand stops, but he doesn’t take it away. He just holds you close as you ride out the intensity of your orgasm, breathing hard against his skin. When you’ve caught your breath, he asks what you’d like to do.
“Do you want to continue?” He says. “You don’t have to finish me. If you’re tired, we can go back to sleep.”
You shake your head, feeling your confidence grow as your cock shortens. “I want you to fuck me.” You state bluntly.
For once, you catch Robert by surprise. “You - you don’t have to, lad. I understand if you want to wait, or never at all, or -“
You interrupt him with a kiss, pushing your tongue into his mouth and letting him know what you want. He lets go of your cocks and reaches up, using his weight to shift you from your side to your back. He spreads your legs around his waist and tugs you by the hips, guiding you and positioning you until you’re in the perfect position for him to fuck. Before he goes any further, though, Robert once again asks if you’re sure about this.
“I don’t want to make you do anything you don’t want to.” He says.
“It’s okay. I really, really want to.” You reply.
“Then we have to keep it a secret, you know. I’m your boss. We’d both get fired.”
“I can keep a secret, but I’m not worried about that. I just want you, Robert, please. Please, Mister Clarke.”
Your begging does him in. He’s already wrapped around your finger, and he can’t say no to you. Not when you’re begging, your soft thighs spread for him. His cock is so hard that it hurts. He wants to plunge in deeply so very badly, but he doesn’t want to hurt you. Instead, he wets his fingers. He makes a show of it, too, looking you in the eyes as he licks his index and middle finger until they’re slick with his spit.
“Breathe, love.” He says to you as he brings his hand down between your legs, sliding them until he feels the heat of your wanting hole. Robert pushes in gently, slowly. You whimper for him and it make him crack a subtly dominant grin. “There you go.” He whispers, slowly beginning to move his hand back and forth. Your whimpering grows louder as he fingers your needy ass, and you have to bite your lip to avoid moaning out loud when he inserts a second finger. He repeats “Breathe, love.” And he continues until he’s satisfied that you’re relaxed and open for him.
“How lucky am I?” Mister Clarke says as he spits into his hand. In the morning, he’ll grab a bottle of lubricant from the pharmacy. For now, though, he’s going to have to do things the “natural” way. He grins as he slicks up his cock, then lines up to press into your hole. You push back against him. “Getting to deflower such a handsome young man, then getting to work beside him. I’ve go a feeling I’ll be working on top of you, though. Would you like that?”
You nod your head, and push back against him. He rolls his hips and slowly, his cock sinks deep into you. Your legs wrap around his waist and hold him close.
“I’ll take that as a yes.” He says, and you nod. He begins to roll his hips ever so slowly, his cock beginning to pump in and out of you. It’s only an inch or two at first. He doesn’t want rush, and it gives him an opportunity to keep talking. “When we get back, I’m going to do this to you in my office. Bend you over my desk. Is that what you want?” You nod your head and moan for him. “Good.” He says, pushing his cock in deeply again. His big balls rest against you and you look up at him with a dazed expression. He smirks, but he also looks rather high in lust. “Because I don’t know how I’ll be able to go without your arse now. So tight and sweet, all for me.”
He reaches up to cup your jaw, gently stroking it as he resumes his thrusting. You nod your head slightly, as much as you can. “You won’t have to. You can fuck me whenever you want.”
“I’ll fuck you whenever you want.” Mister Clarke responds, putting his back into it to thrust a little harder. “I’ll let you play with my cock whenever you want. Suck it whenever you want. Fuck, I can already imagine that sweet mouth of yours around me. You’ll stay under my desk, won’t you?” Again, you nod. “Sucking my cock, licking my bollocks whenever you want.”
“Whenever you want.” You let your hands reach up to rub his chest. Your fingers play at his nipples and it’s clear from the way his hips buck that he likes it. You pinch them and he thrusts harder. “I want to please you, too. Make you feel so good. Whenever you want me, I’m yours.”
Mister Clarke smiles down at you, ever so slightly out of breath, and nods his head. “Fine, then. We’ll fuck when either of us wants it.” He doesn’t expect you to say “I want it all the time,” but it doesn’t exactly surprise him. “Of course you do.” He says. “Lad gets his cherry popped and suddenly he’s like a cat in heat. Silly thing.”
He makes you laugh. Even when he’s fucking you, he can make you giggle. You tug his nipples, telling him to keep going, and he obliges.
“You’re so tight.” He says, now pulling mostly all the way out before thrusting all the way back in. His balls slap against you. You twist his nipples. “I’m going to fill you up, lad. Is that what you want?”
You nod your head. You’d never even think of asking him to pull out. If Mister Clarke needs to cum, you’re going to take it. You’ve already decided. You wonder just how close he is.
“Yes, sir. I want you to cum inside me. Make me so full. Please, sir.”
“God, what a sweet thing you are. Letting a dirty old man fuck you. So fucking dirty, I am. Fucking an employee. Fucking an employee half my age. But you know what you want, don’t you? You want this daddy cock. Bet you’ve wanted it since I hired you. Bet that was your plan from the start. If you didn’t get the job you’d just let me breed you, wouldn’t you? Your tight, virgin ass for a job. Fuck, so fucking dirty.”
The way he’s talking has you feeling light headed once again. You love his voice and his accent, and here he is saying the nastiest things to you. You want to kiss him, to have his tongue deep in your mouth again, but that would mean he’d have to stop talking, and you don’t want that. He’d have to stop fucking you too, and you really don’t want that.
Not when you can feel that heat rising in you again, that tickle of an imminent orgasm. Your cock is still soft, but fuck, Mister Clarke is going to make you cum again just with his cock. Your hole clenches around him and your eyes slam shut as your second orgasm hits you hard. Your prostate throbs, it makes you cry out when Mister Clarke’s cock strikes it, and the tip of your cock dribbles out a small but noteworthy load.
“Oh, fuck.” Mister Clarke growls. “Your first time getting fucked and look at you, cumming from daddy’s cock in your cunt. What are you going to do when his cum is leaking out of you? You’re going to beg for more, aren’t you?” As he gets closer to finishing, Mister Clarke’s words get less direct. It’s less as if he’s speaking to you and more-so speaking at you, his own imminent orgasm wiping any rational thought from his head.
“Please, sir. Give it to me.” You whine one last time, and pinch his nipples as hard as you can. With a heavy grunt, Mister Clarke bucks his hips as deep into you as he can and cums. It’s a hot, heavy load that seems to never end.
“Oh, that’s it. That’s it, lad. Take that spunk. Take that dirty old spunk.” He continues to ramble as he cums, each throb of his cock filling you up more and more and more. It only seems to stop when his erection stops pulsing and his hips stop rolling.
Mister Clarke breathes heavily on top of you, practically bending you in half. He’s tired, hot, and sweaty, but he doesn’t want to let you go. He doesn’t even want to pull out, and he stays inside of you until his cock has gone soft and it slips out. As he pants on top of you, your arms link around his shoulders. You don’t want him to go anywhere, either.
As your legs slowly return to a relaxed position, you feel a trembling all throughout your body. You’re not sure you can walk anymore. Mister Clarke chuckles. He was expecting this, and he doesn’t rush you to move. Instead, he moves to lay next to you. He puts his arm beneath your head, encouraging you to lay on his chest while he cuddles you.
You lay there for a while, listening to the older man’s breath slowly beginning to even out. He must have gotten carried away and overly exerted himself. The thought makes you smile, and you find yourself gently petting his chest. You rake your fingers through his chest hair, all the way down to his fuzzy crotch. It makes him laugh.
“Can’t get enough of it, can you?“ you shake you head. “That’s alright. Indulge yourself. We’ll take a shower soon. I need to catch my breath, and I doubt you can walk yet. I really rocked your world, didn’t I?” Yet again, Robert has made you laugh. You can’t wait to see what other silly things he’ll say to you. You’re already head over heels for him. When you’re able to, he takes you by the hand and guides you to the bathroom.
As you walk, you can’t help but notice that your boss has a rather bottom. Maybe you’ll have a crack at that in the shower.
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