Work Text:
r/relationshipadvice
u/dennysgrandslam
I [27] am in my first long term relationship and want to surprise my boyfriend [54m] for our anniversary
So, like I said above, this is my first real relationship, and I don’t really know what’s customary beyond regular gifts. I have an actual present for him already, but my roommate [25F] and one of my older siblings [32M] keep making pretty suggestive jokes implying I should be giving a “spicy” gift as well. We have a pretty healthy sex life and have been exploring kinks together, but I’m not incredibly experienced in that regard since I grew up religious. Any ideas for possible fun surprises? He’s taking me on a weekend trip on his motorcycle, so it has to be something relatively discreet I can fit in my backpack. Thanks in advance
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BigDawgSteve: Lingerie. Hands down. Sneak something cute and slutty into your clothes for the weekend and surprise him by walking out of the bathroom in it.
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ghoap_fever: if he has a favorite shirt/jacket/jersey whatever, steal it and wear it with cute panties and stockings. dudes love that shit.
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user52340791: if you go on Etsy a lot of jewelry makers do discrete collars and cuffs, you could find something that would make like a nice matching set or something, especially if yall have an established kink dynamic
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dabigcheeze: i wish i had a girlfriend like you damn
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easypeasylemonweenie: holy age gap batman. since he’s old he probably appreciates the classics. wear a lacy little thong and pasties and let him lick whipped cream off your titties or something idk
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xX_daddyslittlemonster_Xx: ooh that sounds so fun! I second what a lot of other people are saying, surprise lingerie is always a great sexy present, especially if he’s not used to you dressing up. Either something sultry or a fun costume if you like roleplay stuff. Kitty ears and a bell collar are always fun. My husband likes when I wear my schoolgirl uniform the most, it’s a classic for a reason and skirts are easy access!
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TriSant69: surprise him by stealing his bike and leaving him at a gas station in bumfuck nowhere with no cell signal
irrationalcherrypi [moderator]: please remember to use tone indicators on comments that are meant to be sarcasm
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Dennis groans into his hands and debates throwing his phone. He’s been scrolling various clothing sites for what feels like hours now, looking at all the different lingerie options that are out there.
Some styles are immediately a no. Latex is expensive and confusing and doesn’t look very comfortable. Tight sheer mesh is definitely not designed for people with dicks. The overly gimmicky costumes don’t seem like something Robby would actually find sexy, even if the slutty nurse one would be a little funny. Bright colors and bold patterns don’t really feel like him, but then again he’s never really thought about what kind of panties would be “him”, considering most days he just wears plain boxers.
Part of him wonders if he’s being pranked, some elaborate internet-wide inside joke he doesn’t know because he’s never really been much of a forum guy before. But almost every single comment on his post suggested the same thing so… hopefully unlikely?
And there’s absolutely no way he’s asking anybody else for advice on this. Trinity would literally never let him live it down, and Mel and Victoria are his friends but he’s not exactly discussing his sex life with them regularly. Hell Trinity only knows he’s with someone, he’s never told her it’s their Attending. Even thinking about asking one of his brothers makes him throw up a little in his mouth, so that’s outright a no.
In the end, he settles on something simple. He kind of liked the one suggestion about stealing something of Robby’s, it makes it easier to hide the plan as a whole and gives him a base to go off of. Robby’s navy blue hoodie is on Dennis more than Robby nowadays anyway, so it wouldn’t even be suspicious. He ends up ordering a pair of lacy white panties, and white thigh-high socks with blue stripes around the top to tie it all together.
And then, just because he’s feeling brave, a steel butt plug with a light blue gem.
When the time comes for their weekend getaway, practiced lies about how their time off conveniently overlaps, Dennis packs his bag and uses his key to let himself into Robby’s place before his partner gets home from his last shift before they leave so he doesn’t ever get a chance to see the contents. He still has no idea if this will actually be a good surprise, but he’s in too deep to back out now.
-
Robby’s made a lot of mistakes in his life when it comes to relationships, but he’s worked damn hard over the last almost year to not repeat any of them with Dennis, or to somehow make new ones. And he’s done a good job, or at least he thinks so.
They don’t fight, except maybe over the remote. Dennis hasn’t said he feels neglected or like Robby is choosing his job over him. They have a date night every two weeks, and have gone away for one or two days here and there when they can both get the time off.
And their sex life is fucking fantastic. Dennis is perfect for him in every single way, and even though he was inexperienced at the beginning his enthusiasm and willingness to try new things more than made up for any arbitrary thing like “being a virgin”.
As their one year anniversary approaches, however, he finds himself excited. They got the time off, somehow not raising any red flags with HR or eyebrows from their coworkers, but god, he really wants to get this right. He’s got a few things planned, but overall he just wants to make Dennis feel good, feel loved, and that’s traditionally been a thing he’s fallen short on before.
When he gets home Dennis looks excited too, if a little nervous. It is their first time truly going away away together and Robby is sure Dennis is feeling some big things, but his smile is enough to confirm that he’s looking forward to this just as much as Robby is.
The long drive up to the mountains is easy and he’s pulling into the little cabin he rented just as the sun starts to set. Dennis is quick to snatch up his bag and call the shower first and Robby lets him go with a little wave.
“Go on, and take your time. I want to get some things set up in the bedroom. Knock before you come out, okay baby?”
Dennis nods, his cheeks a little red, Robby wants to ask him if he’s okay but before he can say anything he’s darting off. Kid is always a little nervous on the bike, probably just wants to go take a cool shower and calm himself down. Robby doesn’t blame him.
He does have to move quickly though, grabbing the things he packed in his saddle bags for the trip and carrying them in. The sheets get replaced with the highest thread count set he could find, pillowcases too. Dennis’ favorite blanket gets laid out on top of the provided comforter and he makes sure to open his hygiene bag and spritz his cologne over it. It was very early on he learned about Dennis’ little scent kink and Robby is more than happy to make sure everything smells like himself just for that.
He places the little bag of gifts he stowed away the night before so Dennis couldn’t see on the dresser by the window, and then kicks off his shoes. There’s a fridge full of food waiting for them, part of the weekend package and he thinks about running out to cook, but he decides to wait. Sometimes the nerves get to Dennis too badly after a ride and he gets a little queasy. Robby can cook later.
For now, he strips down out of his riding gear and puts on something more comfortable before laying back on the bed to wait for Dennis to come out.
-
Dennis stares at himself in the full-length mirror on the back of the bathroom door and, surprisingly, doesn’t hate what he sees. He’s still a little pink and damp from the shower, scrubbing all the road dust and sweat off himself was a priority. His hair is extra curly from being in a helmet all day, which he knows Robby thinks is cute.
During his shower, he stretched himself on his own fingers, letting the sound of the water cover any noises he couldn’t tamp down. And now that he’s out, he’s got the plug into himself with minimal issue, a bottle of lube hidden in his toiletry bag. The metal is heavy and a presence he can’t ignore, which in turn makes his dick twitch a little bit.
The outfit itself is… something. The thigh-highs are actually kind of nice, he likes the way they compress his legs and keep him warm. And he loves Robby’s hoodie, that’s nothing new. Although, the way he intentionally has nothing on underneath it, half-unzipped and falling off one shoulder, exposing his prominent collar bones and just a little peek of nipple, definitely is. It’s the panties he’s still a little iffy about. They hug his ass tightly, making it look perkier than usual, and the front is… well. The front. His mostly-soft length is cupped firmly, lacy material showing little hints of pale skin though itself. Every time he shifts, though, the plug in his ass makes itself known and he can feel a damp spot starting to form on the front of the panties already as he starts leaking pre.
He thinks about saying fuck it and abandoning this little idea, deleting his Reddit profile, and maybe running away and changing his name and career aspirations while he’s at it.
But then he thinks about the way Robby has always encouraged his sexual exploration, and how confident the people of the internet seemed to be that this was the way to go. He can always blame his inexperience if it doesn’t go well.
So he takes a deep breath, steadies his nerves, and knocks like he was told to.
-
Robby’s settled into the bed, relaxed and waiting when Dennis’ little knock comes through. It sounds almost hesitant and he's not sure why, but he does sit up.
“Come on out, baby. I'm all ready for you.”
The door peaks open slowly like Dennis is nervous and Robby’s really not sure why. They've been working on Dennis’ confidence and the kid has come leagues in being more secure in both their relationship and as a doctor.
Robby’s just about to call out and ask if he's okay when Dennis steps the whole way out and he loses all ability to think beyond skinskinskin.
Dennis looks like sin incarnate, pale legs wrapped in stockings, the tops of his thighs peeking out from the bottom of his hoodie, and one pert and pink nipple on perfect display. His cock gives an appreciative lurch and his mouth floods with saliva. There's a pretty blush high up on Dennis’ cheeks and as he shifts the hoodie lifts, showing off a thin line of white lace and Robby almost passes out.
Instead he can feel himself smirk, something hot and dark swelling up in his chest.
“Oh baby,” he coos as he slides over to sit on the edge of the bed. “Is this all for me?”
Dennis nods, eyes all wide and nervous. Robby wants to ruin him.
“Why don't you spin around? Show me the back?”
He does, twirling on his toes, head tilted so those big blue eyes can stay locked on Robby, nervously watching his expression like it would ever be possible for Robby to not love every second of this. Dennis shrugs his shoulders and the stolen hoodie slips down further, bunching up around his elbows and showing off all the faint freckles over his shoulders and upper back.
Robby takes an appreciative look at the way the panties hug Dennis’ ass, licking his lips at just how pretty he is. Then he shifts and the light catches on something. Robby leans forward, not believing his own eyes.
“Fuck baby, is that what I think it is? Bend over. Show me.”
-
Dennis should probably be embarrassed by how quickly he bends to Robby’s will, but he can’t help it. Not when the reward is getting those big, talented hands on him.
The initial reaction he got is already way better than he could have expected, but it’s somehow even more intense when he turns around and Robby sees the plug. The way Robby’s voice drops makes him shiver, blood going hot then cold.
He does as he’s told, planting his palms on the wall and spreading his legs to give Robby a good view of the bright blue gem peeking through the patterning of the lace. He hears Robby get up off the bed and stalk over, each footstep heavy and intentional. Even anticipating it, Dennis is a little nervous and jumps when one searing palm works its way up under the hem of the hoodie and slides up his back, forcing his arch a little deeper, and the other wraps around the front of a thigh to hold him in place, warm even through the thick fabric of the stockings.
“God, just look at you. Prettiest little thing I’ve ever seen.”
Robby’s voice is low and soft, like he’s looking at art in a museum and it makes Dennis shiver.
“All for you,” he manages to squeak out, shifting his weight up onto his tiptoes, giving Robby a better view.
“Damn fucking right it’s all mine.” Robby’s thumb presses down right in the center of the plug through the lace, pulling the panties just a little tighter in the process. Between the shifting of the plug and the fabric around his cock, Dennis can’t stop the reedy little whine he lets out.
Robby sounds like he wants to devour him, and honestly he can’t fucking wait.
-
Robby’s never had someone do anything even close to this for him before. Dennis is the gift that just keeps on giving and he's not going to let this beautiful boy go to waste.
Dennis responds perfectly as he presses into the plug with his thumb, mouth parting on the sweetest noise. Robby can't help but lean over him and capture his lower lip between his teeth and tug on it, licking over to soothe the sting after.
“I ever tell you how perfect you are?” Dennis nods, a little wide eyed and Robby wants to ruin him. “Good, because you are.”
He slips the hand from Dennis’ back, over and around to the front, sliding over his exposed pec to tweak at his nipple, pushing again with his thumb just to see if his boy will arch forward or backwards. He presses back into the plug and Robby groans. It's easy to hold his palm flat to Dennis’ chest and pull him off the wall, stealing all of his leverage to pull him backwards against his own chest.
Dennis scrambles a bit, still up on his tiptoes and Robby leans down to suck a mark right into the side of his neck. The kid mewls and Robby feels his cock twitch in response.
Robby’s hand retreats for just a moment, out from under the fabric and then back around to the front, catching the zipper of his jacket, pulling it all the way down until it falls away from itself. He guides the sleeves down and over Dennis' hands, shushing his confused, nervous noise with more kisses up the side of his neck and over his jaw. “I know how much you love wearing this, but I am going to fucking ruin you tonight and I want you to be able to have it clean and dry afterwards, okay? I promise you can have it back.”
Dennis nods in understanding, eyes wide and eager, and gives up the garment, shivering a little now that he’s nearly fully exposed.
Robby turns them after carefully tossing the hoodie onto the comfy looking chair in the corner of the room, then basically does the exact same thing to Dennis, throwing him on to the bed face-down, quickly getting hands on Dennis’ hips to pull him up onto his knees.
Coming face to face with the little blue gem covered by white lace only makes him a little insane. He’s quick to pull the panties down, leaving them around Dennis’ sock-clad thighs so he can't spread them too far, trapped. Robby runs his hands up and down over Dennis’ ass, squeezing and rubbing before smacking over one cheek just to watch the red blossom.
“Fuck, I can't wait baby. You're just too fucking delicious.” He leans in, spreading Dennis’ cheeks, and licks a hot stripe over the plug, tugging on it with his teeth.
-
Robby starts acting like a man possessed and Dennis should probably be nervous but all he can think about is the hot, wet line of Robby’s tongue.
And the thing is, he’s always passively aware that he’s not exactly a big guy. Not super tall or broad or muscular, but he knows he’s stronger than he looks between growing up on a farm and moving patients and equipment around all day now. It’s not something he’s ever been ashamed of, and if anything, Robby seems to like their height difference what with the way he always exaggerates leaning down to kiss him and makes comments about the size of Dennis' hands.
But right now? Dennis feels small. Delicate. Precious, even.
He literally cannot move beyond some squirming, not with the way Robby has him pinned and overwhelmed.
And he fucking loves it.
As nervous as he was opening that door, he’s getting into it for real now. There’s really no reason to be bashful about the noises coming from his throat, nor the way his dick leaks and twitches in response to everything Robby’s doing to him, because he knows Robby loves getting that sort of response from him.
The scrap of lace now hanging between his thighs still has him a little pink in the cheeks, but if this side of his partner is what he gets as a reward for his little get-up? Hell, he’ll throw away every pair of boxers he owns the second he gets home and replace his entire underwear drawer with various styles of lace and bows if it keeps getting him this.
Robby growls something under his breath that gets muffled by Dennis' ass cheek, but before he can ask what it was, there’s a big, calloused hand wrapped around his dick, stroking in time with Robby’s crazed licking, and Dennis feels his brain melt out of his damn ears.
“F-fuck! Robby!”
Robby pauses his licking to chuckle, low and a little mean but in a good way, and leaves a sharp nip right where Dennis' ass and thigh come together, just above the hem of the sock on that leg, ensuring he’ll feel the mark for days every time he sits down.
“That’s right baby, say my name.”
Christ, Robby’s gonna kill him. He doesn’t need to worry about his future underwear choices because there’s no way he survives tonight.
-
Robby makes sure he’s tugging on the plug inside of Dennis with every lick of his tongue, wants his boy to feel it pulling and pushing so he can’t forget it’s there even if he wanted to. Sure, he’s risking chipping a tooth but he literally cannot be fucked to care.
He does, eventually, remember that there is more to life than trying to see if he can squeeze his tongue in next to the plug, reaching up to get a hand on Dennis’ cock, smirking at the way he’s already so hard and leaking.
Dennis is thrusting forward into his hand and back into his tongue, like he can’t figure out which sensation he wants more, and Robby’s going a little insane at it.
Eventually though, he pulls back, nipping over the curve of Dennis’ ass, kissing his way up his spine, never stopping the movement of his hand but slowing it down.
“God you’re divine. So pretty for me, perfect.” Dennis whimpers, turning to look at him over his shoulder and there’s little tears in his eyes. Robby coos at him. “You want to cum before I fuck you? I do love how sensitive you get.”
Dennis looks conflicted and Robby loves it. They’ve learned that if Dennis cums first, before Robby even gets in him, he gets overly sensitive, crying from every little thing Robby does. It’s a beautiful sight, but it’s only their first hour here, he doesn’t want Dennis to get too much too fast and throw off the rest of their weekend.
He never lets go of Dennis’ cock while he waits for the answer, his other hand smoothing over his ass, thumb pressing into the plug once more.
“Come on baby, Daddy needs you to use your words.”
-
Robby asking him to use his words is actually cruel and unusual torture on it’s own, but to then do something like call himself Daddy in that perfect, gruff voice? Absolutely not fair. Dennis thinks maybe he should contact The Hague about it.
How the hell is he supposed to make decisions now when all of his brain power is going towards remembering how to breathe?
His hole clenches down on the plug and he feels his cock twitch in Robby’s hand, stomach all aflutter and mouth full of saliva he desperately swallows down to stop himself from drooling all over the surprisingly nice pillow cases.
He does want to cum, but he doesn’t know if that’s animal instinct wanting release, or if he’s ready for the consequences of overstimulation. He loves it, but it’s a lot especially so early on in their weekend.
Shit. Shit and also damn and maybe even fuck.
Robby just keeps stroking his cock, methodical, perfect grip, borderline mechanical. Like he’s milking a cow rather than teasing his partner. It’s not getting any easier to decide anything, but then, when he’s been quiet a little too long, Robby kisses him behind the ear and drops his tone a little. “Baby, do you want me to stop?”
Dennis lets out a noise that sounds like the bastard lovechild of a hiccup and a whimper, some embarrassingly squeaky, desperate thing and shakes his head vehemently.
“No, don’t stop! Please, don’t stop Daddy–”
“Okay, okay, shhh, easy,” he actually picks up his pace a little, and Dennis can no longer control the spit in his mouth. “Not gonna stop but I need to know. C’mon, I know you can. Be a good boy for me.”
Dennis whines and nods, thighs shaking. He’s too close to stop now, even if Robby pulls his hands away right this second he’ll probably still tip over the edge, it’ll just be a ruined orgasm instead of a truly satisfying one, and then he’ll be even more desperate and overstimulated.
“I wanna cum for you,” gets squeaked out nearly all as one word rushed together. He can take it, and if it’s too much, well, hey. They’re in a cozy cabin with a beautiful view of the mountain side and a hot tub on the back porch. He can pout his way into being spoiled afterwards so long as he earns it.
-
Dennis falls apart beautifully. It’s one of Robby’s greatest joys in life to see the way Dennis responds to him, the way he falls apart at his touch, the way he calls him ‘Daddy’ with awe and reverence that on most days he doesn’t believe he deserves.
His baby boy asks for what he needs, drool spilling from the corner of his mouth, and it makes his cock twitch hard, desperate to be inside of him.
Robby knows Whitaker enough to see the signs of his orgasm, shaking thighs and flushed skin, and the way he blinks far too fast. It’s a sight to behold and if things go right, there’s a very large mirror in the corner of the room, Robby’s going to fuck him in front of it so he can see how good he looks when he cums all over himself.
He makes sure to keep up the perfect pace, hand wrapped around Dennis’ cock as he drops his face down into the sheets to moan his way through his orgasm. Robby never stops moving, making sure to milk every last drop out of him until Dennis is squirming and breathing hard and choppily before he finally legs go. His hands pull away from sensitive areas, smoothing over pale and soft skin.
“Did so well, baby. Daddy’s perfect boy.” Dennis peeks out one blue eye, wet and wide, and Robby smiles at him. He means it to be soft, but he feels a lot like a wild dog with his prey trapped in a corner. “I’m gonna take out the plug now, okay? As soon as I know you’re ready, I’ll fuck you. Does that sound good?”
There’s only a hint of a nod, but it’s enough.
“Good boy, you just lay there and let Daddy play.”
And play he does. The plug comes out with a wet pop that has them both shivering, Dennis’ hole gaping for a moment with nothing to clamp down on and Robby’s more than happy to fill it again with his tongue.
The gasp that causes is music to his ears and the way Dennis can’t spread his legs any wider because of the panties is even better. Normally Robby holds his thighs for that, with these he doesn’t have to.
Soon enough he gets two, then three fingers in, his boy already stretched out nice and pretty from the plug. His pinkie slips in without much fuss too and before long all he can think about is sinking into the hot hole around his fingers.
He rises us, still buried up to his palm inside of Dennis, and kicks off his boxers, fisting his neglected cock.
“You wanna stay on your knees baby? Keep showing Daddy that pretty hole? Or do you want to be on your back?” Sometimes Dennis likes to be kissed more than he likes to be fucked, and this weekend isn’t just about him. It’s about them.
-
Robby keeps asking him questions, which really is just downright sadistic of him. It was bad before, but now? How the fuck is he supposed to decide anything? He doesn’t even know his own name right now, let alone what he wants, aside from Robby’s cum inside him. He’s been good, damnit! Robby even said so!
But he tries, because he wants to keep being good.
Staying on his knees is nice. It means he can hide his face and the way he’s already crying a little bit, muffle some of his more embarrassing noises, and Robby called him pretty like this. Being on his back is nice too, though, because then he can get kisses, and he really loves kissing Robby. Loves how his beard scratches, how it feels like Robby’s tongue is fucking into his mouth in time with his cock. There’s no way in hell he’s getting on top after already getting off once, he won’t be able to walk for days if he tries.
Robby massages his back while he tries to find two spare neurons to rub together to make a decision, one big warm hand kneading into his lumbar and side, the other gripping his own cock, almost absent-mindedly smearing the leaking tip over and around Dennis’ hole, which is really, really not helping him think straight.
It breaches him, just barely, just for a second, and erases any progress Dennis made in the whole “thinking” thing, and it makes him desperate. Greedy. Stupid.
“Both?” is the word that comes out of his mouth, more whine than speech, it actually hurts his throat a little, and he almost regrets putting that option out into the air when Robby’s already so worked up and apparently determined to fucking destroy him tonight.
Can he actually cum three times in one night? He has no idea. They’ve never tried, not with how overwhelmed he gets at two. But, if there was ever a night to give it a go…
Robby freezes, fingertips suddenly digging in where he’d been petting.
“Yeah? You sure you can handle that, sweetheart?” His tone is stilted, a little odd. Like he’s fighting between just pinning Dennis down and making him regret speaking that possibility into existence, and being a good, responsible top and actually confirming enthusiastic consent. It reminds Dennis of those old werewolf movies his brothers scared him with as a kid, the strange growly way the monster talks right before he transforms.
Dennis is too keyed up already to be anything but painfully honest, though. He keens, sharp and desperate, and shrugs as best as he can with his face and shoulders smushed into the pillow still, looking up at a sharp angle to find Robby’s dark eyes. “I dunno, but I wanna try, for you Daddy.”
If Robby fucks him hard and mean exactly like this, then rolls him over once he’s just a puddle of a man and takes him a little slower and more gentle on his back so Dennis can kiss and touch, he can probably do it, or at least make a valiant try, and if he has to tap out, Robby can jerk off onto his chest and face the way he likes to when he’s feeling particularly possessive.
And if he passes out? Well, hey. He’s in a pretty damn cozy bed already.
-
Robby about blacks out when Dennis says both. All he can think about is wringing that third orgasm from his boy as he cries and whines and begs, it's enough to give him a literal head rush considering most of his blood is somewhere else right now.
He about takes it at face value before he remembers he has to not actually kill Dennis with his cock.
So he asks, confirms, gets real consent beyond a simple suggestion. And perfect, beautiful, everything he could ever ask for and more Dennis tells him he wants to try. And who is he really to deny him anything, to stifle his desire to do more?
His throat clicks when he goes to respond at first, already on such an edge he's not certain he’ll come back down from it, and has to clear it before speaking.
“You know the safe word, baby. Anything feels bad, or you feel bad. You tell me to stop.” Robby won't hit that too hard home right now, he's not planning on brutalizing anyone, but if Dennis can't handle it, he knows how to control himself.
Of course, he thinks that, and then he starts to press into that tight, wet, warm hole, and rational thinking becomes harder and harder. Even with the plug and a mix of lube and saliva, even stretched out, Dennis is still as tight as a fucking virgin. It's sinful, truly, the way his body sucks in Robby’s cock like he needs it. He notches himself, making sure he's lined up, and then holds Dennis’ hips tight as he buries himself balls deep.
It knocks the wind out of Dennis, who releases a sharp exhale of air before gasping. Robby grins, all for himself, as he pulls back and does it again. Over and over he pounds in hard but slow, until Dennis is just gasping into the sheets, clenching down around him in every rough thrust.
Robby leans over, pressing his hand to the back of Dennis’ neck, immobilizing him even further, getting one foot up on the bed in order to get even deeper. He knows he's hitting the right spot when Dennis gasps, hole clamping down tight as it can.
“There it is, right there. Feels so good doesn't it, baby? Daddy’s taking care of you, can't wait to feel you cum, makes you the perfect cocksleeve for me.”
Dennis whimpers and whines as Robby fucks into him as hard as his own hips can take. He knows from experience that Dennis’ ass will be red from it. For good measure he spanks him, hard, watching his own handprint blossom in real time. It looks even brighter than it usually does when he leaves marks like that, contrasting beautifully with the stark white of his thigh-highs.
He does it again, just because he can, right over the mark he left at the cleft of Dennis’ ass and thigh. The boy yelps and Robby groans.
“You need some help baby, or can you cum like this?” Robby thinks he can do the latter, but if his baby needs some help, he's more than happy to tease it out.”
-
It feels like Robby is trying to hollow Dennis out with his cock alone. Steady, methodical thrusts that he can feel in his fucking lungs every time Robby bottoms out. Before long the pillowcase is soaked under his face, a sticky mess of tears and spit as he just takes it.
Robby doesn’t let him hide for too long, though. As soon as he goes a little too long without answering yet another question, the hand on the back of his neck becomes a hand yanking him up by the hair, exposing how red and puffy and damp his face is and making it even harder to breathe.
He makes a noise, it might be a moan, it might be a sob, and tries to nod even though it tugs on his hair even harder. “I can… I can do it,” he finally manages to pant out, tongue uncooperative and brain barely functioning.
Robby doesn’t speed up, keeps his consistent, devastating pace, but his grip tightens significantly, both hands digging in deeper. “Fuck, that’s it, that’s my good boy. C’mon baby, show me, cum on Daddy’s cock.”
He’s already so close, honestly it’d be a little embarrassing if he had any thought processing power left to feel shame. Robby lets go of his hair finally and his head immediately flops back down onto the pillow. With his other hand now free, Robby grabs Dennis by the hips and starts forcing him back onto his cock, using him like a damn fleshlight with a pulse.
The angle is perfect. Robby's cock rams his prostate every time he bottoms out, overwhelming in all the best ways. He can’t escape it, not that he wants to. It’s inevitable. He’s going to get off again, untouched. Robby’s finally speeding up, too, yanking Dennis back faster and faster, fingers tight enough to bruise. His nails might even break skin a little, Dennis has no idea. The slight sting of pain barely registers over the pleasure overriding his entire brain. He hopes it did, though. Wants a permanent reminder carved into his skin.
Someone is talking and it takes Dennis way too long to realize it’s himself, garbled begging between sobs, promising to be good, really just letting his mouth run and hoping it doesn’t get him in trouble.
“Almost, fuck, Daddy, so close, almost there, please please please please plea—”
Robby releases one of Dennis' hips in exchange for his shoulder instead, taking total control of the speed, depth and power, and on a particularly harsh thrust that rattles Dennis’ bones, it happens.
Dennis cums with a wail, body locking up like a vice then going completely slack seconds after. With the way his legs are, it gets all over the gusset of his panties, absolutely soaking the lace still dangling between his thighs where Robby pushed the garment down. There’s no stopping the fresh tears that come with his orgasm, overstimulated and a little dizzy.
Robby slows down, but he also doesn’t stop, drawing it out as long as he can as much as he’s also seeking his own pleasure. He falls forward a bit, and it gets him a few centimeters deeper with the change in angle. Dennis groans, equal parts pleasure and pain, barely able to listen when Robby starts whispering praise and affirmations right into his ear. He doesn’t process individual words so much as the gentle, reassuring cadence they’re delivered in.
At least. Until…
“Beautiful, such a good boy for me baby, you did so good. I can feel you milking my cock, you’ll get your reward after the next one.”
Next one.
He’s gotta survive this all over again.
He might actually not make it.
-
Just as Robby’s fingernails break the skin on Dennis’ hips, a little trail of blood leaking down until it starts to soak into the white lace, Dennis starts babbling, and that’s how Robby knows they’re past the point of no return on orgasm number two.
It’s a good thing he mentally prepares himself because Dennis goes as tight as Robby has ever felt him before, the grip on his cock so strong he almost can’t move, but he does- pushing through the tightness to fuck Dennis through his release.
Robby is sure to praise his baby boy the whole time, even though he can see by his hazy eyes that he’s not being heard at first.
He slows his hips down to a gentle roll, letting Dennis actually come down just a little bit, before pulling himself up to his full height, getting his foot back on the floor, and carefully smoothing his hands up and down Dennis’ red raw ass. He only slows to a complete stop when the rhythmic milking comes to an end.
“Gonna pull out now, just to flip you around. I want to see that pretty face.” Dennis whines a little but Robby is quick with it, pulling out, strong hands on Dennis’ weak body, rolling him away from the mess he made so he’s not lying in it.
What greets him is even hotter than the plug.
Dennis’ face is flushed red, tears making his lashes thick as they clump together, and he can see the crescent shape marks from his nails flamed red and irritated. But that’s pretty normal. What isn’t is the way the lacy panties he’s wearing have gone see-through with his cum, sticking to his now half-hard cock that’s trapped underneath them. It’s a beautiful fucking thing.
“Stay right there baby, don’t move.” He takes a quick step to the side, leaning down to grab his phone where it got knocked on to the floor. He’s quick to open the camera app, snapping a few full body photos of Dennis before zooming in on his cock, the way the lace clings to the curve of it. It’s fucking filthy. “Perfect, so fucking perfect.”
The phone gets discarded again as Robby swings Dennis more towards the center of the bed so he can climb up between his thighs. Logically, removing the panties would make this easier, but he can also just pull them to the side and fuck Dennis while he’s wearing them. And why would he let his present go to waste?
Dennis is so sensitive, even the light touch to move the lace back up to his hips and then off to the side makes him gasp and jerk, legs spread wide to accommodate Robby between them.
He’s a bit of an asshole, unable to help himself, as he slides two fingers inside, smirking down at the way Dennis’ hips jerk and the little whimper he lets out. As an apology he pulls out, leaning over the boy to kiss him softly and sweetly, licking into his mouth before pulling back.
A third orgasm will be hard, but like this he can fuck, kiss, and tease Dennis, with everything all combined he has high hopes. And Dennis does respond so well to having his nipples played with, Robby almost wants to see if that alone would be enough.
“God the minute you cum again, I’m done for. You ready?” Dennis nods and Robby flashes hot. “Good, that’s real good. Show me how ready, play with yourself. Wanna see you touch those pretty tits.”
He suddenly gets hit with the image of Dennis in a matching bra, white lace barely covering up his pink nipples, and has to take a deep breath to stop himself from cumming right then and there.
-
The first time Robby ever referred to Dennis' chest as “tits” he’d been embarrassed, and even a little offended. Now, though, the minor degradation of it is exactly what he likes about it. Something about it just feels dirty in all the right ways.
It’s even worse now, combined with the overtly feminine outfit choice.
His nipples are already sensitive from being chest-down on the bed while Robby had his way with him. Honestly, his whole body is overly sensitive from two rapid fire orgasms. It feels like there’s TV static in his blood.
He has to swallow to unstick his throat before he can speak, which he figures out after a disastrous first attempt that just ends in a sharp whine. Finally, he manages to rasp out, “kiss me, please?”
He’ll do whatever Robby asks of him, even if it’s painful or debasing, he just wants that tenderness that makes it worth the suffering.
Robby has never once denied him kisses, especially not when he’s like this, and tonight is no exception. He leans in and at first it’s just gentle, loving little pecks. Dennis can taste the sweat from Robby’s upper lip, feel the warmth of his breath. It’s heady, damn near intoxicating. And then the kiss gets deeper, more all-encompassing, stealing what little air Dennis has. It’s perfect.
He does as he’s told, then, with Robby’s tongue behind his teeth. He moans into Robby’s mouth while pinching his own nipples, squirming on the silky sheets. He can feel Robby smile against his lips, and the growly moan he gets in return that drowns his own pitchy noises out.
When he can’t stand the direct contact to his nipples anymore, he squeezes his chest with his palms instead, and Robby pulls back from the kiss just far enough to watch, pressing their foreheads together instead of their mouths.
“So fucking pretty like this baby, fuck, how’d I get so lucky?”
Dennis just blushes and pants, no real capacity for coherent words anymore. He’s not even getting hard again, though his dick is still leaking almost constantly, soaking the panties until they’re nearly translucent.
Robby kisses him again and then pulls back to watch properly, and Dennis does his best to put on a good show, forcing what little muscle mass he has to make some semblance of cleavage. Robby strokes his cock to stay hard while he watches, gaze dark and hungry, even re-applies some lube to ease the glide when he gets back inside, and Dennis preens under the attention until finally he can’t take it anymore and begs in choppy, high-pitched sounds that vaguely resemble human speech.
“Inside? Please? Need you again, Daddy.”
-
Robby, on a normal day, isn’t sure he can deny Dennis anything. Like this? He might actually be physically incapable of doing so.
So of course he’s quick to kiss the request off of his lips as he slowly eases his way back inside. This round is less about putting Dennis through the mattress and more about the love and care Robby tries to show him in all aspects of their relationship.
“Oh there you are. Daddy’s got you,” he groans against Dennis’ lips as he fully seats inside. “So fucking perfect. God I love you so much.”
Dennis whines at him and Robby gives a little roll of his hips in response. He’s keyed the hell up, but he’s determined to get one more from his boy before he finishes. Dennis is doing so good touching himself, playing with the parts of his body that feels good without being oversensitive enough to hurt.
Each roll of his hips is met with a breathy little moan from Dennis. He’s not sure what he did in this life, or any of his past lives, that allowed him the privilege of getting this now, but he’s not going to waste it. He moves to nip along Dennis’ jaw, sucking little marks down his throat that should disappear by the time they’re scheduled to leave. He makes sure the touch of his hands is gentler, but no less possessive.
The lace catches on his cock a bit, but honestly he’s willing to deal with that for the moment, rubbing himself raw so that he can continue to watch the way Dennis’ cock leaks inside of them is worth it.
He’s slow and gentle with every move, making sure he’s not away from Dennis’ mouth too long, giving him all the kisses he could ever want, enjoying the hazy look in his eyes when Robby does pull back to look at him.
Eventually he reaches down, running his thumb under the underside of Dennis’ cock through the lace, shushing him when he jerks and whines loudly.
“I know baby, I know. Shh, it’s okay, you’re okay.” Robby kisses the concerned look off of his face. “Daddy wants to give you your reward, you wanna cum again for me?”
Dennis is well beyond words, but he gives a small and barely there nod. Robby runs his thumb down and back up again, feeling the cock under his finger give a valiant twitch, slowly, so slowly, filling back out. Robby kisses him for being so good.
“Just feel it, Daddy’s gonna take care of you. Soon as you cum, you’ll get your reward,” he fully wraps around Dennis’ cock now, not quite fully hard but on its way. “Fuck you feel so good.”
Robby’s holding on to his own orgasm by a thread, but like fuck is he going to cum and ruin this, Dennis said he’d give three, so he’s going to hold out as long as it takes to get there.
-
The thing inside of Dennis' skull is no longer a brain. It is a soupy mush of endorphins and adrenaline, sloshing around in there like a Magic 8 Ball where all sides say “You’re Gonna Die”.
He can’t breathe, every inhale gives him nothing substantial, every exhale just turns into embarrassingly high-pitched sounds. Everything feels so good it hurts. Not just surface level overstimulation but bone-deep, like his own body’s trying to turn itself inside out to give Robby what he wants.
The kisses are the only thing keeping him tethered to this plane of reality, Robby’s mouth a lifeline both from that and his voice promising him a glorious end to this, a reward for his endurance.
He knows he’s crying, but can’t even be fucked to be bashful about it anymore. It’s well past cute little shiny trails that can be gently brushed away, he’s damn near sobbing, face patchy-pink and damp from sweat, spit and tears in equal parts, lashes turned into messy clumps that stick when he remembers to blink.
The fabric barrier between Robby’s hand and the raw skin of his cock should offer some relief but instead it just makes it worse, distributes the sensation all over, forces him to feel the fact that he’s, well, Robby says it best actually—
“Fuck, baby you’re soaked like a girl, so wet for me.” There’s awe in Robby’s voice, honestly approaching rapture territory, and the humiliation of it just ramps Dennis up more and more, makes him squirm and buck up into the steady strokes even though (or rather, especially because) it hurts.
He doesn’t even know how to close his mouth anymore, passively aware he’s drooling all over himself, getting Robby’s beard wetter and messier every time they kiss.
He can feel himself getting close again, the way his stomach cramps and his thighs tremble, but he’s honestly scared of what’s going to happen when he peaks. Normally, the buildup is warm and lovely, even when he’s desperate. Right now it feels like there’s angry bees inside him, body protesting this down to a cellular level.
And yet… never once does he even consider tapping out. He could. Robby would stop immediately and pivot to comforting him without a second thought, completely ignoring his own aching need. He’s proven it.
Dennis doesn’t want that, though. He wants to earn what he’s been promised. Wants to prove to both of them he can handle this. Wants to be ruined for anyone else.
He forces himself to try to steady his breathing. He gives up touching his chest and isn’t reprimanded, Robby seeming to understand that he needs something else instead, although he can’t exactly communicate what in this state. Sweaty, trembling hands wrap around Robby, fingertips digging into familiar, comforting warm skin and muscle, something to ground him when everything shatters.
And it does. He can hear glass breaking in his ears, or maybe that’s just his own mind finally ejecting itself from this plane of reality. Because one second he’s there, somehow both pleasure-drunk and in agony simultaneously, cock feeling like it’s molten-hot under Robby’s touch, one leg up over Robby’s hip to let him get deeper, and then the next—
Nothing.
He’s floating somewhere, high above the roof of the cabin, the tops of the trees, even the stars that remind him of being back home in the open plains. His throat hurts like he screamed but he can’t hear anything, full of cotton and fully unnatuned to reality, so far down into himself that nothing matters but Robby’s voice, the only thing still coming through somewhat clearly, although even that is muffled and too fast to process each word individually.
Then, everything rushes back all at once, like a wave receding off the shore back out to see. Blood roars in his ears, and he can feel Robby’s cock pulsing inside him, filling him exactly how he wanted, cum searing hot and copious. He’s still talking, just one long string of praise and reassurance that Dennis soaks up just as greedily as the spend being pumped inside him.
He finds his own words, or, word, choking out a pitiful “Daddy” that turns into a broken cry, and Robby shushes him sweetly with more kisses, cupping Dennis' face in both hands like he’s precious.
“Perfect, baby, such a good boy for Daddy, you did so good. I’ve got you, you’re okay, Daddy’s here.”
Dennis whimpers and after a few more kisses, tucks his head to hide in Robby’s neck, breathing in the scent of his cologne and sweat and sex, trying desperately to remember how to breathe normally again and wanting to be as close to Robby as he physically can without grabbing a scalpel and making a burrow for himself behind the man’s ribs.
-
Dennis’ cock just keeps leaking, hard and wet, soaked through the panties and all over his hand. It’s something that’s never happened with them before, but he’s also never pushed Dennis this far, two is usually as good as his boy gets, but fuck if it isn’t such a delicious sight to see.
Robby’s never seen anything like it, never had someone push themselves so far for him. He wants to give Dennis the entire world. He wants to lasso the moon like that old black and white movie, wants to make sure his boy never wants for anything, wants to both wrap him up in a blanket so nothing can ever hurt him again but also wants to fuck him to tears like this every night for the rest of their lives.
He shouldn’t be turned on by the drooling crying mess Dennis has become, but he is, painfully so. Every little whimper and whine is music to his ears and when they started all of this he felt like a creepy old pervert, but now? As Dennis moans and cries and jerks pathetically into his hand? He’s never felt more sick in the head.
It only makes him harder, the need to cum rushing down his spine.
Luckily for him though, Dennis doesn’t last much longer. He cums with a literal scream, and Robby winces a bit at how painful it sounds before it just- cuts off. He leans down to press his face to Dennis’ neck, hips stuttering as he, too, cums, babbling praise and love the entire time. It feels like it never ends, just pulse after pulse of release, as deep as he can possibly get inside of Dennis, still rolling his hips like he can fuck it in even deeper.
When he has the strength to pull back, kissing up Dennis’ sweaty throat, peppering his cheeks, he can see that Dennis is gone.
His eyes are open but unseeing, mouth hanging open, drool still leaking out. Robby is so, so careful, as gentle as he’s ever been in his entire life, running his hands up and down his body, kissing over his skin, offering up his praises and love, making sure wherever Dennis has gone, he still feels loved and warm.
Robby’s in the middle of brushing Dennis’ sweaty curls off his forehead when he comes to, blinking rapidly and making a little humming click noise that cuts off a few times before his mouth moves to form a real word.
Daddy has never sounded so good, never felt so right, never made his heart swell as much as it does right there in this moment.
He’s quick to roll them, carefully, letting Dennis bury in his neck, holding him tight and close. He runs his hands up and down his back, trying to encourage normal breathing again.
“Take your time, sweetheart, just breathe. You’re so perfect, so good, just feel it. It’s okay.” Robby kisses the top of his head, humming softly as Dennis buries further into his skin like he can’t get close enough. If it were possible, he’d crack open his ribs and let Dennis inside. He’d literally remove his own beating heart and offer it to him if that’s what he wanted, if that’s what Dennis thought he needed.
As is, he’s not sure he’s got the tools. So he gives him touch and words, holding on to him until he can hear and feel the normal inhale and exhale of breath, how it’s supposed to be. He reaches over to the side table, grabbing his discarded shirt and pulls Dennis back from his throat.
“Shh, don’t whine, I’m just cleaning you up.” Dennis is still a little hazy-eyed and tearful, but Robby wipes the worst of it off of his face, careful under his eyes. “You’re so beautiful, god how did I get so lucky?”
-
Dennis does, in fact, still whine, because while being cleaned up is nice in theory, whatever it is Robby is using isn’t the softest on overly-sensitive skin, and he wants to be back in his favorite place, up under Robby’s jaw, listening to his pulse racing through his carotid.
But Robby kisses him again, and says more sweet things, so he endures more medieval torture, like having the corners of his mouth wiped clean and his hair untangled with deft fingers. He knows Robby likes this part almost as much as the sex itself, his title in the bedroom not just pure vanity and a reference to their age gap. He loves doing the providing and comforting, and Dennis is more than happy to let him, even if he grumbles about it in the moment.
Robby pulling out is awful. Dennis' hole is overly-sore and puffy from the abuse and with how over-stimulated he is the rush of sticky, cooling fluid earns Robby a pitiful noise of complaint and big sad eyes. Apparently his expression is fucking hilarious, because Robby just smirks at him and kisses his nose, very poorly hiding a chuckle. “I’m sorry baby, you just look so cute when you’re pouting like that.”
The worst of it, though, is the two minutes and eighteen seconds it takes Robby to get off the bed, find the baby wipes in his bag, get a water bottle for them both from the fridge, grab his discarded hoodie, and get back into bed. Dennis sits there like a sad stray cat on the porch in the rain the entire time, feeling incredibly clingy in the aftermath and also a little embarrassed about said neediness.
When he gets back, he’s only forgiven after several more kisses and some very lovely head scritches that have Dennis falling back into Robby’s chest like a ragdoll, soaking up the affection after everything he just went through.
Robby helps him get his stockings off first, massaging the faint indents from the seams as he peels them away and tosses them somewhere off the side of the bed. The panties themselves come away tacky with a mix of their cum that makes Dennis blush so bright he can actually feel how warm his face gets.
“God, we’re gonna have to burn those.”
Robby looks scandalized and holds them out of Dennis' reach, childish. “Absolutely not. I’m keeping them as a trophy.”
Dennis groans but doesn’t have enough energy to argue about it and just concedes to the fact that this will absolutely be a bolster to Robby’s ego he will never be free from. It doesn’t matter that Dennis loved it just as much. That’s his business.
When Dennis can stand to be touched again, Robby gets them both cleaned up and rehydrated, and zips Dennis back into the hoodie.
He likes the way it always smells like Robby and a little bit of hospital antiseptic. It’s two things he associates with safety and familiarity, and the worn-soft material is nice on his still tingly skin, loose enough to not feel constrictive but keeping him warm and cozy.
Robby lays flat on his back, away from the embarrassingly large wet spot on the other side of the bed, propped up a bit on the cleanest of the pillows, and pulls Dennis onto his chest, letting him get settled in his favorite spot again, finally. They can deal with food and proper showers later, but for right now this is good enough to be comfortable. Dennis isn’t ready to be a real person again yet anyways, still a little raw both physically and emotionally, and Robby seems to pick up on that.
“Love you,” he says as he leaves another kiss on Dennis' forehead. “Proud of you, too. That was a lot and you took it beautifully.”
Dennis hums, just a little sound of contentment, and presses a kiss of his own into Robby’s sternum. “Love you too. ‘M okay, just tired. Was really good. Thank you.”
Good night be the understatement of the century, but he’s not exactly a poet on the best of days, and he still feels like half his brain is somewhere in a puddle on the floor, so it’ll have to suffice for now.
-
Robby’s favorite thing to do, other than fuck Dennis, is to take care of him afterwards. When he can really give in to everything inside of him that just wants to take care of, and love on, another person. Being a doctor helps it a bit, but there’s nothing like taking care of a romantic partner. He knows sometimes he can go a little overboard, that Dennis sometimes just wants to go to sleep or be held, but that’s not normally enough for him.
Especially not after something as intense as what they just did.
He was intense, Dennis just took a lot, and there’s a bubble inside his chest that feels like it’s going to explode, and the pressure on it only releases when he’s carefully wiping Dennis down or stripping him out of his sticky clothes.
It only goes away when Dennis curls back into his chest, redressed in his favorite hoodie, looking warm and happy.
Ideally, he wants to get them both cleaned up, fresh sheets on the bed, and food in their bellies, but he’s also happy to just cuddle up with Dennis for as long as he wants to. Especially when Dennis looks up at him with those stupidly wide blue eyes and little pink blush still on his cheeks.
“Thank me? Baby I should be thanking you. I think you knocked my brain half way out of my skull when you walked out. I wasn’t thinking about anything at all but you and me, and that’s exactly what this anniversary trip is about.” He tightens his grip just a little, a little voice telling him Dennis will disappear into nothing if he doesn’t hold on. “It was a very good surprise, I never would have guessed you’d dress up like that for me. Where’d you even get the idea?”
Dennis squirms in his grip and Robby just holds on tighter, his voice is quiet when he responds. “I may have asked the internet. Reddit specifically.”
Robby scrunches his face in confusion. “Reddit. Isn’t that just- weird guys living in their mother’s basement?”
Dennis laughs at him and Robby feels a blush form under his beard. He’s not incompetent when it comes to technology, but it is where their age difference becomes a lot more obvious.
“No- it’s- honestly I can’t really explain it, there is that sure but it’s also community and art and a lot of stuff. Advice threads, which is where I wound up.”
Robby hums, ducking down to press a kiss to the shell of Dennis’ ear. “Well, whatever it is, they had some really good advice. You always look good but that was something else.”
Dennis tries to hide his smile in his chest, but Robby sees it anyways, happy that his boy is happy. Pleased to know that he can make him feel at least somewhat as good as he makes Robby feel.
An understanding of Reddit and other internet resources aside, Robby is excited for the rest of their trip. There’s good food in the refrigerator just waiting to be cooked and eaten, a beautiful view of the woods around the cabin from the porch he can’t wait to drink morning coffee on, and a hot tub that will work out the kinks in his back and all the soreness Dennis will be feeling in the morning. And, at some point, there’s a gift on the dresser for Dennis to open. He’s not sure it’ll even come close to the gift he just got, he’s excited for the exchange regardless.
All in all though, with a start like that, it’s already better than anything he could have ever planned himself.
-
r/relationshipadvice
u/dennysgrandslam
I [27] am in my first long term relationship and want to surprise my boyfriend [54m] for our anniversary
So, like I said above, this is my first real relationship, and I don’t really know what’s customary beyond regular gifts. I have an actual present for him already, but my roommate [25F] and one of my older siblings [32M] keep making pretty suggestive jokes implying I should be giving a “spicy” gift as well. We have a pretty healthy sex life and have been exploring kinks together, but I’m not incredibly experienced in that regard since I grew up religious. Any ideas for possible fun surprises? He’s taking me on a weekend trip on his motorcycle, so it has to be something relatively discreet I can fit in my backpack. Thanks in advance
Edit: I just wanted to thank (almost) everyone who commented, you guys were right. He has a hoodie I steal pretty often, and I ended up wearing it with a pair of lacy panties and some thigh-highs, and not to be too graphic but between the aftermath of that and the long motorcycle ride, I actually cannot walk. I have been given the baby deer legs curse. We were going to go on a hike today but instead I am soaking in the cabin’s hot tub and being doted on. He says thank you too, and that he’s glad you’re not all weirdos living in your mom’s basements.
It has also come to my attention that I forgot to tell you all that I am also a man, so, not sure if the advice would have been the same either way, but regardless, it worked out. Anyways, thanks again, people of Reddit.