"Y-you actually went out and bought one?!"
Today is the day you decided to try out pegging your boyfriend. If you think about it, you would have never expected to be here. The strap on is still safely in the bag you brought over. You're straddling his hips and waist, and you know the doubt that comes from him. Acting surprised that you'd actually go out and buy something like that for him, but the twitch you felt beneath your own hips proved otherwise. A part of him knew that you would do anything for him as he would for you.
Tadashi Hamada tends to be a reserved person when it comes to things like sex. To him it's something for his private life and any sexual actions are based on love first over lust. He's a rather romantic person, so why not spoil him? It's sometimes hard to resist him, though you do anyway for his sake. He is great on the eyes, beautiful inside and out. From his broad shoulders and surprisingly slim waist. Plenty of muscle provided between the two; his stomach, chest, and arms being firm. His face is always smooth as glass, shaving when necessary. He isn't a hairy guy, but the hair provided is flattering. From the thin strip from his tummy down to below his hips to when he has that shadow from working rather than attending to his everlasting beard. Tadashi not only has the looks but he also has the personality. This guy tends to usually be selfless, helping anyone he can; his friendly exterior is perfect for it too. The humor he produces can go from math puns to -well- other puns. Summarizing Tadashi Hamada up is simply, "perfect."
"Well yeah, why wouldn't I. You said you wanted to give it a try. Plus, how can you go wrong with having a strap-on in your possession?" You shrug as you reply, drawing circles in the skin near his hips.
After stumbling over his words, Tadashi sighs giving in as he did mention this request before. "I- Well tha- fine, fine. I agree with today but could you maybe take it home with you? I do not need either my aunt or brother finding it and thinking it's mine- or worse."
"Seeing as how you already have your own in flesh, I don't think they'll assume it's yours specifically.." You tease him back, sometimes certain things making Tadashi uncomfortable. His family finding out about sexual events involving him being one.
Tadashi's face burns a light red. You watch his chest rise and fall until he sends an arm behind him blindly, reaching for a drawer. With that hint taken, you go get the strap on and walk back over to him with it. He changes his position from laying to sitting as he hands you the small bottle. After placing the strap on, on the floor next to the bed you take a small drop onto your finger- of lube. With your other hand you run a finger up the center of his chest with little to no pressure, causing him to visibly shudder. Using your full hand you push his chest to get him to fall on his back, which he complies to.
Tadashi's house was empty besides you, him, and mochi. His brother was at his friend Fred's house having a sleepover. All of his friends are actually there. They're having a party to celebrate them doing well during exams. Tadashi would have been with his brother, friends, and you at the party if it wasn't for one thing. Tadashi caught a cold. For a few days he's been sniffling, blowing his nose, freezing, burning up, and coughing. Being the good person he was he decided to stay home so he didn't infect all of his friends. In fact the only reason you're over is because he's home sick, recovering. He's already had soup and cold medicine. You'll probably get sick, but you didn't care as long as you were with him. His Aunt even was out, she was catering at an event. The event won't be over until late so she left Tadashi in your hands. She wouldn't have left if he was alone.
Tadashi rested his weight on his elbows when you got on your knees. He wanted to see what you were doing but by his yelp you figure he must know now, the lube being cold against his heated skin. One finger swirls around the pucker and the other hand takes him and softly brushes up and down in a slow rhythmic pattern. Your hand is ghosting over him at first until you finally decided to do more, your grip tightening. Tadashi lets out a small gasp when you tighten your grip.
Figuring you'd get Tadashi close to the edge first before doing any penetration, you focus mostly on his member. Your hand continues at a faster pace. Leaning forward, you put your face right next to his shaft. Tadashi shivers from your breath, using his own hand to switch between caressing his stomach and brushing against his nipples.
With his legs spread you pull his member closer to his stomach so you can lick from his balls to his tip. You do this two or three times and start again with your hand, your mouth going towards his balls. Your tongue goes all around them, eventually taking them into your mouth and sucking. He groans loudly and grabs at your hair, pulling gently. The pull feels good and you take more in moving from his balls to lick the tip and slit first. Your mouth stretches and your lips surround him as you start taking him into your mouth. The tongue runs along the bottom as you take more in again, sure to let your mouth and jaw adjust to the wide girth.
Tadashi isn't huge, but he isn't average either. His dick would easily go down your throat with its length. Easily hurt your jaw with its circumference. But with his gentle nature, he'd care more about you rather the pleasure he'll receive.
With it three fourths the way in, you hum around him. You force yourself down more than you can handle at the moment, your eyes watering from it. Tadashi arches his back, moaning loudly at your actions. With a quick move you pull your mouth off with a pant as the saliva strings from his member to your lips. At your actions Tadashi sits up some to look at you questioningly. His face is red and his eyes are half open as he pants.
"Do you want to fuck my face?"
His eyes go wide and you know if his face wasn't already red he would've turned red at your sentence.
"W-what?! Why do you.. say it like t-that?" His words come out with pants inbetween, his breath quivering a little from pleasure.
"Because I love turning you on. Do you want to or not? We don't have to but I figured since I'm going to soon be dominating you, I'd give you your own turn first." You see him looking at you, blinking slowly. The gears in his mind are visibly turning as he thinks it over. Eventually he lets out a breath of air, nodding and smiling at you.
"Whatever you need, [name]." His voice is low and deep, send a twinge past your stomach. The velvet words encourage you even more, immediately going back to his member. Taking a deep breath, you smile back at him as his hands go towards your face. It wouldn't be the first time you've done this, but it's as if it'll never get old. Hearing his moans, being practically used by him. Seeing this side of Tadashi is an absolute blessing.
You position yourself over the head, taking another deep breath. Sliding down, you feel it refill you again. Tadashi's hands envelop your cheeks as he slides you down further. You're nearly farther than before, until you feel him reach your throat. You groan at the feeling as Tadashi does the same. It's hard to breath and you try to move your head but he keeps you down for a few more seconds before letting you go to come off and get air. You pant for air, and look back up to him. His face seems hotter than before, as if he could get anymore attractive than he already is.
Nodding back to him he takes his hands and puts them on the same place as before. He hovers you over himself before you take him into your mouth again. This time he only has you go down half way, saving room for the next actions. He slowly moves you up and down along his shaft and he sighs from the feeling. It only lasts for a few minute or two until he starts moving his hips too. Again he starts off slow so you're used to it, but afterwards he goes faster. Your hands lay limply at your sides, having everything come just from him. His hips start thrusting at a decent speed as he goes into your mouth smoothly from your saliva.
Just the movement isn't good enough you want him to feel more. You hollow out your cheeks, sucking as he thrusted. Tadashi usually takes things slow, not jumping to the end quickly. But with his actions, it will probably only last a few minutes more. You lick what you can as your tongue is pressed to his shaft. He groans again, slowing the pace to small thrusts. Your hands go from your sides to his hips. With your touch he starts thrusting fast again. Your head is at a fixed point as he holds you there. He slides in your mouth vigorously, the saliva building up from not coming off of him. You rack your nails down his sides, what you can reach. It encourages him to growl and to go faster, to the point where he is literally having sex with your mouth. It feels unbelievable.
Tadashi is so close, you can feel it with his sloppy thrusts. He pulled off once more, the saliva dripping all over his thighs as he pants loudly. You go back down and you acknowledge that Tadashi will be done this time. He's a mess, his breath hitching every so often. It isn't long before he thrusts all the way into your mouth, your eyes widening a little at the sudden depth. His hips jerk up abruptly with your nose rested into his patch of hair. One hand goes to keep your head at that distance and the other pinches your nose. He moans, basically keening, as he releases straight down your throat. There wouldn't be any other choice than the one he's given you, forcibly swallowing it. Which doesn't exactly bother you, as you would have anyway(probably why he actually did it without asking). He cums but holds on a little longer than necessary as you can't breathe. You groan and try to move away but he doesn't really notice, completely lost in his own blissful orgasm. You pinch the skin on his side and he completely lets go, jerking straight up.
Tadashi starts panicking, his breath even less now. You started coughing a little because you breathed in and choked a little on your spit. Of course Tadashi starts squirming and apologizing many, many times. He gets down from the bed to sit next to you and start patting your back and rubbing your thigh, slightly, for comfort. You stop coughing and smile towards him but his face is contorted into worry and fear. It makes you furrow your brows, you grab his face and kiss him gently on his lips. His eyes widen and then close. After pulling away he hugs you tightly, too tight.
"T-Tadashi. Uh, I can't breath." You say, through your struggle.
"I'm sorry, I'm so so sorry. I just completely forgot what I was doing and I'm sorry. We can stop if you want to, just say so." His words come out rapidly and high pitched from his fear. At last he pulls away and looks down into your eyes, searching for your own fear.
"No it's okay. It's completely understandable. And besides, you did what I said so it's not your fault. This pegging thing was your idea so don't think you can drop out so quickly," you laugh, "but if you want to stop we can." You ruffle his hair as he closes his eyes at the action. He takes your hand from his head into his own hands. His larger ones easily swallow up yours. He brings your hand up to his lips, kissing your knuckles. Tadashi also starts rubbing his thumb over your hand as well, making your hand feel slightly numb in that spot from the repetitive motion.
"No that's okay! If you still want to continue we can. I was just worried if you were ok," as he talks he gives you your hand back to stand up, but offers to take it back once he is up. You take it and smile. As he pulls you up you let go and hug him tightly, burying your face in his chest breathing him in. He's actually really sweaty from what you guys just did but you stay like that anyway. Tadashi's arms wrap around you as well and he kisses you on top of the head? You move your head, so your face isn't pressed into him, to talk.
"We can continue, just get back on the bed in the same spot. It'll be easier like that anyway," you mumble at him because your face is smushed. Tadashi laughs and unwraps his hands, unwrapping yours as well. He smiles and crawls back onto the bed as you go to get the strap on. (Which has been on the floor the whole time.)
This time you actually put it on. It isn't just a plain strap on though. It's one of those that are made for pleasure for both people. The strap on actually going inside the wearer too. You smirk to yourself just thinking about what's going to happen. Tadashi is on the bed, on his back with his legs dangling off the side. You stand up, infront of him and put your hand on your hip. He slightly waves at you with his fingers as he gives a bad attempt at a smile. You sigh a little, knowing that this is the first time he has actually been a bottom.
There have been many times Tadashi thought about bottoming. Tadashi may not be a sex crazed person, but it doesn't mean he is oblivious to it. He still thinks about it, still deals with it. Tadashi is panromantic, demisexual. He has no problem with who he dates. His preference hardly exists, allowing him to be open to everyone. However when it comes to sex, he doesn't give it away easily. It's something more special to him. It's the reason why he hasn't bottomed. Tadashi has been with a few guys, but never felt close enough to attempt be a bottom. He has been with a few girls as well, having the same problem of not being close enough. It wasn't until he met [name], that he actually thought of the possibility. Tadashi trusts his current relationship enough to go as far as he wants, though it doesn't make him any less nervous.
You crawl over on top of him, your hands besides his head and your eyes looking down at his. Tadashi is obviously nervous. You stroke his hair slightly and press your lips gently to his. Pulling back you smile at him, "It'll be fine Tadashi. We can stop at anytime if you don't like it. And I plan to prepare you enough so it feels amazing. Just use the usual safe words and we'll stop." He stares at you and you see him swallow as his adam's apple slightly bobs. After a few more seconds he nods at you and smiles weakly. Kissing him again you crawl back off of the bed and put yourself between his legs.
You spread them slightly more to have more in view and he hesitates but lets you. With the lube still on the floor you put in on your finger, smoothing it around his entrance for the second time. Just as before he jolts a little at the coldness but relaxes after its warmed up. The lube is actually flavored, as you don't plan on just using your hands. Your index finger slowly circles on his entrance after putting more on, finally entering for the first time. Tadashi squeaks a little at it and you rub his thigh a little to comfort him. You wait for him to relax and after a few deep breaths he does.
"Yeah I know it's weird but it's the first time so just try your best to relax or it'll be harder on you," you say, starting to move your finger slightly. He groans as a response and you push your finger in more, wiggling it a little and pressed it against his walls. You pull it back and start fingering him a little with your finger to make him used to the motion. After that you take it all the way out. Instead of your finger this time you lick at him. He gasps letting out a little, 'what.' But you just shush him and continue. With one hand you softly pump him as you continue to circle his entrance. You finally put your tongue in, making him gasp again at the feel of your wet muscle. Tadashi doesn't appear to be in pain, just confused at the weird feeling of a tongue. Your tongue circles inside of him and comes out licking at the entrance again until it re-enters. When you think its enough you pull away getting more lube to put on two fingers.
Tension is practically heard through the silence, nothing is really heard besides his soft pants and the lid of the lube. "I'm going to use two fingers now ok?" He gives a little nod to the warning. You insert the first finger to start from the beginning and then pull it out to insert both. The fingers slowly go in from the tightness and Tadashi yelps. Before he can tell you to stop you thrust them in all way, causing him to yelp again and yell, "r-red light! S-stop!" You stop as he says it, and look up at him.
Tadashi's fists are clenched roughly in the sheets and his face is strained. His breaths come out loudly as he tries to relax and adjust to the bigger size. You start to kiss up and down his inner thighs hoping to comfort him as he adjusts. It isn't until his pants are very light and slow does he say green light. Going along with him you spit in your hand and start stroking him again. This time is faster than before to amount with the more pain he is feeling. The two fingers inside of him start to scissor in the same spot. It isn't until you hear an encouraging moan do you start moving the two fingers in and out. After that your fingers scissor going in and out too. Your middle finger is able to brush against his prostate. It's noticeable because after scraping it his hips jerk up followed by a gasp. You push them back down so he can't thrust into your fingers. The fingers by now have overall mostly stretched Tadashi out. Just in case, you re-enter with three fingers added with lube again. Assuming by now Tadashi is completely relaxed and starting to feel the pleasure. The three fingers stretch him out a little more and he moans at the feeling of the third finger.
Mistakenly after the combination of the fingers thrusting and pumping of his member he's already close to the edge. Quickly you add more lube to the entrance and rim before putting it all over the strap on's member. Your hand still pumps him as you align yourself with his entrance. It already previously stayed open from being stretched out. Slowly you put the tip in and Tadashi lets out a low groan. You start pumping at a vigorous pace and his hips thrust up for more. After aligning yourself, you thrust in to hit him in the specific spot. You don't truly know if you hit it or not but he cums with his back arching off of his bed and his eyes rolling a bit back from pleasure. After his body collapses you pull out the tiny bit you went in and slow your pumps to a stop after he is done cumming. Now he's just a hot panting mess with his own cum all over his chest. It's hard to resist it as you crawl to start licking his cum off. He rests his hand lightly on your head as you clean off his stomach. Tadashi chuckles slightly, you feel the vibrations from his chest.
"Sorry, I guess I came before we even started the pegging," his words were still breathy and you just grin when you look back up at him. That goofy smile as he breathes in and out and strokes your hair. You hardly penetrated him and he came, he's going to enjoy the main dish. After you're done licking him you flop onto your back next time him. He should be done catching his breath soon, but you take the time to relax too. You nuzzle his cheek and hair, pressing light kisses from his forehead to his collar bone. Eventually his breaths don't come out of his mouth and start from his nose. You slide back off the bed and stand at his feet.
"Come on now Tadashi, this is what you've been training for. I believe in you and as long as you try your best you'll always be a winner to me." Tadashi peeks out from underneath the arm he put over his eyes. He gives you the weirdest look and just laughs. He sits up with his elbows and raises an eyebrow.
"I'm sorry but am I in the olympics?" he asks, chuckling slightly. You just nod as you scoot up to be touching him. Tadashi spreads his legs wider, so you can enter. You climb on top of him a little and kiss him. As your waist is in between his legs and your arms right next to each other. You move the strap on so it's touching his entrance and you start kissing him more passionately. Your head tilts and he starts nibbling on your lip. He lets it go and you start sucking on his. Finally your mouths open as your tongues tangle with each other. Taking this opportunity you start pushing it in and it earns a groan from him. After a few seconds of resting you slid in more and you pin him down to the bed. His eyes take a bedroom like look as he looks at you. The final movement earns another groan as it's completely inside of him. You start to lick at his neck, nipping as you go. Your teeth brush against his skin until he gasps as you reach a sensitive spot. Taking advantage of it you graze your teeth and suck on it, hopefully leaving a mark. He whispers out "move" as you continue to bite at his neck. You listen and pull it out. He doesn't get movement until you start facing him again. Your eyes stare into his as you thrust in all the way again. He moans loudly but they get cut off as your mouth covers his. The long thrusts continue until they pick up, just becoming pounding. Tadashi is beyond loud as he leaves his mouth open to pant, as you've stopped kissing him and moved your mouth to one of the sensitive buds on his chest. You can't tell which one is making him moan more but you assume it's the pounding. Your hand reaches down to start pumping him and you calm tell that is going to set him off, but you don't want him to come yet. With each thrust his body moves and the other ends of the strap on move inside of you too. He's about to cum, but you wrap your hand so he can't. He orgasms roughly but fails to cum and he groans at it.
After his orgasm fades you let go and he looks at you with his eyebrows pinched together, "what was that for, why didn't you let me cum?" He asked completely confused at your actions. It's so cute and you're half tempting to let him cum next time but decide against it since it's not your plan.
"Because," you smirk. He groans to himself based on your secrets but starts smiling anyway. Clearly he is ready for more and trusts himself in your hands. Your lips turn into a smirk and get more lube. The strap on gets covered again and this time you rest your arms on his legs. Tadashi's legs are pushed back towards his chest, leaving his red member and entrance out in the open. With a quick lick to his twitching pucker you put the tip in again. You thrust in again as he moans softly. With Tadashi's legs by his chest you can actually kiss him again, so you do. You kiss him multiple times, mostly with your lips just pressing against his. He smiles but is cut off as you brush his prostate. Tadashi groans loudly, "r-right there, p-please." It sounds wonderful to hear him whimpering and begging so you comply with his request willingly. You move around a little to find it again and upon thrusting he moans loudly again. You try not to move from the spot, so you can hit it many times. Your hips seem to listen as each thrust sends him keening. This time has already started and you don't want it to be over so soon. At this angle you use, the strap on is pleasing you a lot more. Instead of continuing on his spot, you start thrusting freely again. Now you start thrusting rapidly, each spot hits your own spot every so often. It feels amazing and you can't resist your own pleasure as you don't let up on your pace.
Tadashi pants and moans your name, "you're too fast, I can't handle it," he says between the gasps. It's clear that this pace is taking a toll on him. Tadashi has moved his hands to his butt, spread himself a little more for pleasure. His member is neglected as it bounces between his legs and chest. It's leaking precum, but it won't be cumming any time soon. You don't stop your thrusts, it feels so good for the both of you. With the fast pace you start to feel yourself getting close. You open your eyes, not realizing they've closed from pleasure, and look at Tadashi's face. His own is contorted in pain and pleasure, his tongue practically lolling out. You move your hand to his member so that when you guys cum, he won't be able to. The pace is quickened and Tadashi stretches himself open even more to get more pleasure as he can't touch his member in the given position. You both start to lose control and before you know it you're cumming, moaning his name as he groans too. Tadashi orgasms too but again without cumming. You finally release his member and pull out. He releases his legs from the awkward position, groaning a little from freeing his stiff legs.
Tadashi looks at you and you smile. This is for sure the last time, if you do anymore you'll pass out as well as him. Of course Tadashi won't know that but that's fine. It'll give him even more pleasure. You live to make him happy. After the short rest you get off the bed and stretch. He looks at you questioning and you just smile.
"Ready for another round?"
Tadashi groans, flopping back down, but nods nonetheless. He is for sure getting tired, but figures maybe he'll cum this time. Besides, there aren't many times where he is home alone.
"Come here!" Tadashi scoots to the edge of the bed, looking up at you. You have him stand up and turn around. With your hands you push him so he's bending over the bed. "You can lay on the bed too if you want, you don't have to stand." He takes your advice and lays on the bed. When he is ready he smiles and gives you a thumbs up. For the last time you get lube and put it on the strap on. Closing the lid you toss it onto his pillows. You grab his thighs and pull him a little closer so it's easier, and insert it into him. He hums and you take it that he's okay for more. This time you start thrusting a little slower. Tadashi relaxes and just enjoys the soft thrusts. They could hardly be considered thrusts, its mostly you just going in and out. Without turning it into something boring you start to go faster.
Tadashi's face was resting on the bed as well as hims arms and chest. He moaned lightly as you sped up. You let yourself fall forward so you were hovering over his back. Your hand intertwined with his as your fingers went together. The thrusts became harder, moving the bed every time. Moving forward more, you rest your chest against Tadashi's back and you hear his breath hitch at the feeling of your breasts on him. You pull back a little and stand up. His hips are being held by your hands as you start pounding into him again. Tadashi starts groaning slightly with each thrust. From there you move him so he's on his side. You hold his leg up as the other stays on the bed. The position opens him up more so you thrust deeper. Finally you take his member into your hand too and start pumping it in time with your thrusts.
"Th-that feels g-great," he moans as his eyes are lidded. Tadashi is facing you, looking at how your hips move and how you work his member. He bites his lips at the obscene image and closes his eyes as you squeeze him in your hand.
"More, p-please more!" he moans out. Agreeing you start going faster and harder, the whole bed moving with each thrust. You're still basically hugging Tadashi's leg to your chest so you decide to change to position. You have him just lay on his back so he isn't sore afterwards besides the inevitable. Continuing in the new position you hover over him. Your lips press against his and he opens his mouth for you. One hand is pumping him, the other toying with his nipples. To keep you in him he wraps his legs around your waist. Your tongues twist with each other's, saliva dripping out occasionally. You pull away to attack his neck. Your teeth scrape against his neck as you nibble and suck. From his neck you go to his ear and you nibble there too, sucking on his earlobe. You part from it, wanting to go harder. The bed groans louder as you pound him harder into the mattress. Tadashi pulls you down towards him, putting his mouth on your neck. You untangle his legs so you can thrust much more, his legs falling down as his feet rest on the floor. You're stilling pumping and thrusting and you hear him keen and he bites your neck. Ridiculously hard. You assume it's to muffle the scream. The bite was so hard you're pretty sure you're bleeding but Tadashi wasn't actually done yet and you can tell how close he is though.
To get him far enough you try to find his prostate and after a few thrusts looking for it he jerks his head back away from you and moans loudly. You grab his legs and hold them as you start pounding away at his prostate and he's cursing and groaning while his knuckles turn white from gripping the sheets; he's literally crying from pleasure. A few more thrusts and he's practically screaming and you pull out, as you get on your knees to swallow him. He cums at a ridiculous rate from holding it in so long, you try to get it all but it's spilling from the sides of your mouth as you slide your head up and down. Tadashi's back was arched, his eyes closed shut tightly. He moaned so loud you're 90% sure that his friend's could probably hear him from here. When his hips and body fall back onto the bed you take of the strap on, putting it immediately into your bag. After that you go to the bathroom and get a wet washcloth and re-enter his side of the room. He's basically still out of commission and when you go up to him you find out he actually fell asleep right after that. Instead of bothering him, you just take the opportunity to wipe down all the sweat and cum on him. Tadashi snores a little and you laugh, typical Tadashi. There were sheets already ready to get changed but it would be pointless to do so with him on it so you just used the already dirty sheet to cover him.
After using his shower you come back to see Tadashi sitting up on the bed, just sitting.
"Good morning sleeping beauty," you call out to him. He immediately looks up to you and you laugh at him because he looks so tired with his hair messed up.
"Oh gosh, how long did I sleep? What time is it?" He jerks himself to get up but when he stands and takes a step he just ends up falling over. He groans on the floor and you laugh again.
"You probably should rest before you decide to walk again. You'll be sore for a while. It's your fault for asking for more. Besides I think it's a fair trade for you practically eating my neck. And don't worry about time, we still have plenty." You crouched down so that your feet were on the floor with your knees close to your chest. The shirt is Tadashi's so it's long and you just smooth it out over your legs.
Another groan. He slowly sits up and looks at you. "Yeah sorry about that, I don't think I realized my own strength with that. Can you change the sheets for me? I think I'll go crawl to the bathroom and take a hot bath.."
"Of course, but hey Tadashi."
"I love you."
"Yeah, I love you too [name]," he chuckles and smiles. It reaches his eyes and they crinkle along with his fading dark circles. You're pretty sure you're sick now, so much for not spreading it.