To Peg Or Not To Peg?

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You lay sprawled out on the bed, legs intertwined with Harry's as you both came down from the incredible high you had just experienced. Both of you were completely spent, you could swear your legs were still shaking. The only sound in the room coming from your laboured breathing making Harry look over at you with a lazy smile.
"You ok hottie?" He asks, his hand now drawing circles on your bare thigh. His eyes were attentively on yours, silently asking if you needed anything.
"I'm good. Just thinking" you reply, snuggling in closer towards Harry. He was sweaty but you didn't mind, all you wanted was for him to be close again and to finally get what you wanted to say to him out. You've been meaning to ask for a while now, you just hadn't had the time to actually go for it; nerves definitely getting in the way.
Harry's arms instinctively go around your body, pulling you impossibly closer as he presses a soft kiss to your forehead before letting out a breathless chuckle. "Oh God, that isn't good" he teases making you roll your eyes and playfully hit at his sturdy chest.
"I'm serious" you reply, furrowing your eyebrows as you rest your head on his chest, hearing his heartbeat. It was faster than normal signalling to you that his adrenaline was still running high, even after those three rounds you just had.
"Ok ok. What was it that you were thinking of, hottie?" Harry finally asks, his eyes on you, his fingers playing with your hair. That's what you loved about Harry, he made sure to let you know that you had all of his attention whenever you spoke to him. It made you feel both safe and secure, everything you ever needed in a relationship.
"I was thinking, that next time we should try...anal but I'm the one pegging you?" You said hesitantly, you knew Harry would be down for it especially after that party you had with your friends where he admitted he'd let you peg him, but then again he was a dom which made you doubt if he actually would. He always took control in the bedroom, on the odd occasion he would let you take over and ride him but that was, key word, odd. So you were scared and overthinking about how he would react.
"Then we'll try it" Harry replies ever so nonchalantly after hearing your confession, making your eyes widen as you look up at him.
"Seriously?"
"I swear, I'm down for it. If my hottie wants me to help fulfil one of her dirty little fantasies, who am I to refuse?" He smirks, making you giggle and sigh. Unknowing to you, Harry had always wanted to be pegged, he's heard some of his friends mention it and it's always piqued his interest. He just didn't want you thinking he's weird for that so when it was mentioned in that truth or dare they had the other day, he took up his chance and let you know that it's ok.
"Wow that went better than I thought it would" you say contently, making Harry roll his eyes and chuckle at how delusional you had been.
"Then it's decided, we'll visit that sex shop again so I can get a strap on and then when we come back home, the fun will begin"

Harry knew which sex shop you were referring to, it was the one in the dodgy area where you sure as hell wouldn't find any paparazzi so he nods, letting you know that he was agreeing to your plan.
****
You were both stood hand in hand infront of the strap on isle of the dodgy sex shop, looking at the wide assortment of toys in awe. Harry wasn't speaking much, already letting you take the lead and get what you needed. He just wanted to be at home, with you, naked. If he was being completely honest, looking at you touch all these sex toys and knowing everything about them was indeed getting him very hard.
He quickly adjusts himself when you send him a wink, "which one would you want big guy? This one is about your size" you point out once you find the biggest strap on there making Harry chuckle.
"That'd be perfect" he says with a coy smile plastered on his face. It was as if he was challenging you making you smirk.
"This one it is then" you grab the strap on without a second thought and then go over to the lube section to pick up a bottle. Once you've done all your sex toy shopping, which included you picking out a vibrator for yourself and Harry picking out a cute butt plug for you, you went off to pay at the register and before you knew it, you were back home.
You warmed Harry up with sucking him off, and now he was sat naked at the end of the bed. His eyes were on you, chuckling as you tried to figure out how to put the strap on, on. He walked, well waddled as his dick was very hard, over to you, helping put the strap on onto you before smirking.
"Ready for this babe?" You ask, gesturing to the dildo you had strapped against your core, eyebrows raised as you looked at your naked boyfriend.
He nods, eyes now training onto the massive dick. He didn't truly realise how big it was until now...he was fucked. "You best warm me up before shoving that thing into me hottie" he warned making you chuckle.
"Of course, I don't want to hurt you baby" you reply making Harry lick his lip. His ass tightened and his dick twitched with excitement and in anticipation for what was to come.
"Fine."
"Get onto your hands and knees, hot stuff" you request, walking over to Harry, rubbing his thigh as he flipped over, getting into the correct position.
"Going to get you nice and ready for this, then imma fuck you. Bet you'd like that, won't you? Want to get fucked in the ass by your girlfriend, babe?" You asked, feeling a bit power-mad with your new role and Harry hummed, nodding his head along.
"I need words baby"
"It's perfect. I'd love that hottie, you know I would" he spoke up again, shivering once he felt your fingers trail up and down his thighs, trailing to his hole. You grabbed the lube that was placed on the bed, besides Harry's naked body and squirted it onto him, using your fingers to spread it out. Once you were satisfied, you started to push your finger into his tight hole.
"Relax baby, it'll be easier for you" you recommended after feeling him clench down around you at the intrusion. You kissed his shoulder and continued, once your full finger was in, Harry groaned with pleasure or pain, he couldn't really tell. He felt hazy, his cock pulsating as you began to move your finger.
You slowly added another one in once Harry was used to have one inside of him and soon you began scissoring, stretching his tight hole out in preparation for what was yet to come. He cock was leaking with precum and his balls were tightening at the feeling of being stretched, a groan left his mouth as his head fell forward.
"You like this, don't you?" You asked, continuing with fingering his puckering hole and Harry nods, moaning out a fuck yes.
"Ready to take the real thing now? Do you want me to fuck you baby?" You ask as you spread lube up and down the plastic dick and the. slathering more into his tight hole. You remove your fingers earning a whimper to fall from Harry's perfect lips.
"I want you to relax, it'll feel good. I promise. But if it doesn't then please tell me. We'll stop right away." You spoke, leaning forward to capture Harry's lips with your own for a nasty kiss. Once you were done, Harry nodded agreeing to what you had said, your hands find his ass and you spank him before lining up the tip of the dick against him.
His mouth falls open as you slowly opened his tight hole up, he wouldn't deny that it hurt but damn seeing you take control over him and actually fucking his ass was more of a turn on and he didn't mind the pain. It added to the pleasure.
"Y-y/n" his voice moaned, eyes closing shut as he allowed you to penetrate him. His cock was now rock hard, ready to be touched/licked whatever.
"Yes baby, does it feel good?" You ask, pushing in a couple more inches making him gasp, clenching and unclenching repeatedly as he tried to adjust to the impressive side of the strap on.
"Fuck, it's a lot" Harry spoke, his breathing hitched and his chest heaving.
"I'll give you time to adjust" you smile, dragging your nails up and down his back before reaching down to stroke his leaking cock, soon Harry was pushing back into you, grinding against the fake dick attached to you giving you permission to move again.
You continued with playing with his dick and then also began moving your hips, thrusting into him at the exact pace his was grinding back with. Harry was a moaning mess, his hair all over the place and his back arched as he continued to take the dick like a good boy.
"Oh fuck" he moaned breathlessly.
"You going to cum baby? Tell me you're cumming" you spoke, continuing the agonising rhythm of the thrusts and the stroking of his dick. His face was reddened upon hearing all the nasty stuff you were saying and he was even more eager to cum undone.

It all felt so good for him and he began to feel a coil in his body tighten. The need to cum growing even more desperate.
"Fuck me harder, hottie. G-give it to me. N-need to cum. Please" he growled, begging for his release and you angled your hips slightly, aiming to hit that one spot you know would drive him absolutely crazy and once you did, he was cumming in your hand.
Harry's hips were rocking back against your thrusts, his cum dripping onto the bed through your fingers. You finally pull out of him once his heaving comes to a stop and he falls onto the bed, a chuckle leaving his perfect lips as he sees you sucking your fingers off.
Harry felt euphoric, it was like something he always needed but had never known it. "Fuck, we need to do that again sometimes" he says, breathlessly as you lie down next to him, snuggling into his sweaty chest.
"Definitely, I liked having that control" you giggled and he smiles, kissing your forehead whilst whispering a quick thank you.

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