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“All ready for me, Hughie?” you ask him, reaching over and placing the small bottle of lube in your hands down on the nightstand. “Yea- uhh, yeah.” he responds with a small nod. You laugh softly and lean in to kiss his shoulder, before reassuring him, “No need to be nervous, babe. I know this is new for you, but I’m gonna be careful. ‘Gonna take good care of you.”
“Wanna face me instead? Missionary? Would that calm your nerves a little?” you question, smiling at him even though he can’t see. “Uhhmmm.... ahhh... I don’t know. Yeah, let me face you. I don’t know if it’ll calm my nerves, but uhhh... yeah. Let me face you.” you laugh a little again after he speaks before he turns himself over, looking up at you with a wary expression.
“Hey, we don’t have to try this if you don’t want to. That’s fine. Or we could try another time whatever you want.” you tell him as he places a hand on one of your cheeks. “No, no, I wanna try this. I really do. How- how about you just do it so I don’t have time to be nervous about it?” he cracks a smile as he says that, which makes you smile back at him. You lean in to give him a quick peck on the lips before nodding, “Alright. Sure.”
Your eyes rake down over his body, his torso still covered in a snug Billy Joel t-shirt, before you focus on positioning the dildo on the strap you’re wearing at his entrance. “Just tell me if you want me to stop, okay? I love you.” you press one more kiss to his lips before bringing your hands to his, lacing your fingers together and pushing the dildo inside of him.
You watch intently as his jaw drops and his mouth opens, a small gasp escaping from him that makes your lips curl into a smile again. “You okay?” you ask, to which he frantically responds, “Oh, yeah, god, just keep going,” and of course you oblige him. You squeeze his hands slightly as you push into him more, up till the dildo is in him fully. You pause, keeping your hips steady as you can see him trying to keep his composure.
“Is this good for you, Hughie?” “Oh, god, more than. More than good.” his reply comes out breathlessly, and you can’t help the tiny laugh that comes from your nose. “Yeah? Yeah?” you question teasingly, pulling your hips back just the smallest bit and pushing back into him to drive it home. He moans at the movement, the sound barely passing through his throat, but it’s there. It has your pupils widening in admiration.
“Sorry, baby, sorry. I couldn’t resist.” you apologize, watching as he swallows hard and shakes his head. “No, don’t apologize, just... fuck!” when he swears at the end of his sentence it comes out as a laugh- it sounds almost like he’s stunned by the feeling. “Keep moving. Just keep moving.” he encourages.
You can never resist him when he’s so sweet. And he looks all the sweeter under you like this. You give an experimental roll of your hips, one that makes his brows furrow and a heavy pant escape him. He looks... so pretty like that. You just have to see it again. So you do the same action, rolling your hips against him and watching as his head pushes into the pillow behind him slightly and the breath he lets out turns into a quiet “fuck.”
You start a rhythm as you thrust into him, and although a slow one, you can feel him desperately pressing his ass into your hips in an attempt to get the dildo to fill as much of him as possible. You lean in to kiss him, and it isn’t long before he’s moaning against your lips, the vibrations against you making your heart flutter.
After a while, you speed up just enough to make his hips jerk up to meet your thrusts, and you pull away to look at him, his eyes shut tight and his neck straining while he moans your name sweetly. Reluctantly, you slip your hands out of his and use them to hold him down onto the mattress, allowing you to keep him still as you fuck him. You swear you hear him whimper when you do that- and then, he makes the same sound the next time you push back into him, and you’re sure that’s what you heard.
A small blush spreads across his cheeks and his nose and his eyes widen when he realizes the sound he just made, but you just bite your grinning lip, not teasing him or saying anything about it. You can see him relax when you say nothing, his eyelids falling back to normal, but the pink tint on his skin doesn’t disappear. Much to your pleasure.
Within minutes, his moans have gotten more frequent and they’ve gotten louder. His long fingers dig into your upper arms, and you don’t think he’s aware of how hard he’s grasping at you, but you don’t care. You wouldn’t dare to ask him to ease up or stop when you have him like this- the thought doesn’t even cross your mind. “Are you close?” you ask him, although you’re fairly certain you know the answer from how he’s struggling to keep his breathing steady underneath you.
“Yeah, ahh, yeah-” he cuts himself off with a broken cry when you snap your hips into his ass, the dildo hitting somewhere inside of him that causes him to react like that. You apologize by kissing him deeply, and he presses his lips back into yours almost feverishly. When you pull away, you see him close his eyes and try to focus on getting to his peak.
You get an idea to help him out. One of your hands moves away from his hip and grasps his dick, making a fist around it and using the pad of your thumb to take the dribble of pre-cum dripping out of him and rub it over his dick. With that, you start to jerk him off, and you watch his eyes jolt open, his pupils blown and his chest starting to rise and fall fast. He moans your name again, sounding almost pained.
“C’mon, Hughie, baby, cum for me. Can you cum for me?” you question him, and you watch as his lips press together and he nods fast. You pump him in your fist quicker, and before you know it, he’s gasping for air as he finishes, cum seeping out of his dick and spilling onto his Billy Joel shirt. You would move the fabric out of the way so he can cum on his chest and not leave stains, but it’s too late now. You just watch the way his face contorts and listen to the sounds he makes.
You keep fucking him through it, making sure his orgasm lasts as long as possible before you slow your hips down, nearly to a halt, but your hips still roll into his ass slightly. Once he’s fully come down from it, you pull the dildo out of him, rolling onto the bed next to him to take it off and place it on the nightstand beside you. You look at him with a loving look in your eyes, and he almost feels embarrassed when he turns to look at you and is under your gaze.
It’s silent for quite some time before you say anything. “Do you want me to throw your shirt in the washer? I can spray it with some stuff before I put it in. Hopefully it’ll help and there won’t be a stain.” you offer, nodding down to his stomach. He glances down at it before nodding, “Oh, yeah. That’d be really nice of you, thanks.”
He sits up a bit so he can pull his shirt off of his head, handing it to you. You take it and ball it up in your hand, before leaning over him and kissing him quickly. “See, that wasn’t so bad.” you say with a smile. “God, you’re right. You’re right. It wasn’t bad at all.” he replies, nodding at you once again.
“Let’s try doggy style next. If you think you can handle it.” you suggest with a slightly teasing tone, kissing him once more before lifting yourself off the bed and leaving the room, heading off to find some stain spray.