Harry : Pleasuring him

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He pushed open the door to his room quietly before leading me into the comfort of his small bedroom. I was already familiar with the room and the indie band posters that littered the wall and ceiling with lyrics from his favorite songs written across the walls. A few shirts and a pair of jeans lay on the floor in front of his bed and he kicked them under as he led me to his king sized mattress by my hand. His grip was tight and a little sweaty, probably from the nerves I thought. I felt tiny butterflies in the pit of my stomach as I sat next to him on the bed. He still held my hand tightly in his and a moment of silence passed before he said, “Are you sure you want to do this? Like absolutely positive? Because you know you don’t have to if you don’t want to and I can wait-“ I cut him off before he could finish.

“Yes,” I said. “I’m positive. I just, I uhm, you know don’t want to do it wrong though…since it’s my first time giving one and you’ve had them from girls that can do it better than me, I just want to make it good for you” I said shyly, my head was turned down to the floor so I could avoid eye contact with him.

“Don’t be nervous, baby. I’ll walk you through it okay? You don’t ever have to feel shy around me you know that. Look at me baby. Let me see those eyes.”

And with that his index finger tapped my chin lightly and tilted my head towards him.

“You’re beautiful and perfect and I’ll enjoy this no matter what babygirl, okay? Don’t be nervous it’s just me. It’s just Harry” he cooed at me, stroking my hair and soothing my nerves and butterflies.

I exhaled heavily at that and then said okay. With renewed confidence from him I looked deeply into his hazel eyes and leaned further into the strong hand he had placed on my cheek, cupping my jaw. I saw him nervously gulp before he leaned forward and placed a warm, electrifying kiss on my lips. He slowly moved his lips against mine before moving his hand to my lower back and pulling me on top of his lap. Feeling frisky from the new position I opened my mouth a little and he took the opportunity to deepen the kiss, making the butterflies return. Our tongues slowly moved against each other’s, feeling each other, tasting each other in a way that felt so familiar yet new and erotic. After making out for about five minutes I finally whispered against his lips, “I’m ready now.”

He pulled his head back and looked at me with obvious concern in his brow and before he could say anything about how he could wait until I was ready I nodded my head at him and removed my body from his lap and lowered myself onto my knees in front of him. He stoked my hair lovingly as he undid his belt buckle, pulling it from his jeans and placing it on his pillow. He undid the button….then the zipper and slowly pulled his jeans down his legs. I helped him get them off his feet and threw them next to his belt. I kept eye contact with him in fear of staring at the large bulge in his boxers. “It’s okay baby. I’ll show you what to do.”

I gulped and then slowly my eyes traveled south until they saw the large bulge shape in his tight black boxers. His large hand moved over my small one and he grabbed my hand and the placed it on the bulge. I pressed down lightly and a gasp came from his mouth, then a small moan.

“Move your hand back and forth okay, that feels good.”

So I did as I was told. I slowly moved my hand over the bulge in his boxers feeling him harden a little bit more until he could no longer take it.

“I-I’m gonna take my boxer’s off now, okay” he stuttered.

“Yeah, okay” I said in a small voice.

Slowly he tugged his boxers down with my help and I couldn’t help but gasp inwardly as his length appeared to me for the first time. He stroked my cheek and I gathered enough courage within myself to take him into my hand. It was the weirdest feeling ever. He was thick, long, and hard. Intimidating. But he was also soft, so, so soft and the tip of him was a glistening pink. I saw a small bead of moisture form at his slit and I looked up at him for guidance.

“U-use your thumb,” he struggled to say as I stroked him up and down slowly, “and, uh, use it to rub it around to make it wet so it’s e-easier to, uh, slide your hand.”

I smiled a little bit as I stared up at him, in this state. His lips were puffy, swollen and red which made me want to attack his lips but I knew I had other things that needed my lips more. So I moved the bead of moisture around his length and continued to stoke him until I poked my tongue out from my mouth and hesitantly licked his tip. He gasped and then threw his head back as sweat collected on his forehead beneath his curls.

“Y-yes, yes. That feels good baby. Just like that” he praised. 

I continued to lick at him like a lolly just like he told me beforehand and the taste of him was like nothing I could describe. Salty, yet surprisingly sweet and musky like the man that he is.

“Can you put the tip in your mouth, babygirl? Just suck it like a lolly, remember. You don’t need to put it all the way in since it’s your first time, o-okay? Just, ah, the tip and uh, use your hands for the rest.”

His instructions gave me confidence I needed and I took the tip of him in my mouth and continued to stoke the rest of him. I had to use two hands since his manhood was so thick and long one hand just wouldn’t do it. I tried to take him farther even though he told me not to so I started bobbing my head on him and his moans…oh God his moans were something I could only dream of in my dirtiest fantasies. The way he vocalized how good I was making him feel made it all the better for me. All of his, “oh god baby’s”, “oh yes, fuck’s” were engraved into my brain and when I felt him twitch in my mouth, I immediately pulled off him and just continued to work my hands up and down his length as fast as I could, ignoring the wet sound it made. His muscles tensed and he threw his head back gripping the bed sheets and crumpling them in his large hands as white strings of cum came out of the tip of his manhood. I stroked him through his orgasm until his muscles relaxed and he opened his eyes looking at me with admiration. He grabbed a tissue from his bedside table and cleaned his mess off my hands and a spot off of his jeans before he tugged his boxers back on.

“W-was it okay”, I hesitantly asked.

My confidence no longer appearing as I looked at his carpet again. Instead of answering me with comforting words, he grabbed the sides of my face and planted a warm, wet kiss to my slightly pouted lips. When he pulled off me, again without answering with words he pulled me onto his lap and we laid down on his bed, with his arms around my shoulder and a hand in my hair stroking a few frizzy strands down. A moment of silence passed before he said, “that was fucking amazing.” I giggled in response and immediately felt reassured and semi-confident.

“You are so good at that, fuck I can’t believe I even lasted that long!”

Now with that comment my cheeks turned a shade of red and I hid my face in his shoulder. He chuckled and kissed the side of my head before saying, “Don’t you ever worry about those other girls, or not being good enough because that was perfect baby and you did so good. I love you.”

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