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Being Dylan OBriens Assistant
Chapter 11
Lunch was good. Quiet and peaceful. I let Dylan and Tyler spend time together and to work out their issues. We had Chinese takeout for dinner. After cleaning up, I decided it was time for me to go to bed. I said goodnight to Tyler and told Dylan I'd see him when he came to bed.
A little while later, I heard Dylan and Tyler coming down the hallway. I heard Tyler say, "Dylan, I can't thank you enough for what you and Jason have done for me today. It means a lot to me. I know I would have been in a bad place if I had been left alone today."
"It's ok, Tyler. It was the least we could do. We both know you were struggling and we did what we could to help you. Just know that we're here for you anytime you need us. Even if you don't think you do."
I heard them hug and then the door to the guest room close. My door opened and closed soon after. "Are already asleep?" Dylan asked.
"No. I don't think I would have until you had come to bed," I replied.
"You're so cheesy sometimes," he said. "But don't you EVER stop. I love it. I'm going to brush and then I'll come to bed."
I heard him use the toilet, then wash his hands and brush his teeth. After shutting off the light he came out of the bathroom and made his way to his side of the bed. I expected him to go to his bag and get out shorts and a t-shirt to sleep in, but instead, he faced away from me and stripped to his boxers, then got into bed. He turned towards me and smiled. "I hope this is ok. I feel comfortable enough with you to be this naked with you in bed."
"I'm comfortable as long as you are, Dylan."
He reached out under the covers and found my arm. He started rubbing it and leaned in for a kiss. "You should take your shirt and shorts off," he said after pulling away from the sweet kiss.
I watched his eyes for a moment. Trying to read his expression. I don't know what I saw, but I quickly agreed and removed the garments. After discarding them off the side of the bed and laying back down I rolled onto my side to face the man I was falling deeply in love with. "Are you sure this is what you want?" I asked.
"I don't know what exactly I want, yet. But I know that I need to be closer to you. And if that just means being held by you without all those clothes, then that's what I want." He leaned in and kissed me again. It was a little deeper than the last one and he moved closer to me.
I reached out and pulled him closer so that we were bare chest to bare chest. The touch of his skin next to mine was amazing. Where he was very cleanly shaved and smooth, I had a chest and belly full of slightly cropped chest and belly hair. The contrasting feel of the two meshed together and I was instantly hard. I know he felt it, because he pushed his pelvis towards me and I could feel his larger hardness line up along side mine. I panicked and pulled my pelvis back enough to break the contact. He followed me. I ended up rolling onto my back. Again, he followed. He was now on top of me pressing his groin into mine like a horny dog trying to hump a stranger's leg.
I turned my head to break the kiss. He moved to the exposed flesh of my neck. "Dylan..." I panted. "Dylan, stop."
It took almost a full 10 seconds for it to register with him what I had said. He stopped his thrusts and pushed himself up onto his arms. Looking me in the eye, "What? What did I do wrong? This is my..."
"Stop!" I said a little more forcefully. I put my hand to his cheek and rubbed my thumb along his cheekbone. "You did nothing wrong. I just needed to make sure that you're really ready for this. I don't know if I will be able to control myself after we get started. And we have a guest in the apartment."
"Oh...shit. I hadn't even thought about it. I just wanted to be with you in any way I could. I'm sorry."
"There is nothing for you to be sorry for, sweet baby boy. Nothing at all. I just don't want to do something that you're going to regret. Like you were going to say, this is the first time you've been with a guy. I don't want to just jump into it, if you're not ready."
He kissed me. "Thank you, Jason. I was starting to get carried away and wasn't sure where it was going to go. I don't know what I'm doing and I don't want to do anything wrong. I should be taking your lead on this."
"Let's just slow down a little and resume kissing. With the understanding that if either of us say it's time to stop, we stop and there are no hard feelings. Deal?"
"Deal." With that, he resumed kissing me and we were quickly back to where we were before, but without the grinding. My hands were roaming over his back and tracing muscles and his spine. I got lost in the sensation of his smooth, slightly damp skin and my hands slid down over his boxer covered ass. He moaned into my mouth and an involuntary thrust into my groin got us going in that department again. I didn't stop it this time. We had a deal and if either of us thought we had gone too far, we would stop.
We were both thrusting into each other and I was so intoxicated in him that I was getting very close to the point of no return, very quickly. I decided I didn't want this to end yet. So I rolled us over so that he was now on the bottom and I pulled away from his mouth. Trailing kisses across his jaw and decided I was going to attack the spot I had found the other day. I found it and Dylan gasped, loudly, and ground his hardness into my stomach. I could feel that his boxers were wet with his precum. I then breathed in through my nose and I could smell him. It was the most incredible smell I'd ever smelled. I felt my cock twitch at the realization that I was smelling Dylan in a very intimate way and it was all for me. Because of me.
I moved down his neck and moved across the base of it until I was on the other side and found the same trigger spot there. Again, he gasped and ground his cock into my stomach. I kissed my way down to Dylan's chest and moved to his left nipple. Sucking it gently and tongueing it to get it to rise to attention. I then moved to his right and did the same thing. Dylan's breathing hitched and he moaned when my fingers starting pinching his erect left nipple while I was paying oral attention to his right.
I knew I was teasing him, but I was almost ready to finish. So, I prolonged the torture for only a couple of minutes, then kissed my way back up to my man's mouth. Kissing each other deeply, I rolled us back into our previous position and Dylan started thrusting into me almost immediately. I knew I was close again and it seemed like he was too.
My hands found their way to his plump round ass and I squeezed them. I wanted to feel them, skin to skin, so I slid my hands under the waistband of the loose fitting boxers and placed a hand on each of his glorious mounds. He moaned into my mouth and pushed back into my hands slightly. Letting me know he approved of the contact.
I was really enjoying the texture and then my fingers started moving towards the sweaty crack of his ass. It was incredibly warm there. Dylan was now rolling his hips, I finally realized he was attempting to direct my fingers deeper into his crevice. I took the hint and dived in from both sides. I instantly made contact with his hole and Dylan lost it. He pulled away from me, arching his back and slamming his hardness into my groin. I felt his dick pulsing as it erupted into his boxers.
I could feel the heat and wetness of his orgasm soaking through both pairs of boxers and his breathing was ragged. I pressed on his hole a little harder with one finger and it slipped in on one of the contractions. Being inside of Dylan made me lose it. I pressed my cock into his groin and had the most amazing orgasm of my life.
I rode out the remainder of my orgasm as Dylan laid his full weight on top of me and as I slowly came down from my pleasure high, I pulled my hands from his boxers and ran my fingers through his hair. He turned to me and kissed me. When he pulled back he was smiling.
"That was amazing," he said.
I nodded my agreement. "Yes it was. I'm sorry I got a little carried away back there."
"WHAT?? That was the best part. When you pressed your finger into me, I think I came again. It was intense."
"As long as I didn't hurt you or cross any boundaries, then I'll let my guilt go," I replied.
"You did nothing wrong. Can we shower together?" He asked.
I nodded. He rolled off of me and towards the edge of the bed. After he stood, his knees buckled slightly and I reached to catch him, but he caught himself and stood still for a minute. Making sure he was steady. He then started walking towards the bathroom and pulling his boxers off and mopping the cooling cum from his torso.
I watched his cute ass walk away from me and I smiled. He was absolutely amazing...
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This is my second attempt at fictional writing, please let me know what you think of it by emailing me redmondgayguy at yahoo dot com.