Chapter 3: Bedtime
After such a hot night, I was horny as hell going to bed. I was sharing Myles's full-sized bed with him and Grayson, all three of us under his covers warming up from having just been nearly naked. Myles was wearing a shirt that was a bit too small for him and blue fluffy pajama pants. Grayson, very surprisingly for how shy he could be sometimes, was still in his small red boxer briefs without a shirt or pants. To put it lightly, I was not complaining about being squished in the middle between the two cuties.
I took a deep breath, thinking about how far I was willing to go with the two so close, neither of them being aware of how horny I would get during the night. Grayson was straight, or at least he said he was, so I told myself not to touch him, in the back of my mind I knew I would break that promise. Myles was bi and there were hints he knew what I was thinking the whole night, so I decided I would see what would happen with him. For all I knew, if anyone noticed me doing anything sexual they would be grossed out and kick me out. Worst case I would be called a creep and they would hate me forever, but the secrecy and slumber were what turned me on.
I estimated both of them were just 2 or 3 inches away from me, all three of us lying flat on our backs. I couldn't reposition myself without making contact with them. I started drifting to sleep, but couldn't fall asleep with my thoughts racing. My cock was only semi-hard at that point. I built up confidence and turned myself towards Grayson to get more comfortable, brushing my ass against Myles, and my arm was now touching Grayson's arm. We remained in contact until I heard Myles snoring softly behind me.
Myles turned away from me, our asses were now touching. I started nearly cuddling Grayson's arm, unsure if he was sleeping yet or not I wanted to be careful not to be too obvious. My dick got harder. I made very slow and careful moves scooting closer to Grayson, my body now an inch away from his body. Half an inch. I moved closer until we were touching. I could feel Grayson's warm body touching mine, his shirtless body soft against my own. I laid like this for a while, too nervous to go further with him. Myles behind me turned to face my back, nearly in a spooning position. Although he wasn't touching me, I could feel his heat radiating behind me. He must be so close. My cock was now fully hard.
The pressure of my cock was almost painful and I needed to adjust it. I carefully removed my hand from hugging Grayson's arm and slowly crept it into my pants. I maneuvered my cock through the hole in my soft underwear, freeing it from the pressure and letting it loose in my sweatpants all while my chest was touching Grayson's side. My fingers were wet and sticky from my precum. I was too nervous to return my hand to Grayson so I kept it at my side. Instead, I slowly moved back and made contact with Myles' entire body, just for a second until I got scared and moved away a half inch.
Myles, still snoring, moved closer to touch his body against mine ever so slightly. I'm sure it was unintentional, but his pressure moved me closer to Grayson, the much larger tent in my sweatpants almost touching his underwear. I carefully moved myself to avoid poking his side. This went on for a while until I heard very soft snores from Grayson, the two boys now snoring beside me. My eyes remained closed as I was essentially half asleep.
At some point, Myles readjusted once again, waking me up slightly. He had turned around again pushing his back and ass into my backside even more, and suddenly my arm was uncomfortable and I needed to move it. The only comfortable spot would be across Grayson's bare chest under the covers unless I readjusted my whole body, which I didn't want to do since facing Grayson was so hot. My half-asleep impulse brain did just that, lying my arm across his chest extremely carefully and slowly, now basically embracing my cute crush. This got me hard again which I couldn't avoid colliding with Grayson's side.
My dick got harder. The tip of my cock through my sweatpants was now very softly contacting the side of Grayson's underwear. I was nearly throbbing from how hot this position was, Grayson thankfully remaining asleep from what I could tell.
I dozed off again until there was movement from Grayson. He turned around facing away from me, my arm still over his body I was now inches from spooning him. My mind said fuck it. I scooted closer until I was, my entire chest making contact with his back. I stuck my ass backward to not let my growing erection collide with Grayson's ass. However, I then noticed Myles was facing me again and with my maneuver, my ass hit his hard cock. His member was poking my asscheek and there was nothing I could do about it being squished between the two, though of course, I wasn't complaining.
I didn't fall back asleep as the gravity of what was happening clouded my mind. I was literally spooning Grayson, my arm around him and my hand resting in front of his abs. Myles's cock was poking my ass, and if I wasn't careful mine would poke Grayson's ass. I opened one eye and noticed Grayson had room in front of him to make more space, but as he was sleeping that didn't happen. I was sandwiched between the 17 and 15-year-old in the darkness of the night. It couldn't get better than this.
Suddenly, Myles moved closer to me, now unintentionally touching me somewhere other than his member. Myles' chest was against my back, and now I was truly sandwiched. Myles then moved his arm across me, still snoring, to sort of spoon me. We were now three spoons in a bed. I pulled Grayson closer to me very gently so as not to disturb his slumber. Myles shortly after did the same, now pressed against me. His cock, still hard, was between my asscheeks now. My cock was throbbing and quite wet at the tip. Myles' cock felt very large through his thin pajamas and I was forced to move closer towards Grayson to relieve some of the pressure it was exerting onto my hole. This resulted in my cock fitting gently but snugly between Grayson's asscheeks, the only thing stopping me from technically fucking him were the layers of my sweatpants and his boxer briefs. How was this happening? It was my dream come true.
Myles and Grayson were thankfully still snoring, unbelievably still asleep, but I was wide awake. I couldn't resist and eventually built up the confidence to feel Grayson's smooth warm hairless body with my hand. His heart felt like it was beating at a normal pace, a good sign he wasn't waking up. His nipples were hard, and his breathing was normal. My cock continued throbbing, each time exerting pressure presumably onto Grayson's clothed hole. I embraced Grayson again, feeling myself close to cumming from how hot this was. Myles being pressed against me behind me in addition to me feeling Grayson was just unbelievable for my dick.
I thought this would be it until it wasn't. Myles stopped snoring and came even closer to me, his head touching my neck. Suddenly, he whispered, barely audible, his warm breath against my ear.
"Do it." I stayed extremely still, unsure if I was imagining it. A moment passed as I laid there frozen, not moving a muscle, the throbbing of my cock paused. I felt goosebumps on my neck. He whispered again.
"Touch him." In addition, Myles moved his arm firmly around my body, enveloping my body in his arms. Myles was awake. My heart raced. I knew Myles was bi, but he was snoring, he must have either been faking it or he was half asleep. I could still feel Myles' bulge gently sitting between my ass cheeks. I was in disbelief.
My heart and mind raced, deciding what the next move was. I was so nervous until the horniness and feeling from my once-again throbbing dick took over. I slowly and carefully started feeling Grayson's chest again, his soft nipples, and his slow heartbeat. His chest was rising up and down with each soft breath. I moved my hand lower and lower, cupping his skinny belly in my hand. It was so smooth. I inched lower, barely above the waistband of his tight boxer briefs. Myles squeezed me from behind and pressed his cock slightly harder into me, which forced mine slightly harder into Grayson. If Myles kept going, I was worried it would wake Grayson up, who may I remind you claimed to be straight- it would ruin everything.
Despite my nervousness, knowing Myles was awake made me feel better and gave me confidence. I wasn't the only one "in the wrong," I convinced myself Myles would have my back if Grayson found out and didn't like what was going on. This gave me the confidence to keep going, giving into my desires. I lowered my fingers towards Grayson's waistband, slipping underneath so just my fingertips were under the elastic. I inched it lower and lower, holding my breath for silence. Myles squeezed me softly as if to say keep going. I felt the start of Grayson's pubes, soft and thin to the touch. I kept going with just my fingers lower until the base of his cock, which unbelievably was hard as a rock.
I sandwiched it between my two fingers and tried stroking, but with the position we were in was quite difficult. I could only get a quarter inch of movement. Still, his cock was smooth, warm, and very hard. I couldn't believe this was happening. I checked if he was still asleep and he was. I moved my entire hand into his underwear and wrapped my hand softly around his shaft. My dick was now throbbing so hard into Grayson, and I could feel Myles was throbbing behind me. Myles had started humping me slightly, rubbing his bulge on my ass.
Grayson's hard cock was fairly small. It nearly fit fully into my hand, probably around 4 inches and thin. It was uncut, soft, and hot to the touch- we were, after all, still under the warm covers. I gave it a soft squeeze and it responded with a throb, almost asking to be pleasured. Grayson may have been sleeping, but his dick was wide awake. I tightened my grip and started stroking him, very careful to make small and slow movements so as not to disturb his slumber. Myles noticed I was stroking him and was now full-on grinding into me, causing me to rub my bulge on Grayson's ass.
I stroked Grayson for about a minute. This was so hot to Myles and me that Myles was now grinding hard into me, so much that I had to stop in fear of waking Grayson. I gave his dick one last soft squeeze and removed my hand from his undies. I pushed my dick away from Grayson's ass, pressing myself into Myles's dick to hopefully send him the message to pause. I didn't feel quite done with Grayson though- I placed my hand on his underwear atop his bulge to feel the outline, moving my hand up and down a few times to really feel it. I moved my hand to his soft belly, up his tight chest to his hard nipples, his heartbeat higher than usual but his breathing calm suggesting he hadn't awoken through my pleasuring.
I embraced him one last time and removed my contact from him, nearly leaning fully against Myles who was still embracing me. I carefully adjusted myself to turn around and face Myles, my back resting against Grayson's back. In the faint light, I saw his eyes looking into mine, sharing the same look of thirst and horniness that I had. While I debated what to do next, Myles leaned over and quietly and deeply kissed me. This was only my second kiss so I let him take control, and we silently made out in the night with Grayson snoring softly behind me. Just then, I knew this night was going to get even better.