It was true. Will was a heavy sleeper and was difficult to intentionally wake. When I was eight, I had fallen down the stairs in the middle of the night going to get some water. Even with my screaming in pain and a visit from an ambulance, it wasn't until I got back home from the emergency room with our father the next morning that Will found out what had happened.
Two weeks after Tyler spent the night, my life took a very unexpected turn.
He had come over again to stay the night. The three of us, along with my parents and sister, were watching a movie in the living room. Somehow I ended up sitting on the floor next to Tyler while Will draped himself over an armchair and our parents cuddled—embarrassingly—on the sofa.
Halfway through the movie, Tyler barely leaned toward me and whispered, "I'm going to fuck you tonight."
"What's wrong?" my mother asked hearing me gasp.
"Nothing," I said quickly. I began to bend one of my legs at the knee and shift around on the floor. "My leg fell asleep."
She seemed to accept that explanation but when I glanced at Will, he had a doubtful look on his face. For the rest of the movie, I sat uncomfortably next to Tyler. It felt like with each passing scene I was creeping closer to my doom, yet I was excited by it. Since he had first brought up the subject months ago, I had been thinking and fantasizing about getting fucked by him. As he had said, I would give in and, now that he had determined when it was going to happen, I couldn't wait. Making matters worse, once he said he was going to fuck me, my dick hardened and I could not find a position that would make it comfortable while not revealing it.
After the movie finished, everyone separated to make preparations for bed. While Will showered, I ended up in the bedroom alone with Tyler.
"I haven't nutted in two days waiting for this." Tyler had walked up behind me while I gathered clothes from my dresser and was gently grinding his crotch against me. Because of our difference in height, his balls and cock pressed against the small of my back, a few inches above the top of my ass. "When you go downstairs, make sure you take a pillow with you. You're going to need it."
He pulled away hearing my sister approaching in the hall. When Will left the bathroom a few minutes later, I left the room vibrating. It was a mix of pleasant anticipation and fear of the unknown. I knew it was going to hurt, being my first time. But at the same time, I was as ready as I could be to do something I didn't quite know how to prepare for. In the shower I cleaned my ass as well as I could, figuring that would be a decent thing to do but otherwise was clueless as to what else I could do.
Once everyone was showered and after we had played a few rounds of a video game, I took my pillow and went to the couch to lay down and wait.
I awoke a few hours later to the sound of voices, surprised that I had fallen asleep. Tyler had gotten a call from his parents that his grandmother had been taken to the hospital. Even though his parents told him to stay with us, understandably Tyler was going to meet them at the emergency room. Once he was gone, I figured there was no reason for me to stay on the sofa so I went up to sleep in my bed. When I entered the bedroom, Will was snoring softly, completely unaware of what had happened. I laid on my bed and smiled softly smelling Tyler's scent lingering in my sheets and quickly fell back asleep.
It seemed like only minutes had passed when I was shaken awake. It wasn't the motion of someone gripping my shoulder, but the movement produced by my shorts being lowered. Lying on my stomach, I glanced over my shoulder and saw a dark shape on the bed behind me between my legs. Firm hands grabbed my ass cheeks and pulled them apart. I closed my eyes and hissed softly when a tongue touched my hole. Gentle at first, it gradually began to work harder against it. I could feel the slickness of spit coating my backside and wet, sucking sounds crackled through the quiet of the night.
Eventually I felt a finger push into my tight ring and I restrained a moan at the intrusion. I had fingered myself a few times but it didn't feel anything like this. There was a purpose and determination behind the movements that was arousing in its insistence. When a second finger breached me, I moaned into my pillow and reflexively tried to pull away. The hand that had been holding my cheeks open moved to grab my hip to hold me steady. I tried to relax as the fingers began to pull against my ring but couldn't. When a third finger entered me I let out a pained whimper that did nothing to stop the assault.
After a few minutes of the fingers moving through me, they were removed and I heard a large amount of spit get expelled. It was rubbed against my hole just before I felt the heat of something large and firm press against my entrance. Biting the pillow, I tried to keep my sounds as muted as possible while I was penetrated for the first time. After the thick crown was finally lodged inside me, I continued to pant into the pillow praying for the pain to subside and hoping that I was not making too much noise. In the quiet of the night, my sounds seemed like they could wake the neighbors and though Will was a heavy sleeper, I doubted that he could sleep through it. Our parents or sister would definitely be awakened by any excessive moaning fearing the worst.
I felt the scratch of pubic hair against my ass but it was short-lived as the cock in me was immediately pulled back. It was pulled out of my ass just as slowly as it had entered me. I registered a new, tugging pain when the flared crown tried to exit my hole. Once the cock left me completely, it was reinserted and pushed fully into me before being dragged all the way out again.
With silent tears streaming down my face into my pillow, I laid there as my ass was slowly fucked open. But even around the raw pain of penetration, I could feel the heat of arousal coursing through my body. There was something inside me being stimulated by the motion of the dick against it that I wanted to both explore and run from. It wasn't until many fucks later that I learned it was my prostate. Beneath me my dick was stubbornly soft but I could feel precum leaking out of me and soaking into the sheet from the constant stimulation. Objectively, I tried to think about how much better it would be next time.
It seemed like forever before the cock in my ass began to move faster as the thrusts became shorter. A heavy, solid body pressed down against my back and an arm wrapped around my neck. I could feel warm breaths pass across my neck and cheek and they seemed to increase in speed in tandem with the motion of the hips.
A soft grunt was all I got before the cock buried itself fully and stopped. A split second later, I could feel it pulse and throb inside me as a warmth spread through my body. I was still hurting but I marveled at the sensation. It was unlike anything I had felt before and I let out a soft moan. After a few seconds, the hips began to move again, shallowly fucking a now slick and slimy dick through my abused hole as it continued to empty into me. The cum helped to soothe my burning ring and just as it actually began to feel better, the softened piece of flesh was pulled out of me. I sighed with a mix of relief and sadness that it was gone but laid there motionless as I felt the bed shift and the body move away.
As I panted through my lingering tension and exhaustion, I vaguely registered Will's bed creak across the room. I turned my head and saw him roll onto his side. A part of me worried that he had seen what had happened but I rationalized he wouldn't have let it continue if he had.
Feeling horny yet satisfied, happy but sad, I slowly drifted back to sleep with a smile on my face.
I had just been fucked for the first time.
