Tyler My Brother and Me

"I don't think I'll ever get tired of this."

I was in Tyler's car in the parking lot one morning before school giving him a blow job when he made the statement. I had arrived at school like normal with Will then after we walked inside and he had gone toward his first class, I went back out to the parking lot to meet Tyler at his car.

I looked up at Tyler and gave him a smile around his cock. After the first time he fucked my face, I had accepted my role as his personal cock sucker. Even though I was surprised by the ferocity of the act, in hindsight it had been one of the hottest encounters I had ever had. Around other people he still treated me with indifference but now when we were alone he was not as offensive as he initially was. There was still no question what purpose I served in his life, but he treated me with a little more respect.

"I wish everyone sucked dick as good as you," he said as he began to gently thrust up into my mouth. "But I guess it just makes this that much more special."

He began to control my head with his hands as he neared orgasm. When he came, he held my head down on his cock but not far enough to choke me. I had gotten better at getting some of his length into my throat but in this position the upward curve of his dick didn't facilitate deep throating.

I swallowed quickly and milked his dick empty once the bulk of his orgasm passed. After mouthing him for a few more moments to make sure he was clean and truly dry, I pulled off and he pulled up his shorts.

As we walked toward the building, he said, "One of these days, I'm coming after that ass."

I nearly tripped over my feet hearing that. "What?"

Tyler smirked down at me. "You've got a hot little ass, Walt. I can appreciate an ass like that. Might be nice to hit that once to see what it's like. But knowing what your mouth is like, I expect it to be pretty good."

My mind reeled and I didn't know how to respond to that. Without being consciously aware that I was going to say it, what came out was, "I've never had sex."

Tyler actually stopped and stared at me. "You suck dick like that and have never had sex?"

I nodded my response.

"Fuck." He resumed walking and said solemnly, "I'm gonna pop that cherry, bro."

"I don't know," I said hesitantly even though it wasn't a question. I had often thought about having sex but I knew Tyler could not be my first. Both because of the size of his dick and the rough way he liked to use it I couldn't imagine him going easy on me my first time. There was also the fact that Will might find out. I couldn't imagine the hell I would catch if my brother found out that Tyler fucked me, that he had been my first, never mind that I had been regularly sucking him off.

"You'll think about it," he said as he turned down a hall to go to his class.

Despite my reservations, I did think about it. Almost constantly. My morning was filled with thoughts of Tyler fucking me. I still thought it was a bad idea but I began to think he might be the perfect guy to do it. He was a friend and there would be no doubt as to our relationship. It would be a fuck and nothing more. I wouldn't have to worry about the awkwardness that might happen afterward.

When I arrived to the history class we shared, it was obvious Tyler had been thinking about it as well. As he sat at his desk, he turned to talk to James but his hand pulled at the hard ridge concealed within his shorts. While he was no stranger to grabbing himself in public, I knew this was for my benefit.

As class started I saw him pull out his phone, keeping it hidden from our teacher, and type a text. I was surprised when I felt my phone buzz in my pocket.

-You think about giving me that ass?

-A little

-So?

-Maybe

-Save us both time and just say yes. You know it's going to happen.

I sighed. Again, Tyler was right. I might not give in today or tomorrow, but eventually he would wear me down. It didn't mean that I was just going to let him fuck me, but I could see the truth in his statement that at some point I would.

For the rest of class, I couldn't pay attention to the lesson. My focus lay a few seats across the room, spying on Tyler slouched in his seat still fondling himself. When class ended, he glanced at me and grabbed himself with a smirk before walking out of the room.

Despite his confidence that I would have sex with him, he didn't mention it again the next time we hooked up. And when a few more encounters passed without us discussing it, I put it out of my mind.

It wasn't until weeks later that he brought it up again.

He was at our house hanging out with Will and was going to be staying the night. While it wasn't frequent, it wasn't uncommon for one of them to stay the night with each other. They often did it nights after soccer games and during the summer sometimes two or three days would go by with Tyler in our house or Will at his.

Will had gone to shower leaving me alone in our room with Tyler. We were playing a video game and he didn't turn to me when he said, "You know I'm going to fuck you soon, right?"

I sighed in resignation. "Yeah."

"Don't. You know you want my dick in your ass just like you wanted to suck it. After I fuck a load or two into it you'll be begging for it."

Typical Tyler. The kid was cocky and sure of himself and I had to admit to myself that it was one of the reasons I liked him. From the first time he had talked me into sucking his dick, as much as I tried to fight it, I was under his spell and he had known it.

"Fuck," he said after a few moments of silence. He reached down and squeezed his growing erection. It was just getting to the point where it was tenting his basketball shorts. "I could really go for some head."

We heard the shower go off across the hall and Tyler did his best to adjust his cock so it wasn't so prominent.

When Will returned to the room, Tyler and I were still playing the game. He gave us an appraising look that for some reason made me feel guilty. Even though I hadn't done anything in the short time he was gone, it was as if he knew what we had been discussing and saw through our facade.

Wanting to escape his scrutiny, I put down my controller and said, "I'm going to shower."

"Sleep on the couch tonight," Will ordered.

Part of me had expected that. It was rare that I slept in the room with them when Tyler spent the night. Tyler always took my bed and, if I did sleep in the room it was on the floor. Occasionally, our younger sister chose to sleep at a friend's house so I could stay in her bedroom but she was home that night which meant I would be on the sofa.

After my shower, I returned to the bedroom and played a few more rounds with them before I was kicked out for the night.

I awoke to something pressing against my lips. Reflexively, my mouth opened and I felt something with a spongy firmness enter it. It took a moment for me to fully regain consciousness and open my eyes. By that point, the item in my mouth was harder and I saw that Tyler was leaning over me with his hands resting on the back of the sofa, gently fucking my mouth with his cock sticking out the fly of his cotton sleep shorts.

"Be cool," he said softly when he realized I was awake.

With nothing else to do, I moved a hand up the leg of his shorts and began to fondle his balls. Tyler sighed contentedly and began to thrust with more determination. It didn't take him long to grunt and pump his load of teen ball juice into my mouth and I swallowed it with ease. After using a hand to milk his shaft dry, he pulled out and left me alone without another word. Dawn was creeping around the curtains but I quickly fell back asleep with his taste lingering in my mouth.

The next night, Tyler stayed over again. Simply from being around him all day, I was a bundle of horny nerves and when he again woke me during the night by pushing his cock into my mouth, I woke almost immediately. Without any hesitation I reach my hand into my own shorts and stroked out a load while he filled my mouth.

As I milked his cum hose dry into my mouth, he said softly, "I can't wait to fuck you. It's going to be so hot seeing how quiet you can be with everyone sleeping and not knowing what's happening. I could probably fuck you in your bed and Will would never know."

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.