Chapter 2
Thanksgiving break was much needed. I got to sleep in, relax, and catch up with my old friends. While I texted with the guys from college I focused mostly on my time away.
As I hung out with my old friends and fell back into old routines, the whole thing with Connor became a distant dream. I tried not to think about him. What I did keeping thinking about was my last words to him
"Take things slow"
What the FUCK was I thinking? It just slipped out in the heat of the moment. What did they even mean? That's something you say to a girl not to a dude. What were we supposed to take slow? Hooking up? Didn't my huge freak out prove that I wasn't cool with this? Saying that to him was a mistake.
I must have picked up my phone like 20 times over the course of a few days to text Connor and clarify. I just didn't know what to say.
I actually went out of my way to hook up with an old girlfriend. Afterwards, I did feel better. The sex was great, I still enjoyed it, and I felt more like a "man".
It was Friday night the week after Thanksgiving and I didn't feel like going out. I had enough of that in college so I figured I would just chill at home. My middle brother, Tyler who is 16, was having some friends over for the night. Having to deal with five 16 year old boys wasn't my idea of fun. So I would just do what I always did...ignore them.
I was a bit startled when I heard a knock on my door and it opened. Tyler walked in and stopped mid stride. We had this unspoken rule about entering each other's room since I walked in on him jerking off a year ago. At the time I couldn't help laugh and he turned the darkest shade of red I ever seen. His eyes darted around and then he relaxed as he saw I was just chilling.
He was wearing a bathing suit and said: "Hey...uhhh...sorry. You want to join us in the pool for some basketball? We need one more for 3 on 3."
"Sure dude. Never pass up a chance to school you boys." I went to grab my suit as he left.
I lived in California outside of San Francisco, so the weather was still good to swim. We put a small basketball net near the water, and "water b-ball" became a favorite of the house.
Downstairs the guys weren't in the pool yet. Standing their in their bathing suits they reminded me of my friends and I at that age. All in good shape, popular, good looking. I had lost my virginity at 15 so I figured some of the guys probably lost theirs as well.
The game started and I was on a team with Tyler and another kid. We were dominating since I was just bigger and stronger than they were.
One of the guys, a kid named Dylan, kept trying (and failing) to guard me. Once or twice I swore I felt a hand or something touch my dick but I couldn't be sure.
The next series, there was no doubt as I felt a hand grab my penis and let go. I quickly turned and stared down Dylan, only to see a sly grin emerge on Dylan's face. Was this some trick to get me to loose my concentration? Was it just an accident?
A minute or two later, he was boxing me out and I felt something hard brush my ass. This time I did loose concentration and he snatched the ball, kicked it out, and they scored. He looked over at me with pride and then blushed when he saw I was really giving him the eye.
Even with the aforementioned distraction, the boys were just no match for me and my brother. We were just too athletic and had played together often to have plays memorized. After the game, it was time to shower and change for dinner. I noticed Dylan look his time getting out of the pool and when he did get out, I thought he looked a little chubbed up.
As I was showering I couldn't help but think of Dylan. What was he playing at? And why now? He has been friends with my brother Tyler for a while now. He was a bit shorter than me with brown/reddish hair, brown eyes, and pretty developed chest and arms for a 16 year old...must work out regularly. While he definitely wasn't a boy, he wasn't a man either.
Downstairs when I saw the guys all changed and showered, I decided that he was just trying to fuck with me and threw a bone from all the body contact. All my brother's friends were little shits
After dinner, my parents turned in early. I was in a damn good mood after the pool victory and had a surprise for these guys. I had brought a few bottles of vodka home since it easier to get at school, so I offered them one. They looked at me like I was a super hero.
I made some mix drinks and we played video games and bullshitted about life.
"Zach, how are the college girls?" my brothers friend Josh asked
"Dude you have no idea. You have all these freshmen girls, and some are just going fucking nuts." I said.
"Haha. Speaking of nuts, how many girls you get your nuts off with?" Josh asked.
"That's for me to know and you not to find out." I shot back.
"Ohh come on dude. Tell us something." Josh begged. They all were staring at me intensely.
"Alright." I said and proceeded to tell them about the Asian girl encounter. I talked about how we met, her awesome body, her tight ass. They were in total rapture. I stopped without giving too many sexual details. While I was feeling like "the man" to a group of boys I didn't want to go too far. I heard a chorus of questions:
"So did you have sex with her?" "Was she a good lay?" "Was she tight"
"That's all dudes. I'm hitting the sack." I just laughed and went up stairs. I saw all of them adjusting themselves due to chubbing up, even Tyler my brother, which was a bit weird for me.
An hour later, I heard a knock on my door. I was laying in my boxer briefs on my bed watching a movie. Dylan walked in and shut the door.
"Dude everyone is calling it a night but I'm not tired. Wanted to see what you were doing." Dylan said.
"I'm about to turn in to man. I was just watching a movie." I said. Actually I was just about to jerk off, but thank god I hadn't started that yet. Last thing I need is to forget to lock the door and get walked in on.
"Can I, uhh, like watch it for a few minutes with you? I'm not tired at all." He pleaded.
He sat on the edge of my bed and watched the TV.
Sigh. "Fine man." I replied. But after 3 minutes I said:
"Dude, if you are going watch you can get more comfortable. Pull up that chair or something." I said.
"Thanks Zach." He stood up and looked over with a sly grin.
"Guess there is a dress code?" I didn't know what he was talking about until he pulled off his shirt and slide down his mesh shorts.
"Dude what the fuck are you doing?" I said bewildered.
"I, uhhh, didn't want to, uhhh, be over dressed if you weren't." He stuttered out turning a little flush.
"Put your clothes back on man." I said. Being in my room with a nearly naked 16 year old was weird.
"Yeah, it is kinda cold in here." He agreed, but instead of putting his clothes on he jumped under the covers on the other side of my full bed.
"Dude..." I said
"Let me just stay for a minute pleeeasssssseeeee" he gave me puppy dog eyes.
"Fine." I relented. It was a bit cold in here so I stood up and also went under the covers. It was MY room, no way I was going to be uncomfortable
We were both sitting up on pillows with our legs and half of our chests under the covers. I felt his warm thigh and leg move next to mine. I moved my leg a bit and felt his leg move back. While it was only a full size the bed wasn't that small.
At this point I was just trying to ignore him and watch the movie. Somehow I was succeeding at focusing on the screen, even though his leg was warm and his skin was super soft. Then I felt his hand rest on my thigh which made me jump.
"Dude..." I said and looked at him. He looked flushed and nervous. He pulled back his hand right away.
This kid is actually making moves on me. Holy shit. Part of me wanted to just throw him out of my room - he was my brothers friend. I gave him 2 minutes.
Just about when I was ready to tell him it was time to leave, I felt his hand move back and he was making small circles on my skin.
Damn, it kinda felt good and immediately sent a small jolt to my cock. For some reason I didn't stop him, part of me was curious to see how far he would go. He had balls, had to give him that. I felt like I would give him this small thing and then he could go jerk off or something.
I felt his fingers making slow circles on the top of my leg, and then he moved his hand and touched my dick. I would be lying to say I was totally soft.
"Dude what are you doing man?" I asked him and looked at him. He just gave me these puppy dog eyes. I realized that he never took his hand off my dick and had massaged it to almost full mast. While my big head was screaming that this was a terrible idea, my little head was like keep going for another minute."
I looked over at him and he grinned. I had the feeling like I was looking at him for the first time. Instead of this annoying little shit head that I ignored I saw a handsome young man. The word that came to mind was cute. Not sure I've ever thought of a guy as cute before, but I just couldn't help it.
He had bright brown eyes and freckles on his face that probably made him a killer with the girls. Well if he was into girls. We were both looking at each other and he looked excited and nervous at the same time.
He was fully jerking me off through my boxers. At this point I needed more. I didn't give a fuck. My dick was in charge and it wanted release.
"Lock the door." I whispered. He shot out of bed and quickly locked the door. As he turned to come back he covered his raging hardon in his boxer briefs with his hand. It was actually kind of hot that he was shy - as I think any 16 year old guy would be in front of an 18 year old. I couldn't stop my brain from thinking these things.
In a quick motion, he stripped off his boxer briefs and then came back under the covers. I only got a quick glance of what he was packing. His hand immediately went into my boxer briefs to grab my bare member. I groaned a bit in response.
"Can I see it?" He asked sheepishly.
I almost laughed at how crazy a question was at this point, and threw back the covers in response. I took my boxers off in one swift motion.
"Wow," he is whispered. It was like he was seeing something amazing for the first time. He was feeling me up completely and fondling my balls.
I looked down as his lap which was still covered with the blanket. I threw it back to reveal his manhood. He was cut, trimmed pubes and about the same length as me, 6 inches long. Damn, the little bastard was as big as I was. I reached over and starting feeling his dick which was super hard and leaking ample pre cum. His balls were about my size but they hung pretty low.
His head went into my lap and he started licking my dick. I looked down at his cute face licking my dick and thought it was so hot. He took me into his mouth and was sucking me like a starving person.
"Ouch," he nicked my shaft with his teeth as he was trying to take more of in his mouth. I could tell he didn't have much experience.
What he made up for lack of experience was his eagerness. For the next few minutes he tried to get as much of me into his mouth as he could. He nicked me a few more times with his teeth, and finally had a nice rhythm going.
He pulled off and returned to sitting up against the pillow next to me. He grabbed my head and pushed it into his crotch and I knew what he wanted.
As I looked at his dick...no stared at it....I couldn't say that I didn't want it. Did I want it? I looked up into his pleading eyes and just thought again how cute this kid was. A thought passed through my mind that I need to show this kids the ropes. Yeah.
I leaned in and felt the heat coming out of his crotch and a smell. It smelt clean like the shower he took not too long ago, but also something more. It was him, his masculine scent.
I started licking his dick all over. I was so horny and just totally disconnected from my brain. I wanted his dick. Fuck the world.
I was determined to make this feel amazing for him. When I licked down to his balls, I really wanted to take one in my mouth. I was totally gone by this point: my dick was leaking precum like crazy, I was intoxicated by his dick. No other word to describe it.
He was moaning as sucked one of his nuts and then the other. I moved up and licked his head and tasted a ton of precum. Damn, the taste was actually good. It was salty and sweet at the same time. I wanted a bit more.
I then started to swirl his head, thinking of everything that I liked. He yelped in delight.
"Quiet man." I pulled off of him and scolded. The last thing I needed right now was someone to hear and wonder what was going on.
He grabbed my head and shoved it back down on his dick. My mouth took him back in and he went thrusting into my throat. I gagged a bit and he stopped.
I went back to work bobbing and down on his cock, trying to get more of it into my mouth. Even though it was an average thickness I still couldn't get it all the way in .
I felt his cock get harder than it was, and he yelped as I felt a blast of warm wet liquid enter my mouth. Holy shit he was cumming. I didn't know what to do There was a lot of it and I had no choice to swallow it all. It didn't taste all that good, not bad but not good either. Pretty salty.
I pulled off his dick in a daze and he started jerking me off. I busted in like 2 seconds send huge blasts of cum all over my chest.
After a few seconds of recovery my brain started working again.
"Dude you better get back downstairs. If someone wakes up and sees your gone...." I said to him.
"Ok man." He said and started to get dressed. He snuck out quickly giving me a sheepish look as he closed the door.
I cleaned up the cum on myself and laid on my bed still kind of in shock. I couldn't believe that just happened. I was so horned up I lost control. While there was no doubt that I liked it, my mind raced. He was underage. He is 16 year, a boy, and I'm 18, basically a man. It's a big difference and I immediately regretted that this happened. I was going to text him to keep his mouth shut when I realized I didn't have his number.
The next morning I made it a point to go downstairs early. Of course, from our late night activity, Dylan was the last one up. He blushed bright red when he saw me and I think I turned a shade darker myself. I shook my head softly. He returned the head shake.
I didn't get a chance to be alone with him like I wanted and couldn't think of anyway to make that happen. So I took a chance when I thought no one looking and made the "lips sealed" motion with my hand. He nodded vigorously which made me feel better.
Then the boys were gone, and Tyler and I talked about the night and how great it was, and he was totally normal. Apparently they all passed out right after I went upstairs. Whew.
A few days later I got a text from a number I didn't know.
"Hey it's Dylan." Ohh fuck I thought.
Dylan: swiped your number from Tyler's phone. Don't worry he didn't see me doing it.
Me: hey. Dude, if you fucking tell anyone I'll kill you.
Dylan: I would never tell anyone. I swear.
Me: like I'm serious, i will come over your house and kill you. Just keep your mouth shut.
Dylan: I promise. Jeez dude. I'll swear on whatever you want. I won't tell anyone.
Me: ok good.
Aren't you going to ask me what's up?
Me: .... Me: Fine what's up.
He sent me a pic of a semi hard dick pressing against some mess shorts.
Dylan: that's what's up. Ha. Me: dude don't send that shit to me man Dylan: what this shit?
Another pic loaded with his shorts gone and a tent in his boxer briefs.
Me: yes dude, that shit.
Another picture loaded with his dick sticking out of the fly in his boxer briefs standing at full attention. I couldn't help but start to get hard. This fucking kid.
Me: dude!!
One last pic loaded with a close up of his head and drop of precum on it. I was getting hard from this kid sending me dick pics. What the fuck was wrong with me?
Dylan: yeah like you don't want to see that Me: I don't dude. Dylan: bet your hard
I started typing and stopped. Why did this kid have this affect on me?
Dylan: ha! I knew it. Where is Tyler? Me: he's at practice with my mom and bro. Dylan: so you are home alone? Me: yeah. Dylan: dude, come pick me up Me: no way Dylan: I'll start sending more picture :) Me: this whole thing is a bad idea man Dylan: pick me up please. Please. Please.
I was very conflicted. On one hand here was someone basically begging to get me off. Why shouldn't I go for?
The other side my brain was no fucking way. This is a terrible idea for so many reasons. In the end, my little head won out since I needed release.
Me: I'll be there in 10 Dylan: ok awesome Me: I don't want anyone to see us. I'll park down the street.
Dylan: ok
I had driven over near his house and parked 5 houses down. The entire time I was going back and forth about doing this. It was nerve wracking and exciting at the same time.
I just kept thinking of him and how cute he was. Sexy almost. Dude, what is wrong with me?
He rolled up in a pair of mess shorts and a hoodie over this head. I couldn't believe I was doing this. When he got in the car he took down his hoodie and looked over with a big shit eating grin on this face.
"Hey man." He said.
"Hey" I replied.
He reached over and grabbed my dick, which was soft. Then placed my hand on his rock hard dick.
"Heys all around. Haha." He joked. I pulled my hand off.
"Let's just get to my house." I wasn't in a joking mood. I was nervous. I was messing around with my little brothers friend against my better judgment, and it was dangerous. I started driving.
"I like can't believe the other night" he said softly.
"Yeah me either." I replied honestly.
"Was that like, uhhh, your first time with a uhh guy?" He asked sheepishly.
"No," I said simply. No reason to bullshit at this point. After all, I had his dick in my mouth. "You?"
"No," he said. "Anyone I know?"
"No," I really didn't want to go into details.
"So who was it?" He pressed. "Pleaseeee. Dude you know I won't say anything I swear."
I just sighed. "Just a guy from college."
"What is his name? What did you guys do?" He was very excited to hear this.
"No way am I telling you his name man. You'll definitely stalk him out on my Insta or snap. We just messed around a bit, you know two horny guys." I said
"Did he suck you? Did you suck him? Was he your first?" He kept digging for info.
"Yes, yes, and yes. No more questions man. Like we shouldn't even be doing this." I said. I really wasn't comfortable sharing the details with this 16 year old.
"What about you? I told." I send after a minute of silence since I was legit curious.
"Just a kid from my grade. We wanted to see what it was like, so we blew each other. Not sure he really liked it, but I did. It was great" he was beaming.
"Anyone I know?" I asked.
"Bet you are thinking it's one of the friends in Tyler's group? But nawwwww you don't know him." He replied.
"Dude your brother is super hot." He blurted out of know where.
"Jesus man. That was something I didn't need to know." I said.
"I know, but you are so hot. And you kind of look like each other. I never thought in a million years you would go for this. I wonder if Tyler would." He continued.
"I have no idea. He's my brother and all, but we aren't that close." I stated.
"Are you gay?" He asked me directly. At this point, I missed the unsure kid from the other night.
"No." I answered definitively. "Are you?"
"I don't know. I mean I've never told anyone this, but guys are much hotter than girls. Like I would love to fuck a girl but I like guys more." He said.
"Well, I'm not putting labels on it. I'm just messing around." I replied. I didn't know what I was.
We pulled up my empty house and proceeded directly up to my bedroom. He stripped off his hoodie, shirt, and shorts and laid down in my bed. I did the same. We both were raging hard.
For a second I was not sure what to do, so I pretended he was a girl. I crawled on the bed and then went to kiss him. Even though he clearly had no experience, it was hot. He started kissing back with earnest.
"Dude not so hard." I said.
"Sorry." He actually blushed.
"Follow my lead. Soften up your lips." I said back to him. I slowly kissed him and holy shit it was much better now. His lips were so soft and I gave him a little tongue.
I was definitely leaking a ton of precum and continued taking the lead. I kissed his neck and ear which made him go nuts. I was really getting into this, like really.
Kissing down his chest, I stopped to suck on his nipple which immediately got hard. He let out a little moan. I proceeded to kiss down his stomach and hesitated when I got to a light treasure trail. This brought me back to the fact that this was a dude, and there was no pussy under there but a raging dick.
I almost stopped right then. This was so wrong on so many levels. But I needed to see his dick again
I took down his boxer briefs and his dick slapped out. All 6 inches were raging hard and leaking precum. I looked up to see him anxiously waiting with a yearning on his face. He was just so fucking cute, I wanted to please him.
I started licking up all his precum, remember the salty sweet taste from the other day. I thought about everything i loved and look it slow. Swirled the head, licked up and down the shaft, and sucked on his big balls.
"Ughh, suck it man. Suck my dick" he said. I was so hot and fired up that I took him in my mouth.
I was beyond thought as I sucked his dick, getting a burst of precum everyonce and a while. I realized he was telling me what to do now and again and I was just doing it. Suck his balls, sure. Suck harder, sure. Try to get more in my mouth, sure. I was just so horny.
"Switch." He said and crawled off the bed. Fuck I needed my dick sucked badly. He smiled and looked at me as he licked my dick. I immediately groaned in delight as he took my head into his mouth.
It was hot to see this cute 16 year old sucking my dick. No, worshipping it. If you had told me a few months ago that I would get off on something like this, I would have beat the shit out of you. Now, I just gave in to the feeling. I just gave into that cute face.
He then started going down on me, taking 2 inches and then 4. He nicked me with his teeth a few times but it felt pretty damn good.
He was getting good at taking more of it in his mouth. I looked down to see his head bobbing up and down on my rod. Then he was totally deep throating me.
All of a sudden he pulled off my dick and fumbling around with something then I felt a cool sensation on my ass. Then I felt something enter slowly. It was his finger.
"Dude...." I said.
"It will feel great. Just go with it." He replied.
It felt totally strange at first, like there was a foreign invader in a place it shouldn't be. Then he started massaging my asshole and I felt an immediate pulse in my dick. Fuck, I never knew my asshole could feel this good. No girl had ever ventured down there and I had never explored the area.
Ok, so I maybe had pushed a finger in there now and again in the shower but only for a few seconds. It felt weird.
He pushed my legs open further to get better access and I didn't stop him. He had a full finger in there and then went back to sucking my dick.
Then I felt another finger enter meeting some resistance joining the other finger. Then he was slowly moving in and out of my ass. Holy shit, was this kid finger fucking me? I should throw him off this bed right now. But I couldn't move, I was just laying enjoying the feeling of my dick in his mouth while he had his way with my ass. I felt my eyes glaze over as I was just lost in feeling. My balls were churning.
He simultaneously pulled his mouth off my dick and his finger as out of my ass. I was confused and wanted him to finish me off.
I picked up my head and looked up to see him smearing some lube, that was the cool sensation from before, on his dick.
"What the fuck are you doing?" I asked,
"Dude I have to fuck you." He said.