Hey guys, you have to be 18+ to read this! This story contains sexual encounters between teenage boys. If this offends you or is illegal where you are from, please don't read the story.
My name is Joey and this story details my high school adventures (some middle school). If you would like more, email me at joeyblow91@hotmail.com, or just give me feedback/comments!
"So you're not dating him?"
"No."
"But you're fucking him."
"Not yet."
"And you gave each other blowjobs."
"Yeah."
"And you kiss each other."
"Yeah."
"And like each other a lot."
"Duh!"
"And you think about him all the time. And he thinks about you."
"I hope so."
"Sounds a whole fucking lot like dating, Joey."
I swear Chrissie and I had this same conversation five times over that day. She couldn't understand the idea of him not wanting to put a label on what we had. I didn't get it completely either, but I accepted it.
Chrissie and I were sitting on the brick wall behind the school after our last class let out. I caught her up on the latest happenings between Emerson and I. Ever since she found out I was gay, she was excited to be my 'fag hag' and enjoyed knowing the details of my relationship.
"What are you gonna do with him next week?" she asked me.
I looked at her quizzically.
"You know... for Valentine's Day?" she said.
"Oh shit. I've never had a real valentine before," I responded. "What should I do?"
"You're the one that's madly in love, how am I supposed to know?" she said. I wondered what to get for him. I knew he liked computer games, basketball, and lacrosse. But I didn't think valentines got each other gifts for their hobbies.
Chrissie looked at me and sighed. "Seriously, Joey? You don't have aaaaaaany idea what he might want? You're both horny teenage guys."
"I thought you didn't know what to get him."
"Come on, you've already rounded third base with him. Maybe let him score a home run."
At home, I thought about what Chrissie said. In porn, I always found anal sex hot but I never felt the urge to actually want to do it. Not only that, but his dick was a lot bigger than anything I could ever imagine going up my ass. Just thinking about it made me clench up.
My daydreaming was interrupted by my mom coming home from work. "Joey!" she yelled from the door. "I brought home dinner!". My mom was cool. She was one of those parents that was like a friend, someone you could talk to about anything.
We sat down at the table and started eating together. "So, how was school?" she asked.
"Normal... you know, nothing exciting."
"And your grades?"
"Still good, mom," I said, answering that question for the millionth time and knowing I'd have to answer it a million more.
We ate silently for awhile when I couldn't help but blurt out, "Mom, I need... condoms." She put down her food and looked at me square in the eye for a few seconds.
Her mouth came up in a smile and just said, "Okay."
"Okay?"
"Yes?"
"Like you'll get them for me?"
"No," she laughed. "Why would you want me to shop for your condoms? I'll give you money, you can get them."
I took another bite of my chicken. "Why aren't you, like... I mean... I thought you'd act differently."
"Well, the last thing I want is for you to get Chrissie pregnant. It's good you came to me about this. I'm glad you did. Wouldn't want your life to be ruined over a baby," she said.
"Actually, it's not..." I faded off, realizing what I was about to say.
"Not...? Not what?" she inquired.
"Nothing," I said. "I forgot what I was gonna say. Thanks for being so cool about this, mom."
That weekend, I walked to Walmart to buy the stuff I needed for my "surprise" with Emerson. I went straight to the pharmacy/medical section and started browsing around. After not being able to find it for a couple of minutes, I asked the older lady at the pharmacy checkout where I could find condoms and stuff. She let out an audible sigh, pointed around the corner, shook her head and started back on what she was doing.
I saw a small shelf with a wide selection of condoms and some lube. I picked out two different kinds of condoms and some KY jelly and was about to head back to the pharmacy when I heard someone say "Hey, Joey?" behind me.
I turned my head. "Holy shit!" I exclaimed. "Will!" I gave him a quick hug, as if it were an automatic reaction.
"Looks like you're getting ready for something serious, huh?" he said, pointing at the condoms and lube in my hands.
"You too," I replied, noticing the condoms he also had. "What's that?" I saw he also had a large cardboard box
"Take a look," he said as he moved the box closer so i could see inside. I pried open one of the corners and saw a purple dildo inside."
"Are you, like, gay now?" I asked.
He started laughing, "Hell no, dude, this is for my girlfriend for valentines! it fuckin' vibrates and everything."
I suddenly really wanted to get that for Emerson and I. "Where'd you get that?"
"Special order. They don't keep it on the shelves. It's in the back. My brother works here."
"How can I get one?"
"Ask me," he winked. "Wait here."
I checked out my condoms and lube and sat down in the corner waiting for Will to come back. He ended up going to a different high school than me, so I hadn't seen him in almost a year. Looking at him, it seemed like a lot more than a year. He got taller, cut his hair, and looked like he was working out. He used to be cute, now he was hot. Just as attractive, but in a different way.
I saw him come out from the back room with another cardboard box. "How much is it?" I asked him.
"Free for you, man."
"Really? Thanks so much."
"No problem. Consider it payback for, you know... middle school."
We decided to exchange numbers to hang out in the future then we went our separate ways.
When I got home, I put all of my new "sex gear" in my closet in my room. I called Emerson to check on what he was doing.
"Hey, it's me," I said.
"Oh, hey cutie, what's poppin'?" he asked. I could hear a smile on his face which made me smile.
"Nothing. Just checking up on what you were doing."
"Funny you ask that, I'm in the middle of rubbing one out."
"Really... you watching porn?" I asked.
"Yeah. It's this hot blonde surfer guy fucking this asian dude."
"What porn stars?"
"Porn stars? Fuck that studio porn shit, it's too fake for me. I can only get off to amateur porn. 'Cause you know the guys want to be there, they aren't getting paid."
"Maybe we could make an amateur video of our own one day," I teased.
"That would be so hot... we totally should!"
"So I was wondering, you know how Monday is Valentine's Day?" I said. "We should skip and just hang out for the day."
"Why not?" he agreed.
On Monday, we both got our parents to call in sick for us. Around 11 am, we met up halfway at a McDonald's and ordered some lunch. When we sat down, I noticed he had his backpack with him. "What's with the backpack?" I asked.
"You'll see," he smiled.
We walked back to my place and went up to my room. We sat on my bed and he opened his backpack and took out a shoebox and handed it to me. "Happy Valentine's Day, Joey." He gave me a quick peck on the lips and I opened the box.
Inside were about ten pictures of him half naked or naked in sexy poses. Instantly, my dick got hard and started buldging in my shorts. "Thought you might want some new jack off material," he said.
I flipped through the pictures. "This is so hot.. you are so hot.. thank you, Emerson. It's awesome." I kissed him and we made out for a little bit.
"So? What'd you get me?" he looked excited.
I walked up to my closet and picked out the cardboard box and handed it to him. He opened it and took out the dildo. "Wow, I've never had a dildo before. This is cool." He took it, put it between his lips, then started licking up and down the length of it. I was certain my boxers were soaked in precum by now.
"That's not all I got you," I said as I went back to the closet and picked out the condoms and lube. "I want you to fuck me."
He looked at me in the eyes and asked me, "Really? This isn't just you wanting to give me a gift, right? You want to do it?"
"I don't know," I replied. "I think I should try it. At first, it was just to give you a gift but the more I thought about it the more I realized if I wanted my first time to be with anyone, I want it to be with you. I've never felt so connected with anyone before."
"Me too," he grinned. "I've never done it with a guy before... only girls. I heard assholes are tigher, though. Especially yours!" He slapped my butt.
"Seriously, though, Joey. I'll be gentle. If you ever want to stop, just tell me," he assured me. I nodded.
"So what are we waiting for? Shove it in there!" I said, pulling his shorts and boxers down. His huge cock stood up proudly. I took off his shirt and he took off my clothes right after.
"Do we need this?" he said, pointing to the box of condoms.
"Better safe than sorry, right?" I said. He complied, opened the box and unwrapped a condom and put it on his cock. "So how do you want to do this?"
"I think you should have control first. I'll lay down and you can sit on it," he said. I felt good about that idea. I took the lube and squeezed a bunch on my hand and coated the condom on his cock with it. I squeezed out a bit more and put some on my asshole.
I started to feel incredibly nervous as I sat on his stomach. I leaned down and kissed him and started to feel better. I raised my butt and took his cock in my right hand. I lowered down and felt the mushroom head of his cock push inside. Immediately, he let out a loud moan. "Hoooly shit, dude." he stammered. "You're so tight and hot in there."
I lowered down a bit more. I guessed about two inches were in there by now. Every time I sat down a little further, he would moan uncontrollably with a slight shiver. I could tell it felt amazing for him. I went up and down on the few inches I was comfortable with at the time. The lube was running out and I could feel it hurting more and more the more I sat up and down on his cock. I came off his shaft completely.
"I need more lube. It's starting to hurt really badly." I took the lube and put some more on his cock and my hole. "Fuck me like this now." I pulled him up and took his spot on the bed. I raised my legs up to his shoulders and exposed my hole to him.
"Ready?" he asked me. I nodded. He held my left leg with his left hand and took his cock with his right hand and pushed it in. He started fucking me slowly when I suddenly felt an incredible sensation and yelled out a moan.
"Are you okay?" he stopped.
I gasped for breath. "I think you just hit my prostate... keep doing that, that was incredible."
He smiled and started fucking me again, going much faster now. He had both of his hands on my legs now. I was in heaven. I laid back my head and enjoyed him fucking my ass. The bed was rocking and squeaking with the rhythm of him fucking me.
"Oh, God, Joey. I've never felt anything like this before," he exclaimed. "I'm going to cum soon."
"Me too," I said as I started jacking myself off.
He started fucking me harder and harder, letting more and more of his cock in. Eventually, I felt his pubes touch my ass when he was going in and out.
"Joey, I'm gonna cum," he moaned loudly. "I'm cumming now!" He stopped thrusting in and out and just let his cock stay in. I felt his shaft pulsate as it was in me and then felt a warmth shoot inside my ass. This pushed me over the edge and I started cumming at the same time. I must have shot over ten spurts of cum. It got in my hair, on my face, chest, and stomach. It even flew over my head on to the bedstand.
He pulled his cock out. "Oh... Joey... look." I looked at his cock and saw the condom had ripped open at the head. The warmth I felt must have been his cum shooting in me.
"It's okay. We're both clean," I said, still lying down and looking at him.
He smiled and leaned in to kiss me. He licked off the cum from my face, then my chest, and my stomach. Lastly, he went down and gave my cock a quick lick over. I gasped and shivered from how sensitive it was when he licked the head.
We enjoyed another makeout session before we decided to shower and clean up.
"So, how was it?" he asked, as we were drying ourselves off from the shower.
"Do you really have to ask? I can't believe I didn't want to try anal. That was the most intense orgasm I've ever had."
"I think it was for me too. Seriously, vaginas aren't shit compared to asses," he smiled.
"Emerson," I said. "I know we aren't dating technically, but I still want you to meet my mom. Like, I want her to know that we're a thing."
"Is she gonna be cool with that?"
"Yeah. But she still doesn't know I'm gay. I just wanted to wait until I met someone before I told her so she knows I'm serious about it."
"Okay then. What about your dad?" he asked.
"I dunno. I hope he's okay with it, but he might not be. I don't want to tell him yet."
We waited until six when my mom came home from work. The usual came from the door, "Joey! I brought dinner!".
"Come on," I said to Emerson. We walked down the stairs together and stood in the hallway. My mom was setting her purse down with her back to us.
"Joey, I spoke to Mrs. Conwell today and she told me she didn't even know Chrissie and you--" she turned around and saw Emerson standing next to me. "Oh, excuse me. Who's this?"
"This is Emerson, Mom."
"Hi," he said and waved his hand.
"Nice to meet you, Emerson. I didn't know we had company or I would have tidied up the house."
"Mom, can you sit down?" I said.
"What happened?" she sounded worried. She sat down on the nearby couch and looked at us. "Is everything okay?"
"Mom, I'm gay. I've been seeing Emerson. We're together, sort of."
"Oh, Jesus!" she sighed. "I thought something awful had happened. It's okay, honey. I thought you might be. It doesn't change who you are to me." She stood up and gave me a kiss on the forehead. She then turned and gave Emerson a hug.
"You be nice to my son, you hear?" she told him.
Emerson nodded. "Of course I will. I would never hurt him."
"Mom, one more thing. I was hoping we wouldn't tell Dad yet. I don't know how he would feel about it. I mean, his only son being gay? And not like, continuing the family name or whatever."
"Joey," she laughed. "Your dad has thought you were gay since you were five! I owe him $10 now that he was right."
Emerson and I laughed at the thought of my parents making a bet over if I was gay when I was five. We all hung out and watched a couple of comedies before Emerson figured he had to get home before his mom came home from work and saw he wasn't really sick.
Later that night, when I was going to sleep, my mom approached me. "So you guys spent the day here instead of school?" I nodded.
"Well, you're grounded for a week for skipping school. But that's not why I'm here. I wanted to make sure you are being safe."
"Mom, you know I bought condoms. You gave me the money for it."
"I meant safe here," she pressed her hand on my chest. "Just know that not everyone is honest and very few people meet the love of their life when they are as young as you. He may be it, but don't change your life and who you are for him. I don't want to see you get hurt."
"Okay. I'll keep it in mind," I said.
Thanks for reading, guys. If you want to know more or leave me feedback email me at joeyblow91@hotmail.com.