What's My Age Again?

"Wait you want me to do what?" Kellin asked to make sure he heard me correctly.

"Give me lessons on how to have sex." I repeated.

"Why?" He furrowed his eyebrows at me and sat on my bed.

"You know why." I rolled my eyes at him.

"No, you're not ready to have sex with Alex yet."

"Yeah I am! We both said we liked each other and I feel comfortable around him." I explained.

"You haven't even known him a month!" He yelled at me.

"You had sex with Vic after one date so what's the difference?!"

"I wasn't a virgin when I slept with Vic. So it didn't matter if I fucked him within the first minute of meeting him."

"I don't understand why you can have sex with whoever you want but the second I suggest doing it, it's a problem." I frowned.

"It’s because it's your first time. It's supposed to be with someone you care about and feels the same way about you." He told me. This isn’t how he would normally talk about this subject. He was, for some reason, trying to talk me out of having sex with Alex.

"We do both care about each other so I'm still not seeing a problem." I said and he sighed.

"You're such a stereotypical teenager. You barely know they guy, but you feel like you two are madly in love with each other."

"I asked for your help, not for you to come over and insult me." I scoffed.

"I am helping you. I'm helping you not make a big mistake." He said.

"You said Alex is a nice guy so it's not like he would just use me and never speak to me again."

"No he wouldn't do that, but-"

"-And you're the one who is always saying ‘sex isn't a big deal’ so why is it one all of a sudden?"

"It normally isn't but I just don't want you to . . . make a mistake."

"A mistake? What do you mean a mistake?" I had no idea what he was talking about.

"No I meant hurt. I don't want you to get hurt." He said suspiciously.

"Okay? Hurt how?"

"It isn't a pleasant feeling the first time. Plus you just don't seem ready to do this. I can tell you're making yourself do this." He sounded really worried for me.

"I am not." I was kind of lying. I was physically prepared to do this with Alex, but not really mentally prepared.

"What happened to your three month plan? You said you were going to wait three months before considering sleeping with him so what made you switch to three weeks all of a sudden?" He questioned.

"I like Alex a lot and I'm ready to take the next step with him. I feel like us just making out is boring him."

"So you're doing this because you think it's what he wants?"

"No it's what we both want."

"You're stressing me out." He ran his hand down his face.

"You don't have to help. I just asked a simple yes or no question not for a lecture." I said stubbornly.

"Okay no I'm not going to help you fuck some guy when you're forcing yourself to do it!" He snapped.

"Then I'll figure it out on my own!" I snapped back.

"Fine." He stood up and made his way to my door. "Make sure you use protection, asshole." He added and left.

I glared at him as he walked out without saying anything. I don't know why he was acting so over protective all of the sudden. I decided not to worry about it for now and I picked up my phone so I could text Alex. I wanted to see if he was busy tonight.

From Jack:
Hey are you doing anything?

From Alex:
No I was actually going to text you and see if you wanted to hang out.

From Jack:
Yeah, what do you wanna do?

From Alex:
I was thinking we could have hot chocolate and watch movies at mines? The guys are going to be out for the night so I have the place all to myself.

From Jack:
Sounds great! I'll be over in a few.

This was the perfect opportunity for me to go with Alex. My mom was working and he had the house to himself. I was just going to tell my mom I stayed with Kellin. Kellin would cover for me because I didn't it for him millions of times.

I took a quick shower and shaved everything except for my arms and legs. Then I changed into new clothes. I put on my best smelling cologne and lotion I had. I wanted everything to be perfect for tonight. I put on my shoes and left, driving to his house from memory.

I made it to Alex’s house fairly quickly because there was barely any traffic this late. I got out and went to the door and rang the doorbell.

"Hey!" Alex greeted me with a hug when. "You smell really good."

"Thanks." I giggled and followed him inside.

"I have everything set up upstairs." He told me and I followed him to his bedroom.

When I walked in his room it was dim with just a few candles lit and a floor lamp on. He had out hot chocolate sitting on the nightstand next to his bed along with chocolate covered strawberries and other snacks.

"Wow this looks great." I said as I sat next to him on his bed.

"Thanks! I tried to make it as romantic as possible for you." He told me.

"It's very romantic." I said and kissed him. "So what movie are we watching?"

"Well I googled 'romantic movies' and one of the first ones to come up was 'The Notebook.'" He chuckled and I laughed.

"Good choice! I actually really like that movie."

"Okay good, I was afraid you were going to think it was corny."

"Oh no I do think it's corny, but it's still cute." I joked and he hit my side. He picked up the remote and turned on the Blu-ray player. The movie screen came on and he pressed play. We moved closer to each other as the beginning credits started.

I leaned over him to grab a chocolate covered strawberry. I took a bite out of it and he grabbed my hand and brought it to his mouth so he could eat the rest of it. I chuckled and my body temperature rose as he stared at me with lustful eyes. I turned my head to face the TV and seconds later I felt Alex placing kisses on the back of my neck.

"Alex!" I giggled and turned back towards him.

He moved to the side of my neck and continued to kiss and lick along it. At first it tickled but now it was beginning to feel really good. I moaned as he kissed up my jar to my mouth. We made out as he situated himself on top of me. I laid on my back and he laid between my legs. Then I wrapped my arms around his neck as we continued to kiss. His hips pushed down more into mine and I could tell he was becoming turned on.

He pulled away from my lips and went to attacking my neck again with kisses. I felt a few bites too, but it excited me more.

"Tell me if you want to stop." He whispered in my ear and then kissed it.

"Don't." I moaned.

He lifted up and pulled his shirt off exposing his toned torso and hairy chest. I was mesmerized by the sight, he looked so perfect. I didn't know whether I should take off my own shirt or wait for him to do it for me. I grabbed the ends of my shirt and slowly began to pull it up. Alex watch me intensely as if I was doing it slowly to tease him. I pulled my shirt completely off and he fell back on top of me. He kissed from my neck to my chest and to my nipples.

"Did you shave?" He asked amusingly and he sucked on one of my nipples.

"Maybe." I mumbled and he chuckled. I did shave, but not my chest. I didn’t grow hair on my chest for some reason.

"You're so perfect." He leaned up to kiss me.

I reached down to unbutton my pants as we made out. I was too nervous to reach for his since last time I did that he stopped me. I pulled down my zipper and he moved my hands so he could remove my pants for me. I lifted my hips and let him slide the pants off of my legs. He stood up, took off his pants, and laid back on top of me.

Now that we were only in our boxers, I could really feel how hard he was and I'm sure he could feel me too. He grinned down and rubbed up and down so that are hard-ons would be rubbing against each other. I wasn't nervous before but now I was because it was setting in that I was about to have sex with him. I wrapped my shaking arms around his torso and he slowed down.

"You okay?" He asked.

"Yeah...I'm just ready for you." I muttered.

He moved down to kiss me and pulled his boxers down. I wanted to look at how big he was, but I couldn't bring myself to do so. He put his fingers on my boxers and looked at me to ask if it was okay. I nodded and he slide them off of my body. I felt self-conscious as he looked at me, but he breathed out the word "beautiful" and it made me feel better. I got a glimpse of him as he laid on top of me and it was very impressive. That might have been a bad thing since it was my first time.

He reached down and grabbed both of our hard-ons and began to run them together. The firm grip he had on me was enough to bring me close. Plus the fact that this was the first time someone else besides me had touched myself before.

I moaned feeling myself about to come, but he let go of us. He reached into his nightstand drawer and pulled out a bottle and a condom. Kellin had nothing to worry about, we were being safe. He popped the cap off of the bottle he pulled out of his nightstand and poured it on a few of his fingers. I read that the label said K&Y Jelly.

"You've been fingered before haven't you?" He asked and I nodded. Of course I was lying to him. The most I ever did was jerk myself off. "Good this won't be so bad." He said.

He brought his index finger to my hole and circled it around a bit. I felt scared, I've never had anything go up my butt. I should have told him the truth. He slowly pushed it in which at first scared me and made me jump, but I realized it wasn't so bad. He chuckled at my reaction and continued to push it in and out. If sex felt like this without the stretching then I would be fine.

"You seem kind of tense." Alex comment and rubbed my thigh with his other hand.

"I'm about to have sex with a really sexy guy so it's kind of impossible to be calm." I nervously giggled and he laughed.

"You're so cute. I can't wait to get inside of you." He said and I bit my lip. I was ready for this.

He added a second finger in and the burning stretch made me unsure again. I exhaled as I pushed off his fingers a bit. It hurt for a little while but I started to adjust to it. It hurt even more when he began to move his fingers apart and around. I laid my head back and closed my eyes waiting for him to finish.

He leaned down to kiss my cheek. "Relax a little." He told me and I nodded. I took a deep breath and unclenched my butthole. I barely noticed that I had it clenched to begin with. It felt better when I relaxed and let him finger me.

He removed his fingers and wiped it on the sheets. I watched in awe as he grabbed the condom and ripped the package open with his teeth. He rolled it on himself and grabbed the lube. He poured it into his hand and coated it himself in it. Hopefully that would help with the pain a lot.

He laid down between my legs and kissed me. Kissing him made me feel some of my anxiety go away, but there was still a lot. Our tongues swirled around each other mouths for a few minutes. It was simple, I felt safe with Alex.

"Are you ready?" He pulled away and asked. All the anxiety that I lost quickly flooded back in.
"I think so." I bit my lip.

He rubbed my thigh soothing. "We don't have tonight."

"No no I'm ready. I'm just afraid of how much it will hurt." I said honestly. "It's uh been a while."

"It only hurts a little bit. It's not unbearable pain." He said reassuringly.

"You've bottomed before?" I asked, shocked.

"Yeah just few times, but I didn't really like it."

"Why not? Because it hurt you too bad?"

"Jack, it wasn't bad. I just didn't like being fucked by another guy. It wasn't for me." He told me. "We really don't have to today. I won't be angry or disappointed." He assured me.

"I'm okay." I insisted and he kissed me.

"Tell me if I’m hurting you and I'll stop." He told me and I nodded. He reached down with his right hand and lined himself up at my hole. Just feeling the tip press against me scared me.

"It hurts!" I called out and he chuckled.

"Jack I'm not even pushing in yet." He said and I nervously giggled. I just needed to relax some more.

He began to rub the tip in circles around my hole trying to get me to calm down. It felt so good and it made me want him to get inside of me already. I laid my head back on his pillow as he continued to do this for a minute. I felt him go forward and try to push in and I pushed away from him. It was a reflex because I did it without thinking.

"Sorry!" I apologized.

"It's okay just try to relax some more." He began kissing down my jaw to my neck as he circled around me more. He was making me feel so good. I hated that I was so afraid of this because I really wanted to have sex with him.

"I'm gonna try again, okay?" He whispered in my ear.

"Okay." I told him.

He kissed me on the lips and opened my legs up some more. I waited patiently as he lined himself up with me perfectly. I felt him attempt to push in again. The tip was almost in but it hurt so I hissed and pushed back again. He stopped and laid his head down on my shoulder. I wanted to apologize again but I knew that would get annoying.

He kissed my shoulder a few times. "Are you sure we shouldn't wait?" He whispered in my ear. We were so close, I didn't want to stop now.

"No it's okay, I promise. Just try it again and this time don't stop if I try to push away." I told him.

"Um are you sure?" He asked nervously. That did kind of sound like I was telling him to hurt me.

"Yeah. I want this, I want you." I brought his face down to kiss me. We made out as he lined up with me for the fourth time. I tried not to think about it so much and instead focus on his tongue in my mouth. He held on to my hips with one hand as he used the other one to push in to me. I cried out as he got past the tip and continued to go in deeper.

"Sh sh sh." He brought his hand up to run his fingers through my hair calmly.

He finally stopped once he reach a certain point. I looked down to see he wasn't all the way inside of me which made me sigh. There was still more to go.

"I'm just give you a break." He chuckled and kissed me. I laughed against his lips with him. He accidentally pushed in more when we were kissing and I groaned.

"Sorry sorry!" He apologized.

"It's okay." I assured him and we continued to make out.

He pulled away from my lips and began to go in the rest of the way. I felt like my asshole was split in half. He sat still and kissed all over my neck.

"I'm probably the most dramatic person you've ever had sex with." I said apologetically and he snickered.

"You are, but that's not a bad thing. It's actually a really big turn on." He said.

"It is?"

"Yeah it makes me feel bigger. Plus you're really tight so I understand why it hurts so badly." He was already big down there do I don't know why he wanted to feel bigger.

As we kissed he slowly began to pull out of me and push back in. The movement still hurt like hell, but not as bad as the initial push in. I rubbed my fingertips up and down his back. I was trying not to cut him with my nails but every now and then I would slip up and scratch him.

The pain started to fade away and it began to feel so much better. He was still moving at a slow pace so I could get used to it. After a minute I decided that I was ready for him to go faster.

"You can go faster." I pulled away from our kiss and said.

"You sure?" He asked and I nodded.

He slowly began to pick up speed. The room began to fill with slapping noises and gasp from me. It felt better with him going faster than before. The pain was almost completely gone. I grabbed on to his hips as he pounded into me.

"Unn oh god!" I cried.

"It feels good?" He asked.

"Yes! So so good!" I exclaimed.

We were both breathing heavy as he continued to fuck me. I didn't think it could better than this and then Alex switched angles and touched something that made me shiver.

"Alex." I moaned. He realized that what he touched made moan like that so he went back to that angle.

"Is it right here?" He asked as he pounded into that area.

"Yes it's right there!"

He smiled and bit down on random parts of my neck. I couldn't even think straight with him abusing that spot. I wasn't going to last much longer. I wrapped my hand around myself and began to stroke myself.

"I'm going to come, Alex." I moaned.

"Fuck, me too." He breathed into my neck.

He thrusted into me for a few more seconds before I was coming all over my stomach and chest. I laid back in bliss as he pushed in a few times then came into the condom. He pulled out of me making me feel completely empty. I didn't like that feeling at all.

He threw away the condom and rolled over on to his back. I felt like I couldn't move because I was still in shock that I actually just lost my virginity to Alex and how good it felt.

"Are you okay?" He asked me after a while.

"Yeah I'm more than okay." I said and he laughed.

He handed me some Kleenex to clean myself up with then helped me roll over so that I was laying on my stomach and on his chest. I looked up to see him looking down and smiling at me. I reached up to kiss him and he bent down a little to reach me. His hands rubbed soothingly on my butt as we kissed.

***

I woke up tightly wrapped in Alex's arms. My face was in his chest and his head was resting on mine as he slept. I didn't want to leave this early, but if I wasn't home before my mom, I would be grounded for life. I slowly slipped from his grasp and quietly got dressed.

“What are you doing?” He asked as he woke up.

“I’m sorry, I promised my Mom and sister that I would meet up with them for breakfast.” I lied.

“You’re leaving?”

“Yeah.” I was kind of jumpy because I was running low on time.

“But I was thinking we cou-“

“I’m sorry I really have to go. I’ll call you later.” I bent down to kiss him.

I left his house and limped to my car. I had to ignore the shooting pain going up my backside for now. When I made it home I saw that Kellin's car was parked in front of my house. He had a spare key so he was probably inside ready to gloat about being right about sex hurting.

I walked in and went straight to my bedroom. Kellin was lying in my bed asleep. I got out of my clothes and switched to my pajamas. I laid down next to Kellin with my back facing him and the next thing I know he wrapped his arms around me.

"Did you do it anyways?" He asked quietly.

"Yeah." I mumbled and he sighed.

"We're you at least safe?"

"Yes."

"Good."

Notes

Jack is making real grown up decisions. And Kellin’s problem with Jack will make sense in due time.