The Day I Met Ryan

Chapter 7- Oliver

~~This chapter contains explicit sexual stuff~~

We sat in silence for a minute before I remembered. Simon. Oh God, what would they do to Simon? I started to panic.

"My cat...oh my God, my cat...God knows what they'll do to him.."

"I didn't know you had a cat."

"..yeah. I love him so much.."

"We could go get him."

"No..my parents would freak out...wait.." I got an idea. "I still have my house keys in my backpack..they're going out tonight..Thursdays are their date nights.."

So, sure enough, at 7:30, when they would be leaving, we started packing up to leave. When we arrived there, we used my keys, and quickly rushed in, grabbed all of Simon's things, him, and got back in the car. As soon as I grabbed him Ryan was in awe. As soon as we were in the car he started petting him and swooning. Simon seemed confused, but let him hold him.

When we got home, Ryan set up his litterbox and food and then immediately stole him from me. He started talking in a baby voice.

"Mr. fwuffy boy aw you're so cute awen't you" Simon meowed softly and nipped Ryan's nose. He giggled. "Is that a good thing?" he said, still laughing.

"A very good thing. He's giving you love bites. The only other person he gives those to is me." I smiled.

"Okay good." Ryan smiled at me before giving Simon a kiss on the head.

My mind began to wander. I had never even thought of having pre-marital sex pretty much ever, but I found myself thinking about what it would feel like to have sex with Ryan. When I came back from my trance, I looked down and saw I had a boner. I thought about it for a second. Did I want to lose my purity? Did I want to perform another sin? Was I ready? I came to the conclusion of yes for all of them. Was it the fact I was insanely horny? Maybe. But, regardless, I tapped Ryan's shoulder. He looked up from Simon.

"..I wanna have sex..if you want to..." I said, so quiet I slightly questioned if Ryan heard me. He smiled, putting down Simon.

"Are you sure?" He asked. I nodded. "Okay baby." He took off his shirt. No binder today. I bit my lip and watched him strip as I began stripping myself. When I was naked, he looked at my dick and smiled at me. He got up to lock the door, and once he came back he got on his knees with his head at my dick. Ryan put his hand around my dick and started pumping slowly. My head seemed to become very heavy all of a sudden, and it fell back, my mouth open, loud moans coming out.

"Is that good baby?" Ryan asked.

"U-uh h-huh." I barely forced the words out.

"Just let me know if you want me to stop or do something different okay."

"O-okay." He started pumping faster and I squeezed my eyes closed, the warm feeling coming back.

"I- I think I'm g-gonna–" I moaned loudly and finished all over myself and Ryan's hand. I took a minute to recover, before laying back. Ryan joined me.

"You still wanna..?"

"Yeah, I just need a minute." I bit my lip. He climbed into my lap and kissed me. I already felt myself getting hard. I soon felt myself get very hard. Ryan could tell I was getting desperate and got off. He grabbed a condom out of a box in his bedside dresser, and climbed back on me. He asked if I knew how to put it on. I said no, embarrassed. He helped me put it on, and then grabbed my hand as he positioned himself over my dick. He lowered down slowly and I moaned.

"Is that okay? Do you need a second?" Ryan asked. I nodded. He pulled my hand up and kissed it. I took my hand away and put them around his waist. He was so beautiful. Everything about him. His scars, his little squishy stomach, his boobs, everything. I looked back at his face and I could tell he was getting desperate.

"Can I help you?" I asked. Ryan nodded. I gripped his waist a little tighter and helped pick him up and drop him on me. He threw his head back and cursed. He helped me when it got to lifting up. We picked up a faster pace and I soon felt the warm feeling. I tried to hold it off for a little while, until Ryan was announcing he was gonna cum. I reached my hand up and started rubbing his nipple. The warm feeling came back and I announced I was going to cum too. I came inside the condom as Ryan came and we both took a minute to recover. Once we had both caught our breath, he got off of me and I sat up, taking off the condom. He showed me how to tie it, and he threw it away.

He laid down and I curled up in his chest.

"Was that okay?" I asked, looking up to him.

"God yes. It was great...was it good for you?"

"Mhm." He smiled at me.

"Well, I'm glad you liked it, baby boy." He kissed the top of my head. I felt my face grow hot, and I nestled my head in his neck to hide it. I yawned and he kissed my head again.

"Aww are you a sleepy boy?" I nodded.

"Can we sleep like this?" I asked. Ryan said of course. "Even naked?" He said yeah. I smiled and kissed his neck. He giggled.

"G'night honey."

The next day I began exploring a lot of other things about my identity. Ryan unpacked his makeup and asked me if I wanted to try some of it. I agreed, and Ryan did my eyeliner and lipstick. I looked in the mirror and I was surprised. I looked ..good? Ryan pulled the scrunchie out of my hair and brushed his fingers through it. I kind of looked like a girl.

"I have skirts and dresses too, if you want."

"No. No, I think I like this." I smiled at him.

"You look really pretty baby boy." I dug through Ryan's drawer and pulled out my oversized I Don't Know How But They Found Me shirt and put it on. I stared at my reflection a little too long. I felt like crying. Ryan noticed something was up and put his arm around me.

"Y'know, baby, this doesn't necessarily mean anything. You can be cis and like makeup." He said gently, I nodded, tucking my hair behind my ear. Ryan smiled.

"You look really pretty with your hair down. You always have your hair up." My face grew hot.

A few hours later, we were laying on the floor listening to Distractible, when I noticed something. I sat up. Ryan gave me a confused look. I pointed at his wall. He had a corkboard, which had tons of drawings on it. Some scribbles, some paintings, lots of weirdcore. But one stood out. The Sally Face drawing I did of Ryan. He kept it.

"Oh, that. Uh.."

"You really liked it?"

"Yeah, of course. I love it." I tackled him and kissed him. I felt myself get hard again. Ryan must have felt it too.

"Do you want help, baby?" He asked, kissing the side of my forehead.

"I think I wanna jerk off.." I got up, my knees around his waist, embarrassed.

"Okay. Do you want me to watch?" My face got hot. I hadn't even considered that was a thing that he could do. I thought for a second before nodding.

"Okay honey." I took off my clothes and looked down at my dick.

"So..do I just..?" I made a gesture of what he did the night before. Ryan nodded.

"Pretty much...Oh um, here." He handed me a bottle of lotion. I tried acting like I knew what to do with it. Ryan laughed. "You use it as lube." I nodded and put some on my dick and started pumping. I closed my eyes, biting my lip. It was weird and I was very embarrassed. When I got used to the motion, I went a little faster, but stopped when I heard Ryan whimper. I opened my eyes and was surprised to see that he was naked, his eyes shut tight, jerking himself off. I kept pumping on my dick, watching him, and his face. His head was back, his mouth wide open, letting out loud moans. It was so hot. I was admiring how attractive he was, when I came. Ryan moved his hand up to his nipple and started rubbing it. He let out a moan and came.

After we both recovered, he kissed my forehead.

"Sorry..I uh.." I gestured to the cum I had gotten on the floor, and his leg.

"It's okay." He wiped up the cum from his leg and put it in his mouth. Then he grabbed a baby wipe and wiped it up off the floor.