Halstead Sister

First Time

This is a request for BrooklynDaniels32.
CW: These few chapters talk about sex and related issues but nothing graphic.

Tess POV 16 years old
I walked home from school holding my boyfriend, Jake's, hand. We've been dating for 4 months and I still hadn't told Jay and Will. I knew how protective they were over me and I didn't need them scaring off the first guy I really liked. It wasn't hard to hide given the long hours my brothers worked and I was left home alone most evenings.
"Wanna sleep over tomorrow?" Jake asked. "My parents are out of town for the weekend and my older sister told me she'll be at a party."
"I sure do!" I replied eagerly. "Maybe we can do what we talked about last time?" I looked at him. Last time I spent the night at Jake's, we talked about having sex. I wasn't quite ready then and he respected that. After talking to my friend who had been sexually active since the 9th grade, I felt more prepared and comfortable having sex with Jake.
"If you're ready" Jake agreed. We went our separate ways and I walked the last few blocks to my apartment.
"Hi" I said walking into the kitchen. Will was standing there in his scrubs. "Work?" I asked.
He gave me a sympathetic smile. "Afraid so. How was school?"
"Fine" I answered honestly. I followed Will as he walked toward the door to put his shoes on.
"That's good!" He slipped on his shoes. "Sorry I have to run. I'll see you tomorrow. Jay should be home before you're asleep. There's some leftover lasagna for dinner." He kissed my head. "Love you."
"Love you too. Have a good shift" I closed and locked the door behind him. I sat down in my room and did my homework. After homework and dinner, I curled up on the couch and watched TV while I waited for Jay to get home. Around 10:00, I heard the front door unlock.
"Sorry I'm so late" Jay said as he came into the room.
"No worries" I smiled. He came over and flopped down next to me. "Long day?" I asked.
"You have no idea." He sighed. "How about you?"
"It was fine." I gave him the same answer I gave Will. "Can I sleep at Lucy's tomorrow?" I asked. Since I couldn't tell him about Jake, I needed another reason why I wouldn't be home tomorrow night and I knew Jay wouldn't say no to Lucy. Lucy and I had been best friends forever and Jay knew her well. Our long friendship also meant that we had each other's backs and if it came down to it, we'd cover for one another.
"Of course" Jay answered just as I expected. "You going straight from school?"
"Yup!" I answered. "Thank you. I'm going to sleep. Love you" I gave my brother a hug before going to sleep.

The next evening, I was laying next to Jake as we watched reruns of Friends. During a commercial break I could feel Jake's eyes on me.
"What are you staring at?" I asked him.
"You" he smiled.
"I got that... but why?" I replied.
"You're hot. And I like you a lot. Plus, you're really hot" Jake leaned forward and kissed me. I turned so I was completely facing him and kissed him back. We continued making out for a while.
"Can we go to your room?" I whispered, my face still close to his.
"You sure you want this?" Jake asked. I nodded. Jake was a year older than me and I knew this wasn't his first time. I really trusted and liked him and knew that he cared about me. Jake stood up and lifted me into his arms. I giggled as he carried me into his room. He put me on his bed and we continued to make out and get undressed.
"You really ready?" Jake asked.
"Please" I kissed him and we proceeded to have sex.
After we were done, I was in pain. People always talk about how amazing sex is. I would disagree. It hurt. A lot. I didn't want to let Jake know how uncomfortable I was so I excused myself. I got into the bathroom and went to pee. I noticed there was some blood but given the fact it was my first time, I didn't think too much of it. I put on pajamas and made my way back to his bedroom. The pain in my pelvis got worse and I hunched over and groaned.
"Tess, are you alright?" Jake rushed over to me and helped me to the bed and pulled the covers over me.
"It hurt, Jake. I didn't think it was supposed to." I looked at him with fear.
"I'm so sorry. You should've told me. I would've stopped." He came next to me and wrapped his arms around me.
"I wanted to do it. I really did. It just still hurts." I leaned into his chest and cried softly. Jake tried to soothe me and I took comfort in being in his arms. I noticed a wet feeling between my legs and pulled back the blanket to reveal a large puddle of blood. "Jake?" My voice shook. He looked over and I saw him turn white.
"Shit Tess!" He exclaimed. "We gotta get you to a hospital!"
I shook my head. We were closest to Med and I didn't want to have to face Will. Plus, bleeding after your first time is normal. Isn't it? "Just help me change?" I asked him. Although he was more scared than I was, he agreed and took a pair of sweatpants and underwear from my bag before helping me stand up and limp to the bathroom. My pelvis still hurt and moving made it worse.
"Here, uh, sit down" Jake had me sit on the toilet as he helped me remove my pants. He handed me a damp washcloth so I could clean myself before he helped me slide on new underwear, with a pad, and sweats. I could still feel myself bleeding and I was getting a little woozy. "Let's go back to bed." He held out his hands and I grasped them. As I stood up, my vision became fuzzy and I felt lightheaded. "C'mon babe" Jake took a step forward. I attempted to follow him but felt myself going down as everything went black.