The year was 1995, it was summer and I just got home from another day hanging out with friends. I was 18 at the time, and I had plans to go to college in the fall. I lived with my mom and stepdad, he asked me to call him Jim, so I did. He had a daughter from a previous marriage visiting for the summer. Her name was Carolyn, and she was 19. The first time I saw her, I thought to myself, damn, she’s pretty good looking. She had a curvy body, medium length auburn hair, and breasts that weren’t too big. She had a nice personality, always putting others before herself. I didn’t really get to know her when my mom and Jim started dating or when they got married.
If I wasn’t hanging out with friends, I would hang with Carolyn and get to know her. Sometimes we would play on the Super Nintendo and other times we would watch MTV. We both would laugh watching Beavis and Butt-head. Sometimes she would unknowingly put her hand on my leg while laughing, I didn’t mind though.
I was sort of seeing someone during the summer though, Amanda Morrison was her name. She gave the best blow job, we still haven’t gone all the way though. At night, I would lay in bed, stare up at the ceiling and think about Carolyn. I wondered if she could give a good blow job. The thought filled my mind and the blood raced to my dick.
I woke up one particular morning to knock at my door. It was Carolyn, who was wearing a revealing night shirt that hardly covered her panties. I tried to concentrate on not looking down. Innocently, she asked for some brotherly advice.
“Hey Jack, I was wondering if I could ask you for some advice.”
“Sure, what’s on your mind?” I replied.
“Well, I’ve been sort of seeing someone lately, and I’m pretty sure that he wants to have sex.”
“Are you asking me what you should do?”
I asked.
“Well, yeah. You’ve been with Amanda for a while now. Have you guys had sex yet?” she asked.
I had to pause for a moment, I felt the heat of embarrassment on my cheeks. Carolyn definitely noticed.
“Oh, I’m sorry for asking, I didn’t mean to embarrass you.”
“It’s okay, Amanda and I haven’t had sex yet.” I replied.
Carolyn seemed to be surprised by my answer.
“Look, just tell him that you’ll take it to the next step when you are ready, he should understand. If he doesn’t, tell him to fuck off.”
Carolyn gave me a smile, I could tell she was somewhat relieved of the predicament that she was in. She leaned in to give me a hug, her breasts pressed against me, I could tell that her shirt had risen up above her panty line. I was having such a hard time not looking down. She stepped back and thanked me before heading back to her room. Thank goodness she didn’t see the huge erection poking out of my boxers.
I had to release the pressure from my aching balls. The thought of Carolyn overwhelmed me. Her smell of perfume lingered on my shirt, she even smells nice in the morning. I quickly ran to the bathroom, closing the door behind me. I sat down on the toilet, boxers at my ankles. I began stroking my dick, the thought of Carolyn on my mind. Faster and faster, I was so concentrated on jerking off, I didn’t hear the door open.
“Oh! I am so sorry, I should have knocked first.”
I looked over, still semi jerking, to see Carolyn standing in the door frame. She immediately looked away. I quickly snapped out of it and pulled my boxers up.
She quickly closed the door behind her, and I was once again embarrassed. After collecting myself, I opened the door. Carolyn wasn’t standing there like I thought she would be. I contemplated on whether to address the situation that had unfolded or just to move on. I ultimately decided to move on from the situation.
Later that day, I was at Amanda’s. We were making out pretty heavily on her bed. Our tongues clashed in each other’s mouths. Was this going to be the day that Amanda and I go all the way?
“Do you want to take this further?” she asked with lust in her eyes.
I was lost for words for some reason, so I just nodded in agreement. Amanda smiled and leaned up to pull her top off. I also sat up to pull my shirt off. Amanda undid her bra to reveal her breasts. They were just the right size with small nipples. She leaned back down to kiss me, her naked breasts pressing against my chest. As we made out, I ran my hands all over her body, feeling the stiffness of her nipples, all the way down to the shorts she was wearing.
I slipped both of my thumbs under the waistband of her shorts and panties, and slowly pulled them down. She followed soon after and undid the belt and zipper on my shorts. She slid them down along with my boxers, my hard dick sprang free. Amanda laid next to me, and began sucking on my neck while she began to stroke my dick. Shit, it felt good, each stroke was a little faster. I quickly maneuvered my hand to search for her pussy since I was keeping eye contact with her. Once I found it, I stuck 2 fingers in her slit. She let out a moan, for the next few minutes, we mutually masturbated each other.
My mind knew that I wanted to fuck her, and so I positioned myself to where I was between her legs. We made eye contact as I slowly moved my dick into her pussy lips, past the outer wall, and finally all the way in. There was a sound of a plop as I entered her. The muscles of her pussy contracted as I began to thrust slowly. She was so tight. We were really going at full speed a few minutes later. Things seemed to be going good until….
“Ohhhhhhhhhhh, fuuuuuuuck Jerry!” she cried out in pleasure. I stopped dead in my tracks so to speak.
“Who the fuck is Jerry?” I asked.
At this point we had stopped having sex. My girlfriend had just screamed in pleasure with another man’s name.
Again, I asked “who the fuck is Jerry?”
Amanda couldn’t believe that she had blurted out that name. I would find out months after that Jerry was someone Amanda knew and also was apparently fucking while we were dating. I immediately pulled out, got off the bed and walked out of the room. Amanda just laid there, upset with herself.
I pulled into the driveway at home and pulled behind Carolyn’s car. I put the car in park, but before I got out, I hit the steering wheel multiple times in frustration. I got out of the car and slammed the door behind me. I tried to collect myself before entering the house, and when I walked in, I was greeted by Carolyn with a smile. She was wearing a white summer dress with roses that went just past the middle of her thighs.
I tried to smile back but I was still frustrated. Carolyn could tell I was frustrated.
“Everything okay, Jack?” she asked. I looked down at my hand, it was red and it hurt like hell. My mind had a million thoughts going through my head. I wanted to throw up, but not here, not now.
“Jack, is everything okay?” she asked again. I tried to speak, but all I could do was sob. “Fucking Amanda has been cheating on me.” I said sobbing.
Carolyn pulled me close to her, I cried into her shoulder.
“That bitch,” she said. “Come on, let’s go sit down on the couch.”
We walked over to the couch and plopped down. I had gotten my crying under control.
“Tell me what happened,” she said.
I had only seconds to decide if I was going to tell what Amanda and I were doing when I realized she was cheating on me.
“So, I was at Amanda’s, and we’re making out, and she asks me if we should go all the way.”
“Go on,” she replied.
“So we’re doing it, and it’s my first time”
As Carolyn is listening, I can hear breathing get a little faster as I decided to go into detail. I almost wondered if she was thinking about me masturbating earlier.
“And then she yells out some other guy’s name as she orgasms.”
“That’s really fucked up,” she replied.
“Yeah, then when I got home, I fucked up my hand hitting the steering wheel multiple times in frustration.”
Carolyn grabbed my hand and noticed how red it was. It still hurt a lot and I winced in pain.
“Shit Jack, you should probably put some ice on that. I’ll get an ice pack.”
Carolyn got up and went to the kitchen, a few minutes later she came back with an ice pack. As she held the ice pack on my hand, I couldn’t help but notice how beautiful she looked.
“You look beautiful,” I blurted out.
She looked up at me, obviously blushing.
“You’re just saying that,” she said with a smile.
“No, I really mean it.”
We looked into each other’s eyes, and a small spark ignited. However, it was quickly diminished when mom and Jim walked into the front door.
“We’re home, and we brought pizza.” My mom said.
We all sat at the table, it was mostly quiet. After dinner we had small conversations and even played a board game. It was getting pretty late when I decided to head to bed. I did have an emotional day after all. I slipped into my shorts and sleep shirt and headed to the bathroom. I was brushing my teeth when Carolyn came in, once again wearing her revealing night shirt. I gave her a glance and she smiled at me. I finished brushing my teeth and headed to my room, closing the door behind me. I fell back on the bed and stared at the ceiling, until I fell asleep.
I heard a faint knock followed by the sound of a slow creaking door open. I looked over at my alarm, it was 3:15 in the morning.
“Jack, are you awake?” Carolyn whispered. I tried to pretend that I was asleep. I heard footsteps get closer until there was the sound of creaking from my bed. She nestled up next to me, pressing her body against mine. This definitely had to be a dream. I felt her grab my arm and place it on her bare thigh. Her skin was smooth.
“Come on Jack, I know you’re awake. I can’t sleep,” she whispered.
I slowly opened my eyes and looked directly at Carolyn. She gave me a sultry smile.
“Why can’t you sleep?” I asked.
“I’ve been thinking about….”
“Go on, tell me, what’s on your mind.”
“I’ve been thinking about when I saw you masturbating,” she said.
I was honestly lost for words. I went back to thinking that I should have locked the door. I removed my hand from her thigh, and yes I had thoughts about Carolyn, but she was my stepsister. Carolyn bit her lower lip before kissing me on the lips. It caught me off guard that she had slipped her tongue in.
“I also got hot when you were telling me that you and Amanda had sex,” she said devilishly.
I tried so hard to resist her advances, but she made it so hard and it made me so hard. I was able to convince her that it wasn’t the right time. She got up from the bed, and walked out of my room without saying anything. Did I just miss my only opportunity? It bothered me until I got really tired and fell back asleep.
I woke up to my alarm, my door was closed, no scent of Carolyn on my bed. It had to be a dream. I went downstairs to the kitchen, Carolyn was eating breakfast.
“Where’s mom and Jim?” I asked.
“They went up to Walton Creek for the day,” she answered coldly.
Earlier that morning was not a dream, I thought to myself. Carolyn was not wearing her revealing night shirt, instead she was wearing black shorts and a white tshirt. There was some obvious tension between her and I.
“Look, about earlier this morning….”
“Save it, I don’t want to hear it,” she replied again coldly.
“Carolyn…”
She turned around to me, she was upset with tears in her eyes.
“We’ve got to hang out this summer and I’ve enjoyed it. I didn’t get the chance to know you when my dad and your mom started dating. Hell, I didn’t really know you at the wedding. But this summer has been the best opportunity, and I found myself attracted to you,” she said tearfully.
I walked over to her, the things she had to say really touched my heart. I looked into her eyes, and without much hesitation, I kissed her on the lips. She pulled back from the kiss. Was she still upset from earlier this morning? She came in close, put her arms around my neck and kissed me. She smiled through her tears as she pulled back. I gently wiped away her tears, and then picked her up.
I carried her to the couch and gently put her down. She pulled me down to the couch with her, I was on top. We made out for a while, wrapping our tongues in each other’s mouths. She would rub her fingers through my hair as we made out. We stopped for a moment to catch our breath.
Carolyn looked away from me and smiled.
“What are you thinking about?” I asked.
She looked up to me.
“Just liking how this morning is going so far,” she said.
“It can get more interesting, only if you want to,” I replied.
“Jack, I want to, my heart is telling me that I want it to be you.”
I leaned down to give her another kiss.
“Not on the couch though,” she said.
With that, we both got up and she led me upstairs, holding my hand. She opened the door to her room, as we entered, I was greeted with the same scent from yesterday. We walked over to the bed, and Carolyn gave me a deep and passionate kiss.
She put her hands on my chest and playfully pushed me onto the bed. I positioned myself to the center of her bed. She stood in front of me, slowly pulling her shirt to reveal her white lace bra. I could feel the blood rushing to my dick. Next she pulled down her shorts to reveal her white lace panties. She climbed on top of me and started sucking on and gently biting my neck. I grabbed her ass, I moved my hand towards her crotch, pulled her panties to the side and stuck my fingers in her pussy. She gave out soft moans as I slowly fingered her.
She looked up to me, “let’s get those clothes off.” I pulled my fingers out of her pussy and leaned up for her to take my shirt off. She got off of me so I could pull down my shorts, my dick was trying to poke through my boxers. She grabbed my dick through the boxers.
“Well, someone’s happy to see me,” she said devilishly. She pulled my boxers off and my dick was free. She threw the boxers on the floor as she got up from the bed. I slid to the edge of the bed, and she got on her knees and started sucking my dick. She started with just the tip, lubricating it with her saliva. She took all of me in her mouth, down to my balls. I leaned back on the bed, grabbing the bedding as she would come all the way to the tip and back down.
I felt my balls tighten and then the release of my hot cum in her mouth. She let my dick out of her mouth as I shot some on her face. She wiped some off and licked her finger. She climbed on the bed next to me.
“How long will it take for you to get hard again?”
“Not too long,” I replied.
She grabbed my hand and placed it on my dick. She held my hand and we stroked my dick together. It didn’t take long for me to get hard again. She sat up to take off her bra, her breasts fell and they looked great; I leaned up to suck on them gently.
After a few minutes of sucking on her nipples, she laid back down on the bed.
I looked into her eyes as I pulled down her panties. She had a patch of auburn hair above her slit. I leaned down nibbled on her pussy lips and she grabbed the sheets with pleasure. I licked her outer wall for a few minutes, she grabbed my hair to pull me up.
“I want you inside me, please.”
I leaned up, grabbed my dick and guided it into her pussy. The tip slipped right in and then I felt myself slide all the way in.
“Oh, fuck.” We both let that out.
I leaned down just enough to kiss her as I started thrusting slowly. She was tight and warm. I looked down to her, she was enjoying it. She smiled but it was taken over by pleasure. I could feel the muscles in her pussy begin to contract and grip my dick hard. I kept thrusting, increasing the speed and pressure. Our orgasm was building and building and building. The pressure blew like a volcano as we both orgasmed.
“Ohhhhhh fuuuuck, Jack!” she screamed in pleasure. “Oh, I’m coming so much!”
I fell on top of her, my dick still inside her, shooting my hot cum.
“Promise me, Jack, promise this won’t be a one time thing.”
“I promise,” I said with exhaustion.
I got off of her and my dick fell out of her. We laid with each other for a while,both exhausted, exchanging kisses. I would play with her nipples, and she would tell me to be careful not to turn her on. I did it anyway.
There wasn’t much summer left, so we would find every opportunity to sneak off, even for a quickie. Summer ended quickly, and it was time to head to college for my freshman year, and she would be a sophomore at a different college. We kept in touch with letters, and eventually email.
The End
Part 2?