Step Family Parody-Chapter 9: Step by Step to Stepmom Cha. 05

She stepped down a bit and asked, "What exactly did you hear?" with obvious concern in her voice.

"That Jackie asked you to hang out with me and set me up with Natalie. That you guys planned on getting me laid. Was anything about that night genuine?" I asked shakily.

"Of course it was. First off, you had no right to be eavesdropping on us. I understand if the door was open and you happened to hear, but spying on us through the door is unfair."

"What would have happened if I didn’t? I would be strung along like a puppy believing that you wanted to have sex with me."

"I already told you that I did. Look, I’m sorry it had to happen like that, but aren’t you glad that it happened? I certainly am."

I stayed silent for a solid five minutes before Charlotte tried to speak again, but I calmly said, "Could you please get the fuck out of my room?"

"Noah, I..."

"Please get out of my room!" I said sternly.

It was clear she didn’t want to, but with an empathetic look in her eyes, she reluctantly left me alone. A wave of depression was about to wash over me. I could just feel it. And in what had become second nature, instead of dealing with it, I simply went to sleep.

The next day, I woke up debating whether I should call in sick or not. It was the day before we closed for the holidays, meaning it would be one of the busiest days of the year. Ultimately, I figured having something to do would be better than doing nothing and having unwanted thoughts in my head.

Going to work turned out to be the right decision, as the conversation didn’t pop up in my head once. I even volunteered to stay longer just for that reason. But unfortunately, I had to go back home. As I was walking out, I heard a couple of my coworkers talking about heading out to a bar. It was uncharacteristic of me, but I asked if I could tag along, and they said sure.

We ended up bar hopping till all the bars closed at 2 in the morning. Not wanting to risk it, I left my car and Ubered back home. I quietly let myself in and went up to my room. When I turned on my lights, I was startled as Jackie was lying on my bed.

The light woke her up, and after rubbing the sleepiness out of her eyes, she asked, "Where were you?"

"Out, with friends. Uhm, what are you doing in my room?"

"Charlotte told me about what happened. I, uh, wanted to talk to you and apologize."

"For what?"

"Wanna take a seat first?" she said as she patted the spot next to her on my bed. "You don’t look to steady." I sat down next to her, relieved that the world had stopped spinning around me for a second.

"I want to apologize for treating you like a little kid. I just wanted to look out for you, but you’re old enough to know what you’re doing."

"I get it. You’re looking out for me, but like you said, I know what I’m doing. I know what I want."

"Cool. Are you mad at Charlotte?"

"Did she send you here to be peacemaker?"

"No. I came here on my own. Look, she was doing me a favor. There’s no need for you to be mad at her. From what she said, it sounds like she’s happy the two of you slept together."

"I am too, but I’m upset at how it happened. But having sex with a girl like Charlotte is worth it, I guess. So, thank you for that."

She laughed and said, "Yes, you did do that, and you’re welcome."

"You know the last time I had sex was the summer after high school. Then my girlfriend broke up with me the next day."

"It’s been 3 years? Jesus, you did need that. In that case, you’re very, very welcome, and I take back my apology. Word of advice: next time, try not to have sex with your stepsister and instead have sex with the girl she’s trying to set you up with."

"I’ll consider it. What’s the longest dry spell you’ve had?" I asked as I laid back into bed.

"For what?"

"Sex."

"Oh, uhm, weird question to ask your sister. But I want to say 6 months, give or take."

"Alright. Was that because no one wanted to have sex with you? Or because you didn’t want to have sex with anyone?"

"Where are you going with this?"

"Just answer my question."

"Ok. Guys made their moves on me, but I shot them down. Now will you tell me where you’re going with this?"

"For a beautiful girl like you, you can get what you want whenever you want. Not just sex. It can be anything. For me, it’s not like that. That first year of being single, I went out with Jordan and Alec to college parties, and nothing ever happened to me. That destroyed me. Seeing people pick up girls with ease while I struggled to even have a conversation."

"You gotta give it time. And you putting yourself out there is a good thing. You should’ve kept at it. Never know when you’ll have a breakthrough."

Feeling the alcohol coming back up, I sat up.

"Ehh, I figured the party scene wasn’t for me. Learned to be happy with what I got. Few good friends, games, job that keeps me busy."

"That’s not all life is Noah."

Not wanting to get a sappy lecture, I stopped her before she could start. "Why don’t you tell me about your college life?"

"Med school. Tough, barely any time to yourself. Swamped in books, lectures, and practicals. I miss pre-med. Life seemed so much easier then."

"You’re not getting as much dick then?" I asked bluntly, the alcohol clearly in control.

Jackie looked at me in shock before smiling. "I didn’t say that. I need something to keep me sane."

"Is this my sister’s admission of guilt to being a slut?"

She playfully slapped me on the arm and said, "I am not a slut. Just a lover of sex. It’s something a person who has sex once every 3 years wouldn’t understand."

"It will not take me another 3 years."

"Why? Is Charlotte’s sister coming into town anytime soon?"

"No, though I’ll keep it in my mind. But I was thinking, why mess around with stepsisters when I have a sister."

"Ok, there. Someone has clearly had a lot to drink and needs to sleep it off. Plus, according to you, I can get dick whenever I want from whoever I want. I think I’ll finally satisfy Alec’s dream. I’ve been dragging the poor guy long enough."

Before she could get up, I leaned in and smushed my lips up against hers. She kept her lips closed so I couldn’t get my tongue in, but she didn’t pull away immediately.

She did push me away after half a minute, flustered and red in her face. "Uhm, that happened."

Subconsciously, I began to rub my hard cock through my jeans. It didn’t go unnoticed by Jackie, who let her eyes linger for a minute. She got up and said, "I’ll let you take care of that in private."

I held on to her hand and asked, "Why not help me?"

"Noah, you’re drunk. It’s not a good idea, even if you weren’t drunk, it’s not a good idea. It’s not like Charlotte. We’re related by blood. This would be crossing a line that there’s no going back from."

"I’m not that drunk. I’m drunk enough where I think this is a good idea. Come on, we don’t have to have sex. What about a blowjob? A handjob?"

She stood there as if she was contemplating it. "I don’t know, Noah. We could end up regretting this..."

"Life is too short to worry about regrets. If we regret it, we live with it." I stood up and put her hand over my crotch. "Your little brother needs help. You said you were looking out for me before. What’s changed?"

Jackie took a deep gulp, her eyes fixed below my waist. Then, she pushed me onto my bed and got on her knees. She brought her hands to my pants before suddenly pulling away and walking to the door. With a big grin on her face, she said, "You wish oh little brother of mine." She slipped out of my room, leaving me with blue balls.

I was rock hard with no one but me to take care of it. Reluctantly, I jerked myself to sleep, using tissues to clean up.

The next day was Christmas Eve, and I woke up to some rustling in my room. I opened my eyes to see Charlotte poking around.

"Someone didn’t get lucky last night." She picked up my crusty tissue to examine it and noticed a few others scattered across my bed.

My flaccid dick was exposed and I tucked it back into my pants. "What are you doing in my room? Get out!"

"You’re not still mad at me, are you? Jackie said she would talk to you."

My head was throbbing, a reminder of how much I had had to drink last night. "No, I’m not. Can you leave my room, please? Close the curtains on your way out. The sunlight hurts."

"Okay, Vampire. I’ll let you get your beauty sleep, but I don’t think your dad will. He sent me up here so we can all eat breakfast together."

She sauntered out of my room while I tried to catch any sleep I could before my dad called for me. It didn’t take long for my dad’s heavy footsteps and booming voice to make his way to my room. He barged into my room shouting, "Noah! Everyone is waiting for you! I sent your sister up here to call you, but she said you were in deep sleep."

"Just give me a second, and I’ll be down."

"Take a shower first, you reek of alcohol." He gave me one last disapproving look and closed the door.

I forced myself out of bed and into the bathroom, where I started things off with a blast of ice cold water to wake me up. It did the trick and temporarily cured my hangover. The shower was a quick one since I didn’t want to risk the wrath of my dad. When I got downstairs, everyone was seated at the table, patiently waiting for me, except for my dad, who was seething.

Samantha started serving food and said, "Here’s to a cheery Christmas Eve breakfast. Isn’t that right, Dear?" looking at my Dad.

He mumbled and ate his food silently. As we were clearing the table up after breakfast, Samantha said, "Hey Honey, can you come with me to the store? I have some last minute items I need to get for Christmas dinner."

"Ugh, fine. Give me a minute to get changed, and I’ll be down." He went upstairs, and she looked at me, saying, "I’ll do my best to calm him down. But you, mister, you need to be more careful. You know how your dad gets."

"Yeah, I know. Thanks for taking care of him."

A few minutes later, they left the house to take care of Samantha’s made-up shopping list.

Jackie, Charlotte, and I were still hanging out at the breakfast table when Jackie asked, "How did you take care of your problem last night, Noah?"

"When I went to wake him up, I found a handful of cum tissues. I assume he did it himself, right?" Charlotte said.

Jackie smiled, saying, "If it wasn’t me and it wasn’t you, then it was him. However, he did ask me to lend a hand."

"Oh, you didn’t, Noah," Charlotte said mockingly. "Asking your sister for a handjob? You could’ve asked me, and I’d be more than willing to help you out."

Unknowingly, I was getting aroused hearing my sisters talk about me. Jackie was the one who pointed it out. "Looks like he can use a hand now. What do you say, Charlotte? Are you all bark, no bite?"

Charlotte locked eyes with me and answered, "I’ll do it. The question is, should we do it in front of your sister or ask her to leave?"

A lump formed in my throat. Things were ramping up fast, real fast. The thought of my sister seeing my dick and watching me get jerked off was turning me on even more. However, I didn’t want to ruin our relationship. Sure, she was playing along, but I wasn’t sure if it was just play or serious. I looked to her, desperately wanting her to make a decision.

"I don’t want to be left out of the fun. How about we take this to the living room?"

The three of us moved to the living room. I sat down on the sofa, and Charlotte wasted no time getting on her knees and working on freeing my cock. Jackie sat on the sofa, facing us.

Charlotte pulled out my penis and looked over at Jackie. "What do you think of your brother’s cock?"

After examining it, she answered, "Impressive. Not the biggest I’ve seen, but definitely towards the top."

"Exactly, what I thought," replied Charlotte. "Let’s try to not cum in two minutes this time." Both her hands wrapped around my shaft and started to stroke me. It was nice, gentle, and felt like heaven. Handjobs always got a bad rep, but if you ask me, if a girl is playing with your dick, it’s a win.

After she made sure I lasted longer than last time, she started going faster. She used precum and spit as lube, making it even better.

The only sounds in the room were of the sloppy handjob until Jackie asked, "Do you not take your tits out? Give guys something to look at."

A smile crept along her face, and she replied, "He’s already seen my tits before. But, I’ll happily show him again if you take your tits out too."

This was the first sign of hesitation shown by Jackie, but it didn’t last long. She reached for the hem of her shirt and pulled it over her head to reveal her beautiful tits held up in a dark green bra. "Take your top off, we’ll drop our bras together."

Charlotte did as told to reveal a red bra. "On three?"

Jackie nodded. Both of them unclasped their bras, holding them up. She then started counting down, and on three, both of them dropped their bras. My eyes immediately went over to Jackie’s tits. They were even more perfect than I had imagined. They were firm, big, and perfectly shaped. She had a small birthmark on her right tit that caught my eye. She lifted them and let them drop as she bounced and jiggled.

"What do you think of your sister’s tits?" she asked me.

"Like..." I managed to stutter. Both of them laughed at my awestruck state.

Charlotte continued jerking me off while they were laughing and caught her by surprise when I came. It erupted out me like never before, with the first few spurts landing on her hair and face. The rest oozed out over her hands and on me.

Her mouth was wide open from the surprise and I saw some of my cum seep into her mouth.

"Oh my god! That was insane," Jackie said. "You came so much!"

Charlotte used her shirt to clean the cum of her face. "You lasted longer but still caught me by surprise."

"You got some in your hair," Jackie pointed out.

After confirming that she did, Charlotte got up, saying, "I’m gonna need to shower to get this out." She left for upstairs, leaving Jackie and me alone.

My dick wasn’t fully erect, but had yet to go down. Jackie put her bra and shirt back on and advised me that I should get cleaned and dressed before Dad and Samantha came back. She went upstairs as well as I sat, processing what had happened.

I don’t know how long I had sat there, but the sound of a car pulling into the driveway knocked me out of my trance. Not bothering to clean up, I pulled up my pants and ran back to my room.