My Sister's Diary Pt. 01

"Hey! Good, good as you can be these days. You?"

"Same, same. So happy to finally get out of the house. You've really filled out since school." She said, punching my shoulder.

"Hit the gym here and there, looks like you'd know a thing or two about it." I said, wondering if this could go anywhere.

She smiled, "Maybe one or two. You never told me you had a younger sister!" She said, leaning down towards Abby. I don't blame her, Abby's small and was holding my hand like she'd be my younger sister, but to Abby that was unforgivable.

"I'm his older sister, you stupid bitch." Abby said plainly.

Jennifer had a surprised look on her face, and I said, "Woah, woah Abby, it's alright. Sorry, Jennifer."

"It's alright, my mistake." Jennifer said. "So you're Abby? All your brother would talk about back in school, nice to meet you."

Abby just stared daggers, and it was awkward silence.

"Well, I should get back to work. Nice to see you again Jake."

"You too." I said to her back, and Abby's grip on my hand loosened.

Abby and I took our seats and I asked, "What was that about?"

She shrugged her shoulders and said, "She was all over you. The whore was going to drop to her knees and perform fellatio right here."

I scoffed and said, "Come on Abby, she was just a friend from school."

"Yeah. Okay."

We ate our food and shared a milkshake, at which point we were both ready to head home. In the car, she asked "How many times do you masturbate per day? And at what times?"

I scoffed as I felt my face getting hot and said "I don't have a set schedule for masturbating, sometimes don't even do it in the mornings."

"Well, you should."

"Why?" I asked.

"Schedule and routine are good for the mind and body."

"Masturbating is more of an on the need basis. Do you have a scheduled time to masturbate?"

She blushed, but nodded. Of course she did.

"What time?"

"It's not important."

"Oh come on, all these questions about me, give me one."

"Sundays, 3 PM."

I looked at my watch, Sunday, 2:17 PM.

"You masturbate once per week? And that's 45 minutes from now. Cutting it pretty close aren't we..." I said, as I started to realize what that was implying. Most Sundays I took her to bingo, and it was a great opportunity for us to spend a lot of time together. And she masturbated right after we'd get home. Every time.

Once home she hurried up to her room, presumably to make an entry in her diary about her morning and, well you know what. The thought crossed my mind to go listen at her door, but I chickened out. I laid in my bed and at 3 PM, I masturbated.

The following morning things took a step in a direction I did not see coming. I was woken up by something touching my hand, and I was surprised to see Abby already standing at my bedside in her tank top and panties, holding my hand. "Abby? Everything alright?" I asked groggily. Usually when she broke her routine, something was wrong, and it worried me.

"Yes." She replied.

"What are you doing in here?"

"Waiting for you to wake up."

"And why are you doing that?"

"So you can look at me while you masturbate."

Awkward silence. "What?" I said after a few seconds.

"So you can look at me while you masturbate." She said again simply. I just looked at her, unsure of what to say. "Come on, chop chop." She said, clapping her hands together.

"Why are you doing this?" I asked her.

She thought to herself for a moment, and said "Because I want to please you, and I enjoyed watching you masturbate and ejaculate. Now are you going to do it?"

I knew I shouldn't, but I did anyway. I pulled my covers away and exposed my erection to Abby, just an arms length away from me. Her eyes flicked down to my groin and I started stroking. She inched closer, and I scooched over so she could sit on my bed.

After sitting she suddenly, and quickly reached out and wrapped her hand around my shaft, I was too stunned to speak. "See? Like I said it's a perfect size for my hand." She said, pointing to where her fingers just barely met around me. She released me just as quickly as she had grabbed me, and I continued.

I felt very strange looking at her while I masturbated, nonetheless, it was exciting. "Would you like me to undress?" She asked after I looked over her body.

"You don't have to do that."

"If it would help, I want to."

"I guess it would help."

She quickly pulled her tank top over her head exposing her breasts, and then her panties down her legs exposing her wiry pubic hair and her beautiful pussy. She was sat a bit catawampus to me, and spread her legs, giving me a better view than I could have possibly asked for. "I hope it looks presentable, I have not shaved for a while." Not that I didn't already know, you could see her pubic hair sticking through the front of her panties on occasion.

"Abby it's amazing. You're amazing." I said, scanning her body thoroughly. Abby's breasts were perfect for her frame, not indiscernible, but not obtrusive either, with pink and perfect round nipples. Her vagina, despite the hair being unkempt, was neat and tidy. Her pussy was surprisingly plump given her size, even with her legs spread a bit her inner lips were barely visible, just two parallel lines covering her opening. She spread her legs even wider as she saw me stare in intrigue, which made her lips blossom like a flower. This also allowed for her clitoris to protrude freely, the erect little bead poking out from beneath its hood.

"Aren't you... horny?" I asked.

"Of course I am."

"Do you want to do it with me?"

Abby bit her lip cutely and she looked a way I've never seen her before. Vulnerable. Open. "Not today." She whispered. "Unless you really want me to."

"No, no that's okay. You're so beautiful Abby." I said.

"Thanks." she said as she watched me stroke myself. "You're... attractive." I smiled, and thanked her. I was already close, seeing the most intimate parts of my sister was having a profound effect on me. She seemed to realize, she excitedly sat up on her knees and said, "There you go. Let it all out for me Jake."

That was all it took to push me over the edge, and I came very hard. My toes curled and my legs tightened as I shot and shot all over my stomach and groin. Abby watched on intently as I came, and put her hand on my thigh which heightened my senses and made the orgasm seem to last longer. She stood to grab a towel from my laundry basket and handed it to me, then to my surprise laid in bed next to me. "I wish I was allowed to just stay naked all the time."

I chuckled and said, "I wish you could stay naked all the time, too." and it made her giggle. She has such a beautiful laugh. She scooched over to cuddle, and I raised my arm to accept her in. Her naked skin on mine was quickly arousing me again. She looked up and pecked my lips three times in succession, and a fourth, I kissed her more than a peck. She smirked and laid her head back on her shoulder. I looked at my phone for the time, 7:47. 13 wondrous minutes to cuddle in the nude with the woman I love the most.