The Milton Diaries Ch. 01

From the Diary of David:

Tonight was a first. I thought of my sister as I masturbated. Sure, there had been other nights where she had come across my mind, but tonight, all I thought about was her. It didn't take long to get excited with the mental picture I had of her in my mind.

She was wearing her little black shorts with "SEXY" written across the ass, and a tight red tank top. I imagined her asking me to take down the straps of her tank top with my teeth, while my hands massaged her ass. In my fantasy with my sister, she kept whispering in my ear that I was a bad boy and only she could tame me. I liked that a lot. She threw me down on the floor and straddled me, her scantily clad pussy grinding against my erection. I buried my face in her tits and her hands grabbed hold of my cock and started stroking my shaft.

The actual sight in my room wasn't nearly as romantic as what I was picturing. My pajama bottoms were around my ankles as I knelt on my carpeted floor. I grasped a wad of tissue in my left hand, waiting for my cum, while my right hand was busy stroking my cock. How badly I wanted it to be my sisters' hand, or even better, her mouth. I was breathing heavily with each stroke, and occasionally her name would escape my mouth.

I'm not exactly sure at what point she walked into my room, but I wish she would have joined me instead of just watched. "What do you think you're doing?" she asked, and I came. Screaming her name, I came into my wad of tissue, which at this point was shredded because of my grip. My sister had caught me masturbating, which in itself wasn't all that bad. But she had caught me thinking of her.

My eyes jerked open, and I slowly looked over at my sister. Beads of sweat dripped down my face, as my cock emptied out into the tissue in my hand. 'What am I gonna do,' I thought. 'What is she going to do? I hope she doesn't tell Mom and Dad.'

With my shaft still in my hand but quickly losing its stiffness, I just regained my composure and stared at my sister. It was all I could do.

--- 3 months ago ---

Lately, the more I look at Amber, the more I realize just how pretty she is. I probably shouldn't think of her this way because she's my sister, but it's true. Her body, her smile, her personality...perfect. I don't know why she's single, but I like it that way. Now, I'm the only man in her life besides Dad...but he wouldn't notice her the way I do.

Being two years apart, we have always been as close as siblings can be. There are fights, and the times that we act like we hate each other. But when it comes down to it, there is a loving bond that exists between Amber and me. We became closer as we got older, and for some reason, I started noticing more things about her than I ever had. Her full pouty lips that glistened from her lip gloss. How thick and rich her chestnut hair was. The way her fingernails and toenails always matched. I didn't know why, but I couldn't help studying her body. Luckily for me, she'll be home more often now that she graduated college...until she finds her own place.

Then it happened...

The first time she entered my mind while I had my cock in my hand drove me crazy. Her body, well her feet, was the last thing I imagined before I came. I didn't know what to make of it. Why had my sister, of all people, invaded my mind while I was pleasing myself? I tried to shrug it off and tell myself it was an accident.

Little by little, however, she crept into my mind more and more while I was masturbating. It might sound weird to you, but the orgasms I had picturing my sister were the best. Every time I came thinking of her, my knees would buckle and I fell to the floor. That hadn't happened since the first time I explored myself. She's the reason that I make sure I'm kneeling every time I jerk off.

--- 2 months ago ---

Wow. Well tonight I did something I can't take back. While everyone was out of the house, I masturbated in my sister's room. It didn't take long at all for me to climax. With the fear of getting caught and her perfume filling the air, I was just about done the second I walked through her door. No one's going to know though. Not now at least. Not until I see if she has feelings for me.

The next morning I wasn't able to look at my sister the same way, and I think she knew something was up.

"What's with you today?" she asked.

When I get nervous, I tend to stutter a little bit.

"W-what d-do you mean? N-nothing's wrong," I lied. (See what I mean about stuttering?)

"You just seem...off," she replied. "Like you did something wrong and you're not telling me."

"Well, uhh yeah, I mean no. I d-didn't do anything wrong," I blurted.

"Then could you please stop looking at me like that?"

I don't think she bought any of what I said. Who would though? I've never been good at lying, and this was a situation where the ability to lie was very important. I wanted to tell her what had happened, but she wouldn't have understood. I still don't understand why I did it. I still don't understand why I'm getting these kinds of feelings all of a sudden. 'Maybe it's just a phase,' I tell myself.

I really need to learn how to lie...

--- 1 month ago ---

I think she might be on to me.

I thought masturbating in her room had been bad enough. This time I stole a pair of her flip flops...while everyone was home. Part of me wanted to get caught so everything would be out in the open. Part of me was glad that I wasn't caught...well not completely caught.

When I came home from work, everyone was downstairs. My sister looked beautiful. She was lying down on the couch wearing a pair of guys' gym shorts (were they mine?), which looked really sexy on her, and a white tank top. I think that's what made me want to sneak into her room. I was turned on, and she, along with my parents, was downstairs.

I started to climb the stairs, but needed to take one more look at her. My mom called up at me, "Are you going to watch some TV with us David?"

Damn. "Yeah, I'll be down in a few minutes Ma," I yelled as I headed up to my room.

Amber's room is across the hall from mine. I kicked open my door and threw my bag in there, not caring where it landed. I needed to act fast if I wanted to take something from her room. In a couple months, she would be in her own place, and I wanted something to remember her by.

Her door was closed, like it always was, and I had to quickly push it open in order to avoid the loud creaking sound her hinges made (a trick I learned when I masturbated in her room.) As the door flew open, her perfume hit me in the face, and I got that feeling in my knees again. Shit.

Get in.

Take something.

Get out.

But what?

Think.

"Got it," I whispered to myself.

When I started noticing more about my sister, I found out that I had a foot fetish. I never had it until I stared at her all the time. Her toes were perfect, and I wondered what they would taste like. Luckily for me, Amber loved to wear flip flops all the time and had quite the collection. She bought multiples of the same color, and I loved her worn green ones.

'I'm doing her a favor,' I told myself, justifying why I was about to steal her flip flops.

The ones I took from her closet are a pair that was well worn. The oils from her skin had left behind a dark footprint. Size 7.5. And now they were mine.

Once I took her sandals, I realized I had no way to smuggle her flip flops back undetected. Why did I have to throw my bag in my room? Even though I knew everyone was downstairs, I didn't want to take any chances. I did the only thing I could to hide her flip flops, and stuck them in my pants. I draped my shirt over what stuck out, and turned around.

Amber was in the doorway.

Shit.

'What am I gonna do?' I thought.

"What are you doing in my room David?" she asked, very unpleasantly.

"I-I uhh, was looking for one of my b-books," I said (I really need to learn how to lie.)

"What book?"

She wasn't buying it.

What came out of my mouth next seemed to take an eternity.

"M-my s-sketch book," I finally mustered up. "I c-can't find it."

"Well, it's not in here," she said. "So get out."

I didn't say anything else. I just left her room.

When I entered my own room, I shut the door. My face was covered with sweat, and my nerves were making me shake. But I was proud of myself. Not only did I manage to get my sisters' flip flops, but I was also able to make up an excuse for being caught in her room.

I threw her flip flops behind my door, and put on some shorts to be more comfortable. I went into the bathroom and splashed cold water on my face. I made my way downstairs and watched TV with my parents. My heart was still racing.

--- Present ---

Amber looked at me, and then stuck her head out into the hallway. She quickly shut my door and locked it behind her.

Confused, she asked, "Were you just thinking of me while..." her voice trailed off.

I simply nodded 'yes.'

She looked away and noticed her flip flops behind my door.

She pointed to them and started to talk. "Are those m-," is all she got out before I cut her off.

"Look," I started. "I'm really sorry Amber. I took those the day I -,"

"Lost your sketch book," she interrupted.

I nodded.

She shifted her weight to her left foot, and started to open her mouth.

Nothing came out.

She shifted her weight to her right foot and pointed at me in a scolding fashion.

Nothing came out.

I caught her looking at my cock, and I started to smile.

I didn't know what to expect her to say. I opened my mouth to apologize, but she cut me off.

"I could've just given you my flip flops had you asked David."

Now I was confused.

She crossed my room and sat on my bed. She crossed her right leg over her left and dangled it a few feet in front of my face.

"I had no idea you had a foot fetish," she said, pointing at me with her toes.

"I didn't...until I noticed yours Amber," I confessed.

She bit her lip and stuck both feet out to me.

"Show me how much you like my feet David," she demanded.

I crawled to her awaiting feet, and I stored the big toe of her right foot in my mouth. I heard her moan as I sucked on her toe. I grabbed her left foot and placed it on my chest. She started massaging my chest and stomach with her foot. Her nails scraped along my flesh each time she brought her foot up to my nipples.

I took her toe out of my mouth and started kissing her soles. Starting at her heel, I gave her feet little kisses. When my mouth reached her toes, I spread them apart with my tongue.

My cock hardened again while I was kissing her feet. Her left foot found my erection, and she slid her toes down my shaft. Her first two toes spread open, trying to fit around my girth.

"You don't deserve to fuck my feet yet David," she scolded.

I continued sucking on her toes, fitting three of them in my mouth. They tasted as great as I imagined. I picked up her left foot and started to give her a massage. My fingers gently pressed into her soles, massaging them in circles.

Amber took her feet away from me and rested both of them on my face. "Breathe in," she demanded.

I took deep breaths of my sisters' feet. They were as fragrant as her room had been, and I didn't want to stop...but she made me.

Amber brought her wet foot down to my thighs, and rested her big toe on the head of my cock. "You can fuck my feet when this foot is wet," she informed me.

My tongue quickly ran along her soles. I needed another release. I sucked on each of her toes, making sure they were all as nice and wet as her other foot. I ran my tongue up from her heel to the tips of her toes, and smiled at her. She told me to lie down on the floor and she would take care of the rest.

My cock was standing straight up in the air as I was on my carpeted floor. Two times tonight I would cum with my sister on my mind...only this time, she was helping.

She sat on the floor next to me, and placed her toes on either side of my cock. Slowly, she would bring them up and down my shaft. When her toes reached my head, she would lightly tap each side with her big toe. I wanted to explode.

She squeezed her toes around my shaft and started to stroke me faster. She began urging me on. Insisting that I cum all over her feet. She wanted me to let her know when I was about to cum, so I could jack off on the top of her feet. She said she had something else in store for me.

We changed around our positions. She was now on her back with her feet in the air, and I was back on my knees. I cupped her feet around my cock, and started fucking her them. Each time I thrust forward, my balls slapped against her heels. I was close to cumming, and it was with my sister.

Amber reached her arms back and picked up one of the flip flops I had stolen from her room. She started teasing me by licking the dark foot print that had remained. I couldn't take it anymore. I held her feet out in front of me like she wanted, and I came on her toes.

Even though I was on my knees, the force of my orgasm caused me to buckle and hit the floor. I was out of breath, and tired. That's when I heard her giggling.

"Did you forget that I had something else in store for you David?" she playfully asked.

'I can't take anymore,' I thought.

"Clean your cum off my feet and I won't tell Mom and Dad what I caught you doing tonight."

I had never tasted my cum before, but I really didn't want my parents finding out anything. I knew what I had to do but I must have taken too long to respond.

"I'm waiting David," she said dangling her feet in the air.

I picked myself up from the floor, beat, and started cleaning off my sisters' feet.

"I could always use someone to pay half the bills at my place David. Just think. We can be together whenever we want without any worries."

I couldn't pass up an offer like that. When her feet were clean, we told our parents I'd be moving in with Amber. They were hesitant at first, only because my sister was 21, and I was still only 19. They eventually came around though. I think the idea of an empty house appealed to them more than anything.

My sister and I walked upstairs holding hands. I kissed her in the hallway, and turned to go in my room. She grabbed the sleeve of my shirt, and tugged me into her bedroom.