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The Anderson Family Journals

Copyright© 2022 by Mr. Here

Timmy #03: Touching Diana

Incest Sex Story: Timmy #03: Touching Diana - A "Journal-Style" story featuring members of the Anderson Family, mostly told through Timmy's POV. ------ I've posted this story to SOL before, though I can't remember how much. I've made some changes, such as making the siblings triplets and aging everyone up to 18. The sex is still hot, won't change that.

Caution: This Incest Sex Story contains strong sexual content, including mt/ft   Ma/ft   mt/Fa   ft/ft   Teenagers   Consensual   Reluctant   Romantic   Teen Siren   Lesbian   BiSexual   Heterosexual   Fiction   Cheating   Sharing   Incest   Mother   Son   Brother   Sister   Father   Daughter   Cousins   Uncle   Niece   DomSub   Light Bond   Rough   Group Sex   Interracial   White Male   White Female   Oriental Female   Indian Female   White Couple   Anal Sex   Analingus   Cream Pie   Exhibitionism   First   Massage   Masturbation   Oral Sex   Tit-Fucking   Voyeurism   Big Breasts   Public Sex   Small Breasts  

Touching My Sister

Monday

I’ll give you a little bit of time to appreciate me.

That’s what Diana had said before closing her door on me last night, and that was the first thought that went through my mind this morning. What had she meant by that? I thought about her words all day without reaching a rational conclusion.

School had started. I was a senior. Diana was a senior and Abbey was a Junior. Unlike like Diana and me, Abbey didn’t have any free periods. So, it’s back to the same old routine at my house. School, pre-season wrestling workouts, homework, relax, rinse, and repeat.

Last night Diana told me to bring her the same water bottle today that she had refused the night before. The same fucking one—and you know what—I brought it to her. I put that water bottle downstairs on the bottom shelf in the back of the fridge, and I left it there so I could bring it to her tonight. What in the hell was wrong with me?

Diana could have taken it upstairs herself. Everyone was in the living room when Abbey went to bed before my mother went to the kitchen. Diana was on the couch, wearing those athletic leggings that were thicker than yoga pants, but not by much. They made the muscles of her thighs pop, and they were only long enough to cover her leg down to the middle of her calves. Up top, she wore an oversized sweater that she had been relaxing in all night.

“I’m going to my room,” Diana said as she got up from the couch and headed toward the stairs, ignoring the kitchen and her bottle of water.

It was nearing ten o’clock, so I rose and went to the fridge to grab the water. I told Mom that I was going to bed, and she hugged me goodnight, something she didn’t often do these days. Though, I have noticed that she’s more than likely to give me a hug or kiss on the cheek when her social life takes a downward turn, and lately, that could happen from one day to the next. Yeah, she was kind of dating again, but thank god she wasn’t bringing anyone home, yet.

I went upstairs and knocked on my older sister’s door. I didn’t knock hard. The idea of my mother or Abbey finding me knocking on my sister’s door made me uncomfortable. What would I tell them? That Diana had told me to bring her water, so I did because I’m a good brother? (I’d do that for Abbey, but I’d never do that for Diana.) So, no, I couldn’t tell them that. And I couldn’t tell them that Diana was acting strange lately, and I wanted to know why. And—maybe—I wanted to know what she had meant when she had said, “I’ll give you a chance to appreciate me for appreciating you.”

So, I waited outside of my sister’s room for a minute. Two minutes. I deepened my breathing, vocalizing my breath as it traveled through my nasal passage and out into the air. Three minutes? I squeezed the water bottle, the plastic crinkling, and I thought about taking the cap off and drinking the water myself. What would my sister say to that? A bead of sweat rolled down my right cheek. I looked down the hallway to my room several times. Fuck this, I thought, but I didn’t move.

Diana opened her door. She had changed into a white T-shirt and nothing else that I could see. It was a plain white T-shirt that hugged her CrossFit body like a second skin, making the bottom swells of her big breasts curve outward as it curved inward to hug her flat tummy. The shadows of her nipples darkened the cotton through her shirt, and they poked upward and outward like two whores in need of attention. The shirt dropped just below her crotch, and one little upward stretch would show off everything from her waistline down.

“Your water?” I told her, lifting my hand.

“Right on time,” she said, taking it.

Diana’s eyes made a slow tour of my body, taking in my gray shirt—tight at the shoulders and all the way down to my waist—and my basketball shorts. Her eyes spent more time below my waist than above.

“Mom said I should try to get along with you,” Diana said. “Do you like how I get along with you?”

Did she mean since she had started ordering me around? And why the fuck was I doing it?

“It’s better than fighting, I guess,” I said. “I like it.”

“You can hug me, then,” Diana said.

I stood staring at her. I could hug her? Why was she giving me permission to hug her? What had I been expecting from her tonight? My sister stood in her doorway and waited as if by letting me hug her; she was doing me a favor. My eyes roamed down her body, stopping on her chest and her thick, standing-at-attention, nipples. Fuck it. I stepped forward, put my arms around her body, and I hugged her.

Diana didn’t hug me back. My sister was only half a head shorter than me, and I had to bend my knees as I wrapped my arms around her shoulders because her arms hung at her sides. It was weird, I won’t lie, but after her breasts touched my chest and her nipples dug into my skin through my shirt as I pulled her against me, I forgot all about the weirdness.

After a second, I pulled triplet sister tighter against me, surprised by the warmth and firmness of her body as she molded to me. I stepped closer to my sister and pushed the entire length of my being against her. A quick thickening of my cock heated my cheeks. Diana just let me hold her. She just let me do it, even as her breasts squished against my hard chest. She didn’t hug me back, and she didn’t stiffen, but the longer I held her, the more it felt as though she were doing me a favor. I liked it, as much as I hated to admit it. I liked it a lot. I wanted more of these favors from her.

“Good night,” Diana said after a minute of this. She stepped back into her room and shut the door on me.

I went back to my room to watch porn and jerk off.

Tuesday

Abbey asked me if I thought Mom would let her have some friends over this Sunday when Mom was at brunch. I asked what kind of friends and she said, “My friends.”

I asked if one of her friends was a boy.

She said maybe.

I asked if this boy had said that she looked like a boy.

Abbey said, “Do you think Mom will fucking mind? Jesus!”

“You know the rules,” I said. “Diana, Mom, or I have to be here, and Diana goes to the beach on Sunday mornings. I don’t know what I’m doing yet.”

“Why does Mom treat me like a child?”

“Because your friends are destructive,” I said.

After some back and forth conversation, I agreed to be there for her on Sunday.

After dinner, Diana told me that her shoulder was sore, and then she asked me if I was any good at touching a girl’s body. I blushed but said that I was while trying to control the quickening of my pulse. She told me that she’d think about it. Think about what? Later, when I brought Diana her nightly water, she told me, “The next time I say that you can hug me, you better hug me right away. You’re not allowed to hesitate again. Understand?”

“Yes,” I said, and I said the word quickly and without hesitation.

Diana put her hand on my chest, her palm flat, and her fingers extended. Slowly, she closed her fingers across my chest, dragging her nails over my skin until she had curled her hand into a fist. A shiver ran through me as my shaft swelled. It hurt, but in the way a good stretching session hurts.

“You can rub my shoulders before school tomorrow,” Diana said, dropping her hand. “Be in my room at six tomorrow morning. I’ll leave the door unlocked for you.”

She closed her door, and I went to my room to watch “how-to” massage videos on YouTube.

Wednesday

I woke up before my alarm went off, and like always, I was hard below the waist, but not rock hard like I usually am. No, in my shorts was a solid piece of steel that someone had heated, hammered, and folded, then heated, hammered and folded a few hundred more times, then quenched in a magic oil that made my dick unbreakable. I had a samurai’s blade in my pants. I had half an hour before I had to be in my sister’s room. I pissed, which is never easy with a hard-on. I jerked off, enjoying the feel of my solid rod in my hands. The word “huge” barely described how big my cock looked this morning. I mediated, willing the son-of-a-bitch to go down, and it did so with only minutes to spare.

With my phone in hand, I waited in the darkness outside of my older sister’s room. My heartbeat steadily picked up speed as I waited for the digital clock to turn from 5:59 am to 6:00 am. The quietness outside of my sister’s doors gave me the chills. Every breath I took fought against the relentless pressure of the moment. My head darted to the left and right continuously, no matter how much I tried to stop myself. Mom would have left to work by now, and Abbey would be in bed until I woke her cute little butt for school—several times— and then finally dragged her out of bed—if I had to. The final minute passed, but that didn’t calm me for a second.

I took the doorknob in my hand and turned, knowing that Diana must have locked it because she wanted to play some sick joke on me. That would be just like her, but she hadn’t locked it, and it turned, and the latch clicked, and I pushed the fucking door open on soundless hinges. My heartbeat thumped harder against my breastbone, and my chest shrank, and breathing was like gulping in air while buried up to my neck in sand. Winning my first state wrestling championship had been easier than this.

Diana lay on her king-sized bed. She slept under several thin blankets without a comforter. Her room was the second largest in the house, and her bed sat under a long strand of paneled windows along the wall opposite the door. The open slats of her wooden blinds let in the faint rays of the coming dawn, giving the room a grayish-white color that made the everything visible.

“You’re on time,” Diana said. “Good boy. Come here.”

Her stupid words gave me chills, but I didn’t hesitate to climb onto her bed. Diana lay on her stomach, her silk and cotton blankets ran a straight line across her shoulders. She gave me no directions, so I rolled the blankets down and hoped this was what she wanted. My hard-on from earlier started to rise again, sensing that this moment called for a second round of jerking off. Maybe it did, but even though my cock flooded with blood until it hurt, I focused my attention on my sister.

I knelt by her left side, the side her eyes faced, meaning that if she glanced downward, she would see the tent that I had created in my basketball shorts. I didn’t care. I needed to massage her shoulders, so I rolled the blanket down her back with caution. I don’t know why I didn’t pull the blankets right off of her, but the need to do everything with deliberate care and clean precision seemed like something my sister would appreciate later.

Why was this bitch in my head? But she wasn’t a bitch, at least, not like before. She was—I don’t know what she was—but she wasn’t a bitch in the menacing way that she was before she had started telling me what to do without yelling at me.

I rolled the blanket down her back, expecting to see the strap of a wraparound bra since no straps hung over her shoulders, but I saw nothing. There was nothing. My older sister of about a minute was not wearing a bra. I rolled the blanket to the middle of her back, and her feline nakedness hypnotized me. I continued rolling the blanket downward, the rush of seeing her body without clothing sent tingles through my arms. The blanket reached her lower back, and still I saw no clothing. I went lower, fascinated by her nudity as I rolled the blanket beyond the downward slope of her spine then upward, past her hips, unveiling the uppermost nakedness of the valley between her cheeks. The start of her crack.

God, but my sister was in great shape. CrossFit shape. Diana didn’t have time for organized sports, but she did use her time to keep her ass tight.

“Stop,” Diana said in a level voice. “I didn’t say you could do that”—and then her words hung in the distance between us—”yet.”

Yet? My balls tightened. What in the hell did yet mean? I pressed my lips together as a teardrop of pre-cum slid through my shaft and dripped from the tip of my cock, making me shake.

Even as I was pre-coming, my hands moved to my sister’s shoulders. I asked her which shoulder was sore, and she told me, “Figure out, or if you can’t, massage both of them.”

Fuck yeah I was going to have to massage both of her shoulders.

Her skin warmed my hands. She was hot to the touch, and that sent a tremor through my arms that turned my muscles to jelly. Diana remained quiet at first, and then she uttered a soft moan here and a little groan there. Here a moan, there a groan, everywhere a fucking sound that made my shaft swell and my balls tingle.

The sides of my sister’s big breasts flattened against her mattress and bulged sideways beneath her body. I came a little at the sight of her tits. This was the first time I had ever touched a girl like this, and the horrible smallness of fear hit me. (Abbey wasn’t the only person Mom treated like a child when it came to dating.) Anyway, it was the fear that I would come, and my sister would know that touching her had made me blow my load. Fear that she’d never let me do this again. Fear that it had to end without it happening again in the following days.

“Mm,” Diana moaned as I pressed my fingers into her muscles. She had closed her eyes. “You’re doing good, little brother.” She moaned again. Her noises sounded real but exaggerated. For me? “You only have permission to—ooh—massage my shoulders today. You’re not allowed to go lower. Remember that.”

I dug my fingers into her shoulders and ground my thumbs across her flesh, soothing her muscles and tendons and sweeping knots away with an intense, but non-painful pressure. I wanted to move my hands lower. I wanted to inch my fingertips toward the sides of my sister’s tits, where I could see their undersides bulging against the mattress. I wanted to push her blankets lower and find out if she really was naked down to her feet. Sometimes her bikini panties had low-riding waistbands, which let everyone know she was smooth between her coltish thighs, so why not her panties? But I knew she was naked, she had to be, but I wanted to see it. I wanted to—

“I need to shower,” Diana said, stopping my massaging. “I want cereal for breakfast.” And she dismissed me before I could even get going. I slid off the bed with my back to her to hide my erection.

By the time Diana came downstairs, I had everything ready. I poured her milk as soon as she sat in her chair. Diana smiled. Abbey threw me a bug-eyed stare. We ate. Diana ignored me. When we left for school, Diana held me back at the front door to our house as Abbey made her way to our sister’s car. My sister slapped my right hand, not hard, and she said, “The next time I invite you into my room, you had better lock the door behind you, understand?”

“Yes,” I said without hesitation.

Diana ignored me for the rest of the day. When I brought her water at the end of the night, she didn’t let me hug her. I think it was was my punishment for not locking her door. It had to be, and she didn’t invite me into her room the next morning. More punishment?

Maybe this was her bitchy behavior coming back, but it was her room right, so her rules, right? Fuck me, but what am I trying to rationalize here?

And why did it feel like she was punishing me?

Thursday

Diana ignored me today. Oh, I hated it. I hated it so fucking much. In the morning, I was staring at her, waiting for her acknowledgment, but she gave me nothing. Not a damn thing. At home, nothing again. I was pissed. I was furious. What had I done wrong? I don’t know, but I’d make it up to her somehow.

Abbey wanted to continue taking wrestling lessons from me. Fuck it. I taught her, and I worked her little ass hard. Offseason wrestling was all about learning, fundamentals, and staying in shape. It’s our classroom before the action. It’s the forging before the quenching. It’s—it’s a bunch of these fucking sayings. But working my little sister wasn’t enough to get rid of the rage burning inside of me because Diana wouldn’t pay attention to me.

Sweat poured off Abbey by the time we had finished. She was into it. She did everything I said, even the conditioning, though that was for me. When we finished, she gave me a sweaty hug and thanked me. I messed her pixie hair up and then I threw her into our pool.

I brought Diana her water at ten sharp and waited at her door until she answered it. She took it and told me to leave her a bottle of water on her nightstand as soon as I returned home from school tomorrow. She said, “I know you were upset that I didn’t pay attention to you, but because you behaved yourself despite being angry, from now on, the only time you need to wait outside my door is when specifically tell you to wait. Understand?”

Fuck no, but I said, “Yes,” anyway.

Friday

“I’m going out tonight,” Diana told me at breakfast—which I had ready for her even though she hadn’t told me to make her breakfast. “I won’t be back until Sunday morning.”

“Where are you going?” I asked without thinking.

Diana looked at me, and she tilted her head as if examining me. She said, “Be a good boy, and I’ll tell you when I get home.”

At school, and after a ride where I had done my best to hide my anger—failing miserably—and after Diana had parked her car and Abbey had left us, Diana turned to me, looked me in the eyes and took my hands in hers. After a deep sigh, she said, “These are good hands, little brother. I don’t need another pair touching me. Okay? Now get the fuck out of my car.”

Holy shit.

I got out of her car, and I decided that I needed to do something nice for her to make up for making her mad. Where was my maturity? I had sat in her car and sulked, pissing her off. That was no good, so I cleaned her room later that night while she was gone. I even changed her sheets. What the fuck was wrong with me? And what the fuck was wrong with my sister? And why didn’t I care anymore that she was my sister? When did that happen? I can’t say because I don’t know. It just happened.

With Diana gone and my mother out with an upswing in her social life—from one day to the next—I spent a lot of time wrestling with Abbey. That kid can roll, her wiry strength was crazy. We watched a few movies afterward, and we fell asleep on the couch together. She asked me some questions about boys, but nothing too direct. I think she was embarrassed. Mom didn’t come home that night, and when I awoke sometime after two in the morning, I carried Abbey upstairs and dumped her on her bed, then I went to my room to finish the night.

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