Anderson Family Journals #15 to 18

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Timmy & his mother: sex, sex, sex, sex, sex.
13.3k words
4.85
135.2k
80

Part 13 of the 17 part series

Updated 06/12/2023
Created 09/03/2021
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#15 Timmy

A Kiss with Mom

Timmy's Thoughts

It's the New Year, but I'm still writing about my life in December. I'm going to keep all but the juicy parts short and sweet. I'm no writer, just a journal keeper, but not for much longer. Maybe, I don't know; it seems like all I do is write about fucking, but Diana likes reading what I write, so maybe she won't let me stop.

Now, on to my life.

Sunday

I'm worried about Abbey. I don't think anything is wrong with her, but what does she know about Diana and me? Abbey and I still wrestled, but not like before. She's not so much into getting her frustrations out and learning anymore. It's more like she's trying to... fool... around with me. She'll jump on me when I'm on the couch trying to watch TV. Sometimes I'm just walking through the house, and she gives me a shove--she's got silent feet. Sometimes, she jumps on me when I'm in my room doing my homework. I don't get home from wrestling practice until after seven, so I don't have the time to go through real wrestling drills with her anymore, not until after the State Tournament ends in March. After that, if she wants to roll, we'll roll, but I don't know if she still cares about learning the fundamentals of controlling your opponent.

The problem isn't that Abbey likes to play wrestle with me; it's the why that concerns me. Outside of straight-up kissing me in front of Abbey, Diana does act like I'm her boyfriend in front of your younger sister, and since Mom already knows about Diana and me, I'm left to wonder what everyone else in the world knows. I don't know who is talking about what anymore. The wrestling moms know about my affair with my sister, that's for sure. For all I know, Diana has told Abbey about us even if Diana hasn't said that she has, and where Diana plans for that information to lead is anyone's guess.

Diana taunts me with how much prettier and sexier, and more beautiful our little sister Abbey is than her. I don't know how you can compare a pair of rainbows to each other, but Diana has made it clear that she thinks Abbey will ripen into one of the few really beautiful women of the world--no makeup needed.

I don't think Diana was a nympho, but I do think my sister loves to experiment, and that makes me nervous. I don't think Diana realizes that we could get into a lot of trouble for this, and fucking with Abbey's sexuality is not something that I think we should be doing. I know, we're triplets, but she's still my little sister.

Fuck--life is tough.

I'm not going to bring up any of this incest stuff to Abbey. Maybe that's what Diana wants me to do, and then what? Then I'm the one who has to explain to Abbey why her older brother is fucking her older sister and our mother?

Speaking of Mom, she's the reason for this entry, so let me go a few more days into the past and let you--my journal--in on a brand new part of my life.

Mom's Kiss

We--my mother and I--didn't speak much following the Sunday pool party, where I'm pretty sure I promised about half of my team's mothers I'd help them get their sons into bed. Mom couldn't drive home from that party, so I did, and Diana helped me put Mom to bed, and then we had our fun, where Diana permitted me to sleep with as many of the mothers as I had too, for a price: She gets to sleep with Lana and later, she gets to have my ass.

Fuck--I don't know if I can go through with that.

Monday came, and Mom went to work, stayed out late, and came home. She curled up on the couch with Abbey and watched TV, not ignoring me but not paying me any special attention either.

Tuesday came around; I was in Diana's room, inside my older sister's pussy from behind. She lay on her tummy in the prone position while I pressed my hips into her ass, grinding my cock between her slick folds as her warmth dampened my crotch. (God, she gets so fucking hot when I'm between her legs.) We had already had sex a few times. Now we were just having fun before going to bed together. I can't remember the last time I slept alone for the night.

At eleven--I knew it was eleven because Diana asked me what time it was--my sister told me to go downstairs and get her some water. I dressed in my workout shorts and a shirt and went downstairs. As I walked into the kitchen, I saw my mom sitting at the breakfast table, drinking a cup of tea. She was wearing a pearl satin robe that exposed her cleavage, and her two thick nipples formed a pair of small headlights against the robe's fabric. She stood when I entered the kitchen, her belt cinched at her waist, but the loose half knot she had tied her robe in didn't do much to keep the lower portion of her robe together.

"Not tired?" Mom asked, but she didn't sound surprised to see me in the kitchen so late in the night.

"Just getting water," I said.

"For your sister?"

I nodded.

Mom walked to the fridge, her long leg slipping out of her robe and exposing her thighs as she turned away from me. The robe's thin satin clung to her weight-trained backside, her twin cheeks outlined beneath her robe like a polished apple.

"Here," Mom said. She brought Diana's water to me. I tried to take it from her hand, but she didn't let go of the bottle after my fingers closed over the plastic above her fingers. "Did you have fun on Sunday?"

"Yeah," I said. "But not as much fun as you and the other moms had, I think."

Mom rolled her head to the right, smiling as she did. "We did get a little carried away in front of our boys, didn't we?"

"More than a little," I said. "But, it was fun."

"And before the other moms showed up, did you have fun then?" Mom spoke in an almost whisper, but her voice seemed to fill the kitchen. She moved her forefinger up the bottle, brushing my thumb.

"Yeah," I said. "Lots." Goosebumps crawled up my back.

"And you're okay with it?" Mom took a shaky breath. Her cheeks flushed. When she spoke again, her voice trembled. "You're okay with helping Prisha get what she wants from her son?"

I swallowed. My heart tripped, recovered, and skipped into a double-quick beat to make up for the beat I had lost.

"Yes," I said.

"What about the others?" Mom asked. "You're willing to help all of the other mothers as well... with their sons?"

"Yes," I whispered, my chest tightening.

"And me?" my mother said so softly I had to read her lips to make out her words. She brushed my thumb again. "You're willing to help me get what I want as well?" As she spoke, a pink blush toasted her light cheeks. A new sparkle ignited within her green eyes, matching the coy smile forming on her lips.

"Yes, Mom," I said. "I am."

Mom let go of the bottle in our hands. "You better go back upstairs. Your sister is waiting for you."

I nodded and started to turn around.

"Timmy," Mom said before I had barely begun moving. "Aren't you going to give Mommy a goodnight kiss?"

Holy fuck.

I turned back to my mother, moving closer to her as I raised my hands to her waist. The water bottle wouldn't let me grip her left hip, but my left hand fell onto the yielding firmness of the hard body beneath her robe. Mom trembled as my lips moved toward her. I wasn't thinking, just acting on instinct. Mom tilted her head upward, even lifting herself onto her toes, bringing herself closer to me. Our lips met. Her lips were warm and soft and full, the taste of her flavored by the mint tea she had been drinking.

"Mmm," Mom sighed in an almost thankful way. The energy flowing through her veins surged into me. She wrapped her arms around my neck and dug her fingers into my hair, caressing the back of my head with an eagerness that surprised me.

"Mmm, hmm, mmm," Mom continued to hum.

I parted my lips further, sliding my tongue forward. Mom pulled herself to me, her big breasts pushing into my chest, her nipples digging through her satin robe and my thin shirt. I wrapped my arms around her back, settling my fingers above the downward slope of her ass. Our lips moved together wetly, creating a piece of soft, liquid music my cock thickened beneath. (Mom was the first woman I had ever jerked off to, and now this... it was a teen's dream come true.) Our kiss ended when I circled the tip of my hard prick against my mother's stomach.

"We need to stop," Mom whispered in a rushed voice. "Abbey's home." She lowered her mouth, resting her forehead against my chest. "But we can talk about this tomorrow when we have some privacy."

"Tomorrow?" I asked.

"Your sister is waiting for you."

Fuck.

"Tomorrow then." I slid my hands back to Mom's sides, and I squeezed her right hip with my left hand. "As soon as I get home from practice?"

"Whatever you want," Mom said.

I broke away from my mother and went upstairs. Diana thanked me for the water and kissed me on the lips, pausing to say, "Mmm, minty." She eyed my hard-on, laughed to herself, then scrambled naked into bed with an unexpected giddiness.

I undressed before joining my sister in bed. She didn't bother opening her water. She did what she usually does when we sleep together: She turned on left her side and draped her right arm and leg over my body. I curled my right arm under her neck and around her back, and she went to sleep. I stayed awake, my hard-on tenting the sheets.

I lay there, trying to will the aching beast that was my cock to softness. At some point during the night, as Diana's soft puffs of breath fell over my chest, my cock began to deflate, wilting, swaying, and crumping to the side in an all-to-slow collapse that gave me time to think about my mother's lips once again. No good. My cock stiffened, becoming a giant ache beneath my shorts.

I brought my left hand across my body and palmed the outside swell of my sister's tit. Diana's warm flesh filled my palm, firm and perky in the ways only an eighteen-year-old girl's could be. I squeezed her breast and turned to my right, gently rolling her over.

"Hmm," was the quiet noise that sounded in my sister's throat.

I rested my sister on her back. Diana's warmth brought a red flush to my skin. How did she get so fucking warm? I ran my left hand down her body and over her stomach, tracing her belly button. She uttered a soft sound but didn't wake. I went lower, over the smoothness of her mound, my pinky and thumb brushing her firm thighs. I hooked a foot over her left shin and pulled her leg toward me, spreading my sister open.

"Hmm," my sister sleep-muttered again.

I slid my hand down her mound and palmed her hairless pussy meat.

Diana took a deep breath. Faint moonlight slid through the cracks in her blinds, but I could only make out the bluish-black shadows making up the contours of her face.

I slid my middle finger between her outer folds and laid my digit across the seam of her inner lips. My sister huffed in her sleep, her breathing turning thick and heavy. The rough sound of her nostrils puffing out air as I curled my finger through her slit spurred my heartbeat to a harder pace.

I played with my sister's pussy gently. Diana uttered soft whimpers as she wiggled her body enough to spread her legs further apart for my fingers. The shallow opening of her twat-hole became as slick as pink butter and just as smooth. Sighing, I slid the tip of my middle finger into her pink hole.

"Uh-umm," Diana moaned. She tossed her head in her sleep. Was she fighting to wake up? Was she dreaming about some man's hands on her body, in her body, not taking no for an answer? Pre-cum slid from the tip of my cock onto her hip. She moaned again.

I caressed her pussyhole, gathering her juices, then I removed my finger to a sigh of protest. I grasped my dick, wiping her wetness over my shaft. When my pole was slick, I cupped her pussy again, sliding my three biggest fingers through her crease one at a time before jerking my shaft again and lubing my prick with more of her warm honey.

I slid over my sister, careful not to wake her from her sleep. I positioned myself on my elbows with my forearms under her shoulders and my hips between her open legs. My cock dangled hard between us, rubbing the insides of her thighs and giving her pussy lips butterfly kisses as I searched for her juicy hole. She had to be aware of what I was doing on some level, right? I didn't know. My sister has never told me if she was, but she has never told me not to fuck her in her sleep again, either.

Diana uttered a soft, confused moan when I pressed the spongy tip of my prick to the smooth curve of her muff and pushed inward. My slippery knob sank into her, pushing through Diana's tightness and spreading her walls open.

"Uhhhhh," Diana moaned.

My shaft continued spreading her dewy walls as her lips stretched over my thick shaft.

"Mmm," Diana whined.

I pumped my hips forward, pushing her pussy lips inward as I loosened her cunny with my shaft.

"Huh, mmm, huh," Diana uttered in several breathless sighs. I think she was trying to wake up now. I think she knew her dreams were no longer dreams.

I pulled out and pushed back in... harder this time.

"Uh," Diana groaned. "What? Timmy, no." Her last two words came out as a whisper, but she didn't say her chosen safe word--RED--which would have made me stop without question.

I pushed deeper into my sister's pussy. She moaned again and brought her knees up around my sides. Her breathing deepened. Her breasts rose and fell against my chest, and her body--her entire fucking body--bloomed with heat beneath our blankets, turning my skin crimson.

"Timmy, fuck," Diana moaned.

Slick wetness coated my shaft as I pushed in and out of my sister's slippery snatch. She grunted when my balls touched her ass, and she wrapped her arms around my shoulders and locked her ankles around the backs of my thighs. I pumped my sister's pussy faster, drawing out her cream in a series of slish-slosh sounds as her pussy turned into soft butter around my cock.

"Uh, uh, uh, uh," Diana moaned. She turned her head, finding my lips, and she kissed me, her tongue snaking into my mouth, licking me up and down.

"Mmm, hmm, uh, uh, mmm," we both moaned and groaned together. I sped up, rocking my sister's bed, as she whimpered into my mouth. I slid my right hand down her body and hooked it behind her knee, lifting her leg up and back and over my shoulder, tightening her little pussy on my cock.

"Fuck," Diana grunted as I slid deeper into her than before. "You're extra fucking hard--ooh--tonight, little brother."

I spread my knees for balance and pumped my sister's pussy with firm strokes, sliding into her as her inner pink kissed and licked the tip of my cock with every inward thrust. I pushed all the way into her wet muff, ground my hips against her crotch, turning the base of my cock around her pussy lips as I bumped her insides with my rigid pole.

"Timmy," Diana whimpered. "Fuck, Timmy, fuck me, baby. Fuck me, little brother."

Minutes passed before the tingling in my balls began. Cream dripped from Diana's pussy, her juices running thick and messy down the crack of her ass. I hooked her right leg over my left arm and bent her double, fucking my cock into her with deep strokes, hitting bottom every time. My sister purred like a kitten. I rose onto my knees, moving my ass up and dropping my dick into her from a vertical angle, feeding my sister's cunny every inch of my fuck-stick on every inward stroke.

Diana started to pant. Then she began to whimper. Then her pussy walls hugged my cock, and she came, crying out as she swung her head from side to side. I found her mouth in the darkness, pressed my lips to hers, and swallowed the sounds of her orgasm as her body shook beneath me. As her pussy muscles spasmed around my cock, I thumped her wet hole as hard as I could three fucking times, making her whimper each time. On the final thrust, I came hard, jizzing up her snatch with one long surge of come.

Diana panted beneath me as I filled her pussy with a big load of sticky cum.

After the last of my seed slithered out of my cock, I collapsed to the side. I slid my hand under my sister's head, clenched her hair, and forced her down my body. She didn't fight me, doing my bidding as though I were the person in charge of us. I didn't let her back up until after she had cleaned my cock and then some. We fell asleep soon after.

Thursday's Plans

Abbey made her own way to school on Thursday. Diana and I parked in the back of the parking lot, where I gave my sister her morning kiss before class. But before getting out of the car, she had something to tell me.

"I can't pick you up from practice tonight," she said.

"I don't mind jogging home," I said.

Diana laughed. "Only a wrestler wouldn't mind running three miles after his practice."

"Jogging," I said, then asked, "Where are you going to be?"

"At Lana's, with Abbey." My sister smiled at me. "Mom's going to pick you up, so don't run away, understand?"

I nodded, thinking of what this could mean.

"Do you understand?"

"I do," I said after a moment.

"Remember: You belong to me." My sister reached over and grabbed my hand. "Only I get to tell you what to do." She squeezed my hand. "No one else. Not even Mom."

"I know."

"You better."

Later, at the end of lunch, my sister and I were in the drama theater, in our private fuck-room, as Lana calls it. Diana had dressed as a sexy schoolgirl, complete with a too-short pleated skirt, thigh stockings, and a gray sweater over a buttoned-up dress shirt. I had her bent over the makeup counter with her skirt on her ass, and her sexy panties pulled over the left side of her firm ass, exposing her pretty, pink slit to me. Lana kept watch for us, but she was doing it from inside the room, cracking the door open and peeking out into the hallway... some of the time.

I pumped my sister's pretty pussy for the last ten minutes of lunch, turning her silky folds into a runny mess of cream and cum. I didn't fuck her hard or fast, just firm and deep, giving her an intimate cunny massage that closed her eyes and pushed moans through her body. She didn't bother cleaning up our cum after I pulled out and cleaned myself up. Instead, she sat on the makeup counter with her panties to the side, and her pink muff glazed as we talked.

"Have fun tonight with Mom," Diana said. "I'll pick you up in the morning."

"I will," I said, and then I had to ask, "What are you going to do with Abbey at Lana's?"

Lana laughed.

"Lana's cousin kind of knows Abbey." Diana smiled at me. It was a warm smile. "They run in the same circles, I guess. Don't worry. We're not going to do anything crazy tonight. I love you, now get lost."

As I walked away, Lana walked toward my sister....

Timmy out.

#16 Timmy

Fucking My Mother

Where I Left Off

Diana had just told me that she was going to spend the night at Lana's and that she was taking Abbey with her, leaving me alone with Mom, who was picking me up after my wrestling practice. Why? To make sure I wouldn't run in the opposite direction? That made me laugh. I knew that wasn't the reason. Not after our kitchen kiss. So why? Was my mother eager to get me home after a hot and sweaty wrestling practice? Maybe. But I think she had decided to pick me up after practice to show the other moms that the game was on.

Before practice started, Diana sent me a text: Take charge of Mom tonight. The first time I read that, I thought it said care....