Anderson Family Journals #22 to 25

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#22 Timmy

MILF Day

Saturday

Today was the day--I was going to help Prisha seduce her son while her husband was away for the weekend. We may have massaged each other's moms the other week--well, I did most of the massaging; Justin left before things got good--I had no idea if he even wanted to fuck his mom. It was one thing to know our mothers were a bunch of horny MILFs; it was another to know that they were also horny for their own sons. I didn't know how I was going to make this happen, but Prisha was set on fucking her boy, as were all the Moms, and most important, Diana wanted me to do this. (Getting others into incest made her pussy so wet I had to towel off my cock between thrusts.)

Fuck, maybe I should have asked Justin if he wanted to fuck his mom, but how do you have that kind of conversation with someone?

We had a wrestling meet on Saturday, a dual meet, early in the morning. I was at school by eight, the competition started at ten, and I had won my match with an hour left to go. The mothers in the stands cheered their asses off. The dads were almost as loud, but when I took the mat, the applause and cheers from the Team Moms erupted in a way I had never heard before. Women's voices flooded the gym. I looked into the stands, where my mother sat center among the Team Moms who liked to bikini party with their sons. Oh, how those eyes envied her, and oh, how they ate me up. A woman walking past a New York City construction site probably didn't feel as small as I did beneath those eyes. The only mother whose eyes I met belonged to Roy, a Wonder Woman-looking lady, and she ran her tongue across her lips in slow-fucking motion.

Holy shit! I was going to fuck Roy's mom! That was going to be some sweet revenge.

After our meet, Mom saved me from having to make more dates with the other Team Moms by dragging me home right away. However, Mrs. Nguyen confirmed with Mom that I'd be at her house tomorrow after our weekly Team Party, where Mom promised to have a long talk with the other moms about their schedules and mine. At Mom's car, while Justin was waiting for his mother by their car, Prisha asked me to come to her place as soon as I could. She even offered to give me a ride if that made things easier for everyone. After politely refusing her offer, Mom drove us home.

Diana and Abbey weren't there. A quick text told me they were out shopping. Visions of Diana trying on tiny panties and lacey bras in front of Abbey came to me. (Abbey may have been a tomboy, but she had great taste in lingerie.)

After texting Diana, I showered.

Mom joined me.

"Shouldn't I be saving it up for Prisha?" I asked as Mom cupped my balls.

Mom laughed. "If Diana hasn't trained you to stay hard all day long, she's wasting your potential."

I laughed.

Mom dropped to her knees and pushed me against the shower's side wall. The water rained down on her, wetting her blonde hair and golden body, slipping down her face and over my cock. Mom took my prick in her hand, holding the base as she shook my floppy meat around, each swing adding stiffness to its length.

I met my mother's eyes as she stared up at me. She uttered a laughing breath right before taking my crown into her mouth, her eyes never leaving mine. My chest rose and fell; my abs did the same, and Mom ran her other hand up to my stomach and over my chest, touching my body in ways a mother isn't supposed to touch her boy.

"Yeah," I moaned, "fuck yeah, Mom. You're--mmm--mouth is so fucking hot."

I placed my hands in her hair, holding her as she bobbed her head up and down on my dick. She licked all around my bell-end, her tongue swirling above and below it in a warm circle of wet flesh. She slid her mouth down my shaft and pushed her tongue past her lower lip to keep it swishing at my pole.

"Oh, fuck," I moaned. "God, you're fucking good at that."

"Good a what?" Mom asked, but with her mouth full, the words came out thick and sloppy and so fucking sexy. Soft, mwah, mwah, mwah sounds followed as she worked my third leg hard.

"You're a good fucking cocksucker," I whispered.

Mom gulp-laughed. She lowered her eyes and bobbed her head back and forth, fucking my dick with her mouth fast and quick. Each brush of her lips sent shivers up my back, while the billowing of her cheeks tightened my sack, and the quivering entrance of her throat cushioned my glans with wet softness.

I didn't want to come in my mother's mouth, but I could have. She was so fucking good at licking dick that my balls wanted to explode. There was something intense and decadent about looking into the eyes of the woman who birthed me while she gobbled down my fuck-meat--meat never meant for the women of my family: Mom, Diana, and--

"Fuck," I growled, tightening my grip on my mother's hair.

I pulled my mother's head from my prick, keeping my grip on her hair as I slid behind her, never letting her get off her knees. Mom's saliva coated my cock, and water splashed against her back as I pushed her head downward, forcing her to her hands with her ass up and head down, her back arched, and her knees spread wide. Her sweet muff hung between her thighs in a soft, glazed hammock of pussy-curved flesh. I grabbed my cock around its base, held my steel-hard pole straight, and aimed my missile-shaped knob at my mother's puffy lips without bothering to warm her up. I didn't have to; she was as soft and slippery as warmed-up butter.

"Uhng," Mom grunted as my crown parted her pink walls. Her slippery clam parted with a tight friction even as her pussy juices added to the slipperiness of my spit-covered dick.

"Mom," I sighed. "Why do you get so wet for me?"

A throaty, unbelievable moan left my mother's mouth as my cock filled her twat.

Mom's pink walls swelled against my shaft, the pressure bringing pleasure to my throbbing rod. I pulled out and pushed in, her pussy lips chasing me as I banged my hips against my mother's firm ass, my sack slapping her clitty with each thrust.

"Fuck, baby," Mom whimpered. "Fuck it, baby. Fuck that pussy! Oh, fuck it good, Timmy!"

I pulled out of her grip and fucked back into her again, my cock stretching her insides, making room for its thickness. I let go of her hair and grabbed her hips, holding her in place as I fuck-pumped her cunny from behind. I stood on my right knee with my foot back while raising my left knee, planting my foot on the tub floor, and swiveling my hips so I could press my dick into my mother's muff as deeply as possible.

"Uh, uh, uh," Mom moaned with each deep, plunging pussy-stroke. "Uh, fuck, oh--oh-oh-oh!"

"Fuck, that's a hot pussy, Mom," I moaned. "Jesus, fuck, you're so hot between your legs."

"Mmm, fuck, ooh," she whimpered as I poked her cunny from different angles. "Get it, baby. Get that pussy good!"

I smacked my mother's ass cheek, her firm and meaty hills rippling. Her big tits bounced below her as the warm water crashed and exploded against our bodies. Her curves and softness thrilled me, and I watched her ass ripple with each thrust. The naughty, clapping sound of our bodies smacking together filled her bathroom with an echo that spurred my thrusting to new heights.

"You like this dick, Mom?" I asked, spanking her butt again, then again. "Do you love it when your son fucks you?"

"Oh, god, yes," Mom growled, expelling her breath from her lungs. "Oh fuck, baby, yeah, fuck Mommy. Fuck Mommy's pussy, Timmy." She moaned several times as I thrust harder. "Oh, it's your, baby. This pussy belongs to you!"

Her asshole winked at me. The little sunken divot of crinkled flesh was pink and clean, making me wonder if she had ever had it bleached. I laughed at my stupid thought and threw a firm fucking into the softness between my mother's thighs. A tingle shot through my glans, and a tight strain ran through my shaft. I squeezed the muscles in my tip as I fought off my need to come.

"Play with your pussy, Mom," I said, spanking her again, forcing a gasp from her lips. "Play with my fucking balls too."

"Oh, baby," Mom whispered. "So fucking naughty with your mother."

Not naughty enough.

I lifted my left hand to my mouth and drooled spit over my middle. Mom stroked my sack with her fingers, giving me a limb-shaking buzz. I moaned, tilted my chin down, and let a wad of spit fall onto my mother's asshole. Water washed over us, but it didn't matter; my spit stayed put. I lowered my middle finger and pressed it to my mother's silky back door.

"Uh, fuck," Mom groaned as my finger wiggled against the snug ring guarding her insides.

"Let me in that ass," I gasped, spanking Mom again and again.

"Uh, fuck," Mom grunted. "Fight it, baby." She grunted again as I applied more pressure to her anal ring. Even with the spit lubing my finger, Mom wasn't gonna give it up easily. "Fight your way--mmm--up Mommy's tight butt."

"Fuck."

But I did as my mother told me to do. I wiggled my fingertip against her rear end. Mom played with her pussy, whimpering, and slapping her clit, rubbing it, then slapping it again, only stopping to caress my balls. My entire body shivered, and the chill of intense pleasure buzzed across my scrotum. Fuck, but my nut was about to bust soon.

I grunted, closed my eyes, and twisted my finger against her asshole. Mom clenched her ring hard as I slowly--so fucking slowly--spread her pucker open. Mom whimpered when the tip entered her insides. She also stopped fighting me, and my finger slid up her snug butt to the last knuckle.

"Oh," Mom moan-gasped as my finger prodded her guts.

I felt my cock through the membrane between her anal cavity and cunny canal. Mom fell to her forearms, dropping her head between them with her fingers threaded for prayer.

"So fucking nasty," Mom whispered. "You fucking nasty--uh--nasty--uh--boy!"

I lost it, growling, and pounding my mother's juicy cunny hard while leaving my finger buried up her bum, the friction against my cock unreal as I rubbed my prick through her fascia tissue with my finger. Jesus, my dick felt big. I thought about Prisha and her son.... What would DPing a girl for real feel like?

"Oh, fuck," I cried out. My body flushed red, and my balls tingled, the sensation starting at their center and staying there, then radiating outward before shooting up my sack and through my shaft to the tip. I came--unable to stop myself--my hips going into overdrive. As my balls emptied load after sticky load into her juicy hole, I continued to fuck my mother's pussy, gasping as my knob grew sensitive and tingled all over.

Mom whimpered throughout my orgasm, taking the hard fucking like a pro. When the last of my cum slid from my cock, I stayed hard within her, kept my finger in her ass, and reached around my right hand to play with the swollen pleasure-nub capping her pussy.

"Oh, oh, oh, oh--Timmy, baby, Timmy!" Mom howled as her cream flowed.

I could imagine what we looked like: Mom and son, locked together hip to ass with my finger up her butt and my cock deep within her twat, our hips turning in circles as she squirmed against me. Fuck, I never went soft, and when Mom came, she surprised me by sucking a small orgasm from my shaft that left me whimpering.

We cleaned up after regaining breath, toweled off, and dressed. Mom wore jeans and a gray shirt with MILF spelled out in pink across her braless tits, her nipples showing. I threw on some basketball shorts and a tight, muscle-hugging workout shirt. Mom drove me to Prisha's house. I texted the Team Mom before we left that we were on our way to her house.

Mom gave me some advice in Prisha's driveway.

"Let her know that you're in charge," Mom said. "Diana's made it clear to everyone--"

--To everyone?--

"--that you belong to her, but us moms don't watch you boys roll around, sweat, grunt, and moan because we want to baby you."

"You don't?" I asked, smiling.

"No," Mom said. "We want our big, strong sons to show Mommy that she's raised a gentleman-animal."

A gentleman-animal....

"We fantasize about you being good sons in public, but in private, we want you to show us just how much you love us and how much you want us to love you back."

"I can do that," I said.

"Yes, you can," Mom said in a throaty voice as a smile widened her lips. "Now, give Mommy a kiss before you go inside and show my friend a good time."

I did as Mom said, then exited her car, the click of the door as certain a sound as the double clank of Justice on Law & Order. I traveled the walkway up to Prisha's front door, and before I could knock, it swung inward. In the shadows beyond the threshold stood the beautiful, caramel-colored Indian MILF who had invited me over to help her convince her son to give her his dick. She was wearing a pink robe, open, leaving her yoga-firm body and small black landing strip bare to my eyes.

"Come in," Prisha whispered, voice shaking a little. "Justin went out for a little bit, but that doesn't mean we can't get started."

Timmy out.

#23 Timmy

The First MILF

Prisha

I stepped inside Prisha's home, looking around the open, wraparound layout of white marble floors and painted white walls decorated with vases and greenery. Prisha slowly backed away from me, her robe still hanging open and her yoga-fit, tennis-trim body slipping into view as she stepped away from me.

I licked my lips as her movements bared her tits one at a time, her dark nipples sticking up long and thick, forcing a reaction in my cock that brought a rise to my shorts, the fabric stretching upward and outward in near slow motion. Prisha's caramel skin complemented her darker-than-dark hair, which she wore up, and the small rectangle of vertical hair centered on her plump mound sent my heartbeat up a notch. A man can only have so much hairless pussy before he wants to rest his cheek on some downy softness.

"I didn't think you had any pubic hairs," I said. Why the fuck did I say that? "I mean, I couldn't tell in those tiny bikinis that you... ladies... wear around the team."

"You mean your 'mothers' wear around you?" Prisha smiled. "You young men seem to like those little bits of cloth."

"We do."

Prisha raised her right hand and held her thumb and forefinger up with the tips opposite each other in a vertical line. "I like just a little bit of hair," she said. "I know how young pussy wants to stay young forever, but I'm a woman." She reached behind her head and let her hair down, its length dropping down her back. "Does your mother have hair between her legs?"

Fuck me. How in the hell was I supposed to control a woman who talked like that? My eyes slid past her to her coffee table, where an open bottle of chardonnay sat next to a half-full crystal glass with a long stem and a shallow bowl.

"Pour me a drink," I said.

"You're allowed to drink?"

"I didn't ask you for a drink." I walked forward, sliding past her as my cock bobbed in my shorts, and the blood-pumping muscle beneath my chest grew to twice its usual size. "I told you to pour me one."

I let my left hand drift to the side and caught Prisha's hand. My momentum forced her to turn with me. She followed, a shaky breath leaving her as she moved toward her coffee table. I sat on her couch, and she grabbed the chardonnay bottle and refilled her glass, then handed it to me with an extended arm, her robe now covering her nipples but sweeping away from her flat tummy, soft mound, and firm thighs. I could see her caramel pussy folds hanging between her legs, its centerline dividing her tender folds as they curved away from me.

I took the glass, fit the rim to my mouth, and drank from it with a deliberate slowness as I tried to compose myself without appearing as if I was calming myself down. Prisha stood between my open knees, looking down at me as I looked up at her, admiring the delicate lines of her face and the small signs of age at the corner of her sloe-eyes and the edges of her lips. As I drank my wine, I used my left fingers to sweep her robe apart, revealing her entire body. She shrugged her shoulders as I touched the silk covering her skin, and the robe fell to the floor, leaving this MILF naked in front of me.

How old was she? Late thirties?

I finished the wine and leaned forward with my right arm extended. My lips touched Prisha's stomach below her belly button as I set the empty wine glass behind her on the coffee table. I opened my mouth and licked outward with my tongue, the tip grazing her flesh and catching the upper wall of her navel. She sucked in a breath, her stomach pulling inward as visible goosebumps rose across her skin.

"Have you ever cheated on your husband before?" I asked. What the fuck kind of question was that to ask--again? I should have practiced with Diana.

"No," Prisha whispered, her flat stomach rolling as she drew in a shaky breath, her big tits shadowing my head.

"But you want to." I pressed my forehead against her stomach; my eyes cast downward along the line of her landing strip. I brushed it with the side of my left forefinger. As she quivered from my touch, a thick, musky scent from between her legs bloomed, her sexual need unmistakable as it filled my nostrils and watered my mouth.

"Is sharing my pussy with family cheating?" Prisha asked.

"Am I family?"

"You're gonna help me fuck my son," Prisha whispered. "You're earning this pussy today."

I moaned.

I lowered my hands to her ankles, sliding them upwards and pressing my fingertips into her calves. I raised them over the back of her knees and thighs, curling my fingers between her legs from behind. My fingers continued upward, her flesh growing warmer and damper, the scent of her sex growing hotter and stronger. A throb of desire raced through my shaft as I breathed in Prisha's pussy-aroma.

"I'll make it happen," I said.

I stopped moving my hands, the swell of her outer labia a breath away from the touch of my forefingers. Her nectar had dripped onto her thighs by then, and I sensed those plump crescents pulse as if reaching for my touch.

"Have you fucked your mother?" Prisha whispered. She put her hands in my hair and smoothed her palms over my head. "Does your sister think that's cheating--oh, boy!"

I had cupped her pussy from behind with my right hand, grabbed onto her meaty MILF ass with my left, then lifted her into the air before she could finish her question. Prisha tangled her hands in my hair as her body rocketed upward, her weight nothing but a feather in my arms. I turned her onto her back as I laid her on the sofa's soft cushions and moved between her legs.

She brought her knees up and wide, calves to hamstrings, and my mouth landed where her mound sloped into her pussy lips, where I swallowed her clit whole. I waved my right hand to the side and brought it back in, my fingers open and pressed together. The stinging slap of my palm spanking the side of her left cheek filled the living room.

"Oh!" Prisha gasped.

I tasted her freshness, along with the vanilla lotion she had used on her pussy, and the inner sweetness of her taboo-craving cunny. Beneath her brown pussy lips, she was a bright, buttery pink color, and I wanted to eat it all up. Prisha's body bowed as I tongued the pinkish gem capping her lips, and she growled when my tongue slid between the caramel curtains hiding her inner wetness.