My name is James, and I live with my father Mark, mother Jillian, and sister Jennifer
It's the summer 1984 in Decatur, Illinois where I've lived my whole life. My house is in the suburbs, and I live with my father Mark, mother Jillian, and sister Jennifer. Jen and I are both seniors, and were both born in the same month, May. We're very close despite going to separate schools, with her going to an all girls school and me going to the county high school. Since I can't drive yet, Jen usually drops me off on the way to her school. My parents married each other very young, when my mother was 18 and my father was 22, yet seem to be happy. My father is publisher for the newspaper and my mother works from home. My mom is a well endowed woman who looks remarkably great for her age. She has thick brown curly hair which she keeps up un a bun at the top of her head, and bright blue eyes.
I wake up early on the last day of school, my father is out of town, and my sister is sleeping in her room. I walk out into the kitchen, where I see something I certainly did not expect. My mother is on her hands and knees, with her ass in the air, scrubbing the kitchen floor while completely nude except for her light blue apron & yellow cleaning gloves. As she scrubs the floor, her ass rhythmically jiggles, giving glimpses of her pussy and asshole. She quickly stands up and turns to face me when she senses my presence. "Sweetie! Why are you u-up so early?" She says frantically while trying to cover her side-boob peaking out from her apron. "I... don't know mom I just... woke up a bit early -- I swear I didn't see anything." She looks down towards my crotch. "Sweetie, I... think your hormones are saying something different." I see the tent shape in my knit pajama pants that she's referring to, and quickly try to obscure it with my hands. "Mom, I'm sorry I can't help it I-" I look up from my pants to see my mother grinning. "Mom, I..." She just laughs. "You're so cute when you're lying sweetie, I'm very flattered that you're sexually attracted to me. To be honest, I'm very attracted to you too." "Mom, I had no idea, really?" She just puts her finger to her lips, and motions me over to her. I get close to her, seizing the moment to reach around and place either hand on her ass cheeks. They're warm to the touch and are pliable under my gripping fingers. She runs her hand over my crotch, and takes hold of my cock under my bottoms. "Let mommy take care of this." She whispers breathily into my ear, her breath very warm to my skin." She plunges her hand beneath the elastic waist band of my pajama pants, grabbing my cock with her gloved hands, then pulls them down to my knees by the waistband. "Let's get you up on the counter so I can take care of you." She says before placing a peck on my lips. I hoist myself up on the edge of the counter top and kick off my pants, still around my ankles. My mother places her sudsy gloved hands around my cock, the sound of bubbles popping as she constricts my shaft. As she pumps my dick with one hand, she uses the other to pull her apron off. It falls to the tile below, revealing her large motherly breasts. While hanging a bit, they are not flat. They still perk up from her chest at the nipple. They seem to be at least 32DD. "That oughta help you, sweetie." She says through a huge smile that appears across her face. She giggles sweetly. "Does my sweet boy like mommy's breasts?" I rest my head back against the cupboard. "Yes mom, oh god yes I do." She pumps faster and faster, then suddenly pulls her hand away. My cock throbs and bobs up and down. "How bout you lay yourself down on the floor and let me get on top of you." I nod and lay on the floor. The cold tile sends goosebumps all over me. My mother places on foot on either side of my hips and looks down at me. She towers above me, her huge breasts bobbing as she giggles. I just look up silently, my mouth agape. "It's time for mommy to ride your cock." She slowly squats down, her full, downy bush hanging past her pussy lips. She takes my cock in her hand and guides it to her pussy, then rubs the head tenderly against her lips and bush before finally slipping it inside. A wave of warmth flies through me as she sinks down all the way until her crotch meets mine, her pussy fully engulfing my cock. "Oh... oh god baby, it feels s-so good." She manages to get out, sounding like she's out of breathe. She sets her hands firmly against my chest and rises her ass up until my cock almost slips out, then sinks down onto it faster than before. She picks up tempo as she bounces on my cock, and the sound her her ass slapping against my thighs grows louder and louder until-- "Oh my god mom, I'm about to cum." I tell her urgently. She only presses her hands down tighter on my chest and pushes all the way down on my cock. "I want you to cum inside of me baby, let it all out inside of mommy." Following her wishes, I let loose. I spurt my cum inside of her, and feel her fill up with my cock still inside of her. She throws her head back and lets out a loud moan before calming her breathing and tenderly caressing my cheek. "You made me feel so good baby, thank you for filling me up." "Mom, you have no clue how good that felt." I tell her as I stand up, and gather my clothes off the ground. She stands straight up, my cum leaking out and running down her inner thigh. "Baby, I'm gonna get cleaned up... We can go again tonight, no?" "Of course mom, I'd love to." "Good." She smiles and retreats back to her room, and I get ready for my last day of school.
I step off the bus onto my lawn. I notice my sister's car missing from the curb, she must be with friends. I step into my living room. "Hey mom." I say to my mother, who is currently on the floor on her yoga mat. She is adorned with her usual pink leotard, the one she wears when working out, but is without her leggings, leaving her bare legs exposed and giving me a peek of her bush peeking out of the sides. A matching pink headband holds up her curly brown hair in a beehive fashion. "Hey sweetie, how was your day?" She asks, sitting up from her stretching position. "It was alright I guess." I tell her as I head back to my room." "You guess?" She asks. "Well," I say loudly from my room as I drop my bookbag on my bed. "Mr. McClure gave us a surprise end of the year quiz and gave us no time to study." "Oh, sounds tough." She says in an almost joking manner. "Yeah well I'm lucky I already had an A in his cla--" I step back into the living room and almost stop dead in my tracks from what I see. My mother is now bent over her yoga ball, facing away from me, her barely covered ass up in the air. She looks back at me and smirks. "Well, after such a long day my baby needs some relaxation, huh?" She winks at me. "Why don't you come here and help mommy stretch out?" "Yeah uh-- sure thing mom." I walk slowly towards her, my eyes fixated on and unable to look away from her tight ass, which engulfs the leotard strap. "Just push your hands down on my back sweetie." I press down hard with my palms onto her spine, she puts her hands to the rug, and brings her ass up until she's in a downward dog position on the yoga ball. Her ass presses up against my crotch as she does this and I instantaneously feel my dick starting to harden under my jeans. After holding this position for a few minutes, she instructs me to lift up her leg and rotate it around. I place one hand at her kneecap and the other on the back of her thigh and lift up. I being to spin it clockwise, every motion giving a glimpse of her rosy pussy lips as the crotch piece of the leotard is pulled to the side. I switch to her left leg and do the same, getting harder and harder every time I catch a fleeting glimpse of her pink pussy and dark brown, thick bush. After I finish the technique, she sits up on the ball, lunging forward and almost running her face directly into my crotch. Instead, her face stops near inches from my throbbing erection, her eyes meeting it's level. She sits in shock for a moment before a smile appears across her face. "That must've been torture for your cock in there sweetie, how about we..." She pulls down my pants and takes my cock in her hand. "...take care of this!" She lays back on the ball, her back arched across it. Her head hands off the side and her arms are reaching out above her head. She pulls her hairband off, allowing her curly hair to cascade to the shag carpet below. Her feet are pushed up against the sofa and her legs are spread eagle.
Today is May 19th, my birthday. Mom has been dropping hints about my "special surprise" all week. She showed me bag from 'Victoria's Secret', but wouldn't tell me what was in it. Yesterday she told me she's gonna "try something she's never done", whatever that could mean. I awoke to a hand lightly stroking my leg. I open my eyes. My mom is sitting on the edge of my bed in her lavender bathrobe. I tiredly say; "Good morning mom, what's' up." "Oh nothing sweetie, I just came to wake up the birthday boy and find something interesting..." She looks towards my crotch. I sit up in my bed and peer down at my tent-pole protrusion in my sheets. "Oh hehe, yeah I guess I had some interesting dreams last night." "Oh is that so sweetie? Could they have been about me and what my special surprise could be?" I smile and lean back with my hands behind my head. "It's a possibility, I don't remember them. I tell her. "Well that's a shame, they must've been pretty arousing, huh? She says, moving her pointer finger in a circle above my erection. "Lets see what we're working with here." She says as she ever so slowly and seductively pulls the covers away to reveal my hardon. She makes a exaggerated fake-shocked expression. "Must've been some dream..." She takes a hold of my cock in her right hand, lays on her side across my legs, and rests her head in her left hand. She slowly strokes my cock and while staring lovingly into my eyes. "Can't believe how fast you're growing up." She says. "I'll always be your boy, mom. Don't worry." "Oh, I know baby, you're so sweet." I just smile and look deep into her eyes, as her hand pumps away, growing in speed. "Mom, you're making me feel so good." I close my eyes and relax my head. "Oh mommy." I moan. "I'm gonna cum." She tightens her grip ten fold, practically squeezing my cock head to base. "Let it all out sweetie." The first spurt of cum shoots out into the air, then falls, covering her hand. She strokes harder and faster, and I buck my hips up as I shoot four more loads all over her hand. She finally lets go and raises her splayed hand in the air, holding it in the light and marveling at it. "You came so much for mommy, I'm so proud of you baby." She reaches over to my nightstand and pulls out a few tissues from my box and uses them to wipe off my cock and her hand. She stands up then leans over and kisses me on the forehead. "I've got to go run errands, but I'll be back soon." "Alright, bye mom, love you." "Love you too sweetie." She slinks out of the room and carefully closes the door. Since there's nothing else to do, I decide to fall back asleep.
The sound of the living-room phone ringing wakes me. I groggily shuffle to the phone and answer. It's my dad wishing me a happy birthday. He tells me all about New York, then has to go to a conference and we hang up. I make breakfast and relax on the couch. What could that surprise be? I ponder. I mean, what could be better than a morning-wood handjob? Plenty of things, now that I think about it. But gosh, my mom is an experienced woman, what could she possibly have not done before? I decide the only way to find out is to snoop around, I am home alone after all. I walk through the quiet house to the master bedroom. The shades make it nice and dark, its cool due to the whirring ceiling fan. The musty red velvet carpet is soft under my feet. I slide open the closet door. My mother's shoes take up most of the closet floor, but there is a space in the corner where the Victoria's Secret bag sits. I reach for it and contemplate opening it. I stop hand, thinking that it would be better to be surprised. Something else does catch my eye, however. A small red felt box with a golden hinge on the front. Inside is a small, silver, metal cone with a rounded top. Connected to it by a short neck is a flat round piece of metal topped with a plastic jewel. After inspecting it for a moment, I remember seeing something similar in a porn flick my friend lent me. In the porn, a girl pulled something similar to the thing I found out of her asshole, then got fucked in the ass. Then it all came together. Is mom gonna let me put it in her butt? I mean, that'd be really hot, but would she let me? Content to wait and see, I close the box and shut the closet behind me. What am I gonna do in the meantime though? i think to myself. The clock on the wall reads 1:00 P.M. I lay down in my parents' bed and sink down into their thick duvet cover. I reach over to the dresser beside the bed and pull out my mom's white lace panties. I pull out my already erect dick, wrap the panties around the shaft, and start to jerk off. A few minutes later I feel myself getting close to cumming. I pull the panties over the head of my cock and unload into them. I deeply sigh and relax my head back into her soft pillow. I feel myself begin to doze off... I am again woken up by the phone ringing. I toss my mom's panties in the hamper, pull up my pants, and walk out into the hallway. I check my watch, it's three o'clock. This time, it's my sister on the phone. She tells me to tell me mom that she's sleeping over at her friend Maggie's house, then wishes me a happy birthday. As I hang up, my mom gets home. "Hey mom." "Hey birthday boy, did you have a nice day at home?" "It was kind of boring, but also pretty relaxing I guess." I tell her. "Oh, well it won't be boring soon sweetie. I can tell you that." She says. She winks at me. "Do me a favor and get the groceries from the car, and I'll start dinner... then we'll get to the surprise." "Sure thing, mom."