Shy Trail Walk to Neighborhood Baby
By Bill
2/8/2026
Cindy walked the neighborhood trails every day and I would her every and I was a shy guy and i could tell she was shy to until one day the neighborhood had a cookout and Cindy was there and she came up to me and she said you don't have to be shy and then she said walk me home and that changed things were started having sex every day until she got pregnant and then she asked what was I going to do about it
I'd spot Cindy on those neighborhood trails every morning—tight leggings hugging her thick thighs, ponytail swinging, tits bouncing just enough under her tank top to make my cock twitch. Shy guy like me? I'd stare from afar, pretending to jog, too chickenshit to say hi. She seemed shy too, eyes flicking away whenever our paths crossed. Then the block cookout hit. Burgers sizzling, beers flowing. There she was in cutoff shorts, ass cheeks peeking out, crop top barely containing her full D-cups. She saunters over, beer in hand, lips glossy. "You don't have to be shy," she says, voice low and teasing, close enough I smell her vanilla lotion. Her fingers brush my arm. "Walk me home?" Heart pounding, I nod. Her place is dark, curtains drawn. Door barely clicks shut before she's on me—hands yanking my shorts down, gripping my hardening dick. "Been watching you watch me," she whispers, stroking firm and fast. I shove her shorts aside, no panties, pussy already slick. She gasps as I thrust in raw, deep—walls clenching tight around my cock. We fuck like animals on her couch, her nails raking my back, moans filling the room. "Harder," she demands, legs wrapped, grinding her clit against me till she shudders, soaking us both. That was day one. Every day after—trails turned to quickies in the bushes, her riding me reverse cowgirl, ass slapping my thighs; nights pounding her from behind, balls deep, till she screams my name. Weeks in, she pulls me close post-fuck, sweat-slick bodies tangled. "I'm pregnant," she says, eyes locked on mine. "What are you gonna do about it?"
I freeze, cock still half-hard against her thigh, her words hanging heavy in the humid air. Sweat beads on her cleavage, rising and falling fast. "Pregnant," I echo, brain scrambling. She shifts, straddling my lap, her swollen lips brushing mine. No fear in her eyes—just heat, challenge. "Yeah. Your kid. Say something." My hands slide up her slick back, gripping her ass, pulling her closer. The thought hits primal: her body fuller soon, tits heavier, that tight pussy mine forever. "I'm keeping you," I growl, flipping her onto her back. She spreads wide, fingers parting her glistening folds. "Fuck yes," she moans as I plunge in, slower this time, savoring the grip. Her heels dig into my ass, urging deeper. I thrust steady, thumb circling her clit, building her toward that edge again. "Gonna fill you up every day now."
Her breath hitches, pussy fluttering around my cock as I grind deep, hips rolling in a slow, deliberate rhythm. "Mine," I mutter against her neck, teeth grazing the salty skin. She arches, full tits pressing into my chest, nipples hard peaks scraping me. "Fuck, yes—claim it," Cindy gasps, nails scoring my shoulders. Her walls pulse, slick heat sucking me in tighter with each thrust. I pick up pace, balls slapping her ass, the wet sounds filthy in the quiet room. Thumb on her clit, I rub firm circles, watching her eyes roll back, lips parting in a silent scream. Tension coils in her thighs, trembling against me. "Gonna cum—don't stop," she begs, voice raw. I drive harder, feeling her break—body convulsing, juices flooding us as she cries out, milking my cock relentlessly. Sweat drips between us, my release building hot and urgent.
As months went by her belly was really getting bigger and then she said a while back in asked what are you going to about it
Months dragged into a haze of raw need. Cindy's belly swelled round and heavy, tits ballooned fuller, veins tracing blue paths under taut skin. She glowed, hornier than ever, craving my cock daily—bent over the kitchen counter, belly brushing the edge as I railed her from behind, her ass rippling with each slap. One evening, sprawled on the bed, her in nothing but thigh-highs, she traces her bump with one hand, the other stroking my throbbing shaft. "Remember weeks back," she purrs, eyes dark, "when I asked what you're gonna do about it?" I kneel between her spread thighs, her pussy puffy and dripping, lips parted invitingly. "Fuck yeah," I rasp, rubbing my cockhead along her slick seam, teasing her clit. She whimpers, hips bucking up. Gripping her hips, I slide in slow, stretching her velvet heat. Her swollen belly presses against me as she wraps legs around, pulling deeper. "This," I grunt, thrusting steady, feeling her clench. "This every goddamn day." She moans, fingers digging into my arms, walls fluttering wild.
Her walls grip me like a vice, slick and scorching as I thrust deeper, her pregnant belly rubbing my abs with every grind. "And then I said," she gasps, voice husky, locking eyes with me, "we need to get married before this baby is born." The words hit like a spark, my cock twitching inside her. I slam in harder, one hand cradling her swell, thumb brushing a nipple leaking a bead of milk. "Hell yes," I growl, pounding steady, her tits bouncing heavy. She keens, pussy spasming, juices soaking my balls. "Fuck—say it again," I demand, angling to hit that spot, her thighs quivering around me. Legs hooked tight, she rocks up, chasing friction, breath ragged. "Marry me... make it official while I can still fit in a dress." Tension ratchets, my release coiling brutal at her base.
Her nails rake my back, urging me on as I piston into her, cock buried to the hilt in that soaked, clenching pussy. "Fuck, yes—I'll marry you," I groan, capturing her mouth in a bruising kiss, tongues tangling sloppy while her belly presses hot against me. She breaks away, gasping, "Tomorrow... chapel down the street." Her voice cracks on a cry as I grind deep, thumb circling her clit, swollen and slick. Milk beads from her nipples, trickling down the curve of her tits—I lean in, sucking one hard, the sweet tang flooding my tongue. Her body arches, walls rippling frantic around my shaft, pulling me under. "God, you're mine," she whimpers, heels digging into my ass, hips slamming up to meet each brutal thrust. Sweat slicks our skin, her breaths coming in sharp pants, release hovering razor-close.
Her eyes roll back, a shattered moan ripping from her throat as her pussy clamps down, milking my cock in vise-like pulses. I bury deep, roaring my release, hot spurts flooding her depths while she shudders beneath me, nails scoring red trails down my back. We collapse, tangled and spent, her belly warm between us. "Tomorrow," she murmurs, fingers tracing my jaw, sealing the vow with a soft kiss. --- The next day, vows exchanged in that dingy chapel, her white dress stretched taut over her swell, we seal it with a ring and a quick fuck in the back room—her on her knees, lips stretched around me, swallowing every drop. Two days later, she pushes out our son, a squalling beauty with my eyes. In the hospital bed, gown hiked up, she guides my hand between her thighs. "Missed this," she breathes, already slick as I slide two fingers in, curling slow against her still-sensitive walls. Her free hand cradles the baby to her breast, milk dripping as she rocks into my touch, breath hitching.
