I was sixteen or so when I first felt it, peeking from my bedroom window, through the gap in the oaks between our yards. She bent over the flower bed, and her blouse rode up to reveal a strip of skin above her waist; I didn’t know what to think, but it stirred a tickle in my underwear.
To me, she was just ‘Mrs. Jamason,’ my best friend Brian’s mom; the woman who made killer snacks. Kinda old, but so pretty. Her smiles were probably for her own kids, but they hit me with a strange excitement, the same rush I got when I was caught misbehaving.
By the time I was a senior, I knew what those feelings meant and how to quell them, alone in my room. Sure, I adored her figure, the small breasts and round ass. But more than anything, it was her voice. That no-nonsense tone when she pointed toward the sink and said, “Go wash up, Steven, if you want to stay for dinner.”
One afternoon, we were supposed to be studying. Brian was sprawled on my bedroom floor doing his history homework, but I could only pay attention to his mom stretched out by their pool next door.
The bikini did nothing to hide the curve of her hips and thighs, and I wondered how easy it would be to pull one of those little strings loose. God, I pictured the perfect white outline underneath, skin that had never seen the sun.
“You know your mom is hot, right?” I asked.
“Dude, not again. Give it a rest.”
“I can’t. She’s a MILF.”
“You’re a fucking perv, Steve. That’s my MOTHER!”
That's right, I thought. That’s exactly what makes me so fucking hard.
“I’m just saying. If I, like, told her… what do you think she’d say?”
“After she slapped you? Tell my dad, who’d kick. Your. Ass.”
Brian was right; the way I thought and talked about his mom was pretty pervy, but I couldn’t help it. Whether Brian was there or not, hanging with him was my go-to excuse. If I saw her down there, I had to get closer. His dad caught on to me pretty quickly, but never called me out. That side-eye smirk he threw my way seemed more like amusement than the threat that Brian warned me about. I think he actually enjoyed the turmoil his wife caused in me.
The way our houses line up, from my bedroom window, I could not only see their pool but also a slice of the Jamesons’ master bedroom. The space between the foot of their bed and the bathroom door became a stage where I discovered she liked to wander naked.
During the day, I had to be super careful. But after dark, with my lamp off, I could watch undetected. If she drifted into view on her way to shower, I slipped my hand into my pants because coming out was the full reveal: jiggling breasts and the dark hair between her thighs that would send me over the edge. Normally, it was a fleeting flash, and she’d be gone, making me wait days, sometimes weeks, for another show.
Then there were the times I glimpsed Brian’s dad, too. I’d get rock hard. Not for him, but for what I knew he was about to do with her. My view was always frustratingly narrow: just shifting feet and curling toes. But that was more than enough for my mind to fill in the blanks. I envisioned her head tossed back with abandon as he railed her, tits bouncing as she rode him. Did she scream or groan when she came? I’d replay those imagined fragments for days, my hand working my dick until my sheets were stiff with cum.
Later that winter, Brian mentioned his dad, an Air Force officer, was shipping out to the sandbox soon. The deployment was a big deal for the family, but selfishly, I hoped it meant the bedroom action might pick up.
Sure enough, on the night before he left, their room lights caught my attention around bedtime. She dropped her towel right before disappearing into the bathroom, and I grabbed a wad of tissue from my nightstand.
From nowhere, Mr. Jamason stepped into view at the window. He stood there a moment, looking out—looking, it seemed, directly at me. He saw nothing, since my room was dark, but he yanked the blinds anyway. Right then, a paranoid thought struck me: Did he know I was there?
Even with nothing to see, I kept watching shadows shift behind the shade. Suddenly, the room went dim, and the blinds rolled open again. A nightlight illuminated a woman’s profile, bent forward, hands on the sill. Just as her husband had, Mrs. Jamason looked directly across to me. Were they putting on a show, or did they not care who saw? A man’s outline loomed behind her. Her stance widened and lurched forward as he entered her. Their bodies moved as one.
Faint details emerged as my vision adjusted to the dark. Her breasts shook and swayed as her man thrust from behind. His hand reached around to cup one, then the other. Still gripping the frame, she bent lower and deeper, stepping her feet wider, arching her back. As she did, her face moved close enough to the glass that I could make out her closed eyes, her open mouth. I imagined her sighs of pleasure.
I stroked my shaft to the rhythm of Mr. Jamason fucking the MILF I worshiped. Strong hands held her hips to plunge deeper with each drive. Even after cum dripped from my hand, he kept going, pulling her hair, driving her tits into my view. I bet I could go like that if I were with her.
Then the action stopped. Her mouth closed into a satisfied grin. Her forehead slumped forward to touch the pane, breath fogging the glass.
She stood and turned to accept her husband's embrace around her naked body. His fingers glided between her bare cheeks, gripping them, spreading them, caressing them as they kissed.
Then, they vanished into the darkness, leaving me wanting more. What are they doing now? Talking? Sleeping? The thought of them making love again, beyond my view, sent a jolt of jealousy through my chest that I had no right to feel. She is his wife. His. But still, I coveted her in ways I hadn’t before. I longed to possess her the way he did.
I couldn’t bring myself to go over again until Mr. Jamason had left, as if he were a rival rather than my buddy’s dad. I told myself it shouldn’t be weird; the Jamasons’ house was basically my second home. But I knew why I’d stayed away, and it had nothing to do with giving the family space. When I finally did go back, I saw her differently. A sensual woman who was not afraid to show herself. Like she’d opened another button or two, just for me.
With his dad deployed, Brian’s place became the block’s after-school hub. The flow of kids in and out was the perfect cover. No one noticed when I slipped away to whichever room Mrs. Jamason was keeping herself busy.
I’d prop myself on the doorframe where we might touch as she passed. As she moved, I’d catch a glimpse of the lace of her bra beneath her blouse, vividly recalling what was beneath. She asked about baseball, finals, and what I was doing after graduation. “Dating?” The question jolted me back to the present.
“Nah, Mrs. J,” I answered. “No one special.” Christ, if she only knew. She was probably relieved I wasn’t sniffing around her daughter. Lori was cute enough, but too young for me. Plus, Brian would kill me if I so much as looked sideways at his kid sister.
Once, from Brian's room, I caught her clipping an earring in front of the hall mirror, getting ready to head out. “Hey, Mrs. Jamason, is that dress new?”
After a quick double-take, she smiled and spun, letting it flare around her knees. “Nope, I’ve had it for a while, Steven.”
“I like the way it… you know…” I started, then cut myself off when Brian rolled his eyes.
“Thanks for that, Steven.” A corner of her mouth curled up as she slipped past me to the stairs.
After that, I made a point to say something flirty when no one else was around. Especially not Brian. I’d already fucked up once by telling him his mom was a MILF. If he caught me whispering shit like that to her now, I’d never catch her alone again.
A few weeks later, spring had finally ushered in swimsuit weather. From my bedroom window, I saw her wrestling the pool cover off the water—my cue for a visit next door. As I had since we were kids, I gave the front door my usual ‘Tappity…TAP’ before I walked in. From the foyer, I shouted, “Brian, you home?”
“He’s not here, dummy!” Lori’s voice carried down the stairs. I ignored the jab. I was there for a woman, not a girl.
I snagged a Coke from the fridge and headed back to where Mrs. Jamason was swimming. Leaning on the deck railing, I watched. With each flip turn, half-second flashes of ass made my prick flutter. After maybe twenty laps, she finally waded to the steps on the far side, wringing water from her hair. When she bent for the towel, her suit crept up; a few curly hairs escaped the strip of Lycra between her legs.
She hadn’t noticed me yet, so I called out, “Hot swimsuit, Mrs. J.” She froze, then spun around with a shocked look.
“Hello, Steven,” she answered with a welcoming smile, but still looking about for anyone else. “Have you been there long?”
“No, Mrs. J, I just got here,” I lied; Brian’s word, perv, stuck in my head. Her suit was a modest one-piece, but when wet, it was nearly transparent. The thin white material clung, outlining erect nipples, and didn’t hide the dark shadow of her mound. I adjusted my shorts, expecting her to cover it all with the towel in her hand. Instead, she bent at the waist to flip her hair and wrap it in a towel like a turban. For one unguarded instant, everything hung loosely, almost uncovered, until she straightened and turned toward the house.
Walking up the steps ahead of me, she told me, “I... I don’t know where Brian is.” Turning away from me, she adjusted the towel on her head and offered, “You want something to eat while you wait?”
“Yeah, I’d like to snack on something,” I said under my breath, sliding my hand from her lower back to the curve of her ass as I guided her up the last step.
I didn’t grab it or anything, but she slapped my hand away and whirled, eyes flashing. "What the hell, kid, you're only seventeen." Not anger exactly, but exasperation, like I'd broken some unspoken agreement. Which? Touching, or my age?
Again, Brian had predicted his mother’s response, making me grateful Mr. Jamason wasn’t there to follow through with the rest of his warning. Totally aware of my misstep, I bolted out the front instead of waiting for Brian.
It was maybe two weeks before I worked up the nerve to come around again. When I finally did, I kept my hands to myself and my eyes where they belonged. No lingering in the kitchen waiting to see what an open button might reveal. But I didn’t stop rehearsing my fantasy. Cupping her cheek. A kiss. No tongue. Just a real kiss, one that said everything.
Brian didn’t know any of this when he offered to host a barbecue for my eighteenth birthday in April. Though I wanted a reason to go back, I was still stinging from the pool incident, so I said, “No, thank you.”
I couldn’t stop ruminating on her words. Seventeen? Like that was the problem. Not that she was married. Not that she was Brian’s mom. Just my age? But when Brian’s birthday came around a few weeks later, I seized my second chance. If she lets me get close again, I told myself, I won’t mess it up.
Brian’s dad usually manned the grill for these things, but that day his wife took over. Cutoff jean shorts and a tank top her husband had sent from overseas—Arabic script above the words: ‘Who’s Your Baghdaddy?’
Someone had smuggled in vodka to spike our sodas, and I’d had enough to make me act stupid. She glanced up from the burgers, fanning smoke from her face, and caught me at the deck railing with my red cup. “No swimming today, Mrs. J?” I asked, hoping I’d get a replay of her stepping from the pool, dripping wet.
She may have tasted her share of the vodka too, because she grinned like she was recalling a secret challenge. She hooked her thumb at her waist. “Forgot the swimsuit,” she said, with a pouty frown. With a quick tug, she flashed the trim of blue cotton underwear.
My wide-eyed reaction made her laugh, somehow erasing the tension from the pool fiasco. Before I could think of a response, one of the guys yelled from the house, “Steve! HALO! Inside!”
As I turned to go, my stare dragged from her cutoffs all the way up to her eyes, which were drilling right back at me. Fuck. Caught. But then she grinned and muttered, “Later, Steven?” like it was an invitation.
Inside, I joined the battle royale on the Xbox. I was pretty handy with the game controller, but after a few cups of vodka and Coke, I kept getting killed. The sun was setting by then, chasing everyone inside. At one point, I saw Mrs. Jamason grab a bottle of wine and head out back. With so many new players, I took the first chance to slip out to the yard and find out what ‘later’ meant.
The deck was deserted, but the jacuzzi jets hummed from behind the privacy hedges. Around the corner, I followed the sound and found her: the back of her head tipped against the tub’s edge. Beside her sat an empty bottle of wine and a small pile of clothing. On top, crumpled blue cotton panties confirmed a possibility I hadn’t dared to consider.
When I approached, she was reclining blissfully asleep. The water was dark and frothy, so I could see the obscured outline of her body, with only bare shoulders visible above the surface.
I tugged off my shirt and dropped to the deck opposite her. The splash of my feet dipping in the water roused her. “Oh—” she gasped, startled by my intrusion. For a split second, her eyes darted to the ridge in my shorts, then snapped to her chest, before she abruptly sank into the water up to her chin. Crinkling her nose, she asked, “I thought you were busy making the internet safe for democracy?”
“I was, but got killed, so I needed some fresh air...” Glancing up to my bedroom window, maybe fifty yards away, I recalled her hazy silhouette when she first raised the shade. Then, lowering myself into the water, I asked, “Saw you out here by yourself… Is this okay?”
Her eyes followed mine to the pile of clothing. When she looked back at me, the cautious guard was gone, replaced by the same curious look she’d had in the window. When my calf nudged her smooth leg, she didn’t flinch…or remind me of my age.
“You know…MY birthday was a month ago,” I announced, and added, “I’m not seventeen anymore, Mrs. J.” An ironic grin spread across her face as she considered the significance of my revelation.
Leaning slowly forward, she let her breasts float to the waterline. “So you decided to take a closer look, Steven?”
In all my rehearsed kisses, I never dared picture her without clothes. But now my hand drifted up, brushing the underside of one nipple, then the other, careful not to overstep. She didn’t pull away, but peered down to where I touched her, and nodded. She tasted of stale red wine when I finally pressed my mouth to hers. Her mouth opened, then fingers curled tentatively around the back of my neck. She pulled me tighter until she was in my lap, our tongues sliding together. Nothing I’d imagined prepared me for the heat between her legs. My lips found her neck, her shoulder, tasting the skin I’d so enviously seen him touch.
Then—whoosh—the patio door behind us slammed open. “Steve! You out here?” Fuck. Brian. He saw me come out here!
Her knees clamped shut over my hand. “GET OUT,” she mouthed. Wild, wide eyes locked onto mine.
Shaking my head, I pulled her tighter, thinking only about what we'd begun. She twisted away, wanting none of it. Without breaking her glare at me, she called out, “It’s just me, sweetie!” in a voice that almost betrayed the frantic look on her face.
“Oh. Sorry, Mom.” A pause. Thank God, the footsteps stopped. “I thought he came out here.” A beat of silence, just long enough for my hand to find the small of her back. “If he does, tell him to get inside. We’re starting another game.”
When the door slid shut, she softened into me, my hard cock pressing into her back. I thought we would resume where we left off until she stiffened and shoved me back. Scrambling out of the water, she didn't even attempt to conceal her dripping body. Water streamed down her hips to her crotch, glistening in her pubic hair. Scant inches from my face, she was painfully beyond my reach.
“Get inside,” she said and hauled me by the elbow up to my feet. I grabbed my T-shirt from the deck and pulled it over my head. Her eyes dropped to the obvious bulge in my trunks. “Here,” she snapped, hurling a towel at me. “Around your waist. GO!”
As ordered, I hitched the towel at my waist and scurried toward the corner. I risked one last peek over my shoulder. Her whole body was trembling, but she made no move to cover herself. Completely bare and exposed in the dim light, her arm remained outstretched, finger aimed squarely at the house.
Five minutes later, I was still shaking, sitting on the floor, trying to be invisible at the end of the couch. Brian glanced over once, his eyes flicking to the towel at my waist. “Dude, you fall in?” he asked and laughed before the screen pulled his attention back. A close call; luckily, the game was more interesting than I was.
The glass door slid open, then shut. I turned in time to see her sneaking past. The cutoff jeans were soaked through. One hand clutched a damp ball of underwear, the other pushed wet hair from her face because she’d thrown her only towel at me. The soaked tank conformed to every curve I’d just tasted. She stared at me for a heartbeat before hurrying to the stairs, but it wasn’t an invitation to follow. That would have to wait.
The invitation I wanted didn’t come. She made it impossible to be alone. Then, one afternoon in the kitchen, with Brian and Lori sitting beside me like chaperones, she squeezed by to get to the fridge. A brief, purposeful brush of her body. I turned, and she looked away, but not before I saw it—the same look from the jacuzzi. She was thinking about it, too.
Then came graduation night, but I couldn’t have cared less. All my friends were out celebrating, meaning she would be at home. Alone.
The house was quiet. I stood at the front door and knocked. Tappity… TAP. No answer. Does she expect me to walk in like I had a million times before?
A television was playing inside, then went mute. I knocked again. This time, I heard footsteps before the handle turned and the door creaked open an inch. I pushed it the rest of the way and stepped inside.
She stood in the foyer, at the foot of the stairs. Hair loose around her shoulders. Cutoff jean shorts. Her arms crossed over the words, ‘Who’s Your Baghdaddy?’ on her faded black tank top. “Hi, Bea…”
I could see her consider that. “Mrs. Jamason, please, Steven,” she finally corrected. She used that ‘mom voice’ that always sent a thrill down my spine, but this time it supercharged every word.
“Yes, Ma’am,” I replied, my voice cracking on the second word. Am I making a fool of myself? A pleased smile confirmed it was not, when her stare dropped to the tent in my shorts.
“Did you come prepared?” she asked. I dug out a single square foil package and waved it like a winning lottery ticket. She smiled approvingly. Taking it, she stashed it in the pocket of her shorts. “Good boy,” she said, wrapping her arm around my neck to pull me in. The kiss started soft—just lips, testing—before her tongue slid past mine, the way it had in the hot tub.
Sliding my hands beneath her top, I caressed the curve of her spine, feeling a shiver. She raised her arms, prompting me to pull the shirt over her head. No resistance, just the soft ‘thump’ of fabric hitting the stairs.
Taking my hand, she guided me up the stairs, where I fumbled at her back, futilely searching for the clasp. She giggled. “Front, Steven.” With a simple flick, her breasts fell into my hands—pale, ringed by the golden tan lines I’d imagined.
Turning quickly away, she led me into her bedroom. “Lock the door, Steven.”
She sat on the edge of her king bed and beckoned me to stand between her knees. Her breath warmed the trail of ginger hair below my navel before her fingers tugged my waistband, just far enough for the engorged head to appear out the top. Her tongue darted out to catch the opaque bead forming at the tip. The slow, deliberate lick made my whole body clench. Then her mouth closed over me, swallowing me deeply as my shorts dropped to my ankles. Her lashes lifted to peer up as she gently coaxed me to that tell-tale quiver before releasing me.
Pleased, she scooted backward to the center of her bed. Raising her legs, she pointed her toes to the ceiling and peeled the denim up her thighs; the damp panties with them. With a kick, they landed in a twisted heap on the footboard.
Brian's mom, who had trimmed the crust from my sandwiches so many afternoons, lay before me, breasts flattened to her ribs. “I waxed for you this time, Steven.”
I followed her hand as it drifted down her stomach, fingers covering the soft folds where I found coarse curls before. Now, only a narrow landing strip remained, dark stubble laced with the silver accents of maturity.
I often imagined her like this, but always with a twinge of guilty delight because of who she was—a wife and mother.
Now I tore my shirt off and crawled across the white comforter to settle on my knees between her spread legs.
When I lowered my face, the scent was warm and musky. She melted, trembling, with the upward strokes of my tongue, clutching my ears with a firm but guiding grip.
“Steven,” she purred. “I have not had a man inside me since that night.” She eased me back with a firm push. “But you know that, don’t you? You watched us make love.”
She knew. The memory of her, pinned to the glass, flashed in my mind. I had replayed it endlessly, yearning to finally have her to myself in the way he had.
"Come here, Steven." She beckoned, palm up, her fingers curling. "You've waited long enough."
I twisted toward the footboard, where the condom still lay in her shorts’ pocket. Before I could reach them, she clasped my wrist and shook her head. “Leave it, Steven,” her voice wavered.
“Are you sure?” I asked; she had been too adamant earlier.
“I want to feel you.” Her gaze lowered to the bare curve of my shaft. “Nothing between us tonight.” Her knees fell open, and fingers found me, guided me. “Yes. That’s it, Steven.” I sank into heat that made my breath catch.
Her small gasp, the look of desire, as I pressed into her, brought me back to her hand on the window frame, bent deep to take her husband. Her teeth bit my lip, and her eyelids fluttered closed. Is she remembering the same moment?
When her hips tilted upward, I stopped thinking about anything but her body enveloping mine. Warm and firm... like her voice. My God, so slick, nothing like my hand at all.
I was barely in when I felt tremors build within me. Her deep moans encouraged me to drive deeper, knowing I needed to slow down. Too fast, Steve. Hold back. My body shook and let out an involuntary grunt. I was helpless to hold back the pulsing sensation, the urge to fill her. The wash of heat was so much more intense than when I was alone, cock in hand, dreaming of this moment. Even after I came, I continued to thrust until I was too soft to penetrate any longer. Too quick. I rolled off, chest heaving, beside her.
"Shh, it's okay." With her index finger, she dipped a dab of my cum into her mouth. “My turn, Steven.”
“You want me to…? My own…?”
“Of course, Steven. That's why God gave men tongues.” She chuckled and steered my face between her thighs, to taste our mingled essence. Outer lips, flushed and glistening, yielded to reveal the deeper, velvety rose within.
I’d seen enough porn to know the mechanics, but nothing prepared me for the way she gasped when I got it right, the way her fingers tangled in my hair, the way she turned my head to angle my mouth where she needed it.
She climaxed with a muffled cry that sounded like my name, her body shaking against my mouth, and I felt powerful in what I’d done to her. The rest of summer stretched before us. Lying naked with her, I was no longer the boy watching from the window.
