Love Street Ch. 03

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Tommy's naughty mommy, the reluctant MILF.
5.8k words
4.46
33.6k
16

Part 3 of the 6 part series

Updated 06/08/2023
Created 04/06/2018
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Jason_NYC
Jason_NYC
86 Followers

"Yes!" I shout to Tom as we toss our helmets and pads into our lockers.

I'd gotten the green light to accompany Tom to Los Angeles for Thanksgiving. The only hitch, I promise to tour UCLA and USC.

"No problem," Tom replies as we walk toward the showers. "I'll drive you. But they're called the Trojans, you know."

"What?" I don't have clue what he's talking about.

"USC. They're the Trojans," he says making a little jerk off sign with his thumb and forefinger. "Do you really want to be known as a Trojan for the next four years of your life?"

I snap my towel at Tom's naked ass, but he's got great athletic instincts and evades it easily.

Tom does have a point. For some reason, I wonder if they distribute free Trojan condoms during USC campus tours.

Not likely.

Tom and I are post-graduate students recruited to bolster the Pine Creek Academy football team. Tom's the starting quarterback, I'm a tight-end.

A few hours later, my tight-end is on the hard plastic seat of a Pine Creek Academy bus bound for Pittsburgh International Airport.

The flight is packed with students and Tom flirts with half-a-dozen girls. (OK, maybe I do a little flirting too.) By the time we land at LAX, Tom has a date with a pretty girl wearing a Penn State sweatshirt and skin-tight yoga pants.

The woman who greets us at LAX is tall, slender, and wears a demure wool skirt with matching jacket that reveals little of her figure. Her face, except for full, expressive lips, is hidden behind oversized dark glasses.

"I'm Tommy's Mommy," she says with a childish giggle that causes Tom to roll his eyes at me. She takes my hand awkwardly, and when I bend down to kiss her on the cheek, she pulls away like a startled doe, leaving me pecking the dry California air.

"Ummmm, I'm Jason," I stutter, a little confused by her skittishness.

"Tommy's told me so much about you," she says. Her voice, though not unpleasant, has a high-pitched, little-girl tonality to it. "Why... don't you call me Maggie," she adds uncertainly.

"That'd be great, Maggie." Maybe I'm being hyper-sensitive, but it almost seems as if Maggie is wary of me.

When we got to their house in Los Feliz, the guest room is already made up. It's also white. Not just the walls, but the floor, the wooden bed, the side table, the dresser, armoire, curtains, bed spread. Even the electric clock. Everything is a creamy white.

Does someone around here have a purity complex?

The second thing I notice, having been raised in "Smallville," PA, where the nearest neighbor is half-a-mile down the road, is the view. Tommy's house is on a hillside and a carpet of lights stretch into the distance to where dark steel and glass skyscrapers are outlined against a glowing sky that makes midnight in LA look like dusk in Smallville.

A fragment of a song lyric plays in the back of my mind:

"Every night when the stars come out

Am I the only living soul around?"

Obviously not.

In the windows of some of the closest buildings I see lights, even shadowy silhouettes through gauzy curtains. It's almost midnight and behind some of those windows, pretty girls must be undressing, getting ready for bed. Behind other windows, lovers must be groping and caressing, climbing desperately toward a noisy climax, toward that one fleeting moment of psychological weightlessness where all is forgotten but the nerve-jangling pleasures of orgasm.

Beautiful oblivion.

And for some reason, I think of Tom's mom and they way she seemed almost frightened of me. How does her body look under her demure dress, anyway?

Does she have love handles around her waist? Has gravity taken it's toll on her breasts? Is she naturally blond? Or does she shave down there? What would she taste like? Would she be wet and slippery? Would I savor the aroma of her sex?

Twelve hours ago Gretchen and were saying goodbye for the holiday weekend with long and languid kisses that climaxed with my sperm spaying across her tongue while her vagina clenched my fingers and her clear liquid cum gushed into my mouth and down my cheeks.

In my rush to make the LA flight, I never showered after our steamy, sticky oral sex. Could I still be carrying her musky scent on my skin and clothes? Is that why Tom's mom backed off so suddenly when I leaned in to kiss her on the cheek?


If thinking about all this hadn't made rock hard, I might be feeling a little embarrassed. But at the moment, all I'm feeling is myself as I stand in the window, looking out over the city of angels with my fingers wrapped around a cock that has somehow escaped through the zipper of my jeans.

I'm about three strokes short of needing to finish what I've so absent-mindedly begun.

Since it's nearly 3:00 AM on my internal clock, I release my cock, pull the curtains closed, hang my jeans across the back of a white chair, and fall asleep immediately.

I dream that Tom's Penn-State girl is teasing my cock. She giggles and squeezes me with a skillful grip, her eyes twinkling in fascination as a little bubble of liquid flows down the tip.

"Are you going to show me your cum?" she asks, her warm hand fluttering softly up and down my shaft, her hot crimson lips hovering inches above my cock head.

I answer with a moan and push my hips into the air, aching for the moist warmth of her mouth and tongue. My cock twitches desperately and I take a deep breath sucking in the electric scent of our arousal. Except it's not the musky aroma of hot sex. It's not even the smell of sex and candy.

It's the fragrance of bacon, eggs and fresh coffee wafting from a tray on my bedside table.

The erotic dream fades like fog in the California sun, leaving me with a pleasant memory and a rampant, twitching cock.

Through half-open lids, I see I'm not alone. Maggie stands by the bed, her attention focused somewhere between my upper thighs and lower abs. During the night, I've kicked off the white sheets and comforter, exposing an engorged cock to anyone who cares to look.

And looking is exactly what Maggie does, studying me with the kind of clinical intensity you'd expect from a teenager at sex-shop peep show. After Maggie's awkward greeting at the airport, it somehow doesn't compute that she's now so transfixed by my erection.

Or does it?

Could Tommy's mommy secretly have thing for younger guys?

Now there's a stimulating thought. It doesn't take long before the exhibitionistic thrill of an attractive woman studying me with rapt attention sends a little shiver of excitement coursing through my erogenous zones.

Her gaze never wavers from my boy-parts which, make no mistake about it, are neither as long as a yardstick, nor as thick as a firehouse. Which makes the fact that she's so interested in me all the more flattering.

And stimulating.

I close my eyes. Imprinted on my mind is an image of my "Maggie's-lips fantasy." Which is to say, the pink tip of her tongue gliding suggestively across their glossy surface of her wet, sensual lips as she takes measure of my manhood. I imagine the steamy, warm sensation of those full lips parting and lowering onto my trembling cock.

I try to push this image out of my mind by thinking about college admissions tours and Pine Creek Academy football plays. I works for, like, 30 seconds.

Then my thoughts wandes back to Maggie's lips. Those plump, inviting lips, and a fresh trembler of excitement radiates through me, causing my erection to quiver and sway. That, in turn, produces an audible little hitch in Maggie's breathing, which ratchets up my own arousal by another notch.

It's a vicious cycle, or perhaps a virtuous one, depending on your point of view. Either way, the result is the same. An burgeoning itch that, sooner or later, I'm going to have to scratch.

There's no subtle way to jerk off when your best friend's Mom is watching you with a look that's part fascination, part undisguised longing.

So why bother?

I wrap my thumb and forefinger around the base of my shaft, and that little hitch in Maggie's breathing becomes a full-fledged gasp.

I don't dare peek at Maggie's reaction, so I just do what I have to do, and let my fingers glide up and down my cock as slowly as possible. The first couple of strokes are accompanied by a sigh of relief as my trembling cock is momentarily calmed by my own caress.

"Hey, Mom!" Tom's calls from somewhere in the house. "Can I use the car?"

There's the soft swish of fabric as Maggie moves with feline stealth, closing the door so gently that the latch makes only the faintest hint of a click.

The coast is clear, and I'm free to finish. Except with Maggie gone, it isn't nearly as exciting. The urgency I felt seconds ago has faded along with the the aroma of bacon, eggs and coffee.

Instead I wait and listen and wonder if Maggie will return. I'm betting she will, especially if Tom is leaving.

Outside, there's the distinctive cough of a diesel Mercedes cranking up as Tom pulls out of the driveway on some errand, or more likely to meet the little Penn State blonde from our flight to LAX. I can only hope he gets a hand job as good as the one I just dreamed about.

The possibility of Maggie returning keeps me hard. Will she want to watch as I stroke myself to a frenzied climax for her?

Or could Maggie want something more?

Perhaps it's just my over-stimulated imagination, but now that she's not hiding behind dark glasses and modest clothing, there's an aura around Maggie that suggests she's struggling with some kind of sexual compulsion.

I hear the door latch click and feel a rush of cool air as Maggie slips back into the room. I haven't moved my hand, which still grips my shaft.

With her return, the dynamics radically alter. Before Tom's interruption, Maggie's voyeurism could be easily explained away as an innocent accident.

Now there's no question of Maggie's intent.

I consider stroking myself to a furious orgasm for her, pretending to be asleep, although we'd both know I'm not. Afterward, she's slip quietly out of the room, leaving me with a cold breakfast and four days of frustrated fantasies and awkward encounters around the house.

There must be a better way.

Without opening my eyes, I give my cock a couple of energetic strokes, then turn my head and whisper, "Maggie, do you want to watch?"

I assumed she'd be shocked, or at least pretend to be. But when Maggie's eyes met mine, I see a desperate hunger, a burning need as powerful as any drug.

"I shouldn't," she says in new voice that is both deeper and more womanly. "Tom could find out."

"Tom will never know," I assure her. "What happens in Los Feliz, stays in Los Feliz."

She smiles at that, then turns serious.

"You promise, Jason. You'll never tell him, no matter what."

"I swear, Maggie."

She sighs deeply. Not exactly a "yes," but far from a "no."

Maggie's body relaxes, and I have my first clear view of her in tight jeans and a simple black t-shirt. She obviously puts a lot of effort into staying in shape. Her breasts are small enough to go comfortably go braless, as is evident from her swollen nipples, but full enough to give her womanly curves.

Everything about Maggie suggests a woman at the full peak of her sexuality.

"Sit down," I suggest, tapping the edge of the bed and scrunching over to make room while throwing the sheets completely off my legs. Maggie accepts my invitation, but places herself at the foot of the bed, perhaps out of my reach, but also directly in my line of sight.

"You knew I was watching earlier, didn't you?" she asks.

"Yes. Even with my eyes closed, I could tell. "

"I didn't mean for this to happen," she says with a hint of regret. "I was just bringing your breakfast in bed. Then I saw your... well you know."

"I know," I say as my fingers slowly work their way up and down my shaft and Maggie's gaze follows them intently, hypnotically.

"I was having an erotic dream," I confess. "A girl we met on the plane was giving me a wonderful hand massage. Do you want to see how she was doing it?"

Maggie doesn't answer. Not with words. But the tip of her tongue sweeps nervously across her beautiful lips, exactly as I imagined.

Three months ago I would have withered in embarrassment at the thought of anyone seeing me do something so intimate, so private.

That was before I hooked up with Gretchen ("Love Street" Ch 01).

Gretchen's insatiable curiosity about my body and the obvious delight she took in watching me cum for her, and on her, swiftly overcame my inhibitions. She was a virgin discovering the scope and power of her newly discovered sexuality.

I wasn't a virgin. Or not exactly.

Sex had always been a furtive, back-seat affair done in dark parking lots. Lots of excited fumbling with bras and zippers and belts and tight jeans and balky condoms, followed by a quick orgasm inside the tight pussy of an equally inexperienced partner. Then dressing quickly, partly out of embarrassment, partly out of fear of discovery.

Of the five girls who'd pulled down their panties and spread their legs in the backseat of my mom's BMW, I'd never had more than a stolen glance at the mysterious space between their legs.

Gretchen's sensuality was the polar opposite.

Maybe it was something about coming of age in the heart of New York City. But while she was in no rush to fuck, Gretchen seemed to savor the act of showing me every detail of her body and the way it responded to her own stimulation. In enticing me to do the same, I became hooked on the thrill of her angelic face studying me with excitement and appreciation as I performed my own most private ritual for her.

So, with Maggie I'm not embarrassed. Just incredibly aroused. And more than a little curious what it's like to jerk off for someone other than Gretchen.

The tension between Maggie's rising passion and her failing reluctance is fascinating. And insanely stimulating. Clearly, there's a little voice in her head saying, "This is Tommy's friend. It's naughty. Not something a perfect mother would do. It's almost incestuous."

Maybe that's why she seemed so awkward last night, and so obsessively fascinated this morning. It's not just Tom somehow finding out that's conflicting her. It's that in some ways, I easily could be Tom.

All interesting thoughts. But one glance at Maggie's sensuous lips, and my languid pace begins to quicken and I let out a little involuntary moan.

"God, Jason," she says with genuine anguish. "I shouldn't be here."

"But you are here," I reassure her. "You need to be here... just as much as you need air and water and warm sunlight on your skin. Indulge your passions, Maggie. Don't suppress them."

"So, true!" she looks at me in surprise. "What makes you so wise?"

"Gretchen," I say.

"A girlfriend?"

"Yes. We do this together all the time."

"Oh, God, Jason. I can't even imagine that. No one's ever seen me do something so... so personal."

"I was embarrassed too at first. But now it just feels natural. And erotic."

With that, I reach down and catch Maggie under the arms. I'm amazed at how light she feels as I lift her off the bed and pull her on top of me until our lips are within inches of each other, and my cock is trapped against her stomach.

"You wanted to kiss me last night, didn't you?" I ask.

"Yes," she moans, pausing a moment. "But I need so more than a little peck on the check. I was afraid you sensed it, and that Tom might pick up on it too. I acted pretty silly, didn't I?"

"A little," I say looking deeply into her eyes. "But what's the big deal. I'm just another of Tom's friends."

"Hardly just 'another' friend," she smiles down at me, I look blankly back at her. "You really don't get it do you?"

"I guess not."

"How long have you been lifting weights?"

"Five years."

"So look at yourself. You have the physique most women around here would kill to get their hands on," she sighs.

"That's why I always carry a can of pepper spray," I joke.

She smiles, then continues, "And those rosy red cheeks, the unblemished skin and innocent blue eyes. My, God." Maggie traces her fingertips across my chin and down my throat. "We could kiss all night and I'd never get stubble burn."

Our lips meet and I know from the way Maggie's forces her tongue between my lips, that she is not about to hold herself back. When we finally come up for air, Maggie rolls off me, exposing my cock again.

"Do you mind if I watch a little longer?" she asks. "You must think I'm a terrible pervert, but I just adore looking at your body."

"No, not at all," I tell her. "I love you watching."

"This may surprise you, but except for pictures, I've never seen a man touch himself before."

There's now a bit of clear liquid on the tip. My balls are aching, my cock is tingling and it is all I can do to keep from grabbing it and jerking quickly to orgasm.

"Do you need to cum?" Maggie whispers, as if reading my mind.

"Yes," I admit. "Badly."

I feel her lean closer, and think she might be reaching down to touch me. But instead, she whispers softly in my ear, "Go ahead, Jason. Let me see you cum."

I sigh, and let the fingers of my right hand drift down my chest and over my stomach and abs. My body shivers as they brush against my public hair. Then I caress the full length of my cock with the back of my hand.

Maggie mewls softly, as if she is feeling the same tingling sensation that courses through me.

The moist drop rolls off the tip and leaves a glistening trail along the smooth skin of my cock head. I caress the shaft with my fingernails and study the way Maggie's pulse beats in the hollow of her throat. We're loosing ourselves in a white-hot erotic fog.

"Is that how you like to touch yourself?"

"Sometimes, at least at first," I say, noticing her stiff nipples are now pressing against the fabric of her t-shirt.

"When I get more excited, I like to do it this way," I explain, turning my hand over and letting the tip of my index finger trace a path along the shaft and over the little ridge at the base of my cock head. This time, it responds by bouncing up and down.

"I'd just about forgotten how beautiful a hard penis can be," she whispers, more to herself than to me. Another drop has oozed onto the tip. Maggie watches with an almost hypnotic fascination while my fingertip dances up and down the shaft.

"Maggie?" I ask, bringing my hand to stop. "Will you squeeze your nipples for me?"

She brings her eyes up to mine, then looks down at the front of her t-shirt, and begins to roll each nipple between her fingers.

"Like this?"

"Yes, just, like that!"

"Jason," she whispers. "Show me how else you touch yourself."

"OK," I say, pulling myself into a sitting position to make more room on the bed. "But first, will you take off your jeans?"

"I don't know..." Maggie hesitates. Before she can continue, I reach over and place my finger on her lips. She swirls her tongue across my fingertip, savors the salty taste, then smiles.

"Then again, maybe I do," she says, lowering her zipper. It takes a little effort for Maggie to lift her hips and wiggle the tight jeans down over them, but when she succeeds, a pair of powder blue panties comes into view.

Maggie's legs are tan and smooth with delicate thighs and perfectly turned calves. She sits down opposite me on the bed, our knees touching, and her swollen pussy lips pressing firmly against the blue satin fabric. Even on the soft mattress, Maggie has beautiful posture, her back bolt upright, as if she's doing yoga.

Almost instinctively, her fingers got back to touching her nipples through her t-shirt. After a brief squeeze or two, she pauses. "I might as well take off this off as well."

My cock answers for me, nodding up and down in agreement.

Maggie grabs the hem and gradually lifts the t-shirt over her abs and stomach. I give an appreciative whistle at her narrow waist and firm, round breasts. The only imperfection is a long, thin surgical scar across her lower abdomen and a few faint stretch marks in the creamy white skin around her areola and nipples.

Jason_NYC
Jason_NYC
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