Date Night [pt. I]

The ride to Sharon’s house is smooth and quiet at first. You’re in the front passenger seat of your mother’s SUV. It’s nearly six, and the sun is beginning to dip below the tree line. Dim, dying rays of orange and red clash with an inky blotch of deep purple. The first stars are just becoming visible, like pre-dusk fireflies.

Mom’s at the wheel, of course. You’d thought about asking her if you could drive, but decided against it. After all, it wasn’t like Mom was going to be staying at Sharon’s.

You take a break from scanning the various houses and trees that flash by the passenger window in a splash of vibrant color to gaze at your mother. Dressed in gray sweatshirt and darker gray sweats, she looks like someone driving home from the gym. Her wet auburn hair is slightly curled. She hadn’t bothered to dry it after she’d showered, which is unlike her. A small grin spreads across your face when you think about the implications of your mother skipping an almost mandatory hair drying session because she was eager to spend more time with you.

You’d had sex with her.

It feels strange to think that, but it’s true. You’ve finally crossed the Rubicon and had sex with the woman who’d given birth to you. It’d been incredible. She’d been an amazing and enthusiastic lover. You wonder how much of that stems from Dad’s neglect.

It’d been really risky to have sex with her while your father and sister were still in the house, but you’d managed to pull it off without being discovered. You’d passed by Tiffany on your way out of the house, and she’d given no hint that she suspected anything had taken place between you and Mom. Dad was still in the TV room. Mom hadn’t even wanted to say bye to him.

She’d taken you by the arm and led you to her car. Once you were in the garage, you’d let your hand drift down her back to cup her juicy asscheek. Mom had gasped slightly, but she didn’t tell you to stop. Instead, she’d looked into your eyes. There was promise in her gaze, a burning willingness you’d never seen from her before.

You’d kissed her, then. Her wet lips had surrendered to you instantly, her tongue reaching out to entwine with yours as she pressed her soft, voluptuous body against you. You’d made out for a minute or two before realizing where you were. Standing in front of the door to the garage. Tiffany or Dad could have decided to open the door and they’d have seen you there.

It was so, so hard to pull away from her. And from the frustrated look on her face that she so quickly tried to mask, she’d felt the same way about you.

Fuck, you wish you had the whole day with her. Just the two of you to iron out the kinks in your relationship and release the tension that’s been steadily building between the two of you since you’d shot your load inside her, coating her insides with your hot ejaculate.

A part of you hopes you don’t have to wait. That somehow, you’ve already impregnated her, and that nine months down the line she’ll give birth to your son or daughter. It strikes you suddenly that any child you have with her would technically be her own grandchild, which is all kinds of fucked up, but you can’t deny that it sounds incredibly hot.

The SUV jolts suddenly, bringing you out of your thoughts. Your mom’s huge breasts jiggle with the movement.

“Oh, come on,” your mother grumbles. She brushes an errant lock of hair out of her face and tucks it behind her ear. “They should really fix this road.”

“I don’t know. It was kind of cool seeing the impact the bump had on your tits,” you reach over and grab her right tit through her sweatshirt for emphasis. She’s not wearing a bra, and you’re sorely tempted to lift her sweatshirt to get a better look at them. You start to lower your hand to the bottom of your sweater, but stop when your mother shoots you a hard look.

“Please, not while I’m driving, okay?”

She looks back at the road again. The car slows and she makes a quick turn. A red minivan with the majority of its seats occupied passes by you in the oncoming lane.

“Sorry,” you say finally.

She shakes her head.

“It’s okay,” she gives you a quick, warm smile to show she’s not angry. She rests a hand on your thigh and gives it a gentle squeeze. “You’re growing to be such a strong young man. You must be so pent up all the time. I can’t even imagine how that must feel, not getting the release you need every day.”

You smile at her.

“Hey, now. I get some release now and again.”

With four – no, make that five – MILFs at your beck and call, how can you not?

Mom flashes you a smile that lasts only for the one unspoken moment drivers are allowed to take their eyes off the road.

“Some release. You almost make it sound like it’s not that fulfilling,” she keeps looking straight ahead. She turns the car again.

You almost chuckle.

“It’s not,” you lie.

That gets her to look at you again, and it’s not the warm look she’d shown you mere seconds ago. There’s a flash of indignation in her eyes. It’s different from anything she’s shown you before. More passionate, but somehow less hostile.

“Well, except for this one time,” you amend.

Her glare dissipates almost instantly. She smiles almost too easily. Like she knows you’re teasing her and is playing. Or, more accurately, she’s teasing you.

She stops at a red light and looks over at you. “One time, huh? I wonder what was so special about it that made it more fulfilling than the others.”

Her hand squeezes your thigh again. She lets it creep upward, between your legs. Her eyes don’t leave yours. She finds your cock soon enough. It’s not difficult. You’re practically hard as a rock. Her fingers grasp your shaft and give it a brief tug.

“Well, that’s the thing. It was special because for once, I wasn’t alone,” you grab her tit. It’s heavy and ripe. You squeeze it harder than before, drawing a gasp from your mother’s throat. You enjoy her softness, the way her soft, heavy breasts yield to your touch and the fact that you can touch them as often as you want.

She shoots you a sly grin.

“Oh, you had help?”

You nod. “Yeah. A beautiful woman came to my room to talk, but we ended up going a lot farther than that. It was easily the best experience of my life.”

Her smile grows.

“Mine too. Um,” she bites her lip and looks away. Adorable. “Sounds like you should try to, uh, get that woman to help you as often as you can.”

You smirk at her.

“Oh, I definitely will. There’s a whole bunch of things I haven’t done that I’ve been dying to try with her.”

“Like what?” your mother asks.

An idea comes to you then. You move your hand upward and press your index finger against your mother’s lips.

“This.”

“Hm. I see,” After a moment, she nods. Then she opens her mouth, allowing your finger inside.

She swallows your finger half-way, sealing her lips over it. She twirls her tongue around your digit, bathing it in her incredible warmth. Her eyes are half-lidded now, and burning with desire. Her tongue snakes out between her lip and the bottom of your finger, and she moves her lips forward, taking more of your finger into her mouth. She starts suckling on it, her cheeks going concave like she’s sucking a cock.

You swallow. God, you can’t wait to experience one of your Mom’s blowjobs. Just imagining your prim and proper on her knees before you taking your cock into her mouth makes you want to tell her pull over and give you head right now. Fuck.

You bite your lip, only barely restraining yourself. Meanwhile, your mother’s eyes haven’t left yours. It’s like she’s trying to convey something to you nonverbally.

You notice the red light turn green in your peripherals.

You’ve got a feeling that the time you’d had sex with Mom wasn’t just a one-off without the assistance of her trigger or repeated trances. She actually enjoyed herself. She wants more. To make it a regular thing and give you and her release as often as she can. Huh. When she was asking you about being pent up, you wonder if part of that was just her expressing how dissatisfied she is with her sex life. That she yearns for you to give her something that her husband, your father, can’t.

The blast of a car horn behind you nearly makes you jump out of your seat. You turn your head to look at the side mirror. A dark green pickup truck is sitting behind you.

The annoying horn blares again.

Your finger leaves your mother’s mouth with a plop. She looks at you for a few seconds before glaring in the rearview mirror.

“Fine. I’m going,” she grumbles under her breath. She shoots you an apologetic look before stepping on the gas. Within moments, you’re past the intersection. Thankfully the truck makes a right turn.

“So, was that good for you?” she says.

“I could have done without that asshole interrupting us, but yeah. I liked it.”

“Glad to hear it,” she replies. “God.”

“You okay, Mom?”

She shakes her head.

“I’m fine, it’s just funny, I guess. I’ve always criticized people for messing around in their cars or holding up traffic, yet when you’re in the car with me, it’s like I can’t keep my hands off you,” her beautiful blue eyes flick over to you for a moment. She squeezes your cock again as if to punctuate her point. “We should be careful, though. Most people will probably assume we’re a couple if they see us touching each other like we were before, but…”

“It’s a small town. I get it,” you take your hand off her breast and rest it on her thick thigh. “We know a lot of people around here. Someone might recognize us and get the wrong idea.”

She nods severely.

“Or the right idea. It’s one of the things that worries me the most. Being discovered and losing this.”

“Me too, Mom. But I think you’re worth the risk. And you’re not going to lose me.”

Not while you have the power to reshape the minds of all those MILFs in power. Damn, you can’t wait until you can tell Mom about that and have her accept it. It’ll make her feel so much more secure with your situation.

She smiles at you lovingly. You have a sudden urge to kiss her. You settle for rubbing her thigh instead.

“I’ve never felt his way about anyone before. Not even your father. It actually scares me a little,” she swallows.

“Really? I never thought you of all people could get scared.”

She sighs.

“Well, I do. Quite often in fact, though I was always good at hiding my feelings from people. When you get to be my age, you start to think you have a good grasp on things. What’s right and what’s wrong. What works and what doesn’t,” she pauses for a few seconds as she turns the car. The houses are starting to look familiar. You’re getting close to Sharon’s. “I thought I knew what love felt like. Turns out I was very wrong.”

She whispers the last words so quietly that you almost don’t hear her. Your heart skips a beat.

“Sounds like we’re both learning something new together,” you take your hand off her thigh and grab hers. Her fingers lace with yours. “I know it probably sounds kinda corny, but right now there’s no one I’d rather experience this with than you.”

She looks over at you, her eyes slightly wet. She squeezes your hand.

“Thanks, sweetie. That means a lot to me. More than you can possibly understand,” she slows the car to a stop. “Mm. We’re here.”

You look right and see Sharon’s house. You smile. The front-facing windows glow with light from the inside. Like an invitation. Sharon’s in there, waiting for you.

It’s strange. Much as you love your mother, you feel like you love Sharon, too. You guess it shouldn’t surprise you. They’re both intelligent, beautiful older women. There’s more than enough room in your heart for both of them. Soon enough, you’ll make sure to implant commands in both of their minds to further cement their feelings for you as well as quash any sort of jealousy that might arise when you finally make them aware of what the other is to you.

You picture yourself entering a restaurant, only instead of just Sharon you have both her and Mom hanging off your arms. You imagine them wearing rather daring dresses that leave little to the imagination, capturing the attention of every man in the establishment. You’d relish their impotent desire and jealousy as both women doted on you and lavished you with their love while pressing their soft, mature bodies against you. Then after you’d eaten, the three of you would retire to Sharon’s house and you’d spend the entire night fucking them, alternating between the two of them as much as you pleased.

“John?”

“Mhm?” you glance back at your mother. Automatically, your gaze falls on her hefty breasts which strain the material of her sweater. Her nipples are poking through.

Your mother shifts slightly in her seat, moving her arm forward slightly to squash her boobs together.

“We’re here,” she says again. “You should go. You don’t want to keep Jared waiting.”

“Yeah. Right.” She still doesn’t know Jared’s away at college. That you’re leaving her to go on a date with Sharon. That you’ve already had sex with Sharon and you’re almost certainly going to do it again tonight. You might not even come home until tomorrow. It surprises you how much it bothers you to lie to her. She’d done nothing but ignore you or treat you like an unwanted guest for most of your childhood. You guess it’s hard to hold on to those feelings after seeing her so **** in front of you.

You check the digital clock on the center the SUV’s dashboard. 6:03 PM.

Three minutes late.

“I’ll see you later, Mom.” You pull the door handle. The door opens with a thunk. The sound of chirping crickets enters the car.

“Wait, honey,” your mother grasps your arm.

You eye her questioningly.

“When do you think you’re going to get back?” she asks.

“I don’t know,” you answer truthfully. “I’ll probably being staying pretty late. I might even sleep over if we end up staying out too late.”

She gives you a hesitant nod.

“Alright,” she mutters somewhat unhappily. It makes you wish you were far enough along with her and Sharon that she wouldn’t have bat an eyelash if you asked her to join you on your date. Your mind flashes back to the time she’d called you while you were at Angela’s. She’d seemed almost **** to see you. You wonder how **** she’ll end up being for your company when she has to spend an entire night away from you. “Just promise me you’ll call me when you know what the story is. Or if you need anything.”

“I will.” It’d be foolish to do otherwise, knowing full well what a stickler your mother could be about such things.

Your mother grins.

“Good. Now give me a kiss.”

Feeling confident, you press your lips against hers. She closes her eyes, accepting the kiss with a throaty moan.

You break the kiss. Her eyes flutter open moments later.

“See you, Mom.”

“Bye, honey.”

You exit the car, shutting the door behind you. You feel her eyes on you as you walk to Sharon’s front door. You glance back when you climb the steps to the front porch. The SUV’s interior lights are off, and it’s dark enough outside now that you only get the barest hint of her features in her silhouette.

She gives you a final wave before taking the car out of park and driving away.

You almost want to call her and tell her to come back.

Instead, you turn and knock on Sharon’s door.

“It’s unlocked!” A muffled feminine voice announces from inside.

You try the door handle. It clicks open without any resistance. You enter the foyer and shut the door behind you. No one comes to greet you.

“Sharon?” you look around, but see no one.

“Give me a minute!”

Her voice comes from upstairs. You guess she’s just finishing getting ready. Nodding, you make your way down the hallway, stopping at the bathroom. You enter and look yourself over in the mirror.

Your blue and white button-down, collared shirt looks almost decent on you. The beige khakis are slightly wrinkled. Mom’s face had scrunched up in distaste when she’d seen that. She had insisted that you wear something else. She’d rummaged through your closet for a minute or so before finally concluding that the pants you’d selected were in the best condition. You’d managed to calm her down by promising to take your wrinkly clothes to the dry cleaner sometime soon.

You snort. Mom will no doubt interpret “soon” to mean “as soon as humanly possible.” You fully expect her to nag you about it when you get home. You’ll probably get it out of the way tomorrow before your dinner at Marissa’s house. Perhaps even you’ll meet a new MILF at the drycleaners. The women in town stop by there all the time to see the seamstress who works there to get their clothes altered.

It’s funny. Normally you’d dread the idea of going to the drycleaners. Most places, really. But now that you have this ability, it’s like every inconvenient thing you’ve had to do before is chalk full of endless opportunities. You’re actually looking forward to doing your dry cleaning. Maybe you’ll ask Mom if she needs anything from the grocery store while you’re at it. No, that’s probably too crowded a place to take advantage of an entranced MILF. Not to mention it’s full of security cameras. Bummer. The store manager looks like she could be a mom, and she’s decently hot too.

You hear footsteps clacking against wood.

Exiting the bathroom, you make your way to the foot of the stairs just in time to see Sharon Thompson coming down.

“Wow,” you whisper.

Her dark hair cascades down the sides of her head in waves, wreathing her face beautifully. She’s wearing a minimal amount of makeup, you notice. Not that she actually needs to wear any. She’s wearing a pair of blue-gemmed earrings that glimmer almost as dazzlingly as her sapphire eyes.

Her dark blue dress leaves almost nothing to the imagination. The straps around her shoulders are thin, showing plenty of her smooth, pale skin. The boob window is generous, stopping almost in the middle of the front of her breasts, showing an amount of cleavage that borders on the scandalous. The material of the dress clings to her body, naturally drawing your eye to her curves.

The length of the dress is probably the only thing entirely proper about it. It stops about a third of the way up her thick thighs. She’s wearing a pair of classy high heels.

Fuck. You feel completely underdressed. Your neck starts to get a bit itchy.

“Hey!” she beams at you as she approaches, greeting you with a tight hug that squashes her huge breasts against your chest. She breaks the hug moments later, but stays solidly within your personal space. “It’s so great to see you! How are you feeling?”

“I’m great,” you reply honestly. “Um.”

You let your eyes rove up and down her body.

“What’s wrong? Do you not like my dress?”

Yeah, right.

“No, no. I love it. It’s just that I feel kind of underdressed compared to you, is all.” You hold your hands out for emphasis. “I mean, look at you. You could cause traffic accidents in that dress.”

She giggles.

“Well, I think you look very handsome,” Sharon replies matter-of-factly.

“Thanks,” you smile at her.

“I mean it. You look great. That’s exactly what I’d expect my boyfriend to wear for a classy dinner with me. And it’s perfectly appropriate for Vito’s,” she says.

You feel a pleasant warmth in your chest. Boyfriend. You really like that word and everything it implies.

“Thanks, Sharon. So, are you about ready to go?”

“Yep. Let me just grab my purse and we’ll hop in the car.”

“Can I drive?” you ask when she starts walking towards the kitchen. Your eyes are drawn to her big round ass. Her dress hugs it snugly.

She looks back at you and smiles.

“Of course,” she takes her purse off one of the kitchen chairs. It’d been hanging on the backrest. She fishes out of the keys and hands them to you. You slide them into your pocket.

“Sweet,” you mutter.

She laughs.

“Sometimes I forget how young you are, though I suppose all men seem to share an innate fascination with cars.”

You smile at her.

“True, but no car is complete without a beautiful woman in it,” you say.

She blushes.

“We should get going. Our reservation’s at six-thirty.”

Not a lot of time to get there, then.

“Alright, let’s go.”

You take her hand and make your way towards the garage. She follows you readily. When you reach the silver convertible you’d driven earlier, you notice the top is up. You open the passenger door for her.

“Oh. And who says chivalry is dead? Thank you.”

She gives you a peck on the cheek and slides into the seat, placing her purse on her lap. Her dress rides up her legs as she does so, and you can’t help but stare at her exposed skin. You can’t believe how lucky you are.

“John,” she rolls her eyes at you exasperatedly, but the upward twitch of her lips tells you she’s more amused than anything else.

You shake your head and close the door.

The ride to Vito’s goes by quicker than you’d anticipated. You and Sharon spend most of it making idle conversation. You really enjoy her company. It’s rare that you meet someone you can talk to about just about anything and not get bored or feel like you’re being judged. But Sharon’s like that. No matter what you say, she listens. Then she replies and you listen. You feel like the two of you have reached a common wavelength, the sort reserved for best friends and the few married couples who actually complement each other.

She’d taken your hand in hers and kept it on her lap through the entirety of the trip.

The first thing you notice upon reaching Vito’s is the valet parking.

“I don’t get it. Why can’t people just park on their own?”

Sharon cocks her head amusedly.

“It’s part of the theme,” she says enigmatically.

“The theme? You make it sound like Chuck E. Cheese’s.”

She laughs.

“You’re actually not far off with that analogy.”

You glide the car into the parking lot and settle in behind the line of cars waiting for a valet to take them to a parking space.

“Seriously?” you look over at her. “I wonder what the manager of this place would think if they heard you say that.”

She keeps her smile, and leans toward you slightly, giving you an eyeful of her expansive cleavage.

“They probably wouldn’t like it, and rightfully so. Most restaurants have a theme. A personality of sorts that their customers associate them with. It helps them remember their time there. After enough repeated visits, they’ll start to associate that theme with something familiar and comfortable.”

“You make it sound like they’re trying to manipulate us. The restaurants,” you say.

“Aren’t they?” she mutters.

You shake your head.

“Sometimes I forget you’re a psychologist.”

“Then maybe it’s time we have another session together so I can refresh your memory.”

You smile.

“I’m down for having another session with you. On one condition.”

“Name it," her lips twitch upwards.

“You have to do the whole thing naked.”

“Oh?” Sharon blushes. She leans a little closer to you. “Don’t you think that’ll be a little distracting?”

“Definitely. That’s what makes it fun,” you say. “You’ll be asking me serious questions about my life and I’ll have to try to ignore the incredibly hot woman in front of me long enough to answer.”

She lets out a chuckle.

“If that’s what’ll get you to open up to me, fine.”

You mentally pump your fist in celebration.

Then someone knocks on your door. A man in a professional-looking white button-down shirt, a black vest, and black pants. The nametag on his vest reads: Josh.

You roll down the window.

“Hey, how’s it going?”

The guy gives you an affable smile. His eyes flick over to Sharon and widen considerably. He swallows.

“Oh, not bad, sir. You mind if I take your car?”

Sharon doesn’t correct him, so you don’t either.

“Sure.”

You leave the key in the ignition and open the door, stepping out of the car. Sharon joins you promptly. She loops her arm in yours.

The valet looks between the two of you. If he’s thinking about your age difference, he makes no sign of it.

He gets in the car without a word and drives it towards the parking lot beyond.

You get a good look at the restaurant for the first time. It’s rather spacious, but the interior looks incredibly crowded, with gaggles of people spilling outside, chattering to each other as they await their tables. There’s a large balcony on the second floor where people are dining outside, flickering candles sitting in the middle of their tables.

“Looks nice,” you say. “Can’t wait to see where they’ll seat us. I hope we’ll end up on that balcony. I kind of like the idea of seeing your face in candlelight.”

Sharon gives you a peck on the cheek.

“Let’s go find out,” she says.

The two of you make your way into the restaurant. She keeps her arm in yours, staying close to you, as if to let everyone who looks at her know who she truly belongs with.

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