Date Night with Mom

"Mom, I have something I want to ask you but I need you to promise you won't think badly of me."

There is another pause. "Think badly of you? Noah, you know me better than that."

"I know, I know. But it's a hell of a thing I'm going to ask you."

"Anything baby, you know I'll help if I can." She assures me. God she was a good mom. "What's going on in that head of yours?"

"Mom, I'm thinking about starting to date again."

"Ohhh, that's wonderful!" Her happiness for me is palpable even through the phone. "Is there a girl you're looking at? He he he. Did you meet someone nice?"

"Yeah...uh, the thing is...ohh boy."

"It's okay Noah, what is it son?"

"You see...I...I'm kind of out of practice. My mojo is at an all time low, ya know?"

"Oh Noah. You are an incredible young man." She says, trying to boost me up. "Any girl would be so lucky to go out with you. You'll do fine!"

"Thanks Mom. But..I just...I just feel..." My heart is beating in my ears. Why was this so hard!? "I feel like I'd like a...practice run. Just to get the feel of things again. Get my confidence up. Get my groove on so to speak."

"Okay." She replies, obviously unsure exactly what I was trying to say.

"Mom. God, I can't believe..."

"Go ahead hun, I'm here for you. I'm always here for you."

"Mom...Michelle...I was wondering..." I swallow hard. "...if you would like to go out on a date with me."

There is a painfully long moment of silence before she finally whispers. "Michelle?"

God this was awkward! "Um, I know it sounds crazy but I just thought if you...if I could take you out, like on a date, like a first date. It would let me shake off some of the rust. If we could...pretend to have just met and...oh man. Just a pretend date so that I can...practice. Uh, um, uhh. Do you understand what I'm getting at? Just a practice run." I was speaking way too fast and I am forced to slow myself down. "Sooo, how about it?"

Another moment of interminable silence, the only sound I hear was my rapidly beating heart. I was bungling this! This had been a horrible mistake! I need to call this off!

"Noah..." My mother's voice is smooth as silk with the kindly patience I was so accustomed to from her. She then actually laughs lightly, not in a mocking way but in a pleasantly amused one. "...baby. My therapist told me you might reach out to me about this. Not like this in particular, but she said you'd need your mother soon. You are under a lot of stress right now. So much is expected of you. You are so busy and don't have time for girls, yet you need someone too. I understand."

I try to pull the plug. "Mom, I'm sorry, I shouldn't have even...it was a stupid idea."

"Call me Michelle."

I am stunned into silence.

I hear her take in a deep breath of her own. "Call me back again Noah. Ask me properly."

"O-okay." I stammer.

Click.

***

I hang up the phone and let out the huge breath that I'd been holding in. This was actually happening!

I could hear Craig showering. I knew I only had another ten minutes or so. This had to be done soon.

Okay, okay, okay. She wanted me to call back and ask her properly. The game was on. She was Michelle and I was Noah. We weren't related. She was just a pretty girl. I'd gotten her number and I was calling for a first date. I pump myself up. It was go time.

The phone still in my hand I redial the same number again.

Ring...ring...ring...

I smile. She was purposely drawing this out.

"Hello?" She answers as if she had no idea who was calling.

"Hey!" I reply in my most chipper tone. "Michelle?"

"Hi...uh, who is this?"

"It's Noah. We..." My mind is scrambling. "...we met at the cafe the other day. I was at the table next to yours. I asked for your number."

She laughs softly. "Oh yes, I remember you. Dirty blonde, blue eyes, brown leather jacket. How are you Noah?"

"Not bad but hoping to get better."

"Oh?"

"I was wondering what you were up to tomorrow night. I thought maybe, I don't know, you'd like to go out for a coffee or something."

"Coffee?"

"Or maybe a dinner. I'm flexible. I'd just like to have a chance to get to know you. How about it?"

"Hmm, tempting but...aren't I a little old for you Noah?"

"Age is just a number Michelle. I felt like we had some chemistry and...you only live once, ya know? Come on, don't let age be a barrier. I assure you I am very mature for my age." I then add playfully. "Not too mature mind you."

"You were pretty cute." She titters.

"You were looking pretty fine yourself Michelle." Was this actually happening right now!?

She doesn't miss a beat. "Mmm, a dinner does sound nice. Hmmm." The way she was talking to me was so...different. Her tone and tenor just...different. Truly as if she were talking to someone she'd just met. "Ohhh, but I may have plans for tomorrow."

My smile widens. She was making me work for it, not too hard but a little. "No problem. I'm free Friday night too if that works better. Saturday is out though, I told my Mom I'd hang out with her that night."

She giggles, genuinely giggles, before saying. "That's sweet." She hums then adds. "I think I can move things around for tomorrow. Sure. I'd love to go out with you Noah. Tomorrow night would be great. Where should we meet?"

"Can I pick you up?"

"Mmm, a gentleman huh?"

"I try."

"Sure." She gives me her address as if I needed it. "Seven O'clock?"

"Perfect. I'll make the reservations and take care of everything. You don't mind French?"

"French, on a first date? Oh my! How bold!" She quips. Was that a bad kissing joke? Was that a flirt? She then titters. "That sounds great Noah. I look forward to it."

"Great!"

"How should I dress? Casual, classy, something else?"

Normally for a first date I'd say casual but this was something different. This was a one off and I really wanted to treat her like a lady for the night. I knew my mother used to love dressing up but hadn't had a reason to do so since leaving my dad. "Something nice." I say. "Not black tie level or anything but...nice."

"Okay. I can do nice." She says. I could tell she was smiling.

"I can't wait to see you Michelle."

"You too Noah." Her voice was soft and sultry.

"See you tomorrow night, seven o'clock."

"You bet. Can't wait."

I hang up the phone and instinctively fist pump the air. "Yesss!"

It is only a moment later I realize just how stupid that was. For just a second I forgot just what the hell was happening here. I'd gotten a wee bit too much into character. I set the phone down chuckling at my foolishness. God, if that got me going I really did need to make time for girls in the near future. This reaction was pathetic.

It might be a pretend date but my lonely spirit didn't seem to know the difference. A beautiful woman just said yes to going out with me, I was feeling on top of the world!

***

With a bounce in my step I march back across the room and return to my book. I continue to mentally berate myself for being so fucking happy right now but something inside of me just didn't care. I felt great and that was that.

My eyes scan the page but take in nothing. My attention was now focused on tomorrow night. What should I wear? Should I show up a bit early or right on time? What would we do after dinner? And all of the usual thoughts that ran through my head before a first date.

I eventually give in to my excitement and allow myself to enjoy the good mood I found myself in. I slap the book closed and give up on any further attempt to study tonight. I take my violin, put it in its case, then take it and the book back to my room to put them away.

I stop a moment in front of my mirrored closet doors and take a good look at myself. Six foot one, slender though not at all skinny, shaggy dirty blonde hair, dark blue eyes, and a few days growth on my face. I rub my chin. I had some work to do before tomorrow night. I briefly lift my shirt and flex. Hmm, the six pack was well and truly gone. With such a focus on my studies this past year my fitness had suffered. I was still in fine shape but not the lean mean machine I was back in my undergrad. I really needed to make more time for myself. A man could not live off of music and academics alone.

Through my open door and down the hall I see Craig step out of the washroom followed by huge cloud of steam. He had a towel held with one hand around his waist.

He sees me looking his way and returns the gaze.

"I've got myself a date." I say impishly.

His jaw drops and the towel nearly does as well. "No fucking way!? Seriously?"

I nod. "Yep, Michelle and I are going out tomorrow."

"Ohhhh shit! Michelle!?" He lets out a great guffaw. "HA! You're crazy man!"

"You said I should!"

"Yeah, but you should know better than to listen to me."

We both share a hearty laugh. "Wanna go shoot some pool?"

"Yeah man, gimme a sec." He hurries toward his room.

"Hey." I call after him. "The fact she's my Mom is just between you and I."

He glances back over his shoulder. "Obviously." He pauses a second. "Fuck that's hot! That is SO hot! Living the dream."

"You are a sick, sick man Craig." I tease. I was learning a lot about my roommate today. Seems like he had a serious Mama fetish, or milfs at the very least.

"Ha! Me sick? Look who's talking." He disappears into his room and closes the door behind him.

Half an hour later we are in our regular pub getting ready to shoot some eight ball at our regular table. Tara, our regular waitress, was serving us. She was a tiny thin figured long haired red head with a personality that was ten foot tall.

"Two pints and a plate of nachos?" She asks, already knowing the answer.

"Yep." I reply. Then, remembering the glimpse of my less than ideal midsection from earlier, I change the order. I non-consciously stroke my tummy as I say. "Skip the nachos today actually."

Craig laughs. He looks at Tara and jibes me. "My man's got a date tomorrow night. Guess he thinks he can shed a pound between now and then."

She laughs.

I roll my eyes and rack the balls. "Shut up."

Craig wasn't done yet. He leans down to Tara and says in a hushed conspiratorial voice. "It's an older woman. In her forties."

She pushes Craig back by the face, which wasn't unusual between us. "Never call a woman older you knob. She's...experienced. Mature." She shoots me a wink. "Good for you Noah. She'll teach you a thing or two I'm sure." She then adds. "I think all you young bucks should be with an experienced woman before you're let out into the wild. Teach you how to fuck if nothing else. They'd be doing us all a favor."

Craig laughs loudly. "Young bucks? We're older than you are! And don't you worry, these two bucks know how to fuck! Don't we Noah?"

"What you two do in the privacy of your own home is none of my business." She shoots right back.

"What us two...!?" Craig blusters. "NO! That's not what I meant!"

The three of us laugh. I shake my head at their shenanigans. "It's just a first date. Nothing big."

Tara just smiles. "We'll see." She then leans over to Craig and says in low voice. "He's blushing."

"I know, he's been glowing since he called her." He whispers back.

"I can hear you!" I protest.

Tara giggles and heads back toward the bar to get us our drinks. Craig breaks the ball with a loud CRACK and we settle in to a good game of pool. We were equally matched so every game was a coin toss as to who was going to win.

Tara returns with our drinks and sets them up on our high table. Being a Wednesday evening the place was slow with mostly just regulars here and there. Tara having nothing better to do at the moment stands and watches us for a time.

"So tell me about her Noah." She prods. "I'm assuming she's good looking."

I can't even begin to reply before Craig horns in. "Good looking? Oh my god Tara, this lady is HOT! I'm talking...GNNGHHH!!" He bites the knuckles of his right hand.

She laughs. "I figured she must be something special to reel in our boy Noah."

I try to ignore them as I line up my shot.

Craig continues. "Nice wide hips, incredible ass, hour glass waist, and god damn she's got a rack on her! Fucking huge tits!" He emphasizes the point by holding his hands out to signify two big breasts in them. My mother was rather well endowed that way. "I could lose myself in them and die a happy man." Just as I pull the cue back for my shot he adds. "I'd love to nut in a big milfy pair of tits like those!"

My shot veers hopelessly off target. I glare at my roomie. "Jesus dude. Do you mind?"

"Ha ha ha! It's true though! You can't deny it." His eyes are full of mischief. "You're lady is smokin hot and you know it."

My eyes narrow and my jaw clenches. "She's not my lady." I growl.

Tara smiles knowingly. "He doesn't like you talking about her like that." She points at me. "You like this one Noah."

"I just met her." I lie as I settle myself and come around the table to let Craig have his turn. "She was...we got along, okay? That's it. It's just a first date."

She nods. "Uh huh, sure." She studies me for a second with her bright green eyes. "Man, you really like this one. This one's special."

"Ha! She's special alright." Craig teases. "Extra special when she's riding that young D!"

This was my mom he was lewding on! I grit my teeth and hold out my cue like a baseball bat. "I swear to God I'll crack this over your empty skull!"

Tara reaches out and guides the cue down again. "He he he! Calm down there Tiger. We don't have a bouncer tonight. I'd hate to have to kick your asses myself." She pats my chest. "I'm happy for you Noah. I hope you have a great first date."

I relax. "Thanks Tara."

She smiles. "You'll do great." She looks over her shoulder toward the bar where one of the regulars looked ready to slump off his stool. "I better go see how Lou is doing."

"Let us know if you need a hand." I say.

She gives me a thumbs up. "I got this, but thanks."

With that she heads back to check on one of her regular alcoholics. When she is out of earshot I point at Craig with a stern look but an amused smile. "You asshole."

"8 in the corner." He winks as he sinks the shot. "Won me the game. You're buying the pints."

I shake my head and huff. "Asshole."

I wasn't honestly upset. Craig was just being his usual dumb ass self. Besides, I was still in way too good a mood to let something like that get me down.

***

We play a few more games with Craig winning every one of them. He had my number tonight. Some more friends of ours show up and the place begins to liven up, but I decide to retire for the evening. I say goodbye to Craig and Tara and the rest of them and walk back home.

The sun was down and the sky dark but the oppressive summer heat still smothered the city. It was the type of heat where you could actually feel the humid air pressing into you. I climb the stairs of the old brick building where I lived and was glad to get inside the air conditioned suite.

I head to my room and close the door. As usual the first thing I do is put on some music. I keep the volume low. Sitting on my bed with my laptop on my lap I absently look over some news stories then check a few emails.

The strange high I'd gotten after arranging the date had finally dissipated and I was back to my normal self again. It was good to be grounded again. Just "going through the motions" as Dr Nelson had put it had a deeper impact than I'd been expecting. Just the act of it had triggered all too real feelings inside of me. The same nerves, the same uncertainty, and the same elation as if I was arranging a real date. It might have been a fake first date but it certainly fooled my emotions. I would have to keep this in mind going forward.

The whole thing had also brought home just how lonely I was. I had friends and colleagues but I hadn't had a real girlfriend in a few years. A partner to share my life with and wake up beside each morning. I hadn't realized it truly until tonight just how much I missed that.

I run my hand down over my face and let out a sigh. Nothing was going to happen around that tonight and there was nothing to be gained from feeling sorry for myself. Besides, false or not, I still had a date to get ready for. I open a new tab in my browser.

I book a reservation at the restaurant I'd been thinking about when I suggested French food. I then make plans to get a good haircut and pick up a new shirt during my afternoon break. I'd fuel up the car in the morning to get it off my plate.

Tomorrow certainly was going to be interesting. Potentially the most cringe inducing few hours of my life but I was still looking forward to it. It would be nice to treat my Mom to a night on the town. Heaven knows she deserved to be spoiled for a night and I was happy to be the guy to do it.

Looking over my schedule for the next day I see that I had a tutoring appointment I had forgotten about later in the afternoon. It still gave me time to prepare but it wouldn't allow me an opportunity for my usual pre-date tug. As cliché as it was I believed in the advice that a guy should rub one out before a date, especially a first date, in order to be more relaxed and less prone to think with the other head at a time he was trying to make a good impression. I consider briefly canceling the session but I quickly wave those thoughts from my mind. It was a FAKE date. I had to keep reminding myself of that fact. And it was my Mom. I didn't have to worry about being horny around her.

That being said...I wouldn't mind blowing off some steam right now. Some quality alone time was just what I needed to take the edge off.

Closing the other tabs and windows I open up a new one and head straight to Pornhub. I roll over and turn off my lamp and pull the box of tissues I had there closer. Ziiiip. I pull down my zipper then slip out of my shorts and underwear. I pull up my t shirt. With my right hand I begin giving my manhood a preliminary rub down as I start to navigate the site with my left. Porn surfing one handed was a skill I'd mastered as most guys had.

I check out a few of my usual search terms but decide I wanted something different tonight. I start to explore more free form than I generally did. I watch a few short clips of hot young girls and I was good and hard. My loosely gripped hand ran slowly up my thick seven and a half inches. I check out another video, then another. Nothing was quite scratching that itch tonight.

My hand freezes as I see a video come up in the suggested section. "Mom catches her stepson jerking it". In a flash my memory zips back in time to when Mom accidentally walked in on me jerkin my gherkin when I was in high school. I remember with crystal clarity that stunned few seconds as we just stared at each other. Her brown eyes wide and locked on my proud standing manhood. We both nearly died of embarrassment as I hurried to cover up and she gasped and scrambled back out of my room. It was the last time she entered my room unannounced.

Fuck, I'd forgotten about that moment. I had cast it out from my memory banks due to the humiliation of it all.

My rock hard cock strains at the memory. A little drop of precum blooms out the tip.

My cursor hovers over the thumbnail a moment. The woman in the picture, the "mom" character I am assuming, had long dark hair...like Michelle. Brown eyes...like Michelle. Big heavy tits...like Michelle. Her hair was straighter and she wasn't as beautiful as Michelle but...

I shake my head and blink my eyes to break the reverie. Fuck Noah, get a hold of yourself!

The next video over was a big titty compilation. I quickly click on it. Big titties I could get into tonight. This would do the trick. I maximize the video and relax back and really start to masturbate. Even as I watch the scenes of bouncing, jiggling, wobbling, flopping fun bags on the screen I can still see in my mind's eye my mother's wide deep brown eyes watching me jerk off. Staring at me. Seeing my big grown up cock for the first time. I remember with perfect detail the tight hip hugging jeans she wore that day along with the pastel green button up t shirt which her huge perfect tits filled exquisitely. I remember the sound she made, the gasp. I remember how her ruby lips were parted. I remember the shade of her nail polish. The moment which only lasted a few seconds when it happened stretches on and on in my rose colored memory. A blissful eternity of my Mom watching her beloved son pleasure himself.