Truth or Dare with My... Mom? Ch. 01

Disclaimer: All characters engaging in active sexual activity are at least 18 years of age. Reviews and constructive criticisms welcome; flames and critiques of no substance will be snickered at and deleted. Enjoy!

Author's Note: This is a slow-burn story. Buckle in for a long ride if you intend to read.

***

Well, that Friday night sucked.

My mom was going out on her own date, meaning I would have the place to myself. So I'd invited the girl I was seeing over and was planning on getting inside her, when she called at the last moment and not only cancelled, but said she was seeing someone else and we wouldn't be dating anymore.

What shocked me was the dude she was tossing me over for- Kevin Layng. He was short, skinny, kinda dorky, and, as I knew from being in the locker room with him in senior year of high school, nothing to brag about in the manhood department. So either she had a thing for controlling wimpy guys, or ol' Kevin had something on her and she was dating him to keep it hushed.

Whatever. Best of luck to him. I'd just need to reel in and cast out again. There were lots more fish out there in the water, and Gina wasn't the catch of all catches. I just enjoyed that she had a speech impediment- she couldn't say 'no'.

The smug satisfaction of thinking about that li'l train wreck of a relationship was soon soured by remembering that my evening had been scuttled. It was getting on to too late to call anyone else, and frankly, I was rather bent out of shape, meaning I'd be less than perfect company for any gal I went out with. Guess I'm stuck at home.

I'd invited Gina over because I was horny, but now I was just grumpy. I sat at the kitchen coffee table, staring sullenly at the far wall and nursing a beer. I wasn't quite of legal drinking age yet, but I knew mom didn't care, as long as I didn't get into the hard stuff and didn't get smashed, leaving a mess for her to clean up. It wasn't even good beer, just Molson domestic.

So here I had the place to myself, and no girl to get laid with. What would I do? Sure, I could go upstairs and watch porn on my desktop, but that seemed like small consolation after getting dumped. Did I watch a DVD or some subscription porn on the big TV in the entertainment room? Only mildly better, really, not to mention that if I paid for a title, I was stuck watching it, even if it turned out to be a dud.

Go and blow shit up on my computer with my friends in some co-op game? That was a viable means of getting my annoyance out. I'd just have to endure being razzed about slinking back to play after blowing them all off to go on a date. And to be honest, I'd deserve it, because I would've razzed any of them. That's the kind of friends we were.

My musings were brought to an end when I heard the front door open and then slam.

Mom back already? I frowned and looked down at my phone, sitting on the table. It was just after nine. Had something gone wrong?

Mom came almost stomping into the kitchen, looking very sullen, and she didn't notice me at first. She was muttering to herself as she futzed around at one of the counters, trying not to smack things she took out of her purse down on the surface. I couldn't help but notice how she was dressed, and had to admit, she was a fine woman for someone who was not even forty, with lush, dark hair, brown eyes, and a great figure. Her outfit was decidedly not one she'd wearing to her teaching job. On anyone who wasn't my mother, that definitely would have been a 'fuck me' outfit for me.

But this was on my mother, and it was still a 'fuck me' outfit. The skirt was snug and rather short. Her blouse was silky and sexy, rather unusually tight across her chest, reminding me that she sported some generous tits. Her long legs were encase in dark stockings.

Yep, definitely a 'fuck me' outfit, even though it was on my mom. My friends who kept making comments about her MILF status weren't wrong, I admit. I'd seen her in bathing suits and bikinis before, and objectively she was hot, but I made sure I was always assessing her through my 'son' glasses, I guess. My friends probably had a more honest perspective than I did. To me, she was mom, the kindergarten and grade school teacher.

"Asshole..." she grumbled, slapping her car keys down on the surface. "I shaved my cunt and didn't wear panties for this?"

My eyebrow was only just rising at overhearing that sentiment. Wasn't very often I heard her swear, and I don't recall ever hearing 'cunt' from her before. Mom turned around and then yelped when she saw me sitting at the little coffee table in the other corner of the kitchen. She fell back against the counter, holding her chest, her eyes wide and starting to breathe loudly.

"Jesus, Aaron!" she gasped, almost clasping her throat as she tried to control herself. "What the Hell?!"

"I was wondering the same thing about you too, mom," I said somewhat dully. "I take it your date night didn't work out either?"

Her eyes darkened at the query and she seemed to be overtaken by grumpy again, forgetting her shock. She scowled and folded her arms, looking off at some indeterminate point on a wall. Despite the scowl on her face, I couldn't help noticing how pretty she was. Even if she was pretty pissed off.

"Mild understatement," she muttered. "Suffice to say that Ted and I are through."

"Holla," I said, holding up my beer. "I got the heave-ho tonight as well, before my evening began."

"Gina dumped you?" she asked, her eyes widening for a moment and then concern coming into them, her mothering instinct taking over. "What happened, baby?"

I shrugged somewhat dully. "She decided to go out with Kevin Layng instead of me."

Mom seemed very confused. "Kevin Layng? But he's skinny, dorky, and has a little dick."

My eyes widened at her. "Why do you know that?"

She shrugged. "Moms talk. But why him? Does he have something on her?"

"I was wondering that too," I sighed, taking another swig of my beer. "That, or she has a fetish for wimpy guys she can control."

"Either way, you can do better than a slag like her, baby," mom announced, turning back to the counter and resuming arranging the contents of her purse. I had a view of her from the side now, and I had to admit again, my friends weren't wrong. Mom kept herself in good shape, clearly, since she had a tight butt under that skirt, and her tits were definitely nothing to scoff at. Even in her blouse, you knew they were good stuff. Her dark hair was silky and thick, made for pulling on when you fucked her from be-

Wait, what the Hell was I thinking?!

"So I got cancelled on by my bitch ex," I sighed, shaking my head. "What about you?"

"I don't think you need to know, Aaron," she said as she futzed with the contents of the clutch. "Not the sort of thing moms discuss with their sons."

"You would if I was your daughter," I pointed out. "Mom, I'm nearly nineteen, and I care," I said, still watching her. "I wanna know if I need to go and kick the crap out of Ted. Because I totally could, you know."

She paused and turned to look at me for a moment, observing me. "You could, couldn't you?" she mused. "No, he didn't do anything to disgrace me, if that's what you're asking, but he was something of a..."

"Douche?" I offered.

"Well, yes," she relented. "He was a douche. We had just started our date over drinks when he began talking about the need for a threesome to happen. He didn't mind whether it was me and another woman with him, or me with him and another guy, but he wanted to make it happen. And, conveniently, he just happened to have the numbers of a man or a woman who would no doubt be game."

She folded her arms again and scowled at her point on the wall. "Needless to say, our date ended promptly. He even had the nerve to ask if I could drive him home afterward. Douche..."

"Yeah, not the best date to have gone to the trouble of shaving for, mom," I laughed before catching myself and shutting up tight. Mom's eyes widened and she blushed rather furiously.

"You heard that, hm?" she mumbled, looking at the floor now.

"I... yeah..." I admitted, feeling like an idiot now. "Seriously, though, it's not a big deal, mom. I know you're not out dating to find a new life partner, which kinda narrows down the reasoning. I mean, I'm not dating to find the right girl for the rest of my life, am I?"

"Well, of course not, but you're a horny teenage boy, you're supposed to be out trying to get laid," she sighed, gesturing somewhat helplessly with one hand. "What's my excuse?"

"You're a human being and a pretty woman with needs who likes the dopamine rush of getting laid," I reasoned. "You're not a nun, mom. Dad's been outta the picture for a long time now, and good riddance. Am I supposed to expect you to act like some uptight old spinster?"

She sighed and her posture sagged a little. "Well, no, but it's hard to admit in front of your own son that you're out there trying to get a little action. I don't want you thinking less of me."

"I wouldn't mom; I'd think there was something wrong if you weren't," I said simply. "And I'm sorry Ted turned out to be yet another douche."

"Seems to be my luck," she moped, ripple-tapping her fingers against her arm while she gazed at our floor. "So we both lost out big tonight. I'm sorry, baby. Yours didn't even get off the ground, and the choice was made for you."

"Probably for the best," I said, shrugging with both hands on my beer. "Since you were gonna be out, I'd invited Gina back here. Was planning on taking advantage of the big screen."

"Naughty boy," mom laughed. "Maybe it's just as well she cancelled, since my date was a dud, and I would've come back to see my son horizontal and superimposed with some little slag on my good carpet."

"Mom!" I laughed, shaking my head while she giggled. "Yeah, might've been awkward."

"Not to mention the hasty retreat I'd have to beat upstairs and stay locked in my bedroom until you finished," she added. "I would've already been frustrated, and knowing that two horny teens were having hot jungle-monkey sex in my living room might've made things... worse."

"Worse?" I asked.

Mom blushed again. "I date so that I don't keep killing off my battery-operated toys," she mumbled. "I have needs, you know, always had 'em."

I knew mom was rather adventurous back years ago when she met dad, but this was a weird conversation to be having a Friday night, but we were both feeling pretty raw and rather resentful, clearly. Venting was what we wanted.

So why not?

"It's gettin' on to too late for either of us to salvage the evening by going out, so we can just sit here at the table and complain," I suggested. "It's what we both wanna do, after all, shred our exes."

"But you're my son, I can't vent about that with you," she said rather uncertainly. "I mean, you don't need to know those things about me."

"Mom, I already know you shaved and didn't wear underwear tonight," I pointed out. "It beats thinkin' you're repressed somehow."

"I most certainly am not, young man," she huffed, looking somewhat indignant at the inference. "It's just a weird situation to ponder."

"Look, you can sit here and bitch about how much people suck with me, or you can go to your room and murder another toy," I pointed out. "Now at the end of the day, which is actually more therapeutic?"

She considered for a moment. "Honey, I have a lot of bitching to do. Tonight wasn't the first night Ted pissed me off. And I may start ranting about other guys as well."

"Well, just don't start crapping on me for the crime of being a guy, and it sounds like we have a good evening planned," I said with a shrug. "Come sit, I'll get you a beer, and we'll warm up some pizza."

"Pizza, beer, and complaining," she muttered, relenting and coming over to the table finally, sitting down across from me. "It's like university all over again."

"That's the spirit," I said as cheerfully as I could as I stood up and went to the fridge to get the beer I'd offered her along with leftover pizza. "Sounds like we both need it."

Half an hour later...

Mom was still grumbling, and I listened intently. She took another pull on her beer, made a face and scowled at it. "Ugh, domestic..."

I shrugged. "Y'want wine, that's something you do with girlfriends while you complain about how much men suck. We can switch to that later. I'm your son, and I offered beer."

"Fine," she said, pointing the lip of her bottle at me. "But after a few of these, you do at least one bottle of wine with me."

"Okay, fair," I said. Wine wasn't my preference, but I was perfectly capable of drinking it when called upon. "You were saying about Ted?"

"Oh right," she remembered, her countenance darkening for a moment before starting in again. "He wasn't keen on giving oral, thought it made him look effeminate. He was more than happy to receive it, mind. And the few times I did manage to get it from him? Hardly worth the effort."

"Three outta ten, would not recommend?" I chuckled.

"Let some other dumb bitch find out he's got the tongue skills of a chimp on Thorazine," she grumbled before taking another pull, and then shoving a piece of pizza into her mouth. She waved the back of her hand at me to indicate it was once again my turn. "Teh muff abouf Gifa."

"Well..." I began, considering what exactly to tell her. She was still my mom, the schoolteacher, after all, but this had been my idea, so holding back seemed unfair. "Like I said, it was easy enough to get her to skin off her panties, so there's that."

"Did you use protection, or was she on some form of birth control?" mom asked after she swallowed her pizza.

"She was on birth control, seemingly, but I always had condoms handy in case she'd had one of her flighty days and had forgotten to take the pill. I used to make her time it so that I could watch her take them at school during lunch. That way I knew she remembered."

"And then it was rawdog city?" she snickered. "Not that I blame you, Aaron, it does feel so much better without a condom in the way."

"I'll take 'things I never expect to hear from my mom' for a million, Alex," I chuckled.

"This was your idea, young man," she pointed out. "And I am indeed venting and getting things off my chest. It's not like I've started fussing over you."

"And for that I am thankful, mom," I said, raising my beer in salute.

"Besides..." she almost murmured, looking a tad awkward and blushing, "I'm a woman, and I like the feeling of a guy busting a nut inside me."

"Make that two million, Alex," I sighed, shaking my head and smirking.

We talked and vented, and I was on my fourth beer while mom was on her third. We'd killed off the leftover pizza and now I was heating up junky Chinese food. Sometimes, it was exactly what you needed, and this was one of those moments.

Mom sighed as she stirred around the noodles in her bowl with her chopsticks. "Aaron, how often do you get laid?" she asked rather quietly. "I just wanna know, because if you're the teenage average, then I wanna see how far behind the curve I am. I used to not be, after all."

I shrugged, not really bothered by the question at this point. "I mean, if I'm honest, I probably get laid a little more often than your average teen, mom, because Gina was always good to go. And what do we mean by 'getting laid' specifically? Do I need to be inside her? Does getting oral from her count in a dark classroom at school?"

Mom giggled. "Questions I've tried to never ponder about my son. Well, okay, not true, I have spent time thinking about your sex life."

"You're my mom, so that doesn't surprise or bother me," I said. "It just means you care."

"I do," she confirmed. "But back to my question. How often do you get laid? Let's define it broadly as another person giving you an orgasm directly."

I had to think about it. Finally I answered. "Well, including getting blown, then about four times a week."

"Definitely more than me, but nowhere near as big a gap as I expected," she said.

"Well, I'm kinda busy, you know," I reasoned. "And it's not like it's one-and-done orgasms, sometimes there's marathon sessions with many orgasms. But I'm lumping those all together as one 'getting laid' event."

"Oh," she murmured, blushing a little. "You must hardly ever need to take care of yourself."

I guess I was feeling unusually honest. "That's a twice-a-day thing at least for me, mom, unless I got laid, in case maybe once."

Her eyes widened at me and then she began giggling and blushing more. "I'm sorry, I forgot about how horny and virile young men can be."

"So get yourself a young man to see to your needs," I reasoned, although I never would've believed I was saying it to my mother outside of this context. "Not like I'm gonna judge you."

Mom was still giggling and blushing. "You think your old mom oughta be a cougar and go out to get fucked by a young man?"

"I mean, don't bring him home or I'll wanna beat the shit outta him," I qualified. "I know young men, after all. But it would be nice to know you're getting your needs met."

"Have you ever been with an older woman?" she asked out of the blue.

That question caught me off-guard. "What?"

"C'mon, boy," she urged, smirking. "Have you ever had sex with a cougar?"

My turn to blush.

"Oh my goodness, you have," she breathed, her eyes dancing with excitement. She leaned forward on the table and put her chin on her hands. "Tell me. No, wait!"

She drained her beer and then got up and wiggled quickly over to her wine cabinet, grabbing a bottle of red and two glasses. "This is a wine conversation, so finish your beer by the time I get back. Go go go!"

I sighed and gulped my beer, knowing there was no point in protesting. Mom was back only a moment later, uncorking the bottle and pouring into the two glasses, making them rather full. This was serious business, apparently. She pushed mine across to me.

"Now, continue," she said, taking a sip and resting her chin on her hand again. "Tell me about my little boy's trip to MILFland."

"Only if you promise to never say that again," I muttered, making her snicker. Mom thought she was the funniest person on the planet. Always had. "Fine. It was... Mrs. Marshall."

"The history teacher?!" mom gasped, looking shocked. "You fucked your history teacher?!"

"I... yeah..." I admitted, now blushing.

She regarded me curiously for a moment. "Was that the semester you were failing History and all of a sudden your grade in the class jumped for no particular reason?" she asked.

I didn't answer quickly enough, clearly, because she burst out laughing, almost spilling her wine. I'd seen my mom laugh countless times before, but not very often like this, losing control to her mirth entirely. It was quite the insight, along with everything else I was finding out about her.

"Ohhhhh, my horny and sneaky little boy," she almost wheezed, her eyes shining, almost glistening with tears of mirth. "You fucked your way to an A? I'm so proud of you, Aaron!"

I waited while mom kept snickering, not feeling irked so much as slightly needled. "Well, didn't you ever fuck someone to get what you needed?" I asked rather pointedly.

Mom finally arrested her laughter and stared at me, trying to decide if she could tell me. "Well, yes," she admitted finally. "More than a few times when I was younger, and mayyyyybe sometimes since then, possibly once or twice at work to nick a project or outcome I wanted."

She blushed a little. "Not ashamed of me for that, are you?"

"Hell no," I replied, shaking my head. "You get shit done, mom. It's just sex, right?"

"How many times did you have to boff Mrs. Marshall to get that A, baby?" she asked, going back to smirking.