Truth or Dare Seriously

Heads-up: this a longer story than my others. It's little more than an extended Truth or Dare tale, with a certain element of slow-burn geekiness. If any of that is not your thing, you'd be better off skipping it and enjoying one of the other fine stories on this site.

By the time the summer of 2020 started gasping out of breath, the great scare of Covid19 started dimming and people began making up for the Great Isolation. None with more gusto than my dear mother. A people person to the core, spending the first six months in isolation was torture beyond description for her. Fortunately, her job gave her unlimited Zoom access, and she did her best to wear out those wires with coworkers, friends and family.

Labor Day weekend was to be the Great Get-Together for her and her three closest office mates--her chicks as I called them (she being the mother hen). Our apartment was close to the smaller pool of our complex, and their hot tub happened to be outside our ground floor apartment's back patio, so guess where the party was slated to be?

As the resident male, all of 18 years, barman duties for these occasions usually fell to me, so I was told to stay home and "volunteer." No hardship in all honesty, because Mom's coworkers were all hot, especially when rocking their bikinis. All were younger, my MILF Mom being the oldest at 38. (Yes, like so many guys, I had "those" fantasies and put them to good use loading the landfills with soaked tissues.) Yolanda, 24, was the youngest. Chubby, she had bulges in all the right places and not shy about letting the world see them. Olivia, late twenties, slim, and classic oriental with straight black hair and lidded eyes, was still at least five years younger than Angela, the single soccer mom of a girl just turning teen.

Still being of tender age, I of course was not allowed to purchase the liquor for the event, but that did not stop my mom from dragging me along as the pack mule. So, even though none of her friends drank beer, a case of Fat Tire stole its way into the cart. When she'd be laughing with her friends, she wouldn't be able to keep her eye on me

all

the time, now, would she? Besides, she was cool with what happened at home... as long as it stayed at home.

Why wait until the actual Labor Day (Monday)? Mom arranged for the party to start Friday, right after work, with a long weekend to stretch the proceedings (code for hangover recovery). Knowing nobody would be driving that night, I 'volunteered' to vacate my bedroom so two of the ladies could share my queen bed while I slept on the couch. Mom and the other one would share her king-sized bed.

Rather than make a heavy meal, we stocked up on finger foods. Not that I would ever cop to it, but I made sure we got the saltiest snacks we could, to inconspicuously cause maximum thirst. Call my mind dirty, but a gaggle of highly tipsy hotties held interesting potential. Who knows what lusty single women might want to do with a strapping young man (no longer just a boy), especially after the deprivation Covid wreaked upon us all?

Speaking of which, I also went hunter-gathering for some potent weed, just in case. Like someone said, luck is preparation and opportunity meeting on the same side of the street.

--

Friday eventually dawned upon us. My freshman college classes would be starting soon, so I spent the day burnishing my tan and getting things ready. My phone dinged. MA text from mom that Angela (the 4th group member) had something come up with her daughter, so it was just going to be mom and the two others. For a few of the games they wanted to play, they would need four, so would I be okay with joining them?

Ha. Does the Pope ride in a convertible?

What games? Hopefully not bridge or something boring. And hopefully not before they availed themselves of the pool and/or hot tub... with a minimum of clothing, of course.

I set the blender on the counter, made up a big bowl of margarita mix, and arrayed the accouterments for the evening's liquid refreshments next to it. The beers languished out of sight at the back of the bottom shelf in the fridge. Next, I set out the pretzels, peanuts and other dry snacks, and got the oven up to temp for the spring rolls, samosas and other salty eats.

All arrived at the same time in Mom's car. No driving for them after the party.

The first order of business of course was liquid refreshment after another rough week. (When it comes to justifying Friday night drinking, aren't all weeks 'rough?') The three women spread out in the living room and I immediately served them their drinks. I brought each one a paper plate and napkin. Then set the salty snacks out on the coffee table, and made up a plate for everyone.

No sooner had I completed that, than their margarita glasses called for a refill, and of course I answered the call. Gossip still dominated the proceedings, particularly one Jenny, a coworker of theirs who apparently started falling for the department's pussy hound, Dennis something or other. Yolanda (chubby, youngest) lowered her voice and allowed as to Dennis being rather well-endowed. To the others' questions, she admitted to having first-hand knowledge.

"So why are you here, and not with him?" I asked.

The looks by all three told me that was not a kind or smart thing to ask.

"What?" I asked with hands spread. "Hey, I'm a guy, and young, what do I know?"

Yolanda came to my rescue. "You're right. How are you to know Dennis may think he's a stud, but he's awful in bed? Even though he's, ahem, big in the britches, he's a total loser. Just thinks of himself, then rolls over and falls asleep. That's why he can't keep a girlfriend. Women who go out with him have two happy moments: when he unwraps his dingamalerie, and when they leave the first chance they get." She paused and raised an eyebrow. "Now you know why I'm here with you--does that answer your question?"

"Yolanda!" Mom groused. "Behave yourself. That's my son."

To defuse the situation, I went to the kitchen to put the spring rolls and samosas in the oven and set the timer before making up small bowls of hot salsa. Yolanda's comment gave my spirits a boost. Nice to think a hot woman thought I was worth flirting with.

I topped off everyone's snacks and refilled their drinks. "So, what games are we playing tonight?"

My worst fears came true--the games the ladies wanted to play were boring. Simple card games like hearts. Hearts? Seriously? To think such hot women had so little imagination? Like, what's so wrong with strip poker?

The good thing about boring games, though, is the girls were never too distracted to snack and drink. The salty snacks did their job and parched them nicely, so I spent the first couple of hours pouring round after round to slake that thirst.

And, as a group of single women facing a long weekend after a boring week at work are wont to do, after like the third or fourth round, stories and jokes turned raunchy, punctuated by squeals of faux-shocked giggles and laughs. More than once, one of them would point at me and say, "Cover your ears, young man." Yeah, right.

I found their stories educational. For one, I had no idea my mom was so aggressive on their girls' nights out. Apparently, she was the first one to hit the dance floor. And apparently, none of them were too shy with the guys who had them out on the floor.

Not surprisingly, Yolanda was the bell cow, pushing the envelope of propriety and scolding the others for lagging behind. Since all were single or divorced, everything was on the table, with no scandals as they recounted their exploits. Other than the odd pair of panties left behind as souvenirs.

Furthermore, their dissatisfaction with the games bubbled to the top. "Hey, Melissa, what other games do you have?" Yolanda asked my mom with the first hint of a slur.

"What kind of games are you talking about?" Mom said with a nervous look in my direction.

"Yeah, you know, more

adult

games," Olivia said with a raised eyebrow. I never learned whether her heritage was Japanese or Chinese.

Mom played dumb, not that she fooled anyone. She had, after all, been out with the others a lot, and I had an inanimate knowledge of her collection of porn DVDs and sex toys she thought she had hidden deep inside her closet.

"I have a game you may be interested in," I ventured.

"What? Not Monopoly?" Yolanda cackled.

"Oh no, an

adult

game," I deadpanned, as if to say, "Doesn't everyone have a stash of those in their closet?"

Mom was shocked, Olivia raised her eyebrows and Yolanda let out a long "Whooooo. Tell us more, tell us more!"

Before Mom could object, I said, "My friends gave me an adult Truth or Dare game as a gag gift for my 18th birthday."

Yolanda waved her hand in dismissal. "We don't need Truth or Dare packaged. We've all played it off the cuff."

Not me. Who would I play it with? The nerd from Central Casting? No friends,

et cetera, et cetera.

"I haven't even opened it yet, but from what my buds told me the benefit of this one is the questions are all pre-formulated. No need to make up lame, wimpy questions." I held up my hands before anyone could float up an alcohol-induced comment. "That's what they told me. Like I said, I haven't opened it yet. Just a suggestion, since y'all were asking."

Before anyone (read: Mom) could turn this into a discussion, I continued. "So, let me go and fetch it, and we can all open it together."

Mom drew in a breath, but before she could utter a word, the other two chimed in with claps and cheers. Confirmation that they'd happily arrived in Margaritaville.

When I returned, the women had placed themselves in a circle on the ground where the coffee table had stood, leaving a space for me.

Noticing empty glasses all around, I removed and replaced them, this time using bigger but plastic tumblers. No chance of anything falling over or breaking. Also higher capacity meant fewer refill trips. Good thing I had a second pitcher of mix chilling in the fridge. Then I added four shot glasses and brought out the bottle of Hornitos Plata (top class tequila) from my closet when I picked up my game.

Whistles and cheers greeted the bottle. In a voice filled with horror, my mom asked, "When and where did you get that? How come I don't know about it?"

I gestured for her to calm down. "First of all, mother of mine, please notice the bottle is still sealed. My buddies pooled together and bought it as my 'real' 18th present, along with a set of eight shot glasses. For special occasions, they said. Well, I think tonight is a special enough occasion, as we celebrate our ending of Covid isolation."

"Enough yakking. Open it up," Olivia said, picking up a shot glass and holding it out to me.

"Hmm... I like the name," Yolanda said with a suggestive wiggle of her hips. "Horny tos. Sounds like the perfect tos to me."

Everyone collapsed with laughter. Amazing what a few rounds of drinks will do for everyone's sense of humor.

I held out the bottle to my mother. "Mom, I will leave the ceremonial breaking of the seal for you as the head of the household."

"Hmm..." Yolanda said. "The ceremonial initiation of your boy into manhood."

Again, laughter and giggles. "With horny tos," added Olivia, to another round of cackles and giggles.

Lightening up with the levity, Mom grinned and made a production of cracking the seal and twisting out the top.

I held out my shot glass.

"That's right, mommy. Make a man out the boy," Olivia said with a grin, bordering on a leer.

When my glass was full, Yolanda said. "Okay, boy. Down the hatch or whatever guys say. Time to man up."

Looking my mom square in the eyes, I downed the glass. Not too bad--better than the cheap stuff my buddies had me practice on. Still, it lit a blazing burn down my throat and settled into warm embers in my stomach. I blinked away the tears that sprang up in reaction to the fire.

"Yay!" all three cheered. Mom, getting into the spirit of things (no pun intended), filled all four shot glasses.

Yolanda held up her glass. "To Gunnar becoming a man." After clinking, all four downed our shots and Mom passed the bottle to me. "Here, you're the bar

man

now. Take care of your women."

Amidst the giggles, I refilled the glasses and unwrapped the game. With great ceremony, I stripped off the cellophane wrapping so all could see it truly was new and unused. Opening the box, I read the instructions. "The game is played in stages. In each stage, a new box of cards are read in turn. Part of the game involves removing clothes, so players should ensure all are wearing the same number of garments before starting. If any player is deemed to hesitate too long, he/she has to take a drink."

To comply with the garment thing, we all ended up with four items of clothing--the women with top and pants, and underwear. I added a baseball cap to my shirt, pants and underwear to even it up.

"Okay, Gunnar, since it's your game and you're now being initiated into manhood, you start," Mom said with a benign smile.

"Okay." I opened the stage one pack of cards and read aloud, "Round one will be truth questions. Each player will pick a card and answer the question. Any hesitation will require a drink or shot."

I picked the first card.

"How many times have you had sex?"

Silence followed some nervous laughter. "Ooooh," said Olivia. "Dirtiest secret out with the very first question." Everyone laughed, although my mother's eyebrows stayed high.

"That's both easy and embarrassing," I said. "None."

"What?" Olivia said, "Never? You're such a hunk. I thought you were getting special discounts buying condoms by the case."

Squeals of laughter erupted. As the ruckus settled down, Mom said, "He's too decent to go with the loose girls, and too respectful of the conservative gals. Right, Gunnar?"

I blushed and simply passed the box with cards on to her, as the player on my left. "Your turn."

Probably to spare me, she immediately reached in and pulled out a card.

"With how many partners have you had sex?"

Mom stuttered. "Well, depends on what you include or exclude."

"Hesitation!" Yolanda cried. "Take a shot."

"What? No, I was trying to clarify the question."

Olivia and I joined the chant. "Melissa needs a shot. Shot. Shot. Shot!"

Blushing, she said, "If you mean actual intercourse, four men."

"Who?" asked Olivia.

"They didn't ask, and I'm not going to tell. Your turn." She passed on the box, but not before emptying her shot glass.

Olivia reached in and pulled out a card.

"Have you ever had anal sex. If so, did you enjoy it?"

Grimacing, she said, "Paul insisted on it, but I hated it. It hurt, so we rarely did it. Maybe that's why he left." I can imagine with her petite little Oriental body her pucker hole had to be teeny. Suddenly the thought occurred to me: hey, I might actually see it tonight.

In the dampened mood, Yolanda took the box.

"When did you lose your virginity, and to whom?

Well, like so many other kids, it was prom night, with Harry Dawkins. I so looked forward to it, and it was great. He booked a hotel room and we fucked the whole night. I was so sore the next day I could hardly walk."

I secretly relished the first time the word fuck made it to the conversation. Hopefully between the margaritas and shots, everyone's tongue would loosen further. The buzz in my head was more than just the drinks. This could get good.

"And that's why you never stopped," Mom said.

Amid the laughter, the box slid my way again. "Second time around," I said. "Everyone take a swig of their drink."

After we all took a sip, I read.

"What kind of porn do you enjoy?

Wow, I didn't see that one coming."

My mother immediately pounced on my waffling. "Hesitation! Shot for Gunnar," she cried, and the others took up the "shot, shot, shot" chant.

I downed my shot glass and refilled her glass and mine. Then I decided to go for broke. What the hell? It was my game, and the worst they could do was banish me. Their loss. I took a breath and replied, "My two favorite kinds are mature and incest. So sue me." I glared around the room with a challenging stare.

"Mature?" Olivia crowed.

"Incest?" my mother followed. "Dare I ask what kind of incest?"

Karma smiled on me, because at that moment the oven timer went off. I scurried to the kitchen to take the spring rolls and samosas from the oven. I arrayed them on my mom's snack dish and filled the two sauce holders with sweet and sour sauce and hot salsa.

Returning, I walked the dish around the circle for each to pick what they wanted while they digested my porn bombshell. Then I set the dish on the floor in the center, and moved the card box to my mother. "Your turn, mom."

She looked at me, started to say something, thought better of it, and read the card.

"Have you ever had cybersex?"

She looked up and calmly said, "Yes," before passing the box to Olivia.

"Whoa!" all three of us erupted in a cacophony of questions. "Who with? When? How?"

Mom just pointed at the box and said, smugly, "They didn't ask. Your turn."

Olivia, looking at my mother with newfound respect, picked her card.

"What's your favorite sex position?

Oh no doubt, doggy style."

Hoots and hollers erupted. "Great taste," Yolanda said. Mom's silent nod affirmed that choice was not without merit in her bedroom. For a moment an image of my mother on her hands and knees, with my hard young cock pistoning in and out of that juicy pussy filled my mind. Whoa! Hot. Who knows? Maybe one day, someday. With a sigh I brought my mind back to the game.

Yolanda reached for the box and read her card.

"When you masturbate, who do you do it to?

Well," she answered, "I have a cast of characters I rotate through, so not just one."

"Is Gunnar one of them?" Olivia cackled.

"The question didn't ask me to name al of them." But she blushed and looked down when she said it. And immediately passed the box to me.

Oh wow! More blood headed Little Gunnar's way. Not wanting to embarrass her, I took the box and said, "Last time around on this stage. Everyone take a sip."

Mom and Olivia emptied their glasses, so I fetched the pitcher to refill them, and a fresh bottle of beer for me.

After taking a swig, I picked out my card.

"What's your most embarrassing sexual moment?

Well, again, that's hard, because I've not had a 'sexual moment.'" I made air quotes. "I guess the closest was almost getting caught spying on my mom's sister when she stayed with us."

Mom jumped all over that one. "When? What happened?"

"They didn't ask for details," I said with an overly pious expression mimicking her earlier evasion, "but it was last Christmas. She left the door of her room open and I saw her naked as she came out of the bathroom. I heard you coming up the stairs, so I slipped back into my room. For sure I thought you saw me but if you did, you were nice enough not to mention it."

All three women laughed as I passed the box to Mom, who picked out the next card.

"How often do you masturbate?"

Her blush and hesitation brought out the calls for another shot. She took a deep breath, emptied her shot glass and whispered, "Once or twice a week." To forestall any discussion, she held out her shot glass and I refilled it. By this time the four of us were definitely feeling no pain.

"Only once or twice a week?" Yolanda said with a laugh.

"Shut up," Mom grinned back. "At least I'm honest. How often do you do it?"

"Definitely more than that. Whose turn is it?"

Olivia took the box and opened it.

"What's the most interesting place you've had sex?

Probably on our honeymoon hotel room's balcony. Paul had me naked, leaning over the balcony railing, and fucked me from behind. I'm not quiet, so that day I had to bite my hand to not draw attention to us."