Truth or Dare with My... Mom? Ch. 03

She grabbed my head, her fingers curling into my hair and pushing down as hard as she could while she pressed up desperately with her hips, virtually planking off the chesterfield. My face was mashed into her crotch, and I couldn't see anything, but I could almost hear her teeth gritting.

Mom shrieked, thrashing around me, and then my face was getting incredibly wet. Mom was not only cumming, she was squirting. My face, my mouth... her fingernails were straking my scalp, but I barely noticed. I just kept licking, kept fucking her ass with my finger. Nothing would stop me until I'd given her the orgasm that matched the one she gave me.

Mom didn't sag or fall back into the chesterfield, she collapsed. It felt as if her body were coming apart, like a skeleton collapsing into a pile of bones in old cartoons. I moved with her, still licking, still fingering. I wouldn't stop until she gave me some indication that it was time. The taste of her pussy, her cum, was all I could think about, coating my mouth and my throat.

Her hands were finally caressing me again, and she seemed to have relaxed. Her fingers were still in my hair, but the touches were gentle, slow, and languid. I began to ease up, replacing my licks with kissing, tiny pecks on her clit while I pushed my thumb gently into her pussy, not depriving her of the sensation entirely, while my middle finger simply stayed still inside her ass.

I looked up and she was smiling down at me, her face radiating what I could only call bliss.

"Come up and let mommy kiss you, baby," she cooed, eyes shining with love. Feel free to keep those fingers where they are, though..."

I nodded and leaned back before coming up onto the chesterfield, sitting beside mom and nestling into her, both of us positioned so that my fingers were still easily inside her. Mom squished into me, her tits against my chest as she kissed me, deeply, lovingly. I shivered as I felt her hand find my hard cock and wrap around it gently.

"Mmmmmm," she sighed through our kiss, her eyes closed. Her hand was stroking my shaft, an expression of affection, not an attempt to get me off. "Best... oral... orgasm... ever..."

"For real, mom?" I asked, my fingers still inside her. "It's okay if it wasn't-"

"Baby," she murmured, pecking at my lips while she spoke. "Mommy isn't lying. You absolutely rocked her world. You gave mommy the best oral orgasm she's ever had, hands down. Even Tracy didn't ever match that."

I shuddered, humbled at the thought. Mom had given me the best beej of my life, so maybe this was fair, but it still stunned me to think a punk kid like me could've done that for her. She was goddam sex queen, after all. Who was I in this universe?

Mom started to lie down, and I went with her, the two of us nestling on our sides into each other. I was still fingering mom while she stroked my cock gently, and we shared a loving kiss. Tongues tangled slowly, just letting one another know how loved they were. And boy, did I feel loved.

"Mmmm, can you feel your fingers touching through me, my love?" she asked through the kiss. I paused long enough to feel around, and indeed I managed to press the tips of the two fingers together through her.

Mom jumped and then giggled, shivering and squirming as I tapped the two fingertips together gently.

"You brat," she giggled through the kiss. "You and Tracy, always gotta push the limits, don't you?"

"Not sure I've found yours yet, mom," I replied, smirking and kissing her nose. "And the day's still young."

"Your finger feels so good in my ass, baby," she whispered, caressing my cheek with her free hand while the other still stroked my dick gently. "Mommy loves anal and anal play. I always have. Always loved having things in my butt, as far back as I can recall."

I nodded. "At some point, I'll have to give you the tenpin."

Mom raised an eyebrow. "Oh, God, is that the one where I lie on my stomach and then you put your thumb in my ass and two fingers in my cunt, like a bowling ball?"

I nodded and mom dissolved into snicker fits, her entire body jiggling against me so hard that she even had to stop massaging my cock. She kept my fingers in her, but wiggled up until my face was secured between her tits. She squirmed them around, smirking at me.

"You're such a funny, good, and naughty boy, Aaron," she sighed, holding me. She smelled like a woman who had cum, and it was Heaven. I could've stayed buried in her tits forever. "I can't tell you how much I love you."

She put her fingers under my chin and then lifted it so that I was looking up into her soft brown eyes, which were shining. "And I've always been in love with you, baby. You've always been my everything."

I smiled. "Is it weird at all if I say it back?"

She shook her head.

"Then I guess I've always been in love with you, mom," I said, my feelings swirling in confusion. How exactly did I mean this? "I guess every boy does, but... who's ever had a more perfect mom than you?"

We were leaning in to kiss again when there was a ping! sound from my laptop indicating the transfer was finished, and my files were transferred to hers.

And mom broke down giggling at the timing.

"Even the electronics agree with you, Aaron," she quipped, still laughing. She moved around until my fingers came out of her, and she was getting out of the way. At least I thought she was. She was on all fours sideways and kneeling over me. She had her hands on my thighs while she leaned down and pushed her mouth down my cock, humming in delight as she did it. I shuddered and moaned, my hand closest to her ass fondling it gently and then strumming over her gooey pussy.

Mom finally came up for air and then moved aside while I went to check on the transfers. Sure enough, they were both completed. All of mom's files were now on my drive, unencrypted, while my files were sitting on hers. I picked up the remote and turned around, pausing as I saw mom knocking back an entire glass of cognac. She exhaled loudly as she finished and looked at me.

"It's gonna take a lot of liquid courage for me to get through this next part, baby," she said, filling both our glasses. "And we did say we were gonna get fucked up, right?"

"True dat," I said, nodding as I came over and got my glass from mom. I followed her example and just knocked it back. We wouldn't get shit-faced by moderating ourselves, would we?

"So how are we gonna do this?" I asked as I sat down.

Mom considered. "Well, sitting side by side on the couch seems boring and amateurish, the only plus being that it'd be relatively easy to jerk you off while you play with my pussy. But it's way more intimate for you to spoon behind me, isn't it? And we can still talk about what we're watching."

"I like it," I agreed, letting mom move out of the way while I lay against the back of the chesterfield on my side, facing out. Mom giggled when she saw Aaron Jr pointing ahead of me, but then got down and snuggled in close, facing out from me. My cock was once again speared between her thighs and poking out from between them. She reached down and caressed the visible head softly for a moment before smiling back at me.

"Truth or dare, my love?" she asked while my hand came around underneath to rest on one of her breasts, cupping it.

"Dare," I said simply.

"Okay," she replied, nodding. "I dare you to show me your naughtiest video."

"Okie-dokes," I mused, thinking about it. "How about..."

I used the universal remote, which was now synced up with my laptop, to find my folder of homemade porn, and started sifting though the folder choices.

"Not many folders," mom observed, her hand on top of mind while it caressed her breast gently.

"I'm probably just lazy about categorizing," I said with a shrug. "I'm pretty sure you have sub-folders within sub-folders within folders, everything OCD categorized."

"It's true," mom snickered. "By date and type of sex act. Tracy has her own folder, for instance, but it's cross-indexed with the Lesbian folder. Oooh, you have a solo folder?"

I almost blushed. "I have a few videos of me jerking off. I don't really watch them, but some of my girlfriends like receiving them on occasion."

"Show me one before you get to the naughtiest video," mom said rather eagerly, reaching down to fondle my cock to make her point. "Show me my little boy in action."

Here we go... I thought as I clicked on one of the MP4s in the Solo folder.

Mom watched intently, while I watched mom. Her eyes were as wide as dinner plates. I was resolutely not looking, but I could hear myself panting and moaning.

"I don't even remember those sheets, Aaron," she breathed, watching rapt before turning her head enough to smirk at me. "How the Hell old were you?"

Her attention was drawn back to the screen by a loud groan. "Oooh, money shot!" she laughed, squeezing my dick between her legs. "He's been a big boy for a while now, hasn't he?"

"Mom, it's just the two of us and you're still somehow embarrassing me," I sighed, thankful that the video was over. "Y'ready for my naughtiest moment?"

Mom nodded, looking at the screen intently. I found the video in a folder and hit 'Play'.

"Oohhhhhhhhhh, niiiiiiiiice," mom said quietly as she watched me going at it with two girls. "When was this?"

"Just before end of fall semester," I replied, watching. One of the girls was sitting on my face, facing down my body, while the other was impaled on my cock, moaning lustily and bouncing up and down. They were leaning in and kissing one another hungrily, fondling each other's tits. "Recognize them?"

"Uhhhh, the one girl spiked on your dick is named Lori, but I can't place the other one," she said, squinting at the screen. "She's Asian, though."

"Yeah, that's Anna," I confirmed, nodding. "Watch this now."

Mom watched intently as Lori turned herself around and now leaned backward so that she was supporting herself on her hands and her feet, while Anna had removed herself from my face and crawled down to take hold of my cock. She sucked on it for several seconds before she held it steady and then Lori moaned loudly as she sank down, taking me in her ass.

"Brave girl," mom said, squirming as she watched. Anna was licking at Lori's pussy as the redhead went up and down on me, her ass on display and distended by my tool. "Lookit her go."

"Yeah, Lori was a real butt slut, always had been," I agreed. "She hated Gina, so any chance she got to stick it to her was a win. I didn't mind too much, especially if Anna was along for the ride, so to speak."

Mom was glued to the action on the big screen, watching in awe and delight as both Anna and Lori got on all fours, their cute butts in the air. I took turns fucking each of them in the ass, moving back and forth between them several times.

"That's the anal roulette you were telling me about," mom said, her voice little more than a whisper, her fingers stroking along my cock slowly, almost absently. "That looks so amazing, baby. Who won?"

"I don't even remember," I chuckled. "I don't think they knew either, look at them making out while I drill them."

"Slutty girls," mom snickered. "But so lucky. Is this your naughtiest?"

I shrugged. "Maybe? I think the anal roulette kinda makes it, you know?"

"Maybe show me a few others, see what crops up," mom suggested. So I did, and it took a few minutes. Since I'd recorded most of the stuff on my phone, none of the clips were super long. A few were several minutes, but most were a minute or two, a few of them hasty, done on the spot.

"Oh, my," she said quietly as she watched one, then turned her head to look up at me. "Not exactly new to the sex game, are you?"

I shrugged. "Pretty obvious I didn't know what I was doin', though."

She smiled and puckered her lips. I leaned in and kissed her, lovingly. I pressed the 'Pause' button since we weren't paying attention to the screen at the moment, then put the controller down and filled my hands with mom. She turned into me, her front pressed to mine. Our tongues tangled and she gently fondled and stroked my cock while I fondled her pussylips with my fingers.

"Mmmmmm," she hummed through the kiss. "Reach behind me and grab one of the liquor bottles, baby..."

I don't even know which one I grabbed, at least until I brought it over. It was Irish cream, and mom took it from me and swigged right from the bottle. She then pressed her mouth to mine, kissing me deeply as she rolled on top of me, passing the Irish cream into my mouth. We passed it back and forth until it was gone, our kisses now tasting like whisky and cream. We'd forgotten the TV for now, groping one another as we made out.

Mom shivered as the head of my cock touched her pussylips.

We were both breathing heavily when she broke the kiss, looking down into my eyes, her face flushed. "You ready to see mommy act like a depraved slut, baby?" she asked, her voice trembling.

I smiled rather evilly. "I dare you to show me what you looked like when you're being a depraved slut, mom."

I guess this bolstered her somehow, with the framework of our Truth or Dare game, but she nodded and then settled down in front of me again, my cock camped between her thighs and resting under her sopping pussy. Mom had seen how to use the controller on the laptops and now was operating it. She opened her folder on my laptop and began scrolling through it. She highlighted one folder and seemed to pause, hesitant.

I looked at the folder. It was titled 'BAD'.

"There it is, baby," she breathed. "All my sluttiest and most depraved moments are in there."

"Open it and hit play, mom," I said, nodding and then holding her close.

Mom swallowed but then reached forward and hit the Play button. The video player program would simply cycle through them in order, whatever mom had done to them.

I watched, dumbfounded, as the screen showed mom's hips and pussy, scissored with a pair of hips and a pussy that looked pretty much exactly the same. The panting that was happening matched the action on the screen, the two smooth cunts mashing and grinding. Mom and Aunt Tracy were whispering and grunting obscene things to one another.

"We didn't have cellphones," mom said, her voice seeming distant. I watched, rapt, as they ground their pussies together, holding one another by the wrists and tugging, bringing them closer together.

Which brought up a question.

"Mom, who's filming?" I asked curiously.

"To be honest, honey, I don't even remember," mom murmured, her eyes glued to the screen. We watched as she and Aunt Tracy sort of sat up, leaning back on their hands and then began to not grind, but pull back and then slam their hips together, pussies hitting one another with increasing force. They both gasped and whimpered as they duelled, seeing who could last the longest.

"We loved one another, but cunt-busting was kind of a competition for us," mom said quietly. "We'd bash 'em together, see who gave first. The person who won had the bragging rights, but we always cared for one another and kissed each other's boo-boos better afterward. Sometimes, we even just hugged close, crying and apologizing for hurting each other."

"Pussies are a lot tougher than dicks," I admitted, still watching them ram their crotches together. Mom seemed to win the round we were playing, because Tracy finally gave in. "Anybody did that to me, I'd fuckin' die, they'd break my dick."

Mom giggled. "I never did understand the whole 'grow some balls' statement. Balls are soft and weak. It should be 'grow a vagina', because these things can take a pounding."

I laughed and reach down to cup mom's pussy, giving it a squeeze. Mom shivered and giggled, squirming back against me. I brought my hand back up to her tits and we continued watching.

Mom's amateur orgy video showed up, and she wasn't kidding, it was next to impossible to tell it was her. If I hadn't become so intimately familiar with her body recently, I never would have guessed, really. She was wearing a radioactive pink wig, and some baroque-style half mask that concealed her upper face and parts of her cheeks.

The other reason it was hard to recognize here was all the movement and writhing going on. Mom was gasping and moaning shamelessly (something I also could now recognize), probably because she was getting railed by three guys at once. Sure enough, as she'd told me the day before, she was lying on top of some dude, her legs pulled wide. He was pushing in and out of her ass from beneath, while another guy was kneeling and sawing back and forth, his cock deep in her pussy. Mom's mouth was latched onto another dude, and she was sucking the dick like it was the last thing she'd ever have in her mouth. Her moans were almost feverish in their need.

"Holy shit, mom," I breathed quietly, stunned by what I was being allowed to witness.

"I know," she almost croaked, her skin red with embarrassment. "Horrible, right?"

"Are you kidding?" I almost blurted. "You're a fucking sex machine, mom, a goddess! Three guys, all at once? And you're not slowing down or being dominated."

The guy in her ass moaned and pushed up, shuddering, and he was clearly cumming inside her. Seconds later, the lucky bastard in her pussy busted, filling her with cream. Mom was gently tugging on the sac of the guy in her mouth, and he popped seconds later, almost whimpering as he nutted, mom swallowing it greedily.

"Dayum," I said, glued to the screen. "Lucky bastards..."

"I can't believe you're seeing me like that," mom moaned, putting her face in her hand. I reached up and pushed my hand inside hers and then took her gently by the chin. Mom didn't resist all that much when I tilted her face up to look at the screen.

"You just dominated three guys, mom," I said firmly. "You made them all cum within seconds of one another. How many women can do that?"

She smiled back at me wanly. "Not disgusting?"

"Mom, if I get off three girls, I'm a god. Guys who don't like that you can do that are insecure boys who will never deserve a woman like you. Ever. You're amazing, and I'm in awe."

"I'm so lucky to have you for a son," she sighed before going back to watching. There was more churning around, and soon mom was straddling a girl and grinding on her while she sucked the cum off the guy who had just fucked her. Mom never showed signs of slowing up, just taking all the pleasure she could get, wearing it like a crown.

The video ended and mom seemed really tense. Whatever was coming up had her nervous.

"This is it, baby," she said, her voice an anxious whisper. "This is where you decide you mom went too far and you turn away from me."

I didn't bother placating her with little assurances or anything. I just let the statement hang. I wasn't torturing her, I simply decided that my words after this video were what counted, not anything I said before. I'd let her ride it out and then tell her what I thought.

I know mom had told me what the video was, but it was still stunning to see mom actually doing it. I watched silently, hoping she couldn't see my eyes widening in what basically amounted to shock. It wasn't a very long video, only a few minutes, but by the end, mom was a trembling wreck in my arms.

"Mom?" I asked. With shaking hands, she paused the video. She looked back at me, her eyes wet with fear.

"Yes, baby?"

I smiled. "Play it again."

Her eyes almost spiralled in her head and she restrained a sob before smiling and nodding. I held her tight and then let her play it again. I let her feel my hands roving all over her body now, caressing her and appreciating her. Mom seemed to be trembling in relief as we watched this scandalous video. I leaned in and whispered to her, making her giggle. I even started making little sound effects, and mom almost peed laughing.