Truth or Dare with My... Mom? Ch. 02

"Wicked boy," she breathed, caressing the boob. "I guess that one was on me, right? I should've known better by now."

Mom looked around for a moment and realized her glass of brandy was too far away. She reached over and took up mine. "Sorry, baby, your brandy is now my brandy."

"Guess you're done breastfeeding me now, since you'll have alcohol in your system," I quipped, giving her a grin. Mom giggled as she took a drink, winking at me. She emptied my glass and put it back down before pulling me up into a semi-sitting position, back against the arm of the chesterfield. She snuggled her body into me, tits to my chest, my cock squashed between us. She gently caressed my face as she looked into my eyes.

"My turn?" she asked and I nodded and asked her. "Truth or dare, mom?"

"Dare," she said after a moment's thought. I put my hands on her butt, caressing it gently while I thought about what I would get her to do.

"I dare you to show me your toy collection," I said finally. "And present it all to me in the fashion of a game show hostess. A naked game show hostess."

Mom leaned into me, making a small rupturing or deflating sound as she began giggling and snickering into my shoulder. Feeling her tits jiggle against my chest was wonderful, of course. It was nearly a minute before she came up for air, her eyes shining with mirth, despite her blushing.

"Oh my God," she breathed, wiping at an eye. "You're gonna make mommy show you what a complete slut she is by displaying all her toys and telling you about them?"

"I mean, I've seen one or two of them," I said with a shrug. "You keep one in your side table, but it was just a little chrome vibrator, and there's a buzzing egg. After today, I refuse to believe you don't own others."

"Well, I happen to know about that Tenga toy you own and keep in your nightstand, mister, so no judgement from you," mom said, smirking and poking me in the nose as she leaned close. She took my lower lip between her teeth and gave it a gentle bite, tugging before releasing me. "Sooooo, are you ready to see what a bad girl mommy is?"

I nodded and mom got up, taking a moment to stretch, exposing her entire body to me. "Don't forget the brandy, baby," she said as she turned and wiggled away. "I have a feeling I might need it, and as you said, it's not like I'm breastfeeding you at the moment, right?"

I got up and followed mom, my cock leading the way. She looked back and saw me, following her, and she put an extra wiggle and a bump in her walk for my amusement. Up the stairs we went, and on to mom's room. She turned to face me and studied me for a moment. Our complete casual nudity in front of one another was most welcome, and also no longer awkward.

"Aaron, go get the Tenga, please," she said, considering something. "Fair is fair, after all."

I didn't bother bringing up that she was supposed to be engaging in a dare. The fact that we were doing any of this at all was grounds for not raising any objections. I nodded and went down to my room, where I went into my dresser and retrieved the requested toy. On a hunch, I also brought the lube it used with me. I went back to mom's room, holding it up and grinning. "Ta-dahhhhh..."

"That poor little toy, trying to deal with your monster," mom said almost sympathetically, looking at the Tenga and then down at my rock-hard dick, still leading me around. It wasn't quite old news, but at least we both weren't bothered by it. "So, I guess sit and I'll put on the show for you."

I could've sat on the bed, but instead I pulled up one of mom's chairs and sat in it, looking casual, like I was a professional voyeur. Mom smirked and shook her head, muttering something to herself before going into her closet and bringing out a few boxes, one at a time.

"Holy shit, mom," I laughed, watching her bring out the third box of toys. They were all different sizes. "Turn on all those at once and your room'd sound like a construction site."

"Hush, young man," she chided, lining the boxes up on top of her dresser. She looked at all the boxes and then began to snicker, blushing. "Oh, my God, you're right, Aaron. I've got three boxes of sex toys, I'm such an unbelievable slut."

"Nah, just a healthy, sexy woman who knows what she wants and needs," I said simply, still sitting casually, having put the Tenga down on the floor beside me. "That's nothing to be embarrassed about."

"Don't say that until you've seen 'em all," she sighed, shaking her head. "Ho-kay, we'll start out with the little stuff and then work our way up. I assume you don't need to see the vibe or the clit buzzer in my nightstand?"

I shook my head. I almost dared her to put the egg in while she did her presentation, but this had to be hard enough. Mom took a deep breath and then opened one of the boxes. It was relatively small, a shoebox. She began pulling out the various dildos and vibrators, making sure to look at me and gesture to them while explaining.

"Here's one you'll want to know about," she said, smiling slyly and holding up a purple suction cup dildo, rather lifelike and veiny. "His name is Steve, and I believe you two almost met."

I laughed. It must've been mom's dildo she'd fucked herself on last night when I was filming her. I still couldn't believe she'd been cool with that.

"He's been very good to me of late, and he comes into the shower with me any time I have more than fifteen minutes to spare," mom said, toying him around her nipples and then dragging him down her lovely body to her pussy. She teased it for a moment before putting Steve aside.

"Is he named after someone?" I asked.

Mom blushed. "I... yes. From a long time ago. The boy who took my virginity. Our first time was in a shower room at a public pool that was supposedly closed. We snuck in and fucked. Since then, I pay tribute to him by taking this into the shower with me. I don't know what happened to Steve, his family moved away. I cried a lot, but I took dildos into that shower room for years after in memory of him."

"That's kinda sweet, mom," I said, nodding. "Who's next?"

Mom held up a strangely shaped one now, it definitely wasn't human. She blushed a little. "So, uh... curiosity got the better of me, I had to know what this felt like."

"What does it feel like?" I queried, curious.

"I can't really explain, just not human," she answered, blushing as she put it aside. "Be a good boy and maybe, just maybe, I'll let you watch me make myself cum with it. It gets pretty intense."

"I believe it," I mused, nodding. "I'll be good."

"I somehow doubt that, and I don't even want you to be," she replied, giving my a sassy wink. Next, she pulled out a double-ended dildo and showed it to me. "My gal pals and I use this bad boy a lot. He gets us where we wanna go."

"Can't imagine why," I laughed. "Have you ever just bent him in half and double-barreled yourself?"

Mom blushed. "You're getting a lot of free truths here, buster."

"Hey, if you don't want me to know," I said with a shrug.

"That's cheating," mom mumbled. "Yes, I have indeed done that on really horny nights."

She showed me several other toys, finally having nearly two dozen lined up on her dresser- dildos, vibrators, strap-ons, anal beads, buzzers, nipple clamps... she blushed a lot, but she kept showing me resolutely. My dick never went down, as I thought about her using them all in various situations. It was so damned hot.

"There's... there's one more toy in there, it's kinda embarrassing," mom admitted, pausing.

I shrugged. "What is it, a sex swing? A telescopic stripper pole?"

She snickered. "No, smartypants, although now I want both of those."

"Mom, go ahead and show me," I said. "I can't possibly judge you after today, can I?"

She considered and then nodded, disappearing back into her closet. I heard her grunt and start hauling something.

"You got a Sybian in there, mom?" I called, smirking.

"No, but I really want one of those too," she called back, wrestling with whatever it was. "Now that we have this understanding, maybe I'll bite the bullet and get one."

"I vote yes," I said with a laugh. "I'd love to see you get off on one of those."

She finally came out, carrying something wrapped in a sheet. It wasn't huge, but seemed rather cumbersome for her. She almost waddled over to the bed, plunking it down. She turned to face me, beckoning me over. I stood and joined her while she unwrapped the linen, now displaying the object for me.

"... oooookay, wasn't expecting that," I said, staring down at the object. "I may need some context, mom."

She smiled. We were both looking at a silicone sex toy, specifically a woman's waist, hips, vagina, and anus. The legs were spread and abruptly cut off. It seemed solid, so no wonder it took effort on mom's part to get it out here. Must've weighed a good eight to ten kilos. It was clearly meant to be a men's toy, since the pussy and ass were both fuckable.

"Before my sister left with that guy, she told me she was going," mom confessed. "She didn't want anyone else to know, just me. We cried a lot, and we fucked and fucked. But one of our last weird things we did was go our and get silicone moulds made of our sex parts, so that we could still fuck one another in some capacity..."

She reached down and caressed the artificial vagina almost lovingly. "Y'know how porn stars authorize sex toys that are meant to look and feel like their pussy? Well, Tracy and I did that for one another. It really does look like her down there, baby."

I gazed in wonder. Honestly, it looked a lot like mom. "So... that's what Aunt Tracy looks like?"

Mom nodded. "Close enough. When I fuck it with a dildo or hump my cunt on it, I reminds me of how she felt. God, I can't believe I'm showing you this."

"I'm glad you did, mom," I said simply and honestly. "I was one of the people in the family who just assumed she'd bailed and didn't tell anyone why, including you."

Mom smiled, and her eyes were a little misty. "She never told me exactly why, but she told me she was going and it was for a boy. We still email one another a few times a month, and we've even done the occasional video call. I tell her about you."

"I doubt you're tellin' her about yesterday and today," I said with a smirk.

"I may just do that," mom said. "Tracy's a perv, we were fucking one another, you may recall."

"And how," I sighed, shivering at the thought, my cock twitching in front of me. "That thought'll keep me warm at nights in the winter."

Mom giggled behind her fingers and then looked at me thoughtfully. "Since you're hard and all, baby... wanna try Tracy out?"

My eyes widened. "You want me to fuck the Tracy doll?"

Mom shrugged. "It's just a doll, it's not actually your aunt. This doll just happens to be what she feels like. Sometimes I've used the double dildo on it, just so I can feel like we're fucking again. I envy you having a dick, since you'll actually get to feel what she's like in there."

I shrugged rather helplessly. "I mean, I guess. It's not really her. And I might've jerked off a few times over the years, thinking about her. Or at least, how I remember her."

"Naughty," mom said slyly, smirking at me. "You know... it's big enough that..."

I looked at her curiously. "What, mom?"

"Oh my God..." mom mumbled, covering her face with her hands. "Aaron, I was... I was going to suggest that she was big enough for us to both use at once."

I tilted my head as I looked at her curiously. "Uhhhh, how?"

"There's a couple of options," mom said in a quiet voice, still blushing. "I could wear one of my straps and kneel just in front of her and fuck her cunt while you fuck her ass just below... or I could straddle her and hump my pussy down on her cunt while you fuck it. I can hold on to you for support..."

She buried her face in her hands again.

"Mom," I said, coming up and pulling her into a hug, both of us ignoring my erect cock squashing up between us. "I'm totally okay with trying this how ever you want. For real."

"You don't think we're being too weird?" she asked.

"After the day we've had, mom? No..." I chuckled. "Not one bit. We should fuck Aunt Tracy together."

Mom nodded. "Do you want me to fuck her, or should I rub my cunt on hers while you fuck her?"

"I'll let you pick," I replied. "Which idea gives you the bigger tingle?"

She thought about that. "Honestly, looking into your eyes as you fuck your aunt is the most amazing turn-on I can think of, baby. I'll hump. We'll start with that. Maybe later we can both fuck her."

I smiled. "Lead the way, mom. Wanna use that special lube on her?"

"Oh, God, yes, good idea!" mom breathed. She almost leapt on the bed and crawled across it to her nightstand, where the massage oil was waiting on top. She grabbed it and came back, looking excited now that we'd made a decision. "So, how're you gonna be most comfortable, baby? Standing at the edge of the bed, or kneeling?"

Mom had a relatively tall bed, so I measured my pelvis against where the fake Tracy toy would sit on the edge. If mom was sitting on it, that would brace it in place, so that was taken care of. My cock was still erect, and I placed my cock against the silicone orifice, measuring carefully. How comfortably could I fuck if I was standing here?

Well, if I'm honest, I'd once fucked a girl on mom's bed anyway, standing here as I was now, holding her legs apart while she lay on her back as I drilled in and out of her. If this doll was about life-size to Tracy (which I could believe, this thing was not tiny), and with mom's body bracing it...

"I can stand and do it, mom, if you're sitting on her," I announced. "Y'ready to do this? I think Li'l Aaron wants to say hello to his aunt."

Mom giggled and swatted my butt playfully, calling me naughty. No idea where I might've inherited that trait from.

She clambered onto the bed again and then turned around to face me. I took her hand as she climbed over top of the doll, shifting and moving around until she was perched directly on top of it, her pussy squashed down on the Tracy doll's.

"Hang on, baby," she said, opening the massage-lube. She leaned back somewhat and drizzled it down onto her own pubic mound and pussy, and then it trickled onto Tracy's. Mom used her hands to rub it into herself and the doll, using her fingers to get it deep inside the doll's opening. She lubed her fingers again and pushed them in, corkscrewing them around until it was glistening with the thick substance. Mom then went back to lubing herself, shivering as she snuck a finger or two inside for a moment.

She straightened up and looked at me, then down at my cock. She bit her lip. "You... you should lube yourself up too, darling."

I moved closer, my erection right below us both. "Drizzle some on then, please."

Mom nodded and sent out a steady trickle, which make my member shine as I put my hand around it and began gently spreading it around. Mom watched intently, her eyes glued to my cock as I lubed it up.

"You look like you wanna make sure I'm doing it right," I mentioned, seeing the spellbound expression on her face. Mom almost shivered at my words and then slowly reached out her hand. Finally, she placed it over mine, clasping it and then just going still, letting me massage back and forth along the length. It was as close as I dared hope to mom jerking me off.

"Okay, baby," she said in barely a whisper, a hint of a tremble in her voice. "Give it to your Aunt Tracy good and hard for mommy."

I nodded and set myself in position. Mom sidled closer until her breasts were pressed to my chest, her hands resting on my shoulders. I fumbled about with my cock, strangely nervous, since mom was about to watch me fuck, after a fashion. I was standing with my legs wide enough that my I was just hovering in front of 'Tracy's' pussy, and the head of my member nestled against the slippery slit. Mom looked down between us, watching as I pushed forward, the synthetic lips giving way before my cock.

"Right on in, baby," she breathed, still watching. "That'll be so hot."

I did as she requested and pushed forward, sliding my thickness deep inside my ersatz aunt, groaning as she enveloped me. I shivered, since I could feel the little bumps and ridges inside acutely. Mom told me it was made to feel like her sister. I don't know how one accomplished that with a sex doll, but she was convinced, and that was good enough for me.

I went into the hilt, my root now pressed against the lips of the doll. Mom pressed herself down at the same time, her pussy touching my pubes. She shuddered and let out a little sigh. Her hands flexed on my shoulders. We looked into one another's eyes. This felt so...

Wonderful.

"So, how do you like being inside your aunt?" she asked in a quiet voice, smiling and caressing my cheek with the back of her fingers on one hand.

I smiled back. "She feels great, mom. Surprisingly tight."

A wicked little smirk flickered across her expression. "We feel the same inside, so I'm told," she whispered. "Now you know what I feel like inside too."

I moaned at her words as I began to pull back, my hard cock almost leaving the pussy before sliding it all the way back in, a long, slow stroke. Mom just watched my face as I began my fucking motion, and I was lost in her eyes. She leaned in more, kissing my jaw and then my ear before whispering in it.

"Naughty boys shouldn't fuck their aunties," she said, that angelic voice giving me chills. "That's for good boys to do. And you are such a good boy, Aaron..."

Mom's weight was bracing the sex device in place, meaning I didn't need to hold it. My arms were wrapped around her torso, holding her against me. My hips pumped slowly back and forth as I fucked my aunt, and mom began to squirm, moving her pussy in little circles over her sister's, like she was tribbing Tracy while I fucked her. My head was swimming with how unbelievably erotic and taboo this all was.

Mom's tits were squashed to my chest, her arms around my shoulders, and her nose touching mine as she stared into my eyes. She leaned in ever so slightly more, her lips barely touching mine as she spoke.

"I love you, Aaron," she whispered, and I could feel the words against my mouth. "I have never loved anyone more than I love my wonderful little boy."

"I've never loved anyone more than I've loved you, mom," I murmured, worried my voice was almost a croak. "I'm so lucky to have you for a mom, and to love you."

She kissed me, a deep and loving expression. The kiss was much longer than propriety would allow for, but it wasn't the kiss of lovers. It was the kiss of a mom and son who loved one another. More than they loved anyone else. That'd be a hard concept for other people to understand, especially since we were naked and going to town together on a sex doll that felt like her sister. Hell, before today, I never would've been able to understand.

It all made sense to me right now, and I couldn't have been happier.

She pulled back from the kiss and she was looking at me, her brown eyes smoldering with a growing lust. "Time to hammer this slut and cum in her, baby?" she said breathily. "Wanna fill up your slutty Aunt Tracy?"

I nodded readily as she caressed my face with one hand. She kept looking into my eyes as I increased the tempo of my fucking motion. Mom bit her lip as she pressed down and squirmed harder.

I could feel her pussy bump against my pubes occasionally, and I think we both shuddered at the contact. It was nowhere near the first time my genitals had touched hers, of course. Hell, earlier, she'd wrapped her pussylips around my shaft during her massage. But this was somehow different. We were fucking together. She was tribbing my 'aunt', while I was sliding deep inside her.