Mom, Aunt Clara & My Wandering Mind Pt. 05

"Oh, I don't even know. Maybe, five times?" Kari said and I could tell she was lying. It was easily twenty times and we both knew it.

"Very well, then. If you don't mind, Kari," Aunt Clara encouraged. "Would you please administer six hard spankings to this miscreant's behind?" I could almost hear the smirk in Aunt Clara's voice, and I definitely heard the giggle that it elicited from Miss Swenson.

SMACK! The blow caught me off guard and purely from reflex, I thrust my pelvis hard into her lap, letting out an 'mmph' sound simultaneously.

"Ooh... I'd be happy to," Miss Swenson giggled after the first swat.

SMACK! She administered the second correction.

"Oh wait, Kari, I almost forgot. You're supposed to make him count off the corrections as you administer them. It helps to keep him focused on the fact that he's being punished and not just the pain from the punishment itself," Aunt Clara explained the supposed reason she made me count off my spanks. "Start over and make him count this time," she urged enthusiastically.

"What?" I blurted without thinking. "That's not fa..." suddenly I realized I was talking back and silenced myself.

"It's not what, Andrew?" Aunt Clara hissed.

"Nothing, Aunt Clara. N-nothing."

"That's what I thought. Now, Kari, please start over and administer seven corrections to Andrew's bottom. He just earned one more for talking back."

SMACK!

A tear quickly formed in one eye, but I fought to keep it contained. "Hmph... One," I squeaked.

SMACK!

"Two!" I yelped through clenched teeth.

SMACK!

"Hmph... Th-three," I croaked and I realized I was holding my breath.

SMACK!

"F-four."

SMACK!

"Five!" I again blurted loudly, my face turning red from not breathing.

SMACK!

"S-six!"

SMACK!

"Seven!" I barely croaked, then sucked in a deep breath of air, before letting it out again and quietly whimpered.

"Oh my goodness. Thank you," Miss Swenson gushed. "It's been so long since I spanked a man's ass. And I do suppose he deserved it. The naughty scamp," she giggled.

"Well, we're not exactly, done," Mom nervously added. "His bottom is so red. We really ought to tend to it. This is the part where we soothe him and let him know we still love him, even though we just punished him."

"Really?! Can I watch?" Miss Swenson seemed giddy with anticipation.

"Watch?" Aunt Clara scoffed. "Mary, if you don't mind, perhaps we should allow Kari to help with this. Maybe she'd even consider being a caregiver for Andrew in the future, like oh, I don't know, maybe this weekend? So we can go shopping?" What had originally begun with a potential call to the cops somehow turned into the recruitment of Miss Swenson to join in on my 'caregiving.'

"Oh! Can I? You would trust me? I'm very fond of Andy, too, you know. I always have been. I'll be sure to do whatever you tell me! I promise I would!"

Her excitement was over the top. She was way too excited about this and I instantly worried.

"I think I'd be very okay with that," Mom said confidently.

"Mom? Aunt Clara?" I quietly spoke.

"Yes, Andrew?" Aunt Clara said. "What is it?"

"Can you... can you please not let Nadia know? About all this? Please?" I begged, hoping against hope that between the three of them, they might have a heart.

"Of course, Andrew," Aunt Clara surprisingly answered. "You see, Kari," she continued. "Andrew is smitten with your daughter. I'm sure this would be quite embarrassing to him and might even prevent the possibility of him ever being with her. Of course, he still needs to gain the confidence to even speak to her, and he needs to learn how to treat her right. But we've started working on those things, too. Still, we wouldn't want to make things even more difficult for him than they already are."

"Oh, I understand. I do. And I do hope you help him. I'm so tired of hearing Nadia whining about how Andy has never asked her out. It's incessant, her constant belly-aching. So if you can help him work up the nerve, you've got my full support!" Miss Swenson shifted beneath me and I felt a tender pat on my butt as she leaned down to whisper "Don't worry, Andy. I won't say a word about any of this to Nadia until the time is right."

The right time? Oh god, just kill me. This is so humiliating. This can't possibly get any worse. I grumbled to myself. And then it did, when I heard the familiar sound of the lube bottle being popped open.

"Here," Aunt Clara ordered and I knew exactly what was going to come next.

A slender fingered hand touched my tender globes and I winced.

"Sorry," Miss Swenson whispered. "It will feel better in a minute," she assured me and that's when I realized she really had done this before. How else would she know to say that?

Again her slender fingers touched, applying the lube to my raw cheeks and very gently massaging it in. Once the entirety of my reddened skin had been lubricated, it indeed started to feel better. The initial sting subsided, replaced with a heightened sensation of inflamed nerve endings, responding to the lightest touches from my beautiful neighbor's caresses.

And that's when I felt a surge, an unwanted churning that started deep in my balls, and before I could begin to try to fight it, my penis was rapidly engorging.

"Oh no. I'm... I'm sor..." I started to say but caught myself.

"Very good, Andy," Mom encouraged. "You stopped yourself. I'm so proud of you."

"Mom, I'm... I'm getting a... I'm not meaning to. Miss Swenson, I promise I'm not meaning to..."

At my pronouncement, one of Miss Swenson's legs started vibrating beneath me, as if it was twitching with tremors.

"Mmmm," Miss Swenson hummed quietly.

"It's okay, Andrew," Aunt Clara said. "It's completely understandable. After all, you're sprawled completely naked across a gorgeous woman's lap. Her fingers look quite sensuous. Her skin... flawless..." Aunt Clara's voice seemed to be fading.

"You really think that?" Miss Swenson asked Aunt Clara.

"Of course, I do," Aunt Clara almost whispered. "You're... splendid."

"Wow," Miss Swenson croaked while shifting herself beneath me as if to get more comfortable.

"Ahem, Andrew," Aunt Clara cleared her throat. "Thank you for being respectful, despite your condition. You're making some very good decisions. Is there anything else you want to say? Anything you'd like to ask for, perhaps?"

I quickly tried to decipher what Aunt Clara was hinting at. I knew it was something specific she was expecting. I just had to figure it out. And quickly. The only thing that came to mind was... No, that couldn't be what she's thinking. Could it? Does she really expect me to ask that?

"Andrew?" she asked again. "You're safe here. You don't have to hide in your thoughts. Just say what you're thinking. Whatever it is. Is there something you want? Something you'd like Miss Swenson to do for you maybe? Say it out loud, Andrew. Say it now."

"Can I please... Would you please let me have a... a pleasurable thing?"

Aunt Clara giggled. "A pleasurable thing?" she teased. "Perhaps, you'd like to be more specific, Andrew."

"Can I, please, have some relief? I... I usually do it, like every morning and... well, I couldn't today... and I'm... I'm really..."

"Really what?" Mom asked.

"I'm really... worked up... Like I feel like I'm going to explode if I don't..."

"Don't what?" Miss Swenson, chimed into the delight of both my stepmom and aunt.

"Oh god, this is so embarrassing," I groaned.

"Ask her, Andy," Mom urged eagerly.

"Miss Swenson?" I nearly whispered.

"Yes, Andy?" she asked eagerly, her fingers still slowly massaging the oily lube into my sore bottom.

"Would you please, let me go, so I can relieve myself?"

"Go?" Aunt Clara quickly interjected. "One of our rules was you are not to pleasure yourself alone, Andrew."

"Oh... right. Just... never mind, then," I hated saying those words. I was desperate for release but I was no longer allowed to do it myself. I wonder if I might die before I had the chance at another orgasm.

"What do you think, Kari? Would you mind helping him?" Mom asked, knowing full-well what her answer would be.

"Help him? You mean... get him off? Would what be... Oh! Really?! I can make him cum!?" she quickly agreed. "Would I ever! Get up, Andy," she tapped my bottom again and I clumsily slipped off her lap and stood.

I was facing away from her, wondering what I was expected to do next, when I felt her hands on either side of my hips, nudging me to turn around.

I turned to face her and immediately, my dick started twitching and flopping in the air, completely on its own.

Miss Swenson positioned me right in front of her and reached for the bottle of lube, opening the top and then reaching for my hand.

I offered my hand, unsure what she wanted me to do until she flipped my hand over so that my palm faced upward.

"I used to enjoy this quite a lot when I was younger," Miss Swenson reminisced. "I could line the boys up if I wanted to. There was never a shortage of young men willing to show their wanking prowess. Of course, I usually made sure I was taken care of first but... well, this is a little different, I think." She glanced questioningly at Mom and then Aunt Clara.

Mom and Aunt Clara seemed to have a silent conversation with each other with only their eyes—a conversation that ended with both of them smirking.

"I assume you're right-handed?" Miss Swenson asked, before squirting a healthy amount of lube into the palm of my hand.

"Yes, ma'am," I replied, glancing back and forth between the oil in my hand and Miss Swenson's face. God she's so beautiful, I couldn't help blushing even more.

"God you're so beautiful," she mimicked almost exactly what I'd just thought about her. "Go ahead," she encouraged.

"Wh... where should I... once I... where should I point it?" I stammered, but proudly did not say 'um.'

"I suppose that depends on what's allowed." She again glanced in Mom's direction.

Mom leaned over and whispered something into Miss Swenson's ear.

"He does? Oh wow," Miss Swenson mumbled. "I'll let you know when the time comes, Andy," she said mysteriously. "For now, though, why don't you just get started?"

I looked at the oil puddled in my palm and slowly pulled it closer to my enlivened cock, tilting my hand just enough to let some oil slip from my hand and onto my shaft. I then moved my hand further down before tilting it a little more spreading the lube onto my balls. With the last of the oil on my hand, I quickly massaged along my shaft, swiftly picking up other puddles of lube before they started to drip away from my hardened appendage and onto Miss Swenson's black leather skirt.

I closed my eyes, hoping to forget three women were staring at me as I started to jerk myself off.

"Eyes open," Aunt Clara commanded.

Upon opening my eyes, Aunt Clara smiled at me, then joined the other two women in staring directly at my cock. Mom and Miss Swenson seemed overcome with lust. Aunt Clara seemed to be studying and, of course, critiquing my techniques. None of the women were looking into my eyes, though, and that gave me a sense of permission to look wherever I wanted, too.

My gaze immediately targeted Miss Swenson's sheer black top which looked almost like the screen material in our windows; it hid basically nothing. Beneath her see-through top, Miss Swenson wore a simple black bra, covering her small, perfectly sized breasts. Above and beneath her bra was flawless skin, tight and supple and begging to be licked, or kissed or nibbled or all of those things.

I continued to stroke, my passion mounting, as I glanced up to Miss Swenson's face hoping she wasn't looking back at me. She wasn't.

Her gaze was still firmly locked on the obscene display unfolding in front of her, her tongue peeking from between her lips.

I scanned back downward, noticing her skirt. It was black and leathery and looked almost glossy. It had four rivets along the side pockets that reminded me of the buttons on my old-school Levi button-fly jeans.

My balls tightened and I could tell I wouldn't last much longer. I was already two hours past my usual first wank of the day and my dick had been charging for action since the prior night.

I glanced upward again and neither Miss Swenson nor Aunt Clara was staring back at me. Both were still ogling unapologetically my quickening strokes, watching my cockhead turn a darker shade as my climax came nearer.

Mom, however, was no longer staring at my cock like the others. She was focused on my face, her eyes taking in my expressions, her tongue wetting her lips as someone had just set her favorite dessert on the table.

I closed my eyes again.

"Eyes open," Mom ordered this time. "I want to see your face when you come," she whispered.

Immediately, the other two ladies looked over at her but she never faltered.

Mom's eyes were glued to mine, waiting to see my o-face, determined not to miss it. She scooted herself forward to the edge of the couch, her skirt shifting up her legs from the friction, showing more and more of her legs.

"Oh, God, Mom," I panted at the sight, so close to revealing her panties.

She slid herself down to the floor and closed the distance between us, her face even with my cock and just a few inches away.

Aunt Clara gawked at my feverish masturbation, my hand becoming a blur as I pummeled faster and faster on my enraged cock.

Miss Swenson groaned the closer Mom got to my rapidly purling cockhead.

"I... where?" I panted. "I'm gonna... I'm going to... cum... but where?"

The image of me cumming on Mom's face flashed through my mind and I nearly came on the spot. Instead, I whimpered and swallowed and halted my stroking for a split second.

Miss Swenson looked up to my face for the first time since I'd started and gave me an impish grin, then pointed and patted her lap.

"There?" I questioned. "On your... your nice... skirt?" I huffed between gasps for air.

"Don't worry," Miss Swenson assured me teasingly. "It won't stain. It's 100% calfskin. I promise," she said lustfully, "it'll come right off."

"Oh god," I muttered, still stroking myself closer to climax.

"Oh, I love that skirt," Aunt Clara suddenly chirped. "And it looks great on you, too. Who is it, anyway?"

"Oh, it's Givenchy," she replied immediately. "I got it at a consignment shop. I could never pay full price. I've always liked it, but now, I think I'm going to love it." She looked up again into my eyes and growled, "It will look so nice to have some bright white cum on it."

"Oh god," I panted and closed my eyes again.

"Eyes open," Miss Swenson commanded, and both my stepmom and aunt giggled.

I opened my eyes and noticed Miss Swenson pointing to the exact spot where she wanted me to make my deposit. "Right here, Andy," she said sternly. "And nowhere else. Do you understand?"

Clearly, she didn't want any to accidentally land on her blouse.

"Yes, ma'am," I panted.

"Or maybe," Mom crooned huskily, her face now an inch at most from my cockhead, now glistening with precum. She reached out her tongue and touched the slit, pulling a sticky string of precum from the tip and making it stretch obscenely between her face and my cock.

"Oh, Gawd, Mom!"

"Shit," Miss Swenson moaned.

Mom closed her lips, breaking the string of precum, then licked her lips and leaned forward again, this time, grasping my thigh and twisting her head until her mouth was beneath my frantically pumping fist.

"What are you...?" I started to ask when I felt Mom's tongue lick the bottom of my balls and sneaking back toward my perineum, that sensitive space between my scrotum and my asshole. "Oh, MOM! I'm... Oh! I'm... I'm gonna cum!"

I squatted down, taking Mom down with me, and pointed my red hot cock toward Miss Swenson's lap, inching close enough to the spot where she was pointing that I was sure it wouldn't go anywhere else.

"That's right, Andy. I want your cum right here. Right where I'm pointing. Don't you dare miss or I'll have to spank you some more."

Simultaneously, Mom sucked in one of my balls and swirled her tongue around it, then started suckling on it.

My cock surged in my grip at Miss Swenson's words and Mom's stimulation and I erupted. Hot cum spurted once, twice, and then a third time, hitting the exact spot where she was pointing, puddling immediately into a gooey translucent glob.

I continued to stroke, slowing slightly and avoiding direct contact with the sensitive cockhead, as more cum oozed from my slit, and streamed down to her skirt.

"Verrry gooooood, Andy," Miss Swenson applauded. "You did such a good job!"

For a split second, I grinned happily, like a schoolkid getting some praise from his Mom for a good grade. Then I remembered my circumstance and the smile vanished.

My knees started to shake beneath me and Aunt Clara immediately noticed. "Kneel, Andrew, before you fall," she directed as Mom released my ball from her mouth with a pop. "Yes, right there, between Kari's legs."

Quickly I lowered myself to the floor, letting gravity do most of the work, while Mom adjusted her position on the ground to be right next to the spot where my cum was puddled on Miss Swenson's skirt.

My thumb and first finger were coated in cum, the only semen that hadn't made it onto Miss Swenson's skirt.

"You should clean that up, Andy," Mom said eagerly, pointing at my hand.

"I... in front of..." I muttered, incoherently.

"You were serious about that?" Miss Swenson asked, glancing at Mom.

"Just watch," Mom told her and again told me to clean myself off.

Embarrassingly, I lifted my hand to my mouth and licked the cum off my thumb, slurping it into my mouth and swallowing before doing the same to my finger.

"You missed a spot," Mom said, pointing to the webbed skin between my thumb and finger.

I lifted my hand and cleaned that spot, too. Of course, swallowing it in front of the three ladies.

"Well, I would've never thought I'd see..." Miss Swenson started to say but interrupted herself as she looked down to the pool of my cum, still resting on her black, 100% calfskin Givenchy skirt.

She reached a finger toward it and somehow I sensed right away what she was about to do.

"No! Please no!" I blurted.

"No? Why not?" Miss Swenson asked curiously.

"I... it's just... oh, please don't," I begged.

"Speak with confidence, Andrew. This is still a safe space." Aunt Clara said assuringly.

"Please don't... taste me... my cum, Miss Swenson," I said lowering my gaze toward the floor.

"Eyes up, Andrew," Aunt Clara chastised. "Now use your words. Tell us why not?"

"Because... Nadia," I nearly whispered.

"Nadia?" Mom repeated. "Oh, Andy."

"That's so sweet, Andy," Miss Swenson chimed.

"Let me get this straight," Aunt Clara seemed the only one not so enthused at my reasoning. "You just got yourself off to the MILF next door, but you don't want her to know what you taste like because you're infatuated with her daughter?"

The way she'd said made me sound almost delusional or warped or some kind of demented that even I couldn't find the right word for.

"You think you'd be what? Cheating on her?" Aunt Clara asked. "You don't even have the balls to ask her on a date! But you're worried that her mother will know what you taste like before she does?"

She was ridiculing me and I quickly remembered why I often thought I hated Aunt Clara. She could be cruel, sometimes, and this was one of them.

"I still think it's sweet," Miss Swenson chirped again. "But there's still the matter of this cum on my skirt." She pointed at it and my gaze followed where her finger was pointing.