Explorers Club

Explorers Club Ch. 8: Sugar Momma

Frank's eyes were wide and bug-eyed. My fingers twisted and intertwined with his. The muscles in my shoulders and triceps bulged as we vied against each other. I shoved against him and felt him start to buckle; I was taller and heavier than Frank, and I felt my weight coming to bear and begin to overpower him. I winced as Hannah's hands slapped the top of my head repeatedly, but her slaps were weak enough that I could ignore them and continue to push.

I could not, however, ignore Jenny. As she sat on my shoulders, her thighs squeezed hard around my neck, constricting my airflow. I could not believe how strong her legs were for someone so petite. She scooted forward on my shoulders, shoving her pelvis against the back of my head.

"YOU'RE GOING DOWN, FUCKERS!" Jenny shrieked, just above my ears.

She leaned forward and wrapped her left arm around my face to hold on tighter, as she flailed wildly at Frank and Hannah.

"I can't... see!" I yelled, gasping for air. Her thighs squeezed tighter.

"Gah!" Hannah yelped, shielding herself from Jenny's whacks.

Frank yelled in response, and his fingers tightened around mine.

"Jenny, I can't-!" I tried to gasp, but the splashing and yelling was too loud, and Jenny's thighs squeezed my neck harder.

"Jenny, I can't see!" I protested.

"YOU'RE GOING DOWN!" Jenny shrieked from atop my shoulders. Her arms whirled through the air as she continued batting at Hannah and Frank. Hannah screamed in response and protected herself. Frank I continued our tug-of-war, hands locked together, each trying to push the other.

But as I gasped for air, I felt my feet slipping. The water was high and I was blinded, deafened, out of breath, and disoriented. Frank roared, Jenny's thighs squeezed, and my foot slipped.

Jenny twisted and fell sideways on my shoulders, pulling my head down with her backwards into the pool. The water rushed above my head and for a moment, I couldn't distinguish up from down. Jenny and I dissolved into a tangle of wild, flailing limbs underwater.

Finally, I found my footing and righted myself. We had fallen backwards into deeper water, and I had to stand on tip-toes just to barely keep my mouth above water. Jenny, however, was still flailing and coughing. I reached out to her, found a limb, and pulled.

Jenny collapsed against my body and gasped for air. Her arms wrapped around my shoulders and then her legs followed around my hips, holding onto me like a support buoy. Her chin fell onto my shoulder and she coughed, wet and loud, expelling water from her lungs. I felt her body, warm, and soft, as her chest snuggled into me. I gasped a little, feeling myself warming as her body pressed against mine.

Frank and Hannah were in the distance, laughing and whooping and splashing each other as they exited the pool on the far side.

"Are you alright?" I asked, as I desperately tried to stay on my toes to keep my balance- our balance.

"Yeah," Jenny nodded, and coughed again. I felt her nipples poking into my chest and looked down. She was topless.

She smiled as she caught her breath. "Sorry for coughing on you."

"Jenny your top-"

She laughed, wiggling as her boobs pressed against my chest.

"What?" I asked.

"Your chest hairs are tickling me," she said, snickering.

I began to speak when I gasped as I felt a pressure poking against the tip of my dick. I could feel the tip of my dick pressing against my suit, and pushing against somewhere on her body underwater. It felt nice and I bit my lip, holding in a moan as her body snuggled into me.

"What's... what's poking my stomach?" Jenny murmured.

"Jenny you... you know you're topless, right?"

"I'm WHAT?"

Jenny squealed and fell backwards into the pool. I reached down and grabbed her arm and pulled her back up.

"This fucking bikini, I swear to god!" she scoffed, and held her arm protectively over her chest. "Where did it go?"

"Oh I think I see it," I said, seeing a black shape on the bottom of the pool. "Let me pull you to the side first?"

Jenny nodded.

Luckily, there weren't many other people in our little corner of the pool. We had been making such a scene with our shoulders game, that other pool goers gave us a wide berth. I swam to the side of the pool, carrying Jenny and put one of her hands to the wall. Her other hand remained underwater, covering her chest. If anyone above noticed, no one gave any indication.

"Be right back," I said, and dove towards her discarded top. The world went silent as I dove underwater, and as I approached the black fabric waiting on the bottom of the pool. I grabbed it and returned, holding it out to her.

"If I put it on here I'll flash everyone..." she looked down at the top, and glanced to the side of the pool, where sunbathers lounged in the distance. Honestly I doubt anyone would care if she made it quick, but she looked unwilling to move her arm in public.

"Oh! You can put it on underwater," I suggested.

"Hrm," Jenny said, unsure. She glanced around the poolside uncomfortably.

"If you duck underwater and keep close to the wall no one in the chairs could see you," I said, and then pointed across the pool. "And the fountain there blocks the rest of the swimmers in the pool."

"I suppose..." she said, hesitantly.

"No one to peep you," I said confidently.

"Except you," she said.

"I won't peek," I promised, and held her bikini top as I made a cross motion over my chest. "I swear it, on your expensive and yet surprisingly shoddy bikini."

Jenny snorted and rolled her eyes. "You're a liar. Funny, but a liar."

"You don't believe me?!" I said.

Jenny continued to regard me cautiously.

"It's not that I don't believe you..." Jenny said, giving me a coy grin. "It's just that I don't think you're much of a gentleman, Perky."

I scoffed, gripping the side of the pool and mustering as much haughty disdain as I could. "Why, I'm a perfect gentleman!"

Jenny just laughed loudly.

"What gives you the impression that I'm not?" I demanded, and for a moment adopted an accent that vaguely resembled a posh British person.

"Well for one..." Jenny waded closer, and her arm covering her chest pressed into me. Her eyes flicked up to mine and she grinned. "Did you like, smuggle a flashlight in the pool, or something?"

"A flashlight!?" I asked, completely confused. "Why would I have a flashlight in the pool?"

"Well if itwasn'ta flashlight then..." Jenny bit her lip and snickered. "Then something veryun-gentlemanlywas poking me under the water, wasn't it?"

I held the side of the pool and tried to stand back straighter. "Well, I mean... even a gentleman can't help it if a pretty girl pushes up against them like that... it's merely a natural bodily reaction..."

Jenny was watching me closely and squinted like she was trying to evaluate me. She seemed more serious.

"What?" I asked.

Jenny's voice had dropped to a whisper. "You really think I'm pretty?" she asked.

Those dark eyes opened wide as they ran over me. Her expression scrunched up her cute little nose as she peered suspiciously at me.

"Of course you are!" I said, laughing. "Is that such a surprise?"

"Well... no one's ever told me that before," Jenny whispered.

"No one? Come on," I said, skeptically. Just looking at how cute she was staring up at me, wide-eyed in the pool, such a thing seemed impossible.

"At least, not a boy."

"Hey!" Frank yelled.

Jenny squeaked and turned, leaning backwards into me.

Frank was walking beside the pool, towel wrapped around his waist. Hannah walked beside him, looking bored.

"What's uh, going on, Frank?" I asked, and moved around, trying to put my body between him and Jenny, to hide her a bit. But I saw from Frank's eyebrow wiggle that he still had a view of Jenny behind me.

"Oh-ho! Lose some clothing back there, huh?" Frank said, standing on his tiptoes to get a better view.

"Just a... minor wardrobe malfunction," Jenny responded.

"Stop staring, you perv," Hannah said to Frank and smacking his arm.

"What?!" Frank protested. "I can't help being observant! I just notice things sometimes."

"Certain very specific things," Hannah scoffed.

Jenny turned to me and whispered. "Your friend isn't much of a gentleman."

"Yeah well there isn't really much of a debate on that front," I responded.

"Were you two uh... having fun down there?" Hannah asked.

"No! I just fell!" Jenny responded.

"Sure, sure," Hannah laughed and rolled her eyes. "You know for such a hopeless virgin you're kind of a whore, Jenny."

"Shut UP!" Jenny yelled as Hannah cackled. Jenny removed her arm to splash Hannah, and I saw Frank's eyebrows jump in excited surprise. Hannah yelped and stepped back, trying to avoid getting her towel wet.

"Oh ho!" Frank just said, wiggling his eyebrows. The water splashing him too, but he was unbothered by it. Hannah whirled on Frank, slapping him again.

"Stop looking!" Hannah said. Frank protected himself from Hannah and turned away from Jenny. Hannah rolled her eyes and gestured to Jenny and I. "Come on, we're going to the beach. You two can bring our stuff, since you lost the game."

"No we haven't lost yet, it's best of three!" Jenny insisted.

"We didn't agree to that, technically," Frank said.

"Fine, double or nothing!" Jenny countered.

"Double what? We didn't bet anything?" Frank said.

"Well you can think of the terms and then double it!" Jenny said.

"Now that's interesting..." Hannah said, tapping her chin thoughtfully.

"Hey that's a dangerous game-" I whispered to Jenny.

"Doesn't matter, we'll beat them twice!" Jenny said with what I thought was rather too much confidence.

"I'll think about it, but if you want to play, we'll play at the beach," Hannah said, and reached down to pick up her bag.

"Okay you go on we'll catch up," Jenny said.

"Uh huh," Hannah said, giving Jenny a knowing look. It looked like they were about to have another spat but Hannah just snickered and held up her bag to Frank. "Okay you can carry my stuff."

"But I didn't lose!" he complained.

Hannah put her hands to her hips and pouted at him. She pulled the straps of her bikini, which was holding her impressive chest. "Well I'll need to get rid of these tan lines. Do you want to come with me or not?"

Frank scrunched up his face, thinking for a minute, confused. "What do you mean get rid of..."

"Frank," Jenny scoffed, shaking her head. "She means she'll be sunbathing topless."

"Oh!" Frank's eyes lit up. "Yes I want to come please!"

"Good," Hannah said, tossing him her heavy bag. "You two lovebirds come out and join us once you're... ready."

Hannah and Frank walked away towards the beach. Jenny turned back to me and nodded to the top of her bikini in my hands.

"So... are you ready?" Jenny asked, still covering her chest with her arm.

"Right! Yes, okay," I said, nodding. I looked down to the top in my hand. "I'll go underwater, sit on the bottom, and hold it out for you. And I'll be a perfect gentleman and won't peek."

Jenny rolled her eyes and nodded to the bottom of the pool. "You first, mister gentleman."

I took a deep breath and dropped.

Soon, I was cross-legged on the bottom of the pool, holding the bikini top in front of me. I dutifully closed my eyes and waited. It was oddly peaceful, and it felt at least for a moment like I could live down here, like some kind of underwater male mermaid. A mer-man, perhaps? In any case, I'm sure my lungs would eventually take issue with that idea.

I felt Jenny's fingers intertwining with mine, and I let go of the top as she took it from me. I still waited, sitting in the pool, comfortable. A little bubble escaped from my mouth, but I felt like I could hold out longer. Then I felt a series of little bubbles over my lips, but they weren't coming from my mouth. I felt something brush my nose and I opened my eyes.

Jenny's face took up my entire view, and I realized her nose was brushing against mine. Her unkempt black hair seemed to take on a new life underwater, twisting and coiling around her head like the snakes of a medusa. Bubbles escaped from her lips, and they bubbled up, creeping over my own.

Before I could process any more, Jenny quickly pushed off the ground, diving quickly to the surface. I turned to see her bare legs kicking above me. Her top was on, but the back was loose and undone, and a loose strap of her bikini was floating behind her.

I followed, pushing off the bottom of the pool and I surfaced next to her. I took a deep breath and shook the wet hair out of my face. Jenny faced away from me, with her hands fiddling with her top behind her back.

"Ugh! This stupid thing!" she complained as her hands fumbled with the strap behind her back.

"Let me take a look." I put my hands over hers, and she allowed me access to the straps. I could see the problem: the suit had some kind of fancy metal rings, and the bikini strap must have torn from it when we played shoulders. I explained the situation and Jenny groaned, sounding much more annoyed than I would have expected for such a little thing.

"It was probably just made for sunbathing not... intense games of shoulders," I said.

Jenny scoffed. "Well you made me pay a lot of money for this stupid piece of junk!"

"I made you? Come on, I don't think so!"

"Fine, you... peer pressured me! You and Hannah! And Frank too, you're all complicit! It was a conspiracy!"

I laughed and began to re-tie her bikini straps. The skin of her back was smooth and taut as my fingers brushed against it. "Well, you've uncovered our evil scheme to get you... to wear a skimpy bikini."

"I knew it! Jerks!" Jenny said. She scrunched her face and I thought she was smiling, but as she turned I could barely make out her expression. She seemed bothered by something that I couldn't place.

I began tying the bikini strap and pulled it tighter around her chest

"Oh," she said, arching her back. "Yeah that's better."

Jenny turned in the water towards me. She stared down at herself and adjusted the straps of her top. Little droplets of water fell from her hair, traveling down her collarbone, and over the swell of her small, cute boobs.

"If it's any consolation," I said, "conspiracy or not, you do look hot as hell in that."

Jenny's face turned up to meet mine. Her eyes seemed to dart back and forth as they watched me. Curious, and suspicious.

"You're really not joking?" she asked.

I laughed. "Of course not!"

Jenny scrunched up her face, thinking. "Well if you really thought that weren't you even... tempted to peek?" Jenny murmured.

"Sure, but I promised to be a gentleman," I said, proudly. "I lived up to it, didn't I?"

"Yes you did," Jenny said, sighing. She looked away, into the distance.

"What's wrong?" I asked.

"Well, I just wanted to know... you know, never mind," Jenny said, shaking her head.

"No go ahead, just say it," I insisted.

"It's just a silly... boy question," Jenny murmured.

"Shoot," I said. "I will answer any and all of your silly boy questions."

Jenny grinned wide and half-turned back to me, watching me from the side of her dark eyes. "You don't know what you're getting into, Perky! I have a LOT of silly boy questions."

"Well you know... one perk of being a sugar momma is that you get to ask infinite boy questions."

Jenny snorted and gave me that inquisitive stare again, a little bikini-clad detective. She leaned back against the wall of the pool. I wasn't sure whether she intended to give me a better view of her breasts straining against the black bikini top, but my eyes dropped to them immediately.

"You're still interested in that little... arrangement, huh, Perky?" she murmured.

I shrugged. "Sure. Are you?"

"Maybe," she said, tapping her lips with her finger. "Unlimited boy questions is an interesting offer. But I'm not fully convinced, yet."

"Well, why don't we start with the question you're thinking of now," I said. "I'll answer it, and you can think about the offer."

"Alright," Jenny said, twisting her mouth. "I just wanted to know if you ever, well... I mean you're such a 'gentleman', so you haven't... probably..."

"What, already?!" I asked. I was laughing but her hesitancy was maddening.

"UGH," Jenny said, clearly internally struggling. She glanced around, making sure nobody was too close, and leaned forward. "Have you ever like... felt unable to control yourself?"

I raised an eyebrow.

Jenny sighed and leaned closer. "You know... ever wanted to NOT be a gentleman? Where like, you just can't help yourself?"

"Are you like..." I leaned closer an inch from her face. "Are you asking if I'm like a secret rapist or something?"

"NO! JERK!" Jenny said and splashed me aggressively.

I shielded myself and laughed. "What?! I don't know what you meant!"

"YES YOU DO!" she yelled, splashing more. She was being far more aggressive than I would have expected from silly playful splashing.

"Okay okay, hold on," I said, reaching out to grab her wrists. It was tricky, like trying to grab an angry cat, but finally I locked my hands to her wrists and held. My hands were big enough to fully cover her small wrist and her flailing slowed as my grip tightened.

"I knew you'd laugh at me for asking something like that," she said, sporting a deep and excessive frown, like a cartoon character.

"I'm not laughing at you," I said, still laughing a little. "I just..." I sighed. "Fine, I know what you mean," I admitted.

"You do?!"

"I mean, I'm not saying I've forced myself on anyone!" I said.

"Of course not!"

"But if you're asking if I've felt the urge to you know..." I hesitated now, struggling to find the words.

"... to take what you want?" Jenny finished.

I nodded, still holding her wrists. "I... recognize the urge," I said.

"Like with your girlfriend, for example? You've felt the urge to takeher, I bet."

I looked her over. She felt so fragile in my arms and no longer made any attempt to fight back as I held her.

"You're a little wild, you know that?" I said.

"Am I?" she said, as her frown transformed into an expression of perfect, doll-like innocence.

Then, she grinned and quickly made a jerking motion that made me think she was about to escape or do something crazy. I gripped her wrists tighter and shoved her, rougher than I intended. My body pressed into hers, hard, and I heard her body hit the wall behind her. Her mouth dropped open and a sigh escaped her lips.

"Hey! Let her go!" a woman yelled from above the pool. I looked up to see a middle aged woman in an outrageously large sun hat glaring at me and pointing. "How dare you!"

"I'm not! I'm not doing anything!" I said quickly, and immediately released Jenny and backed up. I paddled away a few feet from Jenny.

"You're twice her size, you should be ashamed!" the woman continued. I could see her looking around, likely preparing to yell for help, or security.

"It's alright!" Jenny said, calmly.

"You don't have to protect him dear! We can go-"

"He's my boyfriend," Jenny said, quickly, before she could finish. I glanced around the pool. Thankfully I didn't see Gracie or Hale there to witness that comment.

"But..." the lady was processing the statement. Her gaze softened a little, but she was clearly still angry and now a little confused. She shook her head. "But even so my dear, domestic violence is a serious thing. Come with me and-"

"It wasn't violence of any kind-" I tried to cut in but the woman glared at me. It was clear that my opinion was no value to her.

"It's fine, really," Jenny said, laughing.

"No I insist dear, please come with-"

"It was a sex thing," Jenny said, cutting the woman off. "That's what we were doing. We were doing a sex thing."