CH 16: Poolside Meeting

Lila was bouncing up and down on Andrew’s thick cock, her ass smacking against his thighs as his shaft slid deep inside her wet pussy. She was completely naked, not a drop of sweat on her body, her breasts bouncing with each movement, her legs spread wide as she rode him like a cowgirl.

The Bikini she had been wearing was tossed somewhere on the ground as they fucked in their cabana by the pool.

She looked so beautiful, her hair falling around her face, her lips parted, her eyes glazed with pleasure, the sun lighting up her naked skin, making her glow. Her hands were gripping his chest for support, her nails digging into his skin, leaving small crescent-shaped marks on his flesh. Her tight, toned body was moving in a hypnotic rhythm, making his cock disappear between her thighs, only to reappear a moment later, coated with her juices.

She was moaning, but not panting, her eyes fluttering closed, her back arching as she took him deeper, her legs spread wide, her bare feet planted firmly on either side of his hips, her toes curling with each thrust.

She knew he loved it when she crouched over him and did all the work. He would just lie back and watch, enjoying the show, his hands resting behind his head. She knew how much he enjoyed the view, her small, perky breasts bouncing, her flat stomach flexing, her smooth legs spread wide, exposing her smooth, bare pussy as his cock disappeared between her thighs. She had put a lot of work in to be able to ride him like this, and for this long.

“Mmm, I love this,” Lila moaned, her head tilting back, her hair falling over her shoulders. “I love the way you feel inside me.”

Andrew didn’t reply, just watched her body moving on top of him as she sat up straight, her hands moving from his chest to her own breasts, cupping and squeezing them, her nipples hard between her fingers.

“I could do this all day,” Lila continued, her voice a breathy moan. “Just bounce on your cock, feeling it filling me up, stretching my tight little pussy. Mm, yes, yes, yes ... Oh, fuck, Andrew, I’m gonna cum,” Lila gasped, her legs spreading even wider, her thighs quivering as she impaled herself on his shaft, taking him as deep as she could. “Oh, fuck, I’m gonna cum!” Lila cried, her whole body tensing, her back arching, her pussy clamping down around his cock, her orgasm rushing through her like a tidal wave.

Andrew felt the pressure of her orgasm, her inner walls clenching around him, squeezing his cock, making his shaft throb, and his own orgasm was right behind hers, his cock twitching, erupting, shooting his load deep inside her tight pussy.

Lila sat down on his cock, her body shaking, her legs trembling, her breathing heavy, her heart racing. Andrew reached up, pulling her down onto his chest, wrapping his arms around her. He began thrusting, his cock flying in and out of her wet, tight pussy, her body quivering, her breasts pressed against his chest. She moaned and gasped, her nails digging into his shoulders, her mouth falling open, her eyes rolling back, lost in the pleasure of his hard cock pounding into her.

He fucked her harder and faster, his hips thrusting up, his cock buried deep inside her, her body shuddering with each thrust, her juices flowing, her inner walls pulsing around his shaft. He gripped her hips, his fingers digging into her skin, and then he slammed his cock into her, holding his tip against her cervix, his shaft throbbing and twitching, his balls emptying, flooding her womb with his hot, sticky cum.

Lila sat up straight, his cock still inside her, her hair falling around her face. He was looking up at her, his blue eyes piercing into her, his lips curled into a smile. She grinned back, knowing he was satisfied with her performance. After all, Lila had been his companion for over two months now, a full month since the party with Sarah, and she’d never failed to make him cum at least once a day.

After all, that’s why he was paying her.

But his payments didn’t stop everything else that continued to happen and change in her life over the past month.

Amara and Hana were still taking care of Lila, as assigned by the head maid Clara. The two maids continued to assist Lila in her daily routine, bathing, dressing, brushing her hair, and doing her makeup. Lila grew close with the two girls, becoming friends, even though she knew they were simply hired servants, paid to take care of her. This eventually led to them not just bathing Lila, but slipping into the warm water with her, turning a bed time routine into something a far more intimate night time ritual.

On a typical evening, Amara would settle into the large, steamy tub first, her legs spread apart. Lila would then slide in between Amara’s thighs, resting her back against Amara’s large, pillowy breasts. Amara’s arms would circle around, hands slick with fragrant soap as she began gently lathering Lila’s small breasts. She took her time, her dark skin contrasting beautifully with Lila’s lighter tone. Her thumbs would occasionally graze Lila’s nipples in slow, deliberate strokes, coaxing small gasps from Lila as she closed her eyes, letting the dark skinned beauty fondle and tease her.

“Just relax,” Amara would whisper into Lila’s ear, her breath warm against Lila’s damp hair. “Let us take care of you.”

Hana, meanwhile, knelt gracefully at the opposite end of the tub, her body partially submerged, the warm water lapping softly against porcelain skin. Her delicate fingers skimmed along Lila’s parted thighs before exploring the soft heat between them.

She started with the faintest touch, her fingertips gliding over Lila’s opening, tracing the delicate curve with featherlight strokes. The water rippled as she ran her fingers along the length of her slit, teasing and exploring the silky-soft flesh, occasionally grazing her clit. She kept the contact light and teasing, drawing out the pleasure, making sure Lila didn’t climax too quickly.

When Lila’s breath hitched, Hana knew it was time. She would slip two fingers inside Lila, curling them ever so slightly, seeking the spot she knew Lila enjoyed the most. Once found, she would begin a gentle, steady rhythm, stroking and massaging the sensitive patch of nerves while continuing to play with her clit.

“That’s it, relax, and enjoy yourself, miss.” Hana would say softly, her fingers pumping and curling.

“You’ve had a long day. You’ve earned this.” Amara would whisper, her hands massaging Lila’s breasts.

The combination of Hana’s fingers inside her, Amara’s fingers teasing her nipples, and the warm water surrounding her was enough to send Lila over the edge multiple times. They would stay in the bath until the water became cold or Lila had cum a couple times, whichever came first. Then the three of them would get out and dry off.

Hana would towel off Lila’s body, making sure she was nice and dry before wrapping her in a fresh robe. Amara would do the same, making sure Lila’s hair was dry. Both their bodies would shine with droplets of water as they remained naked to attended to Lila first.

After the bath, Amara and Hana would put lotion all over Lila’s body, making sure every inch was soft and smooth. They swapped postions from the bed, Amara focusing on Lila’s lower half, legs, feet, ass, and pussy, while Hana focused on Lila’s upper half, back, arms, breasts, and stomach.

It was a wonderful feeling, being pampered by the two beautiful women, and Lila was happy to let them take control. They would always take care of her, making sure she was comfortable, safe, and relaxed. It was the perfect way to end a long day.

Only after Lila was thoroughly clean, dry, and lotioned would Amara and Hana finally tend to themselves, drying their bodies and applying lotion to their own skin. They would always do this in front of Lila, taking their time, giving her a show as they massaged the sweet-smelling lotion into their flawless skin. But they would also all talk, laughing and joking, sharing stories about their day, or what they had planned for the next day. It was a casual, friendly atmosphere, and Lila always felt completely at ease with the two girls.

Once Lila was naked in bed, the two maids would tuck her in and leave her room. After that, Lila was usually too tired to do anything but drift off to sleep, her body satisfied and her mind relaxed. It was a perfect way to unwind after a long day, and Lila would always sleep soundly, thanks to the soothing ritual.

Lila still met up with Marcus every weekday to continue her workout plan in the mansion’s private gym, just as before, but now, there was a new twist.

It had started as an offhand comment one afternoon, a casual complaint as she adjusted the waistband of her tight workout shorts.

“Ugh, I hate how these feel after I start sweating,” she’d groaned, tugging at the damp fabric clinging to her skin. “They just get all sticky and gross. I might as well not wear them at all.”

“Then don’t.” Marcus shrugged. “We shower together, so what does it matter?”

She had blinked at him, expecting some sort of smirk or teasing remark, but he’d simply gone back to setting up their routine. No reaction, no judgment. Just an honest, straightforward answer.

That was all it took.

The next day, Lila arrived at the gym in her usual workout attire. Her snug shorts and sports bra hugging her petite frame. But as soon as she stepped inside and the doors slid shut behind her, she didn’t hesitate.

With a quick motion, she grabbed the hem of her top and peeled it off, tossing it aside. Her small, perky breasts bounced free, the cool air brushing against her bare skin. She exhaled, stretching her arms above her head, already feeling more comfortable.

Marcus was sitting on a bench, silently watching her, but said nothing.

Then, without a second thought, she hooked her thumbs into the waistband of her shorts and slid them down her legs, stepping out of them and kicking them aside. She stood there for a moment, naked except for a tiny pair of black panties, her hands on her hips, her eyes locked on Marcus.

He was still sitting quietly, but now his gaze was definitely on her. He took in the sight of her bare breasts, the subtle curve of her waist, the swell of her hips. His eyes lingered on her panties, the thin strip of fabric barely covering her mound.

“You’re right, I should take them off, too.” Lila said unprompted, hooking her thumbs under the waistband.

She didn’t wait for a response, pulling the scrap of lace down her legs and flicking it away. She stood there, completely naked, her hands resting on her hips, her chest rising and falling with each breath.

“Ready?” Marcus asked, getting up from the bench.

That was it. No reaction, no teasing, no comment. Just business as usual.

“Always.” Lila smirked and stepped forward.

They started the session as always: warm-ups, stretches, then an intense circuit of cardio and weight training. The difference was that Lila’s bare skin gleamed under the overhead lights, every curve of her body shifting as she lunged, squatted, or lifted. Marcus remained focused, offering praise or correction when needed, reminding her to keep her back straight, to breathe properly, to engage her core. His voice stayed calm, professional, the same as ever. His palm would lightly guide her shoulders if she lost form, no different from how it had been when she wore the tight sports bra and shorts. Yet each time his hand brushed across her back, it lingered just a moment longer than before.

After they finished, they would head to the showers together. As the warm water cascaded over them, Marcus would take his time, his strong hands gliding over her body as he lathered her skin with soap. His touch was firm yet careful, massaging away the tension from her muscles while ensuring every inch of her was thoroughly cleaned. And once she was rinsed and fresh, he would step away, leaving her to enjoy the last moments of the shower alone.

A week after Lila started her workouts nude, and the routine shifted again. When she arrived, Marcus took off his clothes. He didn’t make a big deal out of it, just casually pulled his shirt over his head, dropping it to the floor, then slid off his shorts, stepping out of them. His briefs came next, his cock hanging between his thighs.

Lila tried not to stare, but it was impossible not to. Her gaze flickered over the sharp definition of his abs, the lean muscles of his arms, the powerful curve of his calves, and the broad expanse of his chest. His skin glowed under the bright gym lights, every muscle toned and tight from years of dedicated training. But no matter how impressive his physique was, her eyes kept drifting lower, to the heavy weight hanging between his thighs. His cock was thick, its length impressive, and it swayed as he moved, almost as if taunting her. Even soft, he was big, a hint of girth promising just how much larger he could get.

Their work out would start as normal, Lila stretching her nude body while Marcus stretched his own. But it didn’t take long for the girth of his cock to grow, thickening, rising from his thighs until it was standing proud and erect. It was the way she was used to seeing him in the shower, but never outside the confines of the steamy bathroom.

For the first time he recommended they do partner-assisted stretches. It made sense, the logic behind the suggestion was that they would help improve Lila’s flexibility, and that was true, but he never suggested it when she had clothes on.

Lila laid flat on her back, pulling her legs towards her head. Marcus knelt behind her, his hands gripping her thighs, and then slowly pushed her knees towards her face, moving closer and closer until he was lying right on top of her, she was practically bent in half. The angle was awkward, her thighs quivering from the strain, and it was a struggle to maintain the pose, but his body held her in place, his fingers wrapped around her ankles.

Then she felt his cock pressing against her, the tip slipping between her thighs, brushing against her opening. His hips rolled, sliding his shaft along her slit. He defended it by saying the pressure helped her stretch, that he was simply using the weight of his body to hold her in place.

He made it hard to believe when he told her they were going to do one final push, trying to bend her even further. As he pressed down, his cock slipped deeper, her tight entrance spreading as his thick shaft pushed inside her. She bent in half fully, her feet on either side of her head. But Marcus’ cock was buried deep in her pussy, his balls resting against her ass.

He stayed there, her tight inner walls pulsing around him, his grip tight on her legs. Her face was inches from his, her cheeks flushed, her lips parted. He watched her expression, the mix of discomfort and pleasure as she struggled to maintain the pose.

Finally he pulled back, his cock sliding out of her. Her legs fell back down, her muscles aching, but she didn’t protest, and Marcus didn’t comment. He reached out his hand, helping her to her feet. He comment on their stretch in a professional way, as if he hadn’t just been balls-deep inside her. Talking about her hamstrings and glutes responding well, and needing to keep her back more straight, all things Lila was familiar with from his instructions during previous workouts.

Next her had her turn around, facing away from him, bending at the waist. He got behind her, his hands on her hips, and pulled her towards him, her ass pressing against his cock. As he pressed on her back, encouraging her to hold her ankles, his cock slipped into her once again.

As he pushed her down, her pussy spread, his thick shaft sliding deeper. Once again, her legs were spread, her feet on either side of her, her ass up, his cock buried inside her. He stayed like that, her muscles quivering as she struggled to maintain the position.

After a minute of holding his cock in her pussy, his hands on her hips, he slowly pulled her up, his cock slipping out. He guided her to stand up straight, her legs shaking, her face flushed. Again, he said nothing, his expression calm. More praises, talking about her flexibility, her strength, all the while his cock was still rock hard, a hint of her juices coating the shaft.

Lila was confused, conflicted. Was he actually trying to help her, just accidently sliding inside her, or was this some sort of twisted way for him to fuck her?

Her question was answered when Marcus lay down on his back and put his hands in the air. He had tested the water, seeing how she responded, and her reaction seemed positive enough. He asked her to crouch over his cock and ride him, saying it was an excellent way to work on core strength and control.

Lila had no reason not to go along with it, so she did as instructed, crouching over him, her legs spread, his cock standing proudly. She held his hands for balance, her palms pressed against his, his fingers interlocked with hers. She took a deep breath and then lowered herself, his tip spreading her entrance, her tight hole slowly stretching as she sank down onto him. His thick shaft spread her inner walls, her muscles gripping him, her thighs quivering. She kept going, her pussy swallowing him, until her ass was pressed against his hips, his cock buried deep inside her.

As she sat there, his thick shaft throbbing inside her, his hands holding hers, he went on to explain how this so called exercise was going to work.

“This position works your core, legs, and pelvic floor, Lila. You have to use your quads and hamstrings to control your movement, your glutes to power your thrusts, and your abs to stabilize yourself. Squeeze me as you move—it engages your pelvic muscles more.”

She nodded absently, focusing on maintaining proper form as she began moving. With her quads and glutes engaged, she lifted herself slowly, rising just enough for his cock to nearly slip free before lowering herself back down in a controlled descent. Her inner thighs working, her calves tensed to keep her balanced, and her core tightened to stabilize her movements. Each time she sank back down, she clenched around him, her pelvic floor muscles contracting as instructed, squeezing his cock before pushing herself up again. She maintained the rhythm, each rise and fall requiring precise control, her whole body working to ride his thick cock. Her breathing steady as she focused on working the correct muscles.

“Good,” Marcus observed, his tone still professional. “Control is key. Don’t just drop down. Engage your glutes on the descent and use your legs to power back up. Keep your chest lifted, back straight. Breasts out, shoulders back.”

She adjusted slightly, correcting her posture. After twenty controlled reps, the movement was becoming more fluid, her legs adapting to the rhythm, her thighs steadily building endurance with each controlled descent and rise.

“How long do I hold?” she asked, her breathing steady.

“Ten seconds each time before rising,” he instructed. “That gives your muscles time to adapt and build strength. Squeeze hard, I want a good, strong contraction, like you’re trying to push me out.”

She followed his instruction, lowering herself fully, her ass pressed against his hips, his full length buried inside her. She could feel his pulse throbbing as her inner muscles tightened around him, maintaining the position. The tension in her thighs and glutes was steady but manageable, her core engaged to keep her balance.

“Like this?” she asked, maintaining the hold on his cock.

“Exactly,” Marcus confirmed. “Keep the squeeze consistent. That’s where the real strength comes in, controlling the motion, not just moving through it. Your goal is a ten-second squeeze, no more, no less. You want to feel the burn, but not exhaust yourself. Once you’ve hit ten seconds, lift yourself back up, and repeat.”

She focused, her legs supporting her weight, her pelvic muscles clenching in steady intervals as she followed his lead. When ten seconds passed, she pushed upward, activating her quads to drive the motion, before lowering again into the controlled hold.

Marcus observed her form, nodding in approval.

“We’re going to keep this going for the rest of the session,” he said. “If you can last the full hour.”

“An hour? Please. This is easy.” Lila let out a short laugh, rolling her eyes.

“We’ll see.” He smirked but didn’t argue.

She kept the pace steady, lowering herself slowly, holding, squeezing, and pushing back up. The first few rounds felt manageable. Her core stayed engaged, her thighs worked through the motion, and she controlled every movement like a pro. But as time stretched on, the steady repetitions while maintaining proper posture and slower movements that she was used to, began to ware her down. The burning in her thighs and glutes intensified, creeping in with each hold. Her calves trembled with the strain of balance. Sweat slicked her lower back, her muscles tightening with effort. By the halfway mark, her breaths were coming in shorter huffs, her legs quivering as she fought to stay in position.

“Still easy?” Marcus teased, his cock throbbing inside her.

Lila bit her lip, her legs shaking as she tried to power through another set.

“S-shut up,” she muttered, her grip on his hands tightening.

She managed a few more reps, but when she tried to push up again, her legs wobbled, refusing to lift her. His cock was still buried inside her, but she couldn’t rise up, the tip was pressing against her cervix.

“I—I can’t, My legs are done.”” she panted, releasing his hands and collapsing against his chest as she lost her hold.

Her naked body laid flat against his, her legs resting on either side of his torso, his cock still throbbing inside her. She was gasping for breath, her muscles quivering. He wrapped his arms around her, holding her in place, his strong hands gently caressing her sweat-slick back.

“You did good, Lila,” he praised, his voice low, his hands trailing up and down her spine. “You lasted longer than I expected for a first session.”

“I’ve rode thousands of cocks in my life.” She groaned into his chest, her breathing still uneven. “But that was brutal.”

“That’s endurance training,” Marcus replied simply. “You’re engaging your core the entire time, stabilizing with your legs, and maintaining control over your movements. If you keep this up, you’ll notice an increase in strength and stamina. In tine, you’d be able to ride a cock for hours without tiring.”

“I rode Andrew’s cock for four hours once” Lila groaned.

“With the right training, you could ride a cock all day.” He chuckled, his hands roaming over her back.

She was exhausted, her body drenched in sweat, her legs feeling like jelly. But she didn’t try to move, staying pressed against his chest, her pussy clenching around his still-throbbing cock.

“I should probably get off you,” she murmured, not making any effort to lift her weight.

“You’re fine, take a moment to rest. It’s important to allow your muscles to recover properly,” he assured her, his hands still stroking her back.

They stayed like that for a few minutes, his cock buried inside her, his strong arms holding her against his chest. She closed her eyes, her breathing finally starting to slow, her heart rate calming. She could feel the sweat cooling on her skin, her muscles slowly relaxing, the afterglow of her workout washing over her.

Marcus’ hands never stopped, gently rubbing her back, massaging the tightness from her muscles. It felt amazing, his strong fingers kneading away the soreness, sending little sparks of pleasure through her body.

“Okay, I should get up now.” Lila sighed, finally feeling her strength returning.

“Sure,” Marcus replied, releasing his hold on her.

She took a deep breath, steadying herself, and then pushed up, lifting her weight off his chest. As she got up, his cock slipped out of her, sliding between her thighs. She paused, hovering over him, his slick shaft brushing against her opening, her juices smearing against his skin.

“I mean, I should at least let you cum.” Lila breathed, looking down at him.

“Yeah?” he raised an eyebrow, his lips curling into a smile.

“You didn’t even cum once, and I think I owe you.” Lila smiled back, biting her lip.

“Well, if you insist.” Marcus smirked.

“Just make it quick,” she said, rolling off him and onto her back, her legs spread. “Then we’ll get cleaned up and call it a day.”

“Sounds good to me.” Marcus laughed, getting up and positioning himself between her thighs.

He slid his cock into her wet pussy, letting out a soft grunt, his shaft stretching her. He gave a couple hard, quick thrusts, and immediately started cumming, clearly pent up from the last hour of her workout.

Marcus’s moans deepened as he reached his climax, his thick, pulsing shaft sending rope after rope of cum deep inside Lila. Her body shuddered as his release filled her, coating her inner walls with warm, heavy streams. Lila lay on the ground, her muscles still humming from the workout as she allowed him to fill her completely. His cock slowly retracted, the tip still dripping, a single, glistening strand clinging to her pussy lips.

“Thanks,” he said, getting to his feet. “But don’t feel like you have to repay me. That’s what I’m here for, remember? To help you with your training.”

“I know, but...” She pushed herself up onto her elbows, catching her breath.

“I appreciate it.” Marcus shook his head, walking over to the bench and grabbing his towel. “The other girls in the house do the same. They say it’s only fair. But it’s not necessary. Just doing my job.”

“Other girls?” she asked softly.

“Yeah,” Marcus replied with a slight shrug. “You know, Lila, you’re not alone in this routine. At some point in the week, Amara, Hana, Clara, Eloise, and all the other female staff in the mansion, train naked with me, just as you do now. Amara, with her luminous dark skin and full, enticing curves; Hana, whose porcelain complexion and delicate frame seem almost ethereal; Clara, with her radiant white skin her perfect, heart-shaped ass; and Eloise, with her rich, dark tone and petite, understated allure. They all push themselves to the limit in my gym. But you are the only one who comes to me for daily visits.”

He paused, wiping his hands on his towel before extending one toward her.

“Oh,” Lila blinked as she took his hand, letting him help her to her feet.

“I have to admit, restraining myself from blowing my load while these beautiful girls are using my cock to work out on, each one confident, each one using my cock to push her limits. Their beauty and willingness to train turns every session into an electrifying test of self-control.

What they do at the end of each session is really not necessary, but as a thank-you for keeping my climax in check during the session, they each offer me the same reward. They offer me their holes, inviting me to fill them and unload my cum deep inside their bodies, just as you did. Of course, they are not required to do so, and neither are you, and if anyone doesn’t want to, then I respect that, and I would never force myself upon them once the work out is over.”

“So me offering my pussy isn’t special?” Lila frowned, not sure how to feel about that.

“On the contrary, I appreciate it more. The fact that you offer it freely is very special, and it is the same for the other girls.” Marcus smiled. “Every day, I’m in the gym, My goal is to help beautiful women use my body to push themselves to their limits, working muscles in a way they normally wouldn’t. I expect nothing in return, I am paid by Mr. Barrington to do my job and nothing more. So if any of the girls here are willing to go that extra mile, offering me a thank-you by inviting me to use their tight, perfect holes and fill them with my cum, it’s always special, and it’s an honor and a privilege.”

“Okay, that makes sense, and I’m glad they are willing to thank you. I would feel bad if after riding you for thirty minutes and squeezing your cock, you were left with blue balls. It’s only fair.” Lila nodded.

“I appreciate that,” Marcus smiled, tossing his towel over his shoulder. “But I think you’ve had enough training for one day. How about we head over to the showers, and I can give you a massage?”

“Yes please.” Lila sighed, stretching her arms above her head, her pert breasts lifting.

“This way,” Marcus grinned, heading towards the back of the gym.

After that, Marcus cleaned up up as usual, his hands roamed her naked body, the soap suds coating her skin, his fingers caressing her breasts, teasing her nipples, his other hand gliding along her slick thighs, slipping between her legs. He spent extra time on her pussy, making sure she was nice and clean, his fingers teasing and rubbing, occasionally pushing inside her, coaxing out the cum that had spilled into her.

They didn’t say a word about what had happened, or how they’d ended the session. But after confirming with the staff that they also used his cock to work out, and were willing to give him a thank you, Lila couldn’t help but feel a little better about what had happened, and felt even better about moving forward.