Chapter 45 - Into the Deep End

“You weren’t supposed to cum in her, Jack!” Karen snapped. “What if she gets pregnant?”
He shrugged. “Can’t we take her in like Candice? I know she was a bitch to you, but she’s so tight!”
“Jack, you can’t take every good lay into our family.”
“I know Sammy though, she’s really not a bad person!”
Sammy’s grin was faltering as she closed her legs, “what do you mean?” The natural beauty with a swollen belly became suddenly self-conscious.
“Just ignore this whole conversation and go back into the pool.” He waited as she waded back into the water with a care-free smile. “I’m sorry, Karen, I just couldn’t resist.”
His sister shook her head with a dismissive smile. “You’re cute, you know that?”
Jack was relieved, stepping over to give her a kiss on her lips and then another upon her breast. “What should we do with Jenna?”
 
Karen sighed as she got up, following him to the edge of the pool. He looked to the other inflated girls as she contemplated. Tamara sat with a conflicted expression on the edge of the pool, with numerous diving sticks wedged into both of her lower entrances. Sitting close by, Kelsey had a partially inflated beach ball inside her, but she hid her discomfort far better than the older Latina woman. The normally thin redhead, Harriet, supported a partially submerged belly that was far larger than the others. She was holding a substantial enema she had taken from the pool jets and audible rumbling came from her belly as the air inside shifted.
 
And, of course, Sammy had his seed sitting in her loins. Most of it is probably washed out now, though. She swam around the pool leisurely, her own prominent belly causing her to list side to side. All of them were getting their comeuppance for badmouthing his sister, but Jenna, the snooty blonde, was the only one he hadn’t punished yet.
 
“Why don’t you make her drink that?” Karen pointed to a pitcher of lemonade on the nearby table. “All of it. Make her ‘guzzle’ it.”
He let out a slight laugh. “I’ll go a step farther.” He grabbed the end of the garden hose that sat uncoiled by the edge of the pool. “How about I make her drink from this?”
“Even better! Make her big and squishy!” Karen went back to her seat as he brought the hose to his victim.
 
With distrust in her eyes, Jenna pulled her arms from the edge of the pool. “What?”
He stood above her, his covered erection clearly visible to them both. “Put this in your mouth and drink as much as you can.”
 
The dispassionate girl with a full belly closed her mouth around the hose, awaiting what was to come. Jack eased the handle, allowing a comfortable amount of water to flow. She drank it easily, collecting it in her mouth before swallowing. Her eyebrows raised as he increased the flow. She gulped it down, leaning ahead as she suckled on the hose. While she filled, Jack decided to be a little more mischievous.
 
Searching through the nearby maintenance closet, he found a short pool hose. The flexible blue tube had rubbery white ends, perfect for his idea. He jumped into the water, walking closer to Jenna. She continued drinking the water at a steady pace as he pushed the compressed hose into her behind. She tried to evade the unexpected object, but he followed, making sure it was nestled in her rump. She brought a hand down to remove it, but he surfaced and told her to keep it in place.
 
Bringing the hose beneath the surface, Jack felt it pull lower as water flowed in. He knew by Jenna’s pained whimpering that air and fluid were already rushing into her open asshole. He brought the other end to Harriet, telling her not to remove the hose as he swooped down and wriggled it into her ass.  He arose to see her clenching her fists, waving them frantically as she gasped. Her usual indifference switched to panic, as she was desperately trying to retain her enema. But, from the look on her face, it was only a matter of time.
 
A loud gurgle signaled the start as Harriet leaned against the side of the pool, no longer resisting. She pushed her contents through the tube and into her friend. Jenna stumbled ahead, startled by the feeling. She went to her tiptoes once she stopped, with her eyes wide and her cheeks bulged, filling from both ends. Within minutes the girl’s belly puffed out to the size of a twin pregnancy and she had no way of escape. Jack knew she was reaching her limit, but he loved the sight too much to stop now.
 
In fact, he was aroused immensely. He looked to his sister as he approached Sammy. “Can I please cum in her again? What are the chances anything will happen underwater anyway?”
“Jack…” Karen gave him a look of disapproval.
“Pleaaase.” He intertwined his fingers as he begged.
She let out a long sigh. “Fine.” She said, smiling dismissively as she laid back.
 
Jack thanked her gleefully, rushing over to Sammy. He brought her to the edge and grabbed her legs, making her lean against the edge of the pool. She wrapped her legs around him to stabilize, her expression shifting from skepticism to relaxation. Her big smile showed as he slipped into her pussy. He pushed against her belly as he moved, leaning back to get more of his cock into her warm entrance. Sammy beamed as she watched him, biting her lip as he looked into her squinting eyes.
 
Feeling the cooler water against their privates and water splashing along her modestly sized chest, it wasn’t going to take long. Jack moved slower, feeling the tension build. He came to a full stop as it came, with his cock buried in her pussy. Sammy trembled and gasped, her mouth open as he shot inside her. She pulled him in with her legs, forcing him to keep moving. She grunted loudly as she pulled him against her swollen tummy, moving him back and forth as she enjoyed her own orgasm. She shot forward and latched on, making Jack stumble back.
 
He hastily took a breath as she forced him below the water. She rode him down, still moving her hips as her weighted frame humped him. She pinned him to the pool bottom for a moment, sitting atop him as she moved her hips. He was still hard, but the sensation was too extreme. She didn’t care as he grabbed her side and ass, tensing her pussy upon his shaft. He needed air soon, so he opened his eyes for a moment to look for an escape.
 
It was at the exact moment she found true orgasm, her wild blonde hair dancing around her as she clenched her eyes. Her mouth set in the shape of an O as she squeezed his shoulder. Her covered breasts looking dwarfed by the immense stomach that was squished against him. She looked amazing as she finally eased her hold, using her legs to propel them upward. They both broke the surface with a gasp, wiping away the water as they looked to one another. Her goofy grin made him smile too.
 
“Looks like she liked it more than you!” Karen smiled. “I think you better help her, though.” She pointed to Jenna.
 
Jack turned to see her belly filled tight. She looked like she was carrying triplets now as tears ran along her puffed out cheeks. Water was spilling from her mouth, but he could see she was still taking an occasional drink. Harriet’s belly was nearly back to normal, as he could see through the clear blue water. He directed Jenna to remove the hose from her mouth and for Tamara to turn it off. The stocky, darker-skinned girl awkwardly stood, the diving rods clenched tenuously in her lower openings. She moved stiffly, keeping them in place as she stopped the water’s flow.
 
Returning his attention to the connected girls in the pool, Jack told them to transfer their contents. Jenna’s eyes fluttered as she leaned forward, pushing the collected fluid in her belly back through the pool hose. Harriet showed her teeth in discomfort, moving over to the shallow pool entrance to lean on the steps. She looked aside as her eyes grew, feeling the contents of the weighted tube returning to her. The hose swelled for a moment before smoothing out again. She lifted up, gasping as the obstruction pushed into her bowels. She shook her head as she went back down to rest on her elbows, unable to stop the unpleasant feeling.
 
Jack went to the edge near Kelsey, who was still laying in the folding chair, showing her own unease as she retained the partially inflated beach ball. He told Tamara to remove the rods and come closer. He watched as she slipped the colorful sticks out from between her glistening brown lips. She was still open when she started on the objects in her ass and this gave him an idea.
 
At his request, Kelsey got up, huffing as she laid on a fluffy towel beside the pool. Tamara came over and sat in the opposite direction. They scooted closer until their privates touched, wrapping their arms around one another’s legs. They were scissoring, rubbing their vagina as they got comfortable. He told them to feel excited and then for Kelsey to push the beach ball into Tamara.
 
They Tamara reached a hand between her legs, stroking herself as they rubbed their privates together. Kelsey put her hands down to raise herself, pressing her hips upward. They both moved with purpose, building their arousal. Kelsey paused, taking in a deep breath to prepare for the next step. She let out a loud grunt as she pushed with all her strength. She hesitated before making another attempt to transfer the sizable object.
 
They turned slightly, allowing Jack to get an up-close view of the brightly colored ball crowning from Kelsey’s vagina. They pressed together again and once more Kelsey struggled to birth the toy. This time she made progress, as Tamara gasped, pulling her hand back as she stabilized her full frame. Her belly jiggled as she moved, attempting to work the object into place. She raised up to grab Kelsey’s shoulder, her eyes shut as they both grunted.
 
Looking as if she might burst into tears at any moment, Kelsey whimpered through her teeth as she pushed again. She trembled, fighting to pass the ball, looking like it might not be possible. She let out a high moan, finally making progress. Her mouth hung and she jerked backward, falling away from her recipient. The end of the multicolored ball slipped out of sight into Tamara’s ass, as she also jumped back onto the cement.
 
She clearly wasn’t ready to take it in that hole and Tamara howled as her pliable rear absorbed most of the impact. The ball was more of an oval and with the nozzle buried in her butt, she had no way of getting it out easily. Tamara rolled from side to side, putting her thick legs out rigidly. Her bountiful breasts and big belly pressed outward as she laid on them, covering her ass as she whined. All eyes were focused on her as she begged for help.
Staring in awe, Jack felt his cock stiffen again. He loved watching her bulky frame squish against the ground as she accepted the pain. She went to her side and pushed with a loud gasp, but the object in her ass only peeked slightly before disappearing. He decided to help her, taking the hose and jabbing it into her sore ass. Tamara let out an agonized huff as he fed the hose around the ball and snaked it through her guts. She swatted at him, but she was too weak and pained for it to have an effect.
 
He told her not to remove it as he walked over and restarted the flow. Jack watched her roll onto her back, clenching her fists as she lifted herself with her thick legs. Her chest wobbled as her belly swelled, growing tighter as the minutes passed. Rolling over to find some kind of relief, she went to her hands and knees, letting her distended stomach hang low.
 
“Please stop the water! I can’t take it!”
“It will help push out the ball.” He reasoned.
 
She struggled fruitlessly, complaining loudly in her native tongue as the other girls lost interest. Kelsey took a time to recover, but now without the beach ball wedged in her pussy, she was laying upon the pool’s edge. Jenna and Harriet were both looking a little pale, as they both had puffed bellies and a tube connecting them beneath the water.
 
Sammy, however, was absent from the pool. Jack found the wet woman between his pregnant mother’s legs. The artificially inflated girl pleasured Betty as she sunned herself. With her bikini bottoms moved aside and a hand beneath the top, Betty gave a low purr as she shifted, moving in response to Sammy’s tongue. She looked content, sprawling out and letting her hands sit idly as Sammy gently licked her. I don’t think I’ve seen her that carefree in a long time.
 
Karen noticed his interest. “Maybe she should get some punishment while she’s distracted.” She spoke with mock sincerity.
“Have anything in mind?”
Karen pointed to the garden hose lying on the cement. “She shouldn’t get out of this without some of that.” Karen giggled. “Maybe she’ll like it.”
 
Jack nodded with a grin. He unfurled the hose as he approached Sammy. She certainly heard their talk, but she was intent on pleasuring Betty. He wiggled the end into her butt, making her jerk as it popped through. He turned it on as he thought about what to do next. Harriet and Jenna caught his eye and he summoned them from the pool.
 
The two girls trudged up the stairs, walking sluggishly as they emerged from the water. Both of them reached back to hold the heavy, partially filled pool hose in their backsides. Their bellies danced as they came before him, breathless and pained. At his command, they both got on the ground and raised their legs, opening them wide. He enjoyed seeing their trimmed pussies on display and he decided to go to Harriet first.
 
Crawling atop her, Jack nudged his way inside and rested upon her water-filled midsection. He leaned ahead to whisper in her ear. “Push it back to her.” He went higher again and began fucking her, watching the distress and embarrassment as she stopped resisting. He could hear the water flowing down the short hose, moving into the woman lying beside them. Harriet moaned as she grabbed her legs, holding them back to allow Jack full access. She was still hurting, but having the water exiting was clearly worth the torment.
 
Jenna wasn’t faring so well. She clasped her hands upon her mouth, stifling a burp as she continued raising her legs, lying on her back. Her long blonde hair was still wet, clinging to her shoulders as she turned her head uneasily. She groaned as another bubble of air pushed up her throat. She let out a muffled belch, her eyes shut tightly as she tried to keep composure. Water could be heard in the tube and her open ass was accepting it easily. Her tummy rose and fell, growing ever larger as time passed.
 
Sammy’s stomach was also inflating. She moved her hips subtly as the hose filled her, not pausing as she licked his mother’s pussy. He realized Karen wasn’t in her seat now and he found her next to the hose handle on the side of the house. Unaware that he was watching, she casually twisted it to increase the flow as she passed into the house.
 
Jumping upright, Sammy edging ahead as the increased flow made her very uncomfortable. Betty opened her eyes with an irritated glance, but it faded as Sammy came over her. The filling girl whimpered as she crawled into Betty’s arms, telling her it was too much for her. Betty stroked her hair, hugging her as the filling belly pressed out from between them. He watched Sammy’s plugged ass swaying, feeling his next orgasm creeping closer.
 
He looked down upon Harriet’s bouncing tits, which were still covered by her bikini top. In fact, all the girls still wore their tops, but not their bottoms. He also noticed that she was now holding Jenna’s hand. The girl beside them had a trembling lip as she took more and more of her friend’s wastewater. Her stomach bulged, growing tight as it pushed outward, sagging around her smaller frame.
 
He was in the final throes, feeling it building closer and closer. Jack looked to Jenna, Harriet, Sammy, and then Tamara, enjoying their aching expressions. He loved seeing their bodies filled, their feminine curves swollen past normal limits. This is heaven. He slowed as his cock shot a load into the emptying girl beneath him. She was twitching weakly in time with his releases, her whole body weak from the repeated inflations. He sighed as he collapsed upon her, making her whine as he compressed her midsection.
 
“Did you cum in her too?” Karen cast a shadow upon them, her curves looking equally as enticing from this angle.
“I can’t help it. It was too much fun!” He looked up to her with sad eyes. She can’t stay mad at me. “I think I’m finally done, though. That last one kind of hurt.”
“No! You want to make everyone around you pregnant?” She cocked her head to the side with disappointment. “Well, fine, let’s get you a harem.” She slipped the command rod from her bottoms. “I guess the more kids the better, right?”
“Karen, I didn’t mean…”
“Seriously, let’s try something.” She seemed to calm as she held the command rod. “Everyone except Jack line up right here on your knees.”
 
They all came slowly and clumsily. Jenna rolled her monumental body over with Jack and Harriet’s help and Karen gave her the go-ahead to remove the tube. She was told to retain the fluid, and surprisingly she only let a tiny amount escape as they took it out. The massive amount of fluid collected in her drooping belly and air moved audibly throughout. She was fighting to keep it contained, her face contorted as sweat glistened on her forehead.
 
Sammy walked over, her perfect ass gripping the hose as she moved. Her covered breasts rested atop a large, spherical belly, which shook as she stepped. Her top straps dug into her soft, creamy skin. Karen told her to take out the hose as she turned it off. Sammy paused, reaching back to remove the attached tube, pinching her asshole closed to hold the fluid as it clacked on the ground.
 
Everyone, including Betty took a spot next to the pool. She removed her bikini bottoms to join the rest of them, with wet asses exposed. They awaited her command in varying states of discomfort. Karen directed them to allow her brother to fill them.
 
“Jack, remember the next command I make.” Karen paused to think, “I want you to cum in all of their pussies, one by one, and keep cumming until you physically can’t anymore.” She tucked the command rod into her bikini strap as she stepped back to watch.
 
He had sudden determination as he went behind Harriet. Drained literally and figuratively, she leaned on her elbows with her ass raised into the air. Jack slipped his cock into her vagina, grabbing her wet hips as he pumped her. Within seconds he released a blast of semen that felt uncomfortable. After the first shot it felt suddenly amazing, as if he unplugged a stopper in his body. He repeatedly shot into her loins, feeling his cum collecting around his cock. It was slippery and slimy as he pulled out and moved down the line.
 
Cum shot onto the ground as he moved around Jenna’s legs and stuck his shaft into her mound. She groaned noisily as he stabbed deep and filled her even more. She was supporting herself with her hands, but her stomach was clearly holding some of her weight. Her bulging midsection spread from between her arms and legs, showing weight at the bottom where the water rested. She pulled forward as he came, looking over her shoulder to give him a pleading look. Once he considered her full he continued to Kelsey.
 
She eyed him nervously through her glasses, jerking in surprise as she felt two lines of warm cum blast onto her springy ass. He put the tip into her shaven slit, making her jump again. Blasting semen into her, he worked the tip in her warmth, waiting until she got her fill. Kelsey pulled ahead as she reached a hand back, giving him a worried glance as she then touched her swollen belly. Jack was stubborn, though, and he poked back inside. She howled as he popped into her tight asshole, pulsing as he pushed more cream into her.
 
Sammy leaned down and took Kelsey’s breast from beneath her swimwear, kissing the side to comfort her. Kelsey grew tense, her mouth open with agony as she arose. Her breast slipped free of Sammy’s mouth, but Jack pointed to it, asking her to continue. Sammy moved in front of Kelsey, latching onto her nipple, sucking it firmly. Kelsey was not enjoying it and again tried to pull free. This time she went too far and fell upon Sammy.
 
Her distended belly pressed out from between them and Sammy fought back tears. She tried to keep a brave face, but it was clear she didn’t handle the pain well. Jack slipped out, seeing his thick cum running out of Kelsey’s open asshole. Lifting her legs, Jack wasted no time in going into Sammy’s opening. He fumbled for a minute but finally felt the entrance opening. Sammy started crying suddenly and he realized he was in her ass.
 
She grappled Kelsey tightly as she bawled, digging her fingers into the other girl’s shoulders. He couldn’t hold back, blasting his cum into her overfilled rump. Sammy regained her control finally, blinking away the tears with a sniffle. She let go and looked to the sky, stabilizing her breathing to cope with the distress. Jack thought about putting some in her other entrance, but he decided to move on instead. 
 
Betty awaited him with a playful smile, her malleable ass bouncing as he got into position. He found her excited hole and poked his continually erupting shaft inside. She gasped, working her defined hips back upon him. He took a handful of his mother’s hair as he rode her, enjoying her coos of delight. She slid his shaft deeper, but his seed was already spilling onto the ground.
 
“Fill my ass.” She turned to look at him with her big green eyes and rosy cheeks. “Put it in my ass, baby.”
 
Jack quickly switched holes, making her lean forward as he poked into the hilt. She let out a low moan of mixed pain and pleasure and after a moment she was bouncing on her own. All the while she was taking repeated deposits, and now none of it came out. They both stopped moving after a while and he let go of her hair. He stayed mounted, looking to Karen as he sprayed an unending flow up his mom’s ass. He took it out, ready for the final girl.
 
“Wait! Give me just a little more in my mouth.” She gave him a pouty glance as he shot cum on her legs and feet. “Just a little.”
“Fine.” He directed her to spin around.
 
Betty’s full tummy swayed as she pivoted. Her apple ass raising as she went down on him. She timed it poorly, taking a shot of cum right in her face as she swallowed his cock. She clenched her eyes shut as she gulped down his repeating loads. A line of thick white goo ran along her nose and down to her chin. She opened her eyes to look at him, suckling on his cock as she grinned. She fell behind for a moment, letting some build up in her mouth. Her cheeks bulged before she swallowed.
 
To her dismay, Jack decided she’d had enough and set his sights on Tamara. The broad girl had the end of the beach ball visible from her wet asshole and she was clearly aching. He touched her warm skin, enjoying the feeling as he kneaded her doughy hips. He opened her thick ass and stuck his cock in between her dark lips, distracting her from the pain in her ass. Jack felt a tightness in his balls, but he continued pumping his seed into the displeased woman.
 
He took hold of the partially filled ball and tugged. Making her look back with a harsh scowl. Her red lips parted, showing her teeth as she spoke in her native language. Tamara hit his thigh, her dark nipples erect as her tits bounced. He payed no attention, pulling firmly. She finally relented, begging him to stop. Jack was almost to the halfway mark, though, and he decided to help her by removing it sooner rather than later.
 
Tugging with both hands, Jack dislodged the pool toy, making the big girl yelp and lurch forward. She fell onto her full belly, which caused her plump body to quake pleasantly. Jack continued spurting cum onto her back as she writhed in agony.
 
“Holy crap, you’re still going?” Karen asked with awe.
He shrugged. “Want to get in on this?”
A smile spread across his sister’s face. “Sure, why not?”
 
His pregnant sister laid in a folding chair as he came up and raised her legs over his shoulders. He inserted his cock into her tight backdoor, unloading in her ass. She gave him a beaming smile as he squirted repeatedly. She pulled him closer, touching her nimble fingers to his cheeks. She was always caring, even in the beginning. She just acted tough. We all were acting before the rod came along. He focused on his sister’s caring eyes and frazzled hair. This is heaven. He looked back to see all of the women. They were full and tired, lying in various positions with their full bellies dominating their bodies.
 
“You’re so cute.” She spoke with a giggle. “I think my tummy is growing from all that cum!” She smiled. 
“I love you.” Jack spoke with a gasp as he shot again.
 
Then, without warning, it stopped. Jack removed his cock, seeing her butt tense to hold in his deposits. He sat back, feeling light-headed as he laid on his elbow. His eyes blurred and darkness overtook him abruptly. It was only a second or two until he regained consciousness. Betty and Karen stood above him, their curvy bellies prominent in his view. Their relief was visible as they saw him smile.
 
“Jesus!” Karen touched his arm gently. “What happened?” 
“I don’t know, I guess I went too long.” He sat up, holding his hand out to ease her worry. “I’m fine!”
She took a moment before she calmed down. “We probably shouldn’t do this to our bodies too often then.”
“I guess, but that was fucking amazing.”
Karen smiled with warm assurance. “We will have to do it again. Just maybe not do it all at once.”
Jack agreed as he got up, nestling between Karen and Betty’s soft and rounded bodies as they hugged him.
--
“So what happened with Tabitha?”
“Jack doesn’t know. He wasn’t trying to make her do that.”
Isabel gave a knowing look. “Marcy wants me to take the rod right now and wipe your minds.”
Ashley spoke with urgency. “You can’t take it yet! Jack just made a mistake. He is trying to fix all of these problems-“
“Stop. I’m tired of hearing how he’s trying to be better. He’s a teenaged boy with free reign to fuck anyone around him, he’s not going to get better.” The stoic woman looked aside with irritation. “I’m being a fool for trusting you, but I think you’re the last chance.” Isabel offered the command rod. “Did you know that he got his sister to set him up with a bunch of pregnant women today? I followed them to some rich guy’s place where they were having an orgy.”
“What?” I’m kind of disappointed that he didn’t tell me. “How did you get the rod then?”
“You three aren’t the most observant.” Isabel made a slight frown. “No offense.”
“Well, what happens now?”
“I took it, but I think you should have it for the last few days. I’ll deal with Marcy and I’ll still set you up for the exchange, but there can’t be any more fuckups.”
“We’ll use it carefully.” She reached for the rod, but Isabel snatched it back.
“I don’t want him using this anymore. Only you make commands now.” Isabel watched her for a moment. “I command you to remember all of the commands you’ve been given… and ignore them.”
 
Ashley’s eyes darkened as the memories came back. “He commanded me to be a slut.” Tears formed as she looked to the ground. “Why did I… Oh god I had sex with so many… And he was my first. Jack fucked me and then ignored me and made me be a slut!” Her despair switched to anger and then desperation. “Isabel, you have to make me forget!”
 
The austere woman put a hand on her pregnant belly, thinking back to her own experiences. “No, you should remember what he did to you. It will help you be a better person. Learn from the past.” She placed the command rod in her hands. “You have one week to sever all outside ties and finish your request lists. Once I return you won’t be able to use this again.” Isabel looked into her eyes for a time, checking for understanding.
 
Ashley nodded finally, sniffling as she wiped away tears. “You’ll try to do whatever we ask?”
“I’ll do what I can, yes.”
“Thank you. Thank you for giving us so much time.” With that Isabel turned and left her to decide what to do for the remaining week.