Working In and Out Ch. 07

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Riley tries his hand at swimming.
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Part 7 of the 7 part series

Updated 01/22/2024
Created 10/06/2023
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Working In and Out (Chapter 7: Swimming Lesson)

Riley was laying on his belly, his ass up and glistening as he turned a bit and looked at the little hut where the sound was originating from. He saw the attendant loudly arguing with two very voluptuous futa. The black one had long pink hair and was wearing a white top that looked like it would explode at any moment and expose her massive tits. Her tight little panties were just barely covering her ass and not covering her big cock at all. The white one wore a set of matching red top and bottom. Her top was so small part of her nipples were clearly visible, and her bottom, much like her friends, was doing almost nothing at all. Riley considered walking over to see what was happening and if he could resolve the issue in some way. But the combination of the warm sun, him already laying down and the fact that he was so lazy he decided not to get into it. He did however try to focus on what they were saying. It became pretty clear the attendant didn't want them cumming everywhere while the two defended their actions and what they were wearing. It seemed they finally reached some point of resolution and slowly started walking towards Riley who quickly turned his head down, pretending he wasn't prying.

He closed his eyes and could hear them slowly walk over to him. He could hear them whispering and giggling before sitting down on the chairs next to him. He let out a little sigh, now more relaxed, suddenly he felt a little poke on the side of his left cheek and he shot his head up.

"Huh?" He looked at the black futa who was covering her mouth as she giggled.

"I- I'm sorry. It's just that, there's something between your cheeks." She smiled as she pointed to it.

"Oh, uh thank you. Can you tell what it is?"

"Umm yeah, I think its cum." She tried her best to hold back her laughter as her friend was now giggling too.

"Here take this!" Her friend reached forward to Riley, handing him a small rag.

Riley blushed as he took it and quickly stuck it between his cheeks and wiped away all the cum he could. He looked at the rag as he sat up, now blushing even more as he didn't really know what to do with it.

"It's okay, you can just keep it!" The futa replied as she also sat up behind him. "I'm Lina!"

The black futa, now able to control her giggling also added "and I'm Haily!"

"Thanks for the help. That could have been very embarrassing. I'm Ri-" before he could finish introducing himself he was cut off.

"Oh, we know who you are! You're Riley! You worked out with Macy" They both laughed, although it seemed more genuine than mocking.

"Oh, uhm, you saw that huh?" Riley blushed.

"Are you kidding me!? It's the whole reason we joined!" Hailey laughed out loud.

"So, are you going to swim today?" Lina chimed in, noticing how Riley was getting awkward.

"Yeah yeah! But I'm going to stick to the shallow side, I'm not too good once I get into the deeper water."

"I can help you! I think everyone should know how to swim in deep water, it could save your life!"

Before Riley could respond, Lina took his hand and walked him over to the shallow side. Haily watched as they both slowly got in. She jumped into the deeper side and was quickly below the water. Riley watched her getting comfortable in the water as Lina grabbed him by the waist and pulled him further. The cold water made Riley shiver as he slowly floated above the water not wanting to go further.

"Feeling scared?" Lina giggled as she looked back at him.

"A little. Cold as well." Riley mumbled as he clenched his chest.

"Don't worry, I'll be right behind you!" Lina smiled as she waddled her way behind Riley.

Riley could feel her warm cock rubbing against his back. He felt a bit better as he looked around at the hut. The attendant clearly angry, knowing what was about to happen. Lina embraced him, resting her breasts on his shoulders and leaning forward to whisper.

"Feeling warmer?"

"Y-ye-yes" Riley whispered back.

Lina slowly began walking towards the deeper side, holding Riley. Riley could feel his tiny little cock get hard in the cage as her cock throbbed against his back. He could still feel the cold tile on the pool floor, but it was getting deeper. Hailey had seen enough and swam over to both of them, confused and aroused at how close they were.

"What happened? What's with the hug?"

"Just helping our friend here get comfortable, he was felling a bit cold." Lina giggled a bit as she winked at her friend.

"Oh! Let me help then!" Hailey smiled as she moved forward and hugged Riley as well.

Riley rubbed his face against her breasts as he now felt much warmer. Suddenly he felt Hailey grabbing his waist and rubbing his hips and thighs. He blushed as he felt her slowly rubbing and squeezing his ass cheeks.

"You know there are other ways to get warmer." Hailey whispered into his ear with a smile.

She grabbed his cheeks and slid a finger into his ass. Riley shook his body, but it was pointless as both had a good grasp around him. Riley let out little moans as Hailey stares at him with a wide grin. She pulled him up a bit as Lina helped and slowly slid her cock into his ass. Riley was already well above the water. Hailey giggled as she saw his tiny little caged cock and seeing how Lina was already holding him up, she reached up and grabbed it with just her finger and thumb and laughed out loud. Lina smiled as she began to slowly lower him. She was letting out little moans as her cock slowly made its way inside him.

"Wow this bitch s tight!" Lina giggled to Hailey.

"And tiny too!" Hailey laughed as she played with his little balls.

"Now let's get you further into the water. Hope you stay warmer now!" Lina giggled as she began to slowly let go as her full cock was now inside him.

She took a couple of steps towards the deeper side as Haily swam alongside them for a few steps, but seeing how they had a hang of it now, she swam to the other end. Riley couldn't feel the floor at all and was kicking his feet around to stay afloat. He felt Lina slowly let go of his legs and ass and slowly move her hands up to play and pull his nipples. Haily laughed as she now sat at the edge of the pool kicking the water. Her cock was hard but clearly not fully as t hung over the water, dripping pre cum as she watched the show. Riley watched her as he gasped for air, barely able to keep afloat. The only thing now holding him up were Lina's cock and his feet kicking the water. He shook his arms and tried to swim away but Lina's grip would only strengthen as he tried to get away. Lina smiled watching him squirming and trying to get away. She walked over, now on the deepest side, she began kicking up as well and slowly swam over to her friend and rested by the edge next to her.

"See! You're kicking around so well; you'll learn how to swim just like that!" Lina giggled as Hailey pet his head.

"Let's see how well he can do." Hailey smiled as she grabbed him under the arms as Lina slowly pulled him off.

Riley was cumming as he felt Lina's cock slowly pulling out of him. It throbbed and rubbed against his inner walls. He waved his arms around and forward until he finally grabbed the edge and was pulled off. Lina laughed as she sat next to her friend, Riley hugging the edge between them and huffing.

"Well we still should test you!" Hailey laughed as she grabbed both his hands and peeled them of the edge and licked him towards the deeper side.

Riley panicked and started kicking and shaking his arms trying not to drown.

"Just calm down and focus!" Lina snickered as they both watched him struggling to stay afloat.

Pretty soon the waves and splashes of water died down and Riley was now paddling his hands and legs, more confident and swimming.

"Now! Was that really that bad? You can stay afloat now!" Lina laughed as she watched him and leaned over to Hailey.

"Ya- Yeah! I can finally do it!" Riley exclaimed with joy as he slowly swam towards them.

"Now let's see how well you can hold your breath!" laughed Hailey as she jumped into the water in front of him.

Before Riley could grab the edge Hailey held her breath and dove under water. She saw him swimming above her and grabbed him by the leg, pulling him down under the water. She watched his panicked face as she ripped of her bottom, letting her cock fully hang out and get more comfortable. She grabbed his head and pulled it over onto her cock. While initially scared, Riley was still a good slut, and seeing what was about to happen, he calmed down and grabbed her cock, shoving it into his mouth. She grinned as she swam up and pulled her head out of the water, still feeling his warm lips and throat working its magic on her cock. She relaxed and spread her arms around the edge and closed her eyes. Riley was still under water but his ass was still floating up as he now grabbed her waist and started sucking her down deeper than before. Hailey smiled as she looked at Lina, both realizing what a good little slut they had found. Suddenly Riley pulled out Haileys cock and swam up. He took a deep breathe followed by small pants. He was still holding her cock as both watched him. Now still swimming he put her cock back into his mouth and sucking it down his throat. Hailey giggled and pet his head.

"Wow! You're doing so well; I think we need some rest from the swimming." Lina smiled as she stood up

"Yeah, I'm tired of kicking so much!" Hailey smiled as well, pulling Riley of her dick and grabbing the ladder to get up.

Riley followed behind them and got out. They walked towards the chair and Lina sat down, her cock fully erect as she clearly was not don't just yet. Hailey was about to sit in front of her, but Riley was also clearly not done and sat on her chair. He sat on all fours as he grabbed Lina's cock with his lips and started licking it. Hailey smiled as she walked behind him, admiring the view of Riley's ass and little caged cock hanging below. She grabbed his cheeks and pulled them apart, sticking her tongue into his still gaping hole, tasting her friends precum. Lina was letting out soft moans as Riley's lips went further, his lips licking her shaft and his throat slowly tightening around her cock as it went deeper inside him. Hailey smiled as she began moaning as well, sticking her tongue deep into his hole and swirling it around before pulling out and wiping her mouth with her forearm.

"Fuck! This bitch is too horny!"

Lina just moaned in response as Hailey lined up her cock against his ass hole and slowly entered him. Lina was leaking precum as she watched her friend grip onto Riley's waist. Hailey was going deeper and deeper until her cock finally bottomed out and her hips rubbed against his soft ass cheeks. Hailey began thrusting back and forth, slowly slamming into him and shoving her cock into him. Riley moaned as he took Lina's cock fully inside him. He felt her balls on his chin and began to move back and forth with Hailey's movements. Lina began moaning louder now and so did Hailey. Riley closed his eyes as his cage began leaking. He felt both cocks touching against each other inside him. Hailey smiled while panting as she rubbed her cock against her friends inside the sissy little slut. The cocks throbbed for a few more seconds before finally exploding inside him and filling him up, making his belly swell up with their cum. Both futas panted heavily as the were finally done. Lina gently grabbed his head and pulled out her cock.

"Wow, he's such a good slut." She smiled at Hailey. "Don't pull out just yet! He'll leak all over the floor!"

"What do we do!?" Hailey panicked a bit as she could still feel his insides squishing her cock.

"Well, he does know how to swim right? Lets just throw him in the pool."

"Good idea! Grab his arms!"

Hailey flipped him around as she looked at her cock still stuffing his tight ass pussy, and his perfect sissy body, hard nipples, tiny caged cock and pregnant looking belly. Lina grabbed his arms as Riley was still in a state of ecstasy. They waddled over to the edge and started swinging him.

"One. Two. Three!" They both yelled together.

Haileys cock was yanked out of Riley's ass and he was suddenly plunged into the water. The futas laughed and giggled as they began to walk away.

"This is your final test, lets see you swim and get out!"

Riley struggled and splashed as the cum in his belly slowly leaked out of his ass into the water. It took him a minute but he finally got a hold of himself and was finally able to swim up. Still tired from the fucking and the swimming, he just barely reached the edge and grabbed it tightly. He took a deep breath but before he could pull himself up, he realized he was staring at someone's feet. He looked up to see the attendant. Her cock was hanging just above his head, holding a net and a very angry face.

"You dumb little slut! Look at the mess you made!"

Riley wiped the water from his face and looked back at the pool and how there was a thick layer cum on the top. He turned back bright red from embarrassment.

"S-sorry, I didn't mean to."

"Uh huh! I bet you didn't!" She got lower and grabbed her cock, using it to smack his face. "Now you are going to clean this up!" As she smacked him again and again until she got hard. "And when you're done I'll be checking your work!"

Riley got out of the water and she shoved the special cum catching net into his hands and walked back to the hut. Riley quietly began cleaning the cum. Every now and again he would reach out, dipping his finger into it and tasting how the special cum only pulled out the cum. It took him almost two hours to finally get everything cleaned up. The sun was setting as he walked back to the hut. The attendant saw him coming and got out, inspecting everything with a blue light to make sure he didn't miss a spot. Even though it was completely clean she was still angry.

"Well, it's clean, but I think you still need to be punished!" She said angrily as she grabbed the net from him.

She grabbed his cage and started walking, pulling him along as he tried his best to keep up. She enter the huts back and placed the net in a locker while still holding his cage. She sat on a chair and pulled him over her lap. He blushed as he felt her cock sticking against his belly. She started spanking him on his bubbly cheeks.

"Bad slut! Don't do that again! Bad slut!" She yelled angrily as Riley yelped with each smack.

"Please! I'm sorry!" Riley begged.

"No! You've been a dirty slut!" She yelled and kept smacking his ass. "I'll glue your ass hole shut if you ever do this again!"

"Ow! Please! Stop! I won't!"

"I'm sure you won't! Now get on that table!"

Riley obediently got off of her lap and walked over to the tall table. It was difficult for him to get on top off and as he bent over to get on top, the attendant quickly grabbed his waist. She shoved her cock fully inside him and started slamming against his backside. Riley moaned as he clung onto the table for support but as she continued to ram him his feet got lifted off the ground. She continued to slam into him while gritting her teeth angrily fucking him until she felt she was about to cum. She quickly pulled out and let him drop to the floor. She stood above him, feet on either side and pointed her cock down as she quickly began rubbing it. As she huffed, she released her cum on his face and body. She panted slowly as she grabbed the table for support.

"I better not see you dirtying up that pool again!" She was still a bit angry but watching Hailey and Lina had clearly made her horny.

She leaned down and pulled out a key from her shirt pocket. She unlocked the cage, releasing his dirty wet little cock. She let him get up himself and ripped the top off of him. She pushed him out completely naked and covered in cum and locked the hut door. Riley walked to the front where the changing room and bathrooms were. He quickly showered, still tired and ordered a cab as he changed back into his clothes. He got into the car and reached home, passing out nearly instantly as he reached his bed.

He thought to himself, "Hopefully tomorrow will be a better day."

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