The One Night Stand Ch. 04

The One Night Stand (Chapter 4: One Year Anniversary)

Fast forward to two years later. Riley has been under training and performing really well

It had been two years since Riley was under the tutelage of Naomi. He had undergone many different changes, not just mentally but physically as well. He had always been a little slutty while maintaining a shy demeanor. He was now not only more depraved, but also more subservient and uninhibited. He still had a softer more loving side when he was alone with Naomi.

The sun rose and shined a beam of light through the chink in the curtains of Riley's curtains. His eyes fluttered open as he held Naomi in his arms. Her bare breasts in his face, her taut nipple in his mouth as his lips slowly closed around her rather large areolas. He smirked a little as his eyes fully opened and he looked up to Naomi's gorgeous face as she still slept. Her lips full red lips slightly ajar, her rosy red cheeks, her wild lustrous blonde hair and elegant nose all glowed like that of a radiant goddess as the rays from the sun slowly draped her in light. Riley stared up at her with her nipple still in his mouth as his embrace tightened. She slowly lifted her eye lids and looked up at the roof before looking down at her pet.

"I see someone is already awake?" She seemed a bit annoyed.

"Mhmm" Riley nodded as he kept her tit in his mouth.

"Why are you in the bed? And that too... so close?"

"I- I was feeling lonely." He murmured, finally letting go of her chest.

"Awww, well you're still in training so its okay!" She grinned as she pet his head and then moved her hand down as she hugged him back.

Riley had her nipple back in his mouth as he lifted his leg and put it over her. His tiny little cage tapping against her hard cock between both of them.

"Someone's hard already?" Riley giggled as he lowered his hand, running his finger over her shaft, feeling her morning wood throbbing against his hand.

"And whose fault is that!" Naomi chuckled loudly as she leaned back, letting her cock slink between both of them.

"I can take care of it!"

"Good girl!"

Riley smiled as he let go of her and sat up. Naomi moved so her hard cock was pointing directly at the roof, fully erect. Riley pulled back his hair as he sat on her thighs and leaned down with his mouth open. Naomi let out a soft moan as she felt his warm wet tongue lick her glans. Riley smiled as he gave her another lick, and then another, teasing her with his tongue. She let out another moan before spreading her legs a bit more to free up her heavy balls. Riley slowly placed her tip in his mouth, then letting go to lick her shaft. His tongue followed the shaft from tip to base without breaking contact. His hands gently playing with her balls until he began to lick them. He laid down on the bed as she spread her legs further. He sucked in her left ball as one hand gripped her thick shaft and the other hand gripped onto her pillowy thighs. She could feel his tongue licking her ball in his mouth, going through each nook and cranny. She placed both her hands on his head as she pulled him further. He let go of the now sloppy wet ball and sucked in the other, giving it the same treatment. His lips rubbed against her balls as his hand continued to rub and massage her cock. She grabbed his face and pulled him up with ease as she let her cock slide directly into his mouth. Riley smiled knowing he was doing a good job. He sucked her cock into his mouth and grabbed her thighs with each hand. He started bobbing his head up and down, letting her cock go deeper each time until it entered his throat. Naomi let go of his head as she grabbed the sheets, almost ready to cum. Riley was drooling on her cock as he choked on it, barely able to breathe. Before he could go any further Naomi let out a little yelp and began huffing as she began to pump her full of her cum. She began to hump his mouth as her fingers dug into the bed. She panted heavily as she completely unloaded her seed. The pressure from it was too much for Riley who got pushed off and got a face full of her cum.

"Was I good?" Riley murmured as he wiped the cum away.

"Well, you were better than before." She huffed and caught her breathe, "would be better if you could keep it down."

"I'm sorry, I was hoping I could too." Riley blushed as he felt embarrassed.

"Awww, don't worry baby! You'll get better!" She smiled as she pet his head and laughed. "After all, today is a special day." She giggled as she sat up, shoving her foot in his face.

Riley was a bit con fused as he began to give her a foot rub. He noticed her new anklet which had a key attached to it. "What's so special about today?"

"You really don't know?" Naomi said a bit disappointed.

"N-no, should I?"

"Hmmm, maybe that's a good thing."

"Come on now! You have to tell me now; you can't just half tell me!"

"Wow! You really don't know!?"

Riley thought for a few seconds, "it's definitely not your birthday, or mine. It's also not Valentine's day or Goddess day." Riley was stumped and embarrassed.

"Oh, this is great!" Naomi gleefully smiled. "It means the training is working well!"

"What is it! Tell me!" Riley was growing impatient and more embarrassed by the second.

"Silly! It's the one-year anniversary of your cage being put on!" Naomi smiled, "I was thinking we could even let you free for a while, amongst other activities."

"Really?" Riley was a bit astonished and a little unsure if he even wanted that now.

"Would you like that?" Naomi inquired, waiting eagerly for his reaction.

"I- I don't know, I guess, maybe?" Riley thought about it a bit confused as he continued to massage her foot.

"Hmmm, lets see how you feel later." She seemed a bit disappointed as she freed her foot from her grasp. "But first, I need to test you."

"Yes! Yes of course!" Riley's demeanor suddenly changed as he quickly laid on the bed and spread his legs.

"Good good! Now what is this?" She said as she next to him, poking his cage.

"This is my clitty!"

"Good, and what is its purpose?"

"It is useless! It's only function is to show everyone that I have sissygasmed!"

"Very nice! And what is this?" She grinned as she poked his belly.

"This is my womb, it is storage for all the cum I eat."

"Correct! Now lift up your legs!"

Riley obediently lifted his legs showing of his hole by pulling his cheeks apart.

"And what are these two?" she said as she spanked both his ass cheeks simultaneously.

"These are my clappers!"

"And their purpose...?"

"Too cushion whoever uses me and make massage them at the same time."

"Very good! Someone's been doing their homework!" Naomi grinned as she pushed his legs further back and stuck a finger in his ass, "What is this?"

"This is my assho-" He realized instantly that he had made a mistake.

"No! Wrong! This is your pussy! I guess training still isn't there yet. You need some punishment!"

"I'm sorry! I didn't mean to!" Riley protested but they fell on deaf ears.

"I know I know, but we have to make sure you learn your lesson!" Naomi said in cold-blooded tone as she grabbed his hands and tied them to the bed. "Now, what do we say?"

"Please mistress Naomi, please fuck me for my stupid mistake!" Riley almost yelled as he looked down at her rubbing her cock with lube.

"Good, and what do you want from me?"

"I want your glorious futa cum inside me, I want it to fill me up and make me pregnant!"

"Very good!" She gently lifted one of his legs as she rubbed her tip against his hole, slowly letting just her tip go inside his hole. "And why do you want it?"

"Because I'm a slut and all I want is cum!" Riley moaned as he felt it enter, his cage already leaking precum.

"Well, you did a good enough job, so I'll be gentler." Naomi grinned as she began to slowly move her cock inside.

Riley moaned as he felt it going deeper. He tried to pull his hands to his chest but they were kept tightly in place as Naomi watched him and roared with laughter. She began humping him, making small jerks back and forth, but making sure her cock would go deeper with each thrust. Riley struggled as his moans became louder and he could feel his hole becoming numb as she became faster. Her cock slid deeper, pushing against his inner walls and prostate. She grinned as she grabbed his caged cock.

"Is the useless whore feeling good?" She pulled the cage while grinning and looking into his eye.

"Yes, I love your cock! Please fuck me harder and fill me with your seed!"

"Good slut!" She moaned as she became faster.

The whole bed shook as Riley's began huffing and leaking cum from his cage, spilling some onto her hand as his toes curled. Naomi grabbed his legs, digging her nails into them to make sure he didn't try and close them. Riley's eyes closed tightly as her cock was now fully inside her. He could feel her hips slamming his cheeks as she lifted him up a bit. Riley began drooling as he could feel like he was losing control of his mind, lost in the ecstasy of her movements. She grinned as she began to pant as well, her cock throbbing inside the tight hole, ready explode. She leaned forward, and kissed his lips before biting his lower lip.

"What are you?" Naomi moaned as her thrusts reached her peak.

"I'm a whore! A good little whore! I love Mistress Naomi's cum! I love it when it fills me up and makes me look pregnant!" He moaned

"Good. Little. Slut!" Naomi groaned as she unloaded inside him for the second time this morning.

Riley panted as he felt the warm familiar sensation of Naomi's cum flooding his insides. He pulled his hands with all his might as his body slowly absorbed as much as it could. He could still feel her cock inside him, even though his entire lower body felt numb. He felt it get softer as looked down at her huffing. She finally pulled out with a satisfying pop sound.

"Wow! Always a bit too tight. I think we should move to the next step of your training!"

"Really? You think I'm ready?"

"Well, I did get you this as a gift for this special day anyway! Hahaha!" She laughed as she got up, her flaccid cock swaying beneath her. She pulled out a bag from behind his dresser and pulled out the Jewel® butt plug. "This should be a good starter!"

Riley smiled as he spread his legs, still tied up. Naomi gripped his thigh as she easily slid it into his still gaping hole.

"I think your ass is still sore, I'll let you heal. I'm just going to shower." She smiled as she stared at his new plug loosely stuck in his ass. She leaned forward, hovering her hand above his mouth. Riley eagerly licked up his own cum from her hand. "Good slut!"

She smiled as she left him there, tied up and covered in cum with a buttplug in his ass. She went into the bathroom to shower. Riley regained his breathe and looked to the bathroom door. He could hear the water hitting the floor as it poured off of her body. Just the thought was enough to arouse him. He wanted more than anything to just rush into the bathroom and help her in bathing like a good slave. He tugged his arms to get free but there was no chance, Naomi made sure of it. He continued to struggle for a few more minutes before giving up and excepting his position. Eventually he heard the sound of the tap being turned and then jus the sound of water draining. He could hear the gentle sound of her nimble feet gently moving across the room, putting on clothes and getting ready. Riley looked up as he waited for her to come out and free him, or really do whatever she wanted, he was completely a slave to her. He closed his eyes and focused on trying to hear her movements, meanwhile his asshole was returning to its original form as it tightened around his new butt plug. He suddenly opened his eyes and turned his head as he heard the sound of the door knob turning.

"Since you've been such a good boy, lets go for a walk!" She smiled as she stood in the door, wearing a pair of sweatpants, a tight shirt and a jacket over it, while holding a pink collar and leash.

"Yes! I'd love too!" Riley smiled eagerly as his tiny little cock got hard.

"Like that?"

"What do you mean?"

"Well, if you're going to be seen with me in public, you'll have to look and act the part of course."

"Does that mean new clothes?!"

"Obviously" She smiled as she leaned down and freed him. "And since you are going to be on a leash, like a little bitch, I'll be expecting you to act like one too?"

"Like, woof woof?" Riley asked a bit confused.

"Exactly!" She exclaimed as she pet his head, "Good boy!"

"Woof! Woof!" Riley barked as he sat up with a smile.

"Hahaha! Good boy!" She giggled as she tussled his hair and clicked on the pink collar. She ran her finger through it and pulled him up off the bed and went over to his dresser. "Now what should we wear today?"

Riley, being a good little bitch got on his hands and knees and looked up at her as she went through his clothes, throwing the ones she didn't like here and there. She finally pulled out a tight pink top, the bottoms of a pink lingerie, long pink socks and a pink beanie.

"This! This should look good on you!" She grins as she turns around and forcibly dresses him up.

"A-are you sure? It's a bit revealing." Riley blushes as he looks down at his tiny caged cock clearly visible and sticking out.

"Hey! Did I just hear words come out of your mouth!?" Naomi yelled as she gave his ass a hard, strong spank.

"Woof!" Riley blushed as he felt his ass jiggling from her spank. He got turned on as she humiliated him and even leaked a bit of precum.

"Oh wow! Your clitty is already leaking! So cute!" She tugged his leash as she headed out the door. "Come on now! Let's go to the park!"

Riley followed behind her, he was allowed to stay on two feet since this would be the best way to show off his little clitty. Naomi stopped at a café first to grab herself an ice tea to go. As they wait, she makes sure she pulls Riley down onto the floor to make sure everyone could see what a good obedient little bitch he was. Plenty of people got a good view and laugh out of seeing the little sissy following behind the clearly much larger futa. Naomi and Riley even took selfies with some people as she made Riley spread his legs and show everyone his tiny little clitty. She walked out proud of how well training was going, meanwhile Riley was still blushing bright red as he walked behind her all the way to the park. Naomi walked past plenty of people who enjoyed the view. They walked to the middle of the park which had some benches and plenty of greenery. Naomi sat on the edge of one and sighed as she looked up at the sun.

"Its so sunny today! What do you think?" She grinned as she looked at Riley.

"Woof! Woof!" Riley gleefully barked as he sat next to her on the bench.

"Hey! No! Bad bitch!" Naomi quickly smacked his ass just as he was about to sit down. "Good bitches sit by their owners' feet!"

"Woof!" Riley responded quickly and got on his knees and sat close enough to rest his head on her lap.

Naomi smiled and ran her fingers through his hair, gently playing and tussling it as she sipped her drink. As they enjoyed their time together, they were approached by a jogger. She had clearly worked up quite a sweat as her clothes were soaked. Her cock bulge was also poking out and was more than visible.

"Hi there! I'm Gwen!" She greeted Naomi as she stuck out her hand, still a bit out of breath.

"Nice to meet you! I'm Naomi." She grabbed her hand and shook it as she took another sip.

"And who's this little guy!?" She leaned over and pet Riley's head.

"Woof! Woof!" Riley stuck out his tongue and smiled as he was pet.

"I'm guessing you're here to train this little guy?"

"Hahaha! Is it that obvious?"

"Yeah, hahaha, it happens here fairly often."

"Well, he is pretty well trained, but we're still working out some kinks."

"Oh? Could I be of any assistance?"

"Hmmm" Naomi's gaze went down to the obvious bulge, "I'm guessing you have a bit of a problem that needs to be taken care of?" Naomi smirks as she turns to look to Riley who has also sensed the situation.

"You got me! I figured he could learn more about musk and I could get some... relief." She blushed a bit, not knowing what to expect.

"Woof!"

Naomi suddenly looked at Riley, who was eagerly awaiting her response. "Well, I guess he likes you, so why not!" She smiled as she handed her the leash.

Gwen smiled as she on the same bench at the other end, pulling Riley forward between her legs. The potent scent of her cock made Riley instantly horny as he began kissing her bulge through her clothes.

"Oh wow! You've trained him so well!"

"Hahaha! Thanks! Getting the worship part was a bit difficult."

"Well, whatever you're doing, its working!" Gwen smiled as she lifted herself up a bit and pulled down her sweatpants, her balls were clearly full and her big cock was hanging just above them.

The musky smell quickly went through Riley's nose and penetrated his brain. He closed his eyes as he leaned down and began licking her balls. The instant his tongue touched her sack he could feel the sensational mixture of precum and sweat. He smiled as he grabbed her knees for support and began licking them up and down, sucking them but they were too big for him to suck into his mouth. Her sweaty moist cock rubbed his forehead as he looked up at the futa playing with her tits and huffing gently. Riley smiled as his tongue slowly made its way from her balls to the base of her cock. Naomi bit her lip as she watched the stranger and her pet going at it. Riley started moving his head back and forth as his tongue licked the whole cock from base to tip. He made sure it was nice and wet before he grabbed her cock and stuffed it into his mouth. Gwen let out a little yelp as she pulled her rather heavy breasts out and began playing with the nipples.

"Mhhmm! Good boy." Gwen moaned out as she pet his head.

Naomi had had enough of just watching and leaned forward, grabbing the jogger's breast and licking it, flicking the nipple with her tongue playfully as she grabbed her cock and started rubbing it. Riley was still on the ground, letting his throat open up as he pushed her cock down her throat. Naomi let go as Gwen moaned louder and louder with each one thrust of Riley on her cock. Naomi got up and took out her cock, and grabbing Riley by the waist, she pulled him up and gave his ass a good smack before pulling out the plug. And gently placed the tip of her cock on his hole. She looked up at the scene of Riley sucking Gwen's cock who was moaning and playing with her breasts. Naomi smiled as she slowly shoved her cock into Riley. His ass opened up and eagerly welcomed her cock. Naomi leaned forward as her cock was fully inside her and grabbed Riley by the chest as she started humping like a dog. Riley was leaking precum and moaning as he could feel Gwen's cock and Naomi's cock throbbing inside him. Naomi slowed down as she got closer and started thrusting slower, stronger and more deliberately. The thrusts made Gwen's full cock go down Riley's throat. He could feel her cock throbbing and the flow of cum move from her balls, which were rubbing against his lips, to her throbbing cock in his tight throat and explode inside him. Gwen moaned loudly and lewdly as Naomi grabbed him tightly as her cock slowly pumped cum into him. Gwen smiled and huffed as she pulled out her now flaccid cock and wiped the sweat from her forehead.

"Wow! He's such a good little slut!" She smiled, trying to catch her breathe.

"Th- thanks, Its nice to see how well he can handle two cocks." Naomi panted a bit as she slowly and carefully pulled out her cock, sliding the plug back in to make sure he kept her cum inside him.

"Woo. Oof." Riley moaned as he lay on the soft grass.