Taking Max’s anal virginity

“Now, turn to your back.” Kyle ordered.

“As you wish, my handsome.” Max chuckled doing as what her lover told.

“Good girl.”

Max is lying on her front exposing her entire back and rear to Kyle.

Kyle gulped at the sight, a sight that he will never get tired of. He gently run his fingers through her smooth back, sending chills down her spine until it reaches her firm ass. He cupped and rubbed Max’s ass, then gave it a playful smack. It was not hard yet still enough to left a light red handprint on her cheek.

Kyle continued to trail down her skin, this time reaching her thighs. He grabs hold of both of her legs and gently spread them apart, exposing her still glistering wet folds. He run his fingers between her slit, teasing her a bit.

“A-a-h ah Kyle. Baby!” Max cried out body shaking a little. Seems that her pussy is still sensitive as she still hasn’t recovered from Chloe’s cunnilingus session yet.

Kyle moved, kneeling between Max’s legs and placed both hands each on her Max cheeks. He slowly spread them apart revealing his prize. Her untouched puckering asshole. Kyle could feel his erection becoming harder and harder with each passing minute. He swallowed his saliva and continued.

He lowered himself and pressed his tongue onto her asshole.

Max’s entire body shuddered as she felt something wet along with something hot pressed and breathed against her asshole.

“Ah Kyle what are you doing?!” Max moaned out. Is he going to fuck her in the ass?

Kyle didn’t answer, he instead continued spreading Max’s cheeks probing his tongue into her asshole enjoying the feeling of her tight inner walls clenching and loosened against his tongue.

“Kyle please stop. It’s dirty over there!” Max continued to cry out.

Kyle pulled away from Max’s asshole now coated with his saliva.

“Nonsense, it’s not dirty at all.”

“You sure?”

“I’m sure Maxie.” Kyle reassured her. “But sweetie. Before we continue, I had something that I would like to ask.”

“What is it, baby?”

“Do you trust me?

“Of course I do. Why do you ask?” Max raised an eyebrow.

“Because this is going to hurt a lot.” Kyle said. “But we can stop anytime if we want to.” He added.

“No, I trust you Kyle. I want to do this.” Max turned at looked at Kyle. “I really want to do this. I’m ready.” Max continued.

Kyle nodded. “Let’s get you loosen up a little then.”

Max retracted her legs into a kneeling position arching her back up presenting her ass to Kyle similar to what Chloe did, but Max was a little stiff compared to her.

Kyle trailed his finger around Max’s asshole, her sensitive asshole clenched and puckered as he touched her.

“Kyle stop teasing me!” Max muttered.

“Hey, just relax and take it easy, I’m just trying to loosen you up.” Kyle explained, he inserts a finger inside and Max gasped. He inserts another slowly probing her feeling her tight inner walls clenching and sucking against his fingers just as it did as its with his tongue.

Max slowly breathed heavily and lets out several small moans as he his thrust his fingers in and out of her. She was enjoying it and starting to get used to his fingers inside of her.

“Kyle, I’m not sure what is happening but I’m feeling a little weird.” Max said.

“I think it means that you’re ready.” Kyle replied. “Just try to relax, it will be ok but tell me if you want to stop.”

“Alright.”

Kyle pulled his fingers out from Max’s asshole. He looked around the bed and spotted the vibrator that he previously used in Chloe. He grabbed a bottle of lube and squeezed it onto Max ‘s asshole. Max’s body shivered as she felt the cool liquid made contact against her sensitive skin.

Kyle applied some of the lube onto the vibrator and placed it in front of her asshole. He activated the vibrator slowly pushing it into her. The vibrator easily slipped into her thanks to the lube. Kyle used the toy on her, earning several moans from her as the toy vibrates inside of her driving her crazy.

“Kyle I think I’m ready. Can you please stop?” Max said between her moans. “I can’t take it anymore.”

“As you wish.” He chucked pulling the toy out of her.

Just for more precaution, Kyle squeezed some more lube on her and some on his cock. Max took a deep breath as she felt Kyle’s cock pressed against her asshole.

“Max, one last time. This is going to hurt.” Kyle warned. “But just tell me if you want to stop anytime.”

“I know.” Max exhaled saying. “Let’s just get over with it.”

“Just try to relax.” Kyle rubbed her back trying his best to calm her down. Even so, Max could feel her heart beating rapidly. Max tried to control herself. She took one last deep breath and slowly exhaled, this time her heartbeat decreased and her asshole loosened.

Kyle siezed the opportunity, he spread her cheeks apart as widely as possible and pushed himself into Max, the head slipped into her asshole smoothly thanks to the lube.

“Oh!” Max breathed out as she felt her insides it tore open for the first time.

Kyle continued his push, it was tight just as Chloe’s and Kate’s but compared to his first time with Kate, it was definitely smoother thanks to the use of lube. Even so, it was still too much for Max.

Max’s hands bunched up against the sheets and gritted her teeth in pain as she felt Kyle’s entire length continuing its push. Finally, it stopped after reaching its end.

“Wowser!” Max unclenched her teeth exclaimed in pain.

Kate meanwhile was lying on the ground eating out Dana who is on top with her mouth still latched onto her pussy.

Kate glanced over the bed, she looked at Max and it reminded her of her first time trying out anal with Kyle, she wished she was there to help guiding and comforting Max but too bad she’s currently being occupied. All she can do is wishing Max all the best and pray for her.

“Max, are you alright?” Kyle asked. “Do you want me to stop?”

“No no it’s it’s ok.” Max breathed out.

Kyle leaned in a gave her a quick peck on her cheek earning a warm smile from her.

Kyle felt relieved after seeing her smile. He pulled and thrust inside her, gradually increasing his speed.

“Oh. Ah. Ow.” Max grunted as she felt her lover slowly increasing his speed. The pain was still there but she didn’t want it to stop. Eventually, with each thrust, the pain inside her subsided, with each thrust, the pain was gradually replaced with pleasure and finally with each thrust, her grunts slowly turned into moans.

Max lets out a pleasurable moan. Kyle knew it is time and he increased his speed even more, causing their flesh to slap against one another creating noises.

“Oh fuck!” Max moaned throwing her head up enjoying the new pleasure of her ass being fucked and Kyle’s balls slapping against her pussy. “Faster faster! Faster baby!” She continued to moan.

Kyle did as she told, increasing his speed like he previously did with both Chloe and Kate, the two continued for a few moments until he felt her inner walls clenching against him.

Kyle continued fucking Max hard, his hands gripping against her ass cheeks hard, leaving a deep red mark. Meanwhile Max continued to moan uncontrollably and loud, she couldn’t keep her voice down anymore. Her hands were clenching the sheets hard.

Suddenly, Kyle cried out again. “Maxie I’m cumming!”

“Do it! Cum inside my ass!” Max cried out.

Kyle continued his thrust, then with one final thrust, he buried his cock deep inside of Max and their bodies clenched together with Kyle shooting his hot white load inside of her while Max’s inner walls milked every single drop he had.

Kyle collapsed onto Max, his weight pressed against her small petite body, his head resting on her shoulder. Max too was exhausted, she lets her legs stretch out, her hands were on the pillows with Kyle’s hands above his. Max could feel his heartbeat and his cock still buried inside her ass.

“Oh god I’m cumming I’m going to cum!” Kate meanwhile cried out.

“Me too, I’m gonna cum too!” Dana moaned.

The two reached into their orgasm, spraying their juices onto each other’s face.

After her orgasm had subsided, Dana slowly got up and turned around. He collapsed onto Kate’s chest and wrapped her arms around her body.

“I think I’m going to need a time out before I could continue.” Kyle whispered into Max’s ear.

“Don’t worry baby.” Max turned around looking at her lover’s face. “Pretty sure everyone one here needs a time out.” She chuckled. She turned her head again this time looking at Kate and Dana. “Just look at them.”

Kyle slowly got up and looked towards Max’s direction. Kate and Dana were lying on the ground panting, with their bodies covered in sweat. They saw him and let out a weak smile waving at him.

Kyle smiled back nodding at them before collapsing back to Max.

“Yeah I think you’re right.” He chuckled.

Max smiled back and gave him a peck on his lips.