Cautious Smiles Ch. 03

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Chloe finds pleasure in anal sex.
1.1k words
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Part 3 of the 4 part series

Updated 10/09/2022
Created 09/19/2003
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"Bend over," Alex said forcefully as he moved toward the nightstand. Fumbling around for several moments he found what he was looking for; a new bottle of lubricant.

Chloe's eyes were wide with anticipation. She grinned when she saw the bottle in Alex's hand. "I'm already soaked," she coaxed.

"No more talking," Alex commanded as he knelt behind her on the bed. He loosened the cap before giving Chloe a firm swat on her bottom. Alex watched her creamy white skin slightly redden as he dripped a few drops of lube on his fingers. "All I want to hear from you are yes or no answers from this point on," Alex said with conviction. "I want your ass lower."

Looking back at Alex curiously, Chloe crouched closer to the bed.

"That's good," Alex said as he began to stroke his cock with his un-lubricated hand. "You're so beautiful," he said as rubbed the head of his cock against her pussy. "I love your ass," Alex moaned as the tip of his cock slid between her lips.

Chloe breathed heavily as Alex took his time teasing her. She rocked her hips back trying to precipitate insertion.

Alex pulled away. "I have plans, you'll have to wait," he said teasingly before slamming his cock into her. Throbbing, Alex thrust his cock further, leaving it there as Chloe squirmed and moaned in pleasure. "Is this what you want sweet girl?"

"Yes," Chloe purred as she began to move back and forth, fucking his cock. She laid her head on the bed and raised her ass higher as she squeezed his cock with her tight pussy.

Alex watched his glistening cock slide in and out. Grasping her waist with his left hand, he ran his lubricated index finger along her puckered anus. Slowly, Alex inserted his fingertip into ass. "Does that feel good sweet girl?"

Chloe moaned as her pace picked up and her breaths quickened. Diligently, Alex worked his finger through the clasped bands of muscle deep into her anus. His eyes rolled back thinking of his cock sliding into her ass. The sensation of her pussy dripping onto his balls made him open his eyes and pull out, letting out a sigh. Finger still inserted Alex asked, "Have you ever had anal sex?"

Catching her breath, she turned and looked at Alex while biting her lip. "No," she said inquisitively.

Looking into her eyes, Alex withdrew his index finger and began to insert his middle and index fingertips into her ass. Chloe closed her eyes, enjoying the attention. It was an unusual feeling, but highly pleasurable. Anal sex was something that Chloe had convinced herself that she was not interested in, but what Alex was doing felt good. If there was someone that she would allow to try it with her, it was him; a fantastic teacher.

"Lay down." Alex said as he grabbed the lubrication. Chloe again followed instructions and laid on her stomach. Taking his time, Alex had Chloe relax as he fingered and stretched her anus little by little until he could insert both fingers with ease. He moved his fingers open and shut like scissors, stretching out the bands of muscle so that she could accommodate his cock. Alex stroked himself, getting well lubricated while fingering her ass. "On your knees," he said as he moved behind her.

Alex could feel Chloe's body tense as his cock pushed against her anus. "Relax and take a deep breath," he told her as he pushed a little further. Her ass was so tight, Alex tried to maintain his arousal and take it slow. "Does it hurt?" he asked.

"No," Chloe said while breathing in. She pressed back against him letting him know it was okay to explore deeper although she had apprehensions.

The tip of Alex's cock was not much more than an inch deep when he got the urge to grab her hips and fuck her hard. Her ass felt too good for him to be so patient. He slid the tip in and out several times. "When I push in I want you to push out, okay?"

With her hands grabbing the sheets, she felt his cock pushing deeper. As told Chloe pushed out as half of Alex's cock made its way inside. Chloe's body tensed up against her will, not allowing Alex to move any further.

"It's okay sweet girl," he said allowing her to get use to the fullness in her ass. Her body clenched down on his cock making it hard for him not to fill her right then. Alex massaged her ass and rubbed her lower back trying to calm her. He pulsed inside until her body relaxed. Again he pressed into her ass finally being able to fully penetrate her. Alex let out an anguished sigh as he slowly fucked her.

Chloe was overwhelmed with sensations she had never felt. She almost could not believe how much she enjoyed having her ass fucked. Chloe could hear the pleasure Alex was having and that alone made her arousal peak. She loved pleasing him. Alex was on the verge of climaxing, but tried to hold back.

Both over indulged with pleasure, Alex fucked her ass harder. He pulled her hair as she arched her back. "Fuck," Alex yelled as he grabbed her waist and slammed his balls against her dripping pussy. "I'm going to fill you, isn't that what you want, for me to fill every hole with cum?"

"Mmmmmmm…..yes….," Chloe could barely spit out as Alex grabbed her hips and plunged his cock as far as it could go. With the base clenched, his cock immersed, he erupted squirting thick hot cum.

Feeling her ass being filled, Chloe sighed as Alex finished and pulled out. Giddy and a bit lightheaded, Alex sat on the edge of the bed looking at Chloe's ass still in the air with a tiny bit of cum coming out. With a smile Alex said thoughtfully, "Sweet girl, I haven't made you cum."

Chloe laughed as she laid down on the bed and rolled to face him. "I'm alright really. I had a lot of fun."

"Come here, let me eat your pussy," Alex goaded.

"You want to eat my pussy while your cum drips out of my ass," she giggled as he pushed her down onto her back staring at her perky breasts.

"Mmm…Hmmm…," Alex said as he spread her legs gazing at her wet pussy.

"You're a dirty man," Chloe said playfully as Alex lowered his head above her clit.

"Mmm…Hmmm...," Alex hummed as his tongue licked the sweet juices of her pussy. "I can be very, very dirty sweet girl," Alex said looking up at Chloe with a grin. "You'll see."

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