Her Mom's Hot Friend Ch. 02

Story Info
Robert gives Cara a lesson in anal pleasure.
1.6k words
4.2
71.2k
21

Part 2 of the 4 part series

Updated 10/30/2022
Created 06/26/2012
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Since the night she let Robert take her virginity, Cara began spending more time at his house over the summer during the times her mother was at work.

In spite of her being eighteen to his forty-two, they had a great time together even when sex wasn't involved.

Julie was pleased that Robert showed so much interest in her beautiful daughter and was pleased Cara would be spending the afternoon using his pool.

"Don't stay too long," Julie told her before leaving for work, "don't forget to use sunblock, and be sure to put back everything how you found it."

Cara rolled her eyes. "Yes, Mom!"

She waved as Julie drove away before heading over to Robert's to swim in his large pool. He'd gone to the gym to work out and wasn't expected home for at least another half an hour.

When she reached the entrance to his privacy fence, Cara was taken aback when she heard masculine groans coming from inside.

Curious, she opened the fence door until it was slightly ajar, and found Robert with another well-built male, both of them naked. Both lay together face down on a chaise lounge by the pool, with Robert on top of the other man.

From where she stood, Cara had a clear view of Robert thrusting in and out of the man who lay beneath him and heard both grunting practically in unison before the other man cried out, "Yeah....oh God, Rob, fuck me!"

"Your ass is so tight, Mark," Robert replied. "It feels so fucking good..."

Cara continued to watch in amazement as Robert reached down and stroked Mark's cock while he continued to fuck the other man's ass. Robert's thick shaft was stretching his hole to the limit as Mark got fucked hard by his workout buddy.

She knew about gays, but never actually saw two men having sex until that moment.

Wow, she thought, I'm certainly getting an education!

Cara became turned on by the scene unfolding in front of her as she watched Robert develop a powerful rhythm. Each of his thrusts in and out of Mark's asshole was harder than the last and she couldn't believe how much deeper Robert's cock went into him.

He pulled his hand off Mark's hard shaft, grabbed his hips, and pulled Mark toward him while he continued mercilessly pounding him.

"Oh, fuck, Mark, I'm going to come!"

Cara's mouth dropped open as she watched Robert pull out of Mark's ass and removed the condom. Mark rolled over onto his back and looked up at Robert, who stroked his shaft a few more times before his sperm covered Mark's face, neck, and chest.

Mark then took Robert's cock into his mouth and sucked him until Robert was drained. Robert then kneeled before Mark on the chaise lounge and proceeded to suck his cock and swallow Mark's entire load.

She watched the two men kiss and sit beside each other, clearly spent from the sex they'd just had. After several minutes of gathering her courage, Cara emerged from her hiding spot and walked inside the fence.

Before she had a chance to greet Robert, both men - now dressed - spied her. While Robert gave her a knowing smile, a spooked Mark quickly made his exit without a word.

"Liked what you saw, honey?" Robert asked once Mark was gone.

"What?"

"Ah, don't even try it. My man and I weren't the only ones who were breathing heavy."

Cara felt herself turn crimson. "Oh my God, Rob, I'm so..."

"No big deal. Question is, what did you think about seeing two men going at it?"

"I...uh..."

"It was his first time too."

"You mean..."

"Mark's gay, but lost a bet we'd made while at the gym, so his ass was mine, so to speak."

"Oh. Well, sorry I intruded. I wasn't expecting you back so soon."

He got up and came over to her. "That's what happens when a guy gets horny. Haven't I taught you enough about that?"

She gave him a lopsided smile. "Maybe, maybe not."

"Hmmm, then I guess it's time for another lesson, honey," he said.

He stepped up slipped one hand down the front of her bikini bottoms as they continued to kiss, and she was already wet. He brushed his fingers against her pussy lips and took one slowly up her slit to tease over her clitoris with a fingertip. Cara moaned and bucked her hips against his hand while he fingered her.

Robert took one of her hands and placed it on his crotch. She felt his erection through the cloth of his Speedo and ran her hand over the bulge's entire perimeter before she pulled down his Speedo and kneeled before him.

"Oh, baby, watching me and Mark fuck must've really got you going," he said breathlessly while her mouth slid up and down his shaft.

His cock was fully erect and she kept pulling it back to keep it at mouth level. She opened her mouth wider and moved down Robert's shaft until it hit the back of her throat. His entire cock filled Cara's orifice and he tangled a hand in her hair while he watched his erection slide in and out of her young yet expert mouth.

Cara bobbed her head, pumped him with her hand and caressed his balls. She was proud of her cocksucking skills, but he suddenly pushed back her head until his cock fell from her mouth.

"Get on all fours on the lounge, honey," he said.

Robert spread Cara's ass cheeks with his hands and buried his face between them,licking and sucking her clit, Dani's eager tongue darting in and out of her puckered anus.

She pushed her hips back toward him, her moans and cries getting louder while he ate her ass and pussy. Robert then slipped two fingers in her pussy and pumped them in and out while the tip of his tongue teased the crack of her ass.

Cara gasped when she felt one of his fingers slide into her ass and cried out with delight at the sensations of having both of her holes finger fucked and orally pleasured. She climaxed within minutes.

Robert mounted her from behind, removed her bikini top, and reached around to play with her breasts. He squeezed them tighter as he slid his erection up and down the valley of her crack and teased the opening of her pussy. The moisture from Cara's orgasm lubed up his shaft as as he slid back and forth effortlessly.

When he entered her, her walls enveloped his cock to the hilt. He plowed repeatedly in and out of her pussy, each thrust harder than the last. He turned her face toward his, both licking and tonguing each other's mouths with a fervent wet kiss as he continued to fuck her.

After a few more minutes, Robert pulled out. "There's something else we should try."

Before she had a chance to respond, he placed his dick against her asshole.

"Oh, Rob, I can't..." Cara said nervously.

"Just relax, honey," he reassured her in a low voice. "I'll go slow the same way I fucked your pussy the first time."

"I'm kind of nervous. Are you sure it's okay?"

"I've had a lot of experience with this. Someday, you'll have a boyfriend who wants it. Then you'll know what it'll be like to have a man's cock in your ass."

"Take it easy...don't hurt me..."

"You wanted me to make you a woman, and I'm going to. I promise I won't hurt you."

"Promise?"

"I'll be very gentle."

"Okay..."

"Good girl."

He pushed the head of his cock just inside her pink asshole when she let out a muffled cry. He stopped for a few moments before slowly starting to push again until his entire eight inches was buried in her ass.

The feeling of being in Cara's virgin ass excited him. Robert started slowly fucking her, going in and out slow enough until she was used to his cock positioned in her ass.

He thrust in and out a little more while she groaned beneath him, then he pulled back and pushed again. Robert went as slowly as he could stand while he fucked her a little more each time.

"Rob..." she moaned softly.

"You okay, honey?"

"Uh huh...it still feels funny, though."

"Just hang in there with me."

He pumped his hips a little faster as he drove into her asshole. Once the initial strange feelings of having him in her back door passed, Cara went wild feeling him pumping in and out of her. She pushed her hips back against his cock, meeting him thrust for thrust.

Just like after the pain had passed when he'd taken her pussy virginity, Cara felt exhilarated. She couldn't believe how hot anal sex could be, and it didn't take much longer for her to get into it as much as he was.

Huffing and covered in sweat, Robert's cock began to swell inside her ass. He soon began to come, accompanied by a series of loud groans.

She felt him come inside her, a more intense feeling than she'd ever felt. Cara cried out as his semen filled her asshole, which sparked her own orgasm.

Satiated after he'd finished, Robert's now-deflated dick slid out of her rectum.

"Now I've popped your cherry in both holes," he growled in her ear before he rose from the chaise lounge.

He helped her to a standing position and Cara felt an odd yet glorious tingle in her ass. They embraced and engaged in a long, passionate kiss before he finally broke it.

"So...how about that swim?"

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buttcheeks777buttcheeks777over 10 years ago
Hot as hell!

Wow, you're killing me with these super hot stories of hot people getting fucked in their beautiful asses!

AnonymousAnonymousover 11 years ago

Sometimes, in all these miscellanies full of doggerel and scribble one can find not only some gobbledygook, but also real chefs-d'oeuvres, such as this one for instance.

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