Best Friend's Shy Son

The afternoon was a hot one. It was the middle of summer, after all. Carla was used to the heat though. The retired Marine served two tours in Afghanistan before being honourably discharged. She then went to university, using her GI Bill, becoming an engineer.

Right now she was knocking on her best friend's apartment door.

Carla and Drew were childhood best friends, and actually planned to join the Marine Corps together. But then Drew got knocked up by one of her one night stands, which meant Carla had to enlist by herself.

After just a few seconds, Drew opened the door. The two 39 year old women hugged. Drew was a tall, thin redhead with shoulder length hair. Carla, meanwhile, was a voluptuous blonde with huge breasts and a massive ass, her hair longer than Drew's. Both women were very sexy and in incredible physical shape from constantly working out.

"Hey! Long time no see!" said Drew.

"I know. Been busy a lot lately."

Carla made her way inside. She waved at Henry, Drew's 19 year old son.

"Hi, sweetie!"

"Hi, Aunt Carla." He was reading another one of Agatha Christie's novels - the boy was a massive fan of mystery novels. Carla sat down next to him. She produced a box of chocolates from her purse.

"Your favourite," she said, handing it to him. His eyes went wide and he set his book down.

"Thank you so much! You know I love these."

"I surely do." She ruffled his hair affectionately and gave him a little peck on his cheeks. Her best friend's son was used to this. He smiled, taking the box of chocolates to the fridge and putting it inside. "So any plans for today?" Carla asked her friend's teenage son.

The thin nerd replied "I'm staying in and doing some assigned reading. Mom's got a second shift today."

Carla turned to Drew "I'm so sorry," she said. "I totally forgot about that. I thought I was gonna ask you to go to the gym with me."

"It's okay. You can stay. We can go to the gym together when I'm back from work."

"Perfect! I'll just hang out with Henry until you get home. You don't mind that right, Henry?" Carla directed the last part at her best friend's only child. Henry told her that he did not mind at all. "Wonderful!"

Drew grabbed her packed dinner and left.

Once she was gone, Carla started talking to Henry.

"So! What are you up to at college?" she asked. Henry smiled softly.

"Not much," he said. "I have a couple of group projects right now. Made a couple of friends. Have to, really."

"Hmm, I see." A couple of moments later, Carla asked "What about a girlfriend? Got yourself one yet?"

"Aunt Carla, you know I'm still single. You already asked me that question last month."

"Hey, a lot can happen in under a month," she defended herself.

"True," conceded Henry. "Still, I'm under no delusion about my prospects. Look at me. I'm a plain-faced, socially inept dork who could barely talk to people outside my family. You're the only woman I'm not biologically related to that I can hold a deep, meaningful conversation with, and that's only because we're almost like family."

Carla smiled.

"There is a perfect person for everyone," she said. "You just have to trust me on that."

"Thanks, Aunt Carla." After 20 minutes of reading, with Carla sitting next to him and going through her car magazine, he got up to stretch his limbs. He groaned softly.

Carla looked at him thoughtfully. "Let me massage your thighs. It'll help with circulation."

"No, it's okay. I'm fine."

"Honey, please. Just trust me, alright? Lie down and let Aunt Clara help you."

"Alright then." Henry laid down on the couch with his legs out. Clara placed her powerful hands on his thighs. She began massaging him through his trousers. To his embarrassment, he found himself getting aroused. The closer her strong hands drifted towards his crotch, the harder he became, his member getting stiffer and stiffer every second.

She rubbed his muscles like that for about five minutes before saying "Feeling better?"

He nodded, not trusting his voice.

"Good."

The boy sat upright again, right next to his mother's closest friend. She gave him a smile and asked if he wanted to take a break from studying.

"Sure," he replied. "I think I want to watch a movie."

"Cool, baby. Just pick one here. I've got a Netflix account," Carla told him when he was about to get up and look for some DVDs.

She patted the space next to her and he scooted over, sitting right next to the busty blonde. Carla was wearing a tight T-shirt and he couldn't help noticing how shapely her soft breasts were. Then he realised he was ogling his mom's friend and mentally berated himself, shifting his attention to her screen. He quickly picked a movie and they began watching it together. Her huge butt was right next to him. He fought his primal instinct, struggling to not look at it.

The time passed quickly. He didn't get to watch many movies lately, what with the workload, so it was enjoyable for him. Watching a film with Carla there was much better than watching one on his own, too. He enjoyed her company much more than he did the company of his peers. She had always been someone he went to whenever he had a problem, a trusted confidante, someone who told him he could tell her any secret and she would keep her mouth shut.

45 minutes into the movie, Henry told her "Can we watch the rest later? I think I should get back to some of the reading now."

"No problem."

She tucked her phone back in her purse and he grabbed his textbook. He was very diligent, rereading parts he didn't understand, going back to them to try to make some sense of the words. Carla smiled.

Carla looked at him read for a while. Then she took a crumbled pack of cigarettes out of her purse, along with a lighter. Henry heard the noise. He turned around to look at her and frowned.

"Aunt Carla, mom told me you used to smoke but quit already," he said, voice full of disapproval.

"I did, but then I started smoking again."

"I really wish you would quit the habit permanently."

"And why is that?" Carla asked, putting the end of one cigarette in her mouth and preparing to use the lighter.

"Because I don't want to see you damage your own health like that. You know how bad it is for you."

His mom's friend sighed and temporarily removed the cigarette from between her lips. "You don't understand how addictive it is. I do want to quit but it is just so hard."

"Try harder then. Please? For me?"

Carla said "What will you give me if I try?"

"What do you mean?" he asked.

"People need incentives to do things, Henry. You are a smart boy. Studied economics. Surely you'd understand that."

Henry said "What do I have to do?" The boy was full of concern for his mom's friend, who thought not a relative was like an aunt to him.

"Eat my pussy."

Her words shocked him to the core. He couldn't believe what she said. For a moment he thought his ears deceived him. There was no way she just told him to eat her out like that. "Could you repeat that please?" he asked slowly.

"Eat. My. Pussy," she said. "I'm gonna take my pants off and you're gonna bury your face between my legs and suck my cunt until I cum. If you do that for me, I promise I'll stop smoking."

"But you're my mom's friend. If she finds out..."

"She doesn't have to know about this," Carla interrupted. She unzipped her pants and slid it and her panties down, exposing her hairy pussy. The sight of her bush made him hard again in no time. He knew it would be very foolhardy of him to orally pleasure his mother's best friend, yet the boy also considered what she said to him.

"If you don't eat me out now, I'll keep on smoking. Think of the damage I'll do to my lungs. Maybe I'll even get cancer."

No, he can't let that happen. He didn't want to see her destroy her own health like that. Even though she exercised a lot, smoking would still lead to issues.

"Okay, but you have to promise you'll quit smoking for good this time."

"Promise."

The teenage boy nervously leaned down. He didn't know what to do and so decided to start slow. He began by kissing up and down her thighs, feeling her hot skin on his lips. Then those lips found her labia and he started making out with her lower lips, French-kissing her pussy.

Henry buried his tongue inside her. She moaned, caressing his hair. "Yes, baby. Just like that. Tongue-fuck me." He obeyed her, continuing to slide his tongue in and out of her warm tunnel. Her hot cave constricted around him. He tasted her pussy juices. Fuck, her cunt was delicious. She tasted so amazing. Her pussy juices was spicy, the scent overwhelming, intoxicating him beyond belief.

He then located her clitoris and licked it before sucking the button.

She moaned louder, arching her back. "Yes, suck my clit, baby boy. Suck it. Go on." Her ass rose off of the couch.

Carla fucked his face. She rubbed herself all over him.

The boy's face was getting covered in her nasty fluids. He inhaled deeply, enjoying the powerful scent of her pussy juices. He kept on sucking her clitoris, making her moan his name.

He alternated between sucking her clit and tongue-fucking her, finally driving her to orgasm. She cried out loudly before squirting all over his face, soaking him in her cum.

"That's good, but I wanna cum again," she told him, grabbing his head and keeping him trapped between her strong thighs. He kept on munching away at her crotch.

The boy carried on eating her out and she moaned happily. He used his lips and tongue well for a beginner and she gave him pointers.

She told him exactly how she wanted him to do it. He couldn't get enough of her freely flowing juices.

Henry swallowed mouthful after mouthful of Carla's pussy juices.

It felt like he was drowning in the fluids flowing out of her cunt. He brought her to a second orgasm and then a third one. Her entire body shook, convulsing violently as she sprayed all over his face for the last time of that day.

She grabbed her panties and used it to wipe the boy's face, before putting it and her pants back on. "Well done, baby," she said to him. "I won't be smoking again."

Henry was dazed. After spending what felt like ages with her legs crushing his head, he struggled to see her face clearly. Rubbing his temples, he murmured "Good. Like I said, I just don't want you to, you know, mess up your body like that. Really bad for your health."

Carla smiled, giving him a peck on her cheek.

"When your mom's home, tell her I changed my mind about going to the gym. Say that I went shopping instead, okay?"

"Okay, Aunt Carla."

"Bye, baby."

She strutted to the front door, swaying her huge ass, captivating him.

Once she was outside, he hurried to the bathroom and started masturbating. It was the quickest orgasm of his life. Soon, he was cumming a bucketload.

He quickly cleaned up and went back outside, sitting down on the couch and reading, pretending nothing crazy happened.

When his mom was home, he told her what Carla told him to say. Drew was disappointed. She told him she really wanted to go to the gym with her.

Henry sat there on the couch, deep in his thoughts. He had no idea what was going to come.

That night, Drew asked her son if something was on his mind.

"Is everything okay, sweetie? You look like something is bothering you," she remarked as they had dinner together. He looked up at her guiltily then tried to hide it with a fake smile.

"I'm okay, Mom. I'm fine."

"Sure?"

"Yes," he confirmed, even though his voice told her that he was far from okay. The expression on his face unsettled Drew as well. It upset her not knowing what was wrong. She knew something was bothering her son - something he didn't feel comfortable with telling her about.

.........................

The next day, Carla came over again.

Henry sat silently while she talked to his mom. He didn't trust himself to say anything, not after what happened. She was sneaking glances at him when his mother wasn't looking and her gaze turned him bright red.

"By the way, have you been to that new tennis court yet?"

"The one an hour away from here?"

"Yeah, that one."

"No, I haven't."

"Wanna go there together next week?" Carla said.

"Of course," replied Drew. She then turned to her son. "What do you think, honey?"

Henry said "Yeah, that would be great."

"Perfect. It's settled then."

A few minutes later, Drew asked her best friend "So are you dating anyone right now?"

"No, but there is this one guy I've wanted for years now. Someone I'm really crazy about."

"Make a move on him then. Should be easy. You're almost as hot as I am."

Carla raised her eyebrows. "I think it's the other way around," she teased. Both of them were very proud of their looks. They were the most attractive girls in high school and Carla had no trouble getting laid during her time in the Marine Corps and afterwards. She regularly flaunted her attractiveness, using it to get all the cocks and cum she wanted.

Drew asked "Are you going to tell me who he is? Is he someone who I know?"

"Can't say right now. I'll tell you when he and I get together."

"That's the spirit," said Drew approvingly. Drew then got up and excused herself, saying she had to go to work and that there was an important meeting. Carla and Henry waved at her as she put her shoes on and left through the door.

Once she was gone, Carla rummaged through her purse. She muttered under her breath.

Finally, she found what she was looking for.

Henry looked at her as she produced the familiar pack of cigarettes and her lighter. "I thought you said you'd quit if I, you know, gave you cunnilingus..."

"I'm addicted to sucking things, Henry. If you want me to stop sucking on these cigarettes, you better give me something else to suck," she said. Then she added "Like your cock, for instance."

Henry gulped.

"Alright, Aunt Carla," he said. "If that's what it takes to get you to stop smoking..."

"It is. Just let me suck your cock and I'll quit. For real, this time. I really mean it, honey."

Henry unzipped his pants. She smiled and leaned over, positioning her mouth directly over his manhood. She parted her lips and wrapped them around his cockhead, sliding them down to the base of his shaft. It was easy. Carla didn't have any trouble getting his entire dick inside her mouth.

Her friend's son moaned in shock. "Oh god!" he cried out. She smirked around him before bobbing her head up and down, sucking him off.

The boy couldn't believe it. He was getting fellated by his mom's best friend. She made him feel so good. Her full lips slid up and down his shaft and she slobbered all over him, drenching his member in her warm saliva.

She sucked his cock harder and faster. The warmth and wetness of her mouth sent him over the edge and he cried "I'm gonna cum, Aunt Carla!"

Carla sucked him off really hard. Then she took his member out of her mouth and stroked him, telling the boy "Cum all over my face, baby. Cover my face in your cum."

Once she was done, he shyly said "Let me make you cum too." She raised her eyebrows, before removing her booty shorts. The fit blonde wasn't wearing panties. She laid down and parted her legs for him, letting him find her puffy pussy with his lips. He could taste her urine - she had recently taken a piss.

He ate her out more confidently than he did the day before. She rewarded him with lustful moans, saying "Yes, my darling. Eat my pussy. Just like that."

Her encouragement made him work harder and he focused on her clit. Paying attention to her clitoris made Carla's entire body quiver. She was trembling with pleasure. She gasped and cried out in orgasm, climaxing very hard. Carla gushed all over his face and soaked him in her dirty juices.

The boy didn't stop there. He carried on giving her head, going down on her until she had a second orgasm.

He continued to give his mom's friend oral, only stopping after her third orgasm, telling her shyly "Consider this a thank you for your service."

Carla giggled, ruffling his hair maternally.

She and him then went to wash their faces together in the bathroom. He asked her "Why are you doing these things with me, Aunt Carla?"

"I just get horny," she replied.

"That's it?"

"Yes."

Carla then gave him a kiss on the cheek, before leaving the apartment. He went to his room and sat down, trying to figure out what was happening to him. He was in turmoil. He had no idea what was going on in his life even as the stuff happened to him. The boy was clueless and hated feeling that way.

What he loved, though, was tasting Carla's delicious pussy. Her cunt tasted so damn good and he wanted to feast on it again soon. The way she sucked his cock was amazing as well. He found himself hard again despite just cumming on Carla's face not so long ago. With a sigh, Henry started jerking off.

..........

Drew studied her son's face. She looked at him anxiously. He was sitting on the couch with a textbook in his lap, reading it and jotting down notes. Something told her that he was struggling inside, but with what? She has seen him worried about college work before, but this was different. She didn't know how she knew, she just knew it. It was a feeling in her bones - a mother's intuition.

"Honey, do you want to go to a bookstore?" she asked. Her son nodded.

"Sure."

He got up from his chair with a light smile. The boy was still struggling with his internal guilt. He had no idea who he could talk to about this. Who on Earth could he actually tell about what has happened? There was no way he was going to tell his mom.

No, just no. He couldn't tell her he ate her friend out, or that her friend reciprocated by sucking him off and giving him the best orgasm of his life.

The two of them took a bus. He stood and glanced out of the window, wondering what was going to come next. As he glanced at the sidewalks, the boy wondered how his life had ended up this way. He felt his heart beating rapidly as he thought about Carla and the nasty things they did to each other.

He bought a new book that day and started reading it immediately when they got home. It helped him feel better but he still mentally chided himself over how easily he allowed his mom's friend to use him to satisfy her craving. It sickened him knowing how his mother's friendship with her could be ruined if she ever found out what transpired between them.

The next day, he went to college. He had a class in the morning. There, he met one of his only friends, Jessica. She was a tall brunette with a cute face. She gave him a bright smile, one that he happily returned.

"Hi," she said. Seeing her helped cheer him up and he was able to focus on something else other than the guilt that has been plaguing his mind for hours on end. "Is everything okay?"

Great. He was going to have to deal with both a suspicious friend and a suspicious mom.

"Yes, everything's fine," he lied. He was ashamed of how easy it was to lie to her. She took a sip of her coffee. He went to the vending machine and bought himself a small carton of milk. Coffee never agreed with his stomach.

They went to the library together. He used to have a crush on her but his experiences with his mom's friend had completely overwhelmed him and his feelings for Jessica had seemed to vanish. This made him feel even guiltier as he thought about how he might be falling for his mom's friend, even though his mom's friend was the one who initiated both of their encounters.

As he did some reading, he thought of his upcoming lecture. He had already prepared for it by going over some notes from the previous one and was sure he would understand it well.

Jessica was anxious, but not about the approaching lecture.

She could sense that something was going on in Henry's life - something he wasn't sharing with her.