Best Friend's Shy Son

The girl knew he had a crush on her. That much was obvious. But she thought that what was bothering him was a much bigger issue than that.

They left the library after spending half an hour there. The two walked to their lecture hall together and got their seats near the front. Henry diligently took notes during the first hour before his mind wandered off and he became occupied by thoughts of other matters.

It was starting to make him worried how much he missed Carla's touch, the feel of her hands on his body, her lips around his hard cock....

He cursed himself.

His dick had gotten hard in his pants and he shifted himself around, hiding his boner. The last thing he wanted was for Jessica to notice his erection and get the wrong idea.

The next hour passed more slowly.

Once the lecture was over, they decided to have lunch together. Henry ate his yoghurt and banana while Jessica ate instant noodles. They sat on a bench and ate, and Jessica continued observing Henry. He always ate the same things for lunch every day. She always considered him a creature of habit because of this, one that simply refused to change his routine and stuck by it resolutely, despite her encouraging him to switch things up.

At the end of their lunch break, they went to their next class. It was better than their morning one with a professor who presented the material in a more interesting way - a way that was less likely to put you to sleep in your uncomfortable chair.

Henry arrived back at the apartment later than usual that evening. He went to take a shower right away, before having dinner and doing some more reading on the couch.

He got a message from Carla.

'Hi, baby. Tell your mom I need you to come over and help me move some stuff around tomorrow. New furniture.'

'Okay, Aunt Carla' he texted back.

He then told his mom what Carla wanted him to tell her. Drew nodded, promising to drive him over to Carla's house the next day. She then asked him what he wanted for breakfast the next morning. He ended up helping her marinate chicken.

That night, Henry laid in bed thinking about his mom's friend. He missed her so much and found himself both excited but also feeling guilty. No matter how many times he tried telling himself he wasn't doing anything wrong, he couldn't stop feeling that he was betraying his mother's trust by getting together with her friend. The fact that Carla initiated all their encounters only helped ease his conscience a little.

Eventually he fell asleep, dreaming of her soft lips.

.......

The next day, Drew drove her son over to Carla's house. There, she dropped him off and told him "I'll be back to pick you up in half an hour."

"Make it two hours. I bought a lot of new stuff and also want Henry's opinions on them."

"Okay, Carla. See you." Drew then left the house, heading to work, leaving her son alone with her friend.

Henry looked at Carla shyly.

Carla gave him a lascivious grin. She told him "Come here." He approached her. She wrapped her arms around him and captured his lips in a passionate kiss, stealing his breath. His eyes widened in shock and he melted in her strong embrace. Well, not his entire body. A certain part of him got very hard. Very hard indeed...

"Someone's happy to see me," she teased, rubbing his crotch. The older woman shamelessly fondled Henry's young balls. She groped him. He turned crimson, gasping, moaning out loud.

"Aunt Carla..."

"Shhh," she placed a finger over his lips. Carla then told her friend's son "I want you to fuck me today."

Henry couldn't believe it. He thought his ears deceived him. "Did you just say-"

"Yes. You heard me correctly. I want you to fuck me, Henry, and cum in my pussy."

"But what if you get pregnant?"

Carla chuckled. "That's not gonna happen," she said. "I got my tubes tied two years ago." She then dragged him to her bedroom and pushed him onto her bed, removing his trousers for him. Next she took his boxers off, allowing his cock to spring up.

She stroked it gently, giving it squeezes. While she jerked his cock, she kissed him, forcing her tongue into his mouth. He moaned, growing ever harder in her hand.

The older woman pumped away, caressing his flesh and telling him "I can't wait to feel this inside me." She discarded her booty shorts. Her hairy cunt glistened with desire. She mounted him, holding on to his manhood.

The buxom blonde took him inside her. She began riding him. She fucked him slowly at first, giving the boy time to get used to it. Her pussy was so hot it felt like she set his dick on fire. It burned - but in a good way. A very pleasurable way. The friction was amazing and he moaned, enjoying how tight she was.

She fucked him faster, yanking her top off and telling him "Suck my tits, baby. Suck them." He cupped her round breasts and kissed her nipples one at a time, licking them and sucking gently.

"Ahhhh, your pussy is so tight, Aunt Carla!" he whimpered. Her juices flowed freely, soaking his crotch and covering his cock.

"You like it, baby?" she asked, bearing down on him, bouncing up and down on his dick expertly. The wanton woman has ridden many dicks in her time. His hand found her clit and he rubbed it, making her moan his name.

"I love your pussy. I love it so much!" Carla smirked. Her golden hair cascaded down over her boobs and she pounded him savagely, ravishing him, treating him like a sex toy.

"Cum in my pussy, my boy," she said. Her words were too much to handle. He screamed and cummed.

The boy cummed violently inside her, filling up her pussy with his seed. She was ecstatic and kept on riding him until he finished cumming. Carla lied down next to the boy. She gave him ten minutes to rest. Then she got on all four and said "Now fuck me from behind."

Henry placed his hands on her ass. His cock stiffened. He slowly inserted it inside her, feeling her warm cunt sheathe him once more. He moaned, thrusting in and out of her pussy.

Her slippery cunt was still tight and it remained wet and warm as he fucked her. He held on to her thick asscheeks, plowing her as hard as he could, banging her with all his strength.

Then she told him "Pull out and fuck my ass," tossing him a bottle of lube from her bedside table.

Her friend's son couldn't believe his luck. He withdrew from her pussy, pouring the lube all over his dick and on her asshole. Then he slipped between her buttcheeks with a loud moan. The boy stuck his cock inside her ass. He started fucking.

Rutting into her like an animal, the boy seemed possessed, his hips thrusting of their own accord as he became increasingly lost in a haze of lust.

His balls swung into her cunt as he pounded her tight ass, taking her doggy style the way she ordered him to. "Pull my hair, baby. Pull it. Fuck my ass harder!" He pulled her hair and fucked her harder and faster like she wanted.

"Aunt Carla, I love your ass so much!"

"Cum in my ass, sweetie! Fill my ass with your cum!"

Her words made him erupt. He cummed even harder than he did before. The boy's cock pulsated violently and he fired a massive load of semen inside the older woman's shapely ass. He was spent.

"Lick me clean and suck your cum out of my ass," she demanded. He withdrew his softening prick from her posterior and buried his face in her rump, licking her nasty little shithole. He licked her asshole slowly, tasting his own jizz. Then he buried his tongue inside her and used it to scoop around, cleaning up her diligently.

Henry laid in her arms and she gently kissed his forehead.

"You are mine," she whispered. "I've been in love with you for many years now. I actually quit smoking for good two years ago and lied that I still smoke to trick you into doing things with me. I love you so much and I want you to be my boyfriend. Will you be my boyfriend, Henry?"

The boy was stunned. He looked into her beautiful eyes, struggled for a moment, then found his voice. "Yes," he replied. "I'll be your boyfriend, Aunt Carla."

She grinned, giving him another kiss.

The two of them took a shower together and fucked in the shower stall. They then got dressed and had some snacks in the sitting room while waiting for Drew to come pick Henry up.

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

Henry continued dating his mother's best friend in secret over the next several weeks. He wasn't sure how to tell his mom about their relationship. Somehow, he felt that she wouldn't be so thrilled about the two of them being together. No, she'd probably be pissed about it.

One day, Carla told him "I lied."

"What did you lie about?"

They were sitting on the couch at her place, watching TV together, a bowl of popcorn between them. Carla looked at him and said "I lied about having my tubes tied. You've been fucking me completely unprotected and I'm pregnant now."

His eyes went wide in shock. "What? But why would you do that?"

"Because I'm so much older than you! I was afraid you might get bored of and leave me. I thought that if you knock me up, I'd always have a reason for you to stay around. I wanted to make it so you couldn't leave me."

Henry placed his hand on his chest. "Aunt Carla, you didn't have to do that. I'd never leave you."

"Really?"

"Yes. In fact, I think I've fallen in love with you."

Carla smiled, tears of joys falling from her eyes. "I love you, Henry. And don't you worry about our baby. I have more than enough money. You just continue going to college and contribute when you graduate and land a job, okay?"

"Okay. So when are we telling my mom about us?"

Carla mused. She said "Tomorrow. Your mom just told me she got a raise. It put her in a really good mood. We should take advantage of that while we can." Henry nodded, agreeing with her

"Okay. We'll tell her tomorrow."

That afternoon Carla drove him back to his apartment. She said goodbye to Henry outside the building, kissing him on the lips and then leaving. He smiled as he made his way up the stairs. He spent some time buried in his textbooks, studying until his mother returned from work. She could tell he was in a good mood but didn't know why.

That night he tossed and turned in excitement. When Carla said that she's pregnant, he was very shocked. Yet the way she quickly assured him that it's going to be okay and he can keep going to college made him so happy, knowing she had planned everything out.

When Carla came over the next day, Henry was beside himself with excitement.

Drew frowned. She could see that her son was very giddy, an unusual phenomenon given how he normally behaves. "What's going on?"

"We have something to tell you," Carla said to her best friend.

She entered the apartment and looked Drew in the eye.

Drew stared right back. "Go on then," she replied.

"I'm dating your son."

Carla then grabbed Henry's hand, making him blush. Drew gaped in shock. She stared at the two of them uncomprehendingly. She couldn't believe her ears yet her eyes told them the same thing, seeing their interlocking fingers and the way Henry was blushing madly.

"Are you out of your mind? You've known him since he was a kid!"

"Yeah, well he isn't a kid anymore!" Carla fired back hotly. She glared at Drew. " He is an adult now! He can make his own choices and he chose to be with me! Isn't that right, honey?" The blonde woman directed the last part at her much younger lover gently. He nodded shyly.

He then said to his mother "I know this upsets you, Mom, but she makes me happy. I love her so much and it would mean a lot if you approve of this."

"How can I approve? You are my little boy and she is my best friend."

"Your little boy is grown up now, Mom. I will always love you but she is my girlfriend and I want to be with her. So please..."

Drew held up a hand. She sighed. "Alright," the woman murmured. "If you truly are serious about her, then I suppose I have no choice. I give you my blessing."

Henry smiled. He hugged his mother.

"Thank you."

"Oh, and one more thing," interceded Carla. She told Drew "I'm pregnant. You're going to be a grandma."

Drew's eyes nearly popped out of her head. "How did that happen?"

"I lied to your son that I had my tubes tied."

"Urghh."

"Come on! Don't you want a grandchild?" said Carla, talking to her best friend and trying to make her calm down. Eventually, Drew calmed down and reluctantly said she's okay with it.

Henry moved in with Carla the next day.

The two of them went on to marry a year after he graduated and lived together happily ever after.

The End.