Andy’s cuddling with his 14-year-old sister takes an unexpected turn.
During the coming days, Andy thought about what he had done. He wondered what his parents would say if they found out. But despite all those doubtful thoughts, he was eager to be near his sister again. One night he even masturbated to a picture of her in a bikini. She was so wonderful he just couldn’t stop thinking about her.
Then Saturday came, and Andy had been gaming until 3 in the morning as usual. Just as he was about to go to bed, he thought about her again. His dick responded instantly by getting hard. Maybe he should pay her a quick visit, he thought. Just look at her cute face a bit while she sleeps.
So he silently went out of his room and slowly opened the door to hers. She had her blinds down, so it was pitch dark in there. He wouldn’t be able to see her he realized, but snuck up to her bed anyway. He started to carefully feel around in the bed but soon realized that it was empty. He went to the light switch and turned on the ceiling light. Sure enough, the room was empty. That little brat must be out partying again he thought.
It was past 3 a.m. though, so she must be coming home pretty soon, he thought. She had been home by this time the other times at least. Andy contemplated whether he should stay up or not, and finally decided that he should. So he turned the light off again and sat down on her bed.
After about 20 minutes of playing games on his phone, he heard the staircase squeak. It must be her he thought. Seconds later, she came through the door. From the hallroom light, he could see that she wore a short and tight red summer dress that looked way inappropriate for a girl her age. It barely came down over her butt, and it followed every shape of her body. Andy wondered where she even found such an adult dress in her size, but he certainly didn’t complain.
When she had taken a few steps into the room she jumped out of surprise.
“What are you doing up?”, she asked with a surprised voice.
“I was just about to ask you the same thing”, he answered.
“Maybe I was out having some fun, but I guess you wouldn’t know anything about that”, she said, shifting to more of a cocky tone.
“Well if that’s the tone you’re gonna have, maybe I should just tell Mom”, he said.
“Please! You promised last time that you wouldn’t tell her”, she said a bit anxiously.
“Well that’s cause you made me breakfast”, he said.
“So what, I have to make you breakfast again to shut you up?”, she said.
“Something like that I guess”, he replied.
“Or perhaps you’d like to have one of your ‘cuddling’ sessions again”, she said, really emphasizing the word ‘cuddling’.
Andy’s face turned red from embarrassment, and his gaze fell to the ground. “Maybe..”, he finally said.
“In that case, I want 30 bucks”, she said, getting back to the cocky voice.
“You’re making me pay to hug my sister? that’s harsh”, he asked.
“Not so fun anymore when you’re the one getting extorted huh? Besides, you barely use any of your money anyway”, she said.
Andy thought about it for a few seconds but quickly concluded that he wanted to cuddle her way more than he wanted to have 30 bucks.
“Okay”, he said.
“Also, you can’t threaten to tell mom about me sneaking out ever again”, she added.
“Fine”, he said.
He almost couldn’t believe what had just happened. Not only had she confronted him about his moves on her, but she had also allowed him to do it again, so long as he paid her for it. This had gotten way more fucked up than he had ever expected it to.
Just weeks ago he had never even thought about her sexually, except maybe for a split second some time before remembering she was his sister. He had even been pretty turned off by anything incest related before. But that had all changed so very quickly. And now Elsa knew he was into her, and would be using it to her advantage whenever she could.
Elsa went and closed the door to her room, making it pitch black again. Then Andy heard her sit down on the bed, right next to him. “I’m keeping the dress on though”, she whispered close to his ear. Then she got under the cover. Andy was a bit disappointed but figured it would be nice anyway since the dress was so tight and short.
He undressed until he had only his boxers on and laid down in her bed. He got under the cover and fumbled until he found her. She was lying on her side, facing away from him, just like the other times. He crept up behind her in a spooning position and got his arm around her. He inhaled her lovely scent and hugged her hard.
He lay like that for a good ten minutes until he started to wonder what they had agreed on. Had she meant for him to only hug him or was he allowed to do his humping like last time? He also wondered if he was allowed to feel her, now that he had paid. It was all very confusing, and he was too embarrassed to ask.
Instead, he figured he would just try doing things and see how she reacted. So he proceeded to move his hand slowly down until it was resting on her dress by her butt. So far she seemed okay with it. He grabbed her butt and started squeezing a bit. Andy loved the shape of it. It was so nice and firm. He started moving his hand down even more. The dress ended just passed her butt, but Andy continued down a little bit more. His hand was now on the inside of her thigh.
He began massaging her thigh. Still, she hadn’t made any attempts to stop him, so he slowly started moving his hand up again. When he encountered the dress, he moved his hand towards her butt again, except this time he kept his hand tight to her skin, pushing the dress up as he went. When he had gotten his hand up to her butt cheek again, he realized that it was still touching her skin. She must have been wearing the dress without any panties!
This was starting to get too intense for Andy’s cock. He hadn’t even touched it yet, and still, it felt like he was just seconds away from coming simply from the fabric of his boxers touching it. He had to take it out of his boxers he thought, so he released her butt and proceeded to pull down his boxers.
The tension loosed a bit, but he felt like he had to touch her with his cock now. So he moved forward until his dick touched her thigh, then he carefully lifted her leg so that he could get his dick in between her thighs. When he had gotten it between them he felt that same lovely thing that she did last time.
She was squeezing her thighs together to make it tighter for him.
Holy shit, he thought.
This won’t be a long one. He started to slowly move his hips back and forth leaving a wet trail of precum on her thighs. So what if he had to pay 30 dollars for this, he thought? He wouldn’t hesitate to get an extra job just to be able to feel this every night.
He started pumping harder and harder, which lead to his cock pushing further and further up her thighs.
Finally, it touched what must have been the mound of her pussy, because it was incredibly warm and moist. Just the thought of having touched her pussy sent Andy into the most intense orgasm he had ever experienced. He began cumming violently with every thrust, shooting his load everywhere. Elsa twitched when she realized what was happening and put her hand down to cover her pussy, but it was too late as he had already drenched her pussy lips in cum.
For ten seconds straight Andy continued, until his humps slowly started dying down. He felt like he had emptied a year’s worth of cum, and it had landed all over his sister’s thighs, pussy and butt.
He hugged her hard and kissed her neck a few times while inhaling her scent. “You are the best sister I could ever have hoped for”, he whispered. “Well you better be the most generously tipping brother ever to exist, ’cause you just came all over my pussy, and I’m not on any pill”, she whispered back. “I’m sorry”, Andy replied. “Besides you can’t get pregnant from just getting it on the outside”, he added.
“Well you better be right”, she said and began sitting up. She climbed over him and made a run for the bathroom, trying the best she could with her hands to keep the cum from dripping everywhere.
Andy just lay there enjoying the moment. He had just made contact with her pussy. This was more than he had ever hoped for.
*** END OF PART III ***
