Note: This is the sequel to my first story, Alvin and the Chipmunks: The Sexquel. I suggest you read the first one if you haven't yet.
"I can't beleive THAT'S what they were doing in there!" Jeanette exclaimed as she walked next to Simon. Alvin and Brittany were in Daves room, fully dressed and getting yelled at. They got caught having sex in the boys' room, which Jeanette couldn't believe Brittany would do. At least, she had to pretend that. She knew her older sister too well to really beleive that she wouldn't have sex with Alvin.
"Well, I think I'm gonna go throw up," said Simon, "I mean, seriously, why couldn't they just wait?"
"It IS Alvin and Brittany," Jeanette replied.
"I guess you're right," said Simon with a sigh. "I think I'm gonna go talk to Theo, the poor little guys probably scared out of his wits."
Jeanette hugged him and watched him leave, sighing. How she WANTED him. She wasn't a dumb girl though, and she knew that having sex could get her pregnant. But she also figured out a way to reduce the odds of getting pregnant. The only question was, would Simon be willing to do it?
Jeanette spent the next hour reading a book in the girl's bedroom. She was waiting for Brittany. She wanted to talk to her badly. She had a LOT of questions that her older sister would be able to answer now.
When Brittany walked into the room she looked BAD. Her hair was a mess and she looked like she was in pain. Jeanette looked at her sister curiously. "What's wrong Brit?"
Brittany looked at her sister with an unusual kind look in her eyes, "Nothings wrong Jen," she managed to say.
Jeanette wasn't buying it, "Uh huh, sure. Come on Brittany tell me, I'm your sister, you can tell me anything."
"Fine, I'll tell you. But this stays between you and me. I don't want Ellie to hear about it. It would definitely disgust her."
"Alright Brit, I won't say a word to anyone else, now talk."
"Alvin and I just had sex. But we didn't just have normal sex. When we started, I gave him a blowjob, and then I asked him to fuck my asshole..."
"YOU WHAT?" Jeanette shouted in an excited tone. Realizing her mistake she tried to cover it up but too late.
"Jeanette Miller am I hearing what I think I'm hearing in you're voice?"
"Don't lie to me Jeanette. I can tell, you want anal from Simon don't you?"
Jeanette sighed, she couldn't lie now, "Yes, I want to have anal sex with Simon."
"I knew it! I could tell all along you were wanting him in your ass!" Brittany said with glee in her voice.
"Ok now finish the story about you and Alvin."
"Right. So anyway, he agreed and had me remove my clothes and get on my paws and knees with my tail raised high. Then he stuck his face in my ass and started sniffing my tailhole. That really got me turned on, especially when he told me he had never smelled anything so good in his life before. After he sniffed me, he started rimming me, which was AMAZING! Once he had me lubed up he pulled his tounge out of my tailhole and replaced it with his dick. It hurt, really bad. But after a while it felt so GOOD! But it was also weird because it kinda felt like I was pooping backwards. Anyway, after about 15 minutes he came inside my ass. Then he pulled it out and stuck it in my pussy, which hurt even more, and after orgasming into me, we kissed and cuddled until Dave walked in on us."
By the end of her recollection, Brittany was panting. She also had a pained look on her face.
Jeanette started getting worried with her sister. "Brit, what's wrong? Are you in pain?"
"Y-yeah, a little," Brittany said in a shaky voice, "It's my ass, it aches really bad."
"I'm sorry Brittany."
"I'm fine Jen, I just need to go to sleep."
"Well, before you do can ask for some advice?" Jeanette asked.
"Where do you think I should take Simon tonight if I wanted to fuck him?"
Brittany thought for a minute, then she said, "I would say the bushes in the backyard."
Jeanette hadn't even thought of that. "Thanks Brit," she said in a cheerful tone as she headed for the door.
"You're welcome." Brittany said before getting in bed and passing out.
Jeanette headed towards the boys' room, knowing Simon was probably done with both comforting Theo and yelling at Alvin. She knocked and to her relief, Simon answered.
"Yes, Oh hey Jeanette," said Simon, looking at her with a small amount of lust hidden in his eyes.
"Um, Simon, would you be willing to take a walk with me?"
"Sure," said Simon, leaving the room. "Let's just let Dave know and we can leave."
"Well, I just wanted to go out back," Jeanette admitted quickly, not wanting Dave to know that they were going out. It could ruin everything if Dave knew.
"Oh, well, ok then," said Simon.
They both went out to the backyard and started to walk and talk. They did this pretty often as it were so it wasn't weird or uncomfortable. After a while, the sun had almost completely sunk behind the horizon and Jeanette was ready to put her plans into motion.
"Simon come here," Jeanette whispered, leading him to the bushes.
"J-Jeanette, why are we getting in the bushes?" Simon asked with a worried voice.
"To make love," Jeanette replied, knowing that if he objected it wouldn't be hard to change his mind.
"B-but, what if Dave..."
"Relax, Simon. Dave probably won't know especially if we're quick about it."
Simon sighed, somewhat releived.
Jeanette leaned in and began to kiss Simon. As they kissed, her paw went down to his penis, which was beginning to harden. Once it was completely erect she knew what to do. She lifted his hoodie and pulled away from him. Then she put her face down to his exposed dick and licked it.
Simon shivered, then removed his hoodie completely.
Jeanette allowed Simon to remove his hoodie before continuing. She began to take his dick in her mouth slowly. She started by just bobbing until she was used to the feeling of the dick in her mouth, then began a sucking motion with her lips and tounge. Simon moaned. She knew she was doing well. She continued to blow his dick, sucking faster and harder with each passing second. She wanted to taste him. Simon wasn't going to last long. In no time at all, Simon shoved his dick into her mouth to the hilt and came, his cum shooting down her throat. Jeanette removed the dick from her mouth and smiled at Simon.
"I think you should use you're tounge to pleasure me now," she said with a wink.
Simon wasn't sure what she meant, "What are you asking me to do?"
"Hang on, let me just slip these off," she said, removing her skirt and blouse. Then she smiled and said, "I'll get into position, then explain." Jeanette then got on all fours with her tail raised high, just like Brittany had said. "I want you to put your tounge in my tailhole and lick it until it is soaked. Then I want to feel your huge dick penetrate my rectum and fill my bowels with your seed."
Simon didn't object, leaning in, he put his face near her tailhole and sniffed it a few times. He smelled shit, just as was expected, but found the scent to be enjoyable. In fact, it smelled amazing!
Jeanette sighed as she heard sniffing sounds like she had hoped. She was so lost in ecstacy and Simon hadn't even started! When she felt Simon's tounge on her tailhole she sighed, then put her head to the ground and raised her ass giving him better acess. Simons tongue began circilng over her tailhole. Clockwise, then counterclockwise. He got the outside complete soaked with saliva. Once the outside was soaked, he knew it was time to begin. He slid his tongue into her tailhole and Jeanette began moaning like there was no tomorrow. She began to beg him to lick her clean. He obliged. He spent a full twenty minutes with his tounge in her asshole. Eventually, he pulled out, ready to take her.
He lined the head of his penis up with her tight, virgin entrance and asked, "Ready?"
"Yes, Fuck me."
Jeanette moaned as she felt the head of Simons dick enter her tight anal ring. She couldn't believe just how big he was or how good it felt to be stretched by him. The pain was there, like Brittany said, but it didn't bother her at all. She began to push back against his dick as he insereted his full length into her. Once that was done, he began to pull out until only his head remained, then he rammed back in. He started bucking his hips and soon it became a full thrusting. Brittany had been right, it DID feel like she was pooping backwards, and yet, it also felt AMAZING. She was in ecstacy, and nothing was going to stop her from enjoying Simon's dick in her ass. Not even the strange sensation that her brain gave her that made think of pooping backwards. She begged Simon to cum, to fill her ass, and after thirty minutes of sheer bliss, she came. As she orgasmed her ass tightened and clenched around Simons dick, pushing Simon over the top. Simon moaned loudly as he came into her ass in 10 bursts. He then fell on top of her for a second. Both chipmunks laid there for a few minutes, lost in ecstacy.
Finally, after what seemed like hours, Simon pulled out. Cum oozed out of Jeanettes tailhole and Simon and Jeanette both moaned. Simon looked at his dick, covered in cum and, to no surprise, shit. He quickly pulled his clothes on as Jeanette did the same and they both walked back to the house to clean up.
Dave stopped them before they reached the bathroom, asking them where they had been. They told him they were out in the backyard talking and Dave didn't push the issue. Jeanette and Simon got in the shower together and washed each other off. Simon even fingered her ass to help get all of the cum out of it. They then kissed before getting out and dressing. Then, exhausted, but forever in love, they said goodnight and went to bed.