Learning How to Take It Up The Ass

The movie ended.

"Well, that's not gonna win any Academy Awards," Debbie said.

"Probably not," Cheryl agreed.

"Wanna watch another?"

Cheryl glanced at her watch.

"Better be getting home."

"I still don't understand why you're at my place on a Saturday night, Cheryl."

"Long story."

Cheryl and Debbie, friends at the office, had hung out on weekends until Rance entered Cheryl's life four months earlier. He worked in Chicago but visited regularly on weekends.

"You guys haven't broken up, have you?"

"Nothing like that. At least I don't think so."

Debbie loved gossip. She grinned and scootched into a cross-legged position in the overstuffed chair.

"Oooh! Tell Aunt Debbie all about it!"

Cheryl smiled. Debbie was seven years Cheryl's junior. Her Peppermint Patty red hair and freckles made her look even younger.

"Forget about it."

"Let me guess -- since it's a long-distance relationship he thinks you each should feel free to see other people."

"No, no. Nothing like that! It's just a little thing we have to work out."

"He has a little thing?"

"No. NO! If he had a little thing it might not be so bad."

Debbie uttered a theatrical gasp.

"Oh, my, Cheryl! You must tell."

"I really can't talk about it."

"Why? Does it involve animals or small children?"

Cheryl sat upright on the couch.

"Deb! Of course not!"

"Then what?"

"It -- it's just something I'm not entirely comfortable with."

"You don't give blow jobs?"

"No. I mean, yes. I mean --"

Debbie hopped from the chair and plopped beside Cheryl.

"Whips and chains?"

"No!"

Debbie's eyes widened.

"He wants to give it to you up the ass!"

Cheryl's cheeks flushed before she could reply. Debbie laughed.

"Rance wants to bugger you!" she cried.

"I didn't say that!"

"He's knocking at the backdoor!"

"Debbie!"

The girl shook her head.

"You had me going for a moment. I thought maybe he was into something really kinky."

"That's not really kinky? Um -- not that I'm confirming it."

"Maybe a little kinky, but if someone finds an opening, he's going to take it, right? Why don't I pour another glass of wine and you tell Aunt Deb all about it."

"Yeah, like you're so experienced."

Debbie looked over her shoulder and smiled on her way to the kitchen.

"I am, in fact."

"You're kidding!"

"Not at all. Do you remember Chad?"

Cheryl thought for a moment. Debbie had had several boyfriends since she knew her.

"Chad -- tall, skinny, scraggly little goatee. Hippy guy?"

"That's him."

"I never understood what you saw in that guy."

"Well, he was free-spirited and a poet. He had Cocker Spaniel eyes -- and he was hung like a rhinoceros."

"I don't like the image this is conjuring."

Debbie returned with the wine and plopped back on the couch.

"I was like you, Cheryl. The idea of having a dick shoved up my ass didn't have much appeal. Chad wanted it, but he didn't try to push it on me -- pardon the pun. He'd bring it up now and then. He said he was really experienced and if I'd just let him try, he thought I would like it. Finally, I gave in."

"You're going to tell me all about it, aren't you?"

"Well, I was -- just a minute."

Debbie hopped up and left the room. She returned a moment later with a small wooden chest which she put on the coffee table and opened.

"Take a look," she said.

Cheryl peered into the box and her eyes went wide.

"Oh, my God! What is all this?"

Debbie laughed.

"It's an ass fucking-kit. Chad left it with me. It has a variety of dildos and plugs in different shapes and sizes and this really cool imported lube."

She took something from the box and held it for Cheryl to see.

"He called this the beginner dildo because it's so small. He used it on me for a couple of days before he tried something larger. Here, hold it."

Hesitantly, Cheryl took the small, pink device, held it up and examined it.

"Of course, he lubed it up really good first and put it in me real gentle. It felt really weird -- but not bad."

"I'll take your word for it," Cheryl said and placed the thing gingerly back into the box.

"When he moved up to a bigger one, he didn't warn me. He greased it up and shoved it right up my bottom!"

She giggled.

"That was a shock, I'll tell you! Hey, if you want, you can borrow my little bugger kit."

"Thanks, but I'll pass."

Debbie's eyes got big.

"I know -- what if we get you nice and ready before Rance visits again?

"What do you mean?"

"I mean, we could do all the prep work and you'd be ready for him."

"Whoa! What do you mean we?"

"I mean I could help and --"

"Hold your horses, Debbie. I don't float that way."

"I know. I'm just offering to help. I have experience in this sort of thing."

"I don't know --"

Debbie lifted the small dildo and the bottle of lube from the box. She poured a little into one hand and began rubbing it up and down on the little plastic rod.

"C'mon, Cheryl. You know this is the best way."

"Well --"

Cheryl watched Debbie's smooth pale fingertips slide along the length of the little device.

"C'mon, Cheryl."

Cheryl sighed.

"Okay. You win. What do we do?"

"I get this nice and oily and you get rid of the jeans. I can't very well shove this in your butt if you're dressed."

"You're so subtle, Debbie."

Cheryl stood, unfastened her jeans, slid them down to her ankles and kicked them free. She inserted her thumbs and popped the elastic of her panties.

"I guess these have to go, too," she said.

"You got it."

She slid her panties down and off. Debbie's eyes fell on Cheryl's chestnut muff and she smiled.

"Can't imagine Rance doesn't want that!"

Cheryl ignored her.

"What do we do next?"

"You get on the couch on all fours, ass facing me," Debbie said brightly.

Cheryl did as instructed.

"This is more than a a little humiliating," she said.

"Oh, what's a bare ass between friends. You have a great one!"

Debbie popped her playfully on her bare bottom.

"Stop that!"

"Here goes!"

Cheryl tensed slightly, felt Debbie's fingers pry her left cheek open, then felt the cool touch of the tip of the little dildo at her hole. She flinched and murmured.

"Hang on, girl."

Debbie rubbed the tiny shaft at Cheryl's sphincter, very gently urging it forward. It was an odd sensation, to be sure, but not entirely unpleasant. The dildo made it slightly past the barrier.

"Oh!"

Debbie giggled.

"And we're in!" she said.

Now she pressed it in steadily but gently.

Cheryl tensed.

"OH!"

"Don't do that, girl! Just relax and take it in."

Debbie began pushing it slightly back and forth.

"How does that feel?"

"It -- uh -- feels -- uh -- weird!"

"But good?"

"Um, a little. OH!"

She undulated the dildo around, reaming the inside of Cheryl's bottom.

"Oh, GOD!"

"So much for a virgin ass, huh, Cheryl? I think your little hole likes it - it's really opening up!"

Cheryl undulated her bottom with Debbie's moves and made little noises.

"Mmmmm."

Finally, Debbie popped the little shaft out.

"Oooh!"

Cheryl started to sit back on the couch.

"Not yet, girl. Hang on a minute."

She began stroking Cheryl's pussy gently, sliding her figures along the slit that had grown moist.

"No, Debbie! I'm not --"

"I know you're not. This just makes it easier, you know -- getting turned on a little. Don't tell me it doesn't feel good."

"Um, it does a little, but --"

Cheryl felt the nub touch her bottom hole again.

"I think I've had enough for --"

Before she could finish, Cheryl felt something big ram into her rectum.

"Wha -- AHH. Debbie! What are you --"

"Hang tight, girl! Call this an accelerated lesson plan!"

Debbie had shoved a big rubbery dildo deep into her and began pumping.

"Oh! Oh, God!"

"You're getting eight inches length and an inch and a quarter diameter!"

"I can't. It's too big! I -- OH!"

But Debbie was relentless, ramming with one hand, working Cheryl's pussy hard with the other.

"OH!!!"

Despite half-hearted protest from Cheryl, the ass fucking went on for what seemed like forever.

Finally, Cheryl fell forward on her face as a hard, hot orgasm shot through her. She grunted and pulsed. Debbie pulled the thing out of her with a wet pop.

"I think you done been ass fucked, girl," she said and laughed.

Then she slapped Cheryl hard on the rump and stood.

"Don't go anywhere. I'll be right back."

Cheryl wasn't about to go anywhere. She couldn't move. She stayed obscenely bent, ass in the air, breathing hard, both holes throbbing, gaping. Debbie walked back in.

"How are you doing, lady," she said.

Cheryl glanced up. Debbie wasn't wearing her jeans anymore. Her white, freckled legs were bare. For an instant, Cheryl couldn't tell what the thing was up by Debbie's crotch. As she got closer, she saw the huge, black shaft with ridges and bumps swinging back and forth.

"Oh, no, Debbie -- I can't--"

Debbie grinned.

"Oh, yes you can!"

Before Cheryl could object further, Debbie was behind her.

"No, Debbie -- please!"

"I think you'll be ready for Rance!" the girl said.

Then she impaled her friend.