Who's the Bitch Now?

"Now Jack, what I want you to do is kiss Amy's asshole. Show Amy you understand where your place should have been in the relationship." Amy was surprised. Jack would barley lick her pussy, but he never wanted to do anything with her asshole but fuck it. Amy lowered her panties from under the short skirt she was wearing. She got down on all fours and backed her tight ass up to Jack's face. She looked back and made eye contact with Jack for just a moment. His face was as red as his ass. Jack hesitated for a second and Linda slapped his sore ass hard. That was all it took. Jack started peppering Amy's ass with kisses.

"Good Jack, but not good enough." Linda said as she smacked his ass again.

This time Jack started kissing Amy right on her asshole. Another slap on Jack's ass got him to stick his tongue into Amy's asshole. Both women burst in to laughter at Jack's eagerness to lick Amy's asshole to stop from being spanked. Finally, Amy pulled away. She patted Jack on top of his head in an approving manner.

"Jack, the very last thing we need to talk about is anal sex. Amy told me that you are obsessed with the thought of it. Is that still something you want?"

Jack thought long and hard about his answer. "Many women enjoy it. I don't think it's a bad thing."

"True," Linda replied "but only when it's consensual. Otherwise, it's just degrading."

"I don't think it's degrading. It's just something fun a couple can do." Jack answered still being careful to not upset Linda.

"Ok Jack, why don't we stick something up you ass then?" Linda said with a grin. Amy put her hand over her mouth to stop from laughing at the thought of Jack getting it in his ass.

"No..no.. No I don't want that." Jack repeated as he shook his head no.

"But why? You said it wasn't degrading. You said it was fun. Certainly if you expected Amy to do it you would be willing to do it too."

Jack knew he was trapped. "But, she's a girl."

"So, everyone has an asshole. They all stretch. You even have a prostate back there to stimulate. Can you think of a reason why she can and you can't?" Linda reasoned.

There was a long silence. Jack couldn't come up with an answer. Then Amy piped in, "what if we just stick the tip in?" Both girls burst into laughter knowing this was the exact line Jack, and many men, use to try and talk women into anal sex. Jack knew this was the best deal he could hope for.

"Ok, but just the tip. You promise?" Jack said reluctantly.

"Of course Jack. I'll only put the tip in unless you ask for more." Linda said elated that her plan had come full circle. She left the room and came back wearing a flesh colored strap-on dildo with a pair of fake balls.

"Jack, Amy told me why she left you. When the postman delivered your anal DVD's to me by accident, I knew I had an opportunity. I ran out and bought the chastity cage and this strap-on dildo. I wasn't sure you would put the cage on but when I bumped into the other day I knew you had."

Linda showed Jack the dildo. Jack gulped at the 8" size. "Just the tip," he reminded her.

Linda lubed up the dildo. Then she stuck a lubed-up finger into Jack's tight, virgin ass. Jack grimaced at the feeling. Next Linda positioned the dildo right over Jack's anus. She applied some pressure but it wouldn't go in.

"Relax, Jack. Trust me, your going to love this!" Just as the words came out of her mouth enough pressure had been applied to force the dildo into Jack's asshole. Linda watched as the tip of the dildo spread Jack's rim open and slid in. As soon as it went in, Jack's head popped up and he let out moans of pain.

"Just relax Jack, only an inch or two went in. The pain should go away soon. Tell you what, why don't we let you out of your cage." Linda handed Amy the key as Linda stayed behind Jack with the tip of the dildo stuffed into Jack's hurting ass. Jack was still tied on all fours so Amy had to crawl under to find the keyhole. Soon, Amy had unlocked the cage and removed it. Instantly Jack's dick became rock hard.

"Oh my," Amy said as she saw his dick become erect. "Somebody really likes getting it in the ass." Linda laughed.

Jack's face turned redder. "I can't help it. My dick has been locked up for over a week. That's the only reason."

Amy reached under and took hold of Jack's dick. "I've never seen it this hard before though." both women laughed again.

Slowly, Amy started stroking Jack's dick. It felt so good he forgot about the dildo in his ass. Suddenly, Amy stopped to get a better grip. When she did Jack started trying to hump her hand. He was desperate for release.

"Hold on Jack," Linda spoke up. "If you keep humping like that you are going to hump this dildo right up your ass. Is that what you want?"

Jack needed release. "Please Amy?" he begged.

"Answer Linda first." Amy demanded.

It was clear that if he answered "no" he wouldn't get any relief. "Fine," Jack grunted.

"I promised to only stick the tip in, Jack. I need to hear you say it." Lind asaid with a smirk.

Amy waited. She just couldn't believe what was happening.

"It's ok if the dildo goes in more." Jack reluctantly said.

Linda nodded for Amy to grab Jack's dick again. Amy placed her hand on Jack's member but didn't move it and kept her grip very loose. As soon as Jack felt Amy's hand he started trying to hump it again. Linda leaned forward putting more pressure on the dildo. With each hump Jack's asshole gobbled a few more inches of the strap-on.

"Oh my Gosh!" Linda screamed. "Jack you have all eight inches up your ass. It's balls are touching your balls. I can't believe you are such an anal whore. You took it all so easy." Linda motioned for Amy to move behind Jack to take a look. Even when Amy removed her hand, Jack kept humping for a few seconds. Jack had never been so desperate to cum in all his life. It was only after Amy let go did he feel the full effect of the dildo in his ass. It hurt a bit but mostly it made him feel full.

Amy looked at the big dildo buried to the balls in Jack's ass. She couldn't hold back her laughter.

"This is what you want to do to me, Jack? How do you like getting ass fucked by a girl? Judging by you actions you must love it." That's when she watched Linda pull the dildo all the way back out until just the tip was left in. Then Linda slammed all eight inches all the way back in. Jack groaned as Linda repeated the action. Soon Linda had found a rhythm and was stroking the dildo in and out of Jack's ass. Amy watched as Jack's asshole got smaller when the tip came near then was stretched wide open when Linda shoved it in.

Before long, Jack could feel the dildo pushing over and over on his prostate. It made him feel like he was going to blow his load. The only thing he could think about was getting relief, cumming. He started humping the dildo back in hopes that he would somehow get some friction on his dick, but all he felt was air. The girls laughed and ridiculed him as he desperately humped the dildo with his ass.

Then it happened. Jack felt his dick about to explode. Amy recognized the noises he was making.

"Oh my gosh! I think he's going to cum. He's going to have an anal orgasm!" Amy yelled in complete shock but with much delight.

Jack humped furiously waiting for the moment to arrive but incredibly frustrated he couldn't get any friction on his dick. Then, Jack stopped humping and tensed up. Linda continue to pound his ass. Amy looked under Jack to see Jack's dick shooting more cum than she had ever seen.

"He's cumming! He's cumming from just being fucked in the ass!" She squealed.

"Who's the bitch now?!" Linda screamed as she slapped Jack's sore, embarrassed, humiliated ass.