Kate Pays the Price Ch. 01-02

"You are something else, Jennifer. I can't imagine being so open about it." Kate confided.

"Give it some time. You'll see. Using plenty of lube is the key. Along with relaxing. You have to learn to relax your anal muscles. What makes it painful is when you tense up or if you don't use enough lube," Jennifer explained as she started squeezing the lube between Kate's cheeks.

"Just relax, beautiful." Jennifer said, working a single finger into her virgin rectum. Kate clenched instinctively and then, took a deep breath, and forced herself to relax. She felt her anus relax and Jennifer's finger probed deeper.

"Good girl," Jennifer said. She worked it slowly in and out several times and then slowly added a second. She patiently worked her fingers in and out of her for a few, mostly pleasurable, minutes. Kate could feel her arousal building and a guttural moan escaped her lips as the jeweled butt plug slid into her anus. It felt more strange than painful. Kate couldn't imagine walking around wearing this thing but apparently, she was going to do just that.

"I think I got you wet again," Jennifer teased. Kate could tell the youngster was enjoying this.

"We'll have to save that for later. Want to do mine?" Jennifer asked, rolling onto her belly and looking at her seductively. "Lube me up and finger my tight little asshole."

"You're so bad, Jennifer."

"You know you love it."

"Mmhmm. Maybe." Kate admitted. Her arousal only growing as she readied Jennifer's anus and then inserted her butt plug.

"You've made me really horny, Kate. I hope these guys aren't complete stiffs and that they have a couple of big stiffs for us. Jack wouldn't have mentioned the butt plugs if they weren't planning on buggering our asses," she joked. Kate had already done the math on that one. Another first she wouldn't be sharing with her husband.

Jennifer picked out their dinner outfits. They would be dining with Jack and two other VIP gentlemen. For Kate she picked out a short black dress from her new collection. This one hugged her curves and revealed a lot of her ample cleavage. Jennifer was wearing a shorter, backless red dress. She looked amazing.

Their dinner companions were waiting for them in a large circular booth set back in a private dining room. Jack was sitting between the two men; they were all wearing expensive looking suits. As the ladies walked into the room, Jack held up a hand, motioning them to stop. The men huddled together for a moment and then Jack waved them over. Kate realized they were deciding which whore they wanted. She was motioned to the seat next to the man to Jack's right and Jennifer sat next to the man on Jack's left. She guessed her gentleman to be around sixty. He was tall and thin, with a full head of salt and pepper hair, neatly cut. Jennifer's gentleman looked to be about ten years younger and more physically fit. His head was shaved clean and he had a few days' worth of stubble.

Jack spoke first, "Why don't you beautiful ladies disappear under the table and introduce yourselves properly. We've had a long, stressful day and I think our friends would be very appreciative." Jennifer gave Kate a wink and slid under the table as directed. Kate caught Jack's insistent gaze and, deciding against protest, followed Jennifer beneath the tablecloth.

The older man lowered himself in the booth, pushing his crotch toward Kate and spread his legs to give her more access. She had no problem exposing the man's penis. He was mostly erect and poking through his boxers when she unzipped his trousers. His cock was short but thick, which seemed odd because he was such a thin man. She clearly didn't know how these things worked. She took his penis into her mouth. The smell was pungent as her nose pressed into his pubic hairs. It clearly had been a long day.

She easily took his full length, giving him a good amount of suction and teasing his balls through the fabric of his trousers with her finger tips. After a few minutes of bobbing up and down, he thrusted his hips forward and began filling her mouth with his watery seed. Kate repressed her gag reflex, almost retching before regaining her composure and swallowing it down. She dutifully milked and sucked the old cock dry before tucking it back into his boxers and zipping up his trousers.

She wasn't sure if she should wait for Jennifer. Luckily, at that moment, Jennifer's head stopped bobbing. The younger gentleman's hands were pulling the back of her head into his crotch as he was no doubt pumping his seed down her throat.

Over dinner, Kate learned that her companion was a congressman from Utah and that the younger man was a political advisor of some sort. Jack ran in some big circles. Kate had two martinis in what she would normally consider becoming a bad habit, but under the circumstances, a necessity.

After dinner, Kate was alone with the congressman in his hotel room. Jack had briefed her that the congressman would be getting back to his wife soon. She was to join Jennifer with the political advisor after she finished her session with her gentleman. The congressman surprisingly brought her to two orgasms, first during oral, where he proved to be very capable with his tongue. She thought this shouldn't be a surprise considering his occupation. The second orgasm was caused by him roughly pounding her in missionary. After she came, he had her get on her knees to finish him. After a few minutes, he pulled out of her mouth and stroked another runny load onto her upper lip and into her open mouth. The congressman quickly dressed and left the room without a word.

Kate downed a vodka from the mini bar, stalling as long as she thought she could get away with, before making her way down the hallway and knocking on the door to Jennifer's room. Jack answered the door completely naked with his shiny and enormous erection swinging. He immediately turned and headed back into the room. As Kate walked in, she could see that both men were having sex with Jennifer. She was riding the political advisor and Jack reassumed his position behind her and started pumping into her youthful backside. Kate was shocked by the scene but also curious at how that must feel.

"Get undressed, Kate," Jack ordered, "you're just in time to tag in for Jennifer."

Oh, God. I guess she was about to find out.

"Are you good, Bob? Want to switch?" Jack asked.

"Sure, let's switch."

"Good call, Bob. I hear Kate has never had a cock in her ass. You get to pop her anal cherry. Jennifer, get Kate ready."

Jennifer bounced off the bed, seemingly none the worse for wear, from having the two strong men working her over. She bent Kate over the bed and gently removed the butt plug from her ass and set it on the nightstand next to her own. She then lubed Kate's ass again and sucked Bob's fairly impressive cock back to full erection before lubing it as well.

Kate's first obstacle was taking Jack's big cock back inside her. Thank God he was on the bottom. Kate couldn't believe how wet she was at the prospect of being taken by two men at once. She'd never been interested in anal sex before but couldn't deny her current excitement, boosted by the foreplay with Jennifer earlier. Jack slid into her easily, filling her up and stretching her again. She rode up and down his shaft for a few long, slow strokes before Bob took his position behind her and placed a hand on her shoulder, pressing her body down flat against Jack's torso. Jack held Kate tight against his body as Bob started pressing firmly into her anus.

"Owwww!... Go slow please," Kate begged as Bob's cock slowly pushed into her virgin ass. She was able to unclench, taking a deep breath, and Bob's cock slowly penetrated her until she felt his body pressed against hers. His cock was much longer than Jennifer's fingers and it was deep inside her.

"Jack, she's got a really tight ass," Bob panted, slowly working it in and out. Jennifer was right. She was now thankful for the butt plug. It was a very unusual sensation and a little painful. It wasn't a bad pain. It was incredibly arousing that a strange man was forcing his cock deep into her rectum for the first time.

"Relax, Kate," Jack instructed, releasing his hold on her body. "You need to get into a rhythm to work both of our cocks." Logistically, it was harder than she would have guessed. It did work better when she controlled the rhythm and then they joined in the thrusting.

"Owwww!" Kate screamed again, this time from a hard spank from Bob. He was not taking it easy on her rectum either, thrusting harder and deeper into her and then spanking her again. Kate groaned as Jack latched his lips onto her nipple and sucked hard. So many sensations all at once was causing Kate's head to spin. Without warning, an incredible orgasm erupted and Kate squealed in a tone she'd never heard. It was primal bliss. Her legs were shaking uncontrollably.

After pausing for a few seconds, the men resumed their thrusting. Kate continued moaning loudly as the men pounded her for several more minutes in a steady rhythm. Bob pulled her head back by her hair, and started pumping wildly. "I'm coming in your tight ass!" he announced, just as she felt his warm fluid squirting deep in her rectum.

After Bob caught his breath and pulled out, he backed off of the bed. Jack flipped Kate onto her back and started pounding her hard in missionary. Kate could feel another orgasm building.

"Fuck me, Jack! Fuck me! I'm coming!" she screamed as the orgasm ripped through her.

"Good girl. Me too!" Jack grunted. He was gripping both of her wrists, pinning her arms to the bed and pounding into her pelvis.

"Do it! Come in me, Jack!"

This sent Jack over the edge. He pumped harder and harder, unloading a torrent of warm seed into her womb. Jack collapsed onto his back beside Kate. After a minute to catch her breath, Kate went down and cleaned his cock and balls, sucking and licking up their juices. She realized she liked Jack's taste and enjoyed this part. She felt Jennifer's face between her legs, giving her a start, as the young woman began eagerly cleaning her.

"That is so fucking hot," Bob observed from across the room, buttoning his shirt.

"Don't be greedy, Kate," Jennifer cooed. Kate knew what she wanted and contracted her muscles, sending a mixture of Bob and Jack's seed into Jennifer's waiting mouth.

"Yummy. Thank you!" she teased after lapping it up and swallowing.

"You ladies are the best," Jack praised. "We're going to have a great time this weekend."

"This weekend?" Kate asked, hearing about the plans for the first time.

"Didn't Jennifer tell you? We're taking a trip to The Island. A private jet and a few days on the beach. Wheels up at eight am tomorrow."