Kelly Learns to Beg Pt. 01

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Kelly's journey to becoming a slave to two men.
2.8k words
4.25
19.3k
10

Part 1 of the 2 part series

Updated 06/10/2023
Created 01/22/2021
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Because the conference was at Disney, she'd worn a one-piece, although it wasn't totally modest. The sides were cut high, and the neckline low, and it was a sunny yellow color. This meant that in the hot tub, with those chills brought on by the delicious change of temperature, her hard nipples became obvious. And clearly compelling, because the two men on either side of her - clearly friends, but sitting a polite distance away from her - were staring.

"Here for the conference?" The one with the tattoos asked. Both men were in their 40s, in shape but with a bit of dad-softness over their fit bodies. They looked clean cut, friendly, in a sort of ex-military way. They looked like they were from someplace like Topeka, or Salt Lake.

"Yes, you too?"

"I'm Rob, this is Allen," The both reached out a hand and she leaned over to shake one hand with each of hers.

"Kelly."

They were silent then, sort of smiling, staring into the waters. Some other adults came to the hot tub, trying to escape the kids running everywhere, and both men slid over toward Kelly on the underwater bench until their thighs were almost close enough to touch.

"What do you like to do, Kelly?"

"Oh, lots of things. I was thinking of exploring some of the adult-only nightlife later. I hear there is a party at the tiki bar after 9."

"We are in. May we escort you?"

"Yes," Allen said, "Our wives didn't accompany us this trip. We'd love to make use of our time and have a late night, like we used to."

"Sure. Want to meet me at the lounge at 9?"

"Only if you keep that suit on." Rob smiled at her, and placed his hand on the upper part of her thigh under the water, his pinky finger right up against the line of her suit. He ran his finger slightly, ever so slightly, under the edge.

Kelly shivered. She suddenly felt more turned on than she'd been in years. She couldn't remember feeling this horny since high school. She was wet, sopping, and was thankful that the wetness of her suit would hide it when she got out of the water.

"I have other choices that aren't so wet."

"We'd like to see them."

"Well, I will see you at 9, then."

Kelly stood up. As she climbed up the steps, she made sure to lean over a bit so they could see a hint of her ass in her high cut suit. She squeezed out her long dark hair, and as she did she looked down at herself. Her suit was almost entirely see through. You could see the individual bumps of her hard nipples, the line of her cunt, the shadow of a strip of hair. She stood up taller, wanting them to see her, then she smiled and walked away. Other people were watching, wanting to cover their children's eyes, so she quickly wrapped a towel around herself and walked back to her room.

What the hell was she doing? What on earth were they thinking was going to happen here? She couldn't tell if they had planned some sort of macho competition to see who could win her, or if they were in this together, hoping they'd both have her. Each scenario turned her on, but the latter was so exciting to her, she felt herself flush just thinking about it. She'd never been with two men before, though it had always been a fantasy pushed to the back of her mind. While her sex life had been good, and she and her ex had pushed some boundaries and gotten creative with bondage, roleplaying, and anal, she had always found her head drifting off into more extreme fantasies. But she'd never really thought she'd actually encounter the possibility of one in real life. Was she willing to go that far?

Deep inside, she knew she would. In fact, as she showered and dressed, she practiced how to approach the men, to make them want to take her, together, even if that hadn't been their intent. She chose a black sleeveless dress with a low cut neckline. She wore a thong and a thin bra with tiny cups so that her nipples kept peeking out; if she leaned over, they'd be able to get a view but no one else would see. She wished she had more of selection, or that she'd brought some of her toys from home - she pictured wearing these small nipple clamps under her dress, or inserting a small butt plug for the incredible high it gave her to walk around, knowing that she'd lubed up this small metal bump and slowly pushed it up her own asshole, filling her up. But those she'd left home. She'd just ended a relationship and hadn't thought any opportunity for sex would arise during this boring conference.

At 9 o'clock, she walked into the lounge and saw the two men having a drink at the bar. They smiled at her and waved her over. She leaned in and gave them each a kiss on the cheek.

"A Manhattan, please." She said to the bartender. Allen pulled out a chair for her between them, and helped her up into the high seat. As she arranged herself, she made sure that her dress was pulled enticingly up her thighs, but not enough that they could see anything. "So, how long have you two been friends?"

""Oh, we've been working together for about a decade. We live in the same town, our families spend a lot of time together. We do a lot...together." Rob looked over at Allen as she said this, and it was clear something passed between them.

"How close would you say you two are?"

"Close. We share everything, pretty much."

"Even your wives?"

"God, no!" Allen laughed. "Why on earth would you think that?"

Kelly paused, worried she'd misread the situation, but then Allan leaned over and put his hand on the inside of her thigh. He pushed her legs a bit apart. Rob looked down and continued to start at this as it happened.

"We share most things, but not all. Just...most."

At this point Rob put his hand on her lower back, with his expert pinky inching down, gently rubbing at the top of her thong through her dress.

"Oh, I, um, see." Kelly couldn't get her words. Her drink had arrived, and the bartender looked at her knowingly. She took several long sips. She inhaled, deeply, and a sigh came out of her, almost a small moan. The skin at the tops of her breast turned pink.

"We want to share you. I hope that's clear. What do you think?"

Allen was staring into her eyes. Both men were quite handsome, brown hair, dark eyes, almost nondescript but desirable. They gave off a smell of men, of hardness and of warmth.

Kelly leaned into him, and kissed him softly on the lips. Then she turned, and Rob was there to her left, ready for his turn. Rob she kissed more passionately, she wasn't sure why, except that his lips were open, and wet, and she wanted his tongue.

Then she removed their hands from her and stood up. "

"Well, let's go then. Your place or mine?"

They went back to Rob's room at the hotel. In the elevator up, both men held onto her one of her ass cheeks, gently squeezing. At one point, they both tugged her cheeks apart, in sync, as if they could read each other's mind. Kelly could feel herself spreading open. She wanted to be opened by them, taken and pleasured. She moaned a bit, and the older couple in front of them coughed.

Inside, they made drinks. Kelly flipped off her shoes and sat on the edge of the bed.

Rob handed her a drink and sat next to her on the bed, "Kelly, Allen and I would like to make you feel better than you have ever felt before."

"How would you like to do that?" Kelly licked her lips. She could feel her heart beating hard in her chest.

"I'm thinking we should just show you. That's the easiest way, no?"

Rob took her drink and put it down on the nightstand. He pulled the front of her dress down so the tops of her bra, and her nipples, were poking out. He took a nipple between his thumb and fingers and rolled it, gently, pulling. Then he did the same with his other hand. Allen came up beside them, and Rob tugged her up to a standing position, still gripping her nipples. Allen, from behind, lifted her dress up over her hips. They both paused and lifted it all the way over her head. Kelly lifted her arms and let them undress her. Allen undid the clasp on her bra and Rob rolled her tiny thong down her legs, stopping to gently push his tongue a tiny bit into her slit.

"Mmm, you are so wet already. She tastes so good." Using his two thumbs, he held her pussy lips apart, leaned in, and pulled her clit and part of her lips into his mouth, sucking gently, and then harder. His tongue was rough on her sensitive skin. She felt like she was going to come and she'd been there five minutes. Meanwhile, Allen was behind her, kissing her neck, turning her toward him to kiss her mouth, then back to her neck, all the while manipulating her nipples expertly in his fingertips. Kelly loved nipple play, and she whispered to him, "Harder. It's okay, I like it." He squeezed, pulled, then took his hands away, lightly brushing her. Then again, hard and soft.

She had never been so wet in her life. She was moaning, oh god was she moaning, and the men weren't even undressed. Something about that made it hotter, the idea that she was this wet naked slut and they were still professional, upstanding, licking and pulling at her body. She realized she was grinding against Rob's mouth, almost like she was fucking him.

Allen stepped away and started removing his clothes. Rob pushed her down onto the bed, not hard, but with intent.

"Open you legs, I want to see you."

Kelly spread her legs, her ankles near the corners of the mattress.

"Allen, you need to look at this cunt. I have never seen a more beautiful wet cunt in my life. She wants this. You want this, don't you?"

Kelly nodded. Rob took off his shirt, then his pants, never taking his eyes off hers. She couldn't help herself and looked down towards the end of the bed. His cock was big and thick, and he put his hand around it, stroking it as he climbed onto the bed.

"You like this cock?"

"Yes, very much."

"Because I'm going to fuck you with it now, if you ask me nicely."

Rob rubbed the tip of his cock on her clit. She gasped. "Please, I want your cock inside me. Please. I need it."

He pulled her knees in closer, so her cunt was at the edge of the bed. In one hard thrust, he was inside her. She held his gaze as he pumped in and out of her, pulling her towards him with each movement.

Allen had climbed on the bed next to her, sort of curled up. They kissed passionately, she felt like she wanted to devour him, and then he started gently slapping her clit with his fingertips, in time with Rob's thrusts.

"Oh god, don't stop, I need to come."

"Please, baby, come. It won't be the first time."

Kelly's orgasm felt like it would never stop. She was pushing so hard against Rob's cock and Allen's fingers, while sucking in Allen's tongue, she felt she might hurt someone. She wanted them all over her, inside her, everywhere.

When she finished coming, Rob pulled out, his cock slick with her dripping juices. "Your turn," he said to Allen.

"Get on your knees."

Kelly flipped over, her knees so weak she could barely support herself. Allen turned her around, so her hands were close to the edge of the bed. He climbed on and slid his enormous cock in her wet slit. It was so incredibly big she didn't know if she could take it, she hadn't even noticed when she'd been absorbed with Rob's fucking. Rob, standing at the side of the bed, brought his cock, slick with her come, and said, "I am going to fuck your mouth, and you are going to taste yourself, and you are going to like it." Kelly nearly came again just with his words.

She sucked his cock into her mouth and let him fuck her, causing her to gag a few times. Ropes of spit dripped down her chin, her neck, falling from the ends of her nipples onto the bed. The sensation of her cunt being pounded on one end, and the taste of her own sex being forced down her mouth, was overwhelming. Allen reached over and rubbed his hands over her tits, wetting his fingers with her saliva. She realized what he was going to do, and looked up at Rob.

"Yes, pet, it's too tempting, that ass."

And then Allen was pressing an index finger into her tight ass, just a little, wiggling it down, towards her cunt, which was filled with his cock. She wondered if he could feel the heft of himself through her skin, feel the ropes of the veins of his cock as he pushed in and out, his finger pressing and moving firmly in her ass.

"She likes it in her ass. She's practically begging for it." Allen and Rob smiled at each other and Rob reached over her back, his cock still in her mouth, and pushed his finger into her ass alongside Allen's. They were rocking her back and forth, pulling her towards them, their fingers like hooks in her ass. She started to come again, making inhuman sounds, moaning and guttural, just as Rob spurted his come into her mouth.

"Swallow it. I know you want it."

She drank his come, the salty manliness of it, as she came, feeling her own liquid drip down her legs, hearing the squish and slap as Allen's balls glanced against her clit. She was straining the last few pulses of her orgasm when Allen pulled out and came on her ass.

Rob pulled his cock out of her mouth. "Arch your back and stick up you ass. I want to watch the come drip off you."

She did as commanded. Allen went to the bathroom and came back with a wet washcloth. But before he wiped it across her skin, he swiped his fingers through the come, and held them up to her lips. She took his fingers into her mouth and sucked off the come.

"You are such a good little slut. Rob, how did we get this lucky?" He started wiping away the come on her ass.

"Kelly, you can lay down now."

She flipped over onto her back and Rob and Allen lay down on either side of her. The both caressed her body all over, gently, teasingly, their fingers stopping at her nipples, at her clit, at her inner thigh.

Kelly had never felt so much intense pleasure in her life. She didn't want this to end, but she wanted...more. It was clear that the men enjoyed being in control, and also that she liked submitting to it. She wanted it to be harder, more transgressive, more...bad.

"How long are you two in town?" She asked, feeling silly to ask such a mundane question.

"Friday." So, two more nights.

"I am wondering something, but I am afraid to say it because it might be too forward, and you might not like that."

"Ooh, I'm intrigued. Rob, what do you think? Can she risk it?"

"We want to hear."

"Well, I enjoyed how you dominated me. Told me what to do. It turned me on more than anything I've experienced. And I was thinking that maybe, tomorrow, or the next night, or both nights, I could give myself to you as your...your...slave."

"You are a bad little slave to ask to be a slave! But. We will consider that."

"However, it is your job to go out and secure anything you think we might want to use to play with you. Do it tomorrow, and then meet us back here at 8. Choose well."

Kelly stood up and slid back into her clothes. Both men kissed her and she walked towards the door.

"Kelly, are you sure?" Allen asked. "Really sure? Because we will make a plan if you are, and it may be more than you bargained for."

"Yes, I want this. More than anything."

She walked out the door.

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3 Comments
AnonymousAnonymousabout 3 years ago
mmm

Best story ever, made me begin masturbating. Can't wait for the next chapter.

DeathMaidenDeathMaidenover 3 years ago

Love how Kelly isn't so afraid of her sexuality and goes for it... especially with two men!!

AnonymousAnonymousover 3 years ago

Promising start. Hope future chapters maintain this level of playful erotic fun.

Cheers and thanks

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