Chaste Challenge

Story Info
Sometimes dreams require a payment.
15.9k words
4.06
17.3k
5
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It was one of those annoying things she did that over the years had just become more of a nuisance and less a true bother, but this was one of those days she was more bothered by it. If she were honest with herself, and she usually was, she would admit it was because she had chosen this day, Friday, June 25, to confront her husband. She had known for just over two weeks, but had tried her best to prepare and not jump too quickly. Now she had her plan and it was time.

Diane brushed aside a stray wisp of the brown hair that fell in soft waves over her shoulders before leaning forward and resting her chin on one hand, elbow braced on the table, and sipping the end of her wine with her other hand. Her green eyes had a hint of brown, light makeup highlighting her from eyebrows to cheeks, and a soft pink lipstick on her sexy lips. The little bit of dress up was a sleeveless emerald green dress, with a square cut, that rested just above her knees as she sat at the table. Her daytime attire had been shorts and t-shirt, matching the late June heat, but Jon was home late, as usual on Friday, and did not have time to change clothes before dinner.

Jon still wore his suit pants, but the jacket was draped over another chair. His tie was loose and the white shirt hugged his fit chest snuggly. He had short hair, combed back and squared at his neck. The wide neck told of athletic glories in days past and his biceps were obvious even under the long sleeve shirt. His face was clean shaven, an annoyance he had submitted to with his promotion to upper management. The paychecks were good, the house was more than comfortable, and he was willing to put in the longer hours required to keep his lifestyle and to keep his wife of 33 years happy.

She set down the glass and dropped her smile. "Jon, I need to talk to you about something." She sat back now, letting the upper bulges of her breasts, squeezed just a bit by a carefully tailored tightening of the dress, show. She saw his eyes lock on to them.

"What's the problem, Diane. Do you need a larger clothing allowance? Maybe the closet full of dresses isn't enought?" He was trying to joke, but she frowned at what she took to be a dig at her. "Sorry, hon, I was just joking."

She crossed her arms under he breasts, pushing them up a bit more and providing a more severe image. "What I have to say does include shopping, though. A couple of weeks ago I was out with a friend and we shopped all morning. Don't worry, I didn't break the budget. Before coming home we stopped in the food court and got some lunch. That whas when I found out." She stopped, leaving it hanging. Waiting.

He took the bait. "You found out," he stretched out the word before ending with, "what?"

"Muriel told me you had asked her husband to help you with something." She let him turn uncomfortably in his chair and clear his throat. "Apparently I was taking too long?"

Now he definitely looked uncomfortable, giving her a sense of immense pleasure. Normally, they had a give and get relationship, without a lot of hiccups since he made enough money to cover any issues on that count. This though, she took personally, so his discomfiture was very rewarding.

"I'm not sure exactly what you're talking about," he managed, obviously trying to avoid something. "Roddy and I talk about a lot of things."

Now she smiled. "Of course you do. You're best friends. And best friends ask their friend's wives to put pressure on their wives, don't they?" There they go, she thought, the eyes. He knows that I know. "What's the problem, husband dear, is your wife too slow agreeing to your desire for a trois?"

Now he was actually squirming in his chair. She had to keep from smiling her enjoyment. "Honey, it's, no, you have it all wrong. I was, it's guy talk. We do it all the, well, I mean not ALL the time, but ..."

He was almost relieved when she cut him off. "Jonathan Franklin, you're caught, so shut up." She paused to make sure she had her mental notes in order. "I don't want to share you. How hard is that for you to understand? I don't want you shoving my little friend down there into another woman. Not at all, but certainly not while I'm watching. We've had really good sex for a long time, and I don't want anybody else knowing what I've got. Don't move."

She got up and grabbed the open bottle of wine, pouring a half a gass into her empty goblet before returning the bottle and sitting down again.

"Have you cheated on me?" Her eyes were locked onto his and she saw them widen, but there was no real fear in them.

"Shit, no. Diane, listen, I've had offers but you're the only woman I've ever dropped my pants for. Well, you and my proctologist." He gave a nervous laugh and she smiled.

"Funny you say it like that. You don't remember that we haven't always dropped clothes? You with an open zipper, me with a short skirt, and, oh my, are you getting hard down there?" He was wriggling and his hand suddenly dropped down below the table top.

He gave a lame smile. "Guilty. OH, shit, guilty of getting hard. I'm thinking of us and that time behind the building in Las Vegas. Not, what you were suggesting."

Time to close the door on her trap and see if he would be inside when it slammed shut. "Yes, about that. I'm willing to give you challenge. If I lose, I'll do your damn threesome. Muriel giggled when she thought about her and me trying to act like we're into women."

Jon's eyes lit up. "You're serious?" She nodded. "And, what if you win?"

She leaned forward, resting her breasts on the table and pushing them so the lacy black bra showed. "If I win, I lock you into a chastity cage on the morning of July 1 and unlock you on the morning of August 1. I've done a little research and kind of prefer the metal cage style to the solid plastic."

He laughed and shook his finger at her, gradually stopping as her expression remained unchanged. "You're serious? But that means no sex for you for a month."

Still smiling, she held up two fingers, thumb extended. "I just can't have sex with you. Not having sex with any men is a choice I will probably make. Or I can see if Roddy wants a threesome with me and his wife and you watch."

"That's just cruel. Why would you even say that?"

She finished her wine in one go. "I would say that, dear husband, because Muriel told me Roddy was jealous that you asked him first if his wife would do a three. And if you're so hung up on getting into another woman, maybe I should consider another man in me. Now, I'm going to count down from 5 and I want your decision. If I don't hear a yes, you lose and you don't get sex until September. If I hear no, then no sex until next year. Any way it falls, I want you to learn I don't appreciate your effort to manipulate me into something I've already said multiple time I don't want to do."

He sighed and slumped in his chair, realizing from the look on her face and 35 years of practice that she was serious. "Ok, yes. What's the challenge? And what do I get if I win?"

"As I said, if I win ,you wear a cage for a month. If you win, I'll do the trois, or even a swap if that will make your little man happy. The challenge is HORSE."

"Seriously? HORSE? Your basketball or mine. Oh, I forgot, you don't have your own ball. I supply the balls in this house."

She stood up. "For that comment I should do something to them, too. Let's get going while it's still light."

He decided to start simple, a few feet in front, and made the basket. She made it. He started moving around, making his first four shots, Diane making all the follows, and then he missed. She took up a position about 15 feet from the basket and put the ball through the hoop. He missed.

"That's H," she said happily. "H for, help me, I'm trapped." She made the next two shots with him following, then she made the third and he missed. "HO. Are you a ho now?"

He was distracted by her taunting and the fact of what the penalty would be if he didn't get his shots dropping better. "That's not a very good joke. In fact, I would be caged, but you might be a ho if Roddy agrees to a swap."

That wasn't the answer she wanted to hear. "So I mention it and right away you want some other guy fucking me. You're an ass. How about a follow on?" She missed her next shot, he missed, she missed again. He made his shot and she missed her follow. "H to HO. Have you got the balls to accept a second round if I win?"

"Yeah, sure, since it's unlikely you'll win this round, we can pretend a second round will happen. What have you got?" He missed his shot.

"Ok, if I win the second round, you will do whatever I tell you for that month in the cage. If you win, then we forget the cage, we forget the swap or three, and we go back to me just being pissed off with you." Her shot went in.

"Just being pissed. Wow, there's a vast improvement." He missed.

"Now you're a HOR," she said smiling as she walked to a corner of the patio. "I have some very mean things in mind for you next month."

They kept bantering, but she was simply outshooting him and it was her HO to his HORS. She missed and it got a little closer, but he missed his next chance.

Diane moved to the farthest corner of the patio, bounced the ball, and shot. He was looking at her skirt flying up and her breasts bouncing and turned just in time to see the ball carom off the backboard and drop through the basket. There was no doubt in his mind he COULD make the shot, but he felt the pressure that he HAD TO make the shot, and it bounced off the rim.

"I guess I need to get online and order something so it's here next week," she announced happily.

He looked at her, his head tipped. "You were just joking, right? I mean, you aren't serious about a cage?"

She walked up and put her arms around him. In their gym shoes he was not quite six feet tall, she was just a couple of inches shorter. He needed a year of dating to accept that in heels she was taller than he was. Now she gave him a kiss on the lips and said, "Look into my eyes, honey, and tell me I'm joking."

His sigh said it all, and he mumbled, "Ok, let me try to win it back."

She let him go first and they once again moved around the patio, making most of their shots, but taking turns missing. When they were both at HOR she was tempted to tell him she had played intramural basketball in college, or at least tell him she had been practicing while he was at work, but she decided to keep it to herself.

"HORS to HORS," he declared as her shot missed. "It's down to a single miss now, isn't it, missy?" He chose a long shot and made it. To his surprise, so did she. He tried again and missed. She took the same shot and made it. The pressure made him try to remember how he focused when he was the high school quarterback. Then he remembered that in his two years in that position, the team was a mediocre 11 - 9. He felt the ball leave his hand, watched it hit the backboard, bounce down, hit the front of the rim on the inside, and bounce back out. He was fucked.

The ball bounced off the cement into the fence to the pool. "Diane, I, please ..."

She walked up and lightly kissed his lips. "I'm going to enjoy July." Then she walked back into the house, lifting the back of her skirt to show she had no panties on as a final humiliation.

=======

Diane made sure she enjoyed the end of June as well. Friday night she celebrated her win with several glasses of wine while Jonathan moped. She did finally tell him she had been practicing for the past two weeks, but pointed out that if he did his best she still won a fair contest. He grudgingly agreed, still asking the questions that showed he wasn't resigned to the cage. Surely she wouldn't do that.

Saturday was a mostly normal day and she made sure they had sex in the afternoon and evening, so he knew she still wanted sex. It wasn't an effort. They had enjoyed a lot of really good sex over the years, and now that she was past menopause, she enjoyed not having to take a week off from sex every month. She didn't get as wet now, but a little tube took care of that, or more often Jon's tongue gave her what she needed for lubrication.

They had sex again on Monday, as dessert to dinner. Once again, she wore a dress with no panties, and this time he was ready to look. Wednesday was June 30, they had a wild time in bed once more, and when she kissed him before going to clean up she reminded him that the next time would be in August. She wasn't sure if she was enjoying the tease too much or not, but she intended to teach him a lesson. That second win, giving her complete control, was what she really needed to make the lesson complete. He would fuss, but he had said he would comply with the terms of his loss, and that meant she could count on him to do so.

Thursday morning, she let him shower and dress, got breakfast together and made him a cup of coffee. He was quiet during the meal. She was smiling. As he stood up after breakfast, she pulled out a red velvet bag and told him it was time, he needed to drop his pants.

As expected, he fussed a little, but he needed to get to work and he knew he had agreed to the terms. Breaking from expectations now would put everything in question, and considering he had started this by wanting a threesome, losing her confidence was not something he wanted to do.

Diane held up a metal cage, bent slightly in an arc. "It's two inches long, so it should hold you nicely unless you get excited about something. On the bright said, no matter how excited you get there won't be any tents down there. And see? No spikes. Tell me how good I am to you."

He had to smile. Considering alternatives, like the one she mentioned, she was being good. "Thank you, honey, for being so nice to me." She knelt and he felt a ring of something wrapped around the base of his cock and balls, then held it together and there was the feeling of cool metal sliding over his limp cock. Some metal on metal as she put the hasp of the cage in place and ran the metal bolt through, then a soft click as the lock closed.

He looked down at the metal cage on his cock, the small lock very visible. "I still can't believe you did it."

"Honey, you're going to be late to work. A man in your position needs to be prompt. I'll have a nice dinner ready for you. By the way, I took the liberty of inviting the Rosarios and Bensons over for burgers and a swim on Sunday. We'll have a small Fourth of July celebration at the pool."

His mouth opened. "Diane, you ... I can't do that with this thing on. What if it shows?"

"You'll be fine. Your swim shorts are baggy enough, and we'll put a drop of oil into the lock before we go to bed. It will be fine. The only ones who will know will be you and me. Especially you." She giggled and guided him to the door.

After he was gone, she got another cup of coffee and opened her computer. She loaded a flash drive and typed in a password, then opened the file with her schedule for her husband's torment. Sunday was just the beginning. If he thought it was a good idea to tell their best friends he was trying to get his wife into a threesome, he needed to learn that was going to create problems.

=======

Sunday afternoon he put on his swim shorts and a t-shirt. He was fit, so when the shirt came off, that wasn't going to be any kind of an issue. He was in the best shape of any of the men who would be there. When Diane walked in and saw him, she started laughing. He was in front of the mirror, checking different angles to see if the cage showed.

"Diane, stop laughing. This is really hard for me."

She laughed more. "That's funny, it doesn't look hard." She ignored the look he gave her. "But I have been curious about it getting hard. Let's do a test before anybody shows up." She quickly walked up to him and pulled his shorts down as she dropped to her knees. Her mouth was on him almost before he realized what was happening and she held his ass to keep him in place while her tongue probed between the bars of the cage. She felt him respond, swelling, then pressing against the cage, then that was really about all there was. She took her mouth away and looked.

"Oh, Jon, you're little man here is pressing so hard against the cage that I think it would leave marks if I took off the cage. But there's an extra bit of metal plating under your head, so I can't lick there even if I want to. I bet this is pretty uncomfortable for you."

It was, but he didn't intend to tell her. "You could unlock it and then it wouldn't be uncomfortable any more." He smiled down at her.

She smiled back, stood, and kissed him. "This can't be any more uncomfortable than having your best friend tell you her husband knows about a fantasy I thought was just between us unless I said yes." She walked away and stripped, pulling three items out of a drawer.

Her husband watched her dress, loving the look of her body. She had been really focused on exercise for the past year and she looked great. Only a few stretch marks gave away hints of the three children she had borne. As she pulled on the bottoms, a nice hip hugger style that wasn't overly sexy, he almost gasped. "You're going with a two piece?"

She slipped the bra over her arms and reached behind to clip it. Again, not overly sexy, a tube style with broad straps over her shoulders in a flowery pattern that leaned to purple. "I wasn't working to get a flat belly so I could hide it, silly. Look, what's under the cloth is still for you. I'm only sharing my hard won tummy." She looked down. His shorts were still at his ankles and the cage was bobbing up and down as he filled it again. "August," she said, "now pull up your shorts and let's make sure the beer is ready."

The Rosarios arrived first. Rodriguez, who went by Roddy, was dark skinned and wore black swim shorts with a "Puerto Rico" t-shirt. His grandparents had come to the country, but he was proud of his heritage and showed off whenever he could. Muriel wore a one piece bathing suit, black, and a button down tropical shirt over it. She showed the effects of her own children with a tummy bulge and wide waist, but was pretty, with wavy black hair falling halfway down her back. In her case, it was parents who had come, but she shared the same pride in heritage and they had passed it to their children.

Jonathan was watching and noticed Roddy had an uncomfortable smile and Muriel kept giving Diane questioning looks. They each grabbed a beer and sat down, exchanging the small talk good friends share. Once they were settled, Diane took over.

"Ok, before the Bensons get here, let's clear things up so you two stop giving me those looks. Yes, I know, yes I told him, and we have an agreement on how we're going to handle that between us. Oh, and Roddy, the answer remains no, so you can put your eyes back in your head and aim them at your wife like a good husband."

Roddy bashfully looked at his wife, who did not seem pleased at how much attention he had given Diane and likely did not want any arguments about how good she looked. He just looked at Jonathan and gave him a smile that said how jealous he was.

Jonathan looked at his wife and finally relaxed a little. He had thought the looks were because they knew about the cage, but her statement was either a screen or they really didn't know and his wife was keeping it private, at least for now.

Art and Greta Benson arrived a half hour later. They were another couple in their 50s, with grown children. Art had shorts and a button down shirt with tropical flowers. Greta, born in Denmark and brought to the country when she was two, wore a two piece that was nice, but not as flattering as Diane's. Top and bottom were a matching pattern to her husband's shirt, with the bottoms being waist high and the top a wider, almost sport bra style that supported fairly large breasts.