The Roll of the Dice

Robert Roe
  • 3.2 (9)
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The Roll of the Dice

Hi, I’m Cindy. The “Roll of the Dice” story evolved after I agreed to be the Mistress in my boyfriend’s chastity slave fantasy. Our sex life, after five years together, was no longer much to brag about, so I thought I had little to lose by going along with his game. Who locks their stuff in a cage and gives the key to their girlfriend? So, I held my nose, learned to love denying him, and started an unexpected erotic journey. Wow, who would have thought it would become my fantasy and I would say no to his begging? https://podcasters.spotify.com/pod/show/mchastity/subscribe

  1. 07/27/2023

    18.  Cindy and Teri Do Lunch

    “What was so urgent, Teri, that we had to do lunch today?  Is Gene not taking care of you, Teri?  I saw you added six days to the calendar; what’s up?” “There is no real problem with Gene.  I wanted to cuff his hands behind him and then sit on his face, and he said no.  But, he will come around.  It is kind of fun adding days to his sentence.  I don’t think he thinks he is really going to be in the cage that long. I think we need to have serious talk with him and convince him he is going to be in the cage for two months, and more if he doesn’t start being a better chastity slave.” “Is that what you want to talk about?” “No, I’m just stalling.  Just one more side topic, you don’t care that I cuff him and sit on his face, do you?” “He says he feels like he will suffocate when you sit on his face so long.” “He’s not going to suffocate; he just thinks he is.  I am careful, I watch the clock.  I never make him go more than a minute and a half.  Except maybe when I am getting close to an orgasm, and I kind of lose track of everything.  It just scares him, he's okay." “Wow, you have a sadistic side.  Maybe I need to watch one of these sessions and see if it is safe for Gene.  Although I have found he’s bringing that side of me out, too.” “What side is that?” “I don’t know.  I feel kind of mean when I have him go down on me and I can see the desperation in his eyes.  Part of me feels guilty and I want to free him.  But a bigger part of me enjoys that I am putting him through this.” “It turns you on, doesn’t it.” “Yes, but don’t you feel guilty sometimes what we are doing to him?” “It is what he wanted.” “Yea, but he had no idea what he was getting into, did he?” “A man and his dick get in a lot of trouble.  I am not sure as women we can understand what a man will do to keep his dick happy.  And so far he is still wading in deeper.  I heard he’s got the hots for someone at his work.  His brain must tell him that every time he gets worked up his condition gets worse.  But his dick tells him something that makes him just go for it.  Sometimes as women, I think we just have to respect what the dick wants.” “You are calling it his condition, too?” “Yea, Gene told me you called it His Condition.  It fits.  He is becoming an addict.  He wants to go down on me, and you, and every woman he sees, but it doesn’t satisfy him.  Like an addict, he always needs another hit that is bigger and more frequent.  That is his condition as I see it.” “So, should I worry about Gene suffocating?”   “I don’t know, I kind of get lost in the experience. But he has never passed out.  I mean he is still kicking and twisting around. And he is fucking the air at the same time.  You should try it.  It is a huge turn-on.  I have unbelievable orgasms.” “I don’t think so.  But I can see that it must be a hell of a turn-on for you.” “Why not?  Watch me do it one time and then try it.  Or maybe, we could rotate on him.” “I am not sure I would trust myself.” “You are feeling the same thing I am feeling.  Our power over him.  Does that turn you on as much as it does me?” Cindy found herself thinking about sitting on Gene’s face and him struggling below her.  She was smaller and lighter than Teri, he would probably just fling her off even if his hands were cuffed.  Maybe she could tie him down on the bed?   Her hand went to her crotch, she was suddenly very turned on thinking about all the things she could do with Gene while he was in ‘his condition.’”   She changed the subject. “But that is not what you wanted to talk to me about?” “I am sorry, but Jim got me messed up, and I spilled the beans.”

    15 min

  2. 07/20/2023

    RTD Chapter 17.  Gene and June Do Breakfast

    Gene and Cindy avoided each other for the next few days and nights.  Gene knew Cindy was still upset with him, but she had not mentioned him going away for a few days again, so he just kept his head down and hoped she would forgive him.  He slept on the couch, and she slept up in their bedroom.  Gene woke up every few hours with a hard-on and half-waking dreams of June and Cindy.  He was afraid to bring up the keys to her again so he just tried to keep his mind off of anything female while he was awake.  He had no clue what to do about his dreams and the pain of night time boners in the cage.  He had fallen into drinking more coffee to compensate for the interrupted sleep, but the coffee made the edginess he felt from being horny all the time even worse.   He tried to remind himself of the fantasy he had before he was locked up.  He had imagined serving his Mistress while he was in a cage.  That somehow seemed more romantic and awesome in his fantasy than in his head.  He had imagined a kinky Mistress who teased him constantly and paid him a lot of attention.  Well, Cindy had certainly evolved in a kinky direction, but these days the only attention he got was her opening her legs and expecting him to dive in, which he did.  His erection seemed to get harder and more painful with time and it was hard to make it through the longer sessions with Cindy.  Teri was definitely an unexpected bonus, but he felt very used by her.  She had strong legs that clamped around his head and kept his face buried in her pussy until she got tired of coming.  He was afraid of when she cuffed him and sat on his face.  At times he thought he would suffocate and it was strange how her abuse made his dick so hard and for so long that he wondered if the effect of the near suffocation was permanent the first time it happened.  In short, Teri made him feel like a real slave. The bright spot of being a chastity slave Gene decided was how liberal Cindy had become about other women since he was in the cage.  He was optimistic that his relationship with June was evolving and would include sex after a while.  He tried not to think about sex with her too often because the end of his dick was getting sore from pounding into the end of the tube so often.  The game overall was doing a number on his head.  He was kind of getting more than he had hoped for: a kinky, sexy and liberal Mistress, plenty of sex, at least oral sex, and new women coming into his life all the time.  Something had changed in him and women were responding to him in a way that had never happened before.  Some seemed freaked out by how he looked at them, but many of them seemed drawn to him and hung around him.  He had noticed them standing closer and looking up at him as if they were waiting for him to say something or make a move.   But what should he say, he was never good at these things.  His logic told him he already had more sex, well oral sex he reminded himself, than he could handle.  What did he really want to do with these woman and did they really want him to go down on them or was he just going further down the rat-hole of lust-insanity.  He kept telling himself that the constant urge to fuck was worth all the sexual attention he was getting.  He kept reminding himself that he couldn’t get any more frustrated and that he would still have this harem he was building up after he got out of his cage.  Cindy would get used to him having a harem and it would all work out if he could just endure the journey.  He as not really going insane he told himself a dozen times a day. He also told himself he would feel better if he stopped thinking about sex so much and focused on his job and other stuff he had to do everyday.

    19 min

  3. 07/16/2023

    16. Applebee’s Bar

    Cindy was waiting for him at the bar.  She was in a short red sundress that rippled gently in the breeze when she stood below the single fan that was above the stool she had selected at the empty bar.   The dress was buttoned up in the front, and Cindy had unbuttoned all the buttons down to her navel.   The thin red material gently covered her breasts as long as Cindy sat up straight. She knew when she leaned forward that anyone on the side of her had a good view of her breasts.  She casually opened the dress and looked down at her nipples erect from the cool breeze of the fan above her head and her excitement about what her red dress would do to Gene.  She resisted touching herself, amazed at how much her new perversion kept her turned on.  She realized she could no longer call it just Gene’s perversion.  She loved what she could do to Gene since she had put the cage on him.   Her power over him was real.  It was so easy to get him so turned on that he could not function.  She looked forward to the escalating loss of control he would experience sitting next to her as she selectively flashed parts of her body at him and sat in less than lady-like poses in front of him. What she found inconvenient was how very turned-on this game got her.  She was sucking through a small straw from a drink that was colored orange and red and was mostly gone when Gene arrived.  He gave her a quick peck on her lips. “What's up?” she asked. “Nothing, really.” “Ok, let's spill it.  I have been imagining all day what you want to tell me.” Gene blurted out, "I kissed June." The comment did not seem to register with Cindy. “who is June?” she asked. “I go to lunch with her; we watch birds together.” “Where?” “In the park, two blocks from my work.” “Today?” “No, for a while.” “A week, what? You are not making sense.” “We have been watching birds together for about three months?” “And kissing?” Gene tried to focus harder on what he was saying, annoyed he could not ignore how tight the cage had gotten sitting by Cindy. “No, I mean, yes, we've been watching birds together for three months. But we only kissed today, and oh yeah, and on Monday.”   “Why haven't you ever told me about her?”

    19 min

  4. 07/01/2023

    RTD15 Gene's Lunch with Anne

    Cindy’s body shook with the last of three orgasms.  They were running late and said nothing as they headed for the bathroom seconds after Cindy’s body stopped shaking.  In the shower, Gene stood behind Cindy the water coming over her head hitting him in the chest.  He leaned against the shower wall his legs unsteady and his hips still jerking every once in a while with an involuntary fucking motion.  He asked Cindy, “how is this game working for you?” “I haven’t had this great of sex in forever.  Who am I kidding? This is the best sex I have ever had.  You are fabulous.  It is like you can’t get enough of me.  Sometimes you get a little rough with your tongue, but it is good.  No, it is great.  How are you doing.” “I’m struggling.  I don’t know how much longer I can do this.” “Are you really having that much trouble standing up, and what is with that jerking you are doing?  This is just Wedneday, your fifth day.  You have to be kidding me.” “It takes everything out of me getting so turned on, and so close and then not being able to get off.   I am shaky all over.  It feels horrible.” “Well maybe you should not go so ape-shit over my pussy.  You are like a crazy man, but it is good for me.  Maybe not so much for you.” “I have no brain during sex. I just want you so damn much.  I want to f**k you but I love making you come with my tongue too.” “I can see you want to f**k me, your body is still trying.  That is so damn sexy.  I wish we had more time and you had the strap-on ordered.  You are going to love fucking me with it I bet.  I can imagine you going until you are exhausted.  It should be illegal how wet you keep me since you have been in that cage.” “God you know I can’t keep doing this.  It is making me crazy wanting to fuck you all the time.” “I notice you touch yourself, or the cage, all the time, even in public.  It is embarrassing.  You need to get a grip on yourself.” “I’m horny as hell, you know that.” “But touching yourself doesn’t help anything. You don’t need to let the whole world know you are horny.” “I don’t even know I am doing it most of the time.  There is a constant urge to press against something, anything.  Sorry, I will try to be more aware of my surroundings.” “I understand, how could you not be horny as hell. I can’t believe you are into this kind of kink.  I bet you get better the hornier you get.  I may never let you out. By the way, ten days got added to the calendar because you promised me twice you were ordering the strap-on, and it didn’t happen.  I rolled it twice and got two fives. Good news is that you are meeting your quotas with me and Teri and you are well on your way today.  So you seem to be getting the hang of life in the cage. I didn’t penalize you for not getting your quota on Monday, that was my fault with Jim.  Thanks for being cool about that whole thing.”

    22 min

  5. 06/22/2023

    RTD 14 Cindy Meets Jim

    14.  Cindy Meets Jim Cindy on the way to the bar, regretted the outfit she had put together that morning to meet Jim.  She enjoyed watching Gene get beside himself when she held up the dress to fuel his imagination.  She had gotten the dress out of the back of her closet from her college days almost 15 years ago, and admittedly it looked very short.  “But how short can it be since I used to wear it” had run through her head as she held it up and watched Gene’s imagination go ape-shit.  She knew his imagination could have a more powerful effect on him than her actual body in the dress, so she had not tried it on.  As she had folded the dress and put it in her bag, his hips had involuntarily jerked, and she had experienced a small orgasm.  It was a first for her; she had never had an orgasm from someone lusting after her from a distance. It was made sweeter knowing Gene was desperate to get off and couldn’t.  Seeing him stutter and the robot-like motion of his body as he tried to be cool had kept her on the edge of a second orgasm.  Her sex life was just not that hot, well until this sick game had opened all these crazy doors inside of her brain.  Behind each door was an idea so bold that she felt like orgasms were lurking for her around every corner.  It wasn’t like she had never had the ideas before, but something almost magical had occurred between her and Gene.   It felt to her like their two groins were connected.  She could feel the pressure build in Gene’s groin along with the sensitivity of his penis.  She even felt his urge to push against something, anything, to get relief.  And emotionally, she felt his desperation to escape urges and compulsions that were too difficult to endure.    The flow of feelings seemed to go both ways.  When she had come, Gene’s face had experienced a level of pleasure that mostly registered as pain on his face.  The wave of sensations had rippled back and forth between them.  Her groin had never been connected to a man’s groin that responded to not only what she did but what she felt between her legs.  It was as if she could feel his desperation between her legs.  She had never felt a sex drive as powerful as she was experiencing every time she saw and felt Gene red-line;   what she felt was a mix of pure animal lust and a desperate agony to release an orgasm that demanded release no matter the circumstances in her life at the moment. It was as if she could feel Gene’s penis slamming against the end of the cage and his muscles tighten in his groin and buttocks as he tried to resist f*****g the air.  It was overwhelming the desire that built in her groin and demanded to be released in some decadent show of sexuality.  Knowing that she only could get relief from the lust building between the two of them intensified the urge in her to where despite her best efforts she gave in and did what was necessary to come.  She got two waves of endorphins from what happened as she came.  The first wave was her own powerful orgasm, the second came from Gene as a wave of agony went through him when his body tried to come with hers but only a sharp pain shot back to his balls as his ocean of semen hit the kink in his penis because the cage folded his penis downward.  She got smaller waves of endorphins as aftershocks went through his body, and the sexual tensions inside him raised to a new higher level.  Seeing the contortions on his face contrasted to the waves of joy that flowed through her.   It was almost too intense pleasure to endure.  She didn’t understand what was happening but she wanted it more with each day that passed.  And even when Gene wasn’t there, she could see his body contorting as his psychic pushed pleasure from him to her.

    21 min

  6. 06/08/2023

    RTD 13.  Monday Blues and Birds

    Gene woke up in a deep fog Monday morning.   The night before, he was exhausted and fell asleep quickly after Cindy went upstairs only to wake up with a series of erotic dreams through out the night.  The scenario in the dreams changed but he was always looking at white thighs and pussies all night.  Sometimes he was out on a date with Teri and she had a remote vibrator in her or he was watching Cindy walk down the mall nude.  Most times he did not fully wake up but simply fell back to sleep in another fantasy of a pussy just out of reach.  But three or four times he woke up completely.  He found his shoulders and wrists aching from the cuffs and his dick hard and pulsing with his thoughts mostly on Cindy.  He knew she was waiting for him upstairs but he was so tired.   In his entire life he never remembered being hard for as many hours as he had been this Sunday.  The constant sexual tension had left him where his entire body felt heavy and only his dick seemed to still be alive. He lay there awake picturing Cindy lying legs wide open her body nude underneath her night light.   She didn’t normally sleep nude, but she had told him she would sleep nude as long as he was in the cage.   He could remember her saying, “when you wake up I want you to think about me and stay hard.” Why did her saying it make it true.  As he lay there his dick hard and throbbing he knew that somehow she had believed she had this power over him and it had become reality.  He did not want to believe she had this power, and she wouldn’t if he could just not think about her lying up there with her perfect body nude and a big evil grin on her face.  He knew, that she knew she was making him hard.  It was the mutual knowing that made them both turned on but the sexual intensity was on another level for him because they both knew he had no way to relieve what had become his personal and growing agony.   His agony bound them together even when they were apart; she knew he ached for her and he knew she felt great pleasure in knowing he suffered from wanting her.  Her nudity and evil half grin was her way of telling him that she owned him and that she controlled his dick.  He knew every time she woke up she would smile thinking what she was doing to him, or perhaps even laugh outloud.  And somewhere tomorrow she would remind him of her powers.  He lay there struggling against her powers.  The only way that seemed to work was concentrating hard on something else, but not too hard or sleep would not come, and replacing the thoughts and images he had of her body with thoughts about this new object.  The sad state of affairs of his income taxes worked the best but it was not compatible with sleeping.  Finally a breathing meditation allowed him to return to sleep only to wake what he guessed was a couple of hours later with more thoughts of Cindy and another persistent erection.  Without the cage being there he could just masturbate and relieve all this tension.  He guessed that it took him thirty to forty five minutes to get Cindy out of his head enough to get rid of his erection and go back to sleep.  As he finally passed back out, he told himself over and over that her power over him was not real.  All he had to do was not think about her perfect ass and her sexy confident attitude when a nightly erection woke him up.

    54 min

  7. 06/04/2023

    12 Cindy Enjoys Gene’s Helplessness

    “So, I guess I stay cuffed all night.  It is hard enough sleeping in this cage.  It is about seven thirty; perhaps we could watch a movie and try to unwind from the Jim incident.” “I thought you were going to say unwind from Teri.  How was that for you? Did you ever think I would let you be with another woman, even encourage it?” “I felt like I was just being used as a sex toy.  I am still rattled by her getting me all turned on, and she was so close to coming, and then Jim showed up.  I am still hard in the cage.  And you, I don’t even know you anymore.  I have never seen this side of you.  Couldn't we just fudge the rules a little?  I mean, I really appreciate you going all in on one of my long-time fantasies. In fact,  you have gone way beyond my fantasy. Maybe,  you could take the cage off, f**k me, and then put the cage back on.  I’m in the cuffs, and I’m not going anywhere.  You will surely be able to put the cage back on me.   The fantasy is for me; shouldn’t I be able to make some changes in the way it plays out?” “If I thought you could f**k me without coming, then I would consider it. I can’t believe I am saying this dear, but I don’t want you to come. I never dreamed your fantasy would be this much fun.  I think it may have turned into my fantasy.  To be honest, I am really into this being a Mistress, much more so than being an innocent Princess. Who would have thought?  So, yes, it does matter to me that we stay true to the spirit of the fantasy.  I am really committed to giving you the experience of being a chastity slave, and well, letting you change things because it is a little harder than in your fantasy, that is just not okay.  I am developing my fantasy of what it is like to be a Mistress.  I can’t believe I got Teri to agree to be my slave.  I don’t even know what to do with that. And will she really do what I say?” “I could do it, not come I mean.  I could tell you when I am getting close, and you could get off.  It would feel so good to be out of the cage with a full erection, even if I didn’t get to come.  Wouldn’t you like to feel my dick inside of you all hard and pulsing?” “Yes, it would feel good.  But you are not even listening to me.  Pay attention, I like the way your fantasy is unfolding.  Let’s say I don’t have any confidence in your abilities to stay in control.  After all the teasing you have been through the last two days, no way are you going to keep from coming.  Your tongue will have to serve me.  And what happened to ordering that strap-on?” “I’ll order the strap-on tonight, promise.”

    37 min

  8. 05/28/2023

    RTD Chapter 11: Gene Couch Bound

    Teri jumped from the car and streaked to Cindy and Gene’s back door only to have to wait until Cindy got there a couple of minutes later. “Did you leave me standing out here nude on purpose?” “No, I was trying to encourage Gene to get out of the backseat of the car.  I don’t know what’s in your pussy, but he’s all curled up and mumbling and not all that coherent.” “He’s getting worse.  I bet he went forty-five minutes this morning before he started shaking and still he managed to go another twenty minutes before our first break.  I don’t think he made ten minutes on the car ride before he couldn’t go anymore.” “He’s your slave, and if he doesn’t finish the job, it's up to you to punish him if you think it appropriate.  With both of us using him, and with him getting wound up tighter every day, I think he’s gonna struggle.  Did you try just pulling his head into your pussy?” “No, he was holding his crotch and mumbling he couldn’t do it anymore.  And doing all that shaking stuff he does when he’s f*****g the air. I have never seen a guy lose it like that. And he is like this after just two days of being denied?” “I think it has more to do with how turned on you had him at the IHOP.  You had him looking at your beaver the whole time, except when he was looking at your boobs.  It is impressive how well you can tease a man.  And,  it's got to be a little disconcerting for him to have his body fucking the air and unable to get off when you are moving toward your umpteenth orgasm today.  You just need to guide him to your pussy and his instincts will take over.  You can’t start feeling sorry for him because he can’t get off.” “I don’t think I was getting soft on him. I think he had me so turned on the way he was f*****g the air and moaning that I was in some alternate reality.  I think I was f*****g the air in my own way.  But are you saying I should use the dice because he couldn’t continue?” “I am saying he has to learn to push through his own arousal getting the best of him. And you need to demand that he takes good care of your needs.”     “So, could I use him a little longer?  Can I have a redo? And can we talk after we get inside?  And I am not really comfortable standing out here on your deck nude.” “Sure, but first, I order you to go back to the car and drag him in here and then do with him as you like.” “Can I put on a T-shirt first?”

    35 min
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Ratings & Reviews

3.2
out of 5
9 Ratings

About

Hi, I’m Cindy. The “Roll of the Dice” story evolved after I agreed to be the Mistress in my boyfriend’s chastity slave fantasy. Our sex life, after five years together, was no longer much to brag about, so I thought I had little to lose by going along with his game. Who locks their stuff in a cage and gives the key to their girlfriend? So, I held my nose, learned to love denying him, and started an unexpected erotic journey. Wow, who would have thought it would become my fantasy and I would say no to his begging? https://podcasters.spotify.com/pod/show/mchastity/subscribe

Information

  • Creator
    Robert Roe
  • Years Active
    2019 - 2023
  • Episodes
    25
  • Rating
    Explicit
  • Copyright
    © Robert Roe
  • Show Website
    The Roll of the Dice

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