I recently re-started chastity with my ex. But now as a FWB situation. I plan on being a bit more strict and even have a point system started with him. However, I'm a bit unsure of good ideas for fun and creative punishments. Or even more interesting ways to make him earn his points. Any ideas would be wonderful!
Really depends on what he is into, I assume if he's your ex you have some idea of what he likes and doesn't. For rewards indulge fetishes/desires, up to you if you want punishments to be more funishment or actual punishments -- But if you wanna really make him regret bad behavior, you can always push his limits. Maybe he's into spanking but only with a paddle, use a crop for real punishments. Or make him do things he doesn't want to, maybe he has no interest in cross dressing, dress him up anyways for the day. ¯\_(ツ)_/¯ Good luck, and have fun!
Can you tell us more about your ex Mistress? What does he like and not like? What kinds of things motivate him? What do you want from him?
The best bit is to make him expect the unexpected. Complete randomness, you know the rules, he doesn't. Let him find them out slowly, and once he thinks he knows them, change them. And above anything, don't let him out on a day you've told him.
He should definitely be making your life easier in return for your efforts. And more fun. You are in a good position to be strict (without the emotional portion) and funishments could include some embarrasment or much extra servitude depending on the situation. No doubt he will test you at some point - don't budge! Not only will he learn a new respect but odds are high he will be more turned on by "no" than "ok".
Well, he is the one who initially showed me chastity and the list of things he enjoys is actually pretty long. I know I can use denial as a punishment but he enjoys that far too much for it to be a real punishment. Also, domestic tasks as punishment has been suggested, but thats not really an option. Its hard to tell what he doesn't like honestly, but currently, I control basically all of his sexuality. Like, when he can or can't watch porn and what type of porn he can watch. Because he enjoys watching it, maybe as a punishment I can not give permission. I've had had embarrassment/ humiliation suggested to me as well but Im not sure how without feeling mean about it. I am still quite new to this in general, so understanding fully what I want out of it is hard.
If he likes porn, rather than taking it away as a punishment, just take it away. Spoon feed a little here or there to him as a reward. Then it's positive, and reinforces your control. He wants punishments that he enjoys, things that stimulate him or arouse him sexually. Things that play to his wants. But that's not punishment. It's sometimes called "funishment." Punishment should never be doing something that he should be doing. In other words, if you expect dishes done, then doing dishes isn't punishment. It's duty. If you enjoy being served orally or want your behind licked, then that's not punishment; he shouldn't need to be punished to be made to do what he's expected to do. He should approach his duties and assignments with enthusiasm, not because he wants them, but because you want them, and if any of it involves service to you directly, especially physical service, that can't be punishment. How can serving you be punishment and what does that say about where his head is? Serving you is a privilege. it's a reward. Physical punishments typically involve discomfort or pain, and if they're punishments, shouldn't be pleasant. Corner time is fun for the first ten or fifteen minutes. Less at an hour, and less when put in a dark room and deprived of sound and a clock. Less if placed on one's knees on a dish towel with rice on it. If a spanking is given, it should hurt. not tickle, not tease. It should be unpleasant. A bar of soap in the mouth, capzacin rub on the penis, standing arms outstretched with weights in each hand, are useful. Send him to the store to buy a can of peas. Make him walk. When he gets back, send him again. Give him a glass of water and when it needs to go, tell him to stand by the bathroom door until given permission. Wait. When the TV is on, watch programs you ant, not him. Put it on the hallmark channel and play 24/7 christmas movies and see how that goes. Everything he does is a privilege, because you allow it. Any privilege can be revoked. That includes sleep. Meals. Leaving the house. Sitting on furniture. Have him write a poem. He should beg for anything, and thank profusely. Clothespins on nipples are an old standby that never grows old. Stop using his name. Require him to call you by an honorific or title. Give him the silent treatment. Refuse his privilege to undress. Or keep him undressed. Adorn him in things he doesn't like, or tell him what to wear. If he finds something humiliating, go with that. Write on him. Give him chore lists and treat them like you would a child; give him a gold star, inspect his dishes, have him do menial things. He may be a grown man but he can scrub a toilet or the kitchen floor with a toothbrush. Dogs mark territory; mark him accordingly. Write lines; I will not talk aback, five hundred times, gets old after the first fifty or so. Your choice whether to tack it to the wall or simply crumple it up and throw it away. Go shopping; make him carry your purse, walk a step behind. If it strikes your fancy, put him in panties. If he's resistant to something, make a note. Use that. If he wants something, use that. Withhold what he wants, allowing it only as you see fit. When he approaches you, it should be below eye level, perhaps starting on his knees, kissing your feet. There are endless ways; it comes down to your preference (not his) and your comfort level (not his). His purpose is to honor and respect you. It doesn't necessarily work the other way around.
Put him in the smallest steel and totally secure device that can be fitted to him. Equip the the chastity device with a TENS unit and enjoy watching him squirm as you apply the power. I am in a stainless steel Nub that has TENS pads within the cage, while bound and the TENS modulating pules to my helpless member, it get maddening but sissy has to wait to be released.
Have him entertain you. For example, make one of his duties writing you a story each day, based on one of his fantasies. He'll basically write you a book if you're not careful, and in those stories, you'll have all of the ammo that you need. Also, do not tell my wife this. Thank you. That is all.
Have him do things of value to you. Detail your car. Keep it gassed up. Maintained. Make a meal plan for the week. Shop for ingredients. Prepare the meals and clean the kitchen. Do the laundry. Clean your home.
You could always tie him to the bed and take off cage and then tease him relentlessly but don't let him cum. Edge him to the brink several times and then put cage back on and leave him tied and turn on porn so he is forced to watch while caged. If any pre cum or cum from ruined orgasm, you make him eat it.
How do you control his porn habits? Teasing as always good telling him who is in control and make sure he remembers. Maybe for him to wear panties my ex did that and was super embarrassing had no choice since she bought them for me. Maybe lock his boxers away. Felt super submissive after that like mind control. If he don't comply handcuff him to something and spank him.
I know this is an older post, but he is getting a lot out of chastity, and the woman shouldn't be driven bonkers coming up with ideas. Keep in chastity, but redirect his energy to things that you want. Acknowledge his locked and frustrated status, but find non-romantic favors he can do for you, with no strings attached. Redirect him from thinking you are his fantasy to things you want.
Well these can be punishment or reward or just fun things to try but this is our list we go to MISTRESS PLAY LIST Full condom Sissy is to cum in a condom through out the day min 5x. Then to pour it on mistress body part of choice then lick clean. 3/5 Satin lunch When siissy opens his lunch bag and finds a note or his panty bag. He is to immediately stop and go put them on and send pics to mistress for proof.4/5 Fun trip to work When entering sissys truck and there are panties hanging in the rear view mirror im to change in the truck and send pic to mistress for proof. 4/5 Dirty panties on command When mistress texts her sissy he is to stop everything and cum in his panties and send pic as proof.3/5 Satin handoff When we go out to eat mistress slips her sissy his panties. He is to change in the rest room and give her his guy underwear.4/5 Frustrating day When mistress texts her sissy he is to stop everything and edge with out cumming 5x.3/5 Short sex Mistress sissy is to please her to full satisfaction then he is to masturbate as quickly as possible and lick clean his mess. 4/5 Pure evil Sissy is to put his cock vibe on and kneel in his panties and watch mistress masturbate to her full pleasure with out touching ones self the whole time. If sissy cums before her spankings will follow. 4/5 Long distance fun When sissy has to travel he is to have his panties on him at all times so when she calls him he is to put them on and send pic proof.4/5 Choking hazard When told sissy is to select his cock for mistress strapon. The put it on her and kneel in his panties only and suck off mistress cock. While masturbating in his panties and cum on her cock or in your panties. Then sissy is to clean his mess by sucking the cum off her strapon or licking his panties clean.5/5 Cool treat warm load Save your cum during the day and freeze it to a cum cube. While mistress helps you ypi are to suck on the cum cube and only when it is gone you may cum. Which then you are to lick up the new warm mess you just made.4/5 Pleasure and pain Sissy is allowed to masturbate while mistress helps him. He can take as long as needed. But the number of mins it took to cum is the number of spankings in his panties he must take while over her knee.4/5 Snake eyes Mistress rolls 3 dice the total number is how long you have to cum. If you fail double the number that is how many spankings you must take on your knees in your panties.3/5 Front porch sissy You are to be in your panties with your cum cup. First mistress will roll a single dice to see how many times you have to ruin orgasm in to your cup. Then when done sissy is to go on the front porch in his panties only and must have a full orgasm in his cup. (Blindfold for extra fun) only then can he come in. He must give his cup to his mistress and kneel before her as she pours it in his mouth to swallow or to leave it in his mouth for how ever long mistress wants.4/5 Find the keys Mistress has her sissy in his panties blindfolded on the front porch she tosses the keys in the yard then takes the blindfold and robe. Locking the door as she goes in he must find the keys in order to get in. 3/5 Panty clean Mistress sissy is to make his mistress cum in her panties. Mistress then puts her cum soaked panties ober his head and the cum soaked are over his nose and mouth. Then he is to cum in his panties while licking her cum. He must clean his panties as well.3/5 Cant stop now Mistress ties her sissy down to the bed were she makes him cum but she doesn’t stop she keeps going till he cums again or how ever number she wishes.3/4 Blind fun Mistress puts her sissy in his panties and handcuff his hands behind him with a blindfold on. He is to make her cum the she leaves him there for however long she wants then does it again. After mistress is satisfied she uncuffs him and puts him in his cage till the next day.3/5 Big tease Mistress strips naked and pickes her fav toy. She masturbate while you watch not allowed to do anything but watch. When she is done you are to lick her toy clean and clean her pussy with your tounge. She then puts you back in your cage to cum later when is her choice.4/5 Waiting patiently Mistress blindfold and handcuffs her sissy in his panties. There is to kneel beside her until she is ready to play. Sissy must wait in anticipation and squirm while she reads a book or watches her fav show.3/5 Porn or not to porn Mistress ties/handcuffs her sissy to the queening chair. She then puts on a premade porn collection that he made. He is to sit there in his panties and watch for how ever long you wish. He is then caged and denied a orgasm. (Bonus if he is caged the whole time) 4/5 Panty hanger Sissy is to get hard and stand there next to his mistress while she masturbates. She takes off her panties and hangs the from his cock while she masturbates he must not drop them. Use 1 dice to determine the length of time. If he does 10 spanks 4/5 Hanging on the edge Mistress rolls the 2 dice . One dice is the number of edgings her sissy must do. The sec is how many times in a day he must do the edgings.3/5 Panty shopping Mistress is to take her sissy panty shopping. Mistress can say what ever she wants and have staff help pick out items for her sissy with them knowing there for you. First and foremost All sessions start with satisfaction of mistress. You get no pleasure until she is completely satisfied. Training Sissy is to masturbate for 20 mins total daily. If sissy gets close he must stop and cool down for a min which doesn't count towards the total time.4/5 Beat the clock Mistress rolls the dice (2). The total number is the mins your sissy must last in his duel cock vibrator. If he beets the clock he can fuck his mistress. If not he gets double the number in spankings and caged till tomorrow when he will try again. 4/5 Tasty treat Sissy is to edge as much as he can in his cum cup with out orgasm. Then he hands it to his mistress where she pours it in to his mouth but not swallow. He must then orally pleasure mistress to orgasm with out losing any cum or swallow. Once done he is allowed to swallow. 4/5 Pegging training Mistress fucks her sissy with her strapon. Durning his fucking he is allowed to masturbate till he gets near cumming. He must stop and let mistress fuck him to orgasm. If he cant after a predetermined time the he goes into his cage till tomorrow. He will also be spanked for the same number that the time was givin exp: 30 minutes = 30 spanks3/5 She has the controller Mistress has her sissy on all fours with the fuck machine and his dildo hooked up. Mistress will lay in front of him and he will orally pleasure mistress. She will be running the controller to the fuck machine while it fucks her sissy. If she cums before him he will stay there being fucked while mistress whips him till he cums where he then will clean up his cum. 5/5 Its not the end Mistress will give her sissy a handjob/ fleshlight hooked to fuck machine to orgasm but when he cums she will not stop until her sissy cums again no matter how bad he begs her to stop.3/5 Lone training During his showers he is to practice with his dildo so he is ready to be fucked by his mistress where and when she wants. Also he is to milk his prostate and learn to do it quickly so his mistress can milk him to drain all of his cum out.4/5 Whats in the bag In a satin bag mistress will have 50 black and 25 white stones. Sissy can pick up to 3 stones if its black he will have to do his mistress punishment for every black one picked. Every white one picked is a reward of his choosing. After all have been picked play them out in the order picked from the bag.4/5 Teaser trailer Tie your sissy up in his panties only in the queening chair then do what ever you want to him. Take your cloths off, rub your pussy in his face or lap, jerk him off, play with your self moaning wildly. Then stop get dressed and leave him there for at least 20 mins and do it all over again.4/5 Cant feel a thing Mistress will put numbing cream on he hard cock and then put on a condom he is then to fuck his mistress to pleasure. He is then allowed to cum in a certain amount of time. If he cant then he will get caged up till tomorrow. 3/5 I see the light Mistress will tie her sissy in his panties to the queening chair. He must keep his eyes closed for what ever time mistress deems. If he opens his eyes he will be spanked for the same number of time as in mins. 3/5 Scrabble Play the game as normal. But when it is mistress turn you are to do what ever she wants. When its your turn she will tease you any way she wants. First to 400 wins if sissy can spell orgasm he will get to play if he does not mistress choice of punishment. Sex words are worth double.5/5 No hands Mistress will tie her sissys hands behind his back and place various types of toys on the bed for him. He can only use his cock to turn things on or his mouth. He gets one hr to cum if not then mistress will spank him for equal amounts to mins 60 spanks for 60 mins 4/5 In a form of a question Sissy will be given a question sheet or txt but no questions will be on it. He is only allowed to answer yes or no or a.b.c.d. when completed he will then be given the questions and must do as he answered them.4/5 Between the sheets Mistress will put her sissys flesh light between the matress and box springs. He then will fuck the flesh light as he orally pleasure mistress to orgasm. If she beats him he gets to cum on her breast and clean it up. If not he must stop and get caged up with no orgasm.4/5 To the line Sissy is to milk him self while his mistress masturbate to her full pleasure. When she is done he is to mark on his cup on how full he got it then drink it down. Next day is round 2 you must beat your old goal to fuck your mistress. If not then she will spank you number is her choice4/5 Birthday Cake Wish Mistress will bake a cake. The cake are numbered 1-8 one of the numbers will have the combination to the lockbox that has your chastity key in it. The others will be full play senarios that will happen. Once the candles are blown out she will cut it in to eight pieces. You can pick one. if it has the combo the you will fuck her brains out. If not then that senario will play out for the night. the next day you can pick again and so forth until you get your birthday present Between the legs Allow him to put his hard cock between your legs and pump for x amount minute. No cumming unless mistress says so. Needle in a Haystack You will need: - 1x deck of playing cards How to play: - Male partner in panties may not cum or touch her body/pussy/ass in any way unless first granted. Failure to comply results in spankings. - Female partner reveals the top card of the deck. - If the revealed card is not the ace of hearts, an action is performed based on the revealed card’s value (see below). Afterward, another card is revealed. - Only after the ace of hearts is found may the male partner be permitted to fuck the female partner and/or cum. Cards and their actions: ♣ CLUBS (ass paddlings) - if a number, that many times peddled - if a face card (jack/king/queen), lick pussy with the mistress on bottom for value of the card - if ace of clubs, speedbag: paddle rapidly for 10-20 seconds ♠ SPADES (edging) - if a number, number of minutes to edge no cumming - if a face card (jack/king/queen), sit on his face and have him edge for value of the card - if ace of spades, sit on his face till you orgasm ♥ HEARTS (Cock & Ball Pleasure) - if a number, that many slow strokes of his cock or seconds of ball massaging - if a face card (jack/king/queen), 30 seconds of blowjob, titfucking, or between her legs (her choice) - if ace of hearts, he is permitted to fuck her (won the game) ♦ DIAMONDS (Strapon Pleasure) - if a number, multiply by ten - that many seconds he is take his strapon) - if a face card (jack/king/queen), x amount of mins he is to be on his knees sucking your strapon - if ace of diamonds, pussy/ass privileges for as long as she wants, whichever way she wants ♣♠♥♦ JOKER (Wild Card) freestyle: 10-20 actions of her choosing, all mixed together and in any order she likes the card game Kings Cock Rules: No touching when the game does not allow it. You must both start with the same amount of clothes, which must be more than 2 but less than 12. If you have no more clothes to take off and the card requires you to, you must pick again. No skipping or cheating on a card. Instructions You place the cards in a pile in the middle of the bed or carpet. You simply take it in turns to take a card. Ladies first. Each card corresponds to a different action. You can take as long as you want picking up your card. Here are the cards and what they each mean. A- Solo - Masturbate for your partner for 10min . 2 - You - Your partner must remove one item of clothing. 3 - Me - You must remove an item of clothing. 4 - Girl - The female must remove an item of clothing. 5 - Guy - The male must remove an item of clothing. 6 - Licks - You must lick your partner anywhere you want for 5 mins 7 - Kiss - Kiss your partner. 8 - Object - your partner must use you any way they want for 15 mins. 9 - oral - Give your partner oral for 10 mins 10 - Touch - Touch your partner wherever you want. For 15 mins J - Spanking - Spank your partner over your knee 5x increase by 5 for each additional J pulled Q - worship- guy must worship her kneel and kiss her feet. please her orally. massage her. what ever she wants for 20 mins K - King - she is to submit to his every request for 20 mins. deeper when mistress puts her sissy in chastity she takes his dildo and places the key all the way at the base. in order to get out he must be able to retrieve the key by deep throating his cock till his chin touches the key then he can be released. suck it dry the male sub and the male sub is to put on a dry condom and proceed to ruin into the dry condom three times...put cum filled condom on dildo or strap on being careful not to spill a drop, clip small hole in tip of condom and proceed to suck cock hard and suck and eat out all cum, when all cum is sucked out, sub is to remove condom licking clean both condom and cock clean. jingle all the way Slave puts on his collar with a bell attached. He gets 1 min to start masturbating with no penalty. After 1 min any sound from his bell is 2 smacks with the paddle if he reaches 10 he must stop immediately and no orgasm. Then he must bend over his mistress knee and receive his punishment. little willie Have him make a mold of his own penis. Once made, have him give it a long, intricate blowjob. Then fuck his ass with it, then fuck his ass with his dildo. Ask him whether he feels the difference between his smaller cock, and a real mans cock. time in jail When your sub is allowed to cum, put him in his cage, set a timer for an hour, within this time, he must make you cum 3 times without using his dick, or using only his tongue. If he makes you cum 3 times, he is unlocked and allowed to cum once. If he fails, then that release is cancelled. It should be fun watching him struggle in his cage. 155. Once he’s gotten his cock hard, the slave must coat it with a mentholated gel or “deep heat” muscle rub. Once the rub is on, he must put on a condom and continue masturbating. Im Handcuffed and blindfolded on my knees with a pillow between my legs you place the magic wand under my cock and watch my struggle to cum