How to make play time fun and interesting?

He could ask permission to go to bed every evening suitably dressed with a cane in his hand for your optional use-then be dismissed-takes about 2minutes

 

If you like bondage and total control of your sissy then dress your gurl in a sexy outfit, bind sissy's arms, and put her through her paces. A wireless chastity device would be the ultimate way to control your sissy; pain or a little pleasure will make her do anything you desire. You should have lots of fun while breaking you sissy.

 

put the burden on him.
"i'm bored and want to be entertained tonight. come up with 3 things i should do to you."
"if your ideas irritate me, the can will replace the activity you ask for"

or tie him up and leave him like that for a long time. come in silently, and i mean silent, and strike him with the cane as hard as you know he can take. then leave for a few more minutes. he will sit there thinking seconds are hours, wondering when the next blow will land.

pick up an estim box. those are great for changing things up. hands free orgasms are interesting sensations. you can have electrodes for his cock and balls. or if he is not opposed to butt stuff, a probe on his prostate. when the Erostek 312 is cranked high enough, it milks him without much effort.

if he is into anal, keep him caged and only allow him a hands free orgasm when receiving your strapon, after being caged for a month or three... this ones on my bucket list

 

One of the easiest and most effective tools you have is being unpredictable. Practice mis-direction. He might think you are going to unlock him, lead him on a little, but don’t. Wear your key around the house. Flaunt it. Make him give you a back rub instead. Building suspense can go on for over a week. Mental teasing is as effective as physical teasing. You know what he responds to, so have fun!

 

Have him perform for you unlock him and instruct him to keep hard for an hour no Cumming then straight back in the cage

 

I didn't read the other comments but I noticed you didn't mention anything about massages. That is one of my wife's favorite things; back, leg, and neck massages. Sometimes I get a little tease before hand, but even if I don't it is the best part of my day where we get some physical and emotional bonding.

Something that I really hate and is rarely done is I am forced to eat some food that I really hate. I guess it is a reminder to do better sometimes or if I get something good I need to get something bad as well (ying and yang so to speak).

 

Tens unit, edging, ruined orgasms, sounding, force orgasms.. lots of fun things to do

 

Is there something very close to a hard limit? Something that he was on the fence about? For me, a hard limit in our contract is no caning. So we’re not using “canes,” but small wooden dowels. My point is maybe spend a week pushing limits?

My wife just gave me 30 minutes to write a list of punishments that I would absolutely NOT like. Things that are on there that I wouldn’t mind are things like write a love letter, wear lingerie under clothes, etc.

For my feminization are things like write a makeup tutorial, write a research paper on the negative impacts advertising has had on women’s rights, fashion, body image, etc.

Then stuff like be bound as furniture like chair, footstool, side table, etc. and be left for a while, even if she’s not in the room.

Lastly, chores like cleaning out, or washing, her car out while wearing a tight corset or shapewear, etc.

So maybe have him make a list? I’m sure he’s been making lists like this for years.

 

Tie him to the bed and ride his face till you come. Then stuff your panties in his mouth and go enjoy some ice cream or a shower. Then untie him.

 

The best writing advice I ever got was that when things come to a standstill and you aren't sure where to go, throw in a monkey. The idea is that one does something to break the stalemate. Put something in that story that doesn't belong and see where the narrative goes.

I submit that it needn't be a monkey. They're ill tempered, and in short supply. But you might throw in a timer. Do this by the time the bell rings, or...

Throw in a hot pepper. Or a ball of twine. Or a camera. Or try a different room.

Do the opposite of what your gut instinct tells you to do. See where it goes.

 

Many moons ago, I was an active karateka, or guy in white PJ's that jumps around and punches air and people. We'd hold events called "special training," usually over several days or a week, that were intensive around-the-clock events that left little time for sleep, no time to do laundry, and pushed to exhaustion and beyond.

It was said that the real training didn't begin until we were exhausted. Everything up until that point was a warm-up, because we didn't learn about ourselves, or the limits beyond the limits, until we'd given all we could.

I've heard it said that punishment doesn't really begin until one wishes it would end.

I submit that if indeed enacting a Female Led Relationship is the goal, then when he loses interest is precisely when it becomes the most important. Until then, it's just a fun fantasy to him. Spice.

My wife and I made love one evening, and as the event wore to a standstill, I felt impelled to close my eyes. My wife determined differently. She grabbed me firmly by the genitalia and informed me that "you're not finished yet," and led me to the shower, where she pressed on my shoulders until I knelt. I might have felt the need to sleep, but she felt the need to urinate.

When he feels spent and has lost the will to press on, it is exactly the time to insist. He might find the notion of "cleanup" to be fantasy fodder prior to his last big hurrah, but suddenly see it as distasteful. Insist. He will thank you later, and it will be a fantasy he will return to. He just needs help. As men, we seem to have little resistance to unburdening ourselves sexually in our wife's mouth; a gentleman ought never do that which he is unwilling to have done; it is appropriate for him to devote himself down below, should you desire, until you no longer desire. Good for goose, gander, and all.

Let him cum, let his interest subside, and then remind him that it's not his interest that is important, but yours. Good time to have him go make you coffee, or do dishes, or serve or service you, run your bath, kiss your feet, clean up after himself, stand in a corner if he failed to please, or any number of things to establish the hierarchy of wife over husband. The FLR doesn't begin until it's honest, and what man is honest until his lower brain is no longer driving the ship? Until then, he's done what you tell him because his penis says so. Once he's come, it's time for him to do what you tell him, because you say so.

 

If you’re practicing chastity, maybe get something like thumb cuffs or a small locking anal plug that will only be removed after going back into chastity. Or leave the plug in until he starts to feel obedient again.

Would it work to let him have ruined orgasms during PIV? Tie his hips to something like a tall bedpost or footboard and once he’s begun ejaculating, just push back hard against him so he can’t get a full orgasm, but you get the full amount from him.

For most men this is very effective in maintaining interest. Or at least cutting the rebound time, significantly.

 

He might seem ambivalent, and he might even protest, but if he has any interest in serving you or engaging in a FLR, it will make his day. Maybe even week or month, and he will look back on the moment as a very positive event. Expect gratitude.