A KeyHolder's Handbook (10 page)

You can use the bootlaces to wrap around his his scrotum until the skin over his balls is stretched very tight. You can wrap his penis as well. You can use a combination of clothespins and twine. There are dozens of things you can do. Use your imagination. I am sure you can come up with a few things of your own. Here's a tip; You have heard of putting whipped cream on his genitals (or on your own body) and licking it off, but have you thought of using your favorite dessert? I love using banana cream pie, or even a Boston cream pie (more of a cake really). It is more tasty and more fun than simple whipped cream. And don't get me started on frozen strawberries!

Masturbation:
Yes, masturbation can be used as a punishment as well as a reward. It is all in how you do it. You can let him masturbate to orgasm, or not. You can make him do it in front of you while you kibitz him or just sit quietly and watch. You could video record him doing it and threaten to send copies to his friends or post it on the Internet. You can make it fun by letting him use his favorite lotion for lubrication, or not so fun by adding a few coffee grounds to it. You can make him stop several times, when he gets close to ejaculating. Or do it again, and again, and again.

You can do it for him (using your hand) but refuse to allow him to ejaculate. Or you can ruin his orgasm by stopping just in time. You can make him drink his own ejaculate. That's something many women do as a sign of their control. You can even masturbate yourself while he is forced to watch, but not touch.

There are many many ways to use masturbation as a punishment or a reward. If you have promised him an orgasm, but he did something to make you wish you hadn't, you can make him masturbate instead of getting to feel your hands on his genitals. Whether it is a pleasure or a discipline, masturbation can be used to give him what he deserves.

Rewards:
So what rewards can you use? I think we pretty well covered that in this chapter already. Of course there are other rewards you can give him for his excellent behavior. You can let him watch his favorite TV show. You can let him give you as many orgasms as you would like. You could let him lick your boots clean, or you could have him stand in front of an open window for twenty minutes.

Rewards, like punishments, are only rewards if they arouse him or please him in some way. So whatever you do to tease or arouse him will work as a reward. It is all in how you do it.

~ ~ ~

Chapter 10 – Humiliation Teasing

“
You said you would do anything for me.
Didn't you? Well, Bob is coming over
and I want you to give him a blow-job.”

There are so many ways to tease a chastity boy using humiliation, I don't know where to begin. I suppose I should begin by telling you exactly what kinds of things are considered to be humiliation, and how can you use them in the chastity game.

Let me start out with a warning. Humiliation can be dangerous psychologically! You have to know your partner and what kinds of things would be “over the top” in humiliation for him. That is, what works and what would be too much. Suppose your partner has a small penis and you say something like, “with that tiny thing, how can you ever please a woman?” If he is extremely sensitive about his size, you can make things worse. It would not be fun for him, and he might begin to resent you for it.

Now, if he is secure with the size of penis and you say the same thing, he might just love it. The only way to truly know is to ask him. There are other forms of humiliation that you can use that will be just as effective. For example, if you send him to a lingerie store or boutique to purchase a pair of panties for himself, he will be humiliated, but chances are you will not do any psychological damage. See the difference?

Almost everything you say can be some form of verbal humiliation. If your guy can handle verbal humiliation you have no trouble finding things to say that will humiliate him. But, as I said before, you must be careful not to damage his ego. So keep that in mind when using any form of verbal humiliation and you should be fine. Below are some examples of things you can say to him, some more humbling than others.

The other types of humiliation are what I call “physical” humiliation because it requires that one or both of you actually do something. As in sending him to the store, wearing a butt-plug, or wearing panties to work. All these things require some physical action, even if you only threaten that action. The fun part about using humiliation when other people are around is that what you say doesn't have to be true. For example, you might say, “Is that plug in your bottom bothering you?” even when he is not wearing a butt-plug. After all, he isn't about to show a perfect stranger his bottom to prove it, now is he? If he does bother to deny wearing a plug, all you have to say is, “Honey, I put it there myself.” There will be no reason to deny it at that point.

At home:
These are the kinds of things you might say to your partner in the privacy of your own home, or any other time you are by yourselves, in order to embarrass or humiliate him. I am sure you can think of some other things to say as well.

Is that the best you can do? Scrub that floor, again.

If your tongue were any shorter I would just use the vibrator.

I think a Prince Albert would look nice on your little penis.

You look so cute in those pink panties.

A good chastity slave would have those chores done by now.

We need a penis pump for this thing.

Will that thing even reach the end of this cage?

Oh, I think we are going to need a smaller cage for that thing.

Your bottom looks so spankable!

Is that all the cum you have?

It would take you a year to fill a shot glass.

With Friends:
Here are some things to say when you are among certain friends whom you don't mind knowing you have your partner locked in a chastity device, or that you are in charge.

Do you all know that [his name] is wearing a chastity device?

Honey, show them the new panties you just bought.

Oh, [his name] is wearing crotchless panties right now.

We finally found a way to stop [his name] from masturbating. Didn't we, Honey?

Do you want me to paddle you again when we get home?

Am I going to have to make your bottom sore again when we get home?

Honey? Get that inflatable doll of yours. I want to show them your new girlfriend.

Have I shown you the photos of [his name] wearing his new panties?

Honey? Did you wear your pink panties like I told you?

Out and About:
The list below contains some things you can say that will embarrass him wherever you are. Use them when your friends are not around if you don't think they would understand. The fun part is in saying things that are not true. After all, he can't deny them once you have put them out there. It's kind of like the old trap, “Have you stopped beating your wife?” There is no way to answer that without admitting you, at least, used to beat her.

You would look good in these. [Holding up a pair of panties in a store.]

Is there somewhere he can try this on? [Holding up a dress for the clerk to see.]

Do you carry anything in his size? [Said in a ladies shoe store.]

Is that butt-plug comfortable, Dear? [While sitting in restaurant]

Is your chastity device pinching you? [Said anywhere someone might overhear you.]

I told you to wear the pink panties. You know they don't ride up like the blue ones.

Is your bottom still sore from that spanking I gave you?

I'll need you to fetch my paddle as soon as we get home.

Bi-sex & Cuckolding:
This is a slightly different area of humiliation. I am not going into the actual acts themselves, only what you can say or do at certain times in order to add to his humiliation or tease him about these things, even if you don't do them. Again, I want to warn you to use caution in these areas. If you don't actually cuckold him, he might begin to think you do if you are not careful. So please make sure that he is able to handle some of these things BEFORE you try using them.

You've got the perfect mouth for fellatio. Several guys have told me that.

I have been thinking of asking one of your buddies to come over and stick it to you, do you have any preference as to who it should be?

Isn't that the guy you had sex with last week? [Said loud enough for others to hear.]

Look at that guy, how would you like to suck him off?

Why don't you ask that guy if he would like to have sex with me while you watch?

I am thinking about cuckolding you. Maybe with that guy.

Do you think your boss would like to have sex with me? I have seen the way he looks at me.

If you want me to give you a blow-job, you better learn how to give one.

You like it when I use a strap-on, why would a real man be any different?

Unless you offer to give that guy a blow-job, I won't let you out of your cage any time soon.

I was talking to a guy at a bar last night and he said if I would have sex with him, he would let you watch.

You know, I could cuckold you without your knowledge, or permission.

In an earlier chapter we covered some of the humiliating things you can say or have him do when you are home alone together. So I won't bore you by repeating them here. But what I want you to take away from this chapter is that there are many ways to humiliate your partner and have a little harmless fun. Of course, you probably wouldn't want say any of those things in front his boss, but there are still plenty of places and situations in which you can take the opportunity to say a thing or two to let him know you still care. Yes, humiliation can be fun for you both. Don't overlook the chance to use it.

Don't forget to find out what your partner likes and doesn't like in the way of humiliation. Particularly about personal aspects of his being, like penis size. It is very important that you not step over the line when teasing him verbally. You never want to damage him psychologically.

It is even a good idea to know what his fantasies are about. You can use them in humiliating him as well. After all, no one wants their deepest, darkest fantasies made public. Even in your play, you need to know if paddling him hard is what he wants, or if he can't handle that much pain. Again, you want to keep things within his boundaries as well as your own.

Working together, you can find a very happy medium in which to play the game. So have fun with it and don't over do it.

~ ~ ~

Chapter 11 – Anal Play & Milking

“
I promised you an orgasm.
You have two minutes to masturbate,
or wait until next month.”

I don't know what it is about anal play that men like so much, but many of them seem to really enjoy it. I guess it is one of those things that you either love it or you hate it. But since so many men seem to love it, I felt it necessary to include it in this book.

Anal play includes such activities as running your finger lightly across his anus to using a strap-on dildo to perform anal intercourse with him. The key to doing anal play correctly is lubrication. You will need to have plenty of lubrication handy whenever you intend to stick anything into his anus, even your finger.

There are thousands of tiny nerve endings surrounding his anus. This makes it very sensitive to both pain and pleasure. The objective, or course, is pleasure. That means using lots and lots of lubrication! Some folks say, “You can't have too much lubrication” when dealing with the anus. I agree. When you think you have enough, double it. That's the general rule.

For play, especially when leaving his chastity device in place, anal play is a great alternative to his penis. Since his penis will have far less accessibility, especially with certain devices. Start small. Use your finger (gloved of course) or a small butt-plug. As time goes by you can use larger and larger items such as realistic, penis-shaped dildos and larger plugs.

Eventually, you will want to use a strap-on dildo and harness. There are a number of reasons for this. One, it gives him more of a submissive feeling. And the role-reversal can be very exciting for the both of you. If you haven't tried it, you should. It can be a wonderful experience for the both of you.

I don't recommend experimenting with objects other than those designed for anal use. Emergency room technicians always have stories about folks who used things like light bulbs, or candles, or even small rodents. Believe me when I tell you, you don't want that kind of embarrassment. Although the ER techs would love to have more stories to tell, you don't want to end up as one of them. So stick to things you can purchase that are intended for anal use.

You can strap your guy down to the bed, on his back, and raise his legs up high to gain access to his anus. Or you can put him on his hands (or elbows) and knees if you like. When his penis is not caged, I prefer him on his back, giving me better access to both his anus and his penis at the same time. On his knees, though, has one other advantage, he cannot see what you are doing, nor the device you intend on inserting. That can give him more of a feeling of submission. So there are advantages to both positions. Of course, you can also bend him over the edge of a table or the back of a chair. It is tantamount to putting him on his knees except that you have more flexibility as to location, kitchen, dinning room, living room, etc. You get the picture.