Hi Ms. Jenna,
Jenna said:
How should I bring up that I want to place a chastity device on my bf, and after that which one should I get? I know they come in different sizes but I don't know which to get.
I suggest starting out by treating it as a game. First, check out the local sex shop(s) in your area by yourself, and find one that sells male chastity devices. Don't worry, at this point, about whether the type available locally is the type you've decided will be best for your bf to wear.
If you find they are available locally, suggest to your bf "checking out" the sex shop that sells them. No doubt he'll agree. While there, peruse their various sex toys and, by happenstance, "discover" the chastity devices. Express curiosity combined with ignorance about what they might be for... perhaps say something like, "hey look at this — what do you do with these, anyway?" Your bf, looking awkward, might then hesitantly explain it to you. If he doesn't, and obviously doesn't want to talk about it, get the store clerk — preferably female — to explain it with him standing there. (Or, the store clerk... seeing your interest... might come over and say, "Can I help you?")
If the type available in the sex shop happens to be the type you want your bf to wear, and if he shows interest in "trying it out, just for fun, just as a game," your problem will be solved. With the assistance of the store clerk, determine what size will fit him and buy it on the spot. If possible, get him to pay for it.
If your bf says, "Um... no thanks..." and obviously doesn't want to purchase one or "try one out just for fun," then buy something else. A good choice would be a realistic-looking vibrating dildo that's obviously larger than his cock, but not so large you won't be able to become comfortable using it (when it's well-lubricated).
This will complete your "reconnaissance phase." Next, secretly order a chastity device from an online source, of the kind you decide will be best for him to wear and in the correct size (or, secretly return to the sex shop later and buy it yourself).
Then, invent a sex-oriented game you know there's a good chance your bf will lose (but this should not be blatantly obvious). For motivation, tell him if he wins, he can do something you know he will like... perhaps you could agree to suck his cock and swallow, for instance. If you win, he will have to do something you will decide on... but "you aren't quite sure yet what it will be."
When you "win," drop the pretense of being uncertain what you want him to do. Retrieve his chastity device from its hiding place, tell him to unwrap it, and tell him you want him to do the following "for you."
1) Wear it for several (up to 4) hours on day 1. This could be on the day of the game, say a Friday evening. Then, you will unlock him.
2) Wear it for 8 hours on day 2 (say, a Saturday). During days 1 and 2 you should determine how to adjust it for proper fit, so he can't get out of it and it also isn't painful. Tell him if he completes day 2 successfully, you'll reward him with something he likes (another blow job, for instance).
3) Wear it for 24 hours on day 3 (say, Sun. morning to Mon. morning). Promise you'll again reward him with something nice if he completes his 24 hours successfully, and also promise you'll unlock him for the next 24 hour day.
4) After his "day off," tell him you want him to wear it for 48 hours, and again promise to reward him if he does that successfully.
Etc. Your bf's "penalty" for losing your game might extend through step 4, with intermittent "rewards" by you (as noted).
But, don't stop with step 4. Before you unlock him, seduce him into agreeing to a step 5 (72 hours = 3 days) in his chastity device followed by 1 day unlocked, with a reward. Sometimes his "reward" might consist of you allowing him to masturbate (on his knees before you, with you "supervising," after which [for instance] he must lick up his cum from your feet).
Continue your "increasing time in chastity device" followed by "a reward when he completes it successfully" game until your bf is up to 6 days in chastity followed by 1 day unlocked, with a reward (to be determined by you each time). Then, keep him on this schedule indefinitely.
Throughout, imbue in your bf the concept that chastity for him does NOT mean sexual abstinence for you. Rather, while in chastity he must bring you to orgasm whenever you wish using his tongue for cuninlingus and/or analingus, and/or sucking your clit while fucking you with your large well-lubricated dildo, etc. Be creative! But, do not allow him penetrative sex except as a "reward" during his scheduled 24 hour "unlocked days" (and perhaps not even then, unless you want it).
During your bf's in-chastity days, it will probably be good management strategy to taunt him by looking at him and speaking with him in sexy ways, flashing a breast and your ass and pussy from time-to-time, dressing provocatively (short skirts, scanty dresses, thigh-high stockings, sexy panties, show lots of cleavage).
Good luck! Please keep us posted on your progress.
—Custer