Gradual is better...

...this may seem pretty obvious, but failing to heed this (which some do) is a recipe for failure. Below are a few guidelines that will help. (Disclaimer: These are not hard and fast rules - just guidelines) 

1. Male chastity: If he's used to an orgasm every 2 days, then lock him up for 4, hide the key, and be firm when he begs for a release on day 3. He won't sleep as well, his balls will ache with lust, he'll be unable to concentrate as well. Just remember, he probably has a job, and he'll need to concentrate on work. After a few weeks, you can increase his lock up time to 6 days, then 8 in a few more weeks etc. Push his limits of course, but don't get carried away.

2. Corporal punishment: Start out with a light to moderate spanking 1-2 days a week when he displeases his lady, after a few weeks, add 1-2 days additional chastity lock up time per transgression. After a few weeks, increase the severity of the spanking, and require him to stand in the corner (pants down) for 15 min. After a month or 2 (If you're a lady who sees another man for your sexual pleasure) have your bull take part in the spanking as well - or simply have your bull do the spanking for you!

3. Pegging: Start out with a dildo of moderate size and peg him a few times a week (having him locked in his chastity cage is highly recommended) in the weeks that follow, gradually increase the size of the dildo and as well as the force of your thrusting.

4. Forced Feminization: After finding a dress and lingerie that fits, start out with a few hours a week at home in 2-3 time blocks. Gradually increase the dress up time.

5. Cuckolding: Finding a bull who is bigger and stronger than your locked husband or B/F is a real advantage. Start out with something as simple as a shopping trip or dinner and drinks at a nice place. Bring your (locked up) husband for B/F along. Hold your bulls hand, a few kisses from time to time at first. Get your (locked up) husband for B/F used to seeing the 2 of you together. In the weeks to follow, you can have your (locked up) husband for B/F dress you for your dates, undress you when you arrive back home, and require him to listen attentively and respectfully while you give him the details on how sexually fulfilling your bull is, and (if you want to do some real teasing) reflect on how you wish it could be him if only he were better endowed. This is best done while you're cuddling with him, spooning him in bed, or simply sitting on his lap and kissing him. 

Overcoming his resistance: There will be times when your (locked up) husband for B/F will resist - This can happen even if he agrees to these things earlier (usually because he misjudged the intensity of the experience) A few things a woman can use to overcome his resistance. 1. Threaten to add to his chastity lock up time. He's probably sexually frustrated and aching at this point. The thought of enduring additional lock up time will usually be enough to cause him to obey. 2. Enlist the help of your bull. Bulls who have sex with the wives or G/F's of other men usually like to assert their dominance. Just the threat of a moderate beat down by your bull will usually cause your locked up guy to submit to your wishes.