Just make sure to take it easy on them at first and increase the wear duration over time and start small and increase the butt plug size over time as well.īut why make them wear a butt plug? Here are our reasons why you should make him: Let’s Him Remember Who is Boss That may seem odd or extreme to you because it would be uncomfortable to wear a butt plug that long, right? Surprisingly, men will get used to it and love it. Chastity and anal play often go hand in hand so it’s only natural that chastity keyholders who want to take things to the next level opt to force their men to wear anal plugs. When it comes to chastity relationships, one of the most common ways to pleasure, tease, torture the man is to penetrate him anally using a butt plug or dildo. Forcing your man to wear a chastity cage is a great start towards taking control of your relationship, but what if you want to take it to the next level?