Female led relationships discussion

Hello all! Here are the recent events that led to my boyfriend wearing a chastity belt: a few weeks back, he pleasured me thoroughly with both his penis and a strapon, yet remained utterly unsatisfied. That evening, I prevented him from ejaculating because I chose not to let him finish. He enjoys (as do I) being humiliated by me, so I decided to recount this story in front of him to my best friend—who has previously exhibited “mistress-like” behavior with her ex-boyfriend and can thus relate easily. My boyfriend was deeply embarrassed when I described the intensity of my orgasm while he suffered through denial; it frustrated him especially since I preferred the strapon over his own cock. He got quite aroused watching our conversation, even as my friend laughed at his plight.

Afterward, she introduced us to the “chastity world” and suggested I make him wear a cage. We discussed it, and he agreed only if I could prove that this new arrangement would genuinely benefit me more than just using the strapon (which is slightly larger than his penis). He has a point: at about 6 inches, his size is average and works for me (I have strong orgasms during regular intercourse too), but what really turns me on is knowing he cannot cum and must rely on the strapon. I shared this with him, and L (my boyfriend) replied that he could make me orgasm just as powerfully as the strap-on does.

So we decided to try a threesome to see if he lives up to his claim. It started out like fun for everyone but turned into quite an amazing experience!;) Regardless, I know my friend “P” is attracted to him (L is handsome and sweet), and L harbors lesbian fantasies involving both P and me since she is such a sexy woman. So, P and I teased him for about an hour before we began kissing while he was forced to watch only.

It had been nearly one week without ejaculation for him because the action happened over three nights in August. Even though he isn’t caged yet, I trust his obedience; if I tell him no, he listens (at least as long as the period isn’t too lengthy). Once he was highly aroused again, I commanded him to penetrate me for at least 20 minutes without stopping or finishing. If he failed, he would deserve to stay in chastity… He agreed and stated that being caged is fair if he cannot please his mistress well enough.

He didn’t last more than five minutes (partly due to P’s provocative behavior; I know how much he desires this dynamic).:)

P lent me her chastity device (I believe it’s a CB6000 model) for these nights since she is single and no longer needs it. We invited her to join us as thanks for the loan. The cage fits well enough, but he feels significant pain when his erection starts… I love it A LOT, and P does too. He penetrated us with the strapon while constantly begging for release and cumming permission. It’s a fantastic sensation for me; he seems incredibly turned on by the situation yet desperately wants to finish.

But there is one BIG problem: Yamaha motorcycles. Yes, Yamaha. He is an avid biker, and likely his bike (and cars) are things he loves almost as much as I do!:)

Currently, he avoids riding to test if the device causes too much discomfort or makes biking impossible. He thinks it will be manageable… He tested with the bike stationary and found it hurt quite a bit. Additionally, since he attends track days, it would seem nearly impossible to ride at speeds of 300 km/h or more given the pain.

Does anyone have solutions for this issue? Are there specific devices that allow comfortable riding? I also want your opinion on whether two months is sufficient… I love his energy when we fuck while he’s so frustrated, and it gets even better if P watches. He feels terribly humiliated because he “can’t get fully erect and P sees a smaller dick” (his exact words), which turns him on due to that humiliation. Indeed, both of us agreed that YES, he is quite small for this reason; he deserves to stay locked up without much pleasure except teasing.

HOWEVER, I don’t want to be too lenient with him… When punishing, I can be merciless and firm. Do you think two months are enough for a first attempt, or could he handle more? Naturally, this plan holds only if we resolve the “riding problems”.