One more month in chastity or coupling up with another woman?

Imagine you haven’t climaxed in four weeks and on release day your CH offers a choice: an orgasm or spending the night with her attractive girlfriend while you remain locked up, plus another month of denial. What would you pick? This scenario has become a new fantasy for me, rooted in past experiences where my wife allowed me to sleep with her friends but I could only cum after being with her. It was thrilling yet frustrating simultaneously. Now that I’m in 24/7 long-term chastity, I often wonder what it would be like sharing the bed with someone else and which option I’d select if given the chance. This feels very possible since my wife is bisexual and has mentioned wanting another woman to join us for sex and teasing. Until we find that person, this remains my primary fantasy.

Len, Your lifestyle differs from most of us here, undoubtedly. I believe every man has fantasized about being in bed with two or more women, though few have actually experienced it. The scenario you describe might not appeal to me personally if it ever occurred. If forced to choose between the options presented, despite my love for denial, I would opt for the orgasm from my wife. I found chastity online several years ago when our marriage was still in its early stages of two people sharing a home. Although the kink existed then, I saw potential for it to strengthen our bond. Fortunately, it became real life. She has become everything to me once more. Over time, we have grown within this lifestyle, and since we both agreed on permanent denial for me, our dynamic improved significantly. I hope your fantasy remains just that while you read through my posts. It seems like you and your wife are developing a wonderful new relationship dynamic now that her former partner has moved away.

As someone who enjoys pain slightly, I find appeal in the idea of pleasing my girlfriend while locked up, unable to penetrate her, denied an orgasm and then facing another month without it. This is especially true considering the potential for erotic humiliation and objectification. Actually, a fantasy of mine (likely never realized) involves being compelled to sexually serve a *group* of attractive girlfriends, barred from screwing them or climaxing themselves, while they tease/torture me with various 'humiliating' activities like W/S, enema, strap-on play, and more. What can I say? I'm Twisted.

For me, it's not even close. If in some alternate reality my wife and her friend wanted to link up with them while I paid the price of one month without an orgasm, I see no downside. I don't think such a situation would ever occur naturally for us, but we possess key elements: my wife is bi-curious, we engage in denial regularly, and we've experimented with soft swinging. We frequent sex clubs too. She can be somewhat possessive so she won't let me stray too far, yet I have taken body shots from her friends before. So if I get to link up with one of her friends but go a month without coming, I would accept it.

I don't wish to cheat on my wife but if she presented it as an option I would easily choose the other woman mainly because it hasn't happened yet. For instance, if this choice came up every month, after several months I think I'd opt for the orgasm with my wife. We chose each other and love one another deeply; there is no one else I prefer for life. Our sex life is good to very good. This doesn't mean that in the initial few spans when offered this choice I would pick her over someone new, as it has been more than half of my life (>25 years) since I slept with anyone other than my wife.