Introductions discussion

After getting home from a night out with the girls and giving my wife some foot rubs, we started discussing whether I could actually hold off on climaxing until October’s end. My response was that time will tell; I’m feeling pretty lustful at the moment and wouldn’t say no to an orgasm if one came my way.:) She quickly cut off that train of thought.

We ended up reminiscing about our past sexual life, and she remarked it was a pity we weren’t practicing chastity when we were more open to threesomes. In her view, being locked up during a threesome would likely be harder than just staying chaste between us two. I hadn’t really considered that angle before, but now I think it could be quite the memorable experience: two women teasing you and trying to make you squirm without any hope of relief soon.

This scenario might actually happen if her girlfriend decides to visit again this year. So my wife asked me whether I’d rather stay locked up but get released on their last night together so I can climax, or remain in the cage and just wait another year for a chance at release.

Has anyone here experienced an MFF threesome while wearing a chastity device? If you have, how intense was it? What would you choose? I’m weighing my options. On one hand, being teased and dominated by them like back in the day sounds great, even if I end up left high and dry on that final night. But honestly, it’s been years since I’ve had sex with anyone other than my wife, and I do miss having intercourse with her. Can I have both worlds? Why did she have to plant this idea in my head? Now I’m wondering whether her girlfriend is actually coming or not because they talk on the phone all the time. Maybe she’s planning something specific and wants me to decide, or maybe she’s just playing games with my mind again. She keeps pulling me in different directions every day.

I don’t know if this new direction works for me yet. Right now it feels like a game I’m playing mostly to please her. As my wife put it, it’s tough staying macho while wearing makeup:) Tonight she’ll likely paddle me for what I forgot to do yesterday. As we watch a movie, I’ll be rubbing her feet—something she really enjoys.

She insists that when I massage her legs, I wear panties and a woman’s shirt; now makeup is added into the mix too. Since she’s bisexual with a preference for women, perhaps that influences things. Currently, feminization brings me humiliation rather than sexual arousal, though maybe that will shift as other parts of my sex life evolve.

For most of my life I’d never consider sleeping with another man, but given the right circumstances—especially if a woman who really wants it is involved so she can watch—it’s no longer impossible. My wife wouldn’t necessarily want this, but a former girlfriend/dome used to invite me to her club as her slave to have sex with men there.

I always declined because I haven’t felt comfortable being submissive around guys.

As you can see, our relationship is full of new elements we’re navigating. We seem both feeling our way through this sea of chastity, keeping what suits us and letting go of the rest—much like how we handled BDSM before. Thanks for your keen observation.