Hi everyone, My (24F) boyfriend (26M) asked me back in college if I would lock him in chastity and cuckold him with his roommate. At the time this caused a breakdown from me, as I saw it as him getting bored of me and trying to pawn me off onto somebody else. He apologized, and we basically moved on like nothing happened for 5 years.

5 or 6 months ago I was doing some self reflection and realized my response wasn't really a response to him as much as to my own insecurities, so I reassessed the situation, and we've been trying out chastity/some more femdom stuff since then, and it's been going pretty well.

I know he is still very much into cuckolding, but I'm still somewhat nervous about it, as I've dealt with a lot of self-confidence/insecurity issues in my past, and I don't want to make him have those same issues, as I've always admired how happy-go-lucky, care free, and self assured he is. On the other hand, I've only ever slept with my bf, and I feel like having a little bit more varied experience would allow me to see other guys styles (like position preferences, rhythm, idk exactly what else) which may give us learning to actually improve the already great sex life I have with my bf.

My bf and I have a great relationship, with a dynamic that really feels like we are a team, always working together in everything we do. I highly value this, and don't want to do anything that could mess it up. I guess during sexytime I'm ok being the team captain sometimes, but I still want us to be on the same team doing an activity together rather then like me doing something to him if that makes sense.

I have a tentative plan as to how we'd go about this whole process to try and make things as safe and protective to our relationship as possible: First we'd make a tinder/bumble/ whatever account for me, for this purpose. We'd do swiping sessions together while he's locked as part of a teasing activity, but he'd be in charge of doing any communication with the guys and setting stuff up. This is because I want to have as close to 0 contact with the guy aka bull I guess as possible in case we decide to back out and not do anything/not do it again, I don't want there to be an account or a guy who has my contact info or anything like that out there, I want my bf to have total piece of mind if we take a step back. This also doubles as a way out for him if he has second thoughts or gets cold feet, he can just say it didn't work out timing wise or whatever and I never have to know, which I would tell him beforehand. It also to me makes it feel like more of a team activity, which is super important to me. I don't want to be doing this to him, I want to be doing it with him, even if he's locked in chastity lmao.

We live near Boston, which has a whole bunch of colleges, and I've still got my looks for now lmao, so I don't forsee a problem finding guys willing to have a one night stand. I would only ever want to be with each guy 1 time, again I want 0 chance of feelings or dynamic forming. We would meet then ideally at a hotel, or I suppose we could pick them up on campus and drive them to the hotel.

Safety is obviously super important, so condoms would he non-negotiable (despite my general distaste for them it's an unavoidable part of this)

Bf would be present at all times a. For my safety, and b. Because I want this to be a team activity, as with the planning and communication step it's important to me he's involved as much as possible, while respecting my boundaries of him not being physically involved. (He's bi and I am absolutely not ok with sharing him in any way lmao).

If the guy agreed to it, I'd actually like my bf to film the whole thing, not so we could have the video or anything, but more so he has a job and is an active participant, which will make it feel more like a team activity to me.

I would want him to stay caged through until at least the next day, so he has some time to think on the experience before the dreaded post nut clarity lmao, so no like sloppy seconds, or reclaiming sex, or whatever you want to call it.

After the guy leaves we block him on the app, and never have any contact with him again, to make it ultra clear to everyone involved that the guy was basically just a prop, not ever a romantic threat or possibility or anything like that.

I just want to know mainly if anyone else has had success in basically doing cuckolding without making it like THE defining dynamic/feature of your relationship. Our relationship is about so much more then sex, we've supported each other through rough times, recently bought a house and adopted cats together, so I really don't want to sort of overshadow all the imo more important things we've done as a team with a sexual act/fetish thing and have it come to define our relationship/dynamic.

Sorry this is a really long post. I seem to be incapable of writing anything succinctly. If you have any advice on how/if we should move forward without messing up our relationship dynamics I'd really appreciate it, and feel free to dm me if you have any questions or advice that's too long for a post reply or whatever.