I am new to the kinky side of sexuality, I guess you could call me vanilla but my past relationships have been extremely static - same old fantasies, positions, etc. My current relationship has me in a whole new world and being a sexually active, mentally connected person this throws me for a loop so advice is welcome. My Significant other and I are about the same age, however for the last several years he's experimented with male chastity and feminization. His most recent long term relationship prior to me put him down for this behavior and demeaned him, and while he likes the humiliation aspect she wasn't doing it for the right reasons and made him extremely uncomfortable in his desires. Ultimately, while he enjoyed this portion of himself it made him embarrassed and destroyed any self esteem he had here. Fast forward to him and I, he discussed these desires fully upfront to me fairly early in. Though not as in depth as we have now, he was attempting to make sure none of his desires would scare me off. Here we are still, so obviously none of them have. He wants small supple breasts, something concealable but playful. He wants to be on estrogen and stay limp and caged (even though the cages he's gotten up to this point are slightly uncomfortable for him so we're still searching). I've given everything I can think of to make coming to me with his fantasies a safe, okay, indulged practice. He's welcome to wear my bras and panties, I've purchased us a toy to use besides the ones he has, I've bought him bras and panties and two super sexy dresses. We've danced together, played together, I've loved on him and held him when talking about all this becomes too much and he gets super nervous. He said I'm doing great. I have offered to help in every way possible, I've accepted that he personally doesn't want to be able to get an erection anymore but that he still desires to please me and when we are intimate I get what I desire absolutely and I let him know as much so it's never a guessing game. Here recently he's found different random (non local) women and has asked them to humiliate him & such. Call me crazy but I consider that a break of trust and borderline cheating, especially considering he'll share pictures with them of himself caged, dressed, etc that he says makes him uncomfortable. I'm sure he's looking for something that I'm not doing right given how new in this I am, but what? Insight? It's making me feel insignificant, like I'm the side chick because all of sudden it's a "inconvenience" for me to be involved here and obviously we aren't having a sexual relationship between the estrogen & such.
Hi, I think many males here would give their right arm for what you have done for him. I think you need to stop pandering to him so much and make him work for YOU. I find it amazing that you have helped him so much and yet he still goes online looking for other women. You are are doing nothing wrong, don't feel insignificant. He's being selfish. You are a very open minded and selfless person, he is lucky to have you.
It sounds like this guy wants both a safe place where he gets support and respect along with someone to humiliate him. He doesn't think you're capable of doing both or he doesn't feel comfortable asking you to do both. That's not fair to you. If he wants respect, he needs to give respect. Part of that is communicating his needs. If he can't or won't do that, he's not worthy of your time and consideration. If he tells you what he needs and you find yourself unwilling or incapable of fulfilling them, don't feel bad. You've gone above and beyond what anyone can reasonably expect from a partner. This guy should be worshiping the ground on which you walk. If he's not happy with you, he'll never be happy. That's not your fault. That's his. From his interest in chastity and humiliation, it sounds like he might respond to you laying down the law. That doesn't mean you need to bend him over your knee and give him a paddling if you're not comfortable with that. He definitely deserves it though. Give him rules and tell him he either accepts them and whatever reasonable punishments you decide upon if he fails to uphold them or to get out.
You may be a tiny kitten but believe me when I say, you have a roar in you that can and will surprise him. From what I can see, you have been learning and enjoying this so far. He seems to also have been enjoying it up to a point. Personally I think that he is looking for a more dominant persona. So far you have probably been asking questions and enjoying what the two of you have been doing but he has been the one in charge. Time to get those tiny claws out and start laying down the rules. Get dressed up a bit in some sexy stuff and high heels, put on your best School Mistress voice, point at him, then at your feet and repeat "you and your pathetic little cock get over here and explain to me what on earth makes you think that behaviour is acceptable." Channel Katy Perry and her Roar song. Then tell him that you are the only female in his life and you are not accepting such disrespectful behaviour. After that, you are on your own as I don't know what he will reply. Good luck sweetie x
I can't offer anything more than our two mistresses have already articulated. What he has done isn't acceptable. It's up to you how you deal with that. Good luck.
Any intimacy whether in person, over the phone, via text, messaging or forum boards should be negotiated between partners. If he has done this with you and you both agree and are ok with it ... Game On! If it is not black and white or has been discussed, I would strongly suggest a sit down and discussion. If it involves a third party, I highly recommend that you make sure he isn't horny and is in a relationship state of mind before talking. So the question is (and you don't have to answer it here and I didn't read the other responses fwiw), are you comfortable with the outsourcing of these things? Do the activities add or subtract from the relationship. E.g. there are examples where a stronger and independent woman may not feel comfortable with corporal punishment, so their is an agreement to have the partner visit a dominatrix with set guidelines. Whether the person is there or not is up to you. In short, any action that sexually excites you or him in the confines of the relationship should be consented and agreed to by both partners. If the actions are severe, set up the rules, safewords, and anything else ... and once done ... go and be all-in. I am a natural switch and an alpha male; however, given my life experiences I require love and connection with my sexaul partner. IF my current relationship ended, I just couldn't go and do people via tinder. That being said, there is part of me that wants to challenge and make a woman so secure and safe and confident that we can be in a place where I could go to her and say ... for the next 30 days I want to see if you can break me and my alpha spirit and exit out of it and not think less of me as a man. As a kicker, if you can't or don't make it happen, then the following 30 days you will be a Stepford wife and be very much like a 1950's (it isn't my preference btw ...) .... rinse wash repeat and see who wins the fun and fancy free struggle in the relationship. But if at any time if me or you feel "threatened" .... simple equal partners is what we are .... as the relationship is what is important not the kink. That share is to help you understand the importance of communication and honesty and openness and setting boundaries. If you don't have that ... stop and talk ... since talking and communication is free .... pain due to expectations being gone and lost are eternally expensive.
On reflection I think you deserve a better guy, far less focused on himself. And with all due respect you need to start putting yourself first far more, especially if you are into TTTWD.
Because you have been supportive and caring, helping to rebuild his self esteem, you've gotten him into a safe space. Do you humiliate him at all? It probably feels contrary to do so after being so supportive, but it sounds like it is time for a different approach. You've shown him that you accept and support him and his kinks as he is, so any dominance or humiliation you inflict on him will be from that foundation of respect. You may be reluctant to do this, thinking it makes you like his ex, but he will understand the difference.
Those responses are ten times more than I expected, thanks to everyone that's put in their advice. It's nice to read these and not have to try to figure out what some computer warrior with a superiority complex is trying to type from behind their screen, which I feel like a lot of forums breed these days. I do try to humiliate him (keep in mind I don't know if I'm any good at this portion) but I've read online a bit, of course browsed the memes that Google searches will pull and actually love writing so when we're messaging back and forth at work or something throughout the day I'm probably pretty decent. It's in the bedroom that it does sometimes get me caught up. I'm not always as assertive as I need to be, mainly been tip toeing where I should have gone right in. I think I just need to channel the part of me that is demanding, because when we're really well into these moments I can get fairly aggressive/passionate and he seems to respond exceptionally well then. I just don't think I've done my part to draw that out longer than those spurts. Perhaps it's my inconsistency that's not helpful in this. At the start of this he explained he does "top from the bottom" sometimes, and I think my fault is I've been letting him do so. If he wants me to take control I should be. Thanks y'all.
You be you. The point in loving power exchange is the fact the you should feel fully empowered and doing the things you like and prefer. That is the whole point. If you like to have a partner that provides independence and leadership, that is "ok" too. What you can tell him is that you desire and want a man to delegate some of the decisions and leadership so you can do what you want to do and love best. But also do remember he has an "itch" and "urge" that needs care and love too. So I hate to use the phrase of "top from the bottom" but if you have submissive tendencies that you love to have handled, tell him you want him to be a dominate and if he fails to deliver ... he will pay. E.g. if he like long term chastity and feminization, if he is dominate in the right way he only gets a 2-3 day lockup. If he fails he gets a 2-3 week lockup and one helluva a bitch to deal with Areas where it sounds like your partner wants to drive in can fall into the cuckolding arena (not saying you or he desires it). But maybe a possible tact (not asking for your personal views btw) is to state that you really want to see his male "unit" tucked away so you can find out what it feels like to be with a "real" woman in real life since that sounds better then being with a biological male. Then use the less is more theory in life and say nothing else .... Remember to talk, communicate, and reward honesty and openness ... and punish the "fuck" out of secrets and closed mindedness ....
The only consistency you need is in punishing negative behaviors. The saying "spare the rod, spoil the child" could easily be "spare the rod, spoil the sub". You don't have to constantly indulge him and his needs if you don't feel like it. You're not, to take L-U-C-Y's term, a fetish machine for his pleasure. If he behaves and you feel like it, then sure, do whatever, but don't feel obligated to ever do anything you don't want to.
I would just try being yourself in the beginning and have fun with it. Worry about the leather clad dominatrix he has been fantasizing about later.
You raise two issues... sexuality and infidelity. I don't think you have any problems between you both regarding the former, you're both open about it and discuss it freely. You need to together discuss your feelings about the latter in the same vein.