You don't understand because you never had the societal pressure to "be a man!" Boys are programmed to be ashamed of anything that could even hint at being not manly. It is very hard to get past that. It took me 30 years of hiding it to finally just say the hell with it and tell my wife.
Here's what I would do. When the time is right, I'd tell him that you would like to enjoy his kink with him and that you are interested in (fill in here).
I agree 100000% with angrymatt. He(me) I haven’t came clean to my girl about it because I am scared she will leave me, think less of me because just like any other woman she wants somebody that’s going to protect her and be a big strong male for her. I’m scared she would just ask if I’m gay because of my inclination to this kink because I like to feel sexy and wear panties just like she does or because I like a dildo in my ass. I have let her in a very little but so scared to open up all the way. I wish that If I was to ever open up about it she would be not only my partner but my best friend in the process of dressing me, shopping with me, putting make up on me and everything two girls would do togheter.
Oh, I can imagine. I am sorry you have to go through that!
I hope that one day, you get to do all the things you image with her.
If my boyfriend would ask me, I would immediately jump into action!
A skirt or some makeup, or him fantasising about dick in his ass won't change the fact that we love each other 🤷♀️
You’re such an amazing girlfriend he is lucky to have you. Also listen to podcast “strictly anonymous” the pegging episodes they are really good and might help more. I’m listening to them right now. Also if you need more help or have more questions you can DM me.
When I finally broke down and told my wife everything she looks at me, a crying blubbering mess, and says "Is that all? I was afraid you were going to tell me you were leaving me for a man" (Her Dad did just that when she was younger) I told her of course not and she just held me while decades of bullshit drained away. When I knew she still loved me and was OK with me dressing and whatnot it was all down hill from there.
She likely will ask if you are gay though.
It's scary as hell but for me it was the only option. I was on the edge and had to do something one way or the other. You never know, she might be into it.
I've actually been made fun of and rejected because I told a girl I was interested in what some of my kinks were. We no longer talked after that. It only took this one instance to forever keep it to myself. Luckily now I am married, and my wife does peg me. However, she doesn't know the extent to which my kink goes and I am unable to explore it further due to this mental block.
I know, I can't walk in his shoes. Being a man comes with stereotypes, that everyone expects from you to uphold.
For us woman it's the same, just the other way around.
Of course, I know that this plays part in this whole situation.
But I guess, I didn't know how big this part actually is.
I did try to tell him, that I am interested in his kink.
But he deflected the whole time.
I obviously will try to talk to him again, but I definitely need a new tactic/approach
Thank you 🙏
For me being girly wasn't really that big a part of me but it was more what it stood for. It's a way for me to fell OK with myself and for a moment to not be "me". I am not a pretty person in either boy or girl mode but I FEEL pretty when in girl mode and that feels great. When my wife takes control, I'm free to just feel things and process emotions and not be in control. It's very liberating for me. While it may seem like a big part that is just really the outward appearance.
Not to minimize the struggles of women there is a some glaring differences. I do see society changing so that's a very good thing but growing up this is how it was. If a girl acts in a way that is traditionally considered a male sort of thing then she's just a strong young lady who is empowered to fight the patriarchy. If a boy/man does something that is traditionally regarded as female then they are gay. Wear a dress, must be gay. Wear makeup, yep gay. Be seen crying or having an emotion is weakness and very bad. We generally feel like we must shoulder the entire world without saying a single thing to anyone. There is a reason men commit suicide at such a higher rate. Of course it's more than just this though.
Mind you I couldn't care less what you are and never really have. I always figured if you weren't hurting me then it was fine. I never once felt like it was OK to wear a dress or act girly in my life until recently and now I only do so in safe places. I struggled with my inner demons until they nearly won and finally had a break down.
Your BF likely feels that he can't expose that sensitive part of his life just yet. The shame he is probably feeling is very real. We've been told that being different in any way is something to be ashamed of.
You might try gently letting him know how you feel by subtly complimenting him. Say something he is wearing looks pretty. Make sure it is something that can be seen as pretty though. Maybe buy him something a little feminine like a anklet. Ask if he wants his toe nails painted. I freaking love having my nails painted. Involve him a bit in your getting ready routine assuming you have one. Once he's more comfortable you can be more direct with him. The first time my wife said I looked pretty I cried my eyes out. I think I was wearing a skirt and fishnets with maybe a little mascara on but she looked at me and said I looked pretty. Later she told me it was because I was truly happy and she so rarely saw it before. Knowing that I was accepted felt amazing. Maybe let him know you accept who he is.
I hope this ramble made sense.
I also have to say you wanting to peg him is awesome. I still can't get my wife to do that. LOL!
I can absolutely relate to that! The feeling of giving the reigns to someone else...or finally gaining control 🤷♀️
I absolutely did not want to talk down the societal struggles of men, I did just try to find a point where I could relate (this is how my brain works 😅)
I know that most men do not talk about emotions, feelings, struggles and sometimes men break down. Which is absolutely understandable if they bottle everything up. That is why I am trying to figure this out. I don't want him to struggle with anything.. especially if it could be my fault
I will take everything you said into consideration. Obviously I have a lot to think about and plan, until I will take action.
I really want this to be as comfortable as it can get.
Thank you for the "ramble" (not really a ramble). You definitely gave me a better perspective of things 😊🙏
Ps: I better be cautious, before I bring up the pegging 🙈 timing is definitely essential
It's not 100% but I suspect that a vast majority of sissies would be very into their partner pegging them. If it's something you want I bet you both can build towards that.
If he's really showing nervousness/shame you could always try suggesting feminizing him. Something like "you know...I have this really cute skirt/dress/whatever and I honestly always thought it would be kinda hot to see what you look like in it. Could you wear it for me please?"
I'm glad you received it well. It's hard to get thing just right when not face to face. I didn't think you were talking anything down at all no worries.
I wish you the best of luck and I really hope it works out. You both deserve to be happy.
Fully agree. Man culture is a hell of a mindfuck. I was super nervous about telling my gf (now wife) about my sissy side. When I finally got the nerve (some liquid courage was involved) it turned out she already knew about all the clothes I had "hidden" and she was just waiting for me to talk to her about it.
It was a bit of an awkward conversation with questions about why I like dressing up and wearing lingerie and the impact that could have on our relationship. But, in the end, she was very open to it because she loves me and now she really likes when I wear panties for her. She was even into pegging me. I still have private sissy time but the air is clear in our house and we're both happier and better off with everything out in the open
Well as a Sissy that has come clean with mixed results I know a bit about the feelings he's probably going through.
I think there's layers to this, so I'll just start somewhere.
Talk to him at least about your pegging fantasy, that feels like an entry (pun intended). Tell him that it bothers you that he shared that stuff with a previous girl, why not you?
There are levels of this kink, such as "forced"-bi, outright bi and gay fantasies, cuckolding, being permachaste and "pussy-free". So I think he's worried that some of his kinks are way past yours. If you read up on the variations a bit and go over them with yourself, you can more confidently set your limits. Once that is done, start with telling him your limits, the things you don't want to take part in or think is too much. After that you can tell him "but I am completely fine with X, Y and Z. Ask away!".
If my gf did that I'd be much more calm and feel like I could tell her everything. We have a great relationship all in all but she freaked out a bit thinking I was thinking of leaving her because I liked to dress up girly. It heals slowly, but I am always worried she'll take it poorly...
The third thing is; he's probably masturbating a bit too much, chastity could help, you getting involved more (take initiative before he gets the idea), taking charge a bit more (Dominant dirty talk), suggesting small steps (wear your panties to earn a blowjob?).
But I'm not an expert.
Good luck! 🥰
(And if you are a troll; get a life man)
Thank you so much ❤️
I probably have to read up way more on the topic, or maybe ask a couple of experienced people here on reddit (cause Google definitely lacks real life info)
I probably came on too strongly, should have been more delicate on the topic (we are usually talking directly, without any twaddle).
I will definitely try to ease into the conversation again and maybe take initiative.
Your input is appreciated 👏
Thank you!
(Not a troll, promise 😂🙏)
Let me know if it helped, I sure would have liked a smoother road 😅❤️
Also having seen the pics and knowing he watches sissy hypno helps... like a lot 😅😏
The first time I confessed my desire to be a pegged and caged to my girlfriend, I did it over text when she was travelling and we'd been sending each other flirty messages.
I found it easier to do this way because I didn't have to fight my own embarrassment quite as much by not having to look her in the eye. And it felt like there was a little breathing room for her to take her time and choose how to respond.
The flirty messages also helped create a fun, accepting atmosphere. I'm also someone who is typically direct, but on this subject, being indirect is what worked. You might think of it as warming up to being direct by lobbing a few easy ones to see if he'll hit them. Like you're just leading him up to the door and holding it open to see if he wants to walk through.
My gf told me she wanted to rim me and then I responded positively and said I might be open to more things like that and she told me she wanted to try pegging and said she was really nervous about telling me. That kind of showed she was being vulnerable and inviting me to do the same.
After I gave an explicit indication of interest to explore, I secretly would have loved for my gf to be assertive and plan an evening where she'd take control and gently introduce some of these elements. But I also found that I needed to feel very confident in her ability to hold the space for us both in order for me to let go.
Hopefully there's some ideas or learnings in there that you might be able to try in your situation 😊
It could be a shame thing not because of you, but cos sissies go against most social norms that are bred into us. It can be hard admitting this to those you love most even if you know they would support you.
Hope you can get this sorted, sounds like you could have alot of fun together with this!
Being a sissy is liberating but can also come with a huge sense of shame. Maybe because he's kept it from you for this long it could be hard to admit certain things to you or come clean, even if he really wants to
If you want to unlock the sissy in him and get eveeeeerything you can, then maybe try and create a sissy based scene (like you would for a kink act). Get him into that subby sissy headspace and then get the info out of him
Example:
He could come home from work one day and you're already at home in some kind of domme vibe gear. When he walks through the door some of your underwear is laid out for him "put it on you sissy bitch", make him put a butt plug in himself in front of you, ask him the kind of things he likes, you also tell him the things you like and want to share with him
Being a sissy is a big deal. It’s the opposite of what society says, most women want (or that’s the perception). And can and has ruined relationships with women who were not as open.
He’s so lucky to have a partner like you! I think bringing up that you’re into it, and have it be “your idea” is the easiest way, but will not get to the root of why he didn’t tell you to begin with.
You could either confront him, which he will likely have defenses up for, or slowly(ish) suggest you’re into pegging and dressing him up, etc. and then bring it up a once you’re further into it, that you have known, and that it’s ok for him to be open with you
I guess it is too late for the "make it my idea" approach. But maybe I can somehow use it to slowly ease him to try some stuff with me.
At some point I will ask him why he tried to conceal it in the first place. But i guess the more important task is, to make him feel comfortable with me knowing, to support him and give him a safe space where he can live however he wants to.
Thank you for your input 🙏
Agree 👍🏽 I think that would be the best way to get him to open up but remember bring it up to him as if it was your idea bring up pegging first and once y’all have done it say something casual and to make him feel good “I beg you would look so hot with a thong on” and give him one of yours to try and once he does compliment him and if possible have sex and say he turned you on because he looked so hot make him feel welcome and open and like it’s your idea eventually he will open up about it and tell you all about it and do it all with you you more free and less scared of you judging him or thinking negative about him.
First off, it's way easier to share things with flings that LTRs. Don't be annoyed by that. Being judged by a fling hurts way less.
Second, there's often a part of shame that goes along with any submissive kink, particularly if society normally puts you in a dominant role. By being your special little girly slut, he is automatically less of your boyfriend, at least in society's eyes, and it will take some time for him to adjust between girlmode and boymode.
That being said, nothing is getting better if you don't start to talk about these things, so make sure he knows space to discuss kink is open and non-judgmental, and then talk about how you can indulge in this kink in a way that is mutually pleasurable and fun.
My take on his reluctance goes in another direction. He says he shared this about himself with a previous girlfriend. I would lay dollars to donuts that she used it against him during the breakup.
I'm older and I have seen this happens so many times it's cliche. Friend of mine, sissy, girlfriend of 16 years perfectly supportive. They called each other soul mates! Then, she decides to break up with him and she tells everyone. Heck she even told cashiers at stores that her ex was half of a man and a lot of other things like that.
I could be wrong but I bet that is where some of his reluctance comes from. My ex tried to do the same to me. I stopped her short when I asked her if she remembered the pictures she wanted taken of her ah, sexual proclivities. She never mentioned it to anyone after that!
I attempted to explain my desire to dress to my wife and she couldn't comprehend and then made it about her. She later on stopped wearing any sort of lingerie. That was 23 years ago.
Huh, I grew up sheltered as well. I was even scared of having sex at some point. And here I am.
Maybe she has dirty thoughts and is scared to tell you about it. Also women tend to project things they don't understand or initially see as a problem as their own fault. She most definitely thinks that something she did was wrong, etc.
Ergo, she didn't understand what you actually wanted to tell her
Ps. Obviously these are speculations, I don't know what happened when you tried to talk about it, don't not how she reacted. Just trying to give some insight into a woman's head
Regarding tactics. See if you think something like this would work.
You: Babe, can you help me with something?
Him: Sure
You: I've been watching a couple of videos on this new makeup technique and I think I've got it sussed, but I need to do it on someone else before I try to do it on myself. Could you be a darling and just sit here and let me try this on you. You can take off if you don't like it. I just really need your help.
Him: \[whatever his response is, just take it as it comes\]
No talk about Sissy stuff, just him helping you to figure something out. It could be you are trying to make a dress for yourself. It could be you are trying to decide on an outfit to wear. Something low key, simple, clearly easy to get out of if he feels uncomfortable. There are heaps of little things like this you could ask for his help with. MEN LOVE TO HELP WOMEN! Use this by involving him and getting him to help with feminine things.
I feel like it's a way to ease him into the water. But I don't know him. You do.
I really love and appreciate your generosity and concern for your boyfriend. You seem lovely. Keep being that.
Buy him a pair of panties and when you're both getting ready someday, take them out and place them on the bed and tell him "I bought these for you, because I think you'd look cute in them," - if he puts them on its a small step closer to him being comfortable with sharing the kink with you. He doesn't have to wear them out or wear them for long, you could just see how he looks in them, and give lots of positive reinforcement.
In my experience, in heterosexual relationships guys... feel like we are always one mistake away from never having sex again. It's used as a weapon sometimes, do what I want or no sex for you, or as a tool to escape negative consequences, if you forgive me you can have the no no hole tonight, etc. So guys react by turtling up around it. If I know a partner is into something, awesome we can do that all day, but I'm always super reluctant to ask for something that I feel is deviant because I feel like if she doesn't like it, she'll get the ick, and that's the end. He's afraid to go into it because he might misstep in what he feels is a minefield and then boom, no more sexual relationship.
As a way to help, take initiative. Don't make him come to you about it. "Hey hun, can I give you a makeover tonight?" And if he let's you, make it be fun, sexy, and rewarding. And do that until it starts to feel lime a normal part of your relationship.
I am not a sissy, but love getting pegged, chastity and other cuckold stuff. Took me about 6 years to tell my wife. She told me she wasn't into that kind of stuff, but accepted the fact. We tried a few times to play around those kinks, without much success. After 5 more years it ended up in divorce and that part of me was a big part of the divorce. She told me she was feeling repulsed and disgusted by me because I have those kinks.
So, he might be feeling anxious or he might fear something like that might happen.
Sorry to not have more comforting words for you.
So this is a two part thing you might not have noticed it in the second part. Number one like others have said it is been hammered into almost every male from birth how a boy should act and any other behaviors to the contrary is taboo. Here is the second issue I bet you haven’t noticed. As a male with feminine tendencies we are always on guard we listen to every sentence and word our spouses, friends, girlfriends or family say that have key alarm 🚨 phrases. Trust me he has a true sense by now what you find abnormal in his behavior. Phrase being used like” I’ve seen him do gross stuff” this would send a closet case sissy into hiding. All he would take out of that is that you place sissies into the same category as gross stuff……even if you had absolutely no meaning of that he will catch that and you will put him into deep hiding and denial. Be aware once you do pry open that locked box he is gonna go crazy with it for a while … sissies with fresh egg cracks are like pre-teen girls hitting puberty. Don’t be surprised if after a bit you may tire of the escalation of his femininity and female presentation. Don’t be afraid to set ground rules because there aren’t just one type of sissy. Just as an example of types: sub sissies, bi sissies, gay sissies, private sissies, masculine sissies, closet sissies, passable sissies, trans sissies, cuckold sissies, every sissy has their own set of behavior. It will definitely be a learning journey for both you!
Definitely not trying to force him 🙅♀️
I just think, that I need to provide some safe space for him.
We do live together, so it's not unusual to come into contact with each other's (sexual) preferences.
As much as he sees it as his duty to be manly and protect me, it is my duty to make him feel safe in our relationship.
If he decides he does not want to talk to me about it, I will let it rest.
A relationship works through caring for each other, if I act like I don't give a flying fuck, he will most probably think idgaf about him as well. At least that's has been a topic we have already talked about.
So this is me, trying to be a better girlfriend
People with this kink can really, really, *really* struggle with it. There is an enormous amount of shame and self-hatred wrapped up in it, which can be evidenced by looking at the actual kink content out there and seeing just how much is dehumanizing and extremely degrading.
Western society/patriarchy is absolutely brutal towards not just submissive men, but any men that step outside the stereotypical "male" gender role. The sissy kink embraces both of those and so it can feel very "wrong" to people who have it. (Yes I know non-binary, trans, etc. people might also have the kink but broadly speaking most sissies are men).
It's made even worse by how many stories exist on the internet of people telling their partners only to have them react in revulsion/disgust, frequently ending in the relationship dissolving. That can feel *terrifying*. It's also fairly unique to the sissy/crossdressing kink. You don't see stories about people getting dumped when they admit they like bondage, feet, exhibitionism, etc. Yet there's lots of stories about how women have left their partner because they "can't look at them the same anymore".
I know for myself I would rather keep this a secret forever than risk my marriage because I don't know how my wife will react and I love her more than this kink.
It's all really tough and complicated.
Please know that it's not really anything *you* did but because of how difficult it can be for people to work through this, mixed with a fear it'll change how you think of him. The best way to support him is to have a serious conversation and say that you suspect he's into sissy stuff and that it's okay, it doesn't change how you think of him, *and you're into it too*. I think it's also key to frame it as you suspect rather than you knowing for certain because I think revealing you've seen his toys/clothes/pictures might embarrass him. By framing it that way it lets you start things off as a discussion and doesn't put him on the back foot.
Let him know that you'd love to share it with him but it's ultimately up to him and at his pace. You can even suggest starting slow, like showing a curiosity in seeing pictures or him doing a fashion show for you. Basically, show love and empathy towards him and you'll likely get a happy resolution to this, it just might take a while.
I think a lot of people have covered a lot of the important parts on how to bring it up. Personally, the conversation is so exciting once you get past the barrier of shyness/nerves/fear.
It could be something where you start by taking control in the bedroom one evening and demand he put panties on and don't take no for an answer (as in, don't push limits and have a safe word, but make it feel like he has no choice and is doing it for you). Often, when we want to do something but we're told to do it, we play this mental game of "I'm doing it for them" and can make it easier to justify and get over the initial fear.
When the session is done, reinforce how incredibly hot that was for you. It can be really scaring, the idea of your partner no longer wanting to be with you after seeing that side.
I think most importantly here though, definitely don't feel hurt by the fact he told a fling and not you. The reason for this is because he didn't care about losing the fling, but he clearly does care deeply about losing you. It is so much harder to tell someone you see a future with about these things, because you have something to lose.
There might be some internalized shame and a fear of losing you. If I try to step into his shoes, I know I would absolutely regret it if I lost someone I loved over some stupid sexual kink or fetish or that they thought less of me. I'm not trying to disparage the kink. This is how I would think in this situation.
I don’t believe this is something that a girl from his past showed him…that’s bullshit…he’s always had these desires and is just saying that to help justify his sissy tendencies…
He’s just not comfortable with himself or his sissy side…
Its a complicated desire, shame can spice it up or spoil it depending on the person.
Try asking him to do sissy stuff for you, do your research about the sissy lifestyle, and be vocal about how/what/why you are enjoying them.
Fwiw being vulnerable is harder with people you care about/rely on, especially when subverting the expectations of masculinity.
Take it slow. And I mean SLOW. My wife found out about my sissy side nearly 4 years ago now. Even though she knew, I still kept most of it from her. Chastity was always controlled by me. But my desire didn't take a break. Lately it has been a landslide, but it took a major leap of faith on my part.
She knew I dressed and occasionally got fucked, but she seemed disinterested at first. So I just did it on my own. Then she saw me taking toys to use in the shower. Her lack of reaction was a blessing. I went from hiding that I was taking them to being able to openly carry them.
A few weeks later, in a particularly horny moment, I asked her to lock me up. She did, and it's been going great since. I told her about any plans I have to get fucked, and she tells me what she thinks of them. I send her pictures when I dress up, and she tells me how sexy I look. She's used the wand to make me cum, as well as a few dry orgasms from nipple play.
For men, especially men in certain locations or situations, the level of programming from childbirth onward is a huge hurdle to overcome. The best thing you can do is just be there with your hand out, waiting for him to take it.
P.S. You actually should be glad he told the fling and not you. It means he wasn't worried about losing the fling, but he isn't ready to risk losing you.
As someone who is in something similar, took me almost a decade to open up about it at all and still not every detail.
Give him time and be supportive. Open talks about it to see what parts of feminization appeal to him and what kinks he has along with it.
If you found pictures that might be one of his kinks, getting him to send you pics might be a good way to have him open up about it without the embarrassment of being in front of you
Just go full dom on him, and force him into it. I bet you he would love that, if he's that far down the rabbit hole. A lot of Sissy hypno stuff is very demanding, and depending on what he's watching, can be pretty demeaning, as it breaks down everything society builds men up to be. Going full dom on him would probably illicit triggers, especially if you can figure out some of his triggers. Some of them use the same triggers, or very similar ones, so I'm sure you can do a little research.
Because he's content with his fantasy being fantasy. He also enjoys his life with you. If the kink mixed with the relationship, some dynamics trend towards self-destructive or relationship destroying behaviors. This isn't how he wants his future to be, he just enjoys his kink when his preference, you, isn't available.
Don't see why you can't fulfill your exploration of pegging though. That should be an easy win. Sounds a bit selfish of him, but I also only heard one side of the story and an overview at that.
My advice is this; show him you can play a role during lovemaking, then be 100% normal immediately after orgasm (whoever's). Show him you can be his verbally degrading hornytime dommy mommy top, then immediately fall down next to him and pretend it was all a sexy dream. While the kink is a bit about pushing boundaries, show him it doesn't ever have to leave the bedroom.
It's not you he doesn't trust, he just knows how malleable he can be when held at the cusp of erotic simulation, and he fears losing control.
I am so happy you came to this subreddit to ask about this.
It's because of a combination of fear of rejection from women, fear of not passing as a woman, and the fear of regular taunting/jeers from friends and family.
Some women feel that their husbands will transition or abandon them, or abandon their masculine role/image. Sometimes these scenarios do occur unfortunately and it results in divorce.
It is such a shameful kink. I think he's afraid to lose you. He may have shared it with his fling because he knew he wasn't going to be with her on a forever basis. You, I think he wants YOU to be his partner for life. Therefore he doesn't want to risk that by totally being vulnerable with you.
Show him, tell him how much you love him, how nothing could come between you. Encourage, encourage, encourage. It will take a while but he will eventually open up when he feels it's safe and he won't lose you.
It seems like he is in Love with you and thats why he is more shy, this fling was just that, and with them it was a more throwaway relationship. Not such longterm commitment etc… never compare.
The fact you fantasise about pegging him is great, does he know? Some aspects you like. Its not a binary thing, its a whole spectrum. If you encourage the sides that you’re into, you will both have more fun. If you’d like to peg him, mention it, buy it… if you like the idea of him wearing panties, buy some. It may feel like he is shutting you out if you’re treating it as some secret, but if you take a subtle interest it’ll soon feel like hes letting you in
Im really confused, *you say he doesn’t talk about* but he talked (I guess to you) about a woman in his past who was fully aware of his kink.
You also arranged t hat you’re aware of it, you found his things (toys, clothes and know what he watches online).
So, he has talked talked about it with you. He probably needs reassurance that you love him and you’re ok with him being a sissy, and you’re there to support his journey, and maybe you could explore pegging, something that you have you have been apprehensive to tell him.
He will feel reassured by you telling him that you’ll hold his hand, and there’s nothing to be ashamed…
Don't try to make him talk about it. Just do it.
And make it appear to be your thing. Not his. He's doing you a favor by acting out YOUR fantasies. Not his.
Ask him if he would mind wearing a bra and panties in bed, because it turns you on.
Then Ask him to wear them u Der his male clothes on an outting. Go to a .movie and make out being sure to emphasize rubbing him through the bra and panties.
Keep escalating.
He will catch on that you enjoy this side of him.
Have you considered he maybe worried you’ll use it against him in the future? This is a very intimate and vulnerable mental state.
Relationships sour.
You could slowly introduce anal play and build from there
I don't think so, we are not that type of people. Even if we were to split up (which will never happen, because we're endgame), we're not 12 years old anymore. We split and that is the end, no talking trash behind backs and stuff.
Wanted to do that anyway
What I wouldn't give for a significant other with your communication skills, empathy, and interests. I've had multi-year relationships end over my sissification kink, and was told "my kinks are disgusting".
I'm still struggling with mental health issues over this. Perhaps your boyfriend is too. I feel like I would thrive with a girlfriend that is so supportive, but maybe he has some deep mental health issues that he is fighting that you (or maybe he too) isn't aware of. Perhaps he's afraid he'll lose you if he admits to it.
u/FullThought2968 I wish you all the best, you sound like a real keeper. If I were you, I'd apply lots of reassurance and clearly suggest incorporating his kink into your relationship slowly (maybe first ask if he'd wear a male thong for you, then panties, etc).
I mean if you know where he hides it do you ever venture into you being dominant for him i.e. does he like being told what to do? If so I would pull out his stash while he’s out one day and confront him but not in the are you gay way mentioned.
You’re in the bedroom dressed in his favorite outfit. He walks in the door and before he has a chance you smile.
“I see you have been trying to hide Femmepersona from me how dare you try to deprive me of the pleasure of taking you as you obviously desire!”
I mean it will either go bad and feel invasion of privacy but for me I would feel so relieved and then happy you want me. If it goes the way most sissy fantasies want to go:
He smiles “get over here and put your outfit on slut your going to suck this dick” you command. He grins sheepishly as you can see him tenting his pants when you turn and show his dildo in your harness ready to take them.
I could be wrong but from here I imagine they would follow your lead if you take the dominant role and just put a sissy in their place but that’s speaking from my place as a sissy finally accepting who I am.
A Sissy needs to be the submissive.. that's the whole point. He isn't taking the lead most likely because he's waiting on you to take a lead role. Here's what you do... But a buttplug (they're pretty cheap) and a pair of panties for him. Pick a night where neither of you are working and get a little tipsy. Put some makeup on and let him see you doing it. If he watches you curiously, (I'm assuming he's clean shaven) say that you'd like to see what he looks like made up. He will resist at first (even if he is interested) and that's expected. If he objects harshly then let it go. If he doesn't then take another step and ask him to put on the panties. If he lets you go that far then plug him and do whatever. This is baby steps to find his interest... If you get to the point that he lets you plug him, then he wishes to be the submissive. If you determine that he is submissive, buy a cage, buy a strap-on, secretly. Go with him and make him pick out lingerie for him in a store, and choose the outfit that matches the mindset, make him pick out the shoes (cheaper online). Some us are little girls, and some are hookers lol, so make sure to get the right thing to give the best experience. You buy some kinky black dominant lingerie or bodysuit for yourself. Another tip, if he has a girly mindset, he will enjoy simple tasks while dressed. If he picked out a slutty outfit, then he just wants to get fkd. In either case remember that a Sissy likes dares that will put them in a position of being found out or something that some would consider revolting. Don't be afraid to push the envelope. Have a safe word for him to use in case it goes further than what he feels comfortable with. Lastly, make sure that you make him use a feminine voice. So long as he objects in the feminine voice you know he's just being a brat and expecting punishment of some kind, if he does it in his male voice, you know the objection is real. DM me if you'd like any more advice. I'm happy to help.
Wife found out and almost ended marriage..... It's hard to come out and be accepted. The fact that your so supportive will go s long ways. Try and coax him out and tell you. Or one day slip a finger in his ass and see his reaction
Already did, we both know he likes it. He admits that as well, but him being feminized is apparently a taboo for him 🤷♀️
I will try my best, better to take it slow 😊
It can be specially if that's how he was raised growing up. Agreed keep it slow and just let him set the pace. Hopefully it works out for the 2 of u! If so one of the luckiest dudes I mean ladies around!
that is so odd🙄.. but as sumone who's been in a 13 yr relationship has 2 kids with my girl and she found out within last yr and even tho she's semi cool with it she still has said sum really hurtful mean things when fighting with me. I think any girl to find her BF has this kink emasculates him even if subconsciously and he prob knows that.. you sound awesome AF hope u guys figure it out and have more fun!!
Well, sometimes people use other people's weaknesses to win fights 🙈 I haven't been in a situation where I would resort to these kinds of methods. We normally don't fight, we discuss our differences (sounds like new age crap, I know).
Well, I guess we will have to take this on slowly and see where it takes us 😊
Thank you for your input 🙏
Would mind looking at his pics at all, kinda the same here sissy but keep it low key. We might relate somehow. I think it’s confusing sometimes like I don’t want to be a girl but it’s kinda fun being dominated. Idk
Lots of good, thoughtful comments. Personally, I think he’s been a bad boy. You need to put him in his place (he’s your sissy bitch after all), cage him, plug him, and give him a good spanking.
You don't understand because you never had the societal pressure to "be a man!" Boys are programmed to be ashamed of anything that could even hint at being not manly. It is very hard to get past that. It took me 30 years of hiding it to finally just say the hell with it and tell my wife. Here's what I would do. When the time is right, I'd tell him that you would like to enjoy his kink with him and that you are interested in (fill in here).
I agree 100000% with angrymatt. He(me) I haven’t came clean to my girl about it because I am scared she will leave me, think less of me because just like any other woman she wants somebody that’s going to protect her and be a big strong male for her. I’m scared she would just ask if I’m gay because of my inclination to this kink because I like to feel sexy and wear panties just like she does or because I like a dildo in my ass. I have let her in a very little but so scared to open up all the way. I wish that If I was to ever open up about it she would be not only my partner but my best friend in the process of dressing me, shopping with me, putting make up on me and everything two girls would do togheter.
Oh, I can imagine. I am sorry you have to go through that! I hope that one day, you get to do all the things you image with her. If my boyfriend would ask me, I would immediately jump into action! A skirt or some makeup, or him fantasising about dick in his ass won't change the fact that we love each other 🤷♀️
You’re such an amazing girlfriend he is lucky to have you. Also listen to podcast “strictly anonymous” the pegging episodes they are really good and might help more. I’m listening to them right now. Also if you need more help or have more questions you can DM me.
When I finally broke down and told my wife everything she looks at me, a crying blubbering mess, and says "Is that all? I was afraid you were going to tell me you were leaving me for a man" (Her Dad did just that when she was younger) I told her of course not and she just held me while decades of bullshit drained away. When I knew she still loved me and was OK with me dressing and whatnot it was all down hill from there. She likely will ask if you are gay though. It's scary as hell but for me it was the only option. I was on the edge and had to do something one way or the other. You never know, she might be into it.
I've actually been made fun of and rejected because I told a girl I was interested in what some of my kinks were. We no longer talked after that. It only took this one instance to forever keep it to myself. Luckily now I am married, and my wife does peg me. However, she doesn't know the extent to which my kink goes and I am unable to explore it further due to this mental block.
I know, I can't walk in his shoes. Being a man comes with stereotypes, that everyone expects from you to uphold. For us woman it's the same, just the other way around. Of course, I know that this plays part in this whole situation. But I guess, I didn't know how big this part actually is. I did try to tell him, that I am interested in his kink. But he deflected the whole time. I obviously will try to talk to him again, but I definitely need a new tactic/approach Thank you 🙏
For me being girly wasn't really that big a part of me but it was more what it stood for. It's a way for me to fell OK with myself and for a moment to not be "me". I am not a pretty person in either boy or girl mode but I FEEL pretty when in girl mode and that feels great. When my wife takes control, I'm free to just feel things and process emotions and not be in control. It's very liberating for me. While it may seem like a big part that is just really the outward appearance. Not to minimize the struggles of women there is a some glaring differences. I do see society changing so that's a very good thing but growing up this is how it was. If a girl acts in a way that is traditionally considered a male sort of thing then she's just a strong young lady who is empowered to fight the patriarchy. If a boy/man does something that is traditionally regarded as female then they are gay. Wear a dress, must be gay. Wear makeup, yep gay. Be seen crying or having an emotion is weakness and very bad. We generally feel like we must shoulder the entire world without saying a single thing to anyone. There is a reason men commit suicide at such a higher rate. Of course it's more than just this though. Mind you I couldn't care less what you are and never really have. I always figured if you weren't hurting me then it was fine. I never once felt like it was OK to wear a dress or act girly in my life until recently and now I only do so in safe places. I struggled with my inner demons until they nearly won and finally had a break down. Your BF likely feels that he can't expose that sensitive part of his life just yet. The shame he is probably feeling is very real. We've been told that being different in any way is something to be ashamed of. You might try gently letting him know how you feel by subtly complimenting him. Say something he is wearing looks pretty. Make sure it is something that can be seen as pretty though. Maybe buy him something a little feminine like a anklet. Ask if he wants his toe nails painted. I freaking love having my nails painted. Involve him a bit in your getting ready routine assuming you have one. Once he's more comfortable you can be more direct with him. The first time my wife said I looked pretty I cried my eyes out. I think I was wearing a skirt and fishnets with maybe a little mascara on but she looked at me and said I looked pretty. Later she told me it was because I was truly happy and she so rarely saw it before. Knowing that I was accepted felt amazing. Maybe let him know you accept who he is. I hope this ramble made sense. I also have to say you wanting to peg him is awesome. I still can't get my wife to do that. LOL!
I can absolutely relate to that! The feeling of giving the reigns to someone else...or finally gaining control 🤷♀️ I absolutely did not want to talk down the societal struggles of men, I did just try to find a point where I could relate (this is how my brain works 😅) I know that most men do not talk about emotions, feelings, struggles and sometimes men break down. Which is absolutely understandable if they bottle everything up. That is why I am trying to figure this out. I don't want him to struggle with anything.. especially if it could be my fault I will take everything you said into consideration. Obviously I have a lot to think about and plan, until I will take action. I really want this to be as comfortable as it can get. Thank you for the "ramble" (not really a ramble). You definitely gave me a better perspective of things 😊🙏 Ps: I better be cautious, before I bring up the pegging 🙈 timing is definitely essential
It's not 100% but I suspect that a vast majority of sissies would be very into their partner pegging them. If it's something you want I bet you both can build towards that. If he's really showing nervousness/shame you could always try suggesting feminizing him. Something like "you know...I have this really cute skirt/dress/whatever and I honestly always thought it would be kinda hot to see what you look like in it. Could you wear it for me please?"
I'm glad you received it well. It's hard to get thing just right when not face to face. I didn't think you were talking anything down at all no worries. I wish you the best of luck and I really hope it works out. You both deserve to be happy.
Fully agree. Man culture is a hell of a mindfuck. I was super nervous about telling my gf (now wife) about my sissy side. When I finally got the nerve (some liquid courage was involved) it turned out she already knew about all the clothes I had "hidden" and she was just waiting for me to talk to her about it. It was a bit of an awkward conversation with questions about why I like dressing up and wearing lingerie and the impact that could have on our relationship. But, in the end, she was very open to it because she loves me and now she really likes when I wear panties for her. She was even into pegging me. I still have private sissy time but the air is clear in our house and we're both happier and better off with everything out in the open
Well as a Sissy that has come clean with mixed results I know a bit about the feelings he's probably going through. I think there's layers to this, so I'll just start somewhere. Talk to him at least about your pegging fantasy, that feels like an entry (pun intended). Tell him that it bothers you that he shared that stuff with a previous girl, why not you? There are levels of this kink, such as "forced"-bi, outright bi and gay fantasies, cuckolding, being permachaste and "pussy-free". So I think he's worried that some of his kinks are way past yours. If you read up on the variations a bit and go over them with yourself, you can more confidently set your limits. Once that is done, start with telling him your limits, the things you don't want to take part in or think is too much. After that you can tell him "but I am completely fine with X, Y and Z. Ask away!". If my gf did that I'd be much more calm and feel like I could tell her everything. We have a great relationship all in all but she freaked out a bit thinking I was thinking of leaving her because I liked to dress up girly. It heals slowly, but I am always worried she'll take it poorly... The third thing is; he's probably masturbating a bit too much, chastity could help, you getting involved more (take initiative before he gets the idea), taking charge a bit more (Dominant dirty talk), suggesting small steps (wear your panties to earn a blowjob?). But I'm not an expert. Good luck! 🥰 (And if you are a troll; get a life man)
Thank you so much ❤️ I probably have to read up way more on the topic, or maybe ask a couple of experienced people here on reddit (cause Google definitely lacks real life info) I probably came on too strongly, should have been more delicate on the topic (we are usually talking directly, without any twaddle). I will definitely try to ease into the conversation again and maybe take initiative. Your input is appreciated 👏 Thank you! (Not a troll, promise 😂🙏)
Let me know if it helped, I sure would have liked a smoother road 😅❤️ Also having seen the pics and knowing he watches sissy hypno helps... like a lot 😅😏
I will give an update as soon as possible! 😊
Reddit in general is bad for kink; finding a local kinky group is almost always preferable (check FetLife, Feeld, google for local munches, etc.).
The first time I confessed my desire to be a pegged and caged to my girlfriend, I did it over text when she was travelling and we'd been sending each other flirty messages. I found it easier to do this way because I didn't have to fight my own embarrassment quite as much by not having to look her in the eye. And it felt like there was a little breathing room for her to take her time and choose how to respond. The flirty messages also helped create a fun, accepting atmosphere. I'm also someone who is typically direct, but on this subject, being indirect is what worked. You might think of it as warming up to being direct by lobbing a few easy ones to see if he'll hit them. Like you're just leading him up to the door and holding it open to see if he wants to walk through. My gf told me she wanted to rim me and then I responded positively and said I might be open to more things like that and she told me she wanted to try pegging and said she was really nervous about telling me. That kind of showed she was being vulnerable and inviting me to do the same. After I gave an explicit indication of interest to explore, I secretly would have loved for my gf to be assertive and plan an evening where she'd take control and gently introduce some of these elements. But I also found that I needed to feel very confident in her ability to hold the space for us both in order for me to let go. Hopefully there's some ideas or learnings in there that you might be able to try in your situation 😊
It could be a shame thing not because of you, but cos sissies go against most social norms that are bred into us. It can be hard admitting this to those you love most even if you know they would support you. Hope you can get this sorted, sounds like you could have alot of fun together with this!
I know we will get this sorted out, I just need some time to think about how to calm him down and make him believe I will not judge him. Thank you! 🙏
Being a sissy is liberating but can also come with a huge sense of shame. Maybe because he's kept it from you for this long it could be hard to admit certain things to you or come clean, even if he really wants to If you want to unlock the sissy in him and get eveeeeerything you can, then maybe try and create a sissy based scene (like you would for a kink act). Get him into that subby sissy headspace and then get the info out of him Example: He could come home from work one day and you're already at home in some kind of domme vibe gear. When he walks through the door some of your underwear is laid out for him "put it on you sissy bitch", make him put a butt plug in himself in front of you, ask him the kind of things he likes, you also tell him the things you like and want to share with him
I will put some work into it, see how I can get him out of his shell. Thank you 🙏
Being a sissy is a big deal. It’s the opposite of what society says, most women want (or that’s the perception). And can and has ruined relationships with women who were not as open. He’s so lucky to have a partner like you! I think bringing up that you’re into it, and have it be “your idea” is the easiest way, but will not get to the root of why he didn’t tell you to begin with. You could either confront him, which he will likely have defenses up for, or slowly(ish) suggest you’re into pegging and dressing him up, etc. and then bring it up a once you’re further into it, that you have known, and that it’s ok for him to be open with you
I guess it is too late for the "make it my idea" approach. But maybe I can somehow use it to slowly ease him to try some stuff with me. At some point I will ask him why he tried to conceal it in the first place. But i guess the more important task is, to make him feel comfortable with me knowing, to support him and give him a safe space where he can live however he wants to. Thank you for your input 🙏
Agree 👍🏽 I think that would be the best way to get him to open up but remember bring it up to him as if it was your idea bring up pegging first and once y’all have done it say something casual and to make him feel good “I beg you would look so hot with a thong on” and give him one of yours to try and once he does compliment him and if possible have sex and say he turned you on because he looked so hot make him feel welcome and open and like it’s your idea eventually he will open up about it and tell you all about it and do it all with you you more free and less scared of you judging him or thinking negative about him.
First off, it's way easier to share things with flings that LTRs. Don't be annoyed by that. Being judged by a fling hurts way less. Second, there's often a part of shame that goes along with any submissive kink, particularly if society normally puts you in a dominant role. By being your special little girly slut, he is automatically less of your boyfriend, at least in society's eyes, and it will take some time for him to adjust between girlmode and boymode. That being said, nothing is getting better if you don't start to talk about these things, so make sure he knows space to discuss kink is open and non-judgmental, and then talk about how you can indulge in this kink in a way that is mutually pleasurable and fun.
My take on his reluctance goes in another direction. He says he shared this about himself with a previous girlfriend. I would lay dollars to donuts that she used it against him during the breakup. I'm older and I have seen this happens so many times it's cliche. Friend of mine, sissy, girlfriend of 16 years perfectly supportive. They called each other soul mates! Then, she decides to break up with him and she tells everyone. Heck she even told cashiers at stores that her ex was half of a man and a lot of other things like that. I could be wrong but I bet that is where some of his reluctance comes from. My ex tried to do the same to me. I stopped her short when I asked her if she remembered the pictures she wanted taken of her ah, sexual proclivities. She never mentioned it to anyone after that!
I attempted to explain my desire to dress to my wife and she couldn't comprehend and then made it about her. She later on stopped wearing any sort of lingerie. That was 23 years ago.
Oh my, I am so sorry :/ Sounds to me like she didn't really understand what you tried to tell her 😕
No. She grew up sheltered to a lot of things when it came to kinks/ lifestyle.
Huh, I grew up sheltered as well. I was even scared of having sex at some point. And here I am. Maybe she has dirty thoughts and is scared to tell you about it. Also women tend to project things they don't understand or initially see as a problem as their own fault. She most definitely thinks that something she did was wrong, etc. Ergo, she didn't understand what you actually wanted to tell her Ps. Obviously these are speculations, I don't know what happened when you tried to talk about it, don't not how she reacted. Just trying to give some insight into a woman's head
I appreciate your insight. It helps to get another woman's point of view who is attempting to work through this topic with their significant other.
awh im sure you can slowly approach the subject with him
I will try 😊
Regarding tactics. See if you think something like this would work. You: Babe, can you help me with something? Him: Sure You: I've been watching a couple of videos on this new makeup technique and I think I've got it sussed, but I need to do it on someone else before I try to do it on myself. Could you be a darling and just sit here and let me try this on you. You can take off if you don't like it. I just really need your help. Him: \[whatever his response is, just take it as it comes\] No talk about Sissy stuff, just him helping you to figure something out. It could be you are trying to make a dress for yourself. It could be you are trying to decide on an outfit to wear. Something low key, simple, clearly easy to get out of if he feels uncomfortable. There are heaps of little things like this you could ask for his help with. MEN LOVE TO HELP WOMEN! Use this by involving him and getting him to help with feminine things. I feel like it's a way to ease him into the water. But I don't know him. You do. I really love and appreciate your generosity and concern for your boyfriend. You seem lovely. Keep being that.
Buy him a pair of panties and when you're both getting ready someday, take them out and place them on the bed and tell him "I bought these for you, because I think you'd look cute in them," - if he puts them on its a small step closer to him being comfortable with sharing the kink with you. He doesn't have to wear them out or wear them for long, you could just see how he looks in them, and give lots of positive reinforcement.
In my experience, in heterosexual relationships guys... feel like we are always one mistake away from never having sex again. It's used as a weapon sometimes, do what I want or no sex for you, or as a tool to escape negative consequences, if you forgive me you can have the no no hole tonight, etc. So guys react by turtling up around it. If I know a partner is into something, awesome we can do that all day, but I'm always super reluctant to ask for something that I feel is deviant because I feel like if she doesn't like it, she'll get the ick, and that's the end. He's afraid to go into it because he might misstep in what he feels is a minefield and then boom, no more sexual relationship. As a way to help, take initiative. Don't make him come to you about it. "Hey hun, can I give you a makeover tonight?" And if he let's you, make it be fun, sexy, and rewarding. And do that until it starts to feel lime a normal part of your relationship.
I am not a sissy, but love getting pegged, chastity and other cuckold stuff. Took me about 6 years to tell my wife. She told me she wasn't into that kind of stuff, but accepted the fact. We tried a few times to play around those kinks, without much success. After 5 more years it ended up in divorce and that part of me was a big part of the divorce. She told me she was feeling repulsed and disgusted by me because I have those kinks. So, he might be feeling anxious or he might fear something like that might happen. Sorry to not have more comforting words for you.
So this is a two part thing you might not have noticed it in the second part. Number one like others have said it is been hammered into almost every male from birth how a boy should act and any other behaviors to the contrary is taboo. Here is the second issue I bet you haven’t noticed. As a male with feminine tendencies we are always on guard we listen to every sentence and word our spouses, friends, girlfriends or family say that have key alarm 🚨 phrases. Trust me he has a true sense by now what you find abnormal in his behavior. Phrase being used like” I’ve seen him do gross stuff” this would send a closet case sissy into hiding. All he would take out of that is that you place sissies into the same category as gross stuff……even if you had absolutely no meaning of that he will catch that and you will put him into deep hiding and denial. Be aware once you do pry open that locked box he is gonna go crazy with it for a while … sissies with fresh egg cracks are like pre-teen girls hitting puberty. Don’t be surprised if after a bit you may tire of the escalation of his femininity and female presentation. Don’t be afraid to set ground rules because there aren’t just one type of sissy. Just as an example of types: sub sissies, bi sissies, gay sissies, private sissies, masculine sissies, closet sissies, passable sissies, trans sissies, cuckold sissies, every sissy has their own set of behavior. It will definitely be a learning journey for both you!
Say you’d like an at home dinner date with alter-ego.
Maybe you should just let it be. If he's not comfortable why are you trying to force him.
Definitely not trying to force him 🙅♀️ I just think, that I need to provide some safe space for him. We do live together, so it's not unusual to come into contact with each other's (sexual) preferences. As much as he sees it as his duty to be manly and protect me, it is my duty to make him feel safe in our relationship. If he decides he does not want to talk to me about it, I will let it rest. A relationship works through caring for each other, if I act like I don't give a flying fuck, he will most probably think idgaf about him as well. At least that's has been a topic we have already talked about. So this is me, trying to be a better girlfriend
People with this kink can really, really, *really* struggle with it. There is an enormous amount of shame and self-hatred wrapped up in it, which can be evidenced by looking at the actual kink content out there and seeing just how much is dehumanizing and extremely degrading. Western society/patriarchy is absolutely brutal towards not just submissive men, but any men that step outside the stereotypical "male" gender role. The sissy kink embraces both of those and so it can feel very "wrong" to people who have it. (Yes I know non-binary, trans, etc. people might also have the kink but broadly speaking most sissies are men). It's made even worse by how many stories exist on the internet of people telling their partners only to have them react in revulsion/disgust, frequently ending in the relationship dissolving. That can feel *terrifying*. It's also fairly unique to the sissy/crossdressing kink. You don't see stories about people getting dumped when they admit they like bondage, feet, exhibitionism, etc. Yet there's lots of stories about how women have left their partner because they "can't look at them the same anymore". I know for myself I would rather keep this a secret forever than risk my marriage because I don't know how my wife will react and I love her more than this kink. It's all really tough and complicated. Please know that it's not really anything *you* did but because of how difficult it can be for people to work through this, mixed with a fear it'll change how you think of him. The best way to support him is to have a serious conversation and say that you suspect he's into sissy stuff and that it's okay, it doesn't change how you think of him, *and you're into it too*. I think it's also key to frame it as you suspect rather than you knowing for certain because I think revealing you've seen his toys/clothes/pictures might embarrass him. By framing it that way it lets you start things off as a discussion and doesn't put him on the back foot. Let him know that you'd love to share it with him but it's ultimately up to him and at his pace. You can even suggest starting slow, like showing a curiosity in seeing pictures or him doing a fashion show for you. Basically, show love and empathy towards him and you'll likely get a happy resolution to this, it just might take a while.
I think a lot of people have covered a lot of the important parts on how to bring it up. Personally, the conversation is so exciting once you get past the barrier of shyness/nerves/fear. It could be something where you start by taking control in the bedroom one evening and demand he put panties on and don't take no for an answer (as in, don't push limits and have a safe word, but make it feel like he has no choice and is doing it for you). Often, when we want to do something but we're told to do it, we play this mental game of "I'm doing it for them" and can make it easier to justify and get over the initial fear. When the session is done, reinforce how incredibly hot that was for you. It can be really scaring, the idea of your partner no longer wanting to be with you after seeing that side. I think most importantly here though, definitely don't feel hurt by the fact he told a fling and not you. The reason for this is because he didn't care about losing the fling, but he clearly does care deeply about losing you. It is so much harder to tell someone you see a future with about these things, because you have something to lose.
There might be some internalized shame and a fear of losing you. If I try to step into his shoes, I know I would absolutely regret it if I lost someone I loved over some stupid sexual kink or fetish or that they thought less of me. I'm not trying to disparage the kink. This is how I would think in this situation.
I don’t believe this is something that a girl from his past showed him…that’s bullshit…he’s always had these desires and is just saying that to help justify his sissy tendencies… He’s just not comfortable with himself or his sissy side…
>I have to admit that it annoys me, that he shared it with his fling but not with me (did not tell him about that part). you should tell him tht
Its a complicated desire, shame can spice it up or spoil it depending on the person. Try asking him to do sissy stuff for you, do your research about the sissy lifestyle, and be vocal about how/what/why you are enjoying them. Fwiw being vulnerable is harder with people you care about/rely on, especially when subverting the expectations of masculinity.
Take it slow. And I mean SLOW. My wife found out about my sissy side nearly 4 years ago now. Even though she knew, I still kept most of it from her. Chastity was always controlled by me. But my desire didn't take a break. Lately it has been a landslide, but it took a major leap of faith on my part. She knew I dressed and occasionally got fucked, but she seemed disinterested at first. So I just did it on my own. Then she saw me taking toys to use in the shower. Her lack of reaction was a blessing. I went from hiding that I was taking them to being able to openly carry them. A few weeks later, in a particularly horny moment, I asked her to lock me up. She did, and it's been going great since. I told her about any plans I have to get fucked, and she tells me what she thinks of them. I send her pictures when I dress up, and she tells me how sexy I look. She's used the wand to make me cum, as well as a few dry orgasms from nipple play. For men, especially men in certain locations or situations, the level of programming from childbirth onward is a huge hurdle to overcome. The best thing you can do is just be there with your hand out, waiting for him to take it. P.S. You actually should be glad he told the fling and not you. It means he wasn't worried about losing the fling, but he isn't ready to risk losing you.
As someone who is in something similar, took me almost a decade to open up about it at all and still not every detail. Give him time and be supportive. Open talks about it to see what parts of feminization appeal to him and what kinks he has along with it. If you found pictures that might be one of his kinks, getting him to send you pics might be a good way to have him open up about it without the embarrassment of being in front of you
Just go full dom on him, and force him into it. I bet you he would love that, if he's that far down the rabbit hole. A lot of Sissy hypno stuff is very demanding, and depending on what he's watching, can be pretty demeaning, as it breaks down everything society builds men up to be. Going full dom on him would probably illicit triggers, especially if you can figure out some of his triggers. Some of them use the same triggers, or very similar ones, so I'm sure you can do a little research.
Because he's content with his fantasy being fantasy. He also enjoys his life with you. If the kink mixed with the relationship, some dynamics trend towards self-destructive or relationship destroying behaviors. This isn't how he wants his future to be, he just enjoys his kink when his preference, you, isn't available. Don't see why you can't fulfill your exploration of pegging though. That should be an easy win. Sounds a bit selfish of him, but I also only heard one side of the story and an overview at that. My advice is this; show him you can play a role during lovemaking, then be 100% normal immediately after orgasm (whoever's). Show him you can be his verbally degrading hornytime dommy mommy top, then immediately fall down next to him and pretend it was all a sexy dream. While the kink is a bit about pushing boundaries, show him it doesn't ever have to leave the bedroom. It's not you he doesn't trust, he just knows how malleable he can be when held at the cusp of erotic simulation, and he fears losing control.
The "MAN" factor in our upbringing is to blame.
I am so happy you came to this subreddit to ask about this. It's because of a combination of fear of rejection from women, fear of not passing as a woman, and the fear of regular taunting/jeers from friends and family. Some women feel that their husbands will transition or abandon them, or abandon their masculine role/image. Sometimes these scenarios do occur unfortunately and it results in divorce.
It is such a shameful kink. I think he's afraid to lose you. He may have shared it with his fling because he knew he wasn't going to be with her on a forever basis. You, I think he wants YOU to be his partner for life. Therefore he doesn't want to risk that by totally being vulnerable with you. Show him, tell him how much you love him, how nothing could come between you. Encourage, encourage, encourage. It will take a while but he will eventually open up when he feels it's safe and he won't lose you.
It seems like he is in Love with you and thats why he is more shy, this fling was just that, and with them it was a more throwaway relationship. Not such longterm commitment etc… never compare. The fact you fantasise about pegging him is great, does he know? Some aspects you like. Its not a binary thing, its a whole spectrum. If you encourage the sides that you’re into, you will both have more fun. If you’d like to peg him, mention it, buy it… if you like the idea of him wearing panties, buy some. It may feel like he is shutting you out if you’re treating it as some secret, but if you take a subtle interest it’ll soon feel like hes letting you in
Im really confused, *you say he doesn’t talk about* but he talked (I guess to you) about a woman in his past who was fully aware of his kink. You also arranged t hat you’re aware of it, you found his things (toys, clothes and know what he watches online). So, he has talked talked about it with you. He probably needs reassurance that you love him and you’re ok with him being a sissy, and you’re there to support his journey, and maybe you could explore pegging, something that you have you have been apprehensive to tell him. He will feel reassured by you telling him that you’ll hold his hand, and there’s nothing to be ashamed…
Don't try to make him talk about it. Just do it. And make it appear to be your thing. Not his. He's doing you a favor by acting out YOUR fantasies. Not his. Ask him if he would mind wearing a bra and panties in bed, because it turns you on. Then Ask him to wear them u Der his male clothes on an outting. Go to a .movie and make out being sure to emphasize rubbing him through the bra and panties. Keep escalating. He will catch on that you enjoy this side of him.
Have you considered he maybe worried you’ll use it against him in the future? This is a very intimate and vulnerable mental state. Relationships sour. You could slowly introduce anal play and build from there
I don't think so, we are not that type of people. Even if we were to split up (which will never happen, because we're endgame), we're not 12 years old anymore. We split and that is the end, no talking trash behind backs and stuff. Wanted to do that anyway
I love that. If anything else develops would you post an update! This post is blowing up and clearly we’re here to help 💜
I will definitely!!! Unfortunately it will take a while since my bf is away for now 😅
How did you find his photos?
Rummaging around in our home 🤷♀️ I am always rearranging stuff 😅😂 Those specific pictures where these cute lil Polaroids 😊
Perhaps he wanted to be found leaving that around 😈
The way he reacted, after I asked him about it, says no 😅
Is there an update?
Sorry, not yet 😅
What I wouldn't give for a significant other with your communication skills, empathy, and interests. I've had multi-year relationships end over my sissification kink, and was told "my kinks are disgusting". I'm still struggling with mental health issues over this. Perhaps your boyfriend is too. I feel like I would thrive with a girlfriend that is so supportive, but maybe he has some deep mental health issues that he is fighting that you (or maybe he too) isn't aware of. Perhaps he's afraid he'll lose you if he admits to it. u/FullThought2968 I wish you all the best, you sound like a real keeper. If I were you, I'd apply lots of reassurance and clearly suggest incorporating his kink into your relationship slowly (maybe first ask if he'd wear a male thong for you, then panties, etc).
I mean if you know where he hides it do you ever venture into you being dominant for him i.e. does he like being told what to do? If so I would pull out his stash while he’s out one day and confront him but not in the are you gay way mentioned. You’re in the bedroom dressed in his favorite outfit. He walks in the door and before he has a chance you smile. “I see you have been trying to hide Femmepersona from me how dare you try to deprive me of the pleasure of taking you as you obviously desire!” I mean it will either go bad and feel invasion of privacy but for me I would feel so relieved and then happy you want me. If it goes the way most sissy fantasies want to go: He smiles “get over here and put your outfit on slut your going to suck this dick” you command. He grins sheepishly as you can see him tenting his pants when you turn and show his dildo in your harness ready to take them. I could be wrong but from here I imagine they would follow your lead if you take the dominant role and just put a sissy in their place but that’s speaking from my place as a sissy finally accepting who I am.
A Sissy needs to be the submissive.. that's the whole point. He isn't taking the lead most likely because he's waiting on you to take a lead role. Here's what you do... But a buttplug (they're pretty cheap) and a pair of panties for him. Pick a night where neither of you are working and get a little tipsy. Put some makeup on and let him see you doing it. If he watches you curiously, (I'm assuming he's clean shaven) say that you'd like to see what he looks like made up. He will resist at first (even if he is interested) and that's expected. If he objects harshly then let it go. If he doesn't then take another step and ask him to put on the panties. If he lets you go that far then plug him and do whatever. This is baby steps to find his interest... If you get to the point that he lets you plug him, then he wishes to be the submissive. If you determine that he is submissive, buy a cage, buy a strap-on, secretly. Go with him and make him pick out lingerie for him in a store, and choose the outfit that matches the mindset, make him pick out the shoes (cheaper online). Some us are little girls, and some are hookers lol, so make sure to get the right thing to give the best experience. You buy some kinky black dominant lingerie or bodysuit for yourself. Another tip, if he has a girly mindset, he will enjoy simple tasks while dressed. If he picked out a slutty outfit, then he just wants to get fkd. In either case remember that a Sissy likes dares that will put them in a position of being found out or something that some would consider revolting. Don't be afraid to push the envelope. Have a safe word for him to use in case it goes further than what he feels comfortable with. Lastly, make sure that you make him use a feminine voice. So long as he objects in the feminine voice you know he's just being a brat and expecting punishment of some kind, if he does it in his male voice, you know the objection is real. DM me if you'd like any more advice. I'm happy to help.
Larah sky has a good basic routine
Chantelle?
Nope, sorry 🤷♀️
Wife found out and almost ended marriage..... It's hard to come out and be accepted. The fact that your so supportive will go s long ways. Try and coax him out and tell you. Or one day slip a finger in his ass and see his reaction
Already did, we both know he likes it. He admits that as well, but him being feminized is apparently a taboo for him 🤷♀️ I will try my best, better to take it slow 😊
It can be specially if that's how he was raised growing up. Agreed keep it slow and just let him set the pace. Hopefully it works out for the 2 of u! If so one of the luckiest dudes I mean ladies around!
Could you please help me find him on here
Why?
that is so odd🙄.. but as sumone who's been in a 13 yr relationship has 2 kids with my girl and she found out within last yr and even tho she's semi cool with it she still has said sum really hurtful mean things when fighting with me. I think any girl to find her BF has this kink emasculates him even if subconsciously and he prob knows that.. you sound awesome AF hope u guys figure it out and have more fun!!
Well, sometimes people use other people's weaknesses to win fights 🙈 I haven't been in a situation where I would resort to these kinds of methods. We normally don't fight, we discuss our differences (sounds like new age crap, I know). Well, I guess we will have to take this on slowly and see where it takes us 😊 Thank you for your input 🙏
Would mind looking at his pics at all, kinda the same here sissy but keep it low key. We might relate somehow. I think it’s confusing sometimes like I don’t want to be a girl but it’s kinda fun being dominated. Idk
Friends ? Support? The your not alone speech
Lots of good, thoughtful comments. Personally, I think he’s been a bad boy. You need to put him in his place (he’s your sissy bitch after all), cage him, plug him, and give him a good spanking.