How do I bring it up to my man that I want him to wear Sissy attire?

[lola_plunge]

I've been in an open relationship with a man for several years but he's my main partner and he's quite masculine yet usually open to try new things. I've been getting all tingly with the thought of him dressed as a sissy during our sessions but don't know exactly how to bring it up to him.
I found some great selections here on this new marketplace someone turned me on to and I wouldn't even mind if he started with something like a banana hammock before moving on to the more frilly sissy options but i'm afraid he'll feel too macho to wear any of these. Any suggestions on what might convince him to try?

 

[CaptCharles]

Start with the banana hammock.. see what happens when you *show him* how wet and slutty it makes you.
He may pass on the sissy stuff if he doesn't know what it does to you.

Maybe let him try something on you in exchange?

 

[Mrs_and_mr]

I've been in an open relationship with a man for several years but he's my main partner and he's quite masculine yet usually open to try new things. I've been getting all tingly with the thought of him dressed as a sissy during our sessions but don't know exactly how to bring it up to him.
I found some great selections here on this new marketplace someone turned me on to and I wouldn't even mind if he started with something like a banana hammock before moving on to the more frilly sissy options but i'm afraid he'll feel too macho to wear any of these. Any suggestions on what might convince him to try?

What type of relationship do you have with him?

 

[whenagain]

Is this a situation where you are already dominant?

 

[Stoicbutfun]

I've been in an open relationship with a man for several years but he's my main partner and he's quite masculine yet usually open to try new things. I've been getting all tingly with the thought of him dressed as a sissy during our sessions but don't know exactly how to bring it up to him.
I found some great selections here on this new marketplace someone turned me on to and I wouldn't even mind if he started with something like a banana hammock before moving on to the more frilly sissy options but i'm afraid he'll feel too macho to wear any of these. Any suggestions on what might convince him to try?

A gf of mine just said it would drive her wild if I came by her place in panties and hold ups and it just did, I loved it, I was a bit worried about being stopped som changed in a lay by a few miles away, and yes totally wonderful sex

 

[Mrs_and_mr]

Most of my relationships have been FLRs so I was told to. My wife is also dominant but never had me wear anything until after we lived together. We were having the carpets cleaned and all the furniture was stacked and condensed. We heard some different noises downstairs and I was sent to check. I sleep with no clothes, I was looking for something to put on but couldn’t fined anything so my wife threw me her nightgown told me to put it on and see what was happening. So I did. When I came back upstairs she said she was turned on by my outfit. Now she buys me things to wear.

 

[Shaglus_Ziegler]

Just tell him?

 

[Fifemarriedsub48]

run him a hot bath, glass of red wine and lay it all out with a collar, lead, butt plug and cage and a note to come to you dressed for a special treat.

Sorry that is may wish..

 

[lola_plunge]

Start with the banana hammock.. see what happens when you *show him* how wet and slutty it makes you.
He may pass on the sissy stuff if he doesn't know what it does to you.

Maybe let him try something on you in exchange?

yeah i'm always open to try anything

 

[lola_plunge]

Just tell him?

yeah... I guess

 

[Versa92646]

Halloween is coming up soon. Select a costume, help him dress and enjoy yourselves.

 

[Britva415]

Just tell him?

Where's the part about convincing him to try it? This clearly wasn't a plain-old "how to say words" question.

Which is actually great, because most of the time a "how do I say/tell/talk about" question is almost always really a "how do I do it without getting told No or making her cry" question.

 

[Iwant2havefun]

The "halloween" response is fantastic. Easy to make a suggestion to him and see how he responds to determine your next step. "Just tell him", of course, is the easy answer. But you wouldn't have asked in the forum if you felt you could "just tell him" because he's very masculine. I have found that "very masculine" alpha guys love to wear panties and be somewhat submissive to a woman. Heard it from a friend....

 

[tnn8080]

He might be more inclined to wear something if it was yours rather than his. If I were trying to do this I would tell him how hot it would make me if he wore MY dirty panties for the day. If he was larger than me, perhaps I'd even buy some "for myself" that are too big just for this purpose. Then once he's wearing them i'd send him messages throughout the day telling him how I'm constantly thinking about it. Good chance if he's not turned on by wearing panties he'd be turned on by wearing your panties. After this it would be easier to get him some of his own, possibly under the pretense that you want to try wearing his.

 

[angela40]

Many macho men have another side hidden away. In my situation one of my exbfs wore one of my dresses and caught him in it. He was embarrassed but I hugged him. It both gave us a new sexual world. He wore panties, slight makeup. The panties keeps him hard

 

[Mrs_and_mr]

I have a gripe. I have this beautiful nightgown but only the outside is soft satin. The inside is kinda rough what’s up with that?

 

[lifeis2short2b]

Depends ! Do you want a man or a sissy ?

 

[SissyBrandi19]

I've been in an open relationship with a man for several years but he's my main partner and he's quite masculine yet usually open to try new things. I've been getting all tingly with the thought of him dressed as a sissy during our sessions but don't know exactly how to bring it up to him.
I found some great selections here on this new marketplace someone turned me on to and I wouldn't even mind if he started with something like a banana hammock before moving on to the more frilly sissy options but i'm afraid he'll feel too macho to wear any of these. Any suggestions on what might convince him to try?

Let me try, as a sissy, to help. I don't have too many specific suggestions, but there are two psychological principles you can perhaps use for your goal. One is the principle behind the "mere exposure effect" which states that any stimulus, provided it is not entirely aversive, will become more positively regarded simply by repeated exposure. The other principle is the "foot in the door" (not the official name), which is I think pretty obvious. Of course, the over-arching behavioral principles of positive reinforcement and negative reinforcement (the latter is NOT to be confused with "punishment" - negative reinforcement like it's sibling positive reinforcement will BOTH result in an increase in the desired behavior - positive rein is the simple notion of a reward - do the trick get a cookie. Negative reinforcement is the avoidance of a bad outcome upon doing the behavior - drive at the speed limit you avoid a ticket, well...for speeding, anyway).

I do have one kind of specific suggestion? Start with the "sissy" items/behaviors etc that are most rewarding even outside of being a sissy...so silk panties are very soft, comfortable and pleasant to the touch. That makes them easy to adopt. That's the "foot in the door". Then maybe gently introduce whatever you guys like doing...if you watch YouTube then maybe....hey, there's a sissy related video! There's a popular subreddit (there are a TON of sissy-related communities a.k.a. subreddits a.k.a. groups on Reddit) called "straighttogay" (straight to gay) and it's a lot of guys who are clinging (sadly in some cases) to the "straight" label but admitting to many not-so-straight thoughts and predilections. It's rather...arousing?

What you do NOT want to do is (apologies if I'm too much stating the obvious) come on too strong ("wear a tu-tu!") OR...and this may seem obvious but people do this ALL THE TIME and unintentionally - you do NOT want to punish the very behavior your are wanting to see! So,...say he puts on something "sissy" (in his mind) to please you? Don't laugh, don't criticize...even if it's not really what you want. Find a way to steer him but not punish - that was perfectly vague was it not?

But if you have any sissy-related questions? Not that I"m the only one here but...I am a self-proclaimed sissy so...

OH...geez damnit! Why is this just now coming to me? OK...this is...tread carefully but if he likes porn at all? The entire genre of Sissy Hypno? Holy fuck. That shit is POWERFUL. There's a lot that is maybe weird or something and I dislike a good portion BUT I also LOVE a good portion and if you want some really...good stuff? I know the genre very very well. You tell me what he's into and I can steer you very very well. Your best single source for sissy-related erotica? Hypnotube. They are the king. Not just one area (e.g. trans) but the entire spectrum is well represented.

 

[SissySalina]

As a sissy not sure would classify those clothing items as being "sissy", a sissy clothing is normally women's clothing and those are not that.

If you start just start a conversation and tell him how you feel. In our relationship She and sissy are very open and discuss things often, be truthful, that is key to any good relationship. If he knows how you think it would make you feel then he should be more open to it.

This is this sissy's opinion.