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..