@Wood_Wow I have been trying to think about subtle ways to bring it up. One idea I had was, next time we’re shopping for lingerie for her, I could jokingly ask what she thinks would look good on me to see how she reacts and what she would say. Then go from there?
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@user408 - take it slowly but be honest - start with the underwear aspect first and then move on to the pegging / sub section
Just because you are a man’s man (butch / mechanic) is irrelevant- my husband is 6’3 and again a big man - but he still enjoys wearing lingerie and being dominated by me and pegging him
As others say - don’t overthink it
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@batjamboree did your husband bring the idea of cross dressing initially or was it you? Either way how did that conversation go?
Men in lingerie are hot, don’t have her missing out 
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It’s quite a long story.
My wife has Parkinsons so I was gradually doing more and more of the cooking, cleaning and general household upkeep.
At the same time I had been in female led male chastity for 3 or 4 years so, sexually at least, she was the dominant one and penetrative sex had switched from PIV to almost exclusively pegging.
I put it to her that, since I had taken on the traditional female role, domestically and sexually, I would like to dress in a way which reflected what was essentially a role reversal.
She saw that as a logical extension of our relationship so I began wearing knickers and a gaff (fake vagina) permanently and full lingerie for our sexual sessions and she sleeps in, and occasionally wears outside, men’s underpants and a packer (fake penis).
That is still the current state of our relationship. I wear knickers and a gaff on a daily basis. She sleeps in men’s pants and a packer. She fuxxks (pegs) me regularly and gives herself orgasms as she pleases.
You could also just give it a go and try on some lacy undies underneath your clothes and when the bedroom calls, just see how she takes to it? It sounds as though she wasn’t too fazed by the strap on in general, and since you’ve introduced it to her already, she clearly knows you’re curious in that department.
If all else fails and you can’t bring yourself to talk about it, sometimes it’s easier to write things down - there are online kink lists and quizzes you could both do for fun, and allow that to casually reveal each other’s fantasies in that way? You might find out you’re both into very mutually enjoyable things that neither of you had previously thought about, and perhaps this exercise will reveal something she could be hiding that’s just as nerve wracking x
You’ll be so relieved when it’s out in the open, I hope shower you decide to share this will be an incredibly healing and sensual experience for you both. Wishing you the best of luck, and many happy evenings!~
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He always joked about wearing my knickers so I just said to do it - within weeks he was wearing knickers full time
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You have been given a lot of good advice here, but if I had to choose, I would say Waveyalien’s is best. Unless there is a need for urgency, take it slow. You say you just introduced a strap-on and she took it well. Use that a few times and see how well you both like it. Once you both have gotten comfortable with it, maybe after a strap-on session, ask if she thinks you should step it up and wear the traditional female sexual attire to get more into the role reversal. Her response will likely be positive, and things will go from there. To me it seems you are a little bit shy about introducing it, and this is a gentle way to do it
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I thought I should add that I am not at all into cross-dressing, but I am into pegging, and I wish you well on your adventure
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How do you both like to play games?
Unstrip poker where you are naked to start with all the clothes in the centre of the table and each time you win a hand you pick an item to wear.
Just don’t be a terrible player of cards or you could get cold.
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But I’m all for the advocacy of communication and talking to each other and working through your kinks and wants open and honestly together.
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@Wolf_in_White ive considered the “surpise” approach and just wear a pair of panties in the bedroom but im not sure shed react too positively to that so I’ll hold of on that.
The quiz kink list sounds like a greay idea though. I think I know her pretty well to be honest but it would be interesting to see if there’s a kink that she has that I was unaware of.
The final idea im thinking is to essentially just write everythin I’ve spoken about here in a letter. She can then read everything I need her to hear without me getting too nervous and failing to explain it properly.
Regardless, thank you for your advice!
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@Analizer Yeah taking it slow is definitely how I’m going to go about regardless of how I do it. I think youre right, pegging will come first and then the lingerie wearing can come later when it feels more comfortable to discuss
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@Analizer Thank you so much
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@JGood neither of us can play poker but some sort of game could be a way to introduce it I suppose.
I think it’s just going to come down to communication though if I do eventually bring it up with her.
Thank you for your input
@batjamboree That’s the most simplist approach, but sadly I’m not sure my gf would suggest to do it as I doubt it is one of her kinks directly
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I love letter writing, in a previous relationship at the start we did this alot as we didn’t live close by, so we would write each other kinky letters, it’s a good way to engage and let out your kinks especially if you aren’t sure what your partner will think of something, we actually carried on the letter writing when we moved in together.
My advice if you go the letter route don’t make it all about you at the start, tell her how wonderful she is and how she makes you feel and then gradually get talking about your kink, add some other kinks in first in the letter, so then you can ask her to reply about kink 1 2 3, ask her to reply in a letter so she can have time to think about it, you never know she might get turned on while she is writing the letter as mine always did, and left me signs of it on the letter.
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@teacake thats great advice. I think a letter may be the way forward. Making it about her to begin with and discussing other kinks is a good idea too. Thank you!
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A letter can be good, and might make things easier for you. Could also put on a movie, song or tell her a story about something similar and test her opinion on that type of thing before asking directly if it’s something that might bother her from a partner (more importantly find out why and where it comes from, as worry about things like this can stem from many different places and fears).
2 years is a good amount of time to be experimental in the bedroom and everyone is different in their approach to that. Chances are if there’s something you’re still hiding after 2 years of physical intimacy with her, there might be something she is embarrassed to share too, so an open and honest conversation should only bring you closer.
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@Wolf_in_White shes very open with what she likes, which may be why I’m hesitant to bring up wearing lingerie with her as shes never openly said its something she would be interested in.
But I will approach the topic slow and gently at my own pace.
Thank you for your input, it’s greatly appreciated
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