Moving from strapon to sissy

I just confessed to my wife the other day my desire to be taken with a strap on. She didnt take to it well at first but opened up a little bit and has started using toys on me and hopes to be comfortable enough soon to use a strap on. She is fairly conservative and not specifically dominant, even though I truly believe she has it in her and would enjoy it if she embraced it. I want to find a strap on video to watch with her when she feels more comfortable. The catch is I am also a long time sissy and would to introduce her to crossdressing a bit. I would love to find a video that is mostly just strap on play but may have a bit of powerd dressing maybe just panties. I dont want her to know I bought a sissy video but to be kind of surprised by it to test the waters. Anyone have any ideas?

I would suggest going slow. Get her used to the idea of using a strap-on on you first. Once she does that, then move on to her using it regularly, once a week or so to start. Then, the idea of cross dressing will come more naturally to both of you.

Yeah that was my idea. That is why i am looking for subtle, nothing hardcore. We are taking it slow and when she is ready I want to be able to move forward a little so I am trying to get ideas now. I was hoping for something mild with the female taking off her panties and having the male put them on, nothing more no offense.

My wife recently fucked me with a strapon (its not as easy as it seems). We both enjoyed it but it isnt something we are going to do all the time.

I would love to take the next step and start wearing womens panties.

I think its a great idea to use porn as a way to introduce new ideas. First of all, she will be in a sexually playful mood and be much more willing to consider do it. Secondly, it takes a lot of pressure off of you worrying about what her reaction might be if you brought it up on your own.

I also have been looking for movies that will bring up cuckolding in a positive way. So far no luck. Its all way too extreme to use as an introduction to an unsuspecting wife. However, I recently bought a movie called Housewives Unleashed #4 which is about common womens fantasies about fucking a stranger. I have encouraged my wife to watch it when I am at work and the kids are in school as a way to help her fantasize more and reach orgasm more quickly. So far she hasnt watched it. When she does, I will have effectively been able to introduce fucking other men into her fantasy life. Hopefully, we will have the conversations afterwards where I tell her its OK to have those fantasies and that I have those fantasies of her fucking other men as well. I hope it will be one more step to her fucking another man in real life.

With my wife and I, it came naturally. We started as swingers and slowly moved on to just threesomes with guys. Eventually, she started dating guys on her own. Now, I rarely get sex at all and only occasionally even hear about it.

Permisterally, I liked it much better when she would tell me about it and I would get to lick her clean, but she doesn't allow me that pleasure often.

Consider comedy. Check out this misterg by Tim Minchin - it mentions watersports and wearing his wife's panties.

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Have I got the movie for you!

Its called "Strap-on and Hold Tight". Its specifically about straight guys who like to wear their girlfriends clothes and lingerie while they get fucked in the ass with a strap on.

Do a google search or loook on Ebay. I think I might pick one up to watch with my wife. If you get it, please post a review.