Hey Femdom Community! Long time lurker here, and I've come in search of advice. I'm a dom-leaning switch in a LTR with my boyfriend. I wouldn't necessarily consider our relationship D/s- it's more like I'm (mostly) top and he's (mostly) bottom, with some femdom elements, but for all intents and purposes, he's usually my bitch and I run the show.

I've known for a few years that he has a kink for imagining himself as female during sex, getting fucked, having a pussy/tits... but has been reticent on the details. He's slightly embarrassed about it from what I can gather, so for a long time I basically ignored it for fear of upsetting him. But lately we've been making some slow progress, and I'm excited about taking it to the next level.

It all started when I was sucking his nipples, something that used to make him extremely ticklish within seconds. One night I went for it and he was squirming and giggling, so I commanded him to imagine that he was a girl with a big set of tits that I was sucking on. That did the trick alright. He's loved it ever since. It was like a total 180. I also gifted him several pairs of panties and he wears them quite frequently, especially when he wants to fuck.

That was it for awhile, til one night I decided I wanted to take it further. I told him I wanted to pretend he was my girlfriend for the night. Lots of nipple sucking, 'breast' squeezing/cupping. Dirty talk. I told him I loved playing with his clit while rubbing the head of his cock. I said I wanted to eat him out (code for rimjob) and did so voraciously. I told him to lift his hips for me because I was ready to fuck him. I rubbed his prostate and complimented his tight little pussy and so on and so forth, called him feminine pronouns ('good girl' etc). He absolutely exploded. We've done it a few more times since and he loves it but is still completely shy about it and reticent to discuss it.

It looks like it's up to me to take the reins which I don't mind, but other than the dirty talk and penetration I've only got a few ideas.

Pegging is definitely up there, but finding the right dildo has been tough. He's still pretty tight and too much stretching can cause discomfort. You know how hard it is to find a short skinny dildo that's reasonably priced and can fit into a strap-on harness? I've yet to come across one. But I really do think that he would enjoy the feeling of being actually fucked and it would be more immersive to have my hips slapping into him.

Lingerie/crossdressing. Help him look/feel more feminine. I know he isn't into makeup or wigs but I was thinking stockings and some silky camisoles to make him feel more feminine and sexy.

...that's about it. Like I said, I need some help here. I'd love some advice on making my guy feel like a girl, both psychologically and physically. Links to relevant subreddits or how-tos would be super swell, but hearing from you guys would be great too. Thanks so much in advance.