This is the hardcore NSFW content I come to this Lemmy instance for.
@lemmynsfw.com
Straight man here. I was asked out by a trans woman and we started going out. Somewhat different situation than your question, as I never had particular fantasies of or attraction to trans women. We eventually slept together. I was super nervous, since she was my first date, first kiss, first everything. In the end we got married and are living happily ever after, so I would say it worked out pretty great.
Based on your question I presume you are particularly interested in the aspect of being with a woman with a penis. For me it was alright. It is not my preferred genital configuration for a sexual partner, so I was quite happy when she got SRS several years later.
Like Jersusalemspiderman mentioned, many trans women have a contentious relationship with that part of their anatomy. I am not sure what percentage of trans women are interested in performing penetrative anal sex on a man, but I believe it is fairly low; if that particular act is important to you, you may be going against long odds. It was not something that I desired. While my then-girlfriend was pre-op, we did anal sex with me as the penetrator. I occasionally performed oral sex, though she liked to give more than receive. And the handjobs were mutual. I also topped in a variety of BDSM activities, though that is not really trans-related.
Be aware that estrogen can reduce penis size. It can vary a lot person-to-person, though. My other trans girlfriend actually had a penis larger than mine.
Treat the trans people in your life with kindness. Society is often cruel to them.
Sometimes, when I want to express my deep and special connection to my partner, I will perform an act I call nose finger. This act consists of me extending my index finger, shoving it in her nostril, then holding it there a few moments as we savor the connection. I reason, in this depraved, libertine age, you could sleep with someone and have it mean almost nothing. But who, except your most intimate of intimates, would you let shove their finger up your nose?
She appreciates how deeply romantic I am.
I have gotten good use out of these dog bone cookie cutters, both for making dog treats for dogs and dog treats for people.
https://www.amazon.com/dp/B0B3DKJF8K
You can use any type of cookie mix you like. But if you want a little extra authenticity, these peanut butter dog treats are loved by dogs and fully edible for people, if a little bit bland.
This year I have been subjecting one of my wives to orgasm denial, under threat of intense application of her shock collar. She has been allowed three or four total, on special occasions. She has been loving it. It has left her constantly horny and she says it has been the best sex of her life. She is on day fifty of her current streak, and I am intending to extend it to a full year. When her chastity belt arrives I am eager to figure out the best way to fit it with a remote vibrator, so I can tease her at will.
For me it tickles, and not much else. Pressure from a finger there is fantastic, though. Having sex with my partner lying on her side and me straddling her bottom leg also provides good pressure there.
Last year I borrowed a 3D camera from the library to try making a VR home sex tape. The outdated software led to some double-vision at the edges of the shot, and we are anything but professional pornographers (in one shot, you can see one of my partners knocking over a floor light at the edge of the scene as we moved around 😅). But it was a fun and novel experience.
I recently learned about the stag and vixen terms while looking into the same question. It is nice to have a word for it.
I also enjoy some dominance of my partners when having sex with other people, just as I do in other sexual contexts. But my most prominent feeling when my partners have had sex with other people, with or without my involvement, has just been a joyous "Hell yeah, we got some! Go team!"
Do you think you could just print the mold directly? I haven't looked deeply into the techniques.
The pillory was pretty simple, so I didn't feel the need for a plan. I had the pillory part sandwiched between a pair of 2X4s with regularly-spaced holes on each end. Long bolts ran through the sandwich, and could be removed to adjust the height. Most of the time it was attached to the bed, but I also made a base out of a pallet so it could be used freestanding. Sadly I don't have the bed anymore. I need to find a place for the pillory in my new house and pull it out of the garage. 
I have not used that kind of sleeve before, but earlier this year my wife got me one that fits on the head of a Hitachi-style wand vibrator, like this one. I have enjoyed it. I don't know that it is better than a hand, but much like my electric toothbrush, it is nice letting a motor handle the rapid back-and-forth.
I have made a pillory, a St. Andrew's cross, a spreader bar and a couple collars. I processed and dyed a big spool of hemp rope into nice shibari ropes. Installing a bunch of tie-down points around and above the bed and fitting them with chains probably counts too.
When I was experimenting with a laser cut, I made what I think is my most original design, this tag that goes over the bar of a nipple piercing, and is held in place when you screw the balls on the ends. 
Though this cat toy that I made into a gag for my bunny girl turned out pretty cute, too. 
I don't have any pictures yet, but I am just finishing up a pony play head harness modeled after this one, and am quite happy with how it is looking: https://www.lvxsupply.com/...
Insertables sound interesting, and could synergize with my 3D printing hobby, but the only silicone I have ever cast was a single mold for resin.
thanks for using Leebra!
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