1. Yes, several. Before and after having started transitioning. (The majority of them after I started T).
2. How was it? -It has been everything from horrible to absolutely amazing, depending on the guy, me, our connection, etc. But in general it's something that I enjoy.
Did it cause dysphoria? In what ways? -Anything that involves me having any kind of sex always causes me some degree of dysphoria but I can sometimes distract myself from it with various techniques, but I get dysphoria usually about my genitals and sometimes about how I'm perceived by the guy. I used to get fairly mild chest dysphoria during sex before top surgery, but as long they didn't touch me there (which most didn't) it was fine for me to be topless during sex.
Did he penetrate you? -Sometimes guys have penetrated me (however I don't receive PIV since a few years ago cause it causes waaay too much dysphoria for me that I can no longer deal with) but usually we don't go further than oral.
3. Probably not applicable to me cause I'm guessing you're referring the front, but I was curious about anal for half an eternity (10 years) before I eventually tried and loved it almost instantly, but I haven't yet tried with an actual other person, but I would and will (at some point).
4. I have a very wide sprectrum of experiences when it comes to sex with cis men, as they range from loving, romantic relationships to ->-bleeped-<-ty, intoxicated one night stands, so it's difficult to give a general overview of the entirety of those experiences. Most of the ones I've been with have been older than me as well, they're often between 30 and 60 but some have been younger or older than that. Also another point is that I've almost only been with cis men, with the exception that my former boyfriend was a trans guy like me. Some things that I've found has been a quite common factor with the cis guys I've been with though and that I like, is that they tend to be very direct in what they want/don't want which makes communication easier for me, most of them never had any issues with me being trans (although one guy totally freaked out about it afterwards and asked me to keep our encounter secret... *ouch*) and I've always felt respected by them. I am gay, just in case that needed to be clarified. And perhaps a tad promiscuous.