Have you been with a guy?

[Ceera]

Personally, it sounds more like you want the fantasy and not the actual situation. Though I suppose it is possible that your feminine aspect is more inclined to the idea and might like it. Dressing doesn't change your sexual orientation. But your frame of mind while dressed might make you more willing to explore things you're already inclined to.

My answers:
1. Has anyone done it before?
Yes. Only once while Dressed, and a few times prior to that as a guy with another guy. Never had a girl watching while that happened.

2. Did you feel guilty later about it?
My first few gay encounters were not initiated by me, and they left me feeling very confused and conflicted. I suppose somewhat guilty that I had enjoyed it, but I got over the guilt pretty fast. However, I knew my father would be very unlikely to accept the idea of me being bi or gay. So for most of my life I repressed that urge and tried to live a straight life. I married a nice girl, had a kid... No regrets for that relationship. We had a good marriage, over all. But all that time, although I remained faithful to my wife, I still knew that I found some males attractive. I just didn't act on that attraction. That is VERY different from how you describe yourself.

As fate had it, I outlived my wife, as well as both of my parents. When she was gone and I was single again, I decided to explore cross dressing and to experiment with the bi side of my nature. I found that, when en-femme, I was more receptive to attention from males than when not. But in both cases, I would just as soon have a female partner. Still, I have had one time where I accepted an offer of intimacy from a male while I was out en-femme, and I brought him home with me. I quite enjoyed him treating me like a classy lady that he wanted to be intimate with. I knew what I was doing, and no, I didn't feel guilty at all. There was nothing to be guilty about. I wasn't cheating on anyone, and it was a mutually consensual evening.

3. Did you get addicted to being with a guy?
Nope. It was fun, and we both enjoyed it. But it wasn't any better than being with a girl, and honestly, not good enough for me to seek his company again after that. Since then, I am still open to either gender, with a general preference for girls. I guess you could say Ceera is closer to being a lesbian than being bisexual.

4. Did you decide to go fulltime after being with a guy?
No. I still only cross dress about once a week. The experience didn't change my desire to cross dress at all.

Most Importantly
5. Was it more pleasurable than straight sex? How did you feel?
Honestly, it was about the same. Neither better nor worse than an average-quality encounter with someone I didn't have a deep emotional attachment to. Fun, yes. But not incredible.

My advice to you is that you should try pleasing yourself with suitable sex toys first, to make sure you find the experience of 'being drilled' a pleasant one.

If you do, then you might carefully approach a gay or bi male that you trust, and as the others mentioned, by all means use a condom! Or at the very least, make sure he's been tested recently to be free of STDs and HIV. There are free testing centers that give out cards that certify when you were last tested and what the results were.