I have been on a few dates with men and I am pretty comfortable with how that is going. I really like the way it has a way of making me feel vulnerable and protected all at the same time. I am also attracted sexually to the one I am dating now. But we haven't done anything yet because it is kind of weird for both of us. It is mostly because we were great friends for a year. Almost eight years ago when I was a man. We have only been flirting as of now but I want to go further and he has said he has thought about it. Will nature take its course when the time comes?

Huggs

Emily

At my age I'm more interested in the companionship than the sex but I do realize that if I get involved in a relationship that sex may be involved to some degree

I've never been with a man and so I would feel a bit awkward also and so I have thought about some of these same questions

I wouldn't find it weird if I actually cared about the guy, but I would be devastated if all he was just after was a lil' somethin' somethin'

So possibly what you need to decide is are you looking for the casual sex type thing or should you invest some time to make sure he's the real deal

Hope that helps

I really think that it could be at least a long term relationship. And if it was just a shorter term thing I could live with that too. I just want to be with him. We are going slow for now and I am doing my best to be patient. But, being passive is no longer in my nature! I am trying to

Huggs

Emily

Since you have a history with this guy, I think you need to let him make the first move.  Encourage him in feminine ways.  Hair-tossing, lip-licking, body language....

Hi Emily, This is a very sticky situation that you need to be very careful with. No doubt it has to be a very weird awkward situation for both of you since you where very good friends with him when you where a man. To the positive side, he has respected you now as a woman and has shown interest in you. He already knows you want to take it further, and he has thought about it, but let him make the call. You can flirt with him and drop hints, but definitely let nature take it's course. I'm sure when he is ready and comfortable enough to have intercourse, it will happen. You want to make sure that the sex is enjoyable for both of you, and that you don't lose a good friend in the process. good luck, Chloe

Sometimes we think so much about the difficulty of the changes we have to make, and forget that we're not the only ones who have to make changes.  People we know have to reconcile the person they see now with aaaaall the memories they built with you, and it can be too much for some people.  I'm sure you want to race and get past the awkwardness, but what I've seen tells me that it's best to just being there with him til the conflict isn't so prominent.

Alternatively you could throw a huge fit and find someone else.  This last sentence would probably be the only time I ever take my own advice.

Quote from: Emily Ray on March 23, 2011, 08:58:53 PM
Will nature take its course when the time comes?

Yes it will!    You're both sticking this pressure on yourselves awwww it's completely understandable we all do it because we're scared of losing something precious, but life is beautiful you like each other immensely focus on what is real not silly doubts

Quote from: Emily Ray on March 23, 2011, 08:58:53 PM
I have been on a few dates with men and I am pretty comfortable with how that is going. I really like the way it has a way of making me feel vulnerable and protected all at the same time. I am also attracted sexually to the one I am dating now. But we haven't done anything yet because it is kind of weird for both of us. It is mostly because we were great friends for a year. Almost eight years ago when I was a man. We have only been flirting as of now but I want to go further and he has said he has thought about it. Will nature take its course when the time comes?

Huggs

Emily

Nature will take its course, let us know how it goes, before my transition I used to think it weird having sex with a man, but that all changed after my transition, it just felt so different, I love the way guys interacted with me, protecting me, guys making me feel  ''vulnerable'' in a nice respectful way, treating me like a lady, I could never see myself in a gay relationship with a guy when I was a guy, but Im now a woman and I feel very comfortable in a relationship with a guy, Im now a married woman, hope it works out Emily, its interesting that you have a history with this guy when you where a guy, particularly as you where great friends, theres a good foundation there, see how it works out, best wishes.
Pauline