"Yes we chat quite often and get on well I do odd jobs for her sometimes but it might make things uncomfortable if I told her I fancy her! "
Yeah it's always a possibility. Would you be thinking of a relationship or just a sex thing? |
Reply privately, Reply in forum +quote
or View forums list | |
"I'd like it to be a friendship with the possibility of sex but not essential someone to dress with would be nice she wears lovely makeup but doesn't know I'm a cross dresser. "
Maybe move the conversation on a little at a time. Compliment her a little, ask her if she'd like to share a bottle of wine one evening. You will be able to tell from her reaction if she wants to take things further. Bringing up your cross dressing might be more of a challenge.
|
Reply privately, Reply in forum +quote
or View forums list | |
"I'd like it to be a friendship with the possibility of sex but not essential someone to dress with would be nice she wears lovely makeup but doesn't know I'm a cross dresser.
Maybe move the conversation on a little at a time. Compliment her a little, ask her if she'd like to share a bottle of wine one evening. You will be able to tell from her reaction if she wants to take things further. Bringing up your cross dressing might be more of a challenge.
"
.
Yes I've thought along those lines maybe say something about trans issues and see how she reacts? |
Reply privately, Reply in forum +quote
or View forums list | |
"I'd like it to be a friendship with the possibility of sex but not essential someone to dress with would be nice she wears lovely makeup but doesn't know I'm a cross dresser.
Maybe move the conversation on a little at a time. Compliment her a little, ask her if she'd like to share a bottle of wine one evening. You will be able to tell from her reaction if she wants to take things further. Bringing up your cross dressing might be more of a challenge.
.
Yes I've thought along those lines maybe say something about trans issues and see how she reacts? "
It's difficult to know. People are surprising in what they accept and don't. I know that if a guy started to talk to me in a general way about cross dressing I'd assume it was something he was interested in and ask him if he was. But not everyone's the same. |
Reply privately, Reply in forum +quote
or View forums list | |
Yes I can see your point it's a tricky one as I think younger people are more open minded whereas a slightly maturer person may not be, but you just don't know I wouldn't want to upset her she's a good neighbour I just can't help fancying her tho. |
Reply privately, Reply in forum +quote
or View forums list | |
 |
By (user no longer on site)
over a year ago
|
"I'd like it to be a friendship with the possibility of sex but not essential someone to dress with would be nice she wears lovely makeup but doesn't know I'm a cross dresser.
Maybe move the conversation on a little at a time. Compliment her a little, ask her if she'd like to share a bottle of wine one evening. You will be able to tell from her reaction if she wants to take things further. Bringing up your cross dressing might be more of a challenge.
"
Definitely this. Give it a go. |
Reply privately, Reply in forum +quote
or View forums list | |
» Add a new message to this topic
