When/How do I tell her? A Real Quandary!

[Anneliese]

Hello all.

I should start out by saying I'm 62 and haven't had a girlfriend in ten years.

There was no intention on my part to have one ever again, and to just enjoy my single life and dressing.

Out of nowhere a woman twenty years younger has fallen for me. She is currently a co-worker, but has turned in her notice. She is best friends with my assistant at work, and they regularly text.

We haven't been intimate, but that's only because I'm torn on that subject. She would be in a second. She hasn't been to my place because my cross-dressing would be obvious, unless I hid everything, which I'd rather not do.

We have been going out as "friends" to this point, but I kind of blew that when I kissed her last week.

She has seen and liked "Hedwig and the Angry Inch". She identifies as a pirate, and often dresses up as a female one. She loves thrift stores and wants to go shopping with me at some point, now that Halloween clothing and wigs are being put out. She also told me out of clear blue sky that her ex-husband regularly wore women's underwear. My therapist said that was my opening...to ask how she felt about that...but I didn't say anything.

I really like this woman...although not as much as she likes me...and possibly getting some after ten years sounds good, but I really don't know how to proceed per the CDing subject.

Any suggestions or thoughts would be very appreciated!

[Stephanie47]

I agree with your therapist. That was an opportunity to ask how she felt about her former husband wearing women's clothing. That could have been a bone of contention between them. If you do "out" yourself to her there is the issue of her being best friends with your work assistant. The matter of privacy should be discussed.

As to her dressing up as a pirate, I see that as something to consider for Halloween. Her the pirate, and, you the female captive attired appropriately as an eighteenth century woman.

[DIANEF]

20 years your junior, lucky you! Sounds like you're already halfway there with the CD thing. I'd probably ask about her former husbands dressing, was it just underwear or did it ever go any further? If she likes a bit of dress-up, and who doesn't...that could be a way of introducing your other self to her. She obviously likes you a lot and isn't totally new to idea of a man wearing womens things. Of course theres the issue of her friendship with your work assistant to consider. Good luck!

[Teresa]

Anneliese,
You mention this new GF had a husband who wore women's underwear , was that the problem with the break of the marriage ? If it wasn't then maybe your therapist was right but you can still use that as an opening. As you say Halloween stuff is appearing in the shops, maybe go out and have some fun picking something femme to wear and ask if she has any objections and then take it from there.

Why worry if you have an age gap and you weren't looking for a new relationship as long as she is genuine. Unless you really wanted to continue to live alone to really come to terms with your dressing , if that's the case you have nothing to lose if you tell her, if she's OK with it then that's fine you've found a good partner to share your dressing with.

[BillieAnneJean]

My observation is that any time there is an age gap of that many years, the younger person feels that their primary asset they bring to the relationship is their relative youth. Like You do the work, You bring the money, You put the effort in to the relationship. I, the so much younger, will just be younger and deserve it.

For the reactionary people, please note:
I did NOT say "always the case", "most times", "many times". So don't bother jumping down my throat.

I have seen this scenario with women as the younger and men too as the younger. A 50 year old guy can be more agile and a better dancer without any effort than his 70 year old lady friend. A 30 year old woman, with no effort, can have smoother skin and a more svelte figure than the other 50s gals in the group with their 50s guys.

So proceed with caution. She may have baited you with the previous boyfriend and panties thing. If you have any assets, be careful. Love and sex make people do foolish things.

[Katie01]

I had a similar experience (we're the same age FWIW). You have a great opportunity. I would wait until you were having a regular conversation (not flirting) and casually revisit the subject... "you mentioned your husband wore lingerie, tell me more..." I would avoid "THE BIG REVEAL" or making things more dramatic than it has to be. It's just something you enjoy. That's what I did and it worked out great. When wonderful things present themselves, the trick is to recognize it and enjoy the ride, which you seem to have done. Revealing intimate things about oneself can be frightening but with risk come reward. Good luck!

[Laura912]

Re-read your sixth and longest paragraph wherein lies your answer. We can pass the salt shaker if you need BillieAnneJean's grain of salt caution.

[Jodi]

I agree 100% with BillieAnn Jean. That has been my experience with the dating world to a "T"

jodi

[Leslie Langford]

Lot's of good points raised here. I think the Beatles also covered that topic pretty well in their insightful song "When I'm 64", except that in your case, you might want to substitute "74" or "84" for the "64".

The cynic in me also subscribes to BillieAnneJean's POV. May-December relationships can be fraught with red flags despite all the best will in the world and associated "but our case will be different!" pie-in-the-sky optimism. The age gap (chasm?) existing at the beginning of such a relationship can turn into a veritable Grand Canyon as the years progress. I know of a vibrant, active lady in her early 70's whose husband - now in his late 80's - developed dementia years ago and now resides in a long term care facility in what is essentially a vegetative state. How much fun can that be for her now? I'm sure she never saw that one coming when they got married years ago and their age difference was an "inconsequential" 13 years...

All that aside, when I see the comment "regularly wore women's underwear" and in the same breath hear "ex-husband", the likely connection between the two is pretty hard to ignore.

[Anneliese]

Thank you all. She and I and my daughter (32) just had lunch together, and I they liked each other. They exchanged phone numbers and will likely soon be Facebook friends. My daughter knows. She was the first person besides my therapist to know. Speaking of Facebook, selfies with the two of us are there now, according to one of her friends. (I am not on Facebook)

Thanks for the words suggesting caution. It's hard when your loins say "Throw it to the wind".

[BLUE ORCHID]

Hi Anneliese, For each reason to go forward there are as many reasons to go the other way.

My question is why did she turn in her notice,
Is she planning on moving in with you and playing House ?? Plase keep us advised. ......

[Leslie Langford]

The "loins" may well say "Throw it to the wind", but the "lions" awakened by going into this situation with "Eyes Wide Shut" are apt to eat you alive, once all is said and done.

Just sayin'...

As Leslie Gore once put it in her hit song: "It's My Party and I'll Cry If I Want To"...

[nvlady]

Go thrift store shopping with her. It sounds like at some point she will hold up a piece of clothing and suggest that it would look nice, or fit, or whatever on you. Your response, "You really think so?".

[sometimes_miss]

So proceed with caution. She may have baited you with the previous boyfriend and panties thing.

This was my reaction; she may have noticed something about you that reminded her of her husband's crossdressing, and she just wanted to find out if you were 'one of them' too before going any further in the relationship. Tread carefully. Remember, even if she's OK with OTHER people crossdressing, the Not In My Back Yard feeling is very strong with many, many women. My own ex wife was just fine with anyone else who was gay, ts, crossdressing. But me? A big NOPE. Absolutely not.

So, knowing that she's friends with your co-worker, being out to her may mean being out to everyone. Be careful.

[Tina_gm]

Well, you have already said it yourself that she is into you more than you are into her. So on that basis, losing her if she does not accept the CDing won't be so traumatic I would think. Depending on your level of privacy about CDing.... how many know, how many you are ok with knowing, IF.... you are not overly concerned with how many know, or maybe many in your circle already do, then roll the dice and see what you get by telling her.

What would intrigue me is how did she come up through a convo that made her tell you about her ex husband wearing women's underwear? Was their any reaction to it, not just negative spoken words, but was their a general negative response at all, eye rolling, look of disgust etc etc. And no, you hadn't asked how she felt about that, but I see no reason why you still couldnt.

I do think there is at least a likely hood that her saying that is a feeling out of you as far as the CDing goes. Remember, women are very very very very observant to things and she may already be picking up on things. Eye brows, shaved hands, finger nail length, any other subtleties that might give you away as being more feminine than the average guy.....