Community Conversation > Crossdresser talk

Taking it slow

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Heather N:
I'm very new here (joined today in fact) but I do believe this is the best place to discuss this so here goes:
I'm mid 50's been in a LTR with a woman. I have always felt like (at a minimum) a crossdresser edging toward trans. I  know they aren't the same but I also think its a giant area of gray. A long time ago I made the decision not to do much about it because of my personal life. It's a decision I am frustratingly comfortable with.

About a year ago i had a bit of a health scare and found my leg was swollen, they checked for a clot and it was all good (whew) but the doctor suggested i wear compression stockings. I started wearing those but they pulled the hair from my legs so I started shaving them. I always wanted to, but this gave me an excuse. My SO was okay with it too. well.. I have skinny legs and they kept slipping so I decided to wear a garter belt and also found some compression stockings that were def more feminine and more sheer and just felt better, so daily I started wearing stockings and a garter belt. My SO was just fine with it. In fact, she suggested I become intimate with her while wearing those. I told her how much that excited me and soon she bought me 5" heels to add to the fun.

I was having trouble with my underwear bunching up  so she suggested panties. She had some hipsters that fit me pretty well and I told her how much better they felt on me than my old male underwear. I now have a drawer full of them that she helped me pick out ;D

We got on the subject of clothing and I told her that I loved crossing my legs with my stockings on. I asked if I could try on her skirt, we both chuckled for a bit as I did, but i told her I really liked it. She said she was okay if I bought some stuff for myself.

Currently, I sleep mostly in nightgowns and panties, I have a dress of my own and a couple pairs of heels.

She has put a line up though (that I want to cross so much) that I am respecting
*No Bra (that is a huge turn off for her)
*nothing above the shoulder (no make up or wig)
*no shaving my stomach, chest or arms

Since we have started this in earnest (prob last 3 months or so) I have been super amorous to her. I want to make sure that she knows that the more we go this direction, the better it can be for her as well

I am curious if this is something that others have experienced?
What might I expect from my SO?
Do you think she might relent on her restrictions or is this a fair compromise?

I know everyone's experience is different but I am afraid if I rush it, she will ask me to put a stop to it and this Genie is out of the bottle now...


edit:spelling and grammer


--- Quote from: HeatherNorton on January 14, 2020, 04:46:52 pm ---I am curious if this is something that others have experienced?
What might I expect from my SO?
Do you think she might relent on her restrictions or is this a fair compromise?
I know everyone's experience is different but I am afraid if I rush it, she will ask me to put a stop to it and this Genie is out of the bottle now...

--- End quote ---

Heather, hello and welcome to SP. You are correct, everyone's journey is different. It's going to be a roll of the dice what your S.O. does.

Another aspect to consider: Crossdressing vs being transgender:

If you are cross dressing - your s.o. might be okay with you wearing feminine clothes and the associated joys/thrills/excitement that goes along with it because you aren't doing anything permanent. If you were to discover you are, in fact, trans, you may experience a wide variety of responses and not only from your s.o.

People are funny when someone comes out as trans. Some will be 100% supportive and others will have nothing to do with you. There is, unfortunately, no way to forecast what acceptances you will encounter. Being TG is an extremely complex medical/social/biological atmosphere that no one source has all the answers, mainly due to the fact everyone experiences being TG differently. While there are many factors that influence how someone will experience transition, if they choose that route, a few common pillars of circumstances seem to prevail in most transgender persons, and acceptance is certainly one of those.

You are wise to proceed cross dressing slowly around your s.o. It's a big change and while they might see this as a fun adventure now, however, you never know when the winds of change will blow their minds in a different direction, prompting an unexpected response, one you may not be okay with.

It's great you are talking about your concerns. Everyone here will always be here to offer support and any guidance we might be able to offer.

All the best,


Hi Heather, and welcome to Susan's.

My own wife thought it was all in good fun for awhile, and even went out with me when I was wearing a bra.  But then something triggered her fear that this was more than a game, and maybe I'd make a permanent change.  That shut her down for a long time.

You probably should see a counselor with experience in gender issues and see if you can pin down if you're a crossdresser (no permanent bodily changes) or if you want to change your body and go farther.  My other advice would be to go very slow with any further steps.  Good luck!

Heather N:
Thank you for your responses so far!

There has been a few times where my SO pulled back and made a snide comment, almost made me want to quit the path I am on. I.E. not long after I started shaving my legs , her hand touched my knee and pulled back in disgust. She said it felt like a woman's leg... that was hurtful and I actually stopped shaving my legs for several days after that, but I went back to it and she actually seemed to accept it better.. 

It's a delicate line for sure. I want/need her support on this but at the same time if I don't have it, I don't see myself going back. That's when counseling will come in I suppose.

Heather, I think you are on a slippery slope. I can relate to the joy of dressing in the clothing that seems to provide you comfort on multiple levels (more than sexual arousal if I read between the lines correctly). And, I understand how much it means to you to have the acceptance, and even participation, of a woman who means so much to you and is your lover. But here is the danger: She does not know the meaning of these clothes to you. At this point you’ve not been fully forthright, perhaps sort of guarding the ground you’ve gained. I suspect that you will become increasingly uncomfortable with her limits and she will become equally anxious about what your desire to dress means. At some point you may decide to lay all the cards on the table, tell her that there is a history to these urges that long precedes her and your medical need for compression stockings, and name it as the “gender issue” that it appears to be.

Not easy. It took me years during the course of my committed long-term marriage to come to terms with my “trans-ness,” and admit to myself and my wife that it was way more than bedroom games. She hasn’t taken it well, but we’re still together BECAUSE of what else we have, and although I don’t have her acceptance per se, she knows that I think of myself as trans. Good luck, Nancy


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