Hello Girls, I got the biggest surprise on a recent vacation. A little over a year ago my girlfriend asked me to stop cross-dressing if I wanted to stay in a relationship with her. She had wanted this in our relationship and encouraged it for more than a year. I had been cross dressing in my own home privately for many years. I know being in a cross dressing relationship can be hard on the woman. She just couldn’t deal with it anymore. So I did a purge and decided I would rather be in a relationship with her.
We were on vacation last month at the beach. The nice part about going to the beach during that time of the year is the fact that the beach is not overly crowded in October and the weather is still really nice. So the first night there, we had gone out to eat and had gotten back from dinner rather early.
I was sitting out on the balcony of our condo drinking some bourbon when my girlfriend came out and she said, “Could you come in and help me with something?” So I walked into the bedroom she had some dress stockings and heels on the bed she asked me if I’d like to put them on. I just kind of looked at her. So I went ahead and got dressed for her in those items and we went out onto the balcony where we sat and finished a bottle of wine together. It just felt so nice being dressed again!
The next day we talked about it because she knows it makes me happy, however, she doesn’t know if she wants to let me do it full-time again.
The second day we were there, she painted my toenails and my fingernails She had brought a wig for me to on. We pretty much stayed in all that day and it was nice being seen as a woman again! She has told me when we are on vacation that I will be dressed as a girl all the time, she just doesn’t know if she wants me to bring it into the house again. She knows how happy it makes me feel. She loves me and I love her. It’s the first time she called me Sandra in over a year!
The rest of the vacation I was dressed every night in either a dress or some lingerie.
Please take time to send in comments to my article or answer one or more of the questions I’ve posted you below:
- Have you gotten mixed messages from your wife or significant other pertaining to your thrill of cross dressing?
- Are there certain limitations your wife or SO puts on your cross dressing which you find difficult to adhere to?
- Has your wife or SO come forward positively with her acceptance of your cross dressing?
Thanks girls for reading my article and I look forward to reading your comments pertaining to my article or to any of the questions noted above!
Sincerely, Sondra
Fantastic! “Have you gotten mixed messages from your wife or significant other pertaining to your thrill of cross dressing?" Geez, Sondra, it’s like every day. She changes like the wind. One day, she can be very encouraging. The next, she’ll say that she hates me (as Dawn) & wants me out of our lives. I have a similar story. I guess it was about 15 years ago that we went away, for the weekend, to the beach. Almost as soon as we checked in, she pulls a red, silk & lace, baby doll nightie out of the suitcase & said… Read more »
When I first came out to the wife I got mixed messages like crazy. She was pissed at first then started helping me buy clothes then backtracked and verbally shamed me to the point I was so depressed that I purged almost all my wardrobe. That was over six years ago and now its to the point that she simply has nothing to do with my dressing and I dress casual feminine around the house daily and its no big deal. The only limits are she doesn’t want to see me with big boobs but bras and small forms seem… Read more »
Sounds like fun Sondra!
My wife has always encouraged me to wear girl things. Her one rule is that we keep it fun. She likes to pick out my outfits, I never know if I will be a boy or a girl for the day until I step out of the shower and see what she has laid out for me. I am M/F about 60/40% of the time. When we go away on vacation, she packs only girl things for me
What a fun turn! With her in control, you get to experience anticipation when you know a vacation is coming up and the fun of being girlfriends when you get there! Acceptance is something we all crave. Beyond that, her participation is a huge bonus! Let us know how it goes from here please.
Great thoughtful article, Sondra!!! Vacations with you dressed the whole time…? Ah, have you gone to pink heaven…? Wonderful! So happy for you! To answer your question, this is my second marriage (12 blissful years now!)- (During my first marriage of thirty years I was completely in the closet for many reasons, some real, and some just fear. Sadly, my first wife didn’t know. In hindsight she probably would have been accepting. But I just could not get my self to tell her; probably because at that time I wasn’t really accepting of my CD myself, I suppose.) and my… Read more »
Sondra, I have literally just had the same thing happen. My wife has known of my love of lingerie and heels for over 25 years. Been married for 35 years. Initially she loved the idea, that turned into loathing quite quickly. Fast forward 20 years. Loved the idea of me dressing again, wigs, forms, lingerie were purchased and we were both very happy. A year later and the loathing and hatred of it returns with the words I want a husband not a girlfriend etc. My only option was to stop, I didn’t purge but locked everything away and didn’t… Read more »
So glad to hear of experience for you. I am very fortunate to have a spouse who fully accepts Winter and has even assisted me with makeup hair etc. I see this as a good starting point for you lovebirds. Do not push her, let it evolve naturally and it may come to a point where she is accepting of Sandra and even a regular friend for shopping or Girls night out.
Good Luck with her
Winter
wonderful, I am happy for you both.
Hi Sondra, Your Girlfriend needs to understand this is not something you can turn oon and off like a faucet, at least not for me. I am glad she is coming around I hope. My wife started out supportive, even buying me my first pair of pumps. However since seeing me have feminine mannerisms something has happened and she is barely tolerant. It got fairly serious and we had a serious talk. I had to tell her I couldnt stop if I wanted. we still love each other but it has killed out intimacy. I do dress at home though… Read more »
Hi Sondra, My first thought on reading your article was- PERMANENT VACATION! – relaxing en femme with your SO is the definition of Dream Vacation. That said, does my SO send mixed signals? oh yeah, like a Texas Twister. She knows and has known for over a year when i took her to dinner dressed head to toe in a smart women’s business suit. Since then it’s been fairly casual between us. She’s seen me in various states of dress without any comment. Then on Thanksgiving my daughter came to visit and they were folding laundry and my wife gave… Read more »