Tomorrow's the Big Night

[Bianca Fay]

After several months of planning a makeover, it's finally going to happen tomorrow night.
My ex is going to come over after work & do my makeup. She's not sure if she wants to stay for the fashion show afterwards because she's never seen me all dressed up. TBH I'm not sure if I'm ready to present as a woman in front of anyone else for the first time either. But deep down I'm dying to show off all the outfits that she helped me choose on our shopping excursions.
I think I'm actually more excited about having the experience of a makeover itself rather than just seeing the final results because it will be my first girls night as Cecily.
We're both nervous & we agreed that a bottle of wine needs to accompany the evening's festivities.
Although she isn't sure about a fashion show afterward, she told me that I could wear a bra, panties & pantyhose during the makeover... provided that I have my bathrobe on during the process. So excited!

[Tracy Irving]

Sounds great. I hope all goes well. Let us know...

[Bianca Fay]

Thank you, Tracy, I definitely will.
In case she decides that she's ok with seeing me dressed afterward, I've picked out my first outfit. Knee-length black pencil skirt, white silk blouse & black pumps.
For the makeover I'll be wearing a matching lacy bra & panty set with nightshade pantyhose.

[Helen_Highwater]

Cecily,

This sounds like a wonderful opportunity for you. I would take it slowly with you ex as from what you've written she's more than a bit apprehensive about aspects of this. Try not to get too caught up in the excitement of it all.

Given her time to adjust and get more comfortable and that'll increase the chances of her staying for and enjoying the fashion show.

One last thought. The wine. Please if your ex is driving she doesn't over indulge. What hopefully will be a great night for you could turn into a really bad one for her if she gets stopped for drink driving, or worse.

[Elizabeth G]

Hi Cecily,

Or sounds like you're in for a wonderful time! Enjoy and please come back and tell us how it went.

Elizabeth

[Stacy Darling]

Hi there Miss Lucky,

Here I sit tomorrow night doing my own make-up!

But yes I do hope that things run to plan for you, and the result is as you have visioned!
You may be very nervous and anxious through the whole experience as well, and in that case I would say to you to look in the mirror and tell yourself how truly beautiful you are! Then relax.

Wishes with it,
Stacy!

[Stephanie Julianna]

Oh. I do hope it turns out to be everything you wish. If the stars are aligned you just might have a life changing night. For many here the first makeover becomes a turning point in our crossdressing lives.

[alwayshave]

Cecily, have a good time. I hope that your makeup turns out well.

[Krisi]

I think dealing with an "ex" for something this personal would be a bit weird. The bathrobe part seems a little strange as well.

I suggest dressing as a woman (with the boobs and butt) before she starts even if you have to wear a bathrobe. And shave and wear your wig. You have to have the hair on so she can do the makeup like she would on a woman.

[Jaylyn]

Apparently your ex and you must still be on good terms socially or this would not be happening. I also find it kind of strange that she doesn't want to see you after the makeover if she is willing to help you get to the part where you get dressed. Oh well you know her best so play it all by ear and I wish you the best of luck in the activity. Enjoy the makeover regardless.

[jennifer0918]

Have fun it sounds like a lot of fun. All first times in genderland are awsome sauce ; )

[CONSUELO]

Just relax and have a good time. As she is your "ex", has bought you clothes and is willing to have you sit there partially dressed while she applies your makeup, why not just accept that she has come a long way along the path of acceptance and leave it at that for the time being.

[Bianca Fay]

Thank you all for your replies.
Yes, she & I have remained on good terms over the last few years & has been helpful.
I think she offered to do my makeup because that's something she's always loved & was always getting her sisters/friends ready for parties. She loves makeup.
However, she is still a little hesitant to see me in full girl mode (I am too somewhat). She just doesn't know if she's ready for that so she may leave before I get dressed up. The lingerie is her idea because she knows it will add to my enjoyment of the experience, but she wants me to wear a robe because it would be weird for her to see me sitting in front of her wearing nothing but ladies underwear.
Before she arrives I will be shaved & have my nails painted (which she's expecting) but otherwise nothing else that might be surprising for her. I don't wear a wig, my own hair is about shoulder length & I'll have it tied back.

[Micki_Finn]

So is this going to be your first time in makeup?

[Bianca Fay]

So is this going to be your first time in makeup?

I've tried it twice on my own, with disasterous results

[Sarah Doepner]

I've tried it twice on my own, with disasterous results

Then pay very close attention and ask questions. I've learned a lot from the few times I've been on the receiving end of something like that. One pedicure/manicure was enough to get me doing my own nails after a bit of practice. The same goes with makeup. Don't be reluctant to ask very basic questions, often starting with the word "Why" or "What". It will pay off well in the long run.

But, don't let the learning interfere with having a great time.

[Jenny22]

Hi, Cecily. She divorced you for wearing pantyhose, you say, yet she's almost accepted your CDing (shopping, makeup, etc.). Ask her to see you dressed and suggest that she help you do, as a gradual coming to fruition which she may accept. It could bear fruit for both of you. If she is not now married, propose to her!

[Micki_Finn]

Well then this should be a really fun experience for you. Enjoy!

[Bianca Fay]

Hi, Cecily. She divorced you for wearing pantyhose, you say, yet she's almost accepted your CDing (shopping, makeup, etc.). Ask her to see you dressed and suggest that she help you do, as a gradual coming to fruition which she may accept. It could bear fruit for both of you. If she is not now married, propose to her!

We got married very quickly after we met. I guess our relationship wasn't seasoned enough at the time to weather the storm.
I wish I had been honest with her at the beginning, but (like so many others) I thought marriage would 'cure' my urge.
Unfortunately I was wrong & I began secretly wearing her pantyhose.
It didn't take too long before she caught me... I was being reckless & part of me knows that maybe I wanted to be caught. I wanted her acceptance & to stop feeling guilty. But she just couldn't understand or accept this part of me.
At that time in my life I had no interest in any other article of women's clothing other than hose, but that was still enough to end us.
It was many years after our divorce that we began a new friendship. We reconnected one day on the phone & continued to stay in touch. During one of our conversations she asked me if I still wore pantyhose. I admitted that I did & she said that she didn't think it was such a bad thing anymore.
Times have changed & so has she. I didn't do or say anything to change her mind... she just became more accepting on her own over the years.
When I realized I wanted to take the dressing further, I told her. She's been very supportive but we've been taking baby steps ever since.
We are friends again, nothing more. I have no romantic feelings towards her, nor do I believe she has any for me.
Tonight is just about having fun & enjoying the moment. I have no intention of taking her out of her comfort zone, so if she doesn't want to see anything more than my face in make-up, I will definitely respect that & appreciate what she has freely offered.

- - - Updated - - -


Well then this should be a really fun experience for you. Enjoy!

Thanks Micki!

- - - Updated - - -


Then pay very close attention and ask questions. I've learned a lot from the few times I've been on the receiving end of something like that. One pedicure/manicure was enough to get me doing my own nails after a bit of practice. The same goes with makeup. Don't be reluctant to ask very basic questions, often starting with the word "Why" or "What". It will pay off well in the long run.

But, don't let the learning interfere with having a great time.

Thank you, Sarah - she said the exact same thing!

[tammy1]

Lucky you! Have fun. Your X wouldn't be coming over if she didn't want to enjoy (if only secretly) while she makes you up. What exciting fun.

[Bianca Fay]

This evening was... amazing!!!!

[Helen_Highwater]

Cecily,

Errr, because? Details, we need details.

[Bianca Fay]

It was a perfect evening. I was really nervous but she was very calm & natural which put me at ease.
Before the makeover we each had a glass of wine & sat on my deck. She told me that her mission was to make me feel beautiful. And she did.
She spent a lot of time perfecting my makeup & was explaining everything as she went along. I was initially a little disappointed because I was hoping for a more dramatic look but she kept saying "less is more". She was right.
It was an incredible experience & we had a lot of laughs the entire time. It was an interesting blend of emotions... I felt a shift from masculine to feminine & just started to enjoy the transition.
After the makeup & hair we had another glass of wine & she said she wanted to stay for the fashion show.
I spent the next 2 hours modelling my outfits while she alternately complimented & critiqued me. She referred to me as Cecily the entire time & made me feel wonderful. It was so exhilirating!
There were a few moments of awkwardness because she wanted me to 'walk the catwalk' & strike a pose but I was very self-concious & definitely need more practise. However, I did feel comfortable while sitting with my legs crossed (as lady-like as possible) while she occasionally, although casually, touched my thigh.
At the end of the evening I asked her if we could have another girls night in the future. She just smiled & said "Not sure. It was fun, we'll see".
When her taxi arrived she gave me a quick kiss on the lips & said "Goodnight, Cinderalla"!
It was a wonderful night but after she left I felt a little sad. She will always remember me as Cecily now & I'm worried that her memories of me as a loving husband will disappear.

[Glenda58]

I wouldn't worry about her memories of her husband disappearing. But now she has memories of Cecily. And I bet she'll be back for more ladies night and maybe out for drinks. Glad you had a good time.

[Amy Lynn3]

Good for you, that all went well and I feel, deep down your ex will be back to share more girly time with you. We can only hope anyway. Wish you had a picture to share.

[Beverley Sims]

I was pleased at the reaction of your Ex, I hope it is not the last time for you both.

[Bianca Fay]

If I can summon up the courage I may post a pic from my makeover night.
I was particularly thrilled with how I looked in my red sleaveless bodycon dress.
She took a ton of pictures that evening; I modelled 6 different outfits in total but also had several variations of each by switching up shoes, accessories & various shades of pantyhose.
It's amazing how many different looks can be created by adjusting little details & she had some wonderful suggestions.

[Stephanie47]

I drifted over to this thread while I was reading your thread on church going women looking so beautiful. I think your former spouse is wonderful to realize you're a decent person and not some creep. She may have become more enlightened over the years and supportive of transgender men an women and others, gays and lesbians. It may be simply cross dressing is not something some women want in their men. Perhaps her willingness to do your makeup and see the fashion show validated somethings she has been pondering about you. Maybe further conversations will answer questions both you and her may have.