Short first outing with wife last night

[carahawkwind]

I've been mostly at home dresser, although I have driven places dressed up before, but have never really went out otherwise. Lately my wife has been very positive about my dressing and has encouraged us to go out. This weekend we had an overnight sitter and while the bulk of our evening was a more standard boy-mode date night, later in the evening we decided we should go on a short trip we me dressed up, we decided to go a very friendly dessert place in nearby gay neighborhood. I drove us there, we are able to find parking only about a block away. After getting out of the car we walked right past a large gay bar on the way and the doorman was friendly as we walked past, then we got to the dessert place and we were greeted to "good evening ladies", I'd never been addressed that way before, so it was nice. When we made our order, I let my wife do most the talking and checking out and the guy at the counter asked how the night was going, complimented her earrings she made herself, took a business card from her, while I sort of shyly stood nearby, but it was nice.

After that we decided we didn't have enough booze at home, so we decided to extend the outing to include a trip the drug store across the street. It was late, but there were a good amount of people there, but everyone was focused on their own thing and in that neighborhood a crossdresser isn't exactly the most exotic thing to see anyway. So we got our alcohol and walked back to the car and finished the evening back our place.

It was a small simple outing, but it helped break the ice for me and for my wife and it was all positive, so I expect when he have the child care set up to do it again, we'll probably try to go out again and try to extend how much of it is dressed up.

[JocelynRenee]

What a lovely story and what a lovely relationship you two have. The outing may have been short, but it sounds like a perfect first night out. I hope there are many more to come.

[katlee]

I think it is great that your SO accepts you and embraces the complete you to go out. Any small thing is a big thing when it comes from a person that we care about, especially when it is in the TG community :)

[Amy Fakley]

What a beautiful story!

[Katey888]

What a sweet tale, Cara - thanks for relating it... sounds like you have quite the neighbourhood scene going on and it's great that both of you can share the experience... :D

Katey x

[IamAmy]

That's great. My wife's really supportive too and I would love to go out dressed with her. It's still new for her so I'm hoping one day we will make that step. Baby steps!

[Marcelle]

Hi Cara . . . what a great story. Sometimes the simplest adventures are the most pleasant and it is particularly nice to be able to share it with your lovely wife. CONGRATS on getting out there.

Hugs

Isha

[Megan b]

Nice story. I hope to someday meet a lady like your wife. Your so lucky.

[EllenJo]

What a sweet story. You are so fortunate to have such a supporting wife.
Hugs
Ellen Jo

[CostaRicaRachel]

That's sounds like fun! Congratulations. What did you wear on your first night out?

[Sara Jessica]

Sounds like you went to the Hillcrest district, a place that is in fact overwhelmingly accepting. Glad you got out and that your wife was so on board. There are so many fun places to go in SD, your fun has just begun!!! :)

[Caden Lane]

Sounds like an awesome icebreaker trip for the both of you. Hopefully it will be the first of many outings for the both of you.

Ever & Always,
Caden Lane

[carahawkwind]

Thanks everyone for the nice responses. I wanted to get my positive experience out there, I know when I was lurking this site it was always good to come here and see positive stories and responses, to know you can do what you want things can be ok.


Sounds like you went to the Hillcrest district, a place that is in fact overwhelmingly accepting. Glad you got out and that your wife was so on board. There are so many fun places to go in SD, your fun has just begun!!! :)

Yes we went to Hillcrest, for now if we go out that is where we are going, the easily the most friendly neighborhood for something like this and it's one of our go to neighbors to go out to anyway, although our daughter significantly cut into our going out.


That's sounds like fun! Congratulations. What did you wear on your first night out?

Black top, leopard skirt, some hosiery and flats. The flats were a good low stress choice, so I wasn't overly tall, not awkwardly wobbling around, they are quiet to walk in and just a bit more blending. My wife prefers flats for me too, she likes when we are around the same size. I wore my fake glasses I have too, to be a bit more obscured and I think they are cute anyway. Maybe I'll post a pic of the outfit later, need to get it off my phone.

[Beverley Sims]

Carah,
It is those smal outings that lead to better things.
Enjoy your progress.

[Julie Denier]

That's terrific, Cara! Sounds like a great way to dip your toe in the water. So nice to have that kind of support at home, too ;)

[FemmeMonique]

Does your wife have a single sister? :love:

[carahawkwind]

Does your wife have a single sister? :love:

Yes actually, she gave me one of the tops I'm wearing in the post I just made pics section. I don't know if she's currently looking though. For anyone interested in what I wore for this outing I included a pic of the outfit there.

[Persephone]

:cheer:

Congratulations!

Hugs,
Persephone.