My very first outing anywhere as Natalie was in Chicago in 2023. I had never ventured outside but I wanted to and my lovely partner encouraged me to do so there. Since we were away from anyone we would know, it made sense. The trip was mostly successful so, after returning home, we discussed getting Natalie out locally. I practised my makeup more, with her help, and we made it out a few times.
After getting more comfortable, we discussed trying to get Natalie out again in a bigger way. Since we had already planned on going to California for our yearly trip, we decided to make that trip involve Natalie. Our plans revolved mostly around San Francisco and Sonoma Valley. We made our plans and decided to visit two wineries on Saturday and Monday, with San Francisco on the Sunday.
The first day of wineries, and the trip into the city, would both be done as Natalie. The second day of wineries would be done in boy mode for me. After a lot of planning, we had gotten everything ready from the AirBnB, to the flights, to the wine tours, and even most of San Francisco, planned out.
We made it into San Francisco on Friday night, picked up the rental car, and drove to Richmond where our AirBnB was. This was the best way for us to be in the middle of wine county and San Francisco.
We settled in and went to a local pizza place down the street for dinner but not much else. It was nice and we had some good conversations about what the weekend had in store for us. We then went back, got things ready for the next day, and went to sleep.
The next day we woke up around 8:00 AM. We gave ourselves plenty of time to get ready and drive to Sonoma Valley, so we never felt rushed. As my partner was getting ready, I feigned going to take a shower and then came back out shortly after. She was still getting ready, though I had waited enough that she was dressed and most of her makeup was done—and I asked her to marry me! She, of course, said yes, so the rest of the trip was her and Natalie doing everything as a newly engaged couple 🙂 [Ed: ❤️]
After that, I finished getting ready and I wore the pink and white dress in the photo above. It was one I picked out at Kohl’s specifically for this trip and for the wine tours, though I am still not sure how much I really liked it. It is almost too feminine and makes me seem like I am trying to hard. My partner liked it though so I was, and am, happy with it.
The first stop was at Benziger Family Winery. This was a trolly tour so we were on a tour with 6 other people. The only real misstep I made here is that when booking the tour, I used my male name. So, that is how the guide referred to me during the tour. It didn’t come up much, and I did tell an older couple we were chatting with that I was Natalie for today. But I still wish I would have taken the chance to correct the guide on my name. It was my fault of course, so I don’t blame him for not asking for clarification.
The tour was fun and we learned some really neat information about the winery. After, we had a wine tasting paired with different foods with the group and the guide interacted with me as he would with anyone, which made me feel at ease.
After this, we drove to a local eatery to have some lunch. The waitress was super friendly and we had a good time. We left there and went to our next winery which was St. Francis Winery and Vineyard. This was a bit different in that it was a self-guided tour. So, we got there and checked in, each got a glass of wine, and headed out into the vineyard. We followed the signs and had a great time by ourselves among the vines. We even tasted a couple grapes right off the vine! They said we could and there were only a few out there since we were visiting after some of the grapes had been harvested. The picture above was from that winery.
We went out to dinner that night as a reasonably fancy Italian restaurant and we got our first ever bottle of wine for the table (we have never done anything other than glasses). It was a good night and we had a fun time.
The next day, we got up a little earlier than before since we wanted to get on the bus to get to Chinatown. My photo in my profile is the outfit I wore for the day. We left the AirBnB and parked close to a bus stop, got on the bus, and then had no idea what we were doing. We weren’t completely sure when to tell the bus driver to stop, we kind of hoped someone else would but we didn’t really know where we were, so we actually ended up riding the bus until the route was done and the driver kicked us off! He was really nice about it and explained what we needed to do (get on another bus to take us back) and we ended up just going back to the car and giving up on Chinatown.
While on the bus, a couple of young men commented on me and asked to each other whether I was a man or woman, and then said to themselves that it didn’t really matter as long as I was happy. This was pretty affirming for me as it meant I (sort of) passed and they were accepting either way.
Once we got the car, we drove to the Castro district and parked on a side street. We walked to the Castro and even walked from the Castro to Haight-Ashbury. It is a bit of a trek due to being uphill, but we both wore comfortable shoes and I enjoyed the walk. My partner got tired so we hopped in the car in the middle of the walk (we parked between the two areas) so she could rest. I ended up adjusting my bodysuit since it was chafing and I accidentally tucked my skirt into my tights as I was trying to do everything sitting down in the car. And then we walked 2 blocks like that! Luckily I noticed before getting fully back into the crowds but I know a couple cars got a show…!
The experience in Castro was mostly just walking around, so not a whole lot to tell there. We did meet up with some friends of my partner for dinner at a Mexican restaurant. They were the very first people I “knew” other than my partner who met Natalie. It was exciting and they were both very accepting. One even gave us a ride back to our car after the night was done since it was dark and it was cold, and I didn’t bring any sort of coat, so the outfit I started in was what I wore all day.
We got home without issue and got up the next day for another day of wine tours. These were in boy mode for me which were still fun. We went to Landmark Vineyards first, which was actually just a tasting/wine pairing type thing and we were the only people there; which probably made sense for a Monday. It was fun and the hostess was awesome.
The next winery was Gundlach Bundschu and this was the best by far of the weekend. They had a cave tour, which is what I really love, and the wines were among the best we’d had. I even found a white wine I can actually tolerate (Gewurztraminer) The guide was awesome and it was a nice day. We ended up doing a wine subscription thing and we bought two bottles of Reserve Merlot that we are saving for our wedding!
We ended up ending on an easy note for the day and got up early for the flight home the next day (Tuesday).
Overall, it is so far my favorite outing as Natalie and my favorite trip with my fiancée. There was so much to do, no rude remarks or looks, and I felt mostly at ease for the majority of the trip. I don’t know where we are going next, though I am thinking Portland or Seattle, but I hope it ends up being even close to as enjoyable as this trip.
Tags: Cross dressing while on vacation
Beautiful romantic story, thank you for sharing. I hope it continues to blossom x
💚
Great story Natalie and congratulations on your engagement!
Hugs,
Rachael
The title expresses it all Natalie. What a lovely trip, proposal to a wonderful lady topped with fine wines. Perfect! Oh and you looked great in that dress, definitely not over the top.
Thank you so much. Some of my concern over the dress is probably just getting self conscious more than anything. I need to try hard to be passable (and still don’t quite make it) but I don’t really want to seem like I’m trying too hard 😂
One thing is certain…if a cd wants an outing, SF is the place to do it in. If you’d had any issues it would’ve been unusual. BTW I was born on Haight St. near Ashbury. The place is still there too.😊
Completely agree. We didn’t do much in Haight Ashbury but it was a fun place to be.
First off, congratulations, she sounds like a real keeper. Welcome to California. We are a welcoming, and mostly open minded state. While many love to bash California, it is nearly all out of jealousy. I am not the least bit surprised you had a fun and enjoyable trip en femme. I am very proud of my state’s open and accepting nature. If the rest of the countrywere as accepting our country would be much better off. We are far from perfect, but we are way ahead of the curve when it comes to what everyvody professes, but rarely actually do,… Read more »
While California doesn’t hold a monopoly in this regard (I have gotten along pretty well in Minnesota without issue) I do agree that the “vibe" in the areas was different. Better. I’m not sure how to describe it but if anyone has any doubts about themselves, San Francisco at least is a great place to try out
@nataliecd
I certainly don’t think California has a monopoly as I have been out in many places across the nation and a bit in Europe, just that most of the state is very accepting. Like anywhere, even here there are places I would hesitate to go en femme, at least solo. Mostly, it is just one can go just about anywhere here without worry as long as one uses a little common sense.
Yeah, that is true. I will give you that CA does have a pretty wide range of good places to go. Here in MN I would say that if I am not in the Cities or its suburbs, I would hesitate to go. I still think it would be safe to do so. Just that it would be more uncomfortable I think outside those areas. CA has fewer worry spots we’ll say. Out of curiosity, where did you go in Europe? We are planning to go to Europe for our Honeymoon (if we can pull the funds together) and I… Read more »
BTW, I love the dress, but white stockings for a vineyard tour? My feet and ankles would be a mess.
When I visit a winery, I love to get out in the vineyards and walk the rows and feel the soil. I enjoy the whole wine making process, not just the finished product.
I thought the tights brought the look together quite well 😀 I will say that my white sandals definitely got dirty but I would absolutely do it again. I am glad you liked the dress ❤️
@nataliecd
The reason I noticed was because I was just out wearing black boots and black tights and walking on dirt and my boots were a mess.
Thank you, Natalie for taking the time to write a detailed article sharing Natalie’s “adventures” (the smile in your winery photo says it all pretty lady) and congratulations on your engagement and wish you the best in your life together..
Warmest regards, Leonara 🌹
And thank you (and everyone else) for reading it! I am trying not to be too self-centered here but I do enjoy sharing things with this community and, of course, the successes are more fun to share 🙂 And thank you so much for the kind words.
I love to read positive en femme adventures.. to me you are an inspiration to this lady ready to be out in the “world”
Nice story Natalie and congrats on your engagement. You look nice in that dress and the white accessories are perfect.
Thank you! It is odd. In boy mode, it is dark all the way. I am trying to lighten things up for Natalie (though I still like dark for Natalie too!)
Sounds like an amazing time !!! Congratulations on your engagement too !
so glad that you shared this all with us! such a lovely story (complete with an engagement!) and so beautifully written. The dress looks great on you. Very happy to hear that all the wineries (and fellow guests) treated you so well.