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.

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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.

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Harriette
Lady
Trusted Member
12 days ago

Congratulations on your engagement,  Natalie! 
What a lovely experience to help convince you to go abroad more often.

Caty Ryan
Baroness
Active Member
12 days ago

Well done Natalie. I’m a keen Australian wine fan and over the years have visited many… wineries in various parts of “Oz". But never as Caty. As much as I’d like to try it… Too old and my SO would never accept the idea of me sashaying around wineries in a dress, I think I just have to be content to sipping away in male mode at home or at one of my favorite “eateries". (Where unlike most other countries, I can take a  bottle out of my own collection) Plus, I’ve never done a “proper vineyard crawl" without someone… Read more »

Harriette
Lady
Trusted Member
12 days ago
Reply to  Caty Ryan

Have you ever tried Melbourne Auburn Yellow, an Australian fighting wine good for hand-to-hand combat?
🤪

Caty Ryan
Baroness
Active Member
11 days ago
Reply to  Harriette

@harriette 
Unless you are talking about some cheap Australian “Sunshine in a bottle" wines, eg Yellowtail, sorry you  lost me there Harriete, I have no idea about what you are talking about and if its “humorous"??? well then it went right over my carefully coiffed head
Caty.
 
 

Harriette
Lady
Trusted Member
11 days ago
Reply to  Caty Ryan

Monty Python 😁

Caty Ryan
Baroness
Active Member
11 days ago
Reply to  Harriette

That explains it.Never was much of Python fan

Michelle Kaytee
Duchess
Trusted Member
12 days ago

Congratulations on your engagement! My wife and I have discussed going on a similar wine excursion girls trip in the same area. Looks like you had an amazing time. I need to move this from discussing to planning and doing.

Stephanie Ann
Lady
Active Member
11 days ago

Beautiful

Lea
Lady
Trusted Member
9 days ago

Congratulations on getting engaged!! What a fun trip, getting to be dressed and making memories. How wonderful.

Joanna T
Duchess
Active Member
9 days ago

So glad you both shared a positive experience! Love the white tights with white sandals look.
Joanna 💕

Stephanie Ann
Lady
Active Member
4 hours ago

🍒🍒Amazing & Beautiful story & trip Natalie 💓💓

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