Going to San Francisco - Plan to go out dressed one evening

[SillyPantyMan]

First off, a little bit about myself. I'm a 34 year old male who has always loved women's clothing not only for the feel but also the looks. I've been wearing panties and other lingerie on and off since I was very young. I have worn some clothes on and off but later in my life I didn't have available clothing due to the fact I had no where to hide it from my SO. I have a decent collection of panties and a couple bras I wear when I can but if I buy clothes to wear I usually purge them at some point because I don't have anywhere hide a decent amount of stuff. I don't do makeup or wigs because that has never been a part of what I like. I've don't two transformations, one at Transformations by Rori and one at Wildside, and never felt that was me. I just like wearing the clothing and it is a great stress reliever for me.

I have a trip coming up to San Francisco where I'll be out there for a few days. I want to go out dressed even if it means going to Divas for the late Thursday dance show. I've never been outside dressed but I just have an urge to do it now. I've got an outfit ready including leggings, flannel shirt, black cami, boots, and scrunch boot socks. I've never considered or even think about purses so I picked up a matching phone case wallet to hold my ID and cash.

The issue is I'm staying at a property I rented on AirBNB and will need to use public transportation to get wherever I go and back. I'm actually considering using Lyft because it seems like they actually hire what would probably be the most understanding drivers. They also do extensive background checks on their drivers. I plan to carry a small thing of mace in my boot if I need it.

My question is San Francisco the right city for my first time out?

[Nikkilovesdresses]

Mace??? It's SF for god's sake, not South Central LA. Nobody's even going to notice you, unless you start Macing them- I'm thoroughly jealous, have a great time, and stop worrying so much!

Oh, and welcome !!

[SillyPantyMan]

Thank you for the welcome.

I'm very much looking forward to it because I do need to relieve a lot of stress. I just hope I get cool drivers.

[Lorileah]

It will be fine. No one there even notice now. Public transportation will do too. Go have something to eat, wander the Castro, take in the show.

[SillyPantyMan]

I'm not sure I'm up to doing that much yet. I think I'll be doing good to go to Divas on my first outing. Since I won't be doing anything to hide my appearance I'm worried about someone taking a picture of the man with the cute butt wearing leggings.

[sara.rafaela]

Hi, you might check some of my posts. I have spent a lot of time in San Francisco. Divas is ok for a first night dressed. it was the first place I went. By public transportation, I think you are talking about taxis. I would not be concerned. Hail a cab. Tell them where you want to go. They do not have time to care. I have ridden the BART, Muni, and Amtrak with no events. If you are there on a Wednesday night I might recommend the Cat Club on Folsom St. for the Bondage a Go Go night. It is really low key, nice people and more fun than Divas. I am going to be there twice between now and early Feb. If our schedules mesh...

[Princess29]

San Francisco, I doubt anyone would even look at you. They certainly wont be shocked.

[SillyPantyMan]

Sara,

Based on what you know is it possible to do both Divas and Bondage a Go Go on the same night without being out until 3 AM? Would starting out at Divas around 10:00 get me to Bondage a Go Go too late for the fun?

Also, I'm not a dancer more a spectator, would I still have fun at Bondage a Go Go? I wouldn't want to make a fool of myself.

[kkaye]

You are in luck. Look up Carla's on line. It is a place that serves CD and transgender individuals. They have places to change, makeovers, and all one need for a night out and a place to change back or forth.

[SillyPantyMan]

Is there a place like Carla's in San Francisco? I think San Jose is too far away.

[JessicaFoxx]

I think if its SF i don't see a problem unless you start macing people then that might be an issue. dress up and have fun.

[SillyPantyMan]

Alright, no mace. Anybody want to be my back up emergency ride if I get to where I'm going and get scared to get a ride back?

[sara.rafaela]

Hi, you can go to Divas and the Cat Club on the same night. If you go to Divas at say 9 or 10 PM it will be kind of dead. You will have a drink in the bottom bar. There will not be much going on. Later, on the second floor I think they have school girls night and a lot of attractive girls dancing in plaid mini skirts. From Divas you can hail a taxi very easily from the front door. The Cat Club is located on Folsom and 8th. It is about a 5 minute drive. They have a $10 cover charge. There will be nice crowd, very diverse. The median will be people in various types of black Gothic dress. At one extreme there will be a few people dressed like they are going to the bar at Applebees. At the other extreme there will be people being led around in collars. There may be 2-3 other girls like us there. I believe on the third Wednesday of each month there is a place nearby called wicked grounds, a coffee shop and they have a meet there. If you are at Bondage a Go Go on those nights there will be more girls, as they retire to the Cat Club after their meet. The music in there is typically industrial and Metal. You do not have to dance. If you approach people and talk, people will be nice to you. If you choose to remain on the sidelines, then people will leave you alone, as most people there are straight. For sure, unless you go crazy with your dress, you will probably be one of the least outlandishly dressed people there, and will not stand out. This will be different from Divas. If you are reasonably attractive, and it is busy, you will probably be approached, and most guys there are looking for one thing.

Please do not worry about the taxis. Hail or call a normal cab. Tell them where you are going. They will take you there without comment. Same goes for the desk person at your hotel, your bartender, bouncer. Do not worry.

[Paula_Femme]

...there is a place nearby called wicked grounds, a coffee shop and they have a meet there.

I can certainly vouch for the Wicked Grounds coffee bar! It's located at the 8th and Folsom, a fun, eclectic place as their Yelp reviews attest to. Oh yeah, you really WON'T need the Mace... have FUN!!!

[SillyPantyMan]

image.jpg

This is basically what the outfit I plan on wearing looks like. I have short hair so I won't have the hair over my shoulders like this picture. Am I going to stick out going to Wicked Grounds or Bondage a Go Go. Is it too trendy for either of these? I really don't want to be any more uncomfortable than I have to be on my first time out.

[CONSUELO]

Yes Carla's in San Jose does seem a long way from SF but there is a frequent train service between the two cities and the cost is reasonable. Try Carla's though as it is a very good business and she is very helpful and supportive.

[sara.rafaela]

Hi, This looks like a fine outfit for your first time. Perfect. You want to be comfortable and confident. A dress that is complicated to wear and is fussy will not inspire confidence. There will be so many things running through your mind that you want to be as comfortable as possible. I would feel comfortable in this outfit going out shopping to Union Square, to the museums in Golden Gate Park, or to the bars at night. I have never been to Wicked Grounds, in SF I am typically working during the day. Then I head out to Golden Gate Park to do a 6-8 miles. Then dinner, leaves no time. But, the Wicked Grounds meet is labeled as a "Sissy Meetup", I have seen when they are coming to the Cat Club afterwards and the outfits can range from extra casual, as you are proposing, to crazed Gothic maid with corset anddog collar. About the same dress goes for the Bondage A Go Go night. You will not stick out.

[AnnalieseH]

My first, and so far only, real public outing was in SF. It's my favorite city. I come from a very small community where this lifestyle is not really accepted. I stayed at a hotel downtown, within walking distance of the Westfield mal. That was my outing. My GF and I went out for an hour or so, it was busy, and although I found myself turning my head and hiding behind my hair, I didn't get too many looks. I did have makeup on but I was dressed very comfortable in a casual dress and tights with boots. I did feel a little disappointed and ended up not dressing again the entire week. I thought about Carla's but it just didn't fit into our schedule. My GF was all for it but I opted to just enjoy my vacation without the feeling of being watched. Have a great time. The feeling is amazing and a bit scary. I'm planning my next few outings now. Just need to work on my makeup.

[Racheltvvt]

I don't think anyone would notice at all. I can recommend "The Stinking Rose" restaurant. If you like garlic with a side of garlic!!