Vacation Planning

[AmberCrystal88]

I will be out of town the weekend of June 2/3 and will have some free time aside from work, friends, and general "tourist" type city exploring. Looking for some fun things to do. It will be great since I'll never see any of these people again.

Public crossdressing is of course on my want-to-do list and looking for ideas of where to take selfies while crossdressing (not giving away my location so make it generic - i.e. at a ATM, at a bus stop, etc). Also looking for some more specific dares, tasks, and challenges - the whole reason I'm here is to have some fun at someone else's demand. Likes and dislikes are in my signature/blog but of course I'm open to discussion.

A few details:
- I will be at a hotel, private room, king bed, pool.
- I am driving and will have my own car.
- Not sure about recreation options but it's a downtown/city area so just cityscape sight-seeing type stuff I'd assume.
- It's early summer (I'm in the U.S.)
- Resources - Limited money, a few women's outfits, toys (butt plugs, dildos, vibrator, gag, collar with "slave" lettering)

I will be sharing pics for proof when the time comes.

To-do list: (will be updated as this thread goes on)
- Wear only a bra and panties while driving.
- Spit roast for 1 hour or until I cum
- Have food delivered and answer the door in women's clothes. Eat while riding a dildo, and enjoy a creamy dessert.
- Wear bikini bottoms, speedo, briefs, or skin tight swimwear to the pool. Bright prints, polka dots, or floral prints.
- Edge before leaving and do not touch sissy clitty for the entire trip.
- Change into a new peice of female clothing in a dressing room, leave the store while wearing it (pay on the way out, of course).
- Use women's body wash, shampoo, and body spray.
- Wear a necklace with a heart and bracelets (will need to be purchased on the trip).

[MarvHarvey]

Perhaps if oyu provide some added info like:

• accommodations (hotel, bed and breakfast, etc.)
• how you will be getting around
• types of recreation available (beach, casino, etc)
• weather (summer? winter(could be in the mountains)? etc.)
• your resources, supplies

[AmberCrystal88]

Originally Posted by MarvHarvey

Perhaps if oyu provide some added info like:

• accommodations (hotel, bed and breakfast, etc.)
• how you will be getting around
• types of recreation available (beach, casino, etc)
• weather (summer? winter(could be in the mountains)? etc.)
• your resources, supplies

- I will be at a hotel, private room, king bed, pool.
- I am driving and will have my own car.
- Recreation, not sure... Downtown/city area so just cityscape sight-seeing type stuff I'd assume.
- It's early summer (I'm in the U.S.)
- Resources - Limited money, a few women's outfits, toys (butt plugs, dildos, vibrator, gag, collar with "slave" lettering)

((Added to OP))

[Binky]

What toys/clothes (if any) are you going to be taking with you?

[AmberCrystal88]

For women's clothing I'm bringing a pair of Jean, black pants, black yoga pants, a couple t-shirts and bras. I have gaffes as well I'll be wearing under.

Toys I plan to bring a handful of butt plugs and my two dildos... One is about 5 inches long and 1.5 inches wide, the other is 7 by 2. Also mouth gag, blindfold, and some restraints.

[Binky]

Hmmm ok well here's a few to get you going.

Presumably you'll be driving to/from your destination/hotel from your hometown? You are only allowed to wear your bra and panties in the car during the drive. Who knows how many people will see you If you need to get stop/get out/whatever when you may cover up. If you want to extend this then you must be wearing a bra/panties at all times while you're away.

At one point during the two days get completely dolled up as much as you can, place your two dildos on two opposing surfaces that are close to each other. Now spitroast yourself for at least 1 hour or until you come, whichever happens first.

One night you are to order room service and answer the door fully dressed up. If you don't want to do this then as before bra/panties under your clothes but also have your butt plug in. If said room service is a meal (it should be ) then place one of your dilos upright on one of the chairs, impale/fuck yourself as your eat your meal. Make sure you have a nice creamy dessert

[MarvHarvey]

How feminine a swimsuit can you wear at the pool or hot tub?

Baggies or boardies - NO WAY!
Bikini bottoms - maybe?
Swim briefs/speedo type - yes
Skin tight - yes
Bright prints or polka dots - yes
Floral prints - yes

[AmberCrystal88]

Thank you for all the suggestions, these are all doable and sound very exciting. I'll be taking pictures and videos the whole time too so I'll be sure to send picture proof after the weekend.

Originally Posted by Binky

Presumably you'll be driving to/from your destination/hotel from your hometown? You are only allowed to wear your bra and panties in the car during the drive. Who knows how many people will see you If you need to get stop/get out/whatever when you may cover up. If you want to extend this then you must be wearing a bra/panties at all times while you're away.

Yes I am driving, and my car has pretty dark tint, so panties and a bra would be just fine. Of course I want to have fun with this though, so I'll have the windows down weather-permitting.

I don't actually have any women's panties though, I love em, but I hate em. I have parts that just don't fit, you understand. I do have some sissy panties though, so I'll wear those.

Originally Posted by Binky

At one point during the two days get completely dolled up as much as you can, place your two dildos on two opposing surfaces that are close to each other. Now spitroast yourself for at least 1 hour or until you come, whichever happens first.

This should be a lot of fun, hopefully I can make something work (depends how the room is laid out). I could always move a chair or dresser if needed.

Originally Posted by Binky

One night you are to order room service and answer the door fully dressed up. If you don't want to do this then as before bra/panties under your clothes but also have your butt plug in. If said room service is a meal (it should be ) then place one of your dilos upright on one of the chairs, impale/fuck yourself as your eat your meal. Make sure you have a nice creamy dessert

I don't believe there's room service, but I could always order a pizza or something for delivery. I will do this as well

Originally Posted by MarvHarvey

How feminine a swimsuit can you wear at the pool or hot tub?

Baggies or boardies - NO WAY!
Bikini bottoms - maybe?
Swim briefs/speedo type - yes
Skin tight - yes
Bright prints or polka dots - yes
Floral prints - yes

I own a couple 2-piece bikini sets, not sure if they fit or how well. I'll try those on, otherwise I will order some sort of speedo or briefs.

[MarvHarvey]

Maybe you will get a few more before you go....

And: We will all be watching here for your reports, so we know what works best for your next trip.

[AmberCrystal88]

Originally Posted by MarvHarvey

Maybe you will get a few more before you go....

And: We will all be watching here for your reports, so we know what works best for your next trip.

I won't have cell reception for most of the trip between here and there, but once I get the I will for sure. I'll try to do reports and post pics as I go, if not I'll have a nice big report when it's all done.

Any further ideas are still welcome.

[Mieann]

Hello Amber.

How about getting some sweet/fruit-scented body wash and shampoos to shower before you go out? Don't you like to be a sweet-smelling girl?

When I stay alone in hotel, I like the feeling of not closing the doors except pooping. How about you do the same?

Mm, I know you dislike shaving then, it may be nice if you are open to keeping your body smooth (except your privates since that's your own preference). I think it fits well with feminizing? Your call though.

And I think it is important to powder some talc on your armpits and butt cheeks after your shower (after you towel dry yourself). You may rub the talc on your armpits off (not your butt cheeks!) if you are going out.

Maybe you want to sit and pee all the time. Remember to wipe!

I'm not sure if there's a mall, but if there's one, find 1 female clothing that you think is passable and change in their changing room. Of course, take a selfie of it in the changing room.

[AmberCrystal88]

Originally Posted by Mieann

How about getting some sweet/fruit-scented body wash and shampoos to shower before you go out? Don't you like to be a sweet-smelling girl?

This is great, what about women's deodorant and body spray as well?

Originally Posted by Mieann

When I stay alone in hotel, I like the feeling of not closing the doors except pooping. How about you do the same?

I'll be alone in the room so leaving the bathroom door open won't be an issue, or were you thinking the actual door to my room?

Originally Posted by Mieann

Mm, I know you dislike shaving then, it may be nice if you are open to keeping your body smooth (except your privates since that's your own preference). I think it fits well with feminizing? Your call though.

I'd love to shave and being away from home would be a great opportunity since my living situation doesn't really allow me too, however, it would also be very obvious at work which I'm trying to avoid.

Originally Posted by Mieann

And I think it is important to powder some talc on your armpits and butt cheeks after your shower (after you towel dry yourself). You may rub the talc on your armpits off (not your butt cheeks!) if you are going out.

Talc instead of deodorant, or both?

Originally Posted by Mieann

Maybe you want to sit and pee all the time. Remember to wipe!

This is already one of my rules

Originally Posted by Mieann

I'm not sure if there's a mall, but if there's one, find 1 female clothing that you think is passable and change in their changing room. Of course, take a selfie of it in the changing room.

This would be fun. Are you thinking like I would change then leave while wearing it? Still paying on the way out, of course.

[Mieann]

Hello Amber. I'll vote for no deodorant since I don't use any. If you are up to using body mist, why not?

As for the doors, I mean the toilet doors. Not the actual ones. I think that will be creepy.

If you find it fun to pay when wearing it, I can't really object to it, can I?

Do you wear necklaces? Maybe you want to wear one? And bracelets. Please don't put use chains as necklaces. Maybe something thin and light with a heart.

[AmberCrystal88]

Originally Posted by Mieann

Hello Amber. I'll vote for no deodorant since I don't use any. If you are up to using body mist, why not?

As for the doors, I mean the toilet doors. Not the actual ones. I think that will be creepy.

If you find it fun to pay when wearing it, I can't really object to it, can I?

Do you wear necklaces? Maybe you want to wear one? And bracelets. Please don't put use chains as necklaces. Maybe something thin and light with a heart.

I will add these few things to my to-do list in OP Thank you!

[AmberCrystal88]

Since I can no longer edit OP of this thread I moved it to a blog.

I'll keep that updated and use it to report and provide proof. Still accepting additional dates if anyone has anything else they're like to see.