Crossdressing vacation
 

Hello there!

In the end of next week, I plan to go onto vacation in full Sophie mode (I've only been twice out as a girl, and that was by night, so that's a very huge step up for me).

I plan to go certainly in Amsterdam, since it's not that far and, per my researches, crossdresser friendly (please tell me if it's wrong or if you have a better idea!) x)

Anyway, I'm here because I'd love to ask you to decide what I will wear, if I'll have some specific activities, some rules, etc... Mostly what I'll wear. The rest is up to you :)

Please note that if I have to buy something, I'd give a maximum of 100€ (more to buy some stuff there), and I have to receive them on time to leave (Thrusday or Friday of next week, so 16th or 17th).

Thanks you all! :3

You can also add some bondage tasks, some hotel dares or some sissy tasks if you want to :)

Easy one to start with, you must wear heels (minimum 4"/10cm) the whole vacation, except for sleeping obviously.

Will absolutly do so, thanks!

Get your nails done professionally while there

Definitely go try on clothes at least 5 different places. Don't be afraid to ask for help!

One day wear a thong a stuffed bra black pantyhose a mini skirt and high heels over 4 inch wear a wig and apply make up

Another day wear a thong and stuffed bra pantyhose and a tight dress

Must wear a stuffed bra and pantyhose everyday more daring if there the same pair

Nails done ok, will do on the first day

Try on clothes too, so I'll find the dress for the 3 rd dare!

Thank you! Any idea on the style of the shoes or of the wig? I may still have time for them on amazon... If it's prime :)

For now I have one long brown (not big quality) and a longer brown with blond parts (don't know how to say in English)

Ok, so I think I've founded my hotel for the days (will spend two nights there).

Here are the wigs I own :

https://www.amazon.fr/Perruque-Natur...=beauty&sr=1-5

https://www.amazon.fr/gp/product/B07...?ie=UTF8&psc=1

Well I think you should go explore places. Take in the sites. If things are less restrictive about social distancing, I think you should go to a nice bar or club and have fun. Dress up for sure. We want all the eyes to be on you. ^_^

As for tasks. I think when you get to your hotel, you deserve a bit of stimulation. Watch some porn and play with toys as you plan the itinerary for the next day. This can be repeated. ^_^

For reference we call the second wig a brown one with highlights. ^_^ I think you should rock the second.

Clubbing and dancing? My man part don't like to do it, but maybe Sophie it.. I'll give it a try x) won't be stuck in my room anyway x)

Hotel room play? Nice, thanks!

Highlights, yeah! Thanks xD

The second one is the highlight one so? :)

Consider checking out the red light district? I'm sure they have fun in all shapes and sizes!

Sophie very brave you are!
It is dream of many the vacation only in femele style and you will go in the your car to drive?

For the shoes some tell already heel high thet yes is must for sissy
For the summer you only must bring sandals the more sexy but not slutty

You only summer dresses or skirt allowed with thin camisole is ok?
What meny purse or handbag you heve? If less of 3 you must one more buy in store coordinate with the shoes with heeled sandal.
And when around in old town ask some the turist if they can make some picture to you with the your phone, for the memory of day

If find lollipops buy some and lick in sexy way in street. If some look you, blow one kiss in distance, smile, and the walk you go away.
Turn the your head after 3 step and if he look you again, tell “Hello!”

The wig brown with blonde mèche tips is the more beutiful, use it Sophie, perfect with black velvet choker oround of the your neck
Last question you use fake tits you?

Heve fun and care your self

Real clubbing and dancing is not possible here yet. Bars are open though.

I would suggest to check out some BDSM / fetish shops as well. Have fun over here and I am really curious how it will go, please let us know.
Stay safe and don't go in bad alleys after dark, even in Amsterdam you never know...

Red light district might be a nice place to go, but not sure I'll find something in my tastes as sophie... XD

No clubbing or dancing? Or so, only bars. Thanks for the info! :3

Bdsm stores I'll try to find some... Do you have any adress?

Highlights wig validated, thanks :3

But I'll be safe, yes, thanks for the advice :3

Sabina's big one now :
Thanks for the compliment! That's why I'm doing it.. I need a break and since it's a friendly town, less fear for me :3

No, I do not have a car, I'll go via bus... Since I don't know if they will ask my papers when I'll check in in the hotel, I'll arrive as a boy, but dress up and lock my male clothes immediately after... Since I have to look like my ID I suppose xD

Sandals? Great idea, I'm just wondering if they will loik godd with the black pantyhoses I have to wear? Do you have any idea on rhe sandal style? Showing my painted toenails interest me :3
But do you think I'll find some in shoesize 44 there?

I' ll buy a nice summer dress there so, and thin calisoles are good too, maybe I'll buy one in stores there also.

I only have one handbag for now, a leather aspect one. I'll def buy one!

Ask for help for the pics... Will be stressful but I can manage it, I hope!

Hahahahaha, love the lollipop one, so fun x')

Oh yeah, a chocker... Will def buy one there! The one on internet are always too small :'(
Depends, either just a little padding and I have already a little chest, or if I don' t use a low v neck I use complete fake tits, depends on the outfit :3

Thanks youuuu all! *-*

Check out this site for interesting shops
https://www.tesstesst.nl/tipss/de-le...van-amsterdam/
Especially the mentioned kinky shops. Might have to use browser translate function. :)

Yeah, thanks for the website! *-*

Sophie good morning,
You is already in the travel?
I want tell good stay in Amsterdam the first

All suggestion of Victoria very reasonable and good

Now for the easy girl part the dress code:
Pantyhose is collant? I was think you bare feet with the sandal becous is summer hot climate. But maybe is for hide some thing? You legs shave?
But no collant: stockings and the garterbelt I bilieve you must use.

Sandals style I think like it, sexy but not slut (this time!)
https://i.pinimg.com/236x/1a/88/2a/1...fea7aa9591.jpg
https://i.pinimg.com/236x/15/08/b5/1...b61178d02c.jpg
https://i.ebayimg.com/images/g/dwcAA...2nr/s-l400.jpg
Ok the silver one I love but heel too much high for walk

Size: I lucky small and can easy buy in normal woman shop (is always very emotion) but 44 I not think easy. I bilieve sexy shop maybe or if some shop specific for crossdress people is in Holland? Victoria can help?

Lollipop idea happy thet you like, is very innocent and naugty both
For photo ask people only if you confide, or skip it if not give trust at you

What is most fun enjoy liberty of be the girl, the cloth soft on skin in outdoor, the heels walk and I not see why not, the guys look they eyes on you.

Very very final, is you confide to heve one small buttplug inside the ass? I am sure help posture and make we gurls know the movement of the ass when walk.
When out I love the feel it inside, not must be the very big. One comfort you can wear for hours (many hours dear!)

Ok, enjoyed the vacation and take care yurself

Oh you forget not the choker, it very important accessory is!

The one they use me is like this:
https://i.etsystatic.com/5951944/r/i...51917_ocrn.jpg

But if find some more evocative like this you must really buy, also if this remember very much the ring gag!
https://di2ponv0v5otw.cloudfront.net...40f52acfd4.jpg

Could be fun to walk through the red light district plugged perhaps if you plan on going anyway? Pretty daring but being outside and plugged is a bit of a thrill :)

I think there was a misunderstanding, I'm going from next Thursday to next Saturday (I created the subject so I can buy something online before going if needed).

So, back to the messages :

Pantyhose is collant, yes. I've been asked to be in collant by a previous dare in the first page, but ly legs are shaven three times a week xD so I have no issues going without collant :)

Love your sandals, and mostly the lack of platform! I hope I'll find some, Victoria gave me a list a stores, some are selling shoes that can be the good sizes, let's just hope the price is not that much :p if you find one on amazon.fr that can be delivered by Thursday I'll take it x)

Walk with buttplug, it can be fun, yes! I've already done it, but not for a long amount of hours... In the red light it can be daring x)

Both chokers are tempting! I think I'll take both :3

Happy you like the idea of the choker
Good next time holiday


One dare idea for travel in the bus:
Ok boy clothe but you shell make it spice. I dare you wear only (I say ONLY) femele thong or culottes and it include travels
I dare you wear nylon collant or preferabble the stocking (bas in frence?) with the garterbelt also in the bus, and no boy sock to hide!

Lucky I not tell fishnet, what think dear sophie?

Only thong and female culotte? No problem x)

I feel like the fishnets are even more daring and tempting o:)

Ok if next poste agree, in the travel you MUST use fishnet and is FORBID thet you cover with other type of sock.
The next post decidde!!

do sophie must use fishnet uncovered in the bus travel?

Wear bright red lipstick all the time (except for sleeping, of course) and paint your nails red too. Don't forget to pee sitting down and use only female bathrooms all the time.

I think thet sophie not put lipstick in the travel. Be understanding she not travel crossdressed
It is same for chech in/out of hotel.
If we skip this, I bilieve sophie intend use lipstick and make up all time, is right?

Not lipstick befor sleep: I think sophie can remove lipstick only in one way: in front of mirror, blowjob give it to the preferred dildo.
You like this suggest? If brave, last nite of you stay at Amsterdam, the blowjob is not in front the mirror, it you do in front of window.
You not worry becous is last nite you stey and morning after you go away!

I will wear the fishnet for the travels, yes :p

Welp, for the lipstick / nails, if it can be avoided in the travels, all of the other times it's ok. Same for peeing sitting and on female bathrooms :)

For the blowjobs, it's not something I like to do, it's one of my limits :'(

Sorry sophie, I was read oral is limit.
But I only think suck dildo, not real cock!

But still if you not like, is not problem.

Toilet if femele is sure, when crossdress it is strange and not good if use man toilet. All behaveour must femele be!

While you're there, it would be nice to learn the cultural history. Maybe you could find a place that has traditional Dutch maid's dresses and wear one.

Oww, Dutch maid dresses? Okay! Just wear one or buy one?

I bilieve you shell buy it to remember travel
In France language you call souvenir?

But question is how traditional duch maid is?

Yes, makeup and painted nails only when you're dressed as a woman, not when travelling like a man.
You should wear female underwear and pantyhose (if you wear long pants) even when dressed as a man.
If you're concerned that someone would see female underwear when using an urinal at men's room, pee sitting down in a stall.

Souvenir, yes :) I will do so :)

By female underwear you mean thong or also a bra?

Definitely wear one while there, but buy it if you like it. In fact, as long as your budget permits, any compliments you get extend the time you must wear it. So, if you get a compliment when you try it on, you must buy it and wear it outside for at least an hour. Any compliments after that add another hour to the time. If you get a lot of compliments, you don't have to sleep in it, but continue wearing it again the next day.

Ok, nice dare :) thank you! :3

Is it normal there to wear it outside? :o

I don't imagine that it would be considered everyday wear, but it would certainly be considered acceptable to wear in polite society.

I bilieve in holland people respectful of every else but not sure cosplay is of normal attitude for every one around.
Dare you tell is interest and excitting for the idea of one hour moar add to every single comlement she is telled by other people, but I bilieve she risk the get of some humiliate if around hours and hours in street dressed in the tradition costume.
But my only opinion and depend from the costume also too she chosen!

sophie will go around for days always like girl dressed and I bilieve we all admire her for brave and corauge and much respect her.
I not think she want to appear silly around town, only beautiful girl, free of express the her personality if I littel understand psychology of she.
Correct if wrong interpretate the your holiday idea, sophie!

Hugs

I wouldn't go around wearing a special costume unless it's the pride or a bachelor party. It's most definitely not normal to wear around here. Or you must want to go for the humiliating aspect.
But if you want to go as a woman and enjoy being a woman, act and dress the part. And you will mostly get respect. :)

Btw don't forget the mouth mask on public transport, one of the few places it's obligated here. :)

Female underwear you usually wear when dressed as a woman. If you can hide a bra under male clothes and won't be noticed by people, yes.