Sissy on hoilday

[subforfun86]

Hi GD!

I finally got the chance to go on a short holiday on my own for a full week and intend to live the life as a full time sissy while I'm away. Of course I have a few ideas on how to do so but I would love to get some ideas and dares from you! During my holiday I'll be staying in a hotel near/on a beach in Europe. I haven't booked as of yet so suggestions are also welcome.

[subforfun86]

So I got just one dare as of yet, which is not quite what I had in mind. I will try and work up to it during my holiday though.

Originally Posted by Shuol

Hi, I have a "difficult" dare for you.

I dare you during your holiday to roll a dice.

This is the number of cock you must please other than your own. It can be with your hands, mouth or boipussy.
You must be in chastity during one encounter. Don't forget protection

Have fun

Report back if you have the time

Does anyone else have some more realistic dares for me? Something along the line of; do this while wearing that, go shopping for this and that, and so on...

[Blue Griffin]

I'll see what I can come up with later today/tonight.
For now obviously you should only bring panties and always wear a bra minimum unless swimming.

Make sure to get a bikini tan line.

[Slut_Eva]

How about a beach holiday in spain? Its mostly sunny there so you'll get a nice tan.
You say you want to be a full time sissy... Then pack accordingly! You are only allowed to pack womans clothing, during your stay you have to go shopping for a nice summerdress at least three times and wear them too.

Enjoy your vacation!

[subforfun86]

Originally Posted by Slut_Eva

How about a beach holiday in spain? Its mostly sunny there so you'll get a nice tan.
You say you want to be a full time sissy... Then pack accordingly! You are only allowed to pack womans clothing, during your stay you have to go shopping for a nice summerdress at least three times and wear them too.

Enjoy your vacation!

Thank you miss, I will look into Spain, it sounds like a good choice.
Can I wear male clothing when going there and coming back? I think I would have a hard time checking in for the flight if I'm dressed as girl....

[Slut_Eva]

Hmm, OK. But as a recompense you will add to your luggage your biggest dildo, the chastity cage with spikes, your wrist and ankle shackles, at least 10m of rope, your corset and leather mask. You'll know why soon enough...

[subforfun86]

Yes miss,
I will do just that , thank you!

[subforfun86]

Hi GD! So far I got some very exciting dares for my vacation. I'll be leaving on Sunday so if you would like to dare me, you only have four days left to do so!
Oh, and for those who need a location for, well reasons... I'll be staying at a place called malgrat de mar.

[subaddict5]

Looks like Eva is planning a painful holiday of chastity for you!

[Victoria85]

Do you plan on posting the dares you already got and writing a report about it in the end?
If we know what you are already going to do, it's easier to add to

[subforfun86]

Originally Posted by vincentio

Do you plan on posting the dares you already got and writing a report about it in the end?
If we know what you are already going to do, it's easier to add to

That's a very good point...

So for my vacation I have the following dares and rules so far;

Rules:
1. Only wear panties and a bra;
2. Only take woman's clothing with you (except the clothes you are wearing during flight)
3. Take along your biggest dildo, chastity cage with spikes, wrist and ankle shackles, 10 meter of rope, corset and leather mask.

Dares;
1. Work on your bikini line
2. Go shopping for a nice summer dress at least three times
3. Wear your chastity cage during your entire trip, except for when required not to by dares.
4. Wear your chastity cage, wrist and ankle shackles, corset and shortest skirt. Go out for a walk on the beach until you find a secluded spot. Bring your leather mask, rope, dildo and a sign that says "Play with me?" along. Place the sign next to you, wear the mask and hogtie yourself for at least 15 minutes. Start a timer when you are hogtied. When you release yourself, for every second less than 15 minutes you are to fuck yourself with your dildo 2 times cowgirl style. (I might chicken out on parts of this one)

Maybe dare;
1. roll a dice, please that number of cock other than your own. Wear your chastity cage during at least one encounter

After my vacation I will report back of course, I thought that was pretty much implied when you ask for dares, so yes, I will. (It might take a few days though)

Oh, and only two days left!

[Fiona]

Wear a butt-plug the entire time, except for visits to the toilet. Furthermore you are not allowed to cum during the holidays, except from getting fucked in your sissy-pussy by somebody else. To ease that, put on the chastity-belt at the destination-airport as soon as you arrive and store the key somewhere near (for example in a locker) so that you can only retrieve it when you are back at the airport, which is preferable on the day you travel home.

Finally you are only allowed to sleep with your fully inflated gag in your mouth.

I hope that is what you like. ;-)

[Fiona]

Oh, and you will of course be completely shaved the entire time (except for your head-hair) and where full makeup the entire time between arrival and departure.

[subforfun86]

Originally Posted by Fiona

Wear a butt-plug the entire time, except for visits to the toilet. Furthermore you are not allowed to cum during the holidays, except from getting fucked in your sissy-pussy by somebody else. To ease that, put on the chastity-belt at the destination-airport as soon as you arrive and store the key somewhere near (for example in a locker) so that you can only retrieve it when you are back at the airport, which is preferable on the day you travel home.

Finally you are only allowed to sleep with your fully inflated gag in your mouth.

I hope that is what you like. ;-)

Originally Posted by Fiona

Oh, and you will of course be completely shaved the entire time (except for your head-hair) and where full makeup the entire time between arrival and departure.

Thank you for your dares Fiona!!
However, I won't be doing the inflatable gag. It is too dangerous to restrict breathing while sleeping, I'm willing to do a punishment for refusing though.
Current rules and dares;

Rules:
1. Only wear panties and a bra;
2. Only take woman's clothing with you (except the clothes you are wearing during flight)
3. Take along your biggest dildo, buttplug, chastity cage with spikes, wrist and ankle shackles, 10 meter of rope, corset and leather mask.
4. Wear a buttblug all the time
5. Wear full makeup every day
6. shave top to bottom each day

Dares;
1. Work on your bikini line
2. Go shopping for a nice summer dress at least three times
3. Wear your chastity cage during your entire trip, except for when required not to by dares.
4. Wear your chastity cage, wrist and ankle shackles, corset and shortest skirt. Go out for a walk on the beach until you find a secluded spot. Bring your leather mask, rope, dildo and a sign that says "Play with me?" along. Place the sign next to you, wear the mask and hogtie yourself for at least 15 minutes. Start a timer when you are hogtied. When you release yourself, for every second less than 15 minutes you are to fuck yourself with your dildo 2 times cowgirl style. (I might chicken out on parts of this one)

Maybe dare;
1. roll a dice, please that number of cock other than your own. Wear your chastity cage during at least one encounter

One day left to add dares....

[Fiona]

Okay, another rule: You will wear your long (brown) wig the entire time. The only shoes that you are allowed to wear from leaving the airport at arrival to entering it again at departure will be High-Heels with at least 5 inch.

Also: I don't see that there are any dares for which you have to remove the chastity-cage, so do as I said already and lock yourself in on the airport and leave the key in a locker.

As alternative and punishment to the inflatable gag, you will now have to sleep with your spider-gag in and will have to wear your corset pulled as tight as you get it whenever you are in your bed or sleep.