Sissify Me

[MessySlave98]

I've been away from GetDare for three months now after being quite busy but I now what to get back into it over the Christmas period.

Now I'm back I'd like to give sissification a go but don't know where to start. I have no supplies to go towards it and I had to get rid of the sex toys I had to stop distracting me whist at uni. This means I need to start fresh with some new sex toys and sissification items.

I do however want to keep this as private as possible but want to feel humiliated. I look forward to the dares and will give reports on everything completed.

Also if you have any recommendations on new sex toys to purchase I will certainly look into buying them

[PrincessJessica]

Well if you want to be a sissy you gotta walk like one. As you don't have any high heels do this one on your tiptoes wearing girly clothing...or in your case naked :p Start with a book on your head and on your tip toes. Your aims to get to 100 steps but each time you drop the book knocks 10 off your total (so say you drop the book first after 7 steps you're down to minus 3).

Time yourself doing it. However long it reaches to get to 100 steps is how long you have to finger your ass for. Hope that works out!

(To make sure it's achievable you may balance the book only when turning and cap the dare at 30 minutes max for the walking)

[MessySlave98]

Thanks for the dare. A good one for me to start off with.

I managed to walk the 100 steps in 1 minute 24 seconds without dropping the book once - I must have a good sissy posture!

I fingered my ass for that amount of time and quite enjoyed it. I could only manage 1 finger though because it's been a while since I've done any anal stuff.

Anything else I can do on my road to becoming a sissy?


Well if you want to be a sissy you gotta walk like one. As you don't have any high heels do this one on your tiptoes wearing girly clothing...or in your case naked :p Start with a book on your head and on your tip toes. Your aims to get to 100 steps but each time you drop the book knocks 10 off your total (so say you drop the book first after 7 steps you're down to minus 3).

Time yourself doing it. However long it reaches to get to 100 steps is how long you have to finger your ass for. Hope that works out!

(To make sure it's achievable you may balance the book only when turning and cap the dare at 30 minutes max for the walking)

[PrincessJessica]

Impressive, well now your walking like a sissy you should be peeing like one too. It's the classic "pee sitting down" rule for the next week, however, you must not have any male underwear touching your skin when peeing. You must wear underwear throughout but I'm curious if you'll purchase a pair of panties vs the nuisance of taking them off everytime. If you forget you should write "I want to be a sissy slut" somewhere (hidden) on your legs the next day. If you finish the rule successfully you should write "I'm a good sissy slut" on your chest but may remove after 30 minutes, if you fail once you should write "I'm a pathetic sissy that needs training" on your chest and leave as long as it takes to naturally wash off (or as long as possible within limits).

(As it's over Christmas you may take Christmas day off AND any day you're spending with family, as long as you extend the rule)

[MessySlave98]

I shall start immediately! Update will come once I'm complete after the new year. Impressive, well now your walking like a sissy you should be peeing like one too. It's the classic "pee sitting down" rule for the next week, however, you must not have any male underwear touching your skin when peeing. You must wear underwear throughout but I'm curious if you'll purchase a pair of panties vs the nuisance of taking them off everytime. If you forget you should write "I want to be a sissy slut" somewhere (hidden) on your legs the next day. If you finish the rule successfully you should write "I'm a good sissy slut" on your chest but may remove after 30 minutes, if you fail once you should write "I'm a pathetic sissy that needs training" on your chest and leave as long as it takes to naturally wash off (or as long as possible within limits).

(As it's over Christmas you may take Christmas day off AND any day you're spending with family, as long as you extend the rule)

[Hazman]

You should get a butt plug and keep it in until it starts to get sore and leave it in for 5 more minutes. Everyday you should attempt to keep it in 5 minutes longer than the previous day.

Another one, you should throw out a pair of male underwear every week and you can only buy female underwear.

These can start when you have money/in the new year if that is more feasible

[MessySlave98]

A used to have a butt plug and think it's about time I got myself a new one. I'll try and order that soon. Love the idea of replacing male underwear with womans and will start that just after Christmas! Thanks for the challenge.

You should get a butt plug and keep it in until it starts to get sore and leave it in for 5 more minutes. Everyday you should attempt to keep it in 5 minutes longer than the previous day.

Another one, you should throw out a pair of male underwear every week and you can only buy female underwear.

These can start when you have money/in the new year if that is more feasible

[MessySlave98]

Finally completed this after the Christmas break. I thought I'd be able to remember to take my underwear off but I forgot three times. Perhaps I should've just bough panties! Enjoyed this one though so might give it another go! I've now got "I'm a pathetic sissy that needs training" written on my chest...


Impressive, well now your walking like a sissy you should be peeing like one too. It's the classic "pee sitting down" rule for the next week, however, you must not have any male underwear touching your skin when peeing. You must wear underwear throughout but I'm curious if you'll purchase a pair of panties vs the nuisance of taking them off everytime. If you forget you should write "I want to be a sissy slut" somewhere (hidden) on your legs the next day. If you finish the rule successfully you should write "I'm a good sissy slut" on your chest but may remove after 30 minutes, if you fail once you should write "I'm a pathetic sissy that needs training" on your chest and leave as long as it takes to naturally wash off (or as long as possible within limits).

(As it's over Christmas you may take Christmas day off AND any day you're spending with family, as long as you extend the rule)