long term dares for a sissy

[serendipitous]

You must also modify the way you walk, you need to learn to walk more like a girl with swinging hips, this is good to practice in heels. You should take small girly steps not man strides and wiggle while you walk, don't swing your arms.

[obedience_247]

Originally Posted by vladimir_bz_lion

It is very important as a Sassy sissy to always please yourself in a way that will emphasis your sissiness girly girl ways. By always pleasing yourself in a girly, humiliating or degrading way will ultimately lead you only to climax as a girl would. Scary isn't it sissy? Nonetheless, don't you dream about being a girly, submissive, panty-wearing sissy anyways?

Lets re-cap..

Every Orgasm you know have is as close to the way a girl would cum as possible.

In truth this is the way you want it, to live as a girl, think like a girl, dress like a girl, move like a girl, shave like a girl, have only the prettiest panties and lingerie (the more girly the better), masturbate like a girl, have sex just like a girl and of course have orgasms just like a girl.

you will acheive this buy making sure you follow the sassy sissy girly rules :

1. Never EVER stroke your penis like a boy. You do not have a penis so this is no longer an option. You only have a clitoris. Your penis is now and forever a beautiful clitoris.
2. You now also have a very pretty smooth silky pink pussy. You love your pussy as it is your primary source of sexual relief.
3. You can only climax while having a dildo, a vibrator, a realistic cock or indeed a real cock deep inside your quivering pussy.
4. You may touch my clit but only with ONE finger at a time. you must not rub but caress with a slow circular motion. This may be done through panties or with them pulled around your thighs. If you want to climax through this method you must observe rule 3.
5. You can only masturbate or cum whilst wearing very cute girly attire. At the very least very sassy and pretty panties and bra.
6. You must be wearing very cute girly girl perfume. Try Lacoste "a touch of pink".
7. You must pout and round your lips in to the shape of a letter "o" and only make the sound "ohhh!".
8. You must fantisize about cocks as you recieve pleasure. you want that cock in your pussy to explode inside you
9. At least three times a week you must learn to come from penetration alone, preferably having dry multiple orgasms. Just as a girl would. Touching your clit is forbidden on these sessions. you may however caress your nipples or any other part of your body just as a girl would.
10. When you climax you must cry out and pant (or scream) just as a girl would climax.
11. Of course you must consume any cum produced (this is important) from your (just used) dildo. This must be done slowly and lovingly as you worship the instument of your orgasm.

hmmm I love how feminine and girlie you are making my orgasm and almost all of the above I will do from now on. Rules 1-7 I can do no problem and all future masturbation will be done as you have set out. Rule 8 will be difficult but I will try. Men don't turn me on so I will be deeply humiliated focusing on cock as I rub my little clitty. I will try, can it be shemale cock? Can I use porn?

Rule 9 is a big problem as in my life I have never ever had an orgasm without clitty stimulation. Literally I have never, even after repeated attempts at anal stimulation only. I have never even had a wet dream even as a teenager. I just have never had on orgasm without clitty stim. Of course I an willing to try again. But like many real girls I think penetration by itself will never make me Cum. It will just get me more frustrated. But I am happy to live out the expertise many women have all their life of orgasm free penetration. On these 3 day I will not touch my clitty at all.

Rules 10-11 are no problem. I already obey rule 11 (unless using Cum for another task eg dry on face). I love how during and after masturbating you are making me verbalise my sissy female nature.

Now with the finger circle method an I right in thinking every orgasm is effevectively ruined compared to the normal make death grip method? I am happy to do this as i'm not sure I deserve full male orgasms.

Finally how often should I orgasm? Currently your new rules mean 3 days a week I have probably zero chance of orgasms as they are penatrive only days. But can I Cum all the other days? Or do I need some kind of schedule. I've heard of some scary sissy schedules where each time between orgasms is increased by 1 day. Or they need to complete a set number of tasks to earn a clitty stimulation ruined orgasm. Or should it just be 1 day a week? What do people think?

[obedience_247]

Originally Posted by sissyjulie

Hi honey,

I believe you should keep your pubic hair trimmed in the shape of a heart and died sissy pink.

Julie xxxxx

I live that idea but i have already been ordered to stay completely smooth so i'm not sure which one to do? Which would be more sissy like and humiliating?

[obedience_247]

Originally Posted by serendipitous

You must also modify the way you walk, you need to learn to walk more like a girl with swinging hips, this is good to practice in heels. You should take small girly steps not man strides and wiggle while you walk, don't swing your arms.

I will start working on my walk immediately. I need to be slew and stay on this so I don't lose my job for being odd

[serendipitous]

Originally Posted by obedience_247

Rule 9 is a big problem as in my life I have never ever had an orgasm without clitty stimulation. Literally I have never, even after repeated attempts at anal stimulation only. I have never even had a wet dream even as a teenager. I just have never had on orgasm without clitty stim. Of course I an willing to try again. But like many real girls I think penetration by itself will never make me Cum. It will just get me more frustrated. But I am happy to live out the expertise many women have all their life of orgasm free penetration. On these 3 day I will not touch my clitty at all.

Something you could try, though is difficult to do sometimes is to tuck and fuck. Get a pair of tight panties, tuck yourself away nicely, I'm sure you know how to do this otherwise you'll never be a good sissy, but make sure the head of your itty bitty clitty is exposed. Now when tucked this should be trapped between your legs. The next part may require some preparation. When tucked you wear tight panties to hold it all in, I do anyway, but you'll need to modify your panties.

Cut a hole in them roughly where your beautifully shaven silky smooth sissy pussy is, make the hole big enough for your dildo to pass through. Now when you tuck and our panties are on you should be able to put your dildo inside you (don't forget lube) and as you pump it you should be able to rub your clitty with the dildo. You might need to experiment with positions to be in and angles of the dildo but I have done this and it does work.

This has one advantage if you cum. When your tucked the force of expulsion is much lower so the cum more trickles out, it then gets all over the dildo and pushed into your sissy pussy while you pump. This feels great as its like you get a sudden rush of extra lube like girl cum and you can pull the dildo out and suck off all that lovely cum!

I have done this before too, lots of times, works best on your back as you get the best angle for contact.

[serendipitous]

Originally Posted by obedience_247

I live that idea but i have already been ordered to stay completely smooth so i'm not sure which one to do? Which would be more sissy like and humiliating?

The bright pink heart would be the most humiliating, but you should follow the first dare and be completely bald. Maybe look for temporary tattoos of pink hearts you could apply, or perhaps some at home vagazaling (sticky glittery stars from a craft shop).

[vladimir_bz_lion]

Being fucked is a very important part of being a girly girl sassy sissy. Of course you have thought about it. And you have craved it. Now is the time to start stretching your sissy fuck pussy so it can take big cock like it's supposed to.

If you have never played with your sissy pussy, you are in for a new experience. Sissies need to be fucked like girls. They need to be filled with enormous cock and fucked hard and deep. In order to achieve this all important goal, you will need to stretch out that tight little pretty pussy. You also need to feel what it is like to have your prostate massaged while you have your ass pussy filled with cock, because it will addict you to being fucked like a girl! This is where the aneros cums in!

Once you get your pink dildo and aneros, you can start your training. It's very important to get a good quality lube and to use lots of it. You also should be wearing panties, stockings and another girly items. You must feel as sissified as possible to begin this assignment. If you live alone, you will be able to save your sissy cum like a good gurl. This way, you can use the cum as lube for your pussy the next time you get fucked.

Now we have to get you into a very gurly mood. Only the sluttiest gurls will get their sissy pussys filled. So, on with your panties! If you have some lipstick, smear that onto your slutty lips too.Stand in front of a mirror with your panties on. Rub your sissy clit through the panties. Leave the tip of it sticking out of the top of your panties. If it is big enough that is. You need to see yourself as you really are. A sissy in panties with a hard little clit!

Start shaking your ass into the mirror and saying "Fuck Me, I'm a sissy sassy gurl" over and over. Blow kisses to yourself and wiggle your hips and ass and beg for cock in your pussy. Lets start with the aneros. You will have to determine the best position to insert this. Whatever position you are in, make sure you relax. Relax your pussy hole and let that aneros slide in! Once it is in and situated properly, you can start to play.

Make sure to use the mirror. You must see yourself with this full pussy. You must see your clit leaking all over your panties. You must see the aneros in your pussy and you must know that you will NEVER be a man. Each time you play, leave the aneros in a little but longer. But never leave it in for too long as you could damage your sissy pussy. While you prance around in front of the mirror, stroke your clitty through your panties and wiggle your sissy slut ass, I want you to say "I am training My slut pussy for my new boyfriend" As you squirt your juice into your panties, say that you are cumming for HIM and that you are now his slut. Then slide your hand to your mouth and slurp up the cum.

As you get used to the aneros it will soon start to induse dry multiple girl orgasms, so girly. You will soon realize you can have mind blowing female orgasms with just your pussy alone. You can upgrade to your pink dildo and learn to ride it. As you use your toys, think of how you are preparing your pussy to be fucked hard! Think of how much you will be pleasing Men. And think of how far you have cum in your sissy sassy training. You must use an aneros or dildo whenever you play with your clittly from now on until you are ready to take a big cock.

Finger circling method may give you ruined, full or half-ruined orgasm. It depends for different guys. But it is only way you allowed to touch your clitty. If it will be ruined - it is your sissy destiny! Let me know how it works for you.
Though, you may play with your asspussy and nipples and cum from it (as good sissy) anytime you want.

You may fantasize about shemales instead of males as you asked. But you not allowed to watch straight or lesbian porn. Only shemale/sissy/gay videos for you.

I love you idea about scary sissy schedules where each time between orgasms is increased by 1 day. Let it be so. Also you must post detailed report about each of yours orgasms. Keep me informed about yours actions.

I prefer totally shaved girls.

[obedience_247]

Originally Posted by vladimir_bz_lion

Being fucked is a very important part of being a girly girl sassy sissy. Of course you have thought about it. And you have craved it. Now is the time to start stretching your sissy fuck pussy so it can take big cock like it's supposed to.

If you have never played with your sissy pussy, you are in for a new experience. Sissies need to be fucked like girls. They need to be filled with enormous cock and fucked hard and deep. In order to achieve this all important goal, you will need to stretch out that tight little pretty pussy. You also need to feel what it is like to have your prostate massaged while you have your ass pussy filled with cock, because it will addict you to being fucked like a girl! This is where the aneros cums in!

Once you get your pink dildo and aneros, you can start your training. It's very important to get a good quality lube and to use lots of it. You also should be wearing panties, stockings and another girly items. You must feel as sissified as possible to begin this assignment. If you live alone, you will be able to save your sissy cum like a good gurl. This way, you can use the cum as lube for your pussy the next time you get fucked.

Now we have to get you into a very gurly mood. Only the sluttiest gurls will get their sissy pussys filled. So, on with your panties! If you have some lipstick, smear that onto your slutty lips too.Stand in front of a mirror with your panties on. Rub your sissy clit through the panties. Leave the tip of it sticking out of the top of your panties. If it is big enough that is. You need to see yourself as you really are. A sissy in panties with a hard little clit!

Start shaking your ass into the mirror and saying "Fuck Me, I'm a sissy sassy gurl" over and over. Blow kisses to yourself and wiggle your hips and ass and beg for cock in your pussy. Lets start with the aneros. You will have to determine the best position to insert this. Whatever position you are in, make sure you relax. Relax your pussy hole and let that aneros slide in! Once it is in and situated properly, you can start to play.

Make sure to use the mirror. You must see yourself with this full pussy. You must see your clit leaking all over your panties. You must see the aneros in your pussy and you must know that you will NEVER be a man. Each time you play, leave the aneros in a little but longer. But never leave it in for too long as you could damage your sissy pussy. While you prance around in front of the mirror, stroke your clitty through your panties and wiggle your sissy slut ass, I want you to say "I am training My slut pussy for my new boyfriend" As you squirt your juice into your panties, say that you are cumming for HIM and that you are now his slut. Then slide your hand to your mouth and slurp up the cum.

As you get used to the aneros it will soon start to induse dry multiple girl orgasms, so girly. You will soon realize you can have mind blowing female orgasms with just your pussy alone. You can upgrade to your pink dildo and learn to ride it. As you use your toys, think of how you are preparing your pussy to be fucked hard! Think of how much you will be pleasing Men. And think of how far you have cum in your sissy sassy training. You must use an aneros or dildo whenever you play with your clittly from now on until you are ready to take a big cock.

Finger circling method may give you ruined, full or half-ruined orgasm. It depends for different guys. But it is only way you allowed to touch your clitty. If it will be ruined - it is your sissy destiny! Let me know how it works for you.
Though, you may play with your asspussy and nipples and cum from it (as good sissy) anytime you want.

You may fantasize about shemales instead of males as you asked. But you not allowed to watch straight or lesbian porn. Only shemale/sissy/gay videos for you.

I love you idea about scary sissy schedules where each time between orgasms is increased by 1 day. Let it be so. Also you must post detailed report about each of yours orgasms. Keep me informed about yours actions.

I prefer totally shaved girls.

Ok here is the plan.

Tonight I will try to make cummies from anal penetration only. No stimulation of my clitty in ANY way. I fact I will use an old trick of mine where I slip my floppy clitty into a glass jar the perfect size so that when my clitty gets hard and swell s my clitty acts as an air tight bung. This meanss whilst my clitty is hard I can not take the jar of because of the air vacuum. This had the delicious consequence of stopping me from being able to stimulate my clitty in any way whilst allowing free access to my sissy pussy. I will dress up and do ask the dirty sissy things described above. I will prance and pout and moan and wimper and beg for cock. Hopefully I will Cum from this. I will be watching lots of sissy shemale porn at the sane time. (any humiliating recommendations welcome) this will be difficult as I an so strongly attracted to females.

If I fail tonight I will try serendipitous suggestion of tuck and fuck. I have a dildo with realistic balls and I hope that I can tuck myself in such a way I bounce the balls of the dildo on my clitty tip to stimulate it. If with the sissy porn and the balls banging still doesn't work I will use my finger on my clitty like a girl. I know from experience this always can make me Cum but it always feels like a ruined orgasm to me.

The times when I can Cum have the danger of getting complicated but let me say that I an terrified and exciting about the the opportunity to try. I have not made cummies since Thursday. So by my calculations if I manage an anal cumming tonight I can Cum again on Saturday and the Friday after. If I fail tonight and have to wait untill tomorrow then my next chance to Cum will be Monday then the next Monday then a week and a day the Tuesday after. I quickly will be Cunmming just once out twice a month. Do I need a way to reset my counter some time in the future? Or wait untill I start getting desperate.

I will stay shaven but start decorating with pink glitter.and stars etc.

Anyone got a lifestyle dare not firstly connected to my cummirs but still VERY humiliating?

[vladimir_bz_lion]

I like your plan. Let me know how it went. Maybe you will can can to reset your timer with some dares, but it is to early to think about it, until you really desperate!

Of course, its not all just about the sex, you need to learn to be more girly generaly, this will only add to your Girly transformation, and turn you into a little girly girl minx.

Do you love dressing up and putting on makeup? Well you soon will even if u don't now! It's great for sissy girls to express themselves. This will help you come into your more girly girl side!!!!!!!!!!!!!!!!!!!!!!!!!

1.Substitute clumsiness and jerky movements with graceful and fluid actions. True "girly girls" sort of look like they're floating.

2.Groom yourself every day. A good grooming routine everyday, is taking a shower, and shaving. Apply body lotion. The last step is perfume. Pick a custom scent for yourself to be your trademark.

3.Look after your hair, get some cute pigtails and dye them pink for extra girly looks. (Private)

5.Take care of your nails as well. Treat yourself to a pedicure/manicure. If this is your first time being a girly-girl-in-training, try not to use dark colors like black. Use girly colors like pink, purple, etc. (Paint your toenails at least. Post pics)

6.Use mostly pastel colors such as pink and baby blue. Especially pink. Purple is a very pretty color as well. However, you can still wear, red, green, black, etc. Just because you're a girly girl doesn't mean you have to wear pink or purple all the time.

8.Get girly clothes - skirts, cute shirts, accessories, jeans, cute shorts...anything bright is good. Wear only female clothes at home.

9.Keep a diary. Draw girly stuff in it, like hearts, other cartoon characters, flowers and write poems and stories and so on. (Start your sissy online diary blog).

10.Use only female perfume, deodorant, shampoo etc.

Ok you got the look yet??

[obedience_247]

report on trying to make sissy cummies last night.


So last night I tried to orgasm. I followed all the dares/rules I have established in this thread. I dressed up on the prettiest girliest clothes I own. I wore silk pink panties a tight black mini skirt with fish net stockings. I wore a white lave bra witty pink bows and extra ruffles. I had a soft white silk blouse and write a blonde wig with pig tails made with more pink ribbons. I then spent 30 min trying lots of makeup on. Some shocking street whore styles. other soft subtle methods. All this girlie preparation with lashes of sweet perfume got
my sissy clitty all stiff. I felt so dirty and naughty dressing up like a girl. this was a problem as I wasn't meant to stimulate my clit at all this evening. My plan was to keep my clitty in a glass jar to block all stim for the.full night. But to fit it in I needed to go soft. To make my clitty small I got some ice and put it on my penis. Once I was tiny and small I slide my limp clitty into the jar and returned to the mirror. I started to flirt with my self to get more humiliated and therefore more turned on. I think I looked ridiculous. Silly and sissy and disgusting. A complete sex crazed sissy whore. my clitty still swelled up and the jar was stuck, I was unable to take it off until I made cummies or lost my clitty stiffy.

After prancing around my room for a while doing lots of suggestive possess I got out my dildo. I climbed onto my bed and started a shemale montage on my computer. I started by pretending to warm up the artificial cock with a hand job. Stroking up and down up and down and then giving a few loving tugs like I use to play with my clitty. But my clitty encased in glass was left un cared for. It was deliciously frustrating. then I got out some lube and started to coat my dildo lover in the soft silly liquid.

I then laid back and started my anal penetration. Like a good girl I moaned and wimpered and begged for cock. I tried to only think about men with cocks fucking me but I kept having images of beautiful women with strap ons doing me hard in the sissy pussy. I was so horny I kept changing positions and kept begging for harder fucking. More cock. I tried watching the shemale porn so I could focus on cock and tits but I just kept thinking of women and I then had a realisation. Not only was I dressed as a sissy with an untouchable clitty in a jar. Not only was I fucking myself hard in the bum. Not only was I forcing myself to focus on men who I am not attracted to whilst doing this. Not only all that but also I was doing everything because some stranger online told me to. I am that much of a submissive. I obey random people I have just meet and who may never talk to me again. I just
crave humation.

The next 2 hours of sissy pussy fucking passed in a blur. Humiliation. Moaning. Cocks. Porn. Degradation but NO ORGASM. I did not Cum last night so tonight I am scheduled to Cum.

Even though I messed up and thought about women with strap on s and not just cocks. Please can someone give me permission to make sissy cummies.

PS I found this image today and I got VERY turned on. Is this my fate?
http://xhamster.com/photos/view/2078...73.html#imgTop

mi

[serendipitous]

Wow, fantastic report, sorry that you didn't manage to orgasm through penetration, did you try my tuck n fuck method? I think no cumming for you at all until you've mastered this, the pent up desire to cum will help.

[obedience_247]

Originally Posted by serendipitous

Wow, fantastic report, sorry that you didn't manage to orgasm through penetration, did you try my tuck n fuck method? I think no cumming for you at all until you've mastered this, the pent up desire to cum will help.

i am attempting the tuck and fuck method this evenings, just getting dressed up and looking at some sissy porn at the same time. If that is your rule for permission to cum tonight i will not touch my clitty with my fingers I will only stimulate my sissy clitty with the dildo as it bangs in and out of my sissy pussy. Last night I was attempting to cum according to vladimir_bz_lion desired method of anal only with no clitty stimulation of any kind. I knew it was unlikely to work but i loved the humiliation of trying.

Im finding it hard to only think about cocks and only watch gay/shemale or sissy porn. i keep accidentally finding female pussies. For example i was looking at some sissy rule captions and found this http://xhamster.com/photos/view/2078...66.html#imgTop and now i feel like i have broken a rule about only watching gay/sissy/shemale porn. Is it ok if I accidentally stumble across female porn or should I be punished?

[serendipitous]

To be honest my fantasies generally run to femdom anyway, a cruel and beautiful Mistress who sissifies me and makes me worship her however she feels. My male genetalia doesn't belong to me, it's hers, and will never be used for anything but to pee again. I will worship her pussy because she knows it drives me wild with lust, but she will also make me worship her strap on with my mouth and bare my sissy pussy to her.

There's nothing wrong with fantasising about women with strap ons instead of men, it's what I do, the only time men enter my thoughts is if my mistress were to make me service them, and I would obey.

[obedience_247]

I have just written my very first sissy blog, it puts together all the sissy rules/dares i have now accepted. Some rules need a little clarification/tidying up but it is an impressive start to my life long sissyfication. one things it showed me was i need more sissy rules about when i am not at work but are not all about orgasms. How should a sissy behave when home but not attempting an orgasm. With my dare of increasing periods of denial most of my evenings will be relatively dare free compared to when i allowed an attempt at making cummies! anyone got a suggestion?

[obedience_247]

Originally Posted by serendipitous

To be honest my fantasies generally run to femdom anyway, a cruel and beautiful Mistress who sissifies me and makes me worship her however she feels. My male genetalia doesn't belong to me, it's hers, and will never be used for anything but to pee again. I will worship her pussy because she knows it drives me wild with lust, but she will also make me worship her strap on with my mouth and bare my sissy pussy to her.

There's nothing wrong with fantasising about women with strap ons instead of men, it's what I do, the only time men enter my thoughts is if my mistress were to make me service them, and I would obey.

But i have accecpted vladimir_bz_lion's dare that explicitty says "you not allowed to watch straight or lesbian porn. Only shemale/sissy/gay videos for you." I have accepted the dare so i want to try and follow it. I accepted the dare because I knew it would be difficult and humiliating and humiliation is my biggest turn on. So im going to try but I dont know if I should get a little punishment for accidentally seeing a delicious pussy