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Old 11-08-2017, 12:43 AM   #1
check123
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Default New to chastity - Help!! or make it worse

I have been locked up in a chastity cage for the first time and am already going crazy after three days.

Some tasks were given to me which I have completed and will report on shortly.

I have been dared to create a thread to perform more requests.

Standard household items which can be included as well as a butt plug which I have never used before as I am new to all of this.
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Old 11-08-2017, 12:55 AM   #2
ebsia
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Well lets start with plugging that ass. The first 2 days, keep it in for 2 hours (only taking it out if you cant take the plug any more). The third and fourth day, increase it to 4 hours. The fifth and the sixth day 8 hours and the from the seventh day forward keep it in 16 hours a day (or the moment you wake up, put it in and the moment you go to bed take it out).

If you follow this, within a week, your ass will be nicely stretched
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Old 11-08-2017, 01:20 AM   #3
check123
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You have given the gf the biggest evil grin with that. Wow ok its in and has started. Having never had anything in my ass before it is very different!

As promised another one of the tasks given was to take a shower somewhere in public wearing white underwear so they go see through showing off the cage. The rules were that i was not allowed to cover up but could choose any time as long as the sun was up.

I figured places like swimming pools would be too busy even near closing time so decided to go to a beach shower where people rinse off. Just before the sun went down was my best chance of not being seen so I went there and sat in the car for 10 minutes feeling very nervous. Since the coast was clear the whole time I went for it before someone came past. Running off to the shower i stayed there for what felt like an hour but was probably 2 minutes before running back to the safety of the car.
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Likes: Hidden public, pain, piss, humiliation, alcohol dares, pain, body writing, feminization, anal, toilet slave, bondage

Maybe (never tried): CEI, cum walks

Dislikes (punishments only): heavy pain, tabasco sauce

Limits: Photos or cam, social suicide, permanent, scat

Toys: handcuffs, gag, small plug, large plug, beads, vibrating prostate toy, medium vibrating toy, chastity cage, clover clamps
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Old 11-08-2017, 01:35 AM   #4
ebsia
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Quote:
Originally Posted by check123 View Post
You have given the gf the biggest evil grin with that. Wow ok its in and has started. Having never had anything in my ass before it is very different!
Im happy to hear that (devil)

Also, what do you think about crossdressing?
Because if you are OK, with the idea, maybe its fun to also wear panties in the same manner (1st and 2nd day: 2 hours, 3th and 4th: 4 hours, 5th and 6th: 8 hours, 7th and 8th: 16 hours and from 9th day: 24 hours a day). Maybe your GF borrow you some (if aproximately the same size) but even better, buy some. The dont have to be flashy or slutty or whatever, as long as it clear that they arent ment for guys its fine. I would suggest 2 normal panties and 1 thong to start of with
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Old 11-08-2017, 02:06 AM   #5
check123
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I've never been into it and have never tried it. We did say before starting we would be open to trying new things. I just happened to lose this round. Can't wait for payback.

While I could squeeze into her panties she loved the extra humiliation of making me buy some by myself. Thought I could have got away with saying they weren't for me if someone asked but was told that wasn't allowed.

Tomorrow's shopping trip will include 1 normal and 1 thong. This will be an interesting experience
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21/m/switch

Likes: Hidden public, pain, piss, humiliation, alcohol dares, pain, body writing, feminization, anal, toilet slave, bondage

Maybe (never tried): CEI, cum walks

Dislikes (punishments only): heavy pain, tabasco sauce

Limits: Photos or cam, social suicide, permanent, scat

Toys: handcuffs, gag, small plug, large plug, beads, vibrating prostate toy, medium vibrating toy, chastity cage, clover clamps
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Old 11-08-2017, 02:16 AM   #6
ebsia
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Quote:
Originally Posted by check123 View Post
I've never been into it and have never tried it. We did say before starting we would be open to trying new things. I just happened to lose this round. Can't wait for payback.

While I could squeeze into her panties she loved the extra humiliation of making me buy some by myself. Thought I could have got away with saying they weren't for me if someone asked but was told that wasn't allowed.

Tomorrow's shopping trip will include 1 normal and 1 thong. This will be an interesting experience
To make this trip even more exciting, wear your buttplug doing it. It might add some fun humiliation

Also, when you bought them, make a picture of them and upload it. This way you do not pussy out.

Last edited by ebsia; 11-08-2017 at 02:33 AM.
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Old 11-08-2017, 08:29 PM   #7
check123
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After trying a butt plug for the first time ever yesterday I couldnt bring myself to wearing it out just yet. I did find out that it was a vibrating version and on the lowest level it made my entire body shake before cumming in the cage in minutes. Cant imagine what the other levels will do.

The shopping experience was so humiliating. I went into the store and found the lingerie section and picked two out as quickly as possible before rushing to the front. The lady took forever to scan them in and then it happened. The security alarm went off as I exited the store!!! Luckily I was waived through because didnt want to explain what was bought.

Picture proof here https://imgur.com/a/BJfrX
__________________
21/m/switch

Likes: Hidden public, pain, piss, humiliation, alcohol dares, pain, body writing, feminization, anal, toilet slave, bondage

Maybe (never tried): CEI, cum walks

Dislikes (punishments only): heavy pain, tabasco sauce

Limits: Photos or cam, social suicide, permanent, scat

Toys: handcuffs, gag, small plug, large plug, beads, vibrating prostate toy, medium vibrating toy, chastity cage, clover clamps
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Old 11-09-2017, 12:39 PM   #8
ebsia
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Quote:
Originally Posted by check123 View Post
After trying a butt plug for the first time ever yesterday I couldnt bring myself to wearing it out just yet. I did find out that it was a vibrating version and on the lowest level it made my entire body shake before cumming in the cage in minutes. Cant imagine what the other levels will do.

The shopping experience was so humiliating. I went into the store and found the lingerie section and picked two out as quickly as possible before rushing to the front. The lady took forever to scan them in and then it happened. The security alarm went off as I exited the store!!! Luckily I was waived through because didnt want to explain what was bought.

Picture proof here https://imgur.com/a/BJfrX

That sounds like a fun trip (devil)

Question: How long are you planning to stay in chastity and keep to the bet?
This way we might add some more fun stipulations, in the future (I think wearing plug and panties might be enough humiliation for the first week).

BTW: next time you make a picture of something, it might be handy to put a piece of paper with your GetDare name on it. Then nobody will doubt you ever

Last edited by ebsia; 11-09-2017 at 12:51 PM.
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Old 11-09-2017, 05:51 PM   #9
check123
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Quote:
Originally Posted by ebsia View Post
Question: How long are you planning to stay in chastity and keep to the bet?
This way we might add some more fun stipulations, in the future (I think wearing plug and panties might be enough humiliation for the first week).
I'm locked up until the end of this weekend


Quote:
Originally Posted by ebsia View Post
BTW: next time you make a picture of something, it might be handy to put a piece of paper with your GetDare name on it. Then nobody will doubt you ever
Good point. Will keep that in mind
__________________
21/m/switch

Likes: Hidden public, pain, piss, humiliation, alcohol dares, pain, body writing, feminization, anal, toilet slave, bondage

Maybe (never tried): CEI, cum walks

Dislikes (punishments only): heavy pain, tabasco sauce

Limits: Photos or cam, social suicide, permanent, scat

Toys: handcuffs, gag, small plug, large plug, beads, vibrating prostate toy, medium vibrating toy, chastity cage, clover clamps
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