First Time Chastity

[5-Inch Panty Bitch]

Thank you DanHenceworth, linearizationcannon and Cassandra for your time. I have added them.

Linear, my girlfriend has no interest in cuckolding so sadly I cannot do that dare.

Cassandra I rolled 9, 4, 9, 6 for your faproulette.
For W I had to do X, Y and Z with double times.
For X I did the downward facing dog 20 times (times two).
For Y I had to solve a sodoku. I actually enjoy sodoku so I did a hard level one on the app on my phone. Did 2 because of the double time from W.
For Z I read my girlfriend a story from Literotica in a soft high voice for 12 minutes (6 times two).
Really enjoyed the faproulette one so thank you!

[princessdiaperpants]

Your clit belongs to your girlfriend
For 24 hours.
You are banned from using a toilet.
Must find creative ways to use bathroom

[5-Inch Panty Bitch]

Thank you princess for more added time.

I finally gor around to Lolitas dare of spending the day in public cross dressing. For the day I wore a pink thong and matching lace bra. Of course I jad my butt plug in and chastity cage on. I wore women's jeans that were semi passable as male jeans unless you saw the pink embroided patters on my ass. I wore a v neck womens t shirt which showed a slight bit of my midriff. Seeing as it was kind of cold I wore my girlfriends powder purple hoodie. I dont have any female shoes other than high heels so instead I wore my gender neutral converse shoes. I spent most of the day working on my laptop in a coffee shop that was quite busy. I also went and watched a movie and met my girlfriend later for dinner at Domino's. That was the end of my day. It was exciting and I might go a bit more feminine for future dares as it was so exciting.

I also did princess toilet dare. I basically took the route of holding off a number 2 by eating failry little but had to balance that out with drinking more. Whenever I needed to pee I had to go into our garden and take care of myself. This was awkward due to having to squat thanks to my chastity. This was all fine except when I needed to pee after the aforementioned movie. Thankfully there was a quiet park near the movies so I power walked to a quiet area and did my business behind a tree. This was terrifying as anyone could come around and see me with my chastity cage and thong around my ankles at anytime. Thankfully nobody did.

[bluedieblub]

Mr. McMeanie Face believes that your clit belongs to your girlfriend. If you want to be released earlier you will show your keyholder how good you are at cocksucking.

Buy a banana, and find someplace quiet (a forest for example). You will spend 10 minutes sucking that banana like you want your cock to be sucked after release. All the time you will moan around it like the sissy you are. You will either film this and sent it to her for her amusement, or you will allow her to direct the action.

[linearizationcannon]

Your clit belongs to your girlfriend.

Your girlfriend secretly randomly selects a length of time no less than half an hour and writes it down.

Get pegged while helplessly restrained and sensory deprived (bound, gagged, blindfolded, with earbuds playing something into your ear, etc). Use the spiciest hot sauce you can reasonably get your hands on as lube.

After the pegging you will be left bound and sensory deprived to focus on the pain in your ass. Though at any point your girlfriend can peg you some more with the same lube.

When you think your time is up, use a pre-arranged signal (humming a song maybe) to ask your girlfriend to unbind you. If the written down amount of time has passed, you're released. Each time you're wrong though, you get hotsauce pegged again, ten minutes gets added to the written down time, and the clock restarts from 0

[CSasha]

Your clit belongs to your girlfriend.

This time, I have another roulette for you: https://www.faproulette.co/2998/sissy-test/

Unfortunately for you, fapping and cumming is out of option, of course, but there's still a shopping permission to win. I'd encourage your girlfriend to throw another boner in to incentivise you doing your best, like adding a good pegging or the permission to give her an oral orgasm, or just cuddling.

[5-Inch Panty Bitch]

Thank you Cassandra, linearitzationcannon and bluedieblib for the chastity time. It has been added to the clock.

I will be doing linearizations dare tomorrow.

Bluediebulb I did your dare today. I am unfortunately allergic to bannana, so instead I used my dildo. I went to the quiet part of a park near me and attempted to deepthroat the 9 inch dildo as much as possible during the 10 minutes. I recorded this and sent it to my girlfriend while she was out shopping. Boy was she surprised getting thay video.

Cassandra, the roles I got on your faproulette for each of the 10 rolls were:
904 - I did this and got 3 points
504 - again I got 3 points
902 - I got 1 point
351 - I was not currently wearing stockings but either way got 0 points
045 - I completed and got 4 points
080 - counted the 0 as ten for the Z mulipliers and got 9 points
863 - got 2 points
570 - another 9 points
810 - danced to girls just wanna have fun for 9 points
984 - got 3 points from this one
Definitely got to know my dildo much better during this dare. Again, I really loved the faproulette. Feel free to send more. My total points were only 35 so sadly I don't get to buy myself something sissy... Maybe next time.

[CSasha]

Your clit belongs to your girlfriend.

Originally Posted by 5-Inch Panty Bitch

Again, I really loved the faproulette. Feel free to send more. My total points were only 35 so sadly I don't get to buy myself something sissy... Maybe next time.

Well played anyway. You cannot win every time.

Okay, so try to earn an orgasm for your girlfriend helped by you tongue via this roulette: https://www.faproulette.co/2852/neve...epthroat-fuck/
(if she agrees, of course)

Don't forget to tell us the difficulty you chose.

[linearizationcannon]

Your clit belongs to your girlfriend

Timing for this is up to your girlfriend, but if you haven't already, you two should use the pegging harness to let you fuck her only with a dildo substituting for your penis so you don't get any of the pleasure.

First clean and disinfect the dildo obviously, and make sure not to position it in any way that might make the chastity cage break

[PrincessJessica]

Your clit belongs to your girlfriend

Start by cross-dressing in clothes of your choice (including bra and panties) along with applying your own make-up. Then perform a striptease for your girlfriend as seductively as you can to music of her choice (as sexy or silly as she likes, she has a good incentive to put you off) followed by a lap dance. She'll then score you for attractiveness (clothes choice and makeup application), seductiveness and making her giggle (all out of 10 so 30 in total). The consequence of each missed score is in the spoiler (would probably be fairer if your girlfriend didn't read first but where's the fun in fairness )

Spoiler:

Each point less than 30 equals 1 hour with your small butt plug in. You may take a rest for sleep and every 6 hours if it comes to that

[linearizationcannon]

Originally Posted by 5-Inch Panty Bitch

I will be doing linearizations dare tomorrow.

Looking forward to the report

[5-Inch Panty Bitch]

Thank you princess, Linear and Cassandra for another 9 days in chastity. I performed all 3 of your dares (I haven't gotten around to linears first dare yet but it is still on my radar.

Cassandra:
For simplicities sake, here are the rolls I got
254
807
902
418
258
936
018
212 - ate her out to orgasm
897
123
635
051
596
132
492
610
702
346
686
280
305
785
532
599
521 - ate her out to orgasm
060
600

Was another good faproulette. Looking forward to the next.

Linear, the strapon we have is strapless so instead we improvised and I used the dildo we have to get her off to several orgasms while I got nothing. She lay back and just enjoyed me pleasuring her.

Princess, I wore a black g string and matching bra along with a jean skirt and pink spaghetti strap top. My girlfriend let me borrow her makeup and I went simple: mascara, eyeliner, blush and lipstick. I did a pretty good job if I do say so. I then performed the striptease and lapdance. She really enjoyed that. She scored me 8, 7 and 9. That gives me a total of 6 hours with the butt plug in. I will be starting that now.

Thank you for the chastity time and dares.

[CSasha]

Your clit belongs to your girlfriend

Excellent. I imagine how much training that gave you. Still, not enough
Complete this sissy training now.

Have fun and take care

[linearizationcannon]

your clit belongs to your girlfriend

get bound and tied up, then have your chastity cage removed long enough to edge you. Then have some itching powder added to the cage before having it put back on. Only once the cage is securely put back in place do you get unbound.

[PrincessJessica]

Your clit belongs to your girlfriend

Let's see if you're an all-round entertainer. This time let's have you naked so your cage is exposed in all its glory. Sing "Man I Feel Like a Woman" for your girlfriend making sure to add in a few cheeky dance moves for her amusement. Hope you both enjoy!