Sissy Cuck Humiliation
Good girl. Most sissies are just posers as soon as things get real, but the fact that your master owns you financially means you really are a weak little pansy through-and-through. How much money does he allow you to keep?

Thank you Sir, I’m flattered. Master wants me to handle my own bills and basic living expenses, but the extra money that I would have used for things like a new tv, playstation, movies all goes to him except for my sissy spending allowance. I think it’s very scary for a lot of sissies, which is understandable. But it is also one of the most effective ways to be truly owned and put in our place.

I’ve never actually been with a woman who genuinely enjoyed whipping others. Do they really exist?

I’ve never actually been with a woman who genuinely enjoyed whipping others. Do they really exist?

this Sir is not a cruel Sir so i'll leave that up to you, a damaged sissy useless sissy, but by the end of the week you should be able to keep it in for a minimum of two hours. and remember a picture every night with a date sign to show your keeping your promise
Anonymous

Yes Sir, thank you for your patience. I need to sincerely apologize - an unexpected situation with my work has arisen this week, so I will have to delay my punishment until next week.

it's Sir sissy, now don't forget your plug.
Anonymous

Yes Sir. My apologies. Thank you for your patience. How long should I be plugged each night Sir? 

the next instalment of the master story must be ready by now? if not then i think as punishment you should lock yourself away in chastity for one week and wear your largest butt plug every night for a week at he same time
Anonymous

Sad confession: I am unable to find a chastity device that I am big enough for. I just slip out of them. I read somewhere that inverted velcro wrapped and locked tightly around flaccid penis makes erections painful and nearly impossible, so I may experiment with that. I will keep you posted, Sir or Miss. 

Wow

My sissy balls are sore today. Walking a little funny.

What a good sissy you are becoming! Knowing your place: "a sissy’s place is earning money for her owner" "incredibly submissive and weak" Being polite: "Thank you. *curtsies*" And now licking up your "little cum messes"! I hope you get some pretty lingerie for Christmas, or maybe a festive red or green buttplug!
Anonymous

Thank you Sir or Miss. *blushes*

It’s hard to see much here, but just to prove that I licked up my little cum mess from the floor, here’s a little clip.

I finally came to the unfortunate conclusion that I couldn’t cum from the really soft swats, so I started to give myself real blows that hurt and finally was able to cum. I don’t know if you can hear it, but my balls were so sore at this point that I was starting to cry a little bit, but I kept going. 

The orgasm was sort of partial and not satisfying at all. I’m still really horny right now, but my balls are aching. I’ll have to go to bed a horny little sissy with very sore nuts.

I was so horny and frustrated after the first round that I decided to try again. This was all after having given myself a true spanking with much harder swats that really hurt. A few in this set did hurt quite a bit, but I just couldn’t cum.