1 month challenge: Fate decides my Future
Over the month of August I have set myself a challenge, if I don’t get a date on Hinge then I will continue to sissify myself.
Background:
I’ve been a closeted sissy on/off for the past 9 years, I’m 25 (wow, just realised how long it has been) - this initially just started as jerking off in panties whilst watching sissy Hypno porn, nowadays it’s dildos, butt plugs, outfits etc but still never done anything in person.
I’m a virgin, I’ve had a few dates with women but have typically struggled with confidence. I’ve used hinge before but for the most part I just wait for someone to drop a like, have some small talk, and then usually fizzles out.
My challenge:
Over the month of August, I’ll be trying to get a date on Hinge - alongside this, I’m planning on fully sissifying myself with Hypnos, anal training, flat chastity etc. So, it will essentially it a time challenge to see if my future will be as a straight man or a sissy slut. If by the end of the month. I’ll soft give up on finding a girlfriend and admit that being a sissy is my destiny.
I understand that I’m not giving myself the best chance by sissifying myself during this month and my chances of being straight are already dwindling, but this is kind of like a closing of the door on being straight.
Sissy side:
I’m planning to stay in chastity for the full month - I’ve just ordered a new flat cage which I’m looking forward to trying!!! I’m spending most nights listening to hypno files, training my throat and pussy. Also, I want to get back into BambiSleep - maybe commit to the 20 day takeover plan.
Wish me luck (whatever side you’re rooting for haha) - feel free to pm or ask questions in the comments 💗
Posted Aug 4, 2026, 8:46 AM UTC