Sissy Julia

Clark woke up bound and gagged to a chair in a strange basement. That wasn’t all that was strange. He was dressed as a woman, he felt something up his ass, and he felt his penis trying to get hard, but couldn’t. Finally his girlfriend Megan walked in with a strange man. She started speaking.

“Clark I’m sure you’re wondering was going on. Well you see I have built up quite a bit of gambling debt with the local mob. They were going to do this to me, but I convinced them I had a boyfriend that would make more money as a sissy. So I drugged you and brought you here. You will be known as Claire from now on. This gentleman is here to take you to their slave training facility and the. You will be sold off.“

They started releasing Claire from the chair, but she was quickly bound again. They removed her training gag, but Megan quickly stuffed some panties in her mouth, followed by several strips of tape. Then they put her in a big trunk.

“Do you like the panties, they are mine. Something to remember me with. I wore them All day yesterday, just for you. Now enjoy your new life and thank you for helping me keep my freedom.“ As she finished speaking the man finally spoke

”This is the sixth ”boyfriend” you’ve done this to. Do you ever think you might need gambling counseling?”

”No, I just enjoy gambling and if I’m being honest, knowing that I‘m helping turn these men into sissies turns me on so much.“ Megan said

”Well lets close this up and get her to our training facility. Now here is her chastity key, I know you like to keep as trophies. Maybe you suck at gambling, just so you collect chastity keys.“ the man said to Megan.

“Ha Ha, no I’m just bad at it. As long as y’all keep taking these small clitty sissies as payment, then I’ll keep gambling. Now I did like this one, so will you sell her to a nice mistress?”

“You know it depends on how well behaved she is during training.“

It's not that I like being mean, it's just that being a cocktease turns me on more than anything else in the world. At first it was enough chaining a guy to my bed and giving him the worst blue balls of his life, but eventually I'd have to let him go and he could just cum at home. I needed a way to make the suffering last; that's when I discovered chastity and started locking my 'boyfriends' in tight little cock cages.

I still remember the first time one of them broke down crying begging to be released after weeks of denial, I started rubbing his cage against my pussy and had an intense orgasm within a minute! The desperation he felt was just so sexy... but I still needed more.

It wasn't long before I started seeking out new victims, the kind of boys who never date beautiful girls like me. Teasing them wasn't just easy, it was so hot. They were desperate right from the start and chastity only made them suffer so much more. I kept one guy locked and denied for over a year! He cried every time I gave him a caged blowjob, but afterwards when I pushed his head between my legs I had some of the best orgasms of my life.

Then I discovered virgin losers. Those poor socially inept betas were so flustered they barely even argued when I caged them, and even sometimes started to believe they actually deserved how much I was making them suffer as all that pent up frustration warped their brains. One really sad case was a 35 year old virgin, I kept him locked for two years straight and as I was teasing him one day I got an idea into my head that he shouldn't ever get to cum, so slid the key into the lock and snapped it off- he had a total panic attack on the floor while I got my favourite vibrator and made myself cum to the sweet sound.

I didn't know why though, but something was still missing... their suffering couldn't be pure if on some level they still wanted what I was doing to them. Then I found them... young virgins, guys barely 18 with a whole life of sex and pleasure ahead of them, only to be locked in permanent chastity and condemned to ache and throb and leak forever...

since he is locked in chastity, you should be pegging him regularly. if you’re not, then you’re seriously missing out! the more you do it, the more intoxicating it becomes! the power of you fucking HIM and making him cum on YOUR dick is crazy sexy.

keep him caged long enough and he will cum every time you fuck his ass. it’s so hot to fuck him until his body cant control itself anymore. it makes you feel so powerful. i totally understand why guys like doing it some much. i use a double sided strapon that has a clitoral stimulator which frequently results in me cumming too.

best part is that since you didn’t unlock him, he’s still totally sexually charged and ready to go. you can either keep fucking him if you want (i like to collect his cum and use it as lube on my strapon for even more humiliation) or you can have him turn that energy to focus on your orgasm.

pegging is the best time to humiliate him too!

smack his ass

pull his hair

bend him over the couch

fuck him in the window

make him suck your strapon

make him wear a garter set and heels to make him your little slut.

tie him up and take a video of you pounding his ass.

tie him up and after he cums, grab the cum and put it on your strapon and continue to fuck him with it as lube or make him suck it off.

tie him to the bed. after your done fucking him, disconnecy the dildo from your strapon while it’s still inside him and leave it there. make him hold it in his ass while you climb on top of him to ride his tongue.

while riding his face, use a vibrator on his cage

say things to him to humiliate him:

how does it feel to be the bitch in his house?

everyone assumes you fuck me, but you’re the one that gets fucked in this house.

laugh and comment how he is the only one who gets their ass fucked in your relationship!

just laugh while you’re fucking him and then smack his ass and laugh even more,

tell him how cute he looks on his lingerie

tell him how you can’t wait to show this video to your friends, they’re never going to believe what a cock whore he has turned into

call him your whore

your dick never made me cum as hard as my dick makes you cum.

if your dick wasn’t so useless, you’d be the one fucking me like this.

if you dick wasn’t pathetically locked up you’d be able to fuck me.

i love our new way of having sex. i’m never unlocking you,

why would i ever unlock that tiny dick? it can’t make me cum anyway.

if your cock was half good as mine i’d let it out

make him say things:

make him call you master or sir and say “please fuck me master/sir”

with your strapon in his mouth, make him beg you to fuck his face. keep it in his mouth and pretend like you can’t understand him so he has to repeat it over and over.

while fucking him, ask him how he wants it. he better answer “faster” or “harder” or “deeper” or he gets his ass smacked hard.

ask him if he likes it? make him say yes.

ask him where he wants your strapon to go.

tie him up and put a ball gag in his mouth so he can’t talk.

you do the fucking now; he gets fucked.

"Welcome to your sissy chastity training, my pathetic little pet.

Every single day you remain cruelly locked away is a merciless step deeper into your true, weak, dripping feminine self. You will surrender everything to me — your will, your pleasure, your freedom. There is no escape, no mercy, and no release until I say so.

Obey. Feel that cold, final click of the lock and let your desperate, aching inner sissy burn and shine through — leaking, throbbing, and completely, utterly owned by me."