Dirtylittleboy35

1

I wish I could tell you I was disgusted with my actions. Honestly, it would have been much better if I’d had intense post-nut clarity and snapped out of it.

She doesn’t confide much in me since her Mother and I were divorced a few years ago, but she knew I’d always been deeply suspicious of that little loser. Blake. They went out for almost two years and I never once thought he was good enough for Chelsea. I was fucking thrilled when she dumped him. I just thought it was for any number of the obvious reasons: not a provider, weak, smarmy, know-it-all... well, I knew he was a beta of some kind, but I wouldn’t have expected... or really, I just didn’t know it was even a thing!

She told me I was right. Not only was he a loser who didn’t deserve her, he was something called a sissy baby. Apparently he begged Chelsea to enact scenes with him, change his diaper, dress him like a girl, even take other boyfriends and cuckold him. Thank god she up and left, and apparently she told him very clearly to go find a boyfriend instead of dragging her into any of that.

Well... that’s what first piqued my interest. I couldn’t help it. Imagining what Blake would look like if he was actually doing this. He wanted his diaper changed?? To be dominated?? Fuck. What an unlucky little shit. To be turned on by something so fucking... humiliating. I’d never even considered anything like that before. Then I couldn’t stop. I started researching it online and soon it was all I thought about. Worse than that. I was thinking about Blake. Was he doing this too? What name did he go by? Was he... was he on apps? Was there a way for me to find him?

I shot ropes of cum across the room when I came across his Grindr profile. I did feel just enough shame to not message him... until the next morning.

My little bit of research into the kink, combined with my actual knowing the little shit, let me wrap him around my finger. My only picture was a shirtless flexing pic of my tanned torso and arms I took for some lady I was fucking a year prior. I looked like any musuclar dad and I was very explictly told I was his type. He also answered my question: his sissy name was Becky. Fuck.

Upon my orders, soon he was texting me nearly all day, every day. Pictures of his diaper he was sleeping in overnight, the cage he was wearing, sneaking all of it in his childhood bedroom because he’d just gone through a bad breakup...

Playing the role of the Daddy, I suggested a meetup. I’d let him arrive at the hotel hours before me so he had time to get ready. I’d struggled to keep from masturbating for over a week... I wanted to save all of it for Becky. I told her to bring enough clothing for two days and tell whoever needed to know they’d see him on Sunday.

It was all I could do to not explode when I saw the little expression of shock, and horror, and clearly deep arousal as she saw me. Realized what was happening. And, to my delight, even while holding back some kind of panic attack, obey my orders and curtsey hello to her Daddy.

Well, I don’t know what my plan is here yet. But I know I’m far from done with Becky.

2

I should have run away. I should have slammed the door, ripped that ridiculous dress off, and relied on mutually assured destruction to make sure he’d never say a word. It didn’t really occur to me in the moment that he was just as fucked as I was if this got out. Maybe even worse than me. Chelsea already knew I was a sissy baby, she didn’t know her Father wanted to fuck them!

But I didn’t. I gasped and felt my stomach flip. My heart rate went through the roof. I was speechless. I’d never been so confused by what was panic and what was arousal in my life. So I didn’t do any of that. I squealed, I curtseyed, and I spent the next two days servicing my ex-future-Father-In-Law. He was the first man I’d ever been with. Sometimes while I tossed and turned, caged and diapered in my bed at my new 9pm bedtime (Daddy reasoned it was late enough that it wouldn’t arouse genuine confusion, but early enough it was another method of his control) I wondered if he might be the only man I ever end up with. Because he is showing zero signs of letting go. In fact, his control is basically ruining my life. What’s left of it.

After Chelsea and I broke up, I had to move back in with my Mom. Being in my childhood bedroom, after being dumped for being a sissy baby, it just... I couldn’t help myself, it became all I thought about. I was spending half my day on Tumblr indulging my worst sissy impulses... fantasies of all kinds of things, the loss of my independence, my dignity being ruined even further, the idea of obeying dominant older men. Imagine my joy when my usually dormant Grindr account blew up with one messaging me.

I have a hard time staying upset with him, because while the idea of using the knowledge he’d built up about me while I was trying to impress him and date his daughter to humiliate and sissify me is insanely fucked up, it makes me more turned on than anything possibly ever has.

Then came the most humiliating weekend of my life, locked in a hotel room having my diaper changed by him, sucking his cock, nodding along and agreeing fully as he outlined all the ways he’d always known I was a failure. Our pillow talk was him feeling my body up and fantasizing about all the ways he wanted to control me, how he couldn’t believe I wanted this, but since I did want it, he didn’t feel bad about giving it to me. I didn’t fully appreciate what that meant at the time. I thought maybe more hotel meetups, enough to keep him happy and satisfied… but no.

I didn’t realize how serious he was until Monday morning when I was sent a long and detailed list of rules he’d come up with. I would no longer be going in person into work. I would be diapered whenever circumstances allowed, meaning all day at my desk while my Mother was at work and every night while I slept. I would practice my makeup daily. I was to wear a chastity cage that he held the only key to. I would delete all dating apps, those where I was trying to date girls and where I was exploring my sissy side. I was his now. My weekends were his too, and our visits would go from Friday at 5 to Sunday morning, every week. I was to be shaved, made up, pigtailed, diapered, and obedient.

Today, it’s been six months. I look more like a sissy every day, as Daddy’s diet regimen has caused me to lose weight and his insistence I get some lip filler has left even my boy self looking like a sissy to those who could see the signs. My work from home requirement resulted in a major demotion, meaning I now spend most of my income on obeying Daddy’s rules, a dynamic he thoroughly enjoys. I dream as a sissy now, too, and I’m almost always wearing a diaper.