The Sissy Chastity Diary

Day 1

I was just so tired of the sissy cycle of excitement, shame, then purging. Writhing and moaning and stroking my cock, cum would seep out of me as my mind then rebooted. In front of me: captions, hypno, femdom telling me I'm not a real man, how much I need to suck cock, how being girly was my purpose in life. What had moments before brought my arousal to new heights now made me feel a deep well of shame, and disgust. Something had to change. In a moment of severe horniness, I ordered a chastity cage.

Putting it on was really exciting. Too exciting. I kept getting hard at just the thought as I tried to put the pieces on myself. This led me to some of the more naughty kinds of sissy porn to make myself cum and then, shamefully, putting the cage back over my penis.

Day 4

Fuck. Playing with my tight little hole really is so much better locked up. Every sensation is heightened. My nipples harden, my cage tightens, I moan like a slut. I can't believe it's taken me to the age of 22 to try this!

Day 7

Still haven't been able to cum though.

Browsing through femboys on reddit. I wish I could look half as cute as some of them, or hold hands as we lie in bed next to each other stroking our dicks. Just a thought.

Day 8

I can't find the key! I'm freaking out. I've looked everywhere and anywhere but I just can't figure out where I left it. Berating myself, wondering if those bimbo hypnos are having some kind of effect even though I know they can't. I just feel so stupid. And horny. Too anxious and panicked to even touch myself.

Day 9

Channeling all of my anxiety into increasingly desperate sissy porn. I hump my panty-encased cage as I watch the dirtiest, sluttiest sissy hypno. It's just one of the only ways I can relax, not normally stuff I go that deep into...

Day 10

Slowly beginning to freak out even more. Looking for my key all over my apartment, I honestly can't think of a place I haven't looked. If I can't find it, I might have to consider going to the doctor. God, why! Getting scared. Would I rather it be a guy or a girl? I'm not sure. Any woman who saw me in my cage, with my petite frame would think I was some kind of femboy Twink. That I submit to other men, and call them daddy and other crazy stuff. The thought makes me shiver. She wouldn't see me as a man...But, on the other hand, if it was a male doctor...he'd probably have to touch my cock, even if it were with tools. He'd give me a knowing smirk as he helped me out of the cage. He might call in a female nurse, her in the room while my cock is caged and his...isn't...ugh.

I'd feel so small and vulnerable, I'd want to disappear. And what if they think my cock is small?I need to find the key.

Day 14

God I need to cum. I need to cum so bad. I've never gone this long without an orgasm. The slightest breeze makes my cage tighten. I'm starting to notice that my nipples get harder when I'm erect. My whole body seems to be tightening--my skin just another cage holding in my orgasm...To distract myself, I've been taking cold showers and shaving my legs. I love rubbing them together and taking photos of my cage with them in the background. Super girly!

Day 17

Lost almost 5 pounds since the beginning of my "experiment". Maybe it's all the failed attempts to make myself cum with my ass...

Day 21

Peeling my panties off of my sticky cage (I'm always leaking now), a hand absent mindedly gathers some of my wetness onto my fingers. I tenderly rub my tip's hole, gathering even more. The sensation sends chills up my spine and butt; my thighs jiggle. I'm not even thinking but I'm scooping cum into my lips, onto my mouth, and into my tiny body. The taste makes me so horny. I slurp up more and more as my mind drifts, my body acting of its own accord.

Day 26

I've started riding my dildo as I watch sissy hypno and femdom joi videos. Having to seek out ever more desperate distractions from my predicament, all of which eventually just make me all the more desperate. I'm on edge. Will my little thing even get hard once I finally get this thing off? Am I causing irreversible damage to my manhood? Am I losing length? I can't handle being any smaller.

Day 29

I keep waking up from my dick trying to get hard inside of the cage. Maybe it doesn't help that I'm sleeping in panties every night now but that just feels more comfortable for the time being. Last night, I got so frustrated at not being able to sleep that I humped my pillow until I collapsed, exhausted, unable to cum but finally able to sleep.

Day 36

Well, I hit a new low I think. Bouncing back and forth on a dildo in the shower, femdom porn telling me how much I love and need cock, taking it into my pussy over and over until I have to stop as my legs shake uncontrollably. I don't actually want cock, and I think that's what turns me on so much. The idea of a hot woman telling me I need something so against my nature--just writing that out gives me chills.

So far, I've been able to resist the temptation of eating my precum again, my leaky, sticky reminder that I haven't cum in way too long.

Day 37

Again, so horny I can't think straight. This one sissy video made me feel like I was as close as I've ever been since locking myself up. The female speaker tells me to repeat her words back while the biggest cocks I've ever seen appear hazily behind her. Words like:

"I must submit."

"I live for others' pleasure."

"I am a sissy."

"Women, AND men, are superior to me."

"My sexuality is: cock."

Of course, I'd never do anything with a real cock. But, obeying in this way as I rub my panties against my cage makes me feel like my whole body is about to explode. Only - it doesn't. I feel... so sexual all the time, but, I just can't do anything (besides teasing myself further about it).

Day 39

A strange dream the other night: an older, mid 30s man combing my long hair, telling me how pretty I am. He begins to pull the hair away from my neck with his broad hands, I can feel his breath on my neck - I wake up. The fan spinning fast above my bed. My panties are soaking wet. Clit-drool making my smooth little balls sticky against my thighs.

Day 46

I thought it might be fun to tease some men online and see how well my femininity could attract real men. My Grindr account was simple. A picture of my painted lips; one of my ass in panties, one of my cage, and another of my lithe, petite, smooth body. My phone was instantly blowing up. I couldn't stop shaking. Men were sending me pictures of how hard I was making them. The cocks kinda grossed me out, but seeing how rigid...and veiny I had made them was intoxicatingly new. My cage was soooo tight.

"Hey baby"

"Cutie"

"Sexy"

"Slut"

My hardening nipples tingled at my touch as I read the stream of words directed at me - at my body...I had never gotten so much positive attention.

Day 47

Another dream that's hard to believe came from my own mind. I'm sitting in a dark theater, holding hands with an older man. His strong hand stops enveloping my dainty one and begins to snake its way up my smooth thigh, under my skirt. He begins to rub me in my panties as I try to stay quiet and stop from squirming. But it feels so GOOD. His other hand starts to play and tease my hardening nipples. I feel my mouth open and I wake up as I moan out loud. One hand on my panties, and the other on my chest.

Day 50

Oh god. I'm so fucked up.

I met up with a guy...

He promised to fuck me. I needed him to fuck me. To pump all my pent up horniness out of my body--getting afraid of what else I'd do if I don't cum soon--I know now, somehow, deep inside, that my ass, my pussy is my only chance to cum--to save myself from this spiral of insanity. Bouncing on dildos, rubbing my nipples, rubbing my clit, the most depraved and exciting sissy porn--I leak and I leak and I leak but I just...can't...cum.

I'm dressed up so often now, him asking me to didn't matter. Blue panties, black fishnet stockings.

He might've been 40. Almost twice my age. I knocked on the door of his hotel room and he immediately pulled me in and kissed me against the wall, grasping and pulling at my ass. This was too gay. I just needed something in my ass to make me cum. But his stubble gave me goosebumps.

His hand found its way to my cage inside my panties.

"What's this? Bit of a kinky girl for a virgin, no? Did you lock your little cock away?" he asked me.

He squeezed my balls and I moaned involuntarily.

"Not that I'm complaining of course."

I was shaking with nervousness. I needed to cum so badly. I begged him, like a whore, to fuck me, I couldn't hold back from telling him how much I needed release.

"I know what will relax you, baby, just suck on this, slowly at first." He was holding out his big cock. "It's time you felt up a real cock with those girly fingers and lips."

A little closer to being fucked, I readily gave in. Feeling him expand in my mouth as my hardness was thwarted was intoxicating. I couldn't understand. The panties caressed my hole, as the muscle memory of taking dildos while horny took over.

The taste of my lipgloss melded with his precum.

"Take my cock you little sissy slut. Fuuuuck I love girly boys like you. Slurping on my dick like your life depends on it." He goaded me.

Just a little longer and his cock was going to slide into my boi-pussy, fuck me, and make me finally cum. I'd have release. His heavy balls slapping against my caged little marbles. I could see it. His dick sliding in and out of my slippery lips, but my head was already steps ahead. Suddenly--he was gripping my head tight. Stifled moans barely meant anything to him as he fucked my mouth like a pussy. He growled, hardened to his peak, and released his cum into my closed mouth. "Mmmm," "mmmph" I moaned in alarm. I choked and coughed with all the cum and saliva built up.

"Wha?" I said. He practically kicked me out after. Men suck.

I can still taste the salty flesh of his dick in my mouth; can feel the sensation of being used. My cage tightens, my mouth opens, my mind wanders. I'm not sure what's happening to me...

Day 54

I love cocks. I love feeling their warm veins caress my slutty tongue. I'm a slut for men, real men with big cocks. The thought of a strong man holding my pale, delicate, little body makes me feel intoxicatingly girly.

Day 56

He fucking ghosted me. I feel like I understand women's feelings towards men a lot more now. I sucked his cock and he ghosted me...I just need a cock. I just need a cock to make me cum. It's just what I need, not who I am. I wanted that cock...the one that was so much more than mine to take my virginity. That idiot! If only he knew--then he would fuck me, he would have fucked me so good...

I rub my caged little thing inside my panties while I think about him, his big cock. It was so much more than mine in every way. Like all my life I had only been playing with a toy, and here was the real thing. It filled up my mouth so easily. His complete mastery over my body, the unexpected taste of his salty cum; I relive the experience again and again. It's the closest I can feel myself to getting release, but it's just not enough.

Day 58

Been so insecure lately. The photos of myself in lingerie I post online get some nice attention but somehow it's not enough. Am I not feminine enough? I put a man's dick in my mouth, trying to get him to fuck me, and he ghosted me. Why?

Day 63

After meeting up with that guy...and being rejected, being ghosted, my taste in porn has gotten more embarrassing, more degrading. Sissy hypno telling me I was born to be a sissy girl because of my little body...and little clit. It used to just be a fantasy, but now, I have a hard time not believing it...

I let a stranger use my mouth like a pussy. And I wanted more! And then they stopped talking to me...God!

I submitted so readily to be used for someone else's pleasure without even realizing that's what I was doing. And the more mortified I feel, the more I glide my painted nails across my smooth hips and thighs. The more I shake my ass in lingerie and post it on the internet. I worry I'm becoming the neediest of sluts and that it's all out of my control. It's like some foreign body has invaded my psyche making me more and more feminized as my body responds in unavoidable horror and delight.

Going to a doctor and having them just remove the cage would have been so much less humiliating, life-altering. Now, I drink up all of the clit-leakage I create. I can't get enough. I greedily slurp and swallow it all up in the morning when my panties are always wet. And then, when I'm bouncing on my dildo and leaking again, watching the naughtiest sissy hypno I can find, I suck every last drop into my pink lips.

Day 69

Using Grindr again. It makes my heart race. Showing all these nearby Alphas my little smooth body. I really like the way this one guy talks to me. Almost belittling? But I think I love it. He likes to compare our bodies; how his is so much better an example of a real man's body. It makes my skin tingle. But I'm afraid of being hurt again. I need to remind myself: it's not about the cock or the man. I just need to cum.

Day 74

I couldn't hold on any longer. I met up with him. I could tell he was a good bit older. I wore a plaid, girly schoolgirl skirt, white thigh high stockings, a simple black choker, a lacy white bra, and a cute pink crop top. My head came up to his chest. He ordered me to take off my cover-up boy clothes. Then, he ordered me to rest my cage on top of his already hard penis.

"How cute. That your little thing doesn't even go past those little marbles. Just rests there..."

His rigid cock head pressed upward against my wrinkling scrotum.

"How far does your little cock measure against mine?" He prodded.

"Mmmm. Just past the head, sir..." I muttered, humiliated.

"Your whole cock not even as big as my tip. Jesus. I don't think you should ever go back to pretending you're a man."

"What do you mean?" I was hurt.

"Your little clitty..." he stroked the cage with a finger "isn't meant for a pussy. Has it been inside one?"

"Well no...but--"

He shushed me with the same finger, a little of my own leakage brushing my lips. "Look down and tell me what you see." He tilted my head down.

His big engorged dick was far longer than my little thing, and even thicker, despite some help in size from the cage. My whole body was shaking. Having my imprisoned manhood held up by a big cock, hard because it wanted to fuck me.

"I see my caged clit and a...an actual cock..."

"That's right sweetie, you don't have a cock. And so, no woman is ever even gonna think about fucking you. It just wouldn't even be a possibility in her head. Does that make sense, honey?" He put his hand tenderly on my check.

"I--," I moved to protest and he merely shushed me with his finger. My head was spinning. I just needed him to fuck me already. Squeeze my cum out with his cock. I nodded hesitantly. I could sleep with my first woman after getting all these weeks and weeks of cum out of me. Why did I have to be demeaned for that to happen? But...my mind did keep darting towards all the most depraved porn I'd consumed since locking myself away. Was I born to be a sissy girl? Did I have a little clit women wouldn't consider a real cock? Was it possible to turn back after going this far in my feminization and experiences with men? I was beginning to get even more nervous than I already was.

He told me how obvious it was that I was a pent up bitch desperate to cum. He ordered me to repeat after him. Obediently: "I'm not a man, I'm a girl with a little clit and a pussy that needs real men" while spreading and playing with my lingerie-clad ass. It felt good to feel myself in front of someone but the words filled me with shame. I was a guy! I just needed to cum....how did this get so far.

He held me from behind as he pointed me at a mirror. "A straight boy doesn't shiver when a real man touches the cups of his bra. A girl...might get wet as the space between her ass cheeks is filled by a big cock." I looked down. My cage was leaking like crazy. I blushed. Forcefully, he turned me around, held my face, and kissed my lip glossed lips. I collapsed into his possession of my body. A chill ran down the nape of my neck to the top of my ass. I might have moaned like a completely submissive slut. But I'm not sure, I forgot all of my anxieties as he claimed me with a kiss. I could feel the warmth of his long cock against the chastity's hard exterior, reminding me that he was the man here.

He ended the kiss, but I leaned forward wantonly, wanting to return to that heavenly oblivion. His strong arms held me in place. I wanted to again be tilting my head up to meer his height, to feel his body overshadowing mine. I'd never had it before, but now, I needed it.

I hadn't even held a girl's hand yet and now...oh God. I just needed to cum and then I'd be released from this strange fever dream. I would be free, all I need is a real man's cock to hit that special spot deep inside of me and then I can go back to being a straight boy. Thinking about all the money I'd wasted on clothes I would never use again...

"Are you ready for me to make you into a woman, to make you cum like a girl?"

"Yessss" I urged. "It's all I want, sir."

"'Sir' isn't good enough. I'm your superior, everything your father wanted out of a son but didn't get, I'm your--"

"Daddy," I blushed, accidentally cutting him off.

"Actually" he cupped my cheek "I was going to say 'Master' but I think I like that better, dirty girl."

I swallowed. He continued to lovingly touch my cheek and tousle my hair.

"Now, tell me again what you need."

"I want--I need you to show me what it's like to be with a real man, Daddy. I can't cum like a boy anymore, I need you to fuck the cum out of me. It's been months. I can't remember who I used to be, or what I used to like. But, the only thing I haven't tried yet is being fucked by a real man with a lengthy, veiny cock." Each word made me feel filthier than the last. And more nervously excited.

"Jesus," he blanched. "A+ but you are one desperate little whore. Now that you've gotten all wet," he was coating his cock in my leakage, rubbing it against my smooth thighs and sensitive cage. "I can take your virginity with some natural lube."

He then pulled me over to his couch and made me bend over, my knees propped up on the cushions.

"Oh my god, oh my god." I whispered into the pillows as he lifted up my skirt and pulled my panties to the side. There was a slight sticky resistance from all the precum leaking out of my cage and into my girly panties. Again, I felt naughty and dirty and sexy all at once. I hadn't taken off any clothes but I have never felt so naked or exposed. The cool air gave me goosebumps. His hands touching me in private areas with such intimate confidence made me shiver.

A wet finger rubbed my virgin hole. "What is this sweetheart?" he prodded. The feeling was nearly inexpressible. Suddenly, I was totally okay to be on the receiving end. It felt so good and so natural to be touched there by him. It felt better than when I had played with my dick.

I knew what he wanted: "It's my pussy, Daddy."

"Good girl," he spanked me viciously. I was thrown off thinking that sort of thing was normally a punishment. But, I liked it. Before I could think, he began fingering my hooe as I moaned and writhed against his hand. First, one finger, and then two. Each one making me want to be filled more and more.

"You like being fingered like a slut?"

"Mmmm...I love it!"

"Ask me to fuck your pussy, baby girl." He spanked my ass again and I squealed.

"Fuck my pussy, Daddy" I breathed out lightly.

He spanked me again, harder. "Ah! Please fuck my pussy daddy!" I begged.