The Sissy Chastity Diary

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

As his cock stretched me out, I felt the rest of my body shrink. I realized I was so small, so insignificant underneath this large man. He could do anything he wanted to me. I was afraid. I was excited. I didn't want this to ever stop.

Abruptly, he turned me around, entered me missionary, then lifted my light little body as he fucked me by bouncing me in the air. "Oh my god! Oh God!" I hyperventilated. My arms draped around his shoulders and held on tight. On a dime, my impersonal, degrading fucking was transformed into intimate lovemaking. And I couldn't do a thing. My eyes rolled to the back of my head. Then--his lips were on mine again as my pussy slid up and down his unending cock.

Suddenly--my testicles hugged my body. I surrended and began to shake violently. His arms holding me upright as I convulsed in pleasure. My leaking cage dribbled down my thighs. His length shot load after load deep into me, against gravity, as my pussy gripped him with each release of my own.

Oh my god, oh my god. A man's kiss had made me cum.

"Ughh.....mmmm....ughh," I moaned into his mouth.

I was horrified. The post-sex clarity of months hit me all at once. But it was tinged by the greatest sense of relief and pleasure of my entire life--by far.

I passed out and woke up to his broad body enveloping mine, holding me close. All of my clothes were gone, and so were his. The heat from his body was warming me. This was too much. My first instinct was to squirm away immediately. This was so wrong and after cumming I wanted nothing to do with any of this. But his body was so heavy! I was awake and he wasn't and I still couldn't even budge. God, how embarrassing. My limp, caged cock felt so exposed in the cool, dark air. I could feel months of cum sticky on my inner thighs...ugh. But, as I squirmed, he pulled me even closer, grabbing my chest and rubbing it in his sleep. My body instantly warmed up like a lit match, goosebumps spread across my smooth ass and legs. And my...pussy began to quiver, to pulse and tighten and open as if in memory of its recent deflowering. Oh God, I couldn't get out, but did I want to?

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
FranziskaSissyFranziskaSissy1 day ago

Forgetting about or misplacing the key may happen, but thats kind of really strange …. But it had a good outcome an well deserved descending into sissy submission …. And yeah it takes time until clarity or better the opposite guides you to cock, then one enters your lips the sissy can taste it and this abnormal smelling, an unwashed cock is delivering, a sissy is hooked …. That cock forcefully painfully raping your asscunt and inseminating breeding you, the sissy is lost or better hit the borderline man to sissy pig …. So did the sissy in your tale as well as i had become one myself

💝💝💝💝💝💝💝💝💝✨🌈

AnonymousAnonymous9 months ago

Good story but why didn't you just cut the lock off releases c*** and balls and go on life as usual it would have been a lot more sense

algolfcrazyalgolfcrazyover 1 year ago

Loved the story.Something I have been thinking about myself

JgsexyJgsexyover 1 year ago

Very descriptive writing! Loved the story!

ChloecrossedChloecrossedover 1 year ago

Wonderful story, and very sexy!

Show More
Share this Story

Similar Stories

Lesser of Two Evils A man's choices will transform him into a cum slut.in Transgender & Crossdressers
Feminized by BBC Friend Ch. 01 My BBC friend slowly feminize me.in Transgender & Crossdressers
White Dom Turned Sissy for BBC Alpha white man learns his inferiority to BBC.in Transgender & Crossdressers
Hypnosissy 01: Becoming a Cocksucker Straight guy watches porn tapes that are not what they seem.in Fetish
Down the Sissy Rabbit Hole A reluctant sissy gets forced to be the slut she wants to be.in Transgender & Crossdressers
More Stories