A Sissy Fantasy

Story Info
A curious sissy gets all she's ever dreamt of and more.
1k words
4.09
56.1k
30
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

My darkest fantasy has come true. I'm now a slave to a dominant couple. My ex-wife and her new boyfriend have taken me in, and in return I am dressed as a girl always and their maid and sex slave. Frilly panties, stockings and skirts, babydoll t-shirts, and a blonde wig are parts of my new uniform. Also I now wear a stainless steel chastity cage now encasing my four inch cock. I am enjoying it. After all, it's all for fun, and I can always change my mind. I'm glad I told my ex all my secret fantasies before we were divorced. My new Mistress and Master are good to me.

I'm told, after being in chastity for a couple of weeks, that my last real orgasm was just that. I will receive a limited number of ruined orgasms before my chastity is made permanent and I will only be milked from then on. She doesn't tell me how many until the end.

Far too soon, after the frustration of seeing over a months worth of cum ooze out of my unsatisfied clitty for only the second time, I'm told it's over. Within the day my clitty is pierced with a PA, which is then fastened to my cage and my lock glued shut.

Regular milkings desensitize me, so when my sissy pussy is used I have zero chance of a sissygasm, just pathetic cum dripping out of my cage, all of which is fed back to me. Hormones are added to my daily regimen, so before long my cage no longer holds back my erections, they have ended too.

All my pleasure now comes from service, for my couple and their friends, sometimes even strangers. Sucking cum out of cocks and pussy, even other sissies pussies. I'm trained to swallow an entire load of piss without spilling a drop, a service I give my Master daily, draining his big cock on command. Mistress prefers to just cover my face and chest. My sissy pussy has taken cocks one and two at a time, always cleaned in my mouth when they are done, and my training now includes fisting. I have to learn to clench tight once more after. If I cannot grip a pencil within five minutes of a fist pulled from my hole, I am punished. The cane marks decorating my ass make this a talent I learn quickly.

I am given time limits to make a man cum in my mouth, reducing each month. The few times early on I miss those targets I'm told a penalty count goes up. I don't know yet what it's being counted to. It becomes less and less fair. My time limit counts any time a cock is in my mouth, even after a man has just filled me with a load. My penalty score climbs. My allowed time drops below a minute. I fuck my face viciously on every hot meat given me, my throat bruised and sore, but I fail two out of three times, and only succeed once at thirty seconds. More cane marks, but they tell me that is not the final penalty.

The hormones have given me perky breasts. My nips stick out from arousal constantly, and are stretched, pulled, clamped, and finally pierced. A pair of silver rings hang on my chest, often chained to lead me around. I'm told my tits are still too small. I will be getting implants. I will no longer be able to hide my changes, I will have huge bimbo tits announcing my sissyhood to the world. I tell myself if I ever change my mind about being a sissy slave, I can have them removed, move to a different city, put this all behind me. Everyone here will know. Those who haven't already used me.

The day comes, and I am given my new breasts. I dont know the size, Master and Mistress don't bother my silly sissy brain with details, just that they must be close to the size of my head. I heal from the surgery crying daily, in both despair and joy. My lessons now include titty-fucking, and again time limits are imposed on me.

I miss too many in my first week of titfucking, I'm unsure with these melons and more used to using my mouth and sissy pussy to get men off. My penalty score, I'm told, is now full.

I am taken again to the clinic, where I am bent over and milked of all my cum. My last even potentially fertile sperm I am told, as it is poured into my mouth for me to drink. My cage is carefully cut off, and my clitty falls limp below me as I anticipate the snip to come. It's demeaning but lots of men get a vasectomy I tell myself. A cream is rubbed over my cock and balls and I am left alone for a few minutes with my thoughts.

The cream has numbed me completely. My last desperate fumbling with my clitty, one last attempt at a real orgasm, even a dry one, is doomed from the start. As they return to begin and I lay back waiting, I am surprised as they give me general anesthesia to put me under.

I wake up sore. Looking down between my enormous tits I can only see bandages between my legs. I still have a shred of hope until I look to the side, and see the jar next to my bed, both testicles floating in preservative. I cry a little but have hope now that my sissy clitty may hang free again, that I may stimulate it once more in an almost forgotten way.

I later am shown the new cage, constraining my clitty even smaller than before, held on permanently by piercing. No one will ever touch my clit again.

I haven't been made a girl. I will never again be a man. I am a sissy bimbo forever.

I'm Jeanette. What would you like to do to me?


Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
tomthumpertomthumperabout 2 months ago

What a cute little sissy whore! I love your big tits and eagerness to please, sweetie! I certainly love to flick your tiny clitty and tease you and make you drip tiny little clitty clum tears....

wannabeusedwannabeusedabout 3 years ago

Good story, would have liked to hear more about how Master and Mistress used you and what you did for their friends.

GrrrreatImaginationGrrrreatImaginationover 3 years ago

Oh, wow. Such a rich mix of TS/CD and BDSM. The brevity of the timeline Jeanette offers us teases with glimpses and implications of her/his desires, fears, hopes. The lack of described interactions with Jeanette's Mistress & Master leave a gaping hole for the reader to fill in. A reader might suppose the relationship is abusive, yet Jeanette tells us at the outset her fantasy has come true, so isn't that kindness for Master & Mistress to give that to her/him?

For how short the story is, it's quite complex. Verrrry interesting, and well written.

Thanks.

AnonymousAnonymousabout 4 years ago
Sissy

Oh wow that made me wet my panties

Sissy_JeanetteSissy_Jeanetteabout 4 years agoAuthor
Thank you Antares!

😍 I really like your stories too!

Show More
Share this Story

Similar Stories

Feminized By My Mother Ch. 01 Shemale mother makes son a sissy.in Transgender & Crossdressers
Mother's Greed Ch. 01 Mother gives in to her desires.in Transgender & Crossdressers
Barbie's BBC Beginning A sissy husband gets roped into interracial sex by his wife.in Transgender & Crossdressers
A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
Penis Shrinking from Chastity Chastity leads to penis shrinking an love for black cocks.in BDSM
More Stories