Sissy Whore Stories

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Sissy Whore Pays the Rent

by FrillyMaid on Sep 15, 2017
Transsexuals & Crossdressers

I walked in from the rain, and was confused by the silence. Normally my Mistress would be sitting in the living room with a glass of red wine and her favourite show on, but instead the room was empty and silent. I walked to the kitchen and saw a note on the worktop. It said simply "wear the clothes in the bathroom and come upstairs". Walking to the bathroom...

Sissy Whore Ch. 01

by DebbieDublin on Mar 7, 2018
Transsexuals & Crossdressers

I suppose it started as a game really. Born out of the frustration and boredom of countless meaningless encounters with nameless men from chatrooms who would call to my house late at night. Although each proclaimed themselves to be dominant, still none seemed to live up to my own expectations, leaving me drenched in their seed but ultimately unsatisfied. It...

Sissy Whore Ch. 02

by DebbieDublin on Mar 7, 2018
Transsexuals & Crossdressers

I wrestled with my emotions for the rest of the afternoon, sitting on the sofa trying to distract myself from the mysterious web chat. I'd been at this a long time now and I was used to conversations that went nowhere. Most of the guys that contacted me followed up with a dick pic and were not really capable of continuing the fantasy beyond the scant descrip...

Sissy Whore Ch. 03

by DebbieDublin on Mar 12, 2018
Transsexuals & Crossdressers

I woke to the sound of my cell phone vibrating in the other room. I had no idea how long I'd been asleep there on the bathroom floor. It was still daylight but I felt colder. Jumping up from the floor and running into my bedroom to reach the phone before it stopped ringing, I caught a glimpse of my ruined face in the mirror which was still stained with strea...

Sissy Whore Ch. 04

by DebbieDublin on Mar 14, 2018
Transsexuals & Crossdressers

I stumbled to the bathroom to fix my face, my head still spinning. I reapplied my lipstick and dusted off my foundation. Wiped away the mascara stains from my cheeks and reapplied. When I was done I returned to the living room. 'These are for you.' He said when I approached. He reached into his jacket, extracted a pair of large gold coloured hoop earrings...

Cheap Sissy Whore To Call Girl Ch. 03

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

My first few days at the hospital wasn't the typical hospital stay. I'd get fucked by everyone who worked there. Most of the time I was too dazed to realize what was happening but there was always a cock or a pussy that needed attention. The doctors would come in during their breaks to ass fuck me. The nurses would make me lick their pussies clean. I didn't...

Cheap Sissy Whore To Call Girl Ch. 02

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

The day I woke up after being knocked out was a strange one. I didn't know how long I had been missing but I felt my body had been completely transformed. My skin felt softer, I had breasts, my lips were filled with collagen. I remember waking up in a what seemed like a hospital room and walking up to a mirror and looking at a gorgeous bald woman with a peni...

Cheap Sissy Whore To Call Girl

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

I looked at the throbbing red cock within inches of my face, split seconds before I was to be showered with thick musty spunk on the back alley streets while I thought back to what had happened 24 hours ago when I was a normal 22 year old male living a normal heterosexual life. It all started when my girl friend of the time, Doreen, had filmed us having sex...

PVC Sissy Whore

by Dostoyevshe on Sep 16, 2017
Transsexuals & Crossdressers

One day I was bored and horny so decided to cruise around a local adult store and find some action. I squirted a good amount of lube into my ass, slipped in my favourite 3 ball butt plug and put a pink chastity cage on my tiny cock. I wore hot pink lacy panties and bra, a tight PVC miniskirt, high heels, a pink jacket and heavy makeup like a whore, complete...

His Sissy Whore Pt. 01

by laumadhr on Sep 16, 2017
Transsexuals & Crossdressers

Hi friends, I am Ayesha, a fat, cross-dressing sissy from Chennai. Please send feedback to my profile! The story takes its time to build, so relax :) This is the first part, where I start with my man... The second part will have more juicy stuff ;) Anna (un-naa) means brother in Tamil :) ***** It was a hot, sweaty midsummer night like always in Chennai. N...