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Chapter 14
by Sissydesires
Do I cum and embrace my inner self or fight back against these sensations?
I cum and wake up
My body shot forward in the hotel room. I stare around appreciating that my body wasn't shackled to the bed anymore. The sunshine fights through the cracks of the weak pale curtain colors. I look at my cock still caged. My girlfriend must have the key in her grasps I thought to myself. My mentality went to locate the key and release my cock from this metal prison, but I hardly start to looks for the key and just sat there motionless.
I turn on the tv like a coping mechanism. A sport show talking about how the great Dickens the VI is facing a head on retirement in the masters league. His numbers dropping significantly as he balance his golf life and moving money into his favorite businesses. He was a guy I used to follow when I was little, always loving his confidence on the golf course. Watching him win countless tourneys, and spending a lot of money on charities.
There was a knock at the door. My heart pulses as I knew I was about to face Monica for the first time. I stood up, gathering confidence like my childhood hero Mr. Dickens. I yelled. "Come in."
The door handle jiggles as a short mexican woman, in a long unflattering maid grey uniform, steps in. She looks at my naked body with a broom in hand. Her eyes wanders down my slender pale frame to my crotch area eyeing my caged cock. She giggle then communicated a few words in Spanish as she unexpectedly left the room. I suffer the vast abundance of humiliation as the old maid left with a tale to tell her friends and family.
The bathroom door shot open to reveal Monica in a towel. Her damp sexy hair and uber smooth legs enough to get any men, without a caged, a full on boner. She laughs moving closer to me. She lays a hand on my shoulder, looking over my body. She leans in for a quick kiss then went over to a bag with her clothes inside.
"So we aren't going to talk about last night?" I asked.
She shook her head. "You agree to my offers of helping you discover your true inner self. So, of course we can talk about it but not right now. I got to head to a meeting this afternoon, so we need to get a move on." I place a pair of jeans on with a button up tee shirt. I heard her voice as she gather up her large black bag from underneath the bed. "Damn, John, your ass looks a lot fatter now. Mmm fuck." She came over giving my cheeks a large thrash. "What do you say?"
"Umm thank you, Monica." I say with no correct answer for her.
"Hehe, don't worry. Next weekend, you will be calling me something different." She winks heading out to the car.
...
We drive home in pure silence stillness. I couldn't muster up any statements or conversations. She drops me off at home. She kisses me on the cheek before driving off into the large skyscraper city that King kong would love to ascend. I amble into my uncle home with a gut rumbling sound. I heard my uncle glancing at a reality tv show about pawning items.
I heard his voice. "Back from your girlfriends." He looks over at me. "Mmm you still got your chores to do before heading to work today. I expect my place to be..." He trails off as I went to get the sweeper. "Hey, is your ass bigger. You been doing just squats you dumb dickweed. Bulk up your muscles not your ass cheeks you girly boy."
I thought that his words came out a fraction of pleasantness. Not like how he used to call me a useless scumbag asshole shit face. But a more sympathetic sound came from his gravelly voice as he calls me a girly boy. I knew what porn he participated in, searching throughout the night. This made me feels even worse as I went through his house cleaning.
After twenty minutes, and unseen eyes on my much larger bottom from my uncle Jasper, I got finished with my chores. "I'm done sir."
"Good... Good. If your ass get any bigger, John, I might have to purchase you some new sexy underwear." He flashes a creepy wink in my direction as I quickly hurry to put my work clothes on upstairs.
Oh shit, I'm forty minutes late for work as...
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My girlfriend turns me into a sissy
Girlfriend give me the push into my sissyhood
One night at a rave, my drink get spiked and I ends up in a strange woman's bed.
Updated on Jul 8, 2023
by Sissydesires
Created on Feb 3, 2022
by Sissydesires
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