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Small Steps in Baby's Transformation to a Sissy

A modest journey from a typical individual to a transgender woman.

Spankmasters
May 18, 2024
5 min read
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Sissy Baby Steps
Sissy Baby Steps

Small Steps in Baby's Transformation to a Sissy

I've had a long, tiring workday, as usual. I arrive home around 7 pm to help my wife with the kids. The nightly routine involves bath time, food preparation, homework, and some playtime. The kids are often in bed by 9 or 9:15 pm. Once the children are settled, my wife turns on the TV in the living room, and I set up at the dining table with my laptop to tend to some pressing work-related matters. In the past, my wife and I had great communication, but in recent years, our conversations have mainly consisted of sorted logistics.

Around 11 pm, my wife begins to wind down, softly saying her goodnights and heading for the bedroom. This is when I continue working. I'm well aware that work never ends, but this provides an excuse for me to wait till my wife falls asleep. Midnight is typically when I relieve myself then patrol the house to ensure the kids and my wife are deeply asleep. I sit with my back against a wall, facing the hallway leading to the bedroom and the children's room, my earphones on, the left side pressed against my ear and the right side against my head behind me so I can hear my laptop's sound and any sounds from the house. Then, I open my personal laptop and have a work laptop in front of me just to heighten the illusion of being busy. I open the browser in private mode and access my go-to porn website, teeming with categories.

I start by watching porn featuring enormous breasts, growing increasingly bored with this content. I then move on to interracial and gang bang videos, in which large, black cocks violently penetrate a small, white pussy, screams of both pleasure and pain emitting from the woman. I proceed to watch gang bang after gang bang, cum after cum. I can't help but feel like I could never be as amazing as that.

I'm slightly on the chubbier side, hairy, with a minuscule 3-inch cock when fully erect. According to the measurements on a ruler, my cock is only 3 inches long, just above the bottom of my penis. Thus, screams of ecstasy are out of the question. Whenever I had sex with my wife (three or four years ago), she never knew how to scream exuberantly. She'd say it was fantastic sex, and I played along. One memorable incident entailed her lying on her side and suggesting I enter her from behind. I struggled to even kiss her back door. It took several attempts to get a proper penetration.

Over time, I found myself delving into small penis videos, then small penis humiliation videos, followed by cuckold videos, then sissy videos, and finally conditioning videos. Gradually, my desire for women and their bodies waned. Instead, watching cocks penetrate butt holes, cocks flapping and bouncing, became more alluring. I loved breasts, vaginas, butts, you name it. But seeing the female body, particularly its intimate moments, became uninteresting to me. Instead, witnessing a dick being inserted into an ass, sounding alluring, and observing a mistress instructing me on how to become a sissy, became my preference.

At a particular time, I had to pause and take a shower. My wife complained when I entered bed unclean. The shower felt refreshing, and I washed up, masturbated, and quietly returned to the bedroom next to my wife. I snuck in, shut off the lights, took off my clothes, and got ready to enter the shower. As I lathered up, I indulged in sexual fantasies where my wife was taken by strong men, screaming with joy. Just as I was approaching orgasm, the bathroom door burst open and my wife entered.

"Look at me now! Turn around and face me!" she demanded.

Astonished by her sudden interruption, I ceased stroking my 3-inch cock, turned around, and sheepishly smiled.

"What are you doing?" she inquired.

My heart sank, knowing I had been caught, but also lurked a thrill of excitement. I had expected this to happen eventually, and now that it had, I was more than ready to deal with the consequences. Humiliated, I faced my wife, aroused by the undeniable desire to be a sissy. And knowing that my wife was about to uncover my secret left me on the edge. I'm so aroused by women, breasts, vaginas, and butts. However, my fixation for ass-fucking, cuckolding, and sissy indeed changed me. This was the most foolish and exciting moment of my life.

"Hey, turn around. I know what you've been up to every night." I felt so embarrassed and reluctantly turned to face her. I didn't want her to see my erection, but I also didn't want her staring at my tiny, one-inch-long penis. "Take the water hand shower and put your hands on the shower sides." She reached out, grabbing my penis with a metal ring. I started to get excited and scared at the same time, like I was watching a movie with a predictable plot. She put the ring around the base of my penis and testicles. She turned on the cold water, hitting my penis with a sudden burst of coldness, causing it to shrink almost half an inch. She then reached for a small cage with her other hand and began pressing it towards the ring.

"Wait!... What are you...?" I asked, understanding what was happening. I didn't move, letting her complete her procedure. It was like my body wanted it, while my inner self was silently panicking. She placed the ring down my penis and used the cage to press firmly, crushing my penis into a small case. My penis tried to resist, but my wife's gentle, soft hands were holding it firmly, draining it of power. My penis was crushed into a tiny device, and she turned a key, making a "click" sound - the battle was over.

My wife stood up and stepped back. "Finish your shower and come to bed. It's really late. Don't forget to throw your dirty clothes in the laundry basket." I slowly turned around, opened the hot water, not wanting to show any signs of what had happened. My wife closed the door behind me, and I found myself holding the chastity device, covering my penis and scrotum.

My hand was all over the chastity device, pressing my penis flat and feeling my testicles between the ring and the cage. I realized I hadn't cum, but I couldn't do anything about it. I was also afraid to touch the device. It felt strange. I shut the water and dried off. I put on my underwear and shirt. I got out of the shower, climbed onto the bed, and my wife was already asleep, as if nothing out of the ordinary had happened.

I tried to fall asleep, but my mind was racing, thinking about how to ask for the key back or how to release myself from this situation.

Waking up to my alarm clock, I checked to make sure it wasn't just a dream, but there it was - my tiny, caged penis and testicles. I heard my wife waking the kids for school. I wanted to talk to her, but with a quick glance, I realized I was expected to follow my usual routine.

During the morning, I did everything as I was supposed to, including sitting down on the toilet seat to pee. As I stood up, my pants got wet from drips of urine. Putting my pants back on was a challenge, fearing I might touch the new home of my penis and testicles.

I took the kids to kindergarten and school, then continued with my workday. However, my mind was preoccupied with my current condition, making it difficult to focus on my tasks. One thing was certain - I wouldn't be working tonight.

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