Feminizing First Step Ch. 05

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+.

Chapter 5

Today began like any other. I awoke in my bed with my wireless earbuds still in my ears. The sissy hypnosis audio track was gently playing in my ears. I must have fallen asleep again to it. Oops! This one was from the "Bambi Sleep" sissy hypnosis series -one of my favorites. I normally listen to it for twenty minutes or so before going to sleep. Oh well! I laid there listening to it some more -the words and subliminal messages washing over me. But I eventually snapped out of it and got ready for the day.

After taking care of myself in the bathroom, I got dressed. Just a cute little yellow sundress today. I wore it over a plain, red thong. But no bra today... I'm spending the day at home. Also no shoes! I got my toenails done yesterday and wanted to show off their brilliant red color! They match my thong! I couldn't take my eyes off them. So barefoot it is.

Looking down, I was relieved to see no sign of a bulge... my sissy clit was nice and tucked away in my panties. And I am no longer wearing a chastity cage -there is simply no need! My sissy clit no longer really works. Months of hormone therapy combined with the sissy hypnosis sessions have rendered it pretty much useless. No more nasty erections. No more gross boy thoughts. It just hangs there. A useless appendage that was shrinking with each passing day. Perfect!

My ass -or "boy pussy" as my mom calls it- has replaced my sissy clit as my source of pleasure and sexual release. It has been my focus ever since I started wearing the chastity cage. Around the time I was first locked in chastity, I was also prescribed a butt plug regimen by my "therapist". My boy pussy was subjected to bigger and bigger toys as the months went by. While my sissy clit was shrinking and being rendered impotent, my boy pussy was becoming more sensitive and more... "hungry" so to say.

All dressed and made up, I pretty much spent the day home alone doing chores and sissy tasks. First, I am required to drink 2 liters of soymilk a day -to help promote my estrogen levels. I usually have a couple of glasses with each meal or when I take my testosterone blocker pills. In the afternoon, I also spend another half hour watching sissy hypno videos. All part of my required training.

When I'm not doing those required tasks, I usually tan by the pool or practice applying makeup in my room. I have gotten quite good at doing my eyes and eyebrows. In particular, I've really perfected the whole smokey eye look. Mascara, eyeliner, and fake lashes have really become my best friends. I can't wait to show my mom when she comes home.

She was gone all day and didn't come home until later that night past eight o'clock.

I was laying on the couch watching make-up tutorials on YouTube when the front door opened and she came through. She had been at work all day. Her hair was up in a ponytail and she was wearing a pair of black framed glasses. She must have taken her contacts out at the gym.

She was in her work attire -a light purple blouse with gray women's trousers. She also had on a matching gray vest, all buttoned up. A pair of black Louboutin heels completed her outfit.

Ignoring me, she headed straight to the kitchen and poured herself a glass of wine. Wine in hand, she walked over and sat next to me on the couch.

Mom: What are you watching, kitten?

Me: Make-up videos mom.

Mom: Oh lovely. Mind if I watch too?

We sat there on the couch for a while and watched some more tutorial videos together as she sipped on her wine. After she finished the last of it, she set the glass aside and got up. She reached her hand out to me. I took it and she helped me up. We were about the same height, but with her heels, she stood several inches taller than me.

Mom: Come on and get up, honey. Enough lazing about. Let's go to my bedroom. We have a long night ahead of us.

Without saying a word, I put my iPad down and followed her upstairs and into her bedroom. I wasn't normally allowed in here. Certainly not by myself. This was where she and her many boyfriends... slept.

Having it been months since I was last in here, I nervously looked around. Her bedroom was still sparsely decorated with just a four poster bed, a bedside table and chair, and a dresser. And a large black steamer trunk at the foot of the bed. I glanced worryingly at its large metal padlock. I knew what was in there...

Mom: Now let's get this cute dress off of you and get you onto the bed. I'll need you to assume the spanking position.

Me: What?! But I did all my chores... I've been good.

Mom: Stop worrying and just do as I say. I have something special planned for you tonight.

She helped me out of my yellow sundress and draped it over a nearby chair. I was now standing before her in just my skimpy red underwear. I tried meekly to hide my little "bulge" with my hands. Something deep in my subconscious was ashamed of it.

Mom: Look at you! Kitten, your hips look amazing in those panties! You really are becoming the perfect sissy. Love that little bulge too! Still too large I'm afraid. But we'll get there... for now, on the bed!

I blushed in embarrassment. She then took my hand and help me onto her elevated, king-sized bed. Now, still wearing my red thong, I laid onto her bed face down with my ass in the air. She re-arranged her pillows so that my head was comfortable, and she put another pillow under my stomach so that my ass was kept elevated. She then diligently tied each of my wrists and ankles to the four wooden posts of the bed with some strips of silk fabric. The strips had already been tied to the posts -left over from a previous spanking session. With the last knot pulled tight, I was firmly tied spread-eagle to her bed and not going anywhere.

This was the spanking position she mentioned earlier. She used to tie me up like this for monthly discipline sessions -back when I resisted my sissy training. But she hadn't spanked me in months. Not since I had fully embraced my new sissy lifestyle.

While laying there restrained, I noticed the bedroom lights dim a bit, and I heard her turn on a stereo. Some girly pop music started playing lightly in the background. My mind began to race. This was not going to be a normal spanking session... I was afraid and excited at the same time!

With my face pressed against the pillow, I then heard two distinct snapping sounds as my mother put on a pair of latex gloves. A few seconds passed before I felt her hands on my ass and felt my thong being pulled to the side. I wiggled my ass in anticipation of her paddle. But surprisingly, no whacks came... instead I felt something wet and cold being pressed against my boy pussy.

Me: Ah that's cold!

Mom: Oh calm down. It's just a bit of lube...don't worry, I'll go slow. Just relax. Your pussy is tight.

The rubbing continued. Then I felt a slippery finger begin to press firmly against my little hole. Without much protest, her finger slid right in. And before long, her other finger was in me. I couldn't see it but could definitely feel it -she now had her gloved index and middle fingers deep within my ass. I felt her warm fingers begin to explore me. She was searching for something.

Mom: Just relax. This may feel a bit weird. But it needs to be done. You've gone too long now without a release... without an orgasm. Your therapist and I are worried about you. You need to be milked.

Me: Milked?

Mom: Yes dear. Or as your therapist called it... a prostate massage.

Me: But why mommy? I have been a good sissy. I haven't cum in months. I don't think I can cum anymore...the hormones...

Mom: That's the problem and kind of why we're doing this. Apparently your body needs this... for medical reasons. Doctors orders. Now be a good sissy and stay still. I watched your therapist do this on another sissy boy earlier today. I know what I'm doing...it shouldn't take long.

I lost track of time. Ten minutes passed...maybe twenty. I just laid there, with my arms and legs outstretched, as she worked away on my ass, taking breaks only to add more lube. Tired of staring into the pillow, I closed my eyes and began to daydream. Images from the sissy hypno videos began to flood my mind. Big hard cocks, cute sissies, and feminized boys were the only things I ever dreamed about any more. My brain had been deliciously reprogrammed. As my thoughts began to focus more and more on these images and triggers, I felt something shift in my ass.

Something began to pulsate and a pressure began to build in me...

I pulled against my restraints as I could feel the pressure building and building. My mother's fingers began to rub harder and deeper. She could feel it too! New sensations I had not felt before were washing over me. My eyes rolled back into my head as my prostate began to pulse. More images of sissies sucking cocks began to flood my brain. Just as I began to moan, it all reached a crescendo and I couldn't take it anymore...I went over the edge...

Pulsing waves of pleasure cascaded over me as my ass began to clench uncontrollably on its intruder. My boy pussy was throbbing! As I continued to moan, I began to feel a sensation in my sissy clit -one that I had not felt in a long time. It almost felt like I was peeing. Something was coming out! I felt like I needed to warn her. Or get her permission...

Me: Mommy! Oh my god I can feel it coming out!

Mom: That's it kitten... let it out all out. Let it-

Before she could finish her words, I felt months' worth of cum begin to drip out of my tiny cock. It quickly became a thick, continuous stream of cum. I instinctually thrusted against the bed, humping away in desperation, but my shrunken clit remained limp. It didn't matter anyways. My penis was no longer a source of pleasure. My ass was. And although I could not see it from my facedown position, I could feel a growing damp spot on the sheets as my cum began to pool beneath me. I was now leaking nonstop. This was no orgasm -just a steady flow of sissy cum out of my body.

As I writhed in pleasure on the bed, my mom's gloved fingers continued to explore my ass with her index and middle fingers pressing harder and harder against my prostate. She was determined. I could feel her other gloved hand pressing for leverage on my lower back, gripping hard. More cum dribbled out of my clit.

Mom: Wow! There is still more in you honey. But I guess that's to be expected...all these months and no release. I hope you're enjoying this!

Me: Yes mommy, I am. Thank you. (I barely managed to get these words out.)

Mom: You are most welcome dear. Now... this is how you will be "milked" from now on. Your therapist told me that you must have your system cleared out every few months...even with all the hormones you are taking. I need you to stay healthy. A healthy little sissy for mommy.

She continued for a few more minutes before her pace slowed, and her gloved hand left my ass. I next heard loud snapping sounds as she pulled the latex gloves off her hands. Without bothering to turn around, I began to speak into the pillow.

Me: Are we done now mommy?

Mom: Yes kitten. All done. Now, don't you feel better?

Me: Yes mommy. But can you untie me? I think I want to go to bed. I'm exhausted.

Mom: Oh I don't think so. We are just getting started.

Me: Started?

Mom: You'll see. The night is still young. I have something else I want to introduce you to...

I could barely focus on what she was saying. Feeling exhausted and a bit exposed, I yearned for my stainless steel plug. I sometimes slept with one inside me.

Me: Can you at least put my butt plug in? Please...

Mom: I would, honey, but there is no need for that now. Like I said... we're just getting started. Now wait right here. I'll be right back! Don't go anywhere!

She gave my ass a little swat and hopped off the bed. Craning my neck back towards the bedroom door, I could just barely see her as she left the room. I heard her laughter coming from the hallway. Feeling vulnerable all naked and tied to the bed, I tested my restraints again to no avail. At least she could have put my butt plug in! I almost felt naked without it. My lubed asshole was now up in the air and gaping. Defeated, I rested my head against the pillow. Even as I laid there motionless, I could feel excess lube leaking out of my ass.

After a few minutes went by, I began to hear footsteps. I glanced back over my shoulder as best as I could. Out of the corner of my eye I could see something large and dark emerge through the doorway. WHAT has she done!

My eyes widened in shock as I knew my sissy life was about to change forever... as a final drop of cum dribbled out of my sissy clit.

To be continued.

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