Reader
Open on Literotica

Feminizing First Step Ch. 03

(All characters are age 18+)

***

I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, and bellybutton piercings. Every new addition made my heart race and my "sissy clit" throb. That, by the way, is what I had to call my penis now, at least according to my mother. She felt it was a more appropriate name for the shrinking appendage between my legs. My therapist agreed. And my sissy clit was hard all the time, now that I wasn't permitted to touch it anymore.

I was granted ONE orgasm a week and always under the direct supervision of my therapist. She had a small bathroom attached to her office where she escorted me and watched as I "did my business". During a typical session, I just sat naked on the toilet and tugged away until I came. It never took more than a minute or two. She took great satisfaction in making me flush away my mess, every time I finished. This past week, she had been too busy to supervise, so she had one of her young nurse assistants watch. I didn't last thirty seconds.

Thankfully, today was my weekly therapy session. I had been looking forward to it all week. Or at least until yesterday, when my mom sprung yet another surprise on me. When I went to get dressed yesterday morning, I found that all my underwear had been replaced with women's panties. When I brought this up with her, she frankly stated that this was to be my new wardrobe and I better get used to it. This was the "new normal." Months ago I would have refused, but now after all the hormones and hypnotherapy, I was surprisingly content with this.

So today, I was wearing a pair of these new panties (I would later find out that they were a special brand made for sissy boys). Naturally, my mom had chosen this specific one for me. I found this new panty waiting for me when I came out of the shower. It was a frilly thong with pink lacing and a black pouch for my sissy clit. Little pink bows adorned the front and back.

As soon as I put it on, I felt a little dampness from my leaking sissy clit. I was now dripping precum all the time. Over my new thong, I put on a pair of tiny gym shorts, and then an extra small white t-shirt. I could feel my budding breasts strain against the cotton shirt. They were getting bigger and bigger... would I need to start wearing the bikini tops?

Glancing back at the mirror, I made sure the black gym shorts covered the thong and any bikini tan-lines. Again, looking in the mirror, I thought I could still pass as a boy. At least sort of. But, I then remembered the new footwear my mom required me to wear: high heels. The familiar black pair awaited me on the floor, next to a bunch of shoe boxes. I still dreaded wearing them in public.

Weeks ago, when my mother had mentioned the need to wear "appropriate footwear", I didn't know it would be this extreme. Nevertheless, I made a promise, and so now, on a daily basis, I only wore women's shoes. Most were high heeled, open toe designs. A few were patent leather pumps. I wore them around the pool while in my bikini, and when I left the house to go to therapy or run errands. My mom felt that I could use all the practice I could get. So without further hesitation, I slipped on the shoes, and fastened the ankle straps tight. With my high heels now on, I teetered around the room, feeling the thong wedge itself further up my derrière.

I glanced back at the mirror one last time to sort out my hair. No makeup today. Since I was leaving the house, I was not required to wear my usual makeup. A small consolation. That being said, I had become quite good at applying foundation, mascara, lipstick, and the rest. I glanced down at my makeup case, and eerily felt a part of me desperate to put at least some on. Maybe just some mascara? Regaining my senses, I brushed that idea aside and quickly left my bedroom.

My mother and I had an uneventful ride to my therapist's office. We parked and made our way into a nondescript building at the end of a suburban office park. Thankfully, we found the waiting room to be empty, and we sat down, amongst the chairs and strewn magazines. We had waited a few minutes before I heard the office door open. My therapist, Dr. Natalie Keawe, emerged and motioned to me.

Natalie: Come on in sweetie, I'm ready to see you now.

Mom: Good luck, dear. I'll be waiting right here for you.

Me: Okay, mom.

I got up from my chair and walked over to Dr. Keawe with my heeled shoes loudly clicking on the tile floor of the waiting room. I glanced back at my mom and saw her on her phone, busy chatting with a friend. I followed my therapist through the door and into her office.

Natalie closed the door and made her way behind the desk and sat down. I took one of the chairs in front of her desk and crossed my legs. Natalie was wearing her hair down today and her usual black business suit with a white blouse. After exchanging the usual pleasantries, my therapist asked me if I was ready for my weekly orgasm release. I vigorously said "yes" and she asked me to follow her. She took me out of a back door in her office and then down a side hallway, past several nurse assistants. Something was up -we weren't going to normal bathroom for this. She finally led me into a small exam room and closed the door behind us. It was a brightly lit room with a checkered floor, a pink exam chair in the middle, and several medical cabinets lining the walls. I also noticed a flat screen TV on one of the walls.

Natalie: Please remove your clothes and have a seat. This is a special chair -we normally use it for gynecological exams. But it will work fine for us. We will need to get started soon.

She motioned towards the pink exam chair. I was desperately horny, and undressing in front of her still made me anxious. But I persevered, and slowly took off my shirt and stepped out of my gym shorts. When Natalie saw me in just my thong, she smirked and raised an eyebrow.

Natalie: I see your mother has taken the next step. You look good in women's panties. But they need to come off too, dear. Leave your shoes on though. They won't get in our way.

Without a word, I peeled off my thong and hung it on a wall peg with the rest of my clothes. Now naked apart from my shoes, I walked over and sat on the pink chair, carefully placing my legs in the stirrups.

Me: What is this all about?

Natalie: Oh nothing. Just sit still. Trust me.

She then leaned the chair back and readjusted the leg stirrups -forcing my legs apart. Before I could say anything, Natalie had my arms and legs restrained with some leather straps she had on hand. I glanced up at the mirror on the ceiling. There I could see my reflection: I was strapped to the exam chair, my legs spread wide and my high heels pointing up in the air.

Me: Is this necessary, doctor? I can hardly move.

Natalie: Yes. You'll see. Now, do you want an orgasm or not?

Me: Yes! Yes!

Natalie: Then don't resist. We know what's best for you.

Me: Who's "we"?

Natalie: You'll see.

Before I could respond, Natalie put a ball gag in my mouth and strapped it around my head. A red rubber ball filled my mouth, causing me to drool on myself. My eyes widened and I stared back at my therapist in desperation, hoping she would at least notice my growing apprehension.

Natalie: Now stay right here. Don't go anywhere.

She blew me a kiss and left the room. Not like I had choice, I thought. I laid there, strapped in place, for several minutes. I prayed that one of the nurses wouldn't wander in. After what seemed like an eternity, the door opened and in walked Natalie, and my mom! They were both wearing white lab coats. OH NO! Natalie quickly shut the door behind her, and they both made their way over to me. I tried shouting through my ball gag, but my words were muffled.

Me: Hmmmph!

Natalie: I took the liberty and strapped him down already. Hope you don't mind.

Mom: No, not at all.

They grabbed some metal stools and sat between my outstretched and restrained legs.

Craning my neck, I looked down at them. My sissy clit was standing at attention.

Natalie: In the interest of time, let's just get right to it. We are all gathered here today for an intervention... of sorts. It has come to my attention that you have failed to keep your end of the bargain.

I emphatically shook my head from side to side. What was she talking about? I was starting to get really worried. I felt myself starting to sweat.

Me: Nnnnnmph!

Natalie: You agreed to NOT touch yourself while you were receiving your hormone therapy. Yet, you have failed to exhibit self-control. And we have proof.

I swallowed hard and feebly tried to test my restraints. My heart began to race. As my sissy clit shrunk, I felt a bit of precum drip down to the floor. My mom's jaw dropped when she saw this.

Mom: Aggh! Can we just show it to him now?

Natalie: Yeah. Let's get this over with.

Natalie took her phone out and began playing with it for a while. Suddenly, the large flat panel TV on the opposite wall turned on. She was streaming directly from her phone to the TV. She tapped her phone one last time, and a video began playing on the large TV screen. We all turned to watch it.

It was nighttime footage from a surveillance camera (or maybe a webcam?!) with no audio. I immediately recognized the image on the TV: my bedroom! It was a clear overhead shot of my bedroom, with my large bed as the focal point. They must have hidden a camera on the top shelf of my bookcase! The video itself was black and white -like that of a night vision camera. And yet, I could unfortunately see what was happening. I began to panic. I instantly knew what I was watching...me in bedroom...from last night. It's all over, I thought. I'm finished.

I became morbidly transfixed by what I saw on the TV. As the video played, it showed me walking into my bedroom and laying down on my bed, on top of the duvet. I was wearing a small bikini bottom. It was hard to tell from the video, but it was one of my favorite cheeky pairs. A shiny purple bikini with a little bow in the back. The video then showed me reaching down into the front pouch of the bikini with my right hand. I then played with myself for several, excruciatingly long minutes -tugging and rubbing my sissy clit the whole time.

Then the part came that I had been dreading. With one hand in my bikini, I reached down under my mattress with the other and pulled out a large black dildo. About 10 inches long. It was one I had "borrowed" from my mom's dresser. I then proceeded to shove it directly into my awaiting mouth. I sucked on it as I jerked myself off in my bikini. My head bobbed back and forth as I desperately tried to shove the large dildo down my throat.

Back in the doctor's office, I looked over at my mom and my therapist. My mom had crossed her arms and was shaking her head in disgust. Natalie was wide-eyed and furiously scribbling notes in her journal, with a devious smirk on her face. I felt even more precum drip from my sissy clit.

Looking back at the video, I knew what was about to happen. I saw myself begin to rapidly hump my hand in ecstasy, bouncing up and down on the bed. With the dildo still halfway in my mouth and down my throat, I succeeded in cumming straight into my bikini! Over and over. After a few thrusts, I became motionless on the bed, a large wet spot clearly forming on my bikini. I threw the dildo aside, with lipstick now smeared all over my face.

And now, for the worst part. I watched myself remove my right hand from my bikini. The video showed me cupping my hand and emptying its contents into my awaiting mouth. There was another ten seconds of me licking more cum my hand. And to top it all off, I had a huge satisfied smile on my face. About half a minute later, the video ended and the TV screen went black. Nobody in the room spoke for several seconds. I could hear my heart pounding.

Natalie: There...there is just so much to process. The dildo, the cum eating...where to begin?

Mom: I know. I was shocked when I first saw it. Simply unbelievable. My little sissy son has been a bad boy. And he has no idea where that dildo has been...

Natalie: A very bad boy indeed. And to think I thought he was doing so well with his treatment. Clearly, I misjudged him.

Mom: I hope you are not planning on giving him a release today. Not after watching that.

Natalie: Absolutely not. In fact...I have something else planned. Seeing as how he cannot control himself, I am going to recommend that he is put in chastity.

Mom: Chastity? What's that?

Natalie: A chastity cage. A little cage for his penis -sorry- his sissy clit. Once it's locked on him, he cannot get a full erection, and he cannot masturbate. More importantly, we won't have incidents like that happening again.

Mom: That seems a little extreme...

Natalie: Not really. It's becoming quite the popular treatment for boys like him. I've had great success in the past.

Mom: Really?

Natalie: I've had one patient kept in chastity for years. He was a chronic masturbator. His fed-up mother brought him in here, and after all other treatments failed, we ended up putting him in chastity. He still gets supervised releases every few months, and he has remained a virgin as far as I can tell.

Mom: That does sound nice, but...I'm sorry, this is all new to me. What is the procedure like? Does something have to be special ordered?

Natalie: No, no. We can get him fitted in one today. I keep several on hand for this very reason.

Mom: But what about his...size? Do they make them that small?

Natalie: Ha! You ARE new to this! Enough talk. Let me show you.

I watched as she walked over to the medical cabinets lining the wall, and began opening drawers. She finally opened the bottom drawer and grabbed a pink object and held it out in her hand for us to see. In her petite hand was a tiny pink chastity cage.

Natalie: Tada!

Mom: Oh my god! I love it!

Natalie: Me too! One of my favorites. This is one of our smaller models. We have even tinier ones, but this one makes a good starter cage. Now, shall we begin?

My mom clapped her hands in excitement, and the pair quickly got to work. I was too nervous to watch so I just stared blankly at the ceiling. I could feel their hands pulling and poking at my sissy clit. As my erection subsided, I felt cold plastic pressed against my skin. I could hear my mom and Natalie chatting as they fitted the device on me. A few minutes and painful pinches later, I heard the sharp clicking sound of a lock snapping shut. I glanced down to see my mom and Natalie grinning, each with a tiny metal key in their hands. And, in the middle, a pink chastity cage now poking out from between my hairless legs.

Natalie: Can we take your gag off now? Promise to behave?

I nodded and watched as she reached behind my head and unbuckled the ball gag. She pulled it away from my face, and put it in the sink. She then wiped away the drool, and softly put her hand on my cheek.

Natalie: I'm sorry we had to resort to this, sweetie. But, we cannot have you touching yourself.

Mom: Or eating your cum...

They both shared a laugh at that one. I waited for them to compose themselves before talking.

Me: I'm sorry mommy. I...I couldn't help myself. I was so horny. I don't know why. I think the hormones are-

Mom: It's okay, dear. You are now safe and secure in your new chastity cage. We don't have to worry about that anymore.

Natalie took some snapshots with her phone of me in my chastity cage for her records. Then, both she and my mom released me from the restraints and helped me back on my feet. Standing in my high heel shoes (and nothing else), I just met their eye lines. I wanted to look at my cage close up, but I was handed my clothes and ordered to get dressed.

I first stepped into my thong, careful to avoid snagging my heels on the fragile fabric. When I pulled the thong up my legs and around my waist, my caged sissy clit glided perfectly into place in the front pouch. It felt very snug and secure. After hiking up the pink side straps on my hips, I then glanced back at the women watching me.

Mom: I love how the chastity cage presses against his panties! You can just make out the outline of it!

Natalie: I know right? Adorable!

She knelt down and tapped on the cage through my panties, clicking her fingernails on the hard plastic. When she finished, I quickly put on my t-shirt and shorts. Thankfully, there was no obvious bulge down there -the shorts were loose enough to hide my chastity cage. All dressed, I looked at the women for guidance.

Natalie: Well, I am afraid our time today is up. But we made excellent progress. We really did! Hope to see you all next week. I look forward to hearing how well this chastity treatment works.

Mom: Thank you, doctor. And I agree, excellent progress. You have been a big help.

She then turned to me and glared.

Me: Yes, thank you, doctor.

Mom: Thank you...for what? Be specific.

Me: Thank you for putting me in chastity.

Natalie: Oh you're welcome...happy to help. I am starting to believe that all boys belong in chastity.

Anxious to get home and inspect my new chastity cage, I looked over at my mom.

Me: Are we going home, mommy?

Mom: Oh, we're not done yet. We still have to go clothes shopping. AND I made you an appointment at the tattoo and piercings shop. Got something special planned for you!

Natalie: That sounds wonderful! Have fun you two!

As we walked out of her office and to my next appointment, I felt the weight of the chastity cage pull down on my sissy clit. Something deep within me had changed. Maybe my mom and my therapist were right -maybe this was all for the best! I no longer wanted to be a boy! I wanted to be something else...

*************

Please leave a comment or use "send feedback" feature. Suggestions or ideas for where to take the story are appreciated. Even anonymous. I planned on this being a prequel series to my "Mommy's Chastity Boy" series. I would like to keep it lighter than that earlier, more darker series.
Log in or Sign up to continue reading!