My Transformation- Chapter 09 (Patreon)

My Transformation 

His name was Chris. There was a great sadness on his face and in his eyes. He stood in front of the mirror, a broken person. Years of trauma, isolation, and neglect had rendered him incapable of decision. Faced with an impossible choice, he existed in

limbo. Limbo, however, wasn’t living. There was a glimmer of potential there. But the step over the threshold was more of a leap. A leap of faith. A leap of courage.

He peeled his clothes off, down to his bare skin, diaper and all. He was breaking the rules but he didn’t care. Articles were handed to him and he took them in kind. He stared at each article before he put them on, trembling as foreign materials touched his skin. The more pieces that were handed to him, the more he shook. Tights were a challenge, as was the bra. It was decorated with red lace. Stuffers were added to give definition. The matching panties caused a prolonged pause, but once on, they hugged his body in ways that were unimaginable. The low cut shirt accented the new definition, barely coming down past his ribs. The pleated skirt hung off his hips and extended down to his mid thigh. The heels didn’t fit. He didn’t expect them too, and the thicker carpet would have made it hard to stand. He looked at himself in the mirror, taking it all in. There was a softness to his demeanor, as the feminine clothing stripped away was

little masculinity his body might have had.

His hands fidgeted as he sat down in front of the vanity. Before him lay an overwhelming menagerie of beauty products. He could identify the obvious ones but had no real comprehension of where to start. That’s when I took over. A novice myself, I looked at his face and imagined it as a blank canvas. I could make of him what I wished. I started with some foundation, filling in the scars of puberty and giving myself a smooth page on which to paint. Concealer helped with the trouble spots under his eyes. I choose a light green eyeshadow, skimpily applied as to draw attention but not overpower his hazel eyes. Eyeliner was harder to apply and justifiably so. It felt light any one wrong move and he would be blinded. Mascara was easier; simply bring the brush

in close and let the natural movement of a blink create a stunning lift to his already long lashes. I choose a lip gloss instead of lipstick to have a more grounded look, focused on his natural beauty rather than being overly artificial. As he pursed his lips and looked at the completed work, there was a noticeable shift in his demeanor. The tension in his back and neck eased and his eyes welled up. Using the edges of her fingers, she wiped the tears away, and thus, wiped him away.

Her name was Chrissy. For far too long she had been kept inside, hidden in darkness. She blinked her eyes, clearing the moisture and looked upon herself. Her bottom lip trembled as her mind took in what her eyes could see. She stood and abruptly turned, causing the skirt to fan out before falling back against her smooth skin. She stepped across the room to the full length mirror, each step a poor practice in

elegance and grace. At the mirror, she turned slowly, shifting her weight from hip to hip to get a view of her curves. She looked over her shoulder to see the full view of her butt and stopped at a side view. Her hands went to her chest, gently tracing the curves of her bosom. There seemed to be an internal sadness at the lack of definition, but it was short lived. She awkwardly posed as if unfamiliar with how her body was supposed to move. She made faces in the mirror, soft gestures of portrayed innocence and alluring temptation. At long last, she turned away from the mirror, content with her reflection.

“That went better than I thought.” She said, letting her hands drop to her sides. “You think so?” She asked.

“I do. I have to say that I’ve never done anything like this before.” “Me either. It’s all new…and…exciting. I mean. If you think so?” “I do. I very much do.”

“Really? You’re not weirded out or disgusted?”

“No. I thought I was going to be but the farther into it we got, the more natural it felt.” She said, moving to the bed and sitting down. She patted the spot next to her. “Come. Sit.”

Side by side on the bed, they held hands.

“I…I wanted to thank you for the opportunity. This means a lot to me.” “I think I should be the one thanking you.”

“Let’s just say that we are mutually grateful.” “Agreed.”

They sat there for a few minutes, taking in the moment. “How does it feel?” She asked.

“It…it feels good.”

“That’s good. You had me worried there for a minute.” “Why?”

“There’s something…I can’t really explain it, but you seem different.” “I am different. I think I have a greater understanding of everything.” “Is that good or bad?”

“It’s good. At least I hope that it’s good. I have a lot of questions.” “Me too! I hope that’s okay.”

“Of course! I can’t figure this out by myself.”

“Uhh, okay, well, here it goes. What do I call you?” “You know my name.”

“I know your boy name.”

I looked at her in bewilderment. “I always assumed that my name would stay the same, just twisted to sound girly.”

“Well, Chris is a unisex abbreviation. You could be a Christine as well as a Christopher.”

“I..” At some point, I would have to tell her about Patty and her penchant for making me feel like a girl. “I was called Chrissy before.”

“Chrissy?” Monica said, “Am I the only one who thinks that’s too on the nose?” “I…uh…I never thought about it.”

“You paused there for a second. Are you happy being called Chrissy?” “I don’t know. I haven’t really thought about it.”

“Because…?”

“I’ve been kinda busy. You know, being turned into a baby.”

“Speaking of,” she lifted the front of the skirt and checked the panties I was wearing, “I need to make sure you’re still dry.”

She pulled her fingers back to find a glistening substance. She sniffed it before smiling. “I guess being a girl is exciting for you.” She licked her fingers and my eyes went wide.

“I guess it’s time to share my secret with you. I’m a sissy too.” “But you’re a girl. You are a girl, right?”

“Very much so. But like you, I’m more than what everyone sees.” “How so?”

“Is that really what matters?”

“Maybe. It felt like we were having a moment together.”

Monica sighed. “We were. I mean we are. It’s just that…I don’t tell guys this kind of stuff.”

I took her hand and looked her in the eye. I took a deep breath, gathering my courage. “I am a sissy. I have my manhood locked away, I’ve been fucked in the ass on multiple occasions with a strapon, and I let you dress me like a slutty schoolgirl. Oh, and in my downtime, I wear pink diapers and get breastfed like a baby. I’m the very definition of manly.” I sarcastically said.

“Well, when you put it that way, I’d say you are far from being a man!” She said with a laugh. “You promise not to make fun of me?”

“I doubt you have any secrets darker than mine.”

I was completely wrong in my assumption. Dead wrong. As we sat on the bed she divulged some of the finer details of her exploits. I found myself getting squirmy. I hoped that she didn’t notice and was thankful for the cage. I didn’t know if it was how she told the story or my current mindset, but I was as horny as I could be. That’s a lie. I was imagining myself in her position and it was causing a wetness in my panties.

“…and that’s just the tip of the iceberg! There’s so many things I want to try!” “Jesus…”

“Yeah. I need some of that. But you only live once, right? And if God didn’t want me to indulge, He shouldn’t have made it feel so good.” She said with a laugh. “So,

what do you think? Are we still friends?”

“At this point, I don’t know who likes being bent over more, you or me?” I joked, trying to alleviate my desire through humor.

“Only one way to find out!” She said, bounding to her feet. “C’mon, up, up, up!” “W-wha?”

She pulled me to my feet and spun me around. I was shaking as she put her hands on my hips.

“Is this what you want? To be touched? To be led? To be reminded of your place?”

Her hands dropped and slid under my skirt. My breath caught in my chest and I could barely hear her over the pounding of my heart in my ears.

“Show me you want it. Give it to me.” Her hands worked up to my ass and she gripped each cheek. Reflexively, I pushed my butt into her hands. I inhaled sharply as she squeezed.

“That’s it. That’s a good girl.” She whispered into my ear. “You know what to do; you know what I want.”

One hand snaked around my hip to rub the wet spot. I felt her finger press slightly against my inner thighs and I spread my legs a little. I could feel her grin on the nape of my neck, her hot breath sending tingles down my spine.

I couldn’t pinpoint the exact moment, but I found myself bent over the bed, my butt sticking out, and her hand between my legs.

“Eager girl!” She said, playfully slapping my butt. “Let’s see what we have here.”

She lifted up the skirt and dropped the hemline on my back, causing me to shudder. She ran her hands up the back of my thighs before grasping my hips and slamming hers into me.

“Men are not gentle. They are rough and they take what they want, when they want.” She slammed into me again. And again. I clenched her blanket, recalling how Patty had similarly been as aggressive and the stories Monica had shared. I wanted more. I wanted to feel what she had felt.

“And that’s enough for today!” Monica exclaimed, letting go of my hips and dropping the skirt back where it should be. “Playtime is over.”

I groaned and tried to hold onto the feelings. “That was playtime?” “That was a taste. Nothing more.”

“A taste?” I asked, standing up. I was a little light headed.

“Yes, now kindly take off my clothes. I need to get you back in this diaper before I take you home.”

The sudden shift was as upsetting as it was jarring. “What did I do wrong?” I said.

There must have been panic in my voice because she assured me.

“You didn’t do anything wrong. I have to have you home soon is all.” She said, holding my hands. “Besides, can’t have you getting too much of a good thing, you’ll end up a spoiled brat!”

She pulled the shirt up over my head and tossed it on the bed. I had a chance to look down at the padded bra I was wearing. It was strange to see something protruding from my chest. It blocked my view and seemed unnatural. I did, though, liked the curves it gave me, however artificial they were.

“Take off your skirt.” She said, “Does that sound weird to you? It kinda does to

me.”

“It feels like I’m stripping for you.” I said, undoing the zipper on the side and

letting it fall off my hips.

“You kinda are.” She said as I stepped out of them. She picked them up with one hand and ran her other hand up my inner thigh. She stopped at my wet spot and had a strange little grin on her face. “God you are so wet! Like a girl ready to be fucked.”

I didn’t want to admit that she was right. I did want sex. I wanted someone to bend me back over and take me.

She must have noticed my expression. “Do you recognize that feeling?” I nodded.

“Good. Hold onto it. That’s your first lesson.” “Lesson?”

“Being a girl is more than just looking the part. You have to know and play the part. This is you being a horny toad.” She held her hand up to my face. “This is your little clitty leaking, which shows everyone how bad you want it.”

I’d only heard about the term clitty from the sissy porn I used to watch. It was a degrading reference to an inadequate males genitalia, likening it to a woman’s clitoris. The general premise was that a sissy’s clitty was to remain locked in order to better serve real men.

“And from the looks of it, you really really want it! These panties are soaked! Get them off so that I can’t get you back in your diaper.” She peeled one open, fluffed it and laid it on the bed.

I peeled the panties off, feeling the last of Chrissy fade away. I sat down on the diaper, feeling its familiar comfort soothe my mind. I tried to get the bra off but didn’t have the talent to manage it.

“Here, let me do that. You’ll stretch it out the way you’re going.”

With the last of her clothes off me, I laid back and let her diaper me. I felt a bit of sadness that it was all over. I felt like I had gotten close to something, something I couldn’t quite identify, but something that I wanted.

When she was done, I stood up and pulled my leggings up over my butt. It wasn’t the same as the panties but it helped.

“You need to wash the makeup off. The bathroom is down the hall on the left.” “I will, right before we leave. I just…” I stood in front of the mirror looking at my

reflection, “want to…”

Exasperated, I turned from the mirror and went down the hall. Using a dark washcloth, I wiped the makeup off. I paused for a moment to wet myself before I finished the job. My stomach growled and my baby brain reminded me that it was feeding time. I looked at my phone. It was almost time.

Monica left shortly after dropping me off. Mommy checked to see if I was wearing my diaper and sent her on her way. She took me back into the bedroom to change me.

As she promised, she took the cage off, but didn’t immediately diaper me. She had me lay in her lap naked and I latched onto her breast.

“Did you have fun, baby?” She asked me. I nodded in response. “I hoped so. You really like Monica, don’t you?”

I nodded, swallowing fast.

“Did anything interesting happen?” I cocked an eyebrow in a question.

“I only ask because it looks like you have some mascara smudged under your eyes.” She peeled her nipple out of my mouth and a stream of breast milk ran down my face.

“Uh…” I stammered. “She was testing out some new techniques.” “And this interests you?”

“Not really.”

“It would seem that your body disagrees.” She grasped my erect manhood. “You’re awfully excited for someone who isn’t interested.

“In fact,” she said, sliding her hand up and catching my ooze, “I’d say you really enjoyed it.”

“I…uhhnn.” I moaned.

“I thought so. Very well, go get me a diaper.”

I got up off her lap and tried to walk, bobbing at every step. I was working on calming down by the time I brought it to her.

“Give me that.” She said; I handed it to her and she unfolded it and sat it in her lap. “Over my lap on all fours.”

I crawled onto her lap, hovering over the diaper.

“This will be a nice little funishment for you.” She said, taking my manhood in one hand. Her other hand lightly slapped my butt. “I’m going to ask you some questions and if I don’t like the answer, I’m going to work you up and then spank you.”

To prove her point, she started working her hand. I became trembling almost immediately, still worked up from Monica’s.

“Was she trying a new technique?”

“Y-yes.” She moved her hand and my brain turned to jelly. I moaned and got my ass cheeks slapped several times.

“The truth.” She said, resuming her touches. I moaned and squirmed.

“I…” I paused, breathing heavily. “I…wanted…”

Slap. Slap. Slap. Slap.

“You wanted her to put makeup on you? Why?” “I…”

Slap. Slap. Slap. Slap.

“I supposed that wasn’t the only thing she put on you? Was it?” I shook my head.

“Did you wear some of her clothes?”

She stroked me to the point where I was ready to burst and stopped. I was afraid to answer, afraid to move.

“Not just some, then. A whole outfit. Let me guess, something slutty. Something to make you feel all girly.”

I barely moved my head when I nodded. “Did you take your diaper off?”

I knew the answer to that would be disastrous to me. I shook my head fervently. “I see. And is that what you want? To be girly? I mean, you already wear cute

girly diapers, why not go for the whole kit and kaboodle?”

If I had learned anything about past decisions, saying yes to that question would be the disposal of all of my boy clothes and I’d be stuck in pink diapers and girl clothes forever.

It was one day. One event. It doesn't mean that I’m ready for anything like that all the time.

I hesitantly shook my head. I stared straight ahead, unable to discern if she believed me or not.

“Just experimenting then, I see. Very well.” She let go of my manhood and patted my bottom. “Let’s get you in this diaper before you pee all over the place.”

I ached. I was pent up and desperately wanted a release. “B-but…” I whimpered.

“But what?”

“...puh-puh-pwease?” I breathed.

“No. Dirty little boys that tell fibs don’t get special treats.” “I wasn’t lying!”

“You were, and you still are. Now, I’ve neglected to give you a real spanking, but I wouldn’t push me if I were you.” She said, “I know for a fact that you took your diaper off. Do you think I’m blind? I can see the red marks from the tight panties you were

wearing!”

My stomach sank. I blubbered in agony as I sat back on my haunches.

“I haven’t even given you anything to cry about!” She said, “I’m not even upset that you wanted to dress up like a girl and feel all pretty. I’m upset that you don’t trust me enough to talk to me about it.”

Between sobs I blurted out, “B-because I don’t know if I w-want t-to b-b-be a girl all the t-time!”

“All the time? What do you mean?”

“Every time I want to try something, even for a little bit, it always ends up that I’m stuck that way forever!” I said. My face was red and tears were falling. “I don’t know

what I want but I don’t need every decision made for me. I want to be able to decide what and who I want to be. On my terms! No one else’s!”

“If this is about wearing leggings, I won’t make you.”

“It’s not just that. It’s everything! I made one anonymous profile on YourLife and now I’m somebody’s literal baby! I’m stuck in diapers around the clock and every now and then I want to just be me without being afraid of being punished for it!”

“I can understand that this is a bit of an adjustment for you. It’s an adjustment for me too.”

“What do you know? How can you possibly understand how I feel?”

“Because I know what it's like to have your entire world flipped on its head. I was happily married one day, divorced and miserable the next. It was only by sheer stupid

luck that I came across you and your infantile obsession, otherwise, I’d be single, lonely, and lactating, completely useless and worthless to anyone, much less a man.”

“You are not worthless.”

“And you are not just one thing, Chris. You’re a baby, sure, but I didn’t make you this way. If you want to wear panties every now and then, go right ahead. It’s your life. You live it how you see fit.”

“It’s not that simple! I can’t just take them off and forget that this ever happened.

You’ve seen the boxes. They keep getting delivered and I’m expected to use them.” “Because of your other mommy?”

I nodded. Wiping the tears from my eyes. “Is she here right now?”

I shook my head.

“Then what she doesn't know won’t hurt her.” She said, picking up the diaper. “If you don’t want to wear these, then you don’t have to. I won’t force them on you. I won’t force anything on you that you don’t want.”

“But you know that I want them. You know how much I like being pushed around and forced to do things. That’s why you moved in. So you could breastfeed me

whenever you wanted to.”

“I can go back to pumping.” “That’s stupid. I’m right here.”

“Yes, you are. But it’s clear to me that you are not happy with the way things are working.”

“I…I just want to have a little bit of freedom…to experiment, I guess.” “Okay. What do you suggest?”

“I-I don’t know. I don’t know how to make good decisions.”

“The irony.” She said, “How about this, how about we reach a compromise? How about we make some rules that will let you do what you want to do while maintaining the status quo. Clearly, you are still a baby, I mean, look, you are dribbling all over the couch.”

I looked down to see a dark wet spot underneath me. My sexual arousal was leaking out of me.

“So, diapers are a must, but, let’s compromise and say that when you are out with Monica, you can take them off if you so wish?”

“Uhh, okay.”

“But, all little messes like the one you are making have to happen in a diaper.”

That’s odd, I thought.

She reached over and took a hold of my manhood, which was quick to respond to her touches. She pulled it gently and I returned to my position across her lap.

“I don’t want to hold you back from exploring your identity. I just want you to be safe.” She slowly worked me up again. “And the safest place you can be is in my arms, right?”

I moaned in agreement. I felt her repositioning the diaper. Her other hand then went to my butt where she rubbed and massaged it. “Afterall, who better to teach you how to be a girl than a girl? And who else better to teach you what girls like?”

I moaned louder, picturing how I looked in the mirror. I felt her fingers work their way between my cheeks and I felt a little bit of Chrissy welling up inside. I whimper moaned, ready for release.

“Cum for Mommy, baby. Cum for me.”

I exploded into the waiting seat of the diaper as she pumped every last drop out

of me.

“That’s it. That’s a good baby. Make those messes in your diapers for Mommy.” I

shuddered and quaked, my mind blown from the overwhelming events of the day. “Such a good baby. Come now, let’s get a diaper on you so you can finish nursing.”

I didn’t think about the details as I lay down, letting her put the used diaper on me. I could feel the wetness smear across my butt as I lay in it. Once secured, I spun around and latched back on her breast as she swapped between stroking my hair and patting my butt.

“You are so beautiful, baby. Mommy loves you.”

I murmured in response to her, exhausted from my emotional outburst and my sexual release. I could feel my exploits and its significance wasn’t lost on me. I was too tired to care, but Chrissy was loving it. A full tummy and sleep called to me. I needed a nap before I could process all that had happened.