Turning Sissy - Week 03

ATTN: All characters are purely fictional. All characters are over the age of eighteen. This story contains elements of reluctance and non-consent.

The next 6 days were torture. I was used to masturbating multiple times a day so not only was I horny, every time I started getting turned on my cock would try to grow and cause discomfort in the cage. I did my best to keep everything clean but it proved to be a full time job. At some points I had almost a steady stream of sticky clear pre-cum oozing out of the pee hole. On top of this I realized quickly that I had to sit down to pee and wipe like a girl, which was itself humiliating. Other than that my life didn't change much, it wasn't like I was getting laid before I had the cage. Once again time seemed to move slowly through the week but sure enough it passed and before I knew it I was on his doorstep again.

Upon entering his house for the third time I walked immediately to the bathroom and showered. This time on the counter by the sink there was not only the usual panties, collar and stockings, but also eyeshadow, blush, and lipgloss. In addition to these were a pair of pink lace up high heels that resembled running shoes in my exact size. My mouth gaped. As I applied the lip gloss and blush I couldn't believe I had gone so far for this disgusting man. I told myself I had no choice and if I didn't want to be publicly humiliated I just had to get through it.

I exited the washroom unsteadily wearing the new accessories and was greeted by a wolf whistle.

"What do you say for the new gifts?"

"Thank you" I said quickly.

He cleared his throat and I realized my mistake.

"Thank you daddy" I corrected myself.

"Let's get a better view of how it all works together. Do a fashion walk for me." he said sitting on the couch.

I stumbled through my attempt, very uneasy on the heels even though they were chunky like platform shoes.

"Hmmm try again'

I walked up and down the living room once more leaning forward on my toes for balance, again stumbling more than once.

"Try tightening your butt muscles and relaxing your lower back. Stand up more straight too." he coached.

No dice. Again I barely made it across the room.

"That's okay. I have an idea."

He left the room and returned holding out a pump bottle and something small and pink. It took a second but I recognized it as a butt plug.

"Do you want to put it in yourself or do you want me to help?"

I swallowed hard. It was getting clearer now as if the outfit didn't give it away already. He was trying to groom me. Last week was stockings and a collar, this week it was makeup, heels, and a butt plug. What was next week going to be? I had to take a stand.

"No daddy, I'm not going to wear that" I said as politically as possible.

He sighed audibly.

"Have you forgotten our agreement?"

he asked, "Anything goes for 3 hours a week. You're telling me you want to void our agreement?"

I stood there trying to show no emotion as I thought about what that meant. My end of the deal was clear, do whatever he says. His end of the deal was to pay me but more importantly it was to delete the Grindr profile and not put up a Tinder one. Being in college, everyone I knew was on Tinder so it wouldn't take long for something like that to damage my reputation.

"No" I finally answered understanding the gravity of my situation.

"Then let me repeat my question, do you want to do it yourself or do you want help?"

I took it from him and turned to walk to the bathroom but felt a hand grip my arm.

"No. Right here."

My heart sank as he guided me to the ottoman and had me kneel on it. I looked at the plug in my hand as he hooked his thumbs under my panties and pulled them down. It was pink, translucent and rubbery, and at just under an inch wide and only 3 and half inches long it so it wasn't very big.

"Use some lube on your hole and on the plug. It'll go in easier." he instructed.

I took his advice and made sure to coat the plug in a generous amount of the slippery gel. I took some more in my hand and reached underneath and behind me. As I did I felt hands grip and spread my ass cheeks wide causing me to panic and jerk forward.

"Relax girl" he said and gave the right one a quick slap, "This will help"

He spread them again and I felt completely exposed as the cool air touched my hole. I rubbed the gel on it carefully not really sure what I was doing.

"Push some in honey. Just your finger tip." he guided.

I followed his instructions and breathed heavily as the cool gel was pushed inside slightly. My finger slipped in a little bit and as I tried to guide more lube in it went past the nail almost halfway in. It felt uncomfortable and slightly painful.

"Look at you, now you're just playing with yourself." he laughed.

I held the plug up to my hole and took a deep breath before pushing slightly. It didn't move very far so I gave it more effort. The tip seemed to slip in and I began to coax it in further but even at its small size it was stretching me uncomfortably. The biker must have been getting impatient because I felt one of his massive thumbs over my finger apply pressure and push steadily. The plug invaded my hole and at its widest point seemed to get pulled inside me with little effort. He gave me another spank and pulled my panties up before helping me to my feet.

"How's it feel?" he asked.

"A little uncomfortable but not as bad as I thought it would" I answered honestly.

"You're a little tight. Just means we have to loosen you up. Let's try again, walk across the room for me."

Loosen me up. The words hung over me but I persevered walking steadily forward. As I did I resolved that this was the first and last thing that was going back there. Surprisingly he wasn't wrong about the plug helping me walk in the heels. The uncomfortable feeling in my ass translated to a much easier time balancing and finding my center of gravity. I paced the room twice and looked back at him, feeling pride for a moment before remembering my situation.

"Much better" he complimented, "But still needs some work"

He had me do his dishes, sweep his floors, and then his laundry. There was still another hour and a half left when I found him in the living room, the laptop on the floor in the same spot as the week before. He nodded his head toward it and I found my place on the ground, put my headphones on, and pressed play. I had grown somewhat used to the plug inside me and as the images began flashing I almost became unaware of it. In fact as the music built I found myself clenching on it in beat and felt my cock grow inside its cage. As the words flashed against the screen I kept having to remind myself it didn't apply to me. The phrases were much more obscene than the video from the week prior. "You are a cocksucker" and "You need your ass filled" were repeated moreso than any others.

As I watched I felt my panties being pulled down and a hand pushing my back down, helping me arch. I looked back and he gave me a spank before returning to the couch.

It wasn't long after when I first felt the plug slipping slightly. I clench down and found that I could kind of control it with my muscles and pull it back in, holding it there. This worked a couple times but eventually I couldn't hold it and it slipped out onto the floor. I pulled the headphones off one ear and turned to look at my business partner.

"Hmmm looks like we need to go up a size." he remarked.

"Uhh, no, I pushed it out by accident... it's fine really." I said, sounding more desperate than I meant to.

"Eyes forward. Reach back and spread your cheeks, I'll get it in." he responded.

"No... really, it'll just slip in, I can do it." I pleaded.

I watched as he picked up the plug from the ground and put it on my back as if it were a table before getting up and walking away. I went to reach for it but he turned around.

"If that plug moves, it's going in your mouth." he said in a serious tone.

I focused all my energy on staying perfectly still. He couldn't mean that could he? They did stuff like that in porn but it was always after the camera cut, giving the actors time to clean. His tone showed how serious he was however and I wasn't about to risk it. He returned quickly and I heard him kneel behind me. He fiddled with something for a moment and then I felt something cold and blunt at my hole. At this point he had not picked up the plug from my back yet and I realized he would be inserting a new one. The pressure began slowly and gently but then increased suddenly until I felt a slight pop. There was more pressure after this and I grit my teeth, my muscles contracting until I felt the pressure grow.

"Relax and push out." he said calmly.

"Out?" I questioned and received a quick spank in retort.

I did as he asked even thought it seemed counterintuitive. Miraculously the pain subsided as the pressure grew and he pushed it into me all the way. It felt huge by the time my ass sucked the last bit in and my curiosity got the better of me.

"How much bigger is this one?" I asked, the mix of discomfort and slight pain making my voice waver slightly.

"You'll find out when you take it out later."

I put the headphones back on and focused on images filling the laptop screen to distract me from the new invader. I told myself there was no way this one would be falling out on its own. Thankfully the last bit of time went by faster than expected. I felt the panties being pulled up and a slap on my ass and noticed that I had stayed 15 minutes longer than I had to.

"I didn't want to disturb you, it looked like you were enjoying yourself." he said and gave my cage a poke.

I looked down and saw a dark wet spot on the front of my panties and a string of pre-cum hanging down from it. I was mortified as he continued to speak and reassure me.

"Its okay honey, perfectly natural."

He helped me to my feet and passed me my clothes and I began walking to the bathroom to extract the plug.

"Hold it." he commanded and I stopped.

"You're still not walking how I want you to. The plug stays in, for at least one hour. You should wear it for a minimum of one hour every night before next week's session and practice your walking. Take the heels with you too."

I arrived at my apartment and noticed he had sent me a message on Grindr. It was a link to a Google drive folder filled with videos titled with numbers. I clicked through them and realized they were similar to the videos he made me watch at his house. I put one on out of curiosity and began watching. The content was the same and porn clips would flash on the screen. Mostly straight amateur stuff but occasionally a cross dresser or shemale would pop up for a moment. I felt the plug inside stretching me and as I watched I would squeeze it with my muscles. The music was pulsing and words flashed inbetween pictures and video clips. I had a hard time focusing on them and just zoned out. When the video ended, I saw that once again I had lost track of the time. I had been home for a full two hours. I closed the browser and then ventured into the bathroom to remove the plug.

After some trouble I was able to get it out with only minimal discomfort and when I did I understood why he hadn't shown it to me before. It was remarkably similar to the previous one in texture and shape but that was where the similarities ended. This plug was at least 1.5 inches wide and 4.5 long. A considerable step up for the anal virgin that I was. The other notable attribute of the plug was that it was cock shaped, with a plump head even. I washed it carefully in the sink and then put it down on my desk before going to bed finally.