Turning Sissy - Week 05 Pt. 02

"This is not about what you like or want. This is training. This is about you learning your place. Learning what your holes are for. Now open your mouth wide for daddy's cock."

I opened wide again and stuck my tongue out and he speared his dick back down my throat, easily burying it to the hilt. This time when I gagged, he did not remove it and instead held it there. I began struggling and my arms shot out instinctively and in vain to push him off. He simply reached down and grabbed my shriveled cock and balls tightly as an anchor to let me know he would decide when he left my throat.

"Relax, breath through your nose and relax." he instructed.

I tried my best, but my throat was spasming every few seconds, my gag reflex not allowing me to adjust. Thankfully he did pull out eventually and as he did phlegmy saliva poured out with his cock sliding down my face to the floor. I began whimpering and letting out uncontrollable but quiet sobs, wishing that it was over.

"Shhhhh." he said, "It's okay, just look... just look at my cock." he said in a more comforting tone.

I stared through the tears in my eyes at his cock head, my sobs now changing into sniffles, hiccups, and whimpers.

"Tell my cock you love him." he ordered.

I didn't speak and instead just looked at the cock that had violated my throat for the past 10 minutes, crying softly.

"Tell it." he said, squeezing my balls tightly.

"I love *hic* you." I said, staring right at the foreskin covered head.

"Now ask him if you can kiss him." he ordered.

"No... please. Please, can we *hic* stop... just for a bi- *hic*- it?"

Another hard squeeze and I understood this was non-negotiable.

He released me and pulled me off the bed so I could kneel in front of him.

"Can... *hic*... can I kiss you please?" I asked, staring up at the man's face.

"Not me faggot. My cock. Ask my cock." he laughed.

I looked straight at his cock and repeated the question, fighting back more tears.

He pulled his foreskin back and bared his cock head. It was utterly caked and covered in precum and he chuckled out as he moved it closer.

"You go ahead. Kiss it like you're head over heels in love with it."

I leaned in slowly, tears flowing slowly out of my eyes and allowed my lips to press against the tip. The precum had a strong musky aroma and I fought the urge to gag. I pulled back away slowly before moving back in, this time opening my mouth a little bit and allowing my tongue to rub the underside of the head. I continued this, not just sucking but actually making out with his cock head, treating it like I would someone's lips and tongue. I wasn't sure if it lasted 5 minutes or 50 but eventually just as my own arousal was beginning to build, he pulled it away.

"Oh no. Look at that." He said, looking down at the floor with a look of concern that didn't seem wholly genuine.

I looked down and saw that I was leaking profusely. It confused me for a moment as I wasn't even that aroused. It was when I saw the puddle below me that I realized it was not pre cum or even cum that I was leaking. I flexed my pelvic muscles to stop the stream of pee and looked up at him in horror.

"That's the second time. Like I said before, it happens sometimes. Especially when a new girl is learning her place." he walked over to his closet and began rummaging around before returning with a small purple folded piece of linen.

He began unfolding it and I realized quickly it was not in fact meant to clean up the floor. He handed me the fabric and its inorganic texture told me what I had feared.

"No, please... I don't... I don't need it." I said, "Please, I just need to go to the..."

He placed a finger over my lips.

"Shhhhh", he hushed me calmly and used his free hand to wipe away my new tears, "Trust me, you need this. It's not a negotiation."

I reluctantly stood up and stepped into the pull-ups one leg at a time, feeling more embarrassed than I had up until this point. When they were all the way up he gave a short laugh and slapped my now lightly padded ass hard.

"Good girl. Now you don't have to worry. You can let it all out."

He took the leash off, leaving the collar on my neck and stood me up. My bladder was still quite full but I was determined not to further degrade myself.

"And guess what?" he asked not waiting for an answer, "Good girls get rewarded."

He walked me to the living room again and had me sit in a large well cushioned chair. He had me raise and spread my legs, obviously to provide the camera with the most humiliating view. He turned the TV on and it showed the sissy from the other videos frozen in the frame. I remembered watching him utterly degrade her while wearing her sister's cheerleading uniform and began to get aroused. In this frozen frame she was wearing black nylon stockings with an intricate lacy pattern around the top. She also wore a matching bra and below black, silky, skirted panties. Her cock was encased in a cage similar to the one I had worn and it was exposed through a hole in the panties. I didn't recognize the background, and noticed that the bed she sat on and the room around it was not one I had seen in his house.

My hand found its way between my legs but I caught myself and removed it before he could make a comment. He chuckled to himself as he hit play on the remote. The sissy sat on the bed on her knees and the man spoke to her in a somewhat more enthusiastic voice than he had used with me.

"So, this is our last visit, isn't it?" he asked.

"Yes daddy." she said.

"Are you going to miss Daddy's cock?" he asked.

"Yes, I will sir." she said, the look on her face was strained, it was clear tgere was mixed feelings despite her smiling.

"Get into position 3." he said.

She scrambled onto her back bear the edge of the bed and pulled her legs up and held them. The camera, moved closer and I realized it was handheld, being recorded in POV style. The view angled down to reveal the panties the sissy wore were crotchless, exposing her ass pussy fully. His cock entered the frame and pushed inside her with little resistance before the view moved up to her face.

Just then, he handed me something as I watched the video. I looked at it and recognized it immediately as a magic wand vibrator. It was obvious what he wanted me to do, and I didn't waste any time before turning it on and pressing it through the fabric to my perineum. I continued watching the video, now totally aroused, and despite still having a full bladder finding pleasure in the vibrations.

He fucked her in the same position for a while before he snapped his fingers and she flipped herself around and stuck her ass in the air. Spanking her as he fucked her she began moaning, quietly at first but eventually the dirty talk came out in spades. 'Fuck me daddy' and 'You own this pussy' were among the more tame things she said. My own pleasure was building as well and I was certainly enjoying the video whether I would like to admit it or not. Finally, she was back in tge original position announcing she would cum soon and was begging him, 'cum in my fucking pussy' repeatedly when he withdrew all the way.

"Please... please daddy, fuck me, cuhh... cum in meee..." she begged as her body writhed around on the bed after being denied the orgasm it wanted so badly.

"I have a proposal." he announced to her, "You've finished your 10 sessions. Once I let you go today, you will be free, but..." he pushed his cock back into her balls deep and the look of shocked pleasure on her face almost sent me over the edge.

"But, I'm going to offer you one more deal. 5 more full day sessions, this time with no limits at all at $5000 a day. That's $25,000 total." he offered her.

"Oh fuuuuck." she said, her eyes closing as he began slowly pumping his cock in and out of her.

"If you decline though. That's it. You won't serve me again. Do not contact me, do not ask, do not beg. I promise you will regret even trying." he warned.

"No... please... no, no more deals" she said, surprising me completely.

"Suit yourself" he said and pulled out all the way before shooting rope after rope of cum over her.

Cum hit her caged clit, her bra covered tits, her face, the bed spread. It was a complete mess. and she sat there, with the horrified realization he wasn't going to make her cum. He pulled her by the legs down off the bed on the floor in front if him and wiped his slimy cock across her face as she scrunched her eyes close because of the cum. Then, his cock let go of something else. Piss sprayed out over her, completely drenching her hair, outfit, foot of the bed behind her, and the carpet. When he was finished made one final comment before the camera stopped filming,

"Your mom has good taste in lingerie. Hopefully your parents don't mind their bedroom smelling like piss and cum."

I didn't exactly cum but I did feel sudden leg shaking pleasure upon realizing that this had taken place in the sissy's parents bedroom. This was the deal he had offered her, the one she had turned down. He had pissed on her in her parents bedroom and she still came crawling back to him only to be humiliated even worse! My bladder released fully upon this realization and I felt warm liquid spreading and leaking out the sides of my legs. He chuckled as he watched me twitch in pleasure from the vibrator. I felt my face turning red and as he took the vibrator away from me I let out a whimper. I was still very horny despite the intense shame I felt after wetting myself. I sat on the now damp armchair in shame until he spoke.

"Looks like the days almost done." he announced beckoning over at the clock.

I saw the clock on the wall now read half past eight.

"Before you go I'm going to make a little bet with you. Follow me."

He led me through the house to the kitchen where a single dildo sat, suction cupped to to the tile floor. He carried a camera with him which he wasted no time setting up. He also set up a laptop and began playing a video that didn't take me long to recognize. It was

"The rules are simple. You have until nine to make yourself cum. If you do, you win. If you don't, I win. Fun right?"

I looked at him skeptically.

"What do I get if I win?" I asked.

"What do you want?" he countered before seeing my eyes light up and quickly adding, "Nothing that changes the negotiated length of our deal."

I thought for a moment, acutely aware I was wasting precious time I could be spending winning the bet. I thought back to the offer he extended to the sissy in the video. The amount if money he was willing to pay was quite high so I knew it was something within the realm of possibility.

"Double the money." I said, "Double the money for today."

"Done." he said with zero hesitation and I knew instantly that I could have asked for even more.

"And if I win..." he began, "We go on a field trip for our next session."

I had no idea what he meant by that and I sat on the floor, the confusion written out plainly on my face. I knew whatever it was, it wasn't good but his next words snapped me out of my apprehensive state.

"What are you waiting for? You have just over 25 minutes." he reminded as I scrambled to remove my embarrassing underwear and sit on the phallus mounted to the floor in front of me.

****25 minutes later****

I sat on the cold floor, the dildo still firmly inserted fully inside me as he stared down grinning. I wanted to fall straight through that floor due to the intense regret I felt. He had opened up the idea of him fucking me, and whether I wanted to acknowledge it or not I was in the process if negotiating it when the time elapsed. I had also lost the bet and although I didn't know what a field trip was or how it differed from the errands we had run that morning, I knew it would be awful.

"You can go clean up now." he said, finally.

In the washroom I removed the dildo and cleaned it before taking the next ten minutes to strip down and clean myself up. I removed the thankfully detachable hoop earrings from the studs that would now be in place for at least a few days while my ears healed. I glimpsed my bellybutton, lamenting that the jewelry would be on me for the foreseeable future. Once I was satisfied I was clean enough for the journey home, I grabbed my backpack and reached in for my clothes. Surprisingly, I did not find the clothes I had worn in the morning. Instead I found pink sweatpants and a matching pink sweater that didn't quite cover my bellybutton, as well as a fresh pair of pull-ups. I groaned audibly as I came to terms with the fact that my evening wasn't over yet. I began dressing and even took the initiative of reapplying my makeup before going to meet my tormentor.

"Wow, and I was expecting a fight on the outfit. You even did your make up, good girl." he greeted me.

"What do you want me to do now?" I asked as politely as possible.

He laughed and looked amused before a look of realization swept over his face.

"Oh, and here I thought some brains made it through your training... We are done for the day. Go home." he said.

"But... my clothes? Where are..." I trailed off after seeing his grin.

"Long gone. This is the outfit you wear when you show up, and when you leave from now on. If you show up in anything else, you'll be sorry you did." he said as he handed me my backpack and placed a hand on my shoulder.

He guided me to the front door as I began arguing.

"Bu-but I can't... I mean, my dorm, everyone will see!" I said.

"Not my problem." he said as he ushered me out the open door and into the night.

Before he shut the door, just behind him in the mirror I saw my reflection as I looked over my shoulder. My hair was the first thing catching my attention, initiating a moment of panic that it was now pink, not to mention I now had bangs. With the makeup I still looked like a girl through and through, giving me the confidence I may be able to sneak into the dorms unnoticed. The last thing I saw before the door closed was something that would catch everyone's attention, the tattoo on my lower back that read "Daddy's Butt Slut". I walked slowly to the bus stop, already planning out my journey home and mercifully caught the bus moments later.

After an absolutely embarrassing trip to Walmart, I finally climbed the back staircase leading to my dorm room. Wearing a thick beanie hat, oversized sweater I was able to sneak inside without anyone actually taking notice. Thankfully I lived in a single dorm, so aside from the bathroom that I shared with my neighbor I had plenty of privacy. That was a good thing, because I was so tired from the day's events, I ended up sleeping in the clothes he had provided, my cage leaking as I wished for the orgasm I knew would not come.