Turning Sissy - Week 05 Pt. 02

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

*

I was running out of energy. Glancing over at the clock on the wall I saw it was 8:54 PM. I had 6 minutes left and I'd be able to go home with at least a shred of dignity. I knew it would be hard but it had to be done. My eyes scanned back up to the screen and I watched as the dildo fucked the cum out of me earlier in the day. It seemed so easy then, why was I having such a tough time now?

"Unnngh" I moaned as I slammed my hips down on the dildo suction cupped to the floor. I rocked my hips back and forth trying to build the pleasure back up again.

"Ahem." he cleared his throat and my eyes shot up to him standing beside me.

"I'm sorry daddy!" I said and opened my mouth wide, allowing him to push his cock inside.

He fucked my mouth gently, and I was thankful for it because it allowed me to focus on my own pleasure. Two more minutes had ticked by and I was beginning to get desperate. Riding the dildo felt good but it just didn't feel the same as getting fucked by one. I knew if I worked it for long enough I would cum but trying to get there in 4 minutes was hopeless. I decided to swallow my pride.

I pulled back and let his cock pop out of mouth pussy. Reaching down I pulled the suction cup free and moved forward down on my knees in front of him. I held the dildo deep inside me with one hand and lamented that both cameras had a great view of what I was about to beg for.

"Can you... fuck me with the dildo daddy? Pretty please? I want to cum so badly."

He walked behind me and took hold of the dildo, allowing me to let go of it. I smiled excitedly and genuinely at the prospect of him helping, forgetting the cameras were even there.

"Sure, daddy can help his little buttslut." he said.

Although his words gave me relief, confusion followed quickly when he pulled the dildo all the way out and set it on the floor next to me. At this point I felt something warm and thick press up against my weakened asshole.

"Just say yes" he said.

I turned around and saw his cock, hard and thick pressed up to my hole, the tip just barely beginning to spread my sphincter. My eyes went wide and I quickly looked at the clock. It was 8:58.

"I can make you cum in 30 seconds, just say yes" he promised.

"Please... not that... can you use the dildo?" I asked, knowing the answer.

After he neglected to even answer the question I panicked, watching the clock change again. 8:59. I really didn't want to lose this bet, my mind was racing with how to win. The hard part was winning without going further than I wanted to. As soon as it entered my mind I blurted it out, regretting it immediately.

"Can you..." my throat suddenly felt dry, "Can you wear a condom?"

He laughed at the question. My face went red realizing I had admitted that I would allow him to fuck me with a condom on.

"No" he answered.

I froze, completely indecisive. Moments later his cock pulled away leaving the area where it had been cold and exposed to the air. Seconds later I looked back in time to see the dildo being pressed against my hole and pushed in slowly. I didn't need to look at the clock. I knew it was 9:00pm.

"You lost."

****7 hours earlier****

As I sat on the floor rubbing my pussy, I heard his motorcycle starting up. He was leaving. I didn't stop rubbing, just like he had instructed. Staring into my own eyes in the mirror, I rubbed my swollen little donut ring slowly and methodically. I thought back to the week before and how he had done it, trying to emulate that. Looking up at the clock reading 1:24 PM I wondered how long he would be gone for.

After about twenty minutes it became clear that I apparently didn't have the same ability the biker did. I had stopped repeating my mantra of 'I'm a good girl' and devoted all my brain power to ponder this. He was able to make me cum in a few minutes but I wasn't anywhere close to that. In fact, I wasn't horny at all and I almost had to laugh at the fact that just like a girl, I was drying up. I brought my rubbing hand up to my face and spat in it before bringing it back down to continue rubbing. It helped things for sure but it didn't seem to be enough. I tried spitting into my hand again but I was having trouble producing the much required saliva.

I looked around, realizing there was nothing but the anal beads lying in a small pool of lube on the floor 6 feet away. They wouldn't have been much help in the situation anyway. I looked back up at the camera and furrowed my brow. The camera sat there, still positioned toward me however I couldn't tell if the red light was on or off because of how low to the ground I was.

My memory was piqued and I recalled how much spit I had produced when he had been fucking my throat earlier. I looked at my hands and elected to use the left one, as the right one had been rubbing my hole for the past half hour or so. I may have been accustomed to humiliation but I wasn't about to taste my own ass. I started with a finger but quickly added another, reaching as far back into my throat as I could. It didn't take long to begin gagging and soon after I felt my mouth begin to water. Within another few minutes I was coughing and sputtering as drool was flowing out the corners of my mouth.

As I caught some with my right hand I reached down under my caged cock and rubbed it over my ass. Removing my fingers I spat more spit out into my right hand again and added even more, making sure I was well lubricated. I brought my left fingers back into my mouth and smiled a little, feeling slightly proud of my ingenuity. My eyes raised up and glanced at the camera again and my short lived pride disintegrated. Was that caught on camera? It couldn't have been. I told myself he wouldn't have left it running.

I looked at myself as I continued to rub and noticed the cage raise a tiny bit. A small jolt of pleasure hit me and I could feel my ass muscles tense almost involuntarily. With all the shame I was feeling that day, I couldn't help but embrace whatever good feeling I had. The urge was to strong not to chase the pleasure and soon I was rubbing harder and deeper. While closing my eyes, I let out a soft moan around the fingers in my mouth as I flexed my pelvic muscle again. I focused on recreating that feeling, and repeating the process again and again. The pleasure grew and grew and soon I was approaching the edge. I spat another big pool of thick saliva into my rubbing hand and worked it against my hole, faster now.

I opened my eyes and made eye contact with myself in the mirror. I was seeing the focused and almost aggressive expression on my face as I worked my pussy and it turned me on even more. I felt the orgasm building and right before I could cum I forced myself to pull my hand away. I couldn't let myself cum and there were two reasons why. The first was simple. The camera might have been recording. I was almost positive it wasn't, because he would have angled it for a better view if it had been, but I couldn't take the chance. To give him the satisfaction of cumming this way voluntarily and have a recording of it?

The second was simpler. It was only 2:00 PM and I had no idea when he'd be back. For all I knew he could have walked through the door at any moment. If I had just blown my load, it would make whatever he decided to do to me, or worse, have me do to him all the more harder. So I let my pleasure abate for a moment, rubbing gently and fighting the urge to clench my pelvic muscles. After a cooldown period, I began the process again, operating like a machine. I would rub with my right hand and harvest saliva with my left, building up to the edge of climax and then stop myself, repeating the cycle over and over again.

It was 4:30 PM when I heard the motorcycle coming up the driveway and although I heard it, the sound didn't really register. I had been edging like that for well over two hours and I was an absolute mess physically and mentally. He walked in and looked down at me and smiled with a chuckle before walking out if the room again. This seemed to break the spell I was under and I suddenly realized what I had been looking straight at in the mirror this whole time.

My asshole was still pink and a little puffy from all the rubbing and there was a surplus of saliva coating the entire area. As my hand moved up and down it made a wet shucking noise. When I moved it away, thick strands of spit kept it connected to my hole. A little further up, my cage rested, my limp cock inside contained and a long stream of clear precum hanging off the tip and onto my taint.

As my eyes moved up I saw that the front of the shirt was absolutely soaked in saliva and higher up still, my fingers were no longer in my mouth but rubbing themselves around my bottom lip. That was when I finally realized my lips were moving, and when that sunk in I could finally hear what I was saying.

"I'll be a good butt slut daddy, I'll be a good butt slut daddy"

As he walked in the room and locked eyes with me again I hit another edge and pulled my hand away, my hips bucking and asshole twitching involuntarily. I caught myself still trying to get out the words I had repeating and stopped it. As the edge came down I looked up at him, my mind was jello.

"Dirty little bitch. Lets get you cleaned up." he said.

He came around behind me and I turned my head with my mouth open ready for him to insert his cock.

"Jesus you are a horny bitch." he said, ignoring me.

I looked down, feeling a combination of embarrassment and deep arousal as he hooked his hands under my arms and lifted me up. He led me to a bedroom where he let me brace my arms on the counter as he peeled my clothes off. The shirt came first, followed by the skirt and then the stockings, bra, and sandals. Still unsteady, I was able to at least stand now that I wasn't wearing platform shoes. He handed me a towel and I put it down and turned toward the shower but felt his hand grab my arm tight.

"No. On your own time." he said and I realized I wouldn't be getting to thoroughly wash my body.

I began wiping myself down, drying up all the spit from my chest, eventually working my way to my taint and between my cheeks. I looked up into the mirror and saw my makeup was just a mess of color, barely existent anymore. Dried cum was flaking off on my forehead, nose and right cheek. I saw that he had left out some makeup and a face towel so I used warm water and went to work. Once I had finished, my makeup wasn't as glamorous as May had done earlier in the day, but I was able to make myself look cute again with little difficulty. I paused, leaning toward the mirror again and stared at my new bangs, briefly wondering how I would explain them to my friends.

He entered the bathroom behind me and I felt his hand find its way between my cheeks and his fingers pressing on my hole. I grabbed the counter to brace myself as the pleasure I had felt while rubbing my hole returned, full force.

"Whose pussy is this?" he asked.

"Yours daddy" I replied with zero hesitation.

My hips pushed back slightly to meet him as he rubbed around my pussy. All the edging I had done while waiting had left me in a state of hyper arousal. I had been hoping that by deferring an orgasm I could avoid the intense shame I felt afterward however now I was acting like a bitch in heat. My awareness of this didn't have much of an effect on my actions. As he pushed his fingers harder, I wiggled slightly to allow them to ease into my hole.

As he probed my pussy, I caught a glimpse of his other hand in the mirror. He noticed this and raised it, placing a small pump bottle of lube and the buttplug I had worn that morning on the counter. His fingers slipped deeper causing me to lean forward more and grip the counter harder.

"Unnngh" I let a moan escape.

He slapped my ass hard with his now free hand.

"Tell me what you were saying before while you lube that up." he ordered.

I remembered to breathe, exhaling deeply and raised myself up so I could lube the plug.

"I was saying that I'd be a good buttslut daddy." I said, as I pumped the lube into my hand.

"You like being a good buttslut for daddy?" he asked.

"Yes daddy", I answered, applying the lube generously to the plug, stroking it like a cock.

"Your asspussy isn't as tight as it was before you met me. You've been such a good little buttslut you can take two fingers without any lube." he teased.

My face went red but at the same time my cage felt a little fuller and I tightened my ass around his fingers reflexively.

"Thank me for making your pussy looser." he demanded.

"Thank you for loosening up my pussy, daddy." I said, my eyes watering as I thought of the changes he had made to my body.

"Give me the plug" he ordered.

I passed him the toy over my shoulder and he took it from me with his free hand. His fingers withdrew from my pussy and then I felt his hand grip my ponytail as I was shoved downward on the counter. my head was pulled back so I was looking at myself in the mirror. I gasped as he pushed the blunt end of the cock shaped plug against my puckered hole. As it pushed into me I felt myself stretching to the limit around its two inch girth. I thought of the unwanted effects of this intrusion and opted to beg.

"Please Daddy... it's too big... please..."

He laughed to himself and continued pushing it in.

It felt massive. As I felt myself stretching uncomfortably, I worried this size would become the norm. It seemed to only be getting bigger as it moved bit by bit into me. Finally I felt my ass close up around the neck and let myself exhale. He gave my ass another hard slap and released my hair before walking out.

"Put on the outfit in the bag and meet me in the living room."

I regained my composure and stood up straight. I saw the large paper bag on the counter and peeked inside. Inside was white platform new balance running shoes, two pink hair elastics, a pair of knee high white socks and a white cropped tank-top. At the bottom of the bag was a water bottle that I immediately uncapped and drank entirely. It didn't take long to get dressed and I wasn't surprised to find the crop-top said 'Daddy's girl' on it in girly pink writing. After working my hair into pigtails with the hair elastics, I left the bathroom unsteadily thanks to the large invader between my cheeks. Looking backwards on my way out I saw that the base actually held them open, advertising the fact that my asshole was being stretched beyond reason.

He was on the couch, when I entered the living room and he patted the spot next to him when he saw me. I walked around to the couch and sat down sideways with my legs up, remembering the previous visit on Halloween. He wasn't wearing pants at all, just a wife-beater. He leaned forward, picking up two tall glasses off the coffee table. The one he handed me looked like it had pink lemonade inside it and that was confirmed after my first sip. His glass was filled with beer. The TV in front of us played a PMV compilation of sissies being used in all manner of ways. My first drink went down quickly and it wasn't until I was finishing my second that I realized that there had been alcohol in it.

"Time for another." he said, finishing his second beer at the same time.

"I'm okay actually..." I said, not wanting to get too loopy.

He returned with another nonetheless, handing it to me without words. I took it reluctantly and sipped it slowly. It was seconds later when he pulled out a joint and began smoking it before handing it to me. I didn't even try and argue, taking it and accepting that I no longer had a say in my state of mind. Watching the video on the screen, my mind began to fade.

"You're dripping slut" he said, bringing me back from my zoning out.

I looked down and saw that there was precum on my thigh, dripping in a long strand from my cage. He swiped at it with his finger, and then held it up in front if my face. I opened my mouth to allow him to insert it but instead he wiped the sticky liquid across my lips. My mind, hazy and slow, was not offering much if any resistance in terms of shame. I licked my lips, tasting them, causing him to chuckle.

"Down." he said, snapping and pointing to the ground, "Facing the television"

I quickly moved into position, on all fours with my back arched and gave my ass a little wiggle. My eyes were focused on the television as I felt him grip the base of the plug and ease it out slowly. I focused on the sissy on screen dressed in a maid outfit riding a cock and let out a moan as the plug slid out of me and then stopped at the last inch. I gasped from the wave of pleasure that coursed through me as it was pushed back in. I heard a pattering sound underneath me and looking down I saw a small cloudy white puddle as the last drops of what looked like watery cum dribbling out of my cage. It had felt good as it happened but I knew it couldn't have been an orgasm, I was still as horny as ever and it wasn't anywhere near as powerful. He squeezed my cheeks and spoke.

"Getting a little too excited. Looks like we found your p spot. My little bitch is in heat." he commented.

His hands went around my neck with something and then moved away. I felt a small tug and realized he had collared and leashed me.

"Let's go" he said.

I crawled forward, careful to avoid the puddle when he tugged on the leash again.

"Wait. Lick up your mess." he ordered.

He turned me around with the leash and I lowered my head to the puddle. As my tongue touched the warm salty liquid I felt his hand push on the plug.

"Uhhhh" I let out a girly moan and began licking and slurping with purpose. When the floor was clean I looked up at him and smiled seductively feeling a little woozy from the alcohol. He nodded in approval and with a tug from the leash had me quickly crawling away with him.

He led me to his bedroom and motioned for me to get up on the bed. I climbed up, and sat there, smiling suggestively at him waiting for his order.

"Lay down." he said as he repositioned a camera and tripod on the desk.

Feeling just as he described before, 'in heat', I elected to lay back on the bed and lift my legs up, exposing the base of the plug between my cheeks. He saw this and chuckled.

"Not like that." he said as he came over and pulled me to the edge of the bed and hung my head backwards over it.

As his cock dangled in my face I felt a pressure beginning to build in my bladder from all the drinks. Before I could say anything his cock was pushing between my lips. It met slight resistance at the back of my throat but with some pushing, it popped through. I gagged immediately and he pulled back out for a moment, allowing me to catch my breath before pushing back in.

"Girls have three holes, sissies only have two," he began explaining as he waited for me to gag before pulling out briefly again, "So sissies have to work extra hard. Your mouth should be able to take cock as well as any other hole."

He continued the onslaught of stretching out my throat over and over, and pretty soon it began to get to me. I wouldn't open my mouth as enthusiastically, or I would turn my head away. After a few minutes of me getting increasingly reluctant to continue he shoved it in a little deeper than usual and after I gagged this time, he held it for a little longer before pulling it out slowly.

"Good... good mouth pussy." he said.

I coughed and saliva came sputtering down my face and he rubbed his cock across it, spreading it around. Tearing up, I began to beg a little.

"Please... please, no more."

He chuckled and slapped my face with his cock a few times. All the confidence and arousal I felt entering the room was now gone and he seemed to enjoy that.