56 Start of Training

I moved through the Inn and went to an employee asking for some food for four. I decided that he needed to eat since we had held him captive for a day at least. I waited at a table while she brought out food. The employees were looking worried about something and I almost slapped my face remembering this was a business. I took their manager I will send Rose a message. I did just that as I took my food up to the room telling her to stop by and make an excuse for her husband and do the manager work quickly. I was surprised when my mother sent back a message.

"Honey, Rose, and I have received your message. I have taken your girls for the night so start what you need starting. We will see you tomorrow and talk then. Have a good evening Sweety." The mana dissipated and my eyelid twitched a couple of times. I have no idea what to make of this. I stood a little stunned about the message outside the door to my room. I shook my head waking myself up before entering. The Innkeeper was still tied to the chair as I entered the restraints though had loosened a bit. He was sweating in excursion from trying to free himself.

I wasn't going to really like what I was going to do to the man tonight. Sometimes though you need to do things that you don't like. Though it will have something to do with experiments I wanted to try still on Betsy. She knew it was coming but I needed test subjects first. A smile came to my face thinking of the Data I was going to gather while fulfilling the mission I set for myself.

The Innkeeper heard me walk in and looked at me resentfully. I took out the Gag and put a barrier of mana throughout the room. It wasn't as good a Mally's and without wards, it wasn't permanent but unless someone was trying to peep inside with mana then nothing would be heard. I also would detect it and be able to find the person. I was deciding how to start this when I smelled his stench. I almost wanted yo puke. He had biology all over him and it fucking stank. First was cleaning up with a bath then. I sent a message to the employee in charge to take the private baths. They had already been booked. I went downstairs and asked if I could pay gold to take the spot. I received a message from the person who booked it.

"Chelsea, I knew you would want this tonight and you forgot to book it since I took Emily for the day yesterday. Love, Mom"

'The people around me know me too well,' I thought to myself and smiled saying this message was to say the private booking was for myself. The Employee confirmed and told two others to get it ready.

"Ready in ten minutes Ma'am Have a good evening."

"What a fucking useless prick," I mumbled as I took him off the chair. The restraints free he tried to run to the door. Mana enhanced I was in front of the door by the time he was even halfway there. I looked a the pathetic elf run towards me while looking back. He was astonished not to see me and turned to the door. His face met with my foot almost breaking it. He held his nose and groaned. I sighed as he wasn't going to make this easy. I picked him up by the hair and looked into his teary eyes.

"There are three ways this can go down. First is the way you just started. With lots of pain for you and a fucking pain in the ass for me. The second way this can go down is you do as your told and it will not be as painful. This will eventually even turn pleasurable for you and me and we can enjoy ourselves. The third was is a continuation of the first." My face turned grim and dark, "That is essentially you make this a big enough pain in the ass for me I say fuck it and just kill you. I take my time and find a dark corner with monsters tossing you corpse to them."

I looked him straight in those widened tear-filled eyes. "Now which will you choose," I spoke simply the Threat implicit and hanging between us. The groans turned to sobs and he looked at me looking for mercy. I stared not showing the least consideration to the things I have done to him. This was something I truly detested but I knew the earliest part was the hardest. I did not like myself while I was doing this either. Revenge was one thing this was another altogether.

"The second." He simply spoke between sobs. I dropped the pathetic wreak and looked at the dirty person in front of me.

"Clean yourself up then I want you completely clean. Cleaner then you have ever been in your life little man." The naked man started over to the basins to clean himself up using soaps and shampoos to clean himself up. I used mana to keep him in the baths while I cleaned the residue of our travels over. I then cleaned up the baths after letting myself back in before I started to clean myself up. I used fresh soaps and shampoos to clean my fur and skin. When I was done the guy was scrubbing behind his ears with a red blush over his face. I looked down and the little pecker he had was standing in all two inches of glory. He was looking at me before turning away. I was startled he was looking at me and getting turned on.

My narcissism acted up and I felt good about myself for about five seconds before I brought myself back down. I did not care if he thought I was hot. It would only help what was to come and I sat in the baths relaxing and hyped myself up to what I needed to do next. The little innkeeper finally finished cleaning himself up. He looked towards the door before he felt my stare at him. I could see him slowly remember the last time he tried running. He reluctantly moved back and over to the bath.

I stared commanding just with my look. He moved slowly over to me looking at me in the water once and or twice before looking down at his feet. The sobs were choked back as he made his way into the baths.

I looked at the innkeeper for the first real look I had since I met him. He was a twig with not an ounce of muscle on him. His face was Cute with no sharp angles except the Ears. His brown hair atop his head was short and plastered down with the water during washing. The man was flat as a plank of wood with no clothes. This man used to think he was intimidating to me. He was also taller than me by about two inches I guessed. I cared little though as he made his way over.

He moved so slowly like his reluctance would stop the enviable. "Move your ass here, Now!" I commanded and the spot beside me in the baths was filled with his ass seconds later. The fear in his eye was evident as was his erection. I wrapped my arm around his shoulder before turning my head to him.

His face was looking into the water with a blush and I saw his erection in the steamy water still. I rolled my eyes at the embarrassment. The Resentment though was still in those eyes when he turned to me. I understood that he was attracted to me but still hated me with a healthy amount of fear. These emotions looked at me when I used my hand to turn his face to mine.

"You have a long night tonight the first of many," I looked into those green eyes of his before I brought his face towards mine and kissed him. The confusion in his eyes was evident as I slid my hand down his back slowly coming to his ass. I probed his ass with a finger and when he relaxed his muscles trying to stop me they entered. I felt him tighten on me and I drove it in deep. I kissed him using the kissing techniques I had on my women. His expression was confusing to read as he muscles loosened again I probed a second finger in. I started to stretch him out as I used my other hand to stop him from escaping me.

His barely attempted struggles ended quickly. I probed a third finger into him stretching him more fingering his ass. A moan into the kiss I finally broke it off. I looked at him still not really feeling turned on. I stood on the seat in front of him showing off the nine-inch flaccid doorknocker to him.

"You will suck on it and make me hard," I commanded and used my hand to bring it to his mouth slapping either side of his face. "I fucked your wife now you will get me ready to fuck you, Slut." His face paled a little despite the heat of the bath before reluctantly opening his mouth. I smiled as I placed doorknocker on his tongue. "Suck it, Slut, No Teeth or you will know what real pain is."

He used his tongue to start giving frankly a shit blowjob. Slowly though as I told him more and more how to please me with his face buried in my balls at some points doorknocker got hard. The stark contrast made him look in awe at it for a moment before sobering up.

I pulled him out of the bath and pushed him with his stomach on the floor and legs in the water. I placed my fingers into his ass again. I fingered his little puckered ass until it gaped a little. I noticed his cock twitching to my workings and shook my head. 'Maybe this will not be as hard as I thought' I thought to myself before I lined myself up.

"Take it like the Slut you are Cucky," I nicknamed him since I didn't know his name. I pushed in penetrating him. I moved slowly into the clean hole hearing groans. I pushed till I knew it needed time to stretch to me. I wasn't even a quarter in.

I grabbed him by the hair and turned his head so he could see me. "This is your lot in life no Cucky," I told him and started to fuck him with the length that I could get into him.

"Please don't!" He started to finally beg but I reached around finding his small hard cock. I started to jack him off as I fucked his ass. I started to work my way deeper and the heard the groans start to turn to moans as I hit the sweet spot. I found that spot on all men that make them moan when they get fucked by a cock or when women finger them. I pushed into it each time.

"What- What's happening to me?!" I heard his distress as I felt him tighten on me without ejaculating. I was surprised legitimately. He just fuckin came on my cock with his ass on his first anal fuck.

"Really? This was supposed to be Sissyfying and training you. You are already one in hiding though? Poor Rose. She had a fucking little girl husband for how many months did you fail her?" I started to insult him as I started to fuck him harder and deeper.

"I di-dn-'t Fail!" He cried out as the ejaculation came through for the first time uselessly leaking into the water.

"The Fuck you didn't fail her Cucky!" I shouted as I forced my way to the halfway point filling his ass with a cry loudly coming from him. He tightened up on me again. "You are fucking dry orgasming on your first Anal fuck as a man. This takes training you, little Sissy!" I shouted at him. I pulled out and turned him around. He laid on his back and I put his legs onto my shoulders and tore his hands off his face. He was in tears blushing red and I penetrated him. He was not as miserable as I thought but a more pleasure-filled look. My look darkened as I realized I didn't even fucking need a week to finish this little slut.

HIs hard cock between his legs was dripping precum onto his stomach. I pushed my way deeper taking him deep-diving into the depths of his ass hard. His cries filled the room and I couldn't care less. This was no longer a **** like I thought it was going to be but a Sissy getting exactly what he wanted. I fucked him hard and fast insulting him to be the little Sissy cocksucker he actually was.

"Whats that Slut?" I asked him as more pathetic semen started to pool on his stomach as I reached balls deep into him for the first time tonight.

"I'm not a Slut!" He barely managed to shout out as I looked down on him his hands covering his face again.

"Bullshit!" I called him out, "I have not even cum once in this time while you have had multiple dry orgasms and ejaculated twice! You! are! a! Fucking SLUT!" I told him cementing it in his mind Thrusting with each word. I was working myself to orgasm for the first time tonight. My balls slapped his ass as I fucked him hard forcing cries from him. I was going faster and fast feeling him dry orgasm on doorknocker again. Finally, with another thrust in the midst of his orgasm, I filled his Sissy hole with a thick round of semen.

I filled him and he ejaculated onto his stomach. I have no longer even needed to touch his cock. I picked him up off the Tiled bath floor and brought him into the water still skewered on my cock and sat in the water.

"You will take charge of how fast you get fucked now," I told him as he looked at me but I added something as he looked at me incredulously, "But you have thirty minutes to make me cum or I punish you." I smiled to his expression. This was more fun then I thought it was going to be.