A Sissy's New Daddy Ch. 08

Jennings didn't wait for me to respond she spread her knees and pushed my face into her crotch. She smelled sweat and I wanted to see if she tasted as sweat. Sticking my tongue out I ran it gently across the silk of gusset covering her pussy. The silk tasted like detergent. But when I used my nose to push the panties aside I tasted her pussy and that tasted like candy. Opening my mouth wide I started to suck the skin around her sex. I used my tongue like a mop and liked up every bit of juice the woman would let me have. As the flavor faded and aIl I tasted only my own spit I started to close my mouth. Dragging my teeth along her skin. That sent a shiver radiating out from where I was nibbling. Once my teeth reached her clit I bit down, not hard, gently but it was enough to rock her body with an orgasm.

"Fix my pants." She said. The whimsical tone that had filled her voice when she spoke of Gregory was gone now it was replaced with the demanding tone of a dominatrix. She waited with a patient indifference until I pulled her pants back up and rebuttoned them before she took my leash again and lead me back to her office. Though I had realized at that point that it wasn't actually her office.

I was told to stand in a corner while she prepared my next assignment. Pulling the other woman from the box Jennings stood her at attention and began fondling her body. Once the woman's nipples were hard, Jennings grabbed her arms and pulled them above and behind her head. She then began to tighten all of the ropes crisscrossing her upper body. Pausing only when the woman's nipples would soften. Once the ropes were satisfactory Jennings stood in front of the woman and used one hand to rub her satin panty clad pussy and the other to pull her in for a deep kiss. The woman, who had been so stiff and scared all morning began to melt.

Pulling out of the kiss I watched as the woman leaned in begging for the moment to last just a little while longer. "I was very proud of you before this morning. I had decided to eat your pussy today."

The woman let out a gasp of joy that was immediately silenced with a slap. "I said I was proud. First you suck a cock before you come and see me. Then you only get half of your finger test correct."

"Please forgive me Principle Jennings. I am a stupid little girl who does not deserve your greatness." The woman mumbled.

Taking her hand away from the woman's pussy Jennings slips her glistening fingers into the woman's mouth. "You are a natural at this, So much better than your mother. I will tell you what. To show that I am proud of the progress you have made I will let you get that sloppy pussy of yours eaten today."

I was brought over and with a force full slap on the ass ordered to remove the woman's panties. They pulled away from her pussy reluctantly, the damp satin cloth clung to her sex like a discarded lover. I tried to hand them to Jennings but she just shot me a look of pure disgust. "Put them on."

Hiding the enthusiasm I had at that exact moment was impossible. I jumped to my feet and slide the cool wet panties up my legs. Once they were in place I was directed to lie down on the desk and close my eyes. My hands and feet were fastened to the table and the woman was directed to climb up and sit on my face.

Once the woman was in place but before I could start licking, Jennings set the rules. "OK now Sissy you are you are not to stop licking Cock Slut Jane here until I return."

Jane cringed when Jennnigs called her that, but Jennings didn't care and kept right on talking. "And you Cock Slut, are to make sure that sissy here cums for everytime that you do."

Stepping away from us Jennings said begin and I started licking. Jane leaned down and pulled her panties to the side and took me into her mouth. Bobbing her head up and down with her warm wet lips wrapped around me stiffened me almost instantly. Bobbing up and down on my boipenis made me moan into her pussy. And when I moaned she moaned. Jane then slid two fingers into my panties and plunged them into my boipussy. I came instantly flooding Jane's mouth with my cum. As warm semen washed across her tongue Jane came as well.

"Don't you dare swallow." Jennings called out. Jane's body instantly stiffened. Jane started to sit up, letting my cock slip from her mouth. Jane used her hands to hold herself up so I knew it was Jennings that slipped my boipenis back into the satin panties. "Spit that cum out right onto the sissies panties."

The cum landed on my crotch with a plop and started soaking into the thick white satin. "I said to make the sissy cum not to suck it's, whatever that tiny thing is. Are you really that desperate for a cock."

"No..."

"Are you lying to me?" The question hung in the air neither woman speaking for a long few seconds. "Answer me Cock Slut."

"I am afraid, Principle Jennings." Jane said her voice trembling as she barely got the words out.

"Are you afraid I will spank your fat cock hungry ass until it bleed's." Joy danced around the edges of Jennings voice and I had a feeling that I had just been told what the rest of the afternoon would be.

"Yes Ma'am. I am terrified." Jane said her body shaking with fear.

Jennings let out a sigh and started rubbing Jane's backside, the tips of her fingers brushing against my forehead. "I have not been a very good mistress to you have I Jane."

Again a silence hung between the two woman and then Jane spoke, "You are an amazing Mistress, far better than I deserve."

"You are a very good girl." Jennings said as she slipped two fingers into Janes pussy, "Ok things are going to change starting tonight. You will spend the rest of the morning letting the sissy eat your pussy. Same rules apply you have to give him hand jobs and he has to cum an equal number of times. This will be the beginning of a new life for you."

Jennings pulled her fingers from Janes pussy and after liking the tips slide them slowly into Jane's ass. Jane's body quivered and she begged to be fucked. "Now finish your task and I will be back soon."

By the time lunch had come I lost count of mow many times the two of us came. Jane was out of breath and was laying across me her head inches from my softened and sore boipenis. Cum had soaked through the panties and pooled around her face. He hand was laziliy moving up and down my shaft which would twitch each time she circled around my head. I didn't hear the door open and I don't know if Jane did either but we both heard the happiness in Jennings voice. "Well aren't you too just a picture."

Jane tried to stand up but couldn't. Jennings patted her on the head and told her to stay there. I was ordered to stop licking and Jane used me as a pillow for almost an hour while Jennings left once again.

When she came back in Jennings slapped Jane on the ass making a loud thwack that woke the woman up. Without being told to she climbed off of me and crawled on her knees to Jennings feet. "Thank you for honoring me with that pleasure Mistress."

"You are a good girl. Let the Sissy go." Jennings said as he walked over to the filing cabinet that she had pulled the fresh panties from earlier. She opened the top draw and then the second from the top. Jane release my hands and then my legs. "Ok Sissy give Jane her panties back."

I slipped the soaking wet panties down my legs and handed them back to Jane. Confused she looked to Jennings, "Mistress... I am not..."

"Go ahead a slip those back on." Jennings said as she pulled a matching bra and panties setting them on top of the filing cabinet. Turning back to the two of us she smiled as Jane slid the wet panties up her legs and stood shivering waiting for her next command. "Ok now I need you to listen carefully to your next orders, Jane. I want you to take the bus home, don't worry about your car I will have it waiting for you when you get to my house tonight. When you get home you will pack all of your clothes and only your clothes. Most of those are going to be discarded but I want to see everything you have. You are to pack them and get a ride from Mistress Heather to my home."

Jane sucked in a sharp breath and started to shake. "Don't worry about Mistress Heather, she has learned a lot since the last time you serviced her. And besides as long as you do as you're told everything will be fine. I will be home late so I expect a meal prepared and for you to be wearing nothing but those panties you have on now."

"Yes mistress." Jane said as she scurried away to the outer desk. Jennings and I both watched as she unfolded a pair of slacks from her desk and started to put them on.

"Oh one more thing Jane, come here. And bring those pants." Jane returned and reluctantly handed the pants to Jennings. Pulling a small seam ripper from her pocket, Jennings un did the crotch of the pants. They were now open from the bottom of the zipper all the way through the legs and back up to the waist line in the back. Jennings smiled as she handed Jane the pants. We both watched as she slipped them on and walked to the door to retrieve her blouse and shoes. With each step her bright white panties flashed. When she bent over to pick the items up her pants opened wide and more than just a flash of her panties were visible.

As soon as the door closed Jennings turned her attention back to me. The joy she held watching Jane walk around flashing her panties was gone when she looked me up and down. "Not quite as pretty as a boy are you."

She handed me a pack of baby wipes and told me to clean myself up. It took a few minutes but once I was done she nodded in approval. But Jennings still took the time to actually smell me from head to toe to make sure I was clean enough. Once she was satisfied she handed me the bra and panties she had pulled out a few minutes ago. They were a matching pair, yellow with little sunflowers all over them. The panties were a thong and the bra was a shelf bra that would have put my tits on display... if I had had any that is.

Once I was dressed Jennings asked if I wanted to get fucked today. I enjoyed woman as much as I did men but I knew the correct answer was yes. Immediately she opened the third draw and pulled out a large black rubber dildo. She bent me over her desk and quickly lubed up my boipussy before forcefully shoving the full length of the fake cock into me. "Now we are going to play a game, it is called - I am not allowed to cum while licking Principle Jennings pussy and getting fucked by a big black cock."

Licking my fingers I wet the suction cup base of the dildo as I climbed under the desk. I attached it to the back wall of the leg area and pumped it in and out a few times to test it. Even though I was under the desk I had a perfect view of Jennings as she peeled her pants down. She left her shoes and socks on this time. Taking a seat she rolled the chair into place and snapped her fingers and pointed at her pussy. I kissed her thighs first and worked my way to her pussy. I decided that I wouldn't move her panties, if she wanted them gone I would let her move them. I licked my tongue up the length of her slit and then kissed her clit.

Sucking her clit into my mouth a sucked on it for thirty seconds before pulling my mouth away with a quite pop. I got so into sucking on Jennings pussy that I forgot to fuck myself with the dildo. "Keep pumping on that cock with your sissy cunt. I want you ass gapping when I turn you back over tonight."

I spent the next hour pounding away at my pussy while licking Jennings. IT wasn't long before her panties were soaked with an equal amount of girl cum and sissy slobber. AS she was racked by fourth powerful orgasm Jennings pushed my head back "Ok now sissy keep fucking yourself but I want you to kiss my thighs now."

I did as I was told and listened as Jennings made a call, "Let me talk to Jack."

There was a pause and I felt as the muscles in Jennings legs tensed. "Tell him it is his baby sister."

The room fell silent as Jennings paused once again. Her legs slackened and she leaned back in her chair. "Jack, I know I know I have been busy with a new slut. I am taking the next step. I know you told me to a long time ago. My problem now, and why I am calling,. The slut has a serious cock addiction. I want to break her of it. You told me that you broke that girl in high school with a bukakke party right. Can we hold one at the bar Saturday... Awesome. I owe you."

Jennings leaned forward to hang up the phone and then jerked back speaking franticly. "JACK. Hey hey listen. That bitch that answered the phone. Make sure she is there. I want to teach her a lesson while my new slave gets broken in."

Grabbing my hair Jennings ground my face into her pantied pussy. I licked as fast as I could hoping to continue to get her off. She climaxed another three times before I was pushed away. Since I hadn't been ordered to stop I kept bouncing up and down on the black dildo. Jennings ordered me to remove her pants, shoes and socks which I did while continuing to pump the dildo in and out of my boipussy.

Putting her feet up Jennings leaned back and closed her eyes. She slipped a hand inside her panties and another into her shirt. After playing with herself for a few minutes She started talking to me. "I wonder how many hands were inside Janes pants today while she rode the bus home. Have you ever been groped on the bus?"

"Yes Principle Jennings." I answered still bouncing on the dildo desperate to stop.

"Tell me about it." She ordered. I preceded to tell Jennings about Principle Blackthorn and the week I spent as her slave. Of the girls she had under her control and the days she sent me onto the bus dressed as a slutty school girl. I told her of the gangbangs and the humiliation. She liked the humiliation. When I finished my story Jennings ordered me to come out from under the desk. I reached back and separated the dildo from the desk before I crawled out. I tucked the dildo into the panties.

I did my best to clinch my boipussy tight but I could still feel the feel the dildo sliding out as a crawled. Once I stood up I reached back and gently pushed it all the way back in. "Do you like having your boipussy filled with that Dildo?"

I paused a moment trying to decide how to answer, I was tired and sore so I told her the truth. "I like the feeling of a cock pumping inside of me, but I am tired and sore from the last few days."

"Those panties I loaned you are soaked in your sissy cum. Do you remember the name of the game we were playing?" Jennings said as he slipped a finger back inside her panties.

"Yes, Ma'am." I answered with a hand behind my keeping the dildo in place.

"AND." Jennings slipped a second finger into her panties and alternated their movements. One finger up while the other was down.

"I failed."

Pulling her hand from her panties Jennings motioned for me to step to her. Once I was close enough she shoved the two fingers in my mouth. "I should punish you for ruining my panties. I have heard that Harrold is offer a very nice reward for letting him have his way with you. A fatal visit with him."

My heart stopped and my vision blurred just a bit. "Please no."

"You have spent the last two hours eating my pussy. What more could you possible offer to me." Jennings said as she crossed her legs sealing her pussy off from my view.

"We could make love." I whispered hoping that was where she was leading me. "I will do anything to please a superior."

Jennings lips curled into a smile and she rolled her eyes. A laugh that was combined with a grunt slipped past her lips while she shook her head. "Do you think that I would ever let a tiny little panty clad dicklet, hell it is barely an oversized clit. I would never let that thing inside of me. But..."

Rising up Jennings stepped behind me. She placed her toes against the base of the dildo and her hands on my shoulders. She started pushing the dildo deep inside of me while pushing me down. "I may have one task for you. There are two guards here. The only two guards that I don't have any dirt on. Now they like to fuck you little sissy boys but they have never done it in front of me." I want them on video and I want the video to be as nasty as you can make it. Beg them to do the nastiest things imaginable to you."

Squatting down Jennings wrapped her arms around me and whispered in my ear. "Give me enough dirt to bury those two forever and I promise I won't turn you over to Harrold for being a naughty little sissy."

"I will I promise." I mumbled trying not to meet her gaze.

Smiling Jennings stood up and walked over to the filling cabinet that seemed to be filled with lingerie. She opened the bottom drawer and pulled out a two small black bags. One was obviously a toiletries bag and I was guessing the other was a makeup bag. "There is a small bathroom in the outer office. Go get cleaned up, shave and put on some make up."

Reaching for the bags, Jennings hand shot out and grabbed mine. Her face changed it twisted into an angry sneer, "you cut yourself, you hurt yourself or you try and sneak away with the razor in there and I will make the last few days of your life a living hell before I turn you over to Harrold."

I can't explain why I wasn't afraid in the moment but I wasn't, I plastered a solemn look on my face when I spoke, "I don't want to die, I won't do anything to anger you."

With a sudden bright smile Jennings released my hand and smacked me on the ass as she sent me on my way. "Oh one more thing, when you are applying that makeup, your stupid little brain will say less is more. I don't want subtle and graceful. I want you to look like a trashy little fuck slut."

I hurried into the bathroom and closed the door. It actually closed and the click of the doors handle was heavenly. I felt safe for the first time in well, honestly I don't remember how long it had been. I started the shower and waited a moment for the water to warm up. I peeled off the bra and panties I was wearing and opened up the toiletries. There was a razor, nail clippers, a small pair of scissors. I climbed into the shower and lathered up my whole body. Scrubbing every inch of me for a full thirty seconds. By the end of that my boipenis was stiff so I soaped up three fingers and then fucked my boipussy until I came.

Once all that was done I took a long while shaving my body, it had been a while and I had a feeling it would be a while until I could do it again so I made sure to do it right. Smooth as a girl should be I climbed out of the shower and toweled off.

I hadn't heard her enter but Jennings, or someone else, had come in and taken my clothes. I toweled off and started on my makeup. Bright red lipstick was followed by eye shadow and blush. I applied all three as heavy as I could without looking like a cartoon. Next I did lash extender and then nail polish, fingers and toes of course. Once my toes and hands were dry I gave myself a once over. That was when I noticed the perfume. I spritzed some on my wrists and applied it to my neck. Just as I was about to step out I had an idea. I grabbed the perfume and spritzed my boipenis and my boipussy. Just in case either of the twins decided to go down on me.

Jennings was on the phone when I finally came out. She glanced my way and then pointed to the desk. Laid out before me was a pale pink satin bustier with a matching satin bikini panties. I slide the panties up my legs and shivered unable to hide a smile as the waistband of the panties snapped into place. I wrapped the smooth cool satin around my chest and clasped the back before spinning it around and sliding my arms throw the shoulder straps. Under the outfit were a pair of pink fishnet stockings. Carefully rolling them up my legs. A pair of ridiculous pink platform heels were on the floor next to the desk so I stepped into them. There was no mirror for me to look into but I just knew that the pink satin made me look fuckable. I wanted to touch myself but I was afraid I would start to leak precum and piss Jennings off.