A Sissy's New Daddy Ch. 08

The door burst open and Kenneth flew in. "Sorry Mitch, the stupid deputy warden snagged me about the thing last month."

Mitchell shot Kenneth a nasty look but instantly softened thinking better of it. "No problem, I was just getting started here. Can you handle cleaning him up?"

Kenneth nodded as he reached down and pulled me to my feet. "Oh give me the bra and panties. I auctioned those off this morning. Fredrick's, over in tower three, what a freak offered me an insane amount to keep them."

"How am I supposed to get him over to the showers naked." Kenneth asked turning to Mitchell. I knew Mitchell would win so I didn't bother waiting I just slipped the lingerie off as quick as I could. "What if Gregory sees him?"

"If Assistant Warden Gregory sees him your fucked. Hell we're all fucked. So make sure you stick to the back hall ways. The ladies have some costume for him to wear anyways so who cares if he has these bra and panties." Mitchell didn't give Kenneth time to protest as he snatched the items from me and bolted for the door.

Once the door closed Kenneth turned to me and reached up cupping my cheek, "When we get out there you keep your eyes down and do what I say when I say. I will move us as quick as I can but there is always a chance you understand?"

I nodded and Kenneth ran his finger across my lips. I opened my mouth and sucked his finger in. Iran my tongue around it like it was a tiny little cock and Kenneth closed his eyes. "We have to go."

Moving through the prison was easier than I expected and we made it to the showers without anyone seeing us. Since I was naked I walked straight into the showers. I had to wait for Kenneth to lock us in before he could turn the showers on. I looked over my shoulder and smiled as the water clicked on with a hiss. I called out with my sweetest voice "You know I could use some help."

Kenneth didn't waste any time. He stripped off his uniform and soaped up his hands. Soapy hands rubbed my body from head to toe. Kenneth dropped to his knees and gently fondled my boipenis and my little balls. Slipping his hand between my legs I sighed as he slipped first one and then two fingers into my boipussy. I whispered to him "I want you r cock."

Standing up Kenneth turned me around and started kissing the back of my neck. I reached behind me and took Kenneths cock into my hand. I stroked him softly as I continued to beg under my breath for him to fuck me to make me his.

Once again he didn't waste any time. He pushed his now throbbing cock deep inside me. I let out a squeak and then a moan. Kenneth pumped faster today than he did yesterday but we still cum at the same time. Kenneth pulled out of me quicker this time just in time to hear a woman laughing behind us. Kenneth turns around in a panic and scurries out of the shower. Grabbing his clothes Kenneth ran from the room without a word.

"Well hello there. I heard about your arrival and just had to get a go at you. So can you eat pussy as well as you swallow cock." The woman was tall at least a head taller than me. And slim I could have wrapped my hands around her waist if I really tried. Her uniform was tailored so that it hugged her body perfectly. Her breasts were small not quite a c cup but a very full B. I just stood there naked with Kenneth's cum dripping down the back of my thighs as she looked me up and down. "I don't want a trail of cock slime leading to my office. Clean that hole up and get dressed."

I used a hand towel to clean myself up as best I could. There was a shopping bag just outside the showers, the kind you get at a fancy store at the mall. I decided to go ahead and take a look at the 'costume' I was to wear. Pulling bundles from the bag and was instantly saddened. I could see the plaid skirt of a school girl uniform. I was hoping for something a little less obvious.

Separating out the pieces of the customer I was surprised that it wasn't a cheap Halloween outfit, and then I was almost instantly creeped out. Wondering who the clothes originally belonged too. Under the skirt was a blouse, a bra and a pair of shoes and a pair of white stockings. But no panties. Since all of the items looked used I was ok with the missing panties. I dressed as quickly as I could, My female minder told me I could ditch the bra since it was too big but the rest of the outfit I was able to get to fit.

Once I was dressed she smiled and then pulled a zip lock bag from her pocket. She tossed me the bag and turned for the door. "Tuck that ugly piece of flesh between your legs away. The boys around here may not mind the sight of it, but I can't stand the sight of something so small."

Inside the plastic bag was a wet pair of white satin bikini panties. As soon as I opened the bag I was awash in the aroma of sex. I could smell cum and pussy almost equally. I slide the panties up my legs and as weird as it sounds I felt a little more girl as I settled the wet panties into place and tucked my boipenis away. I started after the woman and for the first time since I had seen her I managed to speak, "What is your name. I mean what should a call you."

"You will call me Guard Jennings." She paused for a moment and turned towards me. "Once we get to my office, you will refer to me as Principle Jennings. Between now and then. I don't want to hear a single fucking word. I hate cunts that can't keep their mouths shut."

We moved through the prisons back halls until we reached an office marked Human Resources. The door was as heavy as one of the ones leading outside. Jennings had to swipe a card and enter a key code to get in. Just inside the door was a young woman, she had a lovely face but her body was quite the opposite of Jennings. She was plump and her uniform looked like it was being worm over something else.

As Jennings locked the outer door, the woman jumped into motion. She stood up and scurried around the desk. That was when I noticed that she wasn't wearing pants or a skirt and actually save for the white satin bikini panties she was nude down to her heels. She peeled her shirt off and I realized why her uniform fit so poorly. Her upper body was wrapped in an intricate series of knotted ropes. The framed her heavy, D cup breasts squeezing them tight. Each nipple was pierced and had a small weight attached to the ring. Silver clamps connected by a chain connected both of her nipples. The woman took a position with her legs apart and her hands behind her head. "Good Morning Principle Jennings, does my body please you this morning?"

"Almost, for ten years I trained your mother, true the first two years I was opening her eyes up to her true place in life but still. Your mother still does not tie the ropes tight enough." Jennings said as she stepped up to the woman. Sliding her hands between the woman's legs and frowns. "How many cocks did you suck this morning?"

The woman looked terrified, she tried to speak but couldn't Jennings started running her hands along the gusset of the woman's satin panties. They quickly started to soak through. "Your pussy is soaking. I could smell it the second I walked into the room."

"Please I am sorry Principle Jennings, I couldn't help it they..." Jennings reached up and put a hand over the woman's mouth.

"It's always someone else's fault isn't it. That is why your mother sent you to me. How much trouble had you gotten yourself into before she sent you to me." Jennings said as she slipped her hand into the woman's satin panties. "Cum is a weakness for you, I understand that. I have tried to show you how to control that craving, but you are such a naughty little thing."

The woman gasped as Jennings slipped fingers inside of her. "Pussy is what you should worship. How many fingers do you feel inside of you."

"I don't know, I can't." The woman's voice came out in halting gasps. "Please not the box, I promise to be better I will practice tonight I swear."

"You will practice today in the box. Mercy leads to weakness." Jennings said as she slipped her hand from the woman's panties. "Besides I have a new toy to give my pussy a spasm today. Don't I."

Jennings turned and walked up to me slipping her fingers, covered in the woman's juices, into my mouth. Leaving her fingers in mouth so moved behind me. While Jennings was walking around me the woman started to roll her panties down. "No no, I think you should leave your panties on today."

The woman never looked up at me as I was sucking her juices off of Jennings fingers. Dropping to her hands and knees the woman crawled into the second room. Jennings slipped her free hand into the back of my panties and started to finger my boipussy. Once the woman had her back to us, we had a perfect view of her pussy as the wet satin panties rubbed against it.

Jennings pushed me into and we watched as the woman climbed inside an ornate wooden box. The woman climbed in and knelt down. Sticking up in the center of the box were five fingers. Lowering herself down onto them the woman sighed and then grabbed two handles at the top. Jennings pulled her fingers from my holes and walked over to the box closing the doors. "Now remember to call out how many fingers so the machine can grade you. And what happens if you fail?"

"I have to wear the belt again." The woman answered as the fingers began to move up and down pushing into her dripping pussy. The door closed and Jennings gave me a slap to remind me I had more important things then the woman in the box.

"I want you to undress me now." Jennings said as she leaned against her desk. She held herself up with her hands and set her feet shoulder width apart. As I unclasped her utility belt I noticed that she was armed with a Taser and I could reach it. A fantasy flashed in my head of escaping the prison and running off into the sunset. It was quickly replaced by a nightmare of death and torture. Pushing those thoughts out of my mind I set Jennings belt on her desk.

I dropped to my knees and unlaced her heavy boots, I pulled them off her feet along with a pair of thick cotton socks. Unbuttoning her pants I was pleased to find a pair of delicate pink lace boyshorts. Her pants were very form fitting and the only way I could get them off was to roll them down her legs. I worked them over both feet and set the pants to the side. Looking up as I was in awe, she was the most amazing looking woman I had ever met. Sitting with her butt on the edge of her desk Jennings spread her legs wide. I reached up to take off her top but she pushed my hands away.

Crawling between her legs I brought my nose right up against her crotch and inhaled deeply. The lace was rough on my tongue but I could taste her through it. Starting at the back of her calves I ran my hands up her legs until I reached the tops of her thighs and grabbed hold. When my fingers dug into her soft flesh and shiver ran down her body. Jennings grabbed my hair and started pushing my face into her body. I ran my tongue in a figure around the gusset of her panties. Sliding a hand between the two of us Jennings pulled her panties to the side and used her fingers to spread her lips. I pushed my tongue into her and she let out a wild moan as he body was rocked by an orgasm.

As she came down off of her high Jennings laid back across her desk. Her feet were dangling and she wiggled her toes as she spoke, "Not bad for a sissy, suck on my toes until I am ready for your next assignment."

I dropped down and started sucking on her toes. After a moment, of sighing and a stray finger or two slipping back into her panties Jennings picked up the phone and made a call. "They are ready."

Jennings gave me instructions for the day as I continued to suck on her toes. I kept at task wit out missing a beat until the door opened, the door she had locked when we entered. I stopped sucking and tensed up. She had said someone would be coming but I had assumed she would unlock the door and send me away. Annoyed that I stopped Jennings kicked me in the head and I started sucking again. A man let out a sigh and then spoke his voice was deep and full of authority. "What would you have done if it wasn't me that walked in?"

"Three people have a key to this office Assistant Warden Gregory, and if I didn't trust you it would just be two." Jennings said as she yanked her toe from my mouth with a pop. Hoping off of the desk Jennings stepped closer to the man, who I still had not looked at, Mitchell's words running through my mind.

"Where is our illustrious head of Human Relations this morning?" Gregory asked not moving further into the room.

"She is in the box, she can't seem to get to her desk in the morning without sucking a cock or two." Jennings said as she slid a finger into her panties rubbing herself. "So tell me Assistant Warden Gregory..."

Jennings drew out the man's name and title making the name sound like an offer for an unbridled marathon of sex. Slowly and with care she slipped her panties off "What do you do with these panties anyway? You're not a sniffer. I can spot a sniffer on sight."

Holding the panties out to her side Jennings allowed me to take them into my mouth and crawl over to the warden. "My wife, she is a lovely woman but has these ideas of her place in the home. I make her wear your used panties as a reminder of her proper place. A little humility learned through humiliation is always a good thing."

Gregory took the panties from my mouth and slipped them into his pocket. "You know that little piece of ass right there is going to be the recipient of a rather long gangbang tomorrow. I could see about getting the panties they dress him in when they are done."

"Those idiots will prove to be your downfall. I wouldn't trust a single one of them with a secret if I was you." Gregory said looking down at me as I started to hump his leg. "I have trained six woman as puppies. Two of them started their lives with me as boys. Stop trying to shock me Jennings."

Jennings shrugged her shoulders and motioned me away. "Why do you trust me if you know they will be my downfall?"

"You are smart enough to know not to turn on me." Gregory said as he watched Jennings legs as she walked over to him she got close enough that the two were standing in the same spot on the carpet. "You would break before I would and after that you wouldn't hold even the slightest fascination."

Jennings wanted to speak but she didn't. I watched as Gregory raised his hand till he was just touching the outer folds over her pussy. Slowly he started to wave his finger back and forth. Jennings grabbed his cock through his pants holding him firm. The two locked eyes waiting for the other to blink.

Ears would have been ringing if the box hadn't muffled the other woman's orgasm. But it was enough of a distraction to allow Jennings and Gregory to back away from the stale mate they had created. "You should check on your toy."

"You would love submitting to me. I could show you a whole new world." Jennings said as she released Gregory's cock and walked over to the box. A small touch screen monitor was hanging from the back. Pulling it up she tapped a few times before letting out a long sigh and rolling her eyes. "Some submissives, they just never learn."

Gregory walked over and looked at the screen nodding his head, "That is why you need slaves. Submissives have the power to submit. A slave has nothing to give, it knows nothing but obedience."

Turning to Gregory Jennings face went from a passive anger to lustful, "Stop flirting with me it you aren't going to let me have you."

Slapping Jennings on the ass Gregory walked out of the room. "You never answered my question about the sissy gang bang panties."

Pausing at the door Gregory tilted his head to the side and then answered, "What is the price?"

Jennings lust full gaze broke into a full smile, "A kiss, a simple one on the cheek."

"Sold, but the panties need to be wet still when I get them." Gregory said as he stepped through the door.

Jennings looked to me and scowled, "You need to get all the guards in this prison to shoot a load into your panties. Can you do that?"

I nodded my head and crawled over to Jennings. As soon as I was at her feet Jennings started around the desk, so I followed her "I met his wife once. Prudish little thing, I don't know how she ended up with him. If I am lucky those cum soaked panties will send her over the edge. I don't care if she runs in terror or breaks and isn't any fun anymore."

Reaching into a desk drawer Jennings pulls out a dog collar and a leash before continuing, "Though if he breaks her completely, then I would have a play thing when he comes running to me."

"Your Angela moment is over, take off her panties and let's get started on our day." Jennings said as she wrapped the collar around my neck and tightened. I didn't ask questions I just slipped the satin panties down my legs and landed them over. Placing them in a plastic bag Jennings placed them in the center drawer of the desk. "Now the rest of the clothes."

It was hard to undress watching Jennings get dressed. She unlocked a filing cabinet and pulled out a new pair of silk panties, a pink thong with a ruffled waistband. Sliding them up her legs I was mesmerized. She settled them into place and looked over to me. She cocked an eyebrow and I hurried to take off the blouse. I started to unbutton my skirt but then Jennings stepped into her pants. Bending at the waist she slid them up her legs. I was transfixed until the settled into place and her ass and panties were hidden from my view. Returning my attention to the skirt I quickly got it off and folded it. I folded the blouse and placed them both onto Jennings desk.

Staying on my hands and knees I waited for Jennings to come over and take the leash from me. Opening the center draw of her desk she pulled out a long thin cigarette and a lighter. Taking a hold of the leash Jennings led me from the office and down a short hall way. We stopped at a small door with a key card reader and traditional keyed lock. Pulling a key card from her breast pocket and then a physical brass key from her hip pocket she opened the door and we went outside.

The sun was so bright I couldn't see at first, for a moment I thought she had just delivered me to heaven. As my eyes came into their own I saw that no I was not in heaven, I was in a small but very well-manicured lawn. Jennings dropped the leash and lit her cigarette. "Go own now, be a good sissy and do your business."

I crawled out to the far corner and squatted down to relieve myself. Jennings leaned against the wall and took a long drag off the cigarette. She held the smoke in and looked to the sky before blowing it out. "Have you ever been in love?"

I wasn't sure if she was talking to me at first or if she was maybe on a Bluetooth I hadn't seen. When she growled that she was talking to me I started talking "Yes, I met a boy and he loved me, even though I am a whore."

"Those are rare. Finding someone that loves you even when they see your most wanton and pathetic side." She took another long drag on the cigarette. "I have never been in love. As a matter of fact I don't think that I have ever loved anything."

Snapping her fingers Jennings pointed at her feet and I crawled over to her. She took another long drag on the cigarette and barely held the smoke in this time before blowing it out. "I mean Gregory, he isn't at all my type. I have never been attracted to a man. I mean I have used my fare share, but woman are so much more fun to abuse."

Pointing to her waist I realized that she had not reattached her utility belt. I reached up and unbuttoned her pants and peeled them down, careful not to bring her panties down as well "Gregory is the first person that I have ever felt a need to have. I need to feel him inside of me. I don't like that feeling... well usually I don't."