Amanda

I started again, running my tongue and lips over her. Her taste was fantastic, musky and sweet. She moaned and started saying things like, "Oh, yeah", "Oh, god", and "Fuck". Then her body started to shake and I could feel her pussy pulsing against my mouth as she reached orgasm. Then a stream of liquid splashed into my mouth, I swallowed the first mouthful involuntarily, and it was hot and acrid. The flow continued, spraying from her pussy to drench me. It was in my eyes, my mouth, and my nose. I realized she was peeing on me. It was, perhaps, the nastiest thing to ever happen to me. Not only was I soaked in her urine, I had swallowed some of it. I thought I was going to be sick.

She grabbed my balls, "Lick my pussy clean!"

When I didn't immediately comply, she applied crushing force to them, "I meant now!"

What could I do? I licked the remaining pee off her pussy.

She got off me, and went over to her cabinets. How many things did she have in there? She came back with a rubber ring with Velcro straps on either side. "Open your mouth," she held it out, "I'm going to gag you while I give you your blowjob."

What I really wanted was a shower to wash off her pee, but I guessed I wasn't getting that. I opened my mouth, and she worked the ring behind my teeth, then had me lift my head and secured it. I couldn't close my mouth. "No, not quite right," she said, and went to fetch a realistic looking dildo. She brought it to the ring, and pushed it into my mouth. "Mmmm, taste my cock," she purred, and started pushing it in and out. It was long, and on the pushes in, I was gagging on it – she didn't seem to care.

I managed to move my head just right to accept the full length of the thing, just to stop myself from chocking. She noticed this, and slid it all the way in, then secured it there, completely filling my mouth and throat. I could breathe, but it was a little difficult, and I couldn't really move my head out of the slightly tilted back position it was in, so I couldn't really watch what Amanda was doing.

I felt her at the cock cage, and there was a click. She took it off. Then I felt warm lips around my dick, and her tongue caressing the underside of my cock and swirling around the glans. Oh god, it felt incredible. I'd had no idea that oral sex felt so amazing. Amanda stopped for a moment, and a new sensation wrapped around my cock. I think it was a condom. "I don't want your cum in my mouth," she told me, "So I've put a condom on you. Feel free to cum when you want." I needed her permission to cum? She started sucking on me again, and added her hand to pump with. It was only a few seconds of this before I couldn't take any more, and I exploded. She didn't stop, however, and continued to suck on my overly sensitive cock. I couldn't take it, and was thrashing under her. "Good fuck toy, cum again for me," she attacked me with mouth and hand. The nearly painful sensations turned back to pleasure, and in far too short a time, I reached orgasm again. This time she stopped.

I felt her grab my shrinking dick, and squeeze the condom off. It made a snapping sound as she pulled it free. She came to my head and showed me the condom filled with my jizz. "You're a heavy cummer – that is good!" I watched her pour the contents of the condom into a syringe, then she put the end of the syringe at the back of the dildo down my throat, "Taste your own cum." She slammed the syringe down, and I felt my throat fill with my own sperm. I had no choice but to swallow it. It tasted salty and sweat, but mostly like wet snot.

Amanda put my chastity device back on me as I was bemoaning the humiliation she was inflicting on me. She had peed on me, made me swallow my own load, ripped all the hair off my body, and shoved a plug up my ass. In return I had seen and licked her pussy, and she had given me a blowjob. I was not sure the scales were in my favor on this.

She took the dildo out of my mouth, and then removed the ring gag. I worked my jaw, which was aching.

"Here is the deal," she told me, "I want you to sign a slave contract."

I looked at her, not knowing what the hell she was talking about. "A what?"

She sighed and pulled a piece of paper out of the cabinet. She read it to me:

"Of my own free will, as of April 3rd, I Josh Miller, hereby grant Amanda Freeman, full ownership and use of my body and mind from now until she releases me.

I will obey Amanda at all times and will wholeheartedly seek her pleasure and well-being above all other considerations.

I renounce all rights to my own pleasure, comfort, or gratification, except insofar as Amanda desires or permits them.

I will seek always to learn how to please Amanda better, and will gracefully accept criticism.

I renounce all rights to privacy or concealment from Amanda. I will answer truthfully and completely, to the best of my knowledge, any and all questions Amanda may ask me.

I understand and agree that any failure by me to comply fully with Amanda's desires shall be regarded as sufficient cause for possibly severe punishment.

Within the limits of physical safety and my ability to earn a livelihood, I otherwise unconditionally accept as Amanda's prerogative anything she may choose to do with me, whether as punishment, for her amusement, or for whatever purpose, no matter how painful or humiliating to myself."

"Why would I sign anything like that?" I was stunned. There was no way. I was thinking I was done with this whole thing with Amanda – no matter what she might blackmail me with. There was no way I was signing a document to let it continue.

She smiled sweetly at me, "I could threaten to make your life at school hell, but I want you to sign it willingly – without coercion – otherwise it doesn't mean anything."

"I don't think so. I think I'm done with all of this. Do what you want, but I'm out of here." It was a rather bold statement considering that my hands were still bound together under the table, and there was no way I was escaping unless she let me go.

Amanda straddled me, her hot wet pussy pushing down on my chastity cage. She undid the laces on her corset and took it off, so she was sitting completely naked on me. I couldn't help myself, I drank in the sight of her. She was absolutely gorgeous, and her perfect round tits with the dark nipples that were sticking out like little thumbs as the skin around them wrinkled a little bit were amazing to look at. "You said yourself that you are a virgin. That you've had no partner but your hand. You'd never even seen a real girl naked before. Now, with me, you've seen me naked. You've had your face in intimate places. You've had a blowjob. Are you sure you want to give that up?"

"You've abused my ass, ripped all the hair from my body, peed on me, and I seriously think you drugged me yesterday. How is any of that an enticement to want to sign a contract making me your slave?"

She leaned down, pressing her tits against me, and bringing her head right up to me, so she was looking me right in the eyes. "First, I find smooth skin sexy," she rubbed her tits against me. "Second, I wanted to mark you with my scent, so everyone knows you're mine." She leaned forward and quickly planted a kiss on my lips. "Third, I like anal sex. I want you to like it too. If I waited for you to want to receive anal sex, I would wait forever. I forced the issue."

I couldn't believe what she was saying, "You're completely mental – you know that?"

She smiled and kissed me again, "Yeah, but the good, sexually deviant kind of mental."

"The answer is no," I told her. I wasn't as firmly convinced as before, her body felt fantastic pressed against me. I wanted to know what it would be like to hold her naked body, really embraced, and make love to her.

She must have read the expression on my face. "Listen, how about this. I will acknowledge you are my boyfriend – in school – which will immediately change your social status and make the last couple months of high school bearable. I will go to prom with you as well – something I think you wouldn't be going to without me. We will have normal sex – as boring as it is – at least once a month, and providing you are a good slave. I also promise you as much sex as you can take. Does that sound like a compromise?"

That was a hell of a deal. I seriously was considering it – which shows both how low and desperate I was on the social scene, and how warped I must be in general. "Once every two weeks," I figured I might as well push the envelope. She was obviously intent on me, for some reason.

"Agreed, provided you do not fight me on anything I want to do to and with you," she smiled.

I was obviously the most stupid person in the entire fucking world. "Agreed."

She bounced up, clapping, "Awesome!" She slipped off me, and unlocked my hands. I sat up, and then she handed me the paper and a pen. I noticed she had already signed it. I put my signature on it as well, and handed it back to her. She took the paper, and wrapped her arms around me, kissing me full on the lips, "Time to play."

She slipped out of my grasp before I could even try to return the embrace. "I thought we were already playing?"

She giggled, "Oh, yeah, well that is sex play – time for games." I was totally confused.

"Take off the wrist cuffs, and untie your ankles," she told me. She was already searching the cabinets, "What size shoe do you wear?"

That was a question out of nowhere, "9."

She tossed a pair of 6" high heels back toward me, "Try those on."

"You want me to wear high heels?"

"Listen, slave," she glared at me, "you do as I say – you signed a contract."

I sighed and tried them on – they fit around the foot, so I did the little strap on the side to hold them on.

"Stand up," she said, and came over to offer me support.

I got wobbly to my feet. The angle down was so much, I was really just on my tip toes. It also arched my hips forward, changing my center of gravity.

"We are going to practice walking," she tugged me forward. I was not steady on my feet, and with the plug still in my ass, it made me walk awkwardly as well. However, it was nice to hold her hands – which was probably the most normal thing we had done since all of this started.

"Swing your hips a bit," she instructed, "stop walking like a man and you're hunting something. Don't pick up your feet so much. Also, go toe to toe, not heel toe, it will make it easier."

It took me about five minutes of this, and I was reasonably sure I wasn't going to do a face plant, "I think I almost got it."

"Good," she beamed, "go back and sit down then."

I did so, the plug was uncomfortable when I sat down, wedging itself in deeper, or shifting or something. "Take off the shoes, and put these on," she handed me a pair of what looked like pantyhose – except there were two of them. "They are thigh highs," she explained.

I shrugged and pulled them up my legs. True to their name, they ended in a frilly band about half way up my thighs.

"Now, slip the shoes back on," I did so, and Amanda grabbed two small padlocks, and used them to lock the buckles on the shoes, "You'll be wearing these for the rest of the day. I didn't want to lock them until I was sure you could walk."

She looked at my legs in the shoes, "You have nice legs."

"Uh, thanks?"

"Now," she grabbed my hand, "Come on, a few more things to do."

She led me from the room and across the downstairs room to a bathroom. We went inside. "Lean over the counter," she told me, "Time to wash you inside."

"What?"

"Time for an enema." She took out a small pump with two hoses. She placed it on the counter where it was held in place by little suction cups. She turned on the water in the sink and let the water run warm, and then plugged the drain. She filled it about half way, and added some scented oils and soap. She dropped the ends of both hoses into the water. She turned the pump on, and waited wile it sucked up the water and was pumping in a loop. She turned it off, and took one of the hoses. It was long enough to reach around behind me, and I felt her attach it to the anal plug.

She turned it on, and I felt warm fluid rush into my bowels. "Let me know when it becomes too painful."

It didn't take long. As the water drained from the sink and into me, the pressure, then the pain increased as well. I had half a sink's worth of fluid in me, and was groaning from it. "Good boy," Amanda cooed, stroking my butt cheek, "Almost there."

"I feel like I'm going to explode," I told her.

She turned off the pump and detached the hose. "Let that mix do its job." She rubbed my belly gently. It was all I could think of not to push, popping out the plug and spraying everywhere. A sheen of sweat was covering my body. "Good, now, sit on the toilet and pull out the plug."

I did so, nearly panicked with the urgency to go. The plug came out, and with a tiny push on my part, smelly water rushed out of me. The pressure vanished. It occurred to me that she was watching me on the toilet – a strangely intimate experience even with what we had already done. I was somehow embarrassed from the experience. Once I was empty, she told me, "Wipe, then put the plug back in."

"Do I have to?"

"Yes, now do it!"

I was mortified, here I was wiping my ass in front of her. I did so, then with a little effort put the plug back in.

"Round two," she told me.

I groaned, but stood up again, and she repeated the process. This time, she let me leave the plug out.

She had me wash my face, then sat me down and applied makeup to me, including eyeliner and mascara. Then we went back to the, what I was beginning to think of as her torture room, and she found me a white frilly neckband, and a short frilly black skirt with white lace crinoline. I realized she was dressing me as a French maid. It included a corset top that she tightened down, forcing me to take shallower breaths than I was used to.

"There," she said, adding the obligatory headband, "perfect. I would kiss you, but I don't want to redo you lipstick." She pulled one final part of the costume out. It was an anal plug with a long fur tail. I couldn't tell if it was fox or wolf. "Bend over," she ordered. I saw that this plug looked wider, and was worried that it was going to hurt like hell when she put it in. It hurt as she worked the bulb in, but not as much as I thought it would.

"Come on," she told me, walking from the room. I followed her, feeling ridiculous in this getup, and the tail was weird swishing against the backs of my legs. The stairs proved treacherous in high heels, and I had to take them really slowly, using the hand rail a lot. I had wanted to watch her climb the stairs, but self-preservation had put an end to that. Finally I made it back to the first floor. Amanda was already in a bikini. She handed me a stack of towels, "Take those out to the pool."

I knew the backyard was fenced, so nobody would see me. I took the towels out to the pool. The sun was high, and the day was warm. I could smell the water in the pool and the rich aroma of the grass and flowers. It was a really nice day. I put the towels down and turned back to the house. I stopped in stunned surprise. Amanda was just coming out of the house with five girls in tow. I recognized all of them from school – they were all the really popular girls. I felt genuine fear race up my spine, and I wasn't sure if I should run or hide or what. Not that running was a possibility in these shoes.

Beth, a tall, leggy blond girl with an athletic build and small breasts was the first to notice me, and she stopped dead, "OH MY GOD!"

The other girls turned to look. The embarrassment I felt started somewhere in my toes and ended well past the tips of my hair. I could feel the blush of shame across my whole body, and I wanted to curl up and die.

"This is," Amanda cast about for a second, "Josie. She will be taking care of us today."

The girls approached me. I could tell that they recognized me, but were going to go along with Amanda.

"Josie," Amanda stood in front of me, "Curtsey to the girls."

I blushed again, as if this could get any more humiliating. I grabbed the hem of my short skirt, and made an awkward curtsey – what else could I do?

"Seems like I was wrong," Beth said slowly, "I didn't think you could pull this off."

Amanda smiled, "I guess that means I win the bet."

Beth looked at her and sighed, "I guess it does."

"Then," Amanda grabbed Beth's wrist and started to the chairs by the pool, "I'll take my winnings."

Jen, Megan, Amy, and Kate took a few more seconds to scrutinize me, then turned to Amanda and Beth. Clearly the wager, and its results, were going to be far more interesting than me in a French maid's outfit – even with my cock hanging in a cage below the crinoline and a tail sticking out of my ass.

"I believe," Amanda stated, "That the wager was a kiss on the lips, with tongue."

Beth looked nervous and was hunched in on herself, "Yeah, it was. Although I don't know why you want to kiss me – it isn't like I'm into girls."

"No," Amanda sat down, "I just want a physical acknowledgement that I won the wager."

Beth looked a little more relieved, until Amanda cocked her hips forward and pulled her bikini bottoms aside, "So, kiss my pussy lips, and don't forget the tongue. I want to feel it inside me."

Megan gasped, "Amanda! You can't make her do that!"

Beth looked like she was going to be sick.

Amy looked excited, and Jen and Kate looked speculative.

"When we made the wager, I do not recall specifying what pair of lips you needed to kiss – did I?"

"No," Beth said, her voice a mere whisper.

"Are you going to renege on our bet? Is that who you are?" Amanda spread her legs a little wider and used her hand to open herself fully, "Or are you going to do what you promised?"

I was painfully aware that my cock was caught in the cage, as it was straining to be free and it hurt to be so pressed against the metal enclosure. Was I really going to get to watch Beth, the queen bitch of the school, suck on Amanda's cunt? It certainly seemed that way.

"Amanda," Megan, the obvious voice of reason in the group, said, "That is above and beyond. Nobody thought you mean that when you made the bet."

Amanda looked at her solemnly, "Do you recall when I said, 'I want a kiss on the lips – with plenty of tongue – as a reward. I get to choose the lips, which will almost certainly be mine, but not required to be mine?"

Beth was wilting, her eyes somewhat panicked, "Is there something else you would take instead? Anything else?"

Amanda appeared to consider it. "Sure," she decided, "You could take Josie's cherry."

"I'm not doing that here," Beth stated flatly.

"No," Amanda waved at the house, "You can take her to the guest room."

Beth considered for half a second, "Ok."

My heart leapt. Beth was a knock out – long legs, wavy blond hair, cute little mouth, and bright green eyes. The fact that they were discussing her fucking me like it was an afterthought didn't change anything. I was going to get to put my dick in her pussy.

Amanda took the key off her neck, "Here is the key to her chastity belt, have fun!"

Beth took it, sighing, "Come on... Josie." She walked to the house, without seeing if I was following her. Of course I was following her. We went into the house and up to the second floor. It was ridiculous climbing stairs in these heels, so Beth was at the top of the stairs way ahead of me. She walked into the first room on the right, and I walked in after her.

She closed the door, "First thing, there is no way in hell we are having sex. I'm not kissing you, touching you, or anything else. We are going to stay here in this room for the next fifteen minutes, then we are going to go back out, and you are going to tell Amanda that we had sex. Got it?"