Freedom is Slavery (20 page)

With that, I felt her fingers going up and down the crack of my ass, massaging my virgin asshole. I didn’t even need to ask what she planned on doing as I felt drops of lubricant hit where her fingers had just been. She used one finger at first but it felt like it might as well have been five as she pushed inside of me.

She started fucking me with one finger and asked me if I could take two. I don’t know where it came from but I nodded in assent. Two fingers became three and, finally four.

"Damn, you little slut, if we had more time, I’d fist your fucking ass," she said, finally pulling her hand out of me and leaving me crumpled on the floor.

As a final act of humiliation she had me masturbate in front of her, her hand cupped at the end of my cock. When I came she held it up and made me slurp it out of her palm.

She took the paper and wrote "B+" on it, giving it back to me and telling me that my grade could have been an A if I had come over earlier in the semester. With that, she told me to get the fuck out of her house.

I thought that it had been a one-time thing. I knew that I thought about her incessantly over the summer. I can’t begin to guess how many tissues I went through, recalling every second of our brief encounter. The amount of time I dedicated to her memory threatened my relationship with my girlfriend. As we held hands and necked like horny teens I wondered if she’d ever command me to go down on her or whip my cock.

I wondered if Mistress ever gave me a second’s pause; had our time together meant anything to her or was it meaningless. September brought me my answer.

She’d moved to the next level of English where I found her at the front of my first hour class. An older, busty woman with hair the color of dying embers accompanied her. Mistress introduced her as "Ms. Kelly," her teaching assistant. Mistress—I couldn’t think of her as anything else—had Ms. Kelly pass out syllabuses. They went over them line by line for our introductory class. However, when they reached the section on grading I started looking around the room.

No one seemed to notice anything amiss. I looked over the shoulder of the girl in front of me and saw that her syllabus differed from mine. Hers didn’t have the line: "Final grade will be determined wholly by level of service to Mistress and Ms. Kelly." Looking up to the front of the room, I caught Mistress glancing at me with a knowing look. Ms. Kelly mirrored this same expression a moment later.

The next week of school proved tortuous. Other than the one missive, I’d not gotten another indication from Mistress that I would be allowed to serve her again. That changed with one word written on the margin of my first quiz: "Tonight."

I showed up on Mistress’s door at 7 PM, guessing at the time. A Friday evening, her neighborhood was a ghost town with the first football game of the season happening nearby. I could hear the echoes of the marching band behind me as I knocked on her door.

Ms. Kelly welcomed me. I realized that my eyes were glued to her. Her hair up, her legs bared, her breasts hefted by her bustier; she didn’t look at all like the conservatively dressed classroom matron I’d gotten used to in the first few weeks of school.

She grinned at me, as if my lascivious thoughts sat plainly on my face. I imagine they did. I’d never seen a woman dressed in such a way apart from those in a few movies I’d caught late at night on cable television.

I can’t picture how I must have looked when I stepped into the living room to find Mistress dressed in the same manner as Ms. Kelly. I prayed that she’d turn around so that I could see the way her garment looked on her beautiful ass.

She quickly obliged me, bending over to retrieve something from a wicker basket near her fireplace. As she straightened I felt Ms. Kelly pulling my arms together behind my back and securing them with something, immobilizing my wrists.

Mistress stepped to us, holding something in her hands. I didn’t know the name of it then, having only seen similar devices in movies like
Ben Hur
where galley slaves are beaten to row ships faster. She came close enough for me to smell the leather of the flogger mixed with her sweet scent.

Without thinking I tried to move and Ms. Kelly held me fast, her nails digging into my flesh with warning. "Stay still," she said, her voice loud in my ear.

Mistress raised her arm slightly, the leather straps of the flogger moving higher and just brushing against the front of my pants. I was embarrassed, knowing she could see my hard on. She seemed to be aiming for it when she turned her wrist and brought the flogger back down across it. The ends of the leather straps brushed against me sending waves of pleasure through my body.

"You like that?" she asked sweetly.

I nodded vigorously and heard Ms. Kelly chuckle behind me.

Suddenly, Mistress flicked her wrist. The gentle straps lashed out against my crotch and it felt like I’d been punched in the groin. My knees buckled. Ms. Kelly held me up, her knee against my tailbone. Mistress flicked her wrist again, slapping the flogger against the front of my pants. I cried out and she smiled.

"Get those clothes off," she commanded.

Though Mistress had seen me naked before, doing it a second time wasn’t any easier, especially with Ms. Kelly present. When I hesitated Mistress raised her flogger threateningly. This quickened my pace. I got down to my underwear before I looked up, hoping she’d say, "That’s enough." She made a small circle with her finger instead, gesturing for me to carry on. I looked to Ms. Kelly who stood with her arms crossed over her chest, a knowing smile dancing at the corners of her mouth.

Once my bottom was bare, Ms. Kelly’s hands were on it, grabbing it, kneading it. "Oh, he’s got a sweet ass," she said to Mistress.

"Let’s get that ass under wraps," Mistress replied. Turning again, I felt my shy cock spring to life as Mistress bent to retrieve something else.

She noticed my hard on as she turned back with a roll of plastic wrap in her hands. "Oh, looks like someone’s excited," she mocked.

She removed the roll from the yellow box and handed it to Ms. Kelly. I felt her press the plastic against my back and heard the unique sound of cling wrap being unspooled. She passed the roll to Mistress who brought it around front of me and then back to Ms. Kelly. They worked with precision, passing it back and forth as they cocooned my entire body in the plastic.

I had stood motionless until I realized just how immobilized I had become. I worked to move my arms and found them held fast. My legs were nearly the same. I flushed with excitement as they worked around my thighs, my hard cock pressing against the plastic. I had delusions of it being so hard as to break through its restraints.

Mistress retrieved a roll of duct tape and used it in strategic areas—my elbows, my wrists, my knees—everywhere I might bend. Once she was done I stood teetering until she pushed me over with one finger.

I fell to the floor, my head landing on a well-placed pillow. I heard the heart-stopping sound of heavy metal scissors being opened and closed and looked up to see Mistress brandishing them fiendishly. She fell to her knees and I felt the cold blade through the plastic, pressing at my thigh. There was a little bit of pressure before the blade slid through the plastic, cool air hitting my already hot skin as Mistress cut away the plastic around my cock.

Handing the scissors to Ms. Kelly, Mistress slid herself up my body with ease, sliding over the plastic and coming to rest with her bare pussy mere inches from my face.

It was slightly difficult to breathe with her legs on either side of my head but it was worth it. I was given the privilege of returning her gaze as she looked down at me, confidently.

She had paid little mind to my cock after she freed it from the wrap, merely laughing when she saw it spring forth after unleashing it and commenting on how pathetic and small it was.

I could only hear her, at first, until she trailed the nine leather straps along her tender thighs. My jerking and jumping from the blow only seemed to amuse her. She chuckled a bit at my misery before caressing my forehead and calming me.

"There, there. That’s a good little pussy boy. You do want to take another for me, don’t you?"

Of course I did. I wanted to do anything for these women. I was theirs. I belonged to them.

"Please, Mistress. May I have another?" I asked.

She nodded and before I could even discern that time had passed another blow landed upon me. And then another. And a third. Each making my body jump with the stinging pain. My breath came in pants, which seemed to intensify her wonderful scent.

"What do you say, slut?" she asked, her eyes locked onto mine.

"Thank You, Mistress. Thank you for the pain."

"Do you like being here?

"Yes, Mistress."

"Do you like pussy?"

"Yes, Mistress!"

"What do you like about it?"

"Everything, Mistress. The sight, the smell, the taste, the feel. It appeals to all of my senses."

"You’re probably hoping that I scoot myself up just a few inches and let you taste me. Is that true?"

"Yes, Mistress."

"That’s not going to happen. A little bitch like you isn’t good enough to eat my pussy. You’re not good enough for my pussy. You’re barely good enough for my ass. If you’re a good bitch tonight, perhaps I’ll let you lick my ass."

"Thank You, Mistress."

"I bet this is a strange position for you, isn’t it? Being between a woman’s legs. We both know you’re a little faggot, aren’t you? Aren’t you?"

I hesitated in answering. I’d been called a "fag" by my friends in a joking manner but never like this. Never in a way that meant it. Her flogger prompted a response, "Yes, Mistress."

"Tell me, bitch, how many cocks have you had in your mouth?"

"None, Mistress."

"No? Oh, that’s a shame. There’s nothing I like better than seeing a sissy like you sucking cock. There’s just something nice to see a faggot get in touch with their inner cocksucker. You really must try it, dear."

Without realizing it, Ms. Kelly had donned a strap-on dildo. She kneeled next to me on the floor where I laid helpless, her rubber cock waving in the air. Though not flesh and blood, I knew that it would give her and Mistress pleasure to see me suck it as if it were. Mistress rose off of me and pushed me over to the side of the ottoman so that Ms. Kelly could use her strap-on on my face. She teased me with it, rubbing it across my face, my mouth waiting in anticipation.

She laughed. "Look at how this faggot wants my cock. Look how he’s trying to get it into his mouth. He can’t live without it."

"You keep his face, I want to fuck this faggot’s little pussy," said Mistress.

After some rearranging and some more use of the scissors, I found myself on my elbows and knees between the legs of Ms. Kelly, sucking her strap on while Mistress inserted her own strap-on into my now exposed ass.

I felt like a pig on a spit, a cock in my mouth and one in my ass, both being worn by beautiful women. Both of them telling me how ridiculous I looked, taking cock like the whore I am. I hoped that Mistress could find the sweet spot on herself where she could get pleasure from fucking me—physically as well as mentally.

Soon, I began to hear her breathing change and knew that, indeed, she was getting off on her thrusts. I tried to meet her pelvis with my ass with each deep plunge. I only live to give pleasure and being used in this way was incredibly fulfilling.

I continued to work on Ms. Kelly’s cock but knew that she was watching Mistress, seeing her face flush with pleasure as she moved closer to orgasm.

I can’t even begin to describe the warmth that flowed through me as I felt Mistress shudder and cross over the brink, cumming while fucking me. She plunged deeper, deeper, into me and I welcomed her and the pleasure/pain. She seemed to cum forever before slowing her thrusts and eventually pulling out of me, leaving me missing the feel of her cock.

I was disappointed to be empty for only a brief moment for soon Mistress decided that I should have the reward she had mentioned.

Ms. Kelly moved to my side, gently caressing my exposed flesh while Mistress moved in front of me, raising her skirt and lowering her panties to expose her lovely bottom to me. "Eat my ass, bitch. Put your tongue inside my asshole and taste me."

I licked and tongued her ass as best I could, dreaming that it was her pussy and getting off on it every second. I only did it with more vigor after Ms. Kelly decided to "motivate" me by placing a finger inside of my own ass, fucking me with her finger while I "fucked" Mistress’s ass with my tongue. She allowed me to do this for a good long while before she simply uttered, "Stop."

I backed away and waited patiently for my next command.

"Has it been a month already?" she asked; her hand on the open door.

She was dressed as she had been last time; white blouse, black skirt, glasses. If I had to choose one word to describe her, it would have been "commanding." It might have been the glare in her eye or the way her other hand was placed on her hip. More likely, it was her tone of voice and the way she managed to look down on me, despite her being a few inches shorter.

"Yes, Mistress," I stammered, still getting used to the term.

In the mornings she was my English teacher. She never communicated with me outside of class save for note paper clipped to my homework. A cipher, it took me a few hours to work out the words: "same place, same time."

"You may enter," she said.

Once I was in the vestibule she told me to strip completely. I still felt incredibly embarrassed, removing my clothes in front of my teacher. She had me kneel, deeply, and kiss the top of her shoe as a sign of submission to her.

She walked around and stood behind me. I could sense her behind me and it excited me even more. If I listened hard enough, I thought that I could hear her breathe. Without warning, she plunged me into darkness as a blindfold was placed over my eyes and secured tightly. Then I felt what I could only imagine to be her shoe on my mid-back.

"Down," she said. Now on all fours, she had me crawl forward, trusting that she wouldn’t run me into any furniture. "Stop."