Freedom is Slavery

by Louis Friend

  I held her down as I came inside of her mouth while she sucked every last drop of it out of my spent cock. She kept her head in my lap, licking at the oversensitive head of my cock for a few minutes, lapping up the last few drops. I stroked her hair and smiled.

  She went to her bathroom and came back with a warm washcloth that she wiped me off with before saying, “That’s the kind of payment I’m willing to give. At least one of those per page of my site. Does that sound fair?”

  “Was that just the homepage?”

  “No, that was just to see how you reacted. We’ll talk about the homepage more tomorrow.”

  Working for Zoe ended up being the best job I ever had. She gave me a whole new perspective on freelancing. After her site was done, Zoe gave me a discount for her services for life and passed my contact information along to a number of her friends who were looking for a similar deal.

  Sybarta

  I always enjoyed my time with Sybarta. While I always knew my place (she would remind me constantly, having me refill her coffee, fetching her mail, standing whenever she entered the room, et cetera), we would have rather pleasant, open conversations to relax us both before the fun began.

  However today, Sybarta was acting a bit out of sorts. As soon as I was allowed in to her cottage, in the rural outlands, she commanded me to fall and kiss her boots; the signal that our session was beginning. Prostrate, she then commanded me to remove my clothes and sit in her bondage chair.

  The wood of the chair was a chilling shock to my bare bottom, as was the metal buckles of the cuffs she used to secure my wrists and ankles to the arms and legs of the tall chair. Another, larger belt was then wrapped around my neck and secured to the back. Sybarta gave this one a bit of a tug, choking me slightly to remind me that my life was now in her hands.

  While Sybarta may have been old enough to be my mother, she managed to maintain an impressive figure. Unlike the Dominatrices of popular myth, she didn’t prance about in fishnets and corset. Rather, she resembled a truck stop patron in her coarse denim shirt and flattering jeans. The only leather she wore were her boots which still carried a strong, heady scent.

  Sybarta displayed a bit more of herself now as she stood in front of me, unbuttoning her shirt and exposing her bare breasts. She leaned in close to me and I could smell her clean scent of roses and peppermint. She allowed her breasts to get close to my open, wanting mouth. I longed to wrap my lips around her succulent nipples, knowing that I could provide her with pleasure and, perhaps, see her visibly shudder with excitement as I had witnessed in the past. She said not a word as she moved in closer, the nipple of her left breast just barely brushing my bottom lip. Finally, she moved in close enough for me to latch my mouth onto her nipple and suck.

  When I first met Sybarta, I had barely done any “petting” in high school. I was always more than cautious when dealing with the female anatomy. I had never done anything more than kiss a girl’s nipples. It was Sybarta who taught me, commanded me, to do more than kiss and lick. I sucked, I bit, and it often felt like I was practically chewing her nipples. The harder I sucked and nibbled, the more she liked it. At first, her moans scared me. I thought they came from pain, not pleasure. Sybarta was the one who first taught me how interchangeable these notions of sensation could be.

  She removed her left nipple from my mouth and replaced it with the right. Her hands gripped the top of the chair; one of her fingers absently caressed my right ear. She leaned in to the left and sent shivers down my spine by telling me that I was being, “a good boy.”

  She straddled my legs with hers, sitting down across from me, her weight on my legs. She stared at me with a look of self-satisfaction on her face. An evil glimmer soon came into her eye as she told me, “I’m going to slap you. I just want to hear the noise.” She caressed my left cheek with her palm before pulling it back and striking a blow.

  Somehow, knowing that it was coming, combined with the fact that I was taking the pain for Sybarta, helped keep the tears from my eyes, despite the stinging pain. She repeated the same thing on my right cheek and then gently kissed the red marks that came up.

  Apparently, Sybarta was in the mood to cause some pain and I was going to try my best to take as much as she could dish out. She liked to push my limits, giving me more pain each time we were together. “It pleases me to hurt you,” she would tell me as she watched the tears streaming from my eyes.

  Bound as I was, I was powerless to do much more than whimper when she reached down and cruelly pinched my nipples. She looked deep into my eyes as the pain shot through me. She loved reading the fear that my eyes revealed. I was oddly quiet during these moments—while I wanted to scream, she didn’t want to hear it. If I was too noisy she would gag me, lowering the chances that I might have something better put in my mouth.

  I kept as still and quiet as I could as she placed the first of many clothespins on me that day. Pulling down a bag from a nearby shelf, she fished them out, one by one, and clamped clothespin after clothespin on my flesh. Initially she put them on my nipples and earlobes. Then she began decorating my hard cock with them. She started at the base, going around and around my cock, attaching more and more clothespins until my sex organ looked more like a porcupine than a penis. With each biting sensation, I would take in a bit more breath.

  “Breathe,” she would remind me.

  Each clothespin felt like a tiny, sharp-toothed mouth on my flesh but the intense pain didn’t start until Sybarta began clipping more of the wooden torture devices to my scrotum. I tried to keep track of the number of them on my skin as I knew that the pain I felt now would be nothing compared to when they were removed. I lost count after she got about twenty attached to the tender skin of my ball sac.

  Sybarta ran out of clothespins before she ran out of bare skin to pinch. When she was done, she took stock of her handiwork and began to play me like an instrument— touching, turning, and slapping various clothespins. Each one provided a different sensation, all based in pain. Still my cock did not falter. Serving Sybarta kept me incredibly aroused, despite the screaming fire of my flesh.

  I tried to maintain some modicum of silence but the pain at times was too great. When I cried out, Sybarta would shush me and carry on. I could tell that she was enjoying it greatly. She got her greatest pleasure when she began plucking the clothespins from my skin. The rush of blood to each little area caused an incredible amount of pain. She plucked them off, one after another, quickly and then slower before going fast again, judging my reaction and enjoying taking me to the edge.

  Once they were all removed I was allowed to catch by breath. Sybarta told me that I did a good job for her and that she would give me a reward. Little did I know it would be one of the best she had ever given.

  She slid her left hand into her jeans and withdrew it a moment later. She held her hand out to my nose and allowed me to smell her scent. It was only the second time I had been allowed to take in the scent of a woman and, this time, she allowed me to taste her as well. She rubbed her fingers over my closed lips before telling me to open wide and take her fingers in my mouth.

  It was my first time tasting a woman. I had tried performing cunnilingus on my high school girlfriend but didn’t get too far before her Catholic guilt forced us to stop. But she was merely a girl. Sybarta was a mature woman and one who had me bound and at her mercy. I relished her heady smell and taste. I couldn’t believe that I was finally getting to taste the thing I had dreamed about for years. And, as fast as it began, it ended as she withdrew her fingers. The scent and taste remained on my lips a bit longer and I savored it as long as I could.

  As I licked my lips, Sybarta released the collar around my neck and wrists. She lowered the back of the chair so that I was now laying flat on my back, my ankles still bound. She bound my wrists to one another over my head before placing a blindfold around my eyes. She told me to open my mouth and stuffed it with something that I couldn’t discern. I would find out later (months later when she d
id the same thing without the blindfold) that she had placed a large dildo in my mouth.

  I held the base of it tight between my teeth while Sybarta, now free of clothes, mounted the large rubber dong and rode it to orgasm. I was again in heaven as I relished the sweet smell of her scent and even felt her fingers occasionally brushing my cock but, as naïve as I was, I really didn’t know what she was up to, despite the moans and the weight of her body on my chest. It wasn’t until Sybarta orgasmed—screaming like a wild beast—that I had a clue what might have been happening. But, by then, it was over. She removed the dildo from my mouth and reversed it, placing the now-wet end into my mouth, allowing me to feast on her flavor yet again.

  I was lost in euphoria, tasting her, my heart in my ears and my eyes blind to the world when I realized that the phone was ringing. I heard bits of a muffled conversation before Sybarta returned to me to say, “I have a special surprise for you.”

  What could have been more special than everything that had gone before? I couldn’t even fathom. I just knew that I was in for another treat.

  Sybarta released me from my bonds and led me, across her floor, still blindfolded. Here in this odd sanctuary of hers, her cot, her bondage chair, and a footlocker were all the furniture the room had to offer. The walls were sparsely decorated with her odd artwork and the cold tiles of the floor chilled my feet as I moved to her cot. She had me on my hands and knees on the cold canvas. She ran her fingers lightly across my back. I was startled by an unexpected knock on the door.

  “Shhhh… shhhh…” she said. “Do you trust me?”

  “Yes, M’lady,” I replied and I meant it.

  “Then you just don’t worry. Know that what happens here is for the best for you.”

  With that, she left my side. I strained to hear what was going on. I heard her front door open and close, a cold breeze from outside turned my skin to gooseflesh. There was a bit of muffled conversation and other indiscernible noise. I could hear Sybarta coming back towards me when she said, “Here he is, as promised.”

  Fingers ran along my back again, but I could tell that they didn’t belong to Sybarta. There was a third person in the room (if not more) and they were touching my bare flesh. I could smell the faint odor of leather and thought I sensed after-shave lotion. The touch was rougher than Sybarta’s, more insistent, as if I was being inspected.

  A hand grasped my hard cock and gave a good squeeze. I couldn’t help but moan from the pleasure it brought. I heard a snort of derision and felt certain that the hands on me belonged to a man. This sent my mind into a tizzy. I had always been self-conscious about my body, especially in front of other men. I avoided gym class in high school and any other potentially embarrassing locker room scenarios. I had never been naked and prone in front of a man before, much less one who was touching me. I felt like I wanted to run out of there immediately. If it weren’t for the soothing sound of Sybarta’s voice, I might have done just that.

  “Shhh, it’s okay, baby. This is something that I want to see. This is something you need to do for me. You’re going to be opened up and taken. Then I will know with certainty that you are Mine.”

  She held my head in her hands. I could feel her warm breath on my skin at just about the time I felt a cold, wet finger on my virgin ass. I had read enough in porn magazines to know that lubrication was being applied to my anus and that I would soon be violated; penetrated by another man’s cock.

  “I’m honored to be here for this and that you’re taking this first cock for Me,” she said. “This will be the first of many, I’m sure. I love to see men together like this. I won’t have you suck him today, but will save that for another time. He’s got his cock right on your asshole. Show me how much you want it. Push back on it and fuck yourself.”

  I really couldn’t believe what I was hearing, much less what I was doing as I leaned my body back into the pressure that rested on my anus. Suddenly, I felt myself yield and open to the foreign object behind me. I gasped but didn’t stop. I pushed back slowly, stopping every few seconds to allow myself to adjust to the cock that was now in my body. I didn’t realize how ragged my breath had become until Sybarta told me to breathe easy.

  Having proven myself a bit, Sybarta had me stay where I was and had the unknown man push the rest of himself inside of me. I had no idea how much cock was in me but it felt like I was being torn apart. Before long I felt the rest of his body up against me and knew that he was completely in. This was the part I feared the most, feeling him now remove a bit and plunge back into me. Here I was, still a virgin in the sense that I had never been inside of a woman, but now opened up to a man who was slowly fucking me. I could feel his hot breath on my back and his hands grasping my ass cheeks, pulling me back and pushing me forward, using my body for his pleasure.

  “Oh, shit yes,” Sybarta hissed, taking in the show. “Now for the part you’ll really like.”

  With that, I felt fingers around my cock again. I couldn’t tell now whose they were, I just knew that they were stroking my cock and bringing me a lot of pleasure. The strokes came in time with the thrusts of the man behind me.

  Could it be his hand? Sybarta’s?

  I have to admit that I didn’t care. I just didn’t want it to end. I felt the burning need to orgasm, now as I was being pummelled by the faceless stranger. Harder and faster the thrusts came. I wondered what it would feel like to have a man cum inside of me.

  Would it be like a flood? Would I even tell?

  Again, I really didn’t care much, as long as the hand stroking me stayed on my cock. I began to feel like I was coming to the edge. Soon I heard myself asking Sybarta for permission to cum.

  “Not yet,” she said.

  Now it became a bit of a struggle to hold myself back. The thrusts got harder and faster, the slapping of the man’s body against my ass filled my ears.

  “Now,” she said.

  It didn’t take more than a second for the floodgates to open. It felt like I wouldn’t stop cumming. Slowly the cock inside of me stopped moving. I couldn’t tell if the man had cum or not, but really I wasn’t thinking about much of anything. My mind was reeling from the sensations.

  Eventually, the cock was removed and—I have to admit—I really missed the sensation of being filled. I knew that I’d have to admit that to Sybarta later on but, for now, I kept it a secret. I could hear what I imagined being a condom removed from a cock. I heard the man behind me breathing heavily.

  “Did you cum?” Sybarta asked. I knew she wasn’t talking to me.

  “Yes,” came the reply. To my surprise, the voice was completely feminine.

  The blindfold was removed and I was told to look over my shoulder to meet Sarah, Sybarta’s main submissive. Her hair lay wet across her forehead from the exertion. Again, I knew I would have to ask Sybarta how a woman could cum from fucking a man in the ass.

  “Next time, Louis, that will be a real cock. I think you’ll enjoy that even more,” Sybarta assured me.

  She had me lay down fully on the cot once Sarah was up and placed a blanket over my spent body. I felt the cold pool of spunk under my belly and realized that this was the first time a woman had ever brought me to orgasm. A smile curled across my lips as I fell asleep, safe in Sybarta’s lair.

  Big Fun in a Small Space

  To say that my apartment was small is an understatement. As the old joke goes, you had to step into the hallway just to change your mind. It always amazed me the amount of things that Kitty could do to me in such a small space. But really, most of the things she did to me took place in the space between my ears.

  Kitty came in carrying a small duffel bag and wearing an evil grin on her face (and not much else). She told me that tonight she would be using me in ways that I’d not been used before.

  I could only gulp a bit and know that whatever she was doing would be in my best interest and more importantly, for her pleasure.

  She instructed me to strip. She stood and watched, with her arms crossed,
as I removed all of my clothes. I reddened under her gaze. Kitty tapped her booted foot impatiently as she watched me remove every inch of clothing. Once I was bare, she had me stand with my hands above my head, facing away from her.

  I could hear her getting items out of her bag. Time moved strangely for me as I stood, staring ahead at nothing, listening for everything that I could and wondering what was in store for me.

  Her warm hand grasped my shoulder. “Turn around and lay across the bed.”

  I felt something slick and hard push against my asshole. Bending over, I felt it penetrate my hole. The invasion wasn’t gentle and it wasn’t quick. She pushed something inside of me, deep and fast. I gasped and she shushed me.

  “Just accept it,” she told me.

  Suddenly, I felt the sensation of warmth and wetness. “Grasp your asshole tight,” she commanded.

  Obeying, I felt myself being filled now. She moved into my peripheral vision where she had a tall rack like one would see in a hospital. Rather than an IV handing from it, there was an enema bag. She loosened the clamp that began flooding my insides with a deluge of water and discomfort.

  “You’d better take every drop,” she hissed before leaving my side.

  I whimpered helplessly as my insides were irrigated. It didn’t take long for the cramping to start. I had never had an enema for “recreation” before and it had been years since my last one. I forgot the intense discomfort.

  I closed my eyes and concentrated on keeping my asshole as clenched as I could make it. I didn’t want to embarrass myself or upset Kitty by disobeying. I tried to keep my breathing steady, though I wanted to pant with nervousness and pain. While I did this, Kitty readied other things in the room.

  “Hold tight,” she said.

  I tried clenching as fast and tight as I could as she snatched the nozzle from my bottom. I felt a few drops of water drip down my legs but managed to hold in the rest of the solution that filled me.