From Cuckold to Collar

by Bob Neils

  All the while, I felt Mistress growing harder and longer against my ass. I couldn’t help myself. I arched my back like a bitch in heat, thrusting my ass up and back against her. She laughed and slapped me, then grabbed my hips and held me there while I feasted. It was pure pleasure and sheer agony at the same time. My cock strained harder against its cage than ever before. I could feel it leaking all over the bed.

  That’s when Mistress jerked me to the side and stepped up beside me.

  “Watch,” she instructed, “but do not touch.”

  Her cock felt hot and hard against my cheek as Mistress stroked herself, faster and harder. I could hear her breaths coming closer together, and I saw precum spreading over the head as she stroked. When she came, it was a small, quick series of spurts. Nothing like I was accustomed to, but still impressive for what had to have been her third or maybe even fourth orgasm of the afternoon. It was more a symbolic act of cuckolding than anything else, but I could tell both her submissives appreciated it, for Heather gasped and trembled as she felt the hot spurts land across her lips.

  She never once uncrossed her arms or opened her eyes.

  A New Life Begins

  Our last dinner before my formal collaring was a casual affair consisting of light food that wouldn’t weigh us down. Mistress had an intense evening planned for us and was insistent that nothing interfere with her plans.

  Afterwards, we packed an oversized picnic basket with a bottle of wine, two glasses, some fruit, a blanket, and a few other items that were wrapped in leather and tied with an elaborate knot that I could never, in a million years, hope to reproduce – not that I would even consider trying to peek at what she was bringing.

  One of her dungeon clients was a maintenance lead at one of the hotels along the river, and he had loaned her a pass-card for the weekend. While everybody else jockeyed for position by City Hall, crowded around the edge of Civic Square, or simply pulled off to the side of the road and illegally blocked traffic, we’d be watching the New Years’ fireworks from the rooftop solarium, which was conveniently closed for renovations.

  It was an unseasonably warm evening for the end of the year, with a mixture of drizzling rain and big, wet flakes of snow. The wind was brisk, though, and you could feel the first real storm of winter threatening. As we stepped out into the roof, Mistress pulled her cloak around herself, sealing out the cold. I’d only been permitted a t-shirt and pants, and I wasn’t going to be wearing even that for long.

  As we approach the glass doors of the solarium, Mistress turned to face me. “Disrobe.”

  I did hesitate, but for only a moment. I was terrified of being seen naked in public, but I also trusted her implicitly. I stopped myself from looking around and instead stared at my reflection in the door. What I saw was an entirely average man. Average size, average height, average build, in average shape. My hair was short, and my face shaved. Maybe there was a grey strand or two at my temples, and maybe I could stand to lose five or so pounds, but I realized at that moment . . . nothing I thought mattered.

  I did as she commanded, my flesh breaking out in goosebumps from the cold, and my already caged cock shrinking even further. If we stayed out there much longer, I feared the cage would simply fall off, with nothing there to hold it in place.

  I pulled off my shirt, folded it neatly, and laid it on the rooftop. Mistress had offered me an opportunity to become hers, and that meant all of me. From this day forward, she would control everything about me. It was an idea that I knew might terrify others, but I was exhilarated. I quickly removed my shoes and socks, placing them beside the shirt. Next, I removed my pants and underwear, folding them and leaving them atop the shirt. Looking down, I saw a typical hotel roof with a myriad tiny rocks, leaves, and bits of trash.

  My nipples popped out, my teeth chattered, and my knees shook. Up here, fifty-nine stories above the crowds, with the wind whipping around the heating vents and electrical boxes, it was far colder than it had seemed down below.

  Mistress unlocked the door, and then turned to face me. She looked excited. There was a dangerous glint to her eyes that I had not seen outside the dungeon. “Tom.” She made sure she had my full attention. “We are assured of complete privacy here. Can you trust that I have made all the arrangements necessary?”

  “Yes, Mistress.” I nodded without question. “Of course.”

  She nodded. As I watched, she tied her hair back in its rather severe ponytail. “Good. It is time to formalize our arrangement. If you are still interested, you will drop to all fours and follow me inside.”

  With that, she turned and stepped through the glass door.

  I dropped to the roof, where small rocks and stones dug into my flesh from beneath the light dusting of wet snow. As I crawled through that door, I knew I was leaving my old life, my old self, outside. I had shed far more than just clothes.

  Inside, the solarium was dark, but it was warm. Mistress nodded once, then pushed the door shut behind me. She turned back and, without a word, without a sound, she opened the picnic basket, withdrawing the leather-wrapped bundle and laying it aside. While I watched, curious, she uncorked the bottle and poured herself a glass of wine.

  She removed her cloak and laid it over a chair. With her back to me, she unzipped the side of her dress, allowing it to pool at her feet before stepping out of it. Dressed only in a black bra, panties, stockings, and heels, she began walking around me, those heels echoing loudly within the glass walls. “This is all so perfectly symbolic.”

  She paused behind me. I trembled before her.

  “The chance to lay bare your very self, for the whole world to see?” I felt her nails drag parallel lines down my bare back. “The opportunity to step from one life, one year, into another?” She raised those hands and hooked her fingers into the gap between my neck and my collar. “The romantics always speak of fireworks when talking of love. Tonight, you and I are going to make that literal.”

  I gasped as she tugged at my collar. She yanked, hard, until the snaps fell open and it came free from my flesh. I blushed, feeling more naked than I had outside. I’d become accustomed to my collar. Not wearing one felt wrong. “What do you say, slave?”

  “Thank you, Mistress.” I was shocked to find tears welling at the corners of my eyes. I felt naked, exposed, and vulnerable. And then her hand settled atop my head and I immediately warmed to her touch. “I have been waiting for this night. There is nothing that I want more.”

  “Up,” she barked. “Assume your first position.”

  I climbed to my knees, keeping them pressed tightly together, with my ankles crossed behind me. I arched my back and thrust out my chest, but kept my head lowered. My arms were held behind me, my hands clasped at the small of my back.

  I could already feel the physical strain.

  Mistress pressed the toe of one shiny black shoe between my knees. “Second slave position.”

  I immediately spread my legs.

  She stepped forward. Her toe began tapping against the plastic of my chastity cage.

  “This comes off tonight. I will not have my property contained in such flimsy hardware.” Her foot traced a path up from my cage and over my stomach. It twisted, pressing the stiletto heel into my belly button. Mistress held it there for a moment, and then kicked hard, shoving me over onto my back. “Arms at your side, legs pressed tight.”

  My body was trembling as I obeyed. I had no idea what she had planned, and that uncertainty, that sense of the unknown, was exciting.

  Now it was Mistress’ turn to kneel, one leg on either side of mine. She reached into her bra and pulled out a small metal key. The sound of it sliding into the tumblers of my cage was impossibly loud. I felt the click of it unlocking as much as I heard it. While she had granted me five minutes of freedom once per week so that I might clean myself, this was something else entirely. This was an act of significance that would redefine our entire relationship.

  I gasped when she wrapped one of those beautiful b
lack hands around my cock and gave it a quick stroke, sheathing it in some kind of thick lube. It immediately sprang to life, filling her hand. It was rock-hard and fully-erect in seconds. The rush of blood left me momentarily lightheaded.

  It had been three months since my last erection.

  Yes, I had attempted to cheat once during a cleaning. I could have gotten away with it. She saw nothing. But I’d confessed and been punished accordingly.

  She leaned forward. Her breasts pressed against my chest. “I am going to ride you,” she whispered. “I am going to fuck one final orgasm out of that useless piece of flesh.” She darted in and nipped at my ear. “You are going to lie there. You are not going to move a muscle. You will not thrust, grind, tilt, or contract. You will do nothing to hasten your orgasm.”

  Mistress sat up. She slid backward down my body. “Not that I expect you to last, but this is my doing, my ride, my orgasm.” Her ass stopped with my cockhead pressed against it. “I trust you appreciate the significance of this. No man has ever penetrated me with his cock. I have ridden my share of dildo-wearing sissies. I have taken loads from shemale and transsexual sisters whom I admire deeply. I have even allowed a dominatrix or two to peg me.” She squirmed against me, rubbing my precum all around her hole. “But no man has never been granted entry.”

  “Fuck.” I tensed, and immediately forced myself to relax. “I will not disappoint you, Mistress. I will never let you down.” My heart was pounding in my chest. This was huge. I wasn’t ready. I wasn’t worthy. “You honor me, and I pledge my lifetime of slavery to repay your trust.”

  Without another word, she pressed herself backward. I’d like to say my cock slipped right in, entering her at a perfect angle, but it fell too low and folded back upon itself. I hissed in pain but made no attempt to correct my position. Mistress nodded gently, almost imperceptibly, but she let me know she had noticed.

  This time, she reached back to hold my cock in place as she pressed herself against it. I had to bite my tongue to distract myself from cumming as I felt the outer ring of her anus open around me. I cried out through clenched teeth, tasting blood as she pushed backward, forcing herself upon me. I felt the head of my cock pop past her inner ring, and then I was inside her. She wiggled herself down my shaft until she was sitting on my stomach, her balls trapped between us.

  “How does that feel, slave?”

  “Like bliss, Mistress.” My head was swimming with sensations I had not felt in ages. “Overwhelming, overpowering.” I smiled. “I feel used, and I like it very much.”

  Mistress rode my cock with long, slow strokes of agonizing tenderness. She didn’t allow me enough friction to build to any sort of orgasm. Instead, she wiggled and squeezed, making sure I knew I was trapped, a tool for her own pleasure.

  “I have thought about just sitting here, letting you grow limp inside me, and calling it done,” she teased, “but that would ruin what I have planned next.” She began riding me faster. “That would ruin my fun, because I have been waiting a very long time to introducing my cuckold slave to his new chores.”

  Mistress rode me harder and faster with each word. My body tensed beneath her. I saw stars as I felt my orgasm build. I wanted it. I wanted it so badly. I wanted to feel that rush of pleasure as my cock exploded. At the same time, however, I dreaded it. I feared that post-orgasm letdown and what it might mean for my ability, my enthusiasm to serve her.

  It didn’t matter.

  She squeezed hard on her last descent and I exploded within her.

  “Oh, my.” Her eyes widened in surprise. “That was quite a load. Not surprising, considering how long it’s been building.” She grinned. “You have performed well, but we still have a long night ahead.” I felt her ass rising, and the pressure, the friction against my softening cock was sweet agony. “I do so hope you won’t disappoint me.”

  The moment my cock popped free from her ass, she turned around. I watched, in horror, as her ass approached my face, coming closer with each shift of her knees. I could see my own cum leaking from her ass. I could see her perfectly puckered little hole winking at me, the muscles inside clearly tensing and relaxing repeatedly.

  I didn’t know if I could do this. Post-orgasm letdown or no, I had never tasted a woman’s ass before. It was a soft limit for me, something that grossed me out, knowing what else it was used for. I had nightmarish visions flash through my head as the warmth of her ass cheeks enveloped my face. I began breathing hard, nearly hyperventilating. Not only was she expecting me to lick her ass, but she wanted me to clean my own cum from it.

  As big a cum whore as I was, as much as I loved feasting on creampied pussies, swallowing anonymous gloryhole loads, and sucking the seed from her magnificent black cock, that post-orgasm depression has always stopped me from enjoying my own.

  Mistress paused when my nose poked itself between her cheeks. “This is a pleasure you will become accustomed to,” she purred, “once you get past your mental block. I am not a sissy. I won’t call it something cute, like my ass-pussy, but it is as much a sexual organ as your cock, your ass, Heather’s pussy . . . or Tricia’s.” She wiggled herself around my face. “You’re too focused on its dual purpose. Guess what. They all have dual purposes, as full of blood and piss as they are cum.”

  It was hard to focus, hard to think, but what she said made sense.

  Mistress sat back and let all her weight rest upon my face. “You need to trust me, Tom. Implicitly and without question.” She did something with her ass. I felt a hot globule of cum dribble out and run down my upper lip. “I always clean myself out when expecting sex, and I chose a light dinner for a reason.” She squeezed out another drop. “You can do this.” She pushed herself harder against my face. “Suck my ass, slave. Fuck me with your tongue. Clean up your mess.” She lifted herself off me. “I want you to make me feel good.”

  That did it. Her rational arguments had made a dent in my resolve. They had started wearing away at my reluctance, but knowing that she wanted it, knowing that it would provide her with pleasure, that was what it took to overcome my fears.

  I raised my head up and licked at her chocolate rosebud. It tasted . . . okay. Good even. There was a slight earthiness to it that, mixed with the musk of her sweat, was erotically powerful. It felt strange against my tongue, tighter and hotter than a pussy, with an unusual texture, but none of that was unpleasant. It was just different. I pressed my face deeper into her cleft and wiggled my tongue inside.

  “Oh, yes.” She pushed back against me. “Tongue fuck me, slave. Get in there deep and lap up every ounce of your cum.”

  I don’t know if it was the novelty of the situation, or whether I was becoming aroused, but even my cum tasted better. I was soon poking my tongue in deep, swirling it around, and sucking at the juices dribbling out with each contraction of her muscles. It became very much like cleaning a creampied pussy, except this was my Mistress, her ass, her sexual organ. I wasn’t worshiping some woman’s cunt, I was worshiping at the altar of the ass of the woman who owned me.

  The first touch of cold metal around my balls didn’t really register, but the first ring to slide over my limp shaft did. I didn’t stop. I kept licking and sucking as I felt ring after ring slide down. I focused on leaving her ass as clean as it had been before I left my mess inside as the cold metal head of the cage pressed down over my own. I did cry out into her ass as she pushed those rings together, compressing my cock even more than it had been in its plastic cage. Bits of tender flesh pinched between the rings, the pain making me even smaller.

  I never heard the click of the pin being locked and snapped, but I swear I felt that vibration shudder through my body.

  “Much better.” Mistress abruptly stood up, leaving me gasping for air. “That is how I like to see my property protected.”

  I looked down between the inverted ‘V’ of her legs and saw the cold, hard, metal cage of my cock. It looked so small, so tight compared to the plastic cage, and yet I could feel just a little
room. I was afraid what my first attempted erection might feel like, but I looked forward to it as well. Mistress wanted this, and I understood what it meant.

  I wanted it too.

  “Lift those legs, slave.” She walked around to stand between them, taking an ankle in each hand. As she lowered herself to her knees, she pressed against my ankles, spreading me wide. It hurt. It was too wide. I feared she would split me in half.

  I didn’t want her to stop.

  “I have wanted to fuck you for so long,” she hissed. “That ass was made for my cock, but I wasn’t about to break the cherry until I owned it.” She let the tip of her cock rest against my shriveled testicles. “Do I own it? Are you mine? Have you chosen?”

  “I am your slave, Mistress.” I trembled with anticipation. “I always was. Always will be.” I thrust myself upwards, granting her a better angle. “Please, Mistress.” I looked into her eyes and saw so many emotions there. Pride, lust, satisfaction, hunger, arousal, and affection. “Please fuck your slave.” I swallowed the tiny nugget of fear I felt upon seeing the contrast in size between her massive, fully erect cock, and my own limp, caged stub of flesh.

  She reached down and, with one sharp tug, ripped the plug from my ass. I cried out, but then it was as if the world stopped as her cock slid down towards my hole. Everything around us faded away as she began pressing against me. It hurt. There was a pressure there, an insistent intrusion that wasn’t getting any harder or deeper, but which refused to back off.

  I knew what Mistress wanted. I instinctively knew what she was waiting for.

  It was hard. Even after cleaning my cum from her ass, it seemed I still had something of an anal hookup. I still had a fear of its other uses. I had to get over it. I had to put it behind me. I had to move beyond it if I was to honor my Mistress.

  I closed my eyes. I took a deep breath. I pushed out with my sphincter muscles, forcing myself open. The moment I felt some give, I lifted myself upward, pressing up against her cock, and welcoming it inside. There was pain. Hot, fiery pain as her head poked into my hole. I was terrified of something tearing, but I put that aside. I blocked those fears. Instead, I took another deep breath, pushed out with those same muscles, and with a guttural scream I thrust myself up again, taking a good inch or two of her cock inside.