From Cuckold to Collar

by Bob Neils

  “Mistress.” I smiled. “You have nothing to hide, and nothing to fear. I laid beside you for half an hour this morning, just staring at your face. Watching you sleep.” I turned our hands over and began gently stroking hers. “What I saw was simply your natural beauty, the shape of your femininity. I saw nothing to suggest otherwise.”

  “I thank you for that.” This time when she smiled, I saw a tear escape her eye. “It’s a good thing we’re not formally collaring you quite yet,” she laughed. “I may need more time than I thought to find my footing with all this.” She released my hand and reached for another slice of toast. “It may take us some time to find that footing together, to balance real life with fantasy, to find the perfect line where affection meets domination, but I am increasingly confident that I chose well with you.”

  We spent the day being a couple – after, of course, she allowed me to dress. We walked the neighborhood together, had lunch at a little café, and even did a little grocery shopping for dinner. She was a strong woman, an assertive woman, but also one with a biting sense of humor and a very soft heart. In one breath she could chastise a waiter for allowing a drop of coffee to stain the café’s tablecloth, and in the next she was cooing and waving at the baby being burped across from us.

  In a sense, it was like a first date, but it was also like a reunion of old friends. One thing that did come up early in the day was the question of how to address her. In my head, in her house, and in her dungeon, she would always be Mistress. She had not told me her first name, and I didn’t wish to know it. That was a level of familiarity we both agreed was unfitting for a submissive, even without having to discuss it. While I would be honey, dear, sweetie, or whatever she felt suitable for the moment, her vanilla term would be ‘Em’ – or, as we secretly knew it to be, ‘M’ . . . for Mistress.

  We also talked, at length, about our passions, our fetishes, our desires, and our beliefs. She understood and accepted mine. Wholly and without question. She already knew most of them from her dungeon. As much as Tricia had always claimed to accept me, she’d never really understood how I could worship women, hold them in such high regard, and yet have such a fetish for cocks and cum. Mistress not only understood, but she pointed out that much of why our relationship worked so well was because she embodied both sides of my fantasy.

  I felt like an idiot, having it pointed out to me like that, but she was right.

  In her, I could worship the feminine form, submit myself to female supremacy, and yet still worship the power of cock. Subconsciously, I must have known that, must have made that connection, but I’d never really thought about it.

  With her, things were a bit more complex, but we were more alike than I had ever expected. She too admired the female form and believed in female supremacy, and she too believed in the power of cock, only for her it was a matter not of worship, but of being worshipped. She described herself as polyamorous, attracted to all genders. She was quick to assure me, though, that she was quite pleased with me just the way I was. Aside from caging my cock and denying me ownership of my orgasms, she had no desire to emasculate or feminize me.

  It didn’t interest her, and she understood that it would be a betrayal of who I was. It wasn’t that I found it to be humiliating or emasculating – the exact opposite in fact. To embrace the feminine, even in something as simple as a pair of panties, would be to lay claim to something sacred. Something above my station. I had nothing but respect for those who could entertain that crossing of boundaries. In fact, I found some sissies, crossdressers, and forcibly feminized males to be just as attractive as any woman. I just couldn’t entertain the disrespect it would mean for me to pretend to such femininity.

  We had many such conversations like that over the following months. At first, it seemed odd to be talking of such intimate and kinky things in public, where any stranger could overhear, but Mistress never failed to make me feel at ease, no matter where we were. The more we talked about our fantasies and fetishes, the more I found myself opening up to her. I learned a lot about what I had always assumed were my limits, and just how far I felt my curiosity might take us.

  Our season of dating, as Mistress liked to call it, was a chance to get to know one another on an intimate level. It was my formal period of consideration, an opportunity to prove myself beyond the walls of the dungeon. While she already knew I was an exemplary submissive and felt confident I would prove to be the perfect slave, she needed to know that I could be a suitable companion in those quiet moments at home.

  One season. Four months. Seventeen weeks. One-hundred-and-twenty-two days. It should have seemed like an eternity, but I treasured every single moment spent in her company. She awoke with her cock in my mouth every morning and came home from the dungeon to my massaging hands every afternoon. Evenings were a peculiar affair that saw us do ‘normal’ couple things like watch TV, read in front of the fire, listen to music, or play games, except I was usually in some sort of bondage, and spankings could come at any time. Every Sunday night she would milk my prostate with her finger, and then have me lick up my own mess. I longed to feel something larger than her digits, to submit myself to her pleasure, but that had to wait until our commitment was sealed.

  I had my difficult moments, as she predicted. My first day back in the office, that collar felt like six inches of neon lead. I was sure everyone could see it, and became completely paranoid. I almost removed it, figuring I could snap it back on before I got home, but that would have been a betrayal of trust. I confessed to Mistress that night, and as proud as she was of my honesty, she did paddle my ass until I cried.

  And, after four days of chastity, I was just as frustrated and sore as I had feared, to the point where I stood in the bathroom one morning, with Mistress’ cum still on my lips, and punched the tiled wall so hard I bruised my hand. Again, I told her the truth, and this time the punishment was a bit more intimate, a bit harder to endure. She had me stroke her cock with that damaged hand all evening long, edging her to orgasm again and again, but denying either of us release.

  One of the most difficult changes to become accustomed to, however, was that she no longer permitted me to drive. That was the only time I even considered asking for my release. Rather than have me repair my car – the police found what was left of it in a field – she confiscated my license and forced me to rely upon her for transportation. Driving, she argued, was too much control for a submissive. That was hard. That was a bigger denial of freedom than collar and cage combined. It was almost emasculating. There was no question, though, that being completely reliant upon her served to enhance my submission, and I eventually came to appreciate my place.

  During that time, I learned to endure – and enjoy – a very different sort of cuckolding. It was less physical than what I had shared with Tricia, but somehow more intimate. I knew she spent her days with a wide variety of male, female, nonbinary, and transgender clients. She told me over breakfast what she was expecting of the day and teased me over dinner with some of the most salacious details of their experiences.

  I was kept at arms’ length, enjoying nothing more the scent of sweat and cum on her leathers, with nothing to clean up. I could picture everything she told me, and it was completely different than what Tricia had tried to force me into. I found myself envious of their time with Mistress. Listening to those details was a challenge to my chastity. Their arousal triggered my own, and I became increasingly jealous. Mistress seemed to thrive on that, but she also took care to remind me that things would change following my formal collaring.

  My first taste of what life might be like following that formal collaring came late in October, when I made one of my twice-a-week visits to my old house. Amidst the pile of junk mail and bills inside the front door was a notice from the bank, reminding me that my mortgage was coming due for renewal. I usually just called the 1-800 number and approved the automatic renewal at the new rate, but I knew that was a decision that needed to be placed in Mistress’ hands.
/>
  She approved. She did not make it an ultimatum, but strongly advised that I sell the house, as she would rather I not have any backup plans or escape routes that would interfere with my overall focus on becoming her perfect slave. It was a big decision, a huge severing of ties with life outside her home, but she was right. Her home would never truly feel like mine so long as I had clothes, bills, and silly possessions across town.

  Mistress made all the arrangements. Her plan was to sell the house and invest the profits in my name, with the interest payments going to her, for a 5-year term – after which, the entirety of the funds would transfer to her, with me as the sole beneficiary should anything happen to Mistress. It was not a backup plan or escape hatch, but a contingency plan to ensure her property remained taken care of.

  The house had only been on the market for a week when I received a text from Mistress. She liked to tease me at the office, to issue tasks that I had to complete, so the message notification itself was not a surprise. The contents of the message, however, were.

  [I have called an Uber to pick you up.]

  [He knows where to go.]

  [You will understand when you get here.]

  [Do not keep me waiting.]

  I sent a quick email to my boss, telling him I’d come down with a migraine and had called a cab to take me home. I did not wait for a reply. I left everything on my desk, grabbed my phone and raced down the back stairs, where I figured the odds of being caught in a bit of workplace hooky would be least likely to be discovered. I nearly slipped coming around the second-floor landing, a used condom squishing under my foot, but quickly righted myself.

  There was a small grey Toyota idling at the end of the alley, an old AC/DC song shaking the windows with the bass rumble. The passenger window rolled down and a freckled, college-aged kid leaned across the seats. “You Tom?”

  “That’s me.” I climbed into the front seat. Fast food wrappers crinkled beneath my feet. He was pulling into traffic before I even had my seatbelt on. “Whoa. In a hurry, are we?”

  He grinned, his knuckles white on the steering wheel. “Broad who called said you’d pay me an even fifty if I got you there before one o’clock.” He pulled into a bike lane to make the right-hand turn. “By my watch, we’ve got about ten minutes.”

  To his credit, we made it in nine, and without breaking a single traffic law. Bending a few, sure, but none so broken that he’d be in for anything more than a warning had he been caught. I handed him the fifty from my wallet – the entirety of my allowance for the day. It was only then that I realized where we were.

  My house.

  Not that I recognized it. Not at first.

  The realtor had cut the lawn, power-washed the driveway, and planted a trio of flower beds around the property. The porch had been re-stained, and the concrete stairs patched. I paused for a moment to take in the larger picture and noticed that the windows all had new curtains, and the wood trim had been painted a fresh white. Probably less than a thousand dollars’ worth of improvements, but it was worth it. It looked like a whole new house.

  The cracking open of the front door caught my eye. I rushed up the stairs and stepped inside.

  “Mistress.” She was standing inside the narrow hallway, a vision in sweaty, disheveled ebony. Her hair was sticking out from its tight ponytail, and her eye shadow had run. I could see sweat beading on her upper lip and resting in the curves of her collarbones. She had on a black bra that had shifted, leaving one chocolate nipple on display. Her cock was glistening with juices, dangling half-limp, and still twitching. Stockings encased both legs, the usually perfect seams twisted. I dropped to my knees and planted a kiss on each of her shiny black pumps.

  “Welcome home,” she whispered. “Time to say goodbye.” She snapped her fingers and I climbed back to my feet. “Undress and I will give you the tour.”

  At this point in our relationship, I could undress in a heartbeat, folding everything in a seamless maneuver, without conscious thought.

  Mistress led me through the house, pointing out all the minor renovations and improvements the realtor had made. My estimate of the outside was bang-on, but there was another two thousand dollars’ worth of improvements inside. Most of it was little things, like paint touchups and scuff mark removal, but I also noticed some new throw rugs, a few tasteful paintings, and new lamps or lighting fixtures in all the rooms.

  “Heather appraised it a two-hundred-eighty-thousand,” she told me as we climbed the stairs to the half-story where my bedroom was. “We listed it at three-hundred-fifty.” She paused outside my bedroom door. Hardly necessary for privacy, being the only room on that floor, it instead served to contain the air conditioning in the summer. “It sold this morning for three-hundred-and-eighty, with an immediate close.”

  The moment she opened the door, I could smell sex. The scent billowed out of the room. It nearly drove me back to my knees. As Mistress stepped aside, I could see a blonde MILF laying on my old bed, her legs pressed tightly together, and one arm covering her breasts. She was reasonably attractive. Most people would likely have said she looked a bit better when she wasn’t tired, sweaty, and covered in smeared makeup, but I thought it made her look alive.

  There was a smart pantsuit draped over my headboard, and a pair of smart heels sitting at the end of the bed.

  In the hand that wasn’t covering her breasts I saw a sheaf of papers.

  “Heather is a regular client of the dungeon,” Mistress explained, her voice dripping and sweet. It was a voice I had almost forgotten about, the powerful, seductive, honeyed voice she used with clients. She had no need to force it with me at home. “She is also one of the select few I have invited deeper, into my private playroom.”

  I shuddered at that. If I wasn’t already jealous of the clearly well-fucked woman, that news made my cock twitch painfully in its cage. The playroom was a place of legend, a rumor to those who had never been invited inside, and a secret to those who had.

  It was a place to which I had never been invited, although Mistress had already revealed that I had earned an invitation long ago. She withheld it, though, wanting more from me. She promised I would set foot inside. In fact, she assured me I would be a regular, discovering new depths of cuckold submission inside. That would not happen, however, until our relationship was sealed.

  Mistress took the paperwork from Heather’s hand. She pulled a pen from between the blond woman’s breasts. “There are stickers where you need to sign.” She pressed both into my hands. “Be quick. Your celebratory champagne is cooling.”

  I scrawled my name in all the places indicated, never pausing to read a word. I knew what Mistress and I had discussed. I trusted her to ensure everything was in order. To have wasted time second-guessing her would have been both rude and disobedient.

  “Heather and I fucked,” she whispered in my ear as I signed. “I used her like the bitch that she is.” She moved around to my other ear. My nipples grew hard, even as my cock couldn’t. “I fucked her face. I fucked her tits. I fucked her cunt. I fucked her ass.” She stepped behind me. I could feel her breath on my neck. A moment later, I could feel her cock rising to brush against my ass. “I left her stretched and well-used, full of hot, thick cum.” As I left a final shaky signature, she reached around to fondle my caged cock, causing me to groan in delicious pain. “Be my cuckold.” She yanked hard on my balls, digging her nails into the tender flesh. “Clean up this mess.”

  “Yes, Mistress.” I handed her the papers and pen. “Thank you, Mistress.”

  “Open up, bitch.” Mistress slipped back into her honeyed tones. “Time to feed the cuck.”

  The moment Heather spread her legs, I could see the wet, glistening, dripping mess that was her pussy. It was a mature woman’s pussy, its hole larger than any I had ever enjoyed, and the lips of her labia draped to either side like fat curtains.

  I didn’t take the time to admire it.

  I dove right in.

  As many times as I had
enjoyed the taste of Mistress’s cum, it was a whole new taste when mixed with the juices of a woman. It reminded me, just for a moment, of feasting on Tricia’s well-fucked pussy. The combination of cock-sweat, thick semen, and female orgasm was familiar, but Mistress’ cum had a taste to it that was like no other. It was almost sweet, less bleach-like than most cum, with just a hint of the peppermint oils that she used to moisten her cock every morning after my breakfast.

  I licked the dripping trails off the inside of Heather’s thighs, catching the pearlescent treasures before they could fall to the bed, and then moved further inward. I sucked on her lips, pulling at them with my own, and used my tongue to clean between them. It was hot between her legs. It was a heat that spoke of sex and satisfaction. As I began carving longer swaths with my tongue, cleaning every drop of Mistress’s cum, I felt Mistress climb behind me on the bed and begin rubbing her cock between my ass cheeks.

  Could it be? Was she finally going to fuck me? The thought caused me to hesitate, for just a moment. It was like she read my mind.

  “Keep dreaming, my sweet cuck slave.” She shoved my head back into the mature pussy. “I told you before, you’re not getting fucked until you’re mine.” Her cock wedged itself between the cheeks of my ass. I felt her lean into me, shoving my face even deeper. “Get in there, my little bitch. Get that tongue in there. I filled that cunt to the brim. You’re going to have to lick deep and suck hard.”

  I gasped into the open pussy and was immediately rewarded with a thick glob of sperm that nearly choked me. It shot right into my throat and lodged there, thick as it was. I had to cough and swallow a few times to get it down but was soon feasting like a king – or a cuckolded prince. I loved Mistress’s cock, but there were moments where I missed the hot, wet, claustrophobic pleasures of feasting on a woman’s pussy.