I can’t remember all their names. I just remember their dicks. Mostly I remember Gregory’s dick – the tiny, shriveled, crying (if a dick could cry) cock trapped in the plastic cage, withering and wasting away as it endured the ultimate humiliation.
It very well could have been the 77 days of consecutive chastity that pushed him over the edge. Or maybe it was just me.
Gregory was easy to manipulate at that point. In fact, he begged for it. He begged for such humiliation and degradation that the mere words made me wet. I made Gregory describe to me – again and again – just how far he would go for me. Sometimes I even made him write it down and read it back to me – a list, so to speak, of the things he’d do to earn just a little relief. I had scraps of paper everywhere – little mini contracts I called them – of the most disgusting and degrading things he promised to do.
Listening to him whimper and moan, sometimes smirking at him, other times teasing him with my fingers hidden underneath my satin panties, it became quite clear what must be done. I couldn’t pull back at that point, I couldn’t back out of the threats. I would lose all credibility as his sadist and his Mistress, and that was simply not an option. I had dozens of pieces of paper with all kinds of humiliating promises at my disposal.
And to be honest, I had never been so turned on. Touch, solid Gregory was before me, begging in the silkiest, sexiest pink lingerie, and corporate Gregory, the CEO, was going to go far beyond simply worshipping my strap-on dildo for hours.
The length, the width, the feel of my thick strap-on had to be second nature to him by that point. Gregory had been sucking it, worshipping it, every night for 74 days before I told him that he’d soon be sucking off the real thing.
Ejaculating dildos no longer terrified him; saved cum cascading over his own face did not degrade him enough to satisfy my growing hunger. The ache in my belly was intense and unforgiving. It was his fault; after all, he put those images in my head in the first place.
Clearly, Gregory wanted it even more than I did.
Hearing Gregory describe to me – between sucking my dildo and worshipping my pussy –just how he would deep throat any real cock was mind-blowingly erotic. His words –how he stumbled over some of them, leading me to sometimes lean over and give his balls a squeeze. The words – they seemed to get caught in his throat, he had to shut his eyes (oh, how I loved to slap his face with my latex cock at those moments). He had to close his eyes as if not seeing would keep him from hearing the words he was speaking.
Illogical, I know. But he was certifiably insane at that point. 77 days of chastity will do that to a man.
**
It’s true. Not being able to cum makes a man insane. A sort of cock-lusting, cum-whoring kind of insane.
There really is no other way to explain it. Around day thirty, a man becomes so weak and delirious that his imagination starts to play tricks with him. Curled up at the foot of my bed, when he didn’t sleep in the cage, I could hear Gregory whimpering in his sleep like a puppy having bad dreams.
The nights that I made him sleep in full shackles, the constant rattling of the chains would disrupt my own sleep and I’d escort him into the basement, cage him for the night, and mutter something about coffee and tea being ready on time in the morning. His cage was unlocked by a timer, and the nights where I felt really cruel after being woken up, I’d force him to sleep in a large, latex dildo gag that fastened to his leather hood.
But I’m not that mean, really. He really was asking for it.
By day thirty, Gregory was trying all kinds of offers and ploys to get me to reconsider our target timeframe of him not cumming for 100 days. He was trying to come up with scenarios that he knew, himself, would push him to the limits of his own masculinity and challenge the far corners of his ego.
Confident, cocky Gregory was a mere facade he played during the day at the office. He’d return home, strip out of his corporate clothes and down into his pink lingerie, and I’d laugh at him as he sucked and worshipped my toes while I talked to my girlfriends on the phone.
I’d tell my giggling girlfriends just how delirious he was getting, sometimes making him kneel between my wide-open thighs and start the deep, methodical bobs up and down the length of my cock, slurping loud enough that my girlfriend could hear on the line and squeal, “That’s so disgusting! I can’t believe you’re making him do that!”
I laughed and said, “Oh this is nothing. I’m getting him geared up and trained to suck a real cock!”
That got silence from my girlfriend and a deep, guttural moan from my Gregory, who was bobbing up and down so fast and furious on my cock that the rhythmic pulsing against the base of the strap on against my crotch was starting to get me hot. Well, hotter than just watching him suck dick.
It was too good to pass up, though, so I continued describing to my girlfriend on the phone what plan I had set in motion. “I put an ad on Craig’s List. Pull it up right now. It says – sissy bitch ready to suck dicks all night.”
I’m sure Gregory heard my girlfriend gasp as she read it – parts of it out loud – and then ask me, in shock, how many responses I had to the ad.
“Most guys just send me pictures of their huge, hard cocks,” I told her. As if on cue, Gregory moaned and gagged on my latex strap-on. I gave his face a light slap and pointed a finger, indicating that it was time for him to turn around, pull down his panties, and lift his ass obediently to me.
Holding the phone between my ear and shoulder, talking to my girlfriend, I squirted lube down his ass crack and began to rub it in place. I did this all so casually, so coolly, you’d think I was just rubbing lotion into my feet after a day at the beach. Surely, my girlfriend heard the distinct squirt from the tube of lube, but she said nothing. She just re-read the advertisement out loud.
“I’m going to meet a few of them at a bar tomorrow night, check them out, make sure they are the real thing. If they are hot, I might just fuck them. After all, since Gregory has been locked up for so long, I haven’t had a real cock in me in ages!”
“I don’t know how you stand it!” my girlfriend Julie exclaimed.
My latex cock popped through Gregory’s tight ass with little more than a defeated whimper from him in the background.
“I know,” I agreed. “I’ve had enough of it. It’s about time I got fucked by a real man anyway, and Gregory is so desperate and horny, I bet he’d beg to lick my pussy clean when the guy’s done fucking me!”
“That’s gross,” she replied.
I could see the cock cage filling up with precum if I leaned over just right and caught a glimpse in the mirror as I fucked Gregory’s tight “pussy.” I couldn’t help but stop and give his tight ass cheeks a few swats, listening to him grunt and moan as I penetrated him again and again, deeper each time, until my cock was sliding in and out of him with a cool, fluid motion.
Sure enough, with eyes closed and the vivid scenarios rolling through my head, imagining what would soon be happening as a result of the ad, it was not difficult for me to reach climax. Just the pressure of the base of the strap on against my crotch and his desperate, sweetly pathetic whimpers put me over the edge.
After I came, I made him roll over so I could sit on his face. I made him use his tongue to worship my pussy as I started dialing the numbers from the printed page I pulled off my computer. Sixteen men out of the 75 that emailed me. Surely, I’d find a few cocks for him to suck.
**
The details are not important, and to be honest, they are quite boring compared to the actual night of dick sucking itself. Because I can assure you, it takes a great deal of planning to get nine guys lined up (yes, nine) for a free blow job and possible a ride in the sack with a woman who is incredibly hot.
After all, I needed to find guys that were both sane and attractive. And they had to have a huge dick. That was the first thing I needed proof of because some guys were sending pictures of cocks that were clearly not their own!
I can’t remember all their names. I just remember their dicks. Mostly I remember Gregory’s dick – the tiny, shriveled, crying (if a dick could cry) cock trapped in the plastic cage, withering and wasting away as it endured the ultimate humiliation.
Gregory didn’t believe it at first, I don’t think. The hotel room, the elaborate set up, I am sure he thought it was all a huge mindfuck. I had him kneeling in his sexiest lingerie, looking like a prissy little tart, and I was humiliating him as I fucked his mouth leisurely with my largest, thickest latex strap-on cock.
“Little bitch likes it!” I laughed, cradling his face in my hands as I often did, holding him steady as my entire shaft slid in and out of his wide-open mouth. His jaw was loosening up, his eyes were watering and he was adjusting so that he could accommodate the entire cock with ease. The weeks of practice certainly had paid off.
Gregory had no idea that the men were starting to filter into the main room of the hotel suite. He was so intensely focused on sucking my strap on that I think he probably didn’t even hear some of the voices nearby. Gregory did just what a good little whore should; he sucked my cock with eager desperation because he knew it made me smile.
When I added the blindfold he didn’t make a fuss. Blindfolds were common for me – I was much more likely to blindfold him when I wanted to focus squarely on the task at hand – in this case, violating his mouth – without the distraction of his pleading, desperate eyes.
The blindfold served another purpose, though. And this was the most turned on I had ever been while applying a cover to his eyes because I knew the reasoning behind it. Surely, deep down, Gregory must have had some clue what I had in store for him.
I made sure he was thoroughly focused on the task of sucking my cock, I coolly gave him seductive commands as my “new boyfriend” Phil entered the room at my gesture. I told Gregory to open wide, to deep throat, to lick and worship my balls. This string of commands made Phil’s already hard cock start to nearly pulse before my eyes, and I marveled at the size and perfect shape of his magnificent cock.
(I have to admit, when I saw Phil’s cock, the first thing that came to mind was how good it would feel deep inside of me. After so many days of not fucking Gregory, having a real cock inside of me was all I wanted, too. And let’s face it – Phil’s cock was much better built than Gregory’s meager dick.)
I took my time, though. Standing half-clothed, my hands on my head, tossing my hair a bit, fucking the mouth of my blindfolded whore, I have to admit I felt a little bit like a sexy porn star. Fucking his head while I held his face in my hands and made him gag a little at a time, I felt quite sexy and empowered, and seeing the naked, well-built man waiting his turn just added to my excitement.
Phil knew the rules. He said nothing. He waited his turn. He just stood there, and I looked at his monster cock, which was, ironically, about the same size as my strap-on cock. But clearly, it would feel much, much different when it filled Gregory’s mouth. My whore would soon be sucking off the real thing – sucking a man’s dick while I watched with delight – and he had no idea it was about to happen.
Yet, he had begged for it! He had begged for it as early as that morning when I teased and denied him, sat on his face, made him lick and worship my asshole because that’s all he’d get from me that day. He begged to suck any dick, as many dicks as I lined up, and I told him I just might have to take him up on it. He had written it down in great detail and presented the piece of paper between his lips.
And there was Phil – Phil with the huge, perfect cock – smirking at me. The way Phil looked at me, kind of checking me out, obviously getting off on the way I thrust my hips with vigor toward Gregory’s face, reminded me of being checked out in college by the hottest guy on campus. Phil’s dick clearly gave him all the confidence in the world, and I decided right there I was going to take him to stage two that night. Phil would be fucking me – hard, fast, deliberately – while Gregory just watched – sad, helpless and pathetic.
My pussy ached.
Wanting to move the production along so I could get as quickly as possible to the grand finale, I stepped back and let Gregory catch his breath, his lips stretched and swollen after sucking my latex dick for a good solid 45 minutes.
“Keep it open,” I ordered as he tried to stop and lick his lips, swallow. “I might get out my ejaculating dick!” I laughed at him and gave Phil a knowing nod. “Open wider, whimper if you want it, beg for my huge thick cock!” I ordered.
Gregory obeyed, desperately, and the moment Phil’s huge, warm cock entered my slave’s mouth his body started to shake all over and convulse, nearly throwing the blindfold off from his mere body spasms. He knew, at once, he was now sucking off the real thing. But he didn’t pull away – no, he didn’t at all – in fact, maybe it was because I was right there pleasuring myself and he knew it. Maybe he could smell my pussy so close because I was clearly more wet than I had ever been in my life.
Watching Gregory suck cock was magnificent. Phil’s dick was magnificent. Gregory choked and gagged on it and Phil held his head steady with big hands as he pumped, and I watched his fine ass thrusting as I teased and rubbed my clit. I realized I could watch this little show for hours, but what I really wanted was Phil’s cock in my pussy. And when I realized how that would push Gregory to the brink of humiliation and despair – a place he so desperately needed to go – it was a no-brainer.
When I sensed Phil was getting close to cumming, I backed him off. It’s not that I had not considered making Gregory eat a full load of cum, or having Phil cum all over my slave’s face. I knew there was time for that later – after all, several men were milling around in the next room, waiting for their “turn.”
I removed the blindfold from Gregory’s face, and he did not dare look up at the big, built man whose dick he’d just sucked. His eyes were cast down, surrendering, so humiliated. To keep him motivated, I let him taste my fingers for a brief moment, and his eyes closed dreamily when he recognized the sweet flavor of my pussy.
“You want me to be fucked by a real man, don’t you?” I whispered into his ear. “You want to see me get pleasure from being fucked by that big, hard dick, don’t you?”
This made him melt in my presence, I could tell. His body started to shake and I swear if he were not in a cock cage under his pink panties, his dick would explode. I could imagine the points of intrigue were nearly piercing his skin as his cock grew as much as it could inside the device, and I could see him wincing in pain, a sure indication that he was liking what he was hearing. Even though it totally degraded him.
“Into the chair, bitch,” I ordered, and I took him by the arm and with a shove indicated where he was to go. He crawled, too, instead of even getting up, a sure sign that his mindset was exactly where it needed to be – total surrender, total devotion, and unrelenting need to suffer for me.
Or to see me get fucked.
I tied Gregory to the hotel room chair with swift ease. In his lingerie, sweating, his lips stretched and full of precum, he looked genuinely pathetic. It was incredibly hot to me. I was more turned on than I had ever been – and all I wanted and need at that moment was a good fuck, one that I would not be getting from my locked-up bitch, that’s for sure. I gagged him, cruelly, and told him that I’d better only hear grunts and moans of approval and that he was not allowed to close his eyes or look away. I told him he had to watch every moment of this glorious fucking so it would be forever imprinted on his pea brain.
Phil seemed to watch this all unfold with a masculine sense of amusement, a youthful arrogance, and he was just standing there with his arms folded across his broad chest, his thick cock standing straight at attention.
Without a moment of hesitation, I positioned myself over the table in the room, pulled down my panties and lifted my skirt. “Fuck me,” I ordered Phil. “I need a real dick inside me.”
The “real dick” comment resulted in a pitiful moan from Gregory, a moan that made me even more excited. Phil was behind me in no time, and his big hands felt fantastic around my hips. His cock, not surprisingly, felt like a jackhammer going into my pussy, and the immediate pounding was a welcome, intense sensation. He fucked me quite hard, and I loved it, listening intently for Gregory’s pathetic whimpers behind the gag. That was all the further lubricant I needed. Every whimper seemed to make me ache even more.
Phil’s grunting was a bit of a distraction because I really just wanted to hear the soft moaning from my pathetic slave. I glanced over at him, my hair disheveled, my body glistening with sweat. I know I looked absolutely stunning to him, my body rocking with the thrusts, the curves of my frame accenting the femininity that he found so alluring in contrast to my cruel and commanding nature.
More men were lurking around by now, some of them casually walking into the room to look, then walking back out. They’d give a look to Gregory and disregard him at once, then look at me, some of them holding onto their hard dick, waiting for their number to be called so leisurely it was as if they were waiting in line at the bank.
“You like this, don’t you?” I said breathlessly to Gregory as Phil picked up speed. His dick felt huge inside me; it was difficult to keep a cool composure, but I managed a smile, despite being ridden close to orgasm. It took self-control but I held off so I could order Phil to pull out so I could turn over, lift my legs over his shoulders and let him finish off fucking me in my favorite position, spread open wide to take his pounding.
This made Gregory whimper so pathetically because it had been so long since he’d ever been that close to me. Sure, his tongue had worshipped my pussy and ass for hours; but his cock had not been in my pussy for months. He probably forgot what it felt like.
When I came, it was loud. I made plenty of noise so it elicited a few chuckles and a soft round of applause from the next room, where the men were now playing cards and getting to know one another, it seemed. Gregory was breathing hard, his body straining in the chair. I had no intentions of letting him loose with a full night ahead of us.
“I’m done with you,” I told Phil, pulling up my panties and adjusting my loose bra straps as I got up. “But if you would be up for round two, stick around a few hours.”
“Cool,” Phil said, running a hand through his hair and giving his body a stretch. His half-erect cock was dripping a bit, and I couldn’t help but look over at my slave, watching us both from his helpless corner in the room. It occurred to me that he should be the one cleaning Phil’s cock, or at least, cleaning out my pussy.
But the night was still quite young. I didn’t bother getting up. “You can clean me out,” I told Gregory, “Once there are several more loads inside.” I chose to be direct, blunt and crass about it because those were the kinds of words he needed to hear.
And I wanted him to know this wasn’t going to be just a taste, so to speak. I was ready to test the full limits of his desperate chastity – and after all, he’d promised me the night before just how many loads he’d eat for me.
And I had made him write it down. Surely he remembered.
