Imprisoned by My Fantasy Ch. 05

If you've ever felt the sheer helplessness of being bent over on in a jail cell with your hands cuffed, wearing an outfit most hookers would have blushed at, while a man behind you flips up your skirt and pulls down your panties, then you'll know what I was feeling. If not, consider yourself to be luckier than I am.

"You got a hot little ass, bitch. Hope you can take this." Paul said appreciatively, resting the length of his cock over my bare ass for a moment.

I gulped in fright as I felt the full length of Paul's cock on my skin. It was one thing to suck him off as I had earlier; I had some experience using my mouth to satisfy men, after all. Watching me suck off men, in particular, black men, excited my wife Lexi the most. I could just imagine her watching me outside the jail cell. Lexi would be rubbing herself at the sight, though Darius would likely be there to do that for her. In fact, they were almost certainly fucking in our marital bed at this very moment. Regardless, I had never done anal before. I fully regretted declining Lexi's offer to use one of her dildos on me in the past. It would have prepared me a little for what was coming, at least.

Paul positioned his cock at the entrance to my ass and began to push forward. I let out an embarrassing and unconscious squeal as Paul's cockhead began to move past my sphincter, to the chuckles of the black man in the cell.

"Please Daddy, go slow!" I pleaded.

Predictably, Paul did the opposite. The large, well-muscled black man forced his cock into my ass, causing me to squeal even louder. It was then that I realized that the super-long-lasting lube that Lexi had applied to my ass earlier still worked. I silently gave thanks to my wife as Paul forced the entire length of his cock into my ass, only stopping when his balls came to rest against my upper thighs.

The experience of losing my anal cherry to Paul was painful, but not as painful as it would have been without the lube. Even so, my ass felt every centimeter of Paul's thick, almost 9-inch cock. I had just barely begun to get used to the stretched feeling when Paul pulled his cock back until only his cock head was past my sphincter before driving it in again, seeming to enjoy the helpless squeals I let out. After a few repeats of this, Paul began to fuck me in earnest. I did my best to relax my ass as much as possible, but it seemed that Paul expected more out of me than that.

"I like my bitches loud. Moan for me, bitch." Paul growled, punctuating his demand with a hard smack to my ass.

Instantly, I abandoned whatever tiny shreds of pride I still possessed and let out a series of embarrassingly feminine moans. I did my best impression of a girl getting fucked hard and loving it, and judging from the fact that Paul's cock seemed to harden even further in my ass, he approved of my performance. And he wasn't the only one. From the corner of my eye, I could see the other black man in the cell had a very noticeable tent in his pants. I would have to satisfy him again, obviously.

"Good girl. You're gonna like selling your tight little ass at my club. The brothers love a white T-girl that does what she's told." Paul said as he continued to fuck me, evidently making plans for the future.

"Y-Yes, Daddy! T-Thank you, D-Daddy!" I answered, stuttering slightly after every hard thrust.

Paul's cock hardened further, and he suddenly grabbed my hips and began pulling me in at the same time he thrusted, pushing his cock even further up my ass. It also caused his balls to slap against me with more force than before, and that let me know that Paul was going to cum soon. I had felt his heavy balls expanding all this time, but now they seemed to be smaller. That could only mean one thing: he was about to blow his load deep in my ass.

Seconds after realizing this, Paul drove his cock as deep in my ass as he could, grunted, and started to cum. I couldn't help but let out another feminine moan at the strange feeling of a man cumming inside me. I thought that my ass was full before, but now I knew otherwise. Every time Paul's cock throbbed, it meant another load of hot semen was spurted deep inside. Paul kept his cock in my ass for more than a minute afterward, only taking it out when he was certain that every drop of his cum had already been deposited. As soon as Paul withdrew, I squeezed my ass shut to keep any of his cum from escaping. I then squatted down on my stilettos next to Paul, remembering not to get off the floor in front of him.

"P...Please, Daddy. Can I cum now?" I begged Paul weakly.

Paul opened his mouth to say something, but I never found out what. That was because the guard outside had stood up and used his keys to open the cell door.

"Alright, Hughes, Mitchell, let's go." The guard said, looking directly at Paul and the other black man, whose last name was either Hughes or Mitchell.

"Sorry, baby. Gotta get outta here." Paul said, shaking his head as he zipped up his pants.

"Fuck that. I want another round with this bitch." The other black man said, looking at me like a wolf does at its helpless prey.

"I said let's go, Mitchell. Ain't askin' again." The guard said, putting his hand on his nightstick.

To my immense relief, Mitchell cursed and walked out of the cell. Paul nodded at the guard but looked back to me before going anywhere.

"B-But...you said I could..." I trailed off softly, knowing it was hopeless anyway.

Paul looked down at me closely. Before, I would have sworn that a man like him had absolutely no sympathy within him. But I saw something that looked almost like pity in his eyes for just a moment. After that, the cold smile Paul had shown me before was back. He reached up and cupped my chin, raising my head to look at him.

"You ever want to make some money, come to the pool hall on West 34th. I'll line up some brothers for you, and make sure you're safe, too. My bitches don't got nothin' to worry about, so long as they listen." Paul said in a very commanding tone, looking directly at me.

"I'll ask my wife, Daddy." I answered meekly, knowing that Lexi's opinion about this was all that mattered.

"You do that, girl. I'll be seein' you, then." Paul said, letting go of my chin.

I watched as Paul walked out of the cell, wishing the guard hadn't chosen that moment to come. In all likelihood, Paul wouldn't have let me cum anyway. Lexi was much the same. Even when she was completely satisfied with my behavior, Lexi would still sometimes decide that I didn't get to cum and that my schedule would be reset as if I had. After the first time it happened, I learned to keep my mouth shut and accept it with a smile. Complaining had changed my schedule from cumming every two weeks to every three. It was an important lesson about how my wife's word was final, and that I would be very unwise to ever question it again.

Since the two black men had gone out of sight, I felt it was safe to stand up again. I walked daintily over to the toilet in the corner with my hands still cuffed behind my back, wincing at how loud my stilettos were on the concrete floor. Thankfully, Paul hadn't pulled my panties up, which meant that I was able to sit down on the toilet and let Paul's cum slowly drain out of me. It was an intensely embarrassing experience, even when the only person around was the Hispanic man that was currently snoozing on a bench along the far wall.

I also took the opportunity to pee. Sitting down like a girl was the only way I did it these days (Lexi's orders, naturally) so the only strange thing was doing it in such a public place. As soon as I was finished, I heard the sound of footsteps coming. It seemed to be more than one person. I panicked slightly, realizing I couldn't pull my panties up with my hands cuffed behind me. It wasn't as though that would be much help regardless, but in my current state, I would take whatever shred of clothing I could that covered me. My rather small penis was still covered by my mini-skirt, but that was the only thing going for me.

The guard came back into view first, followed by one man in cuffs. This man was also black, and he noticed me right away. I gulped as I saw the guard uncuff his wrists and open the cell door to let him in.

"Play nice with her. Girlie here needs to learn a lesson or two." The guard said to the man, locking the cell behind him.

I smiled weakly at the man, knowing that "playing nice" could mean any number of things. The man took in my appearance as I took in his. He was taller than average, seemed to be dressed better than the previous occupants were, and his hair was shaved close to his head. Like most men, he could probably hoist me up onto his shoulder with no more effort than it would take to do the same with a teenage girl.

The black man took in my see-through mesh top, black bra, black miniskirt, neon pink panties, fishnet stockings, and 5-inch stiletto heels. It was an outfit that very intentionally screamed "Fuck me", and so far, 4 different men had taken me up on the implicit offer. It was almost certain that this man would as well. The long-lasting makeup that Lexi had applied on me was still in fairly good condition, and I knew I looked decently attractive with the lipstick, eyeliner, mascara and blush my wife had put on me.

"What's your name, sweetheart? Mine's Jerome." The black man asked, grinning at me.

"M-Michelle, sir." I answered politely, unconsciously batting my eyelashes at him.

Lexi loved to see men flirt with me, and vice versa. One of the things my wife had ingrained in me was to always flutter my eyelashes if I thought a man was showing interest in me. I was too scared to remember to do it with Paul, but Jerome seemed a little nicer. I then did the next thing Lexi had taught me, which was to look him over again and stare, for just a split second, at his crotch. Unsurprisingly, the man's cock was already tenting his pants. Jerome grinned wider as he saw where I was looking.

"Horny little bitch, huh? I was gonna make some small talk, but if you want it that much..." Jerome said, unzipping his pants.

I instantly sank to my knees, figuring that if I did a good job with my mouth, Jerome wouldn't want to fuck my ass. Or at least it would buy me enough time for the man to hopefully be released before he could recover enough to want another round. I smacked my red lipsticked-lips in anticipation, looking far more eager than I really was. Jerome brought out his cock, and I quickly went down on it, taking his only half-hard cock in his mouth and feeling it expand to its full length inside my mouth.

"Damn, girl. I should get locked up more often if they're offering hot little T-girl ass in the cells now." Jerome said, laughing.

Jerome's cock was decently sized. I couldn't measure it, but it seemed to be between Paul's and Mitchell's length. The realization that I could judge cock size by how it felt in my mouth was a momentary shock to me, but it shouldn't have been. After all, this was the 5th cock that I had sucked tonight, and it likely wouldn't be the last. At this rate, I would be able to judge cock to the centimeter just from the feeling of having it in my mouth.

It took about 10 minutes for Jerome to get near cumming. I could tell the usual way: Jerome's balls had gotten progressively larger against my bottom lip, and now they had shrunk. I prepared myself as best as I could, and soon enough, Jerome's cock began spurting hot cum in my mouth. After the punishing experience of having to keep Paul's cum in my mouth, swallowing it was almost pleasant. I was quite used to doing it, in fact, as Lexi had made certain that every load of cum her lovers had ever shot into her would end up in my mouth.

"Damn good job, girl." Jerome said, pulling his cock out of my mouth.

"Thank you, sir." I answered, trying to catch my breath.

"Puta! Ven aqui puta!" The Hispanic man on the other side of the cell called.

I sighed and, with difficulty, got back on my feet. I knew just enough Spanish to know that the man was both calling me over and referring to me as a female prostitute. I couldn't really argue the point, even if I could make myself understood in Spanish. I walked over to him, feeling quite like taking off my 5-inch stilettos, but having no use of my hands, I had to keep them on. I smiled reflexively at the man, only knowing the most basic Spanish.

"Mi nombre es Michelle." I said, hopefully getting it right.

"El mio Hector. Ilegar a trabajar, blanca puta." The Hispanic man said, motioning to his crotch.

My highschool Spanish translated that as "Get to work, white whore", and the motion told me what the intended job was. I sighed once more and sank to my knees in front of the man, thinking Lexi should have given me some knee pads. It was the least my wife could have done, considering that she had successfully trained me into meekly following any order given to me by another man, even someone like this.

After having sucked off the Hispanic man for the second time, I passed the next hour or so making small talk with Jerome. He was quite interested in hearing about my life. He asked for my "real" name at some point, but I told him that Michelle was my real name. It wasn't the name on my birth certificate, but Lexi had made it known that I was Michelle from now on, and that fairly soon, she would draft the paperwork to have my name changed legally. I would have to sign the paperwork if I was going to cum anytime this decade.

Jerome was released soon after that, which left me alone with the Hispanic man once again. Small talk would have been difficult, so after I sucked him off yet again, I was given the chance to nap on a bench. It had been almost twenty four hours since I had woken up the day before, and after all the tiring activities of the previous night, I was ready to sleep for a long time. But it wasn't to be. I woke up about an hour after that to the sound of four men being put in the cell, two of whom were black, the other two being Hispanic. I felt a definite sense of panic at this and scrambled to my stilettoed feet to plead with the guard outside the cell.

"Please, Sir, I've learned my lesson! I swear I'll never sell myself on the street again! Please, please ask Darius to come get me." I begged rather convincingly, having no pride left with which to get in the way of my earnest pleading.

"Alright, girlie. I'll see if I can raise Darius. But I ain't keeping these gentlemen waiting. Entertain 'em till he gets here." The guard said with a laugh, taking what he seemed to think was pity on me.

The guard shut the cell door and left the room. I could only hope that he was going to contact Darius and wasn't heading to the candy machine. One look at the men inside the cell told me that they wouldn't be interested in playing Charades. Did my wife really have to specify that I wear such a slutty outfit? Maybe I could burn some precious time by flirting. I fluttered my eyelashes at the men, aware that having my pink panties down around my ankles probably told the guys all they needed to know. If only my hands weren't still cuffed behind me! The four men crowded around me and wasted no time in feeling me up. One of the Hispanic men cupped my ass underneath my miniskirt, while one of the black men ran his fingers through my hair. He even tugged it a little, as if he thought it might have been a wig. Clearly, I was seconds away from getting even more personal with these guys. There was only one thing I could do to delay it.

"So guys, who's first?" I asked innocently, looking around at each of them.

This had the desired effect of provoking a discussion among them. A slight language barrier helped extend it for me, but eventually, the men had the issue settled between them. The tallest black man stepped forward, and bowing to the inevitable, I sank to my knees for what felt like the millionth time tonight.

My hopes that Darius would come before I needed to suck off yet another man disappeared as the man's large black cock slipped past my lips and nestled in my throat. All the practice I had gotten tonight had given me the ability to deep throat even larger than average cocks, which this man certainly had. I thought about giving the man a long, slow blowjob, so as to maybe only have to suck him before Darius arrived, but I knew that I couldn't. My wife Lexi expected me to give fantastic blowjobs to every man who wanted one, and her training was fully ingrained in me by now.

It wasn't long until the man blew his thick, heavy load in my mouth. I swallowed every drop, of course. As I released the man's softening cock from my mouth and scooted on my knees toward the other black man who had stepped forward in his place, I thought I heard the sound of footsteps coming. I would have liked to stall for time, as the sound could have very well have been Darius, but one look at the impatient expression on the man's face persuaded me to take his hardening cock in my mouth and begin sucking eagerly.

I gave the man a passionate blowjob that would have made Lexi proud if she could see it. It ended as every blowjob I had given tonight did; with my mouth filled with thick semen. The potent male taste of it was overwhelming, and I realized that with every swallow I was performing an act of feminine submissiveness. It struck me that every time I swallowed a man's cum while being dressed as a woman, it irreversibly chipped away at whatever sense of manliness I still had. Now, I felt a sense of familiarity and appropriateness whenever there was semen in my mouth. Lexi would be delighted when I told her.

Whoever had made the noise outside the cell showed no sign of interrupting, and from the way the men surrounded me, I couldn't see who it was anyway. There was no real sense in delaying now, so I scooted over to the Hispanic man who was next. Seconds later, I was eagerly blowing him too.

"Pequena puta caliente!" The Hispanic man said with a laugh, which I thought meant "hot little whore".

I did my best to live up to the Hispanic man's designation of me. Several minutes of desperate sucking ended with him depositing yet another load of cum in my mouth. The strong male taste was hardly objectionable by now. Either my mind or my body, and maybe both, had accepted it as normal. I sucked the last drops of cum out of the man's softening cock and scooted over to his friend.

My mouth knew precisely what to do by now, so my mind could wander a bit as I began sucking off the second Hispanic man. Lexi absolutely loved seeing me with other men, to the point where she would probably forgo getting fucked herself if it meant she could see me getting penetrated instead. Well, if my wife was here, she would definitely be getting an eyeful as I submissively accepted a fourth load of cum from this Hispanic man, whose balls had tightened considerably as he emptied their contents into my mouth. I swallowed once again, knowing that I was in some way losing my own sense of masculinity each time, and I would be unlikely to get it back any time soon.

I released the man's softening cock from my mouth and took a deep breath. The other Hispanic man shifted slightly, giving me a view of the outside of the cell. What I saw made me simultaneously hopefully and completely humiliated. Darius was standing outside, holding up his phone, having evidently recorded the whole thing for my wife. I had thought I was beyond humiliation, but the thought that Lexi had watched me suck off multiple men, looking for all the world like the prison bitch she (and I, to a lesser extent) wanted me to be, made me blush deeply. It also made my penis twitch hopefully. If Lexi was happy, then maybe I would get to cum later.

"Alright, girlie. I think you learned your lesson now." The guard said with a deeply amused laugh, getting up from the desk outside the cell.