Escape From Theos

Escape from Theo's

Author's Note: This is another in my series about Theo's BDSM sex slave operation. It might be my last -- I'm getting a bit tired of writing about that sociopathic asshole and all the things his clients like to do to his slaves, and I've decided to end the series with a bit of a bang rather than just letting it fade away. But it's been fun, and I might succumb to the urge to write a few flashback stories, or maybe take advantage of the open plot-hook I left at the end, if I want to add to the series. Meanwhile, I intend to keep on with Kendra and Kev, and maybe a few more in the Allyson spinoff series.

Like all my stories, this one is mostly self-contained, but you might want to go back and check out some of the earlier ones such as Recruiting Slave Fourteen if you want to fill in the background more thoroughly.

Content warning: As always in Theo stories, expect some more or less non-consensual sex and moderate pain.

1. Serena's Day at Work

It was a fairly typical Friday night. Theo's place was busy, and I'd been chosen fairly quickly from the lineup of naked, bound and gagged women in Theo's showroom. It's always good to get chosen early so I don't have to stand around too long with tape over my mouth, my ankles in a spreader and a dildo pole locked up my twat while men check us all out before selecting one of us to be tied up and fucked.

I'm often chosen early because my appearance makes me stand out: tall and imposing, with coal-black skin and a shower of tight black braids that reach almost to my ass. That might have been one of the things that caught Theo's attention when he first selected me to be kidnapped and put in service almost six years ago.

The client was a medium-sized, slightly portly white man of about fifty. He went up and down the line and stopped in front of me. My breasts are medium-large but firm and carried high, with generous nipples and areolas even blacker than the rest of my skin. He picked them both up in his hands and lifted them as if judging their weight, then ran his thumbs over the above-mentioned generous nipples to make them perk up like little licorice candies. Then he reached around my body and ran his hands over my bum. He picked up my asscheeks the way he had my breasts and kneaded them a bit. Then he ran his hands through my hair, obviously fascinated by my braids. I looked straight ahead without expression, but thought in my head, as I usually do when white men mess with my braids, "Stop fucking touching my hair. Does this look like a petting zoo?" Which, I suppose, it sort of was.

I guess my boobs and my bum weighed in to his satisfaction. He took the hex key Theo handed him, unlocked the setscrew on the pole, and telescoped it down and out of my pussy. He removed the spreader from my ankle cuffs so I could walk, then pinched both my nipples in turn, pulled them out, hard, and clamped vicious nipple clamps on them at the base. He probably thought he was hurting me more by pulling my nipples out like that, but actually he was doing me a favour. The clamps bit down on more areola than actual nipple, which hurts relatively less than just clamping the nipple. Nonetheless, my nipples exploded in fiery pain, which got worse as he pulled on a long Y-shaped chain that was attached to them to form a leash. A smothered "Mmmpphh" of pain came out from behind the tape gag. As he towed me toward the door leading to the entertainment suites, I concentrated on two things. One was trying to keep up with him to reduce the pull on my nipples, and the other was the pleasurable feelings that came along with the pain.

You see, after years of being spanked, flogged, stretched and generally abused by Theo's clients, I found my response to pain shifting subtly. I had never been much of a pain slut before Theo enslaved me, although I had liked some moderate impact play along with bondage in the before-time. But here, something started to happen to me.

One day a few years ago, I was standing bent over the back of the bondage chair in an entertainment suite. My ankles were spread and roped to the back legs of the chair and my forearms were roped to the arms with turns of rope extending from wrist to elbow, and a client was smacking my protruding ass with a leather strap. He wasn't actually using a lot of force, but he was persistent, hitting the same area again and again and letting the pain, which had started out more as a tap than anything else, build and build until I would have screamed for him to stop if I hadn't been gagged.

But then something shifted in my brain. I realized that I didn't really want him to stop. Along with the pain from my abused asscheeks were other sensations spreading slowly through my body, which I gradually recognized as arousal. I felt my nipples on my dangling breasts starting to harden, and my pussy began to tingle and moisten. My clit began to engorge to match my nipples, starting to poke out from under its hood. Somehow the pain, even though it stayed painful, was beginning to merge with a peculiar pleasure of a kind I hadn't felt ever since Theo had enslaved me three years before.

At first I tried to supress the feelings. It didn't seem right that this totally non-consensual abuse should be feeling weirdly good. But then I realized that this could be a gift if I relaxed and rolled with it. I concentrated on the growing tingle in my pussy that was spreading through my whole abdomen, letting it flow over me as the pain in my ass started setting my whole nervous system on fire. My cunt walls clenched, and I started feeling desperate to have something in it -- a finger, a dildo, a cock, anything to deal with what was starting to be a desperate need for release. I started wiggling my ass as if I could force it back onto his cock, and making smothered "Mmmpphh" noises behind the gag. If I hadn't been gagged, those noises would have been me begging, "Please, touch my pussy! Put something in my cunt and bang me with it! Fuck me now!"

Eventually I was rewarded. The client finally figured that he had warmed my ass enough to get him turned on, and he put down the strap and grabbed my asscheeks with both hands, reigniting the burn where he had been slapping me with the strap. He pulled them apart to expose my asshole and pussy, and started running his fingers up and down my asscrack from pussy to asshole and back again. After nearly an hour of building need, of pain transmuted into desire, the feeling of nearing fulfilment was ecstatic. It got stronger when I felt a squirt of cold lube hit my asshole and start running down into my pussy, its lips held open by the client's fingers so the lube could run in to where it was most needed.

The suspense was getting unbearable. What would he put in where? Cock, fingers, tongue, toy? Pussy or asshole? All of the above? I didn't care. I was breathing more and more heavily through my nose, and my whole pelvic region was on fire with need and with a swelling almost-orgasm that was demanding to be released. Finally he slid his cock deep in my dripping cunt and began to thrust. After only a few hard thrusts, the orgasm exploded through me and I threw back my head and screamed into the gag.

When the orgasm subsided, I hung my head in exhaustion, but the client wasn't nearly done. He stopped for a minute to let the orgasm finish washing over me, then started thrusting again. At first it was almost painful as he thrust into my overstimulated pussy that hadn't fully recovered from the first orgasm. Then the sensations started turning back into pleasure. I could feel my dangling breasts sway forward with each thrust, then slap against my chest as they finished the return swing. The effect was strangely erotic, multiplying the feelings that were growing in my pussy and blending with the pain from my tortured bum. Finally a second orgasm, not as shattering as the first but still powerful, ripped through me. Then I felt the load of warm cum hit my cervix, telling me the client had climaxed and would probably start winding down.

Once the session was over and I was back in quarters, showered, dressed, and generally freshened up, I sat on an extra cushion in the common room and thought about what had happened. As I said earlier, I had sometimes enjoyed moderate impact play before being enslaved, but it had never been as intense and focussed as this. And in the first years of my slavery, my revulsion for the whole business of being forced to do things I didn't want had totally soured the whole experience of being bound, flogged and fucked. Now it seemed that I was getting so used to the way things were here that my old pain slut side was coming back to the surface.

Oh well, I thought. This is strange, but if I can get pleasure for myself out of what happens to me on a daily basis, so much the better.

Over the next while, the same thing kept happening. Sometimes the feeling of pain turning to pleasure was more intense than others -- it seemed to depend partly on my mood, and partly on how much the client hurt me and in what way -- but it gradually became the norm. I talked to Angelica, a confirmed pain slut who had actually signed on with Theo voluntarily because she liked the idea of non-consensual BDSM. She coached me further on the art of transmuting pain into pleasure, teaching me how to enjoy all the multiple sensory inputs you can get from a nervous system under assault. Asking around, I discovered that this transition to enjoying pain and forced sex wasn't unique to me. Lots of women hadn't made that transition, but others had, in varying degrees, and like me, had seen it as a blessing.

This long preamble serves to explain why, as my latest client dragged me down the hallway by my screaming nipples, I could feel my pussy beginning to juice with a pre-orgasmic tingle.

The client led me into suite number three, which, like all the suites, was filled with a mind-numbing assortment of bondage equipment. I glanced at the camera blisters on the ceiling, slightly comforted by the fact that I knew Jake, our bouncer, would be keeping an eye on me to make sure that the client didn't do things that could cause serious damage. More than once, Jake and his ever-present baseball bat had had to burst in to rescue me from a client who seemed to think Theo's rules didn't apply to him.

I was positioned in front of a waist-high padded horizontal bar. The client took two short chains from a shelf, clipped one end of each to my ankle cuffs, and the other ends to rings set into the floor. This pulled my legs into a wide spread, at least twice as wide as I had been forced into by Theo's spreader bar, and much less comfortable, an effect that wasn't helped by the fact that I was still wearing the red stilettos. I could feel the stretch pulling my pussy half-way open.

He unfastened my wrists from behind my back and fastened two more chains to my separated wrist cuffs. He bent me over the bar and clipped the chains to two more floor rings, holding me firmly over the bar with all my fuckable bits on display and my clamped breasts dangling. The gemstones worked into my braids rattled on the hard floor.

The client removed the leash clamps from my nipples, causing a rush of agony as blood flowed back into the abused body parts. They weren't getting much of a respite, though. He substituted another equally nasty pair, this time with weights dangling from short chains that stretched my nipples firmly down toward the floor. The sudden resurgence of pain almost got by my carefully cultivated ability to sublimate it into a kind of pleasure, but I focussed hard on the way the sensations raced down to make my pussy walls twitch in little erotic waves.

The client took advantage of my bent-over position to investigate my prominently displayed asshole. He lubed his fingers and my hole, then ran his fingers around and over it in an obscene massage. Then he started working two fingers into me. As they slowly sank farther and farther in, I started making yelps of pain behind the tape that was still spread over my mouth. I wanted him to think he was really hurting me, but actually he wasn't. I really like anal sex, and my anus is now trained to take almost anything up it without hurting more than a little. I would certainly have preferred to do it under different circumstances, ie. not as a slave, but since this was the hand I had been dealt, I had learned to go with it and take in the pleasure that a well-stuffed asshole can radiate.

He pulled his fingers out and picked up a huge ribbed dildo from a shelf. He reached around and held it in front of my face to show me how big it was, and I let out a muffled whimper of fake terror and shook my head violently. He just laughed and pressed the tip against my asshole, already warmed up from his fingers. Following Theo's "no damage" rules, he pushed it in slowly rather than just jamming it up me, and I felt the familiar burn as my sphincter was slowly stretched around it. The burn subsided and turned into an erotic feeling of stretched fullness as the dildo made its way further and further into me until the full twenty centimetres of business end were firmly seated in my rectum, with only the safety flange and handle sticking out.

Any parts of the room's walls that weren't covered in equipment were mirrored, and I could see a mirror behind me reflected in a mirror in front to give me a good view of what was going on at my hind end. He stood aside slightly to let me watch as he began fucking the dildo in and out, first slowly and then faster. The view was supposed to be terrifying, I guess, and I tried to react accordingly, but actually the dildo was sending waves of erotic pleasure through me as the ribs slid past my sphincter and massaged the inside of my rectum and my G-spot.

I really wanted to start screaming, "Come on, fuck me hard with that plastic dick! Give it to me!" Of course I couldn't, but my bottled-up pleading added to the cacophony of sensations coming from everywhere at once. The pleasure spread from my G-spot as the dildo massaged it and merged with the pain from my clamped nipples to begin surging in waves through my body. I finally worked myself into a smothered scream behind the tape gag. It was actually a scream of orgasm as the sensations in my rectum blended with the ones in my nipples to set off fireworks in my pussy, but I let him think it was a scream of agony.

He let go of the handle of the dildo, leaving it pushed to its full length inside me. Since it had no snapback like a butt plug, I'm sure I could have pushed it out with my rectal muscles despite the ribs, but I really didn't want to. I just enjoyed the stretched and filled feeling while I waited to see what he would do next.

He peeled the tape off my mouth, letting me take some deep breaths for the first time in a while. Then he went to a shelf and came back with a black panel gag and a big oval sponge. He pushed the sponge against my mouth, and I obediently opened to let him stuff it in. It was really large, and it took quite a bit of stuffing to get it compressed into my mouth and seated behind my teeth, but when he was done it effectively held my tongue down and blocked speech completely. Then he fastened the panel gag over the top to make sure it stayed in. The gag was neoprene, and I could feel it stretch slightly as it moulded itself to my face. I admired the effect in the mirror, my lips faintly outlined in the stretched neoprene.

He went back to the shelf and returned with a chrome anal hook with a big ball on the end. He gathered up a generous handful of my braids and cinched a piece of rope tightly around them. For God's sake, I thought to myself, don't fuck up those braids. They take hours to put back in.

He went back behind me and slowly pulled out the dildo, causing little ripples of sensation as each of the ribs pushed past my sphincter. Once it was out, he tossed it aside, lubed the ball of the anal hook, and pressed it firmly against my asshole. The ball was big, even bigger than the dildo, but since I was already gaping nicely, it didn't take much effort to force it past my sphincter so it could slide smoothly up my rectum. The shaft seated firmly in my asscrack, and the client threaded the other end of the rope through the ring at the end and used it like a pully to pull my head back and my bum up so my back was arched and my bum stuck out. Then he tied it off.

I was enjoying the sensual feel of the ball that was shoved way into my rectum, plus the feel of the cool steel against my asscrack, when "WHACK!" One asscheeck exploded in pain. He was obviously laying into me with one of the paddles from the shelf. Theo didn't supply whips or canes, which can really do lasting damage, but he supplied lots of other pain devices. It didn't help that my body jerked with the impact and made the weights on my nipples swing back and forth, putting extra pressure on my delicate buds.

The first blow caught me by surprise, and I screamed ineffectually behind the gag with genuine pain. Then I focussed on getting my pain slut back on. I let the pain of the blows plus the pain in my nipples blend with the sensations coming from my stuffed rectum and the erotically helpless feeling of being so thoroughly bound and gagged. The result was another slowly increasing feeling of pleasure in my clit and pussy that gradually spread through my abdomen and over my whole body. I felt my pussy beginning to run with juices as the blend of sensations churned through me.

Then he began hurling insults at me, each punctuated by another paddle strike.

"You filthy fucking whore!" (Whack!)

"Shit-faced cunt!" (Whack!)

"Scrap of fucking garbage!" (Whack!)

Surprisingly, he steered clear of racist slurs, which I was expecting any second. Maybe he just preferred sexist slurs.

I was glad that I was gagged. It helped me contain the peals of laughter that would otherwise have erupted as I listened to his totally unoriginal schoolyard-style taunts. Not only is it always unwise to laugh at someone who has you completely in his power, laughing would have disrupted my build toward another orgasm.

The jerks that resulted from each blow of the paddle not only yanked my nipple clamps but also made the ball of the hook grind inside my anus, pumping more sensation to my G-spot from the other side of my rectal-vaginal boundary. I started to squeal rhythmically through my nose with pleasure/pain as the sensations built up, my pussy on fire with sexual sensation that built and spread until another orgasm exploded through my body. I jerked in my cuffs and felt my pussy contract violently and squirt cum-juice as the orgasm tore through it.

This time, I was sure the client knew that my scream was orgasm-related and not pain-related from the way my whole body went rigid and then shuddered in ecstasy, my head thrown back even farther than it was being forced by the rope in my braids. I could see in the mirror that he had a big grin on his face. Although I'm sure that clients don't pay $2000 just for the privilege of giving us orgasms, pain-induced or otherwise, I think it must give them a feeling of dominance and control to know that they can wring them out of us.

I glanced at the clock that showed he had only twenty minutes of his hour-and-a-half time allotment to finish the preliminaries and get his rocks off. He must have been thinking the same thing; he put down the paddle and started to shuck off his pants. OK, I thought. Moving on to the next act.

I wondered whether he would remove either the gag or the asshook to open up a hole he could fuck, but he opted for the one that was still open, my vagina. That suited me just fine. I don't mind being face-fucked and I quite enjoy being ass-fucked now that I'm used to the rough way most clients do it, but if I have my choice, I really prefer cocks to be in the one place that's purpose-built for the job.