Captive Hacker Ch. 03

"And now the deep test."

From a draw she takes a white probe, not very wide, but at least 10" long. I am scared at the idea that this is going to be forced into my bowels, and even more scared that it is certain to be dirtied and all this indignity is going to be repeated.

The first length slides in easily but then I feel it stop and push against something inside me. Mistress Benny keeps pushing and the pain grows. I plead for her to stop

"Mistress Benny, please stop, no Mistress Benny I can feel it pushing against something. Please stop Mistress Benny" I am so scared I actually try to substitute the pain

"Mistress Benny please stop, I don't mind if you whip me more Mistress Benny"

She just tells me

"Relax you pathetic Dick it'll slide the rest of the way in as you relax."

I am so scared I am thinking of stopping this torture immediately, but make a little effort to relax. I am amazed and relieved as I feel some muscle group relax inside my bowels and the strange feeling as the instrument pushes the rest of the way inside of me.

I am now scared about the result. To my relief and perhaps to Mistress Benny's displeasure it is as clean as it went in. I slump and sigh relieved. After dressing Mistress Benny returns me to Mistress Green in room 6, the toy room.

From the range of dildos and vibrators scattered over the room it appears that Mistress Green has been amusing herself while I was being cleaned. Mistress Benny informs Mistress Green that I have been properly cleaned and punished. She continues

"But Dick is so anally retentive. He squealed pitifully when I had to check his ass, he is going to need a lot more training."

Mistress Green agrees,

"OK then Dick, tomorrow we'll see you take some more of these beauties."

I feel physically sick because as says this her hand is running up and down a realistically modelled dildo, but this dildo is screwed onto a table top and must be 12" high and at least 3" in diameter. If she is going to force that into my ass I know that my whole torso would literally be ripped open.

***

Another day has passed and I feel a terrible despair that I will never be able to find a way out of this. Last night after the sickening games of the day I sneaked around trying to find phone or anything that might be connected to the outside world. Sleeping was difficult anyway because of the amount of punishment inflicted on me in the course of Mistress Green's training.

The day started normally enough, with me acting as Mistress Green's toilet and guzzling her piss when she woke. After my very light breakfast Mistress Benny again takes me to room 3 where I administer an enema to myself. I actually found it easier to hold as she counted down to 10 strokes. I was annoyed that I had to endure even those 10 as I had not actually done anything to require the enema, but I knew better than to complain. When Mistress Benny came to insert the deep probe I felt the same pain as it pushed against some muscles in my rectum, but remembered to relax, so before the pain became unbearable it had slipped all the way inside.

That was just the beginning of a day of anal abuse and varied punishments. The first toy I had to take in my ass was the same small silver dildo used the previous day, and it slipped in without any problem. Mistress Green then required me to beg to be fucked in the ass. I was very embarrassed to have to do this, it seemed gratuitous to make me seem to want it, as well as abusing me. I had to beg hard,

"Mistress Green please fuck my ass, I really need you to fuck my asshole, I love to feel hard tools and cocks pushing into my rear fuck hole Mistress Green."

When she thought I had pleaded with her sufficiently she would push the toy into my ass. Soon I was so accustomed to the act that it entered without resistance.

After that toy Mistress Green showed me a bigger dildo. It was still small, but it was ribbed and designed to look like a penis. I first had to suck the pretend cock as though I was giving it a blowjob. The taste and feel did not revolt me but the thought of the specific reason for the design made me feel nauseous. I sucked and sucked, licking the length of the dildo to fulfil Mistress Green's desire that I treat this like a real cock and pleasure it the way I would a real penis.

When Mistress Green was satisfied that I had properly sucked and worshipped the pseudo-penis, she positioned it over my backdoor.

"Now beg as if you wanted your fuck hole filled with dick Dick," she demanded and I then carried on, as she wanted.

"Mistress Green, please fuck my ass with your cock I so need you fat cock in my ass. My ass is gaping to receive your beautiful long thick dick Mistress Green." While mouthing these sickening entreaties I braced myself waiting for the anal invasion.

Mistress Green waited a little to build the tension, and then I felt the head of the glan against my asshole. As she pushed it I felt the pressure build and then with relief it was inside. She bade me continue with the begging, and this time I had to exclaim how good it was.

"Mistress Green. That feels so great, oh yes Mistress Green, your cock is so good buried in my ass Mistress Green." I am revolted by the idea that I am begging to be ass-fucked something I would never even consider doing. As I told her how great it was feeling she started moving it in and out, truly fucking my ass. The sensation was strange, like I was taking a dump as it slid out and painful as it pushed it's way back in again.

I was very relieved when she finally pulled the dildo from my ass. I thought that was the end of the training. There was a lot more to come. Mistress Green looked at me and told me,

"Dick you penis does not agree with your earnest desires. I suggest you get a hard on right now." Even though my ass hurt from the previous pursuit, I immediately started trying to think of something that would turn me on. With a smile I kept inside myself I imagined fucking this bitch in the ass with my dick as she begged for it. The idea was successful and I became hard enough for her to play with. I had been disappointed many times in my current position as sex slave so I knew she probably wasn't going anywhere with the stroking.

I was right; she let go of my erect dick and went to get another toy. I was apprehensive that she might find an even bigger dildo and was mildly relieved when she returned with something much smaller. The relief lasted seconds as I saw the toy she was holding.

"This is a butt plug Dick" Mistress Green told me rather unnecessarily. "There is no need to beg to be fucked because you only need to hold this in your ass. I'll let you put it in."

The plug was a greater diameter than the dildo she had used previously though obviously not as long. I doubted I could take it but took it from her hand to try. I bent forward so that my ass was as accessible as I could make it. I rested the plug against my ass and started turning it, trying to force my anal sphincter to open enough to accept the plug. I twisted and exerted as much pressure as I dared, but the widest part of the plug wouldn't slip into my ass. I pushed and screwed up my face with effort but couldn't manage it. Eventually I realised that I was going to have to beg Mistress Green to spare me the butt plug.

"Mistress Green I cannot get it in Mistress Green" I pleaded. "I have tried really hard, but it cannot get past my ass, it really won't go in, please don't make me Mistress Green," I begged.

I was surprised when she said

"Very well" but then she continued and realised that I had only modified the pain I was going to feel. She required me to fetch a whip from room 1. Room 1 was the punishment room where all the whips canes and paddles were kept. She made me return with a long whip. I was really scared.

"I can see Mistress Benny has already reddened your ass" Mistress Green tells me. "Lie down on that table. On your side. Now lift that leg up and hold the knee to your chin." As I followed her instruction I realised that my inner thigh was exposed and that was to be the target of her whipping.

"Mistress Green, please no, not there, I'll try again Mistress Green" I begged.

"You certainly shall Dick. But this is to encourage you."

The whip made much more of a noise than the cane as it whistled through the air and cracked against the table and my inner thigh. For a moment I thought that she had missed but then the blinding burning pain makes me scream out loud. I clutch my inner thigh, there is an angry red welt already rising. I continue sobbing and gasping as Mistress Green motions for me to rise from the table. She again presents the butt plug to me.

I bend over and position the plug against my asshole again. I am reluctant to push, but then Mistress Green delicately mentions

"There is always the other thigh Dick," and I summon all the tatters of courage remaining. Grinding my teeth I thrust the plug home with one push. I felt as I have torn my sphincter muscle, but as the pain dies away I am aware that the butt plug is resting, as it should.

Mistress Green takes hold of the plug and jiggles it about. This does not hurt as I expect though my ass feels distended beyond my butt cheeks. She then orders me to skip about. This feels very silly, but better than the anal abuse. The plug feels uncomfortable and strange but does not stop me performing the minor exercises as commanded. Finally she asks me to remove the plug. Taking the same position, I hold the plug and firmly pull it out. I am expecting a lot of pain, but it does not seem so bad. Then, naturally I must reinsert the plug. I managed it last time so again I grit my teeth and push in one movement. I am relieved the plug does not hurt as much as it enters.

"Excellent" I am told by Mistress Green. Mind over body is a wonderful thing when it comes to pain. Lets see what else we can find." I am physically and mentally exhausted as I kneel there. Mistress Green returns with another dildo, long and white and smooth. It looks to be a similar diameter to the butt plug. I am resigned to this perverted game and don't raise any objection, though I feel my heart sink at the thought.

Maybe I am becoming accustomed to this anal abuse. When commanded I easily pop the butt plug from my ass and start the degrading begging Mistress Green requires, begging to be fucked in the ass. She informs me I am in for a treat! And before inserting the dildo she turns the end. It is actually a vibrator and starts buzzing in her hands. The new sensation in my ass is very strange, almost the same feeling as when I shaved the hair from my crotch and butt with the electric razor. Whether it is because of the vibrations, or my ass is loosening, it only hurts a little as Mistress Green pushes the toy inside me.

After entering 3 or 4 inches or so, I have the same feeling as when Mistress Benny tests my ass after the enema, a feeling that I am holding a group of muscles closed inside me. Without being bidden I relax and he toy slides all the way into my ass.

"Good boy!" shouts Mistress Green as she begins to fuck my ass with the vibrator. I have to concentrate on relaxing to let it invade my bowels all the way so my exclamations of pleasure are rather repetitive. Mistress Green notices and remarks that I ought to be more enthusiastic. I try to comply, and keep my back door open at the same time.

After Mistress Green begins to tire of ass fucking me, she notices that my cock is limp.

"But Dick, again I am not convinced of your sincerity. You dick should be as hard as a rock when you are being ass-fucked." I struggle to obey knowing that to fail in this is to invite more punishment. I cannot think of anything immediately arousing enough and begin to get scared that I will fail in to get an erection. The thought I settle on in the end as I cast about is the feeling of lapping Mistress Green's pussy as I drink her piss. This causes my cock to begin to stir, and then I am struck by how depraved I have become using this idea to encourage my tumescence.

"One last toy for you to try then Dick" I am told. My asshole is aching from the abuse and I clench it with the thought of having to anything else in my rear door. The next toy is again a butt plug, but this time it has a long tail attached. "This will go really well with the rest of your outfit" Mistress Green informs me. The plug is bigger and again I am frightened by the thought of ramming it into my ass, but the thought of a whipping on my thighs is an incentive. I bend over to insert the plug, feeling its wider girth against my ass. I am torn in indecision, between the likely prospect of permanently harming my asshole and the surety of the whip on the thighs.

Mistress Green must have seen my hesitation and reaching forward suddenly rams the butt plug into my asshole. I scream at the pain. It feels as though my sphincter has been split it is burning so badly. Part of me wants to expel the foreign object, while another part is fearful of the consequences. Finally as the pain dies to a dull throb I am able to control myself again. Mistress Green requires me t walk around and witch my tail.

"Yes, that looks good Dick. In the future that will always be a part of your costume."

In the afternoon Mistress Green again took the opportunity to sunbathe. It was easy to sit in the shade and obey the commands she gave me. Rubbing oil into her back, bottom and breasts was a pleasant turn on, and there were no new toys or instruments shoved into my ass though the tail butt plug remained in place. It did not hurt, but my ass still felt sore and stretched.

Towards the end of the afternoon, I realised that I needed to pee. I had been trying to avoid the necessity because Mistress Green makes it as humiliating as possible to perform this basic function. I thought I could hold it, but as the need increased I realised that I was going to have to grovel to Mistress Green. She watched me as I crawled over to her sun bed. I began to beg and plead to be allowed to urinate. I thought I might have left it too long my bladder felt so full, but finally Mistress Benny appeared with the cane she used to whip my ass as I relieved myself.

"Take Dick to pee on the grass" Mistress Green directed.

I had become reasonably accustomed to this humiliation and stood with my hands on my head waiting for Mistress Benny to begin the caning. As I felt the first stroke land on my ass I was pleasantly surprised to find that the butt plug tail, though uncomfortable and undignified, helped keep the cane from hurting my ass too much. I was therefore able to easily piss and delighted in the fine stream of urine as it danced in the sun.

Mistress Benny started to return to the house and I crawled back to my original place. Mistress Green must have seen the ease with which I accepted the punishment and called Mistress Benny back. She asks me directly

"Dick, you took that very easily, did the tail help you?" I cannot see how this is going to lead to any more indignities so I oblige Mistress Green by confirming that the tail did help me withstand the blows. Mistress Green muses,

"Well we can't have that, I have an idea.

"Dick, bend over and remove the tail." I bend over and grip the end of the butt plug. It was forced into my ass with a lot of pain so I am reluctant to pull it out.

"Now Dick" Mistress Green commands in a stern voice. Holding my breath and clenching my teeth I give the plug a hard pull. My ass muscles have become accustomed to the plugs presence, and feel cramped as it pulls out. As the plug distends my sphincter I feel a great pain, but it is also a relief to be rid of the penetrating object.

My ass feels really sore as the pain dies away to an ache, and I involuntarily find the muscles tightening and then relaxing back to and open state. I have to consciously squeeze it closed. I suspect I am going to be caned again but I think it will not be unbearable. Mistress Green has other ideas.

"Cane him on the asshole Benny. Three strokes right over his little sensitive anus." I am truly frightened by the prospect, I feel nauseous at the thought of the pain. I don't know if I will be able to hold still and accept the punishment.

Mistress Benny laughs and positions herself so that the stroke is possible. I hear the swish of the cane and feel the biting hot pain as it lands exactly in my butt crack. I gasp out loud at the level of pain

"Mistress Benny, please no more Mistress Benny" I manage to stammer before the second blow lands on my inflamed asshole. The bite of the cane is even more severe this time and I squeeze my eyes and grit my teeth. When I have found the strength to cope with this blow, I try another plea

"Mistress Green I beg you to stop. My ass feels it is on fire, it is burning so much I cannot take anymore, I beg you to stop Mistress Green"

I barely have time to stumble out these words when the third and final stroke arrives on my anus. The fire and bite of the cane is even worse than before and I scream. Through the haze of pain I wonder if I'll ever be able to use the toilet again.

Mistress Green leaves me bent over with my ass in the air for a while, and it is a relief for a slight breeze to cool my burning hot asshole. It twitches spastically as the pain changes from fire to ache.

"The final requirement is to put the tail back in Dick" Mistress Green informs me. I have been holding the butt plug in my hand but I cannot conceive of anyway of pushing it into my tortured asshole. I reach round behind, and merely touching my rear door with the plug is enough to send waves of pain followed by nausea through my body.

"Remember Dick" Mistress Green tells me, "that you can still be whipped on the other thigh, or Mistress Benny could inflict more pain on your little rose bud asshole!"

I know that she is not threatening me and that there is a real will behind the promise of punishment. I take the plunge and without thinking about it thrust the butt plug back in my ass. The plug seats itself home back in my abused anus as I let out another scream of pain. It is only afterwards that I consider how foolish I have been. There is only the slim hope of finding some way out of the trumped up charges that have landed me in trouble that is keeping me here. I could easily resign this terrible situation and return to isolation in the Federal establishment I was held. I think that whenever it gets to the stage that Mistress Green threatens to bind me before inflicting her indignities and punishments, that will be the time to quit this debasing servitude.

***

I have finally been allowed to come, but the experience was not pleasant and the memory of the pain makes me fear the process if it is ever repeated. I continue to endure this tortured captivity hoping that I will be able to extract myself from the unjust situation that forced me into this.

The morning after the day of ass torture my anus ached a lot. I thought I would not be able to insert the butt plug tail that had become part of my uniform and it was only with the application of a lot of soap and willpower I managed to withstand the pain as it slipped home. The overly tight collar and constraining harness on my dick were nuisances I could ignore.

The day stared with an incredible tease that was to turn to my most humbling indignity. When I attended Mistress Green in the morning she was again curled up with Mistress Benny. I waited until they began to awaken. This morning they did not pay any attention to me, and when Mistress Green opened her eyes she tenderly kissed Mistress Benny on the lips. It was a fantastically erotic experience and my cock was instantly aroused.

The show continued as they both became more involved, kissing deeply and touching each other under the covers. Then Mistress Benny sat up so the covers fell away. She was wearing a pale blue camisole top, and her tits were beautifully outlined in the light. The hard little nipples were dark and shadowy through the material. Mistress Green reached up a hand, first cupping one breast gently, and then moving up to the shoulder to slip one side of the camisole off. Pulling it down she revealed Mistress Benny's breast in its glory. Her flesh was pale, and the dark nipple small and hard. Mistress Green sat forward and took the nipple in her mouth. Mistress Benny purred and her hand came up to caress the back of Mistress Green's head and neck.