The Assistant Principal And Instant Messenger

THE ASSISTANT PRINCIPAL AND INSTANT MESSENGER Part 2 by Skip

Its quite terrifying to be left alone helplessly restrained and gagged in a dank basement even though I knew I wouldn't be alone for long. As my mind pondered escape strategies I could hear footsteps upstairs and talking but not what was being said. Within five minutes I heard footsteps descending the stairs but I was faced away from the stairs. Moments later Tom having removed his ski mask and a female were standing in front of me.

The female wasn't dressed like dominatrixes I had seen in web pictures. She was about 30 years old, a brown eyed brunette about 5'10 and 120 pounds wearing blue jeans, tight fitting light blue ribbed pullover sweater and stiletto heels. She clearly exuded an air of intimidating authority without saying a word. With her arms folded in front of her she appeared intent on studying me before she proceeded to pinching my tits, buttocks and fingering my sex in a surprisingly gentle manner.

As terrified as I was I would have been even more so had I known then what I later learned about her. I'll relate some of that at this point. Cindy lived on Long Island and was employed by a New York City bail bond company to track down bail jumpers, arrest them and transport them to jail to prevent the company from having the bail forfeited. Tom as it turned out had lost his accounting license and also worked as a bounty hunter on a free lance basis. Cindy was working with Tom on a particular case and that was why she was in the area.

Cindy was the bad girl of bounty hunters, what Tonya Harding was to figure skaters. She had acquired a reputation for sadistic cruelty in abusing her captives both male and female. In addition she was a self-employed part time dominatrix with a predominately female clientele and a small number of males. They paid to willingly be subjected to her degradation and cruelty. Occasionally Cindy was hired to train an unwilling submissive or at least semi-unwilling such as me. In my case it was purely pleasure as she wasn't being compensated.

After warning me that the no speak without permission rule was still in effect and that she was to be addressed as "Mistress" she ordered Tom to remove my gag. I couldn't help but sense that he was reflexively obeying her commands and that Mistress, not Sir, would be running the show.

Mistress then proceeded to deliver a low decibel but quite matter of fact monologue. Her initial impression of me was favorable and she complimented me on my body. Despite my professed distaste for lesbian sex I would be subjected to it anyway and I was expected to perform vigorously. This would include both oral and strap on sex. If I failed to meet her expectations I would be confined as long as necessary for me to be so trained. Further if I failed to please her she had some uses for my mouth which would be far more distasteful. She opined that most heterosexual females who became involved in BDSM eventually come to enjoy serving a dominatrix on occasion. In any case she emphasized again that I had no choice in the matter.

She commanded Tom to prepare me and walked upstairs while he removed the cuffs attaching me to the bar and reattached the leash to my collar. He led me the short distance to a couch and ordered me to kneel facing it with my hands behind my head and fingers locked together. The leash chain was left dangling from my collar. I knew that very shortly I would be receiving my first taste of pussy.

Mistress returned from upstairs and was wearing a two piece black leather dominatrix outfit consisting of a bikini like top and a waist harness which bared her shaven sex. I correctly assumed that after being forced to take it by mouth a strap on would be attached to it. My three weeks of perusing bondage websites had been quite educational.

The Mistress sat on the couch facing me and removed the leash dangling from my collar. With a derisive expression directed towards Tom she flung the leash to the floor. I sensed tension existed between her and Tom and I was caught in the middle. This did nothing to allay my fears still she did seem to be level headed and I was more concerned as to what Tom had in store for me.

Sitting with her back to the back of the couch Mistress grabbed my hair and pulled me forward and ordered me to begin using my mouth and tongue. I was allowed to place my hands around her legs. Thus I began my first exposure to lesbian oral sex. The reaction of Mistress was quite visible, it was arousing her tremendously as I strained to position myself efficiently. Finally realizing the difficulty I was having she changed her seating position by moving forward towards the edge of the couch. It made it much easier but she also warned me not to slacken my intensity. I continued diligently for nearly ten minutes arousing her to fever pinch intensity and causing repeated orgasms.

Finally I was allowed to stop and Mistress complimented me for my performance. Then came the really disgusting part which was licking her asshole. Sensing my reluctant body language she picked up a flogger which instantly ended my hopes she would relent. She knelt on the couch facing away from me in such manner that I had to strain to perform as required. It was every bit as disgusting as I had expected and made the taste of her pussy gourmet like by comparison. Thankfully I was only required to perform for about three minutes and I was not required to penetrate more than superficially with my tongue.

Mistress then commanded Tom to secure me in the stocks. Very sarcastically she directed him to lead me by the elbow and not to use the leash. Being confined in the pillory device was much more uncomfortable than the overhead bar as my upper extremity was involuntarily arced forward. My head and each arm was in a separate hole but my legs were unsecured. It was the ideal position for strap on sex.

Due to the direction I was facing I could not see what was taking place behind me but the first indication that the strap on was imminent was that Mistress applied a cold gel like substance to my anal area. Then without saying a word I felt the strap on penetrating. The initial thrusts were slow, deliberate and moderately painful but not excruciating as I had envisioned. As the tempo of the thrusts increased I came to the strange realization that I was actually enjoying it and would quickly become an addicted anal slut.

I also realized that climax was unavoidable and I feared the consequences when it happened. In desperation I cried out "permission to speak Mistress". Mistress knew my purpose and to my surprise merely stated that I could do so whenever I was ready. The approval came not a second too soon and a wave of pleasure ripped through me the likes of which I could never have envisioned.

As the wave slowly ebbed I could hear Tom informing Mistress that the suspect was at the apartment. Suddenly there was an abrupt change in Mistress' attitude. She informed me that they were leaving to pick up a prisoner and that I would be left unattended in the stocks for at least an hour. "Don't go anywhere girl" she remarked with a smirk. Then seemingly as an afterthought she added that I should be rewarded for my good attitude and with that a smaller sized dildo was inserted in my sex. I quickly learned that it was equipped with a time delay device so that it would vibrate at low speed for 30 seconds or so, remain off for about a minute, then repeat the cycle.

Considering the bizarre events that had already transpired since I arrived at Tom's home the extended confinement in a pillory seemed to be par for the course. The vibrator buzzing away within my sex made it somewhat more bearable and I least I wasn't blindfolded or gagged not that I would have been permitted to speak had anyone been present.

It seemed like several hours but probably it was no longer than ninety minutes before I heard noises upstairs and then what sounded like someone being dragged down the stairs. Judging from the mmmpphhh like sounds it was a gagged female and from what spoken words I could hear that she was about to be attached to a chair I had seen previously on the basement floor.

Shortly thereafter Cindy removed the dildo from my sex chuckling about not wanting to replace the batteries. Tom then released me from the pillory and I was able to catch a glimpse of the new captive. She was seated on a high backed chair her hands cuffed behind her with steel handcuffs. Her ankles were taped to the chair legs and a leather belt encircled just below her breasts attached her to the back of the chair. Black duct tape was wound around her mouth and eyes largely concealing her facial features. She was a taller brunette, appeared to be in her late 20s and was wearing black slacks and a white blouse in what appeared to be a waitress uniform.

My view of the new captive was brief as Tom attached the leash to my collar and walked me upstairs and into the bedroom where I had first undressed. I quickly found myself lying on my back on the bed my wrists attached to the opposite bed posts. A four foot spreader bar was attached between my ankles and the bar was pulled up over my head so that I was completely vulnerable and helpless. He quickly lowered the bar to the foot of the bed but there was no doubt what he had in mind. Being restrained in this manner was a powerful turn on for me and I couldn't wait to be reconnected to the headboard in the legs up manner. I'd seen this position in web pics and it had instantly aroused me now my being fucked in that position was imminent. From the look on Tom's face I'm certain he realized this and would subject me to prolonged denial

After reminding that the speech rules were still in effect Tom provided some explanation of the days events. Cindy he explained had a two faceted personality one manic and one depressive. They weren't triggered by biochemical or other physiological factors but by the course of events on a given day. The day before they had narrowly missed capturing the fugitive who was currently confined in the basement and Cindy blamed it on Tom. Cindy was a perfectionist when it came to hunting fugitives and any flaw was likely to trigger the depressive phase.

Paradoxically when Cindy was in the depressive phase she tended to treat her submissives with less cruelty than if in the manic phase. Tom stated he was surprised I was treated so gently. For example a common technique of Cindy was to stuff her soiled panties into the mouth of her submissive and tape them in place. Another was to use clamps to inflict various breast and genital tortures. He pointed out that a pair of panties was presently stuffed into the mouth of the prisoner in the basement.

Tom did not apologize for my treatment and it had been his intent from the start to force me to serve a dominatrix. He did concede that ordinarily a submissive would not be left restrained and unattended for such a lengthy period but such were the exigencies of the bounty hunting business. For the remainder of the session I would be serving Tom exclusively as Mistress would be preoccupied with the female prisoner. Needless to say I found this quite agreeable despite my new found attraction to anal intrusion. Still with Mistress now in her manic phase it might prove to be far more painful than I could tolerate.

I continued my compulsive good speech habits. Tom would order me to thank him for the pleasures I was being subjected to and I would respond emphatically "Sir the slave is extremely grateful for the pleasure". Although I refrained from requesting permission to speak Tom made numerous statements requiring such responses and it was clear that my responses were a big turn on.

Tom continued gently stroking my clit with a super sized vibrator carefully timing the duration to arouse me before stopping. I was still under orders not to climax without permission and I knew it would difficult to hold off. The flogger resting on the bed served notice what my punishment would be if I did. At least the cattle prod was nowhere to be seen.

Cindy then appeared in he doorway complaining to Tom that the stupid bitch in the basement had wet her pants and this would necessitate bringing her upstairs for a bath and clothing change. Tom offered to help bring the prisoner upstairs. Cindy responded with her trademark smirk "Tom I wouldn't need any help dragging you to the bathroom and stripping you" before giving him the finger and returning to the basement.

Immediately thereafter I could hear the sounds of the prisoner being dragged upstairs still wailing in her gag and caught a glimpse of her as she passed in the hallway. She was being dragged half by the hair, half by elbow and was still fully clothed, handcuffed, gagged and blindfolded. The sounds of water could be heard from the bathroom. A few minutes later I caught a glimpse of the prisoner being returned to the basement. She was still restrained in the same manner but had been changed into a two piece orange jail type jumpsuit.

Tom ordered me to harden him by mouth and he sat astride and facing my head. Although my Canadian lover was never satisfied with the quality of my oral sex I knew that I had to please Tom if only because it was the proper role of the submissive. As my wrists were restrained I was forced to take Tom's member using only my mouth and I put forth my best effort. Tom was already hard enough to satisfy me vaginally but I did as I was ordered. Surprisingly he did not berate or threaten me over my technique and after a few minutes he withdrew without ejaculating sparing me the distasteful part of swallowing his load.

He then proceeded to attach the spreader bar to a point over my head using a chain he already attached to the bed frame. I was ecstatic being exposed in this position and Tom was determined to drive me wild by using slow and deliberate techniques. To satisfy his own erotic desires he gagged me using a single strip of duct tape and he made it clear he expected passionate moaning sounds. It didn't seriously impede my breathing and it was far preferable to the foul tasting penis gag. He then began a series of slow thrusts. My moaning sounds were spontaneous and he continued to torture me with his slow pace for several minutes. Finally his ejaculation and my climax occurred before he withdrew leaving me in my ball tie position to cool down from the most intense orgasm I had ever experienced.

All good things must end and Tom announced that I would be freed. Half of me wanted to stay but the other half said enough for one day. The later half won out and I showered before dressing. My departure was rather abrupt and unemotional with Tom indicating I was welcome to visit again and that he was quite impressed with my submissive performance.

It was nearing 8:00PM as I began the long drive home and I had plenty of time to reflect on the days events. I'm more confident than ever that I can function in an authoritarian role as an assistant principal and be sexually submissive to a male periodically and in a discrete manner. I still resent that I was deceived and forced into lesbian sex yet the anal part was extremely satisfying and I know that eventually I will seek a similar experience..

Tom is competence as a dom and his sexual prowess is adequate yet I can't help but feeling I could have done better. One thing is for sure is that on my next encounter I will try a motel session first before committing to a home dungeon with a dom.

Arriving home before midnight I check my Email. One letter is from a dom in Harrisburg that I chatted with briefly last week and he is interested in meeting me. Harrisburg is only a ninety minute drive but he is willing to meet me halfway at a motel in Shamokin Dam. I'm going to give this some thought.

THE END