My name is Victor and this is my story.
I was in a great mood as I pulled into the parking lot of Paulson and Associates. It finally seemed like I would be getting out of the deep financial hole I had dug for myself over the past year or so. In addition to my regular 9-5 job, I had picked up a great part time gig as a personal maid/housekeeper for Heather Paulson, an enterprising young accountant trying to build a successful business in the financial consulting field. The gig not only provided some needed extra cash, I had worked out an agreement with Ms. Paulson that she would allow me to perform the cleaning duties dressed as my alter ego, Victoria.
Victoria was a relatively new development in my life. I had spent the better part of my life as a happily heterosexual guy with never any desire to experiment in cross dressing or the like. Then I began dating Julie, who convinced me it would be fun to try it as a sexy accent to the kinky direction our sex life seemed to be taking. Although I was very leery the first time Julie dressed me in silky undergarments, the smooth feel of the silky cloth really kind of turned me on; and by the way, the sex with Julie afterward was spectacular.
The adventure accelerated one night when Julie and I attended a networking event and ran into Eric Paulson who was a college friend of Julie’s. He happened to mention that his sister, Heather, was looking to hire someone to perform light cleaning and housekeeping duties at her suburban home on a part time basis. Julie’s eyes lit up at the opportunity and after several more drinks convinced me to apply for the job, dressed in a French maid outfit and some of the other female accessories we had accumulated for our cosplay adventures.
It took all the nerve I could muster, but I managed to don my female finery and show up at Heather Paulson’s home for the arranged interview. Amazingly, I got the job! I am sure it wasn’t because of my looks or her belief in my ability to keep her house clean, but more likely because she was intrigued with the novelty of the situation. Who else could boast such a unique scenario?
After several weeks on the job, I was summoned to my boss’ office for a meeting. I was looking forward to seeing Ms. Paulson in her professional setting as I stopped by my apartment after work and changed into my best maid uniform. I started with my best black lace bra and panties, added a brand new pair of thigh-high fishnet stockings, my black and white uniform and my finest (and only) 3” pumps. I had no time for makeup as I had to rush in order to make it in time for my appointment. I did not want to keep her waiting!
I entered the building through the side door from the parking lot and went to the second floor to look for Suite 204. When I found it, I was surprised that there was no name on the door, only the number. I knocked gently on the door then entered.
Heather Paulson sat at a small receptionist desk and greeted me with a friendly smile. ”Hello, Victoria. I am glad you were able locate our building ok. How are you today?”
“Fine, Ms. Paulson. Your directions were excellent. Thanks. How are you?”
“I am fine, but I am afraid I have some bad news. Come over and have a seat.”
As I walked across the room to the chair next to her desk, I scoped out the surroundings. I saw no chairs for clients to sit in while waiting, no coffee table with months-old magazines to read, no expensive paintings or sculptures to impress the waiting clients and no framed accounting degrees on the wall. Methinks Ms. Paulson is not what she presented herself to be!
As I sat at the side of her desk, I was able to see that Ms. Paulson was not only well groomed and made up, she also was stylishly dressed in a silk-like blouse and above-the-knee skirt and what looked to be sexy 4” pumps, all in black. It was painfully obvious she was not wearing a bra. Peeking out from under her skirt were the lacy tops of her black nylons. Ms. Paulson was looking Hot!
“I called you in today to discuss your performance on the job as my personal maid and housekeeper. While it certainly is fun and kind of sexy to have a male masquerading as a female maid and I really do enjoy having you around, the fact of the matter is, your cleaning skills are just not satisfactory. I find that when you are done, I have to do several of your completed tasks over. The bottom line is, Victoria, I am afraid I will have to let you go.”
An ominous silence filled the room as the shock of what she had just told me sunk in. She sensed that and waited patiently for my response. She was firing me! I couldn’t believe it!
I tried to force back the tears I was sure were forming. I didn’t know what to say but I knew for sure that I really wanted to keep this job! The only thing I could think of was to beg for forgiveness and a second chance.
“Ms. P-P,” I stammered. “I am really sorry. I did not realize that my work was not pleasing you. I know I can do better if you would give me a chance.”
The next few minutes consisted of me begging, pleading and groveling with corresponding rebuttals from Ms. P. until finally I played my last card.
“Please, please, please, Ms. P. I will do anything if you will just give me another chance. ANYTHING!”
Ms. P suddenly got real quiet and a smirk began forming as she considered this ultimate offer. “Anything??” She enquired.
I quickly calculated in my head, “What is the worst thing she could ask me to do?” Little did I know. How could I imagine what her devious mind might come up with?!
“Are you sure you mean ‘anything’?” she asked.
“Ms. P,” I said, “At this point, this job and my relationship with you really mean a lot to me. So yes, I would do anything!”
She thought for a moment and then slowly responded. “All right,” she said cautiously, “Here is my proposal. There will be two parts to our reinstatement agreement: first, you will perform a personal tribute to me for being such an amazing and forgiving boss; the second part will be the retribution you must suffer for the many times you have disappointed me. The rules will be simple but must be followed to the letter. During our sessions, you will speak only when spoken to and you will address me only as Mistress Heather or simply, Mistress. Additionally, you must follow my orders, immediately as given and without question or hesitation. Can you agree to those conditions?”
My first thought: “What the Hell have I gotten myself into?” My next thought: “This is something I have to do. It might even be fun. I have got to do this!”
“I agree, Ms. P. I will do anything you ask”
“Perhaps you mean, “Mistress Heather?”, she replied.
“Ooops! Are we starting now?” I asked.
“No time like the present! Let the trial commence!”
With that she stood up, took my hand and led me to a door that opened to a small room with a massage table in the center of it. On the four corners and the midpoint of the four sides, I could see black straps attached to the sides of the table that looked like they would either buckle or Velcro together to secure someone in a certain position on the table. On the back wall there was a large set of drawers and cabinets with no indication what they might hold but at this point, I suspected their contents were implements of pain and restraint. The plot thickens!
Mistress Heather hopped up on the table and positioned me facing her between her knees. “I think we should start with your homage to me,” she said. “I have been on my feet all day and they could really use some loving attention. Why don’t you just drop to your knees right there and prepare to give me a really nice, soothing foot massage. Show my feet some love!”
Appropriately, I responded, “Yes, Mistress Heather,” and dropped to my knees in front of her. Immediately I realized my first big challenge. From my new vantage point, I was looking right up Mistress’ skirt at what appeared to be a professionally trimmed pussy just a few inches above the lace trim on her black nylon stockings. No panties! How was I going to keep my mind (and eyes) on the task at hand?!
“Why don’t you start by cleaning those shoes. They are almost brand new so a good once-over with your tongue would really bring out the shine.”
Licking her shoes?? Now there is an item that had never appeared on my bucket list. But I figured I’d better get to it and perform to Mistress’ satisfaction or I will never win my job back! I gently held her left foot and, starting from the front, I slowly licked the outside, then the inside of her 4” pumps while only sneaking one quick glance up past the top of her stockings.
She must not have noticed because she immediately commented, “Very nice job, for a novice! Now do that heel then move on to the other shoe.”
Encouraged by the ‘sort of’ compliment, I finished up the heel of the left shoe and started to perform a similarly good job on the right one. When I finished, I looked up at Mistress Stephanie for approval. Nope! Not this time!
“So now let’s move on to the actual foot massage,” she declared. “Take my shoes off and place them on the floor behind you. Start with a light massage and gradually increase the pressure.”
“Yes, Mistress Heather.”
I followed her instructions and began massaging her feet, one at a time. As I gradually increased the pressure, I could see she was getting a lot of enjoyment from my ministrations as she often tilted her head back, closed her eyes and softly murmured something I couldn’t quite understand. Quite frankly, I was getting turned on myself the more pleasure I was able to provide her.
After about five minutes, I could tell she was getting really turned on (as was I) when she abruptly slipped off the massage table and stood in front of me. To my total surprise, she proceeded to undo her skirt and let it drop slowly to the floor in front of me. Unfortunately, since her blouse was quite long, this latest action did not reveal the trimmed landing strip I had caught a glimpse of earlier.
“Remove my stockings!” she demanded. “I want you to worship my feet. But to make it a little more challenging, let’s see if you can do it without using your hands!”
It was obvious there was only one way to complete this task: by using my mouth. And at this point I was up for the challenge; figuratively and literally!
My first attempt proved to be a little more difficult than I expected! On the second try, I was able to catch a bit of the lace in my teeth and pull down one side a couple of inches. Then once I had the hang of it, it was just a matter of alternating one side to the other till I got them off. It took a few minutes but it was most enjoyable with my face nestled between the lusciously smooth legs of the lovely Mistress Heather.
Once I had managed to divest Mistress Heather of her stockings, she hopped back up on the massage table and offered me her dainty feet with their freshly painted bright red toes. Surprisingly, there was something about them that triggered yet another positive sexual response within me. What the Hell?!
I started massaging her bare feet in much the same way I had done them when they were dressed. Once again, Mistress Heather seemed to really enjoy my services as she was leaning back with her eyes closed; obviously ecstatic in the moment.
“Kiss my toes,” she whispered, “kiss each one, slowly and gently. Then lick them. Run your tongue between my toes and then lick my feet all over. You are so much better at this than you are at housework.”
Carefully following her instructions, I cupped her heel with my hand and began to gently kiss each of her toes in order, then using my tongue, gradually and sensually bathed both feet. Then I took each single toe in order into my mouth and gently sucked on them and ran my tongue between each pair of toes. I totally expected Mistress Heather to get a great deal of pleasure from this but what surprised me was the stirring in my loins. There came a point where I actually thought Mistress was feeling such an intensity of pleasure that she might erupt in orgasm! Just the prospect of such an event caused a sudden flow of blood to my nether region and created a sudden need for “adjustment.”
After what seemed to be an hour but I am sure was only a few minutes, Mistress Heather came down from her cloud of ecstasy and, after a few deep breaths, looked at me through clearer eyes and began to explain how the rest of this incredible session was going to play out.
“You have pleased me greatly with your performance in the first part of our session but you will recall that there would be a second part which I described to you only as retribution. This is where you will receive your punishment for the inferior job you have been doing for me and all the hours I have had to spend re-doing your sloppy work. Trust me, this part will not be nearly as pleasurable to you, although quite enjoyable for me, I suspect.”
“Let’s start with the obvious; a good old-fashioned spanking. Let’s warm that butt of yours.” Mistress Heather moved to a chair against the far wall, sat down and patted her naked thighs. “Come lay across my lap and take the first phase of your punishment.”
It was at this point I noticed a small end table beside her upon which were two paddles, one about the size of a ping pong paddle, and a leather one about four by twelve inches with one end in the shape of a handle. No way I was prepared for that!
But I knew I had best obey so I gently lowered myself into position over her lap. My uniform dress was about knee length so I knew that fabric and my silk panties would provide some protection. However, my first line of defense was removed immediately when Mistress Heather lifted the bottom hem of my uniform and tucked it in under the apron strings at my waist, thus baring my pantied ass for her pleasure.
The first blow was with her bare hand on my left cheek and the combination of shock and pain caused me to call out. “Ouch, that hurts!” I cried.
“Do you recall that one of our rules was that you do not speak until spoken to?”
“Yes, Mistress Heather,” I responded meekly.
“For that infraction, I shall add a few strokes to your spanking, and perhaps you will remember next time.”
“Yes, Mistress, I am sure I will. “
The next stroke was on my right cheek. It hurt about the same as the first one but at least I was expecting it. Mistress Heather continued alternating from one cheek to the other and although the strokes seemed to be about the same and Mistress never seemed to hit in the same place twice, the pain increased a little with each stroke. It became progressively difficult not to cry out or to try to block the blows with my hands. I tried to wiggle out of the line of fire but since I could not see the blow coming, my attempts were futile. Surely her hand will tire of this soon.
“I definitely approve of these lovely black lace panties you are wearing, but unfortunately, they prevent me from seeing just how pretty and pink your lovely buns are getting. Perhaps you should stand facing me and remove them,” she instructed.
The embarrassment of removing my panties in front of Mistress Heather was not nearly as shameful as my semi hard cock that their removal revealed. And there I stood with it waving bravely in her face!
“Well, you seem to be enjoying yourself, don’t you, Victoria? Or is it Victor now?” Let’s turn you around and see how pretty in pink those buns are.”
“Pink and black suit you well, my dear. Those pink cheeks go well with your uniform. Let’s see how we might even improve the look. Climb back across my lap and we will see how well this paddle works”
This time around the task was a little more difficult considering the semi-engorged state of my cock. I managed to get relatively comfortable by inserting it between Mistress’ legs, and she made sure I wouldn’t be doing any jumping or squirming by tightening her thighs around the newfound handle.
Mistress reached over to get the leather paddle from the small table. I could see now that it was smooth leather on one side and a leopard skin-patterned, felt-like cloth on the other. Perhaps this might not hurt quite as much!
Mistress lulled me into a false sense of security by gently rubbing my tender buns with the soft felt side of the paddle. It felt good and cooling against the burning hot skin of my posterior! Then she turned it over and started with the leather side. This time against my bare skin.
It hurt, but not as much as the hand spanking. Maybe I was getting used to it or perhaps Mistress realized the embarrassment was as much part of the punishment as the pain. She provided several more strokes before deciding to move on to the next phase.
“Stand up and put your hands behind your back!” she ordered. “Now that we have some color in those buns, it’s time to test some of your other parts.”
I stood as before, facing Mistress. Only this time I waved a form of salute that I hoped she would accept as a compliment. She did not comment at all. Instead, she reached out quickly and grabbed my balls, thankfully without squeezing too hard.
“Strip!” she demanded. Well, I certainly was not expecting this but after all the other surprises and her previous demands not to question her instructions, I immediately began to undress. My maid’s uniform came off in one piece over my head, leaving me standing there wearing only my shoes, fishnet stockings, a garter belt and a lacy black bra that obviously served no purpose other than aesthetics. Another milestone in humiliation!
After I removed the bra, shoes and stockings, I stood for her inspection.
“Very nice,” she said. “You are catching on.” Now I have some new toys for us to play with.”
At this point my attention was drawn to a large black plastic toolbox that sat atop a chest of drawers in the corner of the room. Mistress opened the toolbox and withdrew two sets of leather restraints, presumably one for my wrists and one for my ankles. They each fastened with a buckle and featured snap hooks for attaching to… whatever. She came behind me as I faced the massage table and fastened each securely into position. Then came a matching black leather collar that she fastened behind my neck and attached a short leash with a snap hook to the small ring in the front of the leash. A ball gag was the final adornment. It consisted of a rubberish gag in the shape of the head of a penis ,which was kept in place by a black leather strap that buckled at the back of my head. I could not imagine what would happen next!
I had seen pictures online of folks similarly restrained, but even my adventures with my fetish-oriented girlfriend Julia had not ventured into this level of BDSM. The level of tumescence of my growing member was suggesting that possibly similar play might well be in my future scenarios with her. But Mistress Heather was not done!
From under the massage table, she produced a spreader bar with eye hooks and U-shaped padded brackets on each end. When placed between my ankles and fastened by the snap hooks on my restraints, they provided Mistress Heather with complete assurance that I would not be leaving anytime soon. She pulled my hands behind my back and clipped the two wrist restraints together, rendering me totally at her mercy. Then she had me lean forward at the waist and rest my forehead on the edge of the massage table. I sensed she was not done with my butt!
Through the corner of my eye, I watched her retrieve a small (thankfully) black butt plug and slather it generously (again thankfully) with some sort of lubricant. I had experimented with these before so the sight of one did not cause extreme trepidation but once again, I was subject to the peak of embarrassment and humiliation. She spread my cheeks and slowly inserted the plug until it was secured by its shape into position in my butt. I was pleased to learn that although the plug provided a certain amount of discomfort, I did not experience anything I would classify as pain.
“Your assignment is to insure that does not fall out as we continue our little exercise here. Do you understand?” Obviously, I could not respond with the gag in my mouth but I nodded my head and did my best to say “Yes, Mistress” through the ball gag. It came out as an indecipherable grunt!
“All right then, let’s see if you can move back there against the wall.”
It took a superhuman display of will and dexterity to hobble backwards to the wall with the spreader between my legs and my hands tied behind my back but with just a little balancing help from Mistress Heather, I was able to make it without falling over or losing the butt plug.
Quite frankly, it scared me just a bit when she went to the toolbox and pulled out a large ziploc bag full of clothespins. I felt sure there was going to be pain involved with this! Then I noticed another new development she must have accomplished surreptitiously while my back was turned. Peeking below her long black silk shirt, was a skin colored strapon. It was pretty lifelike but a little smaller than many you see in the porn movies. I felt I was soon to be thankful for that!
Mistress Heather set the clothespins down and picked up a short black leather crop. The first blow was to my right nipple and stung mightily. The second to my left nipple was no different. Just so no part of my body would feel neglected, Mistress spent the next several minutes testing her aim to just about every square inch of the front of me. But of course, she saved her favorite target for last. Her first upward stroke to my balls sent a jolt through my entire body that caused a mighty flinch and another of those muffled groans. The next few weren’t quite as bad, mainly, I think, because I could see them coming and was expecting them. My cock was next. Each blow stung but did not have the multitude of connected nerve endings like my testicles, and was therefore a little easier to take.
The clothespins came next. First, she placed one on each of my nipples. Now that was painful! Next, she went to work on my “swimsuit area”. Starting at the base of my penis, she attached a straight line of about a dozen clothespins that traveled down the underside of my cock, around my nutsac and all the way down between my legs. She stepped back to admire her handiwork. She then took the crop and toggled each of the clothespins back and forth for several minutes. She did it quite gently but it still definitely got my attention!
I knew from prior experience that the removal of the pins was going to hurt a Hell of a lot more as the blood came rushing back into from whence it came. I was right! Each one she removed sent another message of pain to my brain. Wow! This woman knows her stuff! She seems to know exactly what to do to inflict enough pain to keep my attention directly on the situation at hand, but not enough to push me through my maximum pain threshold.
When all the clothespins were safely back in their bag, Mistress Heather gently massaged the affected area to prepare me for the next test of endurance.
“My newest toy,” she exclaimed. “I think you are going to love this one. Move out away from the wall.” With that, she dangled a menacing-looking flogger featuring long alternating strands of black and red leather in front of my face. I knew from experience that the effect of this implement was in the impact and weight of the strands together, rather than a stinging pain like the crop.
Mistress teased me at first with light strokes of the flogger interspersed with her gently dragging the soft leather strands across my skin.
The first stroke went straight across my back, then one across both cheeks of my butt, then many all over my body. The strokes continued to my back, chest, my thighs and, occasionally, with a slip of her aim, a shockingly painful stroke to my testicles. After the intense pain of the clothespins, these strokes were not near as hard to bear.
When Mistress seemingly tired of this, she reached into the toolbox and pulled out a small leather device with three chains hanging down from it that kind of looked like a tiny parachute with a small circular opening at the top. She activated this device by undoing the fasteners on the side and reconnecting them with my testicles hanging through the small hole on the top of the parachute. That left the three short chains hanging down between my legs and connected by a small ring at the bottom. There was no pain at all at this point but I was pretty sure I knew what was coming. And I was right, as Mistress produced three rather large weights and suspended them from the ring. The addition of each successive weight added a little more pain to my groin. But once again, not enough to send screams through my ballgag.
The dull pain of the weights was exacerbated by Mistress clipping my leash to the ring below the parachute then pulling the weight way out in front of me toward her then releasing the leash thus allowing the weights to swing, pendulum-like back and forth between my legs. Surely my ballsack was going to be much larger after this exercise. She seemed to enjoy this as several times she pulled the weights to the point where they were straight out in front of me then smiled as she watched the descending heights of the subsequent swings and the corresponding winces they produced from me. More fun was added by quickly smacking my cock and balls several times with her crop. Ouch! She might have been enjoying this; I was not. I took solace in that I felt at this point I was pleasing Mistress with my obedience and providing her with fertile practice fodder for her dom skills, so I felt I was perhaps on the way back into her good graces.
Mistress Heather unhooked the “parachute” and unsnapped my restraints from the spreader and from behind my back. She unbuckled the strap holding the ballgag in place. It certainly felt good to have the use of my legs again and at least have the ability to speak, even if I was forbidden from doing so.
“Don’t get too excited, we are not done yet,” she warned. “I have a special treat for you! Walk around to the end of the massage table and grab the sides of the table.” Mistress positioned herself behind me then told me to move forward so that my chest was resting on the edge of the table. I was pretty sure I knew what was coming.
To make sure I got the full benefit of the maximum anticipation, Mistress Heather moved to the side of the table so that I had full view of the whole package. And it was beautiful! She had removed her shirt and I slowly shifted my gaze from her smiling face to her beautiful breasts with their erect nipples, to the lifelike dildo that rose from the harness in her swimsuit area.
From the sidetable, she reached for a squeeze bottle of lubricant that she slowly and seductively spread its contents generously up and down the full length of her ‘member’. Retreating to behind me, she spread my cheeks and slowly removed the buttplug that I had managed to keep securely in place through this entire ordeal. It felt good to be rid of that intruder, but I knew it would only be seconds until it would be replaced with another. And, of course, this one would be much bigger!
Once I was properly positioned, Mistress Heather stepped close to the end of the table and poured a small portion of lubricant down my buttcrack, catching the flow with her fingers when it reached my butthole and gently applying it to my rosebud and the first couple of inches inside. She slowly inserted the dildo. Another first for today’s adventure! She slowly moved it in and out, gently pushing it with her hips a little farther into me with each successive stroke. Again, I was totally embarrassed and humiliated, but surprisingly not overcome with pain. Uncomfortable? Yes, most definitely!
After a few minutes of her slow, steady strokes, she stopped, withdrew the strapon and exclaimed, “Well, that was easy enough! But I think I would like to improve my view. Why don’t you hop up on the table, roll over onto your back and scrunch down here to the end of the table?”
And the view was much better for me, as well, since Mistress Stephanie had removed her shirt, gazing at her beauty was infinitely better than staring at the wall!
Mistress applied more lube to her strapon, reinserted it and began her rhythmic stroking as before. After only a few strokes, I was overjoyed to see her reach her lubricated hand to my engorged cock which had been aching for attention. She gently stroked my cock as she continued a sympathetic rocking motion with her hips that drove her strapon rhythmically in and out of me. I knew I wasn’t going to last very long at this rate. In fact, I am sure it was less than a minute, and I was done. Mistress seemed pleased to watch the hot, creamy liquid escape from my loins and spill out onto my chest and stomach.
I was exhausted and lay there with my eyes closed and a huge smile on my face. Mistress Heather slowly withdrew the strapon, unfastened the belt and let it drop to the floor. Now totally naked, she walked slowly over to the edge of the massage table and gently embraced me. Her soft breasts against my chest sent a warm wave through my whole body. She snuggled her face up to the side of mine and whispered softly in my ear. “That was incredible! I think your retribution will have to consist of doing this again.. maybe even more than once!”
With barely enough energy to speak, I replied, “Indeed Mistress, indeed.”
