New Job, First Lesson With Mistress free porn video

New Job, First Lesson:

It all began when I moved to New York to get a fresh start. Always a shy loner, I was teased throughout school for being somewhat short and effeminate in looks. After my mother passed away right after I graduated college, I no longer had any ties to Chicago, and I wanted to move to New York to find a new life for myself. I had very little sexual experience, and was hoping to be able to find a girlfriend in a new city. Landing an apartment in Manhatten and a job as a personal assistant to the chief executive officer of a small private medical consulting firm, I was looking forward to my first day. My job interview was conducted via Skype, so I was a bit nervous about meeting my physician-turned-business-entrepreneur boss in person for the first time. I walked into her office and was stunned. She looked very different from our Skype interview. She was much taller than me, with an extremely curvaceous body that she flaunted with a skin tight dress. Her breasts were huge and magnificent, and spilled out all over. I found I had difficulty concentrating and couldn’t maintain steady eye contact. She clearly noticed my discomfort and said I seemed nervous. I babbled some response, which seemed to annoy her. I was sitting in a chair in front of her large cherry desk in her plush office. She leaned over the desk, giving me more of a view of those outrageous breasts…no bra…big erect nipples poking through the thin silk dress like hard bolts. She stared right at me and accused me of looking at her breasts. I was flabbergasted, apologizing profusely. She told me that I would have to get more comfortable in her presence or this job would not work. I apologized some more. She looked more annoyed, came around the desk, and clearly saw my erection tenting the front of my loose slacks. She stared…I groaned, trying to cover my crotch and feeling completely out of control and humiliated. She saw my face turn bright red, when suddenly a wicked smile crossed her face. She laughed an evil laugh and said “Well, I have some new thoughts about your job duties. As my personal assistant, some of your tasks will be…well.. personal.” She reached down and lightly touched my tented pants, smiling at me. I thought I would faint. “Now, now, little boy, don’t be ashamed of being attracted to me. Most men are. Now pull down those pants and let’s see that erection of yours.” I couldn’t move a muscle. She came over, pushed me back in the chair and very quickly pulled my pants down. I was mortified, especially because of the pink lace panties I was wearing under my suit. My secret was out. I groaned. She gave another wicked smile. My dick was leaking copious amounts of precum, soaking my stretched panties. She pulled my lace panties down, pushing her breasts into my face, and gently rubbed my cock up and down, her hand well lubricated with precum. I moaned, my cock and body twitching. Suddenly she began furiously jerking on my cock with one hand while squeezing my balls hard with the other. Startled, I yelped in pain and then immediately came all over her hand and dress. “So, little panty boy, it looks like you have no self-control. Bad, bad, bad boy. We’ll have to do something about that.” With a powerful pull, she lifted me out of the chair, sat down, and pulled me over her knee. “Clean this mess off my hand” she said as she stuffed her cum covered fingers down my throat. I gagged, choking on my cum and her fingers, tasting the musky liquid for the first time, then yelped as her other hand came down hard on my ass. Again and again she spanked me, holding me helpless on her lap, saying “You have to learn self-control, panty boy. I will tell you when you can cum. You need to follow my orders as my assistant.” I struggled in vain, the searing pain of her hand sending shock waves through my whole body, then finally I collapsed and whimpered, giving up. She finally stopped, reaching between my legs and squeezing my cock and balls until I became hard again. Her short dress was hiked up and I could feel her bare legs against my body, one hand now gently rubbing my rock hard cock, while the other stroked my burning bright red ass. She rolled me off her lap onto the floor, where it became evident she was not wearing panties under her dress as I lay staring up at her completely shaved pussy, which was streaming her juices down her leg.

“Let me tell you the rules around here, panty boy. You will obey my every whim without question. By the way, I videotape every meeting in my office, so if you don’t want your performance today all over the internet, you will be a good boy and do as you are told. You may answer Yes Mistress, now.”

I lay there silently in shock, when suddenly she came down on top of me, swiveling around and sitting her drenched inflamed pussy and wet asshole right on my face, her powerful thighs squeezing my head, her hands immobilizing my wrists and hands, my breath cut off completely. In spite of the shock of it all, the smell of her juices was intoxicating. “So you have nothing to say, panty boy. I told you to answer now, not at your leisure. Since you have nothing to say, your mouth can be put to better use. Suck me; stick your tongue in my ass, now!” She was crushing my face and moaning in pleasure, as I started to panic without air. I thrashed helplessly, feeling faint, when finally she lifted her pussy to allow me to gasp for air. “Have anything to say yet?” “Yes Mistress I quickly croaked.” “Good, then suck harder and push that tongue all the way up my asshole.” She sat down again, slowing her pace, sensually swiveling her hips and gently rocking back and forth, using my face as an object for her pleasure, without any regard for my comfort, her tight dress hiked above her waist. Back and forth she rocked, my tongue stretching, moving into her pussy and anus, now both soaked with her juices. Suddenly she turned around, facing my penis, and sat down gently on my face, making soft, sensual moaning sounds as she slowly writhed her body to maximize her pleasure. Within a minute she became rigid and tense, pushing down with crushing force on my face, her pussy and ass pulsing wildly, her massive clit throbbing, as her powerful orgasm ripped through her entire body, squirting all over my face and the plush carpet floor. As she came, she grabbed my stiff cock with both hands, pulling it violently back and forth while she leaned over and shoved three fingers straight up my ass while she rocked wildly on my face. It was so overwhelming to me that I couldn’t help it. Her fingers quickly located my prostate, which she manipulated so vigorously that her violent movements inside my painfully stretched rectum triggered throbbing and uncontrollable contractions in my organ. I suddenly felt my balls and asshole tighten and begin pulsing as I came again, my semen shooting in long streaming ropes all over her hands, arms, my stomach and her thighs and dress. She continued to punish my prostate until she felt the contractions stop, then yanked her hand out of my ass.

“Lick your mess up. I did not give you permission to cum. We will have to fix that.” She rolled off my face, turning around and jamming her cum covered hands down my throat, causing me to gag and choke. I then lapped my semen from her leg as best I could, and she rose and told me to follow her. I stood up, my pants around my ankles, and began to pull them up. “On your knees, when I ask you to follow me, it is always to be on hands and knees. Also, I did not give you permission to pull your pants up, did I?” I immediately got on my knees and yelled “No Mistress. I am sorry Mistress.” I began to scuttle awkwardly across the floor as quickly as I could, my lace panties and slacks stuck around my ankles, my now limp cock and balls swinging beneath me, my cock still dripping the last drops of semen. She laughed, saying “Maybe you will learn how to be a good assistant.”

I followed her through a hidden door into a private inner chamber. I was so scared and overwhelmed to see what looked like a sadistic medical laboratory, with a cruel stainless steel table with straps on it, and walls covered with medical equipment, whips, paddles, and many devices I did not recognize. She pulled open a drawer, taking out something I did not recognize. “This is a steel chastity tube that will train that cock of yours.” She told me to get on the table. I yelped as my sore ass made contact with the cold steel table. She locked a steel ring around the base of my cock and balls; squeezing them uncomfortably and making them protrude. Then she slipped the small steel tube over my cock, latching it to the base and inserting a small lock, the key to which she then hung on a beautiful fine gold chain around her neck. As she leaned over me, her breasts rubbing against me, and I began to get hard, I felt pain in my cock and cried out. “Oh, so I see you have discovered the sharpened steel protrusions inside your cock cage. In this device, you can get semi-hard, but you have to pay a painful price.” It felt like nails were pressing all over my cock. I quickly became soft, sighing with relief. “I see you are learning control already, “she said smiling wickedly.

“You will learn how to please me better, panty boy.” I rode the subway home that night with a set of instructions for how to dress for work the next day.

The next day I came in to work having stayed up late the night before, following her instructions. I went to the adult store and purchased a set of steel anal plugs and a harness to hold the plugs in. As I mentioned I was sexually inexperienced and never had anything in my ass prior to her fingers the day before. It was anxiety provoking the night before, lubricating my anus and the plug, and placing it on the hard floor and sitting on it as Mistress instructed, then putting on the belt so it would stay in while I attempted to sleep. The smallest plug was uncomfortably in my ass as I sat on the subway on my way to work, thinking of the events in the last 24 hours. The previous night I had shaved all the hair off my body, except that which was covered by the chastity device. I wore stockings and had a garter belt on under my slacks, as instructed. I was sleep deprived since every time I would get an erection at night, the pain from the steel chastity device would wake me up, or the anal plug would feel heavy and painful as I moved. The thick base of the plug protruded at least an inch out of my ass, putting pressure on my anus every time I was in a sitting position. As I sat on the subway, the vibration of the train seat reverberated on the protruding base of my steel anal plug, vibrating my anus and prostate and causing my penis to swell. Then I would feel the pain of the cage, become soft, become stimulated and then get semi-hard again, over and over. The buildup of sexual tension and frustration was like a growing ache that was consuming more and more of my attention.

I arrived at work, passing her secretary’s desk outside her office. Her secretary, a beautiful girl about 21 years old, greeted me with a knowing smile. I was so embarrassed my face turned bright red, which made her smile more. She asked me to give Mistress a client’s portfolio, and after handing it to me, patted me on the bottom as I walked by and commented “I loved the video.” My face turned bright red with embarrassment as I walked into Mistress’ office, and I was horrified that she followed me into the office and closed the door behind the three of us.

Mistress greeted me with a smile and said she needed to inspect me to make sure I followed her instructions. She had me remove my suit, revealing my stockings and garter, and asked me to bend over. She ordered her assistant to remove the belt holding in my heavy steel anal plug, and to move the thick base back and forth, in and out, painfully stimulating my prostate as I became hard, yelping in pain from the cock cage. “Well, let’s remove that cage and finish your grooming. Follow me.” I got down on hands and knees and followed her and her assistant into the inner chamber. Her assistant seemed to be preparing something over on another table as Mistress strapped me to the steel table, immobilizing my arms, legs, and torso. My legs were up in the air in high stirrups, spread painfully wide, my ass at the edge of the table, fully exposed and stretched.

Then she removed the cock cage. I instantly got hard from her touch, feeling out of control and embarrassed. “OK, time to finish removing all your hair. Now her assistant brought something I could not quite see over to Mistress. Mistress walked over to me, applying cloth strips with hot wax to my penis and balls, and an area by my anus where I missed shaving. She put a thick rubber gag in my mouth with a short fat penis on it, stretching my jaw and silencing me. The penis was hitting the entrance to my throat and I was trying desperately not to gag. “Don’t want you to get noisy, now.” Then she ripped the wax strips off my genitals and anus. I screamed into the gag, but only a muffled sound was heard. “There, much better. We will have to get you laser treatments to permanently remove your pubic hair and the hair on your arms and legs. All in good time. While we have you up on the table, we might as well clean out your insides as well.” Mistress’ assistant Elaine had been out of my sight for a couple of minutes, but now returned with a large water filled enema bag, which Mistress hung from the high stirrup my leg was tied into. My eyes followed the long tube hanging from the bottom of the bag to the end in Mistress’s hands. She was fastening a huge fat nozzle to the end of the tube. With a cruel smile, she came up to my face, removing the gag, and said “ You are going to want to get this nice and wet, so it won’t hurt so much when I shove it in your ass. Open up.” She grabbed my jaw, pulling hard, my mouth opening as she shoved the round, bulbous rubber nozzle into my mouth. Working it into my mouth, she said “Work it with your tongue..get it wet.” My jaw was painfully stretched as she shoved it back and forth, making me gag as it hit my tonsils. Popping it out of my mouth, I gasped for air, and she moved down to the other end of the table.

Without ceremony she pushed the nozzle into my anus, the fat head stretching me painfully as it passed into me. I couldn’t help but cry out from the pain. Once in, my anus closed on the narrow end. “Bear down on the nozzle while I fill you. If you leak one drop, you will regret it.” I followed her orders as the warm soapy water filled my bowels. I felt my colon fill and stretch, and looking down saw my abdomen bulging. Suddenly, the intense inner pressure on the walls of my colon triggered painful spasms, as my body instinctively tried to expel the intrusion. Mistress pushed gently down on my bloating abdomen, rubbing it sensuously as I groaned in pain. She was clearly becoming aroused by my discomfort, the sweet, musky smell of her wet and creamy vagina beginning to fill the air. She said “OK I am going to remove the nozzle. Make sure you bear down as it comes out. Remember, if you leak a drop you will regret it.” She slowly pulled the huge nozzle head out, and I did my best through the painful cramping to hold it all in, but a few drops escaped. Mistress said “Not only does your cock need lessons in control, so does your anus. We can provide that.” Her assistant Elaine, now naked, placed a large basin on a shelf under my ass and instructed me to open my anus to release the soapy water. I did, feeling horribly humiliated to have two beautiful women witness my bowels emptying, and simultaneously feeling turned on by the naked presence of two breathtaking women.

The Anal Control Lesson

Mistress slathered my shaved genitals and ass with conductive jelly, and placed tight electrode collars around my balls, the base of my penis, and just under the head. Next she held out a thick, long, metal electrode and said “Guess where this is going…we are going to plug up that penis of yours and place this electrode down into your urethra until it is aligned with your prostate.” She shoved two fingers up my ass and began palpating my prostate. I cried out as her highly sexually skilled assistant started rubbing and stroking my penis, springing it erect in moments. Next, Elaine firmly grabbed the head while Mistress pressed the steel rod very deep into my penis while continuing to palpate my prostate. When her prostate ministrations vibrated the electrode, she knew it was in the correct place. The thickness of the steel probe held it precisely in place, stretching my urethra painfully. I lay there gasping and moaning and sweating from it all…but my dilemma was just beginning. Elaine had refilled the enema bag with clean clear water, but this time the water was not comfortably warm, but ice cold. As she was filling my bowels, Mistress said “Now you will learn to control that anus. If you leak any water, it will activate an electrical switch I am attaching to your anus and the electrodes. The switch will send a painful current into your balls, penis, urethra, and right down to your prostate where I placed the tip of the electrode. The current will stop when you get control and tighten up that ass, and prevent any water from leaking. This will be fun to watch.” She continued to fill my bowels with the ice water as I watched my abdomen swell from the infusion.

The cold water caused terrible cramping in my bowels. Wave after wave of spasms racked my body. I was moaning loudly as the involuntary contractions tried to force the water out of me, my body understanding something was terribly wrong and attempting to correct the situation. I was writhing in my bonds on the table, when an extremely violent cramp forced a stream of water to surge out of my ass. The pain of the violent cramp was immediately replaced by pulses of lightning like pain ripping into my balls, penis and urethra. I started screaming, when Mistress came and kissed me, ordering me to open my mouth and put my tongue inside her mouth and kiss her back. “I love the taste of your pain” she said in a husky voice, as our tongues swirled around, my body jerking with the electrical surges and alternating with jerks from the water induced spasms. I screamed into her mouth. Mistress kissed me deeply and slowly, my head completely immobilized by a tight strap attached to the table while my body jerked and spasmed in its bonds. Mistress was extremely turned on by my pain, and began moaning into my mouth, sensually rubbing the sides of my face, then pinching my nipples. She ordered me to stop screaming, relax my face and kiss her slowly, to accept the pain and submit to her. She rubbed my bloated, pain-racked belly slowly and sensuously with her hand, her beautiful breasts rubbing against my chest. While she leaned on me, kissing me lasciviously, licking the pain-born sweat from my face, her assistant kneeled down on the floor, inserted her head quickly between her wide spread legs, and furiously licked and sucked her pussy, while putting her fingers gently into her ass, slowly moving them in and out. Mistress grunted loudly, and I could feel her whole body start jerking, her legs shaking, until she moaned her very prolonged and intense orgasm deeply into my mouth. Mistress breathed into me, her body collapsing on top of mine, her relaxation deepening with greater pleasure as she felt the pain-induced involuntary twitching and writhing of my body under hers, her beautiful eyes rolling in ecstasy as the delicious moaning sounds and intensely arousing scent of her orgasm filled the room.

Still strapped to the table, Elaine quickly coated Mistress’ entire body with slippery oil. Then Mistress climbed on top of me, pressing her slippery cunt and rump back and forth from my cock over my stretched abdomen, licking my pain and fear induced sweat, and pressing her mouth against mine while moaning. Her movements greatly increased the pressure on my abdomen to release more water. Back and forth she slid, her cunt sopping wet, which forced more water out of my anus in spite of my extreme but fruitless efforts to keep it in. I felt terrible cramps followed by jolting electricity that painfully spasmed my anus, balls, penis and prostate, as water uncontrollably squirted from my bowels. I was sweating profusely, my mind completely filled with the sensuous movements of Mistress on top of me, and my pain. I begged her to stop. As another shock rocked me, I finally submitted completely, exhausted, unclenching my buttocks and relaxing my anus, allowing all of the water left in my colon to flow out of me. The intense pulsating shocks that immediately ensued made my penis, balls, and prostate contract wildly, over and over, the organs dancing and seizing painfully from the repeated surges in electrical current. Mistress slid off of me, while keeping her tongue lazily still in my mouth, while the electrode down my penis was suddenly and painfully yanked out by her assistant. This was instantly followed by a huge load of cum shooting violently out of the end of my pulsing cock, spilling over my distended slippery stomach, shooting over my face and into my mouth and Mistress’s mouth. Although my typical ejaculation usually lasts only a few seconds, the contractions in my prostate continued for over a minute, driven by the electrical surges. My cock was dancing uncontrollably, spasming wildly with it all, the intense orgasm continuing even though my prostate was completely empty. I was moaning painfully into her mouth, as Mistress continued to kiss me, licking my cum and dripping it back into my mouth slowly and sensuously, making soft pleasant cooing sounds all the while, gently stroking and cradling my head in both of her hands.

I slowly began to awaken, realizing I must have passed out. I was still on the table, but my bowels were empty, the electrodes and bonds were gone, and I must have been washed down and dried. I was completely exhausted from my ordeal. Mistress was dressed in her business suit, gently stroking my head, smiling down at me. “Ok, that’s enough fun for today. Time to get back to work. Follow me.” I got down off the table to follow Mistress back into the office, and asked her “Mistress, where are my clothes?” “You’ll get them at the end of the day, if you please me. You will make phone calls for me and do all your office work naked today. I am not expecting any clients to come in today.” We walked back into her office, only to see Elaine waiting with some work folders, also dressed in a suit. Embarrassed by my nakedness in the presence of two dressed women, I blushed and covered my genitals with my hands. Elaine smiled at my discomfiture, Mistress corrected me sharply for covering myself, when the secretary said “Mistress, I am pleased you have a new slave.” “I give you permission to inspect him,” said Mistress. “You will obey Elaine as if she were me, she added as she looked at me.” “Come slave, and present your balls and that lovely little cock for inspection” Elaine said holding out her hand. I froze, and Mistress gave me a stern look, which made me hurry across the floor and thrust my pelvis forward, placing my sore dick and balls in her beautiful delicate hand. I looked down and turned red all over. “Look me in the eyes slave” I immediately did, as she squeezed and massaged my balls and cock gently. She released my cock and balls and said “Turn around and bend over Mistress’s desk, pulling your ass cheeks apart for inspection.” I did, and she promptly stuck a dry finger up my tortured anus. I grunted in discomfort as she probed, then pulled out. “Thank you for letting me inspect your new slave, Mistress. I hope he pleases you and trains well.” Then she took her work and left the office, leaving me bent over the desk.

At the end of the day, Mistress presented me with her chastity device, locking it in place, and allowed me to dress and go home. This time, a larger steel plug was inserted in my ass for the ride. Sitting on the train, the same pattern occurred: the vibrations of the train to the base of the plug sticking out of my ass stimulated my sore anus and aching prostate gland, causing a partial erection, which deflated with the sharp pains of the cock cage. Over and over again, trapped in a haze of stimulation, I walked off the train to my apartment in a fog.


Next Chapters: Mistress decides to transform me.

As the weeks wore on, Mistress enjoyed her training of me, as I grew to respond more quickly and with greater control over my erections, ejaculations, and anus. Mistress told me one day when I came in “It’s time to begin your transformation.” I asked her about this with mounting fear, but she only laughed and led me into the inner chamber where I was strapped tightly to the steel table. Mistress left briefly, then came back with a series of syringes with needles on the end. She said “You exist to make money for me. I am going to transform your body with growth and sex hormones. Your penis is too small….I will inject it with growth hormones over the next few months to greatly enlarge it. Your ejaculations are too little. I plan on collecting and selling your sperm to sperm banks, but we need to enlarge your balls and prostate quite a bit so you have much larger than normal cum shots I can collect to sell. I will inject your prostate with growth hormones via a catheter inserted into your penis. I will also enlarge that cute little penis of yours by injecting it with growth hormones. Also, I plan on transforming you into a she male, as she male BDSM porn sells for a higher price than regular porn. So I will be injecting your breasts with growth hormones, estrogen, and you will take estrogen pills daily to make your whole body more soft, round, and feminine, and allow those breasts to grow. Once they grow sufficiently, I will give you prolactin and other hormones so they start producing milk. There is a growing market for fresh human breast milk, and this is another avenue to generate revenue from your body.”

Helpless and terrified, I lied there immobilized making grunting noises as Mistress gave multiple micro-injections of hormones into my breasts and nipples. As she was injecting my nipples, she commented that she would enlarge them and make them more sensitive for her pleasure. Elaine came in and started massaging my breasts to work the liquid through the tissues. Mistress then injected my penis and balls with growth hormone, my grunts turned to screams with the pain of the injections in my testicles. Once again, following the injections, Elaine massaged my penis and each testicle firmly to spread the hormone throughout. I had broken into a cold sweat from fear and pain, my entire body extremely tense. Elaine’s soothing touch was such a pleasant relief from the pain, which quickly went away. Elaine kept saying in a soft voice “There, there slave. It’s OK. You’ll be OK,” which took some of the fear away. In spite of the discomfort, her gentle ministrations soon had my penis erect. Finally, Mistress spread some type of jelly between my balls and anus, then placed a cold probe there. “In order to make sure I am accurately injecting your prostate I am using an ultrasound device that will enable me to place the steel catheter with the needle in the correct location. She inserted the well lubricated catheter into my very hard and erect penis, as I grunted in discomfort from the violation, the **** of my penis. In just a moment she had it located correctly, pressed a button, and a brief but sharp sudden sting in my prostate made me lose my breath. She gave me several more injections, explaining “We have to make sure we inject the prostate lobes evenly.”

After my ordeal, Mistress said “You were a good slave, and deserve a reward.” She gently took my now limp cock and kissed the sensitive underside of head gently. She began to alternatively lick and suckle my dick, causing an immediate erection, in spite of how sore I was. She ordered Elaine to come over and deep throat me, which she immediately did, and she started sucking vigorously. Elaine was extremely skilled at oral sex, vibrating her throat and tongue vigorously while my cock was fully embedded, her nose pressed against my body. She slowly withdrew her mouth, slurping on the head and swirling her tongue around in a way that felt so good it was too intense. I asked for permission to come, but Mistress said no. Elaine brought me to the edge of coming over and over. I begged Mistress each time for permission and she just reminded me to control that cock or there would be a big price to pay. I warned Elaine when I thought I couldn’t help but cum, and she stopped her ministrations at least 10 times, slapping my penis and balls hard to prevent my orgasm. Finally, I was so close that when she started slapping my penis and balls again, I had a tremendous orgasm in spite of the pain. Mistress laughed wickedly, scooping up my semen and shoving it in my mouth, saying “I can see you need more training in managing that penis. I am sure I will think of something,” she said as I gagged on her cum soaked fingers she was shoving down my throat.

Next Chapter: My training and transformation continues.