I’m a 50 year old single white male earning somewhere in the neighborhood of $200,000.00 per year from a few good investments I made years ago. I live alone in a very comfortable 4 bedroom rustic log cabin that is situated high on a bluff overlooking one of the most beautiful rivers in this part of the country. I own several classic cars, a stable full of racehorses and a Cadillac Escalade that I drive on a daily basis. I also have a secret that until recently I had taken great pains to conceal from the rest of the world. That secret I have decided to reveal in this manner. I, a successful businessman and a leading citizen (even if I do say so myself), have been addicted to masturbation for the past 30 years. Not only masturbation, but masturbation while wearing women’s lingerie, stockings and shoes and exhibiting myself publicly, yet discreetly, as I play nasty games with my turned on body. A fact that I don’t anticipate changing anytime soon. Especially now that I have finally found the woman of my dreams. The woman who has given me the courage to come out of the shadows and openly, if not proudly, admit to the world that I am nothing more than her personal Sissy Jerk-Off Boy and my sole purpose is to masturbate for her whenever and however she wishes while dressed, or undressed, in whatever she directs. Be it lingerie or leather. For she is my Queen, my Goddess, my Mistress. She is my Masturbatrix.
It’s still sometimes difficult for me to believe that only two short weeks ago I was still living that bleak existence that I’d lived for such a long, long time. Going about my day wearing my $800.00 suits with my nose in the air and with that ridiculous snobbish attitude I was perhaps the world’s biggest hypocrite. After my day of acting as if I was somehow better than everyone else I’d, at last, head to my favorite eatery to pick up something for my supper. Then with bundles getting cold in the passenger’s seat I’d start for home.
Typically I’d only make it about six blocks to the mostly deserted parking lot of an old bankrupt grocery. I’d discovered an excellent parking spot there toward the back of the old building where neither me nor my vehicle could be seen. Here I would shed the stresses of the day as I shed my stiff business suit and put on the silky feminine attire I’d had hidden in my auto’s storage compartment all day. It’s hard to describe the combined feelings of relief, exuberance and arousal that washed over me the instant I’d slide my feet into the leg holes of my pretty panties and slowly pull them up my shaved legs. Or, while I meticulously rolled a pair of expensive nylon stockings on and connected them to my sexy garter straps. I loved it. I truly loved everything about it. The smooth, slick feeling of the material hugging my body. The excitement of changing out of my street clothes here in this open, somewhat hidden, but still public place. Driving home in only my lingerie, nearly naked, and above all, playing with my beautiful hard cock that would threaten to rip through the crotch panel of my tiny panties as I’d slip my feet into the beautiful and sexy feminine footwear I’d chosen for the day, and lay my man clothes on the back seat.
On the day that changed my life I was clad in a pink satin corset with white trim at the boning, white lace garter belt, pink bikini panties, white stockings and black high heeled sandals. No bra as I was afraid if I wore a bra it could be too easily seen by the occupants of the other vehicles. Besides, my nipples are extremely sensitive and I love teasing and toying with them. They tingle so much when I’m aroused that they’re nothing more than hard little pebbles begging for my touch. Just rubbing them lightly with my open palms never fails to cause a steady flow of pre-cum to begin spilling from my cock and almost always is the catalyst for another one of my multiple masturbations during the course of any given day, afternoon, evening or night. As a matter of fact, it was just that very thing that caused me to first meet and experience my now Masturbatrix.
I had just finished changing at my parking lot spot and was leaving, backing my Escalade out of my perceived seclusion when in my rearview I saw her standing directly behind me, blocking my only way out. She was dressed in boots, black fish net stockings, short blue jean cut offs and a tight halter, on the front of which was emblazoned “BITCH” in bold pink letters. Her face and figure appeared to be quite stunning from what I could see in the mirror. On the ground beside her sat a black overnight type bag and in her hand was an envelope of some sort that she kept slapping against her thigh as she stood staring back at me in my mirror. She was obviously waiting for me to stop my vehicle. I supposed so she could approach my driver’s side window because when I did, she did. My excitement at being actually seen dressed as I was by this beautiful, strange, woman made my cock swell to extreme proportions. In spite of my combined feeling of fear at her reaction and the excitement of being seen, I was also decidedly turned on and couldn’t resist my urge to lightly brush my rock hard nipples with my palms before she arrived at my window. The feeling was like no other before it in intensity and stimulation and I was suddenly and unexpectedly cumming. Hot white ropes of sticky sperm erupted from my hard cock and soaked the crotch of my panties. An ever increasingly large circle spread from the top of the tent my jerking erection was causing , soaking the tiny garment more and more completely with each passing second. My throbbing erection was also causing the panties’ delicate waistband to be pulled away from my body which left a clear and unobstructed view of my cleanly shaven abdomen and the root of my thick, wet cock.
Glancing in my rearview mirror it was obvious there was no time to clean up or even hide my mess. I was blushing bright red, out of breath, mortified and strangely satisfied when she arrived at my driver’s window and stepped up close. I was too embarrassed to look at her as I imagined all that she must be seeing right then. Her loud knock on the window glass caused me to turn my eyes her way however, and when I did I saw that she wasn’t looking at me either. Well, I mean she was looking at me, but just not at my face. Her intent stare was firmly locked on my crotch and everything there was to see down there. My nylon encased legs, my tiny pink panties with their load of fresh cum, my still jerking hard-on and my meticulously clean shaven body. As if in some sort of hypnotic trance she motioned for me to roll down my window with her thumb, never glancing away from her focal point on my crotch for a second.
I hesitatingly complied to some extent and lowered the glass between us about 6 inches. “Do you like it?” I boldly asked. Her eyes remained on my hard on as she answered that she’d seen it all before. “I just never knew you were so big,” she added, finally raising her eyes to meet mine. “You’re a kinky little rich boy aren’t you Darlin’.” she said smiling as she passed the envelope she was carrying in to me through my lowered window.
Cautiously I took it from her and opened it. Inside I found an extensive photo documentation of none other than me in various stages of dress and undress as I was changing from my business suits into my lingerie here in my “secret and secluded” spot. There were photos from as far back as six months and spanning what appeared to be each and every visit I’d made here—which were numerous. So that’s what she’s up to, I thought. Blackmail! “I think maybe you’d better get in,” I said calmly. “Yes, so do I,” she smiled and promptly circled my vehicle to climb into my passenger’s seat. I barely had time to transfer my supper bags into the back floorboard before she was sitting there staring at me.
We both just sat for a very long moment eyeing each other. She obviously taking in my naked body clad in the feminine attire, and me attempting to overcome my shock and embarrassment at her substantial beauty, which I slowly admired from head to toe and back. “So,” she said looking me in the eyes. “You like the pictures?” Picking up the stack from my console between us I slowly looked through them again before putting them back in the envelope and tossing them in her lap. “How much?” I asked, contempt dripping from my voice. Or, at least as much contempt as I could manage considering my situation.
“How much what?” she asked, her eyes open wide in mock surprise. “Money!” I loudly responded. “How much money do you want to make you and your pictures go away forever?” Removing the pictures from the envelope she began slowly looking at them one at a time, a broad smile on her face that she renewed with each consecutive print. “Money?” she finally asked. “I don’t want money. And, I’m insulted that you’d think a monetary value could be put on all of my hard work.” she concluded, laying the pictures in her lap and raising her eyes to mine. “No,” she continued “I’ve got something else in mind entirely.” Then added, “My, but you do love to play dress up. Don’t you?” She didn’t wait for my answer. “Well, of course you do,” she quickly went on….. “Just look at how wet and sticky your little panties are. You really should be punished for that you know?” Then again looked into my eyes and smiled. “And I plan to be the one who administers that punishment,” she trailed off into a near whisper and I had to struggle to hear what she’d said. ‘What audacity’, I thought.
“First of all,” I began, “my personal behavior is really none of your business. And secondly, Just what will it take to get rid of you!” I covered my now shrinking cock with both hands and gave her a hard stare directly into her big brown eyes.
“Well,” she started calmly, “It’s like this,……. You can’t! You see I lost my job about six months ago and since then I’ve been struggling to keep up with my rent and bills. To say nothing of my social life falling into total ruin,……….Then one day when I was almost at my wits end I happened to look out of my bedroom window and what did I see but you, one of the upper crust of our little society, hiding behind this old building acting real suspicious. Needless to say, you captured my attention. So I started to seriously watch you then. I saw you look around to see if anyone could see you. You didn’t see me, but I saw you when you started to take off all of your clothes. Now, a fire couldn’t of kept me from watching, and I even decided to go one better as I hurried and got my camera from my dresser drawer getting back to my window just in time to see you putting on women’s lingerie. That’s when I started taking pictures. I didn’t know what I would do with them yet, but I figured something would come to me sooner or later. And, as you’ll soon find out, it did. Also, I discovered I got very turned on whenever I watched your little show and so I started watching for you to come back. When you did, I took more pictures. Only now I was taking my clothes off when you showed up as well, and taking my pictures with one hand while I played with myself with the other. Your little performances really made me hot and I could hardly wait each time to get the film developed and the pictures back so I could masturbate looking at them and fantasize about having a rich boy like you as my personal, sissy slave. That’s when I said to myself…”Why Not?” and worked out this idea that would solve all of my problems. You wanna hear what it is?” she asked looking at me with that same smile.
I was more than a little afraid to hear what her devious mind had conjured up, but I had no choice. “Yes, of course I do,” I said with as much bravado as I had in me at that moment. “Tell me……What’s your great big idea?”
“OH! It’s no longer an idea, you understand.” she told me in earnest. “Now it’s a plan.” She sat for a moment to let her statement soak in then continued. “Now here’s what’s going to happen. You’re going to take me home to live with you in your house. Expense free.” I started to protest but she stopped me saying; “Before you tell me some lie like you’re married or something else as ridiculous you should know that I’ve done my homework on you and probably know more about you than your mother does, ……….so you just sit there quietly and listen. Okay?” She sounded so authoritative and stern that I was mesmerized, and meekly shrank back into my seat and did as I was told.
“As I was saying,” she continued. “I’m coming to live with you at your house at no cost to me. You will see to all my needs such as food and clothing and you will provide me with any money I ask for. As for you, You’ll be expected to dress and behave as I instruct, to be at my disposal whenever I call, (Night or day, morning, noon, evening or midnight) and to serve me in all ways. In other words, you are to become my personal slave in every possible way. Any indiscretion will be cause to suffer my punishment. And, to avoid the personal embarrassment you’d have to endure if these pictures ever got out, you WILL comply with everything. You are to start immediately. Do you understand?” When I started to speak and respond she quickly leaned across my console and delivered a stinging slap across my face. “Did I give you permission to speak?” she questioned sternly. When I again started to respond she slapped me again…………harder. I meekly lowered my eyes and, rubbing my stinging cheek, slowly shook my head to indicate that NO, I hadn’t received her permission to speak.
“That’s more like it,” she said, gloating. Then continuing she said; “You will always refer to me as Mistress or Madam…….That is, of course, when I allow you to speak. Otherwise you will only listen and obey. Just like you’re doing now. Do you understand, slave?” she asked with a smirk. This time however I immediately nodded, but barely heard the question as my mind was going at least a hundred miles an hour considering the possibilities her proposal would offer me. I’d often thought and fantasized about what it would be like to serve a dominant woman as her sissy slave. Being ordered to perform every nasty notion that she conceived, being forced to dress in lingerie when in her presence. Perhaps being commanded to perform kinky masturbation demonstrations for her pleasure while using my tongue to bring her to orgasm after orgasm. I needed to talk to her about it, to reach a mutual understanding with her, to impress upon her the importance of allowing me to fulfill my secret kinks and needs and implement them into my service of her. I just knew that if I could express my side we could come to a mutually satisfying solution in which both of us could have our needs well met. I just needed the opportunity to speak to her. That’s all.
I knew that she had continued to talk to me about how she felt I should behave, but I really had no idea what she had said, exactly. I wasn’t particularly concerned about it either, since I knew without doubt that if I wanted it I could easily have her disposed of without anybody being the wiser. For the moment however I decided to let her believe she was getting her way and she had me over a barrel. Perhaps she might prove to be an entertaining distraction for awhile, I thought. It was surely worth a try anyway. It was this logic that made me decide not to make any demands on her as to what it would take to satisfy me and therefore make me happy to continue in her perceived BDSM relationship. Let’s just see what she comes up with on her own, I thought. No need to give her any ideas. Maybe she’ll even make me happy on her own.
“So are you ready to obey me now?” I heard her ask me when I again tuned into her words. I nodded. “Wonderful,” she exclaimed. “Show me your cock, slave,” was her first commanded. Immediately I stretched the waistband of my panties down under my balls and quickly brought my hands back up out of the way in order to present her with an unobstructed and clear view of my, once again, hardening cock. Just as she had requested.
“Make it hard,” was her next order, and I instantly began to jerk myself like I’d done so many times before, soon coaxing my cock to another full erection for her. “Nice,” she complimented me. “Now take those panties off,” she told me next. “I want to watch you play with your asshole too………….With this!” she added, and pulled a large cock shaped vibrator from the bag she’d brought. As I followed her order and pulled the tight, cum soaked panties down my hairless legs and over my feet I watched her suck the entire vibe into her mouth and down her throat, leaving a thick coating of saliva on it before handing it to me. Although I did enjoy playing with my ass occasionally and had used butt plugs in the past, I’d never tried anything as big or as long as the vibrating dildo she was now holding. The uncertainty I felt must’ve shown on my face because, ( I didn’t even know her name), took one look at me and said; “Oh don’t worry about it. It’ll fit alright. Just relax and let your asshole stretch around it………..Of course,” she continued, “if you don’t think you can get it in,…….I can do it for you.” That was all the encouragement I needed and set my mind and asshole to doing it or bust, (not literally I hoped).
Taking the oversized rubber cock from her I slid my ass to the very edge of my seat to allow me to get to my asshole unobstructed and holding the vibe in my right hand pushed it’s head between my cheeks. I spread my legs as far apart as I could as I massaged the rim of my asshole with the soft tip of the dildo and lined it up for the grand entry. Gritting my teeth and holding my breath I then began slowly pushing inward with both hands holding the vibe by it’s base, and to my relief felt the head open my rear hole and pop past my sphincter and into my ass canal. It hurt a little, but nothing I couldn’t stand, so I consciously told myself to keep my asshole relaxed and resumed pushing with my hands, causing the dildo to slip deeper and deeper, an inch at a time. Finally, after allot of concentration on my part to keep my asshole relaxed in spite of it being stretched beyond all previous limits, I felt my hands come in contact with my spread asscheeks and my fingers holding the dildo felt the stretched rim of my invaded hole.
Taking a few deep breaths and again concentrating on keeping my ass relaxed, I began a slow but steady in and out motion, fucking myself in the deepest realms of my anal canal and allowing myself to get accustomed to the sensations. “He-He-He!” My future Masturbatrix squealed and clapped her hands together. “I knew you could do it. See? I told you……..Now turn towards me so I can watch you fuck yourself with it!”
Struggling to hold the thing in my ass, I twisted my body around to face her. Placing my right foot on top of her seat and pressing my toes against her headrest, I leaned back against my door and rocked my hips upward until she had a clear and unobstructed view straight at my asshole and the monster dildo that was fucking it. By this time I’d gotten rather used to the stretched state of my butt, either that or I’d become numb back there as it was somewhat easier to saw the vibe’s girth in and out. With less resistance I could maneuver the thing with one hand, so taking a firm grip of it’s base with my left hand, I let go with my right so I could return to stroking my amazingly hard and incredibly needful cock. My one girl audience seemed pleased with my move and stopped massaging the wet spot between the legs of her shorts to very quickly unfasten the buttons holding them closed and shove them down her shapely, tanned thighs and past her knees. Moaning encouragement to me she began a vicious assault on her neatly trimmed and newly exposed pink pussy with both of her slender hands.
Watching her as she publicly played with her wet cunt combined with the incredible sensations I was experiencing through the simultaneous stimulation of both my ass and my cock was seriously speeding me toward a very powerful orgasm and one I knew I couldn’t keep from happening – even if I wanted to. I did, however, want to hold out at least until my masturbation mate had achieved her own orgasm, perhaps even cumming together in a mutual explosion of ecstasy. That wasn’t going to be an easy task though. Not unless I either backed off of my own play or found a way to speed her up—So….I decided to try to do both.
Taking notice of how totally she was being consumed by her lust I decided to take my chances and try to get away with some hot, verbal encouragement of her, in an attempt to build her excitement to the boiling point, hopefully propelling her past her orgasm’s point of no return. As for myself I had eased back on my cock stroking considerably and was now doing more imitation stroking to keep up appearances than the real thing. By gripping my cock at it’s base with my pinkie finger and the heel of my hand I’d managed to turn my own orgasm fires down for the moment, which gave me be just enough time to turn her up………..I hoped!
Beginning with a lustful groan and a softly moaned compliment to my lovely companion acknowledging her ingenious plan to survive on my money and telling her how incredibly stretched and stuffed my ass felt I rolled my hips a little higher so I’d capture her attention for the upcoming visual portion of my quest. I had pulled the thing about 3 quarters of the way out of me when I saw her eyes lock on the action. I didn’t waste a split second before adding my narrative to it.
“My Mistress loves to see how her huge cock stretches her bitch’s man cunt. Doesn’t she?” I moaned through gritted teeth. “OOooooooo!” was her only response, but it was enough to encourage me into continuing. “Oh God!” I cried as I started shoving it back in. “It’s so fucking big and thick.” I was giving an Oscar winning performance as I tightened the muscles in my arm and gave her the impression that it was taking everything I had just to be able to force the monster sized rubber cock back into my asshole when in reality it was taking all I had just to be able to keep my asshole from sucking it back in of it’s own accord.
Suddenly, with about two thirds of her dildo wedged up my ass it stopped with a jerk, my rectal muscles refusing to let it proceed any further in any direction. “Umphhhhhhhhh!” I groaned as I used all the force of my left arm to push it in another inch. Letting go of my, once again, very excited cock I leaned forward so I was able to reach between my legs with both hands. Gripping the dildo’s base with my fingers interlaced I groaned, “Nooooooooo!………….I wanted to take it all for my Mistress! Umphhhhhhhhh,” I grunted again as I managed to push a little more rubber into my ass. Her eyes were nearly glazed over as she stared hypnotized at me feeding inch after agonizing inch of the ball bat sized phallus into my aching anal canal. I took immediate advantage of it.
“Oh yes! Look at it Mistress,” I groaned “Look how your slave bitch hurts her ass for you………….Watch me push it all the way in for you my Beautiful Mistress!…………..Watch how far it stretches my poor asshole, Mistress!” I groaned a little louder, but this time it was for a different reason. In my determination to achieve success with implanting the dildo in my ass I kept leaning my upper body closer and closer to my crotch for more and more leverage. However, on my last lean my very excited, turgid cock had come in contact with the slick satin of my corset causing my cock to jerk and jump for joy and me to raise the volume of my voice suddenly. A few quick practice humps with my hips and I knew I was onto something.
My actions became almost animated as I began furiously humping my hips up and down while pulling myself up with my hands on the dildo and thusly putting greater and greater pressure against my cock as it frantically fucked up against the folds in my satin corset and simultaneously pushing the dildo steadily inward toward total insertion.
Mistress’s orgasm was progressing right on schedule as was evidenced by what began as a low moan deep in her toes and was now to a much louder level straight from her pussy and also by the way she was now assaulting her clit with such force I was afraid she might tear it off. With her other hand she was literally pounding four fingers into her gaping cunt hole and doing it so forcefully each down stroke that she made caused a loud slapping sound when the heel of her hand made contact with her saturated cunt lips.
As her moans continued to crescendo and her smell of arousal permeated the air in my Escalade with it’s heady thickness, I felt as if I was about to lose my mind to the extremities of my arousal. I could feel my own saliva slowly cascading down my chest as it flowed from my drooling mouth. I was hunching my cock against my corset now in short, rapid jerks as I hung sexually suspended on the verge of a climax that was already taking my breath away. All I needed was one final push. To catch my cock on the right fold. To tweak my stone hard nipples with the right twist or pinch or pull. I was desperate for any one of the vast array of stimulation it would take to send me over the edge of ecstasy, when Mistress suddenly provided it for me.
“OH GOD!…….OH GOD!…….OH GODAMN!” she shouted at the top of her lungs when the first waves of her own orgasm washed over her. As she began to convulse wildly in my passenger’s seat I gave a Herculean effort to pull myself up one last time and when I did the added pressure exerted by my hands on the base of the dildo caused it to slip and it’s final few inches buried firmly and flush into my stretched asshole. That was the final straw, and I was suddenly cumming. Long ropes of my white, hot semen flew randomly through the cab of my Caddy sticking to everything it came in contact with, yet still it showed no signs of slowing. I came for what I’m positive was at least a full minute, my cock pumping out gob upon heavy gob of thick white cum that both soaked and exhausted me.
Sweat rolled down my flushed face in rivers as every muscle in my spent body quivered and spasm. My cock still swelled and jerked as if still ejaculating cum, although my balls had given up the last of their supply and now hung loosely atop the dildo that was still in my ass. Through foggy eyes I at last focused on my new Mistress, still gasping for breath in the passenger’s seat. “Thank you, Mistress,” I said in between breaths. “That was the most incredibly amazing orgasm I’ve ever experienced. She smiled and wagged the index finger of her right hand at me until she could speak.
“I thought I told you not to speak,” she admonished, a good natured tone in her voice. “Now pull that cock out of your ass and get busy cleaning up this mess …………with your tongue,” she commanded. “Me first!” she said while lifting my console up into it’s place in my seatback and indicating by a sweep of her hand exactly where she wanted me.
Moving as quickly as I could I eased the monstrous cock from my sore asshole with a final pop and turned to lay my head in her lap and began tonguing up her abundant overflow of love juices smeared over her thighs before concentrating my attentions on thoroughly cleaning her succulent cunt. When I had licked her to a renewed state of arousal she took a handful of my hair and pulled my face from between her legs.
“That’ll do for now, slave,” she said in earnest. “Now lick up your mess and drive us home…………quickly,” she added scooping up a finger full of my cum from the seat and feeding it to me. This time I happily did exactly as I was told.
Since then She has completely redone my wardrobe with a vast array of beautiful lingerie that I am required to wear at all times. When in the house it is the only thing I wear and when outside at my business I wear it under my suits. I’m also required to always wear one of the many cock and ball harnesses She has given me, no matter when or where I am or what I am doing. She has proved incredibly ingenious at inventing new and different ways for me to masturbate for her as well as unique and exciting ways to feed my need for exhibitionism. We often host parties for other couples of like minded persuasion where us jerky boys take turns either serving the Mistresses or we are stationed at various locations around the house to stand and masturbate for everyone’s entertainment. Of course we are also required to be of sexual service to whoever has received permission from our individual Mistresses for us to do so.
All in all, I am the happiest I have ever been and with any luck Mistress Natalie (I found out what her name is) will remain with me forever.
…………..Oh yes! As for those pictures. They are now each beautifully custom framed and hang proudly on the walls of our plushy furnished play room for all to see. And, I am extremely proud of each and every one of them. “Thank you Mistress Natalie! From the bottom of my wonderfully sore cock! You are truly my all time best fantasy come to life.”
– The End –