Crossdresser's Surprise free porn video

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A Crossdresser' s Surprise - by: by Deborah Pinto I guess I should have seen it coming. My wife, Virginia, and I were drifting apart sexually, and I should have suspected that she was having an affair. Afterall, we had not made love in over a year except for one night she had come home a little drunk from her office Christmas party and had virtually raped me in the middle of the night. I remember her laughing and saying, "Tim, what's wrong with you tonight? You feel so tiny inside of me!" This comment had been troubling for two reasons: she had never before complained about my size and, more importantly, my name is "Don" not "Tim"! Nevertheless, I just assumed she was drunk and didn't know what she was saying. Still, I had hoped when I awoke the next morning that our love life was about to be rehabilitated, but in the morning light, fully sober, Virginia had no interest in rekindling our conjugal bond. I still assumed that she was just losing interest in sex. That does happen with women all the time. Not that the blame was fully hers. I had always had a kinky side to my sexual desires, and I think that may have been a turn-off for her. I had always loved the sight of women dressed in leather, particularly tall black boots. I guess I was erotically aroused by the aura of dominance such a woman projected, and wanted my wife to dress in that role. One of the things that had first attracted me to Virginia, besides her beauty, was her stature. At 5' 9" she was two inches taller than me and although she was 15 to 20 lbs lighter than my 155 lbs., she worked out regularly with weights and, with her long blonde hair and blue eyes looked like some sort of Valkyrie. Clearly, she would have had no problem physically dominating the likes of me. Nevertheless, although I approached with my sexual fantasies a couple of times, Virginia seemed to have no interest in such aberrant behavior. As a result, I found myself withdrawing into my private fantasies of submission; of being sexually overpowered by dominant women; of being "forced" to wear feminine clothes and adopt feminine occupations like a secretary, maid or (worst of all) streetwalker. Much of my wife's clothing fit me, but her lingerie, mostly white cotton panties and white sports bras (she didn't even own a garter belt!), was not sexy enough, so I found myself frequenting women's stores and buying my own lacy bras and panties, stockings (NOT pantyhose) and garterbelts. Mine were in a variety of sexy colors: mostly pinks, reds, and violets. I had also sneaked a few pair of sexy shoes and boots into the house. These had heels far higher than Virginia ever contemplated. Eventually, my preoccupation with lingerie had led to the loss of my job. Several of the young women in my office complained about my ogling them but I was able to talk my way out of those complaints. Then, some spare shoes and undies that some female employees had left in their desks mysteriously turned up in a file cabinet in my office. I never told my wife the real reason why I had been fired, attributing it to lay-offs stemming from corporate downsizing as well as to affirmative action. (My job was taken by a particularly assertive woman named Anne, who seemed to gloat at the humiliating circumstances of my dismissal.) Nevertheless, the firing had the beneficial aspect of providing me with many hours to experiment with my feminine side, while Virginia was out to work, supporting the two of us. I was home one afternoon, after purchasing a new glossy, red vinyl waist cincher at my favorite lingerie shop, trying it on with a pair of my seamed red stockings and lacy bra and panties. With my face fully made up and my curly red wig in place, I paused to admire my sissified image in the full-length mirror, before sliding my size 9 and 1/2 (women's size) feet into a new pair of patent, over-the-knee boots, with 4 inch heels. It was then that I thought I heard a noise. A prowler, I thought. I started to crawl into the closet to hide, but before I could get in, the bedroom door flew open and the figure of a tall man, dressed in a black leather motorcycle outfit appeared the doorway. "Hello, Donna," the smirking cad bellowed as I cowered back toward the closet door. His dark eyes flashed ominously at me, as he gave me that smug look of complete confidence. It was like he already knew that my resistance would be quickly broken. His brown, short- cropped hair gave him a military look that was emphasized by his trim shape and authoritative bearing and demeanor. "Who are you? How did you get in here?" I shrieked, trembling at the thought of what he had on his mind. "And, err?, my name isn't 'Donna' its 'don'." I wanted to kick myself for giving my real name but I wanted this intruder to know that I was a man , although I wondered how he had come so surprisingly close to my real name. "My name is 'Tim'," the big hulk sneered, "but, as you will soon find out it isn't short for 'Tiny Tim'." And, as he strode into the room certainly looked anything but tiny. Clad in tall black Wesco boots that came up to his knees and tight black leather jeans topped off with a classic Marlon Brando-style motorcycle jacket. The jacket was open, revealing a slightly torn T-shirt, that seemed to accent his washboard-like abs. He was the embodiment of strength and virility and for some reason I though my name should be changed to 'Stella'. "What do you want? I..i?i.. i? er?, er.., don't have any money!" I stammered, knowing full well that my wife kept several hundred dollars in a small safe along with some securities and other valuables. "I want you, slut!" the brutish thug sneered. Pulling on a pair of thick black leather gauntlets he tossed his head back and placed his hands defiantly on his hips. "I followed you home from Belle's Lingerie Shoppe, where I saw you buying your pretty new waist cincher. You told the saleswoman it was for your wife, HAH! But I knew who it was for!" "But how did you get in," I sobbed, sure that I had double-locked every door. "None of your business, bitch," he hissed, slapping me across the ear and knocking me down onto the bed. "But here I am! Just what you always wanted! From now on you will address me as Master or Sir, get it! " "Y-Y-Yes, er?, S-S-Sir," I stammered, "but please.. please. just go away! I'm not a faggot, I'm a Man!" I blubbered, in the unmanly way. But he would have none of it. "You don't look like a man dressed like that," he sneered, "but if you are a man pull down those sweet panties of yours and show me. NOW!" he snapped. Nervously I fumbled with the lacy garment and did as he bid. Luckily I had fastened the garter straps under my panties so I had no trouble displaying my manhood. I don?t know if I was as much embarrassed by the fact that I was bring forced to expose myself to this leather- clad man or by the fact that I realized that I was displaying a rampant (for me anyway) erection. "HAH," he snickered, shaking his head in amusement as I displayed my rock-hard 4 and 1/2 incher, "you must be joking if you think that little thing makes you a man! It's just a little clitty! And if you were a 'man' your little clitty wouldn't be stickin' out at me like that - would it, SLUT!" I wanted to cry at the humiliation of it all, and I found tears were welling up in my eyes. "Pleazzzze, Sir, just leave me alone, and I won't report this to the police, pleeezz, I promise.." I outright lied to him, knowing full well that as soon as I got free - and changed to male attire - I would call the police and report the brute. "By the time I'm through with you, Donna, I don't think you'll want the police involved!" he responded knowing full well the reluctance of all rape victims, particularly closet- homosexual males (not that I would fall into that category) to report their defilement. "Besides, when they see pictures of you at the lingerie shop and dressed in your slut gear, do you really think they'll believe it was rape?" Pictures, I thought, he doesn't even have a camera. He must be bluffing! "You can't fool me - you don't even have a camera!" I spat back at him arrogantly. He just shook his head in exasperation at my silliness and tossed a stack of photos at me. None were from that day, but they had been taken over the period of at least a month, some of me in my "boudoir" and others at the Shoppe holding up lingerie against my body when I thought no one was looking. "Enough evidence, don't you think?" he smirked. "Now get those slutty red, thigh-hi boots on. They'll make you look like a real tramp - just the type of slut I like to bitch-slap around!" he laughed loudly at his crude attempt at humor. I looked aghast. There was no hope. It wasn't even that he was physically so much bigger than me, but the way he exuded strength and authority, there was clearly no way I could resist him. And, in light of the evidence I had just seen, the Police would probably never believe my claim that his assault was non-consensual. I thought back to the old joke that suggested that, "when rape was inevitable, lay back and enjoy it." The joke did not seem so funny now! "Please?.,er.., uh.., " I tried to say something - anything but words failed me. My eyes fell to the floor, and I picked up the patent boots and slipped them on. Yes, I was already following his orders. "Sir, i.. er, i.. ahem, ahem?, pleazzzze!" "Please? Are you asking to suck my cock?" the smug bastard sneered, as he spread his powerful, booted legs a shoulders-width apart and placed his fists defiantly on his hips. "yes that's a good girl, Donna. But I want to hear my sissy beg!" "W...wha?what do you mean? Beg to suck a cock?" I stammered in disbelief, trying to delay the inevitable. I started to stand up. In my 4-inch heels, my eyes were roughly on level with his, but he would have none of it. He bitch-slapped me, knocking me back to my knees, and resumed his haughty stance. "Start begging, bitch or else you'll be missing some of your teeth!" What else could I do? "Please sir I want to suck your big manly cock! Please I let me caress it with my lipstick coated lips and pleasure you with my tongue!" I blurted out not sure of how to beg for such a revolting 'privilege.' "You really are a slut aren't you , Donna?" he cackled. "Now get on your knees and show the proper respect for your Master. " I hesitated momentarily until he bellowed "ON YOUR KNEES NOW!" and I dutifully dropped t o my knees and began to do his bidding. "First, slut, show your complete subservience by licking the boots of your Master!" His boots were truly magnificent. They were Wesco "big boss" boots that came right up to his kneecaps. Shone to a glossy finish, they rose like two gleaming black columns of leather. Whereas my sissy boots contoured to every curve of my shapely legs, his only seemed to make contact at the calf where his powerful muscles seemed to stretch the heavy leather shafts. Greedily I slobbered at the masculine footwear, leaving trails of saliva to confirm that every inch of the foot and shafts of the boots had been fawningly worshipped. "Don't forget the soles and heels, bitch," he added sitting back on the bed and lifting one leg to allow access to the dirt encrusted soles. "Yes I guess you have found a true purpose in life," he sneered, "you're really enjoy being a bootlicking toady - don't you?" "Yes, sir," I cloyingly replied despite picking small clods of dirt, with my tongue, from between the ridges of the thick Vibram sole of the big boot. "Now, Donna, you can unzip me and take out 'Mr. T', and tell him how much you want him!" he allowed as he sat back on the bed. Mr. T? what did he have a nickname for his penis? How juvenile! I hadn't heard of such silliness since Prep school. The moment of truth was at hand. I knelt up straight so that I was almost at eye-level with his crotch. The tight black jeans looked as if the leather would burst from the pressure of the enormous bulge, which they were containing. Slowly I undid the heavy metal zipper and reached into the opening. I found a thin leather pouch, which held his precious jewels. I was able to detangle it from its sheath and gently drew it through the zipper into the light of day. It was Huge, telescoping out at me at least 8 maybe 9 inches and so thick I could barely get my hands around the thick, meaty, shaft. Looking up at my evil master, I started to implore him, "please let me kiss your mighty cock, sir!" "Yes, but first get to know him. Mr. T would enjoy some gentle kisses and caresses, slut." "Of course, Sir, let me kiss and caress Mr. T," I enthusiastically replied. Its evil eye was dripping pre-cum juices and with no encouragement, I greedily licked off the pungent juices an swallowed my first taste of male seed. Then, rolling back the foreskin to fully reveal his thick helmet, I began running my lips up and down the long, veiny shaft, smearing it with my bright red lipstick. Despite my professed revulsion, I found myself eagerly sucking it into my hungry mouth, as my body seemed to respond to some secret cravings, which my mind could not control. I hated myself for letting him bully me like this but what was I to do - he was so much bigger and stronger than me, I would have had no chance to defend myself against him. He had already proven how he could bitch-slap me around like a ragdoll if he wanted. My only consolation was in the realization that while this mindless brute may have physical superiority over me, when it came to brains he was probably the typical airhead-jock. If we were involved in intellectual confrontation, I would have clearly shown my true superiority. But for now I would have to do his bidding. But I had to draw the line somewhere! "You won't cum in my mouth will you, Master?" I nervously asked my eyes looking up pleadingly "What kind of man do you think I am?" he disdainfully responded indicating a genuine revulsion at such a prospect, "I know how to respect a Lady." Genuinely relieved, I went back to my duties. "Umm, ohhh, it's soo good Master, let me please suck your beautiful cock. Ahhh, Ohhhh , PLEEEZE I need it so bad!" I was wailing like a stray cat in heat as any indication that my desire to fully debase myself on his male member would have been fully lost to all but the most casual observer. Suddenly I heard a and saw the flash of a camera. Out of the corner of my eye I saw a willowy brunette, taking aim at me again. "What the??" my inquiry was interrupted by the now all-too-familiar feel of a large, gauntleted hand smacking me across the cheek. "Get back to what you were doing, slut!" Master Tim sneered, "attend to your business and never mind what else is going on." I wasn't sure, but I thought I recognized the figure of the photographer. Was it? Could it be? Oh Noo..h! It was! Yes, it was Anne, the bitch who got me fired and took my job! But why would she be here - with him? Although I continued to attend to the needs of his huge dick, the leather-clad sadist, could sense my distraction so another loud slap landed on my cheek, knocking off my pretty red wig, making me look a bit incongruous in my sissy lingerie and make-up but with short gray hair in an obviously male style. "Pay her no mind! Pay attention to your duties!" Desperately I threw my whole heart and soul back to the job of pleasuring my Master. "UMmmm, Uhhhhh, Ahhhh," I moaned as I tried to slide the entire shaft into my mouth but there were at least three inches of him left between my lips and his crotch as the thick helmet began to crush my tonsils. It had I thought reached my maximum capacity. But now I was to learn the true meaning of "Deep Throat'. "Take it all in, bitch," he ordered as the bastard grasped his hands together and wrapped them around the back of my head. "UMMPPHHH, URPHHHH, ARGGGGHHH," I coughed out as his thick helmet jammed down into my throat almost fully cutting off my air supply. He was now in full control of my head, pulling my neck towards him and then letting it fall back as he massaged my tonsils and used my throat as a pussy. Meanwhile I could see the bright flashes and hear the of Anne's camera as she documented my utter emasculation. "Look at the birdie," she wheedled as she stood directly behind Master Tim and for the first time could see it was definitely Anne. She was dressed far more provocatively than I had ever seen her before: a tight leather mini skirt, fishnet stockings, knee high boots, and, beneath a gauzy black blouse, I could see her black leather bra. Another and *flash* as she crouched to get a better angle. "It's a shame, Tim, that I can't get Donna to smile," she laughed knowing my lips were stretched to the limit just forming an "O" to get around Master's huge cock. "Don't worry, umph..umph," the big brute grunted between thrusts, "we'll get plenty of smiling pictures, umph?umph, when I take him up the ass!" And the two sadists laughed uproariously at the not so gentle threat. Suddenly I felt Master Tim's body start to tense up and he let out a loud moan "AHHHHH, Ooohhh, you bitch!" He started spasming violently driving his cock even further into my throat and then I felt a hot gooey sensation in my throat, reminiscent of the taste of the pre- cum I had licked off of the tip of his dick. I tried to spit out his prick but his grasp on the back of my head was too powerful. It was either swallow the foul liquid or gag. I swallowed for all I was worth - there must have been a pint of the stuff pumping out of his huge balls. Then he let go of my head and slumped down onto the bed. Perhaps I could have taken advantage of him in his moment of weakness but unfortunately I was gasping for air and near drowning in his cum as I tried to wipe off the stream tricking from the corners of my mouth. the damn camera again. "Smile for the birdie, (if you pardon the expression) sweetie," Anne giggled as she squeezed my cheeks with her gloved fingers to force them into a puckered smile. "Bitch," I growled attempting to take advantage of my master's momentary fatigue, but I no sooner had the words out of my mouth when I felt his hand twisting into my long hair giving it a mighty tug. "OWWWWW!" I yelped. "Do as the lady says, slut!" he rasped making me realize that even in his weakened state he was still far more powerful than I. "And my cock is still dripping. Make sure I don't get a drop on these breeches, or I'll make you pay in pain!" "Yes, sir," I mewed, my head bouncing back and forth from my master's crotch to smiling for my photo-op. As I licked off the last of the sticky goo, I noted a change in the size and shape of his flaccid cock. "OH yesss, baby, he moaned you are soooh gooood!" Within seconds his huge piece of male meat was telescoping out at me, its eye again hungrily sizing me up. "Yes my pretty, I promised to take your ass," he whispered in my ear but then violently twisted me by the ear and ordered, "up on the bed, bitch. I want you on all fours, and spread those legs! NOW!" I had no choice but to obey the lewd command. Crawling up onto the bed, I dutifully assumed the position. There was a full length dressing mirror facing me and I could see my Master (was I really thinking of him in those terms) behind me, unbuckling his belt and dropping his leather pants and jockstrap down to his boot tops. Then Anne came up along side of him with a tube of some sort of gel and rubbed it all over his thick and now fully extended prick. (Oh what stamina! - "Mr. T' was back ready for action in five minutes!) Then she came up behind me and I felt her rubber-gloved fingers probing my sphincter muscle. Oh it felt cold and gooey, but I knew that without it, I would be ripped in half by the thick male member now poised to violate me for the first time. (Well, at least since prep school when a few of the football players decided that my male cheerleading squad was fair game.) Anne stepped back and Master Tim climbed between my legs. I could feel his powerful leather boots against thin vinyl shafts of mine, pushing my legs further and further apart, as the head of his cock began to probe my tender bum-hole. At first it felt almost nice - like some sort of a rectal massage. But then he began to press the huge helmet-like head into me and my sphincter refused to yield. "Ahhhhh, owwww, nooo..hh! I can't take it! It's too big," I wailed. The mindless brute would have none of it. WHACK! He slapped my backside with such force that it probably would have knocked me off the bed if I didn't have my legs wrapped around him. "Shut up, bitch, you can take it - you're gonna take it! Whether you like it or not!" the brutish thug laughed diabolically. "Now spread your cheeks with your hands!" I complied with this command but had to balance my torso on my chin as my eyes watched the whole vile scene in the mirror. I could see Anne moving back in front of me her camera taking aim. *flash* *flash*. "Make him smile, Tim!" she screamed. "You heard the Lady," Master Tim ordered as he reached down and gripped my drooping testicles. "SMILE NICE, Donna! Or else!" he hissed in my ear. How could I smile with my rectum in the process of being dissected? I don't know but I made my best effort to raise the corners of my mouth and display my best Shirley Temple smile. *flash* (actually the pictures I subsequently saw indicated a not so bad effort.) Slowly but inexorably, Master's prick probed, until at last my feeble defenses fell. My eyes rolled back into my head as Anne continued to snap pictures. My booted legs flailed futilely trying to drive him back but he was already between them and their useless flailing only emphasized my impotence. "Ahhhh! Ohhhhh! NO?HHHhhh! Pleeeeze DON'T!!!" I wailed pitifully as the Master continued his onslaught. Tears were rolling down my cheek turning whatever was left of my eye make-up into black stripes down my cheeks, but my body was betraying me as my hips were gyrating and my legs bucking to accommodate his every thrust. "OHHHHhh, PLLLEEEEEZZZeee! uhhhhhh, NO?HHHhhh DON?'T! DON?'T !!! Doh... DON?'T !!! DOHHHN'T, PLEEZZZZZE - DON?'T STOP!!!" All my self-respect was out the window. I was moaning for all the world to see how much I wanted it. "HARDER! DEEPER!" I screamed and begged this mindless brute to fuck me like the whore I am. "Yes, BEG slut I want to hear my sissy-slut beg!" he hissed in my ear as he was now slowly pistoning his prick in and out of my ass, and my worthless as gyrated to rise up and fully meet each and every thrust. Finally, I wrapped my booted thighs around him and was using my spiked heels as spurs, flailing at his flanks, to urge him to augment the intensity of his thrusts. My degradation must have continued for a half an hour as my Master verbally abused me and explored my little titties and stomach and thighs with his meaty paws. My throat was sore from my screaming and begging him to intensify his efforts. "HARDER! DEEPER!" I wailed over and over as my body rejoiced at the feeling of fullness yet still craved for more. Despite the generous size of his cock my body bucked and heaved seeking even greater feeling of fullness. I wanted more! A momentary thought passed through my brain, as I realized the emptiness my wife must have felt when she sought to be satisfied by my tiny weenie. I felt bad as I sympathized with the emptiness she might have felt, but I was too caught up in my own fullness to dwell on it. My mind was convulsing with pain, pleasure and my own sexual cravings. Finally, I felt him tense up as his body spasmed and I felt my asshole fill up with hot gooey liquid. The bastard had cum in my ass. Still, I was moaning like a cheap hooker until, finally, he reached around my hips and wrapped his gloved hand around my pulsing clitty. One, maybe two strokes and I was pumping a cascade of white gism onto my wife's favorite quilt. "Thank you, Sir! oooohh, thank you Master, " I moaned deliriously from the most intense orgasm had probable ever experienced. But then I started to regain my senses. "Omigosh, please I must clean this mess up! Virginia will kill me if she finds a big stain on her quilt," I whimpered. "I think she'll be home any minute bitch, look at the clock it's after 5 o'clock," he sniggered, "and I can hardly wait to tell her what a slut you've been for me today!" "You promised not to tell my wife; please you mustn't?let her find me like this!" "Yeah and I also promised not to cum in your mouth. Just shut up and lick up your stinky mess, bitch. And don't worry about it, I made your wife do the same thing last week when some of my cum spilled onto the bed." Tim interrupted me. "What are you talking about - what were you doing here with my wife?" I inquired dumbfounded, as I lapped my own foul gism off of the quilt. "I may as well tell you now, Virginia and I have been having an affair for almost a year. How do you think I got the key to get in here? But she didn't believe me when I told her what a pervert you are. All she knew was that you could never satisfy her sexually and you disgusted her with your kinky perversions like asking her to wear boots to bed. However, after I hired a private detective to follow you, I found out about your C/D adventures and guessed that what you really needed was to be fucked by a real man! The funny thing is that both you and your wife needed the same thing!" Both Anne and Master Tim laughed at his crude joke. "But I thought she was just losing interest in sex?" "Maybe she had lost interest in sex with a sissy-wimp like you, Donna, but, I assure you, not with a real Man!" Master Tim clucked gloatingly. "Or a real Woman either," Anne chimed in. "You mean?," my voice trailed off "Yeah your wife was a real sexual swinger. She just needed someone to swing with!" Master Tim smirked. "And it wasn't you!" Anne chimed in. My ass was still dribbling my Master's cum and my lips and cheeks were still smeared with my own, when I saw the door open. Omigosh, Virginia was entering the room! She was dressed head to toe in black leather - just the way I always wanted to see her, but not now, with me looking like this. She looked down at me and shook her head - not in anger or even disgust - just pity. "My poor Don, or I guess I must say Donna," she cooed compassionately as she reached down and gently tapped my cheek. "Has big old Timmy-boy been rough with you?" "Yes, I have," Tim sneered "but that's the way sissy-Donna wanted it- Isn't it ?" he demanded with an angry look and slight threatening gesture; "Yes, Sir," I tremblingly responded forgetting for the moment that my wife was standing right there. He was humiliating me in front of her! "See, sweetlips. Just as I told you he really wants to be a sissy slut," the wicked brute cooed into my wife's ear. "Yes, darling, I guess I should remember that you are always right!" my wife purred as he enfolded her in his arms and their lips met in an open-mouthed tongue swallowing exhibition of debauchery. I looked at the two of them embracing and recollected on that night when my wife had come home from the party. Obviously this was the "Tim" that she had been craving in her inebriated state. How could I have been so dense not to have guessed? But I also understood why after having had sex with this large powerful man. She could never accept me and my tiny little penis after having been filled with his huge cock. The same man who had raped and fucked me had also cuckolded me! "I'm sorry, Donna. I had hoped it wasn't going to come to this. Initially, I just needed some good old-fashioned sex and Tim was perfect for the job. From the start, he wanted me to leave you but I wouldn't. Yes, I knew you had a few sexual fetishes and with that tiny little dick of yours you were never going to be able to satisfy me, especially after having sex with Tim, but I thought at least that you were a man." "I am!" I whined futilely trying to challenge the specter of my dress and recent performance." Virginia smiled and shook her head knowingly and continued. "Tim told me from the start that he had you figured for nothing but a cock sucking, pantywaist faggot but I never believed him. But then he brought me the pictures. Even then I thought well maybe you still wanted to have sex with a woman but after seeing you today ... - oh you probably didn't realize it but your whole scene with Tim was recorded on a closed circuit surveillance system set up by his private detectives. I was downstairs the whole time watching. I was even able use a remote control to follow you around the room and watch you. Well, anyway, after seeing how you responded to Tim, I know what you really want and I can never fulfill that need!" "But why is it alright for him to have sex with a man and not for me?" I whined. Virginia just shook her head, sighed and tenderly explained. "Master Tim wasn't having sex with a man, he was having sex with a sissy! He was the one in charge; he was the one in the traditional male role. You on the other hand were the "woman"! You were dressed in lingerie; you were penetrated; you in fact deserved to be fucked and? you were! Simple as that." My head filled with shame as I thought of how I had so obscenely debased myself: begging to suck his cock; moaning and gyrating as he penetrated me. My loving wife had been privy to the whole humiliating display. She was right: I had undertaken the female role and could not blame Master Tim for treating me as he did, or even question his manhood. I was the one who had lost not only my virginity and my claim to manhood. "Please Virginia I still love you. I'll try to change and become a man. Don't do this to me, I love you!" I moaned. "I love you too, Donna, but just like you need a man, I need a real man too! To have sex with, and after seeing you in action, I know that you can NEVER be that for me. But don't worry I'm not going to leave you. The three of us can live together - Tim and I as husband and wife, you as our sissymaid-slut." "But how can you support the three of us. I'm out of work and I'm sure this mindless brute doesn't have any decent kind of a job!" The three of them howled. "Master Tim a mindless brute?" Anne parroted. "I guess you don't remember Tim but his company, Genetics, was our biggest client at Textron. He is worth a few hundred million in corporate stock alone! A mindless brute - that's a good one! He is a licensed MD and has a Ph.D. from MIT in cybergenetics." "Where is your Ph.D. from?" my wife chimed in with a giggle, knowing full well that I barely achieved a BA degree at the local state college. The three of them hugged and laughed but all I could think was how this man had bested me at every turn. "By the way you are no longer un-employed," Anne informed me. "We've agreed to send you to secretarial school and when you're finished you have a position as a file clerk, working for me." "You mean as your secretary? Working as your Secretary in my old firm? With you in my old position?" I wailed in disbelief. "Well not exactly," Anne conceded, and I heaved a premature sigh, "you see you'll be starting off as a file clerk, working for my secretary, Evelyn, you know the girl whose panties and shoes you stole! "Everyone will recognize me!" "I wouldn't worry too much about being recognized. After we're through with the cosmetic surgery and breast implants, voice training and other things we have planned for you - no one will recognize you for the sexist pig, who used to work there. Only Evelyn has been told about it and she's already planning to have you do the filing, whenever there are male clients in the office. She seems to remember you saving all the bottom draw filing, which required deep bending, and top draw filing, which required getting up on a ladder, whenever a bunch of horney clients were in your office." I blanched at the idea of sexy little Evelyn evening up the score, but my thoughts went back to my former colleagues. "But my old buddies? They'll have to recognize me!" "Well, most of them are gone. I've fired them and replaced them with capable Women. BUT that does remind me. There are still a few of those male chauvinists there and I think I can get them fired on sexual harassment charges. I just need you to sign off on these affidavits, testifying as to their lewd behavior, and they'll be off site by Monday," she laughed as she shoved three thick legal documents, opened only to the signature page and ordered me to sign each one. "If he were any kind of a man," Tim shook his head, as he watched in contempt as I signed all three documents, "he would probably have at least tried to protect his pals but I guess we all know he's well past that point." The two women giggled at the comment, but Virginia tried to defend me. "Oh Tim, don't make it worse for Donna, she's been though so much today!" "Hey! who's giving the orders around here, Ginny?" he spat back sarcastically as he pulled her into his powerful arms and pressed his body into hers. "OHHH yes.. Tim. Ohhhh. You are the boss! Ahhhh!" she squealed like a schoolgirl and then locked lips with him gagging any further debate as the two of them fell over onto our bed, pawing and grasping at each others leather-clad bodies. It was obvious that passion was getting the better of them as they began to shed some clothing and their hands began to grope into their most intimate crevices. "Sit down at my fees and kiss my boots while your ex-wife gets fucked by your lover," Anne hissed and I dutifully obeyed. She flicked on the VCR with her remote ad began watching the portion of the tape where Master Tim brutally violated my ass. I could hear myself moaning and begging for more on the tape as wails harmonized with those of my wife who was getting fucked on our wedding bed by the same man who was fucking me on the tape. 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A few years ago I was on a weekend trip to Brussels and Amsterdam with some friends, and found out a girl I knew from Ukraine was now living in Lille, not so far away, so I decided to make a quick trip to see her the evening before we were due to fly home. I caught the train from Brussels to Lille and she and her boyfriend picked me up at the station. She was a short, curvy blonde, with equally large breasts and ass. She loved wearing sexy outfits which showed them off. This evening she was...

3 years ago
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Crossdresser in Love

I woke up with my hands bound, my mouth gagged, and my ass plugged. The bed I was on was comfortable enough. This was just a reminder that these parts of my body were no longer mine to do with as I pleased. For tonight would be my wedding night. For months we had planned things out. Picking out a dress, a place for the ceremony, all the things that brides do with their future husbands. But for me, it also included a regimen of hormones to complete my becoming as feminine as can be for my man. I...

Crossdressing
2 years ago
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Crossdresser for mature couple

I am a bi crossdresser....love some pussy or cock. I registered on an fabswingers looking for a meeting with similar people.I was actively looking for an older couple to have some fun with. To cut a long story short, I finally got talking to a guy called Bill. He and his wife could entertain a gurl like me for a fun filled evening, if I was game. We both had a list of dos and donts for the night and we went over a few ground rules etc.I was to be their maid and waitress for the evening. They...

4 years ago
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crossdressers 1st time

hi, im new to this. this happened about 3 years ago now.I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from this simple thought I became massively aroused and started trying on her underwear, make up, and even a wig that was in the apartment. soon enough, I was looking like a slutty crossdresser.I thought enough...

3 years ago
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Crossdressing Karte Hue Pakad Liya

Hello indian sex stories dot net friends , my name is preeti(fake name) age 20. Ye baat kafi purani hai lagbhag 3 saal pehle ki . Mai ek part time crossdresser tha aur mujhe meri chachi bahut pasand thi aur hain . To mai jab vo aur ya koi b ghar pe nahi hota tha to mai unke room mai jake unke innerwear pehnta tha . Aur jaise ki mujhe bondage bahut pasand hai to chachi ke kapde pehnke self bondage karta tha jab ghar pe koi ni hota tha . Isi tarah ek din ghar pe koi ni tha aur mai chachi k room...

2 years ago
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Crossdressing Domina gets a new slave

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained.I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels. The first time I saw him I had brief fantasies of my hands and mouth exploring every inch of his petite and...

Crossdressing
3 years ago
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Crossdresser wanting some dick on the road

I`ve been crossdressing since I was 20 years old.One of my favorite things to do is get all dressed up in womens clothes and drive around on the open road.Several years ago I was mad at my ex wife for doing some stupid shit with our checking account and we were split up for some well needed cooling off time.The more I got to thinking about her stupidity the more I got to smoking some pot and drinking a few mixed drinks to get the crap off my mind.I got pretty stoned and decided to get dolled...

1 year ago
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Crossdressing Charlie Episode 11 Under His Thumb

CROSSDRESSING CHARLIE Episode 11 UNDER HIS THUMB Prue watched him get into the car from the top of the steps. Dave, who was still standing outside of his car, stared at Prue maliciously. She returned the gesture, glaring intently with apprehension before watching him swing into the car. Dave was quieter than usual as he settled himself at the wheel. He looked unnerved, doubtful, and even a little irritated. He turned the key in the ignition and the engine revved up like a vicious...

2 years ago
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Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when she stood up. A box fell from her hands and onto the floor. Being the nice guy that I am, I picked it up...

Crossdressing
3 years ago
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Crossdressing Vignettes True Story

I went through a period in the '80s and '90s when I was very much into crossdressing and being a bottom. I didn't write these events down at the time, but I wish I had. As the events come to memory, I'll write and post them. Here's one such story:In the '90s, I was married, and my wife didn't (as far as I knew, anyway) know about my bi or crossdressing interests. I loved her very much, but I had these other desires I never shared with her. I kept a small bag of lingerie, condoms, and lube...

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