Big Fat Bertha Lou Part 1 free porn video

Big Fat Bertha Lou Part 1 By Cheryl Lynn This is a severe humiliation story and contains some unwanted sexual scenes. It is not for the sweet/sentimental reader. All the usual disclaimers apply and for personal use only. Any other use is strictly prohibited unless approved by the author. Thanks go to Throne for giving me the idea for the main character in this story. Comments are welcome at [email protected]. Big Fat Bertha Lou Bertha Lou had been obese since childhood, very obese. All the females in the family going back generations had been obese and she was no exception. At the turn of the 19th century fat girls made ideal mates for the young men of that era. With their wide child bearing hips men knew they could father large families who could then be used to help farm the land. That was then but now men lusted after shapelier beautiful women. Bertha Lou met none of modern day dating criteria. She was fat and ugly. Her only good feature was a pair of emerald green eyes. Bertha Lou was five foot nine and weighted two hundred and ninety-eight pounds. Her black hair was cut in a unflattering short page boy style, had a large fat nose and triple chin. Making her features even less appealing was a significant gap between her two front teeth. Teased mercilessly throughout her life she had few girlfriends and never asked out on a date. As a result spent her time on her studies and bottled up her ever growing hatred of men. It was always the boys and men as she was growing up that had bullied and teased her the most. The most humiliating day in her life occurred during her junior year of high school. A transfer student, James Archer, asked her out on a date. She was skeptical at first but being new he convinced her to go to a costume party. James told her that he was going as a male ballet dancer and needed her to join him as his ballerina. To prove his sincerity, he showed her the men's dance leotard and tights he intended to wear and presented her with a gift. It was a pink leotard and tights with white tutu since she told him she didn't have one. On the night of the party James called her and told her something had come up and for her to meet him at the party. The party was at one of the most popular student's home and she was the only one wearing a costume. Needless to say she fled in horrified humiliation with James laughing the loudest. Over the next two years of school constant reminders of her ordeal kept popping up. Other incidents over time made her hatred of men fester. One day, she promised, she would get even for the way men treated her. Ooo Bertha Lou was waddling out of the mall Friday evening when of all people, James Archer came stumbling out of Applebee's drunk as a skunk. He had been celebrating at the bar with some of his friends. Bumping into Bertha, he fell doing a face plant on the granite flooring. He was out cold. She wondered where this asshole's friends were but no one was around. Not seeing anyone and no one coming in the nearby entrance door of the mall, she had an idea. Picking him up and putting his arm around her shoulders and grasping around his waist, dragged him out of the mall. Only a couple of people going to the entrance saw them but paid no attention. At her car she dumped him into the back seat. He had a bump on his forehead and totally out of it. Smiling she drove home to what had been her mother's house. The wood framed two bedroom house wasn't much but she had inherited it and the five acres of forest surrounding it. The best thing about the house was its relative isolation where passerby's couldn't tease the fat girl. Bertha Lou had no trouble getting him into the house. Once inside took him down into the cellar which had been converted into a spare bed room. This room was for visiting family members and had a small bath. Bringing him home had been a spur of the moment decision and she wasn't sure what to do now that she had him. Looking down at the snoring man her held in hatred flared into full bloom. "I'm not sure what I'm going to do to you yet but I will figure out something even more embarrassing than what you did to me. No one knows where you are and I doubt anyone that might have seen us gives a shit. The one thing I'm sure of is that you're not going anywhere soon," she said while stripping off his clothing. James Archer wasn't a big or overly masculine man. He was five foot seven, weighed one twenty-five with below the collar length sandy blond hair. He was twenty-two years old with what many would call baby faced good looks, a face that seldom seemed to need a shave. The rest of his body was hairy but not overly so. While she had never dated she knew what a man looked like down there. Reaching out she pinched the head of his penis between thumb and forefinger stretching it out. It was the first adult penis she had ever touched. "Not that impressive I imagine but I guess like all men proud of it. Now that gives me an idea but first I have to make sure you don't go anywhere," she mumbled as she released it. Picking him up carried him into the bath and placed him in the old fashioned footed tub. She found some duct tape in the closet and quickly secured his hands and feet. While secluded she didn't want to hear him yelling and screaming so pulled off her white nylon six "X" sized panties and stuffed them into his mouth. A final piece of duct tape would hold them in place until she could find something better. Back in her room she got ready for her night shift. Bertha Lou was a Licensed Practical Nurse (LPN) at a nearby nursing home. She was tempted to call in sick but she needed to get some supplies. Her plans for him were still in their infancy but the nursing home had things she would need like pharmaceuticals. The night shift meant that she would practically be alone all night. Like most nights she checked on her patients and made rounds but other than that not much ever happened. She used that down time wisely gathering some things here others there putting them into her large tote. Satisfied she had most of what she needed, spent the rest of the evening searching the web and placing orders. It was a very satisfied Bertha Lou that went home. The first thing she did was retrieve the supplies she had taken from the nursing home. He was still asleep which made what she planned on doing so much easier. Taking the large container of Glucose IV solution she hung it from the shower rod over the tub and inserted the needle into his arm. Turning on the drip, she injected the sedative into the solution. A protective cover was put over the injection site to keep the needle from moving or getting wet. "That should keep you asleep, hydrated and fed until I wake you up in a couple of days," she thought smiling down at him. Ooo Over the weekend she checked on him frequently changing out the IV as needed and making sure his wastes were washed down the drain. Other than checking his vital signs there wasn't much more she could do. Late Monday afternoon on her day off she found several packages at her front door. "Finally now I can really fix his wagon," she thought as she carried him to the bed. Grinning she removed the slivery titanium chastity from a box. Her smile widened as she examined the top of the line device. It had been very very expensive but she wanted the best. The woven metal of the penis tube worked like a Chinese Finger Puzzle the more you pulled on it the tighter it became. The underside of the tube was not polished like the outside. It had small points similar to a rasp file that would grip the flesh. If he tried to get an erection the pain would be significant. Attached to the base were two thin titanium chains that went around the waist and connect to the one attached to the front with a cylindrical titanium combination lock. Once on his penis would only be good for urination provided he sat. Opening the next box she took out a florescent pink leotard with round neckline and cap sleeves, white tights with rainbow highlights, stiff white tutu and pair of black ballerina slippers. The last box contained a bright red heart shaped satin purse with a gold chain shoulder strap. She put his wallet, keys and cell into the purse and hung the chain strap around his neck. She left him lying on the bed so she could finish the final details. Bertha Lou had cut out individual letters from magazines and busily began constructing them into a note. James When you read this you probably already know what I did to you If you ever want to get out of the fix you re in call 555-5656 and ask for Mistress Yes you could call the police have me arrested BUT if you do I will have burned the combination to the lock You will never get out without severe deep burns or worse. It takes an especially hot torch to cut threw titanium Mistress Smiling she put the note and several pictures of him in his precious ballerina outfit into his purse. Picking him up carried him to her car. It was pitch black as she drove to the mall with clouds covering the crescent moon. By the time she got to the mall it was closed and she had no trouble sitting him down by the entrance without being seen. Ooo Something tapping him hard on the shoulder woke James up. Stooping over him was a security guard. He raised his hands to rub his eyes and block the bright glare of the flashlight. He came fully awake seeing the bright pink nail polish on his fingers. "Alright buddy, I don't know why you're dressed up for Halloween in the middle of summer but you're not sleeping it off here. Get you fairy ass up and get out of here," the security guard said tapping the heavy steel flashlight in his palm. A very confused and disorientated James staggered to his feet. The last thing he remembered was drinking with his buddies. Now he was standing outside the Mall, with pink nails, worse yet wearing a ballerina outfit complete with flaring tutu and a purse slung around his neck. "What the fuck?" he said hoarsely. His throat was bone dry and he had a pounding headache to boot. "Go on, get outta here faggot or I'm calling the cops," the officer demanded poking the flashlight into his chest for emphasis. James still confused looked at the officer tapping his flashlight menacingly in his palm then scanned the mostly empty parking lot. He saw his car and staggered over to it. It had keyless entry and opened at his touch. Seeing the beam of the flashlight shining on him, he quickly put the car into gear and drove off. "It's bad enough having to chase homeless bums away but now faggots?" the security officer mumbled as he left to finish his rounds. When James arrived at his apartment complex most the parking spaces were filled. He found one at least hundred yards from his. Glancing at the clock on his dashboard noted that it was a little past mid-night. "Crap! No wonder the lots full. Now I have to get to my apartment looking like a damn fool and not be seen. Shit! If I find out who did this to me I'm going to kill them," he yelled banging his fists on the steering wheel. The tutu kept bouncing up and down as he walked sticking to the shadows. Its touch was making him madder and madder. Looking around and seeing no one, he made a made dash for his second floor apartment. He stood before his door panting and wondering how he was going to get in. The leotard had no pockets. It took the confused man a couple of moments to remember the purse. "I've never been so happy to be home in my life. Now to get this crap off me," he said in relief once safely inside. He started ripping off the offending clothing as he walked to his bedroom. He still had the tights on when he looked into the full length mirror on the back of his closet door. His hair was in a bun at the top of his head with a pink satin ribbon tied around the base. His cheeks were circled in pink blush, his eyelids painted in a bright green shadow, thick black eyeliner, long false eye lashes and his lips coated in glistening pink lipstick. What really stood out were the two painted arches over his eyes. His eyebrows had been shaved off. "OMG! Could this get any more humiliating?" he said as he began pulling off the tights. With the tights halfway down his thighs James saw what Bertha Lou had done. He staggered almost falling when he saw the shiny metal encasing his groin. It didn't take him long to discover that it couldn't be removed and that it hurt like the dickens when he pulled on the sheath. Giving up he went into the bathroom to remove the makeup. There he discovered that soap and water wouldn't remove the lipstick. No matter how hard he scrubbed it retained most of its coloring. He cussed loudly seeing that he didn't have any eyebrows or sideburns. Giving up the attempt to remove the lipstick, he stepped into the shower. His hair had been soaked in hairspray and needed to be washed out. He also coated his groin in shampoo hoping to slip the chains down over his hips. Again he was met with only more pain and failure. Taking one last look into the mirror over the sink, he muttered, "At least I have the weekend to see if this shit wears off. It's probably that long lasting stuff I've seen on television commercials. I just hope no one notices that I don't have any eyebrows. I wonder how long it takes for them to grow back. My next door neighbor has some bolt cutters. I'll borrow them in the morning and get this damn thing off me. Shit, I forgot about the lipstick...can't let him see that..I could tell him my girlfriend did it as a joke. Yeah, that'll be embarrassing but probably work. Guess I can scrape this pink polish off my nails with a knife but right now I'm calling Jake. Maybe he can tell me which of those yahoos I was drinking with did this to me." Still naked he opened the purse to remove his cell when he noticed the note. It fell from his shaking hands and he collapsed onto his bed. His hands clenched into fists pounded the mattress as tears began to flow. "Damn it! I'll find out which one of you yahoos did this and I'm going to kill you! This isn't funny anymore you sick fucks!" his mind screamed. When he regained control he sat up and reached for his cell intending to call Jake. Hearing a very groggy sounding Jake finally answer, James lit into him with a burst of profanity interlaced with wanting to know who screwed with him. Jake responded by saying he had no idea of what the hell he was talking about and why he was calling him at this ungodly hour on a Monday night. The phone fell from his hand as he sat on the side of the bed. "Monday night? It can't be," he thought picking the phone up and checking the day app. "OMG! It's Tuesday morning! How did I lose three days of my life and what the fuck's going on? Shit!" he gasped. At seven James went to his neighbor's door and asked to borrow his bolt cutters. When asked about the pink lipstick, he said it was a sick joke done by his girlfriend. It was embarrassing and he got a good chuckle out of his neighbor. Back in his apartment he quickly striped and spent the next thirty minutes trying unsuccessfully to cut the thin chains. Giving up he returned the bolt cutters. After calling in sick to work, he spent the next couple of hours researching titanium, how to cut it and chastity devices for clues to getting them off. What he discovered about titanium scared him as it had a melting point of over three thousand degrees Fahrenheit, stronger than most steels and preferred in body piercings due to its inertness. He managed to find the site selling the device securing his groin. The news there was no better as it explained that there was no industrial built in combination that could over ride a combination once set. "I'm truly fucked!" he screamed in frustration slamming his hands down on the keyboard. Ooo While James was discovering the extent of his plight, Bertha Lou was trying to figure out what to do next. "The pink leotard and dropping him off at the mall had to be humiliating but that's not enough. He plagued me for years and I just can't settle for one good night of revenge. Yeah, the chastity has to be mortifying but not humiliating. He won't be able to have sex but that won't necessarily make him the subject of public ridicule. So what can I do to make his life as miserable as he made mine?" She spent most of her morning and early afternoon going through various sites on the internet. She found a large number detailing ways to extract revenge. She found everything from simple practical jokes to advocating physical harm but the ones concerning petticoat punishment, now that got her interest. When she gave him her cell number, it was only to rub in how dickless he was going to be. However the idea of him having to go to work and appear in public as an emerging transsexual intrigued her. "What could be more humiliating than for a macho man having to appear in public than that? This is really beginning to turn me on. The more I think about it the better it gets." Ooo James spent the rest of the week trying to figure a way to get out of the chastity belt. As embarrassing as it would be he made an appointment to see a blacksmith. He figured who else had the knowledge of metals and ability to get him out of his fix. The blacksmith lived on a remote ranch about three hours away and most likely wouldn't know of any of his friends. He gave a false name only revealing that he had a chain that need to be removed. The experience was more humiliating than he thought and the results even worse. The chain was fastened too tightly for the smith to get any of his cutting instruments in a position to sever them. The cylindrical shaped lock was too small to brace for a chisel to break. It was obvious the smith was holding back his laughter as he told James that he had to have the combination. "Look Mr. Madison, the only thing I can tell you is do whatever your boy..er girlfriend says. Until she releases you, I'm afraid you're stuck," the smith said grinning widely. "It was my girlfriend! Errrrr she...she caught me cheating," he responded not wanting to make his embarrassment any worse. He had caught more unwanted derogatory comments already this week over his brightly painted lips and missing brows than he wanted. He hoped that they would stop giving him shit and bought his explanation of a bar-b-que accident and girlfriend's joke. The idea that anyone thought he was a homosexual made him ill. He hated faggots but smart enough to know to be politically correct. Giving up all hope of getting the device off by himself, he had only one choice left. Friday afternoon he called the number on the note. He was surprised to hear a woman's voice answer but started demanding that the belt be removed. He didn't get six words out before the line went dead. He redialed and got the same response. Deciding that making demands wasn't going to work, he started his next connection with, "Please Mistress." "You are a slow learner but maybe there is hope for you yet. I know why you are calling and if, and I say if, you respond correctly I just may help you out. So let me tell you the rules. You will always refer to me as Mistress. You will do exactly what I demand happily and obediently or you will never hear from me again. You will never be free until you have fully completed the tasks I have set for you. Finally, I don't give a damn if you ever get out of that chastity. Now for the first order of business, I want you to make an appointment to have your body except for your head to be waxed clean of all body hair including your groin. You will set up monthly appointments to get your body waxed. I also want the name and contact number of the technician. You have until Saturday evening to get that done and send me a picture. I'll text you my email. Until then, I don't want to hear another word except 'yes Mistress.'" As the line disconnected, James stood open mouthed trying to make sense of what he had just been told. The buzzing of his cell telling him that a text had been received. Ooo Saturday afternoon James glowed pink but not from the residual effects of a full body waxing. He had never been as embarrassed or humiliated as when the very pretty young woman striped him of his body hair. It had taken all her will power not to break out laughing when she saw his chastity but it was obvious to James. It had been bad when he walked into the salon. His pink lips drawing attention but having a woman he would love to date see his privates almost made him want to die. He was still blushing as he took his naked picture, downloaded and sent it along with the contact information. "OMG! I just hope this is enough and she'll free me. I have never been so mortified," he thought as he pressed the send button. It wasn't long before he received an email. "Very good, now for your second task, go to a fine lingerie store and replace all of your boxers, y-fronts and undershirts with the laciest and silkiest most colorful panties and matching camisoles. Once you have made your purchase, you will cut your male undies in half. Display your shredded male clothing and your new ones. Take pictures and send them to me. You have until Monday to complete this assignment or else. Beginning Tuesday morning and every day thereafter you will take a picture wearing your new lingerie and send it to me. Additionally, when home you will only wear your lingerie and nothing else. I will be randomly calling and you will respond with another picture of you in your lingerie from your cell. If you even think of putting on your old men's wear you will never be free. P.S. You will tell the clerk that you are buying them for yourself. You will provide me with the clerk's name and contact number. Mistress." "Oh shit!" was all he could say slumping in his chair. The only good thing about Monday was that the pink lipstick had finally faded away. It was about an hour before the store closed and James didn't see but a few people moving around in the shop. Nervously he stepped through the doors and approached a clerk. It took him several seconds to regain his composure as he asked her for help selecting panties and camisoles. "How sweet, are you buying them for your girlfriend? Do you know her size?" the cute brunette asked. His forehead broke out in a sweat as the moment he feared arrived. "Err no Miss. Th.....there fo...for me." "For you? Oh my gosh! I've heard about guys like you but you're my very first. Gee, yeah, sure, no big deal. I get a commission either way. Come on this way and I'll measure you," she replied louder than he would have liked. "I've heard the girls talking about these freaks but I never thought one would come to me. Gee, to think I though he was kinda hot when he walked in. Well maybe I can have some fun with this anyway," she thought leading him to a changing booth. In the booth she had him drop his pants so she could get an accurate measurement of his waist and hips. Blushing scarlet he pushed his pants down just below his hips praying that she wouldn't notice the device. It was not to be as measuring his hips the back of her hand brushed his boxer covered groin. "Oh my, what's this," she said brazenly pressing her palm against his groin. He reacted automatically and slapped her hand away, his mouth working but nothing coming out. "Yo...you hit me. Now I'm calling security," the clerk said moving to the curtained doorway. "No, no please, please don't, I'm sorry. It was just a reaction. I didn't mean to.....," he plead. "Okay but you're gonna drop those boxers and let me get a good look at what you're hiding down there," she demanded. James finally left the store carrying several large pink bags. His face an even darker shade than the bags he was carrying. He not only had the most feminine panties and matching camisoles but half a dozen matching garter belts and four dozen pairs of thigh high nylons in various shades and colors. The experience was more humiliating than his salon visit. Not only did she insist that he buy the additional items but had one of her friends help. He was just lucky that she didn't insist on him buying the matching bras. When he had asked for her full name and store's contact number, she absolutely refused. "You think that I would ever want to go out with a pervert like you? No, I like real men, you sicko," she replied when asked. His humiliation was complete as he broke down and told her that his girlfriend wanted to confirm his purchases. The only way the clerk would give him what he needed was if he made those additional and expensive purchases. Totally mortified and his bank account seriously diminished he left as quickly as he could. Tears flooded his eyes as he cut all his men's underwear into pieces. "I don't want to do this but I can always replace them later. Damn! I hope when I send her the picture of these and my new underwear she'll stop all this. I don't know how much more of this humiliation I can stand." He was standing in a pair of emerald green nylon tap panties with two inches of white lace on the leg hems and the matching white lace lavished camisole as the flash went off. He uploaded the pictures and plead to be released. He begged forgiveness for whatever she thought he had done. There was no forth coming reply. Ooo Tuesday he received four phone calls demanding a picture be sent. Three of those calls came while he was at work. Scared shitless he made his way into the men's restroom, entered a stall and stripped. If one of his co-workers came in and caught him wearing panties and camisole his life would become a living hell. "My life is already a living hell but if someone sees the flash as I take this picture I'm doomed. Even if I can get out of here without being discovered, I'll be labeled a pervert. Who the hell, besides a perv would take pictures inside a damn stall anyway?" Wednesday he received one of his calls while in a committee meeting. It was embarrassing having to ask to be excused but he only had ten minutes to send the photo or else. The rest of the week wasn't any better but he was happy to see the weekend arrive. He held a vague hope that after being forced to wear panties and camisoles for a week she would let him go. Those hopes were dashed when he received a new text. "You were very good this week. Now for your third task, I have made you an appointment at Sally's Nails for 10:00 a.m. When you arrive tell the manicurist that you want glamour length nails and fuchsia your preferred color for both your fingers and toes. Before you leave purchase a nail care kit and bottle of varnish as you will be keeping your nails pretty for me. Don't disappoint and don't forget to send me pictures by noon. Mistress Sally's Nails was located in an upscale shopping center not too far from his apartment. It was a place frequented by many of his fellow apartment dwellers and he was very nervous as he neared the doorway. There were a lot of people moving around in the hallway but only one customer in the shop. Swallowing what pride he still had walked up to the receptionist saying he had an appointment. Almost immediately a very pretty Viet Namese girl showed him to her station. When he told what he wanted she burst out in giggles making him blush a brighter shade of pink. "You're joking, right?" she replied smiling. "N....no...I'm...serious n...an..and want them...them and my toes..toes pain...painted fuch...fuchsia," he stuttered while thinking, "OMG! Please don't make a scene this is humiliating enough." "You want me to give you nail extensions and varnish them fuchsia?" she asked much too loudly drawing the attention of all the women in the shop. "Please, not so loud and yes that's what I want," he replied almost in a panic. "Okay, you weird but I do," she answered with a sneer. He had no idea what fuchsia or glamour length meant but seeing one inch long bright pink oval finger nails was more information than he wanted. As he paid and tipped the manicurist his face matched the color of his nails. He curled his right hand as tightly as he could with the long nails as he left the shop. The bright blue bag with Sally's Salon printed in white letters was too big to stuff into his jeans pockets. Almost immediately he discovered what a pain long fingernails can be when he tried to ball his hand into a fist or hold the steering wheel. "Crap! How the hell can I do anything with these talons? OMG! She doesn't plan on me keeping these things when I go to work, can she?" Of course his worst fears were realized but she did allow him to remove the polish when at work. He was required to paint them as soon as he arrived home and send a picture from his cell. The difficulties of having long nails were driving him crazy. Even simple tasks like securing buttons or picking up objects took a major effort. Trying to keep them from being discovered by his workmates was mind numbing. Some how he managed to get through the work week without any comments. Ooo Friday when he arrived home, he quickly stripped down to his pink with white daisy appliqu? nylon panties and matching camisole before sitting down to do his nails. When his nails dried he checked his email. He was surprised that Mistress hadn't sent him any new tasks. At first he was happy but then started to worry. "She didn't send me any new instructions? I hope that means this is all she wanted. Yeah, she's humiliated the hell out of me so maybe now I can get out of this damn thing. I'm hornier than I've ever been and think if I don't get some relief soon my balls are going to burst. Damn that woman!" He didn't hear anything that weekend nor the following week but he did send some pictures on a daily basis. He thought about stopping, getting rid of those ridiculous nails and buying some new underwear but decided to play it safe. Just because he didn't hear from her didn't mean he was off the hook but it gave him hope. Friday he turned down the offer to have some drinks using another flimsy excuse. Thanks to his long nails and lingerie he had to sever all of his outside activities. The only good thing about his week was that his buddies hadn't noticed his long nails although a couple of girls at the office did mention it. His excuse was that he lost a bet with his girlfriend. He had no idea how long "his girlfriend" excuses were going to work but couldn't think of anything better. James didn't like the feeling of exposure wearing just his panties and camisoles. Having to paint his nails when he got home didn't ease those feelings. He wasn't sure of what he would do if someone, especially the landlord or one of his friends from work knocked on his door but he didn't dare stop. His balls were aching for release. He had been an avid masturbator and popular with the ladies. Going so long without relief was madding. When his nails dried he turned on his computer with hopes that there would be a message from Mistress telling him he was free. There was indeed a message from Mistress and as he read it his eyes bulged out in disbelief. "I talked with Doris the woman who waxed your body at the salon and made an appointment for you Saturday morning at seven o'clock. She has agreed to open early so you can have your hair styled. Isn't that sweet of her? So I better hear that you had a happy smile on your face. I told her what I wanted and you will comply with whatever she tells you enthusiastically. Make sure you thank her profusely and leave a good tip. I look forward to seeing your picture. Mistress." James managed to keep a smile on his face at the salon but as he walked out the door shed some tears. Doris had dyed his hair a brassy blonde and set in a mullet style. Making matters worse she had back combed and teased it. The style was bad enough but no real man would have that color. She added to his monthly waxing appointment another set and style. Doris wasn't all that happy about opening so early but what she charged and the tip was more than worth it. "At first I though he was being blackmailed when I saw that chastity thing but when I did that dye job and cut he seemed so happy. Like they say 'it takes all types'. He must be gayer than a three dollar bill," Doris thought as he walked out the door. When he arrived back at his apartment there was a box sitting by his door. Taking it inside he opened it and found a lavender organza with pink floral lace trimmed apron. A note on top written in letters cut from magazines stated, "A gift from Mistress So far you have done well Wear this when home and doing your chores I think a nice thank you is in order when you send me a picture of your new hair style and wearing my gift." "OMG! The bitch knows where I live. Shit!" he yelled slamming his fists down on the kitchen table. When he regained control of his emotions took the obligatory picture. Before he sent it begged her to stop torturing him and he would pay her whatever she wanted if she would let him out of his chastity. He did remember to end it with, "Thank you so very much for the beautiful apron." It wasn't long before he had a reply and it wasn't what he hoped for. "No you cannot get a haircut and you still have tasks to complete if you ever want out of chastity. As punishment for insolence you will wear your fuchsia nail polish to work and I better not find out that you covered your pretty hair. I will be checking up on you. I know where you live. I know where you work. I will call or come by for a visit at any time day or night. Mistress." "I'm so fucked," he said as tears filled his eyes. Ooo Needless to say James' appearance at the office caused a major stir and his boss called him in wanting an explanation. He doubted that his lost bet excuse would work but what choice did he have. If he told the truth he would be stuck for life. He was right. The boss didn't look like he believed his story but told him that the company had a strict anti- harassment policy. "James, I certainly don't approve of what you have done to yourself but the firm has a strict anti-harassment policy and acceptance of differing life styles. So it doesn't matter what I think and if anyone gives you any problems let me know. I'll send out a reminder notification. Now get back to work." He was both relieved that he wasn't going to be fired yet upset that now everyone would probably think he was gay. The firm's affirmative action policy wouldn't guarantee he would still have friends. Worse, any one trying to make friends with him would probably be gay. He hated homosexuals. He wouldn't have to hear any more derogatory comments either but that didn't ease his humiliation. He could still see the disgust in their eyes whenever they met to discuss business. He would be tolerated but that would be the best he could expect while at the office. He was surprised that Jake and William his two best friends grudgingly accepted his story of a bet gone horribly wrong. They tried their best to get him to stop but he told them losing would be too costly. Not accepting their offer to meet Friday for drinks didn't help. Friday evening he had the expected email. "Very good and I loved the pictures. Now for your next task, tomorrow you will go to a thrift store and purchase the following: 3 pairs of stretchy Capri's in bright colors or floral designs. They must be skin tight 2 pairs of satin flare legged slacks, one in purple the other black again must be tight fitting 5 satin or silky polyester floral blouses 1 pair of black pointed toe women's flats 1 pair of 2 inch stack heeled red pumps 1 pair of silver or gold three inch spike heeled strappy sandals 12 pair of panty hose in various shades You have until noon to send me pictures wearing the Capri pants with a blouse and 2 inch heeled pumps. Mistress." "As if I didn't look fruit enough with this fucking hair and nails, how much more of this can I take?" The trip to the thrift store wasn't so bad. He arrived as soon as it opened and the only customer. He was greeted as he walked in by a grandmotherly looking woman. She introduced herself as Betty and the proprietor of the shop. "Oh dear another one of those poor souls that believes he was born in the wrong body. I've had more than my share come into my place but a sale is a sale," she thought then brightly smiling said, "Hello dear, I'm Betty and own this shop. How can I help you today?" "Errr..hello...I...I need this," he replied nervous but determined to get his odorous task completed handing her the list. He walked out of the store with a minimum amount of embarrassment. Betty didn't take long to find the items in question smiling and courteous as she found his sizes. She didn't bat an eye when he asked if he could try them on directing him to the change room. It would be humbling but he had to make sure the pants were skin tight as directed. Wearing a pair of white Capri's with bright floral decorations running up the legs he blushed at seeing how prominent the crotch bulged out and how big his ass looked. The back seam dug deeply into his ass crack separating and plumping up his derriere. It also dug into his groin mashing his balls painfully. Betty saw him grimace in pain as he turned around looking at his reflection. "Excuse me dear, you know I've helped others with that same problem. If you don't mind a bit of advice get a larger size or a girdle. I'll try to be delicate but you need to push your testicles back up inside your body if you insist on that tight of fit. My customers told me that with a good support garment the pain goes away. I'm so sorry if I embarrassed you but would you like me to fetch a girdle to try?" That was humiliating but she sounded very sincere and only trying to help. If he had to wear this stuff he figured he might as well be comfortable. "Ye...yes...errr...please," he answered. She returned with three girdles in hand and a small plastic container of baby powder. "I could only find three in your size dear but it's all I have at the moment. Why don't you take them and give it a try. They're rubber lined like most vintage girdles so use this baby powder to make putting it on easier." Back in the change room he examined the girdles more closely. One was muted white with a bright satin diamond front panel stitched with silver thread in a floral pattern. The second was purple but the same style and the third was yellow but had mid-thigh length legs. He decided to put on the white girdle as it was the least feminine looking. He had never heard of pushing up his balls and stood uncertain as how to do it. "Dear, use the palm of your hand and push up gently," he heard through the curtained doorway. James grimaced as his balls popped back up inside but the horrible pain he was expecting never materialized. As quickly as he could tugged the girdle up his legs and wiggling his butt got it settled around his waist. Its tight constriction felt weird but his front was flatter when he stepped back into the Capri's. The thrift store didn't carry hosiery so had to stop at a drug store on the way home to purchase the required panty hose. Betty had told him what size he would need and explained how to put them on before donning the girdle. The girl at the drug store counter looked at him funny but didn't comment as she rang up his purchases. It was just another day to her but another humbling one for James. Back at his place he changed out of his male attire and put on the ecru panty hose, white girdle, white Capri's with the floral design, black with bright pink daffodil imprinted polyester cap sleeved blouse and black flats. Taking several pictures emailed them to Mistress. It didn't take long before he received a response. "How perfectly lovely, that outfit is definitely you. Now I have another assignment for you to complete today. Buy enough web cameras so that I will be able to observe you wherever you are in the apartment. Make sure they are high resolution. Go as you are dressed right now. You have two hours to purchase and install them or you can forget about getting free. I recommend you buy the wifi wireless low light ones. Mistress. James sat in disbelief as he read and re-read the message. "OMG! She has to be shitting me! I can't possibly go out looking like this! Hasn't she humiliated me enough already?" "Mistress: Please I'll do anything. I can't go anywhere looking like this. Haven't you done enough to me? I'm already a laughing stock at my office. Please don't make me do this," he replied. "I can't see why you are complaining. You look very sweet in that outfit. Besides I still have a few more tasks for you to complete. You have one hour and forty-five minutes left. You better hurry." "That bitch!" he screamed reading the email. He was seen by several others as he left his apartment complex and even more in the crowded electronics store. The clerk that waited on him had a hard time not laughing and had a look that said, "Why do I get all the crackpots." The cameras put a very serious dent into his credit card but had them installed and operating with fifteen minutes to spare. The shopping experience was the worst day of his life and fortunately most people just had a good laugh at his expense. He did receive some derogatory slurs but not many. His face was flushed all the way home and it took all his will power not to cry. "Very good my pet, the camera views are excellent but you seem to have forgotten to put one in your bathroom. Do it now." "My bathroom?" he quickly replied while thinking, "She got to leave me some privacy." "Yes! Now!" "That's much better pet. From now on I want you wearing one of your new outfits every day when you are not at work. Yes even if you have to go out on an errand. By the way I must compliment you on taking the initiative and buying a girdle. The girdle lines make your ass so sexy in those tight pants. Make sure you keep wearing them all the time just like your pretty panties and camisoles. While I'm at it you forgot to polish your nails when you came home. As punishment you will also wear your new panty hose to work and I want you to buy a pretty pink lipstick to match your polish. I believe you have another errand to run dear. I'll give you an hour to make that purchase. Oh you might want to pick up a nice purse while you are out. Your new pants don't have any pockets and you need someplace to put your cell, wallet, keys and lipstick. I'd hate it if you missed one of my calls but not nearly as much as you will. Mistress" Ooo A sharp pain coming from his entrapped penis woke James up early Saturday morning. "Damn that woman! I've got to get this thing off. Every time I get a woody it hurts like hell down there. Gawd! I need relief so friggin bad." Giving up on trying to get back to sleep he got out of bed and headed to the kitchen to make coffee. Other than his chastity he was completely naked. He hated wearing panties and all the other feminine crap but at least he could sleep naked. With coffee in hand he went to check his emails like Mistress instructed him to do first thing every morning. After yesterday's humiliations he was hoping she would leave him alone. Again, no such luck. "You disappointed me this morning. Why aren't you wearing your panties and camisole? Mistress" "Crap, I forgot the friggin cameras," he thought before typing, "I like to sleep in the nude." "That just won't do. Today I want you to dress in your nicest satin pants and that lovely baby blue satin blouse with the red pumps. Go back to that lingerie store and buy three girly-girl negligee sets. No pajamas, nothing in cotton only the softest nylon or silk will do for you. Don't forget to wear your new lipstick or that I am watching you. Mistress." Mumbling curse words James went to the bathroom to clean up with hopes that he could get this task done with a minimum of embarrassment. It took him less than twenty minutes to finish up and was stepping into a pair of silver nylon tap panties with two inches of floral lace trim at the leg hems when his cell rang. "Check your email," was all Mistress said. "Crap! What the hell does she want now?" Slipping on the silky matching cami headed back to his computer. Opening the email let out a groan as he read, "You have a horrible morning toilet routine. While you are out pick up the following items: 1. Dove moisturizing soap 2. Lavender scented bath beads 3. Pink bulb syringe (you'll find that in the feminine hygiene aisle) 4. Panty liners (same place in store) 5. Lavender scented body talc 6. Once you have all these items in your basket go to cosmetics counter. Ask the clerk to assist you in finding a selection of facial cleansing and moisturizing products. Have her recommend a good skin care instruction book. Have a nice day. Mistress P.S. Almost forgot you need to hand wash your panties, camisoles, hosiery and girdles each night. They are too delicate to put in the washer so buy some Woolite." He went back to his bedroom to finish dressing his face flushed. "Damn that woman! It will be bad enough having to go back and face that clerk in the lingerie store but now this. I hate what she is making me do. I have to get this chastity off but how much more humiliation can I stand?" He removed the purple girdle and black panty hose from his dresser and put them on. The purple satin flare legged low rider slacks zipped up the side hugging his skin before loosening up just above the knee. The baby blue satin blouse was fairly plain with a pointed high collar and long sleeves. He had some trouble with the red pumps as he wasn't use to the heel. The heels threw his balance off forcing him to hold his shoulders back. "Here it is Saturday morning probably the busiest shopping day of the week and I have to go out looking like this. People are going to think I'm the world's biggest flaming faggot. If that woman wanted to humiliate me she's already royally succeeded. So how much further is she going to take this? I don't know if I can endure much more but I just have to get her to release me. This friggin chastity is killing me."