Andrew The Unsuspecting Sissy Part IV free porn video

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ANDREW THE UNSUSPECTING SISSY PART IV [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUS FAR..... ANDREW NOW DREW: SISSY SUPERSTAR, SOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIALIST, WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR ALICIA NEWMAN: MEDICAL DIRECTOR OF THE MANOR PENELOPE HUGHES: THE MANOR HEADMISTRESS CLAIRE: DR. NEWMAN ASSISTANT WE'RE OFF TO SEE THE WIZARD Sarah had just witnessed her stepbrother's most recent humiliation and she felt a heat between her legs. Why did sissy love excite her so? She was at a loss, but knew that being roommates with Drew would rekindle her dominant sexual spirit. Putting the faux boy through his paces and teaching him to worship men was going to be a joy. But now, she had to gather herself and head over to meet Jim. She had a very important task and would need the help of yet another sissy. The Manor Headmistress had suggested Kat and told her that the sissy would be ready to meet her in the carport. So, Sarah had to freshen herself. She slipped her panties down from underneath her pencil skirt and carelessly left them on the floor in front of Drew's bed. Drew will be so surprised, she thought, his lingerie is rather juvenile and far too femme for a real woman and besides he was forbidden from wearing black or red under things. Drew was more of a pastel sissy anyway. It's going to be so nice to have someone to pick up after me again, thought Sarah. She dashed into the bathroom and freshened herself and then made her way to the carport. When she opened the door her heart skipped a beat. Kat was as promised: a very polished, poised sissy. She wore a red three- quarter length scoop neck cardigan sweater with chain print silk button- down inset. Pointy collar tops, open neck with covered button trim. Such a pretty sweater thought Sarah and I want it! The sissy's skirt was rucked black satin with detail on front waist. It was a stretch fabric, which always insures a tight fit, so Sarah knew this sissy must be tightly gaffed. The shoes were black peep toe pumps. Luxurious satin 4 ? inch shoes with sexy ankle straps. Under her thin arm she had a stylish black purse. "Kat is that you?" "Yes ma'am", said the raven haired sissy "I understand you'll be assisting me today." "Yes ma'am, I hope I'll be of use." "I think you'll be just perfect. How tall are you?" "I'm 5' 9"." "Hmmm and who styled you today?" "I did ma'am, I'm allowed to pick my wardrobe now." "Think about a nice big belt for outfits like this one. Your waist is so diminutive; you'll be sure to draw attention to it. Plus with your slim hips, it's a can't miss that will have men drooling. Now tell me precious, who did your make up?" "Thank you for the ideas. I went to the salon for hair and make up ma'am." "Very well then." The Driver opened the door and helped Sarah into the limo. The Driver then assisted Kat into the car but Sarah stopped her midway and asked her to raise her skirts. Immediately, Kat lifted her skirt giving the Driver and the Sarah a view of her most private part. "What an adorable panty Kat." "Thank you ma'am." said the surprised but obedient sissy. Sarah slowly but firmly pressed her thumb on Kat's vee from deep between her legs right up to the pretty ribbon flower on the waistband of her panties. The sissy sighed from the intimate ministration. She had no fear of soiling her black lace, French cut satin panty as she was tightly gaffed. Once Sarah surmised as much, she brushed an invisible wrinkle and removed her hand and instructed the panting sissy to drop her skirt, at which point the Driver assisted her into the car. "Sit close to me I have some instructions and I want you to listen closely. " And with that the car left The Manor. THE DOCTOR WILL SEE YOU NOW In her private office at The Manor, Audrey was on her couch preparing for the video conference with Jim, Dr. Newman and today's sissy star Drew. "Jim, can you hear me?", said Audrey "Yes, I have both audio and video", said Jim. "Okay, that's great, our tech staff is top notch as you know and it needs to be with our demand for web content and our DVD sales." "I've reviewed the numbers and they are most impressive Audrey. I had no idea there was so many others who felt as I do." "Jim, you are not alone by any stretch of the imagination. These sissies are very attractive and are in high demand. But enough self-promotion, let's chat about our Drew! As you know, Drew has never been with a man or a woman. The daily milkings have been her only sexual release aside from her not so very private diddlings, which we have monitored. As you know Jim, Drew is not allowed to grip her small symbol. She can rub to her hearts content as long as she's wearing a panty or other approved garment. However, she hasn't held her erection as an adolescent. That's over seven years now. When she goes potty she is of course supervised." "I've seen the video and I found it to be fascinating. No matter what the temptation, she never grips her small penis. I don't think I could handle the temptation." "Jim, you're all man and well, Drew just really doesn't have any manly tendencies. We allow her these silly releases, but on our terms. Just think of it as preparation. Her focus will be on you and that's all the pleasure she'll need. By the end of her training she'll get more pleasure sitting on your lap and pleasing you than she will from rubbing herself. In fact, you'll notice that she'll have strong orgasms from things like oral sex and being taken by you. Yes Jim, you will be the first to deflower our precious Drew. But, prior to that occasion, we'll need to provide Drew with some valuable training in the art of pleasing men. You realize that prior to the episode of just a few moments ago, Drew had no experience with anybody but Sarah (my Daughter), Valerie (her private Docent) and myself. So having those two Candy Striper sissies rubbing the hormone cream all over Drew and causing her to ejaculate in her panties was a first for our little lamb." "I see, Said Jim. No wonder she was crying and even fainted. So what's on the agenda now?" "Glad you asked. Drew will be cleaned and prepared. Expect her to be flushed and overwrought and you should get used to that look because she'll be experiencing new sissy things every day from now until your wedding and I won't even mention you wedding night! She'll be placed on the platform in the middle of the room and we'll talk with Dr. Newman about everything from permanent make up to piercings and plastic surgery." "Will Drew hear me?" said Jim "No absolutely not and she won't hear me either, however she will hear Dr. Newman and that should be a treat what with her high drama. Remember that she still thinks of herself as a sissy boy and has never been with a man before, but we'll change all of that and by the time we're done, Drew will love everything about the penis and more importantly everything about you!" Jim laughed, "I must confess, I find Drew's discomfort most enjoyable." "As do I," said Audrey, "and the exciting part is that you'll never tire of it." Just then a voice came over both headsets, "Testing 1-2-3." Both Jim and Audrey chimed in, "I hear you Dr. Newman." "Very well then, please call me Alicia." "Jim, Alicia is a well-respected Endocrinologist and Board Certified plastic surgeon. She has become an expert at seeing the inner girl in all of these special precious boys and when she's done her magic, even the most discriminating eye can't detect what secrets her creations have between their legs!" Pleasantries were exchanged and then Dr. Newman took center stage. "Well today is an exciting day and our star should be ready in about 25 minutes. We'll just have her powdered and pantied and we can begin what I think will be a delicious decision making session. And Jim, let me be the first to congratulate you." "Thank you Alicia. I've been waiting for this day for quite some time." "Also, Jim don't forget that my Daughter will be by for a special 'fitting'. Of course we've found a way to make it most enjoyable for you." "Audrey, I can always depend upon you to satisfy all of my needs meticulously." A CAT FIGHT Just two doors from Dr. Newman a fight was brewing. Drew had flatly refused to let the sissy Candy Stripers change him out of his wet panties. The Candy Stripers had put their uniforms back on and were now trying to reason with Drew. "If you don't let us change you out of your soaked panties and clean you up, we'll all be in big trouble!" "I don't care!" Yelled Drew as the he/she stamped her heeled foot. "Don't you dare touch me." The Candy Stripers giggled, "But we just did that and more! So please let us change you. All we have to do is take off your panties and clean your ... little area, apply some powder and then dress you in a cute new bra and panty set. Plus we think you'll like what was selected for you." The first Candy Striper held out the matching bra and panty. But, Drew still balked and now all the sissies in the room were clearly frustrated. Just then the door opened and Claire returned with a menacing look on her face. "I see a sissy still standing in a soaked panty. Why hasn't Drew been prepared for Dr. Newman?" Both Candy Stripers said they tried and told on Drew who was now even more frustrated. "Drew is all of this true? Why don't you want to get out of your wet panty? Don't you like the pretty things Dr. Newman has chosen for you?" Drew was shaking again and didn't know how to respond. She just looked down and stared at her heels. Claire was losing her patience and without as much of a hint came toward the pedestal and delivered a barehanded slap to Drew's inner thigh that immediately raised welts on Drew's tenderest flesh. The sissy immediately screamed with pain and fell to her knees. Claire whispered into Drew's ears, "Darling I'd love nothing better then to heat up your behind and goodness knows you deserve it. You're spoiled rotten. But I'll give you one last chance and ask nicely, will you allow the 'girls' to change you out of that wet panty and into the outfit Dr Newman supplied?" Drew was defeated, Drew almost always felt defeated and with a whisper she replied, "Yes ma'am." "Yes ma'am what? You simpering little pantywaist." "Yes ma'am, I'd really like the girls to help clean me up and dress me in the outfit Dr. Newman selected for me." "Will there be any problems?" "No ma'am." "Very well, I'll watch just to make sure." The two vixen sissy Candy Stripers were like kids in a candy store. Drew slowly stood up. With only Drew's little bra and wet panties to remove, the girls took every opportunity to brush up against Drew in the most intimate ways and in a few moments Drew was quite naked in front of the mirror and his tormentors. While they giggled, Drew fought the tears back as her small shoulders started moving up and down. "Drew darling, are you cold?" said Claire "No ma'am," replied the confused sissy. "Well, your little peanut is so shriveled and small I thought you might be cold." "No ma'am." At that point, Drew was being cleaned in her nether region and then dusted with powdered and very quickly fresh panties were slid up her silky, smooth legs. And in that time disaster occurred. Drew felt an erection coming. Her stem was stirring and the little cotton panty could offer no protection. Immediately she wished she could have been securely gaffed. Nothing bad ever happens to me when I'm gaffed she thought. Claire didn't miss the signs and saw Drew's tiny erection. "Don't you dare stretch those panties or wet them." But the more she yelled the more excited Drew became. Claire came forward, stepped onto the platform and reached into Drew's panty. She locked her eyes onto Drew's. "Drew, darling, I know you like these little boys playing with you. I can only wonder how much you'd enjoy being with a real man. Real men are rough and they get their needs fulfilled by real women and sissies just like you!" While she was talking to Drew, Claire busied herself in Drew's panties inspecting his insufficient manhood. Her eyes remained focused on Drew's and Drew dare not look away. However, as Claire manipulated Drew, Drew closed his eyes for just a moment trying to lose himself in the intimate pleasure. Had his eyes been open at that moment, he would have seen a cruel smile on Claire's face. "I see the thought of a real man excites you, your tiny little stem is throbbing in my two fingers. Well, if you're a good girl, I'll see what I can do for you in the man department. But right now we're late and we can't dawdle!" Suddenly Claire reached down further into Drew panties and found one of her delicate pearls, which she squeezed between her thumb and forefinger. Drew yelped in pain and horror and immediately felt the urge to vomit. He crumbled to the base of the pedestal and tried to move away, but Claire pinned the weakling and would not relent. After some moments of begging, Claire got up. "Stand up missy!" Drew stood up and no one was surprised to see that while she was clearly shaken, she was calm in her panties. The girls dressed Drew in a two- piece bra that matched the cotton panty. The outfit was rather drab, so Claire stepped forward and applied red lipstick to Drew's cupid bow lips then placed a tissue between her sweet lips and told her to kiss. "Okay then, let's get our girlfriend here across the room to the main examination room. Oh, and Drew, you'll have to answer for your bad behavior today." Drew once again dropped her shoulders and was defeated. These women were unrelenting. To herself she could admit that she liked looking pretty and wearing her pretty things, 'But they just don't leave me alone. And, all this talk of men. Didn't they realize that she didn't like men, that she was attracted to women especially strong women?' The two Candy Stripers escorted Drew out of the room in just his bra and panty set with his heels clicking rhythmically. Claire admired Drew's cute shape. My, she's rounding out beautifully; I can only wonder what Dr. Newman has in store for her. It wouldn't be long before she found out! UPSTAIRS AT THE MANOR Valerie entered Drew's suite and it was a beehive of activity. All around the space were sissies and security staff. Valerie always admired the security guards/ life guards/ Drivers/ landscapers. The Manor attracted some of the most desirable male specimens. The unfortunate part was that these hulks had a penchant for sissies not women. Sean and Glen were certainly no different and were assigned the task of moving Sarah's things into Drew's rooms and arranging all of the furniture. They were indeed powerful men and their muscles were bulging under their wife beater tee shirts and tight tan chino's. Also assigned to Chambermaid duties were Carly and Suzette. Both of the young sissies were barely twenty. While Carly had embraced her training, Suzette had been far too reluctant and chose the harder route. But today they were dressed in gray day uniforms with scoop necks and short starched sleeves and sensible low heels with appropriate stockings. They had their hair swept back and pinned under smart lace caps. Both wore very little makeup, but what they had on was more than acceptable. Like two little schoolgirls they snuck peeks at the men working and then giggled at their boldness. The feminine creatures were whispering to each other when Valerie announced herself. Carly was so surprised she dropped her duster, then picked it up and curtseyed. Suzette remained quite calm, which quite frankly wasn't the response Valerie wanted. "I guess you two must be finished here said Valerie." Both sissies looked at each other but did not utter a word. "Are you two deaf?" "No ma'am," they chimed. "Well are you finished?" Both hesitated, and then answered that they thought so. "So you've arranged all of Drew's things and Sarah's things and all the linens have been changed and the room has been dusted and the mirrors are sparkling and the bathroom is pristine?" Now both sissies were looking at their shoes. The men had stopped moving and were now watching as well. Valerie enjoyed the audience. "We'll see, and we'll see right now!" Now both sissies were visibly agitated. "Stand still and heads forward please." "Yes ma'am," came the response in unison. Valerie began her inspection and left no stone unturned so to speak. Windowsills were checked, under the beds, dressers, and closets. After a few minutes, Valerie came out of the bathroom. She looked at the two sissies and smiled. "Nice job girls!" The sissies couldn't help but be proud. Valerie was no easy taskmaster and if she was pleased, they had really exceeded expectations! The men chuckled and at that point they were finished as well. The furniture was fabulous. Sarah had a king size bed with beautiful Egyptian cotton sheets in rich beiges. She also had a matching love seat. Drew had her queen size bed removed and was now furnished with a twin bed with rubber sheets and rainbow colored bed linens. She had a small secretary with a little typewriter and a little chair. The bathroom had been modified after Sarah and Audrey agreed that sissies and Mistresses do not share the same makeup mirror or cosmetics. All in all Valerie knew that Sarah would be pleased. Just one more task and it was playtime! "Suzette, gather all of Drew bras and panties and other finery and place it into the locking draws under her bed." Suzette paused, realized her mistake and then went straight to the dresser. The men were leaning against the wall watching as Suzette would take a panty from the drawer snap it between her hands and then fold the delicate item. One by one all of Drew's most intimate articles were displayed. The men were also enjoying the fashion show. After the chore was completed Valerie approached the men. "Gentlemen, you've done a great job. Perhaps you'd like a bit of R & R?" The men smiled and so did Valerie. "Sean, why don't you go into the bathroom and get undressed." "Yes ma'am," replied Sean enthusiastically. "Suzette darling, I'm sure Sean will need your special skills in the bathroom, please don't keep him waiting." Suzette wanted to go into the bathroom; she wanted to feel Sean's largesse and to excite Sean. She wanted to do all of these things, but didn't want to seem eager; She just didn't want to give Valerie the satisfaction. Valerie being experienced with all things sissy knew what Suzette was up to. "I suggest you move your behind or perhaps you'd rather I assign you to other less interesting duties." Suzette bit her lip and lowered her eyes. "No ma'am said the sissy and she scurried into the bathroom." Valerie had now moved behind Carly and had her hands on the effeminate boys shoulders running her fingertips over the shoulder straps of his bra straps through her well starched uniform. "Glen, do you find Carly attractive?" Valerie could feel the flush rise in Carly and when Glen shook his head yes, Valerie could feel Carly shiver. "I'll tell you a secret Glen, I think Carly likes you as well." Glen smiled, he walked up to Carly and took the sissy in his arms and lifted her off of her small feet and kissed her directly on the mouth. Carly was surprised and delighted and willingly accepted Glen's kisses though, she thought beard was far too scratchy, he smelled like sweat and he was very rough. In short, Carly was in heaven. She reached her arms around his neck and let him set the pace as a sissy is trained to do. Her only contribution was a willing mouth and a thigh that was busy rubbing back and forth over Glen's rather sizeable erection. With Carly well in hand, Valerie entered the bathroom and found Suzette in her little pink bra and matching full cut panty fellating Sean in the shower. Sean was clearly enjoying the attention and only briefly looked over when he realized Valerie was watching, but Suzette never realized Valerie was in the room. Her training had served her well; she was concentrating on Sean's penis, as she should be. Valerie found her technique to be advanced. She would tease Sean for several seconds and then apply some rather accomplished deep throat techniques, followed by some hand pumps using her thumb to excite the underside of Sean's manhood and then some enthusiastic head nibbling. Suzette made sure that she didn't close her eyes and left them locked on Sean. He was her man and she was going to make sure that all his needs were met. She had learned her lessons well indeed and Valerie knew that Sean would soon desire something more of her. Valerie left the bathroom to find Carly on Glen's lap. They were on the rubber sheets of Drew's bed. Carly was in just her hose, a peach cotton panty, a gaff and her pretty bra was now wrapped around her skinny waist. She had her arms around the neck of Glen. However, Glen was naked and Valerie could see that Carly was playfully bouncing her pantied bottom up and down on Glen's sizeable shaft while she nibbled at his lips and alternately rubbed his huge chest and shoulders as she freed her hands from behind his neck. Glen was putting his free hands to use, playing with Carly's full a-cup breasts. He was pinching and chaffing the moaning sissies sensitive nipples alternating from one immature breast to another. The more Glen played with the willing she-boy's breasts, the more animated Carly bounced on Glen's manhood. Valerie was happy for Carly. She was the runt of her class and had worked hard on her looks and mannerisms. Her attitude had been excellent from day one and she was the first in her class in so many different exercises, particularly her transition to pleasuring men. She had been so enthusiastic from age 15 and men had found her interesting when she had grown out her hair and finished The Manor's diet and exercise programs. Her ballet and gymnastic training made her an irresistible sprite. And now here she was on Glen's lap and Glen was meeting every bounce of her bottom with a thrust of his own. But, the darling stayed safe with her panty and gaff covering her bottom. Glen was surprised when Carly swung her legs over his thighs and straddled him. His large erection was now between her bottom and Valerie thought that Glen was masturbating himself on Carly's pantied behind... how marvelous. Carly caught on quickly and met each thrust with one of her own. Glen had his hands on Carly's waist and the tips of his fingers were almost touching. His sweaty face was buried in her small cleavage. He couldn't hope to last much longer and to make matters worse for Glen, Carly reached a perfectly manicured hand behind her and grabbed Glen's shaft. She was now looking back and licking her lips unconsciously. Using her bottom and her hand she was creating a frenzy. While her small had couldn't hope to encircle Glen's girth, she made use of her pantied behind by rubbing it against the head of Glen's now swollen and throbbing member. Just a minute later, Glen could stand no more and rocketed his semen onto Carly's back and her bottom. There was so much ejaculate and when Glen had calmed, Carly slipped to the floor to clean him using her mouth. Glen's was twitching with sensitivity and Carly confidently looked into his eyes as she sucked her wet fingers. If only Glen knew how exciting this was for Carly, thought Valerie and she turned and headed into the bathroom. The bathroom was steamy and it wasn't the work of the shower. Suzette's bra was now soaking wet on the floor of the shower and Valerie was happy to see that the tempestuous Suzette was still pantied and gaffed. Sean however, was a demanding lover and enjoyed putting sissies through his form of rigorous lovemaking. He was all muscles and penis and right at this moment he had a handful of Suzette's hair and was kissing her firmly on the lips while his massive thigh was between her thighs training her. His free hand spanned her pantied, wet bottom forcing it onto his thrusting thigh. All the while, the water fell on them. After several minutes, Suzette changed angles so Valerie could see that Suzette, while being handled as she was, had a firm grip on Sean's lance. In fact, she was masturbating him. This activity went on for another few minutes and then all of a sudden, Sean grabbed the fabric of Suzette's panty and with one fierce tug ripped the feminine garment off of the surprised sissy who gasped with shock. Now Sean only had Suzette's gaff in the way of his goal. With his thigh firmly between her's and Suzette pinned up against the shower wall, Sean let his hands roam all over the gaff. First the back of the garment and then the front. Valerie was delighted that Audrey was forward thinking enough to get all of the sissies powernet waterproof gaffs. These garments really held a sissy at bay and were great under the tiniest bikini. But, they were also pretty and just a bit smaller than a regular panty so they fit so well underneath them. A sissy could feel contact on her stem, but the material was so strong a sissy's small bits were kept in hopeless check. However, Sean was an expert when it came to gaffed sissies and he liked nothing better then to titillate their trapped symbols and today was no different. His thick fingers were tracing Suzette's stem and having found her little penis head, Sean was rubbing it like one would a woman's clitoris. All the while, Suzette moaned and continued to masturbate Sean. Sean, being the man, kept the fragile sissy pinned to the shower wall and being pelted by the warm water. Sean stopped the assault on Suzette's nether region and began kissing the sweet girl all over ending at her lips, which he sucked rather intensely. He used his finger to trace the outside of her lips and then stopped pulled his face away, looked into Suzette's eyes and pushed his thick long finger into her throat. He saw her eyes widen and felt her throat tighten. In Suzette's hand she felt him reach a new height of hardness and throbbing. He continued to force his finger down her throat and watched as her shoulders rounded and her abdominal muscles tightened. Her body wanted the offending finger out of her throat, but her mind was telling her to relax. Sean removed the finger and smiled and saw in Suzette's eyes a glint of satisfaction. So, Sean immediately placed two fingers into the willing sissy's mouth and pushed them well into her throat. Suzette began retching, but Sean was encouraging her. He was being sweet. Suzette had by now released her grip on Sean's pulsating penis. When Sean felt that Suzette had learned her lesson, he relented and removed his fingers leaving the sissy coughing and on her knees. Valerie was enjoying the dance and knew that Suzette was about to enjoy the pleasure of womanhood and Sean didn't disappoint. Sean stood her up and grabbed the front of her gaff and yanked it down. Sean was a strong man, but it took several yanks to get the tight garment down to Suzette's thighs. Sean was now looking down into the eyes of Suzette and was holding her stem in his palm. The penis was so small it disappeared. To tease her further, Sean bent at the knees until the two phalluses were next to each other. One measured 2 inches and was just erecting and the other, well that was a man's penis and was well over nine inches. Sean laughed and fell to his knees and sucked on the little peanut until it was as erect as it could be. Valerie thought that this sissy was very lucky to be getting this type of treatment. Sean then turned Suzette around and bent her over. He pull her gaff down just far enough to get at what he wanted and placed himself at her most private opening. "Push back on it," said Sean Suzette hesitated, not out of fear, but because this sissy was proud. "Do it." Then Sean smacked her behind and the sissy turned and looked him in the eye defiantly, but did as commanded. It took some doing but once Sean was in, he began thrusting. One short thrust followed by three long and alternating it. All the while, Suzette was moving rhythmically under the water with him. Their lovemaking lasted some time, until Sean pulled out and placed Suzette in front of him. He grabbed both sides of her small face and started pumping his penis in and out of her mouth. In just a few seconds he launched his seed all over her and into the warm jets of water. Valerie was flushed at what she had just seen. Thank goodness it had all been caught on tape. Suzette then bathed Sean, helped him dress and asked for his help to put her gaff in place because she wasn't strong enough to do it herself. Valerie couldn't figure out if Suzette had climaxed, but it didn't really matter. When Suzette realized that Valerie had seen everything she turned bright red. "Suzette, don't deny who you are. Embrace your submissive side completely. Attitude is everything. Now dry off and return to your room. Be sure to take your ripped panty with you and make sure that you and Carly leave everything in perfect condition. Oh, and do remember to thank the boys." And she winked at Suzette and left the room. "Yes ma'am," replied the acquiescent Suzette. ON DISPLAY The two sissy Candy Stripers led a flushed and frustrated Drew into the room. Dr. Newman asked for the open mouth gag and ordered that this most special sissy be placed on the large pedestal, which had a stool and a chair and was able to rotate. Dr Newman examined the outfit and noticed the welts on Drew's behind and thighs. "Sweetheart were you reluctant to join us today?" "No ma'am." "You're not scared?" "Well, y-y-y-yes I am, ma'am." "Don't fret darling. Rule one is always the best rule for a sissy; let all decisions be made by your superiors, which in your case is well... everyone. Okay sweetheart, I see that you're overwhelmed, so I'm going to help you." Quickly straps were placed around the sissy's neck and wrists and Dr. Newman ordered Drew to clip herself to her neck. Drew did as instructed and Dr. Newman congratulated her on her deftness. "Okay sweetheart, open your mouth as wide as you can." Dr. Newman attached the open mouth gag, which allowed access to her mouth, but kept her mouth wide open. "Good girl!" "How cute." Okay then now up onto the pedestal. Dr. Newman smacked Drew's pantied bottom playfully as she managed to step up in her fetters and heels. "Darling here is the tough part. To keep you still I'll be using a nose hook. It won't be comfortable, but you'll be fine." Dr. Newman showed Drew the nose hook and her eyes opened wide with fear. It looked like a stainless steel double fish hook without the barbed ends. While Drew was looking at that, Dr. Newman fitted the open gag around her head. Instinctively, the sissy struggled, but Dr. Newman was reassuring and with Drew's hands clasped to her neck, she had no choice but to submit. So she was fitted with the gag, which left her mouth forced open. "Her jaws will be hurting tomorrow," said Jim "I think it's delicious," said Audrey. Dr. Newman while still adjusting the gag said, "I think you'll see how effective this bit of equipment is. We'll have responses from Drew without her words." With the gag in place, Drew immediately started salivating and the fluid was dripping onto the floor and her two-piece bra. She was moving around on the pedestal and fighting to free her wrists. "She really is spunky," said Jim "Well, we've tried to keep her spirit intact, but as you know the training is arduous and sometimes these reluctant boys need to be completely broken down until they realize their place in life as a sissy," said Audrey "You're to be commended," said Dr. Newman. With every word spoken, Drew tried to figure out who was listening but she had no idea what was going on. Dr. Newman then attached the nose hook to the overhead metal cable. She then placed the hooks in Drew's nostrils and pressed a foot motor and the slack was removed from the line and Drew's head was forced up. Now Drew couldn't move, and if she fell she was afraid her nose would get ripped off. "This configuration should cut down on the drama and we'll have access to all parts of Drew's body without offending behaviors," said Dr Newman who had now placed her hand on Drew's tummy. Once again Drew was crying and drooling almost uncontrollable. Dr. Newman turned to face the camera, but with a free hand placed her fingers under Drew's pantied scrotum and with her thumb she stroked the length of Drew's tiny shaft. She did this without thought, but the effects on Drew were noticeable as once again our precious sissy began to erect. "All I can say is I never had a doctor like you, Alicia," said Jim. Drew calmed herself and was just sniffling. However, the drool was uncontrollable. Okay said Dr. Newman, I think we're ready to begin Drew's evaluation. NOT YOUR TYPICAL EVALUATION...

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ANDREW THE UNSPUSPECTING SISSY PART II ANDREW'S SISSY EDUCATION BEGINS............ [email protected] Mother and daughter chatted while they ate their breakfast. Several sissies flitted about changing flowers and removing dirty dishes. "Mother," said Sarah. "How many sissies call the Manor their home these days?" "Hmmm," said Audrey as she placed her coffee cup in its saucer. I'd have to say with the school, the modeling agency, the internet dormitory, the domestic...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

2 years ago
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Andrews Goodbye Party

My thirty year old wife Ceras and I enjoy a fairly liberal sex policy. You can imagine she gets hit on a lot which leads to a lot of swinging opportunities. Ceras has an average looking short twenty-eight year old former co-worker friend named Andrew that has always had the hots for her. She would never do anything with him because they worked together plus he wasn't her type and as a rule we don't get involved with friends. He's a funny guy and I get along well with him and always found his...

3 years ago
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Sissy Sex Therapist

SISSY SEX THERAPIST by Throne "But honey," Darren said in a whining tone. "You can't mean that. How could I be a... a sex therapist?" His wife Kelly smirked at him and said, "You have to understand, Darla, that a sissy like you could be very valuable in helping some men to deal with issues they have in their sex lives. For instance, the new guy I just started dating, Brad. He doesn't understand the whole sissy mindset, and how useful a weak feminized husband like you can be in...

4 years ago
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Sissy Stepson Part 4 Stepmothers Test

Part 4 - Stepmother's Test She crossed her legs and began dangling her high heel again and Carl became excited. His sissy stick started to stick up as he watch the dangling show and fashion models prancing on the run way. He had no where to escape and his stepmother noticed her panties bulging with his sissy cock. She nonchalantly let the shoe fall on the carpet and said, "Well, missy are you going to pick my shoe up and place back on my toes or can't you get up!" "Yes, ma'am, I...

3 years ago
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Sissy Therapy

Sissy Therapy by Kate "Great practice, guys! If we keep working hard, we have a real shot at the conference title," Coach Jones addressed the thirty or so high school boys gathered around him. The boys were sweaty and tired, but the coach's praise momentarily raised their spirits. "Smith nice passing out there. Keep up the good work." Fifteen year old Billy Smith grinned cockily. "Sure, Coach. After all, I am the greatest!" The other boys moaned at Billy's arrogance. Coach...

2 years ago
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Heathers Sissy

Heather's SissyMy husband, Bobby, is standing with his nose in the corner, quietly sobbing, as he contemplates the ill-advised temper tantrum that he threw this afternoon. His sobbing is due to a very sore bottom, for which I take credit foróalthough to be fair, my favorite wooden paddle should also take some of the credit too.I'm not sure what it was that finally sent Bobby over the edge today. It could be the fact that I arbitrarily extended his sentence of chastity for another month, or it...

3 years ago
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The White Sissy Slave Society A Walk into Sissyhood

The White Sissy Slave Society: Sold into Sissyhood By Meeah Soo They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car. It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. I'm very easily intimidated. And there I was in a tiny plaid mini and white...

4 years ago
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Andrew James Wellington III Esq Dead Beat Dad

Andrew James Wellington III, Esq. - Dead Beat Dad By Sirbosk1 ? sirbosk1 2009This story is a fantasy that contains scenes of Femdom, oral sex, rimming, cream pie eating, humiliation, blackmail, CBT, bondage, spanking, body modifications, and other erotic activities involving adults. If such subjects are offensive, uninteresting or if you are a minor, (i.e., child) please leave now. This story was written at the request of a sub fem friend of mine who’s husband recently walked out, leaving her...

2 years ago
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Andrew

Andrew by Grimbo Andrew slowly woke to the distant sound of a woman's voice. "Well sleepyhead," it said. "I'm glad you have finally awoken. You may be wondering were you are so I'll tell you. You're back inside Shannon's Boutique. You remember my store don't you? You came in here last week with your girlfriend and knocked a lot of the clothes off the rack. If my memory serves me, your comment was 'Let the staff pick them up. After all, that's what they get paid for.' Well,...

2 years ago
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Andrew Loses It

Andrew walked home from the party. No, he didn’t really walked, he stumbled and staggered, legs held as wide apart as he could, nursing an asshole that only a few hours earlier had been the virgin bud of a true stud, and was now gaping obscenely. Even as he walked he felt it throb and pulse… and he felt the warm liquid leaking down along his inner thighs – liquid that could only be Thomas’s cum. His mind kept going back to the party – a party to which he had been specially invited and to which,...

3 years ago
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Andrew

I met this guy Andrew on a website. He wanted to meet for coffee at the local coffee house. I agreed and met him at 2 in the afternoon. When I got there, he was conducting a meeting with some of his colleagues. I grabbed me an iced tea, then walked towards his table. Andrew pulled me to sit next to him on the booth bench.He wrapped up his meeting, then turned his attention to me. We sat close as we chatted about our likes and dislikes. His hands were all over my legs and arms. I didn't...

4 years ago
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Andrew and James

Andrew helps me put my stuff in my car, then he climbs in the drivers seat, to take me back to his house. Or so I thought. The man drove to the cute little boutique in town. "A Dream for Him" , Andrew lead me through the door with him holding my hand. An older woman built like a brick house stepped out from the back room. "Hi, Louise" Andrew said. Louise came over and kissed Andrew on the cheek and gave him a hug. Andrew introduced me to her and told me to go look around, as the two who...

4 years ago
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My Girlfriend madd Me a Sissy Part3

Here's the 3rd part of my story, I hope I didn't make you guys wait toolong. Hope you enjoy, its best read one handed ;-)My Girlfriend Made Me a Sissy - Part 3-------------------------------------------------I lay on Jess' bed waiting for her and wondering what would happen forages. She was in another room getting ready for her new lover, I wasalready dressed up. Pale blue, see through panties and matching bra, ashort black skirt and a blue vest top. With my make up done to show off mypretty...

3 years ago
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Andrew and Friend

Three months after Andrew and I had had relations I was close to his house and decided to pay him a visit, knocking on his door he answered it and greeted me like a long lost friend. As I walked into the lounge there was a young Asian lad sat on the sofa, they were playing video games. As soon as I walked in Andrew said “This is Ansa” we nodded and said hello. I sat next to him.Andrew made me a coffee and turned the TV off, we made small talk and Ansa worked at the supermarket where Andrew...

4 years ago
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Andrew Running Part 1 of Andreas Stand

Andrew Running (part 1 of Andrea's Stand) Chapter 1: Running I called my Aunt Clara from the bus station. She didn't seem that surprised to hear from me and when I explained why I was there she told me to walk a couple of blocks to the local diner and get myself a cup of coffee. She'd pick me up in about half an hour. I sat and sipped chocolate milk and tried to eat a pastry while I glanced nervously out of the window waiting for my father to show up and force me into his...

2 years ago
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Sissy Stepmother

Sissy Stepmother A Pantyboy Profile INTRODUCTION Cheryl here. You remember me. The 20-year-old pantyboy extraordinaire. Every man's naughty, secret, wet dream. Raconteur without equal. In "Service" and "Test Driven," I told you about Amy and Judy, two of my lovely roommates, fellow pantyboys and like me, covergirls for "Panty Boy," the only publication worth buying, besides some of those Spermco comic books about us "special boygirls" and the "Sunday New York Times." And Panty...

2 years ago
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Andrewrsquos Angel

Andrew always grew up feeling more then just a little different from the rest of the boys. He never felt sexually attracted to girl’s bodies but instead felt attraction for their clothes. He knew he was straight because he never liked guys so he just assumed he was straight. This began his seventh grade year and followed him into his senior year of high school. He started off by reading sissy literotica and watching sissy hypnosis. He then began experimenting by trying on his sister’s...

4 years ago
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My girlfriend made a sissypart1

Hey guys this is my first story ....hope you all like it ...When I was 18, in spite of my shyness and not being in anyway incrediblyattractive, I somehow landed myself a girlfriend 2 years older than me. Iwas quite short for a boy then, around 5'7 and very slim having not yetdeveloped much muscle. I had shoulder length brown hair and bright greeneyes and I simply couldn't believe my luck in getting this girl. She wascalled Jess, a beautiful redhead with a body to die for and an appetite forsex...

4 years ago
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Sissy Mission 4 Southern Belle Sissy

The Sissy Mission series consists of short-short stories designed to give ideas for domme/sub play, solo "outings," or just for your reading enjoyment! The goal is to have a dozen vignettes. --CA Sissy Mission 4: Southern Belle Sissy By Cheryl Alison Mistress believes in community service. So when she dropped the ad on my desk at home, I knew that I would be a faithful community servant within a short while. The ad read: Southern Belles Needed The Ladies' Auxiliary needs...

1 year ago
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Sissy Puppy Fifi Part2

Chapter 2 I tried as best as I could to get comfortable curled up in the corner of the room. At first I kept squashing my tail which either caused the vibrations to start or pushed the plug further inside. I had eventually worked out the best position to lie in when Mistress appeared. "Time for bed Fifi," she said as she attached the pink lead to my collar. I was then led through the house and up to her bedroom. This was a strange feeling to enter her bedroom not in my usual maid's...

3 years ago
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Andrews Girl Goes Black

Larry and Andrew had been friends for about 9 to 12 months. Larry was black, 6 ft tall with dark skin. Andrew was white a little taller than Larry. Andrew was dating Jen, she was Asian probably 5’ 3” with long dark hair and a tight little body. Priya was Indian about the same height as Jen with brown skin, shoulder length black hair, and a very nice little body also. Jen was very much in love with Andrew but very flirty with Larry. Larry thought she was being nice and didn’t think too much...

3 years ago
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Sissy Therapy

My advertisement read: MEN Interested in sex with other men but don't know how to proceed? Looking for a safe, friendly way to find out if this is for you? Obsessed by online bi/gay/sissy/crossdressing porn but frightened to meet someone? Is your marriage at risk because of your desires? I can help! One four-hour sexual therapy session will help you to decide if this is right for you, and will help you to understand your desires. Don't suffer alone, I can...

3 years ago
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SISSY DANI PART3

CHAPTER THREEMistress Jennifer and Mistress Susan's plans to create an entire"harem" of transformed men and boys continued apace. The lure ofTeasing Tammy (the transformation name of Susan's teen-agedbrother Tommy) proved quite effective. Each of the young men (theyoungest just 14, the oldest 22) the little tease brought back tothe home we all now shared was turned into a different kind offeminized sex-toy, all designed to please the Mistresses andtheir dominant friends.The little...

3 years ago
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Andrew CAW 10

Introduction: This is my story for the CAW 10, it is also a true story about a dark part of my life that I am just starting to come to terms with and wanted to share. Please try to be constructive when giving criticism to my story. Thank you to my last minute proofreader and to you the reader for taking the time to actually read my story. Vicki x This is my first attempt at writing my story, I have decided to enter it in the CAW 10 also. Please give me constructive criticism and try not to be...

3 years ago
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My Stepmothers Sissy Daughter

My Stepmothers Sissy Daughter By Malissa Madison The dream was so real, she was being chased by some evil thing that thirsted for her blood. She was cornered with nowhere to hide. She felt its hot breath on her as she tried feebly to squeeze through a hole too tiny to fit. The hot breath as it pushed its nose against her bottom. It felt hot and wet, Wet? She woke with a start in full panic unable to stem the flow. All she could do was lay there and cry in silence. She'd had this...

3 years ago
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Andrew CAW 10

Please give me constructive criticism and try not to be too harsh with me as it is my first story and a part of my life. Andrew I felt so lucky to have someone who loved and cherished me so much or so I thought. In my naivety, I gave him my virginity at the mere age of fifteen. It just didn't click that maybe he was using me for his own twisted pleasures. I always thought he truly loved and cared for me and my ambitions to go to art college. Everything was fine until I turned...

3 years ago
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Andrew to Ashleigh Part 1 The Change

My name was, once upon a time, Andrew McKenna; now it's Ashleigh Barnes, and how that happened is a long story. I figure the best way to start is to tell you about the day I died. At least, I think I died! Even if I didn't die, though, I for sure went to heaven. I never in a billion years would have thought things would have turned out the way they did for me. Stick around and I'll tell you all about it. The day I died (maybe? anyway, let's just say died, because Andrew is totally...

3 years ago
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Stepmothers Sissy Schoolboy

One-Handed Reading: A Step-mother's Sissy School-boy This is a one-sided conversation between an (evil?) step-mother and her delinquent step-son. ------------------------------------------ Author's Note: This is not some attempt at a Pulitzer, or to make some earth shattering literary statement. Nope. If you are looking for deep characterization or nuanced subplots, move on. This tale is not for you. I love exploring verbal humiliation alongside being dressed. This is what I call...

4 years ago
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Sissy Stepson Part 1 Stepmothers Trap

Sissy Stepson Part 1 ? Stepmother's Trap Carl Monet was a shy boy of about 15 when his widowed father married Rita Parker. Mrs. Parker was 20 years younger than Carl's father Larry. Carl was very shy and sheepish toward his new stepmother and the new Mrs. Monet was rather cold and distant towards him. Carl's father was gone quit often on trips abroad for weeks at a time and Mrs. Monet was often gone shopping with her sister Maryann and her mother Regina. Carl was...

2 years ago
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Sharons Mistress Throws a Sissy Party

Sharon’s Mistress throws a Sissy Party(Prior chapter is Sharon’s Sissy Saturday)The next morning Mistress was kind enough to let me sleep in, but an alarm above the door to my little cell went off at 6:30, rousing me from a delicious dream of being naked and fucked in the woods by a handsome, dark-haired man who kept me as his personal sissy slave slut. I woke with the sensation of his hard cock filling my dripping pussy, and I realized I was still leaking cum from my day in the booth. I...

4 years ago
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Sissy dannis birthday party

My last "true life" story was about how I became Heidi's sissy crossdresser "Danni" - I only explained the initial experience of Heidi coming home to find me in one of her dresses - followed by spankings, punishment and eventually getting pegged by her wearing a strapon. Of course there is MUCH more to what happened next (like being taken out in public and going shopping, to hair salons, etc...), but I'd like to for now jump ahead to what happened to me on my 19th birthday. By then I...

3 years ago
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Sissy Therapy Case Study 2

Sissy Therapy - Case Study 2 Shelly's latest client is John who is obsessively addicted to smooth, shaved men's asses, ideally covered by skimpy women's panties. Shelly helps him to come to terms with his desires and learn a lot about himself as well. Oh, lots and lots of sex as usual... ;) Hi, I'm a sexual therapist. Sort of. No qualifications, my only experience is what I've gained on the job. This is my second 'case study' which took place a few months after I started. To recap...

2 years ago
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Crowd Sourced Sissy Spin OffMothers Milk

NOTE: This story stems from an incidental bit in the "Crowd Sources Sissy" story that a couple of readers seemed to be interested in having me explore further. It's just a starting off point. You do not need to read that story first to understand this new work, but of course feel free to read it to get the full effect. Enjoy! Crowd Sourced Sissy--Mothers Milk I knew that my husband had a sissy fetish long before I married him. For many, that would have been a bridge too far,...

3 years ago
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Andrew Lake Part 1 Repost 2 My Kinky Chemistry Teacher

My name is Andrew Lake. I am a junior at Brickton High School, even though I just turned 18 last month. I don't consider myself unhappy, just a little out of place. I'm a smart kid, but I'm not the brightest bulb in terms of social interaction. I only had a few friends, all of which in similar situations as me, and not a single girlfriend throughout my school career. Hense, my porn addiction. Romantic relationships aside, I had a pretty decent life, just not a perfect one. My life was,...

4 years ago
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Andrew Lake Part 1 Repost My Kinky Chemistry Teacher

My name is Andrew Lake. I am a junior at Brickton High School, even though I just turned 18 last month. I don't consider myself unhappy, just a little out of place. I'm a smart kid, but I'm not the brightest bulb in terms of social interaction. I only had a few friends, all of which in similar situations as me, and not a single girlfriend throughout my school career. Hense, my porn addiction. Romantic relationships aside, I had a pretty decent life, just not a perfect one. My life was,...

2 years ago
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Andrew Lake Part 1 My Kinky Chemistry Teacher

My name is Andrew Lake. I am a junior at Brickton High School, even though I just turned 18 last month. I don't consider myself unhappy, just a little out of place. I'm a smart kid, but I'm not the brightest bulb in terms of social interaction. I only had a few friends, all of which in similar situations as me, and not a single girlfriend throughout my school career. Hense, my porn addiction. Romantic relationships aside, I had a pretty decent life, just not a perfect one. My life was,...

4 years ago
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Andrew Lake Part 1 My Kinky Chemistry Teacher

Introduction: Hey guys, this is my first story. Its based off of a dream I had, as will the sequels in this series. Please enjoy, like the story, and comment with any suggestions. My eyes hurt from staring at the small screen all night, but I couldnt bring myself to look away. I had been watching porn for what felt like ages, stroking myself to women on the internet doing unimaginable things to one another. I felt like a sick pervert inside, but I was far too busy to concern myself with such...

3 years ago
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Andrew Lake Part 1 Repost 2 My Kinky Chemistry Teacher

Introduction: And it happened again FFS. Made sure this account will not be deleted, enjoy the story and wait for more. I will be posting more I promise. Apologies for the technical difficulties ???? My eyes hurt from staring at the small screen all night, but I couldnt bring myself to look away. I had been watching porn for what felt like ages, stroking myself to women on the internet doing unimaginable things to one another. I felt like a sick pervert inside, but I was far too busy to concern...

3 years ago
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Andrew Lake Part 1 Repost My Kinky Chemistry Teacher

Introduction: Hey guys, so my account was rejected by xnxx after I had posted this, so for the sake of simplicity I am re-uploading it here. I apologize for the confusion. Feel free to rate and comment again, and stay tuned for the next parts, assuming my account isnt denied again. My eyes hurt from staring at the small screen all night, but I couldnt bring myself to look away. I had been watching porn for what felt like ages, stroking myself to women on the internet doing unimaginable things...

2 years ago
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Andrew

AndrewCouple of weeks ago, we had been down our local having a drink and laugh with friends, Hubby had a few too many, and decided to get a cab home, but I was hungry, and wanted to eat, so I thought a takaway would be the answer, but again having drank a bit, the restaurant was a mile or two away, but my prayers were answered, when a son of our friends offered me a lift there to collect and return me to the pub, well though I was slightly pissed, I got some money out of hubby and said to chas...

4 years ago
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Andrew 1

I was in my front garden in shorts and T shirt when my neighbour Karen came walking towards me very quickly and agitated. “Oh Andrew, can you help me please I’ve got a leak in the kitchen and I’ve left Brooke holding a rag round it? I just don’t know what to do.”Karen, brunette and hot single mum, wearing a short skirt and T shirt was the object of my wildest fantasies and needed my help. I jumped up, eager to do my bit, “no problem Karen, let’s see what I can do”. I followed her to her house...

3 years ago
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My Young Sissy brother for Mens Cum today

sharleesisterboyMY Young SISSY brother in Heat for Men's Cum, today!You used to prance around the house in your white underware, when Mom was gone, shaking your cute ass at me till I caught you, roughly, in My Big brothers arms and carried you to my bedroom floor. You giggled all the way, till I tossed you down on the dirt floor and you tumbled and smiled up at Me and lay on your tummy with your legs spread wide for Man-Cock. You know what I like to do to You, but, instead, I tie your wrists...

2 years ago
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Sissy Sisters Party

SISSY SISTERS PARTY by Throne Bob Clump, the friendly retired guy at the end of the street, was taking advantage of the mild weather of late Spring. He was sitting on his front porch enjoying a fine cigar. Or at least a cigar. Those fine ones cost a lot more than what he smoked. As he sat there, a car pulled up across the street, in front of the house diagonal from his. In the dimming light of dusk he saw two figures emerge. The first was a woman, quite attractive in a slender,...

4 years ago
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Sissy Girl Party

SISSY GIRL PARTY by Throne Danny felt so ashamed, standing there before his wife Melba in a pink and white party dress that would be appropriate for a nine year old girl, not a grown man like himself. He cringed inwardly and unconsciously took one of his short pigtails and wound it around his finger. His feet were shod in pretty ballet-type slippers, pink ones with little rhinestones on them. "You look so sweet, Dee Dee," she said with a smirk that he knew all too well. He had...

2 years ago
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My Stepmothers Sissy Daughter part 3

My Stepmothers Sissy Daughter, part 3 By: Malissa Madison I woke up early, my wet diaper urging me awake as I opened my eyes. Mommy was watching me sleep, and I realized her hand was resting on the crotch of my plastic panties pressing the wet diaper against my skin. "Did Mommy's baby girl wet her diaper," she smiled at me. "We can't have you in a wet diaper now, mommy's just going to have to change that," she helped me out of bed and I climbed up on the changing table, putting...

3 years ago
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AndrewAndrea

My mum and I lived on the outskirts of a small Scottish village. John and his mother Beth were our neighbors, and he and I were best friends from an early age, sharing everything as we grew up. At Primary School and then Senior Secondary School, we were an inseparable pair, supporting each other through the good and bad times. This idyll came to an end when we had just turned sixteen. He and his mom moved away from the area to go look after a sick relative.The house was quickly re-occupied and...

Crossdressing
1 year ago
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Wife and Sissy invited to a party

My wife and I were invited to some friends’ house on a beautiful estate in TX for a weekend party. While we were both well aware of the debauchery that could occur at the event, we had no idea how much participation we would both play. We were just getting off the plane to meet our driver when my wife handed me a slutty little maid outfit, and told me to go into the bathroom in the airport and change before we got out of the terminal. I did as she asked and then tried to walk out without anyone...

4 years ago
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A Sissy and Four Brothers

A sissy and four brothers -What is it like? Mother is very strict about separating me from 'the boys' but they've never experienced a 'sister' in the house before so there seems to be a lot of snooping around. A few of my readers have asked me for some additional information about farm life and living as a sissy with four brothers, and I'll respond to the question about seeing Jack again. Jack's mother called me and told me that I'd done wonders about boosting his self-esteem and she...

3 years ago
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Sissy Bachelorette Party

'You want it again?' She said, as she climbed between my legs, spreading them with the force of her knee. 'Yes Mistress.' I said, turning my head to the side. Her gloved hand grabbed my chin and turned it towards her. 'You want to be my girly lesbian bitch?' She said, as she tweaked my puffy nipples with her other hand, the dry latex chafing me. 'Yes Mistress - I want to be your girly lesbian bitch,' I rubbed my horny cunt against her stocking clad leg, ignoring the pain, wanting, no, needing...

2 years ago
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Sissy Julian Chapter III Further Development

Just when Julian's Lake Orenda experience seemed perfect, even if he is not about to admit it, circumstances change. But then Julian and the twins were very naughty boys, and we all know what happens to naughty sissies. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to...

4 years ago
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Mothers Sissy Teachers Pet

Mother's Sissy, Teacher's Pet By Sandy Brown January 15th, 2012 Dear Ms. Brown, I am Sandy's homeroom and science teacher. I thought I would mention to you that I noticed that Sandy had a small amount of nail polish on the base of his fingernails today. I assume that he was having some fun with you over the weekend, and that before he left for school you used nail polish remover, but inadvertently left some polish on. The color is very pretty, and I'm sure he looked adorable, but...

2 years ago
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The family ndash Sissyrsquos Babysitters Part

The family – Sissy’s Babysitters Part-2Sarah had left, I heard the front door close and her car drive off.....I couldn’t believe what was happening. Sarah and me had done some things, had fun with others, but she had dressed and prepared me not for ‘our’ fun...to leave and let her parents use me, they obviously knew about ‘our’ pleasures....it was James & Helen the couple that I sat with, talked to before marrying their daughter...was it something they always knew, or something they had...

4 years ago
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CDg Sissy Slut Cocksucker goes to local Adult Theater

I love dressing up whenever possible, which is not often enough. But, what I love even more is dressing up as a hot and wanton sissy slut cocksucker and then going to the local adult theater for some great XXX fun. I am not totally passable, but have been told my legs are fantastic and my ass is nice and tight with a hot tramp stamp just above my ass. Most guys say it's sexy as hell while they are fucking me. Fortunately, my wife had to go out of town for a few days and thereby giving...

3 years ago
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My Stepmothers Sissy Daughter part 2

My Stepmothers Sissy Daughter, part 2 By: Malissa Madison I lay there sleeping peacefully, feeling safe for the second time in so long I couldn't remember. I heard voices and I woke up, I was facing toward them on my side. A woman I didn't recognize but looked a lot like the girl in the diner said, "I think she's so sweet. I'm glad Dave brought you here last night. I was afraid to say anything about the bruises on your face, I didn't want to scare you." "Thank you Monica," mommy...

4 years ago
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Being Sissy To My Brother In Law

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...

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