Andrew The Unsuspecting Sissy Part III free porn video

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ANDREW THE UNSUSPECTING SISSY PART III [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 THUSFAR..... ANDREW NOW DREW: SISSY SUPERSTARSOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIAL 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 NEWMAN: MEDICAL DIRECTOR OF THE MANOR PENELOPE HUGHES: THE MANOR HEADMISTRESS Valerie couldn't help but smile as she entered Drew's suite. The poor dear was sleeping like an angel in her four poster canopied bed. Her hair was wrapped in a peach satin scarf to protect her hairdo; she had on pink sissy panties and a matching sleeping bra. She looked positively angelic and at peace, which was really an accomplishment considering her milking ordeal of this morning. Drew's stepmother Audrey had called and told Valerie to let Drew nap a bit. She let Valerie know that the appointment with Dr. Newman was going to be traumatic for Drew. She also told Valerie to let housekeeping know when they had departed so that Drew's stepsister, Sarah could have her things moved into the suite. Yes indeed, thought Valer,ie changes were coming fast and furious for our little sissy. And so she strode into the suite and after admiring the pantied, effeminate boy just a few seconds longer, she leaned forward and whispered into his pierced ear. "Sweetheart, time to wake up from your nap." The sissy stirred and Valerie continued her gentle prodding. She then sat down on the bed next to the sissy. Valerie had changed and was now in side zip chocolate brown tailored pleated pants with some matching pumps and a charmeuse nutmeg silk blouse with darted back and front. She swung her feet onto the bed, letting her stylish pumps fall to the floor. As Drew woke up, he snuggled up to Valerie placing his head on her shoulders and nuzzling her neck. His small pert breasts pressed against Valerie's arm. These are the perfect moments, thought Valerie. Drew is such a sweet girl; she has no idea what's in store for her. "Penny for your thoughts", she said. "Well, I'm not sure I understood what happened to me this morning." "Whatever do you mean, Drew?" " Well, I've never been milked like that before." "Did it hurt you lamb?" "No, continued the puffy eyed sissy, it didn't it, well maybe a little at first." "Did you like it?" "Well, at first absolutely not, I felt so invaded but eventually I did like it, although now my bottom is sore." Valerie laughed and Drew looked cross. "Don't be mad at me little one, I'm laughing because I know how you feel and I know how you're going to feel." As they chatted, Valerie noticed that Drew was deliberately pushing his pelvis into the side of Valerie's thigh and his bare leg and toes were now playing footsie with Valerie's toes! What a minx thought Valerie as she playfully traced the strap of Drew's pink frilled bra with her finger. Drew purred and Valerie took the opportunity to let her hand wander down from Drew's bra to the soft curve of his whisper thin waist then settling amid the many ruffles of Drew's pantied behind. So many rows of lace, how adorable and how fitting. How could this creature ever compete in a man's world? No thought Valerie, Drew was born to be a delicate little feminine treasure. These moments made all the years of training worthwhile. Drew's bottom was rounding out nicely thought Valerie as she continued to gentle caress the pantied bottom. Drew loved the intimate attention and cooed into Valerie's ear. Valerie continued her exploration of Drew's panties sneaking a finger into the leg band ticking the she boy and whispering into the pretty boy's ear how sexy his outfit was and how sweet he smelled. Valerie then moved her other hand towards Drew's belly. Drew offered no resistance and without having to ask or even motion, Drew turned his hips to give Valerie full access. Training is so important, thought Valerie. Valerie placed her free hand on Drew's hairless upper thigh while her palm lay at the vee of Drew's panty almost carelessly. As Valerie suspected, Drew was excited once again. For as femme as Drew is, he is certainly easily stimulated, thought Valerie. Drew, moved his hips a bit more to allow Valerie better access to his small symbol but left his head on Valerie's shoulder and still snuggled. Seconds later, Drew was pushing against Valerie's palm in earnest and nuzzling at her breast thru her silk blouse. The pace was picking up and Valerie had learned that these sissies could rarely contain themselves and anything more than a few minutes of friction could cause an "accident". So, Valerie let the sissy have some fun and then quickly rose from the bed leaving the sissy frustrated. "Okay, enough you evil girl! Get up and into the bathroom." The sissy did as ordered and once afoot, her sissy pants were tented for all to see. "You're spotting that panty", intoned Valerie who had picked up a menacing brush, which she was smacking into the palm of her free hand. "I suggest you move quickly," she warned the sissy. The sissy seeing the brush and then the look on Valerie's face scurried into the bathroom on perfectly pedicured tiptoes, but not before Valerie gave her pantied bottom a playful smack. "Be sure to rinse that panty missy," warned Valerie. Valerie couldn't help but admire how this particular sissy managed to walk on the balls of her feet and keep her arches erect whether in heels or without. In short, Drew was graceful in the most feminine way. Again, it was all about the training, and in this case endless hours of ballet. Drew entered the bathroom and immediately removed the panty and placed it into the sink along with some Woolite and cool water. She put on a pretty robe to maintain her modesty. "My my, its good to see a girl care for intimate things and keep them so pretty. Hurry along though; we've got a lot to do before your appointment. We want you to look pretty for the Doctor." Drew continued to clean her panty and took the opportunity to clean some other delicates. Valerie came back into the bathroom from the adjoining walk in closet. "Okay sweetie I've already selected your outfit for your appointment with Dr. Newman so go potty and we can start to get you ready." Drew looked at the tartan knee length pleated skirt and white see thru blouse and said, "Valerie this looks like a school uniform to me." " Well, darling you're correct, you're starting school tomorrow." Drew looked shocked, "I thought I was finished with school after I graduated from make up and those advanced classes in sewing and fashion." "Now, now we don't have the time to talk about it, we're going to be late. I've selected a darling panty for you, which was already dangling from her finger. Valerie then stretched the panty in between her hands and snapped the feminine garment out for Drew to see. See how pretty. So finish potty, and pick a matching bra, we'll do your makeup, brush out your hair and we can be off. I've also got some new delicious and challenging black heels for you, so pick out some white over the knee hose and a purse." A MIND IS A TERRIBLE THING TO WASTE Audrey and Sarah entered the Headmistresses office and were seated by an intern sissy wearing the school uniform. This was sissy was immaculately dressed and with her 3 inch heels was quite tall at 5 foot 9. "Sweetheart, what's your name," asked Sarah. The sissy lowered her eyes and said, Stefanie. Her voice was barely a whisper. "Are you the sissy assigned to this meeting?" "No ma'am", stuttered Stefanie, "that would be Alison". "Very well then, be seated and resume your duties." The women entered the office and sat down Audrey began, "It's great to visit with you Headmistress Hughes. I'm sure you know my daughter Sarah." " "Yes I do! Now please sit down, I understand Andrew, or is it Drew these days, will be starting school tomorrow", said the Headmistress tongue in cheek. "Yes Penelope its Drew and I'm proud to announce and we're here to create a special schedule for our special missy." "Sarah, I've read your Mother's memo and the gist of it is that we need to teach our young charge to crave the attentions of men and to experience real joy while catering to the needs of a specific man." "Yes, that's it exactly!, Drew experienced her first anal stimulation this morning and achieved orgasm", said Sarah. "How precious! Did the little dear cry?" Yes! However, the milking was so draining and emotional, the sissy was entirely overcome and simply broke down. She's upstairs in her suite napping as we speak. These Nancy boys are fighting their true inner selves, their training and the hormones we give them, it's no wonder they exhaust themselves so. Once they completely give in to their true selves they seem to find their special place in life and feel accomplished and necessary. That's always been my philosophy and why I created The Manor!" "Well, Audrey nobody knows what we do better than you. You designed most of our programs, so what did you have in mind?" Well, Drew has an appointment with Dr. Newman in a few minutes. As the memo stated I want Drew to want, need and crave Jim. I also want her to be able to rock Jim's world whether it be in a tailored suit, a bathing suit or her birthday suit." Penelope smiled. "Audrey, we spend all day doing just what you asked." "I know," said Audrey, "but I need a modified schedule because in the middle of this education is the courtship between Jim and Drew. The wedding is six months from now and Drew hasn't even been kissed by a man as yet!" "I see," said Penelope "and I know we're up to the challenge." " Good said Audrey, I'm going to leave you with Sarah to arrange the schedule while I meet with Jim and Doctor Newman." "Sounds great Audrey, we'll get right to work!" Audrey smiled and left the room and immediately the two women huddled. "So I have Drew's file here. As you know, you step sissy sister was quite a student! She had several bad habits, but once broken she was a model sissy!" Sarah reviewed the folder. As she read, she commented on the various pictures. "Why wasn't Drew gaffed asked Sarah as she handed the picture to Penelope." "Well, as you know, part of the conditioning is exposing these delicate creatures to a myriad of stimuli and then documenting their triggers." w Sarah found the part of the file with Drew's "triggers" and laughed. "Well, I'm not shocked to learn she adores her lingerie, but I wouldn't have guessed that she wants to be a makeup artist!" Penelope was lost in a moment of thought and said, " I remember a time where we caught your naughty miss showing the other sissies how to apply lipstick and even mascara. Which as we are both well aware is a big no no for our faux school girls. Drew excelled in sewing, the salon and walked in every fashion show and competed in three of our sissy pageants and even won one. "Yes, I remember that, it was three years ago. Drew was such a prissy waif. She could barely handle her gown and cried when mother refused her gaff for the swimsuit competition. She was beautiful." "She has also completed her training as an assistant and a party planner. Your stepsister excelled in both art and literature, but was a poor athlete and not very competitive on the field. She should be able to hold her own with her gentleman outside the boudoir, now we need to teach her to hold his," laughed Penelope. Fast friends, after 20 minutes, the women had completed their task. "Okay said Sarah let's review. Drew will have 7 hours of dance/ballet/aerobic activity. She'll have class time with like-minded sissies learning male anatomy appreciation. She'll have a class on male massage and a lab as well. Drew will also have three hours per week of oral training and technique. Sarah, its fascinating how we train our little wards. We challenge them and reward them and stimulate them. I hope you'll make time to visit some of those classes. Also, Drew will have 4 hours a week of modeling training. And, I've asked Serena to spend some sissy quality time bringing our little miss up to speed." "I saw a photo shoot with Serena, she was beautiful and the way the camera loved her and the way the man responded to her, well no wonder men find themselves so attracted to these delicate boys! "Now, I need to have you choose Drew's masseuse and modeling partner. As you know, shortly after our sissies experience sissy love with one another, we quickly move them onto men. We do this using massage. Imagine Drew in her little bra and panties waiting for a masseuse to come to her suite and our little dear trying to sort through all of her emotions and feelings while she is being expertly, erotically massaged by a real he- man. When she gets an erection, and they all do, well it's so much fun to watch. They're so conflicted and embarrassed...its just delicious. So, if you're ready we can begin." Penelope motioned to Allison. "Who is that pansy", said Sarah. "Oh, that's Allison and she's been here for 6 years. She was a handful at first, like most of them are, but adapted to her training and has become the sissy we had all hoped she would be. Her mother is delighted and now spends her days with her girlfriend living off of Alison's estate while Alison stays with us, never placing her mother's style of life in peril. Alison was to be the sole inheritor but as a sissy she realizes these things are better left to her mother who administrates the estate and she's free to pursue her sissy duties here with us. I truly believe that even if she fully knew what she had, she would chose to remain in her frillies and at our service." Alison was five foot six with her heels, a brunette with an elaborate updo very little makeup, yet her face was flushed with excitement. She wore the required school uniform but everything was very tight and very short. She managed her heels beautifully and had an incredibly small waist to go with her round bottom and what seemed to be c cup breasts. "She's really very cute started", Sarah "and that waist is so tiny even I'm a bit jealous." "Well you're right, Alison works very hard on her figure it's a great source of pride for her, but I think you'll agree that she has other talents," said Penelope with a sly wink. Just as Penelope finished, Alison walked the first applicant in. He was a tall handsome man and was dressed in a white robe. Sarah gasped. "I know," said Penelope "this is Steve. He works in security and is a lifeguard at the pool." Penelope again motioned Alison and she stepped forward to remove the white terry cloth robe Steve was wearing and he was then standing just a few feet in front of the women wearing nothing but a black Speedo bathing suit. His bulge was extraordinary. Sarah stared at this hunk of a man and Penelope motioned Alison again, who stepped forward and ran her bare hand across Steve's hairless chest. She caressed all parts of his chest and was standing on the tips of her heels to reach his shoulders. She then stopped and picked up a bottle of baby oil and rubbed it on her and on her bare thighs. She once again because massaging Steve chest and at the same time was rubbing her thighs against Steve's legs. All over Steve began to glisten from the oil. His eyes were slightly shut and he was moaning. Alison ignored everything and continued to oil the chest and arms of this hulk. This went on for a few minutes until the short-skirted sissy squatted on her heels exposing her pantied bottom and began rubbing Steve's member through his Speedo. Steve to his credit responded almost immediately and Alison maneuvered his manhood to the right side of his Speedo and then the left and then back again. Her small hands were very busy pumping his tool and it was obvious she was enjoying her duties as she took every opportunity to look into Steve's eyes. At one point the sissy became quite bold and placed her tiny hand on one of Steve's buttocks. Her fingers stretched towards their goal, but the two women were obstructed although based on Steve's smile, Alison reached her goal. After just a few minutes, Steve's now very erect pole was well above the waist of the swimsuit. Alison was kneading the phallus and licking her lips. It was a shameful and exciting display and just when she was about to place the mushroom shaped head in her mouth, Penelope thanked her and asked that she escort Steve out of the room and bring in the next candidate. "Thank you Steve," said Penelope. The overexcited sissy immediately stood up and stepped back and escorted Steve from the room. "Well, what do you think?" said Penelope. "Of what?" gasped Sarah? "Alison or Steve?" Penelope laughed, "Steve of course. You need to see Steve as Drew will." Sarah smiled and so did Penelope. "On my gosh said Sarah what will our dear Drew do when Steve shows up to give her a full body massage? More like what will Steve do when it's Drew turn to give him a massage or better yet, what will Drew do when she gets her hands on Steve manhood?" Both women laughed. In all, four applicants were seen and each one was expertly oiled and erected by Alison. Each applicant was well endowed and could not hide a sincere penchant for everything sissy. Later Sarah learned that Alison "helped each of the applicants to properly relax" after the meetings were over. "Just another perk for the staff," said Penelope as they headed toward the classrooms. Anyway they do it better than we do. While I adore fellatio, sometimes it can be such a chore and that's when these sissies come in handy, they really enjoy having their mouths filled as well as their bottoms!" Once again the women giggled. "And what of the poor sissy Alison's and her obviously pent up excitement?" "Well, she's well secured behind her gaff and really the pleasure for her is giving pleasure to others. That's why our training is so specialized. Alison has some freedoms here and she has several other sissies who she is allowed to have relations with. Of course it's all closely monitored and I'd be happy to send you tapes of some of her sessions. She's a very passionate lover, especially with her sissy mates." "Fascinating," said Sarah. "Well, we've got it down to a science," said Penelope "a sissy science if you will." Once again the two women were laughing. As they were leaving the office, Penelope stopped at the front desk and handed Stefanie a file. "Stefanie, please send a copy of the course schedule to the numbers listed on the file. Pay special attention to your penmanship and make this your first priority." "Yes ma'am,"replied Stefanie. Across the complex, Audrey was reviewing the file that was forwarded by Penelope. She smiled thinking about the fun they must have had picking out classes and a masseuse for her precious Drew. Somewhere downtown, Jim was also reviewing the file. For him, the excitement was building. He was about to create the lover of his dreams and how could he be more fortunate. He had seen a picture of Drew and from that moment he had to have the precious delicate boy/girl. He couldn't wait to have her and was anticipating the beginning of their courtship. He had to admit that Audrey was the savviest businesswoman he had ever met. He had decided he had to have her as his partner and her stepson as his lover and wife. Who would have thought it could be possible and yet it was! THE DOCTOR WILL SEE YOU NOW Valerie had finally managed to drag her sissy ward from his mirror and they were finally on the way for Drew's appointment with Dr. Newman. Valerie could see that Drew was upset. "Darling what is it?" "I'm just nervous, I'm afraid of the Doctor." "Oh poor dear, there's nothing to be afraid of, look at all the great things Dr. Newman has done for you. She's made you the prettiest girl here at The Manor now hasn't she?" "Well, I guess so." "So you'll be sure to thank her won't you..."? "Yes ma'am I will." After a few minutes walking and an elevator ride, Valerie opened the door to the waiting room. Moments later a Medical Docent named Claire ushered Drew and Valerie into an interior exam room. "Remove everything but your bra and panties. I'll be back in a moment." Drew did as ordered and removed and hung up her blouse and skirt as well as her pretty white hose. Valerie noticed the sissy was fidgeting. "What's wrong now?" "Well," Drew started, "this light isn't very flattering." "Don't be such a silly girl and stand still." Just then, the door opened and Claire re-entered with two very obvious sissies in tow wearing Candy Striper uniforms the skirts of which were far too small to conceal their matching red panties. "Oh, isn't that adorable," said Valerie. "Are they twins?" "Yes they are," said a smiling Claire. "Sissy twins!" "Speaking of adorable, look at our Drew." Claire reached forward and hooked her finger in Drew's panties and snapped the waistband. "So, how's my favorite pantywaist feeling?" Claire had seated herself on a stool with wheels and was now running her hands over the uncomfortable sissy. Squeezing here and thumping there, Claire gave a full exam to Drew. Then, she called for her two sissy assistants and asked them to take measurements. All the while she was asking Drew questions. Two injections were given and some blood was taken. Drew's curly haired head was positively spinning. Claire then abruptly reached out and dipped her hand into Drew's panties and forced her way under the gaff, the surprised sissy gasped but maintained her poise and did not move. With her hand now between his legs, she said, "cough for me sweetheart." Drew hesitated. "It's okay darling, cough for me." Drew forced a weak cough. "There, now that's a good girl." More writing and then finally Claire put her pen away and slid the stool back a bit. Drew eyes were focused on his pretty heels and he was mortified. He dare not make eye contact for fear of being embarrassed to death. And yet, his ordeal had barely begun. The two sissy Candy Stripers were now giggling uncontrollably and Claire shot them an angry glare and they both immediately stopped their unacceptable behavior and focused on the floor as well. Claire then instructed her assistants to weigh Drew and finish with his measurements. The two sissies took every opportunity to run their hands al over Drew's bare flesh. Two sets of busy hands were exploring Drew and both Valerie and Claire were watching Drew's response carefully. After a minute or two, and what must have seemed like hours for Drew, Claire finished her notes and asked the girls to bring Drew to the full-length mirror and place her on the pedestal in front of it. Claire then told the Candy Stripers to remove Drew's panties and his gaff. The twins looked at each other and smiled. Drew's hands immediately reached down to cover himself. He was all sissy and shy. Valerie warned Drew to behave but the obstinate sissy refused. Valerie was about to mete out some behavior modification but just before she could move, Claire had scooped up the sissy into her arms and carried the slight sissy to a chair and sat the pantied boy across her legs bottom up and began viciously smacking the bare backs of his thighs. Claire was merciless. Her eyes were glazed and her breath was short. Valerie knew she was enjoying herself. In barely a minute Drew's bottom was aflame and the room was filled with the sounds of his pleas. This was truly music to Valerie's ear and the two sissy Candy Stripers were enjoying the display as well and were holding each other's hands in anticipation of what they did not quite know. Finally Claire stopped. She pushed Drew off of her lap and placed him between her legs on his knees. "Drew would you like to get back on the pedestal in front of the mirror?" "Yes ma'am" said the sniffling sissy. "Would you like to have my assistants remove your panties and gaff for me?" "I, well, please," the sissy pleaded. And, just that quickly, Drew was again over Claire's knee but this time instead of a spanking, Drew was having his thighs pinched and the sissy was really screaming and trying to get away. He couldn't believe how strong Claire was. She was killing him! That pinching was soooo painful. Again after a minute or so the sissy found himself between Claire's legs once again. Drew could see her garters and her pantied mound. Claire had hiked her skirt up to her thighs. Claire called Drew's name snapping the sissy out of his trance. "Drew, show me," and she pointed between her legs. Drew, wanted to show Claire. Drew decided to show Claire what he had been taught. He placed his hands behind his back and began his journey up her thighs. He licked and sucked and teased and nibbled using his lips, tongue & teeth. Claire was breathing harder now as Drew approached her essence. He'd really have to work now because she was not going to remove her panties and he wasn't going to have the use of his hands. When Drew was getting closer, Claire took her hand and placed it on the back of Drew's head and jammed it between her legs. The two Candy Stripers had stepped forward and were now holding Claire's skirt. Drew just focused on the aroma and the heat, the damp musk and the sounds of Claire's moaning making mental notes of what pleased her and what didn't. Drew snaked his long tongue around the leg band of Claire's silk panty. More nibbling and kissing and Claire was moaning. Drew was bringing Claire to the edge and then backing off time and again. For Drew this was fun and where he found his greatest satisfaction. Claire was now grinding her hips into his face "Don't tease me you little bitch. You know what to do, now do it." Moments later Claire went over the cliff. "Don't you dare move your face, I'm cummming." And then Claire yelled. After recovering, Claire removed her hand from the back of Drew's head. "My god, what a gift you have. You sissies lick our pussies to perfection! Your little dicks are useless, but those tongues! Valerie, my complements on your training techniques. As Claire and Valerie recovered, the Candy Stripers separated, each one serving a different mistress. When order was finally restored, Claire addressed Drew who was still on her knees, "Would you like to have my assistants remove your panties and gaff for me?" "Yes ma'am." "Good girl," said Claire, "I'm proud of you. Now hurry up onto the pedestal." As Drew moved past her Claire she couldn't help but give his round bottom a nice smack. Drew had come to realize that almost everyone was fascinated with his pantied bottom Once up on the pedestal and in front of the mirrors, the two Candy Stripers came forward and deftly pulled Drew's panties to his ankles. Claire and Valerie smiled. Now Drew was down to his security blanket, his powernet gaff. Drew knew he was too small to "tuck", but the gaff pressed everything back and gave her the smooth lines Audrey demanded. He had been gaffed for as long as he could remember and it made life easier. Now these two Candy Stripers were pulling off her last line of defense and Drew didn't know what to do so she began to cry again. "How sweet," said Valerie. "I know," said Claire "it's just precious." After a good amount of tugging, the gaff was removed and Drew was left naked save for his pretty bra. One of the Candy Stripers extended her pinky next to Drew's stem. They were about the same size and the uniformed sissies giggled. "Enough girls," said Claire and she moved forward examining Drew's package, or lack thereof. "Well Valerie I see what you mean, she is so compact." I mean I love the hairless look, but I had no idea how poorly endowed Drew was. You weren't exaggerating." Drew was not doing well under this examination, his heart was racing, he was feeling sick and when Claire stepped forward and took his small member in between her thumb and forefinger and diddled it, that was all Drew could stand. He couldn't look in the mirrors because the girl staring back made his head spin. He dare not make eye contact with the cruel Claire as she was playing with him so intimately and he was ashamed of his small "package". He looked to find Valerie but when he found her the look on her face was pure evil. Not knowing what else to do and overcome by everything that had happened, the waif fainted. Claire looked at Valerie and said, "Just what I expected". She then told the twins to put her panties back on her. "Drew is the ultimate drama queen," said Valerie "Well, if it's drama Drew wants then its drama she's going to get!" Claire snapped the smelling salts under Drew's nose and the sissy immediately awoke. "Sweetheart, are you okay?" "I think so," said a groggy Drew. Immediately Drew realized she had a panty on. Thank goodness she thought. Claire asked Drew to return to the pedestal. She stood right in front of Drew and asked that Valerie join her. "Okay Drew, I know you're modest. But, as a sissy you needn't be ashamed of your tiny penis. It's not like a woman would have a need for it, or a man for that matter. You should be concentrating on making yourself attractive and learning how to give pleasure." "I've tried to reinforce those ideas in the past, said an exasperated Valerie. "I guess I've got a lot of ground to make up and Sarah and Audrey will be so disappointed." "Okay little one I need you to be a big girl and show me how erect you can make your little thing." Drew could not process what Claire was saying. What did she want, he thought ? "Drew, I need you to concentrate and show me how hard you can get, I need a measurement". Pretend nobody is watching and look in the mirror and tent your panties! You've done that a million times! Nothing was happening and Drew's face was tense with struggle. "What's wrong lamb?" Drew could barely speak. Claire looked at her watch and tapped her heel. "We don't have all day, show me what a big man you think you are!" "I'm trying," spat out the exasperated sissy. "I can do it." "Well I guess you're more girl than boy now aren't you." The sissy grunted and beads of sweat were now appearing on her forehead. I mean look at you in your pretty bra and matching panties. Lip gloss, and a full face of makeup. And what about your shape, thin arms, small waist and a delightfully round bottom. No, you'll never be able to handle a real man's responsibilities in the bedroom or for that matter out of the bedroom. Drew was desperate to prove Claire wrong, but the harder he tried the harder it became to get hard. With nothing working, the sissy dropped her head to her hands and began to sob. Okay, calm down. Relax, it's hard to admit what you've become and what you will become. I'm here to help and I guess you need inspiration. So pay attention and let's play pretend. Okay, pretend your boyfriend is feeling you up and reaching into your panties!" "Talk about performance anxiety," said Valerie. Drew was clearly frustrated. "I'm not gay," she demanded as she stamped her tiny foot. Every pair of eyes was on his silk print peach panties. The pressure was intense. With Claire teasing him so, he just felt so frustrated he was afraid he was going to cry again. "Oh, I think you protest too much, said Claire Don't knock it until you've tried it!" Claire now had her hand on his back and playing with his bra closure. She then reached around and dipped her hand into his bra cup and pinched his nipple. "Now pay attention Drew." Drew squealed. Good I have your attention. It won't be often that you're asked to erect yourself and when asked, compliance is expected." Drew was hyperventilating. "Can, I mean, may I....touch myself there?" "Of course not and don't you dare faint or you won't be able to sit for a week." Claire had seated herself in the chair again and motioned the sissy to sit on her lap. What a pretty picture Drew made sitting on Claire's lap in his matching panty and bra. Claire whispered several things into Drew's ear and Drew flushed, arose and went back to the pedestal. The Candy Stripers had a ruler and were waiting at the ready as Claire approached. Looking in the mirror she asked Drew to lock his eyes on hers and not to dare to move. Drew complied, but was shivering. Valerie watching from behind was in desperate need of an orgasm. She watched as one of her assistants applied Vaseline to two of her Claire's fingers behind Drew's back. The same sissy pulled the leg band of Drew's panties back and Claire moved her fingers to Drew's sore rosebud. Claire told Drew to relax as she pushed her first finger into his behind a knuckle at a time. Once inside she moved her finger about, and in the mirror everyone could see Drew's reaction to the invasion. Tented panties! "Good girl," said Claire. Drew however was ashamed by what Claire was doing, and by who was watching and because well he had to admit it felt good. "Okay now darling, push yourself against my second finger and don't be shy. Be a big girl and show me." In a few minutes Drew was really pumping and Claire thought the little miss was at the peak of his excitement. With her free hand she signal her assistants who dropped Drew's panties and measured his "manhood". "3 ? inches chimed the assistants in unison. Drew was once again mortified and tried to push his little member out further. "Oh isn't that delightful, he's struggling to make it look bigger. Sorry darling, tiny is tiny." Now both Claire and Valerie were laughing. "Okay girls pull up Drew panties. And Drew, you'll be delighted to know you're about ready to see Dr. Newman." With his panties now in place, Claire went into the main office to check that the video feeds were working. Dr. Newman, Jim and Audrey were all networked in. Dr Newman said, "As you both know Drew has shown great sensitivity in his bottom. That is a huge plus. Now, we have to introduce the sweet boy to sexual stimuli other than that which women provide and that process is going to start right now. When that's completed, Drew will be freshened up and then we'll have our exam. Jim I think you'll really enjoy what we have in store for Drew right now. But, be careful, these sissies are very "quick" if you know what I mean. Claire entered the exam room once again and Drew was right where she had let him on the pedestal. "Okay Drew we have some cream to apply and it will be a full body application." Valerie immediately realized it was hormone cream and she loved the idea. Claire handed her assistants the cream and told them so as no to stain their uniforms they should remove them. They quickly removed the uniforms and carefully hung them up. The twins wore matching bras and had small developing breasts, firm tummies and trim waists. They were gaffed, but Drew was not and had his sissy camel toe showing. The sissy twins approached Drew and immediately went to work massaging the rich hormone cream into the Drew's skin. After a few minutes, Drew found that he was becoming excited and didn't want Valerie or Claire to see. He tried to think of anything he could. Meanwhile because he was on the pedestal in heels the twins had to really reach and were rubbing their bras against his back and tummy. Finally one of the twins got bold and got onto the pedestal. She was putting the cream under Drew's thin arms and leaned forward and rubbed her panty covered front against Drew's panty front. Drew was now completely erect but was hoping to stay "hidden in his panty". The other twin was now working the cream under the back legs of Drew's panties and toward her rosebud. She was also rubbing her tightly gaffed vee on the back of Drew's thigh. Drew, had to admit the twins were quite beautiful boy girls. They had pretty faces and little breasts and looked like girls with their symbols hidden behind their gaffs. He decided it was fruitless and let himself go. The friction on his panty front was too much and the sissy let out a high-pitched yelp and spurted. "Oh my, he's completely soaked his panties," said Valerie. "I'm so proud of you Drew!' Valerie ran up to the humiliated sissy and gave her a big kiss. "You're growing up so fast." Drew was trying to hide the wet spot, but Claire came up and shooed the Candy Stripers away, slapped Drew's hand away and swabbed a sample and placed it in a cup. She then came back and said "open". Drew looked confused and Claire once again said, "open". Drew then opened his mouth and Claire quickly reached down into his panties and grabbed some of his sissy cream and put it right into his mouth! "Swallow", she demanded and Drew did. "Good girl, is that the first time you've tasted your own cream?" Drew stammered and finally mentioned that he had tasted it on occasion but had never been fed it. Claire laughed, "Just wait till your boyfriend feeds it to you!" Now everyone was laughing but Drew. Drew looked terrified. Claire told her Candy Stripers to clean Drew up, freshen his lingerie and wait for Dr. Newman's call. "Drew, the twins were so nice to you, please give them each a peck on the lips." Drew was shocked. They were boys like him, he couldn't possible kiss them. "I'm waiting", said Claire with arms folded. Before Drew could refuse the first of the twins jumped on the platform and gave Drew a big hug and a kiss. Drew was stunned and before he recovered the second twin also kissed him on his lips and even stuck her tongue in his mouth. Drew was overwhelmed. Valerie clapped. I'm so proud of you Drew! Now get out of that soaked panty before you develop a yeast infection. Claire and Valerie laughed once again. As Claire and Valerie left the exam room, Claire said to Drew, "not such a big girl after all, but you did well even for a sissy with such a small penis!" Valerie thanked Claire and left to make sure the suite was being arranged as ordered. THE DOCTOR WILL SEE YOU NOW.......

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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...

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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...

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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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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...

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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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...

2 years ago
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SlutSport Part III

Part III - Day 1 of Tournament Fighting of the Sluttimay Tournament! (It is suggested you read part I and II for context, backstory and to get primed and ready for Part III you sluts...and as always, comments/suggestions are always welcome!] SlutSport - Part II After the "opening ceremony" of Sluttimay, I had to refocus at the task at hand. So much had happened in so little time on top of which I recognized the number two terrorist in the world in Kong Fi and I couldn't do...

1 year ago
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Meeting Karen Part III

Meeting Karen Part III by MadQuill This is a four-part story is about a woman who models herself on another. I hope readers will enjoy this trans-lesbian tale. All of the characters are over eighteen years of age. This is a work may have an additional chapter. Thank you for your comments. This is a work of Fiction. Please remember this is a copyrighted work and all legal disclaimers apply. Meeting Karen - Part III Preamble : Carrie and Karen meet and ride...

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