Andrew The Unsuspecting Sissy Part II free porn video

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 training school, the beauty academy and the clothing design institute nearly 300 of the little dears." "My word, you've practically doubled the size in the last year." "That's why this marriage is so important Sarah." "Andrew is the key." "With Jim's contacts and bankers we can offer more than just 30 or forty graduates a year, we can be national, or even international!" "Clearly the demand for these special petticoated lambs is at an all time high and we have to expand before competition comes into the market." "I want to be the first and last word in training these sissies to take their proper place in the world." "It's a huge task, mother." "Darling with your education and training, it won't be as hard as you think." "Now, I wonder why Andrew is late?" "Mother, you baby your sissies too much." "Sarah, this isn't just any sissy, this is your stepbrother and with what he'll go through in the next six months, I think I can be a little lenient." "Or maybe I should be the way I was when I caught you dressing him in your panties and stockings when you were thirteen." "Oh my god mother, I had almost forgotten." "You were so mad." "Pretending my darling, actually I was delighted." "Mother, you are evil." "You yelled at Drew so much he started shaking and then wet himself." "It was terribly, exciting wasn't it!?" "I never saw too much of him after that." "Well Sarah, I moved him into the sissy dormitory and then off to finishing school." "Mother as long as we are being honest, I have a confession." "What is it Sarah?" Well, I was playing "games" with Drew long before we got caught." Now her mother was laughing, "Sarah, I knew all along." "I just wanted to wait until the time was right." "Remember, your stepfather had died the year before and the estate had finally settled." "Everything in its time.....but what to we have here?" Drew had entered the room with bouncing curls and a big smile. He immediately presented himself in front of Audrey and did not even see Sarah at the other side of the table. "Hi mommy," said the sissy. "You look so pretty this morning." "Thank you precious, now let's look at you." "Please spin." The skirted boy twirled around and then stopped and was once again facing his mother. She reached forward and ran her hand up his leg and they both watched as it disappeared beneath the terry skirt. "Good girl, you're dry." "Now, I know you haven't noticed, but we have a guest!" Drew spun around and saw his stepsister. He was in utter shock. After all, it had been years since the two had seen each. Now, the sissy was mortified. "Oh how cute, she's embarrassed," said Sarah. "Don't be shy, come and say hello little one." "You look so pretty in your outfit and your tummy is so flat." Come over and let me see you after all of these years. Audrey gave Drew a little smack on her behind for encouragement and the sissy walked around the rather large table to where her stepsister was sitting. Audrey knew this was a seminal moment and was holding her breath. Sarah took Drew by the hands and stood up and gave him a kiss on the cheek. "You look great, said Sarah." "It's been too long since we've been together." Sarah was now running her hands up and down her stepbrother's arms. "These are still the skinny little arms of my childhood play toy." "Make a muscle for me." Drew flushed. After some more cajoling the sissy made a fist and flexed his little arm." "You are still so delicate," said Sarah. "And, I don't remember you being this petite." "Junior Miss department all the way for her, am I right mother?" Drew was obviously upset by the talk and when her stepsister referred to him as a her, he emphatically stated, "I am boy." "No, I don't think so." said Sarah. I think you're much more girl than boy. Just look at your little boobies and tiny waist and those shoes...would a boy every wear sandals like you have on? I don't think so. And, silly, what about your pretty skirt? I bet you have on some really cute panties underneath. Do you? Well, do you? Now Drew was a little scared, Sarah had changed her tone and he felt fear. He knew from a long time ago not to anger Sarah. She could be so cruel. It came so easy to her. Audrey leaned forward a bit. She wanted to speak but wisely held herself back. Calmly her daughter said, "Drew raise your skirts and show me your panties." Drew was beside himself. He didn't know what to do. He wanted to please Audrey but didn't want his stepsister to see him like this. It was all too much. After a few seconds he couldn't take it any longer. His perfectly manicured fingers lifted his terry cloth flowered print skirt. Just then Sarah administered a vicious swat to Drew's thigh. "I said lift your skirt, and I didn't mean halfway and I meant now." Drew obeyed and lifted his skirt well above his pantied waist. Sarah immediately noticed that Drew was erecting. Audrey was smiling now and relaxed back into her chair. "What is this little unladylike thing Drew?" railed Sarah. "Now I know for sure you aren't a man." " My word that's smaller than a babies' dick." "It's better off hidden in a panty and under some petticoats." "How could you expect to please a woman with just his?" "Answer me", demanded Sarah. "I I I I don't know, I guess I could try, I mean I'd want to try." "That little thing hasn't grown at all since we were children." "Am I right mother?" The sissy's shoulders were shaking and he was simpering...on the verge of crying but still holding the terry skirt for fear it would drop. Sarah's words of torment were exciting him further and he could not calm his little stem. Now Drew was in fear of spotting or possibly soaking his panties and that would really anger Audrey. Seeing everything she needed to see, Audrey rose and said, Drew you may lower your skirt and go to the nursery. Repair your makeup and prepare yourself for your milking. Audrey then looked at Sarah and winked. Sarah please join us, and upon hearing that the sissy's mouth dropped. Audrey then looked at the stunned Drew and said, sweetheart, why are you still here? A QUICK TOUR AND THEN RELIEF FOR THE HEAT, MAYBE... Drew turned on his heels and left the room. The two women watched as the sissy minced from the room. Both admitted later that while Drew's legs were short, her little waist and round bottom were meant for skirts and girl things. "Sarah, our little princess will take a few minutes to be prepared by Valerie, during that time we can take a walk through the training halls and you can see some of our up and comers with some of our most promising instructors." "Mother, who is Valerie?" Well, Sarah as you well imagine, we just can't let these sissies run around of their accord. Someone has to watch them on a constant basis. The surveillance by both camera and by people must be handled by deidicated and trusted females who enjoy the journey our petticoated effeminates are taking. For the same reasons as ours, these women are drawn to our cause and they are the nucleus of what I want to build. Valerie is a Docent, a guide with elevated status. She's quite stunning and I have high hopes form her." Audrey picked up the phone and dialed. "Hello, Valerie..Yes its Audrey." "Our little angel is on his way up to you." "Why yes darling today we will begin Drew's preparations for her relationship with Jim." "I agree Drew is an adorable name." " I know, it's terribly exciting." "More good news is that Sarah is back and has agreed to help." "Yes, I'll tell her and I'm sure she's looking forward to meeting you as well." "Give us about twenty minutes and we'll join you." "I'm sure by then, our sissy charge will be absolutely bursting her panties with anticipation!" "Thank you Valerie." Drew turned on his heels and left the room. The two women watched as the sissy minced from the room. Both admitted later that while Drew's legs were short, her little waist and round bottom were most definitely meant for skirts and girl things. "Sarah, our little princess will take a few minutes to be prepared by Valerie, during that time we can take a walk through the training halls and you can see some of our up and comers with some of our most promising instructors and let's do peek in at one of our photo shoots." "Mother, who is Valerie?" "Well, Sarah as you well imagine, we just can't let these sissies run around of their accord. Someone has to supervise them on a constant basis. The surveillance by both camera and by people must be handled by dedicated and trusted females and some males who enjoy the journey our petticoated effeminates are taking. For the same reasons as ours, these women and men are drawn to our cause and they are the nucleus of what I want to build. Valerie is a Docent, a guide with elevated status. She's quite stunning and I have high hopes for her." Audrey picked up the phone and dialed. "Hello, Valerie..Yes its Audrey." "Our little angel is on his way up to you." "Why yes darling today we will begin Drew's preparations for her relationship with Jim." "I agree Drew is an adorable name." "I know, it's terribly exciting." "More good news is that Sarah is back and has agreed to help." "Yes, I'll tell her and I'm sure she's looking forward to meeting you as well." "Give us about twenty minutes and we'll join you." "I'm sure by then, our sissy charge will be absolutely bursting her panties with anticipation!" "Thank you Valerie." The two women left the dining room and in just a few minutes were in front of a double door. Audrey handed Sarah a slide pass and asked her to swipe the card. The doors opened and the two women entered a long mirrored hallway. "Hello Vito", said Audrey, this is my daughter Sarah and her swipe works, please see she gets a pass card for all access." Vito nodded, turned and began talking into his walkie talkie. "He's, well...quite a specimen." "Yes indeed", laughed Audrey. Vito and others like him serve as waiters, lifeguards, security, models, masseuses, trainers and of course training models." Sarah looked confused. "You'll understand after our little tour. But sweetheart, you don't imagine that Celeste just has natural abilities..she had to learn. Drew needs to learn as well if she is to have a successful marriage. We do want Jim happy, do we not?" Audrey and Sarah were now standing in front of the first classroom. Through the two-way glass they could see an instructor and 12 very attentive sissies. "Mother, those sissies are adorable, but those uniforms, I don't understand." "Well Sarah I could see why you'd wonder where their skirts are, but this class is a training class on the male anatomy. So, the instructor is trying to see what excites her students, so we can add that to each student's profile and incorporate that information into their individual training programs. We know they love their feminine selves, now we want them to learn how to love everything about men." Each sissy was perfectly made up, wearing a white blouse with a yellow tie. The blouse had an elastic waistband leaving bare midriff for all to see above their white hipster cotton panties and thigh high white hose. Their little feet were shod in cute patent leather pumps. The instructor wore a navy blue tailored suit. Just a jacket and pants, no blouse. She was talking and Audrey touched the control panel in the hall and now they could hear what was being said. The seats had no desks; the sissies all had small steno style pads and pencils resting in their pantied laps. "Okay", said the instructor, "So raise your hands if you like men?" All of the sissies were hesitant. Not a one raised a hand. "Come on now, I know you girls aren't brave, but which one of you would like to please a man?" "Okay then put your pads on the floor and let me ask you if you'd like a man to please you." "Mother!" gushed Sarah, "look at all of those tented panties!" The instructor was smiling. "Okay, it's good to be honest with yourselves." "You realize that no woman could be interested in you as a lover but that men will adore you and love you and want to care for you." By now all of the sissies were experiencing little tents between their legs. Audrey clicked off the volume and the women continued their stroll stopping at several windows and looking into the classrooms. "Mother, I like that you let the sissies pick their own bras. I saw every color under those blouses and I think it's great for them to have some level of expression. "Well sweetheart its not all work you know for the little dears." The women turned the corner and with another swipe of Sarah's card entered the Studio wing. "We shoot catalogs and web content here". They stopped in front of another mirror and looked in to see a videographer and photographer and several assistants flitting about. They were focused in on a set with a makeup mirror. The mirror was removed so the sissy was looking right into the camera and pretending to apply her makeup. "She's very beautiful." "Yes she is," said Audrey with pride "Serena is quite an accomplishment." "If I showed you a picture of that boy when he arrived, you wouldn't believe it was the same person." PREPARATIONS BEGIN Upstairs, Drew had just entered the nursery and was met by Valerie. "Drew, look at you, you're more adorable with each passing day." "Thank you ma'am." Long ago Drew had learned that being anything less than perfectly docile would set off Valerie and besides being physically intimidating she could be verbally abusive. Valerie was dressed in a white latex body hugging short dress. At 5 foot 10 her heels made her a foot taller than Drew. Valerie put her hand out and shyly Drew placed her hand in Valerie's and watched it practically disappear. "Let's hope I can't find a hair below your eyebrows today Drew." Drew hoped not and now realized everyone would now be calling him Drew. Drew knew that Valerie would use a tweezers on some of his most sensitive spots to teach a lesson in poor hygiene. She was a stickler and noticed just about everything. The nursery was comprised of six separate yet interconnected rooms. One room was for guests to view the proceedings in complete privacy and had still more of the two-way mirrors that were seemingly all over the manor and perfect for access. The first room was a private sitting room. The second room was a connected powder room and dressing room for Audrey so she could relax while Drew was being prepared. The milking room, the larger walk in bathroom and a dressing room where all of the necessary milking outfits were stored was where Valerie was now taking Drew to be prepared. Drew could never keep up with Valerie. Her confident gait forced the petite sissy to practically scurry to keep up. Once they entered the bathroom, Valerie turned on the lights and instructed Drew to remove her clothing. Valerie had admitted to Audrey that she truly enjoyed helping to mold sissies. She couldn't explain it, but training these sissies dampened her panties and today would be even more exciting with the changes in the milking process. "Hurry now sweetie." And so once again, Drew acquiesced and began removing her things. Valerie watched intently and offered commentary and instruction. Sweetie, pretend I'm your man watching you as you undress. Tempt me with you charms." Drew fumed, but followed Valerie's instructions as he always had. "That's right turn away from me and unstrap your pretty bra. Let me see your back with your small waist. Tempt your man and make him wait a moment or two. and then turn to me and shrug it off. "Drew, bra's are delicate mysteries to a real man, make a gift of that garment and lay it on his lap and let him smell the pretty perfume of your intimates." "Excellent, and now hands across your chest and cover yourself and slowly show me your precious little boobies." "Good girl!" "Don't worry," said Valerie, "we'll teach you everything you need to know to make your man crazy with desire." "Now, off with your little panties." Drew was once again fuming but did as instructed. "Knees straight", reminded Valerie. "Just push your panties to your thighs and squeeze them together and they'll fall right off." Drew stepped out from her puddled panties and bent over at the waist and retrieved the pretty garment which she then handed to Valerie who said, "wonderful, now stand still for me." By now Drew was completely erect. "Oh look said Valerie, our small friend is back! I know you're excited, but do please try to contain yourself." With lighting quick hands, Valerie grabbed a hairbrush and applied three vicious smacks to Drew's stem and just that fast; Drew's tiny erection was gone. "That's better said Valerie with a smirk." She knew that she could erect this delicate sissy, as many times as she pleased and poor Drew was helpless. Valerie was now doing a full body examination of Drew, Ear hair, nose hair, breath, make up, skin care, arm pits, pubic area, between her nether cheeks, manicure, pedicure, hair style and finally her lips. After that, the humiliated sissy was weighed in and her measurements were taken. "Drew let me look at you, you are a greyhound. You are so thin, you're about to disappear!" "Okay, let's get you dressed." Drew thought that was a great idea. Her little penis was throbbing from Valerie's abuse and she had never quite gotten used to being so totally exposed in front of Valerie. Valerie produced a very enticing eggshell colored bralette with a matching bikini panty with side ties. Drew quickly donned the items but was still flushing with embarrassment. "Don't be shy with me little one, I know you adore all of your pretty things." Valerie added a satin throat collar with two metal eyelets and two satin wrist cuffs with connecting eyelets. She then shook out a full-length see thru white nylon cape. When she threw cape over Drew's small shoulders and clasped it around her thin neck, Valerie knew that Audrey would be beyond pleased. "Drew, please raise your arms to your neck, but keep them under your cape." Drew obeyed and two clicks later Drew's wrists were snuggly attached to her neck collar. Working fast, Valerie instructed Drew to hold still while she dipped her hands into Drew's sheer panties and placed a condom on her delicate member, which was once again trying to erect. "Thank god for extra small, snug condoms," laughed Valerie as she patted the very small bulge at the vee of Drew's panties. It would be a shame for you to make a mess out of such a pretty outfit. Now's let's repair your makeup, your Mistress will be here directly." THE PHOTO SHOOT Serena had her breast augmentation three months ago on her eighteen birthday. It was a present from her father. She had been begging him for over a year and he had finally agreed after speaking with Audrey and Dr. Newman. Serena was now 5 4 102 lbs with long auburn hair a 19" waist and perfect C cup breasts, the right nipple had been pierced and a small bell attached. Her skin was flawless and her regimen of hormones had given her doe like eyes as well as a heart shaped bottom. As she went through the lighting checks Audrey explained that the internet content and web site revenue was nearing 12 million per year and Serena had a legion of fans. She's a superstar, let's watch. So, after the lighting was set, Serena began by pretending to put on her make up. She stood up to reveal her flat, tanned stomach and a French cut panty of black lace and pink ribbon, which matched her demi bra. To fill out the set was a frilled garter belt with four straps attached to black thigh high hose. Her five-inch stilleto heels gave her some height and as the camera snapped and the lights were changed, Serena put on a show. Her stomach was well defined and the vee of her panty was absolutely flat. After a few minutes, Serena was sat at the make up table once again. "Now watch this said Audrey. I saw the script last night and I think you'll enjoy this." Serena was adjusting her bra strap when a very large man came up behind Her. He placed his huge hands on her shoulders crouched down and kissed her neck. Serena leaned her neck to one side to give the man full access. The man was a security guard and this was clearly a reward for jobs well done in the past. Serena's breast was heaving as she was being titillated. Her chest was now heaving from excitement. His hands moved up and down her smooth shoulders and slender arms and the camera could tell Serena was enjoying the intimate attention, as her eyes were now half closed. All the while the camera and video recorded every movement. Now the huge beast of a male stood up and all he was wearing was a Speedo, which could not even hope to confine his large member, which was laying on the right side of the suit. Serena stood up, turned around and placed her tiny hands on the man's broad chest. It was hairless and Serena busied herself pinching his nipples and kissing his chest. She picked up a baby oil container and squirted some into her hands stopping every second or so for the camera to catch a different pose. She then smiled and rubbed her oiled hands onto the man's chest. "My god her back and waist and bottom are in perfect proportion and she is so toned", said Sarah. "Yes, unfortunately, she's well aware of those facts that these days." With the added height of her heels, Serena could place her arms around her man's neck and receive his kisses, but she'd have to reach a bit and after a few minutes she tired and began to kiss her way down to his waist. Just when tensions were building, lighting needed to be change and the shoot came to a halt. The cameras stopped while the set was rearranged. Serena's make up was touched up and she approached her co- star and they shared a few words and then just a few minutes later it was places for the cameras. Serena was now squatting in front of this huge man. Her hands were on his chest but her face was eye level with his still bulging manhood. His hand was on the back of her head and it practically covered her whole head. Then, Serena confidently peeked up into the man's eyes while she ran a long nailed finger under the waistband of his Speedo. She smiled when she heard him groan and immediately removed her finger only to repeat the tease several different times and in several different manners. Then she boldly took his massive erection into her hand through his suit and use her free hand to grab the surprised male's behind. She massaged it tumescence and played with it for a few moments until it was obvious that he was overcome with excitement. Just then, he quickly picked up the sissy model and cradled her in his arms and carried her to the couch where he sat her on his lap. They kissed for sometime before he unclasped Serena's bra. Serena gave a faux look of surprise when the bra became undone. Sitting on his lap as she was, she was sure to feel his large member through her thin panties and he was moving her back and forth in a rhythm over his turgid member. The action was explosive between these two now passionate lovers. The man busied himself with her breasts enjoying in particular the small bell hanging from her nipple. His hands were all over her lithe frame and when she felt she was loosing control, she flipped herself, spread her tanned legs and straddled him and then gave him an incredible lap dance. After several minutes, having her advantage back, she slid off the man's Speedo and used her hands and mouth to bring him to new heights arousal. Just when it seemed like she would master his large member, she stopped, stepped back and dramatically removed her panties and then let her soon to be lover remove her gaff. He then pulled her again to his lap where he played with her small penis by chaffing it with his thumb and index finger like a tootsie roll. In a few moments the man had Serena completely erect. Right at that movement Audrey reminded Sarah that Drew was waiting for them and that keeping to a schedule was paramount when properly training a sissy. "Besides, we have one more thing to do before joining Drew in the nursery." Sarah didn't want to leave but she knew her Mother was right so off they went. And just a few minutes later they again swiped a card and entered what turned out to be the Nursery Viewing Room. "Jim, how are you?", said a smiling Audrey. "I'd like to introduce you to Sarah Drew's step-sister and new roommate until your wedding." "Sarah, I'm charmed," said Jim. "My god you are as beautiful as your Mother." After a few minutes of niceties, Audrey asked Sarah to sit with Jim until the time was correct and she would know when that was. Audrey then left and moments later was in her sitting room. Sarah made herself comfortable after offering Jim a drink. She could tell he was very excited. "Jim, how long have you been watching?" "From when Drew entered the suite." "She's everything I want in a wife Sarah." "So submissive and soft, a true beauty inside and out." "Yes Jim, she's been created specifically to get pleasure from giving you pleasure." "It's a man's dream." "My Mother informed me that the session would last an hour and a half." "Perhaps we could make you more comfortable." "I believe you met Celeste last night and I'm sure she could get you a robe and we can have your pants and underwear laundered and returned." "How thoughtful of you," replied Jim. "Yes that sounds like a great idea." Sarah reached for the phone and almost immediately was greeted by concierge sissy of the day who after a very professional introduction received Sarah's instructions. Celeste entered the viewing room in her afternoon tea uniform. She had no time to change as she was summoned from her duties. She flushed furiously in front of Jim. Just a few hours ago she had provided her oral ministrations and Jim had practically drowned her with his spendings. Now she was again undressing him and taking his clothes while offering him a robe. She asked for any orders and then left for the laundry only to return a few minutes later. By that time, Valerie had just sat down next to Audrey and the two had a rather lengthy, intimate kiss. Drew was now in the milking room, a room decorated in lavish pastels, satins and silks and everything sissy. He was standing on his small heels with his body fully covered by the see thru cape. All around him were adjustable padded tables and padded benches and a small divan. There were also different machines along the walls. While Drew knew each one intimately, he also remembered the habilitation of being machined milked while Valerie and Audrey looked on and mocked him. The machines were devilish and offered no mercy. Once strapped in and attached the machines did as their masters bade. Just a few feet away, Audrey had discarded her clothing and was dressing in a voluminous chiffon white skirt, which she perfumed, and a sheer pale blue blouse with just two buttons. No panties or bra today. A lot was planned and she wanted to impress Jim and give her most prized sissy some new things to think about. Just six months to her wedding day and the poor little dear has no idea how to satisfy a man! "Okay Valerie, its time." The women embraced again and then entered the milking room. The show was about to begin. "Well what do we have here?" said Audrey. She walked around Drew, casually running her hand through his soft locks, checking a bra strap and finally adjusting the tie on his bikini panty after checking that the protective condom was still in place. "Valerie, our little princess is perfect." "Nice work." Audrey crossed the room and made herself comfortable on the divan. Her skirt billowed about as she sat down and then she motioned Valerie to bring Drew over. "Drew, that cape is so deliciously feminine, especially with your hands out of the way." "Sweetheart, come sit on my lap." "Yes, that's a good girl ...snuggle up close." "Precious you smell so sweet, like lilacs." "Do you like my skirt?" "I wore it especially for you today." "Yes I do, stammered Drew, "its very pretty." "Well that's sweet of you to say," said Audrey as she traced Drew's lips with her fingers. "Darling don't fidget so much, be still." "I'm sorry, whispered Drew. "It's alright sweetheart, I know you're excited." "Let me ask you something and I want you to be honest okay." "Yes Mommy." "Do you think you're pretty?" "What?" "You heard me little one, do you think you're pretty?" Audrey was now caressing her sissy's neck and developing cleavage. "My you're really starting to fill out your bras these days, but please answer my question." Drew hesitated again and Audrey raised her hand. Valerie stepped forward and literally pulled the sissy off of Audrey's lap. The surprised sissy received 10 rapid smacks to her bottom and with her hands restrained as they were, Drew could not defend her and began to cry. Audrey motioned for another series of 10 sound spanks and after they were completed the crying sissy was returned to Audrey's lap. "Now Drew I know it hurts, but be a brave girl and when I ask a question answer it." Drew was still crying uncontrollably. Audrey unbuttoned her blouse, exposed a breast and pressed the sissy to her nipple. Drew greedily sucked the nipple trying to control his crying. "There, there my precious, I know how you feel and I'm here for you." Inside the viewing room, Celeste had returned and was positioned once again between Jim's legs. Her head was gliding up and down, but Jim was transfixed by the actions in the milking room. Sarah was also watching intently but peeked over at Celeste and Jim. She felt dampness between her legs and was waiting for the time when she could come in. Sarah marveled at Jim's largesse. He was really quite handsome as well. Drew was a lucky sissy to have a catch like Jim. Back inside the milking room, Audrey had suitable calmed Drew. The room was filled with the sounds of suckling. Audrey broke the spell and again asked her sissy if he thought he was pretty. Drew hesitated again and once again Valerie mercilessly applied punishment to Drew's now red bottom. It took two more such spankings before the reluctant sissy was ready to answer any question Audrey had without hesitation. "So darling said Audrey as she took his chin in her hand, do you think you're pretty?" "Yes," said Drew. "Well, what's your best feature?" The sissy looked confused and terrified. "Feature uh you mean physical or oh." "Yes princess I mean physical feature." "Well, I think my bottom is very pretty." "Hmmm, that's interesting, and what else is pretty about you." "Well responded the pensive sissy, I have a small waist." "So you like your bottom and your waist...is that what you're saying?" "I g-g-g-guess so." "Drew tell me, do you like being admired?" Fearing another vicious spanking Drew quickly answered yes. "And what about men admiring you?" "I'm not sure replied the sissy now shifting and trying to remove her hands from her neck." "Please don't fight the restraints or Valerie will be upset with you and stop fidgeting. Just sit quietly on my lap and answer my questions, okay?" Drew nodded as best she could with her chin still in Audrey's hand. "So, about men, how do you feel when they look at you?" "I don't mind," said Drew quietly. "But are you aware that they see you as a sexual object, does that excite you?" Drew was trying to answer the question and Audrey reached a hand down into Drew's panty and found a throbbing little erection. "Well, I think we have our answer but I'd like to hear it from your lips." "So, tell me do you like when men look at you?" Drew hesitated and as he saw Audrey's hand about to signal Valerie he spat out, "Yes, I think so, I mean I'm not sure but yes, maybe." "Would you like to be touched by a man?" "I'm not sure." Once again the sissy was reduced to tears and Audrey began breast-feeding Drew anew. Inside the viewing room, Celeste was still on her knees between Jim's legs licking her lips and recovering from Jim's violent orgasm. Sarah was intrigued as well. Audrey was forcing Drew to accept that men were attracted to him and that he might be attracted to them. It was an awesome display of Audrey's power and Sarah was anxiously awaiting her part in this erotic drama to begin. "Men are interesting darling," continued Audrey. "They can make you feel special and loved and appreciated." "It's nothing to be frightened about, why are you shaking?" "But I'm not gay," protested the pantied sissy as she clenched her restrained hands into perfectly manicured little fists. "Oh, now darling, but you don't even know." "I mean have you ever been with a man?" "No, of course not," protested Drew. "Well, then you don't know for sure do you and you do admit that you like men looking at you." "Well?" "Yes, I guess." "You must realize that a young woman would not see you as a potential suitor?" "Well, I'm not sure." Audrey stroked the sissy's clean-shaven thighs and then began to trace the head of her little stem through her panties. Drew swooned. "Drew sweetheart, a woman craves a man, a real man." "You need to put all thoughts of ever being a real man aside." She was now pretending to adjust Drew's bralette. "Drew a real woman wouldn't even give a thought about being with a sissy." "A woman wants to be satisfied and frankly darling you just don't have the equipment." "Its okay princess, you can cry." "I love you and I'm going to make sure you're life is full and rich." Drew was indeed crying again and was nearing exhaustion. Audrey motioned to Valerie and she came forward and positioned Drew on her knees in front of Audrey. Valerie then took Audrey's skirts and placed them over Drew's head. "Darling I hope you like my choice of perfume," giggled Audrey. "Do what you do best" Drew was placed right in front of Audrey's sex and began to lick his mistress. Audrey leaned back and spread her legs and for the next 15 minutes received worship and relaxed. Drew had learned over these many years how to pleasure a woman with his tongue, now he would learn how to apply those skills to a man. Right after her second climax, Audrey abruptly pushed Drew away and went to her dressing room. Just before she left she instructed Valerie to take off Drew's cape and place him onto the padded bench. Drew didn't understand, he had never been placed on the bench and was just hoping for relief and his nap. Audrey changed out of her skirt and blouse and decided the best outfit would be nothing. She knew she had an exquisite body and she wanted to tease Jim. Poor Celeste Audrey thought to herself, Jim will be beside himself. Valerie removed the sissy's cape and now her immature body was on full display. Her bralette and panty were her only defenses. Her hands had been immobilized and were secured to her neck collar. She tried to relax and Valerie lifted her up and placed her on the bench on her back. Having the women pick Drew up made him feel weak and helpless. "Lie back little one." And as Drew did, Valerie diddled his little penis in panties and laughed. "You're not mad at me are you?" Audrey came back into the room and both Drew and Valerie gasped. "So, we were talking about men weren't we Drew." "Please turn over." Drew complied but realized that there was a hole in the bench. Initially he thought it was for a face but now he realized that Audrey and Valerie would have access to his member while he was on his stomach. But, right now, Audrey was interested in his bottom. She was rubbing his bottom through his panty. "Tell me more about your cute bottom, is it sensitive?" "Y-Y-Yes." "And do you like it when I rub it like I'm doing now." "Oh yes!" gushed Drew. "Would you like it if a man rubbed your bottom?" "I don't know." Audrey's hand disappeared into Drew's panties. "Sweetheart I'd prefer it if you didn't clench your bottom." "That's a good girl." "Valerie you can apply the cream now." The cream was a hormone cream and Valerie usually put the cream on once per day right before bedtime, but now the regimen was to be changed and the dosage was to double. The cream was used in favor of a pill because having the cream massaged into the sissy's skin helped reinforce Drew's docility. Audrey checked Drew's erection from under the table and proceeded to explore Drew's bottom under her panties while Valerie began the massage. Audrey boldly began to probe Drew's rosebud. Drew gasped with surprise and clenched. Audrey looked at Valerie and she then gave Drew a vicious pinch on her arm. Drew screamed in pain but relaxed his bottom. Under his panty Audrey made little circles around his little pussy teasing and pressing. She checked his erection and he was responding. "Someone likes her tushy played with," teased Audrey. "Imagine what it would feel like if a man were doing that sweetheart." "I think you'd love it." Sarah knew that was her cue and excused herself. Jim was now standing and leaning against the two-way glass. Celeste had again attached herself to his latest erection. Jim is insatiable thought Celeste as she once again began pumping her head up and down. Just a minute later, Sarah appeared alongside her Mother and just as naked. She too was a picture of fitness and sexuality. She was glistening with sexual energy. "Drew, Sarah came to be with us isn't that nice?" "Uh yes mommy." "Mother her bottom is so red." "Well, we have to get Drew over her shyness." "I see," said Sarah. "You know Sarah, Drew admitted he likes men just a few minutes ago." "Really!" said Sarah. "No, I, well I...." "Drew what are you trying to say sweetheart?" "Hush darling", intoned Audrey. "Anyway his bottom is very sensitive." Audrey once again slid her hand beneath Drew's panties and tormented his blossom. Sarah said, "Mother may I?" and Audrey said of course. She sat down on a chair and signaled Valerie to bring the sissy. "Drew over my knee princess." He hesitated and Valerie again administered a pinch. Drew immediately complied. It was a struggle without the use of his arms but he complied and now Sarah was stroking his panty-covered bottom. "So," she started, "you like men." "Well, I've known that since we were children silly." She continued her verbal torments until the sissy began to simper and then she pulled the bow of Drew's panty to bare her bottom. "Yummy,", said Sarah. And began to rub and massage it. She then reached forward and placed a finger in Drew's mouth. "Make it wet for me sissy." Drew complied as Sarah began pumping his mouth with her finger simulating a phallus. "Good girl, you can really take it can't you." Drew was arched over Sarah naked lap, and she had his tiny erection pinned on her thigh. "Don't you dare cum Drew or you'll be sorry," warned Sarah. Sarah then massaged Drew bottom for several minutes until she spread his cheeks and pushed a finger into his bottom. He tried to pull away, but Sarah was insistent and strong. "Relax Drew, don't fight me." "Go with it and it will stop hurting in a minute or so." And so Drew tried to relax. Sarah began pumping and all of a sudden Drew was pushing back. Valerie was smiling and so was Audrey. They all knew for sure that Drew was going to be a natural. Sarah continued tormenting poor Drew bringing the sissy to the brink of release and then stopping. "Beg me!" said Sarah, "beg me to finish you." "PPPPlease!" said Drew. "I can't take anymore." At that moment Sarah Stopped and stood up and Drew tumbled to the floor. Valerie helped the stunned sissy back up on the bench but this time the sissy was on her back and her legs were placed into stirrups. The woman gathered around the bench and quickly removed the sissy's bralette. Now the poor dear was totally exposed save the condom that Valerie had put on her some time ago. "Our poor little dear is embarrassed", said Sarah. "Well, it has been a tough session," replied Audrey. "Drew's coming to grips with the fact that she'd like to have a boyfriend, right Drew." "Ah ah well, I guess." "Don't be shy we might be able to help you in that department." "But now I'd like to have Drew understand what a man has to offer." Drew looked confused until Audrey gave Sarah the vibrating dildo. "Meet today's boyfriend!" said Sarah. It didn't take Sarah long to insert the vibrator into Drew's obedient mouth. "Open wide honey." "Suck it, show me how you can get it hard, suck it like it was your boyfriend's." Drew was flushing furiously but continued to suck while Audrey was greasing his exposed rosebud. Valerie was now rubbing the hormone cream onto Drew's now naked immature breasts. Audrey was between Drew's legs marveling at how the hormones had shrunken her little pearls and was finishing the process of securing her legs into the stirrups. Inside the viewing room. Jim's eyes were glazed over. His erection was back in full force and he was ramming it into Celeste's mouth, which was filled to capacity. She wanted to tell him to slow down because she was literally choking on every stroke, but she calmed herself and remembered her training. In a few moments she found the peace that comes with total submission. Still, though, the room was filled with the noises of her spasmodic choking as Jim's large member rammed the sensitive area in the back of the pantywaist's throat. Back inside the milking room, all three women were busy with Drew and yet his little staff had yet to be touched. This was not the normal milking thought Drew. But the women had other ideas and stopped in unison. Drew still had his little hands attached to his neck and could not defend his nether region from his female tormentors. With his legs securely restrained in the stirrups, Audrey asked Valerie to remove Drew's condom. Valerie obliged and with a snap the tiny condom was flicked off and placed in the rubbish. "Drew darling, don't be such a showoff." "I do believe that today's erection is well above three inches." Sarah giggled and so did Valerie for that matter. "Drew, as you know we ladies get examined in these very same contraptions." "I'd like to examine you." "While Valerie puts cream on your sissy stick, I'm going to remind you that I will be very angry if you fail to control yourself." As Audrey inserted her finger into Drew's rectum Valerie began to massage the hormone cream onto his small penis. Valerie alternated her strokes with pinches on the head of Drew's sensitive tip. Sarah joined Audrey between the stirrups and the two women took turns violating the now sobbing sissy. After some minutes, Audrey took out a bright pink vibrator and asked Valerie to stop her ministrations. Sarah was given the honor and began to violate the sobbing sissy with the phallus. Drew felt exposed, tortured and yet as excited as she's ever been. Everything was so tingly and yet she couldn't control her tears...why? Audrey and Valerie were now teasing Drew. Nothing was off limits and the air was filled with Drew's crying and the women's jibes and laughter. Audrey then walked to the front of the bench and leaned over and calmly whispered to Drew that it was okay to cum. She kissed his forehead and encouraged him to give in. Now all the others were encouraging Drew. Sarah was pumping the vibrator rapidly and was screaming, "You're boyfriend wants you to cum!" Over and over Drew heard the shouts from the women about dating, her boyfriend, the future. Finally, she heard a shout and then came with several small violent spurts. After a moment she realized two things; it was her scream and that she had cum without have her peener touched. As her crying subsided, the women congratulated Drew on her first experience with her girl pussy. "You loved the vibrator," said Sarah... "All women do!" "Your going to love a real man's penis," said Audrey. Drew was recovering and her sissy seed was all over her stomach. Valerie cleaned her up and she was released from her neck restraints and the stirrups. Audrey asked that Drew thank the ladies and kiss them goodbye. Valerie then took charge of the wobbly sissy. "Valerie, she can lie down for 15 minutes and then I want her to visit Doctor Newman's office for labs and a check up." "Call us when you arrive." After Drew left the room, both naked women hugged. "My god Mother, what we did to that little sissy." "She was so over stimulated, I thought she was going to burst." " The important thing was that she responded so beautifully to the rectal stimulation." "She has a hyper-sensitive bottom and that's a bonus for Jim." "And, this will be a picnic compared to our when angel discovers that you moved into her room." "Mother I can't wait!" As for Jim, Celeste had drained him three times, the last by hand. Jim never let his eyes stray from his fianc?e. He couldn't wait for their wedding night. Celeste had a similar elation......her jaws, neck and knees ached, but she was proud that Jim was happy. An hour later the women were once again dressed as was Jim and they were chatting in Audrey's private study. "I trust you enjoyed the live training session Jim." "Oh yes, it was beyond my expectations." "I'm floored by Drew's progress." "Well, we've got several hurdles in front of us, but I think you'll be pleased." "I believe the schedule calls for a 50's costume party next week, followed by a pool party." "And as Drew doesn't have swimwear, I was thinking you might enjoy that shopping experience." Both women noticed Jim's prominent bulge in his pants. The women then excused themselves and still another eager sissy was sent in to "calm" Jim's situation. As the two women walked down the hall Sarah said, "That must be a record Mother". They both laughed. "While Drew rests and Jim gets relief, let's grab some lunch. We don't have much time because Drew has a Doctor's appointment today." , said Audrey. Mother, what's the appointment for? You'll see, Dr. Newman is very talented! DREW SWEETHEART DON'T SHAKE, I'LL REACH INTO YOUR PANTIES BECAUSE I KNOW YOU'RE SO SHY. NOW DARLING TURN YOUR HEAD FOR ME AND GIVE ME A NICE COUGH. GOOD GIRL! SAID DR. NEWMAN..............