Family Planning free porn video

"Family Planning" The bright sunlight streamed through the window sheers on a mid Saturday morning as Madge stood in her boudoir of a bedroom in front of her dresser. She tied the black satin sash at the waist of her floor length black nylon robe, her slender fingers working and swishing the sash into a gleaming bow as her long gloss red fingernails flashed in the light. She smiled slightly, with satisfaction at her always flawless, feminine appearance as she noticed the light foundation makeup that gave her skin a porcelain perfection and noticed her gloss red lipstick as she fluffed and then smoothed the layered black chiffon creation then checked her look in the mirror. Her eyeshadow was smoky gray and darker at the outer edges making her eyes look larger. They were lined with black eyeliner now and the long false eyelashes she wore further highlighted her dark brown eyes. She ran her hands over her dark brown hair that was now combed and pulled tightly back into a severe bun making sure not a hair was out of place. She was just finishing with a few drops of perfume as a knock came at the back door. The long black chiffon robe swished and gleamed in the light as she turned and left the bedroom with a slight smile. The loud click of the black patent leather stiletto heels was louder than usual and her steps were shorter giving evidence that she was wearing even higher heels than she normally wore. The zipping sound that echoed through the kitchen as she minced and wiggled along gave evidence that underneath the long nylon robe she was wearing a pair of her sheerest hose tightly gartered high on her thighs. She looked out the window to see Henry, Tim's dad from next door trying to hold his excitement as he waited. Madge then opened the door. "Tim just left with his friends. They're going downtown and then going to the matinee at the movie. I told him to be back by supper time and that I'd be gone until late in the afternoon," Henry said with excitement in his voice as he looked Madge over. She closed and locked the kitchen door then pulled the louvered wood shades down as she turned and leaned into him feeling his chest through his old college T-shirt. She then looked into his eyes as her hand descended until she was working the crotch of his baggy sweat pants cupping his dangling ball sack playfully yet carefully with her red taloned fingernails. She cooed with satisfaction as he gasped. "We have all afternoon then. Perfect" she said. "Shall we get started?" she said as she led him downstairs to the basement. Henry followed down the stairs and across the basement to a sturdy, well locked door. Madge opened the door, led him inside and switched on the lights to reveal a modern, well equipped bondage dungeon! She then closed and locked the door securely behind them. The room was done up in dark tones, black leather evident everywhere. The dark gray carpet and the heavy walls giving evidence the room was quiet soundproof as well. She motioned for Henry to get undressed and watched with seeming growing impatience as he stripped off his shoes and clothes then set them aside. It was evident that these two had met under these same circumstances before because it seemed routine and at first hardly a word was spoken. She took a white garter belt and a long pair of sheer beige nylon stockings from a dresser and approached Henry. After moving behind him and hooking him into the garter belt she had him sit then began gathering and working the stockings high up on his thighs and gartering them tightly into place. She didn't favor the hair on his legs but was nonetheless satisfied at the effect. She had him take a seat on a leather padded bondage table then fitted him into a pair of stiletto heeled ankle boots and laced them on tightly. The 8 inch heels on the gleaming black patent leather ballerina boots not only prevented Henry from walking they also forced his feet into a pointed and impossibly high arch! Madge helped Henry roll over onto his stomach and straddle the padded black leather of the chrome metal bondage table that was securely bolted to the floor near the center of the room as Madge quickly went to work. She worked his arms into a black leather arm binder complete with black leather mittens. After folding his arms behind him she laced him tightly then buckled the sturdy cuffs at each of the wrists. Now satisfied she began hooking up the several sturdy black leather buckled straps on the contraption. It took a bit of work but within minutes she had Henry trussed and tied to her satisfaction. "So exciting and enjoyable, out little sessions, aren't they dear?" Madge cooed as she worked Henry to the table. "It's such a shame that your wife has left you though. But at least your divorce is final now. I can't believe it's been over a year!" she said in conversation as she continued. Henry grunted and struggled a bit as she strapped him down and adjusted the metal supports of the articulated bondage table but finally she was finished. She stood back smiling now, admiring her work as she paced around the table. Henry was quite immobile now. His arms now behind him were bent at the elbow cocooned in the tightly laced leather sheath which forced his shoulders close together and his chest out. The several straps of the sheath were tightly strapped to the table. His legs were now spread and strapped tightly at the upper thighs, just above the knees and securely at his leather booted ankles and for a finishing touch a wide leather cinch belt secured Henry's mid section tightly to the table. Madge started by pulling at the black satin sash at the waist of the gleaming black nylon chiffon robe undoing it then worked the robe off her shoulders with a swish and set it aside on a padded chair. Henry watched as she moved to the large wooden cabinet along the wall. He immediately noticed her astounding look for this session. She always looked good but today she looked stunning! He had already noticed the makeup and had smelled the perfume but now marveled at her gleaming black high stiletto heels and the manhattan heeled seamed black hose that gleamed on her long shapely legs. He watched her hips undulate under the form fitting black satin panties as she minced across the room, her perfume following her like an invisible cloud as her nyloned thighs whisked and zipped. He noticed her ample bust jiggling in the cups of the tight, gleaming black satin corset she had on and followed the lines of the garment that cinched her waist tightly then flared out over her wide womanly hips to terminate in multiple black garter straps that held the jet black welts of the sheer nylon hose taut. He watched as she selected then put on the long pair of soft black leather gloves. They went nearly all the way up her arms like opera gloves but these were no opera gloves! He watched as she tightly buttoned the buttons at each wrist and smoothed the leather tightly over her hands and up her arms and became a bit restless when she selected a black leather riding crop from the well stocked cabinet complete with all manner of whips, gags, hoods and restraints all done up in black leather as well. "Today's a special day Henry, a special session," she said as she gripped the riding crop in her leather gloved hand then turned on her heel to return to his prostrate form. She teased his dangling ball sack with the end of the riding crop causing him to squirm. But he suddenly gasped as she raised the crop and brought the square folded leather flap down briskly onto his upturned right cheek causing a loud resultant "Uuunnnggghhhh!" She giggled as he struggled pulling at the straps causing them to creak while she watched the pink welt in the shape of the riding crop form on the now quivering upturned cheek. She then strutted around the bondage table teasing Henry as she continued. "I think it's been long enough now, we could become an item now don't you think?" she said as she continued her walk causing Henry great apprehension whenever she moved behind him as she held the riding crop toying with it teasingly. "I...I g..guess we could," Henry said now thinking about the offer. The crop whistled through the air and hit its mark once again catching him off guard and causing him to grimace and causing another welt to form but on the left side this time. "Did I tell you that you could speak?" Madge cautioned, giggling slightly as Henry fell silent once again. "Good boy," she added as she continued strutting and mincing around the table once again as the session continued. "We get along so famously we should be together. You're single now and with your little boy Timmy you need a woman in your life again. We could make it complete and become a family" she said to Henry's seeming interest. "But there needs to be a few ground rules dear. We can continue on with our little sessions of course and nobody has to know. After all it is fun for the both of us isn't it?" she said as she sent another stinging crack onto another as yet untouched portion of Henry's upturned buttocks causing another pink welt and another "Unnnggghhhh!" she giggled. "But, there is something else," she said pausing with a slight yet excited smile. "What do you mean something else?" Henry questioned. "It's about little Timmy," she continued. "Tim?" He turned as best he could. "How well do you know your son? I mean do you know everything about him?" she questioned. "Yeah, I guess so," he answered. "Are you sure? Are you sure there's nothing out of the ordinary?" she continued adding another slap with the riding crop. "Uuunnnggghhh! No! He's just a regular kid," Henry returned. "A regular 'kid.' He's a nice boy to be sure, but he is different you know?" Madge smiled. "What!? What do you mean 'different'?" Henry returned. "I think your sons a sissy," she continued as she waited for the response, her excitement growing. "What!? A sissy!? You're crazy!" he replied as Madge giggled slightly. "Well if you had no idea about little Timmy, he must have been very quiet and very careful about his little 'hobby.' Haven't you noticed how quiet and reserved he is and how he doesn't like to play the rough and tumble games like most of his friends. And how about the fact that he's smaller and more slightly built?" She continued. "That doesn't mean anything," Henry answered. "That's true Henry," she replied. "But what if I told you that Timmy, your little son likes to wear ladies lingerie? He likes the feel of lacy nylon slips and nylon stockings! Wouldn't you say that if a boy likes to wear soft and silky ladies things that he's a sissy?" she finished. ""Tim's a good boy and I don't like the direction of this conversation. I...I think I've had enough Madge. Untie me, let me up," Henry said as he struggled with the leather straps. "Sickening," she said as she minced over and returned with a leather padded wooden chair then sat down next to the bondage table. "It's a sickening thought at first, your son in panties, nylons and high heels isn't it? I know. I was shocked at first but after it set in for a while I found there to be a certain excitement in seeing your little Timmy trying to walk on high heels," she finished. "You're crazy! You're making all this up! Now let me go," Henry said once again. "I am getting ahead of myself aren't I. After all how could I possibly know your son is a little sissy?" Madge said as she continued. She crossed her nyloned legs with a swish then continued. "It started quiet by accident. Let me explain." "A couple years ago on a warm summer day like today I was in my back guest bedroom changing the bed when I saw a baseball fly over the hedge into my back yard. I didn't think much of it at first, but I watched as Timmy ran through the gate to collect it. I thought nothing of it but, on his way back I watched as he stopped at my clothesline. I had done my wash earlier and was just about to bring everything in when I noticed Timmy pause at the line. He looked around making sure nobody was watching then began to look over a pair of my lace trimmed panties hanging on the line. He felt the sturdy white satin panels of a nearby girdle and looked over the garters then felt the fabric of my white lace trimmed nylon half slip hanging nearby fluttering in the breeze." "Well, boys can be inquisitive it's like when they look through the big winter catalogs at the ladies lingerie. I'm sure they all do it," Henry answered. "But he did more than just look didn't he Henry?" she said. "I watched as he felt the lace trim then felt the cool nylon material of that slip then watched as he gathered the material in his hand and rubbed it against his cheek and smelled the traces of my perfume still on the fabric! It seemed like he was in a trance! I heard his friends yelling from over the hedge then watched as he returned to his senses then quickly trotted back to the game. Such a strange thing, a little boy that's interested in ladies lingerie isn't it?" she said. "It's probably nothing, like the catalogs or panty raids in college," Henry said now becoming tired of the conversation. "That's what I thought too, at first" she continued. "You know how nice a young boy he is and how he always comes over to mow and shovel snow. Well I always leave a ten dollar bill on the kitchen counter on Saturday morning when he mows. I have my hair appointment in the morning so I leave the back door open. That way he can get a drink if he wants and pick up his money if he gets done before I get back." she said as she continued. "I started leaving the back door open for him. I guess I wanted to see for myself if little Timmy was getting interested in girls or if it was just the ladies clothing and the lingerie." "Tim's a good boy he's quiet, reserved and never gets into any trouble," Henry insisted. "Oh but you're wrong Henry dear. It was only a couple weeks after the clothesline incident. I was off to a hair appointment, at least that's what I told Timmy as he mowed the lawn. He watched me leave as he continued mowing. Instead of going to the hair salon I drove to the little caf? that's only a few blocks away. I waited there an hour and a half to give him some time to finish the lawn and to see if something else might happen. And it did!" she said with a giggle. "I don't believe it," Henry said in disbelief. "I parked a ways down the block so he wouldn't hear the car in the driveway then I walked back and quietly entered the front door. I could hear someone in my bedroom as I quietly walked across the living room and as I started down the hall I could see the bedroom light was on and knew someone was in there. I tip-toed to the edge of the doorway and peeked in to see your little boy, your little Timmy wearing a pair of my lacy pink nylon panties and a pair of my pantyhose! I saw the pink bath towel on the chair then noticed his still damp hair combed back and that he had put on two of my pink hair berets. He even had on a pair of my high heeled shoes and was preening and mincing around the room just like a little girl! I was amazed at how well he did walking in those stiletto heels!" Madge giggled. "He was beside himself with excitement, that is until he saw me," she said with another giggle. "He gasped in embarrassment and then stammered and began apologizing as I entered pretending to be angry. But it was what I had planned might happen. I was shocked at the sight but I wasn't really that surprised. He quickly stripped everything off then pulled on his jeans and T-shirt and made for the bedroom door but I stopped him." "So, you like ladies lingerie hummm Timmy?" I asked. "He said he didn't of course but I continued by scolding him, telling him how wrong it was to sneak into my bedroom. I told him that he would have to be punished. He wasn't sure what I meant but I told him that since he liked ladies lingerie so much he might as well do it right. I told him I was going to start dressing him. Little Timmy was soon going to be getting his fill of wearing ladies lingerie!" "He started whimpering and gasping in terror. He fidgeted and put up a fuss trying to pull away and wouldn't cooperate. But I told him it was either that or I tell his parents or maybe even his little friends. What would you do Timmy if everyone found out you were a little sissy hummm? Would you like that?" I said. "A little boy wearing ladies panties and walking on high heels. It was easy after that," she finished. "I'll have a talk with him, straighten him out," Henry said with a trace of anger in his voice. "I already have," Madge interjected as she got up from her chair and took the leather riding crop with her holding it firmly in her leather gloved hand. And then another half hour passed. Henry squirmed still strapped to the table, his upturned buttocks now dappled with over a dozen reddish pink marks evident that Madge had found further use for the riding crop. She now sat at the head of the table holding Henry's chin and tilting his head back with one hand while holding a tube of red lipstick in the other. Henry squirmed and grimaced as she began applying the gloss red lipstick to his lips in broad heavy strokes. She carefully applied the lipstick to his lips until they were full, pouty and a high gloss red. She then set the lipstick aside and produced a large black rubber ball gag. "Open up sweetie," she cooed as she worked the gleaming rubber ball against his lips. "W...we d...don't need the gag!" He struggled and grimaced. "Well today we do sweetie because I have a surprise for you!" she said as she continued. Then taking a tight hand full of hair at the top of his head she pulled hard and then yanked back until Henry gasped in surprise and then yelped in pain. Madge then quickly wedged the ball gag tightly into his mouth and began pulling the black leather straps around his head. She pulled the buckle tight at the back causing the leather straps to sink into his puffed cheeks as he blubbered and "mmmfffed" into the gag craning his neck and turning his head to get away but it was no use. As Henry struggled on the table not sure what was coming next he watched as Madge rolled up a large full length mirror in front of the table he was strapped to. She then returned to the cabinet along the wall and began looking and rummaging through it. She then quickly returned with several items and took a seat at the back of the table then began putting white latex gloves over the black leather ones she already had on. She opened a tube of lubricant and after squirting a large dollop onto her fingers she began working it into Henry's backside! He squirmed at the cold, slippery sensation of the clear gel as Madge worked it into him. He then blubbered into the gag and began pulling and struggling with all his might to see in the mirrors reflection that Madge had now taken out a large flesh colored dildo and was applying lubricant to it as well! "We're going to become quiet a family, you, me and little Timmy too!" She said as she stripped off the latex gloves then began working the large dildo up and down Henry's crack until she found the opening. She then began pushing and twisting it working the slippery dildo against the slippery lubrication already applied to Henry. He "mmfffed" into the gag and began to struggle when Madge found the opening and began to push even harder but soon the large bulbous head began to stretch Henry as it began to enter! "Mmmmmfffff! Unnngggghhhhhh!" he gasped as Madge held the flesh colored rubber stub at the end of the dildo and pressed it harder still. "Don't fight me sweetie, you're all lubricated and you won't be able to hold out for much longer and with Timmy off with his friends we have all afternoon!" She said with a slight giggle then pushed and worked the dildo deeper inside! "Unnnngghhhh, unnggghhhhh, aaarrrrruuuummmmppphhh!" he strained blubbering into the tightly cinched gag with puffed cheeks as Madge pushed the dildo in further. He felt the head stretching him tight and felt the pressure continue to build as he struggled on the bondage table pulling and yanking at the stout leather straps causing them to creak but little more. He gasped again "Uuunnnggghhhhh! Oooommmmppphhh!" as Madge finally stretched him tight and the large bulbous latex head finally entered! He gasped and whimpered twitching at the experience but Madge kept working the vein engorged shaft inching it deeper and deeper inside. He felt it sliding further in! "See sweetie, once we got that head in the rest will be easy now" she said with satisfaction. But the dildo wasn't standard issue. The wide 6 inch rubber appendage was formed a bit larger at the base, it then tapered off quickly to about a third less size in diameter at the handle end to act much like a discipline plug. Henry struggles started once again when he felt himself being stretched even tighter now as Madge continued. "Mmmmmmmffff!" He blubbered into the gag as Madge sunk another inch inside him. "Aarrrgggghhhh, Uuuugggghhhhh!" He squealed as he writhed on the table now until he finally let out a loud pained grunt. Madge watched as his widely stretched bottom quickly tightened around the small end which afforded some relief. She then spread his cheeks and pushed the dildo all the way in until the realistic looking ball sack was pressed tightly against him which caused Henry to squirm and squeal once again. Now satisfied, Madge released her grip on the dildo handle, the dozens of fine decorative black cords coming out of the handle end gave the appearance that Henry now had a tail! Madge was pleased and excited at her control as she wiped his brow with a small fluffy white towel then released his head to let it rest on the padded leather. Looking on to see Henry only twitching now and blubbering weakly into the gag she was satisfied he was weakened sufficiently to continue. She wanted to make sure he was pliable to the plan she had been working on for so long. She then began adjusting the little bondage bench as Henry was forced to look on helplessly in the mirror. He was a sight. His gloss red lips stretched wide around a black rubber ball gag that was tightly strapped in place. His arms in the leather arm sheath were cinched back tight behind him and then strapped to the table making any real upper body movement impossible. The garter belt held the glossy beige stockings high and tight on his legs and the black patent leather ballerina boots continued forcing his feet into a painfully high arch. Madge worked a lever that dropped the back of the table downward. She worked another that spread his leather strapped thighs wide then worked the front of the table up causing Henry's back to bow backwards. She made sure the mirror was in position so he could see everything then quickly re tightened all the leather straps until the grimacing blubbering Henry could barely twitch. She moved around him marveling, studying the gloss red lips held open wide by the black ball gag his tightly gartered stockings and how his thighs were strapped and spread wide to the padded legs of the table. His legs were bent at the knees, his ankles strapped to his thighs as well forcing his booted stiletto heeled toes straight up. His back was painfully arched backwards now and the wide belt strap around his waist held his torso immobile to the table while the leather arm binder further up was strapped and cinched tightly to the upper portion of the table. She took a black spandex and velcro strapped apparatus and moved around behind him once again. She began fondling his dangling ball sack which was now mere inches off the floor. She then began working him, stroking his shaft until it started getting hard! "Mmmmmm, you might be tired but it looks like your little friend here still wants to play!" She giggled as she continued stroking him until he was gasping and his erection was large and throbbing. But before he could have release Madge stopped stroking him and quickly wrapped the gleaming black spandex strap around the root of his penis and dangling ball sack! She worked the tight sleeve around his manhood and the other ends around his ball sack then snapped the three little snaps in place. She then pulled two more straps through the main one around his sack which tightened and separated his testicles! She tightened the straps then pulled and worked the wider velcro strap around his scrotum until it was tight and distended, his testicles now painfully stretched downward and out at an angle from the separator strap. She worked his erection once again stroking it back and forth teasing the bulbous head then quickly cinched off the tight spandex velcro straps around the base of his manhood. "Mmmmmmm baby, all dildoed, plugged and strapped, I could keep you this way for hours. And strapped nice and tight like you are you can't possibly come! Not until I want you to." She giggled at his predicament as he struggled on the table. Then once satisfied he was now totally erect she let go, letting the large throbbing erection strain as it bobbed in the air, a single clear drip of pre come forming at the tip. She then spread out the little fluffy towel on the floor directly beneath him then returned to her chair and crossed her legs with a nylon swish once again. She pulled an ashtray close on a little table, lit a cigarette and began a one sided conversation. If the situation didn't look so absurd it could have passed for a counseling session. "I think we'll get along fine as a new family Henry dear, but there's still the matter of young Timmy. I've been working on a plan and I do think that you'll agree it's all for the best once you understand." "I've been working with him since I caught him in my bedroom playing in my panties and lingerie. I can't believe it's been nearly two years now. And you and your wife never had an inkling that your little son Timmy was a sissy" He put up quite a fuss at first but I knew he couldn't help himself. Little cross dressing sissies can't stop, I guess it's genetic or something. I find it so deliciously kinky. And so exciting to have such total control over little Timmy by knowing his secret." She said as Henry grunted twitching on the table now forced to listen. "I started dressing him whenever I could, usually on Saturday mornings and even some afternoons after school. I bathed and Naired him until his skin was totally smooth and hairless, and aside from the little triangular wisp of pubic hair I allow him to keep he's hairless below his eyebrows now and has been for nearly two years now!" she giggled. "I started slowly at first. I put him back into those pretty pink panties, the pantyhose and my high heeled shoes. He was red faced with embarrassment as I made him mince and wiggle around my bedroom. He wouldn't admit to it but I could tell he was excited beyond belief. I kept my word telling no one which seemed to ease his tension and to get him to relax somewhat. Then once firmly in control and knowing that Timmy couldn't resist I continued my plan by introducing our little sissy to more and more ladies things." Slowly, over time I started adding garter belts, sheer hose, brassieres, waist cinchers, girdles, full slips and everything else. It wasn't long until I had him totally dressed from head to toe and from the skin out every Saturday morning. I can't tell you the excitement I felt when I was finally able to zip the little sissy into a pretty, frilly dress for the first time! It made me twitch in my girdle!" Madge giggled with excitement. I started doing his makeup and fixing his hair in a feminine style once I got him dressed too. Did you know he can now walk on my highest heels effortlessly! Of course I encourage him, but it's funny that he doesn't realize how feminine he is becoming!" "Does that excite you Henry? Hummm? Does it excite you that I am feminizing your little sissy son? I can't believe that you haven't noticed. Haven't you wondered why he wanted his hair so long? It's half way down his back now. I know he keeps it in a tight pony tail and everyone's used to it now but when he spends time with me I love giving him a wash and set and putting his hair up in tight curlers. Haven't you noticed the pierced ears either? He may have told you it was the new style now for boys to get their ears pierced but it was really my idea. He wears a small stud in one ear and a tiny gold ring in the other when he's around you or his friends just to keep the holes open but when he's with me he's always in proper and feminine ladies earrings." Henry wasn't liking what he was hearing and started to grumble and struggle straining at the straps at what Madge was doing to little Timmy. But she only giggled as she continued. "And then we come to the main point of my little plan. Have you notice any physical changes in Timmy over the past year or so? He used to be nearly as tall as his friends but not anymore. Haven't you noticed his change of clothing style, how he likes the baggy jeans and the baggy flannel shirts over his T-shirts now? That's a certain style but little Timmy is hiding something. Haven't you noticed how he has been spending less and less time with his friends and how his voice isn't changing, getting deeper? They talk about growing beards someday but now, for little Timmy at least, that's not going to happen! The long hair, the slightly plucked and shaped eyebrows and the earrings are the easy part. Let's just say that you wouldn't recognize little Timmy now if you saw him naked, if you know what I mean." Henry grunted and blubbered into the gag straining at the tight leather straps causing them to creak once again but he could only twitch as Madge giggled further. "That's right Henry I've been giving little Timmy female hormones now for almost two years! I'm turning your little sissy son into a girl! He began to notice some time ago but really doesn't understand what's happening," she giggled. "He thought his punishment at my catching him in my things would be to have to work it off sweeping my sidewalk or mowing or shoveling snow for free. But when I forced him to dress like a little girl he didn't know that it would be an ongoing process. He thinks the corsets, the waist cinchers and the brassieres are beginning to change his shape! Little does he know!" She giggled again. "His skin began to feel softer almost immediately and his hair seemed thicker and more luxurious while his body hair growth nearly stopped completely. It has been an amazing process Henry, so very fulfilling and exciting for me! His little hips have started widening and his waist is narrowing now and he's even started growing breasts! He mentioned his worries about the tenderness and the tingling sensation in his chest to me and I told him it was nothing to worry about. I then began applying a cream to his tender breasts which took the tingling sensation away. But what I was giving him was in reality a hormone laced breast development cream! I added a topical anaesthetic which took away the tingling sensation but the breast cream is continuing to work at full force. And the more feminine he gets the smaller his little wee-wee seems to get as well! His little testes hanging in his little hairless sack are all but useless now, atrophied by the female hormones now in his system." That's why I wanted this little session today Henry. We are at a crossroads now. We must pack up and move to another town, far away where nobody knows us or little Timmy. He's starting to show now and it won't be long even with the baggy clothes until others will notice as well that he's no longer a boy but changing into a girl. Things will be fine, you'll see. We don't have to get married right away but I think it would be best to give little Timmy a complete family don't you? We'll move away get a nice new house and we'll start calling Timmy by his new name, 'Tiffany.' You'll see to it that all of his boy clothes and boy things are left behind then once at the new house I'll fix up little Tiffany's room nice and pretty, feminine just like a girls room with plenty of lace and frills and dressers full of lingerie and closets full of dresses. We'll get the paperwork on Timmy changed over and get him started seeing a doctor. I've been giving Timmy female hormones whenever I can but I can't give him his pills every day. I'll send them home with you today. You'll have him take them every morning and if he refuses, grind them up and put them in his food or drink. Once he's fully on female hormones every day he'll really start to blossom. We'll get him started on even more concentrated hormone injections too. Then after little Timmy's final procedure he won't be a sissy anymore, because he's going to be a girl for real!" Henry continued to object to what Madge was saying. He fought against the straps as his still throbbing erection bobbed beneath him. Then Madge played her final card. She got up from her chair, came near and began working, stroking Henry's stiff erection once again. "Your little son is a SISSY Henry! But he won't be a sissy for long because I am going to cure him by turning him into a woman! He's well on his way now. Isn't it just wonderful that we got to him before the real onset of puberty? It's going to be so exciting, so totally exciting to see the look on little Timmy's face once we move away to the new house and have a few final procedures done on him. He doesn't know his days of wearing pants are over" she giggled as she continued working Henry. "And then it will be too late." Madge giggled. "I can't wait to see the look on 'Tiffany's' face when we're done and I am in her pretty new bedroom as I put her into a lacy white brassiere and then work a pair of frilly white nylon panties up her smooth shaved legs, over her wide womanly hips and up high and tight on her waist and she sees for the first time that her little mound is now real, complete with lips and a vaginal slit!" With that she stopped stroking Henry, priming him for her final explanation. "It's sickening to you, my dressing your son in panties, stockings and lacy lingerie, but it's exciting at the same time isn't it. Timmy never would have been much of a man anyway. He was always too slight, quiet and reserved. But now things are going to be much more enjoyable now, you'll see. I'm turning your little sissy son into a girl! You should see him as he minces and preens around my bedroom wiggling and teetering on my high heels in a pretty dress and with his makeup and hair all done up nice and pretty. He looks and acts more like a girl than a boy and now with my help he's even more feminine than most girls his age. I can't wait to start taking little Timmy outside when he's all dressed up nice and pretty as Tiffany. I want to take him to the beauty salon to get his hair and nails done and then take him shopping for lingerie, dresses and high heels. Does that excite you Henry? Hummm? Me getting little Timmy all dolled up and taking him shopping just like we were mother and daughter? Just imagine, he's going to know the sensation of the breeze whistling over his shaved and hosed legs and up his skirt as he minces along on high heels. His curled blonde hair will bounce and his earrings will swing with each of his wiggling mincing steps. His pretty perfume will follow him as a constant reminder that he is a young lady now and must act like one. Does that excite you Henry? That I am turning a little limp wristed sissy into a proper young lady? And when I am done nobody will ever know that little Tiffany was a boy. I think it does excite you, and by the way your reddish-purple headed hard on is twitching down there I am almost certain." "I want you to show me, show me now Henry. Show me how excited you are to have me turning your little sissy boy son into a girl. Did you know that under his blue jeans he's always wearing pretty, lace trimmed nylon ladies panties. I keep him in pantyhose all the time too and make sure to keep his pedicure perfect and toenails painted at all times, did you know all of his toenails are now a bright gloss red? When he takes his shoes and socks off you can see them gleaming under the sheer nylon hose! It's another of my feminization procedures. Getting him to wear more and more ladies things. That's what's making him stay away from his friends more and more. He doesn't want them to know his legs are shaved and that he's wearing ladies lingerie under his baggy jeans. Just wait till I put him into a pretty training brassiere!" Madge stepped around behind Henry and began working the handle of the dildo still protruding from his rear end making sure to stimulate his prostate while she continued her taunting explanation. Henry could only blubber into the gag and watch in the full length mirror as Madge worked the dildo, stimulating him further. "I'm feminizing your son Henry, I'm turning your little sissy son into a girl! And when I am done with him he won't even remember what it was like to wear pants!" She giggled. "Show me, show me how excited this makes you. How we'll move away to start a new life as a new family with our new daughter 'Tiffany.' He's almost done. I've been dressing your little boy in ladies panties, sheer garter hose, corsets and brassieres and have been giving him female hormones for almost two years now. You should see him mincing around the living room in a tight skirt and a satin blouse, he's a vision, a feminine doll!" With that Madge began working the dildo pulling and working it out causing Henry to gasp and "Uuuunnnggghhhhh!" As the dildo stretched him wide once again. She worked the length of the shaft out quickly and it exited with a lubricated "splork!" She then quickly undid the tight spandex and velcro straps with a snap until finally his still throbbing member bobbed freely while Madge stood by taunting as she looked on. "Show me! Show me now how excited you are that I am turning Timmy into a woman Henry. Putting him in expensive frilly lingerie and sheer seamed nylons and feminine dresses. Soon he's going to be dressed that way every day from now on. He'll be in pretty feminine clothing every day and every night he'll sleep in frilly nightgowns on slippery satin sheets. He'll get used to going out in dresses, getting his hair and nails done carrying a purse just like a girl! Isn't that exciting!? I'm turning Timmy into a girl! Your son is going to be a lady!" Henry strained at the straps now causing the leather to creak as his manhood continued to throb. Madge then watched as his large dangling ball sack began to pull up tight! "Mmmmmm, Yessss, that's right sweetie, I'm turning your sissy son into a girl, he's going to be a lady! All feminine and proper? Can you imagine watching him putting on his brassiere and panties and slipping into a pair of sheer nylon stockings and then hooking his hose to his garter belt. And then putting on a girdle and a full slip and some pretty high heels before zipping himself into a pretty dress before a day of shopping? I'll have to take a few pictures next time I have him over to dress him, you'll be amazed at how pretty, feminine and lady like your sissy son is now!" She giggled as Henry struggled and began gasping and blubbering into the gag, as his ball sack tightened further. "I'm turning your sissy son into a girl!" She giggled again then looked on with exquisite excitement until finally the throbbing shaft began twitching violently sending thick white ropes of sperm jetting from the tip of the bulbous head to the bath towel spread out underneath him. He fell forward totally spent and exhausted as he blubbered into the large ball gag. Madge then began unstrapping him. "Yes, you see how exciting it is now don't you? I knew you'd see it my way dear, it is for the best you know. I'll be sure to send you home with Timmy's vitamins. There's so much to do now that you see things my way, so many plans to make" she said as she put her long black nylon robe on once again and Henry silently dressed still reeling from disbelief as she escorted him back upstairs more than satisfied at the continuance of her plan and her now controlling influence in her new family. "Since it is Saturday, I want you to have Timmy come over after supper and spend the night," Madge said. "Tell him you have a meeting or something. I'll get him all dolled up in a pretty pink nightie then do his nails, makeup and hair for the evening. Then while we're watching a nice romance movie on television and he's all cuddled up on the couch I'll take a few pictures of our little sissy so you can see how pretty he can be. But I am sure that you can already imagine, can't you Henry?" As they reached the kitchen door leading to the back yard Madge took a paper towel and wiped the red lipstick from Henry's still speechless lips with a giggle. She opened the door to let him out then after closing the kitchen door watched with a satisfied smile as he made his way across the back deck and back to the house through the hedge next door.