A Submissive Sissy

Here you'll find my favorites Sissy & Femdom stories, the best one I've ever read over the net since many years and believe me, that's a lot ! I'm also a wool fetishist, so you may come accross this type of topic around here too... Hope you'll like it !


Sissy Therapy - Chapter 10

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The next day, the Smith "girls" gleefully made their way through the busy mall to La Femme. More accurately, two of them were gleeful. Billy was walking as if it was his final mile until his mother warned him harshly that if he didn't start "enjoying himself", they were going home to call Ms. Walker. Recalling the police officer from the day before, Billy struggled to compose himself and be more cooperative.

At last the three made their way into La Femme, which was every bit as busy as when Billy had been there before. Ms. Gladstone spied the trio and made her way over to them, her gaze directed straight at Billy. She had not looked forward to working , but the day's entertainment had just arrived. While she was still several feet away, she loudly exclaimed, "Billy darling!! How is my favorite customer!! I'm so glad you're here! We have such pretty things in right now—I know you're going to love them!" Billy cringed as she bent down to give him a hug and girlish kiss as the crowd of shoppers strained to get a glimpse of "Billy" who was a regular customer at La Femme. Ms. Gladstone held Billy at arm's length as she exclaimed, "It looks like someone has been busy with the tweezers—and I love your nails!! Aren't they pretty? I bet you can't wait until they're longer, can you." Billy looked pleadingly at his mother, but she and Rachel were enjoying themselves too much to be bothered. After thanking Billy for his "sweet" card and showing him that it was prominently displayed where everyone could see it, she asked the trio if they were looking for anything special .

Ms. Smith cheerfully explained that although "Sissy so loved his girlish underthings, he simply couldn't bear the thought of wearing boy's outerwear anymore. He simply begged us to bring him here to shop, but we're not certain that Sissy is ready for skirts and dresses. We were hoping you could help ."

"Of course ! Anything to help our little princess!" Having heard the entire story from Ms. Smith on her last visit, Ms. Gladstone knew that Billy had certainly not begged to come back, but this only increased her enjoyment of his humiliation.

"All sissies want to wear ballgowns like Cinderella, but they have to learn that skirts must be earned. But I know just the look for Sissy— ultra- feminine, but leaving no doubt that he is a boy...a sissy boy. Ms. Gladstone smirked at Billy as Ms. Smith and Rachel roared their approval. Ms. Gladstone invited the ladies over to a mirrored sitting area to relax while she gathered just the right things for Sissy. Billy, on the other hand, was led roughly by the arm into a dressing room and instructed to strip. Billy meekly complied, knowing that he was only delaying the inevitable. What seemed like hours later, Ms. Gladstone burst into the room, burdened with dozens of items. Pulling Billy to his feet, she mocked, "You're just going to love the things I've picked for you. Ms. Gladstone thrust a black garment into Billy's arms and told him to put it on. Billy was relieved to see that it was a pair of pants. "The zipper goes in the back, dearie ." Billy corrected his mistake and turned the pants around. As he pulled them on, he noticed that that they only came to mid-calf and had little bows at the hem.

"Uh-m, what kind of pants are these?"

"Why Capris pants, of course," said Ms. Gladstone as she zipped up the back. "Don't you love the snug fit? Your girdle gives you a such a sweet girlish front and plump little bottom. Now for a prissy little blouse." Billy recoiled in horror as he saw the blouse intended for him. It was made of a sheer white fabric, and had enormous puffed sleeves that ended in tight cuffs high on Billy's upper arms. The collar was a large round affair. Billy began to whimper as Ms. Gladstone buttoned the blouse up in the back. However, Billy really started to cry when Ms. Gladstone tied an enormous black satin bow under his chin. Clearly, enjoying herself, Ms. Gladstone laughed, "Sissy, darling, we're just getting started!!"

Next came a pair of lacy white ankle socks like Billy had seen little girls wear. Once those were in place, Ms. Gladstone forced Billy's feet into a pair of black patent leather pumps with a one-inch heel. These will give you an adorable little wiggle. Although Billy prayed otherwise, Ms. Gladstone wasn't done. Next came a white pair of girl's gloves . "Don't you love how your pretty polish shows through?" Finally, Ms. Gladstone threaded a little purse over his arm. "See how it matches your pumps?" Immobilized by shame, Ms. Gladstone spun Billy around to get the full effect. "Aww, Sissy dry those tears. I know you'd rather have a pretty dress, but this outfit is darling on you. Now, when you come out, here's what I want you to do..or else!!"

"Sissy, dear, we're waiting." Billy took a deep breath and steeled himself for the humiliation to follow.

Billy's mother gasped when she saw her son. He minced toward them, his left hand resting delicately on his hip. The handle of his purse nestled in the crook of his bent elbow, while his hand was bent fashion-model style, palm turned toward the ceiling. Billy wore a big smile, although his mother could see that he had been crying. She could well imagine. The prissy outfit made him look ridiculously feminine. As Billy's mother tried to restrain her laughter, Billy did a pirouette. "Oh, Mom!! Don't you just love this outfit? Please, I simply must have it !"

"Well of course you can, Sissy darling. It was made for you!! What do you think, Rachel?"

When she was able to stop laughing, Rachel managed, "Perfect!! It's perfect! I love the way you can see his bra! And it certainly seems to have brought out the best in our Sissy!"

Ms. Gladstone quickly led Billy back to the dressing room for more "fun". As the morning wore on, Billy was forced to try on one humiliating outfit after another. Of course, Ms. Gladstone's threats had ensured that he "adored" every outfit and that he begged to buy each one. Billy was forced to don blouses, sweaters, shorts, leggings, shoes, and accessories, all exceedingly fussy and feminine. Finally, Ms. Smith instructed Billy to put on his favorite new outfit for the trip home.

While Ms. Gladstone drug Billy to the dressing room, his mother and sister tried to recover from the hilarity of the morning. Both women had laughed so hard that they cried. As she dried her tears, Ms. Smith addressed her daughter, "Oh Rachel, I don't know when I've had more fun! Ms. Gladstone has picked the most perfect outfits for your brother-they're feminine but don't hide the fact that Sissy is a boy. "

"Mother, I know! I can't decide which outfit is my favorite. I think it's a toss up between the little sailor suit and that sweet little little Chanel short suit! Can you imagine Billy running into any of his friends in either of those two get-ups? He'd explode from embarrassment!! I know- - let's make him go and watch his old team's football practice in that preppy little cashmere sweater set and wool shorts-I'll lend him my pearls! Wouldn't that be hilarious!!"

Ms. Smith laughed as she conjured up the image her daughter had described. "That would be entertaining, wouldn't it," she said , filing the idea away for later. "Personally, I think my favorite outfit is the black velvet shorts and the sheer black blouse-did you notice that his black bra was plainly visible? I could tell that your brother really hated the huge white satin cuffs and collar. And the accessories! Ms. Gladstone has added just the right fussy, feminine touches. I loved the little straw hat with ribbon streamers, and aren't the gloves the perfect feminine touch? I don't think mister Big Shot will give us much trouble dressed in these outfits."

As he retreated to the dressing room one last time, Billy's mind reeled at the thought of appearing outside the store in the horrid clothes. He was utterly exhausted. Each new outfit had brought tears of frustraion and outrage, and the utter humiliation of mincing in front of his mother, sister, and other shoppers had left him emotionally exhausted. Of course, it didn't help matters much that Ms. Gladstone continued her assault on Billy's now fragile male ego whenever they were alone in the dressing room. Billy had begged her to pick things that were less obviously feminine, but Ms. Gladstone had only cackled and explained that someone as girlish as Billy needed the most feminine clothes possible. Trying to collect himself, Billy took whatever comfort he could in the fact that they were finally leaving.

Billy couldn't fathom picking a "favorite" outfit to wear, but Ms. Gladstone wasn't going to let him pick anyway. Instead, she commanded Billy to put on her favorite: "darling" high-waisted pink wool short- shorts that zipped in the back, a matching pink short-sleeved angora sweater with a delicate white lace collar ("Don't you just love the way the sweater shows your little titties?"), and a "precious" pink wool beret with a bow at the brim Shoes, lace ankle socks, white lace gloves, and a purse completed the hateful outfit. Ms. Gladstone fussed over Billy, adjusting and primping, explaining that she wanted him to look just perfect for his mother and sister.

As a final insult, Ms. Gladstone had forced Billy to view himself in the dressing room mirror, while cupping the breasts formed by his bra. "Just look at you! You claim to be a boy? You're nothing but a disgusting fairy!! I bet you can't wait to show the boys your pretty new clothes. Your mother should just have your pathetic little thing cut off...but I bet that's exactly what you want, isn't it?"

Finally, Ms. Gladstone led a dejected Billy to where his mother and sister were sitting. At the thought of Billy having to appear in public wearing one of the outfits selected for him by Ms. Gladstone, both wore broad smiles. " Sissy, sweetheart! I thought you might pick that outfit. It's soft, and pink, and dainty, just like you!" Rachel couldn't resist fussing with the lace collar and giving her brother's nipple a vicious tweak through his sweater and bra. As she saw a flash of anger on Billy's face, Rachel simply laughed, knowing that he was powerless to stop her. Rachel had the amusing thought that Billy was now her doll to dress up and play with—and she intended to do just that. Gaily, she took Billy's arm and led him to where his mother and Ms. Gladstone were standing, watching the exchange between brother and sister with amusement. As Ms. Smith was paying for Billy's purchases, Ms. Gladstone dropped a final bombshell. Clapping her hands and fixing Billy with her eyes, she said excitedly: "You know, seeing Sissy model his new pretties today has given me an idea!! I'm in charge of the mall's holiday fashion show-you know the one. We have girls model fashions from each of the stores. We've never had a boy model before, but Sissy is just so sweet! Besides, he isn't much of a boy anyway. Is he?"

"Why Ms. Gladstone!! What a wonderful idea!! I`m sure that Sissy would love to model for you. Oh, I know he'll be embarrassed to appear as a boy in a dress in front of such a large crowd, but I'll bet the thought of wearing a darling holiday dress with lots of frills and petticoats thrills him! Doesn't it Sissy?"

Billy's knees went weak as he heard Ms. Gladstone's "great idea". He could imagine nothing more humiliating than to appear in a dress in a girl's fashion show. Worse, Billy knew that Ms. Gladstone would not only pick the most embarrassingly feminine dresses for him to model, she would insure that the crowd knew that he was really a boy. " Mom, I'm not so sure. I mean ..." Billy thought desperately of something to say to escape the humiliation planned for him by Ms. Gladstone. "I mean, I've seen the fashion shows here at the mall, and, well, the models are real pretty, and I don't think ..."

"Isn't that sweet! Sissy's worried that he won't be as pretty as the other girls! Well, don't you worry, dearie! We'll make sure that you're the prettiest model in the show!" As Billy's face contorted at the way his mother had twisted his words, Rachel grinned her delight. She had a mental picture of her older brother mincing down a runway, perched on a pair of pumps, dressed in a fussy velvet dress, complete with petticoats and a huge sash that tied in a bow in the back. Rachel could just imagine the laughter and catcalls from the crowd as the former quarterback pranced his way down the runway.

The humiliations of the morning and the satisfied smirk on Ms. Gladstone's face drove Billy over the edge. " That's it!! Screw you!! I won't do it! I'm not going to do it! And you can't make me!!"

Ms. Smith quickly seized Billy's arm and angrily pulled him to her. "You listen to me! If you want to stay out of prison, you'll do exactly what I say. I thought I've made that abundantly clear. If Rachel and I want to see you waltzing down the runway in a pretty dress, then that's just what you'll do! Now, you owe Ms. Gladstone an apology," his mother hissed. Ms. Smith swatted the boy's pantied and girdled bottom.

"I-I'm sorry, Ms. Gladstone. I'd love to be in your fashion show." Billy stole a glance at his mother, and saw that she was still angry at his outburst.

"Apology accepted, dearie. I just know that you'll be the talk of the show." Billy could well imagine. "Although your little tantrum reminds me that your feminine comportment could use a lot of work. If you're going to wear darling clothes, your mannerisms should match, don't you think?" "Why Ms. Gladstone, what a wonderful idea. If Billy insists on wearing pretty things, I don't want him slumping around like some ... boy!"

The women all laughed at Ms. Smith's joke.

"Luckily, I know just the person who can help. Ms. Tuttle is a friend of mine who conducts charm classes for girls. I'm sure that she will be able to bring out the "girl" in your son in no time! I'll simply give her a call to explain that she'll soon have a new student. " Ms. Gladstone thought cruelly that Ms. Tuttle would give Billy exactly what he deserved, particularly if she called with some 'special instructions.' "I must warn you though, that Ms. Tuttle is very strict with her girls. But she does get results! I'm sure Billy will just love being a 'Tuttle girl'."

Of course, Ms. Gladstone's suggestion amused Billy's mother and sister to no end, and once again, Billy was made to thank Ms. Gladstone for her "kind offer." Taking the card offered by Ms. Gladstone, Billy's mother promised to call her that afternoon.

Finally, the trio was ready to leave the store. Each of the three was laden with several large pink shopping bags containing Billy's new wardrobe. As they approached the entrance to the store, Billy stiffened up as he realized that he was about to leave the relative safety of the store. He trembled at the thought. Recalling his sissified image in the dressing room mirror, Billy shuddered at the thought of anyone seeing him dressed as he was. Instinctively, he stopped in his tracks. In the end, ignoring his tearful protests, Ms. Smith and her daughter simply took Billy's arms and forced him out of the store. As they led Billy to a small cafe for lunch, Ms. Smith and Rachel snickered at the teasing comments and incredulous looks directed at he feminized boy.

During lunch, Rachel realized that she was having so much fun that she didn't want the shopping expedition to end. Billy, who couldn't get home fast enough, listened in abject terror as he heard his sister enthuse, " You know, mother, when I turned 13, you started letting me wear make up. I think that it's only fair that you let Sissy do the same. "

Ms. Smith, who was thinking of a way to make Billy pay for his outburst at La Femme, readily agreed. "What a coincidence! I was thinking the same thing. Let me give Ms. Gladstone a call to see what she thinks. She has the most wonderful ideas!"

Billy sat quietly as his mother dialed the store's number on her cellular phone. Billy hoped against hope that Ms. Gladstone would veto the idea. Billy listened as he heard his mother's side of the conversation: "Hello, Ms. Gladstone? This is Sarah Smith. . . Yes, Billy's mother. We were just having a delightful lunch when Billy insisted that he be allowed to wear makeup. I know ... I would think that he would be embarrassed enough to appear in public dressed as he is, but you know Sissy! You do ... I see .... I think that's a marvelous idea, and I know Sissy will too. Bye-bye."

Billy waited anxiously as his mother reported the details of the conversation. "Well, darling, Ms. Gladstone simply couldn't get over how quickly our little girl is growing up! She had some marvelous ideas about your make up, and I can't wait to see the results. Let's go. "

Billy tossed the shopping bags on his bed. His mind had gone numb. Without a doubt, he had just endured the most embarrassing and humiliating day in his life. As he sat on his bed, he caught his reflection in the mirror on the back of his closet door. He was still wearing his "pretty in pink" outfit, but that's not what drew his attention. It was the heavy mask of make- up that the salesperson had laughingly applied under the direction of his mother and sister. As Billy sat at the cosmetic counter in a busy department store, Ms. Smith had explained that her son had begged them to allow him to use makeup and that he was so precious, they simply couldn't refuse him. As Rachel whispered instructions to the giggling salesgirl, Ms. Smith had directed her attention to Billy, who was not allowed to see what the woman was doing to his face.

"Sissy, Ms. Gladstone agreed that you were ready for makeup. Most girls your age use a little makeup-maybe some lip-gloss and some mascara. The idea is to look pretty, but natural. But since you're only a pretend girl, Ms. Gladstone suggested something a little more obvious ... something dramatic ... Something that screams, 'I'm a sissy!' With that, Ms. Smith wheeled Billy around to face a mirror on the counter. Billy gasped with horror. He looked like pictures he had seen of actresses from the fifties-heavy foundation, exaggerated blush, false eyelashes, and the finishing touch, a Cupid's bow of bright red lipstick that matched his fingernails. Transfixed by the horrible image, Billy barely noticed as the sales girl placed all of the products Billy would need to reproduce his "look", as well as a moisturizing mask, in a large bag. Laughingly, the pretty sales girl had added, " We're having a special today. With each purchase you get a free fragrance gift. I've picked one out how especially for you. Here. . . let me try it on you. Don't you love it? It's called Pansy!" Wearing his new " look ", his mother and sister had insisted on dragging him to every girl's clothing store in the mall. As a sample of what Billy had to look forward to, the two women picked dress after dress for Billy to hold in front of himself as he was forced to view his girlish image in the mirror. Billy thought ruefully, the mall should pay him for serving as entertainment for all the customers.

Billy was lost in thought of as the door to his bedroom slowly opened. Suddenly, in a burst Rachel and a group of her friends. " I don't believe it! Look at him? Isn't he the most ridiculous thing you ever saw?"

" Look at that make up! He looks like he's ready for the theater!"

One of the girls shrieked as she started pulling things out of the shopping bags. " Oh my gosh! How precious! No way your brother wears this stuff! "

" Way!"

" How in the world did you make him do it?"

" Oh, that it's the best part. Sissy dearest picked out all these lovely things himself! He's such a...girl!"

Ms. Smith watched with satisfaction as Rachel and her friends made Billy try on his new outfits. Ordinarily, she would have asked the girls to tone down the shrieks and the squeals, but she decided to let them have their fun. After all, Billy had were ruined many of Rachel's slumber parties and had generally bothered the girls when they came to visit— showing off and playing practical jokes. Besides, she was really enjoying hearing the girls make suggestions to improve the Sissy's appearance and their teasing comments. Ms. Smith invited all the girls to stay for dinner, and the girls watched in amazement as Billy donned his apron and did the dishes. His periodic tears all only served to encourage the girls. Of course, the girls insisted on staying and "helping" Billy with his beauty regimen and did not leave until he was dressed in his nighty and his face was encased in the moisturizing mask. Ms. Smith and Rachel assured them that they could stop by anytime and "play" with their former tormentor.

As Billy lay in bed Monday night, idly fingering the bow on his nighty, he reflected on the day's events. Before going to school that day, Billy had seriously thought that any day, he would be able to go back to his old life. He kept expecting Ms. Walker to tell him that she thought he had learned his lesson and he could resume life as a boy. Billy knew that there'd be some kidding about his eyebrows and the bra and panty stuff, but he knew that he could make up some lie that would appease his buddies. He thought that he could rejoin the team, having only missed a couple of games. He'd probably even get his old starting position back. More importantly, Billy had even started to plan how he was going to make Rachel pay for the stuff she had done to him. And that Ms. Gladstone! After he found out where she lived, he and his buddies were going to have some serious fun trashing her house! After that Monday, though, Billy no longer harbored such illusions.