And When I Return Ch. 05

Readers: please be advised that the characters and detail of homes etc in these stories are purely fictional. If there actually is a house with 2 red barns on Amaranthe Road, it is purely coincidental, and Diane will not greet you at that door.

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After abundant small talk and further confirmation of the reasons why Jason had requested this extended stay at Mistress Diane's feminization school, he made his way back to his room to remove his male clothes and wait for Diane.

Not much of a room, he thought, but it did have its own small en suite bathroom with sink, toilet, shower and tub. It was equipped with bondage in mind, with steel attachment points everywhere on the ceiling, walls and even the floor. There was one tall bureau by the bed and he explored the drawers, pleased to find numerous panties, girdles, bras, and hose, as well as tights. Some unisex looking tops and pants were folded in lower drawers. The lowest drawer contained three items that he had only dreamed of owning...red, white, and black corsets, and not just the flimsy commercial types, but the Victorian type, fully boned and with heavy duty laces up the back. Taking one out, he fastened up the front busk and placed it on the bed. It looked small, he thought, so he turned it over and put the two sides of the corset together without tightening the laces. Really small. He did the measurement with his spread fingers and estimated the closed dimension at twenty-four inches.

Damn, he thought; that had to belong to someone else. His waist was thirty inches. He wanted to be laced into one, but he didn't want to be crushed, as these corsets would do. He was disappointed.

The closet, although a small walk-in, was filled with dresses, skirts and blouses, while the floor had several pairs of shoes and boots, all with higher heels than he was accustomed to wearing. He tried a stiletto and it fit perfectly. Then he looked back at the corset on the bed and wondered. Why would the shoes fit and the corsets not? Several garment bags also hung in the closet, but the zippers on them were locked with small luggage locks. One smelled like rubber, another leather. The leather smelling one was heavy, and it jingled slightly when he lifted it off the rack.

Weird place. But then again, this was what he was seeking.

What the heck was she going to do with him for fourteen entire days, he wondered? All he really craved was to be feminized and dominated by this woman. That surely wouldn't be too complicated. As he contemplated this, he noticed two purses hanging by the door. He looked inside and found them filled with makeup and the tools for its application.

A cocktail of emotions flooded over him as he stood there, fear, excitement, anguish, guilt, and his knees and hands started to tremble. Two weeks. This was his dream, to be "forced" to dress and act like a woman. What he hadn't expected was the reality of the "forced" part, and that's what made him shake. It wasn't the clothes; it wasn't Mistress Diane; it wasn't his lack of male clothes that was creating this "force". It was him. He had to have it. And nothing on this earth was going to stop him from having it, no matter what it did to him.

A faint whisper came from the darkness of the closet. "Or to Jenna," the guilt said.

Jason came out of the closet and sheepishly took all his clothes off and sat on the bed and waited. He was trembling slightly and periodically he shivered in the morning coolness. His skin rose up in goose bumps. Nervously, he inspected the red corset beside him, noting its strong boning and contoured shape. Now he understood the determination by Diane to get his measurements precisely. It was not your standard corset. And it was not somebody else's corset; it was made for him.

His emotions oscillated as he sat there, from extreme excitement to extreme shame and despair. And it all became an exotic cocktail, like a new compound, fresh out of a lab, that few could understand.

Suddenly Diane entered the room. He couldn't help it. As soon as he saw her, his penis grew and rose up. He tried to hide it with his hands but it was silly and futile. Diane laughed.

With a grin she said, "Ha, that's good. You want me. We're going to have so much fun with you. I just hope you have fun too, but it's not obligatory. That's up to you. We'll get started right away. First things first, we're going to try you in some bondage. I told you we wouldn't waste any precious time. Put these leather cuffs around your ankles and wrists and lock them on with these locks."

She gave him the items and waited while he did as he was instructed to do. She noted that his hands shook.

"Now step into the shower."

She followed him, as the shower was large. She instructed him to place his feet in a certain position while she connected short pieces of chain to the cuffs, then to attachment points on the floor. Now he could not move his legs.

"Put your hands together," she ordered.

Locking the two hands together, she also locked a longer piece of chain to the cuffs and then pulled the chain through a steel ring on the ceiling of the shower. Without warning she pulled hard and his hands went sharply over his head. Before he knew it, he was locked in place.

She turned the shower on and said, "This won't take too long. You don't have very much hair."

A pang of fear ripped through him as he said, "What? What are you going to do? You can't remove my hair! It won't grow back in two weeks! My wife..."

Diane responded rather harshly, "Look Jason, I don't have a lot of respect or patience for a husband that is doing what you are doing, lying to your wife and all. I do this for the dollars and the fun I get from it. You like bondage. You got it. You want to look like a woman. You're gonna get that too. And you said in one of your comments in our discussions that you wanted to look like a real woman, not like a man in drag. Your hair goes."

She directed the water on his helpless body to wet him down and then she lathered shaving cream under his arms, on his chest, and on his legs.

"No," he yelled, "You can't do this!"

Fiona had walked in now and she giggled at his predicament.

Jason continued to yell at Diane and struggled hopelessly in his restraints. Diane turned to Fiona and said, "Gag him."

At first he would not open his mouth to the penis gag. He had never had a penis in his mouth, mock one or not, and he wasn't about to agree to that. That reluctance ended when Diane squeezed his testicles forcing a scream and allowing the insertion and buckling of the device.

She stood back and listened to his muffled gibberish and gave him some advice, "If I were you Jason, I'd be very still while Fiona shaves you. Just sayin'..." and she smiled slightly.

To Fiona she said, "Okay Fiona, get it done. Might as well do his eyebrows while he's trussed up too. Lots of tweezing to do there."

This last comment drew wide eyed exasperation from Jason as he yelled, "Mmf, mmf!"

When the safety razor touched his armpits, Jason whimpered but remained perfectly still. The whimpering eventually stopped but the shaving continued until he was hairless. She even decided to do his arms after closer inspection revealed some visible masculine hair. When she finally rinsed his body clean, he felt oddly cool, with every movement of air currents wafting with increased sensitivity across his hairless skin.

Oh God, what was he going to tell Jenna, he wondered?

Then the plucking started. Fiona tweezed without mercy, stepping back often to make sure the symmetry was correct. She was tireless in her attack and he grunted in pain with every pull. His eyes watered. It seemed like hundreds had occurred and he knew this would be far more difficult to explain when he returned home, not just to Jenna, but to his clients and friends alike. What the fuck had he done?

When it was over, he was subdued, and he hung there in the shower wondering what he now looked like and what was next.

Diane and Fiona were observing him and shaking their heads. "I can't believe what a difference that makes! All that's left is to give him boobs and get rid of his penis, and he'll be pretty near there," Diane said in wonder.

This brought a new round of struggling to Jason who started creaming again in panic.

"Jason sweetie, don't worry. Fake boobs glued on and we'll teach you how to use a gaff to hide your junk, okay?"

He calmed down as she unlocked his restraints, led him out of the shower and dried him off. He stared in disbelief at his reflection in the mirror. Even without makeup, the eyebrows did it. It was clearly a feminine countenance; his face was made for this.

After he had dried thoroughly, he began to accept his appearance as non-returnable, and excitement started to build again about future changes. He waited alone in the bathroom while Fiona and Diane were elsewhere getting whatever it was that they had planned for him.

Soon they arrived back with a few bags of items. One of the items was a bra which he was told to put on. Again his fetish gave him away and he rose up. Diane slapped his penis aside and put two very realistic silicone breast inserts into the cups, positioning them carefully so that they appeared as a realistic profile. With a marker she marked adjacent spots on his skin versus the inserts and then told him to remove the bra.

Within ten minutes the self adhesive breast forms were in place and he was told to hold them for a few minutes while they "set". They seemed large and he looked down in awe of what was happening to him.

Diane said, "These are called Aphrodite Breast Forms, and depending on the person and their skin sensitivities, once they are attached they can stay on for upwards of seven days. Lift your hands away slowly."

He did so and he felt a very strange sensation. They stayed in place and he felt a pull on his upper pectoral skin due to the realistic weight of them. The feathered edge blended into his skin almost imperceptibly. Very tentatively he tried moving up and down on his toes. They bounced and held firm.

Even Diane was impressed. "That's really good. They've attached well. But I still want you to wear a bra at all times except in the shower okay?"

Jason looked at himself in the mirror again and gasped, "Oh my God! This is unbelievable!"

Diane asked more firmly, "Did you understand what I just said?"

"Yeah, sure," he responded.

"Sure what?"

He looked at her, puzzled, and then answered a little sheepishly, "Yes ma'am. What's next ma'am?"

"That's better. Fingernails, toenails, then corset, then makeup and your wardrobe. Fiona's an esthetician and will do your nails right away in your room. Acrylic I believe. Your fingernails will be extended and then while your polish is drying on feet and hands, the corset gets snuggled up on your beautiful body. From now on, if you want to be a woman, you have to think of yourself as a woman. What would you like to be called?"

"What do you mean?" This was moving too fast for him.

"Your female name. What do you want?"

"Anna," he said, surprising himself.

"Anna. Nice. I like that," she responded, "A very feminine name. No variations that can be masculine there. Very good Anna."

While Fiona was working on him, Diane chatted, "Jason, I mean Anna, I'm not sure if you fully understand the depth of training that I give here, what is required of you, what I demand from you. So, I'll explain a bit of it for you. If you don't agree to it all, you might as well go home, because I don't do half jobs.

Your idea of a woman is, quite frankly, repulsive to me. You think of a woman as a sexual object and a domestic servant, and I've always found it odd that people like you succumb to, of all things, a dominant woman. Anyway, I digress. Now, a woman in your mind has three sexual orifices, vagina, anus, and mouth. A man only has two, anus and mouth. From now on, I want you to think of your anus as your vagina. Now to get you to think like a woman. You have a vagina and we have to train it to be one. And your mouth is also a receptacle. You are an object, a sexual object. Men and women look at you and want to fuck you in either your vagina or your mouth; it doesn't matter to them. Do you understand? You are an object. You will get regular penetration..."

This caught Anna off guard and he interrupted, "Penetration? Anal penetration?"

"Yes, but to you now, it won't be anal, but vaginal. I want you to think of it that way. And your mouth will be used as well to..."

"Wait," he exclaimed in somewhat of a panic, "I'm not going to suck a cock, and I'm not going to let a man fuck me in the ass. No way."

Diane smiled and said, "Typical. All of you people are so afraid of being gay. Anyway, stop interrupting me. Your mouth will be trained and used to serve oral sex to me. Your vagina will be given an enema before your shower every morning, and an anal plug will be inserted for the rest of the day, to be removed only if I choose to peg you. A lady always has to be clean down there, just in case."

"Peg me?"

"Yes, that's where I fuck you with my strap-on. That's the part of this job I really, really like. And it's extremely important to your feminization process. There's nothing like a good pegging to take the masculinity out of a man, wouldn't you agree?"

"But, I, I never thought...I...and if I refuse?" he stammered.

"Then you might as well go home right now, because I won't continue. And all the leather and rubber gear, the restraints, all your clothes that I bought with your money, I would keep for other clients, as I would interpret your leaving as a breach of contract on your day rate due. You could sue me of course, but I doubt you would, would you DOCTOR?" She emphasized the "doctor" implying that his social status might make everything a bit nasty and public.

He got her drift and he sat in silence while Fiona tickled his fingers with her transformations. After several minutes, Diane casually asked the question, "So does this all seem in order for you Anna?"

He shut his eyes and shook his head as he answered, "Yes ma'am." He was astonished to hear himself say this.

"I thought so. Now to continue, you will be required to..."

Anna was only vaguely listening now as Diane laid out her requirements of maid service, entertainment of special guests, and all things domestic and sexual. In short, he was to be her slave for the following two weeks. In return, he got his wish. But what was the true price of this wish? It wasn't just dollars. He was beginning to wonder if he would come out of this alive, not that he would die physically, but psychologically and sexually, emerging to "the other side" with no options available for a return trip. Where would that leave him? Would he be able to relate to Jenna in the same way? Would she see his change? Would he then be even more alone and dependent upon people such as Mistress Diane to make him feel happy and wanted and needed?

His wish. What had he done? But he stubbornly knew he would not be turning back; there was too much of him invested.

Two hours later Fiona had finished his nails and the corset was being fitted around his waist. His penis was continuing to embarrass him and the girls laughingly called it Bob, for obvious reasons.

"This morning," Diane began as she started to tighten the laces, "We'll just tighten it to a snug but tight fit so you can get used to its restriction in movement. Notice how a woman's waist is above the belly button, and for you that eventually means severe restriction on your lower rib cage, so we're going to go slow. Your waist is 30 inches, and I doubt we'll get it to 29 right away, but maybe by the end of the day. You might as well know, your training is going to be relentless and you'll be corseted for at least 23 hours a day. You get out for one hour, or less, a day for your enema and shower. Now breathe out."

He did so, and like a boa constrictor, the space made available was eliminated by a tightening. It felt comforting and exciting. Three more breaths out and she tied it off.

"There. How does that feel?"

"Unreal! I've only dreamed of this, really. God, this feels amazing." He felt his waist and tried to take a deep breath and was limited by its restraint. Also, there was little room for waist bending. It held him straight like an old-school Presbyterian. Looking into the mirror however, he was slightly disappointed, as there was no noticeable change to his figure.

Diane laughed. "This is just the beginning. There's a huge amount of work to do, and you're going to be exhausted, so prepare yourself Anna. And don't worry about your waist. That'll change, and I've bought some hip and buttock padding for times when a super figure is necessary. Make-up is next and don't just sit back and let all this happen. Everything here is a lesson. You'll be required to do everything on your own and like an old fashioned school, if you don't work, or fail at something, there are consequences. There have to be."

"What sort of consequences?"

"I beg you pardon," she answered indignantly.

"What sort of consequences...ma'am?"

"That's on a need to know basis. And you never need to know."

"I see. Ma'am."

Fiona had made some sandwiches for lunch and they all ate in Anna's bedroom while makeup was applied, including false eyelashes. They also sipped on wine and chatted like the three women they appeared to be, as by now, they had him secured in a gaff, his penis hidden away and useless. Anna was not permitted to look in the mirror while the makeup was being applied and it was killing him. Finally, a dark brown wig was applied to his head and brushed out. It fell past his shoulders and tickled him causing him to shiver in delight.

"Turn around Anna," Fiona said, obviously proud of her work.

Anna's heart raced as he turned to look at his reflection, a corseted woman with a tastefully sculpted face, high cheek bones, huge accented eyes and ruby lips. A bra above the corset held large, perfectly formed breasts, and when he brought his hands to his face the fingernails were long and red, matching the lipstick. He brushed the hair away from his eyes and stared, his lips trembling with thoughts of weeping. His hands shook like someone with Parkinson's Disease.

The gaff was no match for his arousal, and, without any stimulation at all, the orgasm spilled out of him uncontrollably, his hips writhing, soft sighs escaping his mouth, and his hands lightly squeezing his breasts. His eyes closed as his gyrations subsided, and when he opened them again, he still saw a woman. This was nothing like his other "dress-ups" where he had an orgasm staring at a woman, and then opened his eyes to see a man in drag. This was real. He sobered and looked around at the two women sheepishly.

"It's okay sweetie. We get that a lot. You lasted longer than most. Your clitoris was over stimulated. Clean yourself up, get a new gaff and panties and put this uniform on. The undergarments are on the bed and you'll wear these high heels until you get used to them. They're about 3 inch heels to start, but by mid week we'll have you at five inches."

He picked up the uniform and realized it was a classic French Maid's outfit. After orgasm, reality tends to shift and he said, "This is silly looking. I'm not going to wear this." And he tossed it back on the bed.

Diane was firm. "You will wear it. It's the best way to be feminized. Remember what we agreed to, you're a domestic and sexual servant that cannot disobey commands. You didn't think you were just going to have playtime here did you? You'll do all the housework for the next two weeks while we supervise and correct your mannerisms and posture. At suppertime you may change into other dresses, skirts and shoes of your choosing for supper and the evening playtime where we challenge you sexually. However, if you haven't performed as expected during the day, your evening wear may be, shall we say, more imaginative and punitive. So, get dressed and when you're ready, come to the kitchen for another coffee while we explain your duties."