And When I Return Ch. 13

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Jason's last day as Anna. A dream goodbye party.
5.4k words
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Part 11 of the 12 part series

Updated 10/29/2022
Created 01/11/2015
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On Saturday morning, everything in Anna's world was blue except the sky, which for the first time in two weeks was overcast and grey. He went through the motions of trying to enjoy all the established morning routines whilst trying to forget that tomorrow he was heading back to reality. Silence hung like limp wet blankets on a clothesline as Fiona tightened his corset.

"Tighter," Anna said, "Please, tighter."

Fiona said, "I'll try, but without someone stronger doing this, I think you're at your limit. You've been 26 inches for quite awhile now, four inches off your regular waist and I just don't know if I can do it."

With extra effort and the use of her knee, she pulled and tugged until her fingers hurt. Finally she tied it off and said, "That's it I'm afraid. I just can't pull any harder."

Sensing Fiona's disappointment in herself, Anna answered, "That's okay ma'am. It feels really tight. It's good."

Fiona measured him once, and looked at the measurement with a puzzled look, and then measured again. "How do you feel?" she asked, slightly alarmed, "Cuz' it's twenty-five and a half inches! The reason I ask is that once it goes past a certain natural resistive point, something has to happen with your insides to accommodate that."

"What do you mean?" Anna asked, slightly breathless.

"Well, your organs in there will move and readjust to new positions. Do you feel different? Is everything okay in there?"

Anna stared at himself in the mirror and felt his hips under the flare of the corset. He had requested that the hip pads be left on for the day and the adhesive was holding them on nicely. Then he noticed something odd; his lower belly was protruding a bit, and no matter what he did, he could not pull it in. "Maybe my belly," he said, "It's squishing out. Was it like that before?"

Fiona looked at his profile carefully and said, "I don't know. I don't think so. Maybe when the girdle gets pulled up over it, things will smooth out a bit."

Indeed, his figure was fine once he donned the panty girdle, garter belt and panties. The only problem he had (and it was a significant one) was pulling on his stockings, as the constriction in his torso savaged his attempts at bending. When he was done, he was breathing raggedly.

Anna pulled on his black-trimmed pink maid's dress and Fiona zipped him up, locking it at the hasp at the back of his neck, continuing the daily symbolic act of domination and submission. When she brought out a pair of 4 inch heels for him to wear that day, Anna said, "Higher. I want them higher today please ma'am. It's my last day."

She retrieved some black stilettos from the closet and wordlessly locked them on as well.

As he stood in front of the mirror, he felt the embrace of the corset and the restrictions it imposed, as well as the extreme elevation that the five inch stiletto heels inflicted. He applied his makeup carefully but with extra applications of nail polish, mascara and lipstick, feeling the heaviness of his eyelashes, and tasting his painted lips. Overindulgence was what he wanted and needed today, for tomorrow he would be normal again, whatever that meant.

In his mind that meant dealing with his personal relationship with Jenna, and it also meant inserting himself back into the schedule of physicians at the walk-in clinic, wearing his little white coat and listening to the complaints of people who didn't take care of themselves, issuing little white and pink pills as silver bullets to recovery.

But he intended to take care of himself from now on. "Physician, heal thyself," he said to himself with a grin.

Now it was 06:30 and Anna stood at the stove in the kitchen making poached eggs for both Fiona and Diane, who sat at the table each with a coffee. As usual Fiona was fully dressed in a dress, stockings and high heels and Diane was in her bathrobe. Conversation was flowing but it was intermittent, like pools and rapids in a stream. There was that proverbial elephant in the room.

Finally Diane said, "Anna, I want you to take the morning off and do what you want to do, within certain self imposed limits of course. I don't think you'll go to town in your maid's outfit, for example. By the way I wanted you dressed in that today, your last day, to maintain some measure of discipline. That uniform is how you learned to be Anna and it deserves some respect. Same with the corset, the anal plug, and the heels."

Anna buttered some toast on the counter and said, "Yes ma'am."

"This afternoon, you just have to do the laundry and the ironing," she said, after which there was a long pause before she continued, "Anna, tomorrow you have to go back to being Jason. Well, you don't have to, but you will. You can be both you know, but that'd be confusing to those around you, unless you're a brilliant actor. And who wants to be an actor 24/7 all his life? You can be both, or you can just be Jason...but we already know how being Jason went don't we? The final option is to be only Anna, and from what I've seen of you, I think you could consider that."

Anna placed the poached eggs on the buttered toast and brought it to them at the table. "You mean sex reassignment?" Anna asked, his interest aroused out of the blueness of his mood.

"Not necessarily. If you wanted to, and you had the proper family and social support, you could take hormones and have the appropriate surgery, but that's not what I meant. I meant that you could live as Anna. You could pass; you've proven it. There'd be the initial shock from friends and family, and in your case, your patients, but once that was over, you'd still have your family, you'd know who your friends really were, and your patients at the clinic probably wouldn't care at all."

Anna was now sitting with them. Rain was spattering against the window and the morning was not as bright as it should have been.

Anna was skeptical and stared out at the cloudy complicated world beyond the window pane. "I just wanted to wear women's clothes, that's all," he said wistfully, "But Jesus, it's out of control now and I can't seem to stop it from evolving. It takes something from me every day, until I have this fear that there's nothing left. At least nothing left of Jason, nothing but Anna. And Anna doesn't have any real place in this world, does she? Do I? I don't know; I just don't know."

Diane placed her hand gently on his and said, "Yes. Yes she does. Anna can visit me and Fiona anytime she wishes. No, I won't charge you; I consider you a friend now. And my friends in Toronto can help you. You're not alone anymore you know."

Anna stood up dismissively and said, "No, this is stupid. All this is just stupid. These are just fantasies, just stupid dreams. I'm a doctor; I should know better." He teetered in his high heels, his calves straining with the support of his angled feet. "I have to get away for a bit. Could I borrow your umbrella?" he asked.

"What? Where are you going?"

"I want to go get the mail."

"There's no mail delivery on Saturday out here," Fiona said.

"I don't care ma'am. I want to go take a walk and then I want to sit in the garden. I guess I just want to be a woman for awhile, free and unburdened by...by things."

"I see. I understand," Diane said, and then she brightened a bit as she had an idea. "Fiona, unlock her shoes and dress please," she said, "Anna, you ARE free you know, always have been. Everything has been, is now, and always will be, your choice."

As Anna was preparing to go for the walk, Diane thought it was time to let him know what the plans were for the last day and she said, "Anna, we're having some people over tonight for a rather formal send off party for you. Bertie's coming, as well as some of our more understanding neighbors (yes, they know what I do here, sort of). Fiona will take care of the preparation and serving duties. You'll be the guest of honor and I have some special clothes for you to wear. You'll be pleased to know that I spent every last nickel you gave me for what you've already seen (well, most of it at least), and the dress that you'll be wearing tonight. Now scoot! Go for your walk." And she whisked him away with hand signals.

There was a steady drizzle for his entire walk to the mailbox, and he thought about what Diane had said about Jason versus Anna. He dismissed it as fantasy and impossible to fulfill and he stood at the side of the road waiting. Bertie didn't come today. Nobody else did either. He stood there alone.

By the time he returned to the house, his stockings were soaked but he didn't care. He realized he was breathing in short puffs today and he occasionally felt light headed, but he stubbornly refused to ask Fiona to loosen his corset. He had to feel the pain of it.

He sat now behind the giant oak tree where there was some shelter from the rain, and he watched several coy swim lazily about in one of the larger ponds in the garden. Drops of water blew off the tree onto the umbrella with plopping sounds, and the moisture from the bench was making its way through his clothing layers to his skin. But he didn't care. Periodically, he strolled about to his favorite parts of the yard, and even stopped once at the lonely piece of concrete to which he had been locked during his deserved punishment. He smiled and moved on.

By the time Fiona called him in for lunch, the rain had stopped and both the sky and his head had cleared. Although his future seemed daunting, he had devised a coping plan, and it was very simple: let the tide take him. He would be who he was, whoever that was, but it didn't need to be decided today.

He walked briskly into the kitchen and helped himself to some tomato soup and crackers. Sitting down at the table, he smiled at Fiona and Diane and said, "It's okay. I'm okay now; I feel much better."

He spent the afternoon in the discipline of the laundry and ironing, folding clothes and placing them in their appropriate drawers and on hangers. There were times that he wished he had not asked for the higher heels and the tighter corset, but he also knew that he could take the shoes off, or loosen his corset. In fact, he realized, he could have taken all his female clothes off, and removed the anal plug. He always could have. But he didn't before, and he didn't now.

At 4:00, the three of them sat in the living room at Fiona's suggestion for a "happy hour" where they could sip some wine and snack lightly on nachos before the evening's party. As the wine flowed, tension eased and the conversation was punctuated with numerous bursts of laughter. Diane watched Anna as he sat on a single padded arm chair with his knees properly together and his ankles crossed below his slanted knees. When not holding food or drink, his hands sat in his lap on top of his skirt, and his shoulders were erect and held firmly back by the corset.

"Fiona tells me your organs are adjusting to the tightlacing now. Your waist is less than 26 inches for the first time."

"I guess so. I feel something different. I'm not uncomfortable though," he answered, almost lying but not quite, as the erotic tightness of the corset more than adequately overcame any physical discomfort that it forced upon him.

"Well," she continued, "I'm actually a bit relieved about that. It'll make it a lot easier to get you into your gown for tonight. It was tailored for a 26 inch waist, and with this design, that zipper was going to be a bitch to close. By the way, I should tell you, your gown is very formal, sort of an Academy Awards type of thing, but everyone else has been asked to wear only business casual. You'll be the centerpiece."

"Gown?" he asked, "Not simply a dress? Sounds fancy."

"It was altered especially for you. Remember all the measurements I asked you to send me before you came here? Well, the only unknown was how far we could get your waist trained, and once that was established, the last alterations were made (just last week actually). The slight give of the fabric will take care of your hips. I can't wait to see you in it."

Anna's skin tingled and his breathing quickened as he listened to her. The basic underlying fetish in his repertoire was cross dressing, and the best way to feel good about cross dressing was to actually look like a woman. He had achieved that, and now Diane was going to dress him as if he were a model to parade in front of total strangers.

"How many women are coming?" he asked.

"Six, including Bertie, so the guest list is eleven."

"What?" The numbers didn't add up.

Misunderstanding his concern, Diane said, "Well, there would have been twelve, but Bertie's husband passed away last year."

"Wait a sec," Anna said, "You mean these are couples that are invited? Like women and men type couples?"

"Yes, why?"

"Jesus," he asked dubiously, "Do they know I'm a man?"

"Of course they do! Why do think they all clamored to come? Look, you have to get used to this. Why do you think people want to see female impersonators?"

"So, I'm like a side show at the circus then." He scowled and took a drink of wine.

"Exactly! And you're going to show them what you're made of, that you're more than a trannie, more than the "bearded lady" at the circus, that you're Anna, a person, who's beautiful as a woman. They won't care if you're having an orgasm under your clothing (well, they would if they knew) but that's private information and they don't need to know that. Besides, that's just gross." And she grinned.

Anna pondered that for a moment and the wine helped him say, "You know, you're right. It's my business; it's not theirs. Damn it; that's right! When is everyone coming?"

Diane replied with a serious face, "There's nobody coming tonight; it's not a sex party."

It wasn't funny enough to cause a belly laugh, but it was enough to make them all chuckle and finish their glasses of wine. Diane said, "7:00. They're coming at seven. It's 5:15 now so we better start getting you ready."

In Anna's room, he was told to strip down completely, with Fiona even removing his corset, after which he had a shower, shaving his chest, underarms, arms, and face for the second time that day. No enema was necessary, but the anal plug was removed and replaced with a larger one that he had never seen before. It was extra long and thick, and when his sphincter muscle finally gripped the small of it at the end, he swore he felt the tip push on his abdomen.

Now Fiona and Diane took turns lacing him up into a corset that was new as well, a gold and black brocade under-bust model that went well down over his hips, which were still fitted with the padding. There were cute black lace features at the base and it came down over his upper thighs so that he suspected walking could be restricted. He wondered about being able to sit comfortably. There clearly was no need for a girdle to hold his penis restrained tonight; it had its place, flattened under the boning of the corset where it had no place to grow.

Between them they got his waist trimmed to less than 26 inches once more, and again, he felt a point where something gurgled and moved in his belly and ended up pushing the lower part of the corset busk outward. It was like his organs were trying to run away for a safe haven.

The stockings were plain, taupe colored and were meant simply to make the legs look soft and smooth, and as he attached them to the garters, he got that familiar rush of excitement he always got when he dressed like this. But this was something else, an atomic rush, something special and elegant, something he hadn't even dared to dream about.

Now the dressing stopped while Fiona did her magic with the makeup. For the first time she applied evening makeup, more glamorous and with heavier shading and highlights. False lashes were glued to his eyelids and the lip liner created a clear and sharp edge for his bright red lipstick. Finally Fiona repainted his fingernails and toenails with a similar bright red polish.

"I better go out and wait for the arrivals," Diane said finally, after watching the process develop.

"What? What time is it?" asked Anna, alarmed and excited.

"6:42."

Anna's stomach churned with butterflies but he didn't have time to fret out loud because Fiona brought the gown from the closet, holding it with one hand on the hanger and the other at the drape of it over her forearm.

"Ta da!" she said as she positioned the gown with the back zipper wide open so he could step into it.

The inside was satin and flowed up his legs like cool water but it met resistance at his hips where he had to wiggle while Fiona pulled upward. Once it went over the hips, she let it fall briefly before holding the gown out in front of Anna so he could put his arms into the long, tight, stretchy sleeves which, when pulled on completely, left subdued little ruffles at his wrists. Then she pulled it back over his shoulders and started on the zipper low on his back, working it up slowly until it was finally secured high on the back of his neck.

He looked at himself in the mirror and got emotional, swallowing in gulps. The taupe colored dress was like two parts, one being solid colored with satin layers which moved with a slippery feel over one another when he moved. It went barely over his breasts, with a plunge between them. The top of the dress was a revealing, light skin-tone nylon with elegant lace patterning, and this persisted from the top of his neck all the way to the bodice and down the sleeves to the wrists. Sequins sparkled in strategic locations at his hips and breasts, also in patterns, and the dress was heavy, very heavy. The hem was at his ankles and when he lifted it from the hips it fell abruptly and heavily downward with a light thump. It felt like it had been painted onto him, layer by layer.

Fiona smiled as she did up three tiny buttons at the front of his neck that secured the top above his Adam's Apple.

The final touches were extremely large dangling ear rings, numerous gold bangles at each wrist, the wig, and the high heeled sandal foot shoes.

The profile of the dress was extremely flattering to his thin body and instead of falling vertically from the hips, it conformed to his legs and was essentially a mermaid design. Now he started to walk and he felt the layers move all over his body, felt the tightness and the restriction, the helplessness a lady feels when she is dressed to be erotic looking but not at all practical.

"Is this even real?" he asked.

"Very. I'm so freaking jealous. I could never look that good, not in a million years. It's not fair," Fiona said, in mock sadness.

"I can't believe this," he said in wonder, "If nothing else happened to me for the rest of my life, I would always remember this. My God!" And he spun around to feel it move, almost loosing his balance due to the inability to move his feet very far apart to maintain stability

Diane entered the room just then and stood there in awe.

"Is it time?" Anna asked.

When Diane composed herself and Anna was standing before her, she said, "Oh, honey, I'm going to miss you sweetie. I really am. You look better than most women I know. Un-freaking believable! I feel like an artist who's created a masterpiece.

"Now, take my arm; we're goin' in."

Anna was shaking and the only thing literally holding his femininity together was the corset and the gown. He virtually flowed into the living room full of guests, unable to take long strides in the confinement of the gown. It swished with every leg movement.

He was introduced to all of the guests one by one, the women all praising him warmly and giving him hugs. The men however didn't really know what to do. They shook Anna's hand and often pulled their hands back quickly, not wanting to touch a gay transvestite for very long.

Once the introductions were completed, Fiona brought in the tapas dishes and directed everyone to take the wine of their choice at the bar and to be seated if they wished while Diane took the "stage".

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