And When I Return Ch. 11

Story Info
The maturation of the Anna persona.
1.9k words
4.6
18.9k
15

Part 9 of the 12 part series

Updated 10/29/2022
Created 01/11/2015
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sublocked
sublocked
700 Followers

Anna felt like he had just broken through a huge barrier, like he had been pushing on some invisible, infinitely stretchable fabric all his life and he had finally reached the other side. He saw things differently now. He saw his own prejudices toward many people that had touched his life, saw them now for what they were, not what he had perceived them to be. It was a paradigm shift for him. He had been looking at himself, disgusted at his behavior with regard to cross dressing, and had at the same time been looking at others that had similar or even entirely different fetishes and been disgusted by them as well. A person couldn't live like that. Now he wanted to hold his fetish in his arms and not be hateful or fearful of it.

His feeling of humiliation, even the humiliation fetishes themselves, drifted away in the summer heat, although during bondage scenes with Diane, she could still playfully trigger them to her advantage, and ultimately to his, but it was now playful, and not traumatic. From this moment forward he could awake in the morning with a fresh look at life, do the things that felt right to him, caress and improve his feminine persona, and serve and obey Diane and Fiona without question, knowing that it was for the best.

There was fun in the day. Anna joked with and enjoyed his teachers, and his use in the bedroom and dungeon was for a greater purpose, a cure for his lifetime curse of being different, which he began to see now as a blessing instead.

As if his body sensed the change and breakthrough, the tight corseting had reached its limit at a 26 inch waist, but with the lovely weight of his breasts hanging over the corset, it was enough, provided he chose the right clothing to magnify the boyish but newly developed feminine curves. Circle and bubble skirts, tight or loose and lacy tops, some wide belts, delicate jewelry, all combined to transform him to Anna, more and more Anna, less and less Jason. It was intoxicating studying the fashion magazines, searching for trends, finding clues as to what the thousands of things were that defined a gender.

In the end, he refined his walk so that it was more natural and flowing, letting his hips relax, not in a forced feminine way. After all, he had concluded, many men and women walked the same; it was subtle differences in other body movements and gestures that created the whole. He didn't even notice the corset or the anal plug any longer as they simply became a part of who he was trying to be, although the anal plug did have a deep symbolism of sexual penetration, generally a feminine issue. Eroticism metamorphosed into something else, like an elevated spiritual sense of being.

He felt calm and contented and that was reflected in his evening conversations with Jenna. She noticed it and one night she said, "You sound, uh, peaceful or something. You sound different. You sound changed."

He hadn't known how to really respond to that but he did the best he could, telling the truth, "I am changed Jenna. This course has changed me. These people have taught me a lot. I hope you understand that when I return. I have something I want to...I mean there's something we need...umm, we need to talk when I get home; that's all."

Although he told the truth, what he said and what she understood were two different things, the course being the crucial lie within, the fabricated one in San Francisco (or was it Los Angeles), and the feminization training.

Jenna answered, "I know sweetie. I know. I have surprises for you, lots of surprises. I'll give you a hint: Victoria's Secret and another little shop I found. I missed you babe."

Anna held the phone away from his face and stared at it in puzzlement. Who was he talking to, he wondered? What had this person done with Jenna? She never talked like that, and she certainly never tried to entice him with sexy lingerie.

"Wow!" was all he could say at first and then, "I missed you too." He was lying. He had no time to miss her. It was impossible to miss someone when you were constantly searching for yourself.

It was over between them, but he couldn't say it here, not now. He knew that even though he loved her, it couldn't work any longer. He had finished the call with the obligatory "I love you" and that was it.

Now it was Thursday evening and the three girls, as they called themselves now, were sitting in the living room with evening glasses of wine and an unlit, very large joint on the table beside the bottle of Cabernet. They smoked a lot of marijuana, Anna noted.

Diane began, "I have a special excursion planned for tomorrow. Got just the outfit for you too."

Anna choked on his wine slightly and exclaimed, "What? You want me to go out in public? You think I can pass?"

"Well, we'll see, won't we? Now here's my plan. We're going to put you in the hip and butt padding that I bought for you and dress you in what more typifies female dress code these days. After all, nothing would draw more attention to you than walking in a park (or down Main Street for that matter) in a formal skirt and blouse with high heels. So we've decided on the Lululemon style: tights, stretchy top to show off your breasts, a wrap skirt so you don't have to wear a gaff, and a pair of patent leather ballet flats. An over the shoulder mini-tote bag purse will finish the look. Oh, and some jewelry and perfume of course. You'll look like you just came from Yoga class."

Anna gulped some wine and said, "I don't know. It's one thing to wear a maid's outfit and serve guests at a fetish party, but it's quite another to try to pass in small town Canada among regular vanilla people. And what would I do? Just walk around town?"

"Don't worry Anna," Diane said, "I'll be with you, and so will Fiona. You're ready. Well, I should say, you're ready if you've learned from your homework."

Anna smiled nervously and said, "So, we walk around town, like three girls. I get to actually BE a woman for a day. Oh my God, I can't believe this could even happen, let alone to me!"

Diane cautioned him, "Well, it's not likely going to be for the day, just the morning. You'll get too hot in the afternoon with the padding on and the corset. We'll have to be finished by 1:00 at the latest. After all, I don't want to be seen walking around town with a man in drag. Even I have my limits."

"You?" Anna said, "You have limits? I'm shocked ma'am! But maybe you do, as I know I distinctly asked you if you would do suspension bondage with me and you said yes. It hasn't happened has it? What the hell...?" And he laughed.

Diane snickered and said, "Femininity first my sweet, femininity first. Perfect that and the world's your oyster."

Then the conversation turned serious and, to Anna's viewpoint, slightly melancholy and fearful. Diane said, "You have tomorrow and Saturday. Then on Sunday morning, we pack you up and send you home to Jenna. How's that going to go, do you think?"

"Funny you should ask, since you're the one who made it difficult for me. My face is a woman's now, I have no body hair, and I have this tan that would do wonders on a gay beach. How do you think it's going to go?"

"Well," she said, probing, "What's your approach? The reason we did all that was to force you to first face yourself, then to face Jenna. What are you going to do?"

Anna let out a heavy sigh and said, "I love Jenna. She's the woman of my dreams, so smart, so beautiful, but I can't go on like this. You've shown me something else, a part of me that has to be expressed. But it can't be with Jenna. Been there, done that, didn't work." He gulped some wine in a rather unladylike fashion. His anal plug, heavy bra, and tight corset always became more noticeable when he thought of Jenna, diametrically opposed ways of life.

"She's going to notice."

"I know."

"Well, what are you going to do?"

Anna got up and paced to the window overlooking the garden, now in dusk's shadows, and after a moment of contemplation said, "I often think I know what to do, but I don't. In my heart, I think it can't work. There will always be this divide between us. To be honest, I think we have to separate, get a divorce. She deserves better. I'm a man, but not a real man in her eyes, and I understand that. I'd be lonely, but then again I'm lonely now. You're the only people on the planet that I've ever shared this with in a healthy way. I'd rather be lonely and alone, than lonely with somebody else. Less lives destroyed."

Diane cast a worried glance toward Fiona and said gently, "Anna, get hold of yourself. If you have learned anything here, it's that you have to accept yourself first. Then, with that, you can be accepted by others. It might be Jenna; it might be somebody else, but it will be someone, and I'll help you. If Jenna and you part, you can call me. I'm often in contact with women who want feminized slaves."

Anna glanced at her quickly and said, "That's a neat fantasy, but I don't want to be a slave; I want to be loved."

"Well, although it is often not apparent, dommes do love their slaves. It's a symbiotic relationship, both needing and loving each other." She cast a smiling look at Fiona.

Anna was done talking. She was slightly drunk and simply wanted to go to bed. "Do you want to use me tonight?" he asked suddenly. As he said it, he realized how completely he had submitted to her will.

"No. Go to bed. We'll have fun tomorrow. Just so you'll know, I want you in an expander plug tomorrow, just in case I want you tomorrow night. You haven't seen this expander though. It's new. You're gonna hate it and love it. I guarantee it."

Anna shook his head in mock dismay and said, "Oh no, what now?"

"Sleep well sweetie."

As Anna crawled into bed, he had that strange sense of dread that most people get when perfect vacations are almost done. It was troubling when dread could ruin two more perfectly wonderful opportunities to be a woman.

That dream taunted him again. He was being hunted down and he tried to run, but he couldn't run. Something slowed him down and they were catching him. He looked down and saw that he was corseted and had large breasts. people were watching him. The high heels wouldn't let him run. They were right there. They could touch him and yet he couldn't move any faster. In the end, he gave up and they took him. They were men; they were women, and they all took him. He moaned in his sleep as the orgasm seeped out and through his panties. "You can't run," a voice said from somewhere, "You can't run."

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3 Comments
BrendaNWBrendaNWabout 9 years ago
very good.. more please

Very nice so far.. more please

kuk4yookuk4yooabout 9 years ago
Suspense...

i'm gonna hate it when it's over. Love story.

AnonymousAnonymousabout 9 years ago

has diane talked to jenna ? it sounds like jenna might be excited adout anna coming home or why would she tell her she went vs . maybe the suspension bondage is how anna is going to be introduced to jenna. which could be while he is in bondage that jenna loves him as he is now and happy that anna is finally true to him/herself with loving arms and does not want him as a cockhold as what the dommes would do

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