And When I Return Ch. 09

Story Info
Feminization continues. Anna serves guests at a garden party.
2k words
4.31
27.8k
13
0

Part 7 of the 12 part series

Updated 10/29/2022
Created 01/11/2015
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
sublocked
sublocked
701 Followers

Diane explained to Anna that his workday was simply to be in preparation for a munch on the following afternoon in the garden, or in the case of inclement weather, in the dungeon. The theme of the munch was a horse show and when he asked what that was all about and where were their horses, Fiona and Diane laughed in as controlled a manner as possible while Diane said, "We have some horses in our stable which you can meet tomorrow."

"Is that why the walks in the garden are cobblestone then?" he asked innocently.

Diane and Fiona glanced at each other conspiratorially and Fiona said with a grin, "Exactly. It's for the horses. There'll be two ponies and four women as well as two male maids, so we need to prepare food for eight."

Before he could question the arithmetic or the sense of it, he was told that the entire morning had to be used for garden maintenance, roughing up the beds and sweeping the pathways, all to create an immaculate setting for the event. The afternoon would be spent creating the appetizers and choosing wines and cheeses for the get-together.

"Well," he said with relief, "that'll be a nice reprieve from housework then. Any uh, special training scheduled for me this evening ma'am?" He was hopeful.

"No, none. I'm sure your vagina is a little tender and needs time to recover. We'll just watch some TV and go to bed early. I might get you to do some posing and modeling. We'll see," said Diane absently. "Or I might change my mind and fuck you again," she added with a twinkle in her eye.

In fact, the day went as planned, the issue of difficulty for Anna being the higher heels and his aching calves. He was beginning to long for male shoes. The torment was lengthened this day because Diane wanted to keep him in his maid's outfit until it was bedtime so she could work on his walk and mannerisms. The hints were simple and intriguing, like a simple light finger brush behind his ear as an indication of caring about one's looks, a flare of the hand, or a toss of the head to fix the fall of his hair. Jewelry, matching and fashion sense were also emphasized as well as different types of makeup for daytime versus nighttime.

It was vastly more complicated being a woman than he had realized. It was also a vastly more durable cobweb of stickiness; as he realized the more he struggled the more entrapped he became. So he let that go, immersing himself in the totality of the experience. Whether he looked it or not, he felt resplendent in his femininity now, fairly confident and unashamed, drinking it up like wine, a light and delicate one, perhaps a good Chenin Blanc.

He awoke Wednesday morning feeling in a rhythm, knowing exactly what to do and when to do it and how, as if a new normality had been established. Enema, shower, shave body, don corset and tighten, do makeup and get dressed in maid's dress. It was all so simple to understand and he enjoyed the freedom within his slavery, the freedom of not having to think.

The last minute preparations for the garden party were frantic and he was kept busy in the kitchen while the guests arrived through the gate to the back yard. It was well after 2:00 before he was instructed to bring platters of food out to the tables that had been set up in the shade of the large oak tree across the yard from the dungeon, and he was extremely nervous about his appearance. He knew there were to be two other male maids and he searched them out now as he placed platters on one of the tables. They stood together by the door to the dungeon dressed in a similar manner to him, but that was where it ended. One was well over six feet tall with broad shoulders and huge hands. He tried to be feminine, but it just did not work. The other was dreadful for different reasons; he was short, fat and (unbelievably) he didn't even shave his chest. Hair curled out over the top of his maid's pink dress bodice. Both had permanent five o'clock shadows on their faces which no amount of makeup could ever hide. Anna was shocked.

They returned his gaze with a jaw dropping, awe inspired stare. They were clearly amazed at his looks and...was that a touch of jealousy? It was a trace of a facial expression or a hand movement that made that suggestion, but all that was forgotten in a second as the ponies came out of the dungeon pulling chariot style wagons behind them, operated by latex clad dominatrices.

Now Anna understood the guest list arithmetic for the first time; the ponies were humans dressed fully in skin tight black latex, complete with leather bridles and bits in their teeth. Their feet were encased in realistic horse's shoes, which meant that the wearer had to be standing painfully en point within them. They marched out clip-clopping on the cobble stones to cheers from all the ladies and the maids present. They appeared to have large female breasts and their arms were folded and bound behind the small of their backs. Upon orders and a tap from riding crops they lifted their feet high and went into a trot.

As they approached Anna, he couldn't help it; he shook his head and laughed. It was so utterly absurd. Upon seeing his reaction, the horses' owners stopped the carriages immediately and there was an awkward silence in the yard as they all stared at him with shocked and puzzled looks.

One dominatrix said in scorn, "Really? You laugh at this? Lady boy?"

Diane came racing toward him and yelled, "Anna! What in God's name are you doing? These are our guests! How dare you!"

Anna went into panic. "Oh my God, I'm sorry. I'm so sorry. It's just that I was, you know, expecting real horses, you know?" And he couldn't help it; he giggled again.

The two pony-girls shuffled uneasily in place, clopping their hooves, but they could not look at him because of the mouth bits and the additional vision restraint of the blinder flaps. Their owners glared at him in utter disbelief.

Diane was in damage control and she continued, "Anna, apologize immediately! You're living in a glass house you know. I can't believe this!"

It was odd how he had forgotten for a short time that there might be something different about him; he was so immersed in his feminine persona. He shook his head in self flagellation as they all stared at him and waited.

"I'm so sorry. Really, I am. I know; I'm a man dressed in this ridiculous French Maid's outfit. Look, I don't know what to say, except please accept my apologies." He bowed his head and put his hands demurely in front of his dress.

Diane was still furious. "You think your outfit is ridiculous, do you? Really? It's what I picked for you. And I suppose you think those maids over there look ridiculous too."

This was getting worse not better. Yes, they did look ridiculous. "No, no, of course not, I didn't mean that. Oh Jesus, I'm so sorry. I'm new to this, and I'm not sure how to react."

Diane started to lecture him in front of them all, "You, of all people, should understand what it's like to be ridiculed for your interests or fetishes, or whatever. One thing we all seek in life is acceptance. You've hurt these people enormously today." She turned toward all of them now and said, "I apologize for my slave's behavior. It was unacceptable and she will be punished." Turning back to Anna, she said, "Now go and apologize to all of my guests individually and give them a kiss on the lips and a hug if they're gracious enough to receive it from you."

Anna shook with very real humiliation in front of them all as she went to each and apologized profusely. It was difficult to kiss the ponies and the maids, but for different reasons; the ponies had gear on their faces and steel bits pulled back in their teeth, but the maids were so obviously men in drag that it almost brought a gag reflex from him. But he did it, and the party continued.

But he was a pariah for the rest of the afternoon, isolated from conversation and forced to only serve drinks and food to all those he had insulted. It was very clear that the wound remained open all through the munch. Diane rarely spoke to him, and when she did, it was with regard to certain tasks or instructions. Anna was genuinely humiliated, and not in any erotic sense at all.

After the guests had left and the three of them were seated in the kitchen, Diane said, "Anna, I was very disappointed with you today. That was awful. If there is one thing that all of us that are different need, it's acceptance for who we are, not ridicule like you expressed."

"I know ma'am. I feel really ashamed. Honestly I do," he said with sincere regret.

"Well," she responded, "I would hope so. But I can't let it go at that. I've decided already what your punishment will be, and I won't tell you what it is. In fact you won't even know what it is until it's too late for you to get out of it or react to it, even if you wanted to."

In his bizarre way of thinking, this actually sounded erotic to Anna, so he said submissively, "Yes ma'am." The translation of this response would be, "I've been a bad girl, and I need to be spanked." He tingled with excitement.

That evening he was told to go to his room and go to bed, as if he had been a bad girl, but that was it; there was no other punishment. He felt cheated.

The next morning, the preparatory routine was awkward and grim, with Fiona simply giving him orders as he went through his motions. When she tightened the corset this morning, the pulls were strict and sometimes violent. He gasped as his waist and lower rib cage shrank under her assault, and he found it hard to breathe when she had finished. It had never been this tight, and when Fiona announced his measurement today he understood why. It was 26 inches, a full four inch reduction in only four days. That was unheard of, and from what he had been told, not recommended; the reduction was way too fast.

When she locked the five inch heels on his feet after he was dressed, he thought he now understood what was going on; this was his punishment for the day.

He loved it.

But as the day progressed, he found that his output of energy to do the housework could not be replenished with food to equal that loss because of the tightness of the corset; there was just no room in his stomach. His energy lagged, causing him to stumble on occasion and to be ridiculed by both Diane and Fiona. It was not enjoyable in any way. Not only that, but he was sent to bed again that night without friendly social of sexual interaction. He felt isolated and lost, like there was no interest in his femininity training from them at all.

Again, he thought about suggesting to them that he leave. But he didn't. The threads of his fantasies kept him there, invincible and strong.

Friday, he got the same treatment, but at lunch Diane announced that there would be another munch the next day with the same people as on Wednesday. When she announced this, she said to him, "You'll get a second chance to make it up to the people you offended, and then we'll judge what your direction will be for your last week of your stay here."

Anna said, "Thank-you ma'am. I'll try really hard ma'am." He mistakenly interpreted her comment as the start of her forgiveness of him, but she had other plans, vastly more sinister and appropriate to his sins of the past.

sublocked
sublocked
701 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Kasey's Legs His girlfriend encouraged his crossdressing and more.in Transgender & Crossdressers
Feminized by My Girlfriend The start of how she changed my life.in Transgender & Crossdressers
Discovering Amber My boyfriend gets caught in my lingerie, changes must happen.in Transgender & Crossdressers
Making of a Porn Queen Ch. 01 Steven takes a job with a wealthy woman.in Transgender & Crossdressers
Wife Converts Husband Ch. 01 She finds out he's into kink.in Transgender & Crossdressers
More Stories