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  • And When I Return Ch. 06

And When I Return Ch. 06

12

Mayhem enveloped him. There was an alarm of some sort and he sat up in the strange bed. Light came through his curtains in a sharp horizontal slice toward his head and eyes. He isolated the source of the alarm at his bedside table and turned it off. It was 0600.

Where was he? He went to scratch his face and almost poked his eye out with his long nails. Then it all came into focus. His lower ribs felt tired and compressed in the corset and he looked down at his breasts in the bra.

Holy fuck, he thought; this wasn't a dream! He looked around the room. It looked different in the morning light, as all female bedrooms do, much more dainty and feminine. His skirt and blouse lay in a heap on the floor along with his shoes and garter belt and hose. His head ached mildly and he was thirsty.

Suddenly Fiona poked her head in and said cheerfully, "Rise and shine Anna-baby. I'll be back in a minute, but in the mean time, get in the bathroom and take your bra off. I'll be in shortly to get you out of your corset. And brush your teeth; I hate morning breath."

The uncertainty of the waking Jason morphed immediately into the erotic and hopeful Anna. The journey had begun. He said, "Yes ma'am." And he stripped in front of the mirror. It was an odd sensation to feel his breasts bounce when he moved and took off his bra. The seal to his skin was nothing short of amazing. They got in his way slightly when he brushed his teeth and he could swear he felt it when he accidentally nudged his nipple with his forearm. It gave him a thrill of perceived reality within all the fantasy.

His face however was another matter and he tried not to look at it. Stubble showed through and the eye shadow and mascara was streaked across his face. It had been a mistake to wear the wig to bed. It was a mess of knots and strings.

Fiona was dressed in her usual attire, unadorned and plain, walking stoutly about, waiting to be used as required by her owner and she was obviously pleased to be doing so. She entered with some rubber tubing and some other paraphernalia and said, "Okay, off with your corset and we have to hurry. We don't want to lose what we've gained in the waist training so far."

The relief was enormous as the corset was slowly loosened and removed, but he had the odd involuntary desire to hold his belly in when it was off. His breasts, now alone, hung obtrusively over his hairless belly and they jiggled like jelly, pulling on his upper pectorals in an unfamiliar way, pleasant in an erotic sense, but partly painful as well. He missed the support of the bra already.

"Step into the shower while I get your enema started. Put this "you know where" and I'll hang the bag with the solution in it. Take the whole bag; hold for as long as you can, and then expel in the toilet. After that, refill it with just warm water and do it again for the final cleaning. Then shower and shave and I'll put a clean corset on you and tighten it up. We should be able to get to twenty-eight and a half inches today I would think."

He had forgotten about the enemas and groaned with dread. Strangely, for the first time he felt awkward standing nude in her fully clothed presence. He did as instructed as he had agreed in the Rules of Engagement. It was not as bad as he had expected other than the humiliating aspect of the act of it all and of course the smell. Fiona seemed not to notice and sang cheery melodies to herself as she assembled his corset and makeup on the counter. He showered and shaved and just as he was waiting for the corset to be applied to him, Fiona entered with a large fearsome looking anal plug made of stainless steel. She lubricated it and faced him saying, "Okay, bend over."

"What? That's what she meant by an anal plug? Jesus, that's going to hurt. I'm not too sure about this. Be gentle; it's my first time," he said with a nervous laugh.

Fiona laughed and said, "Yes, it might hurt at first, but once it's in, from what I understand it's quite erotic for men. Massages the prostate you know. Now try to relax. Sometimes it helps to push slightly as if you're trying to fart."

Anna bent over and his breasts hung like water-filled balloons near his chin. The cold metal touched his anal opening and the relentless push began. He tried but he just could not relax, so Fiona soothed him by talking erotically, saying, "A virgin vagina I see. I like taking virgins. Spread your legs my little girl. Get ready to take it all like the woman you are, yes like the woman you are...that's it..."

It was working but it was painful. He yelled out when the full width of it passed his sphincter and entered him fully and quickly, the muscles grasping it between the inserted bulb and the flared end which still protruded. Now, instead of rejecting it, he pulled it in with every sphincter contraction. The outward end had a small handle and she moved it about, seating it correctly and started moving it back and forth in and out slightly until his prostate realized it was being stroked. He began to push back and moan. Abruptly she stopped and told him to stand straight while she laced him into a clean corset for the next twenty three hours.

"Do I have to have this plug in all day?" he asked between breathless constrictions of the laces.

"It only comes out when we use you there. Diane explained all that to you. There isn't one of our clients who doesn't eventually like the plugging and the pegging. You'll see. If we intend to use you some evening, we'll replace this one with a similar plug but with a wider diameter at your opening. That way you'll be ready for use and get full enjoyment instead of being in pain for part of it. Stretch you out so to speak."

Fiona tied off the laces as Anna struggled to get accustomed to the breathlessness again. When she measured his waist she was astonished to find it at twenty-eight inches. Worried, she asked, "How does that feel? I fear it might be too tight."

With the plug massaging his prostate and the corset compressing him in a womb-like embrace, fantasy overwhelmed his logic and, breathing in puffs, he said, "It's fine. Nice and tight ma'am. Oh God, that's..." He was going to say "like a dream" but he was too embarrassed to show how much he actually enjoyed this.

She applied his makeup, this time requiring him to do certain things, like add the blush or shadow. It was helpful and he learned. Today she locked him into a rose colored maid's outfit with black bonnet and apron, along with lock-on three inch heels.

"Diane was a little upset with your mannerisms with your knees last night. You kept letting them spread apart. She wants you to wear the theraband on your thighs the whole day today. Put it on please."

"Really ma'am? Do I have to? It's so annoying."

"Just do it please." And she watched as he struggled to bend enough to pull the band over his shoes and up his legs. His knees pulled together quickly and he stood, breathing with short puffs of air, as he was momentarily out of breath.

He walked breathlessly into the kitchen at 0840 for breakfast, forced to take short steps, heel to toe, heel to toe, and swing his arms not from the shoulder but more from the elbow, with his elbows in. He stood perfectly with his knees and ankles together and his hands held together in front of his crinolined dress.

"Anna, you look lovely dear! Come and sit down. What would you like for breakfast?" Diane said.

Diane looked awful and Anna was disappointed. She wore a bathrobe pulled tightly around her morning face devoid of makeup. She was still beautiful, but there was a certain radiance that was absent.

He was hungry. The corseting of yesterday had limited his intake of supper the night before, so he asked for a three egg omelet with some tomato and pepper pieces mixed in, cheese on the side. Within minutes it was delivered to him but, again, he found that his hunger was tempered by the corset so he only finished half of it along with a cup of coffee.

He didn't feel quite as silly today in the maid's dress. He knew this was their training tool and he had to just live with it. Besides, it was a private matter, between him and Fiona and Diane. But the anal plug; that was different; with every movement it massaged him in places that made him inhale quickly with pulses of desire. He couldn't take his mind off it as it worked away, building him up but never letting him go.

"What am I supposed to do today ma'am," he asked somewhat breathlessly.

"It's a beautiful morning Anna, so you'll be working in the garden until noon. I don't want you sweating out there in the afternoon. Can't do much with man-sweat. There's a basket on the deck outside the living room. Would you get it please?"

He did so, returning with a Riding Hood type woven basket over his left elbow.

"First chore is to get the mail."

"What do you mean?" he asked cautiously, tilting his pretty head slightly.

"We have a mailbox at the end of the lane. Go get the mail please."

"What? But...umm, it's broad daylight!"

"Yes it is. So? You can do it, but make sure you act like a woman and not a man in drag. That's the test," and then she added ominously, "And you'll do it because I told you to."

"I see. Oh God. Yes ma'am," he said, lowering his head.

"The neighbors see maids like you retrieving the mail all the time. You're like a tourist attraction. I'll walk with you today if you like."

"Yes ma'am, I'd like that. Thank-you."

Diane didn't even bother to change out of her bathrobe. She said, "Come on; let's go. Walk like I told you."

For Anna, who had by now in his mind reverted to Jason in drag, it was 150 meters of delicious erotic hell, if that makes any sense. He hated it, but his gaff was fighting every inch of his penis as he approached the mailbox. Diane walked behind, correcting him on subtle movements and mannerisms.

In the distance he heard a roar and with horror he could see an approaching cloud of dust. He turned and looked pleadingly at Diane. She shooed him forward with a wave of her hand. Only ten more metres. He hurriedly ran to the box, opened it and the mail spilled out all over the ground. He looked at Diane again. She motioned for him to put it all in the basket. He knelt down and the anal plug worked its magic once again. He gasped.

The car approached and stopped. The slight breeze slowly blew the dust away like a magician's disappearing act gone wrong. The car was still there and so was Anna. His dress fluttered slightly in the breeze and his thighs were cool, exposed to the morning air.

The passenger window rolled down and an elderly woman leaned across and yelled, "Good morning Diane. Beautiful day." She sized up Anna, head to toe. "This looks like a good one Dee. How long have you had her?"

Diane smiled and said, "Arrived just yesterday, Bertie. Gonna be here for two weeks. Name's Anna."

Anna just stood there like a servant should, demure and dominated, nervous and subdued. His face burned and he felt sweat under his arms in the cool breeze.

"Well Anna, you should have been born a woman I guess. You look great. Good job Dee! See ya Wednesday." And she drove off.

Anna looked at Diane, who said, "See? I told you so."

Anna was speechless and remained glued to his spot, picking up and dropping letters.

"Anna," Diane said, "I'm going back to the house. I want you to stay here until I call you back. You have to get used to this."

"What? No, please ma'am, don't..." But Diane had already turned and was making her way back, her slippers scuffing the pavement of the lane. He could have simply followed her, but he knew how that would end. She would get angry and maybe send him home. At the very least, his adventure would be over before it really started.

So, for the next half hour Anna stood like a child waiting for a school bus, his basket full of letters over his left arm. Five more cars passed, all slowing down, some rolling down their windows and saying hello to him in polite tones. Two of them were men and one gave him a whistle signifying his approval, or maybe he was being sarcastic. He did not know.

The humiliation of it was intense and deliberate. By the time he heard Diane's call to return, he was almost orgasmic, but the anal plug and its massaging only seemed to get him halfway "up the hill" and left him perpetually aroused but unsatisfied. It was maddening. Why did he like this, he wondered? Why?

Having delivered the mail, he spent the rest of the morning picking spent flowers from the beds in the back yard. It wasn't fun and he soon forgot the erotic nature of his treatment and dress, the fantasy fading away with every painful step in the high heels. His calves ached, and the damned band around his thighs forced him to be very dainty, causing balancing difficulty when kneeling to remove lower hanging buds. By noon, he was exhausted and thirsty.

He was at the back of the yard under a large shady oak when he heard Fiona yell, "Anna, time for lunch! Pick two tomatoes and bring them with you."

He wanted to run to the door, but all his gear forced the feminine walk of what seemed like a million steps. Why did women put themselves through this, he wondered? But then the anal plug abruptly shifted again and his sphincter pulled it up and against his prostate. He shut his eyes and quivered as his vagina went into erotic spasm. He had to stop to catch his breath. His panties were soaked with expelled and unused semen, only lubricant for his dreams so far, a full release perhaps in his hopeful future.

In the kitchen, he was given orders to make bacon and tomato sandwiches for all of them and to make coffee. Diane and Fiona sat and waited while he worked, periodically correcting his hand or head movements, and suggesting subtle waves or head tilts. It was mind boggling to him and he felt overwhelmed. Fatigue began to overtake his ability to react to their comments and finally he said, "Please, I can't do it all!"

Diane laughed and said, "A woman's work is never done. I'm hungry. It's only noon and you're complaining. I'll have none of that missy! Or you'll find yourself in a much more uncomfortable circumstance sooner than you'd like."

It was a sharp rebuke and he didn't respond. His calves ached so badly; he just wanted to sit for awhile. Finally all was ready and he served them both before he sat down with his own coffee and sandwich. Without even thinking he sat with that pose, legs together showing the correct modesty. The gaff held easily; there was nothing erotic going on in his head right now. Hunger and thirst dominated.

He tried to eat as daintily as possible and assumed he was doing so, because there was no criticism. After a few minutes of silence he looked up to see Diane staring at him.

"You're an absolute marvel," Diane said, "You look gorgeous!"

"Thank-you ma'am."

Then with an abruptness that surprised even Fiona, she added, "I want to make a woman out of you tonight. I want to fuck you."

"You mean...?"

"Yes, I do mean. Fiona, after lunch I want you to put the "expander" plug in so that Anna is loosened up nicely for playtime tonight."

"Yes ma'am."

Anna was both surprised and alarmed, "Are you sure I'm ready for that ma'am? I mean, I still feel, umm, full, umm, with this one." He squirmed on his seat.

"Personally I don't really care if you're ready. I am, and the quicker you get fucked the better. It's all for your training...well, not all; I just feel the need to peg you and make you feel like a woman, to make you feel used and dominated like women often are. I already have a plan in my mind's eye about how you're to be taken. Losing one's virginity is always an exciting and scary thing is it not? I'll be gentle. Maybe. Initially. And believe me when I tell you that you'll enjoy it!"

Anna grimaced slightly but said nothing.

The "expander" plug was made of silicone, in contrast to the stainless steel variety that was currently sealing the orifice. Before Fiona inserted it, she let him examine the new device to calm his nerves.

Fiona said soothingly, "See? It's the same width for the bulb that you have inside you now. The difference is in the shank, where it's much thicker. And the flared end keeps you from swallowing it whole. So, when the main bulb gets past your sphincter, it won't be able to close so completely and you'll get stretched."

"I see, but won't that sphincter size be painful?"

"Not at all. You'll just feel more full. After awhile, your sphincter will "give up" so to speak, and you'll be ready for a more relaxing round of "vaginal" sex," she said with a smile.

At this point, Anna flashed back to his male self briefly and he felt odd, like being inside a dream without being able to wake up. He felt like stopping all this and just saying this was too much. But he didn't.

He felt like leaving. But he didn't.

Then he was told to bend over in order to remove the steel plug. He expelled it easily. Fiona added some lubricant to the silicone plug and asked him if he was ready. He said yes and Fiona pushed. It went in easily and he gasped while his sphincter seated itself on the thick shank. It felt very strange and he indeed felt full, a not unpleasant feeling he found.

"Mistress has also instructed me to stop using the gaff and rely only on girdles from now on to flatten you out," Fiona said, "She thinks it's more in keeping with your clothing fetish. But if you wear any tights without a skirt for example, you'll have to use a gaff, okay?"

"Thanks. I hate the gaff actually."

The afternoon housework consisted of laundry and ironing as well as changing the bedding and towels throughout the house. Anna went about these tasks with hardly a thought about the tasks themselves, as the new plug kept him wide-eyed in anticipation. What would it be like to be "fucked" by a woman, he wondered? Would he feel gay being penetrated like that? Would he have an orgasm? Or would it be simply something that was interesting and fun, maybe as mundane as a duty rather than sexual gratification? He felt like a virgin on her wedding night, dependent on the spouse for reassurance and guidance.

Anna's fatigue was almost overwhelming but for the erotic pressure of the corset and the probing of the anal plug. He was on edge as he cleaned up the dishes after supper. He had resigned himself to performing these mindless tasks as was his duty as a house maid, and it thrilled him in strange and erotic ways. He felt his breasts vibrate and bounce, and occasionally the bra straps strained with the weight, depending upon the amount of gravity applied by different tasks. He felt like a woman, the woman of his dreams, immersed in absolute fantasy.

Diane had left the kitchen after eating to change and now she had returned in her very familiar dominatrix gear: thigh-high laced up boot stilettos, black leather under-bust corset with garters and black seamed hose, and breasts free to do as they wished. As Anna observed her in envy and lust, he noticed that there was a precisely trimmed triangle of pubic hair below the corset. He wanted to be there, to drink her in and smell her. This was the woman that would be taking his virginity. Taking it tonight.

"Hurry up Anna," she said, "I want you to tour the dungeon with me and Fiona. Just so you'll know, I'm going to put you in full helpless bondage tonight. I can't have you changing your mind." She snickered and went up behind him at the sink and circled his waist with her arms and pushed herself against him, gradually moving her hands up to his breasts. She took one hand away and placed it in the crack of his behind and pushed hard, the anal plug slipping a little deeper inside him. He trembled.

"Leave the clean-up for Fiona later. I want you," she said, her breath husky and slightly breathless.

"Yes ma'am, I want you too," he answered, "Let me fix my lipstick and we can go."

12
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