The Trials of Dave Pt. 03

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Dave dresses up and eats out.
3k words
4.43
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3

Part 3 of the 4 part series

Updated 06/10/2023
Created 05/16/2021
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Dave found the boutique surprisingly easily, Madame Roxanne's directions and descriptions were incredibly helpful and detailed. The walking was still tough though, particularly after the long periods off his feet throughout the afternoon and his overall feelings of weakness. Blisters appeared to be forming on some of his toes and one of his heels, making his balance even harder to maintain.

When he reached the store's purple door Dave's heart sank, there was a "Closed" sign in the window. Panic set in, he was alone in a strange city, no phone, no money, dressed completely en femme and his destination was closed. He had no idea what to do, he couldn't even catch his breath. Time ticked by, he was flustered and unable to act or even think.

A voice came from behind him. "Have you tried ringing the bell?" Dave turned and saw a huge man, he was all muscle. The man's physique, added to his bald head and tattoos made him incredibly intimidating. With just two fingers Dave thought the man would be able to squish him! He was glad he couldn't see the man's eyes behind his sunglasses.

"Iiit says they're closed."

"Well maybe they are still expecting you."

With those words the giant slowly walked away, jacket slung over his shoulder in the direction of a bar across the street. Dave took his advice and rang the bell.

After about 30 seconds a small brunette woman came to the door with a beaming smile on her face. "Ah are you Davina? I thought you'd decided not to come after all, come on in!"

Dave followed behind as she sashayed into the dimly lit room.

"We close at 5 but I've been looking forward to this all day." She had a reassuring tone that reminded Dave of his Grandmother, but she was much more attractive than that. He really couldn't place her age, her face had some wrinkles, but had fought them back well and her figure seemed athletic despite her petite frame. Most importantly thought her clothes accentuated her perfectly.

She turned on a few spotlights pointing towards one spot off to the side of the store. "Come let me get a better look at you dear" gesturing him into the light.

"Well aren't you a cute one, a little bit of padding but we can handle that. Need to make sure we're showing off your lovely legs, and teasing with your cute little butt. Take your dress off while I go and select a few options, you can hang it on the rack behind you."

Dave was bright red from the complements and then the embarrassment of exposing himself once again. He couldn't help but hold his hands covering his crotch as he stood there on display, realising he could be just about seen from the street if anyone looked in in the right direction. He didn't dare move from where he had been placed though.

Celia spent the next 15 minutes or so walking to different parts of the shop bringing dresses and other items back and forward. Eventually, once she'd filled a rail and collected a pile of other things she turned back to the aching Dave with a wide smile. "You look cute when you're embarrassed... lets start with bringing in that waist a little."

She took out a corset and wrapped it around Dave's middle. "Now this might feel a little uncomfortable, but fashion isn't supposed to be comfortable, it may even push up your little boobs a bit."

Slowly Celia slowly looped and tied the laces on the corset, tightening as she went. Initially Dave felt like he was getting a gentle hug, which got tighter, and then tighter. By the time it was tied he felt uncomfortable, restricted but supported. He no longer quite had the freedom of movement he was used to, the discomfort was coming from being forced into better posture. He could see the difference already though, he appeared to have a slightly thinner waist. He made another resolution to get into better shape for his Goddess.

"Very good dearie, now lets see which dress suits you better."

The next half an hour Dave got a bit of a taste of what a fashion model feels like, constantly changing outfits, being appraised and then have them cast aside as she moved to another. Dave found that he was enjoying himself, all of the different fabrics and fits. He was getting a lesson in style and shapes, what he should wear. What patterns to avoid and which would be okay.

In the end Celia chose for him a pink floral dress which only just came down to his hip. Dave was extremely nervous about this, worried he was going to be constantly on show, but Celia pointed out that Goddess Amelia wanted a sexy sissy, and to be sexy he needed to tease.

He was then even unsure when she moved onto shoes. The two inch heels he had been wearing all day were already rubbing his feet and his calf muscles were burning like he'd never experienced. The first pair she pulled out had at least five inches of heels. Dave knew before he even tried that he wouldn't have the balance to walk in them... Still Celia made him try, and he did better than he thought he would - but still stumbled every fourth of fifth step.

With a tut Celia walked away. Dave felt ashamed that he'd failed the challenge that she'd set him. When she returned she had two near identical pairs, one with a three inch heel, the other four. "Okay honey, we have to go up to at least a three to get the best out of your calves and butt, but I'd rather you made the four, let's see how you cope."

The next 15 minutes saw Dave trip, stumble, sway, loose his balances countless times, but with Celia's support he was starting to get the hang of it, and had been strapped into a pair of four inch sparkling silver heels that showed off his painted nails. Dave was proud of himself for managing to maintain his balance even keep good posture.

"Thank you for your help Miss Celia".

"Oh honey, we're still not finished, you need to accessorise!" She was smiling again as she headed towards a small area of jewellery.

"Now, these aren't the most expensive, or flashiest, but we'll have something to complement you. You really should get your ears pierced darling."

"We don't normally stock this, not my usual style, but I ordered it in especially". She pulled out a pink choker with the word SISSY in large rhinestone letters. Dave was gobsmacked. He couldn't wear that could he? Celia saw the look in his eyes: "Well darling, you should be proud of what you are, it'll look so cute on you and really pull your outfit together."

She also handed him a small clutch bag, with a silver chain to hang over his shoulder. "It may be empty but every gurl should have a bag dearie, and now you look perfect." Dave blushed and muttered some thanks.

"I really don't want to see you go but I think it's time to give you this". She handed him another envelope.

"I'm sure you look a picture my pretty little girl. I can't wait to see you. But first, you must be hungry? Did you have lunch? Well it's certainly time to get something into you. Head over to the bar just over the road and ask if Pete can give you a protein injection. It might be an acquired taste, but if you want to be mine it's a delicacy you'll be expected to get used to. "

Dave was confused, but thanked Celia and slowly made his way out of the shop and towards the bar the bald man had walked into a few hours ago now. His Goddess was right, he was starving, but he couldn't understand what food she might have had in store for him.

He walked into the dimly lit bar and for the first time all day he didn't quite feel safe. Every head in the half full room turned towards him, and for the first time all of the faces were male. Quite a few of the men had that drunken haze look in their face, and were leering at him. One table in particular had three men, who were eyeing him greedily. The men were so alike they could have been triplets. Immaculately styled blonde hair, slight stubble, stylish fitted shirts highlighting their defined muscles. In any normal occasion Dave would have described them as beautiful men, however their eyes displayed the obvious effects of all day drinking and their stares made him genuinely uncomfortable.

Gingerly Dave made his way to the bar. The man behind it was a large man with a huge beard. His outfit shocked Dave as he was wearing a leather waistcoat which showed off his hairy chest. His nerves were reduced somewhat by the guys beaming smile. "I'm looking fffor Dave".

"Then you're come to the right place friend, what can I do to help you?"

"Erm... I was told he could give something to eat."

"Hmmm, was there something specific you were wanting?"

"Erm, I believe it was a protein injection."

Pete leaned in closer to Dave so nobody else would hear them over the music playing through the speakers, presumably from a jukebox somewhere.

"I thought you must be Davina... I can give you that, but I'm not certain it'll be what you want when you realise what it is. Though surely you must already suspect?"

Dave knew, he thought he'd known since he read the words on the letter but hadn't admitted to himself.

"She wants me to blow you doesn't she?"

"Well I wouldn't have phrased it quite like that, but yes, that is the task she's set, how do you feel about that?"

"Scared, I've never done anything like that before, I don't know if I can."

"I'm not going to force you into anything, you either want to or you don't - if you don't it won't be good for me, but this is the task that has been set for you and I believe you need to complete it to achieve your goal?"

"Yes, I do."

"Okay, then let me get you a drink and you can have a while to think about it?"

"I have no money."

"Of course not, don't worry, whatever you want, it's on the house."

"Erm, can I have a whiskey then please? And a pint of water?"

"Certainly love, take as long as you want, then let me know either if you're ready or wish to leave."

Pete didn't just go for the House whiskey, instead poured a generous measure of Glenfiddich 15 year, which Dave appreciated. He took his drink and moved over to a table against the wall, careful to make sure he was keeping his legs closed and not sitting too provocatively. To the left was a large bald man reading a paper, it may have been the same one that helped him earlier, Dave wasn't sure, but didn't want to strike up a conversation right now. To his right two elderly gentlemen who were paying no attention to him. He'd deliberately sat away from the triplets (as he thought of them), but even despite being on the other side of the bar he could still hear they were getting rowdy.

Dave only sat for a few minutes, the day was getting away from him, it must already be 7:30, he was hungry and parched. The water he downed and then he took a sip or two of the whiskey. He'd come so far, he must be near the end now? Women do this all the time, surely it's not that hard? Would it make him gay though? He didn't think so but would other people think that? Was that a test his Goddess had set, to see if he was? No, that would be unlike her. She had set this for him to show that he would be willing to push his own boundaries for her, it wouldn't hurt him, would it? It would just be a mental realignment of what he was capable of.

He took another sip and walked back to the bar slowly. "I'm ready if you are Pete." "Excellent, we'll take this through to the back."

They walked into a dark office, Pete switched on a lamp in the corner, not the main overhead light which Dave was grateful for then locked the office door.

"Now if you're absolutely sure you want to do this, again, I'm not going to force you, however cute you look in that outfit, but if you really want to do this drop to your knees."

After a moment of hesitation Dave obliged,resulting in his corset digging into his ribs a little more. Pete walked up to him and started undoing his belt. Dave closed his eyes, he couldn't believe he was going to go through with this, but he couldn't come this far and back out now. When he opened his eyes again he was met by Pete's 9 inch erect member. He wasn't expecting it to be so large, he'd never seen a real penis before other than his own (which hardly counted) and in porn so even knowing it was coming was a shock. He reached down between his own legs and touched the steel of his small cage below his panties. Like a deer in the headlights he just stared at Pete's penis whilst lamenting the size of his own. "Impressive I know, but it's not going to blow itself."

That spurred Dave into life, he reached and took the base of Pete's long shaft in his hand, wet his lips and put them on the tip of his long cock, before slowly sliding it into his mouth. His first thought was that it actually just tasted like skin, sweaty skin. Why was he surprised at this - after all that's all it was! Not knowing what he was doing he took as much as he could in his mouth. He tried to think back to the last blowjob he'd received, 15 years before... okay that experience was no help for right now, he'd exploded in 10 seconds. Instead he thought of porn and started moving back and forward whilst moving both of his hands over the shaft.

Appreciative noises started coming from Pete, which filled Dave with a bizarre sense of pride. He tried to pick up the pace but found his jaw was hurting already, he was also starting to feel shame and regret. Tears appeared in his eye.

Pete appeared to notice this and pulled out, taking hold of his own penis he told Dave to open his mouth wide and stick out his tongue. Dave closed his eyes again and a few minutes later he felt the splat of some warm liquid hitting his face, some of which made it into his mouth. The tip of Pete's cock touched his tongue again. "Lick me clean and swallow." Dave obliged, trying not to gag or be put off by the saltiness of the cum, there was also a slight metallic taste to it which reminded him of old coins.

He gulped down as much as he could, almost savouring the last lick of Pete's now drooping appendage. Pete was straightening himself out, pulled up his trousers and pants in one action and refastened his belt. "You did okay for a first attempt, I'll pass on a positive message to Amz, now go and get yourself cleaned up in the bathroom next door and join me at the bar where you can finish your drink if you like." With that he unlocked the door and walked out leaving it ajar.

Dave sat for a few moments feeling totally used. He could now smell the cum that felt like it was still on his nose and he found that he was straining as much as he had in a long time against the bars of his own small penis prison. He rubbed himself frustratedly over his panties. It offered no relief yet he kept going and started to weep a bit. He wanted to cum himself so badly.

"What have we here then?"

Dave shocked turned around, one of the 'triplets' was standing in the doorway. "A fresh bit of meat if my eyes don't mistake me, bend over I'm going to make you my new bitch."

Dave wanted to scream but no sound came out, he was terrified, feeling completely vulnerable and at the guys mercy. The look in his eye was pure sadism. Dave plonked himself on the floor and inched away from the doorway. However no sooner had the fear risen in him it was relieved as over the triplet's shoulder he saw the bald headed man appear.

Grasping the triplet by his shirt collar the giant lifted him into the air and effortlessly threw him into a bookcase just to the side of the room. "I think it's time we got you home Davina." He bent and offered him his hand.

For the first time Dave looked at the giant's face and he realised that the guy had been following him all day, obviously some protection arranged by Goddess Amelia. He had been a little concerned that she'd let him go through this on his own, but knowing that she'd looked out for his safety the whole day warmed his heart. He took the man's hand and he helped him to his feet before leading him by the arm out into the bar.

They went back to his table where he pulled out a small bag and passed it to Dave.

"Like I said, I think you've had enough for today, there's a train ticket in here, valid whatever train but I recommend you get the next one at 8:30, you should have enough time. There's also a sandwich and some drink. I'll be following but you have to walk on your own I'm afraid."

Dave thanked the man, and felt more comfort knowing he'd be close by as he took the bag and made his way to the door, completely forgetting he had now dried cum still on his face.

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ChasteFantasistChasteFantasistalmost 3 years agoAuthor

Thanks Anonymous, I usually find other stories too quick so expect the opposite to be directed at me. Part 4 is awaiting moderation. Had always been planning on it as a four part story but now think there are a lot more places I can take it. Still, currently writing a stand alone story first.

AnonymousAnonymousalmost 3 years ago

Originally thought the pace was too slow. Having read, from the beginning, I now know your timing of the development is ideal.

Enjoy your smaller chapters and am looking forward to Mistress further developing Davina to the Sissy she really wants to be.

Well done.

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