Sissy Friends Forever

"What you got in mind?"

She ordered some lavender colored towels and a pink bedspread for the main bedroom. She got some cute photos for the walls and several sets of flowers. She ordered me a huge elaborate vanity in white for the bedroom with a large mirror adorned with lights. It would really make a statement.

"We can spread all our make-up out on that when it arrives. Let's casually arrange some in the main bathroom too, you know, the one that guests will use so when you invite someone round they'll see your lipstick."

"Done. Oh, we should put some maxi pads in there too."

"Definitely, we should also be wearing them."

"Maybe I should permanently keep a pair of stockings on top of the laundry basket in there?"

"Good idea. I want to get your clothing collection more on display in general. A thing of beauty should not be locked away like that." She went into my closet. "Your shoes are incredible and you've got so many pairs. Loads of these are designer. These aren't just shoes, these are art."

"Thanks. But where could we put them?" She thought for a few seconds and went out to the hallway by the entrance. I had a large floor-to-ceiling shelving unit consisting of wooden cubes. I was only using it for displaying knick-knacks and trinkets. "Here would be perfect. The first thing people see when they arrive."

We moved dozens of pairs of my high heeled shoes out into the hall and decoratively arranged them, one pair in each cube until they were all full.

"I'll order some lighting strips. We can make a real showpiece of it. They'll look so nice lit up in soft white. They'll really draw the eye."

I heard a phone beep and automatically reached for my pocket but couldn't find it. I then realized it wasn't there because I completely forgot I was wearing a dress and didn't have pockets. I was so comfortable it was just a natural feeling now. I picked up my phone from where I left it and looked at the notifications. It was from the bank, it was the charges coming through for Cindy's home improvements. "Hmmm... this looks expensive. I am going to spank you five times every time I get a charge caused by you."

"Is that all?" she looked disappointed.

"Ten times?"

"Getting better. We're running out of food. I'd best go shopping."

Later in the evening I had Cindy over my knee. I had her skirt up, her panties pulled down and had slapped her bare ass until it was red.

"That's it. I hope you learned your lesson."

"Not really. Best keep going."

"Nope. I think my hand hurts more than your ass probably does."

"I'll order a paddle."

"That'll cost you ten more spanks."

"For reference, now would be the correct time to use the word ironic".

She pulled up her panties, sat beside me then lay across my lap. I played with the hair of her wig. "You could get hair extensions."

"I'd like that. Can I get hyaluronic acid?"

"I don't do drugs."

"No, it's lip plumping. You know, really filled-out voluminous lips. Bimbo lips. No one could ever possibly take me seriously with lips like that. It's so hot."

I played with her lips and put my finger between them. She started sucking it. I moved my finger in and out. "That's exactly what you need. You're thinking like such a ..." I snapped my fingers. "... good girl".

...

I got home from work and Dr Bimbo was using my laptop. She looked hilarious. She was wearing a man's shirt and tie, no wig and no make-up but she had a bright pink skirt, stockings and heels on under the table. She had glasses on I'd never seen her wear before. She was looking serious and was on a video call with several business people discussing highly technical terms I didn't understand. I stayed quiet and out of view of the camera until she finished.

"Having fun?" I asked when she exited the call.

"Not really. Job interview. I need to earn my own money, I can't keep using your card."

"Why? Your ass can't take the punishment?"

She laughed. "No, I feel useless around here and I guess I can't stay forever."

"You can stay as long as you need," I reassured her "I love having you around."

"I really appreciate that. How'd it go with the new look," she pointed at my face.

"Elouise, of course, immediately noticed and complimented me on my eyebrows when we caught up to discuss her dating. She said it made me look so much softer and effeminate." Cindy seemed really pleased. I was fully cognizant of the fact that she was trying to deliberately sabotage any possible romantic relationship between me and Elouise and I wanted her to do that. It was a game of erotic emasculation in front my crush, but Cindy seemed particularly gleeful about it. She was hiding something.

"What do other people say?" she asked.

"Apart from Elouise they don't really say anything. It's like, you know if you've had a beard and then shaved it off. Often people don't notice even though it's a dramatic change to your appearance. They stare at you like there's something different but just can't place what it is."

"How does it make you feel?"

"Humiliated every time I speak to someone, wondering what they think."

"Is it keeping things at the right level for you?"

"It is for now."

"What did Elouise think of our choices?"

"She liked one of them, the older banker guy. She's going to give him a chance."

"Awesome. Time well spent." Cindy seemed happy and got up standing directly in front of me. I put my hand down her panties. "You need to keep me updated, especially when she tells her best girlfriend about all the sex with him. How he fucks her again and again, like you can never do and she screams with passion for him. When your crush tells you how huge his dick is and all you can think about is sucking it yourself. Maybe you'd like to suck it after he orgasms into her, licking off her juices mixed with his cum. "

Cindy was massively turning me on. "You're such a bad girl." I snapped my fingers with one hand and squeezed her cock cage with the other.

"That does absolutely nothing," she said, shaking her head.

"Well it should." I pulled away from her. "So do you think you'll get that job?"

"I doubt it."

"Think positive. You're very smart, they'll see it. What's your Ph.D in anyway?"

"Bioinformatics "

"That word is way too big for me."

"Maybe you're a bimbo. I can lend you a short pink skirt."

"Come on. What does it mean?"

"It combines computer science and statistics in the analysis of biological data."

"So I heard you say some kind of computer stuff then blah blah blah."

"I'll get you that skirt."

"It's not very sissy is it?"

"Neither is marketing. That's nothing but drinking whiskey and mainlining testosterone I found out from watching Man Men."

"Well there's one sissy who has a job in marketing."

"Touché. So what's a job for a dumb bimbo?"

"Secretary."

"Obviously. The boss' cock isn't going to suck itself. Air stewardess? I've got a thing for the Pan Am look." She touched her head and looked up. "I want the cute little hat."

"Maid?"

"Far too clichéd. I got three maid's dresses, first thing I ever bought."

"Great because the oven badly needs degreasing."

She looked at me wearily. "I think you're confusing a sissy maid with a cleaner."

"I hate cleaning the oven. If you do it I'll spank your ass so hard."

"I'll think about it."

"Retail? Selling something girly?"

"Hmmm ... maybe."

"OK geek girl, do you know how to make a website?"

"Sure, it's easy."

"How about you sell sissy products online? We can find out how many of us there are out there. You can work out of the guest room. Just a little side business while you're waiting for things to turn around. Maybe it'll go somewhere."

"I'd need thousands for cock."

"What?"

"Stock," she slapped her forehead. "It's my sissy brain."

"I got you covered."

"How I am going to advertise it?"

"Erm, excuse me?" I turned my shiny nails towards myself. "Don Draper, right here."

"Donna maybe. Can I really do this?"

"We'll do it together. It'll be fun."

...

All the stuff Cindy had ordered for the house arrived and we'd spent a couple of hours organizing it. We were slumped on the couch, exhausted from moving the vanity.

"Should have got a real man in to do that," I said.

"That is one heavy sucker. Us betas just aren't up to this kind of manual work. Moving furniture is not for sissies."

I got a call and picked up my phone, it was Elouise. "I'm ten minutes away from your place. Can I come up to chat?" she asked.

"It's Elouise, she wants to come here," I whispered to Cindy. I was just about to decline with some excuse when Cindy grabbed the phone from me.

"Hey hon, Chris here, of course. Can't wait to see you again." She hung up.

"What the hell have you just done?"

"We've just got the place nice, we need a visitor to show it off to."

"Get in your man clothes now and take that make-up off. Be manly."

We both rushed to change and were barely ready when Elouise rang the buzzer. Cindy was wearing a shirt and jeans.

"This is so dull. I'm going to put on some lipstick?"

I snapped my fingers. "Clothing lock!"

"Hey, no fair."

"You! On the couch." I ordered Cindy sternly while pointing at her. "Put some kind of sports on the TV and behave."

I rushed to answer the door as Elouise knocked. Cindy didn't stay put and came into the hallway behind me.

"Elouise! Thanks so much for coming over. I don't think you've been here before have you?"

"No. Hey Chris!" she shouted over and waved at him.

"Elouise," Chris saluted her.

I invited her into my apartment hallway. She was wearing a gorgeous satin cami drape dress in red. She was clearly looking to impress, it wasn't just day wear, not for a real woman anyway, it would be for me.

"Love the dress," I complimented her.

"Thanks babe" I expected more explanation but she was suddenly distracted. Her attention was immediately drawn to the now illuminated display of elegant heels. "Oh..." she was open mouthed with awe, her hand resting on her chest, eyes darting across the shelving scanning everything in my extensive collection. "What lucky girl do all these belong to?"

"All Aaron's," shouted Cindy 'helpfully'.

"Did you not want to watch the game Chris?" he didn't move.

"You collect shoes?" asked Elouise, surprised.

I looked at the floor. "Yeah. I mean lots of guys collect shoes, sneakers and stuff."

"This is amazing. Those are Chanel and you have Versace." She picked up one particularly iconic pair with a red sole. "Oh my, you have Christian Louboutin Pigalle pumps. Who did you fuck to get these hella expensive beauties? I've always dreamed of a pair. Can I try them on ... please?" She pleaded.

"Sure. Go for it."

She tried to get into the shoes. "Oh, they're huge," she laughed. "I mean, look at this. They just fall off my feet. What size are these? I didn't even know they made them this big." She compared my boat-sized shoe against her own dainty heels.

"Aaron's size," added Cindy. I shot him a look of daggers.

"So you wear them?"

"Er, not really. Just maybe a couple of times out of interest. It's just a collection," I lied. I wore designer heels like most women wore casual flats.

"Can you put them on please? I want to see how they look." I took my socks off, they wouldn't fit otherwise. I slipped on the shoes and walked up and down the hall, automatically heel to toe, placing one foot in front of the other in confident strides, highly practiced as I was. I should have feigned instability and wobbling. "Great walk, you're like a model. I absolutely adore them, I'm so jealous."

"Did you want to come through?" I tried to change the subject and gestured for her to move along.

"Yeah, sure thing."

I was so completely comfortable in the heels and so used to wearing them daily I forgot to take them off and absentmindedly followed her through to the living room clicking against the wood floor as I invited her to sit on the couch.

"Not putting your shoes back on your display?" she asked.

"Keep them on," interrupted Cindy. "They suit you."

Elouise laughed. "He's right, they are so you."

"Can you maybe find us some coffee Cin...Chris? Please honey?" I tried to get rid of him.

"Oh, sure thing," he made a move to the kitchen.

"Don't want to trouble you Chris," Elouise stopped him. "I've not got the time to drink it." Cindy sat down again, opposite us. "I just called in real quick to tell you in person. Had my first date today. Exciting! It went really well," squealed Elouise in a spirited fashion.

"Oh, I'm so happy for you Elouise." I said, mirroring her enthusiasm and high pitched tone.

"What's he like?" added Chris.

"As you probably saw from the profile, his name is David, he's 42. He works in finance, he's divorced and looking to get back on his feet. He does charity work and he's into photography. He's introverted and quiet, he's a bit vulnerable, it's really cute. He goes running a lot, keeps himself in good shape."

"So, fuckable then?" Chris asked slyly. I glared at him.

Elouise laughed. I couldn't believe he said that. "We'll see, depends if he's a good boy." She pointed at my shoes and looked at them with envy. "David might be taking me shopping tomorrow, although he doesn't know that yet. I have been inspired." She glanced at her phone. "Sorry, I have to get going. I just had to drop in and tell you in person since I was so close by. He's taking me to the opera."

"Do you like opera?"

"Nope, hate it. He's trying to impress me, to show he's refined I think. So do think these rags are good for the theater? Tell me honestly," she said with mild self deprecation, obviously hoping to elicit a positive response.

"Absolutely stunning," I said truthfully.

"You're sweet ... a liar but sweet."

"No, you look amazing."

"Can I just use your bathroom real quick? I just need to fix my make-up. It doesn't go with this."

"Sure," I said. I couldn't really refuse. I pointed her the way. "You're perfect already." Chris was rolling his eyes at my compliments to her. She didn't see.

Elouise came back about ten minutes later, her make-up done differently, matching her dress. "I found this. Whose is it?" she asked holding up a tube of red lipstick we had deliberately arranged in plain view by the sink. Before I answered she asked "Can I maybe be a total thief and steal it? It just goes so perfectly with my outfit and I haven't got the right color."

"Erm, sure, take what you want." I said anxiously.

"Are you absolutely sure? It's brand new and it's Yves Saint Laurant. One of you has great taste."

"Wouldn't be me," added Chris, trying to clarify it was mine.

"No problem."

"Thanks," she kissed me on the cheek. I got butterflies but I saw Chris furrow his brow.

"Well you definitely need to take that with you if you're going to go around kissing people like that." She smiled and wiped her lipstick imprint off my cheek.

"Best get going. Great to see you guys and thanks so much for helping me find David. I know how much hard work that was. I bet you had something to do with it Chris. Thank you."

"Who me? All Aaron," he lied.

"Hmm ..." she didn't believe him and looked at him with a suspicious expression. "Thanks Chris, I appreciate your help."

We both showed her out. Cindy maintained a pleasant smile until the second I closed the door, then his face instantly slumped like it had been an effort to maintain the expression. "I don't know what you see in her."

"She's hot," I said directly. "That's what I see in her. And she's sweet." Cindy clearly didn't like her but wasn't saying anything about it.

"I'm going to get changed. You should too," he said, with some tension in his voice. I wondered if it was because he was in male mode that he was being guarded about his feelings. I remembered to 'reset' him and waited until she was a girl again before asking her about it, thinking the mental shift might open her up. We were having dinner and she was broody, playing with her food.

"Anything you want to talk about?" I asked. "There's a problem with Elouise isn't there?"

"No, it's fine." When a girl says it's fine, it's obviously not fine, but she quickly changed tack and wasn't going to tell me the problem. "So, your crush has seen you with your nails done, your eyebrows shaped, now you're wearing heels and she suspects you wear lipstick." I smiled. "You are totally blown out of the water sissy. You've not got even one shred of masculinity left. Might as well just go into the office wearing your sexiest dress and do a twirl. Get it over with."

Cindy knew exactly how to turn me on. I imagined gliding through the office in heels and a dress, smiling at all the guys, just like Elouise did. It was a fantasy, but there was reality to deal with. "I can't go that far."

"She's going to tell everyone what she saw."

"I really hope so."

Cindy was back in a better mood. I wanted to keep it going. "I had some charges come through on my credit card again." She grinned. "Get over my knee. Now!"

...

A month later not much had really changed for me. I had long settled into complete comfort with my look. I was climbing the walls, ready for something new. Cindy though, was just coming to terms with some recent changes. I'd bought her the lip enhancement she'd always dreamed of. She had a permanent duck face and was loving it. She painted her voluminous lips glossy pink and couldn't stop pouting at me at every opportunity. I had learned something new, you could just walk into a cosmetic surgery specialist and if you had the cash, they'd do what you want without questioning your sanity even once. It was so quick and easy it was terrifying. I could just think of something crazy I wanted done to my body and they'd just do it? That was dangerous knowledge, I had to keep myself in check.

I'd got her long extensions for her natural hair, which she'd had dyed blonde and styled. She was turning into the bimbo she always wanted to be. I think Cindy was going to have to stay a 'her' now. She couldn't pass as Chris anymore.

Cindy was unpacking panties from a box while wearing a shiny pink PVC dress and heels. We'd started the sissy business together to keep her distracted from her job problems. We had the guest room stacked with boxes of stockings, make-up, cock cages, butt plugs and things I wasn't even sure what they were. I got her a photographic studio set-up as she needed some product photos for her website. Of course, that necessitated a model. She was handing me pairs of elaborate sissy panties to wear and then taking a photo of me in each one.

Cindy was wearing her fake silicone breasts and every time she leaned over to take a photo I looked down her dress. "I got a bad case of boob envy," I told her.

"You want a pair like this?" she pointed at her chest. "There's some in the guest room in a box."

"No, I think I'm desperate for real ones."

"You could do it. It's one phone call away."

"That's what scares me. I need something less dramatic."

"How about you start taking hormones? They'd make your little titties bud. It would take a long time, maybe a year or more."

I thought about it. "How about a game, we both start taking hormones every day and watch the changes. When it gets too much you can stop but you lose the game."

"You are so going to wimp out first."

"I think you're probably right."

"Let's do it. I'll order them." She stroked her ass.

"You got boob envy huh? I have something that's just right for that. You need a break, we'll come back to this later."

Cindy ran me a bubble bath and filled it full of salts that smelled nice. She told me to get in and she lit candles and dimmed the lights. It looked romantic. I hoped she was going to get in with me, but she didn't.

"I'm going to put on one of my special tracks." She sent some audio to the bathroom speaker from her phone. "Now you stare at a candle and don't get out until it finishes."