Sissy Friends Forever

"It's not sexy when you make fun of my kink. Quit it."

"Sorry." I carefully snapped my beautifully manicured fingers. "Reboot! No. I meant restart! What was it?" Cindy rolled her eyes with contempt.

It was evening and I was getting nervous about tomorrow. We watched some junk TV to take my mind off it. In one scene there was a dramatic marriage proposal and I noticed Cindy was glued to it and absolutely in awe. I went to my closet and came back with a cheap gold ring with fake diamonds. As a joke I proposed to Cindy, mocking the style of the TV show and asked her to be my sissy wife. She accepted and made a big show of it. She wafted her hand in front her and tears welled up. I put the ring on her finger. I thought we both knew I wasn't being serious but she seemed to take it to heart. She kept the ring on all evening and looked at it, playing with it constantly and admiring it.

I went to bed early as I had work. I heard the door to the guest room close shortly afterward. I got up and knocked on her door. "Cindy?"

"Hey," she answered. She was still wearing the ring. "Since how you're now officially my sissy wife do you think we should sleep together as a regular thing? I mean it seems the appropriately sissy thing to do."

She smiled. "I'd love to."

She got ready and slipped into bed next to me, rolling onto her side to face me. "When you licked my clitty, that was so hot I nearly exploded."

"Your dick is so tiny, it's cute."

"Thanks," she blushed. She felt between my legs. "I can't even find yours, is it even there?"

I smiled at her. "You say the sweetest things."

"Good night kiss?"

I pecked her on the lips and we went to sleep.

...

In the morning I sheepishly made it into the office, hands firmly in my pockets, but I quickly couldn't get away with that. I typed away at my laptop with my long red nails but it was difficult to concentrate on what I was doing. A humiliating experience was impending, it was just a matter of when. It was like crawling up to the first peak of a rollercoaster. You panicked you had made a bad decision but you were committed now and the experience was inevitable. I was filled with gut wrenching anxiety but of a kind that was intertwined with excitement. I was waiting for the ride to start.

A co-worker looked over with interest.

"Anything I can help you with?" I asked, pretending I couldn't understand what he was looking at.

"No, no." he said. "Good weekend?"

"Yeah, fine."

"Do anything special?"

"No."

The awkward conversations persisted. I was waiting for the first person to be bold enough to make a comment. About an hour later, I heard the distinctive clip of high heels and my crush happened to stride by. I got butterflies in my stomach and felt sick. I rolled my fingers back into a fist to hide my nails.

"Aaron! Great to see you on Saturday. What a coincidence."

"Yeah, nice to see you out too Elouise. Did you have a good evening?"

"I had an awesome night. I hope you don't mind but I mentioned Chris to a couple of close friends. I hope I wasn't indiscreet." Translation: she took out an ad on TV.

"No, no. It's fine." My words masked my inner shame and in an entirely unconscious display of body language that betrayed my true feelings, my hand went to cover the side of my face to shield myself from her. The gesture did the opposite of shielding me and my five colorful digits were spread out on full display in front of my temple, directly facing her. Perhaps it was for the best, I couldn't hide forever.

"Absolutely love the nails Aaron!" she shouted far too loudly, drawing unwanted attention. That was it, I was over the first crest and the rollercoaster was careering down uncontrollably.

"Er, thanks." I winced with crippling embarrassment. I wanted the earth to swallow me up.

"Where did you get them done?"

"Erm, Lidia's"

"Great choice. That's my favorite place! It's really upscale and they're so talented in there." She showed me her hand and by coincidence her nails were near identical to mine. I kept up with her fashion, had I subconsciously copied her style without realizing it? "Are those acrylics?"

"No they are ...er ... " what were they? I remembered. "gel."

"Same here! Great minds think alike. They're so durable. It's so much harder to chip them."

"Is that so? First time I got them."

"Well, you'll need to go back at least every three weeks to keep that color flawless. You should let me know next time you're going. We'll go together."

I was about ready to die of humiliation. "We must do that."

"I'm sorry we couldn't have a drink Saturday but I'm going out for lunch today. There's a few of us going. Do you want to come?"

How could it get any worse. Might as well let everybody see. "Sure, why not."

"Great. I'll book an extra seat and message you."

Elouise gave me a ride to the restaurant and the server seated us. Her co-workers were running late and it was just the two of us. As she sat down she got a call. She looked at the name on the phone with revulsion but answered it.

"What?" she snapped brusquely. "... uh huh ..." I just heard one side of the conversation but she was angry at whoever it was. "... well, that's your problem isn't it ... you should that thought of that before." She pulled the phone away from her face and shouted "dick!" before disconnecting.

"Are you OK? What's wrong?"

"I split up with my long-term boyfriend. He wants to collect his stuff from my place." So she was available then? I suddenly felt an overwhelming wave of joy but I kept my emotions well hidden from her.

"Screw that. Burn his stuff in the yard," I said.

She laughed but looked like she was about to cry. "You know I think I might. It would be cathartic."

"Do you want to talk about it with someone?" I asked tenderly.

"That's sweet, and, I will take you up on that but I'm just not in the right place now."

She put her hand on mine. I felt a tingle, it was the first time she had ever touched me in any way. "Let's talk about something else. So how did you meet Chris?"

"We sucked off a male prostitute together," I translated into: "A mutual acquaintance introduced us."

"How long have you been going out?"

"Just a few days."

"Oh I thought he said he was your boyfriend?"

"What? Oh, no, yes, well he's just, you know, really keen. It's early days. Very, very early days." I didn't want to make myself seem too unavailable.

"You know I consider myself a pretty good judge of people, I never had you pinned as a gay guy."

"What does a gay guy even look like?"

"Oh, you can spot them a mile away. They all have bright red nails."

She made me laugh. I wiggled my fingers at her. "I'm not sure that's true."

"It's subtleties in his mannerisms and style. I don't think I can even describe it, it's just instinctive when I can tell. You just don't give me the gay vibe at all."

"I'm bi-sexual." It was both an answer to the question and a hint I wasn't closed to her as an option. "Maybe that's throwing off your gaydar."

"Perhaps." She looked at my hands again. "So I am puzzled, I've never seen you express yourself before. Did you get your nails done especially for Chris?"

"Yeah ..." I thought for a moment. That was a good explanation. "He really likes the femme aesthetic on a man."

"Oh does he?"

"I don't do this when I go out with women. Not at all."

"Yeah, that'd be the right call for me. I like 'em rugged and manly, femme wouldn't do anything at all for me. Pretty much the opposite." She looked me up and down and took in my visage fully. "You know, sans the nails, you could ..."

At that point Elouise's co-workers arrival interrupted our conversation. We had lunch and I finished the afternoon at work. Eventually one of my more assertive colleagues asked about my nails but I'd got over the humiliation hump now. I brushed it off and just said I felt like it.

...

I went home and my 'sissy wife' was cooking dinner.

"Honey, I'm home!" I shouted playfully. I was in a great mood

"So how did it go?"

"Pretty well I think."

She was at the stove. I approached her from behind and put my arms around her. I put my hand down her skirt and into her panties, playing with her cock cage. House rule: disrespect Cindy.

"Don't ever stop doing that."

"You are a genius."

"I know," she agreed 'modestly'.

"It was deeply humiliating, but in a fun way."

"Great!"

"And my massive office crush asked me to lunch."

"Oh?" Cindy suddenly seemed downbeat. "Erm, who's that?"

"Elouise, you met her. Remember?"

"Sure. So you think she's pretty then?" Cindy asked warily.

"She is about the hottest woman I have ever seen in my life. You don't think so?"

"Erm, she's cute I guess," Cindy added without any real conviction. She turned away and stirred the pot. "Are you thinking straight? Have you forgotten you're a cocksucker?"

"You might understand this. Do you ever look at a woman and just get so jealous of her that you wish you were her? I mean you actually wished you had her body and her life."

"Every single day."

"I get this kind of weird double feeling with Elouise. I really really desperately want to fuck her..." As I said that, Cindy pulled away from me with a serious expression and concentrated on her cooking. I went and leaned against the kitchen counter facing her. " ... but I also want to be her."

When I completed the sentence Cindy's dejected demeanor completely changed and she became animated. "That's my sissy! So, what you need to do is get into a dress and book a session with Matteo just to remind yourself who you are. Get those deeply confused thoughts clear in your head."

I considered the suggestion for a moment. "I think you're right". We had dinner and I messaged the Italian stallion. I told him I had an emergency as I was having straight thoughts. He said he was tired but he would fit me in at short notice. I booked a hotel room and went out to suck him off. His cum was thin and watery, he said he'd already been blown three times before that day. I don't know how he did it. He was certainly a real man.

I got back late and Cindy was already in bed. I snuck in beside her and thought she was asleep but she rolled over to face me.

"Feeling better now?"

"No more thoughts of women for me. I'm on a strict cock only diet."

"Good girl," she said. She paused for a moment. "So who do you think is more good looking, me or Elouise?"

I got out of bed and went over to the full length mirror on the back of the closet. "Mirror, mirror on the door who is the hottest of them all?" I cupped my hand to my ear and pretended the mirror was whispering to me. "It says you're the hottest girl in the world. Can't argue with the mirror." She started giggling. I turned back round to face it. "Hey mirror! What am I then? Ugly or something?" That got a full belly laugh out of her.

"Come back to bed you beautiful mental patient."

She quickly kissed me on the lips. "Good night."

...

By the end of the week Elouise and I were increasingly becoming close girlfriends. She sent me a message. "Is that offer still open to unload on you about my ex-boyfriend?"

I replied to her: "I'm here for you honey whenever you need me."

I met her for coffee and she told me at length all about her ex-boyfriend, all of his flaws and what had gone wrong. As an objective observer in these situations, it often sounds like six of one and half a dozen of the other, but objectivity was the last thing that was needed right now. I comforted her, told her she was perfect, forcefully agreed that it could not be clearer that everything wrong in the relationship was exclusively his fault and that leaving him was the best decision she ever made.

"Thanks for that Aaron. I really needed to just get it all out there. You're a great listener."

"Anytime."

"But I don't want to sit here feeling sorry for myself. I'm going to get right back on that horse." She placed her phone on the table and twisted it towards me. "Last night I signed up with a dating app." I was instinctively disappointed she was dating but tried to dismiss the feeling. I should be pleased for her. I reminded myself she wasn't for me.

"That's the spirit babe. We are going to find you a man who is going to give you all the love that you deserve." I picked up the phone. She had a beautiful set of glamorous photos on her profile. She looked sexy as hell. "These are gorgeous," I was her girlfriend now, I didn't want to comment on her body. "I love your make-up."

"Thanks but it took me hours to get a photo where I didn't look disgusting."

"You could never take a bad photo. You are flawless." That was the truth.

She blushed. "You tell such outrageous lies. It's been a couple of years since I dated. I forgot how much online dating sucks." I didn't understand what she meant. She moved to the other side of the table to sit beside me and took the phone back. She showed me her dating inbox to explain it. She had the kind of problems I would never have in my life: hot girl problems.

"Oh ... my ... god." Every guy in the world from here to Fiji had matched with her. She scrolled through the list, there must have been over a thousand messages. "Nice to be popular. I think last time I signed up to this app I got one message from a romance scammer. All of this is seriously less than 24 hours of messages?"

"Aaron, where do I even start with this crap? How do you deal with it? And look at this ..."

She tapped the top message and a blurry photo of an erect penis popped up on the screen. "Isn't that gross? Who does that?" She kept scrolling and showed me another one and another. "I am so done with online dating and I've not even started. I just can't cope with this bullshit. I'm forever alone."

I had an idea. "Why don't I go through all of these for you, filter out the crap and forward you the good ones?"

She thought for a moment. "That would be exactly what I need right now but I can't ask you to do that. It's going to take you hours, days maybe, I don't know."

"I'm your friend and that's what friends do."

She put her arm around me and hugged me. Certain feelings welled up inside. I tried to suppress it. "So what kind of guy are you looking for?" I asked.

"I want purely your judgment Aaron. I want someone you approve of, I want someone who is just like you." She preened my suit jacket and fussed with my hair. "Chris is such a lucky man, I can see what he sees in you."

I was having straight male thoughts again.

...

Back at home I explained it all to Cindy. "So let me get this clear. You are going to search for another man to bang the woman you lust over?" I nodded. "This is peak sissy! New achievement unlocked. I am so proud of you."

"Thank you."

"Can I help?"

"Sure. So, it's Friday night. Are you feeling confident to go out? I mean, go out properly? We can do this in a bar."

"This time I'm ready, but I need to change." Under my guidance, Cindy had been taking baby steps outside all week and was quite comfortable now. She came back wearing an outfit so slutty even I would be too embarrassed to be seen outside with her. She was instinctively drawn to the hyper-sexual end of femininity. I was going to have to get round to buying that girl some new clothes. I convinced her to tone it down and got her something from my collection. She was petulantly refusing to wear anything but pink and I didn't have much to offer in that color, but she settled on a square neck midi dress with a lace-up back. She was complaining she wanted to attract attention, I assured her this would do the job. It was a very sexy dress by any regular standard but more within the normal range of what a woman might really wear. She looked quite elegant for a bimbo.

We went out to a relaxed bar. I was logged into Elouise's dating account, swiping away the dregs of humanity. Cindy had wanted to go experience the ladies' room, she'd never been in before. On her way back some guy approached her and she was chatting to him. I was glancing over over occasionally checking she was OK. After a couple of minutes they parted and she returned. "So who's your new friend?" I asked.

"He asked me if I wanted a drink. I said I couldn't tonight and then he wanted my number."

"So the dress works. See, you don't need hooker haute couture get some cock." She snarled at me. "So when are you going to meet up to suck him off?"

"I'm not."

I looked at her disappointed. "What's the first rule of sissy club?"

"Erm, you do not tell anyone about sissy club?"

"No. The first rule is you may not refuse the sexual advances of any man. It's the law."

"I didn't. I told him straight up I was a trans girl to not mess him around. I didn't think he'd understand 'sissy'. He said he was sorry but it wasn't his thing."

"Oh babe, I'm sorry."

"He said I was pretty though."

"Stating the obvious. You're incredible."

She smiled. "Now sit over here and help me with this." We sat side-by-side, scrolling through the list of 'options' for Elouise. We played a game with the dick pics, rating them on size and suckability. It didn't work well as a game for us as it turned out both of us would suck all of them.

Looking through a hot girls dating inbox was illuminating the say the least. What guys thought a woman might find attractive was just unbelievable. Some were filthy, some deluded, most couldn't spell but mainly they were just uncreative. I think there were fifty messages that just said the word "hey" with varying quantities of the letter 'E'.

"What about this one?" I asked.

"Strong candidate. Lovely personality, polite, tall, writes well, but ..."

"What?"

"He reminds me of us."

"Yeah, a total femboy fag."

"What do you think?"

"Nah, he's out. She wants a manly man. She told me she hates femme."

"Oh really?" said Cindy with great interest. "Useful information."

"How so?"

"Nothing. Yep, swipe him out of the game. Sorry dude, wasn't your fault."

After a few hours and several glasses of wine, we got the thousand hopeful contestants down to five lucky gentlemen who may have the privilege of possibly dating the delectable Elouise. I forwarded the list to her.

Cindy leaned on my shoulder after a tough night's work. "You know, in a way, you got your fantasy. You became her, in a virtual sense."

"Huh. I guess you're right." I hadn't even thought about it like that.

She looked at my hands. "How are the nails going at the office?"

"I don't know, it's lost its edge."

"You can just file that down."

"No, I mean I don't find it humiliating anymore. It feels normal, it's become part of my identity now. I'm just the guy with red nails. It's too comfortable."

"That's good. Time to escalate."

She picked up my phone and did something on the web for five minutes. "Can you pay for this?" I authorized a $30 charge. "What did I get?"

"You'll find out tomorrow."

...

I had no idea what eyebrow threading was but I do now. My eyebrows had been completely reshaped into a feminine arch. "Oh wow!" said Cindy when I got home. "That is a transformation. I never realized how much effect eyebrows had on the gender of your face. You're a girl. Are you comfortable with that?"

"Too late now."

"Get some eye make-up on. I want to see the full effect."

"I went and got changed into a dress and did my make-up routine in full."

"Absolutely stunning," said Cindy when I did the big reveal. "I badly want mine done now."

"Thanks. Book what you like. In fact, give me your phone." I added my credit card to her phone payments.

"Sucker. You just gave your sissy wife your card." She wiggled the cheap ring on her finger. "Big mistake. Yeah, I won't bankrupt you ... probably."

"You better not or you'll get your ass spanked," I said provocatively.

"Well in that case I'm definitely in a spendy mood." She thought for a moment. "What say we sissy this place up a bit?"