Sissy Friends Forever Ch. 02

I got off Eric and stood up, taking the phone from Cindy. "Your turn." I winked at her. She took up position next to him, kissed him on the cheek and put her hand on his crotch and I took a photo of them together. I got Eric's number and sent him the images.

"A little something to remember us by."

"Put us on your social media. Say you fucked us both," offered Cindy. "Don't be shy. We'll totally confirm it."

Eric laughed. "I don't know about that. Thanks, you've both been so nice to me."

"I'm sorry for messing you around. I will get back to you with your dream girl," I promised him.

We left the house and got in the car. "I'm so proud of you for getting picked up," said Cindy as we drove home. "That's major progress."

"Oh wow that was good," I beamed. Being hit on for the first time in my life had really given me such a boost. "I feel so girly."

"You have become a woman tonight." Cindy put her hand on my leg and stroked me. "Bet you anything little Eric is a virgin," she speculated.

"Totally a virgin," I agreed. "Well actually, does a blowjob count?"

"Yeah kinda I guess," Cindy considered. "Oh. You've stolen a poor boy's innocence."

"I have defiled a delicate flower," I laughed.

"He's so cute. He's like a little puppy dog. Can we keep him Aaron? Can we? Can we please?" she joked.

"No, we'll have to find someone to adopt him. We'll send him to a good home."

"Awww, I wanted a pet Eric," she pouted. "So, how are you going to find him a date?"

"I got my sources."

Cindy had an idea who I meant and glanced at me with a look of exasperation. "Oh Aaron, do you have to get her involved?" I was planning to contact my friend Elouise, a co-worker that I regularly hung out with who had a large social network and I was sure could help out. Cindy had met her many times and was always very polite and sociable around her but deep down in her heart, I knew she despised her. The source of the friction was Cindy was well aware I found Elouise very attractive. I was addicted to emasculating myself in front her and the fact she was a hot girl just enhanced the whole experience, but she'd once made a pass at me and was the one person in the world that Cindy felt threatened by. In truth, being friends with Elouise probably wasn't the greatest idea when it came to maintaining a healthy relationship with Cindy.

"I'm sorry, I thought it was all OK now. If you don't like her, I'll stop seeing her. You come first."

Cindy reflected for a moment. "No, I regret saying that. I'm in the wrong. You go meet Elouise. I'm never going to be that girl, I'm not going to try and stop you seeing your friends and I'm not going to tell you who you can play with." She lifted up her free hand and formed her fingers into a cat's paw shape with her long, razor-sharp, pink nails on display. "But you understand if she ever tries to steal you from me again I'll claw her face and slap that bitch into the next dimension."

"Cool it psycho," I said, laughing. I grasped her hand and kissed it. "I put a ring on you. I love you and you alone and nothing will ever change that." I tapped the side of her head. "One day I'll get that through your bimbo skull."

"I just love you so much, I don't want to ever lose you," Cindy started to tear up a little but then composed herself. "But anyway, that's not happening because you're deep in the friend-zone with Elouise."

"I've fallen through the bottom of the friend-zone, I'm in the girlfriend-zone now. There ain't no zone below that."

"Oh yeah? Let's see if we can get you into the sissy-zone," Cindy countered. "That's the supermassive black hole of zones. Nothing can escape."

"I don't know that zone even exists in her mind. Not sure what I have to do to get there."

"I'm sure we'll think of something," Cindy smiled slyly. I didn't answer as I was lost in my own thoughts for a few moments. "What are you thinking about?"

"Oh, I was just reminiscing about all the times I got friend-zoned when I was trying to date girls. Do you still remember the first girl you dated?"

"It's seared in my mind. Gabriel, she's French. I lost my virginity to her in college."

"What would she think if she could see you now?" I gestured at Cindy's chest.

"She would be ... surprised." We both started laughing. Cindy thought of an idea but didn't realize I couldn't read her mind. "Oh ... I'd love to do that."

"Do what?"

"I want to go and show my ex-girlfriend what a massive sissy I've become." Cindy bit her lip. "Oh wow! That is such an unbelievably hot thought. I mean I was desperately trying to be a real man back then and look at me now."

The thought of it turned me on too, we were always on the same wavelength. "It's like burning some bridges as well. Word would get around like wildfire. Everyone in your former social circle would find out you're now a cocksucker. You could never go back." I turned to her. "You should do that."

"I would if I could but she's back in Europe now."

"You could send her a photo or something?"

"Maybe, but wouldn't it be so much better if you could see her reaction in person? I'm just imagining it now."

"So, how about having our honeymoon in France?"

Cindy lit up. "Oh Aaron!" she beamed. "Really? Could we?"

"We'll go look up your ex-girlfriend and I'll make sure you're so thoroughly humiliated in front of her that you'll soak your panties. Then we'll go shopping in the most exclusive places and pretend we're influencers. I'll rent an old château with some rustic charm. We'll both wear French maid's outfits all day and take photos of each other as if we were serving there. Then we'll drink Bordeaux in front of an open fire while I spank your ass until it's raw."

Cindy's mouth fell open and her eyes glazed over. The car started veering to the right. "Cindy!" I shouted. She sharply corrected the steering. "Mind on the driving!"

"How can I drive straight when you're filling my head with such fantasies."

"What fantasy? This is your future reality."

She started swerving in the other direction. "Cindy! Stop the car."

"I'm fine. I'm fine. I'm good now." She was breathing heavily and glanced at me. "But you better come through with that sissy! Promise me now."

"It's set in stone. We are going to France. Anything for my girl."

"Oh... my." Her face was pure delight. I saw her visibility shiver before she recovered. "But what about you? Have you got any former girlfriends around here?"

"Yeah. The first girl I dated is still in town I think."

"Set something up. I dare you."

I scrolled through my phone. "Huh. I've still got her number in here."

"Do it." Cindy thought about it in more depth. "Actually, I guess she's probably just going to ghost you. This might not work out how we think."

"Yeah, you're right. Is she really going to reply to an ex-boyfriend from years ago?" I tapped out a quick message asking her if she wanted to meet up and talk about old times without much expectation. Two minutes later though my phone beeped. "Huh. That was fast." I read the first part of the reply.

"What does it say?"

"She said yes."

"Really?"

I read the remainder of the message. "We are totally on the wrong track. Ex-girlfriends do want to reply to ex-boyfriends. She's recently got married, that's why."

"Oh I get it. She's desperate to show off her new husband, lord him over you, show how she's moved on and is blissfully happy now with the perfect life and blah blah."

"Exactly."

"That only makes sense. I mean your girlfriend has got herself a real man now. Must be a big upgrade from a little panty-wearing beta. A big strong alpha male who can finally satisfy her in ways that you just never could." Cindy knew how to push my buttons because hers were the same. The thought of the humiliation made me immediately start tapping on my phone. "I've asked if she wants to go to a restaurant on Saturday." I picked up Cindy's hand. "I've got my own beautiful fiancée I'm desperate to show off."

Cindy smiled. "Thank you, babe, but I've just been thinking. You're a sissy. What if we try going in a different direction?"

...

"Cindy! Have you seen my socks?" I'd pulled open the drawer where I kept my male underwear for work but they weren't there.

"Bottom of the garbage chute."

"What?"

"I threw them out. You've got three choices: bare-foot, pantyhose or stockings. Pick one."

"It's because I'm meeting Elouise later, isn't it? You're thinking she would notice if I wore pantyhose."

"Yep. She will, straight away."

"How would she ever see my ankles under my suit."

"Bet you she'll notice."

"I'll take that bet." I put on some black sheer pantyhose with my suit pants over them. "You're so wrong, they're just going to look exactly like socks unless you check closely."

"Uh huh," said Cindy. "You keep believing that. We'll see. Got your bra on?"

"Yeah, it's under my blouse."

"Good girl. We need to get you a thinner blouse. It's not obvious enough."

"See what you can find me please." I kissed her. "Got to go. See you later."

I had agreed to meet up with Elouise after work to go shopping with her, just two girlfriends spending some quality time together. I took the opportunity to ask if she could help Eric.

"I got it," said Elouise. A light bulb had just illuminated in her mind and her eyes lit up. "There's a new woman in HR. She's twenty, single, and into cosplay. She likes all that Japanese cartoon stuff. Is it manga or something they call it?"

"Oh, she sounds just perfect. Eric will love her. Thank you so much. I'll send you his number. Can you put them in touch?"

"Sure thing. I'll big him up to her and nag her incessantly until she calls him."

"I knew I could count on you."

"Elouise's matchmaking services aim to please. So how's Chris doing?"

"Cindy."

"Sorry. I keep doing that." Elouise slapped herself on the wrist. "I'll get used to it eventually."

"Don't worry about it. I know it's a big change."

"Is her, erm, gender affirming surgery all good now?"

"Couldn't have gone better. No problems. She's completely healed."

"She did not go for subtle did she," laughed Elouise.

I smiled. "Nope. She's not a subtle girl."

"Did you know she was going to go trans on you before you two got engaged?"

"I'd love her no matter what she did."

"You're such a good man Aaron." I smiled. We'd just called by a make-up counter and I'd picked up an expensive lipstick. I told Elouise it was a gift for Cindy but she didn't believe me. "So, going to try on your new lipstick for me?" she teased.

I loved being emasculated in front of her, but part of doing that involved denial. "I told you, it's for Cindy."

"Uh huh, for Cindy" she repeated, making air quotes with her fingers. "You know, if you wanted to try on a sample at the counter, they wouldn't mind." I'd so like her to see me wearing it but I couldn't do it. My mind wandered into the idea of getting a full makeover in front of her. In my fantasy, a store assistant was applying make-up that Elouise had picked out for me. My crush would giggle at me and take photos for her social media. I'd been out wearing make-up many dozens of times now, but somehow the idea of it was so much hotter in front of her because I found her so attractive. It was even more erotic because it pushed me further away from being her male ideal, it would make her see me as even less of a man than I already was. I started to feel an erection coming on. I breathed deeply until I relaxed and then changed the subject.

"You'd look good in that." I pointed at a rack of clothing.

"Oh, I like," she picked up the sculpted, scoop-neck dress in white I had indicated and put it in front of herself to show me. I knew her fashion tastes intimately and was fairly sure she'd go for it. "This is the one."

"Beautiful."

"I want to try this on." She went through the hangers and found her exact size but then looked confused. She held it up for me. "That's got to be a mistake. Looks kind of big."

I double-checked the label for her. "It says it's your size. I don't know."

"Whatever, I'll try it."

We went into the changing rooms. She picked a free cubicle and closed the curtain. I waited outside and she emerged a couple of minutes later laughing. I immediately saw the problem. The dress was about three sizes too big for her thin frame.

"It's like a tent on you."

Elouise handed me her phone. "Take a photo. My friend Sienna is going to find this so funny." I took the picture. "This brand is taking vanity sizing to the extreme. There is no way in hell this is a size six."

"You wait here, I'll go change it for you," I offered.

"No." She looked at me piercingly and started cracking a wide smile. "Bet I know who it would fit." I started feeling a mixture of excitement and fear coming over me.

"Oh no," I said, shaking my finger at her. "No way."

"Come on, don't lie to me. You've tried on women's clothes before. I know you have. I've seen your shoe collection." She was oblivious to just how right she was. My work suit was the only item of male clothing I still owned.

"No way."

"Just do it. Quick while there's no one around."

"I can't."

She slipped back inside the changing room and shortly afterward emerged with the dress on a hanger. She smiled and gently pressed me into the cubicle, thrusting the dress at me. "Go on. Do it. Now!"

I closed the curtain between us and took off my suit, slipping into the dress. What was for her three sizes too big was for me one size too small. It was a tight fit but I squeezed into it. It was a form fitting dress but I'd been on hormones for months and was just starting the get the merest hint of curves in the right places. I looked in the mirror and admired myself. Maybe I actually looked good.

I stood there for a moment with trepidation. How was it going to change our relationship when Elouise saw me in a dress? Would she see I was just the tiniest bit shapely? I wanted her to see me this way but it was still hard to make the commitment. My heart rate increased. This was it, there was no backing out now. I turned towards the curtain and slowly slid it open but was startled to be met with a camera flash.

"Surprise!" said Elouise laughing. She had been waiting for me, holding up her phone and had taken a photo as soon as I revealed myself. "Very pretty. You're gorgeous," she said trying to embarrass me.

"Thanks," I said sarcastically. I posed for her and tried to own the situation.

Elouise suddenly went from smiling to looking puzzled. She scanned me with her eyes from top to bottom and brought her finger to her lip. "Just one question Aaron."

"What's that?" I was sure she had noticed my slight curves and I had an explanation pre-prepared.

"Where did you get the pantyhose and bra from?"

I looked down and my face dropped. Shit. The top of my bra and my bra straps had been revealed by the scoop neck of the dress. My pantyhose were no longer hidden by my suit pants. It had never occurred to me to take off my underwear. I had seen it so clearly when I was changing but the danger hadn't registered in my thoughts. I'd been completely oblivious and my sissy brain had just blanked it all out. My mind hadn't alerted me to anything unusual because there wasn't anything wrong. The underwear was naturally associated with a dress, it was exactly what I should be wearing.

I racked my brain. I panicked. I couldn't think of any plausible explanation. I was out of ideas for how to slide out of this situation. I was on the humiliation rollercoaster and reaching the peak. I looked at Elouise, she waited expectantly. I needed words to fill the void, any words. "Magic?" I suggested meekly out of pure desperation.

She doubled over with laughter. "You were wearing those the whole time under your suit weren't you?"

I went bright red as a tidal wave of humiliation washed over me. My knees started to buckle. To me it was a strange double feeling composed of two different emotions inseparably intermixed. On one hand I wanted the ground to open up and swallow me. On the other hand, the feelings held a certain pleasure. I was caught. There was nothing else to do but confess my guilt. "You got me."

When she recovered from laughing, she looked at me with suspicion. "Aaron, now tell me honestly, do you enjoy wearing women's underwear?"

I thought about saying I just did it occasionally and downplaying my degree of interest. Perhaps I would try and claim that this was my first time. Maybe I'd claim Cindy wanted me to do it and try and transfer the responsibility. In the end, I decided to just brazenly roll with it and tell the truth. "I love it."

"You actually like wearing a bra? By choice?"

"Yeah," I looked away from her with shame at the admission.

"I don't. I wish didn't have to." She thought for a moment. "But why? I don't really understand it. What do you possibly get out of it?"

"I just want to feel more feminine and it helps me. To you it's just clothes, but to me it's like a symbol, reminding me about a part of my identity that I have to keep hidden." That turned out to be the right thing to say.

"Oh Aaron. To be honest, with your recent gender expression, it's not a huge shock." She looked at me tenderly. "I feel a little guilty now for laughing. Don't worry, your secret is safe with me. I won't tell anyone." She was lying, she would tell anyone and everyone. I also sincerely hoped she would. She started tapping on her phone. She hadn't even lasted ten seconds before her desire to gossip had overtaken her. "Does Cindy know about all this?"

"We tell each other everything. She's really supportive and she encourages me." This was the truth, I couldn't have wished for a more understanding partner.

"That's so great you have someone who understands this side of you." She finished what she was typing and showed me the screen. "Can I send this message?" Elouise asked with a grin. "It's just meant as a little fun."

I looked at the phone and laughed. "Go for it, she'll find that hilarious." She'd composed a message to Cindy with the photo of me in the dress together with the photo of her wearing the same one. The caption was 'Who wore it better?' Within seconds I got a reply sent to my own phone that made me smile. It read 'Sissy-zoned' followed by several heart emojis. "Cindy says we both look hot," I lied,

"Bless her. Tell her she's sweet and we must meet up soon." She thought for a moment. "You know, if you want to go shopping for clothes anytime, I mean clothes for you, I wouldn't mind. It'd be fun."

Her offer made me melt. I wanted nothing more. Up until now our clothes shopping trips had been somewhat asymmetric, but now we could be true shopping girlfriends, trying on dresses for each other. "I'd really, really love that. You're such an understanding friend."

Elouise noticed two women coming into the changing room and slipped into the cubicle with me closing the curtain. She picked up my shopping bag and took out the lipstick I had bought. "This is really for you isn't it?" I nodded shyly. "I knew it. Might as well complete your look."

...

Cindy was on all fours on the bed, her head resting on a pillow with her backside high in the air. I was kneeling behind her, gently sliding into her, but not with my cock. She'd given me a dildo she was considering stocking in her shop and she wanted to test it. I'd attached it to a strap-on belt and was pegging her. She'd started out panting in time to my thrusts but in the last couple of minutes had gone silent.

"How are we doing down there?" I asked.

"That one's not bad, but it's just not hitting the spot."

"Rating?"

"Hmmm.... three out of five stars." I slid out of her and cleaned up. "That last one we tried was awesome though. You could fuck me with that all day long. That's the one I'm going to recommend."