Floodgates Ch. 01

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Our wine glasses had been topped up, set upon the coffee table. I had put my clothes back on, and Lucy had just wrapped herself back in her satin gown she had greeted me with earlier. We'd moved to the living room, in an attempt to calm me down. After my outburst, it was clear we were probably not fucking but Lucy being the kind person she was wasn't kicking me out onto the street in a mess of tears, so here we were just chilling and talking. Not the Friday night I thought I was going to have when I accepted a hookup request with a sissy stranger on Grindr.

"I'm sorry to ruin your night, I know this isn't exactly what either of us probably needed tonight."

"Don't worry about it. I don't like seeing anyone upset like that, of course I'm happy to help."

"I can't explain what that..."

"Carl. Stop. I think I can explain what this means for you, but even if you want to disagree with everything I say, please don't not share anything with me out of embarrassment." She stood up and parted her gown, dangling one hand down to cup her chastity cage. "I mean look at me. Nothing you say could be more embarrassing than this. I'm not going to judge you in any way, so don't not let me help you because that's what you're worried about."

Having shown such vulnerability before, I was still desperately trying to keep my guard up and intact, but there was a logic in what she was saying. And besides, I'd already come this far.

"OK, I get that. Well, thank you Lucy."

"So hear me out. Carl, have you ever worn women's clothes before?"

"No, I haven't," which was the truthful response.

"Have you ever thought about it?" As I was shaking my head, she gathered her thoughts and rephrased the question. "OK then thinking about it now, how does it make you feel? Does it feel like something you'd like to do?

I didn't know what to say. We sat there in silence for around ten seconds. Lucy rolled her eyes, clicked her fingers and pointed to her cock cage again.

"Carl, come on, think who you're talking to. Whatever you're feeling right now, I get it! That look on your face before and the way you reacted, I know it because it was me when I was a kid figuring out who I was. This is buried really deep in you, I get that, and it can be painful but I promise you it will feel so much better if you let it out".

"It excites me, OK?! I think it would turn me on to wear that stuff." Lucy's face lit up.

"Well done Carl! I'm proud of you, that's the hardest bit done. I think there's a possibility that maybe you're like me. A sissy."

"But I don't want to be a sissy, or like you. I just wanted to come over and fuck you, not dress up like you."

"How do you know if you've never tried it?"

"I would maybe like to see how it feels to be in the clothes, I'll admit that. But the rest of it, I dunno. All the submissive stuff."

"It turns you on to watch that, doesn't it?" I nodded. "What if I told you it felt ten times better being that? Being the sub on your knees."

"I'm sure it is. But not for me."

"Carl, I'm not going to make you do anything you don't want to do. You can leave now and never speak to me again and I won't try and message you or anything like that. I'll completely respect your decision not to pursue this. Maybe I'm wrong, and normally no one knows you better than you know yourself. But a lot of us have denial over big shit like this, and it takes a lot to uncover that denial and realise something about yourself. And I think what happened earlier could be the first start of something for you. Maybe something really beautiful?"

Her words were washing over me, half of me wanting to embrace what she was saying, but the other half still in complete defence mode. I think I knew everything she was saying was true, and she was clearly coming from a good place, a place of empathy and understanding. Maybe that's what scared me the most, the amount of similarities I was starting to sense between us. Was that going to mean I ended up locking my dick away in a pink plastic contraption if I listened to Lucy?

"How about this, Carl? One night, one night of completely letting go. Trying it out. With me, there to guide you. And then if you don't like it, you can walk away. Walk away safe in the knowledge you tried it and it wasn't for you, and no one has to know of the one night you experimented with a crossdresser. There's no harm in that right?"

"There's no harm in that, no." I deliberated before finally giving in on one condition. "I... do wanna try. But can we just take it slow?"

Lucy beamed at me and nodded, jumping up and clapping her hands together. She ran over to me, grabbed me by the arm and pulled me back up to her bedroom. Back to the pink walls and make up tables and full length mirrors and girly things strewn over the floor.

"OK, Carl. First thing you're gonna have to do is take those clothes off. Strip! Completely out of boy mode."

Tentatively, I pulled my white tee over my head and slid out of my jeans, leaving me standing there in just my boxer shorts. Lucy looked up and down my naked form approvingly. She gave a little cough.

"Those too. Otherwise, you won't be able to slip into something prettier!"

She had already seen my package, I know, but this felt different somehow. When I'd entered the house and she'd gone straight to sucking my dick, I'd felt like such a man. Now I was stripping down, stripping away my masculinity for this beautiful sissy to feminise me for the night. I slipped my fingers into my waistband and pulled them down.

"Please don't mind me saying, as much as I enjoyed sucking you, you have to admit that it's maybe better suited to being a sissy cock."

"Is it really that small?"

"I've seen bigger..."

"Did it disappoint you when you saw it?"

"A little, but you know what, playing dress up with a sissy sister is way more fun!"

I blushed but it just did feel good hearing her talk about me like that. What the fuck was going on in my brain? I had no idea but there was no point denying anymore that I liked it. I fucking loved it. My cock, the focus of humiliation in the room, was growing harder the more she spoke of feminising me.

Lucy swivelled and threw open her large wardrobe, crammed with so many wonderful garments. Dresses, sparkly tops, skirts, all hanging up. Would I really be allowed to touch any of this stuff? A man like me able to try this on? It seemed too good to be true. She knelt down and pulled open a drawer at the foot of the wardrobe. To my delight, it was filled with the most sumptuous lingerie.

"This is a very important stage in your sissy journey, Carl. Which ones would you like to try on?"

I knelt down beside her to peer in. I could see knickers and panties of nearly every colour, cotton, lace, a couple of satin, but it seemed like Lucy was a lace girl primarily. My hands lingered on a purple pair. They felt so nice in my palm. These were the ones.

"Nice choice. I think I have a matching bra for them, hold on."

While Lucy rummaged, I stood up and walked over to the other side of the room to where a mirror stood. A naked man stood there before me, holding a pair of purple knickers in his hand, still undeniably a man. This could have been my reflection, just after I'd fucked Lucy relentlessly and deposited my load in her. I might have rolled off her and walked over to the bathroom to grab some tissue, just catching my reflection in the mirror as I did, admiring myself, feeling flushed with adrenaline and manliness.

But that wasn't what had happened, I had broke down crying because the suggestion that I might enjoy crossdressing had triggered a mental breakdown in me nearly. And the purple lace panties clasped in my fist were the result of that. Ever so slowly, I unfolded the underwear, holding it in both hands. Even the shape of it turned me on, so different to male trunks, made for different bodies, bodies not like mine. I wasn't meant to be wearing these. That didn't stop me stepping into them, as if in slow motion, closing my eyes as I did so. Limiting my sight just to relish the feeling of the illicit material as it glided up my legs. When the lace felt snugly nestled around my balls, I opened my eyes to see the sight of me.

A sissy stood before. With one little slip of material, my whole appearance was different. Surprising as it was, it felt completely natural. While I was completely lost staring at myself, I didn't notice Lucy standing behind me until she began to gently rub my shoulders.

"You look great, Carl. Try this on next." She handed me a bra made of the same material. "Know how to do it?"

I did, having watched my ex-girlfriends in the past. I took the cups and lined them up where my boobs would have been, then moved it round my torso, so the clasps were on my chest. I did them up then pulled it back round so that it sat snugly on my chest, if a little tight.

"You look amazing! Lucky we're roughly similar sizes. How do you feel?"

"Honestly? I feel wonderful."

"Carl, baby, I'm so proud of you. Honestly, if you like this, you really might love being a sissy."

I just couldn't stop blushing, and yes it was partly embarrassment, but for sure a good deal of it was pride. Pride at how good of a sissy I was, how I was pulling this matching lingerie off. Pride at what I could become. Lucy nuzzled into my neck and gave me a soft peck.

"Carl... how would you like it if I called you Carla tonight?"

I didn't have to say to say anything. The stirring in my panties gave my feelings away. I nodded anyway, ready to fully commit now, my misgivings slipping away by the second.

"Good girl, Carla. We are going to have so much fun. Welcome to the sissyhood!"

To be continued...