Floodgates Ch. 01

Why is a straight guy downloading Grindr on a Friday night? That was the question I was asking myself right now, as I hesitated on the log-in screen, questioning if I really wanted to do this. It's not like I was homophobic or anything. I had close gay and bisexual friends and people would say I was a pretty metrosexual guy, if anyone used that term anymore. But I was pretty confident I was straight. Super confident. The word confidence even implies some level of chance I might not be, so scrap that. I was straight, end of.

But after a peruse of Grindr, according to the profile names, there were plenty of straight guys on there like me, all after exactly the same thing I was after. Trans women, crossdressers and sissies. As I said, I'm a pretty liberal, metrosexual and politically correct guy, so of course I recognised that trans women are women. If anyone saw the app on phone, its plausible then that I could say I was looking for trans women to date. Except I wasn't... what attracted me more and more those days, as you could tell by my internet history, was the people who were flirting with gender boundaries and toying with norms. Androgyny, overt crossdressers who didn't try to look passing but embraced their femininity while being unashamedly male, being men, if normally always submissive men.

And the gold standard, sissies. Sissy boys who locked their dicks up in pink cages rather than hide them away and pretend they weren't there. Sissy panty boys who wore the most hyper feminine clothing possible, with the reddest lipstick and the tightest corsets and revelled in their fact that they were neither real women or real men, but a pathetic and subservient other.

I'd only ever been with women, and not very many of them. My sex life was nothing to be ashamed of, at 23 I'd had two what you might call serious relationships and a couple of one-night stands which had been fun, but the whole amount was nothing to boast about. It was true I hadn't had sex in a while when I fell down the sissy rabbit hole in my porn viewings. It's only a couple of leaps from watching purely girl on girl action, to girl with TS videos, to nearly exclusive shemale content and from there, the world of submissive sissies.

I had my favourite videos, I had sissy porn star names I knew like Jessica Fappit and Sasha de Sade and a couple of amateur ones too with no names, but I knew every feature on their androgynous bodies. But I hadn't ever been with one. I sensed, deep down, that it may be something that once I did it, it would be something I didn't turn back from. It would be a bridge crossed to a new part of my identity. I was straight, I had only fucked women and I didn't want to fuck other guys. I was just absolutely fascinated by sissies.

As submissive as they were, and the aura of weakness and shame that my favourite porn videos fetishised in the sissies, I found myself admiring them. Admiring is maybe the wrong word, but I felt there was a courage in choosing that life, to put your face on camera and tell the whole wanking world that you were a sissy who had succumbed to a life of feminisation. Once your image was on the internet owning up to that, it didn't seem like it could be reversed. And here they were, owning that, even if most of the time it meant other people were taking ownership of them. I had to meet a sissy for real and see just what it would be like.

The Grindr interface was full of men of all shapes and sizes, all looking for one thing I presumed. Handily, there was a filter of different 'Tribes' you could use to slim down who you were looking for. To my delight, there was a 'Trans' option, which once selected, completely refreshed the interface. Gone were the men I had no interest in, replaced by new profile pictures, many of them splashed with pink. There were still male profiles, other admirers like me, but now I could see a whole range of more feminine personas, from the out and out gorgeous trans women looking to date men who accepted who they were, to kinky crossdressers who just got off on being fucked while wearing their wife's stockings. I didn't know where to start.

I needed to calm down, so I decided to put my phone face down on the sofa and leave it for a second, go and get myself a beer to ease my nerves. My flatmates were all out partying somewhere so I had the place to myself. I got myself an Amstel from the fridge and took a sip. When I returned to the sofa and gingerly picked up my phone, I didn't have any messages. It looked like I'd have to make the first move. Conscious again that I was taking some real first steps here on a path I hadn't gone down before, I swigged my beer eager for its loosening effects to kick in.

Living in Manchester, there was a decent LGBT scene around so there were a lot of girls to talk to on the app, more than I'd expected. Grindr was so different to Tinder or Bumble or any of the other dating apps I'd used. There was no swiping, anyone could talk to anyone. Gay guys were just a bit more forward and to the point than women I guessed, understandably as there wasn't the one-sidedness of male on female sexual violence to worry about here. I struck up the courage to message three sissy profiles who were nearby to me, but they either went offline or didn't reply.

About half an hour in, I hadn't had a reply from anyone, a bit dispiriting. I fetched another beer and reclined all the way on the sofa. Netflix went on and I stuck on a film I half paid attention to, occasionally checking Grindr to see if anyone had replied or there was anyone else I was interested in speaking to. It was only about halfway through the film that my phone buzzed and I saw that 'Lucy' had messaged me.

"Hi sir," was all her message read.

I clicked on her profile. 25 years old. Super skinny slim build, a dainty face with mousy brown straight hair that stopped just short of her shoulders. In every pic, she had fairly natural makeup and a welcoming smile, but each one a different outfit. A navy blue polkadot dress, a white top and a red skirt, and the cliche really of a maids outfit. I couldn't type my reply fast enough.

"Hi, Lucy. I'm Carl."

"Are you looking for NSA, baby?" I had no idea what that meant.

"Um, not sure, is that a chemsex thing? Not actually into that." That got a few laughing emojis.

"No sir," Lucy replied, "it means No Strings Attached. Are you looking to fuck basically?"

My heart skipped a beat. This was just falling into my lap.

"Yeah, I'm looking for that."

"You like sissies, sir?"

"I love them."

"You fucked many sissy boys like me, Carl?"

"Yeah loads." I'm not sure why I felt the need to lie, but I wanted to impress her. I didn't want to seem like I was a virgin at this stuff.

"Do you travel?"

"Like do I go travelling?"

"No Carl, as in do you travel to meet or do you accom?" Oh. The penny dropped.

I couldn't feasibly bring her here, my flatmates weren't going to be out all night. What would they say if they saw who I was bringing back.

"I can't accommodate, but I could come to you?" Suddenly a little map icon popped up in the chat window.

"I've sent you my location, sir. How fast can you get a cab here? Your sissy is desperate for a real man's dick."

Jesus Christ, I couldn't believe what was happening. This passable, gorgeous sissy was throwing herself at me, and all I had to do was jump in a taxi and she was mine. My hands were shaking, I was so nervous even though it was clear I had everything I wanted at my fingertips. Pulling myself together, I looked at the map and to make matters even easier, it really wasn't far.

"About 10 minutes I think. Do you want me to come over?"

"Yes, daddy. Ring the doorbell three times so I know it's you. See you soon xxx." And with that the little green dot showing she was online vanished.

It was like I couldn't think straight, like this wasn't actually happening to me. First things first, order the cab. Driver on his way, 5 minutes. Enough time to sprint into my bedroom, change my top, throw on some aftershave. I admired myself in the mirror and thought I looked good. I didn't want to disappoint Lucy, although a voice in the back of my head reminded me how desperate she confessed to be and that she probably didn't care what I looked like. That was fine with me.

The taxi ride was a blur, my heart pounding the whole time, so much so that I nearly forgot to pay the driver as I got out. When he pulled away, I was left on the dark street alone, standing opposite the red door of the address Lucy had given me. I raised my shaking finger to the doorbell. Before it made contact, a wave of doubt flooded through me, making me pause. This was the turning point. Once I rang the doorbell, there was no going back. If I hadn't had that second beer, maybe I would have reconsidered but the alcohol in my system overrode my inhibitions and I pressed down. Once. Twice. And on the third time, the door swung open and there stood Lucy.

My hookup for the evening was standing in there in the most outrageously feminine outfit, illuminated in the doorway for all her neighbours to see, without a care in the world. Her brown hair was a little longer than it had been in her profile pictures, this time it had been curled, with the last of her curls just resting by her collarbone. Across her shoulders, what looked like a black satin gown, only loosely draped over her and tied at the waist, with a red lace bra on her flat chest. Below, a red panelled skirt which flared outwards, stopping just short of her knees. Her legs were wrapped in black fishnet stockings, with the whole outfit culminating in black high heels.

"Hi, Carl. Would you like to come in?" She stepped to the side to welcome me in, and I did the only natural thing and stepped inside her home.

When the door was shut behind me, I felt her arms on my shoulders, gently slipping off my coat, which she hung up on a hook by the door. She took my hand and led me through the hallway and through a door into the kitchen.

"Would you like some wine, sir?" My cock twitched at her calling me that.

"Um, I've had a couple of beers already, so mixing with wine might get me even drunker. Have you got any beer?"

Lucy let out a giggle at that.

"We don't really drink much beer in this house, sir. I'm sure getting a little tipsier won't hurt?"

"Sure, I'll take a wine then."

"Have a seat and I'll bring it over to you."

The kitchen window had a cushioned bench under it which she beckoned towards and I took my seat there and just gawped at this feminine vision as she opened the fridge for a bottle of white wine. With two glasses in her hand, she strolled over to me.

"This is a really nice place," I stammered, reaching for conversation to make it look like I knew what I was doing. "Is it yours?"

"I share it with my housemate, they're at work and will be out with work drinks all night. It's just you and me sir." She handed me my glass and I took a much needed sip.

"Thanks. I really like the aesthetic in here." Just as I had lowered it from my mouth, she took it off me and placed it on the windowsill, next to where she had just placed hers.

Lucy slid her sissy body onto my knee lap and snaked one arm around my neck, pulling her weight onto me so that she was firmly now on my lap. Her mouth was close to my neck and when she leant in to leave a soft kiss on it, I knew a faint shade of her pink lipstick would be there.

"I don't think you came here to talk about my housemate and my choice of kitchen styling, did you Carl?"

I shook my head and reached for my wine, taking a big gulp to steady myself. Within three swigs, in which time Lucy had moved from my neck to my ear, I was done. I may have felt incredibly out of my depth but at least I was feeling drunker and drunker, the combo of wine and lager always something that pushed a lightweight like me over the edge quickly.

"Let's go upstairs, Carl."

"Okay." I was speechless, and my sissy seemed like she wanted to lead the way.

Lucy slunk off my lap and onto her hands and knees, while I remained seating. Slowly, she turned her head back to face me and lifted her skirt. Where her sissy hole was, a diamond was gleaming, what I knew must have been a butt plug.

"I got myself plugged and ready for you, sir, ever since you said you were coming. I hope you like it."

"I do, Lucy. I love it."

Not only was I staring at what filled her hole, but my eyes lingered on what hung between her thighs. I had expected to see a cock but all I could glimpse was pink plastic. A chastity cage. While I stared at it, it began to move away from me as Lucy began crawling out of the room on all fours, showing me just how submissive she was.

"Follow me, sir."

We proceeded like that, her leading the way on her hands and knees, me following behind marvelling at her sissy body, all the way up the stairs until we came to her room, the walls painted pink with a black double bed standing on the far side of the room. She stopped at the foot of the bed and waited for me. I walked round her and sat down by where she was kneeling. Everything was playing out like the porn films I had watched. I knew what came next and sure enough, Lucy began pulling at the belt to my jeans.

"I need a real man's cock in me so bad, sir." I didn't know how to respond so I just nodded.

The first sign that this wasn't going to be the sissy porn experience from my dreams came when she pulled down my boxers and fished out my hard cock. I have to admit now that when hard I'm a little over four inches. Not a micropenis or anything but probably below average. And the look on Lucy's face confirmed that she thought the same.

"Is it okay?" I asked, knowing exactly what was on her mind.

"Yeah.. yeah of course, sir." Her carefully curated sissy persona had dropped for a second with that flash of disappointment on her face, but she pulled it back like a pro and without flinching swallowed me whole.

Oh my god, I let out such a moan as Lucy sucked me like the true sissy cock addict I could already tell she was. This sissy was bobbing up and down with so much energy, taking all of my admittedly small cock in one go, spit all over it and moaning herself. I laid back down on the bed and let her go to work. While I laid back, Lucy took one of my hands and placed it on her head. She wanted me to feel her hair.

Her curls were so silky and felt so smooth to my touch. I stroked it gently as she stroked me, her small hand clenched round my cock, pumping me while her tongue teased my head. From the initial onslaught, she slowed her pace to long, slow glides up and down my shaft, deepthroating me and holding it down the back of her throat for over a minute. Did this sissy slut even have a gag reflex? After about twenty minutes of her worshipping my cock, she let it slip out of her mouth and stood up.

"I don't want you to cum yet, baby."

Her hands fell down to her waist, unknotting and slipping out of her gown, then smoothly unclasping the front of her skirt, which fell crumpled to the floor. No knickers underneath, but the glimpse I had before of pink plastic was now revealed to be a cute cock cage, encasing her little clitty. She saw my eyes had been drawn to it.

"I'm not a real man like you, sir. That's why I have to lock it up like this, so I don't cum and forget who I am."

She climbed onto the bed with me laying down next to her as she crawled parallel to me, with a little wiggle of her ass showing where she wanted my attention. I raised myself onto my haunches and got behind her. Her bare bottom was just there waiting for me. Her skin was paler than average, and not a hair on her body, just a smooth white peach ready for me to take. It was all so delicate I could only lay my hands on it gently, when I did I felt a wave of adrenaline jolt through me. If my hands had been shaking from nerves before, they were full on trembling now.

"Carl, are you OK? You seem a little on edge."

"Haha, just the wine I think." She had craned her neck back to look at me.

"Do you want to stop?"

"No! No... I want to... feel you."

My hands slipped down her legs and felt the fabric of her stockings. Life-changing moments never feel like life-changing moments when they're happening, how was I to know what I had just set in motion? The feel of those fishnets to my touch was something totally intoxicating, like something was unlocked in me. So soft, so delicate, so feminine. I had gone in to squeeze hard but now I kept my touch light, not wanting to break them or stop this feeling that had come over me. It was only when I heard Lucy call my name that I realised I had stopped breathing for a second.

"You're acting a little weird, Carl. Are you sure you're okay?"

Hearing my name snapped me out of it slightly and I gave a vigorous nod, too vigorous maybe, the alcohol exaggerating everything. Still on all fours, Lucy leant over slightly to access her bedside drawer and handed me a bottle of lube.

"Come on baby, just fuck me!"

But as she went to hand me the bottle, my shaking hand failed to grasp it and it tumbled onto the bed. I winced with embarrassment. Lucy rolled over and sat up on the bed.

"OK, look, let's slow down. It's absolutely fine, we can take it slow." She scooted back so she was leaning against the headboard and patted the space beside her for me to join her.

"Sorry, I'm a little drunker than I thought I was."

"Don't worry, we can go as slow as you need."

That made me feel a lot better. I sidled up next to her. Lucy brushed a curly strand out of her eye and smiled at me. I felt completely non-judged in that moment, which hadn't been the case in most of my sexual encounters with women before.

"I'm guessing you don't do this that often, is that right Carl?" When I hesitated, she rushed to fill the silence.

"It's okay, don't worry! I'd rather you were honest, I promise."

"Then I guess maybe not as much as I let on. I've never been with a sissy before, I just really wanted to try..."

"Everyone's gotta start somewhere! What made you want to try a sissy boy like me?"

"I'm straight. I only ever date women, never men. Not that there's... I'm not homophobic, just... I don't know I've been watching a lot of sissy porn recently."

"Like sissy hypno?"

"No, not sure about that," I lied. I had watched a couple of hypno vids, but just because they had the best girls in.

Lucy nodded, a look I couldn't quite figure out passing across her face. It was knowing, but God knows of what.

"And am I everything you hoped I'd be?" She rolled onto her side, so that she was lying down showing me her whole body.

"You're incredible. I think you're so, just, so... brave for accepting what you are." She giggled at that.

"I'm a sissy, darling. Plain and simple. And I love it."

"Can I touch you again?"

When she nodded, my hand automatically went back to the only place it would - the feel of her stockings again. As I gently stroked the material, I sensed she was watching me and I looked up and met her gaze. There it was, that knowing look again.

"You really like that, don't you baby?"

"What do you mean?"

She didn't reply, but just took my wrist and placed it on the red lace bra gently. My fingers brushed against it softly, with that same tingly feeling rushing through me.

"Feels good, doesn't it? Feels so nice against my skin. Carl... would you like to feel what it's like against your skin?"

My whole body froze and I stopped stroking at once. What the hell had she just said?

"It's completely fine to say no. But I recognise that look in your eyes, Carl. I know it intimately."

Lucy looked into my eyes and we both knew exactly what she was gently trying to imply. She held my gaze, smiling warmly, for some time, neither of us saying anything. Until the first teardrop rolled down my eye. Ten seconds later, I had begun to bawl, completely unable to stop the tears coming and the floodgates were open...