Plans Change

I can't believe I'm finally going to have my first meet with a man!

I downloaded an app in a haze of horny expectations, I never expected to hit it off with a daddy that's just my type!

I'm so happy he's not pushy, AND he likes me dressed up in girl mode. I would've been okay with meeting him in my casual boy clothes, but this really is the dream scenario. I've had so much practice at home on my own with makeup, girly clothes and toys - the entire time fantasising about sharing it all with a big chubby daddy.

So here I am in the hallway of my flat, late into the night, just waiting on the taxi to come pick me up and take me to my first ever man meet. I've got my hair back in a hairband with a cute black bow, hanging down to my shoulders. I've got a little black dress on that hangs just above the middle of my thighs; hence the taxi! The heavily-padded push-up bra I'm wearing is giving me just the hint of a cleavage, which I accented with a series of necklaces dangling down towards my "boobs". I've got black tights on underneath - which if I'm honest may not survive to see tomorrow - with my absolute best pair of cotton panties underneath (black with pink trim, and they make my ass look nice and extra round). I really wasn't sure if I should wear heels or not, but I finally gave in and threw on some modest little heels as they really do add to the slutty feel. Plus I'm getting a taxi so I won't embarass myself falling over in the street!

If I'm perfectly honest, it took quite a while to get the make-up right. I was so nervous my shakey hands really made a winged-eye liner look difficult to apply! But in the end, once I applied the finishing touches and my black lipstick, it all came together and I feel amazing. I can't wait for my new daddy to make me his little girl.

Which reminds me, I need clothes for tomorrow morning! This make-up and outfit may look very different after a night with a big horny man! I throw some easy boy clothes in a bag with a pair of converse and re-take my position in the hallway.

I check my phone. The taxi is nearly here! My heart is pounding like crazy, I need to breathe. In through the nose, out the the mouth. Chill. It'll be fine. He's a good guy and he already said if I get too nervous or need to leave then I can at any time. I'm in control. I've waited long enough to meet my destiny as a sissy girl. I might be 10 times more excited to go next time! ...That thought alone brings my heartrate down.

Taxi's here.

I throw on my jacket that covers most of my outfit, although it can't hide the click clacking of my heels on the pavement. Luckily it's just a quick few steps from my front door to the car. Climbing in the back, I immediately settle into the back seat and check in with the driver.

"Hey! Thanks very much for being so quick!" I exclaim to the figure in the front. His area is barely illuminated by the dashboard of the car, whereas my area of the taxi feels very well lit! Perhaps I just feel a little exposed in this outfit and makeup...

"No problem. Off to 116 Easter Street, yeah?" I can hear from the front the driver is a middle-aged man perhaps? He sounds pleasant.

"Yeah, thanks."

As we pull out of my street I wait a moment to see if the driver wants to talk. It's quiet for a moment, so I pull out my phone. I check the route, and check my messages for any updates from my date. No new updates. Okay.

I take a moment to flip the phone to front-facing camera mode. I hold the phone up and check my make-up and hair. I can feel my heartrate going up again, so I take a second to breathe deep.

"Going on a date?" I hear from the front seat.

"Sorry?" I ask, having heard exactly what he asked.

"You just seem like you're going on a date, or something like that you know?"

"Ha ha, how could you tell?"

"Oh I've been doing this long enough, I can tell. You look good, just keep breathing."

I look up at the rear-view mirror and see the driver's eyes. He's looking right at me, and I realise we're both smiling at each other. He seems genuine, so I take the compliment and do, indeed, take another breath.

"I'm just nervous. It's a lot of firsts today." I reply, meekly.

"Well they're very lucky, miss."

"Aw, thanks." I'm smiling again.

We drive quietly for a while after that. I have stopped shaking. I'm just calmly checking my social media. I check my messages again. Still no updates. That's good. Just to be sure, I send a little message

["I'll be there in just a couple of minutes :) x"]

Read.

The taxi starts to pull in to the final street. Breathe. I check my phone. The driver asks if I know exactly where I want to be dropped, but I'm reading a message.

["Sorry, I won't be able to meet tonight. I think it best to just be discreet. This is just safer. G"]

My heart drops. I'm staring at my phone.

"Miss? Do you know where you want to be dropped off?" I hear, maybe for the third time?

I look up into the eyes in the mirror. I can feel my eyes filling with tears.

"Oh."

The taxi pulls over into a little side street, just a little away from my destination.

["But I'm just outside"]

["Sorry, babe"]

It was at this moment I had never cried in make-up before, and I'm now realising why I always saw women using a cloth to carefully catch their tears.

"I'm sorry Miss" the driver says, symapthetically.

"Ech, no I'm sorry I'm just trying to..." between sniffs and careful knuckle placement to catch my tears.

"Don't worry, it happens to the best of them. And I can see this person has just lost the best of them."

"Heh, thanks." I always liked to laugh through tears, it's nice to smile in a moment of embarassment. Kinda takes you out of it for a moment.

"I assume you'll need a lift somewhere else?"

"...uhhhh... I *sniff*... I dunno... emm..."

"You know what, take your time. You're my last customer today and I can check on a few things here on my phone."

"Wait no, that's okay... are you sure?"

"Yeah it's fine just collect yourself. Figure out what you wanna do. Take your time."

"Thanks so much."

It was at this point I realised; I'm angry, I'm fully dressed, and I'm still horny. I put so much time into getting ready for this! I'll find someone else! I pull out my phone and fire up the usual chat apps. I start looking through online faces and old messages. Maybe him? No too pushy. Him? No he ghosted ages ago. Him? Offline.

A few moments pass of me angrily scrolling on my phone before I hear the driver's voice back again.

"So any new ideas?"

"I... wait no... I... Bleh, sorry! There's no guys I can find! They're all busy, or offline, or don't like crossdressers or trans girls, or... Sorry heh. I'm just a bit lost."

"You should be careful with dating apps. There's some very pushy types on there and you should go to a meet with a good amount of trust and boundaries."

"...Yeah. It's just... I spent sooo long getting ready for this! It took ages! I was finally ready to take the first step. Sorry if this is all too much info heh"

"No don't worry! As someone who has been on the other end of a meet with a trans girl, I find it's extra disrespectful to not give notice ahead of time for stuff like this. All we have to do is show up!"

"Yeah! I put on all this make-up like 15 times and he just has to wipe his ass!"

"Hah! Some don't even do that!"

I laugh, and look up at the mirror again. He is looking back at me, and turns the light on in his front seat. I see his face fully now, and he seems genuinely nice.

"Listen if you just want to go straight back then that is fine, I won't charge you for the second half of the trip. It's pretty much on my route home anyway."

"That would be amazing, thank you." I make sure to smile earnestly at him, as he has been great in what would have been an otherwise stressful and overwhelming experience.

We drive back together, chatting about our experiences. He tells me about the kinds of dates and meets he's had, of all types, and I tell him about what it's like on my side of things - even though I've never actually made it to the meet part.

"So you don't like boys your age?"

"Nah, lol, maybe that'd be better? I'm just only really into older guys. Proper dad types. The dadbod-ier the better hehe"

"Aw well I've been cultivating quite the dad bod these past few decades!"

I scootch forward out of my seat in the back to lean and see his body. He's right. A big belly and thighs! Just my type...

We pull up to my house again, and we sit outside my house for what feels like an age! We chat about all sorts. It's lovely, and relaxed, and I forget all about the night I've had. This feels more like "the night I've had".

"I'm sorry I've had you sat here listening to me talk and talk."

"No it's been really lovely - thank you."

There's a pause. I hear myself ask,

"Do you want to come in?"

--------------------------------------------------------

"Do you want a drink or something?" I ask, my heels clicking on the wood kitchen floor.

"Just water would be good, thank you."

I am in my kitchen, fully dressed up, coat thrown over the back of the chair, filling up two glasses of water for me and A Man Who I Wasn't Planned To Meet Tonight. I bring the glasses over to him and hand him one. As he drinks, I take a glance up and down him. He's a little older than middle aged. Still got most of his hair, grey at the sides, and a nice big belly underneath his sweatshirt. He'd be taller than me if I wasn't wearing heels right now. I take a drink from my glass, then stop as I remember my lipstick!

"Oh- woops! Ah damn. I still forget. I'm not totally used to this whole make-up thing, you can tell." I say, wiping off the black lip marks from the glass and setting it down.

"Well I think you look amazing." he replies placing his drink down.

"Thank you, for a lot tonight, you helped."

"That's perfectly okay miss"

"Lili."

"Miss Lili. I'm Steve."

I stepped forward and kissed him, my hands placed on his chest.

"Hi, Steve." I say, smiling.

I felt his hands wrap around my hips as he gently pulls me in. We stood in my kitchen, my arms around his neck as I slid my tongue into his mouth and felt his hands hold me and slide over my back and ass. This goes on for a good while, as I just enjoy kissing him and feeling his belly press against my body. I lightly pull away and we releases each other.

"You have... uh... on your..." I say pointing at the black smears around his mouth.

"Hah, don't worry about it. I'll just clean up and get comfy if that's okay?"

"Yeah me too."

I proceeded to go clean off my lipstick, and take off my heels. I considered changing into more comfortable clothes but to be honest I was really enjoying this look, so I kept everything else the same. I fixed the bow in my hair and went back through to the living room. Steve had done the same as me, cleaned up and taken off his shoes, sitting on the couch.

"Do you want anything on the TV?" I asked. "I could even... put on some porn if you want?"

"Oh yes, that'd be good."

The laptop sat on the table in front of the couch. I bent over to open it up, very aware that I was basically presenting my ass to Steve on the couch.

"What kinda thing would you like?" I asked, opening the laptop.

"Just whatever you like is fine."

"Sure, Okay." Now my mind is racing with possibilities as I type open pornhub, casting to the big screen. Does he want gay porn? Twinks? POV blowjobs? Or should I play it safe and go for something a bit more softcore? I clicked on the search bar, and my entire slew of favourites and recent searches come careening down the screen.

""Daddy and Sissy" sounds good" he says, before I get a chance to start typing something else.

"O-okay!"

The TV plays raunchy images of sissy girls pleasuring big cocks, but Steve turns the volume down, thank god. I join him on the couch and immediately lean in to start kissing again. I can feel his tongue in my mouth, so I purse my lips and start sucking gently on it. I feel his hand reach under my dress and squeeze my ass cheek. I am so turned on by this I let out a girly moan. I pull back from his mouth and look him in the eyes as I walk my hand down to his thighs and take his bulging crotch lightly. I hold his gaze as I gently start moving my hand in circles as I very softly squeeze his package. I feel my ass being taken in both hands and massaged, a finger wandering underneath the lining of my panties.

I put my hands on his belly and sit up, reach behind me as I start to unbutton my dress. Steve takes off his sweatshirt and top, revealing his bare, hairy chest and big round bulbous stomache. I let out another moan. I pull my dress up over my head, revealing my smooth body dressed in a black & pink bra and panties set, with crotchless tights. We lean in towards each other at the same time, but I was just a little faster. I lean down and start kissing Steve's belly. I massage the full shape of it, and kiss it all over lovingly. He sits back and allows me to lose myself in worshipping his body. I feel him brush my bra as he reaches down and starts undoing his belt. He struggles with getting his jeans off with me on top of him, so I give him room as he stands up to fully undress. As he turns back to the couch, he finds me - kneeling on the floor in front of him.

My face is directly at his crotch height, and I am looking directly up at him, smiling. He smiles back at me, and takes a step towards me. I look down and see his fully erect penis right in front of my face. Reaching up I place one hand on his belly, and one hand under his balls. I look up at him longingly. He steps forward again, engulfing me with his stature, and I disappear under his stomache as his cock is delivered right to my lips. I kiss the tip of his cock and take a second to fully inspect it with my hands. It's very girthy and thick, and I'd say it'd be above average length if his chub wasn't engulfing the base of it. I hear him moaning from above me as I start to massage his fully erect dick.

I bring my hands off of his cock and place them on the front of his thighs. Leaning in my forehead bumps his belly as I start to take his cock into my mouth.

I have never actually had a real cock in my mouth before! I have fantasised for a lifetime, and practiced plenty on my dildos, but I became very aware in this moment that I had Steve inside my mouth right now. I try to remember all the little rules about blowjobs I had absorbed over the years of porn and movies and receiving from girls. No teeth, lots of tongue, keep it well-lubed, breathe through your nose. Gentle.

I start to take him further, feeling my mouth fill with his girth and have to open my lips and jaw wider to take him in. I get another confirmation moan. I pull back slightly, then back forward. I breathe, and I try and get my saliva all over his foreskin. Gentle. Repeating. I'm sucking off a big daddy! Oh my god my cock is going to bust right through my panty fabric.

I wan't doing this for too long before I felt a hand on the back of my head, running through my hair. My bow had been knocked off by his belly above me, and I feel it being removed entirely and fingers run through my hair. He doesn't push me deeper, but I can tell he's enjoying it the more I go. I release my lips from around his cock, his head resting on the back of my tongue. I take a few breaths, grip his thighs with my hands, and push all the way to his hilt. I know I can take quite a bit of dildo, lets see how this goes!

I feel a combination of two things at once. One is the sensation of my throat closing around the head of his cock reaching way past my tongue, and the other is my nose reaching his chub and lightly touching it. That flicked some sort of horny switch in my brain, as I didn't come back at all, in fact I pushed deeper as I wanted more than anything to feel more of him on me. I scooted my knees forward as I leaned in to him and felt my entire face pressing against him and disappearing into his chub. If he was moaning I couldn't hear it because I was so focused on this incredible feeling. I held there and wiggled my head a little, before gagging and pulling back off of him. I felt that reassuring hand on my head again.

"You okay?" he asked, a little out of breath himself!

I nodded my head and let out a weak "mhmm!"

My entire mouth was flooded with saliva, as I focused on not letting my gag reflex go crazy. I felt a trail of spit coming off my chin and caught it with my finger, before looking back up at Steve. Tears starting in my eyes, I smiled at him and wiped the spit across my nose.

"I like to make a mess." I said.

"Then let's make a mess." he retorted, stepping forward and bringing his cock back to my mouth.

It was for the next eternity that I sucked, kissed, licked, and was face fucked into becoming extremely familiar with the area between Steve's thighs. Every time I coughed or gagged he pulled back, never letting me feel roughed up or pushed to the limit. He knew I was fragile. But I always pushed that little bit further each time, and by the end of it - once I had reached my limit - I fell down off his cock and to the floor absolutely covered from forehead to chin in saliva and precum. Lord knows what my make-up even looks like right now but if it's anything like his crotch I'll be looking like a well-used fleshlight full of food colouring!

I pull myself onto the couch and take a minute to catch my breath.

"Do you want any water?" Steve asks, handing me his glass.

"Mhmm" I confirm, drinking with both hands.

I notice he's looking at the screen as it shows a closeup of a large cock into a smooth asshole. Steve looks back at me as I lower the glass on my lips. I smile at him, confirming, and excitedly put my glass down. I flip around to face the back of the couch, my knees on the edge, with my feet pointing outward slightly to give some space. I wiggly my ass like a bitch in heat, as he steps in between my heels and lifts pulls down my tights and panties with his hands.

In my haze I suddenly realise, and whip round to look at his cock. I notice he has a condom in his hand already, but I watch as he takes my panties down and step towards me. He takes his cock in his hand and wipes allllll of my drool and spit up between my cheeks. He is lubing up my asshole with my own spit on his cock! My cock is drooling precum right now.

I feel electricity run up my entire body as his cock brushes against my little virgin anus. I can feel myself being well covered, and I feel a final glob of spit drop from his mouth onto my ass as he takes a moment to apply the condom on his now-dry penis. I reach back and start lubing up the rim of my anus with the concoction, poking in there slightly just to get myself started a little. I had that thing in my mouth, I know it ain't going in like this.

Steve applies the condom, and takes over with his finger. He widens my ass more and more as I start moaning like crazy - completely lost in the moment as he plays with my little girl pussy. I feel his fingers leave me, then a second later his legs brush past mine and I feel an entire cock push up against my tight pussy. With a lot of patience, and slow invasion, I start to take him inside me. With each passing minute he gets deeper and deeper, until we're both confident in our progress. I feel him start to change rhythm.

He pulls out, and slides back in, and out, and in. We're both definitely in it now. He's fucking me. Oh my god I'm being fucked by a big daddy! Oh my god. Oh my god. Oh my goddddd

Steve has now grabbed on to my hips and is pulling and thrusting with horny fervour. I can feel his balls start to swing and brush up against mine! He's so fucking deep I feel like I'm going to burst open. And just then, he switches his footing and I feel all the weight of his stomache land on the small of my back! He is well and truly docked in to me, and I have leaked all over the couch. My panties are around my thighs and are covered in precum stains and drool slops. Steve is engulfing my pussy and I am loving it.