tagTransgender & CrossdressersIn from the Rain Pt. 02

In from the Rain Pt. 02


Well shucks! I got some positive feedback from the first entry, and a couple people were even nice enough to comment asking for another one! Let it be said that I'm not above placating the masses. By which I mean cute crossdressing smut. A little bit shorter than the first one, but I don't really have to introduce the characters too much this time. Don't worry. In the event that I do a conclusion, it'd be an emotionally draining humdinger.


Enjoy smut.


"Casey, I'm home!" Mike closed the door behind him, setting his briefcase on the ground next to the hatrack. He loosened his tie and hung up his hat, feeling good to be home after a long day at work. He swore he could hear cheerful incidental music and applause as he came through the door. But that might have been the fatigue of an honest day's wage earned for his household.

"Hi Honey!" came a voice from the kitchen. More ethereal applause followed. "I'm just finishing up the roast now. You're just in time for dinner!"

"Wonderful!" Mike declared. Casey was a gosh darn good cook, after all, and there was nothing like a homecooked meal after a long day slaving at the factory. Or the bank. Or whatever it is he did for a living. For a moment he remembered that he worked from home, but that didn't make sense because he just arrived from work. Oh, but that roast sure did smell lovely!

He entered the kitchen to see Casey bent over a hot stove, taking the roast out of the oven. The only clothes she was wearing was a frilly white apron, showing off her shapely ass. Diamond studs touched her earlobes, and a big, old-fashioned pearl necklace dangled down around her neck. Placing the pan on the stovetop, she skipped over to him to give him a big hug. The kitchen table was already set for two, but there were four chairs available. They didn't have kids...did they?

"Did you miss me?" she asked. What was Casey to him? Mike ducked down for a firm but wholesome smooch on the lips, squeezing her body close to him. For a moment, he felt the pressure of her adorable erection against his leg. Poor Casey must have gotten lonely...

Mike let his hands slip from her lower back to her rump, squeezing her tight cheeks and making her 'Eep!' in her adorable voice. "Of course, sweetheart," he reassured her. Deep, carnal lust bore into her adorably perky body. He didn't see her as a crossdresser anymore. She was just Casey. His girl. His sweetheart. His slut.

He couldn't take it anymore. He pressed her down against the counter, where a selection of side dishes awaits getting served. He stuffed himself inside her ass, which is somehow felt no resistance or friction to the act. Like it was a proper, shameless fuckhole on his pretty little wife, begging to be taken by a real man like Mike. He bit her earlobe and got to thrusting, his superior strength keeping Casey pressed down and presenting.

"Ngh~ Screw me, sweetie. Take me as hard as you did on our wedding night~"

Mike was only too happy to oblige, pumping in and out of Casey's yearning hole until she was quaking and quivering. The room filled with 'gosh's and 'golly gee's as he hammered his little cutie. He wasn't gentle. He fucked her hard and stuffed his entirely length inside her with every deep pounding thrust. His efforts mashed at her pleasure bud inside her body, forcing her to leak excitement down her shaft.

"Ngh~ Honey, you're gonna make a mess if you keep going like that!" she teased. Mike tightened his grip around her diminutive body and kept up his remorseless pounding. She felt so warm and wet inside, like a proper girl. And like a good, well-trained wife, she'd be the one to cum first.

She squealed as her little cocklet squirted her sissy seed weakly against the cabinet below the counter. But Mike wasn't done. He slammed himself deep inside her, her butt pressed firm against his waist as he felt himself throb inside Casey's flesh.

"Tell me how much you love it, you little trollop," he breathed into her ear.

"I love your dick so much," she said in a dreamy voice. Somehow, he wasn't stuffing her ass anymore. In a blur, her makeup-laden face was pressed against his erection, perfect ruby lips encircling his shaft. "And I love tasting myself on you. Makes me feel like a dirty girl~"

"You are one," he responded. He coaxed her mouth to slide over his shaft to suck him off in earnest. She was only too pleased to comply. "A dirty little slut for me. Fuck, I love you Casey."

Mike held her head and thrust himself inside, fucking her mouth with every intention of breeding it. He yearned to plunge his pole past her tonsils and unload a thick batch of his seed down into her stomach. Only a few moments before he exploded, emptying himself into Casey's waiting throat. The wet slurping and needy whimpers spurred him forward. His head throbbed in a steady rhythm that he couldn't place, but Mike ignored it. He was so close...so close...


Mike's vision disintegrated with the throbbing pulse of his phone's alarm. Awful, irritating EDM dragged him from the fantasy and back into his bed, alone. He wasn't in a 50s family sitcom with a crossdresser wife. Unfortunately, he was just in his own bed.


And harder than adamantium.

"Damnit," he swore, pressing his fingers together at the bridge of his nose. That wasn't the first Casey-related dream he'd had, and it probably wouldn't be the last. He had to get over him. Him and her. Both sides of Casey had their appeals. But it wasn't going to happen. Casey had a boyfriend. And Mike just had to deal with that. He couldn't reason with his boner, of course. Erections were notoriously immune to common sense.

He nearly tried to roll out of bed, but his current erection would have made that a difficult prospect. Instead, he slid out on his rear and stumbled to his feet. For a moment, he could see that moment when Casey crossed over to his bathroom to shower. He fought the memory down and looked for some goddamn coffee.

Three weeks. It had been three weeks almost exactly, given that this was Saturday morning and they'd met Saturday evening. Every day after work Mike thought about calling him, but he knew that it was wrong. Wrong because he was at least 80% sure he was straight. Wrong because he wasn't the kind of person to do the whole casual sex thing. And wrong because Mike didn't want to be the one in between Casey and his boyfriend. Their fling was just a one-time slip up. Fuck, he was barely sure he wanted a relationship to begin with.

Mike sipped a stiff mug of dark blend straight, not with the creamer he usually enjoyed. He needed clarity. He needed the bitterness to chase away the remaining hints of sweetness still remaining from that Casey-related fantasy. He stared at the little post-it with the cute crossdresser's phone number, which he'd placed under a magnet on his fridge.

"Damnit..." He tore his mind away. Maybe some boring, soulcrushing paperwork would help him forget.

He blazed through reams of digital documents until Noon, laser focused on the details. He was so lost in his world of signatures and clauses that he almost didn't hear his phone ring. He'd left it on his nightstand in his bedroom, and he was in the guest bedroom turned office space. He made a quick dash over to catch the ringing, not even looking to see who was calling first.

"Mike Scott speaking," he said in his best professional tone. The following laughter on the other side made him blush a little. Oh no.

"Well, pleased to meet you Mike Scott. I'm Casey Clery. I don't suppose you can fit me in to your busy schedule~"

Daggers pricked up his back. Fuck, how was he gonna get out of this. Did he even want to?

"Casey, hi...how do you know my number?" Mike asked. His voice was calm, fairly expressionless. Keeping it relatively professional.

"I took it off Larry's phone, dummy. I'm calling to see why you haven't called me."

A billion excuses of varying plausibility ran through his mind. "I've been..." the words melted in his mouth. Why would he lie? "I can't. You've got a boyfriend."

The line was quiet for a few seconds. "What if I told you he wasn't here this weekend? What if I said I had the place to myself?"

Mike shifted in his seat. The idea of Casey alone for the whole day making the paperwork on the screen in front of him significantly less appealing. Which was saying a lot, considering it was already pretty mind-numbing. "I'm not some kinda homewrecker...person. Guy. Whatever. If you don't want to be with him, leave him."

Casey sighed. "Why are you making this so hard, Mike? Consider this a Formal Booty Call...you're still into me, right? Not having second thoughts?" A little of his precious perk drained away as he asked the question.

Mike was quick to allay his fears. "No no no, I'm super into you. I can't stop thinking about that night. I just had a dream about-" He cut himself off. Why the fuck would he mention his dream? What is wrong with him?

"Well isn't that something. Glad I left a positive enough impression!" It worked though. Casey's voice was cheerful again. Realising that made his awkward blunder worth it to Mike. It's tough to reveal stuff like that to another person, but he'd do it if it put a smile back on Casey's pretty face.


He might have had a crush.

"I...um...yeah. I'd love to see you again," Mike said, fumbling over his words like an awkward teenager.

"Good!" Casey rattled off an address, which he had to repeat because Mike took a second to find a pen. That and he'd been in slight emotional turmoil over his epiphany. "See you tonight, say, 6:00 PM? Should I be Casey?" He pronounced his name with a forced deepness, which sounded a little like a kid trying to imitate his Dad's voice. "Or should I be Casey~" she offered, pronouncing it with the feminine lilt that poked at Mike's pleasure centres like some kind of specifically designed medical probe.

"D-do whatever makes you most comfortable," he stammered. Damnit. Why was he so easy to manipulate?

"Well then, I guess you'll be in for a surprise. Dress nice, but not nice that it'd be hard to take off in a hurry. See you soon, sweetness." With that, the line went dead.

So much for getting work done today.


The next few hours crawled for Mike. All he could think of was what he was going to do that afternoon. Work was out of the question. All he could think of when he stared at an accounting spreadsheet or a white paper was Casey's silky smooth thighs and the musical sound of her laughter. He tried coding for one of his hobby projects, and he had slightly better luck with that. He made games, or at least things that would at one point in the distant future become games. Mike loved piecing together the parts to make a successful trigger, or lurking forums devoted to the exchange of ideas for like-minded people. None of his projects had made it to completion, but he kept working at it. One of these days, he'd have something he was proud of.

The hours finally passed. By the time he'd gotten really into solving a glitch in his game's inventory system, his phone's alarm went off and told him it was time to get ready. After showering and really getting himself sparkling clean, he took off for the city in his old but well-maintained sedan. He had a knot in his gut all the way to Casey's place, which was about two hours away if you took the highway. On the one hand, he really wanted to see him again. Casey's arrival that night in the rain had been unexpected, but it certainly hadn't been unwelcome. Mark hadn't had a decent fuck in too long, and the ensuing feelings that resulted had undoubtedly left him in a better state of affairs.

But on the other hand, what did this mean, exactly? In his heart of hearts, he was still straight. He wasn't about to start trolling male/male dating websites for hard dudebods or whatever. Casey was just...special. The chink in his heterosexual armour. He couldn't deny that he found him attractive, even outside of the whole crossdressing thing. Did this mean he was bisexual, or was this just an isolated incident? And if he carried on with this relationship...how long could it go on? Was this something he wanted as a serious thing? Was this just casual sex? For Casey, it very well might be. But Mike wasn't sure he could pull the whole casual thing off.

A part of his whole introvert thing was that it took him a while to open up to people. In his previous relationships with women, it had usually been them to initiate the first sexual encounter. It sort of made Mike feel like he was terrible at being a guy, being so beholden to touchy-feely bullshit rather than getting right into the meat of the issue...so to speak. But with Casey, within the first hour of meeting him, they'd fucked. The bedressed ragamuffin on his doorstep had been an anti-tank grenade tossed against his introversion armour. It was another issue he'd mulled over for days after their climactic encounter, as it clashed with his very firmly entrenched self-image as a consummate cold fish. But what if he wasn't?

What if he was just waiting for someone like Casey to come by and sweep him off his feet?

Dangerous thoughts lead down that line of questioning. He cranked his radio to disrupt his introspection, jamming out to something hard and kept his eyes peeled for the next turnoff. He only missed one the entire way, a remarkable feat considering how bad a sense of direction he had.

His sedan slid past the address in question. It looked like a duplex, with Casey's address on the right. He had to drive around the block a bit to find parking that would last the whole night. Y'know...just in case...

The street was just getting into its evening groove. A small flock of young adults, freshmen by the looks of them, crowded out the sidewalk in the direction of a restaurant. Likely one with bad carding policies. The pizza place to his left had impatient customers waiting in booths and a uniformed stringbean of a man with three of those insulating bags stacked on top of one another looking heading for his car to make some deliveries. Cars and bikes fought for supremacy on the road, occasionally forcing reflexive honking from motorists and muffled curses from the cyclists. All the things you'd expect in a city.

Mike hated the fucking city. Too noisy, too polluted, and everyone hated each other. But he'd survive this urban hell, so long as it meant he got to see Casey again. As he ascended the steps to Casey's (and Larry's, he reminded himself) home, he suddenly realized he should have brought something. Wine, flowers maybe? Isn't that what people did? Too late for that now. He straightened out his clothes, made sure his hair didn't look like shit, and knocked on the door. He pressed the ringer button for good measure.

The door pulled open, and Mike had to keep his jaw from hanging open. Casey was definitely Casey~ at the moment, considering the shockingly gorgeous dress she wore. Slit up the sides from waist to ankle, it only hinted at elements of her subtle sensuality. Brilliant, platinum blonde hair spilled down her back in a way that had to be extensions, but he couldn't see where the real hair ended and the fake began. She wore red lipstick, just like his dream, but the jewellery was different. It was gaudy, costume numbers that lacked the subtlety of simple ear studs, but practically shouted femininity from the mountaintop in a way he certainly wasn't going to complain about. She batted long, dark lashes at him, as her ruby lips curled into a grin.

"Hi there. Long time; no see. Care to join me?" she asked, holding the door open. He moved like an automaton, entering the townhouse on autopilot as he tried to get a handle on Casey's new appearance. He'd seen her drenched but still wearing an adorable fetish number the first time they met. This one was just sensual, almost womanly. The click of heels on tiled floor made him look down to see that, sure enough, she wore red pumps as well. He uttered a silent prayer of gratitude to whatever deity was looking out for him. Maybe one of the Greek ones, given the circumstances. He wasn't complaining.

"Glad you could make it on such short notice," she said over her shoulder. Mike removed his shoes and took his time looking around before joining Casey. The walls were painted in dull shades, which contrasted nicely with the esoteric nature of some of the artwork. More traditional pieces that looked like they might be prints of famous watercolours hung alongside more abstract takes on similar scenes. He noticed that some of them were the same landscapes done in two separate, opposing styles. He couldn't tell more, being a complete rube when it came to fine art. But it certainly classed up the joint.

"Uhh...yeah. I didn't have much going on today, thankfully." What a poet he was.

The kitchen and dining room formed one contiguous whole, all done in a cozy wooden panelling that reminded Mike of his parent's place. On the circular hardwood table sat two plates with their assorted cutlery and dishware. Hot steam rose from what looked like chicken and vegetable dish, which smelled heavenly even from here. Two glasses sat beside, filled with a white wine whose bottle sat between the two chairs. The lights had been changed to dim to allow the glow of two candles to shine through.

"I...Casey, this is...wow," Mike stammered. The crossdresser motioned for him to sit, and they both did.

"I thought I'd make it up to you by making you dinner."

"I'm flattered. And greatful. Thank you!"

She shrugged. "Dig in now, before it gets cold. You'll need your strength for tonight, after all~"

Mike blushed a bit at that. But his stomach knew no loyalties, and soon grumbled at the food before him. He stuffed the first few bites into his mouith before he realized there was something familiar tasting about the chicken. Then he turned to see that there was a giant crockpot sitting unplugged on the kitchen counter, with a red-spattered ladle hanging inside its confines by a milimetre. It looked all the world like a failed attempt to make a tomato sauce, something that was not present currently on his plate.

"Wait...is this takeout?" he asked gingerly.

Casey laughed. "Okay, you got me. I'm actually kind of a bad cook." Mike shared the laugh, shaking his head as he stuffed another forkful of chicken into his mouth. So a part of his fantasy wouldn't be coming true anytime soon. That was fine. Casey was so much more than a stereotypical 50s housewife.

"No problem. Next time you come over, I can cook you something good. I make a dynamite chicken paprikash."

The silence that fell afterward wasn't awkward per se. More like the two of them ddin't know where to start the whole introduction process. Neither of them knew eachother that well, despite the fact that they'd had sex...more than once, if blowjobs counted towards the final tally. How do start from there?

After clearing half his plate, Mike cleared his throat and went for a safe icebreaker. "So...what do you do for a living?"

"Oh, a little bit of everything," Casey said around a fork-worth of broccoli. "I used to work retail, but I lucked out and bought into one of those Crypto-currencies before it exploded, so I have a small nest-egg while I figure out what to do with my life. I daytrade a bit, and I make some money off of my art."

"Your art?" Mike asked.

Casey nodded over to the side wall at one of the paintings. It looked like a landscape of a lighthouse on a seaside cliff, but the details were jagged and angular in a way that Mike had legitimately never seen before. He was a layman when it came to paintings, but even he could see that there was legitimate talent going on in there. "That's one of mine. I'm kinda proud of that one, don't think I'll sell it. But some of the others have gone for a few hundred bucks. One went for $1100, but that one was special. Don't think I can replicate that kind of work, but it's nice to know your stuff is appreciated."

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bydreadknots© 5 comments/ 14080 views/ 32 favorites

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