tagTransgender & CrossdressersIn from the Rain Pt. 03

In from the Rain Pt. 03

bydreadknots©

Author's Note: As far as I know, this is the end of the Mike/Casey saga. It's also the longest part, but there's some sex in it! Don't worry, I wouldn't want to leave you all hard and unsatisfied~

There's some Very Unsexy meanness in the middle of this story, during the bar scene. Might want to skip that if you're made uncomfortable by that kinda stuff. Otherwise, the rest is sweet and ultra-squishy. I hope it can make you feel good. Or maybe just make you cum. Either/or.

Thanks for reading, rating, and leaving sweet comments.


***

"You look fine!" the high-pitched voice from the bathroom said over the sound of a hairdryer.

Mike adjusted his new white shirt for what might have been the seventeenth time. It wasn't exactly his beloved t-shirt and jeans. Slimfit black chinos, tasteful black shoes, and a black jacket rounded out the ensemble. In the stylish clothes he now wore, he felt totally out his element. He'd also shaved, and Casey had used something called 'product' to style his hair in some fashion that he couldn't quite understand. He gawked at himself in the bedroom mirror like a tourist seeing an ape doing something human-like.

"I look like a dork," he grumbled.

"No you don't, goofus."

"A goofus is someone who is a dork. I think."

The tap in the bathroom turned on, then off, then on again. He heard her mutter something about 'dollar store eyeliner' in a much less chipper tone. That made him smile, despite himself.

Things were going well between Mike and Casey. Although Casey said she was still in an 'it's complicated' with her old BF Larry, they were seeing less of each other. Apparently he'd gotten a promotion, which meant more money, but it also meant he was away a lot more. Mike didn't exactly enjoy the idea of being the one breaking up a relationship like this, but he was too smitten to do anything but whine about it on occasion. In truth, the days he was spending with Casey were some of the best times he had had in...ever?

Casey was special. It wasn't just the attractiveness, though being a passable crossdresser certainly didn't hurt things. Casey, at least the pretend version, had a deeply charming innocence to her. Not necessarily childlike, more like a sense that it hadn't been scarred by the scalding heat of reality quite yet. Maybe that was partly the make-believe they played when she was 'she' and not just a cute 19 year old guy with a great butt.

There was definitely a layer of escapism for them both. Casey hadn't told him much about her past, but he could glean enough to say that it hadn't been an amicable split from her parents, and that the relationship with Larry had been one of the things that had kept her going. Now that it was faltering, something Mike blamed himself for but didn't do anything to stop, she was leaning into the role a little more. He'd told her that any time she'd wanted to just chill and be guys for a bit, he'd be down for it. But she'd just boop his nose, call him a goofball, and get back to being the girl version of Casey that crawled into Mike's libido and set up camp there.

She emerged from the bathroom. She had dyed her hair a raven black colour from its previous blonde look. Apparently that was closer to her natural hair colour, though she preferred to show as little of that as possible. Her makeup was perfect, though Mike was a layman and really could only help out when she'd smeared her lipstick really bad. She had a whole smokey eye look that certainly agreed with her complexion and the hair dye...sort of a Mall Goth meets Noir Femme Fatale. Definitely hot, though considering she didn't wear anything else, the dark and mysterious act would be a little difficult to pull off.

"No starin'!" she admonished, then wiggled her butt the whole way over to the clothes on her bed. There was a part of him that just wanted to take her. Just...press her down and fill her until she squealed. That was a far cry from their first encounter, when he'd been all fumbles and stutters. He'd stopped worrying about what to label his orientation. As far as he was concerned, he was Caseysexual, and that would be good enough for now.

He did, however, follow her over and grip her shoulders with his hands lightly. He was almost a foot taller than Casey, something he took advantage of in almost all of their 'encounters'. Moving in to press a kiss to her cheek, he remembered she'd just gotten all made up and smartly angled his smooch downward to her naked shoulder. She gripped his left hand with her right.

"If you're going out like this," he said with a grin, "It might cause a scene."

She rolled her eyes. "Always with the jokes. No, look, I got perfectly normal clothes right here."

Fishnets. Pleated black denim skirt. A bellytop with the name of some dumb K-pop band Casey adored on it. Fingerless gloves. And a spiked collar. It was almost exactly the opposite of perfectly normal clothes.

"You're not just wearing this for my benefit, are you?"

She nudged him backwards with her butt, then slid a pair of neon green panties up around her waist. "Trust me. This is my standard uniform when I go out to a club."

She dressed in front of him, Mike's hands manoeuvring to get out of the way temporarily, only to find themselves back onto Casey at the end.

"How are you feeling?"

"I was feeling pretty good until you put on clothes," he deadpanned.

She spun around to playfully slap him in the ribs. "About going out with me. You know. In public."

When Casey had first proposed the idea, the lizard brain part of Mike wanted to make every excuse in the book to get out of it. Not only was he a person who shunned public displays of affection...the occasional clandestine blowjob notwithstanding...but he'd never really thought about what being seen with another guy would mean, even if Casey was a quality pass in terms of crossdressing. What if someone he went to school with saw him? What if a member of his family did?

But the more he thought about it, the less he cared. So what if some rando from his past saw him with Casey? The fuck did they matter if they didn't approve? He'd found a cute person who made his heart throb like some sappy romance novel. Plus anyone who ragged on him for liking another dude wasn't worth listening to anyways. And his family? Well...it wasn't like he brought around a massive procession of girlfriends in the first place. He wasn't super close with his folks, but he still did The Holidays up at his parent's place. The thought of Casey in her cute pajamas opening up something heartfelt on Christmas Morning...fuck yeah he could do that.

"You know I'm not exactly a social butterfly." She nodded for him to continue. "But I think I'll be okay. With you and I, I mean. Together. In public."

She turned around, her arms folded and her lips a flatline. "You don't sound entirely convincing there, sweets."

He forced a laugh. "Sorry. Again, it's not being seen with you. It's just going out in general. Not really my scene."

"Well, we can make it your scene! Or at least give it a try. Can't spend your whole life cooped up in your house in the middle of nowhere!" She saw him open his mouth to interject, but she cut him off to add: "Or cooped up here, at my place. No cooping, either way. You're gonna socialize and meet some nice people, and that's all there is to it!"

"You're cute when you're bossy. You know that, right?" He rubbed her shoulders, sliding his hands down to her bare, hairless arms.

Casey, for her part, felt that twinge in her heart when Mike showed hints of his strength. He wasn't a musclehead like Larry, but the way his hands gripped her...

"Uhh...Casey?" Mike asked, popping her out of her reverie. She looked up to see him giving her groin a meaningful look. Her eyes slid down to see a small tent poking out of her pretty skirt.

"Oh...whoops!" she said, blushing furiously. "How did that happen?"

Mike let her shoulders go. "Were you thinking about the football team dream again?"

"No! Not this time...umm...sorry, hang on, I can make this go away." Casey closed her eyes and scrunched up her nose, trying to think of the least sexy things possible.

Calculus.

Cleaning a kitchen sink.

Smash Mouth lyrics.

Despite her efforts, the boner remained. Her bashful smile when her eyes opened only half reigned. On a super-macho and masculine guy, her diminutive member would be a source of disproportionate shame. But not on Casey. Far from breaking the illusion and being undesired, Mike heart beat just a little bit faster. His grin grew wider, and Casey saw a little spark of something more than the affection that she saw in his eyes on a regular basis.

"I guess we're going to have to do something about that, aren't we?" he said, his voice so powerful and commanding. Casey's own heart pounded, skin flushing all over as a wave of arousal washed over her. His arms slid around her, keeping her close, then pressed his lips to hers. She melted in his embrace. She was like jelly when he got dominant on her.

Pushing her lightly onto the bed, she translated the gesture into an exaggerated flop. Like he'd really tossed her hard onto the mattress. Her head snapped back in a pantomine of fear, like she was at the mercy of some rough beast waiting to take her. Judging by Mike's feral expression, that wasn't altogether wrong.

He lifted her ass up off the bed, making her knees support herself so that her rump was thrust into the air like an invitation. She felt his fingers tug down her pretty neon pink panties to expose her amazingly smooth, adorable butt. He let go of her for a moment. She bit her lip, all sorts of naughty scenarios playing out in her head for what was next. Her prick was still stiff and needy. After some rummaging, Mike returned a heavy hand to her hips. A half empty purple bottle of warming, lubricating jelly hit the comforter next to her shoulder. The next indication of what was going to happen was the lubed up finger pressing against her rump.

"Aaah~" she cooed, stiffening as his finger probed her hole. She relaxed instinctively, allowing him inside.

"Good girl. We're going to find a way to get your prick limp. Let's see what we can find in here..." His finger (Casey guessed it was his middle finger but she was a little too preoccupied to tell) pressed deeper into her hole. After long practice and with Casey's eager coaching, Mike had gained the ability to find her prostate almost every time. Attempts to let her do the same to him were met with raised eyebrows and awkward laughter. For now at least, Casey was the only one of the two would be enjoying this particular kind of fun.

The pad of his finger pressed against the special patch of skin next to the source of her lewd fluids, and she felt that strange sensation arise in her body. It wasn't quite the same as a stroke of her shaft, but it was pleasant. The feeling only built up as he slowly, carefully continued to stroke it. He moved his finger in circles, up and down, and occasionally giving it a prod, not letting Casey get used to one particular sensation. It took an effort to keep herself presented for him, as the aching heat in her body was building and making her want to pop.

The first lazy strand of fluid dripped out of her quivering tip. He used his left hand to drag her's to the spot directly under it just in time to catch the weak rope in her soft palm. "Keep your hand there until we're done, okay? We're going to milk you dry, and I don't want you to make a mess all over these nice sheets."

She gave him a nod, but a vocal affirmation devolved into a moan as his prodding continued. Somewhat frustrating that she wasn't getting that proper orgasm that would come from rubbing her dicklet until she shot, this was a long, milking session that drained her prostate out onto her hand. It was an act of total submission to cum like this. To get wet, to gain pleasure from being penetrated...this was what girls did. And in this moment, she was a cute, helpless girl, getting wet from being fingered~

"Ooh Mike," she cooed, breath catching. "Ooh...oh gosh..."

"Maybe we should lock up this naughty little cock?" he teased, finger flexing and making another drizzle of watery seed slide out of her. "After all, the only thing it's going to be fucking is the bedsheets while I plow you from behind. Why bother letting it get hard when you should be training your ass to be your main sexual outlet?"

If she wasn't trying desperately to keep her composure, she would have folded like wet noodles at the image of becoming a captive, caged crossdressing cutie. Her hand was overflowing now, partially due to her losing concentration and failed to keep it cupped. But even if she did, there was only so much lewd juices locked up inside her. Before long, she felt the telltale gentle aching that she had run out.

"It's...it's all out," she huffed.

Ever so slowly, Mike withdrew his milking finger. "You did great, sweetheart. But there's one last thing you have to do."

Casey looked over her shoulder, but Mike was ahead of her. He raised up her hand, the one dripping with slippery cum. Turning over to sit on her slightly sore bottom, she stared dumbly at the substance. "W-what do you mean?" she asked.

"This is cum," Mike explained in a tone befitting a teacher. "You know where all cum goes, no matter how girly."

Casey's heart hammered. She looked down at the transparent cream in her hand. Her cum. She'd eaten his own before...but this...Mike was in control of her. His clean hand casual stroked her hair with his other hand, fingers dancing softly along her scalp. It was affectionate, but the hint of domination was clear. She was his submissive. She leaned forward, tongue out, and lapped at the puddle.

"Good girl! Make sure to swallow every drop, okay?" She nodded weakly, still focusing on the seed. When there was nothing but sticky residue left, he gave her a kiss on the forehead. "Such a good girl. And look, your noodle is already shrinking."

It was true. Once her load was spent, Casey's cocklet was on the retreat. She was definitely a grower, not a shower, which helped a whole heck of a lot for when she wanted to dress like this. Her maleness in retreat, Mike pulled up the pair of panties from her knees and slid them around her nubby prick.

"There we go. Nice and small, just like a clit should be." He patted the little lump in her underwear, then finally broke character with a laugh. "Fuck, okay, sorry, I got sorta carried away."

Casey, who was still trying to catch her breath from the long, dragged out prostate orgasm she'd just had, waved him off. "It's...God that was hot. Have I mentioned that I love when you take control? Mnf." She shuddered, exulting in the feeling of total submission that had overwhelmed her. She was still recovering when Mike lifted her into his arms and gave her a tight, squeezing hug. It took her slightly by surprise, and she tensed up for a moment. But feeling the reassuring strength around her, the earnest expression of affection that lay within, and Casey relaxed into the embrace.

"What is this for?" she asked.

"I just wanted to show...y'know...I didn't want to think that I was actually being an asshole."

She laughed. "It's okay! I get off to being talked down to, you know that."

He hugged her nonetheless, only letting go after a final squeeze of assurance. "I know. It's just...I'd never do anything to hurt you intentionally. You know that, right?"

Casey nodded again, but hesitantly. This was getting dangerously close to the line they'd tried to maintain. Or at least Casey had tried to maintain. The last few weeks, Mike had constantly been straining at the border between casual sex buddies and budding romance to the point where they'd had two more conversations since their first dinner together about the nature of their relationship. Like an adorable, strawberry-scented ninja, Casey had dodged the issue at every opportunity. But given this step of going out in public with one another, as more or less a couple, it was getting harder to deny that there was something more than sex going on between them.

"I know, I know. You're a good egg. And I trust you. Plus, I mean, it's super fun to drag you down into my sinister world of bisexual debauchery." Casey tented her fingers like a criminal mastermind. Admittedly, not a very menacing image given her clothes and the fact that she'd been moaning like a whore a few minutes ago.

After their sweaty shenanigans, Casey had to fix her clothes, her makeup, her hair, and after some thought, threw on a new pair of panties too. Mike just had to wash his hands. They gathered up their things and headed for the car. Casey even had a purse, though it was for purely practical purposes given the complete lack of pockets in her outfit. Emblazoned on the bag's side was a Hello Kitty Skull and Crossbones design.

"The thing I hate most about girl clothes," she said, zipping up the handbag and sliding the strap over her shoulder. "I swear, it's some kinda conspiracy by Big Purse."

Their destination was a few minutes by car, or less than thirty by bus. Neither was particularly enamoured with the city's public transportation, however. And since one of them had a car, it was mutually decided that they should just use the darn thing.

A couple times during the relatively short drive, Casey had to point out a turnoff. Some of that was the unfamiliarity (and general dislike) that Mike had for driving in a city. Narrow streets, bikes, and pedestrians, it was like navigating through a sea of flesh and metal icebergs. But he events of the night loomed in Mike's mind, more than he was outwardly letting on, distracting him from the task at hand.

They reached the nearest lot to their destination, sliding into one of the few spaces left unoccupied. Mike sighed as he worked the key out of the ignition.

"You alright?" Casey asked. Girl voice mode still in place, but the worry there was genuine.

"Yeah, sorry. Just psyching myself up."

She patted his hand. "This place is full of cool people, dude. Nobody's gonna judge you, if that's what you're worried about."

"I get that. It's just...ugh."

She smiled reassuringly, moving her hand to his neck and rubbing it a bit. Mike couldn't help but relax a bit. "I appreciate you doing this for me. But if it's really bothering you, we don't have to go."

Mike turned to her. "Really? I mean, you had your heart set on the club, I thought?"

"I just wanted to do something outside the house with you. Got any better ideas?"

Mike chewed on that. He did feel a bit guilty at sinking the prepared night, but if he had a chance to spend time with Casey without having to deal with a cramped, noisy club... "What about, like, a movie?"

Casey fished the phone out of her purse. "Lemme check. There's no megaplexes around here, but there's an indie one that occasionally does fun stuff. Their site says...oh shit!" She landed a series of extra-light punches to his shoulder. "It's a Slaughterworld Double Bill!"

"Well that's way more awesome than a club. Which ones?" He leaned in to look at the small screen in her hand.

"Slaughterworld 3: Bone Harvest and Slaughterworld: The Die is Cast, which I think is the one with the gratuitous orgy scene?"

"You had me at 'gratuitous'," Mike said through a grin. One thing that had surprised them both was their shared love for horror movies. Both the good, actual scary ones and the goofy awful ones. "You sure you don't mind the change in plan? We can still go to the club if you got friends you wanna see."

"We were planning on meeting up after at a bar for lowkey drinks and to catch up, anyways. Howsabout we skip the club, meet them after the first movie, and I can introduce you to some of my friends in a less obnoxious environment?"

Report Story

bydreadknots© 4 comments/ 5037 views/ 12 favorites

Share the love

Report a Bug

Next
3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel