In from the Rain Pt. 02

"That's incredible, Casey!" Mike blurted out. She blushed, picking at the food on her plate.

"It's really nothing. Not enough to live on, of course, but it's still fun to do. Do you have any hobbies?"

Now it was Mike's turn to be embarrassed. "Nothing worth mentioning. Not classy like being an artist or whatever."

She rolled her eyes. "Oh, c'mon! I've seen you naked, goofball. Don't get bashful on me now!"

"Alright, alright. I code games on the side. Nothing massive, but...I like it."

"Neat! Like, puzzle games or something?"

"Sims. Running theme parks, space colonies, that kind of thing. Balancing and testing elements to keep systems in operation is relaxing to me, I guess. Weird, I know, sounds like busy work to lots of other people. But I enjoy it well enough. Hopefully I can polish up my next game to be worth putting out there for sale."

"Awesome! Well hey, you ever need someone to do art for your stuff, you know who to call!" she said with a laugh. That actually got gears in his head turning. He wasn't too good with art himself. If Casey could do some simple pixel stuff, it'd make his product look a lot less amateurish.

"That'd be...Damn, Casey, that might be fun. I'd love to work on a project with you, I think," Mike said.

Casey smirked. "It would also give us an excuse to keep talking to each other outside of the occasional hookup session."

"Yeah..." Mike rubbed the back of his neck, feeling shame bubble up in his gut. "About not calling you-"

"It's not a big thing!" she said, holding up her hands. "I totally get it. Our first encounter was weird, and honestly I didn't know if you were down for a second visit. But I got to thinking about you the last few days...and since I had the place to myself..." She looked up at him with those eyes...those dark, sultry eyes. Mike swallowed hard without any food in his mouth.

"It's not that I didn't want to see you. I was just...I didn't really know how to proceed. I'm kinda shit at relationships in general."

She nodded. As Casey drained some of the wine from her glass, Mike got inappropriately fixated on her perfectly pale neck. A lot of guys liked the tanned look, but there was something about creamy skin. Especially when paired with the bright red of her dress and lips. Everything came together to make her the object of his dreams. She couldn't have looked better to snare his attention if she tried.

She must have caught him staring. "See something you like?"

"N-no. Just...never mind." As lewd as there first encounter had been, he was still the hard-patterned introvert inside. Being caught ogling someone, even someone he had every intention of fucking, rubbed his sense of decorum the wrong way.

"It's okay! Honestly, I'm flattered." Casey's voice dropped a bit down into her more masculine, still adorable register. "It takes a lot of work to get this cute. I got sorta blessed genetically, and having a fetish for looking like a girl certainly helps. But having such a visible effect on someone is the ultimate compliment. Is there anything in particular you like about ol' Casey here?~" Her voice returned to feminine for the question at the end. She batted her long, dark lashes, and Mike had to resist the urge to either disintegrate into jelly or bound across the table like a panther and take what was his.

"I...umm...I really, really like your dress. You wear it so well," he said. She held out the fabric from her body to examine herself, like she just noticed she was wearing it.

"Oh, this old thing?" she said with a slight Southern accent, then laughed. "But seriously, thank you. It was hard to find this one. Most classy outfits are designed for women with, y'know, tits. I could wear padding, but I didn't really want to wear something that had to be super-fake. There's stuff made for classy trans broads, of course, but it's usually speciality work. Pricey stuff with long delivery times, and it assumes some hormone tits."

"And that's not something you'd be interested in pursuing?" he asked.

Her answer took a while to come out, her fork worrying at the remaining food in front of her. "Hormones? I thought about it. I like the way these clothes make me feel, and, y'know, being a shameless girly slut is fun. But I'm pretty okay with who I am. The dichotomy is fun, y'know? Being a serious, grumpy dude in public, being a sweet, happy girl with the people I care about...it's like having a secret identity kinda."

Mike grinned. "So...does that mean you care about me?" he teased.

She rolled her eyes. "Don't let it go to your head, mister. I'm legally obligated to care about someone with a dick that thick."

They shared a laugh, finishing off the dinner in quiet. When the last of the chicken was gone from his plate, he bit his lip. He had spent caught moments between mouthfuls taking in her gorgeous makeup, her skin, her pretty red nails. He wanted her. Bad. "I don't know how to proceed from here tactfully, but I can safely say that I'm done with dinner."

"So...mind if I take the lead?" Casey asked, sliding up from her chair. She crossed the distance between them with a sultry, hip-swaying walk that made Mike's heart pound. He started to speak, but she pressed a finger to his lips. "Shh...it's alright sweetie. I'll clean these plates up after. I'm hungry for something else besides broccoli right now, and I think you can help me out~" She held out her hand, and he let himself be guided to the living room. It felt a little strange to be lead by the hand, but there was also something profoundly attractive about Casey's sheer confidence. She knew what she wanted, and she knew what Mike wanted too.

In moments, Mike was on the comfy couch. Remembering their previous couch-related encounter brought back good memories, though this time was different. This time, Mike wanted every bit of Casey. He yearned for her, had increasingly erotic fantasies about her, and was now about to take what he needed from her body. Her dress was on the floor in moments, and he'd tugged down his pants to reveal his boxers. He was only half erect, but there was still some bulging around the fabric. She settled into his lap her underwear, which included a white bra to match a pair of white lace panties. She draped her arms around him.

"I really missed you," Mike admitted, leaning up for the kiss. She gleefully accepted. Her lips tasted like cherries, which only made him hunger for more.

"Likewise, cute stuff. I got worried when you didn't call me after a few days." The spaces between their conversations were taken up by smooches. Some were quick affairs, merely pressing of the lips together. Others turned to open-mouthed, tongue-dancing displays of oral affection. The latter greatly outweighed the former by the end as both grew in visible excitement at being together once more.

Casey's finger's found his hard-on, making Mike groan into her open mouth. With the grace of practice, she slid his shaft free of its fabric confines and began to stroke. A few licks of her palms done in a theatrically long, sensual manner meant her impromptu handjob was plenty wet and warm. Bucking gently, Mike was rock hard in under a minute with her. Working dicks was a magical power, Casey would be a wizard. A slutty, slutty wizard.

"Could you pass me the purple container over there?" Casey asked, pointing to the end table. Mike reached over and handed it off. Tingling gel glided out of the tube and onto her hands, where she spread it onto his cock. As it reached his skin, it started to tingle a bit. It wasn't unpleasant, either. Just a gentle, warming sensation on his erection that only made his desire to shove it inside someone even more present in his mind. Casey turned around, presenting her thoroughly squeezable ass.

"Also, could you...ehm...help me out?" she asked. Mike took the container, applied a generous portion to his fingers, and prepared to dive deep inside her waiting ass. As he pressed the tip of his index finger to her eager hole, he got a wicked idea. Why not have some fun with her to start?

His first finger slipped in with some pressure. Already slathered with lubricant, he went to work applying it to Casey's insides. But he went about it in what was clearly a slow, methodical way. And every time he pressed his finger inside, he was searching for that patch of skin that he'd read about in the many, many erotic stories about fucking crossdressers that he'd read (for research purposes only) after their first encounter. There was supposed to be a place in here...if he could just find it.

"H-hurry up," Casey whined. Mike could tell there was a little anxiousness behind his tone, like he wanted to get started.

"Calm down, cutes. Don't want to hurt you now, do we?" he said in a patronizing tone, squirting more lube onto his fingers and pushing two of them inside this time. Casey was making the most pleasing little groans by the time Mike found what he was looking for. "What have we here?"

She instantly tightened around him, but there was no escaping his touch now. Not that Casey wanted to. She visibly quaked as he stroked her prostate from within. Getting pleasure this way was something she was altogether familiar with, but it felt good to do it to her on purpose. A little something for his crossdressing sweetheart that was purely selfless. Well, not purely. Mike did enjoy the noises she made as her joy buzzer was teased.

"Ngh!~ T-that's for later, don't milk me dry with just a finger!" Her legs were looking rubbery by the time Mike stopped. He watched little beads of pre drip onto poor Casey's carpet.

"There we go. All lubed up, I think." Mike flashed her a playful smirk as she spun around. She wore a predatory grin herselg, straddling down onto him and pressing her small shaft against his for a moment.

"You're gonna pay for that," she declared, lifting her rump up and angling his throbbing erection to slip inside her. "I'm going to make you empty yourself into me, and there's nothing you can do to stop it~"

Casey slid down Mike's cock and instantly he felt that warm hole clench around him. Long, vigorous practice sessions had no doubt given her ample control over he ass, so the teasing tightness could only have been intentional to squeeze his muscle for their mutual enjoyment. Mike thought he'd be the one doing the work, but as soon as Casey was halfway down his slightly above average length, she lifted herself up to do it all again. She was going to fuck him into the couch at this rate.

"God, you're desperate for it aren't you?" Mike grunted. She nodded vigorously, making her position clear by stuffing him deeper inside, letting gravity impale her. She stroked her little dick, but Mike slapped her hand away lightly. "Just from anal this time. Let's see how much of a needy cockslut you are."

She did all the work. All Mike needed or wanted was to hold her close and support her back as she rammed her rump down onto him with a steady pace. He leaned in to take one of her adorable nipples into his mouth. She squeaked at that, but he didn't bite too hard. Just a little nibble to let her know she was his. He tried to imagine her with proper, girlish breasts. But the image fell away. To him, Casey was perfect the way she is...flat chest included.

Mike couldn't think straight. All his attention was focused on the sensations coming from his body. The warmth of Casey's ass wrapped around him, the smell of her perfume, the cries and girly moans offered from her perfectly red lips. He was hilted inside her now, his head mashing at her prostate with wild abandon every time she bottomed herself out. Weak precum drizzled out of her own cock, but she obediently kept her hand away from it. He wanted her focused entirely on her ass as her primary sexual organ, and she was more than willing to oblige.

The last few bounces provoked a steady stream of seed from Casey, her little cock twitching as her grip around his back intensified. Her mouth was pressed against his ear, so he heard every sweet, needy noise she made as his head prodded her prostate and triggered an adorably lewd anal orgasm. Her muscles clenched down around him without direction from her, and he let her stroke herself to completion. It moments, she'd collapsed against him. Her breathing was ragged and hot on his skin. But he wasn't done. Not quite yet.

He lifted up her hips and settled her down on the couch. Lifting her ass up so that she was pressed into the fabric, he reinsterted himself with a hard thrust, resuming the penetration and regaining what hardness had been lost as he let Casey come down from her climax. Like his dream, she had cum before him. But she wasn't getting away that easily this time. She was getting a full dose of cream.

"Ngh~ Are you gonna pump be full of cum again, honey?" she asked rhetorically. A hard thrust against her insides answered her question, forcing a shrill squeak from her mouth.

"Of course I am. Gonna paint you white inside. Going to...fuck~" He was unable to hold his control for much longer. Casey hugged him long enough to push another kiss against his lips, then nodded her consent.

"Fuck me as hard as you want, babe. Never pull out~"

That was good enough for Mike. He vigourously pounded her into the couch, causing her to moan and writhe and shake with the resulting sensations. There had to be a little bit of pain there, but there was no evidence of that on Casey's face. It was pure, shameless bliss all over her expression. That and something else. She was looking into his eyes and he felt something stir inside him. It wasn't from his balls, either.

"Casey," he said through ragged breaths, "I...I love you."

"I love you too, cutie. Now fill me with cum!" she cried, squeezing his dick with her hole as if begging him to unload inside.

It only took a few more seconds of blessed penetration before he had reached his limit. he shoved himself deep, feeling the spunk burst from his tip and pump out of his body in a quest for a woman's womb. It wouldn't find anything like that inside Casey, but his body didn't know that. All it knew was that he had fucked a girl hard enough to force a hard, shuddering climax from him. Gouts of seed coated her inner walls, and he slid back and forth weakly to milk his orgasm to completion. Once he was drained, he collapsed on top of her. Fucking was a lot of work!

***

Casey and Mike spent the next half an hour in another drawn out, sloppy makeout session. Still resting inside her, Mike occasionally felt his softened shaft get squeezed. Casey's own cum had gotten over them both with the power of his submissive release, but they didn't mind. It just felt nice to have made the cute crossdresser lose her load from just getting fucked.

Mike swept some strands of hair from Casey's face. God she looked pretty. "Where do you see this going?"

"Hmm?" Casey asked, his voice distant.

"Us. You and me. Me and you. What's the endgame here?"

Casey shrugged. "Does it have to have one? Can't it just be casual fun?"

Mike hesitated, his hands absently stroking her back. "I...don't think it can. I don't know how to turn feelings on and off like that."

"You don't have to turn your feelings off, silly. Just keep it light, unattached. Just enjoy the moments with me, while we can."

He smiled back, but it was pretty weak. That didn't sound like something he could do, but he'd give it a shot. Casey seemed fine with it, going in for some more sappy kissing action. Mike reciprocated. There was something there that was more than just sex. He could feel it...and he was afraid of it.

Tired out from the fucking, they untangled themselves from one another. Casey's rear dripped with spent cum, and they both needed a shower. Casey invited him to join her inside, and Mike could think of zero reasons to resist that suggestion. Hot water washed away the residue of their shared passion, and both took turns fondling each other a little too long to be considered an earnest attempt at washing the other's body. They ended up jerking each other off, splashing each other with fresh cum for a moment before it too was washed away. By the time they stepped onto the bathroom rug, they were both refreshed and thoroughly pruney. Casey took a moment to reapply some light makeup before joining Mike in the living room.

Mike hit the power button on the TV remote. Casey didn't have cable, but she did have one of those streaming boxes that let you steal content and not get arrested. After a brief run through of their shared tastes, they settled on a horror movie neither had seen before. Casey spent the duration nestled into Mike's chest and looking away from the scary parts. But she was giggling and smiling throughout at every jumpscare. By the time the credits rolled, both were sleepy enough to consider adjourning to the bedroom.

"Wanna go again?" Casey asked, though Mike could tell it was half-hearted. Poor cutie just wanted to be a good host.

"That's alright. I just...wanna cuddle with you for a while longer. At least until we fall asleep. Is that alright?"

She hugged him hard enough to nearly take the wind out of him. "You are just the goddamn...ugh, you're too much Mike. I'm calling the Diabetes Foundation on you, because you are too sweet."

They were soon under the blankets. This time they didn't spoon, but they did get nice and cuddly with one another for a while. Eventually he heard the telltale sounds of deep breathing that indicated Casey had fallen asleep. He couldn't help himself. He stroked her hair, watching her chest fall in and out. The last thing Mike thought about before he fell asleep himself is how good Casey's body felt against him, and how he wanted to feel that sensation every day. He drifted off, snuggling close, dreaming of what strange, wonderful future the two of them could have together.

And if he could teach her how to cook a roast.