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3 Word Prompt #02 M/M: Questioning, Crossdressing, Cuddles.

Questions

Dylan could see his companion's figure resting on the bed through the clouded glass door of the hotel bathroom, but wasn't sure whether or not he was still crying. The sink's running water masked any noises from the bedroom as the skunk brushed his teeth and wiped his face clear of the strings of his client's cum before it could begin to congeal. He sighed as he set the toothbrush down and began towelling his face dry. Taking a step back from the sink and mirror, Dylan left the water running as he regarded himself. The skunk's left paw toyed briefly with his bangs, and with a flick of his neck his long raven hair flowed down naturally across his shoulders. He groped at his chest, trying to get a little more volume out of his bra's padding before running his paws down the front of his skimpy spaghetti-strapped top and flowing summer skirt.

Glancing to his purse resting upon the bathroom countertop, the skunk sighed once more. He'd been paid up front for the whole night, and was well within his rights to keep it all. But if the John sitting out there had buyer's remorse now that he'd cum and the realisation of what he was doing was no longer concealed beneath a flood of lustful temptation, Dylan feared he wouldn't have the heart not to at least partially refund the wolf. There were fewer things in this life quite so sad as a middle aged man fighting not to accept his sexuality, and the skunk had no interest in adding to the poor bastard's already substantial mountain of woes.

Stepping forward and turning off the tap before he drained the city dry, Dylan fiddled with his fringe one more time. He turned on the spot, placed on paw upon the bathroom door, grabbed his purse tighter in the other, and pushed it open. Padding out into the bedroom itself with his best comforting, soothing smile spread across his face, Dylan didn't even wait to see the look on his client's face. He murmured softly to the plump, grey furred wolf sitting at the edge of the bed and staring in a daze at the carpet between his feet.

"How you doin', sugar?"

The wolf raised his head, and Dylan's heart sank. His eyes were still bloodshot and tearful, and he sniffled miserably as he shook his head at the cross-dressed prostitute who not ten minutes before had sucked him off to the most spectacular orgasm of his life.

"I don't know. I... I don't know anything any more."

He paused for a moment. What escaped his lips next though did totally surprise Dylan. It wasn't a demand for his money back, or a curse at the skunk for corrupting or confusing him by pretending to be a woman. Indeed, it wasn't anything remotely negative.

"Would you... would you like to sit down? If it's okay... I mean, if my money is okay for this r-rather than... anything more physical? I'd like to ask you a question."

Dylan took a step towards the bed and the wolf upon it, then paused.

"You ain't gonna ask me about my relationship with Jesus or anyone, are ya? Coz, to each their own man, but religion and politics aren't topics I get into on the clock. Not for any price."

The wolf raised his eyebrows, and gave a dry, half-hearted chuckle.

"No. Nothing like that. I wanted to ask you... was there a moment? Like, a specific second, when you knew that you were... t-that you preferred the company of men?"

The skunk smirked, and he was pleased to see his client relaxing slightly rather than getting more tense as he approached the bed, turned on the spot and sat down delicately by the wolf's side. He left his right hand, the one nearest his current companion, resting flat upon the bed between them. Not to push the wolf into any physical affection, but wordlessly and subtly letting him know that the option was there should he wish to take it. His client, Jeffery. No. Fuck. Jerome? Jerry? Jeremy! That was it. Jeremy, didn't seem to notice the proffered paw though. He was staring off into space again, just waiting, maybe lost in his own inner turmoil once more as the skunk tried to find the simplest way possible to answer the question which basically defined his existence to this older man. Right now, intentionally or not, the wolf wasn't seeing him as a person. Right now he wasn't a person, nor even a prostitute to this man. He was gay. A gay man, and thus a font of information; a portal to a world which this closeted and married... or at least ring-wearing... male clearly did not feel that he understood.

"I guess... I was fifteen. At a friend's place, and he showed me this magazine. One of those porn mags that should have gone out of business as soon as the internet came along. The kind that teen boys like me back then always seemed to come across at some point. Anyway, the less said the better given how old we were. But... he started to enjoy what he was showing me, y'know? And was saying that I could enjoy myself too. And I did. Only, I wasn't looking at the porn mag. I was looking at him, doing his thing to his thing. He caught me looking. He asked me why I was looking, and if I was gay. And... even though I genuinely hadn't ever asked myself that question, I still felt like I knew the answer straight away. So. I said yeah. Yeah, I was gay."

Jeremy nodded, glancing towards the beautifully dressed skunk out of the corner of one bloodshot, still slightly moist eye.

"Was he... okay with it? You watching? You... um... b-being... gay?"

Dylan snorted with laughter, harsh and dry.

"Fuck no. He called me a sick faggot. He accused me of planning to fuck him while he slept. Only being his friend so I could try and get at his ass on some sleepover like that one. He tried to kick my ass, and when I kicked his in return, his parents threw me out of their home and said they'd call the cops if I ever spoke to their son again. By the time I got home, his parents had already phoned mine and told them what my so called friend had told them. That I had tried to rape him, and had beaten him up when he refused to let me. After that? Well... by the time I was sixteen I was living on the streets, and I was already doing what I've been doing for the last seven years to try and pay for a roof over my head."

The skunk was smiling as he fell silent. Not a happy or genuine smile by any means, but the smile he had long since learned to put on at times like this. His nothing hurts me smile. Either the wolf didn't notice it though, or he just didn't buy it for a second.

"Holy shit. I mean... holy shit. I... I'm so sorry I made you tell me that."

He grabbed the skunk's paw where it was still resting beside him, and squeezed it first with one, then both of his as he growled in frustration.

"I'm such an asshole. Acting like my fucking world is ending. All because... b-because I... fuck. And you, so young... out on the fucking streets. Fuck!"

Dylan shook his head, trying to tug his hand free from the wolf's grip.

"Don't give me your pity, man. I don't want that shit, or need it. No, my life ain't perfect. But it's not half as bad as it could be. You know what you're paying me, and none of that is going on drugs or shit like that. It's paying for an apartment. A pet dog. Classes at fucking community college so that when I'm not young and hot enough for this, I don't end up right back where I started."

He looked up at the wolf, Jeremy still staring at him with horrified guilt. Their eyes met, and though both men blushed neither looked away. Dylan chuckled dryly again.

"Fuck. Now I'm telling you my current life story on top of the old one. Sorry."

Jeremy squeezed the skunk's hand tightly where it was still locked between his own.

"Don't. Please, don't be sorry. I... I needed to hear that. Sorry if I sound like a total asshole, but... hearing how fucked up you've had things, and how you've pulled it back? It's the kick up the ass an entitled old prick like me needs. I'm afraid. I'm scared that I'm... I'm gay, and that I'll have to leave my wife. Tell my kids. My colleagues at my cushy fucking office job. What the fuck do I have to be afraid of, really, when I compare my life with yours?"

Dylan smiled, this time a more genuine and warm smile at the wolf.

"Doesn't mean its not hard for you too though. I had to build a new life from the dirt up. Yeah, you'll have a head start on that. But, you've got... what? A couple of decades more baggage than me, too. I had to fight to build my new life. You'll be fighting to escape your old one."

Only after he'd fallen silent once more, and seen the fear returning to the middle aged lupine's eyes, did Dylan curse under his breath.

"Shit. I didn't mean... holy fuck, I'm sorry. Didn't mean to make it sound so fucking difficult for you. I just mean, y'know, everyone goes through shit at some point. Straight or gay. Young or older. Skunk, wolf, or magical motherfucking unicorn. But you can get through it. You can find the strength to get through it."

The wolf nodded, though he didn't look entirely convinced.

"Yeah? Y-you think so?"

Dylan nodded firmly back.

"Yeah, I do."

He pulled his hand free from the wolf's grip, but only so that he could wrap that arm around the larger male's shoulders. The other hand fell upon Jeremy's thigh, bare below the extended of his check-patterned boxer shorts. He gave the furred flesh a squeeze, and felt a familiar, longing shudder run through the middle aged man. Jeremy blushed, and looked up and down Dylan's body with a soft growl.

"I... I still have the night, right? I mean, if you don't think I've totally killed the mood?"

The skunk leaned over, resting his head on the wolf's shoulder and planting a peck of a kiss on the top of Jeremy's arm.

"I'm yours till checkout. And hey, it's my job to keep us in the mood. So, what do you want us to do?"

Jeremy's cheeks got redder and redder, but to Dylan's surprise and a little pride the wolf didn't lose his nerve.

"Maybe... o-other stuff, later? But for now, and... sorry if this is super lame, but... c-could you just... cuddle with me?"

Dylan smiled, and this time there was nothing remotely fake or forced about it.

"Sure thing, Jeremy. Here? On the bed?"

The wolf nodded, but remained still as the skunk began to scramble properly up onto the bed on all fours. His eyes followed Dylan, particularly the skunk's lush tail where it was lifting the back side of his skirt.

"But..."

He drew a deep breath, shivering slightly, and drawing himself fully upright where he sat before letting the breath out again.

"...could you take off your clothes? A-all of them I... I think you're beautiful dressed the way you are, but..."

Dylan peered back over his shoulder. He giggled and lifted his tail all the way up, flashing Jeremy his panties and the bulge of his balls within them.

"But, you don't want to sleep with a man dressed like a woman. You want to sleep with a man tonight."

Jeremy swallowed, and nodded quickly. The front of his boxer shorts were already beginning to tent as he too dragged himself up onto the bed and knelt upon the sheets, watching as the skunk's ass waved erotically and hypnotically back and forth before him.

"Yeah. Yeah, I do."

By Jeeves