Last Chance

Devon, you're an idiot! A fucking idiot! Why did you...

gah!!!

Yeah, Devon barely slept that night. Tossing and turning he went, looking at the hotel's clock every hour or so. He wagered he finally slept two, maybe three hours by 4 AM before just kind of stirring in his bed. Some shitty dream he kept waking up from as if he was in some kind of live action Grand Theft Auto game, but driving haphazardly by some cliffside where he kept inadvertently diving off the side of the cliff into the water and/or jagged rocks. So yeah, he jerked off once to again the not-faded-at-all wonderful - if bittersweet - memory of Jason pounding away at his ass two days before. That probably wasn't going away anytime soon, for sure. It was definitely fertile material from which to blow loads to be wiped away by hotel sheets that would be cleaned by some maid that would come when he wouldn't be there.

Wow. But that actually happened, didn't it? I still can't believe it.

Finally resolved that he wouldn't sleep any more, Devon hopped out of bed, rubbing at his temples. He was unfortunately reminded of his place in the grand scheme of life. He'd lost everything. The girl of his dreams, a pretty OK job if not a great one, a pretty decent place to move forward from. All of that. This was a thing he'd have to dig himself out of and he hadn't lost sight of that.

He grabbed his phone and looked at it, almost dreading doing so as he did.

Messages! Holy shit, he really did message me.

He'd actually assumed it might come in the form of a phone call, or most likely nothing at all.

Devon looked at his texts. There it was:

HEYA DEVON. YOU STILL DOWN TO DO WHATEVER IT TAKES TO MAKE THIS WORK?

And it was only sent 30 minutes beforehand. He smiled broadly, even giggling a little then. Yeah, the giddiness was back. Butterflies, even, if that could be a thing. He responded immediately:

WHATEVER IT TAKES. I'LL BE A GOOD GIRLFRIEND. 

He then waited. He could see Jason was "typing" almost right away. Was he as excited as Devon was? This was all so mysterious.

THAT'S EXACTLY WHAT I WAS HOPING YOUD SAY. :D CUM BY MY PLACE AT 9 PM AND BE READY.

Devon set his phone down then, nodding resolutely. The smile never left his face.

Oh yes, I'll be ready.

Then the smile ebbed a bit.

Just don't... do that again, Jason. Please. I can't take that again.

He knew he deserved a lot of things but he didn't deserve that. Not again.

---

9 PM came so quickly. Devon spent a few hours "doom-scrolling" on his phone before getting ready for his "date." That mostly consisted of giving himself a hot bath where he did some basic maintenance. You know. Cleaning his ass, shaving his pubes (even crack) outright, and soaping up for a good hour and half to ensure he would smell nice. He wanted to at least present himself as fresh as Jason had in their first night together. He afforded himself only 3 shots of Tito's vodka before departing.

After a drive, he was there. Quickly he rushed to Apartment 2B, clambering up the steps to the second floor. He knocked, eagerly. Before even five seconds passed, the door opened, not swiftly but rather slowly. And then there was those piercing blue eyes looking into his own.

"Awesome. Right on time," Jason said. Smiling tightly. He gestured inside. "Come on in."

"Okay."

Devon noticed right away, of course, that his old friend wasn't clad in just a towel like last time or anything. Though as he passed him going in, he noted he still smelled as spectacularly as before. Just as fresh. Not wanting to presume anything, he began to head toward Jason's living room.

"Ah-ah!" Jason said. He then pointed the hallway bathroom. For which the door was closed. "Go in there first, please. If you will."

"In

there?

In the bathroom?"

"Yeah," Jason said with a nod and that grin again. "I know, I know. It'll make sense when you go in there, I think." Devon - surprisingly - wasn't really nervous until that exact moment. "You'll know what to do."

"Eh... okay. Like I said, I'll, uh... do whatever. I want this to

work."

"So do I." Jason turned to head to the kitchen then stopped, turning back to him as if a new thought just popped into his mind. "And look, if it's not for you, if you're not feeling it... I totally get it. I've already been shit to you. No harm, no foul. After you go in there if you don't like it, we can hang out, play video games, take shots, whatever you want, or you can just get. Again, totally get it."

Okay, now I'm

really

nervous!

Devon only gave a nod. He headed into the bathroom and Jason went to the kitchen then. He flipped the light switch inside as he closed the door behind him. He decided against closing his eyes but, instead, just looked at the floor until the door was firmly closed. Then he looked up.

Oh, shit... what the fuck! What the fuuuuck...

Arranged neatly atop the closed toilet, the counter, and across the towels on the wall was an assortment of... women's garments. Fishnet stockings, generic pantyhose, panties, bras (for these, all in black), elegant bracelets and jeweled necklaces... and three wigs. All three mostly in the same style, below shoulder-length mostly straight hair with slight bangs that might angle down into one's cheeks. One was pretty standard brunette, one was sort of a dirty blond, and one was like fire hydrant red.

Devon felt his heart pounding now.

Oh my god, he wants me to... oh my god!

He then saw a sticky note by the rim of the sink, where the wigs were next to:

BE THE GIRLFRIEND YOU WANT TO BE.

- J

Devon slowly collapsed on his haunches, running a hand through his hair, eyes wide and freaked out as never before.

Good god, what the fuck?! This was nothing he'd ever even considered, let alone fantasizing about - ever! I'm not some kind of fucking weirdo! I'm not! And yet...

Jesus... maybe... maybe it's worth a try?

he pondered then, with a little bit of a clearer head a few moments later.

If I hate it, then... whatever. Right? It's never too late.

He looked at the undergarments first. So frilly! So girly. What could

possibly

have made Jason think this would be something he'd be into? Oh wait.

You said you were happy being his girlfriend. His fucking

girlfriend.

Remember that? Duh. Idiot. Hello? Though... how would he even know my size?! Did he study me

that

closely? That's kind of a turn on, I guess.

He thought to Shannon, suddenly. He'd seen her close up, intimately, from all angles and over a very long period of time. Yet, if gun to his head and if he'd have to walk into like a lingerie shop... there's no way he'd have been able to buy stuff for her without some kind of a "cheat sheet."

His outstretched hand hovered over the three wigs, then. First the blond one.

No way, that's not me. Plus I'm pretty enamored with a certain blond right now!

Then the fire hydrant red one?

Pretty hot, honestly. I'd look like Jessica Rabbit. But... too much, right? I don't want to look like a porn star

. Then the brunette, pretty natural looking one.

Yes. Yes, I think this is the one.

In the mirror, he put the wig on and looked at himself. It actually suited himself pretty well.

"So I guess we're doing this?" He gave a deep sigh as he continued staring at himself with the wig on. Like a mini pep talk. "Okay. Cool."

With that, he got naked and began getting dressed. First in the basic pantyhose, then slipping into the lace panties, then spending more time than he'd feared figuring out how to get into the bra and fasten it. When he was finished, he looked by the light switch where he noticed for the first time an unmarked bottle of what had to be perfume. It had a sticky note: "WEAR ME." He did so, spritzing some across his neck and collarbone area.

Devon then struck various poses in front of the mirror, now in full women's wear. He actually didn't look bad, he decided. He poked out his butt a bit and turned, looking at himself again.

Yeah, not bad at all. Wait, what the fuck am I saying? Good lord... I'm kind of liking this, aren't I?

He even had a little bit of a "bubble butt," depending on the angle. He'd always tried to stay fit with a lot of cardio but he'd never really packed on much muscle... so in the angles he was wearing these articles of clothing he noticed he could totally pass as fairly feminine. Even... an actual woman. It gave him a bit of a shock, but he rolled with it within the energy of what was going on and possibly what was at stake.

I hope he likes it,

Devon worried. Though he noted it was strange that he was no longer worried about how weird this was. It honestly seemed to just feel like a fairly natural glove for him to slip into, given the circumstances and his feelings for Jason.

Smiling in the mirror at himself, he channeled his inner "girl" and winked. He was ready then, he decided. With a little twirl as he went, he opened the door and dove headfirst into whatever the rest of the evening would bring.

He wouldn't have long to find his answer. It would be Jason's arms. Jason's tender, loving arms, which he was feeling for the first time all over his body, almost plucking him up from where he exited the bathroom. He felt so warm, so nice. He felt immediately comforted, in a happy place he didn't know existed let alone one he deserved or would be walking into. He was literally swept off his feet to an extent.

"Oh my!

Ooh!"

Devon yelped as he was grabbed. He made his voice sound higher pitched and more girly without even realizing he was doing it. "So I think you li -"

Jason's mouth quickly found Devon's, hungry, and he was silenced.

"Mmh!"

But it was a blissful silence then. A moment later Jason broke from the kiss and looked him in the eyes, parting the bang that had fallen directly in his eye and cupping his cheek.

"You look

perfect,

baby," Jason said. The grin was back, but now there was real hunger behind it. Devon felt taken aback by his clear need. "Are you okay?"

So many emotions were exploding in him he found it difficult to take a moment to remotely look inward... but he

tried.

As he looked back into Jason's eyes, he nodded to him. "Yes." Another moment. "Yes. This is perfect."

Jason reached down and hoisted up Devon, holding him in his arms now. "Are you ready, m'lady?" he asked.

Devon gave a girlish smile. "Yes, my love. I am yours."

"You smell so good, Devon."

"God, so do you."

"Thank you."

"You know I will always take care of you, right? You know that?"

"Yeah?" Devon took a deep breath. Also gulped. "Well, I know it now."

"Look, your problems? Forget about them. They're in the past now. All of them."

"You're so sweet, Jason. God, I..." he stopped himself then.

Devon gave Jason a kiss on his neck, as was easy to do from his position. God, that felt so right. Jason responded by leaning his head into him a little further. He felt his hand caressing one ass cheek and he moaned in his ear.

And off they went. Slowly, deliberately, to the bedroom. Real, true love would be made, and Devon was sure of it. And nothing had ever felt more natural or right to him. As they passed a hallway mirror and he saw himself being held by Jason in it for a moment he smiled again. God that was hot.

To be continued...