A LOST GAMBLE

Story by ragewolver on SoFurry

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#1 of WRITING PROMPTS

A writing prompt from Tayu's Telegram writing group. My first post from a prompt from his group. https://t.me/joinchat/CPoeZhclggenrOEh0yYwvg


"You can't be serious," I said in exasperation, looking at the package my friend had sent me.

"I'm very serious, Scottie," Hale was saying to me. "You still owe me. And I don't forget."

"That was years ago!" I stressed. "We were stupid kids back then!"

"And now we're wise adults. And, correct me if I'm wrong, but I believe you said you'd pay me in full."

"How much was it exactly? Three hundred?" I reasoned. I remembered quickly clearly how much I owed him now Hale brought it up. Technically, it was three hundred and seventy eight dollars, lost in a single hand of Texas Hold-Em. I had been so sure that I would've won with three jacks, but that lucky tiger had managed to draw a full house.

His luck, not skill, was going to get me in trouble.

"Actually, I believe once we settle up, you'll owe me a tad more than three hundred," Hale was telling me. I winced. I probably had racked up quite a debt to him in the past several years. From asking for rides to having him tutor me through college, to the several times he'd loaned me money just to keep my apartment.

"So, let's say a thousand and I'll pay you back by the end of the year."

Hale let out a hearty laugh that made my hackles rise. I was sure I was growling when he spoke once more.

"If you had the money to simply give me, you'd have paid me back by now," Hale deduced. And he was right. I was already thousands of dollars in debt in my student loans, my rent, my car payments. I can't afford what I have, let alone to pay anybody back.

And being a loser dog with a gambling addiction only made things worse.

"Okay, okay, you win," I breathed. "But it's just this once, right?"

"Hmm, we'll see. Show up tomorrow in...uniform and we'll see how much you've paid back."


I fucking hate Hale.

No, that's not true. Hale is a wonderful tiger with a heart of gold and eyes so pretty, I've gotten lost in them before. He's my best friend, the only person I can think of who's always taken my side and been with me through thick and thin. From the moment I came out in high school to our graduation from college, Hale has always walked beside me.

But right now, I really dislike Hale.

He has me standing here outside the door of his apartment in dressed like a maid. A French maid. A female French maid! I knock hurriedly, trying to get used to wearing this frilly skirt and the silky panties he has me in. My face burns with embarrassment as one of his neighbors returns him just in time to see him invite me inside.

"Why do I have to dress like this?" I whined. "Can't I just clean in my clothes?"

"Nah, I wanna see you like this," he said. "You can start my picking up in the living room."

I huff. "You actually just want me to clean?"

"For now."

"And what later? You want a five-star dinner?"

"Not just yet. For now, just pick up the living room. Vacuum, dust, et cetera. Whatever you need to do to make this place spotless."

It struck me as I looked around that his apartment wasn't messy. Hale had always been a neat freak, but his apartment was immaculate. There was a bit of dust here and there, but nothing a quick wipe down couldn't remove. His carpet was clean and white and soft.

Then I noticed a pair of his underwear on the floor. Surely he didn't call me over here just to pick up his undies. If he did... I had leaned over to pick up the briefs and it took me a minute to realize something--I'd never known Hale to wear briefs. Almost immediately, an unbidden image of Hale wearing these tight, low-cut briefs filled my mind and I swallowed. I was about to ask if they really were his when I felt his body press against my back.

"What're you doing?" I exhaled, my heart starting to beat faster.

"Wondering why you're playing with my underwear. That's a kinky thing to do."

I felt his paw start to reach up into the skirt he had me wear and pull at my--the--panties. My body shivered as his paw hook onto them and started to lower them.

"What're you...?" I managed to say in a breathy, heavy voice.

"I'm collecting on your debt," he said huskily into my ear. "Just shut up and enjoy it. You're really cute in this skirt."

I could feel myself starting to get aroused and I felt my member start to rise from its sheath as he teased me with his rough, calloused touch.

"Want to?" he asked. "Just tell me to stop and I'll--"

"If you stop, I'll never pay you back," I countered, my voice saturated with lusty desire.


"So, what now?" I asked after we had cleaned up and showered--together, I might add. I was dressed in his clothes that carried his masculine aroma (which gave me a certain excitement) and reveled in his closeness. I admit it--I love him. And my mind is reeling, wondering if he loves me too.

"Dinner and a movie?" he asked.

"Definitely," I agreed.

"My treat," he offered. "Oh, and Scottie," he added. "Would you wear that skirt I like?"

I took a coin from my pocket. "Care to make a wager. If it's heads, I'll wear the skirt and panties. I'll even suck you off in the theater. If it's tails, then no."

He leaned forward and kissed me. "Sure."

My face burned and I flicked the coin and caught it. Tails.

"Is that I no?" he asked teasingly.

I smiled. "I'll still suck you off because you're cute."

I can't wait to lose another gamble with Hale.