GAMBLER’S DEBT

Wow I just learned about this place – neat! have been posting my stuff in another spot, hope to get good feedback here! Unlike most things I write, this is a single chapter story…Enjoy!

I first saw Isabella Guerrra in the foyer of the Ocean Sun Casino, Panama City, as she walked elegantly down the staircase. I was there as my firm was the Casino’s legal representative. I was never one to gamble, as any good lawyer only bets on sure wins. Isabella was about average height with the usual long, dark hair of most Hispanic women, and it was expertly styled, framing her face and her plump red lips, that were under a cut little button nose. She wore a low cut dark green dress with a cleavage showing her ample breasts and a hem line cut three or four inches above her knee. It was enough to suggest that she had a shapely pair of legs. In fact, she was altogether an attractive young woman, probably, in her mid-thirties I guessed. A gorgeous Chica Latina, the staff treated her as though she was a regular, and that got me thinking.

She walked past me to the gaming tables and I got a second look at those brown eyes and a pretty face, before a whiff of her expensive perfume assailed my nostrils. I turned, just in time to see her hips sway back and forth inside her tight fitting dress. The wolf (me) watched until she disappeared around a corner. Now the little head was doing the thinking, heh-heh.

I wandered into the gaming room and saw her standing at the roulette wheel. Her modest pile of chips seemed to be dwindling fast. I stood and watched her for a bit, until her last chip was gone. Every time she lost, she seemed to go a shade whiter in the face. I had seen that same look of desolation and loss in this Casino before, and now I had a plan.

I casually followed her, as she walked, defeated, out of the room. Isabella sat down heavily in the nearest chair and started to search frantically through the contents of her cocktail bag. I knew what she was looking for, a chip or the like, anything that would get her back to the table. I knew then that she was well and truly hooked on gambling.

She hung her head in defeat and closed her bag. The answer to her problems wasn’t in there. It was a good moment to approach her.

“Hey, don’t look so down, need a drink?” I asked. “You sure look as though you could use one.”

She looked up at me was about to politely give me the brush off, when she saw me toying with a few high value chips (I just so happened to keep handy), and changed her mind.

“Sure, why not,” she sighed and accompanied me into the bar. I sat her in a corner booth and ordered drinks. Then, I introduced myself and she told me her name was Isabella.

“Gambling sucks,” she said, bitterly, as she took a heavy swig of her gin and tonic.

“You’ve had a bad night, then,” I probed gently, to see if she would open up.

She said nothing at first, but, after a second drink, it all came out. She had been gambling for weeks, and, after a few wins, was now into some heavy losses. Then, she had borrowed some cash and had tried to win it back, without success.

“How heavy is heavy?” I enquired.

“About $3000 or so.” she sighed. Then, she sang the usual sad story, of how her and her husband had moved here to open a restaurant in Panama City Beach. At the end of an expensive refurbishment, Covid hit. They just got back up & running, but never seemed to make enough to cover overheads, the interest on the bank loan and make anything of a profit. Isabella had a few good nights here, but tonight, it came crashing down, and she just wasn’t sure what to do. With that, she finished that drink in one large gulp, and asked for another.

She babbled a bit more after the second drink. Apparently, none of her friends or relations knew of their financial plight. It was amazing what a drinks would do to loosen the tongue. And, to be fair, she’d had such a poor night’s gambling, that she just had to unload onto somebody. I had seen it all before.

“I don’t suppose you could help me,” she implored, thinking of the chips she knew I had in my pocket. “I’m rather desperate, I’m afraid.”

Her dress had ridden up her thighs and her ample bosom was heaving with her anxiety. I could see she had assets in abundance. “Well, Isabella, there is a way I could help you,” I said. The little head was really doing the thinking now. “desperate times call for desperate actions, you know.” To that I saw her hang her head and glance away. It was too much, but I was feeling generous “I’ll give you one third of what you need, or $1000,if you’ll spend the night with me, upstairs.”

I saw the anger flare up in her eyes and felt a painful slap on my face. “How dare you,” she fumed and stomped off in anger. Luckily, there was no one around to witness the scene, so, I shrugged my shoulders and smiled. It was a take it or leave it offer and it was up to her, & I noticed she went to the restroom, not out the door. Let’s see how desperate she is, I thought. So, I nursed my drink a bit while I toyed with my phone.

It wasn’t even half an hour later, when I became aware of Isabella’s presence. I looked up and there she was. She looked more composed and had obviously re-done her make-up. She looked positively stunning.

“I’m sorry I slapped your face,” she said.

I nodded, accepting her apology and waited for her to go on.

“I’ve been thinking about your offer. I wondered whether you would give me half, in advance. To see if my luck has changed.”

I thought about it, before shaking my head. It wasn’t in my interests to do that. I liked her better this way, broke and vulnerable. I shook my head, and returned to my phone.

After a minute, Isabella slid into the seat opposite me. “O.K.” she sighed heavily, I’ll do it.”

‘Sometimes it’s good to listen to the little head’ I thought to myself.

I turned off my phone, then got up and guided her through to the reception area. I topped up my money at the front desk, as they knew me, and got a key. Then, we were riding up in the lift in silence and looking for the room. It was 804, a top-house room, oceanfront.

She walked ahead of me into the room and I could see she was really impressed with its high standard of décor, but she was understandably quiet and subdued and I could tell that it had been a desperate decision for her, and she stood at the open door to the deck, looking out at the moon over the Gulf.

“I’ve never cheated on my husband before,” she suddenly confessed, with pang of guilt in her voice.

But, if she wanted me to give her the money out of pity or something, she had picked the wrong guy. I was determined to get my money’s worth out of her, every last penny.

“Well, think of it like a business arrangement. You’re using your female assets to service a debt.”

I let her consider this, while I unzipped her dress all the way down. As she stepped out of it and hung it over the chair, I could see what a superb body she had. And it’s all mine, I thought as I unhooked her bra and threw it on top of her dress. Then, I quickly knelt behind her and tugged down her flimsy green panties. “You like green, don’t you?” I said, with an evil-boy grin.

“It’s my favorite color,” she admitted.

I made her stand with her legs apart and facing me, as I inspected what I had purchased for the evening. She had gorgeous long legs and I concentrated on these, at first, as I stroked, kissed and fondled her thighs. Then I stood up and started on her breasts; holding them, squeezing and kissing them and toying with her nipples.

Isabella had that olive complexion, her pubic hair was a sweet little landing strip, and her areolas were large, and really dark. She was complete with almond-sized nipples, and my mouth watered. On her own accord, she undressed me, seeming to pause around my fit chest, running her fingers thru my chest hair was particularly nice.

I guided her to the bed and went back to kissing and stroking the inside of her thighs. Then, I spread her knees further apart and leaned in between to lick her pussy. She was already quite wet, which was great, but again, I wanted my money’s worth, and so I began to work my tongue up and down her slit, then between her labia, then working my way back to her clit. Isabella was beginning to moan, and shift her hips.

“My husband should take lessons from you,” she said, and moaned louder.

I carried on, enjoying her slow writhing beneath me. I then used my fingers to push inside her vagina. Her moans increased to a yelp, and now she was panting too. Isabella got a real good fingering, until I felt her juices start to squelch around my fingers. I said “Come on Isabella…” and as I began pumping her vagina with two fingers I held her clit in my lips, and tickled it with my tongue. That did it.

Isabella’s yelps went to a solid cry as she felt the orgasm coming. She didn’t want to, but she couldn’t help it, and she thrust her hips powerfully into my face as she screamed “OH GAH-H-H!!!” she bucked and writhed and reached her orgasm. Her shrieks echoed around the large room, her pussy clutching my fingers for a full 5 seconds before she fell back onto the bed

I knew she would be sensitive just as I wanted, so I mounted her and heard her gasp a tiny “no wait-” as my solid cock, one that didn’t belong to her husband, slid inside her. She turned her head away, her face red and grimaced, then began to look from side to side, as I began to mercilessly pound my thrusts into her. I was going to get my money’s worth, no doubt.

And as I rammed into her, I felt her post-orgasm body respond to my cock. Isabella began to push back sub-conciously, and in a few minutes we were fucking frantically. She had lost all her inhibitions. Isabella was caught in the moment and her hips were tightening. She was taking all I had to give, and I was giving it hard, so I added a grind to my stokes, and I felt her shudder beneath me as another smaller orgasm overtook her, her pussy squeezing my cock as she had my fingers

I wasn’t too far away myself, but I did not have a condom. The feeling of Isabella cumming on my dick like that, plus the look of sexual defeat on her face was too much, and my strokes were shortening. I was on top, and I whipped out, and got my second surprise when Isabella reached down and gave my dick a pair of pump-squeezes. She must do this a lot, because she did it expertly, and I shot a rope of goo that hit her breast, then across her stomach. My turn to furrow my brow as I grunted loudly. Isabella gave it several more pumps. Rubbing her thumb over the head, as she milked the last of me onto her sexy brown tummy.

We lay there for a bit, then Isabella got up & refreshed herself in the bathroom. Another surprise as she obediently came back with a warm wet washcloth and cleaned my dick and balls. I then followed and talked to her, as she had her shower. We got onto her favorite subject, gambling. She loved talking about it, forgetting for a while, all the heavy losses that brought her here.

“Does your husband know?” I asked.

“No,” she said quickly “and I don’t want him to.”

“He won’t hear it from me,” I said.

“Something else I should tell you,” Isabella admitted “I’m on the pill.”

She dried herself and came out of the bathroom, still naked. It was just the way I wanted her, as I feasted my eyes on her lovely figure. The old boy was up for seconds it seemed, so I guided her to the end of the bed and, putting a pillow over the low foot rail, I had her grasp it. She understood and bent over.

Her legs straightened this way pushed her ass up and boy, was it a sight. If I got the chance, I would love to smack that pert backside. I took time to feel Isabella up again, For someone who had been so reluctant earlier, the fact that she was so wet made me wonder. Also, Isabella had almost naturally obeyed me at every step of the way, just like a good submissive girl should. So I decided to test something.

I had brought with me the sash from one of the hotel robes. As Isabella was grasping the bar on the railing, I quickly tied off one hand, tossed the sash over her back, and got the other. Isabella looked back at me silently, and smiled.

THAT made my cock fully hard again, and it was time to put it to good use. I eased pu-uu-shed into her pussy from behind, going all way in straight away., grabbing her hips and pulling her onto me, her ass against my stomach. And there was that delightful little shriek again, as I impaled her with my hard dick’s entire length. She groaned as I held her hips and began to fuck her in earnest, with all the lust that had been building up inside me, since I had first encountered her predicament. There was nothing quite like a bound submissive to bring out the beast in me. And, I kept it going for a long time. I rolled my hips and varied my pace, I wanted this one to last, and Isabella was groaning and yelping and whimpering, especially as I would slow, hold, then ram into her, pick up the pace for a bit, then do it again.

Then, as before, I felt her starting to thrust back at me in encouragement. This was a lady who liked fucking and her body wanted it desperately, I could tell. So, I held nothing back and pounded her relentlessly. As I did so, I reached forward and cupped her dangling breasts. They were more than a handful for me as I squeezed and enjoyed them. I switched it up a bit, grabbing a handful of hair, and pulled it. It made Isabella cry out, asking for more.

I felt myself going over the edge. I gave her another couple of hard thrusts and proceeded to dump everything I had into her, slowing my pumps and milking my dick dry. She shuddered and cried out in a long moan.

She collapsed onto the bed, moaning softly, while I helped myself to a drink of water. I then untied her, and offered her some. Taking my hand, Isabella led me into the shower, and proceeded to soap her hands and caringly wash every bit of me. If I could have mustered up an erection, I would have had her again, but the old boy was tired

We were so tired and dropped off to sleep alongside each other on the bed. We must have slept deeply, because, the next thing, her phone alarm woke us up at 6.30 a.m. We had managed about 4 hours sleep at most. Isabella mumbled something about an early start at her restaurant.

Isabella had started to wiggle free, but I pulled her back in to the spooning position, and slid my dick between the top of her legs. She responded, licking her fingers as she rubbed herself. Keeping her held like that I continued to grind my hips for a moment, then, as I shifted back, Isabella groaned as I pushed inside her. I held that for a moment, as she was not as wet as the night before, but after just a moment, Isabella began to push back against me. Damn she liked to fuck, I thought.

We stayed like this for a while, and she was moaning, but I wanted to make sure I left her wanting, and of course to get my money’s worth, so smoothly, yet with power I rolled Isabella onto her stomach. Her knees together, I mounted her flattened body. Grabbing her biceps just above the elbow, I held her trapped as I began to shamelessly, ruthlessly thrust into her, power-pounding her pussy. Isabella was yelping “Ah-Ah-AH-AH-AH!” as I continued to thrust into her with out slowing. I was using her, and she surely knew it.

After a few minutes of this, Isabella’s body tightened, and she screamed out a wail that sounded like I was killing her as the rush of an orgasm caused her to shake an convulse even more than the night before. The twerking on my dick pushed me over the edge, and I again dumped my full load inside her, not rolling off until my dick went soft.

“I’ve never had sex like this before,” she informed me weakly, as I got up. I grunted in satisfaction & smiled.

“So you intend to make good your losses, somehow, before he finds out?”

“Yes,” she sighed, “I have to. Fortunately, he’s not interested in the money side. He leaves it all to me.”

As she dressed, I slipped her the money. Isabella smiled as she took it, then again and brighter as I added the chips from last night

“Well that’s a bit more than a third. We can continue this arrangement for the remainder, whey chance it on the tables here? They’re stacked against you, you know.”

“won’t be easy to explain my absence overnight,” Isabella replied, “although I have to say, it’s tempting”. I liked that she took my card.

I enjoyed watching her as she did her make-up, & I could see her self assurance had returned.

Isabella walked ahead of me down the corridor and that wonderful sexy walk had re-appeared. I watched her disappear out of the front door, heading for her car. She treated me to another leg show as she maneuvered herself into the driving seat. I also noted her car number as I waved her goodbye.

***

It had been perhaps a week since I “ran Isabella’s tables” at the Casino. I was at home on the upper veranda of my home, alternately pecking away at office work on the laptop, and taking in the gorgeous view of the Gulf of Mexico on a fine fall day, when my phone rang. It was the number for the St. Georgian Group security at the main entrance gate of the community. “Yes”? I asked. “Mr. Roberts? This is David at the front gate. There’s an Isabella Guerra here, says she wasn’t expected but that you know her.” “Yes David” I replied, please give her directions to my home, let her thru, and thanks.”

‘Going to be a busy afternoon,’ I thought to myself, as I signed out of everything. At the front door, I say a dusty Toyota pulling in to the drive. Isabella smiled as she got out. She was carrying the little shirt she must have had on at the gate, but now she was wearing a very skimpy bikini ‘Going to be a busy time indeed.’ I said aloud.

Source: reddit.com/r/eroticliterature/comments/m1gl2g/gamblers_debt