Shayna Pays a Debt

by Naughty Shayna

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Reluctant, Coercion, Gang Bang, Oral Sex, Anal Sex, Voyeurism, Size, .

Desc: Sex Story: Shayna's boyfriend Jimmy was in trouble. He owed a lot of money to some very nasty people. Shayna wanted to help, but what could a poor schoolteacher do?

I stood there on Jimmy's front porch, pounding frantically on his door. When he had called a few minutes earlier and asked me to come over quick there was a nervousness in his voice that told me that he really meant it. Something unusual was going on. I had dropped everything and run over to his place as fast as I could. Now he was making me wait in the hot sun.

Finally the door opened. "Hi, Shay." No smile or hug or kiss on the cheek. Something was definitely up.

"What's goin' on, Jimmy? You sounded like the sky was falling when you called."

"It is, for me anyway. Come on in."

I followed him into the living room. There were three guys sitting there. From the way they were staring at me, it looked like they had all been waiting for me to arrive. I like to be the life of the party as well as any girl, but this was a little creepy. I thought I knew all of Jimmy's friends, but I didn't recognize any of his visitors. They looked like they were waiting to audition for parts on The Sopranos. The fat, ugly guy filling up Jimmy's favorite recliner would be the don, or capo, or whatever they call the boss now. And the two young guys on the sofa looked like they would be perfect for the role of bodyguards ... no, muscle, or whatever they call goons now. Nobody was smiling, and Jimmy didn't bother with introductions, so I was pretty sure that having the Three Stooges in his living room had a lot to do with his frantic phone call. I still didn't know what all of it had to do with me, but I was getting a very uneasy feeling. All three of his visitors were still staring at me. I felt like the main attraction at a slave auction.

"Yeah, Jimmy, you weren't kidding. She's mighty fine." It was clear that the fat guy, in the cheap-looking sports coat, was in charge. So Mr. Big Shot liked me. Big deal, most guys consider me eye candy, creeps like him included. But why had Jimmy been telling them about me?

I tried not to respond to their unwanted attention. It was hard not to laugh though. The big guy looked like a monkey, with body hair sticking out of the top of his open shirt and on the backs of his hands. Bet nobody ever tells him that though, not if they want to keep their face on the front of their head. He looked like the kind of guy who negotiates with his fists.

I tuned my attention to my very nervous boyfriend. "Jimmy, what's goin' on?"

"Come on, I'll explain in my bedroom."

I followed him down the hall. His "buddies" watched me like I was Miss America walking down the runway with my new crown on, and a boob hanging out of my gown. I was starting to get pissed, and I unloaded on Jimmy as soon as he closed the bedroom door. "What's with the creeps? And what does it have to do with me?"

"I've got a big problem Shayna." Jimmy was avoiding eye contact, which meant he was either lying to me, or telling me something that he really didn't want to. "You know how much I like to bet on sports, right? Well, I'm having a really bad season with college games this year. I owe my bookie quite a bit of money."

"Let me guess, that would be the big, ugly ape, right? The one who's here with his friends to break your legs?"

"That's him. And it's no joke, these guys really do mess people up if they can't pay."

"Jimmy, surely you didn't ask me over here to borrow money. Hello, this is Shayna, the schoolteacher, remember?"

"I know you can't help me that way, Shayna. It's more complicated than just money anyway. I kind of used you as collateral."

"Collateral? Kind of? Just what exactly the fuck does that mean?"

"OK there's no easy way to say this ... and I know you're gonna hate me ... but here's the deal. If you don't do these guys, they're gonna hurt me, bad."

"Do them? You mean you want me to fuck that greaseball and his friends? Just to get you off the hook? Yeah, Jimmy, somebody's gonna get fucked here tonight, but it's not gonna be me. I'm outta here."

"Wait. It's not that easy, babe. Those guys aren't just gonna let you walk out the door now that they've seen you. They aren't the type to take no for an answer."

I hated it, but I knew he was right. I could tell as soon as I had seen those bozos that they weren't the kind of people you invite over for Thanksgiving dinner. I was stuck between a rock and a hard place. Well, three hard places was more accurate. Jimmy had said I had to do "them", which I took to mean all three. Don't get me wrong, it's not like this would be the first time I had taken on more than one guy at a time, but before it had always been my idea, and not something I was being forced to do. I didn't want to be passed around like a cheap whore by those gumbos, but Jimmy was really sweating bullets. He was really worried. I finally decided that I'd done worse things in my life, and I would be helping my guy.

"OK, let's get it over with," I reluctantly agreed. "But you're not getting rid of your debt, Jimmy. You're just transferring it, because you are gonna owe me, big time. Got that!"

'Thanks, Shayna. You're probably saving my life, or at least my face. And I don't blame you for being pissed. I never meant to get in this deep. I thought USC was going to run the table this year. How was I to know..."

"Jimmy, just shut up. I don't care how you got yourself ... no ... us, into this. I just want to get it over with. So, who's first?"

"I don't know. We didn't talk about that. Let me go tell them that you are ready and see what happens."

I glared at Jim's back as he went out the door, but he was smart enough not to turn and look at me. As I stood there in Jimmy's bedroom waiting, I felt kind of stupid. I didn't know what to do first. Should I wait for the first guy to show up and just take it from there, or should I take off my clothes and get on the bed, to save time? That seemed a little clinical, but then the whole deal wasn't exactly a weekend at Club Med. And what if the first guy wanted to take my clothes off for me? Or maybe they wanted to watch me strip. They looked like the kind of guys who might be hanging out in a titty bar when they weren't about to collect an account receivable by raping the debtors lady friend.

I was still standing there trying to decide what to do when the door opened. All three of the Gambino brothers walked in. A gang-bang, huh - I should have seen that one coming. Oh well, I had wanted to get it over with quickly.

The old fart was still in charge. "My, look at you, darlin'. Are you a little shy? Come on, show us what you got. Let's see those tits."

I really didn't like that guy. I would have liked to wipe the smirk off his face, but he was holding all the high cards. I tried to read his mind to see what he wanted. I couldn't decide between just getting undressed as fast as I could, or putting on a show for him. I decided to put on my stripper act, something that I'm pretty good at if what my boyfriends have told me is true. I concentrated my attention on the gorilla. He was the one that I had to please to save Jimmy's sorry butt. The younger guys were just standing there, looking kind of embarrassed about the whole thing. They were well trained though, patiently waiting for their instructions like a pair of guard dogs.

I took my time pulling my sweatshirt over my head. I glanced at Mr. Hairball and saw his baggy eyes eating me up. I even gave him a slight smile as I slowly unhooked my bra and held it over my breasts for a moment before dropping it. I wanted to tease him, but knew I didn't dare go too slow and incurring his anger. So far, he still seemed to like me, and I considered that a good thing.

"Oh yeah ... those are nice and natural, honey. I hate plastic." He snapped his fingers, like summoning a slow waiter. "Now let's see some pussy."

He was showing impatience, or excitement, or both. It was hard for me to read his expressionless face. Probably a good poker player, I figured. I decided to drop the strip-club routine and get down to business. He was beginning to creep me out by just sitting there staring at me. Usually by the time I show a guy that much skin he can't keep his hands off me. I have breasts that men just seemed to love to fondle and suck on. They're not that big, but my large, puffy nipples seem to make up for what I lack in overall bulk. But this guy, sitting inches away from me, hadn't even tried to touch one of my tiny titties. The other two guys were still standing there like department store dummies. They seemed to be afraid to do anything without the bosses okay. I had expected all three of them to be all over me already, like dogs fighting over a bitch in heat. I was beginning to wonder if I had lost some of my sex appeal.

"Come here, sweetheart. That's right. Now turn around and bend over."

.... There is more of this story ...

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Story tagged with:
Ma/Fa / Reluctant / Coercion / Gang Bang / Oral Sex / Anal Sex / Voyeurism / Size /