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."

Well, I wanted his attention, and now I had it. With my beautifully round ass practically in his face, I braced myself for a few smacks on the butt. He seemed like the kind of guy who enjoyed spanking as an appetizer. Instead, without warning, I suddenly felt one hard, callused finger working its way into my ass. He was exploring my colon like a proctologist who forget the rubber glove, and it didn't feel very good. Fortunately, it only took him a couple of seconds to find, or not find, whatever he was looking for, and he turned his attention to a place that I preferred to have explored. He started rubbing the outside of my pussy. Before my body could react to his caresses with a tribute of self-lubricant, he rammed his finger into that opening too, in the same hurried, insistent manner. He just wasn't a very patient man, which made all of his efforts at foreplay useless. I was still dry as he tried to finger-fuck me, but I didn't dare say anything. Instead, I turned around and gave him another half-smile. Make him think I was enjoying it, I reminded myself.

"All right, boys," he growled, at last giving me the smack on the ass I had been expecting, "she's all yours."

That was a surprise. Apparently he had just been warming me up for his puppets. While I had been occupied by Mr. Big Shot using me for a bowling ball, his "boys" had taken their clothes off. They weren't bad looking guys, not at all. It looked like they both spent a lot of time in the gym. I like guys with tight bodies and bulges in the right places.

Speaking of bulges, they had nice looking dicks too, which never hurts. Not too big, nice and smooth, and from the way they were standing straight out, they must have been glad to see Shayna. I was beginning to think that this evening might not be so bad after all. They still seemed to be a bit shy, so I decided to encourage them. "Don't just stand there with your wands waving in the breeze boys, come to Shayna."

Once they got within range of my hands I confirmed that they were indeed, stouthearted men. What's that saying, a hard man is good to find? Now I had two. Good for me. Tweedledum and Tweedledumber were as quiet and emotionless as a pair of bookends, but that didn't bother me. It wasn't conversation that I was looking forward to. I hadn't heard them say a word since I had first seen them. Maybe Monkey-Man had their vocal cords cut so they could never tattle on him (I really have to stop watching so many Mafia movies). Even with their dicks in my soft warm hands, they still stood there just watching me, like robots waiting to be turned on.

"Don't be shy, boys, I won't bite. Nibble a little maybe, but that's all." I smiled up at them, hoping that they were ready to relax and have some fun. But all I saw were the same vacant expressions that apparently were the only ones they were programmed for. It looked like I was going to have to do something to get the show rolling or we might have been there all night, staring at each other, while I held their dicks. Even King Kong was silent, content to just sit back and watch.

As I said, this wasn't the first time I had entertained two studs at the same time. The trick is to use everything my mama gave me. Eeny, meeny, miney, moe, who's the one I want to blow. I gave their equipment one more quick inspection and found that the taller one had a weird looking mole or something on his dick that I hadn't noticed before. I didn't think I wanted that in my mouth if I had a choice.

I slowly laid down on the bed, keeping my grip on Mr. Mole and pulling him down between my legs, guiding him straight to the Promised Land. I smiled at him as he settled into position. "That's right, honey, just slide that thing right up Shayna's love canal."

Those guys acted like they had never shared a lady before. Was I going to have to do everything for them? Now that I had one of them comfortably tucked away in my juicy pussy, I had to find a way to keep No. 2 busy. Trying not to disturb the guy who was already working energetically between my thighs, I slide over closer to the edge of the bed. I got close enough to get my hand wrapped around the shorter guy's dong. I pulled it toward my face, and with more effort than I would have thought it required, got my lips around his marble-like unblemished organ. He acted like having me give him head was not something he was looking forward to. I suspected that maybe they weren't used to performing with an audience, and perhaps that was holding them back.

Once I got busy giving the No. 2 pencil a header, I was able to relax a little and begin to enjoy the enthusiastic fucking my new friend was giving me. He had a real nice rhythm going, and I was starting to get hot. I really wanted to just lie back and concentrate on what the Adonis between my legs was doing to me, but I had to keep the guy in my mouth happy too. Since I couldn't get in a position to give him a proper blow job, I started using my hand also. He didn't seem to mind my combination hand job/header, because he started to moan and push his dick into my mouth. I let him fuck my face for a few seconds, but when he started to go too deep, I used my hand to restrain his enthusiasm. I don't do deep throat, at least not on purpose.

I concentrated on what I was doing, and in a couple minutes had both of them huffing and puffing like the little engine that could. I didn't think it would be long until both of them would be filling me with hot man cream, top and bottom. I wondered if I could get them both off at the same time, and cum myself too? I do enjoy a challenge. But just as I was getting close to achieving that goal, I heard that gravelly voice from across the room again.

"Get on top, doll."

I had almost forgotten about our one-man audience. I almost made the mistake of telling him to mind his own business and not stop a good thing just when I was starting to enjoy it. But I bit my tongue, remembering the situation and the fact that we were all puppets in his show. If he wanted to see me give his buddy a little cowgirl action, I could do that. I kind of like the feeling of power being on top gives me anyway. My partner put his arm under me, and easily flipped us over one handed. He was a powerfully dude, and he looked every bit of it lying beneath me now, tight abs and rippling biceps as he held above his erection, like a virgin about to be sacrificed. He lowered me down slowly, as I felt every inch of him sliding into me. Once our pubic patches were touching, I started working my hips as I hovered over him.

I was having so much fun now that I forgot about his brother in arms (or cocks) for a few seconds. I looked around and saw him standing beside the bed, looking somewhat like a forgotten puppy — with a big dick. I motioned for him to get closer so I could go back to sucking him off while I continued trying to screw his buddy into the mattress with my pelvic action, but he had something else in mind.

He got on the bed and stood behind me. For a moment I was confused, and wondered what he was doing there, but then I realized what he was up to. He slapped my ass, not harshly, but enough to get my attention. It was Silent Sam's way of getting me to stop my hip movements for a second while he hopped on board the Shayna express. I thought I knew what he wanted now, and felt it was only fair to warn him.

"Hey, listen," I said, turning around as best I could. "I'm really not ready for anal. I mean, you know a girl should be prepared, clean and all that, and you guys don't seem to have any lube, and I just think the whole thing is a bad..."

"Who said anything about anal," the gorilla growled again. (Can gorillas growl ... oh, whatever) He was still running the show.

No anal? Well then, just what was that guy doing behind me? That mystery was soon solved. He moved closer to me, feet on either side of his partner's legs, then crouched down and tried to push his hard cock into my already filled pussy. Yep, he was trying to DP me. I'd never tried that, not that the idea hadn't crossed my mind, but I had never had the itch at the same time I had two horny guys available to scratch it. Now, like everything else that was happening in that strange evening, it looked like I had no choice. And I didn't care. I was coping with a fetish that I hadn't even known I had.

I stopped and waited, unsure of what else I could do to help anyway. My body was just being used as a playground by a couple of overgrown adolescents, and there wasn't much I could do about it. It wasn't like I could flip a switch inside myself and make my vagina suddenly expand. I felt the second guy prodding around, seeking a way to slip inside alongside the already man-sized member in me, like the last passenger squeezing onto the subway. He seemed to be struggling, and I began to wonder if maybe I just wasn't built for that kind of action. He was persistent however, and eventually I felt myself widening to accept another body part.

I've always wondered if guys who like sharing a woman have some bisexual tendencies, or if they are just able to ignore the pressing of one dick against another in the interest of accomplishing the deed. Whatever, once the second guy breached the gate and was lodged firmly within my strained opening, he started to go to work. For a moment I was afraid that if they rubbed their dicks together too fast, we might catch fire. The whole thing was not as uncomfortable as I had feared it might be, but it wasn't exactly a walk in the park either.

"Ow, take it easy fellas. I'm not exactly a virgin, but I'm not loose as a goose either."

"Shut up."

I was really getting pissed at King Kong, and couldn't hold back my anger any more. "You shut up, Pops. No part of your body is being forced wider open that it ever has before, so just back off."

I cringed, waiting for the slap or punch or whatever. What I didn't expect was hearing him laugh. "You've got some balls, for a broad. Now shut up and show my boys a good time."

By then I was getting used to the odd feeling of having that much man meat in my tender parts, and felt myself actually responding positively. It felt like I was wetter than I had ever been, which definitely helped. I began to get that warm and tingly feeling all over my body, and knew my orgasm was not far away. I ignored the warning the ugly dude had given me. I couldn't help it - when I get close to cumming, I get vocal. "Don't stop, boys," I encouraged them.

That was probably an unnecessary thing to say. They were both pumping hard, and I was trying to match up the tick-tock of my hips to their syncopated thrusts.

"Unnnn ... yeah ... I'm cumming ... fuck me boys ... harder ... unnnngggg." Or something like that. You can't really expect a girl to remember every thing she says at a time like that, can you? Let's just say that I experienced a very big climax, and it was quite a surprise. Half an hour earlier I had been sitting at home watching some dumb movie, and then, pow, zoomie - my poor little pussy was being stretched by two guys I had never seen before. Life is interesting sometimes.

From the way he reacted, I was pretty sure that one of my new friends, the guy on top, came at the same time I did. He pulled out, his dick making an ugly, sloppy-sounding slurp as he did so, and collapsed on the bed next to me. I would have joined him, but his buddy, the one under me, was still working at getting his nut off. He must have been plowing through a very wet and sticky field by then, but he seemed really determined to get off. I decided to give him a little special Shayna hip action to help him out.

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