Middle-Aged Hooker, End of Story

Author's note: I may have gone too far with this one. Hope it doesn't ruin the series for you. Look for more stories about Rita next year in a new series, Middle-Aged Wifey.

*****

This is the story of a foolish woman who stepped into trouble with both feet. But you know I come out on top, thanks to an undercover lover.

The detectives left me alone with the pimp. Not my choice of company but it was important for me to pick his brain, to learn what I needed to know to pass as one of his girls. They had shaved me below the waist and lubed me up with a viscous protective gel, dressed me in clothes that would have been flattering on a woman half my age and a tenth of my income.

"It's not too late to change your mind," said Ellie, the lady detective. "We're going to raid them tonight, regardless."

"You need intel. If you raid them and the girl is somewhere else... I want to do this. I want to help."

"I respect that, Rita. Glad to say, though, that you won't be alone. We have a man on the inside."

"How will I know him?"

"Oh, you'll know him. Remember Lieutenant Dick?"

*****

I was facing a potentially deadly situation. This pimp had provided the gang with women before. They came back roughed up but well paid. That is, they were roughed up and he was well paid. But this time they asked him for someone not so young, not so pretty, someone who wouldn't be missed. That's when he found a conscience and started cooperating with the informant. The agency saw their opportunity but only if they knew a chubby fifty-something woman who could fuck like a beast. Of course I agreed.

Despite my growing fears, though, I found myself distracted by the thought of crossing paths with Lieutenant Dick, as I called him. My husband would say that was just like me, to set out to do something selfless and somehow make it about me. A few years ago, Richard, because that really was his name, seduced me and exposed me, causing me to lose a job that I really liked. Even then, knowing what a dick he was, I took him back to bed, dragged him back. Now he was working for the very agency I hired to take him down. What will he think when he sees me?

*****

As the sun was going down, around eight o'clock, a white sedan pulled in through the garage door. A big mean-looking man got out of the passenger side. I had been shown his picture and told that his name was Marlin. Of all the known interactions with the gang he had been the point man. After exchanging small talk with the pimp he came over and frisked me thoroughly. Then he examined me like I was a brisket at the meat counter.

"You're in pretty good shape for a whore." He spoke finally. "You been doing it long?"

"Not long," I replied, recalling my cover story. "My husband couldn't keep a job so I have to pay the rent."

"What's your husband do for work?"

"He's... dead." I kept my tone neutral.

"How 'bout your kids? Can't they help?"

"We didn't have kids."

His mood lightened up hearing that and he exchanged a furtive glance with the pimp. He went to my purse and started rifling through it. The burner phone he pulled out and left on the table. Then he found the ivory-colored hard plastic vibrator.

"You think you're going to need this?"

"Sometimes guys like me to put on a show."

"You can put on a show right now." He had me turn around and pull down my panty-hose and bend over the table. Pushing my slutty red thong to the side, he inserted the vibrator deep into my pussy and twisted the base to turn it on. Then he pulled my hose back up. "All yours, Smoky."

His driver zip-tied my wrists and led me to the car. He lifted me into the trunk and I heard the car doors close, the engine start up. No turning back now. I was about to get a taste of undercover life and maybe I would live to tell about it.

*****

I was glad that the vibrator slipped past their scrutiny. It was awkward and not at all sexy to have it buzzing inside me while I lay in the darkness of the trunk. But that little toy had a secret. When the time was right, when I had the needed information, I could manipulate the vibrator to send a signal to the waiting detectives. But I hadn't counted on them leaving it running in my snatch. How long would the batteries last? I could have turned it off but I thought Marlin might not like that.

We drove around for what seemed like an hour. I could tell by the way they kept turning randomly that they were trying to make sure they weren't being followed. Ellie assured me though that they could reliably track us. Agents had previously followed them to various safe houses along the coast. With the ransom deadline approaching they were confident that where the gang was congregated the girl would be found as well. Confident, but not certain.

I heard an overhead door open and the car pulled into an enclosed space. Smoky helped me out of the trunk and freed my wrists. Marlon helped me remove the vibrator from my snatch and turned it off. He made me clean it with my tongue and slipped it back in my purse. Then he took me through a heavy metal door into a dimly lit industrial space. A half dozen rough-looking characters waited for us there, all dressed the same, black pants and dark gray shirts. They looked like a police lineup from a crime drama with one very handsome exception. Richard's eyes briefly widened when he saw me and I was afraid he might make a mistake.

"Where did you dig up this old fossil?" One of them sneered.

Marlin shoved me in his direction and the man caught me in powerful arms. "That's no way to talk to a guest. Apologize this instant."

"I'm sorry, babe," he said, not with sincerity, and forced his tongue into my mouth. His breath was not good. He shoved me to another man who also kissed me roughly. I was desperately trying to decide how a real hooker would respond to this. I decided to go along with it but try not to act too enthusiastic. To the sound of derisive laughter I was passed around and kissed and groped by some or all of them. It was hard to keep track.

When I found myself in Marlin's hands again he marched me over to a thin narrow cot and stripped me in a matter of seconds. He pushed me down on the soiled canvas and pointed to one of his men. That one undid his pants and climbed between my legs. No preparation, no teasing, no condom. He just stuck it in me and started fucking. I was so glad for the protective lubricant I had been treated with. Ellie said that not only was its slickness long lasting but it would offer some protection against physical damage and 'contamination', as she put it.

I wondered what would help my current partner finish faster, acting like I enjoyed it or acting like I didn't. I kind of went down the middle and acted like he was hurting me but turning me on at the same time. I closed my eyes so I wouldn't have to look at the ring of leering faces that surrounded us. I lifted my spread legs and wrapped them around the guy, pushed back against his thrusts even as I moaned in apparent pain. That worked for him, but to my surprise he pulled out just as he came and finished on my stomach.

I wasn't given any time to catch my breath before another man took his place between my legs. As he began thrusting, another man took his position at the other end of the cot and placed the head of his cock at my lips. I took him in my mouth and he pushed insistently to my throat. The onlookers gave a murmur of appreciation as I let him past my gullet and his balls were quickly pressed against my nose. He started fucking my mouth and throat and my considerable oral skills were seriously put to the test.

I had to concentrate so much on sucking this guy's dick that I couldn't give the one between my legs any special moves to help him along. My pussy was just a hole for him to fuck. I did want to hurry him up so I reached down with one hand and ran my fingers through his pubic hair, felt his slick penis as it screwed in and out of my cunt. With my other hand I reached up and caressed the ass of the guy whose cock filled my mouth. He let me guide him with my hand on his hip so that he wasn't bottoming out in my throat on every stroke, allowing me to find a good rhythm.

My pussy fucker finished first. He also pulled out as he came and I grabbed his dick and jacked it off for him, all over my stomach. Another man had taken his place before the one in my mouth filled it with semen. I guess if there was a rule about not coming inside me it didn't apply to my mouth. I didn't want to swallow but I didn't think I had a choice so I quickly choked it down. No sooner had I smacked my lips then another cock was pushing between them. I was getting comfortable and moving my hips so I brought both hands up to guide the newcomer in and out of my mouth.

Despite the fear and disgust I felt I was starting to get turned on. This got my juices flowing and helped ease the sexual beating I was taking. I felt hands on my stomach and legs, hands groping my breasts and pinching my nipples. So I guess my partners were enjoying me as well. All the better. The one in my mouth pulled out and brought his hairy balls to my lips. It was gross but I opened wide and licked and sucked them for all I was worth. He managed to get his mushroom head back into my mouth as he came but not before gracing my upper lip with a spurt. Four down, I thought, four to go. My ordeal wouldn't be over then. Not even close. But I thought they might let me rest a bit and I could have a look around.

I was pleased that my next customer for head was my old friend Richard. At last I would have a cock in my mouth that I actually wanted to suck. As he slid between my lips I received a third load of come on my belly and I prepared myself for the next. This one turned me sideways on the dirty cot and took me scissor style, which is actually one of my favorite positions. This forced me to rearrange myself for Richard. It wasn't the best angle for throat action but it did give me the opportunity to stroke his balls and squeeze the base of his cock.

My other hand went behind me to stroke the other man's thigh. While he screwed me he ran his hands over the cheeks of my ass and in response I started rotating my hips. I felt his thumb run up my crack and come to rest on my lubed-up bung hole. I was expecting this at some point. In fact, I started stretching myself out back there as soon as I agreed to serve in this capacity. The problem was that his thumb probing deep into my anus was sending my arousal into overdrive. I didn't want to have an orgasm but one was coming and it would take more effort to suppress it than to just let it happen.

I still tried to hold back which only built up the tension higher. I focused on giving Richard the best blowjob I could while my pussy and ass ached with pleasure. When my climax came it was violent and noisy. I shivered and convulsed so much that when they guy fucking me came he almost didn't get it out in time, spilling his semen all over my crotch and inner thigh. Richard had the opposite problem when he followed a moment later. He couldn't keep it in my mouth and ended up coming on my face and in my hair. All sweaty and come-streaked I slumped on the cot between them. Under other circumstances it would have been a great finish.

*****

The onlookers had enjoyed the show and they hooted and cheered. I briefly basked in their backhanded admiration before Marlin angrily cut them off. "The fuck is wrong with you shits? You surprised that a whore is good at being a whore. Don't fall in love with the bitch. She's just here to drain your balls."

He grabbed me by the hair and pulled me to my feet. He dragged me over to a corner of the room and picked up a length of chain that was anchored to the wall. The other end of the chain had a collar which he fixed around my neck. I wasn't enjoying this part. He picked up a hose from a coil and turned on the spigot. "Let's get you cleaned up, huh?"

The water was cold and the stream knocked me off balance. I covered my breasts and bare pussy while he sprayed me down. He turned off the water and I was left standing there, dripping and shivering from the cold. He got the cot and dragged it over to me. He had me get on it short-wise on my hands and knees. I knew what was coming next when he walked around behind me. Smack! His hand came down on my ass. Smack! Smack! Smack! Again and again he slapped me. Not going to lie, I love being spanked but not like this. He was hurting me. He wanted to hurt me. He wanted to mark me. But I stubbornly resolved to endure.

I was anticipating yet another slap on the ass when I felt his big hands on my hips instead. He rammed himself into my asshole, getting several inches inside me on the first try. It hurt... badly. I couldn't hold back the cry of pain which was drowned out a moment later by Marlin's triumphant laughter. He pushed and pushed his cock into my ass and there was nothing I could do to stop him. I had a moment of clarity then, thinking about the woman whose place I was taking tonight. She didn't always have a choice of who fucked her, and how they fucked her. I thought about women who were abused and enslaved and how I really had been pampered all my life.

And now I was literally being raped in the ass by this living piece of shit. As he began thrusting in and out of me, making a cock stroker out of my colon, I vowed to get even with this motherfucker. But first I'd have to survive. And to do that I had to let him do whatever he wanted. The pain was already subsiding somewhat. I was able to master myself and relax enough that the brutal fucking was not quite torture. It still hurt though. I was going to feel his first penetration for a long time. The other men urged him on, reminding me that I had an audience. I thought about the things I did when a lover took me this way, the things that would make it more pleasurable for him. But no use doing those things for Marlin. It wasn't about pleasure for him.

I was so relieved when he slammed into me extra hard and followed up with a few shallow thrusts. But then he yanked it out of me as hard as he had rammed it in and it hurt just as bad. I felt tears in my eyes as I wondered how a man could even want to treat a woman this way. I didn't have much time to cry though because another cock was in my ass without delay. This fucker was more gentle than Marlin, thankfully. But whoever it was had already come in me or on me so I knew it wasn't going to be a quickie.

I stayed up on my hands and knees but I hung my head while he fucked me. Marlin strutted around to the other side of the cot. Without warning he grabbed me by my hair and shoved his dirty cock in my mouth, still warm from my bowels. I turned my head away and spit out the filthy taste. He hit me so hard that I saw stars. He actually fucking hit me. The guy in my ass stopped mid-stroke.

"I didn't say spit, bitch. You clean me up right now."

I thought for a moment. His cock was dirty from my ass and I knew my ass was relatively clean. I'd seen girls do this in dirty movies, and guys too. I'd licked my husband's ass and he's licked mine. I could do this. I fought down the disgust that struggled against self-preservation and opened my mouth for him. I licked and sucked and swallowed and pretended it was something other than what it was. I kept at it until he was happy and stepped away. Then the guy behind me resumed his fuck.

After that there was no technique, no arousal, no variation. Some fucked my ass and some fucked my pussy. Some came around to let me suck them off and I no longer cared which hole their dicks had been in before then. They weren't pulling out of either hole and as they came in my mouth I just let it drool out on my hands. I felt defeated, broken. And the worst thing was that it was all for no use. I learned nothing from coming here and could only hope to provide a distraction until the place was eventually raided.

Finally the dicks stopped coming and Marlin helped me up on shaky legs. Then he forced me down on my knees for one final humiliation. The eight men formed a semi-circle around me and got out their cocks. The realization hit me and I lowered my head in shame.

"Look up, bitch!" Marlin barked and I lifted my face just as the first stream of urine hit me. Soon I was drowning in it. "Open your mouth, bitch!"

I opened my mouth and kept it open as long as I could. I knew I would have to swallow but I didn't want to do it more than once. As the streams began to subside I finally choked down a mouthful of acrid piss.

"Good job, slut. That wasn't so bad." He made it sound like it was over and I felt a glimmer of hope. But then he pulled out a wicked-looking knife and my heart plunged into icy water. "All right, let's cut this bitch up and feed her to the sharks."

"Hold up," a voice dissented. It was Richard, finally coming to my rescue. "Why don't we keep her until the morning? Then we can have some more fun."

"We're gonna have fun with the rich bitch tomorrow morning." Marlin replied. He gestured with his knife toward a row of doors on the opposite wall. A light was burning behind the one farthest from the garage entrance. Hot damn!

"But what if they pay the ransom tonight?"

Marlin laughed and several of the men joined in on his mirth. "It doesn't fucking matter, that's what."

The big man turned toward me, his eyes glittering with malice. So close I had come and fallen just short. Then something flashed before my eyes and I heard a sickening crack. Marlin howled in pain and fell to his knees, clutching his arm. Richard was swinging a mop handle like a martial artist and several of his former gang were already stretched out on the wet concrete floor. I grabbed the knife from where it had fallen and quickly unfastened the collar that confined me.

I streaked across the room to my discarded purse and retrieved the vibrator. I turned its indicators to say that the girl was present and that the situation was urgent. Just as I sent the message I felt a big hand on my neck. Marlin grabbed me and threw me backward, hitting my head on the floor. He retrieved the knife with his left hand, his right hanging uselessly at his side. He glared at me and I thought he would kill me right then. But he turned instead toward the heavy metal door at the entrance of the room where Richard struggled with another man over a rifle.

There was a thump that shook the ground beneath me. I sprang to my feet and ran up behind Marlin, fearful of his knife but desperate to help Richard. There was another thump, louder this time, and for lack of a better idea I grabbed on to his knife hand and threw my weight on it. It didn't have the effect I was hoping for. Even injured, he was incredibly strong. He tried to shake me off with his good arm. Once, twice, he shook me. Then there was an enormous thump and a doorway of light appeared where a door had not been before. Marlin shook me again and everything went black.

*****

I'm told the raiding party encountered minimal resistance. They bypassed traps and sentries by blasting their way through the wall, only to find Richard's surprise attack had largely neutralized the threat. The gang members were taken alive and were providing priceless information about an organization that spanned several countries. Marlin, sadly, did not survive the interrogation. Apparently he attempted to escape and had some kind of freak accident in the process. I understand a "flash-bang" is like a bomb. Not sure I want to know what a "prison pocket" is.

They found the girl in good health, thankfully. Her wealthy parents were very appreciative. Offered a reward, I persuaded them to make donations instead to charities that help women escape sexual abuse. I know I will be spending some of my own money and time helping these groups in the future. It was beyond time I stopped focusing on my own pleasure and comfort.