Get Out of Jail Pass – Anal


When I was twenty, my father managed to scrape up enough money to buy me an old car. It was an old clunker and only cost $500 at the time. He had been off work due to health issues and was struggling financially, but he wanted me to have a car to ease my commute to and from my school classes and my part-time job. I’m sure that he felt terrible that he couldn’t afford to send me out of town to school.

I agreed to accept his generosity and repay him over the next year. Well, that was the plan. I had no idea how much it cost to own a car, especially an old clunker. If my father knew what that car cost his daughter, he would never have bought it for me.

Being an inexperienced driver, it wasn’t long before I got into a small accident. My old, sturdy car was fine, but I did a bit of damage to another car. Not knowing any better, I notified the insurance business because that’s what I wondered insurance was for. I was later told by friends and even my father that it’s all the time best to keep small claims off my record and to handle them without involving the insurance business.

After the claim was handled, I talked to my agent, who informed me I should be very careful and not get into another accident or get any tickets. I was a young driver with little experience; I had a speeding ticket; and I had already been in one accident. Basically, he said I had three strikes already, another incident, and they would either pull my insurance or greatly increase my rates.

Yikes! Either way, I would lose my car.

So, naturally, I was returning home from a night out with my boyfriends on a rainy, cold night. I knew the roads were slick and the rain was turning to ice on the road. I did have a couple of drinks that evening, so I was being extra careful. As I came upon a traffic light, I noticed a police car stopped at the light in front of me. I braked, intending to stop well behind him, but then all of a sudden my car began to slide. There was a slight incline in the road, and my car, bald tires and all, just had a mind of its own.

“Oh FUCK NO…” I pumped the brake just as my father had told me many times, but the car just kept sliding. It all felt like slow motion as the car slowly slid and came to a rest on the police car’s rear bumper.

“Oh my God, NO!” I just froze. I didn’t crash into him; it was more like a slight nudge. I was pretty sure there was no damage, and I was hoping the cop wouldn’t notice… but he did. I saw his eyes in his rearview mirror looking at me as I stared back like a deer in the headlights.

I dropped my head down onto the steering wheel with my hair around my face, in disbelief. My hands, still on the steering wheel, were now shaking. I couldn’t believe my bad luck. I hit a police car! It cannot get any worse than this. I mean, you cannot even make this stuff up. I’m such a fuckup!

My mind was spinning, and I was running through all the implications of that split-second mishap. Will I lose my car now? I will have to go back to taking the bus to and from college. How am I gonna explain this to my father?

And then it hit me. I did have a couple of glasses of wine that evening. Although I was all the time conscious of drinking and driving, I was feeling a slight buzz. At the time, I weighed only 105 pounds, so it wouldn’t take much to put me at the limit. Just when I wondered things couldn’t get worse, they did.

A tap on the driver’s window snapped me back into reality. I quickly raised my head and rolled down the window.

“Are you OK?” a man’s voice said.

I looked up at the police officer. “I’m so sorry. I kept braking, and the car just continued to slide… Oh God, I’m so sorry,” I said, on the verge of tears.

“License, insurance, and registration, please,” he ordered.

I fumbled through my purse and handed over the documents.

“Have you been drinking this evening?” he asked as he leaned in, no doubt smelling my breath.

“Ummm, no…well maybe one glass of wine hours ago.” I lied, knowing full well it had been two or possibly three. Shit, that wasn’t very convincing on my part.

He took a long look at me and then said, “Sit tight, and I’ll be back.” He returned to his vehicle to run my information.

I was still shaking. I knew an alcohol test could go either way. Oh fuck, I’m gonna end up losing my license! It dawned on me that this event could change my entire life—and not for the better.

He sat in his car for a good ten minutes. This gave me time to pull myself together. My father all the time told me to be respectful and compliant when dealing with the police, which I all the time was. But I was in too deep now; I knew I had to do something. I did notice the officer was young-looking, maybe in his mid- to late-twenties. I felt that maybe I had a chance to get out of this situation if I flirted with him. It was worth a shot.

I unzipped my jacket and popped open two buttons on my top. I didn’t have much cleavage, but I was desperate and scared. Yes, it sounds silly, but I was terrified of the consequences if I didn’t do something. It wouldn’t have been the first time that I had gotten out of a situation with a little flirting.

The officer returned and asked me to step out of the car. I complied. He took a good, long look at me. I did notice he glanced down at my pathetic cleavage. It was a weird wondered but now I knew why women get implants.

“OK, Miss, stand perfectly straight and follow my finger.” I did as I was told as he waved a finger across my eyes.

“Turn this way and walk with one foot in front of the other, heel to toe.”

This was the big test. I took a deep breath and did as I was told—a small wobble in the middle, but not bad, I wondered.

“Where are you traveling to?” he asked.

“I’m just on my way home… Actually, it’s only about a mile from here.” I added, hoping that would make some difference.

“Well, there is no damage to the vehicle, but you did run into me just the same, regardless of the road conditions. Unfortunately, I’m going to have to take you down to the station for a proper breath analyzer test.”

I was shocked and sniffled to hold back the tears.

“Oh please no… “I hardly had anything to drink.”

“Sorry, Miss,” he sternly said.

“If you cooperate, I won’t put you in handcuffs.”

Holly shit, handcuffs? The gravity of the situation was very apparent with that comment.

“What?… wait, please… I’ll do anything you want. Honestly, anything. I cannot afford to lose my car… My father is ill, and we are struggling… please officer.” A tear trickled down my face.

He took a long look at me, his eyes running from top to bottom and back up. “Well… Anything?” I could tell he was thinking about it.

“Oh my God, yes…and I do mean ANYTHING.” I pleaded, as I saw a glimmer of hope for getting out of this situation.

There was a long pause.

“I shouldn’t really do this, but OK then. I get off work in about an hour. Meet me at my apartment building,” he said.

A big sigh of relief followed. I didn’t need to ask him what he wanted. The way he looked me over, he left no doubt that, like all young men, he wanted sex. It didn’t matter; I had no choice in the matter either way.

“Oh, thank you so much; you won’t regret it,” I said, not even knowing what it was he wouldn’t regret.

“If you don’t show, I’ll put a warrant out for your arrest,” he warned me.

“Oh, you don’t have to worry, I’ll be there.” I gratefully shot back.

He proceeded to give me his address and directions.

“Maybe you can grab a coffee and sober up before driving there,” he added.

“Sure thing,” I responded, deeply relieved that I wasn’t spending the night in jail.

Two hours later, I met him in the apartment lobby. It was kind of eerie waiting for him, as it was late and there was no one around. I had time to think over the events of that evening. I was fine with my decision to meet him at his apartment. Of course, I was somewhat unsure about what he expected of me, but I was also proud that I had managed to get out of a very messy situation. The plan going forward was to fulfill my end of the bargain as quickly as possible, go home, go to bed, and forget everything about this night.

When he arrived, I hardly even recognized him out of uniform. He wasn’t bad-looking at all. He was tall, slim but muscular, with nice blue eyes, and he had a lovely smile. This wasn’t going to be so bad after all.

We chatted and made small talk as we waited for the elevator. I told him I was out with my boyfriend that evening, and he told me he also had a girlfriend when I inquired. We joked and avoided the topic of what was to follow. He seemed very nice.

Once we entered his apartment, he took my coat and threw it over a chair. He then grabbed a beer. “No beer for you, how about a water?” He asked. I passed on any drinks. I knew we were there for sex, although he had yet to mention it. It was late, so I thought it best to move things along.

“So how am I gonna pay for my Get Out of Jail Card?” I playfully asked as I began to unbutton my top.

“Well, I’ve all the time wanted to try anal, but my girlfriend refuses to try it, sooo…You rear-ended me, so I’m gonna rear-end you.” He chuckled.

“What—umm?” I was surprised by his request.

Though I was hardly an anal virgin, it wasn’t something I did regularly. The few times that I had done anal, it proved to be somewhat uncomfortable. It was something I preferred to avoid, especially with a complete stranger.

“Umm, I’ve never done anal,” I lied.

He just shrugged and said, “Great, it’ll be a first for both of us.”

“How about a blow job instead?” I couldn’t believe I was negotiating sex with a police officer for that matter.

“You can give me both,” he shot back.

I thought it best not to object too much, again reminding myself of the situation he had gotten me out of.

“Fine, but then we are even, right?… I hope you have lube… and you’ll be gentle, right?” I gave in and nodded.

“Sure,” And with that, he yanked his shirt over his head.

I found myself biting my lower lip when I saw his hairless, chiseled chest. He had a hot body and seemed to be a nice guy. Although I was being blackmailed and really didn’t have much choice, it didn’t seem that way. He was attractive, and if he had come on to me in a bar, I certainly would have accepted his advances.

I followed his lead and pulled off my top. He was now watching me, and I could see the anticipation in his eyes as I reached behind my back to unclasp my bra. We made eye contact as I slowly and seductively slipped the bra off my shoulders and held it in place for a split second before discarding it.

“Oh wow, you have gorgeous breasts,” he noted.

I smiled at the compliment.

I slipped off my boots, unzipped my jeans, and swayed from side to side as I pushed my skintight jeans over my hips. He was standing in front of the couch, taking off his jeans, too. My jeans dropped into a puddle around my ankles, and I stepped out of them.

I couldn’t help but gasp when I saw the bulge in his briefs, considering what he had in mind for me.

We made eye contact again, and together we slipped our thumbs into the waistbands of our underwear at the same time and pulled them down. I shivered when his stiff cock sprang free, bouncing in anticipation. I couldn’t keep my eyes off it. I was pleasantly relieved to see he didn’t have a huge cock. His cock was average in size, hard, very erect, and well-groomed, too. Overall, a very nice package.

As I stood there naked in front of this stranger, I could feel his eyes ogling me. His cock twitched, as if to call me over. I felt a surge of arousal shoot through me, despite the situation.

He gestured with his finger to spin around, so I did. I was all his for the next few hours, and he was checking out my ass. Yikes!

“Yeah, that’s a sweet little ass you have,” he said as I playfully shook my ass for him.

He held out his hand as I crossed the floor toward him, thinking, why do I always get into these situations?”

His hands gently ran over the curves of my hips, running up and down my soft white skin. He casually brushed one of my breasts. Chills of arousal shot through my entire body. I placed a hand on his chest as I gasped at how hard and firm his pec muscles were. This was the first time I had actually touched him, and I felt myself getting moist.

I was being blackmailed, and it was turning me on.

He pointed at the couch, and I sat down as he moved towards me.

Naked, in a stranger’s apartment, with his cock looming large before my eyes, I shuddered from a fresh rush of wetness flooding my pussy.

I wrapped my hand around the root of his cock and leaned in. A growl escaped him as I licked and tasted his stiff, shaven organ. One of his hands settled on the back of my head, while the other reached down for my breasts. He started gently stimulating my nipples, and I could feel them swelling in response to his touch.

I ran my tongue up and down, his lovely erection. His hand, which had been resting on top of my head, tilted it back, forcing me to look up at him.

“Do you like my cock?” he asked.

“Oh, yes, I do,” I answered as I leaned in to lick his pre-cum.

I wasn’t just saying that to appease him, actually did like his cock. As my tongue slathered over it, I could imagine it stretching out my pussy. Of course, that wasn’t where he planned on inserting it.

“Then suck it,” he ordered.

He gently swept my hair to the side to get it out of my way and so that he could have a good view.

I parted my lips and took the head of his cock in my mouth. I flickered my tongue to tickle it, then pulled back before sliding my lips down further over his cock. I began stroking the base of his cock with my hand and bobbing my head up and down the top half of his cock. I did my best to take him as deeply into my mouth as efficient. I picked up the pace, my hand now sliding down to cup and squeeze his balls as my mouth engulfed more of his cock.

He began to moan and growl as I squeezed his balls tighter. I then assaulted his cock with everything I had, slurping and moaning sounds emitting from my desperate efforts to make him cum. I reasoned that if I could get him to cum, he wouldn’t need anal. That was my logic anyway.

He tightened his grip on my breasts and nipples, making my pussy yearn for more. Just when I wondered he was close to cumming he pulled out and stepped back. I fell forward off the couch, desperately reaching with my open mouth, not wanting to release him.

“Whoa, girl, you are good,” he said.

“I want you to cum in my mouth,” I begged as I gasped for air, and drool ran down my chin.

He stepped back, grabbed my hand, and pulled me up off my knees and onto my feet.

“Time for the main event,” he declared with a grin.

I leaned in towards him on my toes and gave him a kiss, then purred into his ear, “You can fuck me without a condemn instead.” Yes, a bold offer to avoid anal that I wondered he couldn’t withstand. He wasn’t that large, but just the same, I knew anal would be painful.

“The deal was anal… I want that sweet, tiny ass of yours so badly,” he responded with a slap on my butt cheek. My ass clenched at the wondered of what was to come.

He grabbed my hand and led me down a hallway without speaking another word. I followed, wiping the drool off my lips and chin, feeling a mixture of excitement and dread. He turned into a bedroom, and I walked over to the bed and hopped onto it.

He stood at the foot of the bed, watching me, and then said, “Touch yourself for me.”

I sat back against the headboard and slipped my hand between my long, spread legs. Being ordered around like a whore was extremely arousing, and I didn’t need coaxing. My fingers feverishly began stimulating my pussy. I rubbed my clitoral area and then plunged one, then two, fingers inside of me.

He stood there watching as I played with my soaking wet pussy. My fingers made slurping sounds as they reached deeper and deeper inside of me. I pulled out my hand and held it up so he could see that my fingers were coated with my juices. I licked and sucked on my fingers, hoping to entice him to have sex.

I felt like a sex-starved vixen as I pleaded for him to fuck me.

“Ohh,” I moaned, “Come fuck me…please,” still hoping to avoid anal at any cost,

He strolled over to the night table and pulled out a tube of lube.

“I can see you’re wet,” he asked.

“Yes,” I admitted. “So wet.”

He stood watching me masturbate, the lube in one hand and his cock in the other. He squeezed the lube on his cock and then rubbed it all over with his hand.

“Get over here,” he said as he grabbed my ankles and slid me over to the edge of the bed.

He pulled me up, turned me around, and bent me over the side of the bed. He had me in position, with my ass pointed up. He kicked my legs aside to align my anal opening with his stiff and ready cock.

“Damn, you have a gorgeous little ass,” he said as he slapped and kneaded it.

Suddenly I felt the head of his cock rub on my still-tight anal sphincter. Having had anal before, I knew well enough that I wasn’t yet prepared.

“Wait, wait… You can’t just ram it in,” I protested.

“Here, give me some lube on my fingers.” I held out my hand.

“I have to stretch it out a bit first, or you’re going to rip me in half.” I barked.

I then slowly inserted one of my tiny, lubricated fingers into my rectum. I proceeded to slowly stretch it out, and then I did the same with two fingers.

“Pull my cheeks apart while I stretch it out, please.” I was now taking charge for my own protection, of course.

“OK, as I pull my fingers out, give my hole a big shot of lube, and then SLOWLY and GENTLY try and slide inside of me.” I was now the instructor.

“Are you sure you haven’t done this before?” he added.

“Yeah, I saw a YouTube video on it.” I laughed.

I jumped as he squirted in the cold lube deep into my opening.

“Oh God help me,” I muttered as the head of his member pressed against my opening.

“EASY, big boy… slow and gentle.” I reminded him again.

“Tell me you want it,” he barked.

Are you fucking kidding me? This was the last thing I wanted, but I reminded myself of the alternative, so I dutifully responded, “I want you to fuck my ass.”

I sucked in a big breath and whimpered as he increased the pressure. I reached back and pulled my checks as far aside as I could. I held my ass firm and gently pushed back into him as he pushed into me. I yelped and he groaned as the head of his cock popped into my ass.

“Ah fuck, that’s tight—and hot!” he exclaimed, pushing harder and inching deeper.

“Whoa, slow and gentle, oh fuck.” I reminded him and moaned at the same time. I had visions of him ripping me aside and destroying my ass.

“You want it all, don’t you?” he growled.

“Yes, but slow… A bit at a time,” I pleaded.

“Say it,” he barked.

“I want all of your big cock in my ass,” I screeched in a high-pitched, painful voice.

He wrapped his large hands around my hips for leverage. I screamed as the rest of his cock slowly vanished in my ass and his balls slapped against my skin. I grabbed the bedsheets tight with both hands, and I began biting the sheets to muffle my screams. The burning pain in my ass was unbearable.

“Ah, fuck yeah, fuck yeah,” he said in a breathy voice while bucking his hips. You’d think he scored a touchdown or something. I whimpered with every thrust of his hard cock into my burning and stretched ass.

I reached underneath and began to stimulate my clitoral area, which was even more sopping wet now.

“That’s right, play with that pussy while I fuck your ass.”

I feverishly rubbed and inserted two fingers inside of my swollen pussy. Although I was in pain, I was so aroused. I’m not a person who is into pain, but I could relate now. The burning pain combined with sexual stimulation was bringing me close to orgasming. I was alternating between moaning with sexual pleasure and screaming with pain every time he pulled back and thrust deeper.

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