Gypsy Cab

by Jefferson James

So, I boosted myself a car. I did my homework and was sure to get a model that had tinted windows and child locks, those doodads that make it so the back doors can only be opened from the outside. A couple of blocks down the street and around the corner I swiped a new license plate for it. The city I live in has a fleet of gypsy cabs that use magnetic signs on the doors to identify them. Getting a sign for the side of the car facing the sidewalk was a cinch.

I had to cruise around for a couple of hours before I found the right girl; one on her own who was hot enough to be worth the risk. From the way she was dressed, the one I found looked to be an executive-type who had been putting in some overtime. I’d say she was in her early to mid-thirties.  …pretty face, long legs, and a nice set of sweater puppies. I negotiated a good rate and she got it. Five minutes later and I was sticking a gun in her face.

The brass plate on her jacket said her name was Stephanie and she was a comptroller, whatever that is. I didn’t know, and I didn’t care. She was a cunt donor as far as I was concerned. Grinning, I watched her try the door handle. I was real glad I’d thought of that little detail. Next, she went for her purse.

Just hand it here, Stephie,” I said. “You can’t get anything out of it fast enough to do you any good, anyhow.”

The expression on her face didn’t change, but I could tell she was wondering if what I was telling her was true, or whether I was bluffing.

“If you want to get out of this car alive, you’re going to do what I tell you,” I said, giving her an icy stare. “It’s as simple as that.”

Her big brown eyes closed and she offered up her purse. When she opened them again, the fear and helplessness in them was as clear as day. The traffic light I was stopped at had changed and it was time to drive again. I kept a close eye on her, though. She sat back in the far corner as far from me as possible and tried her best to be invisible.

“You’ve got my money and credit cards,” she said finally, in a loud whisper. “Let me out. My cell phone is in there too. You’ll be long gone before I could possibly call the police, and I won’t anyway. Just let me out.”

I ignored her. The next time I had to stop for a light, though, I turned around and told her, “I haven’t gotten all I want from you yet.”

I let her think about that for a while. Once we were moving again, I adjusted the rear view mirror so I could look her in the eyes.

“Show me the twins,” I said, making sure she heard the firmness in my voice. “…jacket open, sweater up, and bra too if you’re wearing one.”

Stealthily trying the door handle again, she said, “You don’t want to do this; armed robbery is one thing, but…”

“Murder is another,” I said, turning down a dark side street. “Did I mention that if you want to get out of this car alive you’ll do what I tell you? I’ll empty this gun into you, find another car and another girl without thinking about it twice. You wouldn’t be the first silly bitch to think her honor was worth dying for.”

I was lying, but she didn’t need to know that. I wouldn’t shoot her, if it came to that. I hadn’t even planned on the armed robbery part of it all. It would be my first rape, but fucking her was the plan. Fucking a hot chick, a hotter chick than I could get any other way, was what I had in mind from the start.

Stephanie shrank back into the corner, trying to do the I’m-invisible thing again. At the next stop sign, I turned around, pointed the gun directly at her head and said, “It’s decision time. You going to do it, or not?”

My sexy little captive shuddered. Her eyes closed and she swallowed. Then, just a heartbeat before calling my bluff, she gave me a little nod. Trying not to look too surprised or excited, I smiled, turned back around and drove on.

For the next couple of blocks, Stephanie didn’t move a muscle or make a sound. After about the fiftieth glance in the mirror, her jacket was open and her sweater was on its way up. At the next stop sign there was nothing between her melons and me but a bra.

“Keep going, Stephie,” I said, noticing the look of apprehension and humiliation on her face. “This scenic tour isn’t over until I’ve seen the real estate.”

Her eyes flitted from side to side as if she was looking for a knight in shining armor or something. I took a quick look around too. The area was totally deserted. There was no one for as far as the eye could see in any direction. Even so, it was almost a full minute before Stephanie sighed in defeat, undid the clasp between the cups of her bra, and I found myself looking at the biggest, most beautiful tits I’d ever seen in person. They were so white they seemed to almost shine in the dark.

After a real good look, I drove on. We were getting deeper and deeper into the part of town where anyone out as late as it was would be minding their own business. The only guys around would be dealing drugs, fencing stolen stuff, or raping a girl of their own. Stephanie knew it too. I could practically taste her fear and dread.

“Don’t worry,” I said, to her in the mirror. “If you’re a good girl, I won’t be leaving you here. I’ll let you go in a better part of town.”

She didn’t thank me or anything. I think she was too worried about my exact intentions to be grateful. She may or may not have known for sure that she was going to be raped, but she more than likely suspected that was the case. I thought about spelling it out for her, but I was kind of enjoying the game of whittling away her hope a little at a time.

“I’m willing to bet that a classy girl like you wears matching underwear. I’m right, ain’t I, Stephie?” I asked, glancing back at her.

Not surprisingly, she didn’t answer. I heard a sniffle, and then another. She knew at least what was next. The sniffling turned into quiet sobbing and my dick got harder. Grinning at her in the mirror, I said, “That’s right, sweetheart. They’re the next stop on our little guided tour. You can pull your skirt up around your waist, or take it off, but I want to see what you have on under it. You’re going to show me too, if you know what’s good for you.”

This time, she pretended to be invisible a whole lot longer. I thought I was going to have to threaten her again, and was just about to when I heard her pitiful, cracked and shaking voice say, “Please don’t hurt me. I’ll be cooperative. I’ll do whatever you want, just please don’t hurt me.”

I felt like whooping with joy, but I knew I didn’t dare. I had to stay scary or I could blow the whole thing. I didn’t want to blow it. I wanted her blowing it, if you know what I mean. Keeping my poker face on, I looked at her in the mirror and calmly, coldly, said, “Panties.”

For the next minute or so, Stephanie didn’t say another word or budge an inch. Except for the occasional whimper, the backseat was so quiet you could have heard a pin drop.  Then, as I slowed to a stop at the next intersection, I heard a soft mewling sound and a nylon zipper going down.

With tears streaming down her cheeks, and me turned around and watching closely, Stephanie began scooting her way out of her skirt. It was obviously too tight to have been pulled up far enough to do what she knew she’d be doing before getting out of that car – spreading her legs. The fact that instead of just giving me a beaver shot she was actually getting ready for the inevitable, made my cock throb. Things were going smoother than I dared imagine. That one little detail proved she’d made up her mind to let me fuck her.

Her underwear didn’t match. The bra was white and her panties were black, probably because they matched her skirt and sweater and she had been worried about show through. I didn’t care whether they matched or not, though. Her bra was out of sight, having disappeared behind the lapels of her jacket. Her panties would be disappearing soon too.

“Nice,” I said, gesturing to the skimpy bit of lace that was barely covering her pussy. “Give them here. You can leave your heels and knee-high stockings on if you want; I’m not into feet.”

She hesitated, and I looked around making sure no one else was out and about. Then, turning back at Stephanie, I gave her a look that said we weren’t going any further until I saw some pink between her creamy white thighs. She cringed, gave me a little nod like before and slid her panties to her knees, to her ankles, and off, placing them in my waiting hand.

“Let me give you something in trade,” I said, setting them aside and retrieving a pair on handcuffs from the console between the front seats. “Put these around one of your wrists and turn around with your hands behind your back.”

Stephanie shuddered and shook her head, saying, “You don’t need to do that. I’ll cooperate. I told you that.”

“Cooperating is doing what I say,” I told her. “Do it.”

She did.

“Please don’t hurt me,” she said again, shaking like a leaf. “I won’t give you any trouble, I promise, and I won’t tell anyone, I swear to God. I’ll do whatever you say, just don’t hurt me.”

I took yet another quick look around to make sure that no one had noticed a cab sitting way too long at a stop sign. There was not a soul in sight. Leaning way over the back of my seat I closed the other cuff around her trembling wrist. She started crying harder. I reached around her, gave her tits a good, firm squeezing and moved my mouth close to her ear. She tensed up for a second and then quickly relaxed, offering what I suspect was a token of cooperation.

“Just lie down and get comfortable,” I whispered. “I’ll be joining you as soon as I find a nice quiet place to park where we won’t be interrupted. It shouldn’t take long.”

Again, she did as she was told, lying down across the back seat.

Putting the car into gear, I called to her in a soft, almost seductive voice.


It was a good thirty seconds before her choked reply came.


Smiling to myself, I pulled away from the stop sign and asked, “You know I’m going to fuck you, don’t you?”

She answered with blubbering instead of actual words.

A few blocks later I spotted a drive-through behind an abandoned building that used to be a bank. As I turned around and headed back toward it, I called to her again.


It took even longer for her to stifle her crying enough to answer.


“You know I’m going to fuck you, don’t you?”


“…mouth, cunt and ass. You’re going to take it in all three and not give me any trouble, right?”

“Please! Not in the…”

I interrupted her.

“You said I could do what I want,” I said, with a patronizing tone. “I’m sure you weren’t lying to me. You meant it, didn’t you?”

Her voice was so low I could barely hear her, but she sounded quite adamant as she said, “Yes.”

“Yes, sir,” I said, correcting her.

“Yes, sir,” she repeated without a hint of sarcasm.

“You’ll let me fuck you and you’ll cooperate fully?” I asked, stopping the car and switching off the engine.”

She made a pitiful whimpering sound, choked back her tears and whispered, “Yes, sir.”

Turning in my seat, I smiled at her.


She nodded


She nodded again.


No longer able to keep from crying, her pretty face contorted and she started bawling.

“Ass?” I asked again.

She was carrying on so much I could barely understand her when she finally choked out, “Yes.”

A few seconds later, she gained a little control over herself and added, “Sir.”

“You’re a smart lady,” I said, opening my door. “That means I’ll be dropping you off at a public restroom somewhere so you can clean yourself up before you call another cab. First things first, though. My dick wants in you so bad it aches.”

When I opened the rear door of the car, Stephanie didn’t even look at me. She kept her eyes clenched tightly shut. I touched her shaking calf, and she opened her legs enough for me to get between them.

“I’ve never done it in the backseat of a car before,” I said. “Have you?”

She didn’t answer, but her legs lifted slowly until the left one was on the back of the rear seat and the right one was on the back of the front seat, indicating she knew the position necessary for such cramped quarters and had probably learned it from experience.

“Spent some time in backseats during high school, didn’t you?” I asked taking my dick out of my pants and feeling around with its slippery head for the mouth of her cunt.

I could tell she was bracing herself for penetration, more mentally than physically. She had all but stopped shaking. Most of her tears had dried up. She was still breathing hard, but more regular than when I first laid over her.

“I’ll bet that’s where you lost your cherry,” I said, pushing into her. “I didn’t get any when I was in high school. You might say I’m making up for lost time.”

Stephanie didn’t moan or groan, or anything. She went rigid and stayed that way as I stroked my way deeper into her sweet little cunt. Normally I hate it when a woman just lies there like the more strung out hookers do. On the other hand, knowing how much Stephanie was hating have a guy like me in her more than made up for any movement she could have done. She was slumming tonight whether she liked it out not, and she obviously didn’t.

“Are these real?” I asked, squeezing her tits and pinching her nipples.

She winced and nodded.

I mauled them good, crushing them together, pulling on them, and twisting them. She started squealing and writhing around. Now I was getting some hip action out of her, and plenty of it. The car seat was doing a good job of bouncing her up at me too. I drilled her like I’ve never drilled a girl before, pounding her cunt just as fast and as hard as I could.

It didn’t take much of that before one of us was cumming, and you can bet it wasn’t her. She was doing all she could do; screwing up her face in disgust and taking the slopping she was getting. I pumped her so full of scum I wouldn’t have been surprised to see it running out of her ears. I hadn’t creamed a girl like that since losing my own cherry to my drunk and passed out stepsister. Unlike her, though, Stephanie probably was using birth control pills and wouldn’t get pregnant.

When I was done, Stephanie was wet at both ends. Her cunt was drenched with semen and her face was soaked with a fresh batch of tears streaming from her clenched eyes. Her sexy body was quaking with humiliation and loathing. I could sense her dread too. Grinning, I caressed her moist cheek, thumbed her plump lower lip, and asked, “Are you ready to taste that mess between your legs? You’re mouth is next.”

Stephanie’s face twisted up even more. I pulled out of her and got up on my knees, tugging on her shoulders a little. Grudgingly but cooperatively, she scooted and squirmed her way down the seat, no doubt being forced to lie in her own slime trail. I’d shot so much into her, a lot of it had to have leaked out.

Because of how cramped it was in the back of that car, I had a hell of a time getting into position, but finally managed to. Using the backs of the seats for support, I lowered myself over her. Stephanie’s eyes stayed shut, but at the right moment her lips opened just enough to let my half-hard, cream-coated cock slide in. The feel of her gagging with disgust was awesome.

I stayed in the front of her mouth for a while so that her tongue got a good coating too. Then, I went for the gold, using my stick to play tonsil hockey with her, whether she still had her tonsils or not. I loved the gurgling sounds coming from her throat and the cute little way she whined. She was a good girl, though, cooperating by not just letting me fuck her face, but actually sucking gently like she probably knew she better. She saved herself a painful yank on her hair.

“Good girl,” I told her, over and over. “Good girl.”

My dick got hard in no time. Slipping it out of Stephanie’s mouth, I rubbed it on her face. Then, I scooted back and gave her tits a squeeze.

“Nice ones,” I told her. “Push them together for me. I’m going for a drive in Cleavage Canyon.”

As I titty-fucked her, I asked, “Does that feel good? Are you liking it?”

She shook her head.

Grinning, I said, “That’s too bad. You’re not hating it as much as you’re going to hate what’s next, though, are you?”

She cringed and shook her head again.

“That’s too bad, too,” I told her. “It’s time for you to turn over.

“Please don’t,” she whispered, the dread in her voice so obvious a deaf man would have heard it.

“Up the ass,” I said, still fucking her big, firm tits. “I told you that, and I told you I’d let you go someplace safer than this neighborhood, alive and well. You don’t want to make a liar out of me, do you?”

Cringing, Stephanie shook her head slowly.

“Good,” I said, moving off her. “Butt up and cheeks spread. Don’t take too long getting that way, either, or I won’t spit on it. An uncooperative girl gets her rump dry fucked.”

Stephanie tried her best, but the handcuffs made things real difficult for her. Even with my help, it took longer to flip over than I would have liked. A car drove by and I saw some people down the street. Still, things remained private enough and I didn’t have to abort my mission. Wetting my hand with my mouth, I lubed up the head of my dick and laid over her.

As I nudged Stephanie’s little wrinkled rear entrance, she kind of half sighed and half whinged. Then, I felt her relax rather than tighten up. She apparently had at least some experience in that department. I pressed on and in. She gasped a couple times and squealed a little, but took it a lot better than I expected. The head was in and the shaft was following it with no muss, no fuss. She was definitely not a first-timer.

In and out, in and out… I pumped her sweet little butt deep and slow, serenaded with whimpers and sniffling. I don’t think she was hurting, not in a physical sense. Having her tushie tapped by a total stranger, on the other hand, was a little more than her ego could take. She was a high-class businesswoman and had probably never even considered the idea of someone like me cornholing her, not in her worse nightmares.

I started going at her harder and faster. She rode out her butt pounding like a champ, adjusting the angle as I plunged into her as deep as I could. She was mortified, but obviously knew she only had a little more to endure and she was determined to do it with as much dignity as she could scrape together. She was clenching her fists and cringing deliciously when she felt the slippery wetness of my cum, but waited for my cock to lose some of its stiffness before squeezing me out. Her body shook and shuddered with revulsion when I used the crack of her ass to squeegee my dick, but other than that she didn’t move a muscle and didn’t make a sound as I climbed off of her and out of the backseat.

I drove her to a better part of town, like I had promised, pulling into a parking lot and stopping. After boosting another set of wheels to make my escape, I replaced the handcuffs with rope loose enough that she’d be able to get free with a little work. Then taking her earrings as souvenirs, I stuffed one end of her panties up cum-filled cunt and the other end up her cum-filled ass. When she squealed in complaint, I asked her, “That’s a lot better than a bullet in the head, isn’t it?”

Nodding, she whispered, “Thank you, sir.”

Winding some duct tape around her head to keep her somewhat quiet, even though I was pretty sure she didn’t want to draw any attention to herself, I gave her a kiss on each of her butt cheeks and disappeared into the night rather pleased with myself. Stephanie was the prettiest woman I’d ever fucked, but there were plenty more like her and some even prettier just waiting their turn to get it in the backseat of my next phony gypsy cab.

The End

(c) Copyright December 2010 by Jefferson James. All rights reserved. No portion of this story may be reproduced in any form without written permission from the author, except for a single copy, by and for the person reading this notice, for private reading.