Caught in the Crossfire Ch. 04

I guess, given the age of PC we are momentarily trapped in and the tortured snowflakes who might, inadvertently read something they consider icky, I should provide a trigger warning for this chapter. I know some of you are a bit squeamish when it comes to sex through the 'backdoor.' If so, reading further may irreparably damage your psyche and cause your eyes to melt from their sockets. In other words, beware; this chapter contains a lot of anal sex.

With that out of the way, Jack continues his punishment of Brittany using his favorite, disciplinary tool of choice. All is not lost for Brittany or her well-formed behind, however, as a very large puzzle piece falls into place.

**

The following week, Brittany answered Jack's knock dressed the way he wanted: a very short, light blue skirt that barely reached her thigh, along with a black, pullover, spandex top. The low cut, tight spandex hugged her massive breasts sensuously, leaving nothing to the imagination.

It was obvious she went the extra mile sexing herself up for their meeting, given that Jack liked her to parade around the room for him before they got started. She figured, 'Give him what he wants, and maybe he won't be such a prick after the fun-time session was over.'

It was also obvious she came to the motel braless, as her large, heavy tits noticeably jiggled and bounced as she stepped about the room. Jack told her to lift her skirt in order to check the other detail.

She was, indeed, pantiless. Jack took a moment to run his fingers across her bare mons and down her outer folds, feeling nothing by smooth skin. "Slick," he said, close to her ear.

Seeing the satisfaction in his eyes, Brittany was feeling good about herself, and asked, confidently, "So, what's it to be today, fucking, sucking, or both?"

"Money first," Jack answered, "Put it on the table."

Taking the brown-paper bag of money out of her purse, she noticed Jack taking his own brown bag out of his suit coat, laying it next to hers on the table.

She asked, "What's with the bag?"

"Something we might need for later. Give me your keys."

"What?"

"Keys, car and motel room, give me both." When she handed them over, he added, "Okay, let's go."

Brittany took a step back, saying with shock, "Wait...What?"

"Let's take a drive. I've been cooped up all morning. I want to feel the sun and wind on my face."

Brittany turned toward the small coat rack in the bathroom area.

"Where are you going?" he asked, grabbing her arm.

"To get my rain coat, I'm not going out in public..."

"Shut up," Jack said, as he pulled her out the door.

Jack drove around the city for a while, mostly using the expressways. He made a special effort to drive faster than normal with the windows down. Brittany spent most of the time trying to keep her short skirt from blowing up above her thighs and exposing her bare groin in the breezy interior.

"You know, you're really being an asshole," Brittany finally commented, while holding the hem of her skirt tightly against her legs.

Jack said, laughingly, "Why, just because I want to show off my girls sometimes?"

"Show me off? And what about that? It's pretty irresponsible of you, don't you think. What if you get pulled over because you're driving too fast? What if the cop recognizes me, my car, but you're the one driving? What happens toour secret then, if Santos hears about this?"

"For your information, I'm sticking to another precinct. This area's controlled by the fourteenth. Your asshole husband's precinct is located across town. So, I doubt anyone we may meet would recognize you. Still, you have a point. I don't like trusting to luck." Jack finished his statement by taking his foot off the gas.

Now, Jack drove well below the speed limit, and in the passing lane. It wasn't long before irate drivers behind him had to pass him on the right. Of course, when they did, and turning to flip off Jack and yell some obscenity as they passed, they got a good look at Brittany and her magnificent jugs.

When they caught a glimpse of her, most of the drivers honked their horn in celebration. A few even slowed down, matching Jack's speed so that they could get a nice, long view of Brittany.

Brittany's face turned as red as her hair. For each passing car that honked, she slumped further down into her seat, trying to remove, if not herself, then her breasts, completely from view.

Jack halted her slumping by putting his hand on her bare thigh, while commanding, "Sit up straight!"

She did as told, while pleading, "Please, could you move into the right lane or go faster, at least."

"Faster? Now you want to go faster. Make up your mind. And why should I get into the right lane? You're a beautiful woman. You should be proud to show yourself off. No one will see you if we're in the right lane. "

"Please," Brittany said, emphatically.

He sped up and drifted back into the right lane. However, Jack kept his hand on her thigh and continued to slide it, and subsequently the hem of her skirt, up toward her crotch. Brittany tried to pull the hem down, but Jack wouldn't allow it. Finally, Brittany clamped her knees together, wedging Jack's hand tightly between her thighs.

Jack pinched the soft, sensitive flesh of her inner thigh, making Brittany yelp in pain. Then he said, harshly, "Let go of your skirt and spread your legs. I said spread them! Now! Stay that way until I say otherwise. If I have to tell you again to sit up straight with your legs spread, I will pull over along the side of the expressway and make you suck my cock. Understand?"

Brittany only nodded her head in response, sitting rigidly with her legs spread, the skirt hiked up around her hips.

Jack kept his hand high on her thigh, and kept a mischievous pinky finger gently touching and rubbing all around her outer labia in a playful manner. Even with the breeze blowing through the opened windows, cooling the interior, he could feel tremendous warmth radiating from her groin.

Taking and exit into the downtown area, Jack found a wide street with a lot of businesses, ensuring there will be a lot of delivery and semi-truck traffic, loading and off-loading merchandise.

Jack pulled up to the first truck he saw stopped at a light. The truck driver, situated much higher, could easily look down and into the car at Brittany.

From her low vantage point, all Brittany could see was the driver's arm resting outside of the open window and the top of his head. The driver had yet to notice her. Brittany flinched while comically looking around the car for a place to hide. She trembled in dreadful expectation at being discovered.

Seeing Brittany shift about in her seat, Jack reminded her, "Don't you dare move."

When the light turned green, Jack drove alongside the truck, matching its speed. When they both had to stop for another light, Jack told Brittany, "Ask the driver if this is the way to State Street."

She gave Jack a wide-eyed look of disbelief.

Jack barked, "Do it!"

Not daring to look up at the driver, she asked, "Hey mister, is this the way to State Street?"

Minding his own business as he waited for the light to turn green, the driver of the truck either ignored or didn't hear Brittany's question, and continued to stare at the light.

Brittany asked a second time, and then a third, before getting the driver's attention.

The driver finally turned his head toward Brittany, looked down, and said with irritation, "What the hell, lady, you're on State Str..."

The driver stopped in midsentence. Staring down at Brittany, the driver first noticed her large breasts and well defined cleavage. He just about stripped a gear when he noticed her skirt jack-up above her hips, legs spread, and her cute, naked, camel-toed labia protruding away from her groin.

Before the truck driver could say anything, Jack sped forward as the light turned green, then stopped for the next light. The truck came lumbering up alongside the Mercedes, screeching to a halt several car lengths behind the next car in front of him.

Brittany didn't make eye contact, keeping her eyes forward, but she felt the driver's gaze all over her. Whispering harshly to Jack, she said, "You really are a fucker!"

"Be nice to the guy. Don't be shy. Say hello. You're giving him a thrill."

When Brittany looked up, she saw the truck driver wearing a big, Cheshire cat grin. She did as Jack told, and gave him a weak smile back. Leaning further out of his cab, the driver asked, "How much for you to come up here and work on my drive shaft?"

Insulted that the driver would pay her like a whore, Brittany dropped her smile and said, "Fuck you, pervert," but her voice was drowned out by the other cars honking behind her as the light had already turned green.

Laughing, Jack sped up and turned down a side street, losing the truck in the process.

He spent the next hour repeating the pattern with other truck drivers. Overall, Brittany ended up receiving more than a few solicitations for sex, as well as one marriage proposal.

"Well that was fun," Jack commented, nonchalantly, after they were done.

Brittany didn't answer. Too angry for words, all she could do was sit with her arms crossed, fuming.

As Jack turned onto a main thoroughfare that would take them back to the motel, he asked, "All this driving's made me thirsty. You thirsty?"

Brittany wouldn't answer.

"I'll take that as a yes," he said, pulling into the nearest convenience store.

Jack held the car door open for her.

Brittany shot daggers into his face with her eyes, and barked, emphatically, "I'm not getting out of this car until we get to the motel."

"Yes you are. I'm not going to carry your drink out for you."

"I'm not thirsty! I'm staying here."

"Get the fuck out of the car, or I'll throw you out and leave you here."

Once inside, Jack took her on a long, winding walk through the store, while continually yanking on her arm so that she would keep up. Throughout the whole ordeal, Brittany's face remained a brilliant shade of scarlet.

Jack stopped their trek in front of the soft drink dispenser, and taking an inordinately long time looking over the selections.

Brittany asked, with both frustration and embarrassment in her voice, "What are you doing?"

"I'm seeing what they have."

"Well, pick something so we can get the hell out of here. I swear, everyone can see right through this skirt and right at my bare ass."

Ignoring her comment, he asked, "What do you want?"

"Nothing."

"You sure," Jack said with suspicion, "I'm thirsty. Aren't you thirsty?"

It was obvious Jack wasn't going to leave until she got something, so she relented, "Yes. Fine. I'll have something."

"What?"

"Anything."

"Diet?"

"Yes, diet."

"Diet what?"

Brittany hissed, "Anything! Diet anything! Coke! A diet fucking Coke, okay? Please, just get me anything so we can go."

"What size?"

Brittany would have screamed expletives in his face, but figured it would draw too much attention. Instead, she replied, quietly, "Small...a small diet coke."

It was about this time that a middle-aged man entered the store and went over to the bottled drink coolers. Brittany's back was to him as he stood about ten feet away, giving no particular attention to either her or Jack as he looked over the store's selection. He was about five to ten years older than Jack, balding, a little taller than Jack, but not nearly in as good of shape.

Jack didn't notice a ring on his finger, although it probably wouldn't have mattered if he had. He'd been waiting for this precise moment. Pretending to have butterfingers, Jack fumbled and dropped a cup. As it bounced on the floor between him and Brittany, Jack said to her, "Pick that up for me, will you."

Brittany understood the situation immediately, and stayed still as a statue.

Jack whispered, harshly, "I said, pick it up!"

Brittany tried to lower herself by bending down at the knees, but Jack stopped her, saying, "Keep your legs straight. Bend over at the waist, and pick up the cup, bitch."

Brittany quickly bent over and grabbed the cup. She would have stood up just as quickly, except Jack put a hand on her back and held her down.

It took a few more moments before the other man noticed Brittany. Once he did, he continued to stare right into Brittany's bare ass, taking no notice of Jack.

Jack finally said to him, "Like what you see?"

Having been caught as a 'Peeping Tom,' the guy quickly turned back to the coolers without making eye contact with Jack.

Jack asked again, more firmly, "Do you like what you see?"

The guy turned as red as Brittany, and stammered, "S...sorry...I didn't mean to look, but it's...it's kind of hard not to notice."

"No problem man. The girlfriend gets a little rambunctious when I take her out. She always likes to give guys like you a show. I've given up trying to stop her."

Jack waited for a response, but the guy only continued to silently stare at Brittany's rump. Jack then asked him, "Looks like you're interested? How much would you give me to tap that fine ass?"

"What? Here?"

"Bathroom's open. So, how much?"

The guy looked around nervously, before responding, "I-I only got a twenty."

Jack slid his palm lovingly across, as he commented, "That's all, only twenty dollars to tap this fine piece?"

The guy swallowed hard, and said, "There's an ATM. I could get more..."

Brittany had enough. Straightening up, she bolted out the door.

She was waiting for Jack in the car, and didn't say a word to him on their drive back to the motel.

As soon as he closed the door to their room, Brittany began slapping him about the face and neck, saying with real panic in her voice, "Goddamn it, don't ever do that to me again."

Jack easily grabbed her flailing hands. Wrapping them, and his arms, around her, he pulled her tight against his chests, saying, "All right, enough. Now, wasn't our drive fun?"

Brittany yelled into his chest, "No, it wasn't! It was degrading and humiliating, and what if someone recognized me."

"No one recognized you. How do you feel, knowing that?"

"What do you mean?"

"How did it really make you feel, dressed like you are, seeing all those guys drooling over you and honking their horns in approval?"

"I told you. It was humil..."

Jack cut her off, "Besides that. Deep down inside, how did it make you feel? What was it like knowing you gave that guy in the convenience store a raging hard-on, and that he would have paid anything for a little turn with you? How did it feel being desired like that?"

"I keep telling you, it was all humiliating for me."

Jack put a hand near the front of her groin. Even through the heavy fabric of the skirt, he could feel her warmth. Giving her a knowing smirk, he commented, "You're such a liar. You're going to have to do better than this if you want to keep secrets from me. Now, once more, how does it feel being desired?"

Even though caught in a half-truth, Brittany still tried to answer with deflection, "He wasn't that good looking."

"That may be, but he wanted you badly. I bet he would've given you his credit card for just a small taste of your fine ass. Just like the others who saw you in the car. All those guys probably have to rub one out just to get on with their day, wishing they could have just five minutes with you. Was it really that humiliating, seeing their looks of desire, or was there something else you felt?"

"It was nice, I guess, once I got past being ogled like a whore," she answered shyly.

"It was more than just nice. It turned you on." This time he slid his hand up her skirt. Cupping her vulva, he felt nothing but a steamy heat. Tracing a teasing finger up and down within the groove of her folds, he said in almost a whisper, "Even now, just thinking about their looks is making you wet."

She blushed, turning her face away from his gaze.

Tracing her profile with a finger, he said, "It's all right to feel that way. There's nothing special or bad about those feelings. It means you're human. You're just like the rest of us, Brit, men and women alike. We all want to feel special. Most women want to be desired by men, and men want to be seen as virile by women. It's that simple."

Jack crooked a finger under her chin, pulling her head around so that she had to look at him. Her face was still flushed with embarrassment, but her eyes smoldered with barely concealed arousal. Smiling, he added, "You should get used to those looks from men and their reactions when they see you. You're a sexy woman, Brit. You've been hiding it up until now, but over these last few weeks, I've been bringing it out of you. So, get used to those leers, it will happen more often from now on."

Brittany was going to ask him what he meant by his last statement, but she felt him unzip her skirt, letting it slide down to the floor. The time for questions was over. It was playtime.

Jack sat in one of the chairs facing the bed, and commanded, "Keep your top on, and get into your favorite position on the bed. I want your ass pointing right at me." Once Brittany was situated on her elbows and knees, Jack told her, "Now, play with yourself. I want to see you play with your bald pussy like you do at home."

Brittany was already turned on and wet over what Jack had just put her through, but the thought of him watching her masturbate was sending her arousal into the stratosphere. The old mixture of lust and loathing was welling up inside her again. And, as with the last time, she was sure the lust would quickly win out.

She went right to her little button, massaging her clit vigorously. At the rate she was flicking, she'd be squirting in no time. So, Jack put the brakes on. "Not so fast, emerald-eyes. Slow it down. Let me see you fuck that tight pussy with your fingers. That's it, slip them all the way in. Now, play with your clit with your other hand, but do it slowly." Jack continued to bait her with erotic talk, "If only those guys could see you now. I bet every one of them would come in their pants. You should have seen the look on that guy in the convenience store, I mean, he got wood the second he saw your fine ass. After you left, I saw him go straight into the john, and I'm sure to jerk off."

His words had an astonishing effect on her. She never realized what kind of erotic effect she had on men. Yet, thinking back on the day, she definitely saw it in the faces of those who ogled her, and she could hear it in Jack's voice, now. Men desired her. Real men, like Jack.

Before she realized it, she was back, vigorously massaging her clit while rapidly pumping her fingers within her pussy...she came.

A fine trickle of ejaculate ran down her thighs and dripped from her fingers. She continued to play with her pussy, massaging the outer folds with the flats of her drenched fingers, bleeding as much of the euphoria out as she could.

Finally, she collapsed onto her stomach, momentarily satisfied.

Jack commented, "That was nice. I'm glad you're getting more comfortable with me and letting yourself go. This isn't so bad, is it?"

She was panting with her head resting on the bed, and trying to formulate an answer. Deep within her she knew what her answerwould be. Instead, she told him what her answershould be, "Yes, it is bad. I don't like it or you."

"You're lying again," Jack commented, laughingly, "Stop lying to me."

Brittany heard the paper bag on the table rustling. Seconds later, Jack threw some items next to her.

Brittany turned her head and saw that one of the items was a dildo, shaped exactly like a dick. Although much smaller than Jack's cock, and slightly larger than Santos, it had a nice shape and size—about six inches and well proportioned. The other item was a bottle of lubricant. Looking back at Jack, she asked, "What's this for?"