Caught in the Crossfire Ch. 04

"It's better if you get your ass worked in first with the dildo."

Brittany had little trouble catching Jack's drift, and said with ire, "Hey! Wait a minute! I'm not...I-I don't even let Santos fu...do that to me."

Jack asked, surprised, "Ever?"

"No!" she answered, forcefully.

"Wow, true virgin territory."

Brittany almost choked on her words, "I mean it, you're not fucking my b..."

Jack rolled his eyes, and cut her off by asking rhetorically, "Do we have to go through this whining every time we try something new? Brit, you know how this is going to go. You say no. I threaten you. Of course, we end up doing whatever it is that you think we're not going to do. In the end, you like what we did." Jack finished while laughing at his unintended pun, "In the end, you'll like it in the end."

Brittany remained adamant, "No!"

Jack warned, "It will be easier if you do this yourself."

"Why do you do this? Every time I think I'm beginning to like you, you start acting like a total prick."

Jack answered, amused, "Interesting. Do you want to like me?"

She hesitated for a long time before answering, "It makes it easier for me."

Jack began laughing.

Brittany could never accept being mocked, and screamed, "Stop laughing at me!"

Jack couldn't help himself, and continued laughing. This enraged Brittany more.

She started scrambling off the other side of the bed, but Jack grabbed her ankle and pulled her back. Pressing his knuckles hard into her spine, and thus, crushing her into the bed, immobilizing her, he said, "I'm not laughing at you, Brit."

"Right, I suppose you're laughingwith me, you arrogant fuck," she answered, sarcastically.

"No, I just find the circumstances funny. It's always the same with you housewives. You all bitch, moan, and whine that you can't do that or won't do this, but you really don't have a choice. So, you end up doing it anyway. Truth be told, most of you end up enjoying the ride, and can't wait for me to stick it in, again. You're all such shitty, little hypocrites."

"Is that what you tell yourself so you can sleep at night? That we end up liking it."

"No, that's what every one of you has told me over the years, so that I'll fuck you in the ass again, and again, and again."

"Please, I can't do this."

"Gee, where have I heard that before? Now, do you want to work the dildo in yourself, or do I have to hold you down and do it for you? And if I hear you whine one more time, I'll just stick my cock in your ass without a warm-up. You'll be screaming to use the dildo before I even get the head in."

When he felt her relax against his hand in compliance, Jack sat back down in the chair, and said, "Good girl. Now, don't be scared. I'll walk you through it. Start with your fingers. Put a healthy dab of lube on one or two and work them in and around your ass."

Brittany got back onto her hands and knees. She worked a lubed finger around her asshole first, before slipping just the tip in. When the initial entry didn't hurt, she slid her whole finger in.

"There you go, emerald-eyes," Jack commented, soothingly, "That wasn't so bad."

"God, this is sick, and it doesn't feel good!"

"Yeah, I heard that before, too. Usually right before you horny bitches start screaming in pleasure."

"I bet, screaming, but more like in pain..."

"Just shut up. It will go easier if you relax. Now work your finger around real good. Slide it in and out and all around, just like you're doing...very good, emerald-eyes. Okay, take it out and put some more lube on your fingers. This time, try to put in two."

Jack was patient with her, talking her all the way through the procedure. Of course, Brittany complained the whole time, but did as told. When it looked like she could manage two fingers with ease, he told her to try it with the dildo.

Although the dildo wasn't too thick, only a little more than two of her fingers around at the widest part, it still gave her a tremendous amount of trouble with insertion. Most likely her trouble was psychological, rather than strictly physical, as she tightened up from nerves each time she tried to insert it deeper.

She got it about a third of the way in, before she gasped through the pain, "I can't. It hurts too much."

Jack stifled a laugh. The visual of her kneeling, ass in the air, and with a dildo partially sticking out, was striking his funny bone. It was moments like these, her struggling in a good-faith effort with the dildo that made the past weeks with her incessant bitching all worthwhile.

There were more than a few times when Jack questioned whether Brittany was worth the effort. In his eyes, she remained unbearably whiny and combative. Worse, she continually questioned his decisions, and remained infuriatingly naive about sex.

Most of the other housewives he'd coerced would have already been going along with the program Jack laid out. It was logical to do so, given they didn't have a choice. Doing what Jack demanded allowed them to avoid inevitable hardships that went along with his wrath if they didn't comply.

Logic didn't apply to Brittany, however, who seemed to lack the necessary skills or mental aplomb for sexual survival that the other women possessed. Even after three weeks, she retained both an obstinate and obtuse nature, as if these characters were a matter of pride for her, rather than ones born from innate character, alone.

Jack continually found it difficult to endure all the frustration and trouble she brought, for a payoff that was still well in the future, and one that had little probability for real success. It was no longer about the sex, and never really about the money. No, Jack was enduring Brittany because she was his only means at revenge against Santos. Unfortunately, the truly frustrating part for Jack is he still hadn't a clue exactly how she could be used to meet those ends. He just knew she was his only means to those ends.

By now, Brittany was laying on her side, still whining about the pain. She jiggled, and pushed, and prodded the phallic device as much as she could, but it refused to slide in further.

Sitting next to her, he spanked her ass, making her yelp, and commented, "It's not going to go in like that with you lying on your side. Get on your knees."

Besides her self-imposed pain, now Brittany was nervous about how much pain Jack was going to inflict taking over the reins. She sobbed, apologetically, "I'm sorry, but it really, really hurts. I don't think I can take much more."

Jack didn't touch the dildo as it stayed inserted, lodged halfway into her behind. Instead, he put a soothing, massaging hand on the small of her back, and another on her pussy. "You've got to relax, emerald-eyes, or it's never going in. Just lay your head down, relax, let your body float free, and let my hands do their thing."

Her pussy was dry at first touch, making it obvious her pain and fear were real and dampening her arousal in the extreme. He continued to massage her for a long while, always saying, "Relax," in a soothing, hypnotic monotone. When he felt her vulva moisten again, he asked, "How's the pain?"

"Better," she answered, dreamily.

Using a comically detached tone, Jack teased, "Well here's your problem, baby, you've got some weird thing sticking out of you." Jiggling the dildo, he added, "It looks like an itty bitty spear. Were you speared in the ass by a wildling band of Pygmies? How'd that happen?" Brittany began to giggle as Jack continued to move the dildo back and forth. "Wait a minute, this isn't a spear. It looks more like a horn. Now I see, you're some kind of deranged unicorn, with your horn growing out the wrong end?"

Brittany laughed harder, making the dildo jiggle against Jack's fingers. Then wiggling her behind for effect, she said, "Shut up, that's not funny. Keep laughing and I'll gore you with my horn."

"It's funny from where I'm sitting." Jack pulled out the dildo, noting that it was too dry. "Now that's your real problem," he said, squirting a liberal amount of lube into her asshole and on the dildo, "Next time, don't be so stingy with the lube."

Jack straddled her back with his legs, kneeling just enough to restrain her movements without putting his full weight on her. Patting her rear in comfort, he said, gently, "Just relax. Put your ass higher in the air. Can you reach around my legs and grab your ass? Good. Spread those rosy cheeks for me. Nice!"

Jack gently worked the dildo into her, applying only a bit of inward pressure. Every so often, he worked it around, side to side, to relax her sphincter. A massaging hand always stayed at her pussy, causing her to relax even further. Slowly, with only a little added pumping to go along with everything else, he could feel her resistance slacken. It wasn't long before she relaxed all together. After that, the dildo slid all the way in as if on rollers.

A soft, breathless, "Oh," escaped Brittany's lips, as the stop at the end of the dildo touched her ass.

"Does it hurt?"

She answered, breathlessly, "N-No, but it f-feels different."

"See, I told you, you'd enjoy it."

"I didn't say that, I said i-it feels different."

Having the dildo fully in her ass wasn't the earth shattering, orgasmic-inducing revelation Jack had implied, but it wasn't all together unpleasant. Mostly it was a different kind of full feeling. Not the pleasurably intense fullness she felt when a man entered her vagina. The feeling in her behind is dampened, softer, more subtle in its intensity, as if the fullness were rooted much deeper inside of her.

When Jack slid the dildo within her, working the phallus in order to loosen her muscles further, she could feel the bulbous head pressing and tickling the near side of her vaginal wall. It was an odd feeling, an indirect stimulation of her sex that slowly, ever so slowly, ramped up her arousal. The pleasurable euphoria wasn't intense, but it was pervasive. She could see how some women came to enjoy the experience.

She hiked her buttocks further into the air in order to meet this new feeling.

With her eyes closed and head lying on the bed, Brittany was beginning to enjoy the subtle unfolding of bliss deep within her, when Jack's voice came stark and loud in the former quiet of the room, "Play with the dildo for me, emerald-eyes."

Rolling over onto her side to better manipulate the dildo, Brittany continued to slide it within her. Jack was standing above her, removing his clothes, his eyes never leaving hers.

That same sexy smirk donned his face. The one that made her melt into a puddle of over-sexed jelly. All her inhibitions disappeared into those curled lips. She saw the look of desire in his eyes—desire for her. He wanted and needed her in the worst, best way.

Ramping up the tease, she spread her legs wide for him, giving him a better look at what he most desired. With a wry, half smile, she said with a smoky tenor of allure, "You like what you see? Wanna fuck it hard with that fat cock, don't you?"

He smiled back, saying, "Read my mind."

Seeing Jack's cock spring to life because of her sexy banter, she felt the whore, and loved it for the first time. Although everything she was doing now felt cheap and dirty, it was also making her feel alive. Like the first time she gave up her cherry.

He stood for a moment looking down at her. Fully naked, with his hands on his hips, his massive cock standing out straight and stiff, pointing right at her. It pulsated from the heavy course of blood flowing through it—needing her slutty attention in the worst way, like a twitching junky needing a fix.

Brittany had rarely seen Santos look at her with such raw, animalistic passions as Jack did now. Comparisons no longer mattered, because there could be no comparison between the man she had as a wife and the man who was now standing before her.

Her mind reeled at the implications of that fact, and she thought,I did that to him, me, meek little Brittany Medina, full time suburban homemaker and part time whore, wife and mother of one. I made his cock hard as oak, bound by steel, and his eyes blazing like hot torches, burning a hole into me.

Staring back at him with her eyes mimicking his, full of desire, she knew that nothing could quench the heat that sparked between them, except for her own willing needs to be used as he saw fit.

Pumping the dildo ever faster, it took all of her self-control not to tell him to stick that rigid plank of oak into her, ram it home, fast and furious, until the sweat and sex dripped off them as a torrential rain. She wanted to tell Jack to thrust into her until she forgot, never to remember, she vowed devotion and life to another, but something still held her back.

Her voice lacked the courage to shriek like a slut and demand he fuck her as if she belonged to him, as if owned by him—chained forever to him, like a beast of burden. Tell him he can do her anywhere and anytime he pleased. Yell at him to make her scream and cream like he did the others—like he did to her the last time.

For a moment, she thought Jack would do just that, as he sat on the bed beside her and took control of the dildo, again.

"Yeah, fuck me," she rasped, finally finding her voice, "Pull it out and fuck me."

As he teased her greased hole with the end of the dildo, he asked, slyly, "Where?"

"You know where."

"Say it, bitch, or I'll stop."

"Fuck me in the ass!"

"I am fucking your ass."

"N-N-No."

"What? No? What does that mean, emerald-eyes?"

"W-With your f-fucking big c-cock. I want your cock in my a-ass!"

Jack continued to taunt her, "Such a dirty baby, now you want my cock in your ass. First it was, 'Don't drive so fast,' then, 'Speed up, you're driving too slow.' Then, it was, 'I can't take it in my ass,' and now, 'Give it to me in the ass.' I don't know what to do with you. I wish you'd make up your mind and stick with it."

"P-Please," Brittany whined in frustration.

"Do you want it nice and easy like this," Jack went silent to augment his gently pumping with the dildo, before finishing, "Or hard and fast?"

"Yes," she whimpered, comically ambiguous.

"Sorry dirty baby, no cock for you yet, your ass needs more of a work out." Chuckling, he added, "It's torment, isn't it?"

She moaned another, "Yes."

"But nice."

"Oh yes. If I can't have your cock, go faster, then. Please!"

Smiling at her, he continued to slide the dildo in her ass using a slow, even glide. "What's the rush, emerald-eyes? We have all afternoon."

Jesus, he's going to torture me with this. She threw her head onto the bed in frustration, arching her back to the glacially slow ramping of her arousal.

It wasn't long before she pleaded again, "Do it faster. Please!"

"Slow and steady wins the race, emerald-eyes, and if you talk again, I'll stop."

Whimpering, she did the only thing allowed her, closed her eyes, arched her back further, and prayed he would show mercy.

As he continued his slow pumping with the phallus, Jack wetted a finger with her arousal. Placing the tip lightly on her clitoris, he massaged her using a smooth, circular motion.

"Oh God, yes," slipped from her lips, as her arousal screamed up to the pinnacle.

Just when her thighs began to tremble, Jack pinched down on the thick outer labia surrounding her clit, tamping her arousal back.

Before she could whine about Jack's torment, he pumped the dildo a little faster. The increased tempo took the edge off his treatment, as she felt a renewed climb in her arousal. The climb was still slow, but the blissful feelings were spreading outward, becoming more pervasive throughout her groin.

Touching her clit again, while using that same light circular massage, sent that now broad, pervasive bliss racing once more up to the pinnacle. However, just when she thought her climax inevitable, Jack pinched her clit back into submission.

"Jesus," she whined, "Don't stop like that."

Jack didn't respond verbally, but he did set the tempo of the dido a little faster still.

His actions were louder than words, and Brittany responded to them immediately. The blissful tingles bloomed even further outward, matching the rhythm of the phallus, caressing everything deep within her groin. Arching her back further to meet the climbing ecstasy, she moaned wildly as she fell deeper into a sexual fog.

Again, Jack applied a light touch to her clit, only to back off at the last second.

He did this several more times, bringing her close to climax with his gentle rub, but never pushing her over the edge, and all the time, gradually increasing the sliding tempo and force of the phallus.

Toward the end, and fully in a fog so thick she wouldn't be able to recognize her own name, Brittany had rolled over onto her back. Pushing onto the bed with her feet, she arched her back as if the climbing arousal within her were pulling her hips ever closer to the ceiling. She stayed like that, body flexed to the extreme with her hands clamped tightly onto her breasts, crushing them together and into her chest, as Jack continued slamming the dildo up into her.

All it would take to release the dam would be one more, tiny tap to her clitoris.

Through the fog and over her own loud moans, she heard Jack say, "Are you my dirty baby now, emerald-eyes?"

Some other person, not herself, but sounding like herself, yelled, "God, I need you in there!"

With that, Jack plunged the dildo all the way in, and got up.

It took Brittany a few moments to realize she was alone on the bed. Her body still arched toward the ceiling, she could feel the phallus lodged deep in her ass, caressing her insides with that soft, sweet, pervasive bliss. Flexing and tightening her ass cheeks around it, she felt her arousal climb a little higher, and with just a little more effort she could...maybe...get herself off.

Jack watched her with amusement as she twitched and writhed about, moving and flexing her legs in a continual effort to push herself over the edge and into climax. When he noticed her hand moving toward the sweet spot on her pussy, he barked, "Don't even think about touching yourself!"

Brittany uttered a loud whimper. Without the use of a helping hand, she would never bring herself off. Frustrated, she slumped back onto the bed, panting heavily from exertion.

Sitting in a chair, Jack waited until Brittany's breathing returned to normal. Neither of them spoke.

Brittany spent most of the quiet time waiting for Jack playing with her breasts, and feeling the sweet massage of the dildo deep inside whenever she flexed her buttocks. Her arousal dripped continuously onto the bed sheets.

It was an odd feeling, but one she was beginning to enjoy. Even though the phallus wasn't in motion, it was still imparting a low glow of continual pleasure, keeping her at a higher state of arousal that wouldn't slacken, no matter how long she had to wait for Jack. She knew about anal plugs and considered their use strange, and the women who used them even stranger. Now, she seriously entertained the idea of buying one, and inserting it before her next meeting with Jack. The irony made her giggle.

Hearing her laugh, Jack got back on the bed and knelt at her side. Passing a soft palm along her abdomen, he said, "Sounds like someone was having too much fun by herself."

Brittany's hand immediately went to Jack's cock. Although semi-flaccid after their brief rest, the feel of his heavy tool in her hand still made that low glow of pleasure she felt, expand.

Running playful fingers along his shaft, she coyly responded, "I was just lost in my thoughts for a while. I bet you can't guess what I was thinking."

"Why don't you show me."

Shifting around, she deftly pulled Jack's semi-erect cock fully into her mouth. Tonguing and sucking it all about the shaft and head, she stared up at him with a ravenous light in her eyes.