Once You Go Black...

She ended up going to bed early, still exhausted from the night before. Despite the fearful dilemma she was facing Amy managed to fall asleep easily and slept through the night. The next day she called a friend and spent the day shopping with her to keep her mind off her problem.

On the drive home she could think of only one thing and was shocked to find her panties were soaked when she got home. Subconsciously, her body seemed to like the idea of anal sex with Karl. Her poor over worked pussy was still far too sore for any kind of masturbation but she smiled thinking she would be able to go though with it next week after all if her body was reacting in this way to thoughts of another encounter with Karl.

By Tuesday her pussy was ready for her to resume her normal routine of masturbating herself to several orgasms each night. Amy knew it was important she try to prepare her ass for what was to come this Friday but had been avoiding it until now. With only a few days before her next encounter with Karl she knew she was running out of time. That night she watched some of her movies again and played with her pussy until she achieved several satisfying, though unspectacular, orgasms.

Once her motor was well warmed up she moved to her bedroom to begin working on her ass. The only toy she owned was Big Ben and this was her main source of hesitation. She wished she owned a smaller toy to start with but was unwilling to visit the adult store again and one ordered online wouldn't arrive in time. The thought of using something else crossed her mind, but she had no idea what to try. She was also afraid of losing a smaller item and having to explain the predicament to her doctor. At least with Big Ben there was no worry of that.

Gazing at the intimidating 12 inches of rubber she had an idea and rushed to the bathroom. She returned to her bedroom with a bath towel she doubled over to sit on and her bottle of baby oil she liked to use as a moisturizer. For now she set the huge toy aside and used a small amount of the oil on her hand to begin lubing her ass. The cool sensation on her sensitive rear entrance felt great as she rubbed it gently all around her asshole. Soon she was able to ease a finger inside and then another, which she began sliding in and out comfortably.

It did feel good, but two of her tiny fingers were a far cry from Karl's massive tool. In preparation for the dildo she rubbed her clit with her other hand to increase her excitement. When she felt another orgasm approach she stopped what she was doing and took the toy in her hand. Squirting a liberal amount of the oil on it she ran her hand up and down coating the shaft, making sure the tip and first few inches were covered completely. She held two fingers pressed together next to the toy to gauge the difference in size and guessed that it was three or four times wider.

This was going to hurt, but there was no way to avoid it. She needed to see Karl again and she needed her ass to be ready for him. With a nervous deep breath she moved the tip to her ass and applied pressure. Pushing very gently at first, she slowly increased the pressure until she was afraid to force it any harder. It didn't fit she realized in a panic! Amy tried backing away and trying again but the tip just bumped ineffectually against her tight ass causing the flexible shaft to bow. Even when she tried gripping it closer to the tip she had no luck.

A new approach was needed because these initial clumsy attempts were getting her nowhere. Setting Big Ben aside she smeared oil all over her ass and went back to fingering again. When she was ready again she tried sliding the toy in while using her fingers to spread her ass. She was able to line up the tip of toy with the entrance to her ass, but it snapped shut soon as she removed her fingers for the forward thrust.

Dropping the toy once more she reposition herself to face her mirror and propped her head up with her pillows. Now she had a much better view of what she was doing and set about devising a new plan. Amy began exploring her body and soon discovered what she hoped was a break through. When using her fingers on a straight in approach the resistance was high. If she slid her fingertips over the patch of skin that separated her pussy from her ass, then her ass opened invitingly allowing her easy access. She was able to penetrate her ass using a fraction of the force required for the direct angle.

Greasing the small patch of skin above her ass with a big squirt of the oil she massaged it in until her entire orifice was well lubed. Then watching her movements in the mirror she held the dildo near the tip and slid it down towards her ass. She felt the toy catch as it dipped into the indentation of her ass and watched her asshole spread open to accept the wide head inside. It hurt like hell but she forced herself to continue, wincing as her ass screamed in pain to protest the intruder. Using firm, steady pressure she forced the toy deeper until the pain became too much.

She had managed to slide three, maybe four, inches of the dildo into her tight little ass before stopping. The throbbing pain in her ass was intense, but soon began to subside. The longer she left the toy inside the less pain she felt. Without touching the toy again yet she began to rub her clit and slipped a couple of fingers into her fiery pussy. Her pussy tingled in excitement as she started fingering herself thoroughly. With her ass stuffed full of fake cock the sensation was incredible.

When she had finally mustered the courage to continue with the toy, she found the slightest touch or movement sent waves of pleasure rippling through her body. Releasing it once more she sagged to the bed in bliss. The sensations she was feeling in her ass were unreal. She seized the bottle of baby oil once more and squirted it all over her nether region, covering her ass and pussy. Then she took hold of the toy and wiggled it from side to side in an attempt to loosen the tight grip her ass held it in. Slowly, the side-to-side motion morphed into a circular one and she found she was able to take a little more of the toy into her ass.

She wished Karl would walk through the door at that moment and fuck her senseless. As it was she had to make do with the 12 inches of rubber at her disposal. With short, quick strokes she began fucking her ass with a two-handed grip. Every stroke threatened to send her over the edge into orgasm, but she held out wanting it to build slowly. Her head swayed side to side as the pressure built and she chewed her lip against the intense mixture of pain and pleasure. She released the dildo with her left hand and let it stray to her pussy where plunged two fingers inside 20 or 30 times before withdrawing the rub her clit. Then with a few open-palm slaps on her drenched pussy lips she shoved the fingers back in for more.

Grunting in pleasure, like a crazed animal, she thrashed about in the throws of pure sexual bliss. She fought to hold off her impending orgasm but in the end it was an unstoppable force. Her panting and moaning ceased as every muscle in her body locked tight and she held her breath for what seemed like an eternity. Both her ass and pussy pulsed with wave after wave of intoxicating release. From her pussy, a seemingly endless stream of juices gushed forth to soak the towel she sat on. Gripping the dildo with both hands again she pulled it from her ass in one quick motion making a loud popping noise and dropped it on the towel before slumping to the bed completely spent.

For a several long minutes she basked in the afterglow of the amazing orgasm. It had been good enough to rival her experiences with Karl from last weekend, a fact that truly shocked her. Even now she could still feel her body contracting over and over. Lifting her head from the pillow she focused on her reflection once more and watched as her glistening oil-covered asshole opened and closed in tiny pulses as if winking at her. It was beautiful and yet disgusting at the same time, like wisps of steam rising from a sewer grate on a cold winter morning. When the involuntary spasms finally ended she rose from the bed and stumbled to the bathroom.

She enjoyed a long soak in a hot bath while fantasizing about her next encounter with Karl. There was no doubt in her mind she would go through with it now. If she could drive herself to such heights of ecstasy then she needed to see how much better the real thing would be with him. The water was cool by the time she got out and dried off. That night she went to bed sure of herself and more at ease then she had been in months.

The next two nights she continued to prepare her ass for Friday. Each night she started early in the evening to make sure she has plenty of time to take care of her needs. She went to bed Thursday night knowing she had done everything she could to get ready for him and was brimming with excitement. The prospect of a totally new experience with Karl led her to approach tomorrow's meeting with as much anticipation as the first.

Work the next day sped by in a blur. Earlier in the week she had arranged to leave a couple of hours early with her supervisor Dave. She hurried home after work and set about using the kit Karl had provided her with. It was something she had never done before, but she had read the directions and researched online enough to know the basics. There was an uncomfortable bloating sensation while using it, but she was left feeling refreshed once done. While Amy had no idea if it would actually help her or not, there seemed to be no harm in trying.

After a quick shower, she dried herself and put on some makeup. This week Karl wanted her naked so she skipped lingerie altogether and chose a simple black dress which she could easily slip out of in case he was the first to arrive. She styled her hair and left with an overnight bag containing a change of clothes and her bottle of baby oil. As she rode the elevator down to her car she smiled knowing that the long week she had endured until this second night with Karl was finally over.

At the hotel she checked in like she had the week before and headed to their room. Thankfully the clerk at the front desk was different this week. She didn't want the people there wondering why she was there any more than they were already. It was about twenty minutes before their scheduled meeting time so she was not surprised to find that she had arrived first again.

Once inside she stripped out of her dress and slithered onto the bed. Eager for the night to begin she started playing with her pussy to get herself ready for his arrival. She remembered the baby oil and got up to retrieve it, placing it on the nightstand next to bed. While she was confident she could go through with the anal sex, she knew she would need the help of the lubricant. By they time she heard him at the door her pussy was dripping wet and ready to be fucked.

He entered and closed the door behind him. Wasting no time she hurried to greet him and sank to her knees without a word after welcoming him with a deep kiss. She quickly unfastened his belt and undid his pants, pulling them and his boxers down to his knees to expose his wonderful cock. He wasn't hard yet, but she planned to rectify that little problem as soon as possible.

Kissing up and down the length of his shaft, she cupped his balls and licked the head. She could feel it firming in her grip and she took it into her mouth while stoking the long shaft. Staring up into his eyes she sucked him like a cock-starved whore. Holding him in both hands she began forcing it deep into her throat on her own accord. Gasping for breath she continued to try deep throating his monstrous cock, even though she knew it was far too big for her to engulf completely. She could tell he appreciated the effort from the moans that escaped his lips.

The blowjob continued for good 10 or 15 minutes with neither of them making a sound, save for the grunts and gasps. By then her jaw was starting to ache, her knees were sore from the carpet, and his cock was covered in a slick coating of spit. Amy stood up and returned to the bed spreading her legs wide and using her fingers to pull her pussy lips apart.

"Come fuck me Karl," she pleaded.

He responded by kicking off his shoes and stepping out of his pants. Then he lifted his shirt off dropping it to the floor. She admired his chiseled physique and he strode to the bed cock in hand. Kneeling between her legs he guided the head to her pussy and started to feed its length into her. Gently he slid inside and stopped when he felt her body resist his movement. Already she was on brink of orgasm as her pussy stretched to contain his thick prick.

Griping her tightly around the waist he began pumping in and out of her. Her lips clung to his shaft on each stroke as he worked to loosen her up. Soon he settled into steady pace that forced her to fight the urge to cum. Taking care not to hurt her by forcing too much of his cock inside before she was ready he slowly increased the depth of his thrusting. In order to give her a respite, he would pull out and guide his cock to her mouth from time to time returning to her pussy when his cock has been sucked clean of her juices.

Each time he returned to her pussy he would fuck her a little harder, a little deeper until finally, when she could take no more, she wailed in pleasure and squirt all over his incredible cock. As he sat next to her she took his cock with trembling hands and lovingly licked her thick juices from it.

He finally spoke saying, "Nice to see you again too."

They both erupted in laughter and she was overjoyed that this weeks session was going far better than their first night together had started. They chatted as she continued to stoke his cock in order to keep it hard. When he asked her if she like his gift from last week she knew it was time. She rolled towards the nightstand and snatched the baby oil in her hand. Drizzling it all over his cock she rubbed it in until his cock was thoroughly lubed. Turning her back to she knelt down in front of him. She rose to one knee and exposed her ass and pussy to him. Looking back at him over her shoulder she held the bottle of oil above her ass and with a soft squeeze sent a thin stream of it trickling down the crack towards her pussy. Spreading it around with her fingers she fingered her ass before clenching an ass cheek in each hand and pulling it open.

The shocked look on his face was priceless. When he failed to do anything but stare at her upturned ass she decided to urge him along. "I'm ready if you are," she said. "Be gentle with me and I should be able to handle about half of it tonight. Oh and don't be afraid to use lots of this," she added as she tossed the bottle of oil to him.

The bottle struck him in the chest and that seemed to jar him from his trance. He squirt some oil into his open palm and masturbated with it as he positioned himself behind her sitting back on his haunches. The anticipation was driving her wild. As she watched him stroke his greasy pole she craved it more and more. She thought she might cum in anticipation as he rose from the bed and positioned the tip of his cock at her asshole.

"Spread your cheeks and hold still," he warned. "I'll be careful but if you start moving around there's nothing I can do."

Nodding in agreement she pried her ass cheeks wide as she could and awaited his entrance. The head of his cock felt immense against her ass. She could feel the pressure build as he pushed forward. It wasn't going in, so he backed off and sent a stream of oil down over her ass rubbing it in with his hand. He gripped his cock near the tip and slid it down the crack of her ass while applying pressure. The tip caught in her ass and opened it up letting him slide in, just as it had when she used a similar technique with her toy earlier in the week.

"Ahh... it's so tight," he sighed as the head of his cock slipped inside.

Amy could feel her ass stretching to accommodate his huge cock. He held steady for a few minutes so she could start to adjust before pushing forward again. After forcing 3 or 4 inches inside he stopped again. He stayed where he was for a few minutes, then started fucking her ass slowly. It was no worse that the dildo and over time she began to enjoy it as the pain subsided. By the time he reached a nice steady rhythm, her body was tingling in delight. As his strokes gradually became faster and deeper, she started fingering her hot wet pussy and rubbing her throbbing clit.

"Fuck me," she panted as he continued to ravage her body.

Just as she was ready to achieve another orgasm, he pulled his cock out completely. She spun around to see what had happened, thinking maybe he was ready to cum, and was shocked when he lunged forward swinging his cock towards his mouth. Turning her face to the side she resisted his advances until he seized her by the chin and forced her to look up at him.

"I asked if you liked your gift from last week. Why the hell do you think I gave it you? I told you it was for your benefit, not mine," he explained in an even voice. "Now look I won't make you do it, but I'll be leaving if you're not sucking my cock by the count of three."

Looking into his eyes she knew there was nothing she could say to sway him. Their first night together he had warned that he was going to make her his whore. As her eyes filled with tears she knew he was right and there was nothing she wouldn't do to keep fucking him at this point. His incredible cock had trapped her and she needed it so bad that sucking his cock after it had been in her ass was a small price to pay. When he started his countdown at one, she leaned in and sucked his cock inside as far as she could take it. Focusing on the hours of fucking that would be her reward, she tried not to think about where it had been a few moments ago.

"Good, very good," he praised her efforts, "Now get back on your knees for some more fuckin'."

Doing as she was told she turned around again and spread her ass. She let out a gasp of surprise when he plunged his cock, not into her ass, but deep into her pussy. Circling her waist with his strong right arm he fucked her hard and fast for a few minutes before pulling out again. Breathing hard she started to sink to the bed for a rest, but he held her hips steady and went back to her ass again. This time he slid inside easily and started fucking her ass much more forcefully than he had before. Each powerful stroke drove half his wonderful cock into her ass.

Closing in on orgasm again, her hand returned to pussy and frigged her clit wildly until driven over the edge. When her pussy started to pulse and squirt he pulled his cock out of her ass and drove his cock into her cunt again. He fucked her pussy fiercely as she came and came and came. Finally, when she could take no more she lunged forward to escape his cock and turn over collapsing to the bed a complete wreck.

"Stop, stop, no more," she pleaded in a daze as she tried compose herself.

"That's just a little taste yet," he promised with a laugh and he sat next to her on the bed.

Smiling in bliss she crawled to his crotch and latched onto his cock again. Jerking the skin below his head up and down she sucked the tip into her mouth. She would lick the bottom of the sensitive head and grip it with her teeth in playful nibbles. Using her other hand she massaged his nuts inside his scrotum. Leaning back he slid he ass forward exposing his buttocks to her. It was a hint she easily picked up on and after sucking his balls for a few moments, she licked the skin that led down to his ass.

Beyond caring at this point, she tongued his asshole without a second thought. She continued to stroke his cock with one hand and rub his balls with the other. While licking his ass she could feel his cock tense with each flick of her tongue. Recognizing her opportunity to take control she quickly shifted her mouth between ass, balls, and cock licking and sucking wherever she went. The entire time she never stopped stroking his cock or rubbing his ass and balls. When she felt his ass clench tightly she jerked his cock violently spewing thick streams of cum all over his torso as he grunted loudly.