With someone familiar...

Brad followed his instructions, not wanting to piss off the blackmailer. Even in his drunken state, he knew leaving Sarah behind was a big mistake. As he rode the elevator down to the coffee shop, Brad remembered that the blackmailer did promise that if he cooperated, he’d enjoy it also. He worried about what would happen to Sarah, lying there totally naked, and tied to the bed, with the door left open. He continued to imagine the scene as he entered the dimly lit coffee shop. He wearily looked at the waitress behind the counter and ordered a large coffee. As the nice looking, elderly clerk poured the coffee, Brad scanned the shop for his “next set of instructions.” He didn’t see anything out of the ordinary, other than the single patron sitting with her back to him. His scanning was interrupted by the waitress handing him the coffee. He shoved a couple of crumpled dollar bills across the counter and said, “Thanks.”

He sipped at the strong, sobering brew, resuming his scan of the facility. He still found nothing, but returned his gaze to the long blond hair of the girl sitting with her back to him. She looked familiar. Brad rose from the stool and slowly walked towards her. He could tell she was fairly young by her relatively small frame. His **** hazed brain was slowly putting the pieces together as he neared what he assumed would be a good looking girl. He came up just over her left shoulder and could see a set of generously sized cantaloupes, barely encased in a tight fitting black spandex top. He stood motionless, captivated by the wonderful view, content to be a voyeur for the moment, until the lady felt his presence and turned to see him staring. Brad nearly fell over, “Jenny?” Blinking his eyes in disbelief and shock, Brad did three or four double-takes to ensure it was indeed his baby sitter sitting in the coffee shop. “J-Jen-Jenny,” he stuttered, “What are you doing here?”

“Oh my,” Jenny squealed as her hands went to cover her rapidly blushing face. “Mm-Mm-Mister Goodwin,” she stammered at the sudden shock of seeing her illicit lover standing before her. “I, uh, I’m here … ,” she paused a moment to gather her thoughts, “I’m here to meet someone.”

The fact was that Jenny was sent there by Mark. He had sent Jenny several emails containing photos of her and Brad. Each email had a threat of exposing her to her parents, to her friends at school, and worst of all, to Mrs. Goodwin. There were also photos of her with her boyfriend at the Goodwin home, when she was supposed to be watching the kids. Mark threatened to show the pictures of her with her boyfriend to Brad, and the pictures of her and Brad to her boyfriend. Neither one would appreciate seeing the photos. The last email told her to come to the hotel and check in. She did, and there was a room already waiting for her, fully paid for. When she entered the room there was an envelope on the bed, with her name on it. She nervously opened the large envelope and read her next set of instructions. It detailed for her to primp and preen and head to the coffee shop. She was to buy a drink and sit there reading until her ‘contact’ arrived. It didn’t specify who her contact was; it only said that she would figure it out once he arrived. It then ordered her to ‘convince’ him to return to her room. Once there, she was to suck him and fuck him, and drain him completely dry, until he had nothing left. Once she had completed her task, she was to send him on his way. The next part she thought was very odd; it said to douse him with the cologne on the bathroom sink before he left, ‘in order to cover the smell of sex.’ It also warned of dire consequences if she divulged any of this arrangement to anyone.

Jenny sat there dumbfounded, not sure what to say, as the reason for her **** stood directly in front of her. “Why are you here?” she nervously quipped.

“Ah. Too much to drink at the bar.” Brad laughed nervously as he moved across from Jenny. “Mind if I sit down?”

Jenny looked around nervously seeing if her contact was there. Not seeing anyone else around, she nodded. As Brad sat, Jenny asked, “Where’s your wife?”

Brad lied, somewhat. “She had too much to drink also. She’s upstairs passed out.”

Trying to make small talk, Jenny asked who was watching the kids. Mark had told her that since they were spending the night here his mom had taken the kids. Jenny found it odd, that they would plan on spending the night at a hotel relatively close to home. But then again, so was she. But she was being blackmailed … Then it slammed her in the face. Was he the blackmailer? Or was he the contact? She continued making small talk as she tried to put the pieces together. Could this be an elaborate scheme to get Jenny into bed, since all their secret rendezvous’ had taken place in a car? If that was the case, then who took the pictures? That didn’t make sense, because he would have known about her boyfriend in the house. Bu then again, it could be his way of teaching her a lesson. Her mind was spinning, not once really listening to anything Brad was saying.

“So, who are you here to meet?” Brad repeated, noting how Jenny seemed to be deep in thought about something else, not answering him the first time he asked.

“Just a friend from school,” she lied. “It seems he’s running late,” she mused. Was he the one she was supposed to take back to her room and fuck the night away with? The mere thought sent a tingle to her pussy as she imagined him roughly slamming his cock into her tight hole repeatedly, making her cum like a running faucet. Fleeting images of Brad, forcing her head down on his cock as she swallowed him whole, flashed through her mind. Was her boyfriend the blackmailer? But how? Someone else had to be taking the pictures? Was this just coincidence, or was Brad, “the one”? She could possibly blow everything wide open if she made a mistake. She looked at her watch. She looked around the tiny shop. There was no one around, and it didn’t look like there was going to be anyone else around. This must be it, she convinced herself. “Looks like I’ve been stood up,” Jenny stated with puppy dog eyes. She drifted her hand across the table, felling the electricity course through her veins as she touched Brad’s hands. “Walk me back to my room,” she half pleaded, half asked.

Brad wondered for a moment. Was she the one he was to meet? Was this the plan? Did she have his next set of instructions? Then it occurred to him that she could possibly be involved in the **** scheme. Could Jenny be one of those psychotic young girls destined to break up a marriage so she can get the man? But then who took the pictures? Who is the male voice that keeps calling? Why would Jenny go through all this to get to him? Why would she put Sarah through all that? Did she want Sarah to start fucking other men, so that he would get pissed and leave her? Brad’s mind was spinning as he heard Jenny ask again, “Please walk me to my room.”

Brad decided to ‘play along’ and see if he could figure out what was going on. He didn’t want to reveal to Jenny that there was a blackmailer out there who had pictures of the two of them. If he was all wrong about Jenny, and told her about the pictures, she’d dump him in a second. The two walked side by side through the lobby and to the elevator, up to Jenny’s door.

Jenny inserted the card key and popped open the door. Halfway in, she spun around and said, “Thank you.” Within a split second, she wrapped her long arms around Brad’s neck and kissed him hard on the lips. She pushed her tongue into his mouth and entwined it with Brad’s tongue.

Brad’s resolve had quickly faded, in his **** induced mind. The coffee didn’t sober him up any, it just made him more awake. Now, with Jenny wrapped around his neck, his cock sprang to life while he dueled with her worming tongue. They were till standing in the open doorway as Jenny’s hands undid the buttons on his shirt, tugging the ends until she could run her hands over his muscular chest. Brad could feel his nipples harden into tiny pebbles as Jenny’s hands danced over his chest. He forgot they were in the hallway until the ding of the elevator reminded them they better step inside. Brad pushed forward, quickly slamming the door behind him, knocking Jenny to the floor.

Jenny quickly recovered and pushed Brad back, slamming him into the door with a thud. She scrambled to her knees and undid his buckle and zipper, swiftly tugging his trousers and briefs down to the floor. Wasting no time, and no opportunity, Jenny wrapped her hands around the gelling shaft. She gobbled the soft meat, suckling it as it hardened and grew within her talented mouth. It was only moments before Brad was hard as a rock and fucking forcefully into Jenny’s hungry mouth.

The voraciousness and heated passion of the young lover was too much for Brad in his weakened and drunken state. He felt his lava boiling as Jenny snaked a hand down to tickle his balls, moaning around the cock filling her mouth. He cried out his pending volcanic eruption, warning Jenny of the intensity. She ignored his signals and doubled the intensity, almost begging him to fill her mouth with his prized pearly protein. Brad slumped against the door, thrusting his hips into Jenny’s mouth when he popped his nut. Jenny kept pumping her fist along the shaft as it throbbed, catching most of the first jet blast in her mouth. Rather than swallow it, she kept bobbing on the hard cock, letting it slosh through the cum-filled confines of her mouth. The excess cum was drooling down her chin onto her heaving breasts, staining the black top she was wearing. Jenny continued purring as the subsequent blasts were fired from the torpedo. She aimed the lessening intensity spurts over her face as the cloudy liquid spittled onto her cheeks and neck.

To Brad’s amazement, Jenny never stopped sucking his cock. It was as if she were possessed by some demon, ferociously sucking on the cock. She didn’t care that her face was plastered in cum, Jenny kept up the attack, as if he had never popped. Brad stood there dumbfounded and numb as he watched his baby sitter’s cum covered face hungrily gobble his cock, keeping it hard and stiff. She brought the cock out occasionally, rubbing it across her cheeks, face, and neck, only to return it to her hot mouth. For the next five minutes, Jenny cleaned herself and the loving cock, never letting it lose its rigidity.

Jenny rose to her feet with a devilish grin on her face. Holding Brad by the cock, she dragged him towards the bed, letting him step out of his pants. Once they were at the bed, Jenny turned to Brad. Locking her eyes onto his, she grabbed her skin tight shirt and teasingly raised it, exposing her beautiful breasts to Brad’s gaze, unencumbered by any other clothing. Brad’s mouth drooled at the likelihood of latching onto those ripe, red, cherry nipples perched atop the perfectly proportioned melons. Jenny then undid her pants and peeled out of her tight fitting blue jeans. For the first time, since they’ve ever met, Brad stared at Jenny in her entire nudity. He was tickled pink to have such an opportunity to view such a work of art. He was speechless as Jenny brushed his shirt and jacket from his shoulders, hearing them thump to the ground behind him. The two were now totally naked, together, and neither one could have been happier.

Jenny sat on the bed and pulled Brad to her, guiding his wet prick to her moist slit. She rubbed the head up and down along the slit, spreading her lips open for his entry. Once she and his cock were nice and wet, she placed the tip against her tight opening. Once again, with puppy dog eyes, Jenny pleaded to Brad, “Fuck me!” Brad was not about to lose such an opportunity and pushed forward. Keeping his eyes glued to Jenny’s he watched her face transform as she continually repeated, “Fuck me, fuck me, fuck me…”

Jenny wanted to be fucked. Never mind the **** note. She had her ‘experienced’ lover with her and she was going to take advantage of it. She loved the feel of his hot come as it covered her face; now she wanted it fueling the fire in between her legs. She knew Brad was a sucker for the pleading eyes, but when he pushed forward, she became even more determined to have him fuck her hard making her cum in rivers as she had just daydreamed earlier. It was as if she were possessed by the devil himself, as she barked for him to fuck her, not make love, fuck till she exploded and exploded and exploded. Ever since the two began their little trysts, Jenny had always dreamed of this day, where Brad would make a real woman out of her! “Fuck me hard,” she screamed. “Harder,” she demanded. “Harder.”

Brad was fucking into Jenny as she lay sprawled across the bed, her legs dangling off the side. He stood there, repeatedly driving his dick in and out of the tight opening, squirming as it clenched onto his pole. Jenny’s legs rose up and wrapped around his hips as he was bucking into her. Her ankles locked together in the small of his back, controlling his tempo, always forcing him in to the hilt, his groin smashing into her pelvis. Brad reached out and grabbed hold of Jenny’s tits for support. He mauled the firm flesh, feeling it spring back into place before concentrating on her bright red, eraser sized nipples. He pinched each teat between his thumb and forefinger, eliciting a yelp from Jenny as her hips bucked up to meet his thrust. He rolled the flesh as he pulled them from their puckered bases. Jenny’s hips rolled, and her muscles rippled, milking Brad’s cock entrenched in her furrows.

Jenny was glad she had gotten Brad to cum on her face, because now he was fucking her royally, and was not cumming too quickly like he did when they were in the car. This was not going to be a quickie session for Jenny. She was going to take a trip to the stars as her lover fueled her rockets. She was calling out to every god imaginable as the cock pummeling her pussy rammed repeatedly in to the hilt. Stars were exploding as her body quaked and her pussy convulsed, trying to milk another ejaculation from Brad. As she panted, recovering from her first orgasm, Jenny rolled over and jutted her ass high in the air. “Do me doggy,” she barked, reaching between her legs and guiding Brad’s stiff rod back into her waiting hole. Brad eagerly complied humping her, much the same way he did over the hood of the car. He pounded into her pussy watching her ass jiggle as he bounced back, returning for another pounding. He ran his hands over her smooth back, pressing her into the bed as he continued to fuck the young pussy. Reaching her head, Brad tangled a handful of her long hair around his fist and gently but forcefully pulled back. Jenny yelped, “Oh yes,” as her head snapped up, making the cock stabbing in her feel like it was going to pop out her chest. “Yeah … do it,” she grunted between heaving gasps of air. “Give it to me … FUCK ME!” Brad was fully into it now, having been fucking Jenny forcefully, for nearly fifteen minutes, non-stop. He could feel the friction begin to tingle his senses, and timed his thrusts and movements to maximize his pleasure. Jenny could sense his cock throbbing and twitching as Brad became even more forceful. “That’s it … awww FUCK … yeeeeaaaahh cumminmeeee.” Jenny was rambling now as her second orgasm was building. Brad reared back with his hand and smacked Jenny’s glutinous ass, just as his cock started throbbing. Jenny erupted, falling forward as her legs ceased supporting her. The thunderous crack across her ass unleashed the waves of pleasure Jenny was so accustomed to. She flooded Brad’s prick with her fluids as he shot his second load into the murky waters. Brad fell atop Jenny, sweating and panting, his cock still trapped within her tight snatch. The two remained motionless as they recovered, waiting till their heartbeats beat as one, and they breathed in syncopated rhythm.

Brad’s flaccid cock slipped from Jenny’s loosening grip. Jenny moved to the side and flipped Brad onto his back so she could look into his eyes. She knew it was wrong, but she did love him! She loved him for the sex! He knew which buttons to push, and she was always willing to please him! She just wished things were different between the two so she could spend her entire life with him. Still looking into his eyes, she let a wicked smile creep across her face. Her hand drifted down to the limp, slimy shaft and grasped it firmly. Brad looked at her in disbelief, totally exhausted. “Jesus, Jenny. What’s gotten into you?”

“I’m really, really horny,” she replied before engulfing the limp sausage covered in her pussy juice.

“I can’t …” Brad panted

“Oh yes you can,” Jenny replied, holding his prick up for him to see, “See?”

Brad looked and was flabbergasted to see his cock getting hard again. “Oh, Jesus Christ,” he sighed as his head plopped down on the bed, resigning himself to relax and enjoy Jenny’s insatiable appetite. Jenny gobbled the flesh, sucking the head as her hand milked the shaft. She mewled like a kitten as she toyed with Brad’s cock. She licked and sucked his balls, sending Brad into a frenzy as he bucked his hips and thrashed his head. Jenny then surprised Brad by lifting his nut sack up and darting her tongue around his crinkled hole. The new sensations were so erotic for Brad that his cock sprang to full mast. He was the one moaning now. Jenny had been going at him for nearly half an hour since the last time he blew his load, and now Brad found himself primed and ready. Jenny held his stiff cock up for inspection and then looked at him, “Ready for round three?”

Brad nodded enthusiastically. It was Jenny’s turn to be in control, so she climbed atop Brad and dangled her tits in his face. Brad latched onto the milky orbs nibbling on the turgid flesh as Jenny guided his prick back into her watering hole. Jenny rocked back and forth as Brad continued feasting on her generous offering, squeezing and pinching the tit he wasn’t eating. He alternated between the two as Jenny continued riding the bronco, pushing the saddle horn further in her clenching crevice.

The two rocked back and forth for nearly five minutes, building up pressure, and flooding her with wetness. Brad caught a glimpse of the fire in Jenny’s eyes as she grasped the base and pulled herself off Brad’s cock. Brad wondered what was wrong as Jenny looked worriedly into his eyes; but she still had the lusty fiery embers burning there. Jenny scooted an inch forward and pushed Brad’s cock an inch further back, before sitting back down on the cock. Brad’s mouth hung open, unable to speak as Jenny’s face contorted. He saw her eyes roll, and her lids flutter as she let her body’s weight push her down onto the rod spearing her ass.

By the time gravity took hold, Jenny had Brad’s cock half way into her ass. Jenny was scared but also very grateful that Brad was the one taking her anal virginity. She wanted to give him something special from her. She had heard her friends talk about it, and was originally disgusted by the thought. But now, with Brad here, and in the heated passion of the moment, it seemed the right thing to do. Before she knew it, Brad’s cock was all the way in her ass. Jenny’s eyes sparkled as the new full feeling enveloped her body. She had done it. She had taken him in her ass. Now she was going to ride him. She planted her feet on either side of his waist and put her hands on his chest for leverage. She then began a slow methodical up and down bobbing motion as if she were rising and sitting on a chair. Jenny felt the friction and pain replaced by a warm, wet, squishy feeling as Brad’s cock slid effortlessly through her back door. She began bouncing in earnest now as the electrical sparks began erupting throughout her body.

Brad could not believe he was ass fucking the beautiful baby sitter. He was in seventh heaven as he watched Jenny have multiple orgasms as she continued bouncing on his cock. He could feel her ass clench at the base every time her body erupted. Brad, however, was totally spent. He didn’t think he had anything left in him as he began bucking back up into Jenny, pushing his cock, seemingly deeper every time he did that. Jenny seemed to know better. Once she got into the rhythm, she started toying with Brad, destined to push him over the edge. “That’s it. You’re fucking my ass. It feels good, doesn’t it? It’s nice and tight for you. You like fucking my ass don’t you? C’mon FUCK MY ASS!” She slammed up and down on the cock erupting as another orgasm washed over her body. Brad never relented though, feeling his electrical circuitry begin to arc and spark. Jenny sensed his twitching as he bucked his hips up in steady tempo. She sat up, burying his cock to the hilt and squeezed her ass muscles in rhythm with his rolling hips. She put her hands at her crotch and started rubbing her clit as she stared into Brad’s eyes. She didn’t have to say a word. She knew Brad was ready to blow over once again, watching her play with her pussy as she took him up the ass. Brad didn’t say a word either as he tensed the muscles in his face; his cock twitching uncontrollably as Jenny’s ass squeezed every last bit of juice out of his reaming poker.

Jenny slowly and somewhat painfully freed herself from Brad’s quickly wilting member. Once she was free, she curled up on Brad’s chest as his hands caressed the sensitive skin across her back. She knew he had to be the contact. She knew she would have to let him go back to his wife. She knew she had succeeded in fulfilling her blackmailer’s orders. Yet, she didn’t want to let him go. She wanted to be with him, and she’d do anything to make that happen.

Brad knew he had to get back to his wife, despite the comfort he felt lying naked with Jenny on the bed. He wondered if the blackmailer had set this up to fuck with his brain. If so, it was working. He loved his wife and kids, yet he couldn’t deny the hunger he had for Jenny’s body and her touch. “Jenny?” he softly whispered.

“Yeah, I know,” she whined as she scraped her nails across his chest. “Just don’t say it.” She didn’t want to hear that he had to go back to his wife. She sat up in bed to let him roll out. She even helped him get dressed, even adjusting his tie. Then she remembered the odd instruction from the blackmailer. She padded into the bathroom and located the cologne. She returned to Brad and wriggled her nose as if she were sniffing him. She almost laughed, because he did smell of sex; her sex! She told him so and doused him with the sweet smelling cologne. She even playfully tugged on his pants and sprayed his wilted willie to cover up the unique odor. She kissed him deeply before regretfully watching him walk out the door.

Brad shook his head in disbelief at the events that had just transpired. He couldn’t remember ever having a night of sex like that before. And as an added bonus, he just enjoyed what he hoped would be his first of many anal fucking experiences. Brad rode the elevator to his floor and quietly padded to his room. He checked the door handle for a do not disturb sign, and found none, signaling it was clear for him to enter. He inserted his key card and nervously turned the knob when the light turned green. He wasn’t sure what he would find inside the room, and the knot in his stomach twisted tightly.