The Best Tip He Ever Got

Editor's note: this story contains scenes of non-consensual or reluctant sex.

*****

Drew lie in his bed completely naked, the morning light from the sun cascading across the white sheets illuminated the room. The familiar sound of the alarm from his phone slowly began to fade into his ears, gradually growing louder and louder. He sat up and started to rub his eyes. Then flashes from his memory of the night before invaded his mind. He jumped and began darting his eyes around the room, but of course he was alone. He shot his eyes between his legs and his hand quickly followed, seemingly grasping at nothing. He wondered if it had all been a dream. He spotted his phone on the bed just beside him, unlocked, with only 7% battery left. As he did, he saw the time and the label on the alarm, Office Work 9:46 AM.

"FUCK!!!" He exclaimed, realizing that he only had 14 minutes to get to his day job. He had completely forgotten that he had gotten chosen for the Saturday shift.

The concern he had about what possibly happened last night quickly faded. He sprang out of bed and plugged his phone up to charge, at least for the few minutes he would need to get ready. He got himself dressed with haste, losing his balance slightly as he tried to put his pants on with both legs at the same time. He yanked a shirt off of one of the clothes hangers in the closet before quickly shuffling his way back over towards the bed. He tripped over his shoes which he had kicked into the bedroom from the bathroom last night. He fell to the floor with a loud thud.

"Motherfucker!" He yelled to the empty room.

After taking a moment he got up and sat on the edge of the bed while he donned his shirt and socks. As he bent over to grab his shoes, he felt a soreness in his abdomen and lower regions. He didn't think about this too long as he glanced over at the clock on the dresser. It was now 9:51 AM.

"Fuck fuck fuck!" he yelled again, knowing that he would be a few minutes late.

Luckily his phone had charged to 15% as he grabbed it and darted out of the room, the end of the charger yanking out of the phone as he took off. He swiped his keys and wallet from off the kitchen counter on his track through the house. The front door slammed behind him and he quickly fumbled with his keys to lock the door. He ran to his car and whipped the door open, while in the process of trying to put his wallet and phone in his pocket.

He drove quickly to the office that he worked in during the day. He worked for a company that provided credit card processing terminals to convenience stores and gas stations. Most of his day was spent on the phone at his cubicle desk. It was a small privately owned company, so he did not worry too much about repercussions of being late. Moreover, he just didn't want to have to hear his bosses mouth this morning. He sped into the parking lot and came to a screeching halt as he pulled up in the parking space. No sooner did his car stop, his car door flung open and he took off towards the door of the building.

He was lucky, the clock on the wall of the lobby read 9:59, which brought him a sigh of relief. He hustled to his desk, tapping his badge on the "clock in/clock out" machine. He plopped down in the chair in front of his computer, not even acknowledging his cubicle mate, Alexandria.

"Well hello, you're here late today." She said, as Drew heaved to catch his breath.

"Yeah... I overslept... And forgot to plug up my phone... It's been a hell of a morning." He said back to her, pausing in between to take breaths.

"Oh, I see. I just thought it was weird because it's not like you to be late." she replied, turning in her swivel chair to face him.

"Yeah, well... It happens." He said back to her, turning slightly in his own chair.

She laughed a little bit to herself, then turned back to her work. Drew took a few moments to feel normal again and then logged onto his computer. He looked to his left and noticed a small stack of folders. Usually the stack was much taller, so he knew he could take his time today. He let out a heavy sigh and then rose from his chair, making a beeline to the break room. He grabbed his mug from the cabinet and filled it with coffee. He drank it rather fast, even being quite hot. Once he finished the cup, he filled his cup again and went back to his desk.

Alex chuckled to herself a little bit, seeing that he was obviously distraught this morning. He was glad that he didn't have to work tomorrow. He already wasn't happy having to come in on Saturday, but hopefully it would not be a reoccurring thing. Alex turned to him and threw a paper clip at him.

"What the hell?" Drew asked as the paper clip bounced off the back of his head.

"Just seeing if you are awake." She said, laughing.

"Ha. Ha. Ha. Yes I'm awake dummy, how else would I have driven here." He said back to her, slightly annoyed but the humor of the situation was not lost to him.

Ever since she had become his cubicle mate several months ago, they had gotten quite close. She obviously had a crush on him, but she knew that he was married and would never make a move. Although she was fully prepared to cooperate and give in to him if he ever made a move on her. Drew had picked up that she had a crush on him, but he always did his best to politely make it known that he wasn't interested. Of course it didn't stop her from flirting with him.

It wasn't that she was not attractive, because she definitely was. She was about 5'2" tall, and wasn't necessarily the definition of a "small woman". She wasn't overweight or anything, but she did have a little bit of a belly and thick thighs. She has huge breasts, at least a DD, and a bubble butt that Drew often found himself staring at if she was walking in front of him. She had a tiny round face, with the cutest dimples on her cheeks. Her long straight brunette hair stretched down to the waistband of her jeans, that she would often fling over the back of her computer chair. Drew had caught himself checking her out on multiple occasions, but resolved that he would never make a move on her, wanting to stay faithful to his wife.

The day seemed to drudge on, what felt like a couple of hours was only about 45 minutes. Finally it was time for lunch. The other three employees that were lucky enough to receive the weekend shift had already finished their work, and were on their way out the door as Drew and Alex walked towards the break room to have lunch. Before they reached the door to the break room, Alex split off towards the restroom. As she did, Drew glanced over and watched her shapely ass bounce with each step until she disappeared behind the door.

He went into the break room and sat down in the same chair he always did. It was the one on the far end of the room in the corner, facing towards the door. He laid his head back against the wall, resting it in the corner for a few moments until he heard the door open. Alex walked in, not looking at Drew but towards the refrigerator and the snack machines. Drew immediately noticed that her shirt was extremely low cut. The deep V extended passed her cleavage, and the top inch or so of her belly could be seen where the fabric met.

Drews mouth fell slightly open, watching her large breasts jiggle ever so slightly with each step she took. She walked over to the refrigerator and swung it open, then bent down way further than she needed to, pointing her ass directly at where Drew was sitting. His cock twitched for a moment as he gazed at her heart shaped ass. The tight jeans she wore accentuated her curves quite well, and Drew noticed every inch of them.

"Goddamn that looks juicy." Drew thought to himself, imagining what the view would be if he was slamming his hips against her cheeks driving his cock in her ass.

His cock twitched again as he thought of this, but he shook his head quickly and averted his eyes as she began to stand. With her food in hand, she walked over and sat opposite of Drew. As she arranged the different Tupperware containers, Drew could not tear his eyes away from her breasts, threatening to bust at the seams of her shirt. It was obviously much too tight for her. He began to wonder if this was another one of her ploys.

The two of them began chatting, mostly about work stuff. Drew noticed many times while they were talking, especially while she was speaking, that she would press her arms tightly against her body, making her breasts squish together.

"So is Amanda still out of town?" She asked.

"Yeah, she'll probably be back Monday evening when I get home from the pizzeria." he replied to her, his eyes dropping to her chest every time she looked away.

"Oh, a weekend all alone? I bet that's got to suck." She said back to him as she finished the last bite of her meal and began to close up her containers.

"What makes you say that?" He asked, not quite sure what she meant.

"Oh nothing really. It's just that I know that if I had to go four days without getting laid I would go crazy." She said, standing up quickly from the table and taking her bag of empty containers over to the counter.

Drew didn't quite know how to respond to that. He just sat there, and stared at her ass as she walked away from him. Again his cock twitched in his pants, but this time it started to rise. He dropped his hands to his lap and tried to adjust himself so that his dick coming to life would not be noticeable through his pants.

"Oh well that was a boring lunch. Time to get back to work!" Alex said with sarcastic enthusiasm.

Drew groaned at her statement. He laboriously pulled himself up from the table and started walking towards the door. He immediately noticed that his cock was already about half hard. Alex stepped in front of him and opened the door, as he stepped forward, he bumped into her. His half awoken dick bumped into her ass. He froze, wondering if she knew what it was that had bumped her. She laughed, turning her head back over her shoulder slightly.

"In a hurry to get back to work I see." She said to him before turning her head back forward and continuing to walk towards their desks.

His heart skipped a beat, concluding that she had to have felt that. Having nothing else jutting out of his pockets, it had to be obvious. He couldn't deny that he enjoyed it though. He let her take a few steps in front of him so that he could admire her ass as they walked. Doing this of course did nothing to help the situation in his pants. By the time he got back to his desk, he was rock hard.

Luckily he only had two more folders to do and then he could go home and jerk off. As he continued his work, he couldn't help revisiting the images of Alex bent over at the refrigerator, or how luscious her big tits look as she smashed them together during their conversation. His dick strained against the fabric of his pants, forming quite a pronounced tent in his lap.

"Ugh, this day needs to end already." Alex said, breaking the silence.

"For real." He replied.

"So, do you have any plans tonight?" She asked.

"No, not really. Just gonna sit at home, probably watch some TV or play some Xbox or something. Then probably shower and jerk....." he started to answer, but stopped talking when he realized what he was about to reveal.

"Uhhh.............do what now?" Alex quipped, laughing and turning around again to face him. She unnecessarily leaned a little in his direction showing off her cleavage.

"Uhh, nothing. Forget it." He said, obviously a little embarrassed.

"Awww don't be shy." She said back to him, still laughing. "My night is probably going to go about the same. Minus the video games."

"I see." Said Drew, envisioning her on her bed fingering herself.

"You might want to get started early." Said Alex, looking towards his lap noticing the way he was hunched over attempting to hide his arousal. She then cleared her throat dramatically.

"I just might have to." He said back, winking at her. He immediately regretted doing so as he turned back to face his computer. She just giggled and resumed her work.

Finally he finished the last folder. He plopped it down in the pile designated for completed work and began to stand up, still sporting a rigid hard on. He started to walk towards the bathroom, right as he started to move, Alex turned her head and noticed the bulge in his pants sticking out quite far. Drew went to the bathroom with the intention of adjusting himself to hide his boner.

He entered the bathroom and stood in front of the mirror. He mentally chastised himself a little bit for flirting with Alex, something he had always tried to avoid. Then a memory flashed into his head. It was the strange woman from last night. The image of her popped into his head as clearly as if he was looking at her in front of him. He remembered what she wore and how she playfully bounced her tits for him putting on a show. He then remembered the object she had given him, and then the memories from last night flooded his mind. He tried to piece back together how the night went. He remembered laying in the bed jerking off to a picture of his wife's tits, and then being attacked by something.

He turned on the water of the sink and ran his hands under it, and then brought a small puddle up to his face and splashed the water against it. He shook his head trying to push the thoughts out of his mind. It had to of been a dream. He woke up absolutely normal, other than feeling a little bit sore in his groin area. He shook his hands off in the sink and then reached for his belt buckle undoing his belt and the button of his pants, he then grabbed the zipper and pulled it down. His aching cock sprang free and began bobbing in the air.

"What am I supposed to do with you right now?" He asked mockingly, looking down at his cock pointing directly towards the ceiling.

With his hands still slightly wet, he grabbed his dick and held it against his stomach while he attempted to buckle his pants again. Then, out of nowhere, he felt some thing stirring in the pit of his stomach. The feeling was very strange, as if something inside of him was moving and trying to get out. In an instant, a long black tendril shot out of his ass. He gasped and jumped back slightly, releasing his cock from its position. The tendril snaked from between his legs and rose in front of him. The tip of it open slightly, revealing what looked like a mouth with no tongue.

He swatted at it, but it dodged his hand. As he brought his hand back towards himself, the open tendril attached itself to the tip of his cock and began to engulf it. He immediately felt intense pleasure is it pulsated around his shaft. He couldn't help but let out a deep moan as it reached the base of his cock. He fell back slightly against the wall across from the mirrors. He looked into the mirrors watching what was happening. Something had come out of his ass and was attached to his cock and was now servicing it. His eyes began to roll back and his knees began to quiver as it pumped his cock.

Suddenly, the door to the bathroom flung open and Alex stood in the doorway. Her jaw dropped as her eyes took in what was happening in front of her. She brought her hand up and covered her mouth letting out a loud gasp. Drew looked over and noticed her in the doorway, he tried to move to cover himself, but he was completely immobile due to the immense pleasure he was feeling.

"Oh my God Drew! What the fuck is happening? I heard noises and came to check on you." She said, obviously shocked at what was happening.

Drew couldn't respond, only loud moans of pleasure came from his mouth when he opened it and tried to speak. She began to walk towards him, as if surveying exactly what was going on to better understand. He managed to lift his arm and attempted to waive her away, but she persisted. She stepped in front of him, watching the long, black, slimy tendril coming from his ass pumping his cock. Just at the moment that she noticed where it was coming from, two more tendrils shot out of his ass.

Alex jumped and started to take a step back when she saw this. She started to take another step back and the two tendrils shot towards her. They wrapped around her wrists and began to lift her in the air. She started wildly kicking her feet, one of her shoes flinging off and slamming against the wall of the bathroom. Two more tendrils shot out of Drew's ass and immediately wrap themselves around her legs. She struggled as much as she could, yelping and screaming, pleading for Drew to make it stop. But he couldn't, he was just as helpless as she was.

Another two tendrils came out and started moving towards Alex. Drew was powerless, all he could do was sit and relish in the feeling. Slowly they crept towards her, until they were only inches away from her waist. With blinding speed, one of the tendrils made its way up her shirt from the bottom, and slid up between her bouncing breasts before ripping her shirt completely off of her. Her huge breasts jiggled in the open air. She let out a yell when the second tendril started to go down her jeans. Just as the first one had, it ripped her jeans and thong off. She was now completely naked suspended in the air.

Drew admired her exposed body, finally getting to see what he always wished he could. Her huge tits swayed as she struggled. Her large dark nipples became erect from the cool air blowing from the air conditioning vent above her. His eyes followed her sensuous curves to the small patch of light brown hair just above her pussy lips, which were bald. He spotted the hood of her clit, tucked between her lips. Jolts of electric pleasure emanated from his balls at the sight of her struggles.

The tip of one of the tendrils began tickling her inner thigh, which made her shriek as it touched her. Slowly it crept its way up her leg until it finally met her shaven pussy lips. It gently prodded against her twat, which made her kick her legs even more. It slid between her lips and began lubricating her tight hole.

"Oh no.......no no no no no!" She screamed, but her voice was suddenly silenced by the second tendril jamming itself into her mouth.

Her screams quickly turned to muffled grunts as the tendril began rapidly pumping in and out of her mouth. The tendril between her legs pushed inside of her and as far as it could go, and began making the same rapid pumping motion in and out of her pussy. Through the muffled screams, a clear moan escaped from around her lips as it rammed it self in and out of her.

Drew stood there, unable to do anything but lean back and enjoy the sensation on his prick. As fucked up as the situation was, he could not help but to be extremely turned on by the sight in front of him. The tendrils attached to her limbs that were suspending her in the air began to turn her body. She was now upside down, her long hair gently brushing the floor as the other tendrils and her holes continued their onslaught.

The tendrils started to slowly bring Alex's body closer to his. Drew then noticed Alex's eyes go very wide. What he could not see was the much larger and much thicker tentacle that had emerged from between his legs. It's size was enormous. It was easily as big around as his leg. As he began to wonder what the new arrival would do, he got his answer. The tendrils holding Alex's body in the air began to bend her. Pushing her knees against her chest and slightly tilting her body towards Drew. He now had a perfect view of the thinner tendril pumping in and out of her pussy right in front of his face.

The large tentacle moved up under her, reemerging in front of him as it slid along her back towards her ass. The rounded tip of it met her asshole and began to prod. This brought more struggle from Alex. The tip of the tentacle popped into her asshole and began entering her at lightning speed. It seem to only go in, not pulling back out and pumping like the tendril in her pussy was doing. Drew watched her asshole stretch in amazement as more and more of the tentacle buried itself into her. Drew started cumming at the sight of this. He bucked his hips uncontrollably as his cock spurted semen into the tendril wrapped around it.