A Tough Pill to Swallow

Hello, everyone! It's been a while since I uploaded. I'm sorry about that. Fair warning up front, this is a non-con story so if you don't like that sort of thing, just stop reading. It's all fantasy and I don't condone it in real life. That said, proceed at your own digression. For everyone else, I had a lot of fun writing this and I hope you all enjoy. Be sure to comment what kind of stuff you would like to see in the future. Thanks!

All characters are 18+.

Jenna sighed and leaned back from her computer, stretching and shaking out her shoulders. As the personnel executive for a large law firm in her city, most of her work consisted of looking at and reading through job applications from young, aspiring interns and employees and setting up interviews to evaluate their fit for the position. The rest of her time was spent occasionally terminating employees or making herself look busy when there wasn't anything else going on. Jenna didn't mind firing people. Usually the person in question had been recommended to be let go by their respective department head so she would simply push the blame up the chain and say there was nothing she could do. Overall though, her job was very easy, well paying, and afforded her own office and a lot of free time to watch Netflix on her laptop. She stopped her perusing of profiles as her desk phone rang.

"Personnel." She answered, slapping the receiver up to her face.

"Hey, Jen. It's Kate from front desk. How's your day going?" came the voice from the other end of the line.

"Oh, hi Katie." Jenna replied. "It's going. You know how it is. Always work to be done." She lied.

"Yeah, I feel ya, hun. You know you're allowed to hire an assistant, right?"

"I know, I just don't trust any of the kids that come in with something this important. I'd rather just take on a higher workload."

This was another lie. In reality, Jenna just didn't want anyone seeing how much position really required. There would never be enough work to justify having her own assistant and she would have to spend more time looking busy than she cared to.

"Hey, it's your funeral if you work yourself to death. Anyways, I've got your two interviews for the day. Should I send up the first one?"

"Yeah. Jason, right? Send him on up"

She pulled up his resume as she waited for the elevator to bring him to the twelfth floor where her office was. A few minutes later, there was a knock on her door and the young man walked in. Her first appraisal of a candidate was always of their dress. She noted positively that he was dressed in a nice full suit that fit his muscular body well. He stood across her desk, respectfully, waiting for her to ask him to take a seat. Another plus.

"Sit down, Jason." She said.

The young man sat down and smiled a warm, confident smile.

"Thank you, ma'am."

"Well, I've gone through your application and resume and your qualifications are more than sufficient to warrant the interview. How about we start with you running me through your profile and give me some more detail on your education."

Jenna sat, poker-faced as she listened to Jason speak about his resume. She was thoroughly impressed. Not only was he well qualified and educated, but he was a charming and charismatic speaker. He confidently worked his way through point after point about why he would be the perfect fit for the position and Jenna couldn't really argue. As Jenna laughed at his occasional jokes, she noticed him looking at her body appraisingly. Every once in a while, his eyes would flicker down her thirty year old body and pausing on her generous chest. She always left the top two buttons of her dress shirt unbuttoned underneath her blazer. The result was a generous yet professional amount of cleavage that made men wish for more. The glances were so subtle, most people would not even perceive them, but Jenna caught Jason. She held in a smile and continued the interview as normal. She was sure if she had offered, he would definitely like to take a closer look at her breasts, but unfortunately for him, Jenna didn't swing his way. Still, she had to admit that he was quite a catch, even if he wasn't her cup of tea.

Eventually the interview came to a close. Jenna thanked Jason for coming and led him to the elevator, informing him that they would call him in the next couple days to let him know their decision. That was all just for show, though. She had already all but decided to give him the opportunity. She knew that he would do very well at the firm.

Back in her office, she sank into her chair and began to absentmindedly daydream. She was snapped back to reality a few minutes later by a sudden knock on her door.

"Come in." she called out.

The door opened and a girl stepped through. Now THIS was more her type. The girl was a cute little thing. She couldn't have been more than five-foot-tall yet as she turned to close the door, Jenna noted that her ass was absolutely incredible; thick and pronounced from the rest of her body.

'She must do a lot of squats.' Jenna thought as the girl stood across from her desk.

"Hi, I'm Amanda. I'm here for the job interview." The girl introduced herself.

"Ah, yes." Jenna recalled. "Take a seat, Amanda."

Jenna pulled up Amanda's application and prompted the girl to begin going over her resume. Jenna had quite frankly forgotten about the appointment. She was already pretty confident that she would be giving the job to Jason. As the girl spoke, Jenna began to zone out and subtly check her out. She was really quite adorable. A tiny, twenty-one-year-old blonde. Her skirt was a business style, but its form fitting style had already clearly revealed her substantial ass-ets to Jenna. Her button up dress shirt was appropriately conservative for the office and, like Jenna's, showed off some creamy cleavage. Her breasts were smaller than Jenna's but still a good size for how petite and skinny the young girl was. Jenna could feel herself getting excited thinking about what she would like to do to the little beauty, but she maintained a mask of professional attention to presentation. When Amanda had finished, Jenna cleared her throat and began.

"Well, I appreciate you coming in, Amanda, but I think I have already found someone for the position just before you arrived."

Amanda's eyes turned a bit panicked, but she tried to control her facial emotions.

"Please, ma'am, I really need this job. I have a ton of student debt from college and haven't made a penny at any of my internships. This was my last chance before I have to move back home with my parents. I promise I can perform at this position and will do anything necessary to get the job." Amanda pleaded.

This made Jenna perk up.

"Anything?" She questioned.

"Anything." Amanda promised. "I will work whatever hours, whatever is needed. I need this job."

"Well I have been feeling pretty stressed out lately." Jenna sighed. "I'll tell you what. You get me off, and I'll find you a position here at the firm."

Amanda's jaw dropped a bit before she clenched her teeth and thought it over. She hadn't expected this line of extortion from a woman of all people. She chewed on her bottom lip as she mulled over her options. She could not move back with her parents and admit that she had failed. Although she was straight, she had had a couple drunk encounters with females before in college so she wasn't clueless in lesbian sex. And Jenna was a very attractive woman. How bad could it be? Lick some pussy for an hour and get a job? She had no choice at this point.

"All right, I'll do it." Amanda reluctantly agreed.

"Wonderful!" Jenna broke into a big grin. She slid her panties off and down her legs, leaving her skirt on.

"This is a nice, big desk. Why don't you come crawl under there for me."

Amanda sighed and walked behind the desk. Jenna wheeled her chair back and allowed Amanda to sink to her knees and back herself into the space where the chair would be. Jenna scooted herself back up to the desk and looked down and grinned at the tiny girl knelt before her.

"Why don't you take that sweet mouth below my skirt. I'm sure you'll find something to do down there."

Jenna felt a thrill run through her as the young girl leaned forward and began to work her head under Jenna's skirt. She knew that Amanda was expecting to eat some pussy, but Jenna had a surprise for Amanda and she could already feel it growing down her leg, now that it was free from her panties.

She heard a tiny shriek of surprise from the girl as her lips unexpectedly bumped into the head of Jenna's large and growing penis.

"What the fuck?! You have a dick?!" Amanda exclaimed.

"Surprised?" chuckled Jenna.

"Yeah, you're a woman. I didn't sign up for this. I thought you just wanted me to eat you out."

"Amanda," Jenna's tone grew serious as she rolled her pencil skirt up her thighs and bunched it at her waist, freeing her rod. "If you want this job, you will stop talking and wrap those sweet lips around my dick."

Amanda closed her mouth and whimpered but she knew she had no choice. She attempted a mean glare up at the woman who held her cards and reluctantly leaned forward to wrap her luscious lips around Jenna's monster head. Jenna groaned as she felt the girl's warm mouth envelop her member. She leaned back in her chair and basked in the feeling of a young mouth surrounding her gently. Amanda started bobbing her head lightly. She had very limited experience when it came to oral and that was with regular to semi-large sized organs. Jenna's member was monstrous. Now fully hard, it stuck down past Jenna's knees. Amanda figured it had to be at least a foot in length and thick around as her ankle. The head alone completely filled the young woman's mouth and strained her jaw. The best she could do was apply some suction to the tip and hope it would be enough. Unfortunately for her, Jenna was already growing tired of the meek attempt to please her.

"You gotta do better than that if you want to get this job, sweetie." Jenna warned.

Amanda felt a nervous shiver run down her spine, but she brought her right hand up to stroke at the length as best as she could. Finding her hand didn't even wrap around the monster in front of her, she brought her other hand up as well and began to slide her soft, curled fingers up and down while her lips remained suctioned around the head.

Jenna was quite enjoying herself despite the amateurish actions from Amanda beneath her desk. She didn't often receive blowjobs. It was difficult to find girls who liked chicks with dicks. Occasionally she would get too pent up and resort to hiring some poor escort to absolutely ruin for the night. Be that as it may, it had been too long since she had found a partner to blow off some steam with and she could feel her aggression starting to build a bit. However, she resolved herself to be content with Amanda's mouth and not take any of her other holes. No need to break the young thing's body at such a tender age. Besides, she quite liked receiving oral and, unfortunately for Amanda, it was going to get a lot more intense.

Jenna enjoyed another minute or so of Amanda's efforts but she was ready to take things up a notch even if the girl kneeling before her wasn't. She reached down and took a firm grasp of Amanda's head, thrusting her hips forward a bit and holding her in place. Her bulbous head jumped forward in Amanda's mouth, contacting her throat and triggering her gag reflex instantly. By the time she had reacted, bringing her hands off the girthy pole to slap and push at the shapely hips it was connected to, her uvula had already been battered by three additional lightning thrusts, each eliciting a retch. Jenna released her head, preferring to tease the girl more before really going all out.

"Sorry, sweetie. Aww, did that hurt you?" She said as she gently brushed the reflexive tears that had formed from the girl's eyes.

Her voice dripped with sympathy, but Amanda was too busy recovering to notice the mocking tone hidden within and the barely contained glee that lay in Jenna's eyes.

"Yes, that hurt! She complained. "I was choking!"

"I'd better be careful then. We don't want that to happen. Back to work, honey."

Amanda hesitated for a moment but complied. Her lips re-captured the head and one hand resumed stroking while the other firmly gripped right in front of her lips. Jenna left her hand idle for a bit, just gently stroking the girl's silky hair and letting her work. Eventually though, she wanted more and attempted to push her head down to gain more depth. To her surprise, Amanda had learned her lesson and kept her right hand locked around Jenna's shaft directly below the head, preventing her own face from being skewered again.

After a few thrusts that resulted in Amanda's lips bumping into her fingers but nothing more, Jenna released her. She bit her bottom lip to contain the smile that appeared. She liked a girl with some fight. She could tell Amanda was determined to maintain control and that would make it so much sweeter when she broke her. However, the hand blocking her advance did pose some annoyance. Jenna was confident that she could easily overpower the diminutive female but what fun would that be? No, Jenna much preferred to trick and tease before taking over completely. All she had to do was find a way to dupe her into removing her hands and she would once again have access to pummel her entrance and soften it up for her main course. Jenna's hand resumed its idle stroking of Amanda's blonde locks as she mimicked an apathetic demeanor to lull the girl into a sense of security.

"Amanda, what color is your bra?" Jenna asked, innocently.

Amanda paused and looked up, worriedly.

"I didn't say stop. Keep sucking." Jenna chastised. "Unbutton that shirt of yours for me. I'm...curious."

Amanda re-applied her suction and removed her left hand from its stroking motion to unbutton her shirt. She quickly found that she was unable to complete the task with only one hand. In a lapse of judgement and memory, her right hand also joined her other to begin unbuttoning her shirt. Jenna's eyes shone with glee as her plan came together before her. Her delight only grew as she was struck by sudden inspiration that would only make her plan even better. As the last button separated, Jenna stood up.

"Let me help you remove that troublesome shirt." She explained.

Reaching down, she began to slip the dress shirt off of Amanda's dainty shoulders and down her back. The motion forced Amanda's arms behind her back as the garment slipped down. In a lightning movement, Jenna grasped the sleeves as they slipped off her and twisted them around Amanda's wrists tightly, tying the ends together in a secure double knot. Amanda realized her mistake in the following moment as she found her hands tied together behind her back. Her eyes flew back up to Jenna's face where her evil grin sent a chill through her. She began to back off of the dick in front of her but it was much too late. Jenna's hands grasped either side of her head, immediately stopping her progress and forcing her back down the inch she had lost. Her worried expression became scared as she looked desperately into Jenna's gleeful eyes.

"Oh, sweetie, you're much too gullible." Jenna giggled. "Although, I will admit it was rather clever of me. Time to take things a bit more seriously."

With that, Jenna's hips thrust towards Amanda's face, smashing into her uvula and ripping a gag from the girl. Amanda tried to wrench her head free from Jenna's but she didn't have the leverage nor the strength to free herself. Jenna continued thrusting, each time gaining additional purchase further into the young girl's mouth. Every movement stretched her lips a bit more as the girth increased with the length. Amanda's throat had never been entered before and its tight, virgin entrance was loathe to give way to the massive battering ram knocking down the gates. Eventually, though, the muscles defending her esophagus began to tire and one particularly powerful impact gave way a bit as the head squeezed into her trachea.

Jenna smiled as she felt the girl's opening give way under her exertions. Pinning Amanda's skull to the edge of her desk, she increased the pressure assaulting the girl's entry. Shoving and pressing, Amanda's gateway finally gave up the ghost and Jenna's length slid several inches down her gullet. Amanda's eyes, which had been clenched in discomfort up until that moment, flew open in shock. She began to trash as best she could in a desperate attempt to liberate herself. Unfortunately for her, she didn't stand a chance against Jenna's lust enraged strength and she was held steadily in place. Her arms tugged and wrenched at the cloth binding her wrists, but the material didn't budge. Her last hope was to send a message through her eyes to Jenna, hoping for a reprieve. Jenna smiled down at the desperate look on Amanda's face, her cock flexing in excitement and drawing another choked cough from the girl.

"Don't worry, hun," she said, stroking the girl's face. "At least one of us is going to enjoy this."

The worry in Amanda's eyes increased but they clenched shut again as Jenna's cock once again resumed its path down her throat. Her slim neck was already plainly showing the monstrous intrusion from the outside and it continued to grow. Jenna bit her bottom lip as more and more of her shaft disappeared in Amanda's mouth. She choked continuously as the seemingly endless pole slid onwards toward her stomach. Amanda's nose suddenly bumped into something and she opened her tearful eyes to find herself face to face with Jenna's abdomen. A quick glance down confirmed that her nose was pressed against Jenna's crotch. Shock briefly overrode the discomfort as she realized that meant the entire fourteen inches had been forced down her tight, virgin throat. She hadn't thought it would be possible for the beast to fit in her but Jenna had given her no choice.

Jenna's emotions were on the opposite end of the spectrum. She was elated and lost in the blissful sensations of the tight throat surrounding her length. She ground her hips against Amanda's face, smooshing her tiny nose into her crotch and making her whine and choke even more. She kept the girl pinned against her desk while her hands stroked the girl's cute, pained face in glee. Amanda, for her part, returned her gaze with one of desperation, silently pleading for mercy. Jenna had no plans to release her toy any time soon, unfortunately. Keeping Amanda in place, she reached down and grasped the designer belt that was around Amanda's waist.

"Can I borrow this?" she asked, mockingly waiting for a response that she knew wasn't coming. "Thank you! That's so kind of you." She laughed.

Removing the belt from the girl, she brought it up to her own waist and wrapped it around herself and the little blonde head attached to her. Amanda, realizing what Jenna's intentions were, whined franticly and resumed her frenzied attempts to free herself. Unable to do so, she felt a chill as the belt tightened behind her head and clicked into place, securely locking her onto Jenna's crotch.

Jenna let out a sigh and beamed with pride. Pulling her chair up behind her, she took her seat again, Amanda's trapped head following her crotch. She ran her fingers through her prey's frazzled, blonde locks and smirked down at the girl. She was truly in heaven. Every convulse and contraction of Amanda's tortured throat sent a jolt pleasure through Jenna. The tight, little throat surrounding her cock was constantly constricting and massaging her and every pained gag sent a shock of a bliss through her.

Amanda, on the other hand, was not having a good time. Her neck was bulged obscenely by the thick cock filling her windpipe. Her poor throat, which had been untouched by anything up to this point in her life, was now being stretched and extruded by the woman she was attached to. Her only source of oxygen came from the inconsistent breaths that whistled through her nostrils and left her feeling a bit light headed. Unfortunately for her, she had plenty of air to remain conscious for the entire torturous ordeal.