Office Wish, Gangbang Fantasy

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
HeyAll
HeyAll
22,154 Followers

"Okay, I think I better go now," Leanne said, this time with a real smile. "It was nice meeting you. For a doctor, you have a great sense of humor."

"Nonsense. We're all here for a purpose."

The doctor moved his hands. For a split second, Leanne thought he was going to shake her hand, or maybe even give her a great big hug and laugh off the prolonged gag.

Instead, he reached up and undid the top buttons of her blouse. Her weakness for hot doctors and corporate scenarios made her body freeze as Dr. Williams kept unbuttoning her blouse down to the point where it tucked into her skirt. She looked down and saw that her bra was exposed.

She looked over to Mr. Klein, who was still on the phone talking business. Surely he would put an end to this, since he was well-versed in company policies regarding sexual harassment.

Instead, the boss gave them both a thumbs-up as he kept talking to someone. Leanne was left feeling helpless and alone, yet strangely aroused.

Dr. Williams flung her blouse open and gazed. "So far you look like you're in great health and incredible shape."

She should have slapped his face, but instead answered, "I eat well and workout at the gym in my apartment building."

Her voice squeaked as she answered. Meanwhile, the doctor seemed completely unphased. He had seen this all before. And his comfort level showed as he pulled her blouse behind her shoulders, and removed it completely, leaving Leanne standing in her bra and skirt.

"I'm going to remove your bra," he said, staring at her chest. "Hmmm... Let me guess, 32 b."

"Precisely."

"I thought so."

He reached back and unclasped her bra, letting free the small tits, with the pink nipples already erect. Both the doctor and the boss stared openly at the tits.

"Are you cold or aroused?" the doctor asked.

Leanne clenched, and her nipples became harder. "Both, I think. I've never been topless in an office before."

"A surreal feeling, I'm sure. Now for your skirt."

The skirt!? As the doctor bent down, every muscle fiber in Leanne's fit body screamed to use her kickboxing training and knee this guy in the face. Instead, her body betrayed her. She felt stiff as a board. Maybe it was fear, or maybe it was something else entirely...

Whatever the cause, Leanne stood still as the doctor pulled her skirt down to her ankles. Then down went her panties as well, revealing her private ladies parts to the men in the room. She was always self-conscious about the first reveal to men, and she was glad that she had cleanly shaven herself two days ago.

"Can you step out of your clothes please?" he asked.

Part of her wanted to give him a karate chop to the throat.

Instead, she said, "Sure."

She lifted one foot, then the other and then she was bare, except for her stockings and heels.

"Heels too," he added.

"Okay..."

He bent down and removed each heel, as she rested her hand on his shoulder for balance. He also took off her stockings.

When it was done, Leanne was completely naked and barefoot in her boss's office. What was even more amazing was that no one seemed shocked by her nudity. In a weird way, she was kind of offended that the men weren't gawking at her. She worked hard for this body and felt the men should be paying more attention to her hard-earned figure.

"Now for a brief check-up," he said.

"That...umm... won't be necessary. I get a check-up regularly."

He raised an eyebrow. "Were your check-ups for 'Airtight' gangbangs?"

Those words made her feel light headed.

"No sir," her voice squeaked. "They were not."

"Well then, hold still."

The doctor used a small light to examine Leanne's eyes, nose, and ears. This wasn't a fake examination. He studied her intensely, the way any good doctor would.

"Now stick your tongue out," he said. "Say 'aaahhh'."

Leanne complied and stuck out her tongue, against her better judgment. The doctor used a wooden tongue depressor and a penlight to inspect her throat.

"Your dentition is outstanding, and your pharynx is in perfect condition for deep throating," he said, pulling away his tools. "Nothing over 6 inches though. Your gag reflex is average, it seems."

Leanne's eyes widened. Deep throating? What the hell kind of doctor is this? Although she stood naked before him, she still had a hard time believing this was real.

Then the doctor put down his instruments and moved on to her breasts. He pressed two fingers around the firm tissue of each tit, cupped them gently, and examined the skin around the hard nipples.

"Your breasts are in good health," he said. "Now, I'll need you to sit on the table. Lean back and open your legs, just like an ob/gyn appointment."

"Why? I already have a gynecologist. I go every year for an exam."

Again, he raised an eyebrow. "Does your gynecologist check to make sure you can handle a hard pounding?"

"No," she said, defeated.

"Well then, on the table you go."

The condescending nature of the request had Leanne feeling miffed. Especially in front of her boss. But complaining seemed moot, since she was already butt naked and had allowed half of the medical exam to occur.

She sat down on the table, which felt cold against her butt, and scooted back so she could lay on it. She raised her knees and put her feet on the edge of the table, so that her pussy would be completely exposed to the doctor. He pulled up one of the chairs that sat in front of the desk and placed himself in front of her crotch.

"You need to scoot down a bit more, so that your bottom is on the edge of the table," Dr. Williams said.

Leanne groaned and followed his instructions; it really was just like a doctor's office. His hands began to move her labia from side to side. Her clitoris was not touched.

"Externally, everything seems to be in order. Your vulva appears healthy."

Dr. Williams then grabbed the metal speculum and positioned it at the opening of her pussy. It was predictably cold, and caused her pussy to tighten.

"Aren't you going to use lubrication?" Leanne was a bit alarmed.

"I would, but it looks like lubrication won't be necessary," replied Dr. Williams, without any sarcasm in his voice.

His clinical demeanor both reassured and stimulated Leanne. She was sure he was right. It had been a long time since any man had touched her pussy and her fuse was pretty easy to light.

The speculum was inserted, carefully. As usual, it was put in sideways, then twisted and opened. Leanne felt every movement because she was so tight from lack of use. As the speculum opened, she felt pleasure. It wasn't just the physical presence of the speculum, but also the knowledge that a trained professional was staring directly into her most private place.

"Mr. Klein, could I trouble you to assist me?" said Dr. Williams.

Mr. Klein replied immediately, putting his free hand over the speaker of his phone. "Of course. What do you need me to do?"

"I would like you to hold my penlight so that it's shining directly on her vaginal area. It will make it easier for me to determine her fitness for a proper pounding."

Mr. Klein ended his phone call, walked over to the desk and picked up the light which the doctor had used to examine Leanne's throat. He stepped behind Dr. Williams and held the light over his shoulder. In the process, Mr. Klein leaned over so that he, too, stared into the dripping wet pussy.

"Thank you, Mr. Klein. Could you move it a little to the left? Yes, that's much better. As you can see, her cervix is pink and appears to be in excellent condition. I don't see any issues to rough vaginal sex."

The speculum was closed and removed. Leanne breathed a sigh of relief.

He continued, "One last thing, Ms. Caulfield. I'll need you to flip around so that you're bent over the table. I'll need to examine your anus."

The color drained out of Leanne's face. Despite her reluctance, she did as instructed. Then the doctor's hand pulled her left cheek to the side. Immediately, she felt something cold press against her anus.

"What are you doing?" Leanne asked, gasping for air. "I don't think you need to examine that part of my body, Dr. Williams."

Dr. Williams halted the examination.

"Perhaps I didn't make myself clear. 'Airtight' refers to the placement of a penis in each of your three cavities. My job is to make sure that your anus is healthy enough to take a penis. Have you ever had anal sex before?"

"Well, sure I have..."

It embarrassed her to admit this in front of her boss, and reflexively, her butt clenched.

"Ms. Caulfield, please relax your anus. The exam will be much easier if you do."

Leanne tried to relax. She was shocked again by her natural inclination to follow the physician's orders. In an odd way, it felt like she was pursuing her destiny.

"I'm about to insert a small probe into your anus. It will allow me to determine the health of your rectal mucosa. Mr. Klein, I could, again, use your assistance."

"I'm ready to help in any way," the boss said. "She is one of our most valued employees."

Turmoil swirled in Leanne's brain. Had she arrived in an alternate universe? Was her superior really about to gaze directly into her rectum? And why did the idea of that turn her on completely?

"Please hold the flashlight exactly as you did before," instructed Dr. Williams.

Leanne felt pressure in her anus as the probe entered her small puckered hole. Though horrified, she was eager at the same time. The fullness that followed was unlike anything she'd ever experienced. She moaned as the probe was inserted completely.

"Mr. Klein, this is pristine rectal tissue. In fact, it's one of the healthiest rectums I've seen in years. I'm certain she can handle rough anal sex, if done safely, as well as double penetration."

With a reverent tone, Mr. Klein replied, "Ms. Caulfield has an outstanding reputation. I would expect nothing less. It's a privilege to see her anus in all its glory."

Leanne was initially shocked to be the object of such a discussion. But knowing that Mr. Klein was looking into her rectum, along with the sexy doctor, almost had her orgasming on the spot.

The probe was slowly removed, and Leanne groaned. She was hornier than she had ever been in her entire life.

"Please, stand up Ms. Caulfield," the boss said. "With your clean bill of health, we're ready for the next step."

She stood upright and faced the two men, naked and perplexed. "The next step? What would that be?"

"A gangbang in the office area."

Was this for real?

***

High heels were definitely the bane of every corporate woman's existence. Leanne enjoyed looking sexy, but her feet were left aching at the end of her busy days.

It was strangely comfortable to walk barefoot across the carpet, past Mr. Klein's secretary. However, the comfort she felt from walking barefoot was offset by the surreal nature of being totally naked in her workplace. Mr. Klein held her hand to guide her through the department, while the doctor followed behind.

Her pussy pulsated and her heart raced as she was taken to the open space office area. Parading around naked in front of her subordinates left her feeling oddly liberated. After a few tentative steps, Leanne began to sway her hips, which made her breasts jiggle for all to see.

Bizarrely, no one freaked out over her naked body. Under normal circumstances, everyone would be shocked at the sight of their manager walking around unclothed, especially with a killer body like hers. Instead, all Leanne received were nods of appreciation from men and women, along with a few winks.

A young male employee briskly walked towards them with a folder in hand.

"Ms. Caulfield, I've completed the report you requested," the young man said, holding up the folder.

Leanne gulped and tried to maintain her composure. "Very good. Put it on my desk."

"Yes, right away."

The young man nodded and walked away, as if Leanne's nudity was of no consequence, though he did briefly glance at her nipples and pussy.

"What is going on here?" she whispered to her boss.

Mr. Klein looked puzzled as they kept walking. "What do you mean?"

"Why is everyone behaving in such a peculiar manner?"

Leanne realized the absurdity of her question, given the fact that she was the only one naked, in front of an office full of people.

"All I see are hard working, dedicated employees," he said proudly. "And they're going to be given a treat for their loyal service."

They reached the main, open office area, which was under Leanne's command. She continued to feel out of place, yet very at home. It was an unusual feeling. Down deep, she hoped her instincts were correct and that a very special dream was about to come true. As she entered the center of the common space, the employees seemed mostly nonchalant by her appearance.

"Right this way," the boss said.

They entered a conference room with clear glass walls. Assuming an actual 'Airtight Gangbang' would take place, it would be in full view of Leanne's underlings.

She tried to relax inside the conference room where she regularly held meetings. It became more challenging when she saw Mr. Klein standing by the door, signaling to people in the office area. It seemed the time had come.

In perfect order, three men stopped what they were doing and lined up at the door. It was exactly as Mr. Klein had instructed. The men exchanged handshakes with the boss as the doctor observed from the sideline.

On cue, the men began undressing and Leanne stood wide-eyed at the nudity unfolding in front of her. These men worked beneath her, and she was overwhelmed at the notion that they'd soon make her 'Airtight.'

When the employees were completely naked, the boss gave the first of several orders.

"Bryce, lay on the edge of the table," Mr. Klein said.

Bryce had spent the last three years working for Leanne. He was incredibly attractive with brown eyes and jet black hair, and his body reflected hours spent in a gym. Leanne briefly closed her eyes, shook her head, and then blinked several times as she tried to clear what she thought was an apparition. When she refocused on Bryce, he was moving toward the table.

He did as he was told, laying on his back on the edge of the table. His muscled thighs hung off the side. His cock was semi-erect and aimed upwards. Leanne gulped, as she considered the implication.

"Leanne," the boss said. "It's your turn. Mount him. Don't worry, the table is secure, it won't flip."

"You mean... sit on his lap?"

The boss seemed slightly amused. "His cock. Sit on his cock, Leanne. This is the first entry point to your gangbang."

Leanne's eyes stared at the cock as it suddenly sprung to full mast. It had been a while since she had a cock fill her pussy, and this was more than adequate. All eyes were on her, as she weighed her options. This still felt like an odd dream, but the wetness and aching in her cunt was real. She needed to be fucked, and by some miracle there was a hard cock on the table, waiting.

She stepped forward, climbed on the table and positioned herself just over Bryce's cock. The doctor grabbed Bryce's dick with one hand and Leanne's shoulder with the other. He guided Leanne down until the cock docked into its steamy destination. Leanne's pussy was treated with the utmost delicacy and care by both men.

Leanne lowered her body, under the direct supervision of the doctor, until it was all the way inside of her pussy. The sensation of a thick cock wedged tightly in her underused hole almost made her orgasm immediately. She looked around and saw her audience, then looked back down at Bryce. The earnest look on his face put her at ease, even though he said nothing. His hands began to caress her arms, and soon moved to her tits.

Leanne moaned and stayed perfectly still in order to enjoy what Bryce had to offer. She felt a bit light-headed by the entire situation, but her pussy would not be denied. Even though she was in a precarious position, balanced on her knees at the edge of the table, she began to smooth her body in an attempt to create a delicious friction where the two bodies joined.

"Perfect!" Mr. Klein stated with joy. "Now for your asshole."

The words startled Leanne. Just as she was becoming accustomed to the joys of the big cock stretching her tight pussy (after a several month lay-off), she was now expected to take a dick in her asshole at the very same time! Double penetration was a fantasy of hers, but it wasn't something she ever expected to happen, especially under these circumstances.

Paul stepped over from the doorway. He had been at the company for just over a year. Leanne knew little about his personal life, but he was tall, with dark hair and an angular face. She turned her head as he approached, and gauged the size of his dick. It was large and already primed for action.

Dr. Williams removed a small packet of lube from his pocked and coated his finger. He applied a generous amount to Paul's cock. Thank goodness, Leanne thought, that someone was prepared for anal.

She jerked forward as the doctor's lubed fingers pressed against the outer ring of her anus. After a quick coating, he pushed two fingers inside of her rectum, causing her to gasp as the fingers lubricated her private passage.

"Ready?" the doctor asked, pulling his fingers away.

Leanne tried to relax. "Yes, I'm still loose from earlier."

Paul pressed the tip of his hard penis against Leanne's anus then pushed until the tip popped into the pucker. Once again, this penetration was handled under the doctor's supervision. He took great care in making sure that her rectal cavity was not overpowered by a sudden intrusion. As a result, Paul slowly inched his way forward.

Leanne did her best to remain still as her asshole was stretched by the cock claiming her rectum. Sure, she had enjoyed anal sex before, but having her asshole stuffed, while her pussy was full of cock, was something she'd never forget. The pressure in both pleasure holes felt heavenly, especially as the cock bottomed out inside her ass. She was briefly overcome by her crammed tunnels.

Leanne's face contorted from the intense feelings, both physical and emotional. She wanted more, but needed to adjust. For a moment, she reigned in her passion, determined to proceed at the physician's recommended pace.

"Are you holding up well?" the doctor asked.

Leanne gulped. "It feels... intense... oh... I like it..."

The doctor knelt down behind Leanne and carefully examined her vaginal and anal tissue, making sure that her body could handle the double penetration.

"Looks good," he said, rubbing the skin in between both holes. "In my professional opinion, your body is well suited for this type of sexual act. We can move on to the next step."

Finally, the third man approached with a smile on his face. It was Jack, who was the youngest person in the department, having been hired a little over a year ago. Though Leanne didn't know much about him personally, she knew he was between girlfriends.

As he approached, Leanne was able to glance at the busy office through the glass walls. Oddly, work went on as usual. Despite the spectacle, no one stared and gawked while she was being double-penetrated in the conference room. Even though she saw a few men and women peek quickly, it was as if this was a perfectly normal occurrence.

Jack stood before Leanne. His cock was directly in front of her face. As she studied the erect cock, she was awestruck by its size. She never would have guessed that Jack was so well endowed, because he carried himself in such a humble manner.

Leanne realized this was the exact same office fantasy she had used for her masturbation fantasies. Had someone read her mind?

"Open up," Jack said.

The irony struck Leanne immediately. Jack was someone she enjoyed ordering around because he was so quiet and meek. Now here he was, telling her to 'open up' so he could stuff his hard cock into her assertive mouth.

HeyAll
HeyAll
22,154 Followers