Mad Men: Joan Makes Don Submit

Story Info
The head secretary forces the boss to give her pleasure.
2.8k words
4.17
18.7k
4
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

Joan, the head of the secretary pool, entered Don's office with the usual stack of files ahead of his daily meeting. She wore a form fitting blouse with buttons in the front. Her red hair was neatly tied up in a bun. Don was in his usual starched shirt and black tie.

As she bent over to place the documents on his table, he took the opportunity to covet her ass.

"I saw that," she said, glancing back at Don with a raised eyebrow. "What?" Don said, rudely dismissive, then returned attention to his desk.

Joan stepped over to the window overlooking dozens of desks full of secretaries, and pulled down the blinds. A routine habit that usually precluded Don taking a nap. But instead of leaving, Joan locked the door.

Hearing the click, Don looked up. He thought he was about to get a chewing out for some recent mishandling of a fellow employee. "What?" he asked, this time firmly demanding an actually answer.

"I have something for you," Joan said, more sweetly than usual.

Don raised an eyebrow, curious. "Okay?"

"Stand up, and go to the corner," she said, pointing to a corner. Don contemplated this for a few seconds, but Joan's unrelenting smirk, and finger which continued to wave to the corner, quickly won him over. He stood up, mumbled, "Is someone in trouble with mommy?" and walked to the corner.

"Close your eyes," she said. Don did so.

She heard the light scuffing of her skirt as she walked up right behind him, then she whispered in his ear, "Remove your clothes." Don tried to look back at her, but she grabbed his head firmly with both hands, pulling his ear closer. "Take off all your clothes," she said. "Do it for me." She wiped on hand over his eyes to close them again, then let go and stepped back.

Don squeezed his eyes shut as he cooly unbuttoned his shirt, then pulled an arm out of each sleeve. Just as he finished with the second sleeve, he felt Joan tug it away. He then unbuckled and pulled off his pants. Again, Joan tugged them out of his hand as he finished. Then his boxers and socks. "Okay," he said, fully nude.

He could hear as she moved around and away from him for a dozen seconds. He imagined she was disrobing as well. He felt her place a soft material in his hand, which he immediately recognized as nylons.

"Put these on," she said.

Don opened his eyes and looked down. Indeed it was a pair of pantyhose. He also quickly noticed that his clothes were no longer on the chair. Instead panic set in.

Don spun around to see Joan, still fully clothed, by the door. "Put them on, or I open the blinds," she said, her smile gone. "Quickly." Her hand was holding the cord to the blinds.

It registered this was probably some sort of blackmail, but he saw no other option. He clumsily attempted to pull them on, leaning over to pull them over one foot, then fell to the floor. Joan watched him wiggle into them, clearly frustrated after they bunched up at his knees.

"Stand up," she said, and he stood, still tugging at them. "And stop moving." Don dropped his arms to his sides, and froze.

Joan walked to him and reached down, pulling the pantyhose into place around his waist, then tugging along his legs to ensure they were smooth. Satisfied, she dragged her fingers up from his feet to his ass. He sighed out of ecstasy.

"There, that wasn't so hard, was it?" she asked.

"What are you doing, Joan?" she asked.

Joan snapped straight up in perfect posture facing Don and smacked him. "You don't get to ask questions."

Don was stunned. He began to mumble, "Okay" but was stopped with another smack.

Joan added, "You don't say anything unless you're asked directly."

She grabbed him by the scalp and forced him to his knees with little resistance. She leaned down to his ear. "Do you understand?"

"Yes," he whispered back.

She turned to face him, their lips an each from each other. Don couldn't resist and pressed his lips against hers. She pulled back and smacked him again. "You do nothing unless your told," she said. This time she spoke as if she was addressing a petulant child, disgusted at his ignorance.

"You think you can have anyone you want, anyway," she said. "But you're about to learn, you can't."

"I've seen you watching me," she continued. "Fantasizing about me, pretending you could have me any time."

Don played coy, but stayed silent.

Joan loomed above him. Her right hand reached up to her bosom, her nails tracing their outline. "I know you've longed for these."

She unbuttoned her blouse, and pulled down her bra, allowing her ample breasts to spill out. She leaned over, swaying her chest so her nipples almost brush against Don's lips. He opened his mouth, yearning for them.

"Which one do you prefer?"

Don took this as an invitation, and wrapped his mouth around an areola, suckling madly. Joan smacked him again and pulled back. "I ASKED which one you preferred, I didn't tell you to suck on it!"

She grabbed him by the scalp again, tugging his head back. He grunted at the combination of frustration, pleasure, and pain.

Her free hand reached down, and with her nails traced his balls and cock through the nylons. She pulled down the nylons enough to free his cock. She smacked it up, causing Don to again moan out of ecstasy. She rolled her finger tip around the tip, pinching off the pre-cum that had collected there, then rubbed on her left nipple.

"Lick it off," she commanded. Don leaned to her left breast and licked. While Don was occupied, she reached down, teasing his cock and balls with her nails, smacking it, until more precum appeared. She wiped this on her right nipple.

"Suck it off," she commanded, and Don did as instructed. For the first time, Joan emitted a groan of delight. She let Don suck for a few moments, then pushed him back. "Get on your hands."

Don leaned over to be on all fours, and looked up at Joan. Already tall, and in high heels, from his new perspective she now completely towered over him. He watched as she pulled a small dildo out of her bag. "Open your mouth," she needed to say only once. Don closed his mouth around it as she slid it onto his tongue. "Do not drop it."

Joan leaned down to slowly remove her panties from below her skirt. Don eagerly watched hoping to catch sight of her private parts, but she was quick and discrete. She gently drew the dildo in and out of his mouth. "Get it wet," she commanded.

Satisfied, she pulled the dildo out, and then stuffed her panties into his mouth. She leaned down again to be face to face with Don, purring, "That's to muffle you while I fuck you in the ass."

And muffle it did. Don groaned at those very words.

She went behind him, with one hand spreading his ass cheeks, the other rubbing the dildo along his crack. Finding the hole, she slowly guided it in. It went in with more ease than she expected. "I see you've done this before," she said. Don snapped his head back, offended. Joan smacked his ass, raising her voice, "You don't move unless I say so."

With one hand on his waist for support, her other reached below his balls, lightly touching them. Even with the panties in his mouth, he couldn't help but moan in delight. Out of sheer reflex, he bucked his ass back, driving the dildo in deep.

As promised, Joan slid the dildo in and out of his ass, using her thigh for pressure. Feeling this, Don pressed back against her with each slow thrust. The harder he pushed, the more he could feel the soft heat of her thighs flush against him. Once a rhythm was maintained, she ran her fingers along his cock and inner thigh, and he began pressing harder, speeding up.

"You may be enjoying this more than me, " she said, finally stepping away from Don. His light moans became desperate grunts as he watched her walk to the office chair and sit down. She leaned back and spread her legs.

"Crawl over here," she said. "And if that dildo falls out of your ass, I swear I'll open those blinds and walk out."

Don began to crawl over. Joan stopped him with the heel of her shoe. "Remove this."

He slid her foot off and gently placed it on the floor.

"And my stocking."

He reached up to the top of her thigh. Touching skin, again she let out a moan.

"Wait," she said, and Don paused. She pulled the panties out of his mouth and tossed them aside. "Continue."

As Don began slowly rolling her nylon off, he saw Joan had reached down to run her fingers up and down her vagina. It was glistening. With her free hand she caressed her breasts.

By the time he was at her ankles he saw she was centering on her clitoris, circling it with an index finger.

As soon as the stockings rolled off her feet, she lifted her toes to his mouth, and commanded, "Suck."

Don rolled his tongue from pinkie to big toe, then took it into his mouth, flicking it hard, then soft, in a variety of motions. Joan moaned louder than before, causing Don to pause, worried the office would hear.

"Don't you fucking stop," she said in pace with her escalating stroke of her clit.

Don lingered on her toes for a bit more. He expected her to come at any moment. Realizing, perhaps, how loud she was becoming, she pulled her hands from her pussy and breasts, and let them swing to her sides. She took a moment to enjoy Don's devotion to her feet before issuing her next command.

"Make your way up my thighs," she said. "Slowly."

Don didn't hesitate, and made his way up her leg, making small kisses up her foot and ankle, licking from her ankle to her knee, then nibbling and more kisses up to her crotch. She grabbed him by the hair and stopped him before he could taste her.

"You don't get to taste my pussy," she said. "Just yet."

She stood up and pointed to the couch. "Crawl to the couch and lay down, face up."

Don made his way over, careful to not let the dildo penetrate to fall out, or penetrate too deeply when he laid down.

Joan walked over to Don, with one leg bare, the other in still in nylon. She lifted her leg up and let her nyloned toes tease their way from Don's balls and up the backside of his erection before pressing her sole to his cock, mashing it against his belly. She used it to steady herself as she slowly rolled off her nylon.

"I'm afraid you'll cum before I'm done," she told him. "But if this happens I want to make sure your cock stays nice and hard."

Once the nylon was off, she stood up and looped it it around his balls, knotting it so that it tied them off into a bulge, then used the remaining slack around the base of his cock, making it even firmer than before. Still, his cock throbbed with each of Don's increasing heart beats.

She leaned over to come face to face with Don.

"Do you want to fuck me?" she asked, politely.

Don grinned and nodded.

She scowled, and smacked his cock. Don moaned.

"Answer me when I ask you a question," she said, sternly. "Do you want to fuck me?"

"Yes, Joan."

She smacked his cock again.

"I'm going to fuck you first," she said.

She tossed her knee over Don's head, straddling his face, her hands resting on his chest. She lowered her pelvis til she could feel his breath on her pussy, teasing him each time his head arched up to reach.

She squeezed his nipples tight enough to make his moan escalate into a yelp.

"Make me cum, Don," she said, finally pressing her pussy to his face, her own head laying against his belly. Don's tongue plunged inside of her, lapping her vagina from each angle, each lick sloppy and hungry. She bucked as his tongue went in and out of her, directing Don to her most sensitive spots.

Feeling her almost lose her balance, Don took a chance and grabbed her by her thighs to offer support. She didn't protest. He used the opportunity to even pull her tighter against his face.

Zeroing in on her clitoris, he resorted to a simple technique he felt he'd perfected and spelled the alphabet with his tongue. His hands also began to wander, stroking up and down her thighs and across her buttocks.

Joan wiggled almost uncontrollably as Don came closer to bring her to a climax. Her hands held his hips in a firm grip. Almost only to focus herself, she wrapped her mouth around his cock, stroking it with her lips and tongue in rhythm with Don's own oral activity.

Don continues with his alphabet technique. When he got to "M", Joan pressed his pussy tight against his face and began bucking and moaning. Don knew he had hit the spot, and worked quick so he wouldn't cum before her. Don repeated the letter M a dozen times, until Joan sat up arched her back, and tossed her head facing up. She panted out a series of hard, squeaky breaths that Don was afraid would break into outright screams.

She came for so long Don nearly passed out for lack of breath. He was saved when the intercom buzzed.

Joan pulled off of him and stood up.

"Is everything okay in there, Mr. Draper?" his secretary asked aloud.

Joan nudged him, whispering, "Go answer her."

Donshuffled over to his desk, holding his hand behind him to keep the dildo in place. He pressed a button on the intercom,"Yes, Mindy. Everything is okay in here."

"Okay, Mr. Draper," Mindy buzzed back. "By the way, Peggy is here waiting to talk to you."

"Just give me a couple minutes. I'm finishing a meeting with Ms. Holloway."

"Yes, Mr. Draper."

Don looked back to see Joan was neatening up her dress, buttoning up the top. She pointed in front of her. "Come here."

Don shuffled back over and kneeled down in front of her. She leaned over and whispered in his ear.

"Here's what happens next," she said, her hand reaching around to the dildo. "This doesn't come out all day." She pulled it in and out a half dozen times, as if to make sure it was firmly in place. She then slowly untied the nylons from his cock and balls.

She moved her head to Don's other ear. "But first, put these back on me." She placed the nylons in his hands, leaned back, and pressed her bare toes to the tip of his cock.

Don slid the nylons over them, and glided them up her leg. The task wasn't made easy as Joan teased his cock with her foot.

When he was done she stood up, and slid back on her heels.

"I may be checking later to make sure the dildo is still there," she said. "For now, though, I'm going to walk out, and tell Peggy to give you sixty seconds then go right in. Your clothes are in the bottom desk drawer."

She blew Don a kiss, unlocked the door, and walked out, closing it behind her.

Don scrambled to his desk as he heard her outside giving Peggy those exact instructions. He'd barely finished buttoning his shirt when Peggy walked in. Fortunately, he was sitting behind the desk. This actually wasn't the first time a secretary was unaware he was without pants in the office.

"I was wondering if you had reviewed the Coors pitchdeck?" she asked.

More politely than usual, Don replied, "I'm halfway through," he said. "Let's discuss it after lunch?"

Peggy nodded, and turned to walk out. "Thank you, Mr. Draper."

As she closed the door behind her, Don said, "But it looks great so far!"

She looked at Don like he was an alien, and forced a smile back.

Don didn't leave his office all day, nor was able to focus as he anxiously awaited Joan's return. When she did, it was promptly at 5pm, when she said "Good night" as if nothing had occurred between them, then heard her giggle with the rest of the secretary pool as they made their way to the elevator.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousabout 7 years ago

Not bad. More mad men plz

Share this Story

Similar Stories

Blackmailed: Cheerleader's Cherry A Principal disciplines a stuck-up hot bitch cheerleader.in NonConsent/Reluctance
The Compliant Groom She owns him.in BDSM
Office Boy Pt. 01 A young employee submits to a new role.in BDSM
Surprised by Samantha Samantha dominates her submissive neighbor.in BDSM
Conquerors - Justice League Ch. 01 The god of the Amazons awakens to make the world right.in Celebrities & Fan Fiction
More Stories