MILF in Office Trouble Pt. 06

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"I love my cock sucked, so we should get along great!" the last one said and whistled when he went by.

Mary was mortified but kept her head down as they passed. Her tits were beginning to ache from being bounced around for so long.

They reached the halfway point and found a bench out of the way and took a rest. Mary was sweating profusely and red in the face from the exertion and humiliation. Shelby was in much better shape and was barely breathing heavily at all.

"You are a champ. See, it's not so bad. They have no idea who you are." Shelby said, trying to cheer her up.

"A couple of them saw my back tattoo, that was the worst!" Mary said, trying to catch her breath.

"Shall we head back?" Mary said after she felt able to continue. She did not want to be out looking like this any longer than she had to.

Mary was surprised when Shelby handed her a mask. It just covered the eyes and looked like a mask for a princess costume.

"Well, it's a little late for that now!" Mary said as she took it.

"You are going to want it, Mary. Kelly wants you to run back without your top, so I brought this mask to hide you." Shelby said, looking sad.

"What! No fucking way am I running back with my breasts exposed." Mary said, now really upset.

"Look, Mary. If you do, Kelly will let you cum today. The mask will hide your face, plus I will also take off my top so you will not be the only one. If you refuse, then she said you will not be allowed to cum for weeks! It's only a ten minute run back to the car, and most of it is through the trees," Shelby said, trying to convince her.

"This is so messed up. OK, but I am going to run as fast as I can!" Mary said.

"If you feel like cuming, try and reach down and pinch your clit while running. That way, you don't have to stop." Shelby suggested.

"OK! Let's get this over with!" Mary said.

They waited until no one was seen, then they pulled their tops off, put on their masks and dashed back to the car as fast as they could.

Mary's tits were flying up and down as she picked up speed. Shelby let Mary hold her tits by the bottom so she could run faster. They passed a few men running the other way.

"Holy shit! Look at those tit's," one guy said to another.

"Did you check out the tattoo? What a slut!" Another said.

Mary looked over at Shelby's tits flying up and down also. Her tits were not nearly as big as Mary's. Shelby just let them bounce as she ran beside Mary.

"Quite a pair we are, huh!" Shelby said, smiling at Mary.

The whole situation was so absurd that Mary returned the smile. Here they were, running for their life, half-naked with their tits flying up and down.

I couple more guys saw Mary when they came running around a corner, pinching her clit while running to fight off another orgasm.

"Look at that Slut! She is masturbating while running, what a whore!" The guy jeered.

Mary had to keep pinching or she would come. Both guys got a clear view up close as they ran by, she was crying at this point.

"Just a little farther!" Shelby encouraged. Shelby was strangely jealous. The attention from the guys focused on Mary even though her tits were also flying up and down.

"Well, her tits are amazing. I guess if I were a guy, I would be looking only at her! Still, it makes me mad she has such an amazing body, especially for her age!" Shelby thought as she looked at Mary perfect DD's bouncing.

They came out of the trees and flew towards the parking lot. Unfortunately, there were nearly a dozen people gathered for a group run. They all stared at the par running by. Several of the men broke out their phones and took either photos or videos of them. At this point, they only cared about making it to the car. They ran right past the group at top speed and made it to their vehicle. They quickly got in.

"Holy shit! Did you see all of them gawking at us? Thank god for the masks!" Shelby said as she pulled her top back on.

"That was just awful!" Mary said as she broke down and cried.

"There there! It's OK. Listen to me!" Shelby said as she lifted Mary's chin.

"I know it was bad, but it was also exhilarating. When was the last time you felt so alive? We had masks. They have no idea who we were. I don't know about you, but I am wet with excitement. Feel." Shelby said as she took Mary's hand and thrust it down her spandex shorts to her soaking pussy.

"Wow, you are wet! I guess you are right. That was a thrill, but I would not voluntarily do that again." Mary said.

"I bet you are just as wet!" Shelby said and surprised Mary by sliding her hand in Mary's shorts and fingering her pussy. Her hand came back out, dripping with pussy juice.

"See, don't tell me that it wasn't exciting!" Shelby said as she leaned over and gave Mary a long wet sloppy kiss.

They broke the kiss a few minutes later. Mary's head was spinning.

"Wow, Shelby, you really laid one on me!" Mary said.

"You are as sexy as hell, Mary. I would go down on you right here in the parking lot if it was allowed. Now let's get out of here before anyone else notices us!" Shelby said.

Mary drove away quickly out of the parking area and back to her house. She still felt shame but had to admit it excited her.

"See you at work! I had a great time!" Shelby said as she got out of the car.

"OK, Shel, I'll see you later." Mary said, not agreeing with the "Great Time!" Statement from Shelby.

She walked into her house, took a shower, and got dressed from work. She had to wear red thigh highs today with garter belt tops with little bows in them. The stockings were the retro kind with a line running down the back. Her long legs looked sexy as hell. She did not eat as Kelly told her that the only thing she needed for breakfast was a belly full of cum from her daily morning blowjobs. The order sent thrills up her spine at the dirty nature of it all. She set up her shelf bra with her see-through blouse and positioned her breasts for maximum cleavage with the top three buttons open, it was the most exposed she had ever been. It was beginning to feel OK for her. Her barbell piercings were only hidden by her see-through blouse as the shelf bra did not cover her nipples. She stepped into her 5 inch black high heels, applied red lipstick and eye shadow, to give her that sultry look, and headed out the door. She did not bother with wearing her blazer while driving. She caught several glimpses from drivers of both sexes staring at her massive cleavage. Her clit was already throbbing by the time she got to work.

She walked into her office. Shelby was already there looking over the schedule for Mary.

"Well, good morning, sunshine! We have a busy day. You are a little late, so you better hurry and take off your clothes and get on the treadmill quickly, or we will run out of time before your first meeting!" Shelby said as she opened the closet to pull out the treadmill.

"But, we already ran this morning!" Mary protested.

"Sorry, Babe! Orders are orders!" Shelby said as she motioned to Mary to hurry up.

"Well, OK, but I really don't feel like shocking my clit this morning and take it easy with that paddle. It doesn't take much to bring me down from cuming with that thing!" Mary said as she stripped and stepped up on the treadmill.

"Kelly wants me to use my bare hand this time. I think she wants handprints all over your ass." Shelby said as she positioned herself behind Mary.

"Great! She is a sicko!" Mary said as Shelby started the program.

"Yes, she is, but she is also our boss!" Shelby said, relishing the idea of spanking Mary's perfect tight ass, which was getting more toned as Mary exercised more.

Shelby's favorite part was seeing Mary big tits start to bounce up and down to the beat of Mary's footfalls as the treadmill picked up speed. After only a few minutes, Mary felt her first orgasm building deep in her lions as her clit was bombarded with stimulation from the clit rods. The clit rod embedded in the top center of her clit hood was the worst as it was not a straight rod, but had a curly etching, all the way down the rod, to cause an extra sensation. When she ran, her whole clit got worked hard like she was masturbating.

"Oh god...here it comes...it feels like a big one!" Mary moaned.

SMACK!

SMACK!

"Oww!" Mary cried but kept on running. Her orgasm subsided, but another one started to build almost immediately.

Two bright red handprints appeared on each butt cheek, much to Shelby's pleasure.

The next climax took five full minutes to build. Shelby had cranked up the speed. Mary was running at a good pace, with sweat dripping off her forehead. Her tits were really flying, keeping pace with her increased speed. The barbells were straining her nipples, only adding to Mary's excitement.

Mary was caught up in the pain of her nipples and forgot to warn Shelby in time. She was going to cum!

"Oh god, I think I am going to cum!" Mary said but kept on running.

SMACK!

SMACK!

SMACK!

SMACK!

Shelby really laid into her ass to keep her from cuming. Mary screamed in pain as the orgasm was just headed off by a hair. Mary's ass was on fire.

"Holy shit! Yeow! Fuck, that hurts!" Mary screamed.

"Sorry, but you almost came!" Shelby said as she really enjoyed smacking the hell out of her perfect ass.

Mary's needy clit was throbbing, and her nipples were raw by the time the treadmill stopped. Shelby had to smack her ass several more times before the end. Her ass was bright red with hand marks all over each butt cheek.

"Wow! My ass is on fire. I guess that morning run really had me worked up!" Mary said as she finally was able to stop.

"You did great, Mary, and just to let you know, you have managed to fight off 42 orgasms over the last two days. good work slut!" Shelby said.

"Forty-two! Holy shit! But you said that Kelly was going to let me cum today!" Mary said, looking hopefully at Shelby.

"Yes, Mary. I will talk to you about it after your morning meetings!" Shelby said.

Mary did not have time to argue. She hurriedly got dressed for the imminent morning meetings with her team. She was also starving, but she was not allowed to eat typical food for breakfast as Kelly thought her first meal of the day should be cum. The thought disgusted and excited Mary at the same time as her duel personalities fought for control, one was winning so far.

While Mary was sucking her morning cock, Kelly was in her office reviewing the camera footage from Mary's office. She had one installed under Mary's desk, with an LED light focused on Mary's pussy and another mounted on the treadmill, both with sound. She also watched Mary's big tits bounce up and down on her morning run. Shelby had uploaded it just an hour ago. Kelly was glad she had diverted all the budget for the new server to Mary's office. Kelly was able to get Markus to agree to all fund her upgrades and let Kelly pick the contractors. Little did Markus know all the upgrades she installed. It was paying off big time. Kelly loved seeing Mary humiliated but also found herself getting entirely turned on by all the crazy antics she forced Shelby to have Mary perform.

"Wow, you hot bitch!" Kelly said, as she fingered herself, sitting in her office chair watching Mary fight off orgasm after orgasm on the treadmill.

"Oww, please not so hard," Mary wined in the video. The camera caught Mary's big tits moving up and down on the treadmill. The look of anguish on Mary's face was priceless as climax's built up and then got denied as Shelby smacked her red ass time after time.

"Pure torture, I love it!" Kelly thought to herself.

Kelly finally drove herself to orgasm, watching Mary's pussy getting licked by Shelby in the board meeting. The camera was set to focus in close to Mary's wet pussy, and clit rods as Shelby drove Mary crazy. Shelby would build her up and then give her a short break and start all over again.

"How does Mary do it! She must be crazy with lust after all the orgasms she fought off!" Kelly said as she came hard.

"Oh..ya..that's it!" Kelly said as she fingered herself to a nice orgasm.

Kelly knew that since Mary was very desperate to cum Kelly could make it hard for Mary to choose how and when she was finally allowed. Kelly informed Shelby about Mary's options and could not wait until later today.

It was little after 10am when Mary finished her morning cocksucking and finally had "breakfast;" Kelly's version, consisting of six large loads of cum from the team of six. Mary had to admit she was no longer hungry, but sucking that much cock only turned her on more. She was getting used to this special breakfast and looked forward to it each day.

Next came the daily board meeting, which was only an hour. Shelby changed her technique and now sucked on Mary's clit like a small cock driving Mary nuts. Still, like usual, she took it like a pro and barely let on that anything was happening under her desk. Kelly viewed the action live from her phone app and knew what was coming up next. Kelly could hardly wait for the fun to begin.

After the board members left, Mary was horny as ever. Shelby could see how desperate she was, and since she was under her desk eating her out, she knew how wet she continued to be.

Shelby came out from under the desk and sat in one of the desk chairs.

"Well, Babe, today is the big day. Are you ready to finally cum?" Shelby asked with a huge smile, knowing what the conditions were.

"I was ready fifty denied orgasm's ago!" Mary said, feeling on edge after Shelby's clit sucking for the last hour.

"I know, Babe! I Know. Kelly, of course, is not going to make it easy, but she thinks you will have a bigger orgasm this way," Shelby said as she handed a list of ways Mary would be allowed to cum.

The letter read:

Dear OFFICE SLUT,

I know you want to cum, so pick one of the ways below, and I know you will have an earth-shattering orgasm!

All of the following options will be witnessed by the team of six, Shelby, me and Dave. Yes, Dave, he is coming back from an overseas trip. Aren't you glad!

Tied to the desk- spanked by the team of six, then Dave fucks you in the ass while Shelby sucks your clit until you cum! I know, I know he has a very thick cock! Think about it, though!

Fucked in the ass by the team of six, but not Dave. They can cum in your ass or on your face or tits. In the end, Shelby gets the honor of licking you to orgasm.

Run-on the treadmill until you cum. Then blow all the guys and have them cum on your tits.

Choose none and continue to be denied, but it will be two weeks until you get another chance.

Sorry but you cunt is off limits!

Your wonderful boss!

Kelly knew that Mary would probably pick number 3. She hoped anyway.

"Well, shit, these all suck, and my is my pussy off-limits? I would rather have Dave fuck me there!" Mary said

"Kelly knows that you like Dave's thick cock in your pussy Mary, so it's her way of denying you. You have been fucked by Dave a couple of times already, Mary, in front of the team of six, and you blow them daily. What is the big deal about doing it again? Having Dave fuck your ass would be tough, but you don't have to pick that one!" Shelby said, trying to convince her.

"I guess you are right. I make these guys cum daily, so why not me! I pick the treadmill. It seems the easiest, but the most humiliating because the guys have not seen me on it yet." Mary said, thinking about her orgasm.

"Good choice! OK, I will let the team know, everyone will be here right after the office closes so it doesn't raise suspicion." Shelby said as she walked to the door to leave.

"OK, sounds good. I have some actual work to get done, so this will give me a chance to catch up!" Mary said as Shelby left her office.

About an hour after Shelby left, Mary was still working on the team's latest progress report. Again they were ahead of schedule. They will finish the second to last milestone two weeks ahead of the estimate. She was pleased! If things kept going this well, she would end her servitude to Kelly early! She couldn't wait. Fortunately, Kelly had an iron fist when it came to the team of six, and Mary's sluttness was still only known by a few. She hoped anyway. She was just thinking about her new title of Partner when the door chime rang.

She pushed the button on her desk, and, to her surprise, Dave strolled in.

"Well, hello, Mary! Miss me!" Dave said as he walked over and sat in one of her desk chairs.

Mary pussy clenched as the site of Dave's bulge in his pants. The memory of getting her pussy reamed by his wonderfully thick cock with all those veins running up the shaft caused her pussy to gush. She resisted the temptation to lick her lips.

"Man, I am a slut!" Mary thought to herself.

"Hello, Dave. You are early. The team meeting is not for another two hours. What do you want?" Mary said coldly, giving Dave the cold shoulder, but she had only so much willpower at this point. She wanted to cum desperately.

"I know! We all get to see you cum, and then you have to blow all of us with your great cocksucking mouth. I feel I deserve a preview, Mary. You owe me. I'm the one who convinced Kelly to hire Shelby, and it was me that brought you to the Tattoo parlor to meet her in the first place." Dave said as he got up and walked around to the two-foot entrance at Mary's desk.

Mary swiveled her chair around to face Dave. "Slow down, Dave, please! Kelly would kill me if she knew you were here! Just wait, and you will get yours, I promise. I don't want to blow my chance at cuming!" Mary pleaded

Little did Mary know that Kelly had sent Dave in to test Mary's resolve. Kelly was viewing the whole event from one of several hidden cameras in Mary's office.

"Oh, good girl! Trying to fight him off! Very good!" Kelly mused, sitting in her office with her fingers playing with her wet labia.

"You know you want it Mary! Just wrap your cocksucking lips around my cock for a few minutes, just enough to get me nice and hard." Dave said as he brought out his flaccid cock and hung it right in front of Mary's nose. Mary could not back up as her chair was fixed in place. She stared at his cock and this time licked her lips.

"OK, but just enough to get you hard!" Mary said as she engulfed his cock and started to suck it. Mary's talented mouth gave Dave a raging hardon in only a few minutes. Dave was playing with her tits and twisting her piercings as Mary throated him.

"Holy shit, that is great!" Dave said, still impressed by Mary's ability to swallow his whole cock so easily. He held her head and pumped his cock in and out of her cocksucking mouth, thoroughly enjoying face fucking her again.

"Oh, you bad girl! Sucking cock like a cheap slut." Kelly said as she got out her dildo and licked it before inserting it into her wet cunt.

Dave pulled his cock out of her mouth.

"That was great, Mary. I am rock hard. Tell you what let me fuck you for just a few minutes, and I will make it worth your while. You know you want your pussy filled. It's been a long time since I fucked you. Remember how it felt?" Dave said as he looked down at Mary with drool hanging off her lips. She looked to be in a trance from sucking Dave thick cock.

She could not deny it. She was crazy with lust and the fact that she had not cum for a long time. She recalled how Dave worked her pussy into an earth-shattering orgasm that had her squirting for the first time in a while. She wanted to feel it again so badly. She looked up at Dave for a while, contemplating, while unconsciously stroking his cock.

"This is a threshold moment, Mary!" Kelly moaned as she worked the dildo in her dripping pussy while looking at Mary's stroking Dave's pulsing pole.

"Oh god, it's so hard!" Mary said quietly to herself, but Dave heard.

"Come on, Mary! I know you want it. No one will know!" Dave said, hoping for the best.