MILF in Office Trouble Pt. 08

Helen forced Mary to stay on all fours next to her and petted her like a dog while speaking with Mike.

"I want to keep our slut here today, Mike, so you can go into work and let them know that she will be in later this week," Helen said while petting Mary's head and scratching her behind her ears.

"I'm her fucking dog now!" Mary thought as she sat there and took it.

"Sounds good! Take care of our slut! I have to see about the details of the server room contract anyways, so the slut does not need to come today." Mike said.

Mike and the others left for the respective jobs. Helen was the only one who did not have a job.

Mary had a sinking feeling in her stomach as the others left her alone with Helen.

"Well, it's just you and me, I was going to take you out shopping right away, but I have been waiting for this for a long time. Follow me slut!" Helen said as she led Mary out to the garage.

Helen opened the chastity ap and unlocked the chastity cage.

"Take the cage off slut." Helen said

Fearful, Mary reached down and released her pussy lip rings from the cage and then pulled the vaginal vibrating plug out of her wet hole and handed the cage to Helen.

Helen guided her over to the center of the garage and told her to raise her arms above her head. Helen then lowered a rope from pulley system made just for the occasion, it seemed to Mary.

"What does this crazy bitch have in mind!" Mary wondered as she raised her arms.

Helen came over to her and attached a pair of padded cuffs to the hook in the rope. Then she cuffed Mary's hands, walked back over to the wall by the door, and pulled the rope until Mary's arms were stretched above her head. Helen secured the rope to the cleat. Mary still had both feet on the ground at this point. Helen walked over and opened a cabinet, and pulled out a long rod with cuffs on each end. She walked back over and told Mary to spread her legs as wide as they could go, then cuffed her ankles on the spreader bar. Her feet were about three feet apart from at this point.

Mary was getting more worried when Helen came up behind her, forced a ball gag into her mouth, and secured it behind her head.

"Wait here, won't you! I will be back in a bit." Helen said and left Mary hanging spread-eagled in the garage.

Mary's mind raced as she hung there waiting for Helen to return.

Helen came back fifteen minutes later dressed as a dominatrix. She wore a black latex jumpsuit and looked very pleased with herself.

"I thought I might as well dress the part. I spent quite a while thinking about this when I first heard of your proposition. The others were not so into this, but I sure am." Helen said as she walked over to the cabinet and brought out a riding crop and a leather whip with several tails. Each tail on the whip was made from a two-inch-wide leather strip, and there were eight in all.

Mary began to protest into her gag but only muffled pleads were heard.

"I think I know what you are trying to say, but this is what I have been waiting for, Mary. Don't worry, I have read enough to know how to give pain without marking you.

A wide-eyed Mary with tears streaming down her face looked at Helen with a pleading expression, shaking her head and struggling against the ropes and cuffs.

Helen walked up to her and got right into her face.

"Didn't expect this from a bored suburban housewife, huh Mary? Mike told me everything, Mary. He told me what you thought of me and how you were so much better. The truth is, Mary, I do think you have a fabulous body and wonderful breasts with such suckable nipples." Helen said and surprised Mary by bending down and sucking each one until they were red and erect. She then cupped them and massaged them for a good while talking to Mary.

"Tell anyone about this, and you will be in here every day paying the price!" Helen said.

Mary shook her head in agreement, and Helen laughed.

"I bet you won't! Now let's see what else we can do before the real punishment begins." Helen said as she walked back over to the cabinet and retrieved what looked like weights.

"It's great that you already have these lips rings on your pussy, Mary. These are one-pound weights, Mary, and they should work nicely to stretch you home wrecking cunts lips." Helen said as she hung two weights on each pussy lip. Mary groaned a muffled scream as the weights pulled down on her outer pussy lips.

"How does that feel, Mary? Not as bad as having your husband leave for a slut I will tell you!" Helen said.

Next, she attached a smaller weight to each nipple then.

Mary looked pathetic, hanging spread-eagled with weights on her poor pussy lips and nipples. Mary sobbed as Helen sat back and enjoyed the sight, then took several pictures to help savor the occasion.

"Ok, Mary, I think it's time. Don't worry, I have been practicing." Helen said as she picked up the riding crop and stepped to the side of Mary.

"For each strike, I want you to think about all the things you did and how sorry you are. Can you do that for me, Mary?" Helen said as she took some practice swing with the crop.

Mary shook her head vigorously with a look of terror in her eyes as the first blows from the riding crop landed on her poor breasts. Mary was grateful she was not a complete sadist as the blows were painful but not nearly as painful as they could have been.

Each stoke left and triangle pattern of red on her tender breast flesh. Mary squirmed as each strike landed in a different spot. The most painful was the two that landed on her tender erect nipples. Mary screamed again, but weirdly she was getting used to the pain and was horrified to feel pussy juice running down her leg. Helen finished only when there was no place on Mary's tits that did not have a bright red triangle from the riding crop.

Helen finished with a satisfied look on her face and then looked down between Mary's spread legs.

"Well, what do we have here, my slut?" Helen said, kneeling down on the floor to get eye level with Mary's pussy.

"You are very wet down here. Well, well, maybe this is too good for you?" Helen said she removed the weights and then, to Mary's shock, proceeded to eat out Mary's tender pussy, right there in the garage. Helen licked her juicy pussy as Mary hung there. After licking and sucking her pussy lips and wet hole, she attacked her clit. Mary's moaned and groaned as Helen sucked Mary's clit until it was fully erect, giving it a mini blow job while fucking her hole with two fingers.

Helen was amazed at the tightness of Mary's pussy. She could barely get two fingers in there to finger fuck her. She finally removed one finger as that is all she needed.

"On top of a huge rack of tit's, perfect ass, and a model body, this bitch also had virgin tightness in her cheating pussy!" Helen thought as she continued the assault on Mary's wet hole.

Mary trashed about as Helen munched on her pussy and came hard on her face.

"Man, this woman can eat pussy!" Mary thought after her orgasm. It was a bizarre mixture of pain and pleasure for Mary as she looked down on her poor breasts, totally covered in red riding crop triangles.

"Tell anyone what just happened, and the next time, I will not be so nice," Helen said as she stood up and wiped the girl cum from her lips.

"I think we can be done. I was going to use the other whip, but I might as well save that for tomorrow. After all, I have twenty more days!" Helen said as she went behind Mary and took off her ball gag.

Mary was grateful, as her jaw was starting to hurt.

"Thank you, mistress!" Mary said truthfully.

"Thanks for what? Helen asked.

Mary was going to say "for taking the gag out" but thought better of it.

"Thank you for the orgasm and my punishment," Mary said, still swinging from the ceiling.

"Well, it sure made you wet. I guess that is why you are a huge slut!" Helen said as she lowered Mary down and took off the cuffs.

"Yes, Mistress!" Mary said.

"Follow me slut." Helen said after she put everything back in the cabinet.

Mary followed her back into the Living Room.

"Make me a drink slut. I'll take vodka and coke. It's in the kitchen next to the frig." Helen ordered.

"Yes, Mistress...right away," Mary said.

Mary came back into the living room to see Helen completely naked. She was laying back on the recliner with her legs hooked over the arms, with one hand fingering her hairy pussy and the other pinching her tiny nipples on her A-cup breasts.

"She must wear a padded bra." Mary thought as she now saw that Helen, laying back naked, was utterly flat-chested.

Helen noticed Mary looking at her chest and then back at hers.

"Ya bitch you have big fat tits, but I am the one who gets to whip them." Helen thought, smiling to herself.

"Your turn to make be cum slut! Get that tongue to work!" Helen said as she took the drink from Mary and stopped fingering herself.

Mary knelt down between Helen's spread legs and started by running her hands down Helen's inner thigh toward her very hairy pussy. Helen's public hair was thick and ran down her legs and up her public bone quite a ways.

"Apparently, Helen never wore a bathing suit!" Mary thought as she used her long tongue to dip into Helen's jungle to find her pussy lips and clit. Finally, Mary had to use her hands to spread Helen's pussy open to find her tiny lips and tiny pebble of a clit.

Helen was very turned on by this point. Her pussy hair near her entrance was matted with pussy juice. Helen tasted good to Mary; however, her juice was sweet, and Mary got into it, lapping up Helen's nectar.

Helen finished her drink over the next ten minutes while Mary dutifully ate her out. Mary had to come up for air and split out pubic hair every-so-often, but Helen did not seem to mind. Helen's moaning grew as Mary worked her pussy and clit. Mary then inserted a finger into Helen's wet cunt to finish her off. Still, she found that she had to insert three more fingers to get any kind of friction going.

"Man was a loose pussy she has!" Mary thought but dared not say anything about it to Helen.

Mary finally found her internal G-spot and rammed all four fingers into her increasingly wet cunt as Mary did her best to suck on her tiny clit. Helen's hips began to buck as Mary drove her toward orgasm. Helen reached down and held Mary's face tightly against her pussy. Mary's face was deep in a jungle of wet pussy hair when Helen finally climaxed.

It wasn't a huge gush, but Helen's girl cum went straight to Mary's mouth as Mary slowly lick Helen's opening while Helen finished cuming.

"No more...no more!" Helen said as she pushed Mary's face away from her post-orgasmic hairy pussy.

"I aim to please Mistress," Mary said as she remained on the floor at Helen's feet.

Helen got up off the couch and went into the kitchen to retrieve some pills.

"Here, take these slut." Helen handed her three pills and a pillbox divided up into the days of the week.

"What are these, Mistress?" Mary said as she took the pill and pillbox.

"Well, I thought it might be nice if your tit's filled up with milk, so these are hormones and estrogen pills. The hormones, along with suction, should get you producing milk very fast, and the others are to up your sexual desire to keep up with my needs. Although you seem to be wet from the abuse I give you. anyway, a wetter pussy is always better to help you serve as our slut. Now be a good slut and take the pills every day. You will have to show me you are taking them; if you miss a day, then it's back to the garage for more punishment, and before you complain, I already spoke to Kevin, your lawyer. He said there is nothing to prevent this in the contract as long as it's safe." Helen said.

"You can't be serious! That is so fucked up," Mary said and instantly regretted it.

She tried to apologize, but it was not good. In ten minutes, she was hung upside down in the garage with a spreader bar holding her legs wide open. Mary's cunt was splayed open, front and center at eye level with Helen, and she prepared for the worst.

Mary's eyes blinked her terror, and Helen broke out the riding crop. Helen sawed the leather thong of the crop back and forth across Mary's wet pussy. Her huge pussy lips and ring piercings moved back and forth as Helen teased her before the impending punishment.

"Please, Mistress! I am sorry I will obey and do my best to fill my fat breasts with milk!" Mary begged with tears dripping down her forehead and onto the floor. She was no stranger to getting her pussy whipped. It hurt like mad, but it made her cum when done right, but that was a very long time ago before going corporate.

"You will obey after this cunt! The inner thigh is so sensitive, is it not?" Helen said as she ran the crop up from her pussy up her thigh.

"Yes, please don't whip my pussy!" Mary whimpered.

"Your what?" Helen said.

"My cunt! Please don't whip it!" Mary begged again.

"To date, but if you don't yell when I whip you and don't have to use the ball gag, then I may be merciful. I like the sound of your suffering." Helen said.

"I will try, mistress!" Mary said, thinking that this was indeed payback she never thought possible from the innocent Helen.

Helen landed strikes on her inner thighs, leaving red triangles going up both sides.

Crack!

"Yeow!"

Crack

"ouch!!..damn, that hurts!" Mary yelled but as reasonably as she could.

She landed ten more on her thighs before she stopped.

Crack!

Crack!

Crack!

Crack!

Mary's subdued screams pleased Helen as Helen could tell it hurt, but the slut knew better than to yell loudly.

"And now for the final part! My favorite. I was looking for an excuse to whip the very pussy that stole my husband," Helen said as she returned to stroking Mary's cunt with the crop in preparation.

"You get five for being insolent and for generally being a whore. Ask for each one by saying, "Please whip my home wrecking cunt Mistress," and then start counting. Understand cunt?" Helen said sadistically.

"Yes, Mistress, Please whip my home wrecking cunt." Mary said and involuntarily clenched her vaginal muscles in anticipation.

Helen moved behind Mary so she could not tell exactly when the strike would land. She teased Mary by tapping her pussy many times. Helen noticed the fluid building up in her pussy and was amused.

Then Helen positioned the leather thing right over Mary's hole and then brought the whip up and landed a solid blow right on her cunt entrance. Helen saw the blow land, and Mary's cunt lips quiver as the crop hit.

It took all of Mary's effort not to yell loudly. She could tell it was not as hard as it could have been.

"Yeow! Oh, shit, my poor pussy!" Mary yelled, almost forgetting to count but quickly added, "One, Please whip my home wrecking cunt!" Mary said as fast as she could.

"Fuck! Ouch! Two, Please whip my home wrecking cunt" Mary continued, but Helen was backing down at this point, and Mary felt her cunt respond and not in the way she hoped.

"I see a lot of fluid here slut! Looks like you might like this!" Helen said.

Helen landed three more, with the last one fairly hard right on Mary's engorged clit. That one hurt Mary the most, and she yelled the loudest.

"Holy fuck, my clit is on fire; thank you, Mistress. I will obey from now on. Please stop!" Mary sobbed.

Helen came over and looked at Mary's fire red pussy lips and clit. Then she got an evil expression on the face and started to lick Mary's pussy. Mary moaned in pain as Helen licked and sucked Mary's abused pussy for five minutes. It was nothing compared to the whipping, but it still hurt. Mary's lips and pussy were red and painful without licking, but she hung there upside down and took it from her tormentor.

She let Mary down and released her from the bar. Mary looked haggard.

"Ok slut! I have to go shopping for a few toys I forgot, so I will leave you here to rest for a while. Come over here." Helen said and led Mary over to the back corner of the garage. She moved a piece of plywood out of the way to reveal a sort of pen. It looked like a stall for a goat or chickens with a bar and shackles attached to a bench about knee-high.

"Ok Slut kneel down in front of the bench," Helen said.

Mary knew better than to complain. Her pussy was still on fire as a reminder about disobedience. Only her unflinching goal of becoming a Partner was keeping her there.

Mary knelt down on her knees in front of the bench. Helen bent her forward, so her head was just over the bar about two feet up from the floor, then she shackled her neck and wrists to the bar, so Mary's huge tits were hanging down. Helen left and soon came back. Mary looked down to see Helen attach what looked like breast pumps to each nipple. Shortly after, Mary heard the sound of an electric motor being turned on and felt her nipples being pulled into the suction tube attached to her nipples. The suction came in intervals, one cycle every few seconds. Mary realized that this must be a goat milking machine, and she was the goat. Humiliation, embarrassment, and shame coursed through her along with a very wet pussy as her tits were being milked like a farm animal. She did not have any milk yet, but she assumed that the drugs and suction would change that very soon.

"Look up and smile slut!" Helen ordered.

Mary looked up at the camera, forced a smile, hung her head back down, and sobbed.

Mary felt Helen finger her pussy and was ashamed to admit that her pussy was gushing even though it had just been whipped.

"You are such a slut! What in god's name do you want to be a Partner for? You make a much better slut?" Helen teased without needing an answer.

"I'll be gone for a couple of hours. The machine is set to alternate the suction to simulation a real baby. Hopefully, in a week, your fat tit's will be even bigger and full of milk. Enjoy slut! I know I am having a blast!" Helen said, and with that, she was gone.

Mary was so exhausted from all the morning events that she actually fell asleep soon after Helen left. The bar was thankfully padded under her neck. The milking machine went on sucking Mary's nipples harder and then softer as Mary slept.

While Mary was being turned into Hucow, Shelby was getting ready for a busy and different day at work.

Shelby looked at herself in the mirror and liked what she saw.

"Are you ready to suck cock, Shelby?" She said to herself in the mirror. She was still very apprehensive about the whole thing, but she also knew that Mary was probably going through hell right now. She could not let her down.

"The team needs to stay focused, and if that means I have to suck more cock in three weeks than I have my whole life, then so be it." Shelby thought resolutely.

She did her best to copy Mary's look. After all, if she was going to be her proxy, she might as well look the part. She had to buy most of the missing pieces of the outfit, but it was worth it. The hardest part was getting her pussy waxed, not that the Team would get a shot at her bald pussy; she just thought it would help her become Mary. She was indeed wet ever since getting waxed, and she kind of liked the look. Her tight little pussy and pea-size clit were extra sensitive now as a bonus.

She picked white thigh-high stockings, and short grey pleated skirt, and a matching white blouse. The new shelf bra gave her more cleavage than she ever had before; even though she could not hope to match Mary's rack, she still adjusted her blouse. It just covered each nipple and showed maximum cleavage. She stepped into the red high heels, brushed out her hair, and applied makeup to match Mary's with red lipstick and black eyeliner. She looked sexy as hell. She took a deep breath and left for work, more nervous and wet than she had ever been.

She got to work and succeeded in avoiding Kelly for the time being. Shelby knew that Kelly was not happy about losing control over Mary. Still, when the CEO dictates procedure, you follow orders. Of course, Markus had no idea what he was doing when he asked Kelly to ease off and leave her alone for the duration of the server install.