MILF in Office Trouble Pt. 08

Shelby went into Mary's office and worked on the list Mary had left her. She really had a lot to do and never realized how busy Mary was when not pleasing the Team or getting tortured by Kelly. Her admiration spiked for Mary and tightened her resolve for the up-and-coming meetings with the Team of six. They had no idea about the change, and it was up to Shelby to pull this off.

She looked in the mirror and touched up her makeup, and adjusted her breasts for the last time. Shelby walked into Mary's circular desk and sat down on Mary's unique chair. She had a few more minutes before the first meeting with Ron. Shelby spread her legs and stared down at the hole where the dildo rested. She knew she really did not have to impale herself on the dildo when sucking off the Team, but Shelby felt a rush in her pussy as she thought about Mary and what she went through.

"If she could do it, then so can I!" Shelby said as she fingered her clit to get her pussy even wetter. She knew the dildo was thick, and she needed all the lube she could get. She pressed the button to raise the dildo out of the chair and into her waiting wet pussy. It raised slowly and poked at her entrance. She wiggled her hips, and the dildo started to stretch her tight pussy lips open. Shelby moaned when the dildo finally popped in. She kept the button pressed, and the dildo continued to penetrate her hole. Up and up it went until it pushed against her cervix.

She felt a rush of shame, feeling fully stuffed with cock, but more turned on than ever.

"No wonder Mary's did this!" Shelby thought as she saw Ron enter.

"Well, hello, Shelby! I was expecting Mary behind the desk. I'll come back when she is here." Ron said and turned to leave.

"No, wait! Mary is out of the office for the duration of the Server install. It is the last step, and Mary needs to supervise. Mary knows that you and the Team need to finish the software by the time the Server is installed, so she asked me to step up and take care of the Team in her absence." Shelby said shyly, not knowing how Ron would take the news.

"Not just management but all of Mary's activities? Are you sure about this, Shelby? I have only seen you witness our meetings and never thought you could "support" such an activity." Ron said apprehensively, hoping that he would still get a morning blow job.

"Yes, Ron. I am taking over ALL of Mary's responsibilities. If you accept me as her proxy, please step up so I can get started. I have a hectic day." Shelby said with as much authority as she could muster with a dildo shoved in her pussy and rattled nerves.

"Accept you! Hell ya! I don't know if you noticed, but I looked at you when Mary's was blowing me, imagining what your lips would feel like." Ron said as he walked behind the desk and up to Shelby. He saw the thigh-highs and heels, and his cock grew even harder.

"Glad to hear!" Shelby said, blushing furiously from Ron's comments. Ron thought it was so cute and sexy to see Shelby embarrassed.

"Wow! You do look a lot like Mary!" Ron said as he got his almost hard cock out and hung it right in her face.

Shelby reached tentatively out with her hands and pickup of the end of his cock and stroked it a couple of times, then she sucked it into her mouth and moved her lips back and forth down his hardening shaft.

Ron was overcome by the innocence of her technique to give her a hard time and decide to offer advice.

"Look up at me the whole time while sucking and cradle my balls until it gets really hard. You are doing a super job. Keep sucking!" Ron encouraged.

"Ahuha!" Shelby muffled with a mouth full of cock, and she cradled his balls and licked up his shaft.

Ron let her suck away as he bent over and unbuttoned her blouse. Shelby started to object, but Ron told Shelby it's what Mary allowed.

Ron managed to open her blouse and lift her tits out of the shelf bra to play with them as she started to get more confident. She sucked and licked as a woman possessed. Her technique was nothing compared to Mary, but Ron did not mind. A fresh set of tit's and lips compensated.

Shelby kept her eyes on Ron the whole time, even when she gave his balls a tongue bath. Ron held both breasts in his hands and pinched her nipples. That, combined with the dildo, had Shelby going now. She was in full slut mode. She slurped and sucked as hard as she could. She tried to deepthroat a couple of times, and Ron appreciated the effort, but in the end, Ron pulled out just enough to fill her mouth up with a massive load of cum. Shelby let him have a good look at her cum filled mouth before she swallowed it down in one gulp.

Ron gave her tit's a last squeeze before standing up to leave.

"You did great, Shel! First-class blow job, and you have great tits! Just lovely. You can suck me off anytime!" Ron said sincerely.

Shelby blushed bright red and the compliment.

"Well, I aim to please Ron. Send in Jerry, will you please?" Shelby said as she closed her blouse.

"Just a piece of advice, take off the blouse and bra. They will want it off anyway, and you get them harder faster looking at your fantastic rack!" Ron said as he left.

Ron left, and Shelby took off her blouse and bra, heeding Ron's advice.

"It made sense, as she was here to suck cock, not talk." Shelby thought.

The following four team members all filled Shelby's stomach with large loads, and they were all thrilled to have Shelby suck them off. Her stomach was getting full, and her jaw was aching. Since she could not deep throat, it took a lot of sucking to get the team off. The worst part was that Sandeep was last, and she knew by experience that he had by far the biggest cock and longest staying power. She hoped he went quick.

It was getting late by the time Sandeep hung his massive cock in Shelby's face. Sandeep encouraged her and gave her tips as she licked and sucked his enormous dick to full hardness. She tried to get her mouth down the shaft but only made it halfway.

"How the hell does Mary deep throat this guy!" Shelby thought as she turned toward his balls to lick them while jacking his shaft, trying to get him off.

Sandeep was patient but soon realized that little Shelby was not going to get him off anytime soon. It took a good deep throat to get him to cum with a blow job. He could tell she was getting frustrated.

"Hey Shel, hold up for a second," Sandeep said as he pulled her off his cock while she was trying to ram it down her throat for the fifth time.

"You are doing a great job, but I don't think this is going to work. I wish Mary were here, but if you can't get me off, I will have to speak to Mary and let her know that she needs to care for me. Don't feel bad; you gave it your best shot." Sandeep said as he started to put his cock back in his pants.

Shelby was panicking, but then she perked up as an idea came to her. As big as Sandeep was, she could not let Mary down, so she reached over and pushed the button to retract the dildo and stood up as Sandeep was walking out from behind her desk.

"Sandeep, wait. I can't let you leave without cuming. How about I let you fuck me, but you can't tell any of the others, or they will all want to. Then when you are close, you can cum in my mouth, and we all win. Deal?" Shelby said as she bent over the desk and lifted her skirt to show Sandeep her freshly waxed wet pussy from behind.

"Worked like a charm!" Sandeep thought. He had techniques to hold off cuming, and he used them all on Shelby, hoping he would get a shot at her young pussy.

"Well, if that's ok with you, then yes, I think that would work perfectly!" Sandeep said with a broad smile.

"Ok, but go slow, big guy. My pussy is not used to a dick that big. Really, I don't want to get hurt!" Shelby said as she turned back around to face the desk and stuck her ass out with a wiggle.

The last time she took a big dick, it took a lot of help from Mary to get her to relax enough so her pussy could expand and take it.

"Thank god I was sitting on the dildo to prepare me for this!" Shelby thought as she felt his hands on her hips, then she felt his dick sliding up and down her slit to get it lubed up enough.

"Ok, I am ready, be careful with my pussy please!" Shelby begged.

Ron looked down at Shelby's little pussy while lining up his cock with her wet hole after the tip was covered in pussy juice.

He pushed in, and Shelby let out a moan. She felt her pussy expand and expand as it opened up more and more just to get the head inside.

"Slowly, big guy...oooo...you are so big...my pussy feels like it's being split open...hold up stop...give me a second!" Shelby said through gritted teeth as Sandeep stopped with just the head in her vice-like grip of a pussy. It felt great to him.

"Ok... go ahead...but slowly now...I have never felt so stuffed with cock!" Shelby groaned, thinking that this was not such a great idea after all.

He massaged her back and cupped her tits, pinching her nipples to distract her as he fed more and more of this cock into her.

"You are doing great, babe, and your pussy feels fabulous. Just try and relax your pussy and let it expand." Sandeep said. He had about four inches in and start to fuck her with just part of his dick to help open her up.

"Ok...I'm trying...it's starting to feel good...don't go deeper yet, but you can fuck me faster now!" Shelby moaned as she relaxed, remembering what Mary said about not clenching down and not being afraid of letting a big thick cock into her.

Sandeep spent the next ten minutes fucking her, slowly but firmly, going a little deeper every time until he finally bottomed out on her cervix. He could not get it all in, but he didn't care. Shelby's cunt felt like a raging furnace, and she was constantly moaning as she had her first orgasm.

"Oh god! Your cock...it feels great...yes fuck me...it's so deep...I feel it all the way up to my stomach! I'm cuming..oh fuck!" Shelby squealed but realized she needed to keep it down.

Sandeep smiled, looking at the girl cum on his shaft. He knew he had this little admin. He slowed down after her orgasm, rubbed her back, and told her how sexy she was and what a great job she was going and that Mary would be proud of her.

Sandeep slowly picked up the pace until he was again driving her to another big climax. He was getting close also. He lifted her hips and fucked her hard with her legs in the air. Shelby was mumbling at this point. Her legs shook as another orgasm racked her pussy.

"Oh fuck! What are you doing to me!!!" Shelby cried a final time. Her legs flailed in the air from the intense orgasm.

Sandeep pulled out and spun her around, and set her on the floor with her still cuming. He pointed his cock at her mouth. She noticed just in time and opened her mouth for the jets of cum that filled it up. Cum also landed over her pretty face. She dutifully swallowed all she could and crumbled on the carpet, totally spent.

Sandeep picked her up off the carpet. Cupped her hot, abused sex and kissed her hard. Shelby was overwhelmed and just stood there and kissed him back. She was a mess but enjoyed the kiss anyway.

She regained her composure as Sandeep put her down and got dressed.

"Well...thank you, Sandeep...that was...well that was...." Shelby was cut off by Sandeep.

"It's okay, sweetie! You did great, and that is one hot pussy you have!" Sandeep said, and he zipped up and left the naked and well fucked Shelby to get on with her day.

"Oh god! I cannot believe I fucked him!" Shelby thought as she fingered her wet pussy, thinking about all the intense orgasms she had in the last hour.

While poor Shelby was getting her stomach filled with cum and her hole drilled by Sandeep, Mary woke up to the sound of the milk machine sucking her tits. She did not know how long she had slept, but her nipples were aching from the constant suction. She looked down at the clear plastic tubes with rubber sleeves milking her nipples. The suction pulled on one nipple and then the other in a never-ending cycle. The suction also varied. On the highest setting, her poor nipples were extended almost 2 inches as Mary watched in dismay.

Mary despaired with tears falling freely from her swollen red eyes. So far, she had been forced to drink piss and get pissed on, humiliated in innumerable ways by evil Helen, including her latest, turning Mary into a milk-producing slut and being locked to a bar on the floor of the garage to a milk machine. To top it off, she had her precious tits and pussy whipped. She looked down again at her poor tits decorated all over with red triangles from Helen's riding crop.

"Well, hello there. Are we awake?" Helen said as she came back into the garage, turned off the milking machine, and unlocked Mary from the bar restraints. Mary got up slowly and looked down at her distended nipples. They were twice as long as usual and bright red.

Mary was relieved, to say the least, until Helen came up and sucked hard on both nipples while cupping her tender breasts.

Mary winced as Helen continued to play with her fun bags.

"I fell asleep but woke up a little while ago. My nipples are aching, Mistress." Mary said in a pathetic voice.

"Don't worry slut. You're free for now. I brought some new clothes and toys for you to try. Follow me." Helen said as she released her grip on Mary's nipples and walked out of the garage and back into the living room.

Mary followed with aching tits, sore red pussy, and head down, hoping nothing worse was on the horizon.

Helen had Mary stand in the middle of the Living Room, and she rummaged through her bag and brought out two small gold bells with clips. Mary sucked in her breath in pain, and Helen clipped a bell on each nipple.

"Shake'em slut. I want to hear how they sound." Helen commanded.

Mary shook her breasts back and forth, and the bells jingled, making Helen smile.

"There, now everyone will hear you in the house no matter where you are," Helen said.

Next, she had Mary pull up bright red lace thigh-high stockings with an extra thick band to hold them up on her thighs. Then she brought out two gold-colored chains with clips at each end and told Mary to spread her legs. Mary widened her stance and looked down as Helen clipped one end to the band at the top of her thigh-highs. She reached up and pulled one of Mary's large fat outer pussy lips down, adjusted the length of the chain, and clipped the end to her pussy lip, so it was stretched tight. She did the same to the other pussy lip. Now both ring pierced pussy lips were stretched down toward her stocking and much more visible. The clips did not hurt that much, but the humiliation and shame she felt over her large lady parts were now amplified tenfold.

"There now, everyone will clearly see your fat ring pierced pussy lips and know what a huge slut you really are. What do you think slut?" Helen said as she played with both lips, pulling and teasing them.

"It doesn't matter what this slut thinks, Mistress." That was all Mary could say. She hated them and was again astonished at the level of perversion that Helen was capable of.

"Exactly right slut! I found this gold chain in your suitcase. You never told me about this! Bad slut!" Helen said as she attached the chain to her barbell nipple piercing and then the other longer end down to her clit. She clipped the end of the clip directly on the sensitive end of her huge clit. Mary was more used to this chain but still felt humiliated. Helen reached down to stroke Mary's clit and wet slit.

"Looks like you hate all this, but your slutty pussy loves it," Helen said as she went back into her bag and brought out a corset.

Mary had nothing to say as she stood there wishing she were anywhere else and wondering how Shelby was getting along. Little did she know that Shelby's sweet little pussy was pried open by a huge cock not one hour ago.

Helen had Mary lift her arms, and she fitted the corset around Mary's waist. It had many laces up the back as most corsets had and two small shelves for Mary's tits to sit on. They made her tits more prominent by holding them up higher on her chest. Helen pulled the laces tight, squeezing her midsection, forcing an exaggerated hourglass figure that caused her tits to thrust out even more than they usually were. Helen adjusted the gold chain on her tits and clit, so they looked to be part of the outfit. Finally, Helen broke out leather straps and pulled Mary's arms behind her back. Helen started by strapping Mary's wrists. She then wrapped another strap around her elbows and cinched the strap until Mary's elbows were bound together. Mary's shoulders were back forced and together, causing her chest to be thrust out even more if that were possible.

"Well, I think you look perfect slut. Your tits are much more visible with your tiny waist, and the corset holds them up and out splendidly. We have a special guest coming over tonight, and he will love you for sure. Don't worry slut, you will be masked; he doesn't know you anyway." Helen said.

"Yes, Mistress," Mary said, looking down on her chest and feeling her pussy lips stretched by the evil stocking chains.

"Ok slut, now go clean the bathroom toilets. There are four of them, two upstairs and two downstairs." Helen said as she started to pour herself a drink.

Mary was relieved. At least cleaning was not getting punished.

"Yes, Mistress, please release my arms so I can clean," Mary said, turning around so Helen could get to the straps holding her arms locked behind her back.

"I'll do no such thing slut! I want all the toilets to be sparking in one hour. If not, then it's back to the garage, and I would not want to be your pussy if that happens." Helen sneered.

"But how Mistress, my hands are tied. What do I use to clean?" Mary wondered.

"I don't care how you do it slut. Turn backward and use a towel, and if that does not work, you will have to use your tongue! No more questions! The timer starts now!" Helen said and pointed Mary out of the room and set the timer for one hour on the microwave oven.

"If I find one hair or stain, then it's off to the garage!" Helen said, finishing her drink.

Mary walked dejectedly upstairs and found the first toilet. She grabbed a towel and backed up to the toilet. She tried her best and got some of it clean. She used her teeth on the toilet brush but eventually had to use her tongue to get hair and stains from parts she could not get to otherwise. She winced, and she ran her tongue along the porcelain rim and down the sides to get hair and clean spots down low. She cleaned the first two toilets with a minimum of tongue use, but she ran out of time. She had no time to use her hands and a towel, so she was forced to tongue most of the toilet. It tasted rancid, but at least she finished on time. She had never felt so gross in her life. It was made worse by Helen forcing her to smile while licking the rim of the bowl for a photo.

"Please release my arms, Mistress; they are killing me!" Mary begged after they were both downstairs.

"Eat your lunch first slut. Helen said as she put another bowl of what looked like stew down on the ground.

Mary knelt down carefully, but her pussy lips, chained to her stockings, still hurt from the maneuver as they were stretched even more when she bent over.

Mary lapped up the stew the best she could but still got drops of stew on both tits. Her face was covered with stew before she finally finished.

Helen made her stand up and only then released her arms. Mary felt a flood of relief and stretched her arms, making sure they still worked.

It was past mid-day by now, and Helen had to prepare the house for guests.

"Ok slut, you can rest for the rest of the day; follow me," Helen said.

Mary dejectedly followed Helen back to the garage. In five minutes, she was shackled to the bar, and her tits were being sucked on again by the relentless milking machine. Helen turned down the suction as Mary was going to be there all afternoon.