MILF in Office Trouble Pt. 08

Becky and Helen's assholes clenched in sympathy as John started to push in. They both understood all too well what Mary was feeling. Mary hung in there fairly well as she knew what to expect to a point. John's head was far more expansive, and everyone heard when Mary passed the threshold. It was only about ¾ of the way in when Mary really started to vocalize.

"Ohhh....shit... yeow...ok..ok..stop let me get used to it...Please...it's so big. My poor ass!" Mary begged. John stopped with his head not entirely in. He could not back out too much, or her ass would close back up.

Mary was clutching both Becky's and Helen's hands as she fought off the pain and tried to remember to relax.

The main problem with this position was that Mary had a front-row seat, and she could not help but stare, and her tiny ass opened for this monster.

Both women liked her paying the price, but they also wanted her to take it all, so they both bent down and sucked on Mary's nipples, hoping to detract her.

"Umm, yes, that feels good...Ok, keep going; I can see it's almost in!" Mary painted, licking her nipples sucked. Becky and Helen both got milk, and Mary cried as John's head pushed further and further. She saw her asshole expand to what must have been 3 inches in diameter.

"Suck on my clit, please. It's almost in, and it really hurts!" Mary begged. Becky and Helen bumped heads, trying to get to Mary's engorged clit. Helen made it first and sucked on it while John gave his cock a final push. With a loud scream from Mary, John's head finally popped into Mary's poor ass.

"Arrrrgh..holy yell....Yeow... fuck that hurts..don't you dare move your cock!" Mary screamed, and she looked down at her ass as she cried. They were all amazed it even made it in.

"Ok, this ends now unless I get some real help. There is no way he can fuck me without help from all of you!" Mary yelled.

"Ok, Jill, whatever you need!" Helen said as she wiped the sweat from Mary's forehead.

"Before he moves his cock another inch, I need Becky to suck on my clit.John, hold my legs up so Mike can help suck my nipples. Helen, get a dildo and fuck me with it, then maybe I can take this monster!" Mary said, recovering a little from the intense pain.

They all moved with great speed to accommodate Mary. Mary's nipples and clit were being sucked in minutes, and Helen was pushing her favorite dildo into Mary's pussy.

In a few more minutes, Mary's asshole was expanding, and the sensation from her clit and nipples being sucked helped her a lot. Helen was also driving a reasonably thick dildo into Mary, but it was missing the target.

"Helen, angle the dildo toward me to hit my g-spot...that's it. Ummm, it's starting to feel good. Ok, let me cum then we can continue." Mary moaned as she started to build toward the climax.

"Ooooo...yes, I'm starting to cum...John..as soon as I cum push it a few inches..but wait until I am cumming or it will hurt too much!" Mary moaned as she came hard. She lifted her hips as she came, which drove John's cock in more than he wanted. Mary let out a scream.

"Yeow! Shit...shit...shit...my fault...It's ok...keep going; this is not supposed to be fun for me!" Mary yelled.

John was rock hard as he stared as his cock buried just two inches into her ass. It was a vice-like grip. This was only the second ass that he ever got his dick into.

They were all loving the pained look on Mary's face as she struggled with the pole entering her ass. Mary was in the throes of a drug-induced sexual craze where the pain was intense but was offset by the waves of pleasure from her breasts, pussy, and ass.

John slowly fucked her ass, pushing it just a little each time. Becky stopped sucking her clit as she wanted to view the spectacle up close, and Helen pulled the dildo out, wanting Mary to deal with the large cock without the extra stimulation.

Mary reached down and started to finger her clit, and John drove deeper.

"It's so big...it hurts like hell...but keep going...I deserve it...fuck my worthless ass!" Mary sobbed as Helen and Becky smiled in satisfaction, knowing full well how much Mary deserved every inch of John's cock in her ass.

John kept pushing his cock, and Mary kept sobbing. After ten minutes, John was sawing 6 inches in and out of her asshole. They all saw her sphincter pull up and then get stuffed back inside as he started to really fuck her.

Just as Mary was about to pass out, John started to cum.

"Oh fuck..here it comes, Jill...I am going to cum!" John groaned.

"Thank fucking god...I don't know how much more I can take...cum in my ass!" Mary blubbered with tears of pain streaming down her face as she stared at her ass being stuffed full of the thickest cock she had ever taken.

John could not help but plunge his cock in a few more inches, and his shaft expanded, and he pumped her ass full of hot seamen.

"Argh..oh fuck here, it cums...my balls are going to explode!" John said, and he came hard.

Mary felt her ass expanded in pulses and her insides getting filled with hot cum. The final stroke and pulsing cock was very painful for Mary, but it signaled an end to the anal abuse.

"OOOOUCH...Yeow!! Fucking hell.. it hurts so bad!" Mary sobbed as John slowly pulled his cock out of her ass. Mary's gaping asshole was slow to start closing. Becky and Helen felt great as they finally had some real payback as the bitch suffered for what she did.

"That was the greatest fuck I have ever had!" John said as he looked at Mary and smiled at her.

John let her legs down to the floor, and cum started to run out of her ass. Mary had a look of pure relief on her haggard face, and she was covered in sweat. She laid back, not moving as muscle as she let her ass drain cum on the floor. Mike and Ronald saw her gaping asshole pouring out cum and thought it was so hot looking.

Helen took Mary upstairs and let her rest in a real bed. She paid the price and deserved a rest, Helen thought, and she turned off the light and closed the door.

Before John left, he begged Helen to let him come can fuck Mary again. Helen was jealous of the request as she wanted John's dick in her pussy, not Mary's cunt.

"If you fuck me first, then we can talk!" Helen said.

"Of course, your pussy is always on my mind! I just thought you would enjoy the look of Jill's pussy being stretched open again for your pleasure!" John lied. All he was thinking about was Mary's wonderful pussy. It was tight and massaged his shaft in the most fantastic way, but if he had to fuck Helen to get to Mary, that is what he would do.

"Deal! I will contact you soon!" Helen said with a very wet pussy and thinking of how envious she was of Mary's cunt that seemed to take any cock and remain tight. Still, it was more than that, thought Helen; it was the way her pussy seemed to pulse and massage its way down the shaft of a cock in a way Helen's loose pussy could never possibly hope to do.

Helen turned back around to see Becky staddle Ronald's nice size cock on the sofa. Becky turned toward Helen as her pussy slipped down his shaft.

"She may be a home wrecking cunt, but that was the hottest seeing her ass get squired by John's cock!" Becky moaned as she started to bounce her pussy up and down on Ronald's man meat, making squelching noises.

"Agreed!" Helen said as she started to blow Mike, who was standing up watching Becky get a cunt full of cock.

Helen had Mike sit on the sofa next to Ronald, then she mount Mike and bounced on his cock in time with Becky fucking Ronald. They talked casually while fucking until Mike and Ronald lifted their hips together and filled their wives up with cum. Everyone was tired after all the action and went to bed. Helen had one more chore before going to bed, however. She opened her bag of tricks and went into the room where Mary slept like a baby.

Mary slept soundly with dreams of all things orgasmic. Her mind played a reel of all the recent events while she tossed and turned. She woke with a start when she dreamt of her tits growing to a great size filled with milk.

Her eyes opened, and she soon found that she was tied spread-eagled on the bed, still naked except for the correct and lace thigh-highs.

Her breasts were aching, but she could not soothe them with her hands tied. She looked at them in dismay. They looked huge, swollen, and almost dome-shaped from all the milk production, Mary guessed. She wiggled her chest, and tiny drops of milk came out of each nipple.

"Yes, that confirmed it." Mary sighed; they were filled to aching with milk.

She lay back wondering how long she would be tied to the bed when Helen came in with a cheery smile.

"You were passed out last night, so you probably did not even feel the injections; well, they certainly seem to be working. Look at those udders; they are so full! It must be uncomfortable?" Helen teased as she sat on the bed next to Mary.

"Yes, Mistress, they ache badly. Please untie me. I really need to soothe my breasts." Mary begged.

"Not a chance slut! You will remain here all morning until our next activity. You need to get used to your breast being full. Even when I free you, you cannot touch them without my permission. But I am not without sympathy," Helen said as she bent forward and started to suck on Mary's nipples. At once, Helen got a good flow of milk out of both nipples, which relieved some pressure. It also sent waves of pleasure down to Mary's pussy. Helen cupped her sex to feel the heat after feeding off Mary's tits for a few minutes.

"How does that feel slut? Your pussy surely seems to like it well enough!" Helen said as she fingered Mary's hole, which, to Helen's chagrin, was amazingly tight considering the dick that plowed it only twelve hours earlier.

"That feels much better, mistress!" Mary said, relieved that her tits did not ache as much.

"Well, that's the thing. The more they are stimulated, the more milk you make. Pretty cool, huh!" Helen said as she got up to leave.

"I will see you in a couple of hours with some food. We have to keep you fed to make milk, dear!" Helen teased and left the room.

Over the next few hours, her breasts seem to fill again and regain their dome shape as her hormone-induced milk ducts worked overtime.

She stared at her tit's, hoping they would someday be normal.

Becky came in four hours later, and Mary was starving by then. Her breasts were aching again as she looked up to see her come in and sit next to her on the bed.

"Sorry for the delay, but I wanted to make sure these puppies were nice and full. How do they feel slut." Becky said in a tone that made Mary uneasy.

"They ache, Mistress. I can actually kind of feel my breasts expand while laying here." Mary said, still wary of where this was going.

"Glad to hear it. I have food for you, open wide." Becky said and spooned thick oatmeal in Mary's mouth. It wasn't delicious oatmeal, but it was far better than nothing, and the way Mary was producing milk, she needed all the food she could get. Mary accepted each spoonful willingly. With her belly full, Becky put the bowl down and reached for a bag on the ground.

"I see the marks on your breasts are almost gone. Helen had a wonderful afternoon with you, I hear. Well, it's my turn, open wide!" Becky said as she broke out the bag gag. Mary was filled with fear, but there was nothing she could do, tied spread-eagled on the bed, she opened her mouth, and Becky pushed the gag in and secured it behind her head.

"I tell you honestly, Mary, ever since you have been here, my Ronald has taken excellent care of my pussy. I even let him ass fuck me, but that does not make up for the day I caught you!" Becky said as she stripped off her clothes, got on the bed, and straddled Mary's hips. She pressed her wet pussy against Mary's clit, so both their clits were touching and continued to speak while grinding down on Mary.

"It's a paradox, Mary, here I am, getting off on your clit, but I still have anger inside me. "Hell has to fury like a woman scorned" is the best way to put it," Becky said as she lifted the riding crop and ran it along Mary's tender milk-filled breasts.

Mary tried to speak into her gag, Becky only smiled.

Mary thought back to Shelby warning her saying the same line- "Hell has no fury like a woman scorned."

"I do want to suck on them, but I want your tits as tender as they can be for now," Becky said as she raised the crop and hit both heart-shaped areolas in quick succession. At the same time, she moved her hips back and forth to get friction against her clit. She was getting off torturing Mary, and it showed.

Mary screamed into her gag as drool poured down her face.

"You took a cock in your ass for Helen, but this is for me and only for me!" Becky said and struck the side of both breasts right in the most tender part, where the swelling was the worse. Two deep red triangles appeared as Mary gave a muffled yell.

''Umm, that looks better," Becky said as she grabbed both breasts and squeezed them, feeling the milk inside and smiling.

"My god, they have filled Mary! Your clit is really hard also and is driving me crazy!" Becky said she ground her hips faster and continued to squeeze Mary's tit's, forcing milk to spray out of each nipple.

Becky then began to pepper her breasts all over with the crop, and she drove her pussy to orgasm against Mary's hard clit.

Mary thrashed under Becky and tossed her head from side to side as her tits were once again covered in bright red triangles. It hurt much worse than last time before her breasts were aching from all the milk; Mary was sobbing but close to orgasm as Becky kept up the pressure on her clit the whole time.

Through the pain and pleasure, Mary felt Becky cum on her clit. Becky slowed her hips and came to a rest. She stopped whipping Mary's tits as she recovered.

"Aww, didn't get to cum? Too bad, maybe next time." Becky said as she bent down and sucked milk out of Mary's whipped breasts while squeezing them. Mary moaned as Becky worked her breasts and sucked her sore nipples.

Becky had her fill of milk and looked up at Mary's red swollen eyes.

"I will take the gag off if you promise to be silent," Becky said, reaching back as Mary shook her head in agreement.

"Thank you, Mistress!" Was all Mary said.

"Welcome slut! Now I feel better, and your fat tit's look the way they should." Becky said as she got off Mary and got dressed.

After pulling on her blouse, Becky looked down at Mary's still erect clit, still throbbing from all the stimulation. It stuck out a couple of inches and did indeed look like a small dick.

"Wow, Mary! Everything about you is exaggerated. Mind if I suck on it?" Becky said and bent over, not waiting for an answer, and sucked Mary's clit into her mouth. Mary responded immediately by moaning and lifting her hips, and Becky sucked on it like a cock.

"Umm, but you don't deserve to cum, not yet," Becky said as she stood up and untied Mary's bindings.

Mary wined in frustration but soon stopped as she did not want to get into trouble.

"Time to get up and do your chores slut! You know what to do!" Becky said and left the room.

Mary got up and started to clean the whole house from top to bottom, then she was giving her evening meal without further punishment.

After the retribution from Helen and Becky, they did not torture her much for the duration of her servitude. She was able to get progress reports on the Server room install and speak to Markus. The server room was progressing nicely and was on schedule.

Mary was beginning to wonder what was happening. She still had to endure the breast torture and whipping in the garage every day, but no more ass fucking or really painful punishments.

Toward the end of the three weeks, Mary was hanging in the garage being whipped by Becky when Helen came in to talk to Becky. Mary had endured being beaten so often it was at least bearable. However, Becky still enjoys berating her and whipping her "fat tits," as she likes to call them.

They left Mary hanging alone as Helen filled Becky in with the news.

"No shit! That is a fantastic idea!" Becky's eyes lit up when she heard the news.

Mike had suggested to Helen that they should hold a project completion party at their house for all the construction workers who finished the Server room project on time and budget. They could convert the garage by bringing in a pool table and dartboards. Helen was not overly excited until Mike mentioned that Mary could be the entertainment. She would need a mask, but they could all have their final shot at Mary before the end of her servitude.

Becky and Helen came back into the garage and took turns whipping Mary. They were excited again, and Mary paid the price with her tit's and ass, both of which were very red by the time they were finished.

Soon after, the night of the party came, and they gathered together in the living room to talk about Mary's participation.

"Ok slut, this is the final party, and you will be done. You will be the serving girl until later in the evening when, based on the action, you will be required to pleasure any number of the partygoers, and don't worry, you will be masked or hooded based on what you are doing. " Helen said.

Mary was very excited that the end was near. She would finally be free and able to enjoy her new life as an official partner of the company. This last party sounded like she might be giving a lot of blow jobs, and if so, that would be a small price to pay to end this torture. Her tits were still full of milk, and Helen enjoyed seeing Mary suffer by whipping them or the humiliation of getting her nipples sucked on constantly. They were all far kinkier than she had ever imagined, but at least they were not into orgasm denial. Mary had cum more in the last two weeks than she could remember, but she also drank a ton of piss and had been whipped daily. Some of it was stimulating, but keeping four kinky people happy took its toll.

Mike and Ronald had set up the garage with a couple of flat screens, a pool table, and a dartboard, plus a small wet bar for Mary to serve guests drinks.

They had also set up a curtained area leading to a door that leads into the living room. Mary wondered what that was for but dared not ask. She spent her time helping Helen and Becky decorate the garage.

She was dressed by Helen, who tightened her corset until she could barely breathe, but her tits stood out proudly, swollen and bursting with milk. Then Helen dressed her in Black fishnet thigh highs with a garter belt and short black leather skirt that came just below her pussy. She was allowed to wear a thong to cover up, which Mary was relieved to see. For a top, Helen had Mary wear a black leather crop top with no bra that wrapped tightly around her chest and had a gold zipper. Helen pulled the zipper down, so just her nipples were covered. At the last minute, she changed her mind about the gold chain and made Mary undress and put the chain on. Now the gold chain was visible connecting her nipples and going down over her bare stomach into her skirt. It was utterly slutty as it is evident that the chain joined her nipples under the crop top and the other end went down into her dress to connect to her pussy. In the end, she was just happy to be more covered up than she had been for three weeks. They gave her a party mask that covered most of her upper face. Mary was ok with it as none of the construction guys had ever seen her before and probably will never see her again. To finish off the look, Mary had to walk around in six-inch red heels. It would be challenging, but again this was the finale for Mary.

Mary started the party out behind the bar serving the guys as they came into the garage.

"Wow! You are one sexy girl!" It was one of the more excellent comments. Others were crasser.