Milf in Trouble - Copied

[hirarandi]

Later that day, Shelby called, wanting to come over to inspect her rings. Mary had a feeling that Shelby had more reasons for the visit. Mary was just fine with it as she liked Shelby. They had become close over the weeks since Shelby started to work for her.

Shelby came over that night dressed in blue stockings, plaid skirt, white button-down top, with circular black frame glasses. Her perky B cup breasts and long jet black hair added to her down-home college girl look that Mary loved. She was showing a lot more cleavage than usual. Mary stared down at the view of her well-formed breasts peeking out of her innocent-looking blouse.

"Hey there! You look fabulous!" Mary said as she walked up to Shelby and gave her a big hug. Shelby felt good, wrapped in her arms with their breasts pressed together.

"Thank you! Good to see you, boss!" Shelby teased, returning the hug tightly.

They went into the living room and chatted about the usual work stuff for a couple of hours. Mary made them more than a few drinks, and they were both feeling the effects.

"Sorry again about Kelly. She just has it out for you. I did not expect her to make you take it in the ass!" Shelby said as she got more loosened up by all the alcohol.

"Ya, well, that's our Kelly! She will get hers someday!" Mary said, also feel the effects of drinking the whole night.

" And I must say, Mary, you are a star at sucking cock. I hope you are not offended, but, well, I am kinda jealous!" Shelby said, looking down at the floor beet red in the face.

"Jealous of me having to suck all that cock! You can take over anytime!" Mary teased.

"No...not really...just at how good you are at it. You seem to have an amazing talent, and you take any cock straight down your throat. Very impressive. I love the control you have over guys!" Shelby said.

"Tell you what, if you want, I can show you if that's okay? It took a while, but yes deep throating is the best way to suck a guy, especially if you want to make them cum faster!" Mary said, amazed that little Shelby was admitting all this to her.

"I would love that, but how?" Shelby said.

Mary went to her bedroom and came back out with a pillowcase full of items.

"Here is my secret stash!" Mary said as she dumped out the contents on the sofa in between them. Several dildoes fell out of the pillowcase, from small to quite large.

"Now, let's start with the smallest one. At first, loosen your throat and just try and get past your gag reflex. It seems impossible at first, but just keep trying." Mary said; she picked up the 6-inch dildo and slowly pushed it down her throat to show Shelby how it's done.

"Right here is the tricky part," Mary said as she pushed the dildo past the back of her mouth and into her throat.

"You make it look so easy!" Shelby said.

"I have sucked a lot of cock in my life, sweetie! Here try. Lube it up real good first." Mary said, handing her the cleaned-off dildo.

Shelby was pretty drunk, so she got it down her throat after the fifth try with many tips and tricks from Mary. She turned toward Mary smiling with the dildo all the way in.

"Very good, you slut! Now let's try a bigger one!" Mary teased.

It took an hour, but Shelby worked up two dildo sizes. She gagged many times, but each time she could get past the "zone" in the back of her throat easier.

"Okay, now for the granddaddy!" Mary said she took the eight-inch dildo and stuck it to the wall at knee height above the floor, then got on her hands and knees and slowly swallowed the dildo until her nose touched the wall. Shelby saw her throat expand as the dildo disappeared. Mary turned to Shelby and tried to smile, challenging with a mouth full of plastic cock.

"Amazing, Mary! Just truly amazing how you can do that!" Shelby said, getting more turned on by the minute.

Mary backed her mouth off and licked the end of the dildo playfully.

"Okay, it's your turn now Shel. Just remember everything I showed you. Loosen up and go slow! Oh, and here, take another shot; it will help!" Mary encouraged handing Shelby a shot of tequila.

Shelby shot down the tequila and moved into position on her hands and knees in front of the dildo sticking out from the wall.

She crawled up to the dildo and licked it up and down to get it lubed up, then started to suck it into her mouth. Shelby was very buzzed at this point, which helped hold her gag reflex at bay.

Mary thought Shelby looked very sexy in her blue stockings and plaid skirt crawling up to suck a plastic cock. Also, her black lace panties came into view as she struggled with the dildo.

Shelby tried several times to get the thick head of the dildo past her gag reflex, but she came up gaging and coughing every time. She was drunk and very frustrated.

"I just can't! It's too thick!" Shelby complained, with tears in her eyes.

"Remember when you had a hard time taking Dave's huge cock in your sweet little pussy? You have to relax and believe that your throat will open up even when it seems it won't. Also, if you let me, I can help you while you try again." Mary soothed.

"I guess I do. I remember when I relaxed my pussy, instead of fighting it, Dave's cock went in a lot easier, but how will you help now?" Shelby asked.

"Just start again, and I will show you," Mary said as she moved beside Shelby.

When Shelby started to slurp up the dildo, she felt Mary's hand cup her sex and rub it through her stockings and panties. The sensation distracted her as she tried to force the dildo deeper.

"That's it Shel....just think about my fingers rubbing your little nub." Mary cooed as she adjusted Shelby's head, so the dildo had a better angle. Mary massaged Shelby's throat to help loosen her involuntary contractions.

"That's it Shel...just relax your throat and pretend it's a nice juicy cock." Mary continued.

Shelby pushed a final time, and, with a little nudge by Mary in the back of Shelby's head, it finally slid past her gag reflex. Shelby tried to back out, but Mary held her on the dildo, which was only just in her stretched throat.

"Don't move! Hold on a sec; I have to get better access to your pussy. This is the final stage!" Mary said as she pulled off Shelby's stocking and underwear, spread her legs, and started to lick her wet pussy.

Shelby gave no resistance as she lifted her legs, one at a time, to let Mary expose her pussy. Shelby backed off the dildo, gasping to catch a breath of air.

"Now move slowly down the dildo Shel, and I will do my best from back here!" Mary said as she started to lick and suck Shelby's sweet young pussy.

Shelby, thoroughly distracted by Mary's tongue, started to gobble the thick dildo down. Tears were in her eyes as she pushed harder, trying to get inch after inch down her stretched out throat and moaned around the dildo as Mary slurped up her sweet love nectar. Mary was proud of her as Shelby eventually made it down the eight-inch plastic cock. Mary stood up and saw Shelby up close in her moment of triumph.

"Now, if you can, try slowly fucking yourself with it as I bring you to orgasm. I want you to cum with it in your throat." Mary said as she petted Shelby and stroked her cheeks with a mouth full of dildo.

'Ummmp...uhm" Shelby mumbled, nodding her head. It felt extraordinary to have her throat so stuffed.

"It must be half to my stomach!" Shelby thought as she started to fuck her throat with the dildo. She pushed her mouth deep and then came back out only to push it deep in her again. She was getting into a rhythm, and Mary was eating the hell out of her at the same time. 

"I am throat fucking a huge dildo, and I love it!" Shelby thought.

Mary sucked her clit and licked her juicy pussy until Shelby came all over Mary's face with the dildo deep in Shelby's throat.

"Ummmmph!" Shelby moaned as she came, then backed off the dildo. She needed air badly but wanted to cum with it deep in her throat.

"Wow, that was a big one. Thanks for the help!" Shelby said as she sat back on the floor, exhausted.

"The pleasure was all mine. Seeing you swallow that thing while munching on your sweet Vulva was a real turn-on!". Mary said while sitting down next to her on the floor and wiping the girl cum from her lips.

She thought it was so cute how Shelby turned bright red at her description.

"Well, thanks for teaching me. I hope to put my new found skills to the test someday soon!" Shelby said.

"You will do great! You are a natural! Most girls spend weeks swallowing down a cock that big!" Mary said, impressed.

"Thanks! I have a great teacher! Now I think I'd better take a look at your rings." Shelby said.

Mary got up off the floor and laid back on the recliner. She spread her legs wide to give Shelby full access to her diamond-studded pussy.

Shelby looked down at the sexual goddess spread out before her. Mary starred up, cupping her breasts, pulling on her barbell piercings. Shelby thought that the OFFICE SLUT tattoo on Mary's pussy fit her perfectly, plus her massive DD breasts tattooed with 'I LOVE TO SUCK COCK' looked fantastic. After a long stare at her boss, Shelby got down on her knees to take a closer look at the eight rings lining Mary meaty labia.

"Wow, these really do look inflamed. Have you been a good girl? It looks like these rings have been abused lately." Shelby said as she lifted each ring carefully to look at the penetrations.

"I have tried to be good, I have played with myself, and it hurt too much, so I stopped altogether a few days ago," Mary lied, not wanting to admit impaling herself on the very same dildo that Shelby had just swallowed down her throat.

Shelby applied some antibiotics to her ring penetrations, which stung Mary.

"Ouch!" Mary said.

"Hold still! I am almost done. Now I want you to wear underwear to keep the rings in place, so they don't pull on the ring holes. You should be better, very soon. Keep applying the antibiotic twice a day for three days. In a couple of weeks, they should be fully healed. Don't do anything to yourself...you know what I mean...and you should be good." Shelby said as she finished.

"Thanks Shel! It feels better already!" Mary said as she got up off the recliner and put a robe on. She did not tie the robe closed, so her massive cleavage still showed clearly.

"No problem! I will see you soon! Call me anytime! Kelly is going to be back in two weeks, so that should give you enough time to heal. I will see you at work tomorrow for your morning meetings." Shelby said.

"You mean my morning protein breakfast cock sucking!" Mary mocked.

"Sure, Mary...for your breakfast!" Shelby said, smiling as she walked toward the door and left.

The next day, Mary got up, applied the antibiotic to her labia rings, and left for "work." She dressed for success as usual in white lace thigh highs, short pleated skirt, shelf bra, and a see-through white button-up blouse, showing copious cleavage, and drove to work. Kelly said she could not cover up until she got to work and had to smile and turn her chest toward anyone who saw her while driving. Guys in many cars stared at her tits, so blatantly on display, during the crowded morning commute. The roses on her breasts showed clearly to anyone who happened to look over at her at a stoplight or driving by. She could do nothing to hide her breasts and was beet red from embarrassment, especially if she got cat calls, or when she saw the girlfriends/wives hit the guys for staring at her and her breasts. Her pussy moistened as the humiliation flowed through her body.

She walked into her office right on time and soon was sucking cock. Sandeep's thick cock slid down her throat as he manhandled her naked breast and twisted her barbell piercings. Mary moaned around his shaft from the pain.

"Boy, Mary! I sure...missed...your...cock...sucking...mouth!" Sandeep grunted in time to Mary throating his thick cock while he continued to massage her perfect breasts.

Mary loved sucking cock, but was still not happy about having to suck so many all the time. Sandeep usually had a large, good tasting load of cum, so he was her favorite of them all.

Mary sucked and licked his thick cock for several minutes before Sandeep pulled out to fill her mouth with cum instead of blasting it down her throat.

Mary obediently stared up at Sandeep with her tongue out as he shot ropes of cum into her mouth.

"Oh god, that was great!" Sandeep said as he stared down at Mary. She let him view her mouth full of spunk before gulping it down in one swallow.

"Glad you liked it. Now you better get back to work and keep up the accelerated schedule as we agreed!" Mary said, switching gears from office slut to manager as she put her blouse back on, covering her massive DD's.

"Yes, Ma'am!" Sandeep said, knowing performing well might mean another shot at fucking her sweet tight ass.

Mary spent the next forty-five minutes sucking cock and swallowing the cum from the five team members left. She let Jerry shoot a couple of thick ropes of cum on her tits as a favor to him. He was her second favorite, but managed to scoop most of it off her breasts and into her mouth anyway. She finished swallowing the last load and now had a belly full of cum and therefore was not hungry for lunch.

"I guess sucking cock is a true substitute for a balanced diet!" Mary thought, rubbing her full belly, amazed at the amount of cum her team shot into her stomach daily.

She drove home with her tit's practically hanging out to the pleasure of every guy she saw and even some women. It made her feel cheap and slutty, but most of all, wet. Denial was in full swing as she tried to justify her actions toward the end-game of becoming a partner. She was enjoying acting like a slut, but the enjoyment was sub-conscious and fully covered up by a layer of made-up reality. She still thought of herself as a future Partner in a major company.

Over the next two weeks, she sucked down over fifty loads of cum by blowing the whole team daily. She got used to loads of cum blasting down her throat and hadn't eaten a regular breakfast since. All eight labia rings were now fully healed by the end of her "vacation." Kelly would be coming back on Monday, and Mary was nervous as it was now the Sunday before returning to work. Shelby called to come over and consult with her now that Kelly was returning. She had not cum since the beginning of her break, and she was very horny now that she could play with her pussy freely. The clit hood piercing rods and now the eight rings lining her labia made her pussy much more sensitive to even the slightest touch. All she had to do was strum the labia rings with her fingers to send her pussy down the path toward climax. She held off cuming, even when she had a chance. She did not fully understand why, but her subconscious knew well enough; Kelly was returning and did not allow climaxing. She drove her pussy to the edge of cuming more than once while waiting for Shelby to arrive. Her pussy was leaking by the time she got up to answer the door.

Mary only wore a loose-fitting red silk robe, her extra-large, perfectly shaped breasts barely hidden with the rose tattoos showing clearly. The jingling labia rings had Mary cringing as she walked to the door, her face flush with embarrassment. The heavy rings also pulled her large pussy lips down as she walked; this was a new sensation and not one she expected. Mary was very self-conscious about her pussy lips as they hung down like meat flaps, even lower than before.

Mary was surprised as she opened the door and saw Shelby standing there in a professional-looking, but short, tight black skirt with a matching white top that showed more cleavage than Mary had ever seen. She was not wearing a bra as her B cup breasts and little nipples poked out of her blouse. Gone were her cute back framed glasses. Her black lace thigh highs were also new and matched her red high heels perfectly. She looked like a wanna be Mary.

Shelby had a new look and a new attitude now that Kelly was coming back. She wanted to reset her relationship with Mary. Kelly had been in contact with Shelby over the last couple of days and was impressed by Shelby and wanted to expand her role as Mary's "assistant." Shelby had many ideas about how to deal with Mary. Kelly agreed to let Shelby control Mary's daily tasks and duties. Kelly told Shelby that she would take on more of Mary's duties surrounding office and employee management. This would give Shelby more responsibility and allow Mary more time for "other" tasks. Shelby's pussy moistened at the thought.

Shelby really liked Mary and was very grateful to her for the job, but Shelby also loved humiliating Mary. It excited her, and loved the way Kelly treated Mary. Shelby now knew that Mary, deep down, loved to be dominated, and she also knew that Mary, while a slut, still wanted to be a Partner in the company, so she had to be careful about pushing her too far, especially at work.

Shelby looked Mary up and down, soaking in her red robe and huge, barely hidden breasts.

Mary could tell right away that she was more business-like by the way Shelby stood and reacted to seeing her. The suddenness of the change excited Mary. She did not know what to expect.

Shelby walked right past her into the house and into the living room without saying a word. Mary followed behind her, not knowing what was happening.

"I hope you enjoyed your vacation, Mary. How do you like my new look?" Shelby said, in a formal tone as she sat on the sofa facing the recliner.

"You look great, but you seem different besides the clothes, Shelby. Is everything okay between us?" Mary asked tentatively.

"Well, Kelly is giving me a promotion, more responsibilities, and said I should start dressing and acting the part. Part of the job is taking over some of your responsibilities. Of course, we are still friends, but I think we should talk about my new role and how you fit in. I don't want this to be a surprise back in the office." Shelby said with fake confidence. She was very nervous about this but was driven by the potential...the potential to dominate Mary.

"I am sure that whatever Kelly said, you will be a friend to me, Shelby. I really value our friendship and would be sad if that changed." Mary said.

"Great! I need you to know that I will always be your friend, but Kelly wants certain things. I want you to know that it's Kelly and not necessarily me. I can't say I mind some of the directions from Kelly, but you must know my situation." Shelby said in an overly sad tone. She was trying hard to get Mary to think it was all Kelly's idea. In reality, all was all hers.

"It's okay, Shelby. I know all about Kelly, and she has made me promises she cannot back out of. Do what you must, and in the end, I will get what I want, and hey, it looks like you will also get what you want, so it's a win-win!" Mary said, staring through her spread legs at a sad-looking Shelby.

"That makes me feel better, thanks, Mary. First, since your rings have healed, I have to put the chastity cage back on. This is a new one. It's lighter and goes on easier than the old one." Shelby said as she got on her hands and knees between Mary's legs.

Shelby stared at her pierced Vagina. Both labia were lined with four gold rings each, and six diamond studs lined her clit hood holding three clit stimulating rood. Shelby thought Mary had a beautiful pussy. Her thumb-size clit and large pussy lips complemented the piercings. It seemed like her pussy was made for it even if her OFFICE SLUT tattoo was not emblazoned over her public area.

Shelby got the new chastity device out of her purse and held it up for Mary to see. It was smaller in size but had a plug attachment and a claw-shaped piece that fit over her Vagina.

"That does look different. What is the plug for...you can't be serious!" Mary said as she started to close her legs involuntarily.