The Manstress

A man is hired to help a celebrity in need

Chapter 1 by Tip Tip

An unemployed Michael came home one day and found a letter in the mail. Inside was a letter offering a job that would pay a significant income but would require a year of service. All other details would be kept confidential absent a screening test. An address was provided with instructions to go the next day at a specific time.

, Michael arrived. It was an obscure office building. Michael walked into the building which seemed empty and was met with a single secretarial desk containing an extremely gorgeous redhead wearing a classy red cocktail dress. When he approached, she said he must have been Mr. Smith and asked him to follow her. As she got up, Michael noticed that she had model-like features, an amazing bust, an incredibly thin waist and an incredible behind. A complete knock out.

She led him down a series of hallways until they entered a single doorway into a room. The room was laid out with a bed in the middle containing a single set of white sheets, two small tables on each end, a desk and a table with some paper on it, a single trash can and a door at the end. Finally there was a one-way glass mirror taking up an entire wall with a light above it.

The redhead followed Michael into the room. She announced, "Good afternoon, Mr. Smith, this is now your test to see if you are qualified for the position. First, please take off all your clothes and place them on the table afar from you." Michael wasn't sure what was going on but he saw that she started unzipping her dress and taking off her shoes and, having no underwear, was entirely nude and looking at him patiently. She looked even more amazing without any clothes on.

Whatever this was, Michael wasn't going to pass up any chance at that girl. He immediately stripped while the girl went and got on the bed, lying down and spreading herself to him. After he got naked, she instructed, "Mr. Smith, your first test shall be cunninglingus." Michael immediately jumped on the bed and started eating out the gorgeous redhead. Michael had always been excellent at serving the ladies and she was soon panting and moaning from a series of orgasms.

She told him, "That is enough. Ten out of ten. The next test is eating my ass. Proceed." She turned herself over and leaned her ass up, directing Michael to go to town eating her ass out. He was also excellent at that and within minutes, the redhead was again panting and moaning from his tongue. She told him again, "That is enough. Ten out of ten. The next test is stamina during a blowjob." With that the redhead patted the bed and Michael then sat on the top while she proceeded to take his cock into her mouth.

Michael was very well-endowed with both significant girth and significant length. The redhead had a difficult time with the size of his cock, both at the start getting it into her mouth and then as she tried to deep throat the entire length. She accomplished that and was amazing as sucking his cock but Michael was able to keep from blowing his load. She stopped and announced, "Ten out of ten again, for stamina and for size. The next test is vaginal sex."

With that the redhead move on top of Michael and slowly tried to take in his monster cock. She groaned at the size and length of his cock but once it was in, she then proceed to fuck Michael as hard as she could in every position that two people can have sex in. Eventually she stopped moaning and told him, "Whew, ten out of ten again. The final test is anal sex."

The redhead then rubbed quite a bit of her fluids into her asshole and proceeded to put Michael's cock straight into her ass. His cock was well lubricated from her prior sex but she still had a difficult time with the girth and length of his cock. She eventually bottomed out on his full cock and moaned repeatedly as they then had sex in every position imaginable.

While Michael was fucking her in a doggy style position, she stopped him and said, "Now, stick your cock all the way in and cum inside my ass." Michael then pulled almost all the way out before ramming his cock straight into the depths of her bowels and cumming every single last bit of sperm he had into her. He pulled, watching her gaping ass leaked his cum all over her sexy body.

The redhead then proceeded to lick his cock clean. When she finished she told him to get dressed. As he did so, she cleaned herself with a wipe and put her dress back on. She looked at the mirror and a green light came on. She nodded and went to the desk and told Michael, "here is your 125-page employment contract, one hundred and twenty pages of which are a confidentiality and nondisclosure agreement. Say anything and expect to be sued for at least a hundred million dollars. You will be employed by a shell company owned by a holding company owned by a shell company and then another holding company. Your actual employer, I don't know who, but I was told is a female celebrity. The word is, while she publicly may be single, dating or even married, that relationship is just for show and she desires to have a male mistress or manstress be with her all the time and take care of her needs. She desires that this individual also have certain - ahem, physical - characteristics that you possess."

"You will be paid one million dollars for a year. You start immediately and your apartment and car will be taken care of. Your family and friends will be told you have won a worldwide cruise and they will receive postcards from around the world as such. If you wish to take the position, please sign here, here, initial every page hence and sign at the end."

Michael jumped and started signing. He handed over his keys, cell phone and wallet to the redhead. She immediately threw that into the trash can, threw the bedsheets in and then set all of that on fire. When Michael finished the signatures, she thanked him, wished him luck and took the contract with her as she left.

Once she left the room, Michael looked around lost until the other door opened and he met his employer.

Who hired Michael?

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