Escalation and Capitulation

by Phil E. Hebe

Copyright© 2014 by Phil E. Hebe

Erotic Sex Story: Would you let your boss see your wife naked if he offered you $500.00? what if he wanted more for more money?

Caution: This Erotic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Drunk/Drugged   Heterosexual   Fiction   BDSM   Safe Sex   Oral Sex   .

"Mr. Hemming wants to see you naked."

"What's the punch line?"

"No joke. Daniel wants to see what you look like without clothes."

"Just like that, out of the clear blue sky, your boss wants to see me naked."

"We were talking about our wives. One thing led to another and I mentioned what a cute little body you have."

Little? Yes. Cute? She didn't think so. She was petite, and slender, with small boobs and skinny legs. Angel could not image why anyone would want to see her naked. "You know the answer about a cold day in..."

"He is offering five hundred dollars."

"He wants to pay five hundred smackeroos to see me naked. What is he, crazy?"



"He said it would help my raise review that is coming up."

"The answer is still no."

The discussion did not end there. Ron begged and pleaded. He promised her anything if she would only do this. She was softening.

"So, how is this miracle supposed to take place?"

"I thought we would invite him over for dinner and drinks, and sometime after supper you would take your clothes off for him."

"A strip tease?"

"No, of course not. You can go to our bedroom, take your clothes off, and come back naked. Please, pretty please."

It took another week of sniveling by Ron before she agreed and immediately regretted it. He wouldn't let her change her mind. Then the Friday night came and Angel was a bundle of nerves. She wasn't sure she could do what her husband asked.

Supper would have gone better if she hadn't burnt the steaks.

"Where is your lovely wife tonight?" Angel asked. She really wanted to say, trophy wife. The woman was a good twenty years younger than Daniel.

"Out with the girls. Probably at some male strip club." He chuckled.

Her husband kept nodding his head toward the bedroom, and she kept ignoring him. She went into the kitchen to make up another round of drinks. Ron followed. He told her in no uncertain terms to go upstairs, get undressed, come back down, get the tray of drinks, and serve Mr. Hemming buck naked, or he would forcibly strip her in front of his boss.

That is what she did. It took all of fifteen seconds for her to down her margarita. She sat in the easy chair across from Mr. Hemming as if she were made of stone. He complimented her. "You are beautiful. You are the perfect pixie." She knew if she tried to talk she would stutter so she kept quiet. She was sure she was a bright red color from embarrassment. The booze was making her head spin. She went into the kitchen and made another drink. She came back and sat down again. That was quickly followed by another drink, and another trip to the kitchen.

When Angel joined them she saw that Mr. Hemming had his penis out of his pants. It was stiff. It was noticeably bigger than her husband's. The glans was split lengthwise in two down to where the shaft joined the glans. Each hemisphere was pierced with a gold barbell. His thick shaft was tattooed in a patchwork of bright colors. It was weird, freakish even, and she was mesmerized by it.

Whether it was the booze or his cock or both Angel loosened up. She became talkative and giggly. She went into the kitchen to get another round of drinks. While there she played with her pussy getting herself aroused. If the boss man wanted a show, that is what she would give him. When she sat back down across from Mr. Hemming she opened he legs, which, up to that point she had tightly held together, and displayed her swollen open vulva. She heard her husband start coughing in mid gulp. Fuck him. He got me into this mess. The smile on Mr. Hemming's face was priceless.

Angel got up and on the pretext of getting more chips she sashayed her way to the kitchen. She knew her butt was her best physical asset, nice and round. Much better than her small twin peaks of a bust that never grew any larger once she graduated middle school. 34A. Ugh.

In spite of her husband thinking that she went too far, he was a tiger in bed that night.

Monday when Ron came home from work he gave Angel an envelope with five hundred dollars in it. "You earned it, it is all yours to do what you want with it. Mr. Hemming is already talking about a repeat performance.

It wasn't long before Ron came home with another request.

"He wants to see me naked again?" she asked.

"A little more involved than last time."

"How much more?"

"He wants to spank you."

"Uh uh. No way."

"He is willing to pay a thousand dollars for the privilege."

"Did you say a thousand just to spank me? Maybe I should reconsider."

"Wait there is more. You will both be naked, you will be tied face down to the bed, and afterward you will give him a hand job."

"All that for a thousand? I got to think about it."

"Let me know soon. He wants to come over Friday. Oh, one more thing, I have to make myself scarce while all this goes down."

She thought and thought. A grand sure did sound good. On the other hand she never been spanked in her life. And then again, what was it like? She would get to see that unusual penis again. "Ron, I have a question. Are you all right with your wife carrying on like this with another man, even if he is your boss? Let's face it, this is much more involved than being naked in front of him."

"I love you. If my love only meant sexual fidelity it would be a sad state of affairs."

"If you truly mean that, for a grand I am game."

Angel prepared herself by drinking several margaritas and taking a tranquilizer even thought she knew she shouldn't mix the two. It was an emergency. Mr. Hemming arrived carrying a valise and after hellos Ron left. Angel was only wearing a robe. Mr. Hemming undressed himself. He was hairless including his pubic area. Not only was the shaft of his cock tattooed, but also his scrotum. The gold beads on his glans glistened in the light. Angel was again mesmerized by it. She stood stock still as he removed her robe. Opening the valise, he took out fur lined leather cuffs for her wrists and ankles and put them on her. He had to give her a slight tug to get her walking to the bedroom. "Lay face down on the bed with your arms and legs stretched toward the corner posts." When she was situated the way he wanted he took out lengths of rope from the valise and tied her spread-eagle. In spite of Angel's fortification, her heart was beating rapidly. "Just relax," he said, and then added, "Have you ever been told you have a very nice ass? It will be my pleasure to spank it." He stuffed a washcloth into her mouth. The spanking began. She didn't realize it would hurt so much. She screamed, she cried, she begged for mercy, but all that could be heard were muffled unintelligible sounds. When he was done he untied the ropes and helped her sit up.

Her ass burned. She continued crying. He took her in his arms. That she didn't expect. He hugged her and apologized for enjoying spanking her. She wished he would have apologized for hitting her so hard. He kissed her on her forehead and then wrapped her hand around his cock. It didn't even reach half way around. "You know what you have to do," he said.

"Yes, Sir." She did what needed doing. His semen shot half way across the room. He left her sitting there, naked. Ron came home a half hour later and she was still sitting there, all cried out.

"Was it that bad?"

"Did you get the money?"


"I guess it was worth it."

"Mr. Hemming would like you to have your nipples pierced. He would take you to the tattoo parlor, and bring you home. He will pay for the piercing plus give you a thousand dollars."

"He would give me a thousand dollars just to have my nipples pierced."

"That is a thousand dollars for each nipple."

"So that is two thousand dollars for both nipples."


"Is he made of money that he can just blow it like this. He already blew fifteen hundred to see me naked and give me a spanking, and now you are saying he wants to give us two thousand more just to see my nipples pierced."

"Honey, he has tens of millions. A couple of grand is pocket money for him."

"You would be okay if I did it?"

"You know I don't pay much attention to your breasts. It wouldn't bother me at all."

She could not understand why Mr. Hemming would want her nipples pierced. They were small with hardly any areolas. The nipples reminded her of the erase on her number two pencils she used in grammar school, just about as small and almost as pink. The only nice thing was that they sat at the exact apex of her conical breasts.

"We could use the money," she said.

"It would buy that new stainless steel, six burner, gas stove with the double oven you been wanting."

"Good point."

She agreed. It sounded better than scrubbing semen out of the bedroom carpet. Daniel took her to the parlor the following Friday evening. While they waited Mr. Hemming tried to talk her into getting the nether lips tattooed. "Absolutely not."

"Then what about a rose bud tattooed on your butt?"

"I would have to give that a lot of thought before I agreed."

The proprietor came up to them at that point and the subject was dropped. She had both nipples pierced with what was called starter rings. They were small. The man who pierced her said she could get bigger rings once the piercing healed in six to eight weeks. Mr. Hemming showed her the rings he wanted her to wear, they were an inch in diameter and had a ball at the bottom. The proprietor showed her how the ball moved aside to allow her to take the ring off, if she wanted. Angel was given an antiseptic cream to put on her nipples twice a day. It took a week for the pain to subside, but the nipples were still very touchy for weeks after that. The compensation for the pain was the shiny, new stove in her kitchen.

"Where is Mr. Hemming?" Angel asked. "He has not visited recently or made any sexual requests."

"He is going through the throes of a divorce. it seems her Friday nights out with the girls turned out to be with the boys. He has her dead to rights and does not want to jeopardize it by being caught in a compromising position. He is trying to be Mr. Perfect Husband."

In a way she was glad he wasn't making any unusual sexual requests of her and in a way she wondered what he had next in mind for her.

Mr. Hemming showed up on a Wednesday night completely unannounced. "I am sure I gave the dick my wife hired the slip. I am so horny it hurts. It is worth three grand to me if you help me out."

"What do you have in mind?" Ron asked.

"Like that one time I gave her the spanking, but instead of a spanking I want to use a whip, and instead of a hand job I want a blow job. It is especially important that she swallow."

Angel and Ron went into the kitchen to discuss the proposition.

"I am afraid of the whip. The spanking was bad enough."

"I promise I will ask him to go light on you. With three thousand we can buy you a matching refrigerator and dishwasher."

"I got a feeling I am going to regret this.

"Please. This one night only."

She agreed.

It started out just like that one time. He cuffed her and tied her face down to the bed. He took a quirt from his valise and, as the saying goes, tanned her hide. It was no easier to take than the spanking. Afterward he untied her, and had her get up. He laid face up on the bed and had her straddle him with her mouth above his cock. Her tongue explored the cleaved area of his cock and the gold balls. She sucked his cock as best she could. When he came, she swallowed as fast as possible. She thought that would finish it, but before she could move he pulled her up until her pussy was in his face. She quickly learned that Mr. Hemming knew how, when, and where to lick pussy. What he did far outweighed the pain of the whipping. Her own husband was a rank amateur when it came to doing the same thing.

Mr. Hemming paid Ron the three thousand dollars as Angel laid on the bed with a big smile on her face.

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