The Job – Interview Day

Shelly and her husband were in real financial trouble. His accident at work had left him unable to do the roofing jobs he used to do. His employer hadn’t paid his worker’s comp insurance, so there was no money to support them. They had gone through their savings and maxed their credit cards, and had reached the point of desperation.
When Shelly saw the ad in the paper for General Office Help she knew she had to get this job. She dressed in her professional best – a very pretty floral skirt that floated almost to her knees, a white, short sleeved top that showed her figure very nicely, and a short navy jacket, just long enough to skim her round hips. Shelly was no beauty, but she had a nice figure, and pretty auburn hair. She took care of herself, and always tried to look her best.
Mr. Riley reviewed her resume, and asked her some questions. Although he seemed to be somewhat quiet and reserved, he was pleasant enough. He was the CEO of the company, and his phone never stopped ringing. If she got the job he would be her new boss, and she would act as his administrative assistant, sitting right outside his office. A good looking man, he was tall, with dark hair, just beginning to go a little gray at the temples. He looked like a man who took care of himself, perhaps a runner or someone who worked out at the gym.
“Well, Shelly, I’m impressed with your resume, and this has been a good interview. The job is yours if you want it,” Mr. Riley smiled.
Shelly closed her eyes for just a moment, so he could not see the relief there. “Thank you, sir. I really do want the job very much.”
“Great, that’s settled then. Now, before you go there is something I need to discuss with you.”
Relieved that she had the job, Shelly settled back in her chair, thinking he would be telling her when to report to work and about the benefits.
Mr. Riley got up from his desk and began to walk slowly around the room, talking as he went. “Shelly, I’m in charge of a very large company. As you might imagine, my job is very stressful. Over the years I’ve found that the stress I experience makes me less effective at what I do. That’s something I simply can’t afford.”
Shelly wondered where he was going with this line of thought.
“I’ve found a solution to this problem, and I want to explain it to you, because I will be asking for your assistance.”
“Whatever you need, sir. I’m happy to help.”
“Perhaps you should wait to hear what I have to say, first,” grinned Mr. Riley. “I will periodically intercom you, asking you to come in and take dictation. When you come in, you will lock the door. I will then ask you to bend over my desk, raise your skirt, and allow me to enter you through your ‘back door.’ The sexual release I will have keeps my stress levels down, making me more effective at my job. And or course, if I’m more effective, everyone who works here will benefit.”
Shelly was stunned. She couldn’t find the words to express her shock. How could she possibly take this job if this was what he expected her to do? And she had never had anal sex, so the idea of doing what he suggested frightened her.
“I know you’re shocked,” said Mr. Riley. “And I would not expect you to participate in this without additional compensation.” He walked to the back of his desk and opened a drawer, removing an envelope. “This envelope contains $500 in cash. You will receive an envelope like this each time you make yourself available to me. And I want it understood up front that there will be no romantic relationship between us. I consider this part of our business relationship, nothing more.”
Shelly’s mind was spinning. She needed this job so badly, but how could she possibly accept it under these terms?
As if reading her mind, Mr. Riley said “Let me make this clear. The job is yours, whether or not you choose to participate in this other activity. You are not required to do this. In fact, I would hate to lose your skills because of this; I think you’re going to make an excellent employee. If you do decide to do this, though, I have only one requirement. I would ask that you not wear underwear to work. Dealing with underwear just slows things down. A garter belt to hold your stockings is fine, but no panties and no bra”
Shelly knew she had to decide right now what she was going to do. She thought about the money she and her husband owed, and how close they were coming to being out on the street. And the $500 each time combined with her salary would go a long way towards getting them caught up. Maybe it wouldn’t be so bad. But anal sex? It just sounded so scary.
“I – I – don’t know what to say,” Shelly stammered. “You’re asking me to do something I’ve never done before. I very much want this job, and I think it would be a pleasure to work for you. But I’m just not sure about the other.”
“I understand. May I suggest something? You can tell me no if you want, but this might help you make up your mind.” Mr. Riley had walked around behind Shelly, and lightly rested his hands on her shoulders. “Would you consider an audition, a tryout – whatever you want to call it – here, today?”
“What?” Shelly gasped.
“Well, I think it would help you to make up your mind about everything. And it would take a lot of pressure off of your first day of work, wouldn’t it?” He leaned across Shelly and reached again into his top desk drawer, pulling out another envelope and laying it on the desk next to Shelly. “There is $1500 in this envelope. What I’m asking is very difficult, and I think you should be adequately compensated for it.” Very gently, Mr. Riley slipped Shelly’s jacket off and began to massage her shoulders. His touch was like an electric current going through her.
Shelly looked at the envelope. How could she refuse this money, when they needed it so badly? But could she do what he was asking? “You’re asking me to do this with you right now?” she asked in a small voice.
“It will be okay, I promise. I will be very gentle with you.”
Sighing, Shelly closed her eyes, silently apologizing to her husband for what she was about to do. “Okay. Tell me what you want me to do.”
Mr. Riley walked around in front of Shelly and extended his hand to help her up. “Why don’t you go into the bathroom over there and get yourself ready. Take your time.”
Shelly went into the bathroom and closed the door. She undressed completely and washed herself at the sink. Putting her shirt, skirt and high-heeled sandals back on, she looked at herself in the mirror. Her eyes were frightened, but her heart knew she really had no choice. Taking a deep breath, she steadied herself and walked back into the office.
Mr. Riley walked toward her, taking her hand and leading her back to the chair next to his desk that she had occupied during the interview. “Please, just sit and make yourself comfortable.” As she sat he adjusted a pillow behind her lower back, bringing her cheeks forward in the chair and causing her to recline at an angle. “Now I’m going to do something to help you relax. This isn’t part of what we’ll do in the future, but I think it only fair to help you relieve some stress here today. Could you slide your hips forward just a bit more, and then open your legs real wide?” Resting her arms on the arms of the chair and closing her eyes, she did what he asked. Riley knelt between her legs and began to unbutton her blouse. Opening it wide, he leaned forward and very gently kissed all over her breasts, first the right, then the left. Taking her nipple gently between his lips, he used his tongue to tease and tickle her. With his right hand he rubbed the flat of his thumb over her other nipple, circling around and around, then pinching the nipple between his fingers and pulling. Switching sides, he took her right nipple into his mouth and sucked hard. Shelly could feel it all the way to her toes, and moaned.
As Riley’s mouth began to move its way down her belly, Shelly felt his fingers exploring under her skirt. They traced a path up the inside of her thighs, and gently stroked her lips. Parting them, he gently pushed forward towards her clit, finding it and taking it between two fingers. Pulling gently, rubbing, pinching, his fingers were relentless, driving her desire higher and higher.
Riley lifted his head and pushed the skirt up around her waist. Pushing her legs farther apart with his hands, he leaned forward again and gently stroked the spot between her front door and her back door with his tongue. Shelly shivered. She was so wet, and so ready for him to enter her. Riley moved up and began to explore her with his tongue. He pushed it gently inside her, running it along her tender inner walls, sucking out her juices. Shelly began to squirm and moan softly.
Riley put his hands under her ass and pulled her toward him. He began to tongue her fully engorged clit, flicking it at first, then taking it into his mouth and sucking hard. Shelly gasped as she felt something enter her ass. He had pushed a finger in there, and was slowly moving it in and out. Oh my god, it felt so good! Now he was moving it harder and faster, even as he continued to suck her clit. Shelly felt the orgasm welling inside of her and cried out “don’t stop, don’t stop, don’t stop, don’t stop!” Suddenly her body was bucking in the chair and she was moaning a deep, guttural moan as the orgasm exploded throughout her body.
Riley didn’t stop until Shelly reached out a hand and gently touched the top of his head. He sat back and smiled. “Well, I think you relieved quite a bit of stress just now! Why don’t you just sit back and enjoy your endorphins while I get myself ready.”
Shelly really didn’t have a choice; she couldn’t have moved at that moment if she tried. She lay back against the chair with her eyes closed, trying to slow her breathing, feeling the after effects of the massive orgasm she had just experienced. She couldn’t remember ever having it feel like that. She was absolutely limp.
It seemed like half an hour, but had only been a couple of minutes when she heard Riley’s voice. “Shelly, are you ready to help me now?” She opened her eyes and saw him standing with a hand extended to help her up. He was naked from the waist down, and had a tremendous erection, easily nine or ten inches long, at least five inches around. Shelly couldn’t help but stare as she took his hand and stood up.
Riley walked her around to the back of the desk, and Shelly noticed that he had lined up a number of items on the surface. There was a tube of some sort of lubricant, a condom, and a pair of latex gloves. In the center of the desk there was a pillow and a wedge-shaped piece of foam with a pillowcase over it.
“Are you ready?” Riley asked.
Taking a deep breath, Shelly nodded. “What do you want me to do?”
Riley took her by the shoulders and turned her to face the desk. He pulled the foam wedge toward her and asked her to bend forward, stretching her arms across to the other side of the desk and resting her head on the pillow. He positioned the wedge under her hips and raised her skirt, exposing her lovely round ass. He caressed her cheeks with his hands for just a moment, then gently positioned her legs as far apart as they would go.
“Please try to stay as relaxed as you can. I know it’s not the most comfortable position in the world, but this won’t take very long.”
Shelly heard him snap on the gloves and open the tube of lubricant. “I’m going to put some of this on two fingers and push it inside of you. I’m going to be a little rough, so your muscles get an idea of what’s coming, but it shouldn’t hurt. Tell me if it does and I’ll stop.” Shelly felt one hand pulling her left cheek to one side, then some pressure as his fingers began to push at the opening. She felt the fingers enter, then stop as her sphincter tightened around them. Riley wiggled his fingers, which felt very strange to Shelly, but not painful. He removed his fingers, applied some more lubricant, and entered her again. This time he pushed harder, and she felt him pop through the sphincter. He deposited his gel and then pulled out.
Riley put his condom on, and squeezed more lubricant onto his hand. He generously coated himself, then took the gloves off and threw them away. “Okay Shelly,” he said softly. “It’s time.” He used his hands to separate her cheeks and lined himself up against her opening. Pushing firmly and steadily, he entered his tip, feeling her sphincter contract again. He grabbed her hips and pulled her back toward him, even as he pushed forward. Shelly let out a cry as he popped through her outer, then her inner rings. Riley gave one more hard push and buried himself fully inside her. Shelly was trembling. There was pain, but the sensation of being filled up by Riley overwhelmed everything else.
Slowly, Riley started to stroke in and out, almost pulling out but then pushing himself firmly back in. He developed a rhythm, holding her hips and pulling her close with every stroke. Gradually he increased both speed and intensity, until he was banging her hard enough to shove her into the desk with every stroke. There were tears running down Shelly’s face, because the harder he pushed the more it hurt, but she didn’t say a word. She could feel the tension building in him and knew he would cum at any moment.
Riley was grunting with each push, and his balls were slapping against Shelly’s cunt. Riley leaned forward, laying on top of Shelly and pinning her to the desk. There was a final flurry of brutally hard thrusts and then the explosion, as he shot stream after stream of hot cum. Shelly could feel him shudder deep inside her, as he let out a long, low moan.
After a few moments Riley sighed deeply, let go of her hips and pulled out. He helped Shelly stand up, and handed her the envelope with the $1500. “Can you be here Monday morning at nine?” he asked.