Shy Assistant


This erotic sex story published on Feb 1, 2009 was written by stoneypoint and is from our Longer erotic stories section.
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"They were on the bed her legs were spread out, and she fucked him as though that day was the last day on earth"
Delores, answered her phone, said yes sir, and quietly stood up. Pressing her skirt against her to iron out the wrinkles, she slowly and silently headed for his office. Unaware of what was about to happen the woman who was short of forty wore her hair fairly short as well as glasses which were outdated.

Conservative in her fashions she never let anyone know her too personally. She preferred it that way. She was not entirely comfortable with herself and she was the most introverted woman in the office. As well, she dressed in older fashioned, traditional styles for she was not aware of the true beauty which she contained.

However, he saw it, he appreciated it, but never did he allow himself the benefit of complimenting her. He couldn’t. He wouldn’t. He was married, older, and there were others to consider. Plus she had a hidden agenda of her own.

She knocked. “Yes sir…you asked to see me” she said meekly carrying a paper and pen. He was not smiling, not this time. He told her to sit. He didn’t look happy or well. She noticed the look on his face, but said nothing. She sat prepared to write. He collected his thoughts. He told her. She was shocked. She couldn’t believe what he had told her. She knew the books, she knew lots of things, and she knew she was the highest paid worker besides him at the company. “But why sir?” she said. The tears hadn’t formed. Sales were down, she knew that, but business was still decent. Prospects and contracts were still coming in and she knew that of all things. “Why…why me sir?” she said. Her voice was shaking. She couldn’t understand. She didn’t want to understand.

“It’s complicated…it is just a complicated mess, Delores” he replied sorrowfully. He looked towards her, she was looking down. He could tell. He could see what was about to happen. He apologized, said he was sorry about fifty times over. She didn’t ask why, she started thinking, but she couldn’t and wouldn’t ask why. He knew why. There were two reasons why. One, the recession was upon them, prospects and fallen off the face of the earth, and so no contracts had been signed hence no revenue…blah, blah, blah. “I am so, so sorry” he told her for the umpteenth time. He didn’t tell her the other reason. It wouldn’t matter and he loved her. He loved her like a friend, sister, and confidant.

Then it happened. Instantly he stood up as he watched them roll down off her cheek. She had no where to go, no job prospects, and the upcoming Friday night was supposed to be the time of her life. Not any more it wasn’t. He didn’t know that, but then no one knew it…except of course Delores and the two men she came to know at those parties she let herself go to. But for the time being, she was beside herself. She was bawling, his arm was around her, and he was trying as hard as hell to comfort her as best as he could. God he loved her, like a friend that is, but he did care for her. She had gone over and above the call of duty for him countless times. She did some of the most extraordinary work most employees would do for their boss.

He continued holding her, continued comforting her, and continued apologizing in the best tone of voice he could muster. Maybe I can figure something out he wondered. Just maybe, maybe I could.

She continued crying, but it had reduced itself to simple sniffles as he pulled her against him telling her or trying to tell her if there was another way, he would do it, and he also said it would be okay. His voice was comforting. He was so gentle with her and his arm around her felt so nice that she felt at ease being as closely held by him. The whimpering slowed and only occasionally did she sniffle. She felt the warmth radiating from him. He felt nice even though he was the “enemy” now. Not that he was but he was to be her ex-employer in three days, the day of reckoning for her, the day she was to host two men she casually met at a social engagement she was at, and she hadn’t even thought of it, yet.

“I’m sorry” he told her quietly and then he sprung it on her.

Then he finally told her the other reason. She had an occasional fantasy about it, but that’s all it ever was, was an occasional fantasy. She never ever made anything out of it. He was her boss and she was his employee and he was married and he had children too. So seeing as she was an honest, sincere employee first and foremost, she never once considered anything seriously.

“Me, you?” she asked. She was surprised to hear that. “She…she thinks we…we…you and I are…are romantically…no, no sir. You tell your-” but he was looking into her eyes.

He was watching her response. And for the very first time in his life he really saw it. He saw it for the first time. Her eyes glimmered behind those big outdated glasses she wore. And he couldn’t help himself. Yes, like her, it had crossed his mind, but it was only a thought and nothing else. She was a shy and quiet employee, however she was pretty if you got passed the glasses, you got by the lack of necessary makeup, and if you could get over her lack of fashion sense then she was adorable and prettier then you might expect.

And she was speechless. He was gazing into those big brown eyes, he was looking at her slim but pretty parted lips, and he was caught up in the moment. And he surprised himself, he surprised her. He kissed them. He leaned in and surprisingly kissed her parted lips. And she did not stop him. She did not resist it. She did not push him away. She joined in. She kissed him back. And the two kept on kissing, kept on enjoying whatever moment this was, and before either knew it she was holding him and he was holding her close. They were embraced in a heated and passionate forbidden kissing fest both knew was entirely wrong and immoral. But it felt wonderful and fulfilling to kiss the woman he had to let go. He wanted to do that, once in a while, for a long, long time. And yes…yes she wanted to kiss him as well, but she knew like him it was never going to happen, but it did. And it was exciting and wonderful as ever.

“Oh god, Delores…I’m…I’m sorry. I am so sorry I did that. That was inappropriate. What I did was uncalled for, out of place, and in no way was t meant to…to make you feel better for…for what I have to…” but he didn’t finish his sentence. And he didn’t have to either.

“It’s okay” she said in her typical demure voice.

Inside she felt whole and excited as hell. Her boss who generally regarded her not only as an employee but his top assistant had accidentally kissed her passionately and aggressively as well. But that one kiss was a superb kiss. And that one kiss had her floating on air as she walked out from his office fixing her hair and skirt before leaving.

What did I do he wondered? Why did I just…ohhh you idiot, you idiot he told himself. He couldn’t believe he just did it. But it felt awesome, she felt great, and he wondered if it could ever…no, no it wouldn’t ever happen again. Ohhh you stupid moron he thought.

I want…ohhh I want…ohhh I wish I could she said with a faint smile on her face. She had just been given notice of her impending lay off, effective in three days too. The same day as her rendezvous with her two new friends she had met. She hadn’t even considered that. She hadn’t even considered what that would consist of. And for that matter, why two of them? What was actually entailed? She wasn’t thinking clearly. She wasn’t thinking about her Friday night “date.” All she could think about were his lips, his kiss, and how he held her, closely and passionately and so aggressively. Ohhh god…I want…I want to…to go back in there.

“Sir…may I see you a moment?” she asked him on the phone.

He said no and apologized. He was overly polite. She understood. Her intentions were totally out of line. She wanted to go back in there. She wanted him to hold her again. She wanted to press her lips against his. She wanted to feel what it felt like again to be kissed by a man, she knew, but didn’t realize how extraordinary it could feel…inside her. She apologized for interrupting him. She apologized for the call. She sounded as if she lacked that confidence she always seemed to have…but she wanted him or more to the point…wanted to kiss him again if he would let her.

He knew why she had called or he thought he knew why. And so he emailed her. He apologized for overstepping his boundaries. He apologized for the imposition. He apologized for violating the boss-employee line of conduct. He knew better, she did too, but it was an impulsive move…one in which in a thousand other incidences he wouldn’t have ever done with another employee…regardless who they might be.

She read it. It aroused her. It aroused deep hidden desires within her. She hadn’t realized she had them towards him actually, but she did. And all she wanted, all she cared for were his lips, his clutching arms against her, and pulling her passionately inward so they may kiss and enjoy the last of their union with one another. So she wrote a reply. She told him it was alright. She told him she was not put out. She told him she felt no resentment. She told him, if she had to do it again, she would, and she would do it twice as fervently as before. And she told him he was beautiful. She told him she felt wonderful and feverish inside for it again. She wrote in her reply how she would love to be alone with him, all night, all alone, and kissing and holding, and…and…and touching, yes touching one another as passionately as two loving individuals might do. She reread her email.

Then she canceled it, but she forwarded to her home email first. She then canceled it wishing she had the confidence to actually send it to him telling him just how she felt. But she could not. She knew it was wrong. She knew he would scorn her. That’s how she felt, but she wished and hoped and she imagined that moment so many times throughout the next couple days, but it would die out. It would temporarily pass. For she had plans… one enjoyable night with two nice gentlemen and an evening of romance and possible sexual pleasures she couldn’t possibly fathom they had told her.

Me…me and them she wondered? Why me, why not some beautiful and sexually more attractive woman who is younger then me she asked herself. That was always on her mind. But they insisted she was a pretty woman, younger then her years indicated, and she was touched and excited by the prospect that two men found her potentially an exciting sexual magnet actually. They had talked her into it. She let herself believe she was, but deep inside she doubted it. She was not a sociably outgoing woman. She didn’t date. She didn’t know any men. The last time, if you want to call it that, that she had sexual relations was six years back, and it wasn’t even that to be honest.

He only felt her body’s tangibles. He only felt her tits, at first from the outside, but then she allowed that man to touch her bra and then to feel the warmth of her crotch. Oh it excited her. She could have let the young man inside them, but she was not experienced. She did not know much better so she only allowed him to feel her warm panties and thick white embroidered bra. Either way it was enjoyable. Either way he enjoyed it too. But he was young, probably much too young for her. But he was nice and a gentleman and that was all that mattered.

The woman, a few years younger then Delores, had recently moved in. Out in the yard she saw Delores and introduced herself. While talking she opened up to Delores, telling her almost everything, and maybe too much about herself. But Delores liked her. She was all that Delores wasn’t. Outgoing, self-assured, and upbeat not that Delores wasn’t a positive woman but she didn’t promote it well enough so the two “hit” it off. They’d talk frequently and in those discussions, Delores learned of the associations her neighbor was connected too. She was envious of her, but in a nice way and wished she belonged to one or two of them too. And soon enough she brought it up to her neighbor so her neighbor invited her to two of them.

One was a woman’s group and topics ran the gamut including meeting men. And that led to another group, a specialty group. That group was a group to meet men, nice men, but men who liked more then relationships and that was the delicate part of it. Not all women were crazy about it, but Delores’ neighbor was. She loved meeting men, she loved meeting women, and she loved developing casual relationships hence she convinced Delores to try it out.

Delores did and immediately was in love with the second group. She liked seeing all the nice, handsome men who fell for all the women. Yes, it was all a matter of men coming up to women, introducing themselves, and striking up conversations, but with a twist…care to have sex sometime in the near future? That was the delicate part and Delores’ neighbor handled it well, but Delores didn’t, not at first she didn’t.

She was neither experienced enough nor was she confident in her social and sexual abilities allowing herself the opportunities. But after the third get together and after seeing him, them that third time round she was “ready.” She wanted to take “it” to the next level. She wanted to gain that confidence and she wanted to learn how to have the best experiences possible.

“So where are they meeting you?” her neighbor asked. “Are they coming here, to your house, or are you going to meet them at a nice hotel?” she said.

Delores hesitantly replied. She said at a hotel. Her neighbor reassured her it would be fun, intimate, and a wonderfully exciting climatic evening. That more then anything for a long time had Delores walking on air, until notice of her impending lay off burst her bubble…she wished that day hadn’t come…until he kissed her and kissed her hard, harder then any man ever kissed her before.

She received the key, parked near that entrance, and carried a small bag with her. They hadn’t arrived and she had time to put on any finishing touches she thought needed. For the first time in her life, thanks to the healthy advice of her neighbor, she felt prettier then ever, sexier then she would have felt if she went it alone, and she thought of her neighbor and how she would proceed with it all.

Then he popped into her head. Why now, why not some other time? Why, why she wondered? She saw his face, she saw his eyes, and she felt his embrace. He was kissing her. It was so arousing, so passionate, and suddenly she wished he was the one. Suddenly she wished he was the one coming to her room to have sex with her. She was beside herself. This wasn’t what she was. Was she prepared to be with these two men? Was she ready to have sex to two men she did not really know all that well? Oh god, I made a mistake. I have to leave…I have to” but then the knock at the door startled her.

She froze, looked at herself in the hotel room’s mirror, but couldn’t move. She was unable to move at all. They knocked again. She turned, looked at the door, and questioned what she was doing. “Delores” she heard, “hello Delores” he called out. He knocked again, but no answer. He called out announcing that it was him. It had begun to drizzle and he let her know so she walked up, opened up the door, and looked at him. He was handsome and looked even younger then the other three times they had been at the social events. Where was his friend, she wondered? He couldn’t make it, the young suitor had explained even though she hadn’t asked. But he did have a huge bag. What was the bad for, she asked herself. She looked at it, he saw her staring, and he wanted to suitably explain it.

“What?” she said comfortably for the timid woman that she was. “You and I will be making love, but on camera?” she said astounded. “Oh no, no…I couldn’t. I couldn’t do that” she told him. He smiled, nodded, and he assured her it would be alright. He assured her she would enjoy making love. He assured he loved foreplay and that was a must when being with a woman.

“But, but how…how…how many women…do you do this with, Jason?” she said. He was always honest, truthful with her. “Ten, ten women, but how…how many times with those ten women?” she asked him. He told her, smiling while responding to her.

He had comforted her. He rubbed her arm, told her how different she looked, and he told her she looked prettier then all the other times they had seen one another. And as he did, he started putting up the three digital recorders he brought with him. They would cover it all. It would take some doing, but he would get her comfortable with him and being on camera. And it did. They conversed, for a long while, but eventually he broke her down and put her at ease and he finally began asking her personal questions.

“May I ask you something of a different nature?” he said. She said yes. “You told me you don’t or haven’t dated in a long time.” She nodded and said yes. “So you haven’t kissed a man for what, several years now?” She nodded and said yes again, but stopped in mid-sentence. That was a lie. She forgot about him. It was a mistake, an accident, and although it was as exciting as hell it was something she wished she could experience again. “Tell me about it.” He could tell. He knew she didn’t tell him the truth and he almost insisted she be truthful. He was gracious as ever and a charming younger man.

“I’d rather not” she said initially. He caressed her arm, put his hand on her lap, and he rubbed it too. She looked down. That felt good. That felt almost emotionally uplifting. “Well, it wasn’t supposed to happen” she said before pausing. “In fact, it was meant to be a bad day, but it turned out to be…to be a wonderful day in the short run?”

“In the short run?” he asked.

She nodded and proceeded to explain what happened when she was called into his office. The guy was impressed. The guy felt it to be a great lead into making a play for her. The guy felt a need to run his hands through her hair and even stroke her cheek if possible. He saw how pretty she was actually. He listened as she explained how he accidentally kissed her lips and how she kissed him back and neither pushed away from the other and before they knew it they were holding each other closely, passionately kissing. She wanted to do that again she had told him.

“Like this” he said as he leaned in and carefully, casually kissed her small tender lips.

She allowed him the pleasure, but the pleasure was hers and she let him kiss them. It felt nice. And she allowed his lips to tenderly cross over hers, feeling them as she went, and pulling them into him, against his lips more and more passionately almost as if it was her and her former boss kissing again. Oh god this was getting better by the moment. Oh keep doing that she thought. Keep on kissing them, kissing me. Don’t stop. And he wouldn’t stop.

He continued, at the same exact pace, kissing her lips while holding her delicately, and pulling at her carefully, thoughtfully. Not too passionately, not too feverishly, but leading her on and leading her astray as if he cared for her and that was exactly what he did.

But she misled him. She tugged at him. Her lips gradually attacked his. She was the one who feverishly, passionately wanted more. She wanted something she wasn’t sure she was prepared to give of herself. She started kissing more ardently. She started pulling at his body. She began doing things she hadn’t realized, yet. But to him, ohhh to him, what she was doing…well it felt great, sexually more exciting, and when she was ready…he would be too. Wow, could this woman kiss. She was becoming almost animalistic. Her hands, slowly, rummaged across his back as she kiss him, pushed him around, and almost pushed him back against the bed. She wanted something, anything so she could unleash whatever inner desires she had caged inside her.

Her breathing grew intense. Her body, chest, and her legs began to seize his body. Her hands fumble recklessly through his hair as her chest and legs feverishly approached his body wanting, groping, and desiring him. All while kissing him, all while holding whatever it was she held dear, and he loved every moment. He loved the foreplay being established. He let her be her. He let her grope him. He let her kiss at her own free will, her own volition. God was she good, god could she kiss…oh wow, oh yes kiss me; do me Delores he almost shouted out. Fuck was she good at this.

But he took over. It was his turn. And he pushed her, shoved her off him, and set her on her back as he quickly lifted off the top she had on. Mmmmm, she was special. An older but slim woman in his grasp, he lifted it and flung it to the floor. He immediately laid his lips against her, kissing her fresh flesh and doing so very lightly making sure he aroused her gracefully. He kissed below them, beneath her covered bosoms, careful not to disturb their elegant beauty quite yet.

But he stopped. He knelt up. He looked into her quiet eyes seeing her uncertainty and he smiled. He reassured her it would be fine. He told her he had no intention of violating her. It was his intention to show respect for her beauty, he gorgeous maturity, and she believed him. What choice did he have?

He removed her slacks exposing her slender and smooth legs, exposing her beautiful underwear as well. She was gorgeous. She never thought she was and when he told her she was he had to reassure her it was true, and several times.

Then he kissed them. He kissed her toes. He kissed each one before kissing her feet. And it continued on up. He kissed this and that and this as he wandered upwards over her slim gorgeous legs. He loved how her flesh felt. He moaned to indicate she was special. He kissed around her hairy vagina, kissed her tummy, and then kissed around her boobs making a point not to touch them yet.

Finally at her neck, he kissed it. Finally at her mouth he kissed it too, but she surprised him. She went nuts and she pushed him over, mounted his body, and she took control of the situation. She was crazed. She wanted to explode, but she kissed his lips forever.

She continued kissing him as her hands explored his upper body. She wanted something he may not have been prepared for. And then she stopped. Straddling him, she looked down on him. She gazed upon him, smiling. He asked her what was wrong.

“Nothing, but when will I get the chance to do things…real things…you know…those womanly things a woman does to a man?” He knew she really hadn’t done them in the past, but gave her the benefit of the doubt. He asked what she meant. “Do you like your cock sucked? Don’t you want to have sex with me? Because I know I want to have sex with you. I know I want to be…to be” and she looked away as she quieted down…”to be fucked by you.” She never could say that word. It was very hard to say it.

He wasn’t sure she was ready, but went ahead anyways and took off his pants as well as the boxers he sported. She stared. He amusingly watched her while she ogled them. Hadn’t she ever seen a man without his clothes on? Hadn’t she ever been in…oh that’s right she really hasn’t not in “full uniform.” He asked her what she felt like doing next, but she didn’t reply. She only looked at it, its form, and its length. My god, he was long. Not thick, but it was long, really long actually.

“Delores?” he said. She didn’t respond. He nestled closer to her, reached behind her, and he undid it. Boy, now talk about perkiness he thought. For a woman closing in on 40, hers were quite astounding. They were fuller, perkier then normal, and engaging. He immediately felt like seizing them, but in a loving manner. He told her she had gorgeous tits. She blushed and turned away, but he quickly took her chin and made her look at him. He smiled, looked at her, and then her breasts. He made her stand up. Whether the recorders would pick this up he didn’t know, but he didn’t care at the moment. She had a fabulous figure. Slim as slim gets, she had wonderfully aligned hips, curving modestly upwards and towards her covenant, her bosoms. He used that phrase as well.

He saw her blush as she turned around to look at him. Was he just saying that? It had made her hornier. She really wanted him more then she expected. And that’s when he suggested she feel him, feel his organ. He wanted to see how gently she would hold it. He knew she would do it in a non-aggressive manner and he was right on the mark.

She held it, outside of his boxers, and her fingers fiddled with the limpness. It turned her on more. She moaned. It was a long desiring moan. He took her hand, carefully, and he eased it, slowly, cautiously down towards his floppy appendage. Oh shit that felt awesome. Ohhh grab me harder he tried showing her. His hand was on her hand. He clamped down on hers indicating it. Ohhh god harder he had told her. Harder Delores, harder he said as calmly as possible, but he was giving out. He was giving in.

He wanted her to get down on her knees, put those humble but sexy lips on his floppy penis. Make it harder, firmer, and longer. See its manliness. He was horny.

He was as aroused as he could ever be, but he didn’t want to get hard without her getting him that way. He wanted her to do it. He wanted her to feel like the woman she could be. He wanted her to feel sexy and assured and hornier then she ever had been in her life.

“Put your lips on it” he exclaimed. “Delores, please put your lips over it” he begged her.

And she did. Where her confidence or desire or whatever it was came from she pulled herself closer and she squealed a heightened squeal as if never feeling the euphoric emotions she felt at that moment. But her lips remained on it. She was a natural. She felt it, began sucking it too, and before either knew it the hardening cock was inside her mouth. She was sucking it as if it was a pacifier. Sucking and pulling at it as if it might explode at any moment. He was almost pushing it towards her. Oh god, oh shit she was good. Yeah oh yeah she’s good.

“Wow…oh wow, Delores that is…oh wow you are soooo good” he exclaimed. He pulled her up. Pulled her nakedness against his and he kissed her lips. He smashed her sexy bosoms against his chest, kissing her and hugging her and…and…and she spoke up.

“Fuck me…oh god I want you cock inside me. I want it now, now” she demanded.

He didn’t hesitate. They were on the bed, her legs were spread out, and she fucked him as though that day was the last day on earth. Her legs were spread out, mounted against his shoulders, and his cock was implanted inside her swollen pussy as the two fucked passionately. She screamed and kept asking for it more and more. He kept plunging her cunt and she loved it, loved this man for making her feel whole. He made her orgasm. He made her feel as if she was a real woman. And he made her feel complete.

She came from this experience an entirely different woman, a fulfilled woman, a whole woman. She was proud of herself, proud of her accomplishment. The forced passion she had throughout it had made her want him again. He told her she came out smelling like roses. He told her he was impressed by her and that she was as sexy as any woman he knew. He told her she was more then capable of women she didn’t think she was as sexy as. “And it really doesn’t matter. You find a man you like… and if you two feel like it’s right… then just do it.”

He kissed her, said goodbye, and later on sent her copies of how good she was in bed. She watched it maybe two dozen times. But the following morning after waking up, Delores was all smiles. She looked at her email she originally typed to her former boss. She made a few revisions to it and smiled. She sent it to him. He read his email later that day. By late Saturday afternoon, she was at his office.

She had him in a hold he didn’t relinquish. Her lips and his lips were against one another’s while her hand was rubbing his crotch passionately. She brought it into a hardened state and there clothes were off in minutes by that point. Wow was she good or what he told himself afterward.

“I want to do this again” she told him “but you have to hire me back first” she insisted as they cuddled on his office couch.

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