Anything for Him: at Work

So what that meant on the third Monday was that she was half crazed with thinking about a way to get him to use her asshole. She'd been using the dildo on her asshole at home since a couple of days after that first meeting. And on that endlessly long weekend without him, she found herself using it more times than she could count, each time imagining that it was his cock and that he was groaning in pleasure behind her. By the end of the weekend she could almost bring herself to orgasm with just that asshole dildo and without even touching her pussy. She just knew—it was amazing, but she really was sure of it—that if she actually had his cock in her ass she would come like a volcano.

So when she received the Monday morning text that she was waiting for, it wasn't just her mouth that began to water with anticipation. Her tight little butthole began twitching and quivering, too—she'd never felt anything remotely like it before—and in an impulsive moment, just before she got out of her car to go in and wait for him in the supply closet, she took out the jar of lube that she had brought with her, put a generous dollop on her index finger, and then slid that finger several times in and out of her ass. He had told her to be there 30 minutes earlier than their 8:00 usual, and she hoped that meant that he had missed her over the weekend and was going to spend an especially long time with her, time enough to use her twice.

As usual, she waited for him on her knees, and when he came in just walked over to her to be unzipped and serviced. She pulled down his pants—sometimes he just had her bring his cock out of his boxer shorts, but she liked it best when she could get at his balls and butt, too, licking at the balls and stroking and kneading his ass cheeks to pull him deeper into her mouth. This morning she had full and glorious access to him, and she quickly got to work doing what she always did, which was to make this blow job the best and most loving one ever. The fact that her asshole was on fire with hopeful anticipation must have helped her to do that, because if anything he came even more and even harder than usual, groaning loudly—the basement supply closet was good for that because they didn't have to worry about being overheard—and then thrilling her with unusually explicit praise and a new request. "That was wonderful, Jane. Keep sucking because I want to stay in your mouth for a bit longer. Let's see how fast you can make me hard again."

She went joyfully back to work on his cock, more gently now because she knew how sensitive it must be after that first big climax. She rolled it around in her mouth, humming and purring and savoring the thick, heavy semi-hardness of it, which permitted her to hold it all in comfortably, in a way that she never could when it was really hard. After a few minutes, she dared to lift her mouth off of his cock for a moment and to begin nuzzling and licking at his balls, while she held his cock gently in her hand. And then—she hadn't known in advance that she was going to do this—she arched her back to slide under him and to begin working her tongue towards his asshole. He laughed quietly and rewarded her for her daring: "What a nice idea, Jane. Let me just get a bit more comfortable." And then he took a few steps back, and sat down on an old armchair—it must have been the place where the custodian took his coffee breaks—slipping off his pants completely as he leaned back into it. At that point, Jane almost dove forward, wrapping her hand around his knees, from the inside out, and lifting up his legs to drape them over her shoulders and to open a path to his waiting asshole. She plunged her tongue eagerly into it, lapping round and round, teasing and lapping both at the tight hole itself and at all the sensitive tissues right around it. She'd never even considered doing this to another man, but she took to it eagerly, thrilled to have a new gift to offer him, thrilled to taste and worship him in this new way. And doubly thrilled when she reached her hand up to begin caressing his cock again and she found it rigidly at attention, as hard as she'd ever felt it. She worked his asshole with her tongue for as long as he would let her, careful not to let her hand's movements on his cock turn into anything that would make him come before he was ready—or before he was inside her. After five or six wonderful minutes of rimming his ass, she heard him speak her name in his usual voice of quiet command, and she instantly stopped to be ready for his next instruction. There was a padded bench of some kind in the other corner of the supply closet, and he gestured for her to get over there and bend herself over it. They hadn't used the bench before, so she wasn't sure just what to do, but she quickly saw that it was low enough for her to stand flat with her legs spread wide and then to reach all the way around it to grasp her own ankles. Her loose dress was flipped almost over her head, and her pussy and asshole were completely open and exposed. She could only imagine what a picture she must make.

Thinking of that picture, she did everything she could to call his attention to her asshole, sliding her butt back and forward the few inches that she could move it, and at the same time clenching and unclenching her asshole so that he couldn't help seeing how ready it was to open for his cock and then to close tightly over it. It seemed to be working, too, because as soon as he walked over to her she felt his hand reach out to stroke her butt cheeks and then kind of circle in towards her asshole. "It looks like there's something that you want, Jane." He was rubbing his finger over her asshole as he spoke, kind of teasing her with both his voice and his finger. "In fact, it looks as if this glistening little asshole has been all prepared for me with some nice slippery lubricant." He was working his finger in and out of her butt as he spoke, and she was shuddering with pleasure and anticipation, sure that she was about to get the ass-fucking that she craved so badly.

But what happened next was a shock, a terrible disappointment—but also the beginning of another, incredibly exciting phase of this very special relationship. He took his finger out of her asshole and walked around to the other side of the bench, where her head was hanging down. And then he spoke to her in a new tone that she hadn't heard before—not angry, exactly, but hard and clear and strong, a voice that penetrated her as deeply as his cock ever had. "Lift up your head, Jane; you need to hear this." She took her hands from her ankles and struggled to a kind of half-standing position, still draped over the bench with her bare ass exposed, but lifted up on her elbows so that her head was at the level of his cock, which he was handling and stroking very slowly just out of reach of her mouth. "I think we need to understand each other a little better, Jane. You've been lovely so far—really you have—but it's time to firm a few things up and make some small changes to this arrangement." His talk of "firming up" seemed almost like a teasing reference to his incredibly firm cock, which he was jacking slowly back and forth as he spoke, causing little droplets of come to begin forming at the tip, just five or six inches from Jane's face.

"First of all, it was a little presumptuous of you to put that lube in your ass. Maybe I'll want your asshole lubed up when I fuck it, and maybe I won't. Second, it looks like you need a new way to tell me about things that you want me to do to you. I'll do what I want, of course; that's the only way this relationship works—but I'm interested in what you want, too. Who knows? Maybe you'll come up with some things I haven't thought of. So from now on, this is what you're going to do. You're going to write a letter for me every night, telling me what you hope that I'll do to you in the course of the next day. It doesn't have to be very long, but it should be very explicit. Then you'll print out that letter and leave it for me on my desk the next morning. Don't put it in an envelope, just leave it on the desk. Don't use my name—I wouldn't want to be embarrassed or incriminated if these letters went astray somehow—but just address me in the letter in the way that seems right to you. Oh, and one more thing. You should sign your own name, first and last, to show me that you're fully committed to what you're requesting."

Jane couldn't believe what she was hearing. She also couldn't believe how excited it made her to hear these instructions and to know that he was talking about their relationship as if it was going to last for a long time. It was scary to realize that she'd be signing her name to those letters—she never considered for an instant not following his orders—but she loved exposing herself to him, and this was just another kind of complete and trusting exposure. Her mind was racing excitedly as he went on, and she felt almost consoled for the deep emptiness in her asshole where she had wanted his cock so badly.

"Third," he said, "we need to finish up this morning's encounter, so here's how that's going to go. My hard-on is almost painful"—he was still stroking it as he spoke, a little faster now—" but because of your error I'm not going to be relieving myself in one of your holes." Jane struggled to choke back her little whimper of disappointment. "Instead, I'm going to jack myself off right here in front of you and shoot my load here"—he pointed to the leather covering of the bench that she was bent over—"and maybe on the floor, too, while you watch me. Then I'll leave but you'll stay behind for several minutes to clean up every drop of my come—I think you know how to do that, don't you?" Jane quickly nodded her understanding. "And then, after you're sure that you've done a thorough job, stay waiting here, on all fours, with that shiny little asshole lifted up high, while you count slowly to 200 and think about everything I've said. Then you can come upstairs to your office and begin your letter. Oh, and one more thing. Let's get you completely naked for this exercise. I'd like to take a better look at you while I jerk off."

Jane stood quickly and lifted her dress over her head and handed it to him. She had no panties of course, but she was wearing a bra—a sexy push-up one so she hoped it would be ok—and she tore that off, too, leaving herself completely naked. He signaled her to remain standing for a minute, looking her up and down with close attention—and, she hoped, with approval. His cock was harder than ever, standing straight up now against his stomach, so that seemed like a very good sign. With just a glance, he signaled her to kneel down at the bench again, and he began to stroke his cock more regularly, so close to Jane's face that she could have craned her head forward to lick it, but she knew better than to try that. His voice was husky with desire now as he stroked his cock and told her, "Speak now, Jane, and let me know that you understand me."

She wasn't even sure what she said, but she told him again and again, in a low urgent moaning voice, that she understood him completely, that she would do everything that he said, that she was so sorry about anticipating his wishes and putting the lubricant in her asshole, that she was eager to go upstairs and write him a letter and tell him more and more about what she wanted to do for him. He wasn't looking at her anymore, but he was listening to her as she went on, and in another two or three minutes he let out one of the deep groans that she already knew so well and loved so much, and his come began to splash out in several big, steady spurts, landing mostly on the padded bench cover but also dripping down its sides and onto the floor. She watched each jet of come as it shot out of the tip of his cock—it was like it was all in slow motion, somehow—and she noticed the special rhythm that he used, stopping and starting, alternating fast and slow, as he squeezed the maximum pleasure out of his orgasm, down to the last creamy drop of come. And then he held out his hand to her—she wasn't sure why until she noticed that there was some come on his fingers, which she slurped up eagerly.

And then he put his pants back on and left the room, taking her dress and bra with him, she noticed. "I'll leave these just outside," he said, and then he was gone. Jane went immediately to work, carefully licking every pool and drop of come off the top and sides of the bench, going over the major spots twice and three times to be sure that none of it was wasted, then finally pressing her face to the floor—which wasn't as dirty as she expected, though she noticed with surprise that it really didn't matter to her whether the floor was dirty or not. His come was on the floor, and his instructions had been clear, and she followed them unhesitatingly.

When she was sure that she had done a thorough job—and she didn't hurry at all even though a part of her mind was wondering nervously when the custodian would be arriving for the next shift—she arranged herself on all fours, face and lips down at the spot where she had found his last bit of come, ass lifted high and with her knees far enough apart to open her ass and pussy fully to view. She counted slowly to 200, then waited and counted to 50 again just in case she had been rushing in her excitement. Then she stood up in a daze, noticing as if for the first time that she was fully naked, in an unlocked room at her place of work. She picked up her shoes and opened the door carefully, peeking around it to see that the hallway was still deserted and that her dress—but not her bra—was lying on the floor a few feet from the door. She stole out to pick it up, but then caught and corrected herself, standing at full height and unembarrassed in the empty but public hallway. She waited another few seconds to make sure that really felt and appreciated the degree of her exposure and her obedience to his instructions. Then she slipped her dress over head and went upstairs to her office. It was a little after 8:20.

When she got to her desk she opened up her word processor and began to type her letter of the day. She hesitated a little at the opening. She knew what she wanted to type. She wanted to type, "Dear Master," because she felt so thoroughly and completely submissive to him. But after her mistaken presumption of the morning, she intuitively knew that that would be a mistake and that it was up to him to decide and to tell her if she was his slave, and if that was the form that he wanted to give this relationship. She was going to do everything he said as eagerly and unquestioningly as the sex slaves that she had read about; and she was going to submit to his every wish. But she knew now that he wouldn't wish her to take that big step on her own, so "Dear Master" was out. She settled on "Dear Sir," which seemed both businesslike—this was all happening at the office, after all—and very clearly and fully submissive.

After that, the letter just flowed, and she told him that she hoped very much that she would be sucking his cock again that day, that it would especially please her to be able to lick his asshole again since he had seemed to enjoy that so much, and that, although she understood completely that it was up to him if and when to use her ass, she was most excited by the thought of having him in her asshole. She told him that she was almost an asshole virgin, that there had just been one insignificant and un-memorable previous experience. She told him that he had been working on her ass with a small dildo, much smaller than his cock because she wanted to keep her asshole super-tight for him. And she told him that even though she was nervous that it might hurt to take him up her ass, the discomfort meant nothing compared to the pleasure that she hoped it would give him and that she knew it would give her. She didn't tell him how sure she was that she would come when he butt-fucked her—she didn't know if that was important to him or not. And then she added, thinking back to her morning mistake again, that she was going to leave work as soon as possible and purchase an enema at the closest drugstore so that she could be sure her asshole was clean and lubrication-free for him, as it would be from now until whenever he decided, if he decided, that he wanted to use it. Then she dated the letter and with a small thrill at the new line that she was crossing, she both typed and signed her name at the bottom. She was at his office a few seconds later, where he was on the phone taking care of some business or other. He didn't even look up as she walked in, laid the letter carefully on his desk, and went out.

After taking care of some other necessary business, she left almost immediately for the drugstore, rushing to be ready for his next message, rushing to make sure that her asshole would meet with his approval if and when he next wanted it. She was a little bit scared to think what it would be like to take him up the ass without any lube if that's what he wanted; but she was really scared to think that she might have missed her opportunity and that she might not be using her ass at all. As it turned out, she didn't need to worry about anything.

At 10:15, she was in a stall in the lady's room administering a portable enema to herself and relishing the feeling of the warm liquid coursing into her asshole. Why had she never noticed before how good it felt to have your asshole filled up? She wasn't going to worry about it now, but just enjoy this whole new category of pleasures. And boy did she enjoy them. At 10:30 she got a text from him that just said "My office." She was there in about 30 seconds, and within 30 seconds after that he had locked the door behind her—a first—and gestured to her to remove her dress so that she would be completely naked—also a first for his office. In a flash, she was standing there before him, legs slightly spread—he hadn't said anything but it just felt right—shoulders back to display her nice, well-shaped tits which sagged against her frame just enough to prove that they were real. Her nipples were rigid with excitement, especially after he took them appraisingly between his thumb and forefinger stroking and flicking at them gently. She was looking down, of course; she could never really meet his gaze and now more than ever it seemed right not to try. But even with her eyes down she could feel the intensity of his gaze, and she thought she could feel that he liked what he saw. Certainly, his cock seemed to like it, and as he passed in front of her downcast gaze while he circled and inspected her, she saw with a little spasm of satisfaction that he was hardening again in his pants.

He left her standing there in the middle of the room and sat back at his desk. "Jane, I just don't know what I'm going to do with you." She would have been worried if it weren't for the tone of his voice, which was almost playful now, more intimate somehow than it had been before. "You're really causing me problems. I came twice this morning, and that should have gotten me through to lunch time at least. But here I am, uncomfortably hard again, and hardly able to concentrate on my work at all after reading that letter of yours—and after thinking all morning about that shiny little asshole. You're creating some significant scheduling difficulties for me, but I think I can manage them. Anyway, I'm going to have to come again now, and given that this will be the third climax in two hours, it's probably going to take me a while. And I'm probably going to have to fuck you very, very hard to get off. I just have to decide where." Jane's knees were buckling and she was afraid that she was going to faint. Fortunately, the next thing he said was, "Come over here and suck my cock for a few minutes, while I decide where I'm going to leave this next load." Partly because she was so weak-headed, partly because it felt so right, Jane dropped to her knees where she was standing, and then crawled to him on all fours, dropping her head almost to the ground as she approached him, feeling her bare, tender nipples grazing against the carpet. And then she lifted up and took him into her mouth. His powers of recovery really were amazing—his cock was as hard as if he hadn't come in weeks, and she had to keep pushing and pushing to hold it in her mouth, working her tongue rapidly at the same time. She loved having it in her mouth as much as ever, but both her pussy and asshole were on fire now, from all the dizzying events of the morning, and from that enema, and from the thrill of what he had just said to her about a hard, hard fuck.