The Trial Week

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

He tried to avoid her clit because he did not want to give her so much pleasure at this point, he already knew he had turned her on. He ran his fingers back and forth over her dripping wet slit and then removed his hand from between her legs. All of a sudden in front of her face she saw his fingers, "open" he said, his face was still not giving anything away as to how turned on he was or how much he was enjoying this, but she was going to do whatever he said; so she opened her mouth and he put them inside.

She enveloped her lips around his fingers as she tasted herself on them. She started to lick his fingers seductively, sucking on them and showing off to him what her mouth could do. He continued to keep a straight face, but he could feel pre-cum escaping from his rock hard dick. Then he pulled his fingers out of her mouth and coughed a little, trying to disguise to her how hard it was for him not to bend her over the desk and fuck her right there and then, she was wet enough for him to slide right in to her pussy but he wanted to make her wait and to make himself even more ravenous for her.

He went back around to the other side of his desk, and asked her to sit back down, he was impressed with his own will power at this point. She could feel the warmth of her pussy juices on her body as she sat, she was dripping wet for him. He opened the drawer and got out a toy, placing it on the desk in front of them. She was not expecting that and was a bit disappointed because she really wanted a fuck; it had been so long since he was inside her and they had been building up to this for so long with their sexy messages, so why couldn't she just have him?

The toy was pink, and looked like a U shape. He told her that she was to wear it at all times, for the whole trial week. She stared at him in disbelief, and nodded. He told her to put it on now, and not to take it off. She picked it up, looked at it and worked out that one side of the U would be in her pussy, next to her g-spot and the other would be outside of her pussy, resting on her clit. He told her not to touch any of the controls. She stood up next to her chair, and although she was not getting his dick, she decided to make him watch the toy going inside her and wanted him to know how aroused she was. She placed a foot on to her chair, and pulled her skirt up to reveal her wet pussy, which he saw was glistening against the lights in his office. She looked at him and saw he was just staring at her crotch. She was so wet, she could have put it in so quickly. But no, she wanted to encapsulate him and tease him.

She rubbed it up and down her slit, slowly before letting out a gasp as she inserted the vibe into her pussy. His eyes were fixated on it and he wanted to see more. He was jealous that it was the vibrator going inside her and not his dick. Once the vibe was in, the front part which would sit on her clit needed to be helped into position. She started to use both hands, as she gently rubbed on her clit, back and forth, with the head of the vibrator. She could feel it was swollen and it was hard not to keep rubbing and bring herself to orgasm.

She thought he would stop her soon because he would know that she did not need to rub herself to put the vibe on. Now she had to grip the U shape so it stayed in place. As she clamped her fingers around it, she let out a yelp because of the pressure on her already aroused g-spot and swollen clit. All she wanted to do was to be fucked by his large and girthy cock, but if this is what she needed to do to impress him all week and get the job, then so be it.

All of this was making him so horny, he needed to get her out of his office so that he could massage his dick and cum. He told her to be back at the branch between 9am - 6pm each day for the next week. He ordered her to wear that skirt and top to work every day, with no underwear. She nodded and said "yes, Sir". She was feeling full from the toy inside her but was excited to turn up for work in the morning. When she left, he sat back in his office chair and he got his throbbing dick out, stroking it up and down; thinking about what had just happened in his office before having an intense orgasm and cumming everywhere.

She had gone back home and had slept in the toy all night. It had been rubbing on her clit as she was moving around in her bed, and while getting ready for the day, making her so sensitive. She was getting her top and skirt on ready for her shift. She felt sexy, especially with no panties on and no bra, but also nervous as she had not met anyone from the branch apart from her ex. She walked in and was greeted by someone else, she couldn't see her ex anywhere, but in that moment she decided not to tell anyone that she knew the manager personally. It had been well over a decade since they were together, so none of the staff were aware of her and she did not wanted to be treated any differently.

She was told that her uniform was yet to come in, so the manager had requested she wore what she had on. Of course he did, she thought to herself with a smile...this is something he had already requested personally. She was standing by the customer service desk, and shadowing another staff member, when she suddenly jumped. The toy inside her had vibrated.

What?! How was it going off? She hadn't touched any of the controls? It stopped and then started again. "Are you okay?" questioned the other member of staff. She reassured them that she was fine. She hoped that they hadn't heard the toy go off but realised very quickly that he had the control. From that moment, throughout the day he would flick it on and then off. She was finding it so hard to concentrate on her newly learned tasks and talking to customers was so difficult when she stuttered over her words if it happened to go off while they were right there in front of her. He was reminding her that the toy was very much there and that he was most definitely the boss.

He was enjoying every moment, watching her on the CCTV and seeing her suffering, knowing that she was getting more and more built up and frustrated every time he flicked it on, sending vibrations all over her pussy. However, he had felt pangs of jealousy too, because while wearing the sexy skirt and top everyday; she was getting some attention from the other males who worked alongside her. He wanted her to himself, she was his submissive; he thought.

The males were doing their best to chat to her, get to know her and of course, flirt with her and she was allowing it. She wanted to wind him up and despite being under his control, she wanted to make him wild for her. She would laugh loudly at their jokes, being tactile with her hands and of course, sweet. She acted so innocently and really she knew that she was nothing but guilty...guilty of wanting to fuck the boss. He occasionally heard her high pitched flirty laugh, or saw her gently touch the other males and at those points he would let her know that he was getting restless for her.

He would come out of his back office and his face would be stern, like she needed to be punished. She immediately stopped flirting and her eyes were on him. She couldn't help but touch him in some way; she would brush past him at any opportunity but always keeping a straight face. Each time she did, she felt his hard dick against her body and knew that he was only teasing himself more by coming out on to the branch floor. He remained calm and acted normally, making this even more naughty because no one else knew what was going on except them.

Wearing the toy was taking its toll on her. She was in a pre-orgasmic state all of the time and all she could think about was cumming. Why wasn't he letting her cum? She never knew when her pussy would feel the intense vibrations and for how long for. Every time they came on, she would try and make an excuse to leave the branch floor just in case this was the time that made her climax, so she could enjoy it completely. It was like she was living on the edge of orgasm and she secretly loved it, being submissive to him and knowing she would only get what she wanted if she let him have full control. It turned her on just as much as the vibrations.

She had made it to the end of the week, her last trial day was tomorrow. She decided that she needed to make sure she had made a good impression. She went to his office door at the end of the day and knocked on it, cautiously. "Come in", he said with his deep and totally captivating voice. She entered the office and saw that he was sat alone. He looked up at her over the top of his computer screen. She said "Hello, erm, as tomorrow is my last day I was wondering if you wanted me to stay a little later to help with the customer database?". He smiled. "We could always do with more help. Report to my office at the end of the day tomorrow and I'll show you how you can help me".

She smiled and turned around, then walked slowly out of his office. She walked out to her car and as she did, she felt those intense vibrations of the toy inside her. She had stopped still for a bit to enjoy the sensation on her swollen clit and throbbing g-spot. This was so good. She thought he would stop the vibrations soon because he seemed to not allow her to cum. But this time they didn't stop. She quickly realised how close she was to cumming all over her toy and ran to her car, opening it and jumping into the driver's seat so she could orgasm without anyone noticing.

Oh wow! Those intense but short vibrations turned into long pulses and then to a continuous vibration which took her breath away. She was closing her eyes and holding on to the steering wheel; then the feeling overtook her and she lost all composure, letting out a satisfying moan. She felt that warm feeling starting in her clit which radiated over her pussy and then she felt her pussy contracting on her toy. The release was immense and she was filled with pleasure in that moment.

She was trying to calm her breathing but it wouldn't slow because he hadn't stopped the vibrations. With the toy still on at full speed, she wondered what was happening. She was dripping wet as the cum had started leaking from her pussy making her feel like such a dirty slut. She looked around at the empty carpark, her eyes darting in every direction to catch a possible glimpse of him. She thought he might be watching from somewhere, because he was bound to know exactly what he was doing to her.

There was no sign of him - she became even more flustered as she was desperate at this point to beg him to stop the toy. Her pussy was now so sensitive and the sensation was starting to overwhelm her. She felt herself build up again....tingling all over, her pussy becoming warm; she wanted to rip the toy off but she also wanted to obey his orders. Fuck. She couldn't help it, she was cumming again! This time she tipped her head back on to the headrest, arching her back with the intensity and moaned loudly as she gasped for air; her breathing was still fast and deep. It was too much. Then the pleasure hit her in a huge wave-like release and it was amazing. She had never felt an orgasm like it, she was totally satisfied.

Finally, the toy stopped vibrating and her body started to relax. She could still feel the occasional pulse as her throbbing pussy clenched the toy while coming down from the orgasm. She wondered if he knew what he had just done to her. She took the opportunity to drive home as quickly as she could to shower herself and get ready for the last day of her trial, where she had already asked to stay late to help.

The next day, she walked into the branch wearing the same outfit. But she had freshly shaved her pussy for her ex, just in case he wanted to examine her again. He was in early and had made sure he was trimmed for her, too. He knew that they would be alone at the end of the day and he was excited. The end of the day came and she decided to get dressed into another outfit. The one she had been wearing all week at his request was feeling a bit, erm, samey. So she wanted to switch it up.

She waited until everyone had gone home and then locked the doors from the inside. She got into some stockings and suspenders, with a little lace apron on top. The lace apron was white and see through, and had a black satin ribbon to secure it behind her back. Her breasts were visible through it and so was her pussy. The dark outline of her nipples was showing as they hardened due to the cold air conditioning. The apron ended just below the pink toy which was still inside her. She added a pair of black heels to complete her look and admired herself in the mirror. A little slut maid, she thought. She was excited to report to her boss.

She walked through the branch and into his office, holding the handle of his door and then swinging it open, she saw him sat in his chair. He was relaxed back in it, but he had his trousers undone and his large girthy cock was out and hard in his hand. He was stroking it and looked up in shock when she walked in to find him enjoying himself.

She wasn't sure if he was shocked because she had caught him playing or if he was shocked at what she was wearing. She knew he had a thing for stockings and suspenders and the whole maid outfit probably topped him over the edge. His shocked face turned into a smile and he continued to stroke his dick.

She walked up to his desk slowly, their eyes locked on to each other while she got closer. She then got to his desk and placed both hands on it's wooden top, leaning over it. She then stared at him as if to say "come and have a look at this". He stopped playing, and he opened the drawer beside him. He said "Stay still" to her as he got up, his dick still hard and hanging out of his trousers - she did not move but her eyes were fixed on his erect cock, it was so appetising to her; she wanted to take it all in her mouth.

She was ready for an examination. What she didn't expect was what he would get out of the drawer. He pulled out a metal butt plug and her eyes widened in anticipation. She remained still like he had asked her to be, but she was getting nervous. He walked around so he could see her from behind. In this little maid apron, he had very easy access and could do whatever he wanted. He started by putting a hand on her arse cheek and gently rubbing it.

He then got some lube out and added it to the plug before pushing her back down so that the side of her face was flat against his desk. This meant her arse opened for him and he could see her tiny hole, ready to take the plug. He inserted the plug slowly and she gasped. He loved watching her arse take it in and once it was fully inside her, he asked her to stand up. He went back around to the other side of his desk and she could see that his dick was still rock hard. She was now wearing the vibe in her pussy and a plug in her arse. Perfect. She loved feeling so full and really wanted him to let her suck on his cock just to make sure every hole was filled.

He told her that the branch reception really needed a good clean, and said that he would be out to inspect her work soon. He gave her a little feather duster to use and she gave him a cheeky smile when she took hold of it. He went back and sat down, just caressing himself gently and watching her walk out of his office in that sexy outfit. He was thinking about how good she looked and how much he wanted to just grab her and fuck her. He was totally smitten for her in those stockings and suspenders, too. He knew he was already taken but he could not resist the temptation of her.

He kept turning the toy on and off again while she was busy cleaning, just to tease her. She was enjoying it and it felt so slutty; she loved being the maid. He waited a little longer and then he went to get her. He could see her reaching up high and just exposing the edges of her arse cheeks as she did, then bending down low, crouching in her heels and giving such a naughty view of her just ready to be fucked, he could see the toy and the plug from that angle and at this point he just wanted to make her scream his name.

He coughed a little to let her know he was watching. She looked around and then stopped, stood and said "Hello Sir, have you come to inspect my work?". He could see that she had actually cleaned for him and it was better than before, but he told her that she hadn't done a good job. "You've missed several areas...I think you need to be punished; come over here right away". His voice was stern but so deep and enchanting. She loved the sound of his voice and she could listen to it all day.

She walked over very shyly and he pulled something out of his pocket. "Show me your wrists, palms down". She showed her wrists wondering what would happen next. He then revealed some rope he had rolled up and proceeded to tie her wrists together with it. She really enjoyed this as he did it so gently and with such care that she felt closer than ever to him. He completed his knot and led her back into his office. She was excited as to what would come next.

He stopped next to a wall. He pointed to the hook on the wall. She had seen it previously but had thought nothing of it. But this time, he pushed her towards it and she was face to face with the wall as he lifted her hands up and the rope caught onto the hook, with a hand either side. She stood there in her heels and she could feel that she was becoming aroused. Her heart rate was climbing, but she didn't know what to expect so her excitement was combined with a tiny bit of fear which made her even more horny.

He decided he wanted to take full advantage of her, so he took off her heels and her whole body dropped. She felt her arms all stretched out because of the height of the hook; with no heels on, she was only just able to stand on her tip toes. She decided to stay as still as she could, as she could only just touch the floor. She realised very quickly that she was helpless to him and he could do whatever he wanted with her, while she was suspended there and she could not do anything to stop him.

Just being there and ready for him to take advantage of her made her want him so much, she was his slave in this moment and she loved it. She was yearning to please him with her body and she wanted him to use it in whatever way he needed. He could see everything and he was enjoying the view. He loved her body and he especially loved all the toys he had made her wear because she was submissive to him and he had all the control.

Just as she was getting used to the hook, he turned her toy on again, up to full power straight away. She flinched and let out a small yelp, nearly losing her footing. But she loved those vibrations and had learned from the week long trial that they could send her into a blissful state very quickly. Enjoying the toy, she started to feel herself building up to an orgasm. He could not help himself but make sure she knew he was the boss; so he got out a paddle out of his drawer and started whacking her naked arse with it. She went wild for that and started to make louder moans of pleasure. Her arse was turning red, and moments later she was cumming so hard right in front of him, all over her little toy. He watched as her body shook while being held up by the hook and rope. His dick was as hard as rock now and was ready for what he was about to do next.

He pulled the butt plug out of her tiny hole, and he saw that her arse had now been stretched a little, so it would be easier for him to get inside. He still had the toy on fully and she felt just like last time when the vibrations were left on, she was over sensitive but building back up ready to orgasm again. He then moved closer towards her body and took both legs, wrapping them around his body to allow his dick to push into her already stretched arse. He held her legs while he fucked her so hard, and all she could do was hang there and take it.