He sat back in his chair breathing heavily while she was still quivering on his desk from the aftershocks of orgasm. He wiped his chin and looked at her still sitting on his desk with her hands cuffed behind her, legs held wide by a spreader bar and pussy dripping. It was the least he could do after the 30 minute blow job she gave him. Feeling mostly dry he reached down and tucked his cock back into his pants and zipped them up then pulled out a box of wipes from his drawer and set them beside her. This motion seemed to draw her back to reality and she pulled a handcuff key from somewhere and set about unlocking herself. It wasn't the first time he'd returned from his end of the week debrief to find her horny and restrained in some way waiting for him. He wasn't sure what he'd done to encourage such action from his new assistant but he somehow found that the combination of an incredibly sexy 20 something cuffed and on her knees begging him to let her suck his cock hard to resist. He'd never been unfaithful to his wife before, in fact he was very happily married as his wife had an above average sex drive and was easily the more adventurous one. Still he was enjoying this weekly treat from his assistant and she also seemed to get something out of it and since he still got home at a reasonable time his wife never suspected. But it was times like this when he wasn't sure what to do. Should he leave while she was still unlocking herself and cleaning up or should he wait for her? Should he offer to help? She didn't seem to need it. She thankfully noticed his awkwardness and smiled. "So, any plans for this weekend?" He smiled, "Yeah I'm thinking of taking Janet down to Charleston and watch Clemson smash CSU on Saturday. Then enjoy some of the amazing food down there." "You really think Clemson will smash CSU?" "That's right! You went to school there didn't you? Well sorry to say but yeah Clemson is going to win by 30 or 40." "Want to place a little wager on that?" He always enjoyed sports betting so this more than got his attention. "What did you have in mind?" "How about if Clemson wins by 35 or more, I'll wear handcuffs all week next week (don't worry I'll be discrete if anyone comes to visit and I won't be any less productive) but if they don't then you have to let me tie you up for once? I'll let you pick when but it has to be next week sometime." "That's ... not the type of wager I'm used to..." "Well what if the number was 25?" "That's...tempting but..." "Oh come on. Do you doubt your team or is it that you don't think it's an even bet?" He chewed his lower lip considering. He'd never been faced with this type of wager and the thought of her working in handcuffs was an odd one. "Okay fine 20 and if you win I'll wear handcuffs and give you the keys and be naked from the waist down whenever I'm in your office, and that's practically all day, for a whole week!" She looked at him hungrily and the bulge in his pants answered her before he ever said a word. It was an offer he couldn't refuse. Clemson 29 - CSU 14 He was shaking as he entered the office on Monday. He had not slept well as all he could think about was being helpless before her. He was terrified and at the same time a part of him was amazingly turned on by the idea and he'd been moderately to exceedingly aroused all morning. She was waiting for him standing in front of her desk and he couldn't help noticing she was wearing pants and her hands were free on either side of her as she leaned back on her desk. She stood up to greet him and he noticed a CSU cheerleader top being worn under her suit jacket and her hair was pulled back in a blue and white ribbon. She was stunning. "I guess you might have heard how the game ended? I was hoping you might not have known." She arched an eyebrow at him. "Really?" He blushed. "No. Not really." She smiled wolfishly, "So you wanna do this now and get it over with?" "I think you know my schedule this morning and know that isn't exactly the best idea..." "Oh I could reschedule every meeting you thought you had today..." "I..." He laughed nervously at that because she was probably telling the truth and the idea was more than a little tempting. "I told Janet I'd be working on a project this evening so we should have some time after meetings are done for the day." "I can wait if you can. Just remember..." she reached out and tapped his hard and bulging cock. "...no sneaking off to the restroom and taking things into your own hands. I want everything you got." Then she walked to her desk chair and sat down and got to work. He almost told her to cancel all his meetings because he wasn't sure he could wait 8 more hours but eventually went to his desk and grabbed the folders he needed for his first meeting. As he walked back past her desk he noticed a set of leather wrist and ankle cuffs sitting on the corner of the desk and he almost dropped his folders. She pretended not to notice and he left. He did all he could to not be in his office all day. Every time he did enter there would be another restraint on the desk. At one point she had removed her suit coat and was just in her cheerleader top which did an excellent job of highlighting her generous chest. She never said a word to him except to tell him his 3:30 meeting had been switched to a virtual one. She told him this as he was walking out to the conference room for that very meeting and before he could suggest anything different she let him know that the meeting was already waiting for him on his desktop there in the office. She shut the door and he sat down with fear in his eyes. The meeting started as soon as he sat down and he thankfully lost himself in caring for his client. That lasted all of 10 minutes though as his assistant stood up from behind her desk and was now wearing her cheerleader skirt but it was much too short and pulled up a bit too high and her bright baby blue thong was showing. She walked to the front of her desk bending over to show her ass as she picked up the leather cuffs then brought them over and set them on his desk. She walked back and forth several times bringing over various belts and ropes and spreader bars, gags and plugs, every now and again he would remember he was in a meeting and responded to questions and made motions like he was paying attention. Eventually he forced himself to focus on the meeting and blocked her out. At least until she noticed he had tuned her out then she strutted to the middle of the room and slowly took her top off revealing a very lacy bra that let her nips peek through. She then turned around and slid her panties out from under her skirt. His meeting partners and client had all paused and were asking him what was wrong. She put a finger over her lips and shook her head. He swallowed and then said he got a text from his wife that distracted him but then she followed up and let him know everything was alright. He apologized and asked them to continue. She then began to crawl around to his side of the desk and under his feet. She took off his shoes and then reached up and undid his belt and zipper. She reached inside and stroked his cock and he almost exploded right then and there but she then moved to his ankles and started tugging on his pants. He awkwardly sat up just enough that she could remove them. Next she was after his boxers and trying to focus on his meeting he pushed her hands away and then looking across the room at her desk raised his voice to say "If that could wait just a bit I'm on a meeting right now." She giggled a bit then resumed her attempts at his boxers. He pushed her hands away again so she crawled out from under him. The next thing he knew she had a handcuff around his wrist and the arm of his chair. It happened so fast he didn't even realize what she'd done until she grabbed his boxers again and he tried to stop her. His eyes bulged and he tried to keep his cool but again he was being asked if he was okay. He apologized and said he wasn't feeling himself and asked if he could reconnect with them in the morning. They deliberated a bit and while doing so he let her take his boxers. Then she was strapping a leather cuff around his ankle as plans were made for what time tomorrow and whether or not everyone could meet in person. By the time they graciously excused him his ankles were held wide by a huge spreader bar. As he clicked off the screen he looked down ready to let her know in no uncertain terms that business came first but the words died on his lips as she wasn't there. Suddenly his open mouth that was full of reprimand was filled with a long thick rubbery object. He tried to spit it out but it was held fast and being strapped into place. He gagged and reached with his good hand to pull it out but couldn't budge it from the buckles in the back. He then tried to let his rebuke fly only to gag again. He reached back to grab her and she caught his arm in a chicken wing and held him painfully there. When he could take it no longer he relaxed and altho gagged cried for mercy. She held him still and whispered in his ear. "You lost the bet now its time to pay up. Remember you said you'd allow me to tie you up however I wanted right? Now stop fighting me. Okay?" He nodded and she let him go. "First things first I need you to take off that silly shirt and tie." He nodded and began to do as she asked. She then walked away and when she returned he had it all off but the one arm that was cuffed. She took his free hand and slid a padded ball over his hand and then cuffed it into place. He looked at it and experimented briefly to find that his hand was useless. She then put a very tall collar on him that strapped over his face and gag holding it deeply in his mouth. He struggled not to gag. "Remember to breathe through your nose and just relax." He did and felt his arousal rising. He had never experienced anything like this. She then attached another long spreader bar to the collar by its midpoint and his padded right hand onto one end. She then released his left hand and took his shirt off before padding that hand and attaching it to the other end of the bar. She then put a leash on the collar and tugged on it until he stood up. She lead him out to the middle of the floor. "Want to go for a little walk around the office? See who all is still here? I bet almost everyone is as its not even 5 yet." He tried shaking his head but his collar prevented that and instead his whole upper body moved. He tried to say "No!" but gagged again. "Relax Im just teasing. Not on your first bondage experience. We'll work up to public humiliation eventually." He tried to give a sign of relief but gagged again. At this point he totally missed the innuendo of future experiences in his relief to not leave the office. She asked him to kneel and tugged down on the leash until he knelt and even fell forward. She then tied the leash to his leg spreader bar keeping him folded with his ass in the air. He felt completely ridiculous and not at all as turned on as he had been before. He was not enjoying this at all. But then she laid down underneath him and said, "Time for some fun. I want you to enjoy this so if you can get your dick in my mouth I'll gladly suck it for you." He rocked up onto his forehead to see her laying directly beneath is dick which was hanging about 3 inches above her open mouth. He sprang back to life at this which had the unfortunate effect of raising his dick away from her. He tried to relax and arch down but the chain connecting his legs and his neck prevented him from dropping down hardly at all. Squirm and wiggle as he might his efforts usually only resulted in him raising up not dropping down. He got close enough for her to kiss the tip once and lick him but that was about it. When she did that his dick shot erect away from her and towards his belly. "What's the matter boss? You've never turned down a blow job before?" He tried again even harder but got the same results. "Well at least your pre-cum is delicious. But that gives me an idea." She rolled away and came back and using her hand milked a bit of pre-cum onto her fingers and then rubbed it on his asshole. Even sliding a finger in. "Relax boss I think you're really going to enjoy this." She milked a little more pre-cum and used it to lube his ass even more sliding in a finger a little further then her finger was replaced by something larger pressing against him. "Relax and let it happen. Just relax." Never in his life had he ever thought about something going up his ass. He wasn't sure he liked it at all. Still he tried to relax and eventually it slid in a bit. She pulled out then slid it in again this time a little further. Out a bit and back in, out and in. Then all the way out and back in. She noticed he was losing his erection. "What the matter boss? Is this not what you expected? Does this help?" She reached down and slid her hand down his cock as she moved the plug in and then up as she pulled out. Her hands matched movements and despite his best efforts he felt like he was fucking his own ass and he hated saying it but the dual sensation felt amazing! He even moaned a bit. She kept working him in and out, up and down. He felt an enormous orgasm building and as he got closer she stopped working his cock and just worked his ass as the orgasm faded she'd resume her work on both. Soon he was so lost in the sensations he barely noticed when she would stop massaging his cock and started rolling his hips riding the plug in his ass. As he rode he felt his orgasm building and he began to feel the need to release it. He started to roll faster. "Go on. Ride it. Take it in the ass like a bitch." That snapped him right out of it and he froze. "Don't stop now you were so close." She reached forward and grabbed his cock massaging it again and his orgasm came rushing back. His hips moving involuntarily. But without her stroking his cock he just couldn't get there. He rode harder and it started to hurt a bit he rode faster and still nothing. He then realized what he was doing and that she had stopped moving the plug at all. It was all him longing for anal. Then it occurred to him that she wasn't even there anymore. He rolled up on his forehead again to look back and she had used a plug on a stick. Well actually it was a dildo if he was honest about it and she'd tied the stick to his leg spreader. How long had he been doing all that on his own? "Sit up and come over here. Stay on your knees tho with that dildo still in your ass as you walk over." He realized his leash had been removed or at least untied and he could sit up. Sitting up though shoved the dildo deeper, much deeper. He sat up taller and almost felt the dildo fall out and sat back down a bit. The way it twisted and moved inside him as he walked on his knees, ankles spread wide, over to her was intoxicating. When he got to her she smiled and said, "Now it's my turn." She removed the part of his collar that held in his gag then removed the gag. She wrapped her long legs around his head and over his arm bars and pulled his face right up under her short skirt and his tongue arrowed directly into her pussy. She moaned and held him tighter and he licked vigorously. Licking her pussy was intoxicating and he loved every second of it. He felt his own orgasm spark to life again as she got closer. He started to ride the dildo as he licked her and he felt his orgasm grow. His own dick bouncing as he rode getting so hard it barely moved and then back to bouncing again. She arched her back and moaned loudly orgasming all up in his mouth and he drank it in and kept going riding harder getting closer himself but his ass was not lubed anymore and it started to hurt. He was so close his bouncing dick ached for release but the pain in his ass grew as he rode harder the pain both spurring and quelling his own orgasm. She squealed in delight orgasming a second time crushing his face against her soaked pussy. She eventually released him and asked him to wait a moment. He caught his own breath and squirmed a bit trying to make the dildo in his ass comfortable again. He froze as that thought sank in. He was trying to make a ...dildo… comfortable...in his ass...again! He shook his head at all that had transpired so far and the mindfuck he was experiencing. Did he dare ask for lube? What would she think? Would she even give him any? She returned and said "open wide" from behind him before he could ask for lube and he did so expecting his gag to be replaced. Instead it was a huge Jelly dildo that went far down his throat and still hung down onto his chest. "I need some actual penetration. No offense to your oral skills but well I think you probably understand now don't you? Altho I bet that's getting a bit raw now isn't it? Don't you wish you had a wet pussy to ride that dildo with instead of your dry ass?" He started to nod but caught himself and looked at her with wide eyes and a dildo hanging from his mouth onto his chest. She knelt down in front of him and said "kiss me" as she put the other end of the dildo in her mouth. She was a professional cock sucker and worked her way quickly to the midpoint and even a little past it then stopped and waited. He tried to replicate what she did and gagged and gagged again but then made progress and then a little more. The key was staying relaxed and letting things happen, not trying too hard. He gagged again then felt the dildo slide a little down his throat as his nose reached hers. He backed off then went in again taking pride in his progress and feeling the dildo go further down his throat almost reaching her lips then again this time actually kissing her and she grabbed his head and held him there for a second or two. Then holding him there she reached up with her off hand and closed his eyes. She then grabbed the dildo right where her lips had been holding it down his throat and sat back on his desk and then slid her end into her wet and weeping pussy. She slid her pussy all the way to his lips and said, "kiss me again!" He did but by now he was struggling to breathe and starting to gag as she held him. Finally she released him. "Kiss me 50 times. And I'll give you a reward." He eagerly swallowed as much cock as he could again and pushed the rest into her. It was much harder than he ever expected to kiss her pussy it took him swallowing more dildo than he expected and was quite the learning process as she wasn't holding onto it like before. He actually had to suck it in and down before pushing into her. She lost count pretty quickly as orgasm after orgasm rocked her body. He could have stopped at 30 and she'd never have known the difference but he was determined to show her he could kiss her repeatedly. Like he was getting good at it. It was a challenge and weirdly the better he got at it the better he felt about himself and the more turned on he became by the idea that his cock sucking skills were bringing her orgasms. He felt his own orgasm returning and tried riding his own dildo again. Pushing it into his ass as he pushed into her pussy and pulling out in rhythm as well. It would have worked if his ass wasn't squeaky dry. Still he could bounce his own dick around a bit for stimulation but could never get past general arousal. He managed the last 8 kisses in a row and held the last one for a second until her legs held him there for another orgasm to rack her body. She quivered and convulsed and he felt her pussy initially try to pull the dildo deeper inside her before pushing it deeper into his throat as she held his head tight against her crotch. He started to see spots as his airflow was restricted and she no longer had any concept of time. She did eventually collapse onto the desk as the orgasm passed and he let the dildo fall to the ground as he also almost passed out. He caught himself tho and tried to pick up the dildo but his hands were useless so he bent down and picked it up with his mouth again. She was still staring at the ceiling when she said. "Dear God that was awesome! Remind me next time to pick a smaller number tho... or maybe a bigger one..." She sat up and smiled at him. "Aww you've still got your dildo. Well as much as I'd love another round I honestly need a break for a second and I did promise you a reward." She got up and took the dildo from him and patted him on the head. "Do you want your gag back?" He didn't but at the same time his throat was pretty raw and he wasn't sure he was up to another round of pussy licking so he nodded. "Really? Well okay. I was just joking but... here you go." She strapped the large phallic gag back in place and even refixed his collar straps over his face holding it in place. "And now for your reward." She unhooked his wrist cuff from the arm bar. He shook his arms a bit not realizing how tiring it was to have them in that position. He accidentally bumped his still semi-hard cock with one of his padded hands and then started to rub his cock back to life. Honestly he wasn't even thinking, more just acting by instinct when she yelled "Stop that right now!" He froze realizing what he was doing and tried to apologize but couldn't. But he didn't gag on his current gag anymore! "Well I think that stunt might earn you a little extra reward. Arms out" he moved to oblige and she knelt in front of him and clamped both of his nipples in tight clamps then she slid a leather straight jacket over his arms and chest. And strapped it snuggly around him. She then pulled the dildo on a stick out of his ass and told him to stand up. She then took the extra long dildo that they had shared and slowly slid it in. It went in so smoothly. It seemed to glide in and out deeper and deeper and since it was lubed properly it felt so good. She then hugged him sliding her we pussy down his body but not letting his dick side inside her. She was sitting on top of his dick and it throbbed up her crack and she would slide down a bit forcing it down then allowing it to rise back to a horizontal position. He could feel her wet pussy dripping on the base of his cock but the tip never touched anything. The whole time she slid the dildo in and out of his ass. He began to quiver. He needed an orgasm so badly it began to hurt. The longer she teased him the more he ached for release. She was so slow and methodical keeping him right on the edge. Teasing his ass, nibbling his ear, and riding but not riding his cock. He began to beg her to ... do something different but it just sounded like moaning. He was right on the edge. He had been for basically the whole day but especially this last bit. The ache in his balls grew. And a horror of an idea began to brew in his mind, he began to think she might be doing this on purpose and didn't have any intention of letting him cum even after all he'd done for her. He stopped. He asked her to stop. She looked at him and asked, "are you done?" He nodded...-ish. "Are you sure?" He nodded again. "Well okay then. One last thing then we're done. Do you want some ice?" He sagged back down against the desk and she walked away and came back with some ice. "What hurts?" He managed to somehow say his balls through the gag and she knelt down in front of him and held the ice against his balls for a moment. His erection that had been there all day finally subsided and his balls tightened up. He closed his eyes and let her massage his balls and cock with ice. Between the numbing agent of ice and the general overall ache of being on the edge of orgasm for hours and hours he didn't notice that some of the ice wasn't actually ice but rather cool steel and the clicks weren’t just ice cubes rattling but a steel cage being fit together. The tightness wasn't just the shrinking caused by ice making him smaller than he'd been in quite a while but also the small steel cage restricting his size to its smallest form. When she walked away he even thanked her. She came back over to him with her phone in hand. She showed him pictures of him in his various positions enjoying anal stimulation and sucking on a large dildo. The last picture made him pause. He didn't understand why she had a picture of a dick in a cage. Then understanding hit and he tried to look down but couldn't. He could feel it now though. His dick was locked in a tiny steel cage. "You see, when we made a bet we never set a time limit on how long I could keep you restrained. Just that I could do it sometime this week. Now don't worry it's not permanent or anything and I'm sure we'll find a way for you to earn your way out again but until then you need to be prepared to keep me very happy. And if I ask you to do something, I won't change my mind and the request won't go away. You will eventually do everything I ask you to no matter how outrageous it may seem. I don't expect you to understand all that right away. Let's get you untied so you can go home. I'm sure Janet is missing you by now." She held up his phone to see a message from his wife saying, "I know you are working hard today but save something for me when you get home. I'm feeling more than a little frisky." And another saying, "You know how I said I'm not comfortable wearing lingerie around the house well..." Followed by pics of her in a very sexy teddy and stockings in several different rooms. His eyes bulged. She's never done that before. "Shall we respond?" He tried to shake his head and say no but her fingers were so fast. How's this? "Wow. You look amazing. Thank you for allowing me to work late tonight. I'm almost done. Headed home soon. I promise to make you feel like a queen tonight. I've got a little something special in mind that I've been wanting to try for while now." He was speechless. He'd have to give his wife multiple oral orgasms or something after all this. "...And send. Well now at least she knows to expect something. You'll just have to convince her you want to remain locked in chastity for a while and also do everything you can to keep that nymph satisfied." She smiled at him with a genuine joy. She was enjoying this on an almost spiritual level. "Now let's get you untied and on your way home to that hot wife." Once he was untied he gently touched the cage. Then looked quickly at her to see if she noticed. She had and she was still smiling. "By all means go right ahead. Play with it all you want. Try to pull out. Try to break it. Try giving it a wank! It's on there and it's real and it's not going anywhere for a long time. Give my love to Janet!" And with that she was out the door. He looked around at his office. It was a mess and it smelled of sex. Restraints were strewn about and dildos. Computers and papers in disarray and even on the floor. He'd make her clean this up in the morning... or would he? Could he make her do anything anymore? He reached down and touched his tiny steel cock. He did try to pull out. He did try to bend it. He felt himself growing or at least trying to grow inside the cage and he was reminded of how incredibly horny he actually was and tried to massage his balls and tug on the cage and while he could feel his arousal brewing it seemed an impossible task to get off. He looked around again and saw a picture of his wife. He needed to get home to her. As he got dressed he pondered, could he tell her what had happened? About the bet? It would crush her. He couldn't bear causing her that kind of pain. No he'd have to find some other way of dealing with this. He grabbed his things and as he was headed for the door he stopped and looked at the double sided dildo on the floor between his feet. Then he bent over and picked it up. Took it to the washroom and then in his bag as headed to his car. Janet might need more than his tongue and fingers could deliver tonight. Penetration is a good thing. He knew that first hand now.