My Female Boss Takes Control 6
[Another chapter in the story of Darren's submission to his boss Jane. This starts the morning after an open air release from his cage, and builds up to their long-awaited business trip.]
MONDAY
On Monday morning my phone beeped as soon as I turned it on.
'Wear the underwear I bought you every day this week. Save the light and dark pink pairs for Wednesday and Thursday, I like those the best.'
My boss Jane was taking me away with her to a conference at the end of the week. We were travelling down on Wednesday and would be away two nights.
The underwear was a cross between silk knickers and nylon boxer shorts. There were two super smooth triangles back and front linked by the section between the legs. The rest was nylon, like thick stockings, but still fairly see-through. The legs extended half way down the thigh. They looked feminine but were obviously designed for men. The front triangle had a pouch set into the otherwise close fitting material.
I pulled a yellow pair out of the packet. I thought it was an odd colour but if anyone ever saw them that would be the least of my embarrassment. I sorted through my shirts to find the longest one. I definitely didn't want it to come untucked and show off the silky finish of the yellow waistband.
My loosest fitting suit trousers weren't the best for the warm weather forecast, it was my thickest suit. But this was my first time in the office wearing the cock cage and I was scared that someone was going to notice something strange.
The underwear had another feature that wasn't helping with that. There was a wide elastic section that ran down from the waistband, under my balls and back up. It was like a stretchy stirrup that lifted my package up and forwards. It made my cock and balls feel a lot more prominent.
I paced up and down in front of the mirror, trying to see if I could make the shape less obvious, but then I looked like I had some terrible back pain. I tried adjusting the position of the pouch so that the elasticated band was in front of my balls. But that just hurt and after a few paces they popped back out into the pouch anyway.
Would anyone work out I was wearing a chastity cage? How many of my colleagues knew such things existed? I was convinced people would notice.
At work I scurried to my desk and sat down to get out of sight. I gratefully accepted the offer of a coffee rather than have to walk to the kitchen and make my own. I scanned my calendar to try and work out how much time I could spend behind my desk. The morning was pretty good, but there was a staff meeting after lunch.
I decided my best tactic for that would be to go in last so I would have to stand at the back. Then everyone except those running the meeting from the other end of the room would be looking away from me. It was a good plan but, of course, Jane had a plan too.
After lunch I got the text message I'd kind of been expecting all morning - she wanted to check I was properly dressed.
'Pull your zip down at your desk. Walk over to me and talk about something. Hold your trousers open the whole time you are in front of me.'
My cock gave an involuntary spasm, pushing against the metal cage. Why did being embarrassed by her turn me on like this?
I sat there trying to work out the best possible route. Pulling my zip down first was actually helpful. Doing that standing up could easily be seen for what it was from several angles. Taking one last look at what my colleagues were doing, I pulled my zip down. I held a cardboard folder in front of me and walked over.
She smiled and we started talking. As casually as I could, I slid my other hand to my crotch, used my fingers to hold the sides of the zip apart and moved the folder out of the way. Jane kept talking and talking, giving the most detailed possible answer to my question before letting me retreat. I sat back down at my desk and zipped up. My face was hot and my cock had filled its cage. I looked down trying to work out whether its doomed attempt at an erection was pushing my trousers out further. My phone beeped.
'Good boy. Ghastly colour. Glad you got those out of the way first. I could only just see them though. Your shirt was in the way. We'll have to think of a better way tomorrow.'
Staff were beginning to assemble for the meeting. Letting everyone else get there first, I walked slowly to the doors at the back of the room. But Jane had hung back too. She was also heading for the back of the room, which made no sense at all because she needed to be at the front.
She must have checked that we were the last two, because as we approached the doors she began to grope my buttocks. Her thumb stroked my right cheek while her fingers pushed into my crack and stroked vigorously up and down over my anus. My cock was really pushing on the cage now. I groaned quietly, knowing that it must be pushing outwards against my trousers. My face was glowing again and I felt sweaty in the thick suit.
As we went through the doors her hand dropped away. She strode down the room to the front while I slipped in and stood at the back. I sighed with relief and hoped my cock would start to relax. As another colleague on the top table sorted out their papers, I could see Jane was doing something with her phone. I frantically fished mine out to turn off the sound in case she texted. I certainly didn't want everyone turning round and staring at me. She had texted me a picture.
I quickly clutched my phone to my chest and glanced round to see if anyone was looking. The picture was of me the night before when I had met her out on the moor. I was wearing pink shoes, harem pants and a crop top. As she'd instructed, I had my hands on my hips and I was blowing her a kiss.
Satisfied that everyone's eyes were on the front of the room, I eased the phone away from my chest slightly. I was confused. As well as the picture of me, I could see the date and time. Then I got it. It wasn't just a picture, it was a screenshot. My picture was the wallpaper on her home screen.
I screwed my eyes shut, wishing I could just disappear. I opened my eyes and stared at the table in front of her. Where had she put her phone? Was the screen blank? My treacherous cock was loving it - just as hard as it had been when I came in. I stared at her and she smiled back.
As the meeting ended, I shot out and practically ran down the office to get past the other doors so my back would be to anyone coming out.
As Jane returned to her desk, she had a quick look round the office to check no one could see then, mimicking my pose in the picture, she briefly put her hands on her hips, thrust her chest forward and blew me a kiss.
My eyes widened as I stared at her, even after she dropped the pose. The end of my cock hurt. I could feel the tip being pinched as it tried to force its way through the slot in the end of the cage. My balls ached for release. I spent the rest of the day staring at her desk to work out where her phone was and how visible it was if anyone came to see her. She was a devious bitch. And I was devoted to her.
TUESDAY
Tuesday started like Monday with a message waiting on my phone.
'Good news pet. I've solved our little problem. Isn't that great?'
I stared at the message trying to work out what 'our' problem was. After a minute or two I decided that the question mark meant she expected a response.
'Yes Goddess.'
'Wear a belt today. Then as well as undoing the zip you can undo the waistband too and slide the top of your trousers apart along the belt.'
I sank down on to the bed and held my head in my hands. I'd only just dealt with the attempted 'morning wood' by turning the shower cold, now my embarrassment-craving cock was filling its cage again. My phone beeped.
'What colour are today's knickers sweetie?'
I look across at the open packet. '
'Dark blue Goddess.'
'Lovely. Can't wait to get a good look at them.'
A moment later she texted again.
'Hey! Like your balls right? lol.'
I hadn't noticed anyone staring at my crotch on Monday, so I was feeling a little braver today and moved around the office more. Just after I'd arrived Jane had texted to say she had changed her phone screen so that I would get some work done rather than spend all day staring at her desk. So I was feeling a little less tense, despite knowing I still faced some danger of exposure when Jane decided to inspect my underwear.
In the hour before lunch several of us had a meeting, led by Jane. Mounted on one wall ofcthe meeting room was a massive TV screen. Jane sat below it. I was sat opposite her at the other end of the room. One side was all window, with thick vegetation outside.
At the end of the meeting, as colleagues began to leave, Jane announced that she needed me to stay in the room over lunch and help run through her conference presentation.
When we were alone Jane grinned and said, 'right pet, inspection time. Plus, I've got a little treat for you!'
I was immediately wary of this treat but kept my reply to a respectful, 'yes Goddess.'
'Move your chair out of the way, then stand with your back against the wall.'
As I moved into position she disconnected her work laptop from the network. Producing a memory stick from her jacket pocket, she plugged it into one of the sockets on the side of the TV screen. She navigated to the memory stick with the remote. She was leaning against the door now, her tall frame blocking the thin window down the middle. She turned her head toward me.
'Pull your zip down.'
I couldn't help glancing at the windows as I did. There was a path down this side of the building, but no staff ever used it, knowing how overgrown the hedge was. Occasionally a member of the public would try and force their way through, thinking it would provide a shortcut to the bus stop.
'Now undo the waistband and slide your trousers apart as far as you can along the belt.'
She wasn't satisfied with by first effort.
'Come on, further than that, I want to see silk.'
I slid the two sides as far apart as I could.
'Now pull the pouch section out so it's hanging out over the bottom of the zip.' I grasped the cage round my cock a pulled it forwards, hoping that she intended to stay where she was, blocking access to the room and any view through the window.
I looked down feeling embarrassed. But even hidden in the cage and the shiny pouch, this was the attention my cock craved. Unable to escape the metal confines of the cage, it tried to expand by pushing the cage and ring outwards from my body. The silky pouch stretched forward with it, giving me a royal blue stub sticking out from the black of my trousers.
'Put your hands together behind your head.'
I raised my arms up and laced my fingers together. Even though I hadn't removed any clothing, I felt as naked as I'd been on the hillside a couple nights before. I was breathing more deeply, my chest rising and falling. Her ability to get me posed like this in the office in the middle of the day felt like some magic power. I didn't feel ridiculous, I just felt .... hers.
'Good boy. Now, watch the screen.'
She pointed the remote at the TV and opened a file on the memory stick. The screen turned black, or rather a dull grey. Then suddenly a hand appeared holding a thick pink rod which was held against the screen, as if it was a window. Then the screen turned a fleshy pink.
It was a body. With a cock. My cock. on Sunday night she'd had a video camera in the car. It must have been attached to the sun visor. That's why she'd left the cabin light on. Then the cock was pressed forward more firmly, spreading it against the glass. Was that when she grabbed my buttocks? Jane paused the video. I stared at the two foot high image of my cock.
'You do actually have quite an impressive cock pet. Some guys are submissive because they're small, but not you.'
She set the video going again and I watched my screen cock start to squirm around before settling into a short up and down movement. With each upward movement, the glans rolled towards the glass and the opening gaped wide and then closed. I was terrified someone would pick this moment to walk by, but I was fascinated by the enormous image.
Then my cock seemed to press harder against the glass, squashed flatter and wider. The body around it began to shake. In response, my caged cock started to jerk about too, my pelvis thrusting forward and back. I could feel the weight of the cage swinging and the drag of the pouch restraining it.
My onscreen body froze, then cum started to pump out of the cock. There was nowhere much for it to go with my body pressed against the glass. Most of it seeped down the sides of my cock, the rest gradually got smeared across the glass. I desperately wanted to cum now as well. I was bucking my hips as if the weight of the cage dragging on the skin of my cock would be enough to do it.
Obviously it wasn't going to come close and I felt there was something essential missing. I wished I was wearing the plug. I wished I could be clenching and unclenching my buttocks round its heavy mass, pulling it backwards and forwards inside me.
'This is my favourite bit.'
As she said it I realised I'd closed my eyes. I opened them to see my face filling the TV screen, systematically licking the window clean.
'I amazed you didn't notice the camera at this point pet. I guess you're just really committed to cleaning up after yourself! Great video though. My husband Michael loved it. He watched it three times.'
My head snapped round from the screen to her face. My mouth hung open in surprise. She just shrugged.
'It's only fair sweetie, he spent ages setting up the camera.'
Before I could even think of what to say or ask next, she closed the video file and changed the subject.
'Your arms must be pretty stiff now. Put them down by your sides. Don't close your trousers up yet though, you seem to have made quite a mess of your knickers.'
I looked down. I may not have had the orgasm I wanted so desperately, but I'd leaked a lot of precum. There was a large wet patch at the front of the pouch.
'Leave it out in the fresh air while I tell you about tomorrow. I want you here at 7am sharp. I want to make an early start. You can leave early today to get your things ready. Make sure you're wearing your plug when you get here.'
The question in my mind must have shown on my face.
'What is it pet?'
'I don't understand why we need to start so early. The conference is only two hours away.'
'There's something we need to do here first and a couple of shops we need to visit on the way. Just trust me pet and be here on time. Oh, and for goodness sake wear a lighter suit. You must be sweltering in all that black wool.'
WEDNESDAY
Getting to the office for seven meant a very early start. We were travelling to the conference in Jane's car so I'd come in via two buses and the tram. Despite the hassle I was excited for the day ahead.
I was worried about just what shopping we were going to do on the way. Was she going to humiliate me in a woman's clothing store? I hoped that whatever she had planned was going to take place well into the journey, where no one would know me.
At this time we were the only ones in the office and should be for at least an hour. There were two colleagues who occasionally liked to make an early start though. I shuddered at the thought of one of them walking in on me in an embarrassing pose.
I found Jane at her desk and as I appeared she checked her watch and smiled. 'Good boy. Slightly early. Right, follow me.'
She strode off down the office and I hurried after her. I'd expected us to go into the disability bathroom as before, but we ended up in one of the meeting rooms. The room was square and one side was just windows. Apart from a six inch deep horizontal piece of frame at waist height, it was all glass. I followed her in and turned to close the door.
'Leave it open pet. We're the only ones here.'
Only ones here so far, I thought.
'Now, strip and greet your Goddess.'
I knew I was going to obey. My hands moved to start removing my clothes but I couldn't help glancing outside. This part of the building wasn't overlooked by any other building or visible from the road. But on the other side of the glass there were two parking spaces. Anyone choosing one of them would see into the room. They were popular spaces too, it was easy to swing in and out of them. I thought there was quite a high chance that any early arrival would pick one of them.
I had this greeting routine established in my head now. I made a careful pile of my folded clothes on the floor. Once I was naked, I turned away from her, bent at the waist slightly and pulled my buttocks apart to show that I had my plug in place.
I did this briefly without pausing. I wanted her to know I had obeyed her instruction, but not to think I was making any request of her. I turned back to face her and dropped down on all fours at her feet. I kissed the top of each one then raised my head and stayed still, like an obedient dog come to heel.
'Stay on your knees but straighten up.'
I pulled my self upright and instinctively put my hands behind my back. She leaned down over me.
'Judging by your response on Sunday, I think we can add a new element to your standard greeting pet. I know you want this. Tilt your head back and open wide.'
She sucked around her cheeks a few times, then slowly drooled her saliva into my mouth. I savored it with my swirling tongue and then swallowed.
'Thank you Goddess.'
She ruffled my hair and pulled my head upright. Then she sat down and crossed her legs. She made a slow circle with the raised foot and watched my eyes follow it.
'Take my shoe off pet, hold me in your mouth and listen carefully.'
I was thrilled at this honour. She had removed her shoes herself before, but now she was letting me. I gently eased the pale pink shoe off like it was a delicate treasure, breathing in deeply as I did to try and capture her sweaty fragrance. Putting the shoe down, I went back on all fours and sucked her big toe into my mouth.
She pushed forward and I opened my mouth as wide to accept its penetration as deeply as I could. Her big toe was at the back of my tongue and I fought to suppress any gagging action. My tongue massaged the ball of her foot. I knew my jaw was going to ache if she made me hold this pose for long but I didn't care. I used to dream of fucking Jane Redding, but now it was her penetrating foot that turned me on.
'Today's the big day sweetheart. The day you get up close and personal. Until this afternoon, this has all been about you learning how to behave. Learning about punishment and reward. You've been finding your true submissive self pet.'
'It excites me to watch you learn what you really desire. Pushing you to accept each new experience, and punishing you when you fall short turns me on. It makes me wet.'
I shuddered. My glans was tingling and I knew there would soon be a wet string of precum swinging from the end of the cage. Looking up past her legs and into her eyes I had this weird fantasy image of swallowing her whole foot, of her beautiful leg fucking my face like a crude deep throat video.
'But this afternoon you're going to start serving a more basic need. You're going to be obsessed with physically satisfying your Goddess above anything else.'
'You will take pride in how often I cum. You will strive to make my body shake longer and harder. Every time I cum, you will be overwhelmed by gratitude and thank me for letting you to be part of it.'
'I think you're already beginning to feel that obsession aren't you? I can see it in your eyes pet.'
With her foot spearing my face I couldn't speak, so I just tongued the bottom of her foot as lovingly as I could in agreement. I did already crave to satisfy her. My locked up cock was swinging gently as I sought even the tiniest satisfaction of feeling the weight of the cage. My buttocks were clenching rhythmically against the plug. My mouth was blocked, so I was breathing hard and fast through my nose.
I thought of the times I had watched porn videos of women on their knees swallowing huge cocks and wondered if there were videos like this too. She looked into my eyes, waiting silently for me to work through this moment and calm down.
'But there's something we need to get out of the way first pet. Something that would spoil the mood later. It's time for those gorgeous buttocks to pay your debt.'
She shook her foot very slightly and I moved my head back to release it. As it slid from my mouth I dutifully lapped up all my drool from it.
'Good boy. Use your shirt to dry it. Make sure you get between the toes.'
Without hesitation I picked up my shirt and gently patted her foot dry. I carefully separated each pair of toes and wiped in between them. When I was done she told me to stand and face the window. She put a chair in front of me.
'Bend over and hold each side of the seat.'
I bent over and grasped the sides of the chair. 'Feet apart, wider than your shoulders.'
When she was happy with my stance she said, 'this is going to be hard and fast pet. I'm sure you don't want to risk having an audience halfway through. I want you to thank me straight after each blow or I'll do it again. Lift a foot or bend your knees, and I'll do it again. Understand?'
'Yes Goddess. Thank you Goddess.'
She leaned down over me. Her breasts pressed into my back. Her right hand slid from my hip along my right side, then underneath to my chest. She toyed with my right nipple. She whispered softly in my ear.
'You need this sweetheart. You need this discipline in your life and you're pleased it turns me on to do it. You know your scarlet bottom will have my damp knickers clinging to my pussy by the time it's done.'
She pulled my nipple away from my chest and slowly licked my ear.
'Remember to breathe.'
Then she stood up behind me and to my left. Moments later her first blow landed, her right hand crashing into the top of my left buttock. The physical shock of the first blow intensified the searing sensation. I screwed my face up and fought to keep my legs still before blurting out 'thank you Goddess'.
'Faster than that boy. I'll let that one count but the thank you needs to faster.'
The next three blows landed on the same spot. My eyes felt damp as a quarter of my bottom burned. My 'thank you' got faster but came out as a high pitch squeak. There was a pause as she stepped across to my right. Then she delivered the same treatment to the top of my right buttock with four blows from her left hand.
I'd thought the first spanking she'd given me had been incredibly painful, but now I realized that three weeks earlier she must have been holding back. This was far worse. She finished the second four blows and stepped back. I could hear her breathing from the exertion, or was it her excitement, and I realised I'd been holding my breath. I let it out, trying to stop it turning into a groan.
'You're doing well pet. Just need to keep this up until the end. Now, bend over further until your forehead is on the chair.'
I followed her instructions and gasped. Bending over further stretched the skin on my buttocks tighter, sending a new flash of pain across them. She returned to her first position and delivered the next four blows to the lower half of my left buttock. I tried to just shut out the pain and concentrate on keeping my legs still and saying thank you as quickly as I could. I just wanted this to be over.
She switched to the right side again to spread the same agony to the bottom of my right buttock. My bottom felt like I was sat on a hotplate, cooking my skin. My eyes weren't damp, I was crying. Through the pain I wondered what would happen next. Jane had spread sixteen blows across my bottom, but I was due seventeen.
'Nearly there sweetheart. You need to be very brave for this last one. Spread your feet another further apart and arch your back.'
Blinking tears from my eyes, I did my best to comply. I felt her fingers and thumb pushing round the base of the plug to grip it. Twisting and tugging, she took it out and I heard her put it down on the table.
'You can do better than that pet. Get a real curve in that back and push your balls backwards where I can see them.'
I was gripped with fear now. Was she really going to smack my balls? Surely this was too much.
'Pet?'
I'd come this far and I really wanted to spend the next two nights serving her body. I longed to win that intimate prize. I sighed and pushed back as far as I could.
'Good boy. Who owns you pet?'
'You do Goddess.'
The blow came as soon as I said it. Her right arm must have already been raised in readiness. She swung it down hard, striking my anus with the back of her hand. My legs started to buckle and I struggled not to collapse. The new pain was worse than the previous sixteen blows. But alongside that searing pain, a strange detached part of my mind was grateful she hadn't chosen my balls.
I realized I was ignoring all her instructions and straighten my legs. I babbled, 'Thank you Goddess. Thank you. Sorry Goddess. Please Goddess. I'm sorry I was too slow Goddess.'
She said nothing, waiting until I shut up.
'Don't panic sweetie, that was the end of your punishment. Now, stay still.'
Suddenly I felt a cool thick liquid land on my right buttock and then another blob dropped on my left. It was some kind of cream which she used both hands to spread and then gently rub into my bottom. It felt so good. Her palms glided over by buttocks, her fingers gently flexing over my skin. It slowly began to take the edge off the pain.
One hand left and then I flinched as another cool blob dropped into my crack. With the fingertips of her right hand she spread cream over my anus. It was the most fantastic thing a woman had ever done to me. I'd experimented doing this to myself and it had felt like a revelation. Bent over at work with Jane's finger silkily circling my hole was way beyond that. I hoped this would go on and on and let out a long groan as if I was cumming.
'You are learning fast aren't you pet. Your learning where your greatest pleasure comes from. I think you're ready for the next stage. Wait there.'
Her finger disappeared and she walked out of the room. I felt an immediate sense of loss. But then she was back and kneeling behind me. She was busy between my legs. I looked back to see what was doing. She was stretching something over my cock cage. Her right hand was covered by a black latex glove.
'It's an unlubricated condom pet. Can't have you making too much mess if your needy little bottom really is ready for this.'
I was completely lost about what was going on now, but that didn't actually matter. Jane was in charge and I trusted her. Satisfied that the cage was now covered up, she told me to stand whilst she sat down on the chair.
'Come and lie across my lap pet.'
I staggered to her. My legs were stiff from being locked straight throughout the spanking. I bent over and she guided my naked body into position across her thighs, head to her left, legs to her right. I put my hands on the floor to steady myself. She pulled my legs apart and I felt fresh air on my anus.
Her latex covered finger and thumb rolled each of my balls in turn between them.
'These must be aching a bit by now.'
They really were - after two days of her teasing with no relief from the cage.
'Right sweetie, let's see if you're ready for another first. Let's see if we can drain these swollen balls.'
She leant down to her right. I saw her pick up a bottle of clear lubricant and then felt her squirt some right on my anus. Then two gloved fingers swirled round in the lube and teased my hole.
'This little hole's been on quite a journey hasn't it? No one had ever touched you here before had they pet?'
'No Goddess.'
'Had you ever touched yourself here?'
'Not until you gave me the first plug Goddess.'
'Wonderful. I do love a virgin arsehole. But this is so more than just an arsehole now, isn't it pet.'
Her fingertips exerted more pressure now. Not pushing in yet, but working the ring of muscle.
'It's been fingered now hasn't it? Just like a woman's pussy. It's had two exciting toys pushed inside it. Like a hungry pussy. On Sunday night, when I held the vibrator against the plug, it pulsed away through an amazing orgasm, didn't it pet? Just like a pussy should. And tonight,' she started to push both fingers in together, 'it's going to get fucked.'
She pushed both fingers in as far she could. My hole was stretched tight round them. I realized it wasn't stinging. It gripped at her fingers. It felt ok. Better than ok. Special. Intimate.
I could feel pressure inside me from the ends of her fingers. It felt like she was pressing down on me, moving them round in a circle.
'So, where are my fingers now pet? Are they stroking your arsehole, or your pussy?'
Her fingers curled slightly and she began to move them in and out. Pushing backwards and forwards over my prostate.
'My pussy Goddess.'
'Good boy. Now just relax and let your body respond to my fingers.'
I didn't need telling. I was exploring a completely new sensation. I felt like I was floating. It felt good, but it was hard to define why. It felt deeply sensual, but at the same time like I wanted to pee. My balls felt ready to cum, but my cock was soft. I had started to pant, as if I were have a slow, steady fuck, but I wasn't thrusting.
It felt like something was flowing through my cock. It wasn't the same as cumming, though the end of my cock felt permanently sensitive these days so there was a gentle feeling of pleasure. Despite the tension in the muscle wrapped round her fingers, I felt incredibly relaxed. I had a nagging fear that sooner or later one of our colleagues might turn up, but I'd lost track of how long she'd been stroking me deep inside and just lay there. Trusting her.
Eventually her fingers paused and I felt her lean over to look between my thighs. She slowly slid her fingers out.
'I think you're all done pet. Stand up.'
I got up on my feet and stood in front of her, watching as she pulled the glove inside out and off before tossing it onto the table near the plug. She leaned forward and carefully manoeuvred the condom off the cock cage, the held it up between us. I was amazed how much fluid there was trapped inside it. Maybe twice as big as a marble.
She pointed out a box of tissues and told me to wipe my 'pussy' and get dressed. As I did, she carefully tied a knot in the condom, which had to signal another embarrassing challenge. When I was dressed she gestured me stand in front of her.
''Open wide pet.'
She pushed the bulging condom in my mouth and pushed my jaw back up.
'Keep it intact until I tell you to bite on it. Now tidy up in here, wash your plug and put it and the lube in your case. We need to get moving.'
I did as she said with a smile. I was glad the spanking was out of the way. She was right about my balls aching less after draining all that fluid. I felt refreshed and longed for us to be alone at the hotel.
Despite the condom filling my mouth, life felt pretty good. As I was finally ready to leave I noticed the air drop logo appear on my phone. She had sent me two pictures. They both showed me bent over the chair. One was my bright red bottom, the other a close-up of my anus.
She walked up to me, office keys jangling, ready to leave too.
'Make one of them your phone wallpaper today, then swap to the other tomorrow.'
[I love to get feedback on my stories and two readers have already added to the tale of Darren and Jane. So do tell me in the comments or by private message which bits really worked for you. Thx.]
- The sight of the yellow underwear in the packet sent a wave of embarrassment through me, knowing I would be wearing it to work.
- The wide elastic section of the underwear made my package feel more prominent, causing a noticeable bulge in my trousers.
- The staff meeting after lunch was a serious test of my submissive skills, as Jane required me to walk with my trousers open and my zip down while in front of her.
- The humiliation of having my picture in a feminine outfit displayed as her phone's wallpaper made my cock fill its cage, despite the embarrassment I felt.
- On Wednesday morning, I was worried about the shopping trips Jane had planned for us on our way to the conference, fearing she would humiliate me in a woman's clothing store.