My Female Boss Takes Control Ch 08

[The morning after Darren's first pegging.]

I hadn't bothered looking at the next set of underwear before going to bed. I'd seen a brown bag on the chest in my room but hadn't looked inside. My head had been too full of what just happened.

I had licked and kissed an arsehole for the first time, working my tongue deep inside. Then Jane had taken my anal virginity with her strap-on. It had hurt. Really hurt at first. The butt plugs had prepared me for the sensation of being opened up and penetrated, but not the constant movement of being fucked. The backward and forward stretching sensation felt like repeated burns and through the initial thrusting I had an image of being ripped open by a cock as large as her thigh.

But the physical sensation had eased and changed. The feeling generated by the head of the dildo pressing backwards and forwards over my prostate had felt deeply satisfying. It wasn't as intense as an orgasm, but it felt like something satisfying that my body really needed.

When Jane had built up to her climax I had wanted to come too. But the constriction round my cock had shut that off. It was like a destination I could see but knew I couldn't reach. I'd read about guys cumming whilst caged, but I hadn't felt close to that. If anything, I'd felt closer to cumming immediately after Jane did.

The way she had flopped down onto by back and held me as her orgasm faded had made me feel pleased with myself. She had used me to get the sexual high she wanted, and I'd felt proud. Then she'd hugged me tight, pressing her breasts into my back and whispered 'good girl' in my ear. At that moment I'd pictured cum flowing out of my cock through the end of the cage. Not a pulsing orgasm equal to hers, just the response of a contented pet. The image felt so real that I actually inspected the end of the cage to see if there was any cum there, but was just slick precum.

I didn't sleep well. Despite Jane milking my balls dry in the morning, the repeated stimulation through the day had got them really aching again and to start with my arsehole was sore and swollen. I could actually feel it puffed up between my buttocks, before the weirdest of stretching sensations as it pulled back into shape.

This morning in the shower my hole didn't feel so bad. I bit tender maybe, but normal otherwise. After drying off, it was time to investigate what underwear she had chosen for me today. I assumed it was in the brown bag.

The bag itself was confusing. It was too big and posh just to carry the underwear, so I assumed she expected me to use it during the day. But that didn't seem too much of a challenge. It wasn't too obviously feminine. It was a shoulder bag made of soft brown leather but it wasn't shiny or decorated.

Inside the bag was a mass of black nylon, lace, and straps, none of which seemed to be knickers. I laid it all out on the bed. There was a pair of stockings. They were darker than yesterday's but looked a bit shinier. I was going to have to be careful when I sat down not to display my ankles.

There was a suspender belt that seemed bigger and thicker than any I had seen before, with six straps rather than four. There were no knickers. Jane obviously expected me to go commando, which immediately made me anxious about being noticed by other people. Any serious stimulation was going to mean a wet spot from precum leaking directly onto the inside of my trousers. After the activity of yesterday I was sure that stimulation was exactly what Jane had in mind.

I didn't think about not wearing any of it. I was past my initial inhibitions now. Jane had pushed me through some barrier of resistance. I would do this because doing what she told me to do felt right. She also understood how much I was secretly thrilled by the prospect of embarrassment and exposure. So what occupied my mind now, was how to get the underwear on rather than whether to wear it.

I put the suspender belt on first. I struggled to get it fastened though. I'd never worn anything with hooks and eyes and doing it behind my back was impossible. I was cursing in frustration when I remembered watching a girlfriend putting on her bra. So I did the hooks up at the front and then pulled the belt round 180 degrees.

The stockings took several goes just to get them up my legs, let alone fastening the straps on. I finally had the front and side ones on but was defeated by the two at the back. So I wasn't dressed at 8:00 when Jane walked straight into my bedroom.

'Come on pet, you're late.'

She looked at me standing there in stockings and suspenders and walked around me.

'You need some help don't you. Stand still.'

She sat behind me on the end of the bed, fixed the rear suspender straps and the adjusted the others. She ran her hands up and down my nylon clad legs and smiled as she saw my cock jerk the cage in response.

'Feels so good doesn't it? You'll have to set up your next appointment with Nicky soon though to keep your body all smooth and hair-free. Maybe I can negotiate you a special deal on the cost. A bartering of services perhaps!'

She winked. My cock flexed again at the thought Jane might offer some sort of service to Nicky from me in exchange for a waxing. The way things were going, I was going to be oozing precum before I even finished dressing.

'You look gorgeous pet. Now, one last thing. I want you to try a new cock cage today.'

She took the chain and key to my cage from round her neck and delved in black bag she had brought in with her, producing a new cock cage. She held it up briefly so I could see. It was metal like the one I had on, but it was more curved and twice as long. It was still far short of my erect size, but would allow my cock to expand much more.

The main difference was that it was far more open. Rather than being a metal cylinder with holes, it was made from thick long metal wires that curved together at the end where they joined on to a small ring. It looked sort of like a food whisk with a curve.

'It's called a birdcage pet. It will still keep you locked up but could allow all kinds of fun. Who knows what might happen. Now, hold still, let's do this quickly. We haven't got time for you to go all hard and then soft again.'

She undid the padlock and roughly pulled my cage off. I gasped at the discomfort, then yelped as she immediately used her thumbs to quickly squash each of my balls through the retaining ring. I was sure the pain was deliberate, to discourage my cock from swelling, as she then did the same in reverse to fit the new ring and then fed my cock into its new wire tube.

'There we are. Very sexy. Now hurry up and finish getting dressed, we need to get on. The shoulder bag is for all the things you normally stuff in your pockets. Far too hot to wear a jacket today.'

She left the room and went downstairs as I put my shirt on. So that was the plan - the bag wasn't meant to be embarrassing, it just meant I'd spend all day wondering whether anyone could see the top of the suspender belt through my shirt.

I pulled my trousers on and began stuffing things in the bag. Instinctively I slipped my phone into my pocket, and then yelped a moment later as it landed on my foot. I put my hand in my pocket to see if there was a hole. There was a big hole. In fact I didn't seem to have a pocket at all. I put my other hand in the other pocket. It was the same. About an inch of material and then I was touching my leg. She must have cut the pockets off whilst I was in the bathroom using the enema and douche the night before.

I put the phone and all my other stuff in the bag and went downstairs. I stood by the mirror and tried to work out whether anyone would be able to see into my pockets. I thought it would probably be ok. Although when I bent forwards you could clearly see the outline of the rear suspender straps through my trousers. I was obviously going to have to stay standing or make sure no one was behind me when I sat down. I was going to be on edge all day. She blasted the car horn and I hurried out to join her.

Over a coffee shop breakfast we planned our day. Jane was speaking at a seminar at 11:30 and I would go and listen. Apart from that she was mainly at invitation only events.

'So apart from listening to me, you can spend your time networking round the exhibition. I do hope you're going to be more outgoing and helpful than yesterday. I'll see you after the seminar.

She stood up to leave.

'You don't look too excited about the day pet. Get out your phone, I've got something that might perk you up a bit.'

She airdropped me a file. It was quite big. When it was done she smiled, raised her eyebrows and walked off.

It was a video. The file was called 'Darren's big adventure.'

I looked around to check that no one was heading my way and tapped the screen. The opening shot showed the soles of two feet. A man's feet. Mine? Then the shot slowly moved up the back of the man's legs until you could see his bottom.

It was me. It was from last night. I was kneeling on the floor wearing pink crotchless knickers. The shot was already quite tight, but now it zoomed in even tighter until it was just the pink knickers, my crack and, the shiny metal end of the butt plug peeping out from between my buttocks.

I hadn't even seen the camera when I'd walked into the bedroom, but admittedly I had been more interested in Jane's bare legs. She must have been operating it with a remote control. My nerdy self was quite impressed with how she had been able to pan and zoom.

The video cut to a new shot. My head was between her knees, with the pink hairband over my eyes and ears. Just ahead of my mouth was the end of her strap-on cock. How had she done that? Two cameras? Doh! Two people. Someone else was filming.

I paused the video. It had to be her husband. She said he'd fixed the camera in her car and watched that video. Now he'd actually been in the room watching. I was actually a bit turned on. The fact that she just had exposed me to someone else, like at the waxing session, reinforced how she owned my body. It was even hotter that it was her husband this time. I was still intrigued about he fitted into this weird life of hers.

Meanwhile, my cock had started to explore its new prison. I could feel it extending slowly down the curved cylinder of wires. I restarted the video. The camera view zoomed in on my face. I watched my tongue poke out and lick the end of the strap-on cock.

The video had been heavily edited and made me look like an expert cocksucker. The hesitations, all the times that I'd gagged and jerked my head back were all omitted. In the video you would never know this had been my first attempt. It showed a smooth progression from licking and kissing the end, to sliding backwards and forwards down the whole length. When I pulled back the final time it cut to me smiling. I knew that had been in response to Jane's praise, but with no sound it looked like I was one proud and enthusiastic cocksucker.

I stopped the video and checked again that no one was paying close attention, but the cafe area was fairly quiet now as most people had gone off to their conference sessions.

I was disappointed that the cocksucking section revealed hardly any of Jane's body. The carefully framed closeups only showed her arms and thighs. The next sequence made me stop the video again and stare.

The action had moved on to when Jane was crouched over my face and nearly the whole screen was taken up by her magnificent bottom. She had obviously only just leaned forward. I could see her whole crack and brown puckered anus. It was moist from my tongue, which you could see sticking up at the bottom, waggling around trying to relocate her hole.

I don't know how long I stared, transfixed by her bottom. The image of her most secret flesh. I smiled. I didn't have a picture of her face, but I had one of her anus. I guess that showed me my place in life. I furtively looked round the cafe again and then, feeling quite guilty and embarrassed, I spread two fingers out across the screen until it only showed her hole and relived the thrill of seeing it up close for the first time.

I was concentrating so intently that when the phone beeped with a text I almost dropped it.

'Enjoying the video pet?'

'Yes Goddess. Thank you Goddess.'

'Glad you like it. Don't spend all morning hiding in the cafe though. I will be most put out if you aren't there to listen to my speech.'

I looked at my watch. There was still time to watch more, but it felt a bit too exposed do it in the cafe. My cock had now filled the wire tube and was pushing at the end. I really wanted to touch myself while I watched the video.

Holding my bag in front of my crotch I decided to find somewhere quiet outside watch the rest of the video. Eventually I found an unoccupied bench and got my phone out.

The video restarted with me lifting my head up to get my tongue back into Jane's hole. The camera position followed my head and zoomed in on my tongue stretching out, searching for her hole. Then it disappeared as my head leaped forward into her crack. For several minutes the screen was filled with her large buttocks wrapped round my face. My head and her bottom shook in tandem, locked together by my determination to thrust my tongue as far inside her as I could.

I longed for a better image, fantasising of some sort of micro-camera in my nose that could film my tongue pushing into her. I paused the video and slid my finger over the screen, going back through the images until I reached the point where it just showed Jane's bottom. Without even looking around me first, I greedily expanded the image until her hole filled the screen. I was lost in the moment when I had first touched it with my tongue, kissed it like a passionate lover, then wriggled my tongue inside.

My eyes flicked up from the screen to check I was still alone, then I slipped my right hand into my pocket. I stroked my fingertips along the top of my cage. Feeling the bumps of tortured skin trying to push out through the gaps. I realised that I could feel the contact much more through my fingers than my cock. The flesh of my cock felt numb, pressed tight against its metal prison.

I really needed to calm down and let my cock go soft, but I couldn't stop staring at the image on the screen. I stared at the picture of Jane's anus, every wrinkle, every change in colour and texture. I tried to remember what it felt like when I first ran the tip of my tongue over it. I wished I was really alone, somewhere private. I think I would actually have stuck my tongue out and touched it against the screen. I wished my cock was free so I could stroke it.

God my head is so fucked up I thought. I looked up from the phone, relieved to see no one else had discovered this spot. No one to witness a sweaty grown man torturing his own aching cock whilst studying a picture of his boss's anus.

I put my phone in the bag and decided to go for a walk round the car park. Hopefully the fresh air would dry my precum-stained crotch and the exercise ease my blue balls. There was still an hour to go before the seminar.

I wondered how ridiculous I was, wondering around with stockings, suspenders and a cock cage beneath my trousers. Should I stop this? Ask Jane for the key and leave? I knew I wouldn't. Not yet. I could stop later when I wanted to. God, that's what addicts say, I thought.

I wondered what happened to old submissives, and had a vision of old men in a home, restrained in their wheelchairs by strict, busty care assistants feeding them teaspoons of cum. I realised that I hadn't watched the whole video yet. On both attempts so far, I hadn't got past the image of Jane sitting on my face.

I was on the far side of the car park now and spotted one of those benches you wonder who on earth is going to sit on them. I smiled.Obviously architects knew they were needed by shy perverts to sit in peace and watch themselves being fucked on video!

Satisfied that no one was going to disturb me here, I settled down and restarted the film. When it reached the moment where Jane had raised herself up and sat back on my face, the camera zoomed out a little showing her the bottom half of her naked back.

Apart from the strap-on harness she had been naked. I wondered how much more of her would be revealed. On screen, Jane leaned forwards again and the video zoomed in on her hole. The image faded to black then reappeared, only this time the backside was mine. I was bent over the end of the bed. One of Jane's hands appeared and quickly pulled out my metal butt plug. I was fascinated by how my anus didn't immediately close up. Before it could, I watched her push the neck of a bottle of lube into the gaping hole with her other hand and squeeze the contents into me.

The camera view cut to a view from above and zoomed in on my hole. Jane's hands were holding my buttocks apart and my crack was shining with lube. The head of the dildo appeared, slick and shiny, and pushed into me. I watched the angle of the cock change as she rotated her hips. I could see how my hole was being stretched round and round. Then the whole cock leaped forward into me. I remembered the pain of her first thrust and the steady transition from the stretching and burning through to the satisfying rhythmic movement backwards and forwards across my prostate.

The camera shot changed to a rear view of Jane hunched over me. There was a fleeting view of her bare back before it zoomed in on her bottom pumping up and down above mine. The camera jerked around a bit as Jane's husband must have knelt down behind us, then zoomed in to a view up between her thighs.

My cock twitched in its cage as I watched her strap-on cock thrusting in and out of me. I could see how it pushed my hole in then dragged it out. Backwards and forwards. The skin of my taint shone as lube spread down from my pummeled hole. I watched how my caged cock and balls swung in time with her thrusting. I could see a strand of precum swinging from the end of the cage.

I had my right hand in my pocket now, my fingers stroking my balls and then sliding over the surface of the cage. The climax of the video was Jane pushing the cock in deep, then holding in there as her bottom clenched and shook up and down through her orgasm. It was an awesome sight. My powerful Goddess cumming with her cock buried deep inside me.

Then her bottom lifted up out of shot and the flesh coloured plastic cock fell from my crack and hung alongside my own. The screen when blank. I stared at it, panting a little, aching for some kind of release. I pulled my hand out of my trousers and looked at my fingers all covered in precum. I licked them clean. So much for letting my cock soften!

I filled in the rest of the time before the seminar meeting just walking purposely around the conference centre as if I were late for an appointment. I hoped the exercise would ease the pain of my blue balls and that my keeping moving I would avoid anyone noticing the outline of my suspenders. I kept an eye out for Mike, but wasn't sure whether I wanted to see him or avoid him.

When I found the right room for the seminar it was nearly full, which was quite a problem. I really didn't want to edge my way along a row of occupied seats. Being that close to people as I moved slowly by would provide many opportunities for people to notice the outline of the suspender belt, or the straps against my trousers.

The room sloped up from the platform like a lecture theatre. I wondered if I could just sit on a step near the top of one of the side aisles. As I got near the top I saw an even better option. Right at the back there was a passage behind the last row. It ran from one side to the other and was partially screened off by a partition that came up to chest height.

As I walked to the middle, I could see it was an even better spot. There was a small bay in the wall. Standing there I had a great view down to the platform and no one could see any of my body unless they came right up to me.