Jamie's Descent Pt. 02

I scuttled away to the washrooms and after quickly checking there was nobody else there, I washed my face and clumsily reapplied the lipstick.

I got back to my desk and Vanessa had closed the door to her office, so I sat outside, terrified that somebody would notice that I was wearing lipstick. Yet again, a couple of the girls stopped by my desk and complimented me on the colour of my lipstick. I was mortified that they had noticed but nobody seemed to worry or make a fuss.

Vanessa returned after lunch, again smelling of drink. She called me into her office and asked how the morning had gone. I told her about the few calls she had received and that nothing else had happened. She waved her hand at me to dismiss me, but I hesitated. She looked up with a frown, 'What is it sissy?'

'Well Mistress, I dont understand why, but nobody seems to care that I'm wearing lipstick, I even had a couple of compliments.'

'So you should, its a lovely colour.'

'Yes, Mistress, but why doesn't anyone seem to mind?'

She leaned back in her chair, 'Well I suppose you'll hear about it anyway. I have told everyone that they will see some changes in the way you dress and look.'

'But why?'

She glared back at me, 'Why what?'

'Oh, I'm sorry. Why, Mistress?'

'Because I've told everyone you are beginning to transition. You came and told me you are transgender and you wanted to act and dress as a girl.'

I felt like I was going to faint, 'But why did you tell them that?'

'Because that way everyone accepts that you're wearing your hair like a girl and wearing lipstick. They think it's cute.'

I felt tears flooding my eyes and I wiped them away.

'Don't snivel, girl, its better this way, you'll have to learn to trust me, now go and fetch me a coffee.'

I did as she asked and sat outside her office for the rest of the afternoon, trying and failing to make sense of what was going on. I had fallen under the spell of this woman, I felt powerless to resist her and I had no idea where this was going to lead.

At the end of the afternoon she called me into her office and handed me a new panty and bra set, but this time a suspender belt and a pair of stockings.

'I want you in the office wearing these tomorrow, ready to do what we discussed this morning, complete with lipstick. is that clear?'

I nodded meekly.

'I didn't hear you say anything, sissy.'

'Yes Mistress,'

'That's better, and you had better make sure your seams are straight in the morning.'

I returned to my flat and collapsed on the bed, unable to process what was happening. A few days ago, I was a bored but happy intern, one of thousands no doubt, just doing what they have to do get by. Now, I am the submissive slave to a mistress, who seems bent on feminising me. Well, it has to stop now, I said to myself. I won't do it any more. I fell asleep determined to stand up to Vanessa.

The next morning I woke early and looked at the pile of lingerie that I had left on my bedside table. I reached out a hand and felt the shimmering nylon of the stockings and it was as if they were calling to me. I shook my head but the desire to just try them on kept growing and growing. I showered and shaved, made some coffee and tried to ignore the voice in my head telling me just trying the stockings on wouldn't be so bad, I could always take them off again.

So, I slid the suspender belt around my waist and remembering what I had seen in porn films I rolled the stockings into a doughnut shape and slid them up my legs. I alost fainted from the sensation they created. The smooth nylon electrified me as I pulled them tight up my legs and managed to fasten them to the clips on the belt. I walked around and the gentle tug of the straps on the belt was so arousing I was soon hard and I had to stroke my cock until I came, my knees almost giving way beneath me.

After that, I had no choice in the matter, I pulled on the panties and fastened the bra before putting on my work clothes. I would put the lipstick on when I got to work. The journey to the office was a nightmare; the pull of the suspenders, the tug of the bra strap and the silkiness of the panties was enough to keep me in a state of permanent arousal. I dashed into the washroom and applied my lipstick, hopefully a little better this time.

Vanessa arrived and I followed her into her office.

'Good morning, Jamie, I hope you have done what I asked?'

'Yes, Mistress.'

'Alright, prove it my pet.'

I unbuttoned my shirt to show her the bra and I rolled up a trouser leg to show her the stocking.

'No, no, silly girl. I want to see it all.'

I removed the shirt and trousers and stood there trembling, clad only in the lingerie. She walked around me sliding her fingers over the front of my panties and, of course, my cock began to respond.

She giggled, 'I see my little sissy girl likes wearing pretty lingerie. Well. don't worry, there's plenty more where this comes from. I see your seams are straight too, you must have dressed carefully this morning. Now on your knees and get under the desk.'

I felt so exposed, on my hands and knees under Vanessa's desk, dressed in bra, panties and stockings bringing her off with my tongue. I felt vulnerable, yet the whole thing was so exciting, serving my mistress in such a slutty outfit. My cock was rock hard by the time Vanessa poured her sweet juices onto my face.

I crawled from under the desk, my neck aching and my face slippery with her cum.

'Good girl, that was better than yesterday, you're learning fast. Now when you go to freshen up I want you to wear this.'

She reached over and pulled from a bag what appeared to be a skirt and blouse.

'No, Mistress, please, I couldn't wear those, everybody will laugh at me.'

She slapped me hard across my backside. 'I will spank you if necessary Jamie, I promise you. Nobody will laugh because they think you are transitioning. The expect you to wear this. Now go and do as I tell you, and use the ladies washroom.'

I ran off, hoping that no-one else was in yet. I made it to the ladies washroom and leant against the wall for support. I couldn't do this, could I? I realised had little choice in the matter now, I had been manipulated into this and I could see no way out. I slipped on the white blouse, and was horrified to see that my bra was visible through it. I pulled on the skirt and managed to get it fastened. it was black and came to just above my knees. I let my hair down and looked at my self in the mirror.

I was shocked to see a girl looking back at me. I couldn't believe it, I didn't look that bad. Sure, I could see it was me, but a different me, softer, more feminine than I could have ever believed. I fixed my lipstick once more and walked out of the washroom right into one of the other office girls.

'Jamie, you look great, that blouse and skirt really suits you. I wanted to tell you yesterday how brave I think you are doing this. let me give you a hug.'

She pulled me towards her and embraced me.

'Look, I hope you don't mind me saying but you could use a little more makeup than just that lipstick, a little foundation and blusher maybe? Do you have any?'

I shook my head and she grabbed my hand and dragged me back into the washroom. She opened her bag and within a few minutes she had made up my face and reapplied my lipstick.

'Now that looks better, just something simple for the office. What do you think Jamie?'

I looked back into the mirror and this tine it was somebody different looking back at me.'

'Thank you,' I stammered,'it looks so nice.'

'You're welcome honey,'she said, 'Got to rush, good luck girl.'

I returned to Vanessa's office and she looked up and did a perfect double take.

'Well, don't you look good, what happened?'

'I met one of the girls and she did it.'

'Well all you need now are some shoes, and look what I've got for you, my pet.'

She produced a pair of black shoes with what looked like a ridiculously high heel.

'Your task today is to learn to walk in these babies. Because tonight I have a surprise for you, so cancel any plans you have.'

With that she disappeared and I didn't see her until late in the afternoon. She called me into the office when all the others had left.

'Have you learnt to walk in the shoes?'

I had spent the day practising and although my feet were now extremely sore and my ankles ached, I had mastered them more of less. I walked across the room and she clapped her hands, 'Perfect, I'm very pleased with you. Now, take off the skirt and blouse and leave your lingerie on.'

I obeyed and stood there feeling very embarrassed, not knowing what to do with my hands, and I ended up holding them across my chest, just as a girl would do to cover her breasts I realised.

'Jamie, your training has started very well and will continue this evening. Tomorrow you won't need to come in to the office, as I have made you an appointment with our company doctor for a medical as well as a visit to the hairdressers.'

Vanessa moved over to the office window and closed the shutters so that no outside light could get in.

'Yes Mistress,' I began to worry what was going to happen next. Vanessa handed me a small box.

'I want you to wear this at all times.'

Inside the box lay what looked like a small gold chain.

'It's called a slave bracelet. You wear it around your ankle.'

I looked closely and there was a tiny inscription 'Sissy'.

'What's it for?' I asked.

Innocent or stupid? I don't know even now.

'You don't need to know, just make sure you wear it all the time, is that clear?'

Vanessa's tone was sharp and I quickly bent over and fastened the bracelet to my ankle. She took the opportunity to slide her hand over my silk covered backside.

'So smooth,' she whispered to herself. Vanessa reached into a desk drawer and held something behind her. She moved behind me and she asked me to put my hands behind my back. As I did I felt a sharp pain as my wrists were cuffed together.

'What the hell?' I said, startled.

Vanessa gave me a smack across my bum with something hard and I yelped.

'Next time you swear at me it will be ten across your arse,' she growled. 'I promise you will not get hurt if you behave yourself. This is part of your training and you must learn to trust your mistress, is that clear? There is no pleasure without some pain but if you do well then the pleasure will truly outweigh the pain.'

Chastened, I nodded. 'Yes Mistress.'

'Now, I am going to turn the lights out and it will be very dark, so don't be frightened.'

Vanessa moved to the door, locked it and turned the lights off.

Immediately, the room was plunged into absolute blackness. I could see nothing at all, and despite the warning I became very nervous. Almost naked, handcuffed, in total blackout; who wouldn't be nervous? I suddenly sensed a new presence in the room. I couldn't see anything but I knew there was somebody new in the room. I opened my eyes wide but I could see absolutely nothing, but I sensed someone moving around me in the darkness.

'Who's there?' I croaked.

'Silence!' a male voice commanded.

I almost jumped out of my skin as I felt a hand glide across the back of my panties.

'Be still!' the voice ordered.

This was not a voice to argue with for sure. The hand stayed where it was and began to gently rub to and fro across my bum. I began to feel aroused as it relentlessly kneaded my cheeks. I felt a second hand brush across the front of my panties. This hand began to rub my swelling cock through the panties and I thought I would faint with the sensation that was being generated.

My knees began to wobble as I struggled to contain the feelings caused by the attack on my front and rear. The hands now moved inside my panties and I almost could not cope with the waves of pleasure that surged through my nerve endings. I whimpered with ecstasy as a finger slid down between my bum cheeks and probed my anus at the same time as my cock was being stroked vigorously - whichever way I moved it seemed to intensify the pleasure I was feeling.

The darkness was no longer frightening; it produced a sense of isolation in me that added to the erotic quality of what was happening to me. Suddenly, the hands moved away and I stood there panting, desperately wanting the climax I had been heading towards. A hand pushed me to my knees and I almost fell over because of my cuffed hands and unfamiliar heels.

The man moved in front of me and I felt my nipples twisted and tugged by strong fingers. My nipples had always been sensitive and I almost fainted as they stiffened with the man's assault. The hands moved to the back of my head and as I felt my head pulled forwards, I instinctively jerked back.

'Do not resist me!' The voice hissed out of the darkness.

The pressure continued and I felt my head slowly move forward. Something brushed against my lips and I gasped aloud as I realised what it was. The man's cock felt warm against my lips - totally unlike the cold unyielding rubber of the night before. Almost with a life of its own, my tongue pushed its way out of my mouth and flicked out to touch the cock.

I was rewarded with a soft 'Aaaahhh' from the man. I continued to explore with my tongue as the man held his cock in place. The cockhead felt like velvet as my tongue lapped and slid across the surface. The man pulled again at the back of my head and I opened my lips and allowed his hard cock to enter my mouth.

This felt completely different from the previous night. Then the phallus was cold and lifeless; a pathetic substitute for the object I now held between my lips. This was the real thing. I could feel the veins standing out from the surface and felt the cock twitch as it slid deeper into my mouth. I could feel the heat and I could smell the man's odour as well - an aroma of pure masculinity.

Although this was the first time I had ever held a cock in my mouth I remembered what Vanessa had done last night and began to move my head up and down the shaft. I gagged once or twice, and the man sensing my inexperience pulled back to allow me to recover. Once, I brushed the cock with my teeth and the man hissed in anger. Despite my inexperience I quickly found a rhythm and slid my mouth along the length of the shaft, once feeling my nose graze the man's pubic hairs.

Despite my lack of skill the man moaned once or twice so I guessed I was doing OK. I began to feel I was dreaming. As if in an out of body state, I felt myself rise above my body and look down on the scene below. I saw myself, wearing stockings, panties and a bra, kneeling with my hands bound in front of a tall well built man. The man had his hands round my head and he was pushing his large hard cock in and out of my mouth.

I watched as the man tensed and approached his climax, moving his cock faster and faster as the moment of release approached. I heard the man grunt and saw his knees sag slightly as he came and I watched with detached fascination as the man climaxed. I saw myself suck the cum eagerly from the man's cock and swallow greedily. I watched as the man withdrew his cock, saw him wipe it casually across my face and myself smile as I licked my lips to collect the last of the cum that had spilled from my mouth.

I had found my destiny.

To be continued