Jamie's Descent Pt. 02

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Jamie slips further under Vanessa's control.
6.7k words
4.63
45.2k
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Part 2 of the 5 part series

Updated 06/08/2023
Created 06/18/2016
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'That's it, baby,' Vanessa purred as she snaked her hips forwards and back, gently sliding the strapon in and out of my mouth. I could no longer think rationally, as any self control I still had slipped away and trance like, my eyes closed, I sucked the rubber phallus in and out of my lips.

'Baby, you love this don't you?' Vanessa's voice took on a hypnotic tone, gently encouraging me to take more and more into my mouth.

I was too far gone with lust and desire to even register the question let alone give her any answer.

'This is what you want, isn't it? You want to be a cocksucker don't you? This is what you've dreamed about, baby. This is what you were born to do.'

She placed her hands around the back of my head pushing me deeper and deeper onto the strapon. I gagged as I took nearly the whole length into my throat and she relaxed a little to let me recover and then continued her penetration of my mouth. I couldn't describe what I felt as I knelt in front of my office supervisor, my nose buried in her crotch sucking on the large black strapon she was wearing. I felt shame, certainly, and fear mixed with a sexual arousal so strong it was scrambling my senses.

From somewhere deep in my brain came faint messages of alarm and warning. The rush that flooded through me as I gave myself to the woman I knelt before instantly swamped these feelings and I felt my willpower sliding away. Incredibly, I felt my cock rise and harden and I knew I had lost the battle with my last remaining inhibitions. How had this happened to me? At this moment I neither knew nor cared as I greedily licked and sucked the rubber tool in my mouth. I had never done this before but it seemed so right, so natural. How could something that felt so good be wrong? Vanessa was right; I was born to do this.

How had she known? How had she seen right down to the depths of my soul? Vanessa took her hands from the back of my head and slipped the strapon out of my mouth. I swear she could see the disappointment flash in my eyes as the object of my worship was removed. I felt lost without it's presence in my mouth.

'Don't worry, baby. If you liked that, it won't be long before you feel the real thing.'

Vanessa replaced her finger in my mouth and I heard myself sigh as I sucked it gently and gratefully between my lips.

'Jamie, things will begin to change for you now. If you don't want your colleagues to see the pictures I took posted on the company intranet, then you will do as I say without question from now on. Do you understand me, Jamie?'

Her tone became sharp and she lifted my chin with a finger and locked her eyes back onto mine. I could not resist this woman who seemed to see right through to my darkest desires.

'Do you understand me, Jamie?' she repeated as she lowered her face to mine and I could not tear my eyes from hers. I vaguely knew that this was my last chance to regain control. But her eyes burned into mine and I felt any remaining resistance dissolve away and I nodded my head.

'Ye... yes,' I managed to croak.

'Yes Mistress!' she barked straight into my face. 'From now on when others are not around, you will call me Mistress. Is that clear?'

I swallowed and nodded again.

'Say it,' she snapped.

'Yes, Mistress,' I replied, realising just how much my jaw ached from the sucking I had given the strapon.

'Good, very good, Jamie. Now I want to repay you for what you did earlier. Stand up.'

I climbed unsteadily to my feet, my legs trembling from what had happened. Vanessa took my arm and led me to the armchair that sat in the corner of her room.

'Sit, Sissy.'

Her tone of voice was all I needed to make me sit down sharply in the chair. Vanessa quickly knelt in front of me and she undid my zip and belt with practised hands. She reached inside my trousers and she felt me harden straight away.

'My, my, you did enjoy that didn't you, you filthy little sissy.' Vanessa smiled as she spoke and her tongue slid across her lips. The way she said sissy made me shiver with fear and anticipation.

'Watch, feel and learn, Jamie. I promise you will enjoy this.'

Her head dropped into my lap and she took me into her mouth so quickly and so deeply I thought I would faint. I looked down to see her head bobbing up and down on my engorged cock and I could feel her tongue swirling across my cockhead. I moaned with pleasure as she reached up with one hand and stroked the base of my cock as she licked and sucked the head. I had become so aroused I knew it would only be seconds before I came. My body tensed as I felt the pressure build deep inside me and my cock grew even harder.

Vanessa sensed the climax and closed her mouth around my shaft. I jerked clear off the chair and came as I had never come before and I moaned as the cum flowed from my cock into Vanessa's mouth. She took the load into her mouth and with lightening speed rose and kissed me on the lips, forcing her tongue between my teeth and transferred the cum into my mouth. Before I could react, Vanessa had clamped my mouth shut and I swallowed automatically. I opened my eyes wide as I realised what she had done and I began to struggle. She slapped my face hard and I stopped moving, shocked into immobility.

'Jamie, that's only the first of many you will swallow, so get used to it.'

She rose and picked up the camera, snapping more pictures of me as he sat, now mentally and physically exhausted on the chair.

'That's enough for today my little sissy,' Vanessa whispered almost tenderly. 'From tomorrow, you will be promoted to the role of my personal assistant and you'll sit outside my office. I would advise you to accept this new role, unless that is, you want pictures I took of you tonight to end up in everyone's email.'

From somewhere I summoned the wits to nod. That wasn't enough for Vanessa, who said, 'Say thank you properly, Jamie.'

'Thank you Mistress,' I responded, my eyes downcast in abject humiliation. Vanessa turned to her desk and took from something from a drawer.

'Jamie, my little sissy, I want you to start wearing something suitable for your new status. These will do wonderfully, I think.'

Vanessa handed me a pair of silk panties. I felt my face burn as I realised what they were.

'Oh, so sweet... I love it when you blush, Jamie it makes you look so shy and innocent. Yes, that's the look we will go for - sweet and innocent by day and a cocksucking sissy slut by night.'

I blushed again as I realised how much I liked the sound of that.

'I'll see you at 08.30 tomorrow morning and if you're not wearing those panties I will be very, very angry.'

Vanessa stood there with her hands on hips.

'Now, shoo and go home you silly little girl. I need you fresh for tomorrow.'

Vanessa turned to the mirror on the wall and retouched her make up as I left her office, but I don't think she meant me to see her smile and wink at the mirror as I closed the door. I don't know how I managed to get home that night. My mind was reeling from the sensory overload I had gone through that evening.

I stumbled back to my tiny flat and I collapsed on the bed. I felt tears of shame prick my eyes as I remembered how Vanessa had humiliated me. She had made me kneel in front of her and suck her rubber cock, and I had not put up much of a fight. I was a pathetic snivelling little excuse for a man. The bitch, the bitch, the bitch. I said it over and over. Well I would show her. If she thought she could do this to me she could think again. I just wouldn't put up with it. I would leave. I would resign and just leave the company.

What could she do? I had made my mind up to just not turn up the next day when I put my hand in my pocket and found the silk panties that Vanessa had given me. It was true they were the loveliest shade of peach and the lace trim felt exciting as I ran them through my fingers. I turned them over in my hands and I looked at the label - La Senza. I had often stopped in front of the La Senza shop in the shopping centre and I remembered how turned on I had felt looking at the beautiful lingerie in the window.

Without thinking I brought the panties up to my face and rubbed the silk over my skin. It immediately made me remember how I had felt on my knees sucking the strapon, and I felt a frisson of excitement as my cock betrayed me as it twitched and hardened at the memory of what I had done. It wouldn't do any harm just to slip them on, I thought. I'm not going through with this so I'll just see what they feel like. I stripped quickly and stood looking at myself in the full-length mirror in the bedroom.

I had never been exactly an athletic type of guy but I had pretty good muscle tone and had looked after myself pretty well. I ate the right things and hadn't gone to fat like my brother. I looked down at the scrap of material in my hand and I felt my cock twitch again. I looked in the mirror and watched as my cock began to grow before my eyes. I bent down quickly and put one foot and then the other into the panties. I pulled them up my legs and the silk and lace fluttered over my skin, sending shivers through me. I gasped as I pulled the panties up to my waist and as they cupped my cock and balls I felt my knees turn to jelly. The silk and lace felt so light and cool - yet it held me so delicately.

I turned and looked in the mirror and fell in love with what I saw. My ever-stiffening rod tented the panties out, but I though they made me look so pretty. I did a little twirl and looked over my shoulder and my bum filled the panties just so. I had kept my hair long for as long as I could remember and wore it normally tied back in a ponytail. I now shook the hair free and it tumbled down over my shoulders. I shook my head and the hair moved free, my whole body seemed to soften before my eyes. The angular lines of my masculine body blurred before my eyes into soft and gentle curves.

I was now fully erect and as I ran my hands over the silk covering my bum I shivered and moaned aloud as I felt the material slide beneath my fingers. I closed my eyes as my hand moved to my cock and I began to stroke. I felt harder than I had ever been before. My cock felt like a rod of steel. My breathing shortened and I opened my eyes just in time to see my cock spurt for the second time that night.

It was as if I were watching someone else in the mirror as I saw the half man half girl touch a finger to the cum stringing from the oddly familiar figure's cockhead and lift it towards their lips. I stared as I saw the figure in the mirror lick the cum from the finger, smile back at me and suck the finger deep into his mouth. I knew then that I would be at my new desk at 08.30 sharp the next morning.

I had half expected Vanessa to be surprised when she turned the corner and saw me sat at the desk outside her office the next morning. However, she merely nodded to me as she walked up to my desk.

'Good morning, Jamie. How are you this morning? Did you have a good evening?' she asked without even a trace of irony.

'Yes, thank you,' I replied, equally deadpan. I looked around and as we were the only ones in, added, 'Madam.'

'Jamie, very good. You will do very well in this new job I think. Now come in to my office we need to organise the day's work.'

I hastened in behind Vanessa who closed and locked the door. I stood in the middle of the office as Vanessa circled me, looking me up and down several times in a frankly disconcerting way.

'Yes, there are a few things we can start to work on straight away,' she murmured to herself. 'But first, did you do as I asked, Jamie?' She stood in front of me and looked me straight in the eye, unzipped my trousers and slid her hand inside. She nodded in approval as she felt the silk and she squeezed my balls until I squeaked in protest.

'Good, Jamie. A very good start to our new relationship.

'Thank you, Mistress,'

Vanessa walked behind me and took off the plain elasticated band I used to tie my hair back. She pulled my hair back and replaced it with a salmon pink scrunchy. This time though the ponytail was fixed at my eye level; much higher than I usually wore it. I moved my head from side to side and I felt the pony tail swing gently behind me.

'It will make me look like a girl,' I whimpered.

'Don't be silly,' she said, 'If David Beckham can wear it like this, so can you.'

I had to admit later as I preened in front of the mirror in the staff cloakroom that it did look good on me. It seemed to narrow my face, make my cheekbones more prominent and my eyes somehow larger. I quickly got used to the swing of the ponytail as I moved my head and soon I had forgotten it completely.

The day flew by and it was obvious that my new role wasn't that demanding and I wondered just how Vanessa managed to get away with doing so little work. She had gone to a lunch meeting that had lasted three hours and she had arrived back looking a little flushed. I thought I could smell drink on her breath. The biggest problem I had to deal with all day was hiding the erections I was getting from wearing the panties. Some of the other staff noticed my new ponytail, but nobody said anything to me, and a couple of the girls said how nice it looked.

Five o'clock came and the rest of the office staff departed leaving Vanessa and me alone in our part of the office. About six, Vanessa asked me to come into her office. I again stood in the middle of the office as Vanessa walked around me. She reached up and took off the scrunchy from around my hair so that it fell around my shoulders. She looked closely at my hair and pulled a face.

'We'll need to get your hair cut properly, it's a disgrace. Luckily it's long enough to do something nice with,' she moved away from me and sat in the chair I had sat in when she blew me last night. I couldn't help but tremble with the memory.

'Now for tomorrow, I want you wear these for me.' She handed me another pair of silk panties, but this time she handed me a bra as well.

'But, Mistress, people will see it.'

'Your problem, not mine, sissy. Remember I have those photographs and I will be happy to use them if necessary.' She put her finger beneath my chin and raised my face to hers. 'It wont be necessary, will it. my pet?'

I shivered with fear and excitement at the thought of wearing the bra. The panties, and even the pink hair scrunchy were one thing, but a bra? What was I getting myself into?

She dismissed me and told me to be in early the next morning for a special assignment. I scurried home to my flat, swearing yet again that I would not do what Vanessa wanted. However as I let the silk of the panties and bra slide through my fingers, my cock began to tingle and I thought, what harm would it do if I tried them on. It wouldn't change my mind of course, I still wasn't going to wear them for Vanessa.

I slipped off my work clothes and pulled the panties up my legs. I sighed as the silk cradled my cock and balls in it's sensual grip. I let my hair down and even brushed it so that it had some shape to it. I picked up the bra with trembling fingers and wondered how I would put it on. I remembered seeing a girl do this thing in a porn film. She did her bra up at the front and then twisted it round. I managed to control my trembling fingers long enough to fasten it at the front and then pull it round so that the cups were at the front. I slid the straps up my arms and over my shoulders and at the first tug of the straps, I was lost. It felt so erotic, the material soft and silky against my skin and the straps tugging at me as I moved. How weak was I? Vanessa knew exactly which buttons to press.

I scuttled into work early the next day, my jacket concealing any sign of the bra under my shirt. Vanessa strode straight past my desk and into her office, leaving the door open.

'Well, sissy, what are you waiting for? We have work to do.'

I looked around, terrified that sonebody had heard, but we were the only ones in at that early hour. I scuttled into her office, after which she closed and locked the door before pulling down the blinds.

'Take that jacket off, sissy, I want to see if you have done as you were told.'

I removed my jacket and Vanessa came and stood very close to me, her fingers running over my chest so that she coud feel the bra under my shirt.

'Good little girl, Jamie, you're doing very well so far.'

She moved her head forwards, her lips almost brushing mine.

'Do you like my lipstick, Jamie?' she whispered. 'It's pink, all sissies like pink. Do you like pink Jamie?'

I felt myself nod, too scared to speak. her tongue flicked out and she ran it along those lovely pink lips, my eyes following the action.

'Do you want to wear pink lipstick, Jamie? Tell me if you do and I'll put some on you now. If you dont say anything, I wil take that as a yes, my little sissy.'

My tongue was frozen in my mouth. I wanted to say no, but my tongue wasn't listening to my brain, and I said nothing.

'So thats a yes, Jamie. You want to wear my pink lipstick today.'

My mind was screaming NO! but my voice wouldn't comply. I was hypnotised by her voice; low and dark, full of sexual promise, it bored into my brain. She picked up a tube of and held it right in front of my eyes as she slowly unscrewed it. The pink tip of the lipstick emerged from the tube and as if on cue my cock began to harden.

'Pucker up baby, you're going to love this. It will make you look so sexy.'

She grabbed my chin with one hand and squeezed, forcing my lips forward. so that she could smooth the slippery lipstick onto them. She let go of me and stood back, 'Yes, that will do nicely. Now I want you to do something for me, Jamie.'

She pushed me down onto my knees and she sat behind her desk.

'Jamie, every morning, I want you to get on your knees and eat me under my desk. Do you understand?'

I was horrified and excited in equal measure.

'I said, do you understand me. Jame? Its a simple enough question.'

I finally found my tongue, 'Yes, yes, I mean yes Mistress.'

'That's better, sissy. So, get on with it.'

I crawled over to her desk and lowered my head so I could get underneath it. She had hiked up her skirt and opened her legs. I could see her white thong pulled tight into her pussy.

'First you need to pull down my panties.'

I reached out and with shaking hands I gripped the sides of her thong and pulled it down her legs. She kicked it off and opened her legs even further. I coud see her glistening pussy right in front of my eyes.

'You may begin, sissy.' she ordered.

I inched my way towards her and I could smell her wetness as I came closer. I bent my head forwards and my tongue flicked out to gently lick her.

'Harder than that, you'll never get me off doing that.'

She reached under the table and put her hands behind my head and pulled me hard into her pussy. My tongue began to lick her harder and I heard her hiss with pleasure above me.

'Thats better, my pet. Just keep doing it that hard.'

She ket one hand behind me head locking me into place and she brought the other one down and began to rub her clitoris just above my nose. I had no choice but to keep licking and she brought her legs together, trapping me between her legs. My neck and tongue began to ache, when Vanessa grunted above me and she came, her juices coating my face with its sticky sweet nectar.

'Enough, sissy. you can come out now.'

I crawled out from beneath the desk and knelt before her.

'Thats a good start, my pet. A bit rough, but practice will cure that. Now, go and wash your face and here,' she handed me the tube of lipstick, 'go and freshen up your lipstick.'

'But Mistress. what if someone sees me?'

She frowned, 'When will you learn to do what I tell you with out arguing? Just do it, you silly girl.'

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