Changing Roles
By Julie Dawn Cole
Chapter 31

Emily took my hand and led me into the bedroom that she had allocated to me that was luxurious compared to my apartment and the one I’d grown up in at home. It was even better than most hotels I’d ever stayed in and I’d been excited by the prospect of sleeping under the freshly laundered and crisp white sheets in the large inviting bed. Emily sat down on the bed and gently pulled me to her side.

‘Jules you were amazing tonight and you did everything I’d hoped you’d be able to do and more. My memories of growing up with a brother melted away as I watched you two chatting and I saw I had a beautiful sister and she was bonding with you and as you relaxed in her company I saw just how feminine you are when you let down your guard.’

I smiled but stayed silent. Whilst the smile was to acknowledge the complement the silence was because I was concerned that she had commented on my femininity that she had clearly accentuated since her arrival at work. I was realising that she was turned on by our reversal in roles and she was a new age of woman who needed to be recognised as equal or superior to colleagues, especially the males. She spoke softly whilst holding my hand.

‘I realise now that George has always been Georgina and that when we were growing up he behaved like a big sister and was happiest when we did things together. In truth I never saw the girl or the boy just someone I adored and who I followed around and hugged every day. I was probably ten years of age before things started to change and arguments between George and our parents started. Sometimes they were loud and intense with lots of cursing and shouting. Dad would get really angry. I would sneak into Georges bed at night and hug him until he fell asleep. In a matter of weeks dad insisted that I go to private school whilst George was sorted out and by the time I returned everything would be calm again. It never happened and my time at private school went on until I left for college and university.’

I could see a softer expression on Emily’s face than I’d seen before in the short time we’d spent together at work and increasingly socially. I couldn’t imagine what it would have been like to go from a loving family environment with a caring sibling, brother or sister, to a school with dormitories 7 days a week, filled with other children and no parent to snuggle if you hurt yourself or to give you advice or assistance. What on earth had been going through the minds of her parents to send her away whilst they sorted out her brother?

I could only begin to imagine the hurt that Emily went through every day seemingly being punished. I had no reason to complain or deny help to my own parents for the love I’d received in my life even if I had no siblings and now felt all alone. Clearly the private education and the lost family connection was a factor why Emily had become strong and independent that perhaps had been one of the objectives of her father. But from what I’d learned he finally gave up on George and abandoned his family after an affair at work What on earth had George and Emily gone through and what was the effect on George and his mother after Emily was sent away? I dreaded to think.

Emily noticed my quiet and spoke up to bring me back from my reverie. ‘Jules you are quiet. Are you feeling awkward because I kissed you and told you that I love you? Have I embarrassed you?’

‘No Emily. I was just thinking of how life must have been for each one of you these last years and how you all suffered in your own way. You all lost each other’

‘Well we all struggled I suppose and mum was almost at the point of a nervous breakdown so she relied on my uncle to get through it. I did too and he took me under his wing and visited me regularly. He paid all my fees. Anyway that is by the by. More important than that did I embarrass you?’

‘Not really but you surprised me with the kiss. It’s not the sort of thing I’m used to experiencing so I didn’t know how to react. Maybe it was a natural reaction after such a nice evening with Jina, I realise it was a very emotional experience for both of you.’

‘You make me smile sometimes. You are so naïve. I think you missed out a lot growing up. Did you never feel like you wanted to kiss somebody or even to be kissed?’

‘I guess not. I didn’t really have close friends in my school or college days just casual acquaintances.’

‘It does show Jules and that is a reason that I want to help you. I kissed you because I felt the urge. You are so vulnerable, and you’ve just accepted the changes in your appearance and your lifestyle without any resistance or complaint. Not one attempt to resist the changes in your job and you just accepted me as your boss and supported my decisions without any objection.’

‘I didn’t have much choice and besides I soon saw that you were a strong leader and a decision maker. It’s hard to believe that somebody so inexperienced in the business can take charge and become instantly effective. It’s not normal.’

‘Thanks, but maybe it’s because the foundations were set by you and George and it was only that you missed what was going on under your noses.’

‘Well I can see that some of the changes have helped identify an element of fraud or corruption but it doesn’t explain why you singled me out and trusted me to come here and meet Jina and why you have spent so much time with me outside work.’

‘I guess I showed my true colours and let my guard down for once. I was intrigued from the first time I met you and took the trouble to find out more about you. I had no intention to take the role of CEO or to move North but when my uncle asked my opinion on the business that you and George were running I saw an opportunity to meet you and find out about you.’

‘I hardly recall meeting you except in passing when a group of you visited us with your uncle.’

‘Well, I did remember meeting you. It didn’t seem like you were cut out to be a Managing Director and I wondered if you had the job because you were a man rather than give a woman the job. I did soon realise that you had a lot of feminine traits, and my mind wondered a bit as I watched your reactions and the way you carried yourself. It was as if you were a woman masquerading as a man and I sensed it from the moment we shook hands when we were introduced. You have such small hands and slender long fingers that are very feminine. I wanted to lean across and kiss you because you reminded me of one of my girlfriends at university. She is married now with a baby on the way.’

I was surprised and didn’t know how to respond but then Emily placed a finger under my chin to hold my face still and leaned across to kiss me again. This time I tried to push back a little and show that I liked the affection. Emily put her arms around me and held me close and I didn’t want to break free. I guess we stayed like that for a few minutes before Emily pushed me gently back to lay on the bed where we stayed a while kissing each other. This was all new to me, but Emily wasn’t perturbed at all and just took charge.

Eventually I managed to speak fearing that things would go too far. Emily had already placed my hand on her breast and was stroking my inner thigh. She pushed her tongue into my mouth seeking a response I did my best before coming up for air. ‘Emily we should stop this and get to bed. It’s getting late.’

‘Whatever you wish Jules. I suppose we should remove our make-up and use the bathroom.’

With that she got up and headed to her bedroom and I sat up completely confused. What was Emily expecting of me? How could a beautiful woman like her show affection for me? Especially since I was en femme. I looked in the mirror and saw my lipstick was smeared and my hair dishevelled. I went into the bathroom and slowly removed my make-up and undressed. I still looked more female than male even after removing my bra and putting on my sleep shorts and t shirt. My stomach was churning as I cleaned my teeth and used my mouthwash. I had never felt like this before, and I wondered if I’d be able to sleep.

I turned off the lights and slipped into the huge comfy bed and lay there reflecting on the events of the day and what Emily had said to me. Was I really so feminine that people noticed even when I was dressed in male clothes? Did I really have feminine traits that were obvious. Why had nobody ever said this and was this why I enjoyed cross dressing and going out to gay bars?

As I felt myself drifting off to sleep I sensed the door opening and I sat up as Emily entered. ‘Are you still awake Jules? I thought you might need some company for a while. I couldn’t let you go to sleep without saying goodnight and having another cuddle. Do you mind?’

‘No Em it’s fine. But I was almost asleep, and I guess it’s the wine that did it.’

‘It has the opposite effect on me it makes me feel alive. I could just snuggle up with you if you feel tired. I promise to behave.’

‘Well I’m embarrassed but it’s difficult to refuse since this is your hospitality weekend and I’m a guest. But I hope you don’t expect much since I already admitted to Jina that I have no experience and to the best of my knowledge it’s because I’m impotent. Also, it seems now that I’m half way to being transgender if there is such a condition. So I don’t have much reaction to approaches by women or men.’

‘Well why don’t you just relax and we can explore things together. I’ve had plenty of time under the sheets with girlfriends but that doesn’t mean I’ve slept around and especially not with men. You have stirred something inside me, and I hope that I can stir something inside you. How do you feel when you see me? I find that I want to hold you and never let you go when I see you. Even at work when you come into the room, I find I’m distracted and it’s not like me.’

‘I do find myself being distracted too but at the same time I’ve been trying to deal with my demotion to a PA and being treated more like a female member of staff. It sounds like you had a reason for retaining me that wasn’t just because of my experience in the job.’

‘Well if that’s the impression I’ve given you then I hope that you can forgive me. I think this was you all along and I just gave you a little push.’

Emily moved towards me climbing under the sheets and then leaned over to kiss me again. I liked it and held my position on the bed until my back started to ache a little. I lay back and Emily rested on her elbow on the pillows so her face was close to mine and she put her hand underneath my t-shirt and touched by ‘breast’ stroking it gently and taking my nipple between her fingers until I felt it respond and it became firm.

‘See there is some response. I’m sure I can stir something down below if you let me touch you. Would you mind?’

‘No but please don’t be disappointed since I’m not as developed as most adult men or many teenagers for that matter.’

‘Would you like to touch my breasts and explore under my panties to see what reaction you might get. Don’t be shy.’

I returned the favour and her breasts felt warm and inviting so she suggested that I kiss them and see the reaction. Her nipples seemed to treble in size and as she covered them again they pushed through the silk of her nightdress. She lifted it and pulled me beneath it until I could reach her nipples with my tongue. I kissed and sucked on both of them amazed by the response. She was almost purring like a cat.

She then took my hand and drew it towards her thighs and then gently stroked her pubic area that seemed freshly shaven and well-trimmed. ‘Let me explain the parts that you are touching and you should be able to see by my reaction which are most sensitive. Don’t be scared.’

She started by moving my fingers gently across her outer lips and then explained about her clitoris that seemed like a small penis. She widened her legs and pressed my hand so my fingers explored inside her. Suddenly my hand was wet with a light sticky substance and she closed her eyes and groaned. ‘See what you do to me Jules. This is how I feel sometimes when you stand close to me. Imagine if our relationship was to develop further. Do you mind if I touch you?’

Her hand moved beneath my shorts and beneath the panties I was wearing and for the first time in my memory I sensed a response and some stiffness. As she stroked me the soft and flaccid appendage that was part of me came to life. It felt as if it had doubled in size and as she stroked it I felt it become as rigid as a stick.

‘Well,well Jules something is happening below deck. Are you sure this is a first time for you?’

‘Yes the first time it has ever been so hard like this. Before it has been a bit floppy sometimes like a sausage out of a fridge. This is like it came out of the freezer.’

‘Well let’s see if we can defrost it. It just needs a cuddle. Let’s just remove those sleep shorts and panties.’

I didn’t resist and lay back as Em prompted me to lift my hips whilst they were removed and discarded. She then slipped out of bed and crouched and inserted something inside her that she said was necessary as a precaution at this time of the month. Clearly she meant she was inserting a condom of some sort. Then she pulled back the sheets exposing my lower body and my erection We kissed again and Em placed my hand on one of her breasts and then the other stroking her nipples. She then lifted my T shirt and removed it and kissed my breasts. I was still stiff as she lay on top of me and rubbed her tummy against mine. She carried on for quite a while before lifting herself and holding my erection so she could position it in the right place to connect.

Then she made love to me and clearly had several organisms before I suddenly exploded myself. I had never experienced a feeling like it.

‘There you are Jules now you will find that you are fully de-frosted. You do realise that you just lost your virginity don’t you?’

Of course I did and I wanted more. What an experience. I clung on as long as I could until we automatically disconnected and Emily kissed me and lay back. In moments she was fast asleep and I lay for a while wondering if I should go to the bathroom to clean myself. Whoever would be laundering the bedding would know what had taken place. Still on the positive side the bedding in Emilys room was still fresh. It took a while for me to relax and fall to sleep. I felt so relived that I had finally ejaculated and could be considered part normal.

I recalled a song from a musical ‘Why can’t a woman be more like a man?’ I think Emily ticked that box and I was looking forward to the next day.