What happened to me during the following week

Suzanne’s cousin Clare:
and how she changed my life

by Louise Anne Smithson

Chapter 7

With Debbie at work

---

I was the office junior at work having only been appointed to a one year contract at the beginning of March, and I was also the only male on the staff. Karen, who was in her early thirties was in charge, Helen who was a few years older was the second in command, and then there was Debbie who was only a couple of years older than me. She worked hard and was good at her job but liked to chat a lot at the same time. She was always keen to discuss what everyone had done over the weekend, although I rarely had much of interest to contribute in return. All the same, I enjoyed my work and got on well with my three colleagues and got the impression that they appreciated my efforts. The main disadvantage with the job had been that I’d not been permitted to take any paid leave until I’d completed my first six months of probation, which meant that I had a sizable chunk of leave entitlement remaining which I planned to take from mid-December, as by then the pre-Christmas rush was over. I’d originally planned to return to Northumberland for a couple of weeks and it was only after I’d arranged everything at work that my Dad informed me that he would be going away for Christmas and the New Year.

I arrived at my job at the usual time on Monday morning, having first carefully taken out the studs from my ears, and scrutinised my face to ensure that we’d removed all trace of the makeup from the previous day. On this occasion our two seniors were out visiting clients and so I had Debbie’s undivided attention, although after various non-committal replies in answer to her enquiries about the dinner party on Saturday, she gave up her attempts at making conversation. Mid-way through the morning, we stopped work for a while to have a cup of coffee. After a few minutes of awkward silence Debbie decided to try again on a new subject.

‘Tom, if you’re going to have pierced ears then you’ll need to put in a pair of studs to stop the holes from closing up,’ she commented in a matter-of-fact way.

I coloured a little, wondering what to say.

‘You’re very observant. I do have a pair of studs which I’ve been wearing at night but they’re a little too ‘girly’ looking for me to wear in the office,’ I replied.

She smiled.

‘I’ve some transparent nylon sleepers that I could put in for you if you wish. Once they’re in place they’ll barely be noticeable, but they will stop the holes from closing.’

I agreed and she found them in a small tin box, which she kept in her handbag. She drew close and started to insert the tiny pieces of plastic into the holes in my ear lobes. As she did so she looked closely into my eyes.

‘If you’re worried about looking girly then why did you pluck your eyebrows?’

My cheeks were now bright red with embarrassment.

‘Your eyelashes also seem to be darker than they were before. Just what have you been doing over the weekend, Tom?’ she demanded.

I sighed, then answered.

‘It’s a long and complicated story.’

Her face brightened up at the prospect.

‘Good! In that case you can tell me all about it. It’ll give us something interesting to talk about this morning, for once,’ she said.

‘If I do tell, you must first promise me not to tell the others.’

‘Alright then, I’ll promise, but in that case you had better give me the whole story before either of them returns.’

---

Over the next hour or so I told Debbie about my last two weekends and even showed her the photos of Clare taken by Suzanne.

‘Tom these are amazing, you look so much like a young woman that I’d never have guessed it was you, or indeed any bloke.’

I was still blushing slightly, but also feeling quite pleased by her reaction.

‘I suppose I did look fairly good by the time Suzanne had finished with my makeup,’ I commented diffidently.

‘And you also managed to persuade two of her friends that your name was really Clare?’ she said a little incredulously.

‘Yes, I believe so, at least they showed no signs of having any suspicions about me,’ I added.

‘That’s such a bizarre story, and what did you feel about it all?’ she asked.

I shrugged my shoulders.

‘At first I was a little anxious about the idea and was frightened that I would be found out. However, as time went on, I got used to wearing the clothes and makeup and began to relax a little. I even began to feel like a different person and gained in self-confidence, so in the end I had quite a good time during my evening as Clare.’

Debbie smiled and shook her head.

‘Yes you must have enjoyed yourself as you went out in public dressed as Clare on the two Sundays as well?’

‘The first occasion was just a trial to see how I got on and whether I would be recognised. Yesterday Suzanne took me out for lunch to thank me for standing in as her cousin, and to celebrate our success. I must admit to having had a really good time.’

‘Did anyone recognise you then, as you were in broad daylight?’

‘No, I don’t think so. I was aware of some people looking at me, at first, but not in a nasty or sneering way. I don’t believe anyone recognised me as a man dressed in women’s clothes,’ I answered.

‘I would tend to agree with you,’ said Debbie looking at the pictures from Sunday once again. ‘The guys were probably admiring your good looks and wondering what you would be like in bed, and the girls were just sizing you up as a potential competitor.’

I blushed at this thought.

‘In some ways I felt like a different person when I was dressed as Clare, and I also discovered that people are generally nicer in the way they respond to women. They’re chattier and friendlier, and hold doors open for them,’ I replied.

Debbie smiled.

‘You only saw the half of it though, guys also tend to patronise us and expect us to do all the menial tasks in return for a little attention,’ she said ruefully. ‘But I wouldn’t want to swap places with one.’

I continued to blush so she looked at the pictures once more.

‘So you appear to have had a good time as Clare on Sunday as well as the Saturday night?’ she asked.

‘Yes, I suppose so.’

‘And when are you planning to go out as Clare again?’ she asked

‘What makes you think that I shall be doing so?’ I countered.

‘The holes in your earlobes of course, and the fact that you’re still trying to keep them open. You don’t strike me as the sort of bloke to wear one, let alone two studs. That’s what attracted my attention in the first place.’

I hesitated before answering.

‘Suzanne has asked me to go with her Christmas shopping in Regent Street next Saturday. She has asked me to dress as Clare again so that I’ll be able to go into the changing rooms with her and help her to try on some clothes.’

‘In that case why don’t you come into work one day before Christmas dressed as Clare? We could see whether Karem and Helen recognise you.’

I shook my head.

‘I’m sorry but you can forget about that idea; remember that I’ll be using up the remainder of my leave from 12 December. In any event, the clothes I wore belong to Suzanne, and I don’t think Karen would approve of her junior assistant coming in to work in drag.’

‘I don’t think either of them would mind if you looked as smart and convincing as you do in those pictures,’ answered Debbie.

‘I only looked as good as I did due to Suzanne’s help with my makeup,’ I replied.

She paused for a minute, continuing to look at the photographs.

‘Alright then, but now I’ve heard the story and seen the pictures I would really like to meet you when you’re next dressed as Clare. What if I were to come into central London next Saturday, could we perhaps meet up for lunch together?’

I’d been working with Debbie for the last seven months and she’d never once suggested that we met up outside of work before now. In fact on the one occasion that I’d suggested we might have a drink after work she’d rather dismissed the idea.

‘I don’t know Debbie; I’ll have to ask Suzanne this evening to see what she thinks of the plan.’

Karen returned to the office at that point and so further discussion about the previous weekend and Cousin Clare was curtailed for the remainder of the day. Nothing more was said about the holes in my ears and neither Karen nor Helen seemed to notice them.

---

That evening, after I’d finished my evening meal and cleared up, I locked my bedroom door and proceeded to change into the clothes loaned to me by Suzanne, putting on a bra and knickers, a pair of tights, and a camisole before sitting down in front of my bedroom mirror. I took out the nylon sleepers and inserted the two ear studs. I then carefully made up my face in the way that Suzanne had shown me, paying particular attention to my eyes. It took me some time to achieve satisfactory results, and there were a couple of false starts, but eventually I was pleased with my look. I wished that I had longer hair of my own to complete the image, but instead I put on Suzanne’s wig and brushed it into place. It was now almost nine o’clock and most unlikely that anyone would call for me, so I finished dressing and then picked up my mobile phone to call Suzanne.

‘Hi Suzanne!’ I said when she answered

‘Oh hi Clare, I’m glad you’ve rung’

‘How did you know it was Clare rather than Tom that was calling?’

‘I don’t know, it must have been something about your voice, but I was quite sure as soon as you mentioned my name. I trust that you’ve been practising with the makeup that I bought you.’

‘Yes, if you could see me now I do believe you would be quite pleased with my efforts.’

‘In that case why don’t we speak to one another on Skype? I’ll then get a better idea of how you are doing.’

‘Alright then, I’ll log-on.'

A few minutes later the connection had been made and both of us could see one another.

'Well I must say that you appear to have done a good job again on your appearance again,' said Suzanne.

'Thanks,' I said.

‘So what can I do for you young lady?’

‘My workmate, Debbie, noticed my pierced ears and my plucked eyebrows this morning — you know, the ones which you said would never be noticed.’

‘I’m sorry about that Clare, but I’m sure that nobody made a great fuss about it though, did they?’

‘No. Fortunately the others in the office haven’t noticed, but Debbie was quite determined to find out what I’d been doing and so in the end I had to tell her the story of my weekend and even showed her your photographs. She was really cool about it all and has promised to keep my secret at work, but says that she’d like to meet Clare. She has asked whether she could join us for lunch in the West End next Saturday. What do you think?’

Suzanne hesitated.

‘I don’t want to sound unfriendly but I think it might be difficult for us to meet up with your friend on Saturday, especially in one of the cafeterias at lunchtime. I know there are still three weeks to go before Christmas but the stores get very crowded at that time and it can be a problem with a wheelchair and so I would rather not commit us to being in one shop at a given time. If she’d like to meet you as Clare, then why don’t you meet up to have lunch with her on Sunday when I’ll be having lunch with Christine and Eleanor? Alternatively, I should be happy to entertain you both to an afternoon tea on that day at my flat.’

‘Either of those options would mean my having to stay a second night in your flat as Clare.’

‘Yes, but I’d rather hoped that you would do so, in any event, since you won’t be able to come and stay with me the following weekend,’ said Suzanne.

I thought for a moment before answering,

‘Alright, I’ll put your suggestions to Debbie in the morning and let you know what she says tomorrow night.’

‘Good; it’ll be another opportunity to have a chat to my cousin Clare.’

---

The following morning I was able to have a brief conversation with Debbie whilst our colleagues were otherwise engaged, and explained Suzanne’s reservations about her plan to meet us on Saturday.

‘So it’s a choice between Sunday lunch with Clare alone, or else afternoon tea with the pair of you, at your friend’s flat,’ said Debbie.

‘Or indeed both, if you wish,’ I added.

‘In that case both would be nice. We may as well spend some time together as I shall be making the journey into central London. Then we could have a wander around the West End together in the afternoon. I don’t often get the chance to come into central London at weekends.’

‘Alright. Shall we meet at about 12.30 at the entrance to Leicester Square tube station?’ I asked.

‘That would suit me. I’m quite looking forward to it. What will Clare be wearing?’

‘I’m not sure, it’ll rather depend on what Suzanne will loan to me, but from what I know of her wardrobe, I imagine Clare will be quite smartly dressed, and in any event she’ll be able to recognise you.’

‘So you’ll definitely be wearing a dress?’

‘Not me, but I expect that Clare will.’

‘In that case I’ll probably do the same.’

I confirmed the arrangements with Suzanne that evening during another chat session using Skype.

---

Nothing more was said between Debbie and I on the subject of Clare until the Friday afternoon, I continued to practice wearing makeup each evening although I had to lay off the mascara brush somewhat as I couldn’t help noticing that my eyelashes appeared to be gradually growing thicker and darker. Debbie appeared to have noticed as well as she fluttered her eyelashes at me in a significant way on one occasion in the office. However, I don’t think my two older colleagues noticed, or at they least didn’t say anything if they did. On the Thursday I purchased a tube of hair removal cream. That night I ensured that my legs, arms and armpits were once again smooth ready for another weekend to be spent as Clare.

On Friday afternoon, just as we were packing up for the weekend, I went over to Debbie and quietly said to her.

‘So you’ll be meeting Clare on Sunday lunchtime.’

‘Yes, and I’m quite looking forward to it,’ she replied enthusiastically.

‘Me too,’ I mouthed.

---

I hurried home and quickly showered and changed into a t-shirt, jeans and trainers. I then collected the various item of apparel and cosmetics loaned to me by Suzanne, and made my way to her flat, arriving about twenty minutes earlier than I’d predicted.

‘Hi Tom, I’m afraid dinner won’t be ready for forty five minutes,’ said Suzanne.

‘That’s alright, would you like me to get myself changed whilst I’m waiting? I’ve brought with me your clothes and wig’ I asked.

‘My goodness, you are keen to become Clare again!’ she commented.

‘I just wanted to show off my newly acquired skills in using cosmetics’ I said.

‘Alright then, but first of all let me show you what I’ve been doing over the last few days sorting out my wardrobe. It has been a major task for me and one that I’ve been putting off for a long time.’

She led me through to her spare bedroom.

‘All of the clothes in this room are surplus to my requirements, as I now have to restrict myself to wearing items what I can manage to put on by myself without difficulty. They should all fit you alright and you’re welcome to wear anything you choose from them.’

I noticed a substantial range of female clothing hanging in the wardrobe or else neatly folded in the drawers.

‘My goodness, I wouldn’t know where to begin with all these clothes or know what is going to suit me.’

‘Don’t worry, you’ll soon learn by trial and error, and I promise to tell you if you make any disastrous mistakes. You’ll also find that there’s some costume jewellery and plenty of makeup in the top drawer, as long as you don’t mind using stuff that I’ve already used,’ she added. ‘You’ll find the lingerie that we bought for you last week is in the second draw. I’ve also added a few items of my own that were almost new, but you may prefer to buy some more for yourself tomorrow. So now you’ve everything you might need for this coming weekend.’

There is enough here for the next six months, let alone a weekend, I thought to myself. Whatever has she got planned for me?

‘Alright, I’ll see what I can do,’ I replied.

---

I quickly changed out of Tom’s clothes and put on a bra and knickers and carefully inserted the false breasts, and tucked my penis out of sight, and began to feel like Clare once again. I put on a pair of tights and a camisole top, before selecting a dark blue dress and matching shoes. Before putting them on I sat down and carefully applied some makeup and fixed the wig in place. Finally I found myself some items of jewelry including some dangling earrings which I was now easily able to insert into the holes in my earlobes and put on the dress and shoes. I emerged just as Suzanne was serving the meal.

‘Well done Clare, your timing is spot on. You have chosen your outfit well and your makeup looks most proficient,’ said Suzanne. ‘Does that mean that you’ll be able to get yourself ready to go out tomorrow morning?’

‘Yes, I should think so,’ I said, feeling quite pleased by her reaction. ‘But I’ve not had time to do anything about my finger nails, and so I wondered if you could help me them after dinner tonight.’

‘Yes of course, but let’s have our meal first and sort out what we’re going to do tomorrow.’

---

The evening passed quickly. During our meal we each talked about what we’d done over the previous week and made plans for the coming weekend. I explained that I would be bringing Debbie back for tea on Sunday afternoon, and Suzanne said that she would be happy to meet her. Once we’d washed up and cleared away the dishes Suzanne carefully affixed some false tips on to my nails once again and polished them for me.

‘I’m gradually getting to enjoy having longer finger nails and wearing nail varnish’

‘In that case why don’t I give you a pedicure and paint your toe nails as well?’ suggested Suzanne.

‘Alright, as long as everything comes off on Sunday night. The last thing I would want is my father to discover that I had painted toenails when I go and see him next weekend,’ I replied laughing.

‘It’s strange,’ commented Suzanne, ‘I’ve known you as Tom for several months and although we always got on well together, we were never going to become close friends. However, now I find that I really appreciate your company as Clare.’

I could feel myself blushing.

‘I suppose I should thank you, for the compliment,’ I answered. ‘To be honest I also feel more relaxed in your company as Clare than I did as Tom, and am quite looking forward to the weekend.’

‘In that case let us hope it’ll be the first of many such weekends in the future’ she replied.