tagTranssexuals & CrossdressersThe Thomas Thompson Affair

The Thomas Thompson Affair



A series of stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me!


1.... The Present...

"Now. I want it now;"

"Shut up Geoff;"


My voice was getting louder and my pose was becoming sillier. My pants were at that moment on my head.

"Shut up Geoff, you look totally stupid" called out Louise, trying to stop laughing at the ridiculous sight in front of her. "Go and get shaved, and dressed, You'll get it later. I need my coffee first."

So I shaved, and dressed, and realised I needed to speed up just a little or I could be late for work, birthday or no birthday. In the kitchen, Louise was sat at the table glancing at the paper and drinking her coffee. I grabbed mine.


"No I won't. I want it NOW"

I shouted, I hopped up and down, I pulled funny faces, I repeated my desire in several silly voices. The sort of behaviour you wouldn't attempt with someone you wanted to impress, a new girlfriend, a newly-married wife and so on. But the sort of behaviour which is perfectly OK with someone who knows you well - as well as a wife of more than twenty years standing does, for example.

I didn't need to ask the question. She stood up and glanced out of the window to make sure no-one was passing, then turned to me, pulled the string on her night-dress and pulled out her ample breasts.

"Is this what you want? You'll have to be quick, it's the right one this morning I think."

Private joke. I started to laugh, then realised she was distracting me.

"No you don't, I want my birthday present. Now!"

"OK darling. I've got you a date."


"Yes, a date"

"Date? What sort of date?"

"Well, how many sorts are there?"

I wasn't getting anywhere with this, Louise was being deliberately obtuse. I knew then, this was going to be a bit special as birthday presents go. If I ever got it, that is.

"Well, there's dark sticky fruit dates, there's October 25th type dates, I am sure there are more. So what type is it?"

"It's a date. For tonight. You're going out."

"Oh, a going-out type of date. Why didn't you say?"

Then I realised. OK, that sort of date, but this didn't make sense. Going out? I looked at Louise, puzzled.

She looked straight at me. I could tell something dramatic was about to escape from her mouth, that whatever it was she knew it was going to surprise me.

"Geoff. How long have you been a cross-dresser?"

That didn't follow. I didn't see it, but I answered anyway.

"About four years."

"Right. And what have you done with it?"


"What have you done with it? You dress up, you look lovely, roughly once a week these days. We sit in the garden and have tea together, you sometimes cook or iron."

"And we make love" I butted in, smiling.

"Yes, we make great love, it's stupendous. I do so LOVE being screwed by you, in a bra and panties and all. But I keep telling you, you need to do more. To get out and about."

Suddenly I realised where this was going. Louise had several times recently, when I had been in 'femme mode', suggested we go for a drive, or go shopping or something. I had said no, every time.

"Well, Geoff, you've got a date. That's your birthday present. I rang up an escort agency, they are sending a man round tonight. Eight-thirty. And 'Gemma' is going out."

I sat down.

"A man?" I muttered.

"Don't worry, it's all taken care of. I asked the agency rep on the line. The guy who's coming, Peter, knows. I told them my husband is a cross-dresser and I want someone to take him out. Just out to a pub for a drink or two, then bring him, or rather her, home. That's all."

"All? ALL? You mean I am due to go out tonight - with a man. Look, Louise, we sorted this. I may tart myself up, but I am strictly a one-person guy, indeed a one-woman guy, and that's you. Totally hetero and very happily married."

Louise got up, came round behind me and kissed me, nuzzling my neck.

"I know that, silly, this is a one-off. I thought you would like the idea. Look, think about it, if you want to cancel then ring me later today. But if you like the idea try to get home a little early, we have to get 'Gemma' ready. Please, think about it. Now, come on, you're going to be late if you don't scoot."

And scoot I did, staying mainly just under the speed limit I did get to work on time. But I was distracted, all morning, thinking about it. What a hoot! And Louise, what had made her come up with this. But just one outing, to a pub, could I do it?

Of course I could. At lunchtime I rang Louise.

"Hi, Geoff, you want to cancel? I can ring the agency now if you want."

"Louise, no. Look, I'm sorry if I didn't seem grateful this morning. It really is a great thought. And yes, I'm going through with it. Love you."

I was distracted all afternoon too but managed to get my desk cleared early and left exactly on time. I drove home quickly, and carefully, to find Louise beginning to prepare for the evening already.

"OK Geoff, let's eat first. I know it's early but I want to have a good run at getting you dressed and made up."

Within twenty minutes we had dined and cleared away, and I was heading up to the 'spare room' where all my femme clothing is. Louise had beaten me to it - the outfit she had chosen for me was laid out on the spare bed. She followed me in.

"OK Geoff, get undressed and shower while I finish sorting here. Use my shower oil, it smells nice, we do want you to look AND smell good on your first date, don't we?"

She was winding me up, OK, but I was by then delighted to go along with the whole thing, positively looking forward to it.

Until about 8:25, that is. By then I was getting definite cold feet. Literally too, I was sat in the kitchen, all dressed up and nowhere to go - yet. And my feet were a little cold. My heels were fine, black, chunky heels, fairly fashionable, about 3" heels and rather chunky. But I was wearing thinner stockings than I was used to, about 15 denier and black. Louise had always said I have good-looking legs in stockings, and had suggested a couple of weeks earlier that I shave my legs and arms carefully so that I could expose them more when dressed. I always wore black stockings or tights, they had helped cover my slight leg hair. Apart from actual slightly cold feet I was feeling rather apprehensive.

"Don't worry, - Gemma. You look great". Gemma, that is my 'femme' name, from 'Geoffrey' really, Louise has been very good in nearly always calling me that when I am dressed.

In truth, I had felt pretty good, we had done as good a job as ever on my overall 'look' that evening. Short-ish skirt, a few inches above the knee, a dark denim, a pale blue blouse over my black bra and undies, a mid-blue tailored jacket, nice make-up and accessories, I was very impressed with the general appearance of the woman I was pretending to be. Louise had taught me to moderate my voice, take it up a tone, I could speak in a very convincing though slightly husky, and maybe female, register. Everything had gone OK for an evening in doing our usual 'role-play'.

But I wasn't staying in, I was going out. It really was a great idea for a birthday present, I just had to summon up my nerve to do it. Louise had insisted that I didn't have a drink to boost my courage, she said that Peter would be buying me drinks later. Peter. My date! I had asked about the arrangements with the escort agency, she really had been clear about the special circumstances on the phone. Peter was one of their experienced escorts, apparently he had not actually been out with a cross-dresser before but he was quite happy with the idea. He is gay himself, and had some experience of being with others who had the same hobby, even one who had gone the whole way and changed his, or rather her, gender.

The doorbell rang. I shivered slightly, not from the actual cold, just nerves.

"OK Gemma, you stay in the kitchen for a couple of minutes, I'll make sure this guy knows properly what is expected of him. Don't worry.'

Easier said than done. I sat there quietly, listening to the conversation, trying to peer through the crack in the door. Louise went through the usual pleasantries, then got to the point.

"Peter, you do realise don't you, this is a different sort of escort. They did tell you at the agency."

"Patrick. My name's Patrick, not Peter. I'm sorry, Mrs. Thomas, I only have the ordinary details from the agency here". I heard the rustle of a sheet of paper. "Escort Mrs. Thomas to a golf club dinner. That's all I know."

There was a short pause.

"Thompson, Patrick, I'm Mrs. Thompson. And I don't know anything about a golf club dinner."

"Shit!" I heard Patrick say. There was another pause. "Er, excuse me asking, Mrs. Thompson, I do apologise if I have got something wrong myself - you said 'different sort'. You aren't by any chance expecting a gay man for an escort?"

"Yes, I am. I had made very specific special arrangements."

"Look, Mrs. Thompson, I am really sorry about this, there has been a mistake at the agency. I have a colleague called Peter, I think we have been given each other's assignments. May I make a call?"

I heard the beeping of a mobile phone as buttons were pressed, then heard half a conversation.

"Hi Peter. Patrick here............... Yes I know, I've just found out ....... Gloucester...... about an hour, that's not on is it? ...... OK, you go ahead, I'll try to sort things this end.... OK. Bye."

Peter spoke again to Louise.

"Sorry, there has been a mix-up. Peter is going to go ahead with his escort, we haven't time to swap over. I really am very sorry, I can't apologise enough, someone back at the agency has messed things up somewhere. Obviously, you may be offered a free replacement 'date'. Might that be acceptable?"

"Yes, but I did really want it to be tonight. Hang on a moment."

Louise came into the kitchen and spoke quietly.

"Did you hear that? Great shame, you really do look great tonight my darling."

Then she paused again and went back into the lounge, I heard some muttering, then she reappeared a few moments later with Patrick. He looked at me. I was not expecting that at all, I just assumed that the whole thing was off. He turned to Louise.

"I am amazed, Mrs. Thompson. Yes. Definitely. I was expecting some sort of drag artiste but ... well."

"Right then - er Gemma. This is Patrick, he's taking you out for a drink or two. You had better get your handbag."

I was by now totally unsure about the whole thing and decided I should have a say in this.

"Hang on, I'm not sure about this."

And what amazed me, Louise noticed too, was my voice as I spoke. It was my 'Gemma' voice, as if I was reluctant to speak normally when dressed like that. Louise had always encouraged me to speak in that more gentle way when I was dressed and doing the cleaning, or having tea, or whatever. It seemed that it had become almost automatic.

"Please, Mr. Thompson. I assure you. I am totally happy about this, and not just because I need the money. Actually that is a large part of the reason. But you do look great, you even sound convincing. If I didn't know what I do know, maybe I would even, in a different situation, try to chat you up anyway. You really do look great. Honestly."

"There, Gemma, I have been telling you that for ages. Now, come on, this is going to work. Go get your handbag, it's on the bed upstairs I think. I'll just finish briefing Patrick."

I really was in two minds at that stage. Patrick seemed a totally presentable young man, though over-dressed for a pub visit. Apart from him not being gay, and I had not been at all sure about that when Louise had told me what she had tried to arrange, well, there really was no reason not to go ahead.

I came down and went into the lounge, Patrick and Louise were still chatting, quietly. I must have still looked doubtful. He came towards me and took my hand.

"OK Gemma, love. Come on, we'd better be off."

I looked at Louise, we both raised our eyebrows. Patrick's tone of voice had been exactly right, a man encouraging his girlfriend to get a move on.

"Patrick" interrupted Louise "You said you were a student. What are you studying?"

"I'm doing a Business course. Why?"

"You should be doing acting, you are very good - indeed."

She turned to me.

"Now Gemma, you take care, have a good evening. There shouldn't be any problems outside, the Sandersons are away and Mrs. Davis can't see over the road from her kitchen, not in this light anyway. And don't be too late." I looked at her - she was grinning. I tried to.

2..... The date...

Outside, Patrick kept hold of my hand. We walked together along the drive to his car, a rather swish affair.

"It's not mine, er - Gemma, it comes with the escort job. This was supposed to be for the golf club trip, to impress the friends of my escort."

He opened the door for me. I had been somewhat flustered up to then but remembered - bum first, swing my legs in, not to show my stocking tops. Patrick went round to his door, got in, and drove off.

"Mrs. Thompson has given me clear instructions. As far as I am concerned, you are Gemma - all evening. OK?"

"Yes, Patrick, that's fine. I suppose this must seem weird to you."

"Oh no, look, Gemma, in this job I have had really weird escorts to do, this is OK. And you really do look very attractive this evening, Gemma. Mrs. Thompson suggested we should go to the 'Red Dragon'. Is that OK with you?"

I knew where the pub was, though I had never actually been in. I agreed it sounded fine. It was about four miles from home, I tried very hard to relax as Patrick drove.

There are many moments in a life you will always remember. Proposing to a partner, the birth of an offspring, a specially good exam result, when your favourite football team does phenomenally well. And for any guy who has actually done it, going out, walking into a pub dressed in a tight top and skirt, tights and high-heels, that has to count as one of those special moments. Despite all that has happened since, that moment lives on in my memory.

It would be wrong - very wrong - to say that all the conversation stopped, everyone looked at me, all the men's eyes lusting after my body and so on. That didn't happen, nothing like.

So what did happen? Nothing. Well, nothing out of the ordinary that is. Patrick held my hand, or maybe it was the other way round, I was too nervous to let go.

As we stood at the bar waiting Patrick turned to me and muttered quietly.

"I never asked - I should know of course, what would you like to drink, Gemma?"

"G and T " I replied quickly.

A young barman spotted us waiting and came over, Patrick ordered the drinks. As he was getting out his wallet I realised I should be paying, really he was on a job here. He saw my concern and muttered that he had a float from the agency, and we would sort it out later.

As we made our way over to a table near the window I had to release Patrick's grip- I had my drink in one hand and my handbag in the other. We sat side-by-side facing inwards, I sipped my drink, still a little nervous. Almost automatically - I had posed that way many times at home - I crossed my legs and enjoyed the feeling of nylon sliding over nylon, as my skirt slid up a little to reveal my knees and a short length of thigh. I smiled internally.

"I told you, Gemma. No problem at all, you look really good tonight".

Patrick squeezed my hand and looked at me.

"Come on now, cheer up, don't be so nervous. This is our first date after all. Any girl should be happy to be out with a hunk like me."

I had to laugh a little. OK he was tall and not too badly built but in no way could Patrick be described as a hunk. Then I realised he had said it to break the ice and smiled again as I looked at him.

"That's better, you look even lovelier when you smile."

He really was good, obviously practised at this sort of thing, well, at the 'real' version of it. I sipped my drink and relaxed into the role. And time flew, they always say it does when you are enjoying yourself. We talked together, closely but not intimately, quietly, mainly about football. Louise had said that was a sure-fire common interest we may have, steering clear of anything contentious or any topics which could cause problems if overheard. It was a few minutes before closing time when one rather loutish customer came into the bar and announced loudly to a friend that he had just come from 'the match', and that Villa had beaten City.

There was a huge cheer all round the bar - Patrick and I turned to face each other. Everyone else was hugging each other - so we did too. As we parted I looked him straight in the eyes and wondered just for a second if that hug had been a little more than platonic. I didn't have time to do anything about it, because...

"Hi there Gemma, you two seem to be getting on well, then."

I knew the voice, obviously. I didn't need to look up but I did, we both did. Louise squeezed into a chair facing us and leant over, speaking quietly.

"I'm sorry to interrupt your date, I just had to see how you were getting on."

"We are doing famously, Louise" replied Patrick "Gemma is doing so well. Can I get you a drink?"

Louise leant over again, conspiratorially, as Patrick went in search of a vodka and tonic for her.

"Seriously Gemma, how are you doing. Any problems?"

"None at all so far, this is a real buzz, a great birthday present."

Patrick returned with Louise's drink, we chatted for just a minute or two, then trouble did intervene - oddly, without my wife being there it just wouldn't have happened. We all heard it - a loud voice from the other side of the bar.

"Louise! Hi there!"

She looked across automatically, then looked at Patrick and I.

"Bother, it's Kelly, from work"

But Patrick had been ahead of us, he stood up between me and the approaching Kelly.

"Gemma, darling, come on, we should go. I want to show you something I saw in the 'Gap' window. Let's go have a look."

So, shielded by Patrick's body, I grabbed my handbag and shuffled out. I heard behind us 'sorry Louise, I hope I didn't interrupt anything ...'.

But we were away, heading out of the pub. Patrick's hand round my waist to encourage me along.

"Well done Patrick" I said as we turned the corner outside the door.

"It seemed the best thing to do" he said. "Come on now, let's go have a look in that window anyway"

And so we did, Patrick hugging me round the waist, just like any other couple window-shopping, walking and laughing together when Patrick started going on about Kelly and her piercing voice. After that he drove us home, and brought me to the front door. Louise was just putting our car in the garage and met us on the doorstep.

"Young man" she said, looking at Patrick. "On Monday I am going to ring your boss and give you a seriously good report. You have done brilliantly this evening, especially getting Gemma away from Kelly. But all the other things too."

She moved towards him and kissed his cheek.

"Right, Gemma, let's go in. I'll let Patrick off the last part of the contract."

When we both looked puzzled she continued.

"When I rang and arranged for tonight, I wanted a pub outing, and a walk in town - and a goodnight kiss for Gemma. But we'll let you off that last part."

"Why?" asked Patrick.

And then, without waiting for a reply, he grabbed me, not too firmly by the arms. And pressed his lips to mine, Just briefly, just for maybe two seconds. But it was my first kiss!

Then he did say goodbye. I was concerned we were there, rather exposed outside our house albeit in the dark.

"Right Gemma, tell me all about your evening" Louise asked as we closed the front door and retreated to safety.

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