Watching the Detectives

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

He pressed play again, 'This is footage taken after two other attacks on Transgender women in the last three months. It appears to be the same two men running away after each attack. These were the three attacks we know about, because they were reported. I think it's fair to assume that there have been other unreported attacks on the community by these two men.'

Despite the U.K. possessing the highest number of CCTV cameras per head than anywhere else in the world, there's still doubt about how effective it is in fighting crime.

'You haven't got any better footage?'

'No, this is the best we've got.'

'So, there's a couple of lunatic dickheads on the loose targeting the TG community?'

'My bosses don't really want to say so, but yes, I think there is. I'm afraid that if we don't catch them soon, then another victim may not be so lucky.'

I snorted, 'Lucky? You think ending up in hospital is lucky?'

'I'm sorry, poor choice of words, but at least they survived.'

'And you think these two attacked me?'

'We can't be sure, but the other attacks were within a three mile radius of each other and that would take in where you were attacked. However, there was no record on any CCTV this time.'

'What are you doing to catch these two bastards?'

'I was hoping that's where you would be able to help.' I must have looked puzzled, because he hurried on, 'We're having trouble reaching out to the TG community. There's not much trust around that we are doing much to stop these attacks and there's a reluctance to talk to us.' 'Are you doing much?'

He looked away and said, 'I shouldn't tell you this but, no, not a lot. But I want to change all that. I want to build some bridges to the community, get to talk to people, to find out if they have an information that can help catch these two men. They need to be stopped.' He spoke the last few words with passion and I could tell he meant what he said.

'How can I help?'

'Can you help me to meet and talk to some of the community, help me to persuade them I am serious about catching these attackers. I thought that if you introduced me I might get more information. The only thing is that isn't an official investigation yet, I'm kind of moonlighting, so I couldn't do it as a policeman.'

'Look, Tim, you aren't going to get anyone to talk to you dressed like that. They will make you for a copper in five seconds flat. No offence, Tim.' It was true, he would stand out like a pimp at a vicarage tea party.

He looked crestfallen. 'How can I get them to talk to me?'

Perhaps there was a way, but I wasn't sure how keen he would be when I told him.

'Tim, there may be a way. T-Girls aren't going to talk to a copper, but they will talk to one of their own.'

He looked puzzled, 'What, you mean you?'

'No, Tim, I mean that if they thought you were one of them, they are more likely to open up and tell you something.'

He looked completely baffled and then the penny dropped. He blushed bright red and started to splutter. 'You mean me, dressed up? No, you can't mean it, I could never do that.'

'Why on earth not? You're not too big. You're slender enough and about the same height as me. You have a nice bone structure, and I know girls who would kill to have those eyelashes of yours.' Me included, I thought.

I started walking around him, imagining what it would take to make him presentable.

'In fact, I think that you would look pretty in the right dress, makeup and wig.'

He held his hands up. 'No. no, it's not going to happen, I'm telling you right now.'

'What are scared of Tim?' I asked, now back standing in front of him.

'I'm not scared, well, yes I am, no I'm not. It's not going to happen.'

He was still blushing, probably down to the soles of his feet.

'What's the worst that could happen? You're not going to run into anyone you know. We'll do everything at my place and we go straight from there. I'll be with you all the time. Look, do you want to talk to them or not?'

'Well, yes, but surely there must be some other way? Can't you do it for me?' He was now virtually pleading.

'No, I can't, you have to listen to the girls yourself. I can be with you, but this may be the only way to get them to co-operate.'

'Even if I did do it, it wouldn't work because I would look so bloody ridiculous. I would look like a bloke in drag.' His tone had changed now. Instead of outright denial these were now objections and, as every salesman knows, objections can be overcome.

'Yes, you might look like a bloke in drag, but that's what we all look like when we start. Some are better at it than others, because they have had more practice, like me, but everyone has their first time. I think I can help you to make yourself presentable to go as a first timer.'

'I don't know, it seems to be such an extreme step.' He was now accepting it might be possible.

'Look, Tim, I know you might be reticent about it but why don't you let me show you what could be done. Come round to my place tonight and we can give it a go. If it turns into a disaster, then that's it, I promise you. I will do my best to make you look as good as I can, remember I've had a lot of practice. Please, it won't go any further than us, I promise. What do you think?'

He had gone quiet and wasn't looking at me. 'I don't know...'

'Come on, just you and me, what harm can it do?'

He looked up at me and I could see he was going to do it.

'OK, but if I look ridiculous, then it's not going to happen, right?'

I clapped my hands together, 'Sure, sure, but I promise you it won't be.'

On a whim I leant forward and kissed him on the cheek. 'Thanks, Tim.'

He blushed so prettily and said, 'What for?'

'For what you're doing, of course.'

We made arrangements for him to be at my place later and he walked out, leaving me wondering, not for the first time in my life, what I had let myself in for. I knew Tim was about my size but maybe if I had a few more options for clothes it would be useful. I called Emily and told her what I was planning and when she stopped howling with laughter and making jokes about Dragnet and J Edgar Hoover, I asked if I could borrow some gear from her for tonight.

'Only if I can be there. I have to see this.' she was still giggling by this time.

'No, you can't, I promised him it would only be us two.'

'Spoilsport, OK, I'll drop some stuff round. What do you want? Hot pants, crop tops, that kind of thing?'

I started to think calling Emily had been a big mistake.

'No, you idiot, just some skirts and tops, I know you have some. Not too short, you understand.'

Still giggling she rang off and promised to do as I asked Soon enough the bell rang and Em was outside with an arm full of clothes.

'I hope these are OK, 'she said, 'I've brought some shoes as well, just in case. Please let me stay and watch, I won't say anything, I promise.'

'Em, you are not going to stay. He's nervous enough as it is, if you're here making jokes about Policeman's helmets, he'll bolt like a scared pony.'

'Little me? Surely not.' Emily does not do innocence well.

'Em, thanks for all this but please go now.'

'OK, I'll go, but at least take pictures, I want to see what happens.'

I shoved her out of the door and I could still hear her outside, pleading for me to take pictures.

I sorted out the clothes and came up with a few alternatives: a couple of dresses, a few skirts, tops and blouses that were presentable and not too showy or revealing. I gathered them together in my bedroom and covered up the mirrors. I didn't want him to see anything before I was finished. I had a couple of wigs that would be OK for tonight, but if this went ahead I would have to sort out a better wig for Tim.

I sat down with a glass of wine to help settle the nerves I was feeling about the idea and started to wonder why I was doing this. I wasn't absolutely sure that it would work. Who really knew how the girls would react to Tim? On one hand, I wanted to give it a try as if it could do anything to help build some bridges between the police and the community then it would be worthwhile. He would have to look good though, otherwise they would feel they weren't being taken seriously. On the other hand, I thought Tim was cute and I did think that he could look really pretty if I could get him to accept and embrace it.

It wouldn't be the clothes or the makeup or the wig that would make the difference, it would be his personality. He would have to be confident enough to make them think he was serious, not just playing them along.

Ah, well, I thought, we'll see what happens soon enough.

4 Tina

The bell rang a little after 7 and Tim stood at the door, looking less than eager to be here.

'Hi, Tim, come on in.'

He followed me into the flat and stood in the middle of the big open plan room and looked nervously around.

'You don't know how many times I thought about going straight back home and how long I stood outside the door before knocking,'

I smiled at him and said, 'You're here now and that's good. Fancy a drink before we get started?'

I think he would have said yes to anything at that moment to delay what was about to happen.

'Oh, I forgot, I brought this.' He handed me a bottle of white wine. 'I didn't know what you would like, I hope it's OK.'

'Tim, it's great, let me get a couple of glasses.'

We sat and sipped the wine, which I hoped was going to relax him a little. I reached out and touched his hand, 'Don't worry, it's not going to be as bad as you think, you are going to look good. OK, first thing I want you to do is to shave again, as close as you can. I can see you don't have much growth, but I want you to be as smooth as possible. I've laid out a razor and some shaving foam in the bathroom.'

He nodded, that wasn't too difficult, he was thinking.

'The second thing is that after you've shaved I need you to strip and put these on.' I handed him a pair of white cotton knickers, nothing too girly at this stage.

'What?' He now looked really startled.

'I have to see what I'm working with, Tim. Think of them as a pair of speedos if it helps.'

He held the knickers in his hand as if they were a live hand grenade. 'Do I have to? Can't we do it without going this far?'

'Tim, I promised you I would do my best to make you look good. To do that I need you to get right into the spirit of this, it won't work unless you really commit to it.'

He looked like he was ready to run so I gently took his elbow and led him through to the bathroom. He seemed dazed and I suspect he may have had a drink before he arrived at my place.

'When you're done there's a robe on the back of the door, just put that on and come back out.'

He nodded and I heard him exhale as the door closed. I had another glass of wine, put some soft jazz on and waited for him to reappear. About half an hour had gone past and I was at the point of knocking when I heard the door open. Tim was wearing the robe which was pink silk, very feminine and quite short. He was beetroot red and looking tense.

'Very nice, you have great legs,' I said and handed him a glass of wine. His hands were shaking and I began to wonder if this was going to work. He did have good legs though, the short robe showed them off and they looked very smooth.

'I shaved my legs too, I thought I might as well go the whole hog,' he said.

Well, well, I thought, there is hope yet.

'That's perfect, Tim, come over here and sit down and finish your drink before we go on.'

I had to stifle a giggle as he sat down as the short robe rode up and revealed his legs. He didn't know whether to cross them or to keep his legs together.

'Probably better if you keep your knees together when you're sitting in something short,' I said. 'Crossing your legs is on the advanced course.'

He looked startled and then saw I was smiling and he actually began to smile back.

'Thank you, Philippa, you're being so nice about this. I don't think I could go through with it without your help.'

'Tim, I want this to work too, so I'm more than happy to do this at your speed. Now bring your glass and come through to the bedroom.'

He grabbed his glass and followed me, now seeming to accept what would happen. I sat him down in front of my dressing table and said, 'OK, now I'm going to make you up, not too much, just enough for you to see what it looks like. I've covered over the mirror so you can't see until we've finished.'

I slipped a makeup hair band over his head,

'This just keeps the hair off your face while I'm applying the makeup.'

I didn't bother with primer as the makeup wasn't going to have to last that long this evening. His beard wasn't too dark but I started with a heavy foundation working it in with a sponge and followed that up with concealer and extra emphasis on the beard area and the neck. I talked to him at every stage gently telling him what I was doing and why. He seemed to be in something of a trance at this stage, just nodding slightly as I told him what I was doing.

I applied some bronzer to his forehead, cheeks and neck to give a little definition and then some pink blush, brushing up the cheekbones towards his ears. Working as quickly as I dared, I used nude eyeshadow to begin with on the lid and just below, followed by a light brown eyeshadow to complement his hazel eyes on the eyelid itself, working it a little beyond the eye as I wanted to make a kind of cat's eye effect. Using a darker shade I added a line just above and below the eyelashes and worked outwards to create the effect. I sat back to have a look and thought so far so good. I was still talking gently to Tim and he seemed to be taking it all in good stead so far. I thought I wouldn't use eyeliner this time, sticking a pencil close to his eyes might just disturb his mood. There wasn't much I could do with his eyebrows at this stage although they were quite light and thankfully not too bushy.

I did want to do something with those wonderful eyelashes, so I curled them and applied mascara working it outwards and the effect was transforming his face. I knew his patience might be running short so I moved onto his lips using a lip pencil to make them look a little fuller and then finished off with a light pink colour lipstick applied with a brush.

Even though I was going fast, I thought I had done a good job and Tim already looked very different from when he walked in. I had earlier decided not to try nail polish at this stage as it would take a bit more time than we had and I didn't want to stretch his patience. So, I slipped off the band and told him we were finished with the makeup and that I needed him to stand and take off the robe. I thought this might provoke some more resistance but to my surprise he stood and slipped off the robe and laid it on the bed. He turned to face me and I could see a look in his eyes, pleading with me not to laugh at him.

I said, 'You've done fine so far, not too much more to do.' I thought he looked really sweet in the white cotton knickers which stretched nice and tight across his bum and with a bulge at the front. I wickedly thought of giving him a squeeze there, but thought better of it.

Instead, I picked up and held out one of my bras. He looked down at it and then back to me 'Do I have to?'

'Tim, it's all about belief, you need to believe in this if you're going to get away with it. It's something you need to feel comfortable with.'

I gestured with me hand for him to take it and he held by his fingertips as if it would burn him.

'Turn round and I'll put it on for you.' I took the bra back from him and as he turned away I slipped it around his chest. 'The best way to put this on is to put it on back to front and then when you've done it up, swing it round and put your arms through the straps.'

I eased the bra up over his chest and then pulled the straps up and over his shoulders. He gave a little shiver as the bra straps tightened and started to tug at him. I stood behind him and slipped a pair of breast forms into the cups. He looked startled as the weight from the forms pulled him forwards and he looked down almost with wonder at his new chest.

'Wow, I didn't realise they would be heavy.'

I grinned, 'Welcome to my world.'

I think he had given himself up to this completely and I began to think that he might also be enjoying all this despite his initial protests. My hands were on his shoulders so I just let them run down his sides and as my fingers gently flicked across his skin he gave a little shudder and I swear I could hear a little moan. I held my hands on his hips for a second and he moved slightly backwards towards me.

Shit, I thought, what have I done?

I coughed and said 'OK, let's go the next stage, have you ever worn tights? Sorry, silly question.'

Tim blushed and said, 'Well, yes actually I have. I went on a school skiing holiday and my mother made me wear tights under my skiing gear for warmth.'

I just couldn't stop myself laughing and he grinned shyly back. 'I know, I got a lot of ribbing for that, but I was warm.'

I took a new pair of black tights from its packet and handed them to him. I had thought black would be a more forgiving colour for tonight. He sat on the side of the bed and expertly rolled them onto his legs and then pulled them up tight.

I took a risk and said, 'Feel good with shaved legs, don't they?' He shot me a look, but I could tell he thought they did feel good.

I hurried him on and picked up one of the skirts from where they lay. I had already thought that Em's clothes would fit him better than mine, so I choose a simple black pleated skirt and handed it to him.

'Let's try this on for size and fit. Put your hand on my shoulder and step into it and I'll pull it up for you. he did so and I pulled the skirt up to his waist and zipped it up from the back. It didn't fit too badly, a little bit loose in the waist, but that could be fixed. I grabbed a safety pin and pulled it tight at the back and there it was. The skirt came down just above Tim's knee and it looked OK. I knelt down and straightened the hem and looked up to see Tim's eyes shining down at me. I smiled to myself because I knew that look and what it meant. It was how I must have looked the first time I was dressed all those years ago. He was enjoying this now.

I knew I had seen a white, sleeveless top amongst Em's things and I though that would match with the skirt nicely. I found it and helped Tim to put it over his head, being careful not to get makeup on it. It hung loose over the waistband of the skirt, had a lovely scoop neck and fastened at the back. Having helped Tim to get it fastened, I thought about which shoes to try. I knew that mine would be too small for Tim, but I thought Em's might be closer to his size.

I found a pair of black patent leather ballet pumps with bows that would look good with the skirt and top. Tim sat on the edge of the bed and I knelt at his feet and took his foot into my hands and eased it into the shoe. It just about fitted and would do for tonight. I did the same for the other foot and I get a definite thrill from brushing my hands along his calf as I fitted the shoes. Stop it, girl, that's not what we're here for, I said firmly to myself.

That left just the wig to complete the transformation. I occasionally had to change my appearance when working, so I had a brunette, shoulder length wig which would do the trick. I had combed it out earlier so all I had to do was to shake it out a little and it was ready to go. Tim's hair was cut short so I stood behind him and gently smoothed the wig onto his head. It wasn't the greatest of wigs to be honest, but I thought it would be sufficient for our purposes tonight. I came round in front, adjusted the fit, fluffed it out a bit with my hands and I thought it looked sweet on him.

123456...9