Watching the Detectives

'Almost finished, Tim, then you can finally get a peek.'

'I'm sure I can wait,' he looked up at me, 'what do you think Philippa?'

To be truthful as I was getting Tim ready I hadn't paid too much attention to how it all looked. I asked him to stand and look at me and as he did so with a very shy smile on his face I realised just how pretty he was. I knew I was no professional, but I thought I had done a good job with the way the makeup and the wig framed his face to minimise many of his masculine features. I could still see Tim in there but I was astounded at what a difference it had all made. Don't get me wrong, it had not made him into a model, but it had softened and feminised his features as well as emphasising his eyes and those eyelashes were to die for.

'To be honest, Tim, I think you look terrific.'

I bent forward and gave him a peck on the cheek. His eyes widened and I thought he was going to say something, but he stayed silent.

'Oh, there's one more thing, I almost forgot.' I ran to my dressing table and picked up a pair of dangly clip on earrings which I fastened to each ear. He swung his head from side to side and could feel the earrings pulling on his ears as they moved.

'Now, that's better. Are you ready Tim?'

He swallowed, looked at me with a scared look in his eyes and nodded. I walked with him across to where I had covered my full length mirror. I paused and said, 'Remember, I think you look terrific.'

He swallowed again and then, 'Let's do it, Philippa.'

I whipped away the sheet covering the mirror and he saw himself for the first time. I expected some kind of response from him, but for a good few minutes he didn't show any reaction to what he was seeing. Oh my God, I thought he hates it, it hasn't worked. Then, slowly his hand came up and with his fingertips he gently touched the skin of his face, as if to check that it was actually his reflection in the mirror. He touched the wig and moved his head slightly so that the earrings moved.

I felt as if I hadn't drawn breath since I took away the sheet and let out a big sigh.

'Well, what do you think, Tim'

He turned to me as if noticing me for the first time.

'Philippa, I can't believe it. When you took away the sheet I didn't recognise who was standing there. It took my breath away. I was prepared for a freak show, but you've done a fabulous job. I am still speechless.'

I grinned, 'I wanted to do more, nails and stuff, but in the interest of time and your patience, I kept it simple.'

He was now turning from side to side, still looking at himself in the mirror.

I could hear him saying, 'Oh my, oh my,' over and over to himself as he gazed at his reflection.

I was thrilled with his reaction and about how he looked. By pure chance the black pleated skirt, the soft white blouse, black tights and shoes looked smart and suited his slightly angular frame. The skirt and blouse softened his shape and the skirt was short enough to show off some of what I thought were very good looking legs.

Tim was still in there but someone else was emerging in front of my eyes. It wasn't the clothes and makeup, there was another personality coming through from inside him. I could see his confidence growing as he watched himself in the mirror, as bit by bit, he was releasing something that maybe he never knew before was there. The dressing had been the catalyst for a reaction that was still going on; it had caused a dam to burst in his subconscious which was flooding his body with sensations he had never experienced before.

I took him by the hand and said, 'Come on, let's have a drink and talk about this.'

He nodded and followed me through to the lounge and as he walked I could see he was experiencing the thrill of nylon rubbing against nylon and the tickle of the skirt against his legs.

We sat down on the sofa and he drank the first glass of wine like it was putting out a fire.

I smiled, 'Steady, girl, we have lots to talk about.'

'Philippa, you're a genius, I cannot believe what you have done. If I couldn't see it with my own eyes I would not have believed it.'

'So, do you think you look good enough to go through with our plan.'

He waved his wine glass about, 'It may be the wine talking, but I feel great and you've convinced me that I don't look like a lorry driver in drag, but do you think I could be good enough to go out like this?'

The excitement was bursting out of him and I just had to smile.

'What? Did I say something funny? Don't you think I could do it?'

'No, nothing funny at all. I was just remembering you when you arrived, I thought you were going to run for the hills. Sweetie, you're more than presentable, you are pretty and cute and I think you would be able to go out and mingle with the others with no problem at all. In fact, with more work and practice I think you would be able to pass.'

He looked puzzled, 'Pass? Is there a test?'

I laughed so much I nearly snorted my wine.

'What did I say?' he looked crestfallen.

'No, it's just the idea of having a test, that would be awesome. Passing in our community means that you're able to go out and be taken for a woman in everyday life. It's the Holy Grail of crossdressers, being able to pass as a woman.'

He was wide eyed at this, 'You seriously think I might be able to pass, then.'

'Steady, sister, it's not that easy. It's not just the clothes and makeup, it's learning how to walk and talk and move and behave as a woman. It takes time and practice, lots and lots of practice, but, yes, I think given time and coaching and practice, I think you could pass.' He looked down at his hands and was obviously thinking about something.

I refilled his glass and we clinked glasses.

An idea flashed into my head and before I had time to think about it, I said, 'Tim, this is Thursday, are you doing anything tomorrow and Saturday?'

He looked up and said, 'I am off for the next three days, why?'

'Well, if you're up for it, we could do a crash course in crossdressing, actually more like a kind of immersion course. I mean, you would spend the whole time as a woman and I could coach you on how to walk and sit and become a bit more passable maybe. Then, on Saturday, we could go out to one of the TG friendly pubs I know and you could see how you get along.' I giggled, 'a kind of coming out party.'

He looked doubtful.

'Tim... no, it's no good, I can't call you Tim while you're dressed like this. We have to do something about your name. You'll need a femme name for when you're dressed as a girl. Anything take your fancy?'

He shook his head and his earrings swung and he looked startled, as he had forgotten they were there.

'Let's keep it simple, something that isn't too far from your name. I've got it. Tina, why not Tina?'

He smiled, 'Yes, I like Tina, I had a school friend called Tina. I liked her. Tina is fine, let's go with that.'

I refilled our glasses, 'Hello Tina, I'm Philippa, I'm pleased to meet you.'

He smiled shyly and said, 'Hello Philippa, I'm Tina.'

I leaned in for a kiss on the cheek as he did the same. Somehow we missed cheeks but ended up kissing each other on the lips. We giggled, drew back a fraction and then we were kissing for real, lips and teeth mashing against each other, tongues fighting between our lips. I felt his hands go round my back, instinctively my arms went around his neck and pulled him closer into the kiss. I felt his lipstick sliding against mine as the kiss went on and on. I nipped his tongue between my teeth and was rewarded with a moan from him. His hand moved and I felt him begin to massage and squeeze my breast through my t-shirt.

I broke the kiss, drew back and pulled the t-shirt over my head. I put his hand back onto my breast and kissed him again. There was no time to wonder, or think about was happening; this was instinctive, primal desire pushing all thought from the mind. He pulled the cup of my bra down to free from my breast and he broke the kiss, his tongue finding my nipple and it became my turn to moan as I felt his mouth engulf the tip. His teeth nipped my nipple and then his tongue lapped the new rock hard nipple. I really moaned this time as he nipped it again and then moved across to the other side for the same treatment.

I have always been sensitive there and Tim was driving me crazy as he licked and suckled on my nipples. I had to pull him up to give me some relief and we kissed again, slower and more gentle this time, taking our time to explore what each other liked. I tilted his head back and licked up his neck, then nipped his lip with my teeth, stretching it back and letting it go. I wondered how he felt, feeling his lipsticked lips sliding over someone else's lips for the first time. I dropped my hands to his legs and ran my fingers over his nylon clad legs and I felt him shiver as he felt that sensation for the first time also.

My hand stroked up and down his leg, pushing higher and higher each time as we continued to kiss. He groaned as my fingers found his cock, now hard but constrained by the tights and as I stroked it harder he began to move his hips, trying to rub it against my hand. What sensations he must be experiencing for the first time in his life, I thought. Surely nothing he has done before has prepared him for the incredible feelings he must be going through.

He had his hand back on my breasts by this time and the bra was making me uncomfortable, so I broke the kiss, took my hand from his cock, unhooked the bra and let it fall to the floor. His eyes were now wide and shining and when he smiled at me at me with his hazel eyes and those lashes I melted.

I managed to straddle him so that my breasts were level with his mouth and I leant forward and placed the right nipple in his mouth. I pulled the back of his head onto my breasts and he buried his face in them. I was writhing now as he attacked my breasts and nipples with his mouth, teeth and tongue. I could stand it no longer, stood up, grabbed his hand and said, 'Bedroom, now!'

I dragged him into the bedroom, stood by the bed and unzipped my skirt and dropped it to the floor, leaving me with just my knickers. I saw his eyes widen as he saw the red and purple bruises on my side and he said, 'Oh my God, I'm so sorry, I didn't realise, that must be so painful, we don't have to do anything if you don't want.'

For an answer I grabbed him, kissed him hard on the lips and muttered, 'I'll manage.'

I pushed him back onto the bed and he ended sitting with his legs over the edge of the bed. I leant forward, kissed him once again and then slipped down to my knees in front of him. As I did so, a thought flashed through my mind. I was on my knees about to give a blowjob to a copper, a male copper, dressed in women's clothes. This must be wrong on so many levels. I thought about it for a millisecond and decided, 'Nah, nothing wrong with that.'

I looked up into Tim's face and his eyes were wide open as he realised what I was going to do. Our eyes still locked together I slowly pushed my hands up his legs under his skirt and he tensed as he felt my fingers through the nylon tights he was wearing. I stroked my fingers back down to his knees and then back up again two or three times. He began to moan a little as I continued to tease him, my fingers riding a little higher up under his skirt every time until I finally touched his hard cock through the tights and his knickers. I knew that the constriction would be adding to the sensations he was feeling and I allowed my fingers to stroke and rub his cock as he began to move his hips to increase the feeling.

I stood up and straddled him in the bed, grabbed his head and kissing him hard on the lips, I began to move my bum over his cock which I could feel through my knickers. He moaned from somewhere deep in his throat and as I moved his head down to my breasts, he took a nipple between his lips and began to suck until it was hard then nipped it between his teeth, and it was my turn to moan. I teased his cock some more with my bum and it slid between my cheeks and I could feel him getting harder and more excited.

I slid back down from his lap onto to my knees and this time I ripped at the hem of the tights and tore a hole in the crotch. His cock was now constrained by his knickers and I slowly pulled them down at the front with my fingers until it sprung free. The head was already glistening and Tim jumped as I leant forward and blew gently across the head. I looked up to see his beautiful eyes with those gorgeous eyelashes widen even further as I licked the head and swirled my tongue around before sucking it between my lips. I knew he would be close to his climax so I tried to keep him on the edge as long as I could, licking and sucking the head and the shaft until I felt his cock thicken and he grunted and came into my mouth. I tried to swallow as much as I could but some splashed onto my lips. I stood up, straddled him and kissed him and could feel his cum sliding across lipstick covered lips.

We rolled onto the bed and kissed for what seemed like hours until he pulled back and looked at me.

'Philippa,' he whispered, 'i want to pinch myself to make sure this has been real and not just a dream. I'm scared that I will wake up soon and that this will have been a fantasy.'

I kissed him and said, 'No dream and no fantasy, this is all real, sweetie.'

He stroked my face with his finger tips and I drew one of his fingers into my mouth and sucked it. He shivered a little, closed his eyes and murmured, 'Please be there when I open my eyes again.'

My heart skipped and I wrapped my arms around him and drew him close to me.

'I'm not going anywhere.' I whispered back to him.

He stroked my tummy with his fingertips and my insides fluttered as his fingers slid gradually lower and lower.

'You know what's down there, don't you?' I asked, feeling stupid as soon as I said it.

'Mmm, Yes I do and, you know what, lying here with you like this, it feels right and I'm not scared but a little nervous. This is all new to me.'

We kissed and I said, 'I don't want you to do anything you're not OK with. I understand if you don't want to do anything, it's OK.'

'No, I want to, but you might have to be patient with me.'

His fingers traced their way lower until they met the top of my knickers. This slow march of his fingers down my tummy had got me excited and I could feel my cock swelling as he got closer and closer. but when he slipped his fingers under the waistband of my knickers, I gasped. He drew back and said, 'Sorry, did I do that wrong?'

'No, no, you were fine, it was a surprise, please don't stop.' He kissed me as he pushed his fingers back under the waistband and I could feel him drawing closer to my cock. His fingers flicked the head and he drew them back an instant before pushing down again onto my cock. I must have stopped breathing at some point because I took a huge breath as he encircled me with his fingers. I could feel through his kissing he was nervous but he kept going, his fingers gently stroking the shaft.

'It won't break,' I whispered.

I wrapped my fingers around his and began to move them faster and harder up and down my shaft. I knew this would be very different for him, but I kept his fingers moving up and down and I began to move my hips so that my cock slid through his fingers. He broke our kiss and looked down to see my hand around his fingers as I got harder and harder. His eyes were wide as he watched me grow and get more excited. I felt my climax building deep my groin inside and then that irresistible feeling travelled up through my cock until I exploded into his hand. I grunted and pulsed a couple of times, before I slumped back. His fingers were covered in my cum and I took his hand and gently licked most of the cum from them. Tim still had not said a word and I wondered if this had just been too much for him. He brought his hand up to his lips and I was surprised when he pushed out his tongue and began to lick the remaining cum from his fingers.

It struck me that I was down to my knickers by now and that he was still almost fully clothed. I unbuttoned his blouse and slipped it off his shoulders and unzipped the skirt and he raised his hips to let me pull it off. His tights were now torn so I rolled them off as well. Tim was silent throughout this undressing and he seemed almost dazed by what had happened. I lay on the bed with him pulled the covers over us both and spooned up behind him with my arm over his waist.

We lay there for a few minutes in silence and then he said very quietly, 'Philippa, thank you.'

I kissed his shoulder and interlocked his fingers with mine and said, 'You're welcome, Tina.'

The sun woke me up, pouring in through a gap in the curtains. I stretched and touched someone's foot. Half awake, I thought Em must have stayed over again. Then I remembered what had happened last night and my eyes snapped open.

Oh my God, I'm in bed with Tim, or is it Tina. The memories of last night flooded into my brain and I closed my eyes again. What have I done?

I could hear his steady breathing behind me so I slowly turned over to look at him. He was still sleeping and his makeup was messed up and the wig slightly crooked but he looked so sweet as he lay there. I reached out and gently stroked his cheek with my fingers and he stirred, then opened his eyes. I prayed that he wouldn't freak out completely waking up next to me. I saw his eyes focus and then a huge grin spread over his face.

'Morning gorgeous,' he said.

I grinned back at him, leant forward and kissed him on the lips.

'Mmm, that's nice,' he said, his grin getting even bigger. We kissed for a while, just enjoying the touch of each other's lips.

I said, 'You haven't changed your mind from last night, then? Do you still want to go through with getting ready for Saturday night?'

He leant forward, gave me a kiss and said, 'No, I haven't changed my mind, I'm a little scared but I want to try.'

I jumped up off the bed, 'That's great, let's get started. First, I need to show you how to clean that makeup off your face and then we can have breakfast and after that we'll get you dressed and then...'

'Whoa, whoa,' he held up his hands. 'Can I have a coffee first, please. I can't think without a coffee.'

I made us both a coffee and showed him how to clean off the remains of his makeup from the previous night. I was determined to make him do as much as possible these next two days, partly, I admit, because I wanted to see how far he would go down this path. I went out to fetch some breakfast from a cafe round the corner and when I returned I caught Tim looking through the the clothes that Emily had brought across.

'See anything you like?' I said.

He laughed, 'I have two suits, one jacket, two pairs of trousers, oh, and a couple of pairs of jeans. I never realised there were so many different types of clothes for women.

'That's what makes being a woman so great, you'll find out for yourself soon enough.'

He blushed but said nothing. It was over breakfast when I felt I needed to clear the air about last night

'Tim, you haven't said anything about last night, I'm worried that you aren't OK with what we did. Are you? OK, I mean.'

He took a sip of his coffee, giving himself time to think about his answer.

'If anyone had told me two days ago that within 48 hours I would be wearing makeup, women's clothes, touching a penis that's not my own, and sleeping with a transgender woman, I would have had them committed as mad. Yet, that's exactly what happened. I don't think I understand what's happened myself, so I'm not sure I can talk about it rationally right now. What I do know is that before I dressed in those clothes I expected to feel awkward, embarrassed, maybe even disgusted, if I'm honest. At first, yes, I felt embarrassed, especially in front of somebody that I was so attracted to. Instead, as you made me up and I put on the clothes, something changed inside me. I began to feel calmer, more relaxed, less stressed, gentler even. It was almost some kind of a release, something I had been waiting for without knowing it for years perhaps. I've never felt drawn to crossdressing and, I have to admit, my sex life has been pretty uneventful over the past few years, but when you put on the wig and I looked in the mirror, it felt so good. I still don't know how good I look, but it made me feel pretty and nice and happy, yes, happy. it was if I had stepped outside of Tim and stepped in somebody else's shoes, literally I guess.'