Two Nights in Spring

The last thing was my wig. The wig transforms me and completes the disguise. But I had two with me that night - an exuberant golden-brown long curly wig which clearly drew attention away from my large nose, but also drew attention to me, or a more realistic darker, shorter straight silky wig which worked in a different way. I chose the long one, what the hell. It was actually pretty much how my hair used to be as a teenager, many many years ago. If only I'd kept it that way. If only a lot of things...

I looked in the long mirror now, my heart beating loudly in anticipation of the evening to follow, an evening just of wandering streets that yet would be so fulfilling and perhaps also thrilling. Stevie looked back at me, and I felt good. I put on the fleece - yes, that worked OK, and gathered up a few bits of make-up for last-minute adjustments in the car. My car keys, my room key, my emergency bag. I didn't need a hand-bag as the fleece had pockets, in any case I didn't have one.

I stood by the door and listened. No one about. Just 20 yards to the car. I took a deep breath, and opened the door.

My mouth was dry. I could hear my heart. But I moved calmly, I didn't hurry. Nothing unusual, just a tall woman. I could not walk too quickly even in those modest heels, anyway. No one about, just get in the car. Shoes off, easier to drive. Shit, is that a woman in the car opposite that I just walked past? Too bad, she's looking in her mirror anyway, doing make-up, probably just arrived, didn't notice. Surely if she'd noticed a tranny she'd be looking now? And she wasn't.

In the car I felt safe. As I drove away I noticed that the car opposite pulled out and followed me down the drive.

I drove about 3 miles to Didcot, the car was still behind me but so what, it is the main road and the only place really to go was Didcot. I parked in Sainsbury's car park. It was quite well-lit and of course there were plenty of people about, doing their grocery shopping in the evening. I felt good that night and planned to strut around the pedestrian streets at the other side of the supermarket, maybe even onto Broadway, as far as I dare. But as confident as I was to start with, I began to wish I had chosen the less obvious wig and adjusted my fleece so that it was over my hair, with no long tresses showing. not easy when sitting in the driving seat. I zipped it up tight and wondered why I hadn't brought a scarf as well. I checked my mirrors and saw some people walking behind the car, I didn't want to leave yet.

I checked my eyes and eyebrows - they would have to do - I'd shaved well and the foundation gave me an almost-too-perfect skin, lips were good. I hoped the hair drew attention away from my large nose and masculine jaw. My lipstick needed a little attention and I spent a few minutes carefully making my lower lip a little thicker, with a clean line which was difficult because my hands trembled a little. My hold-ups seemed not to have moved and everything between my legs was still tidy. I didn't check around again to see if people were about - that was pointless, I had come here to be seen, surprise was part of the thrill. This was it then. I got my keys, opened the car door and swung my legs out. I stood up and locked the car. I walked carefully in the direction of the footpath by the supermarket, trying to be as cool as possible, but my heart beating hard and my breath too shallow as I put one foot in front of the other, trying to be dainty, trying to wave my hips and wiggle my all-too-small buttocks, and thinking 'shoulders back, chest and bum out, tummy in'.

I realised I was walking directly towards a woman who was standing at the footpath, as if waiting for someone. She was tall, very tall, and red-headed, in fact she looked stunning, wearing a tight-fitting dark red flared jacket over a white blouse undone at the top revealing a little tempting cleavage, a black pleated wrap-around skirt that showed off long, slim nylon-clad legs, and dark red high heels that matched her jacket. She had the sort of figure a fashion model would want, but not as skinny. Slim, athletic, but with just the right amount of curves in the right places. She had a small black shoulder bag over her left shoulder. Dressed like that she could have looked tarty, but her height and build made her look classy. A dream. I love redheads. She reminded me of Pete's daughter, perhaps how I had imagined Pete's ex-wife, although he'd told me she had black hair and Emily took more after him. Anyway, I was close enough to see all this, she was close enough to see me as a tranny. I didn't care, but I didn't want to walk right up to her, so I cut between a couple of cars, to join the footpath a little further along. I didn't rush, perhaps walking half the speed I normally would as a man. So far, I was enjoying myself, just being free in these clothes, feeling the hem of my dress move against my nylon-clad legs, feeling the air on my buttocks and the tops of my thighs, still feeling the thong where it pressed against me, aware of the bra around my chest, tasting my lipstick. It all felt good, and I didn't register the click-click of hurried heels behind me.

Then there was a hand on my shoulder, and a breathy voice.

'Hallo Stevie' she said.

----

3. Penny

I froze, heart in my mouth. I had been discovered, someone I knew had recognised me! I didn't want it to have happened, my instinct was to run, but I didn't, accepting fate. It was the woman I'd just avoided, I knew before I turned it must be. Up close I saw the freckles, a real red-head. She looked familiar somehow but I couldn't place her.

'Stevie, sweetie, you look lovely'

The voice was different, accent gone, replaced by more than a hint of Essex. I really hadn't recognised him.

'Pete?'

'Call me Penny' she said quickly.

'Penny - I didn't recognise you'

I didn't know what to do with my voice. Stevie didn't usually speak, I attempted some sort of strangled falsetto.

'Just speak in your normal voice, just lighter.' Advised Penny. If this was her normal voice, Pete was a total fake.

I just couldn't stop staring at her. She looked so feminine. And the freckles - I didn't think Pete had freckles, at least not that many - just looked right with her hair, her skin, everything. Surely those pale breasts were not fake? She laughed, a girlish, light laugh, but confident and self-assured.

'I put more freckles on, the same each time - it's easy with practice' she explained. The same difficult 'r's, but she didn't attempt a 'th', so 'with' became a 'wiv'.

'And these ' - she cupped her breasts proudly - ' are mostly all mine! A little padding underneath'

So much for well-developed pecs.

'But darling, you're hiding your lovely hair!'

I was still tongue-tied, she'd already unzipped my fleece half down and was retrieving the long curls of my wig so they hung in tresses down my back for all to see. As she arranged my hair with both hands either side of my face her nearness was overwhelming. She smelled divine - I wished I had remembered to put on some perfume, I had brought some but I'd forgotten. I smelled of shower gel, she smelled of flowers with a hint of sandalwood. Her hands felt soft and delicate, mine felt large and clumsy.

'There.' She said, leaving my fleece half undone and picking off a stray hair she stepped back and regarded me brightly.

'So - are we going for a walk?'

I caught her hands, not wanting to lose this moment of contact, and for a moment we just stood and looked at each other.

'Penny, you look stunning. I mean, just.. stunning' I finally managed.

'Well thanks! I do my best'

She took my left arm and we started walking around the corner to the busy front of Sainsbury's. My mind was in a whirl.

'We're not going in.' I said, quickly. Penny looked startled.

'Don't worry, sweetheart, I'll look after you...'

I'm fairly particular about my demographic, I prefer darker streets and avoid any children. The last thing I want is some kid shouting out 'Mummy, why is that man dressed like a lady?'

'...but there are a few things I want to buy later' she added, mischievously.

I think there was a look of horror on my face as she guided me past the entrance and on towards the pedestrian streets. As we rounded the corner opposite Argos a man almost walked into us. I tensed, but Penny was as cool as anything. As he side-stepped to avoid us, the man gave us an appraising glance and smiled. Penny smiled back. I heard his steps stop as we walked on and felt Penny swaying her hips more than before - she knew he was looking at our legs. A little thrill ran through me and I tried my best to walk nicely in my modest heels, to be honest I had started to feel my calves, after a while they would ache and experience gave me respect for those that walk all day in high heels. I wished I'd worn different panties and tucked things away better, because I was getting aroused. Not hard, but kind of big and heavy. At least my dress was loose and pleated. I suddenly realised I'd hardly said a word to Penny since we met, I had no idea where we were going or what we were doing, but this was the happiest I'd been in a long time.

'Penny, we've got lots to talk about..'

'So serious!'

'How did you know?'

'Emily saw you drop your shoe.' She said, simply.

'What, that was enough, and she told you?' I was incredulous.

'I said we are close. I used to hide stuff in my car like that, she sussed you out'

'She knows you...?'

'We have no secrets any more.'

I was quiet for a moment, thinking of my own duplicity, and what 'no secrets any more' would do to my life. That always made me sad. I could only guess at what upheavals Penny had been through.

'So you came to check me out right away?'

'Yes' She smiled. 'and I knew straight away you weren't totally straight, then you were so evasive, I think you thought I fancied you, but you never pushed me totally away, and then you had to "do stuff"'

I remained quiet, a little dumbfounded that I was so transparent.

'And do you?' I eventually said, quietly.

'Yes' she laughed. 'Both as a man and as a woman'

'I do you'

'So - here we are!' she said, brightly

'Yes - but where are we going?'

'Where would you have gone?'

'Just for a wander'

'Then that's what we'll do'

Her arm was in mine and as we walked our steps were in time. People passed, not many looked, and I became a little less self conscious. I wanted to do this every evening. A sudden thought hit me.

'We should..'

'swap numbers?' She finished my sentence, it was uncanny. In a flash, she'd fished her iPhone out of her bag.

'That wasn't very feminine!' I said. She looked at me quizzically.

'You found it straight away!'

'It's a very small bag' she laughed and I gave her my number. We had stopped about half-way down the street and at the end on the left was a cafe with tables outside, and even on this cool evening it was quite busy.

'You go on' she said, 'I've got a call to make'

I looked at her, puzzled. She finished dialling and put her phone to her ear. Mine started to ring.

'Go on, and answer it' She waved me away. 'I want to watch you'

Oh! a new game!

I answered my phone.

'Hello?'

'Just walk up the street, shoulders back, and do as I say. One foot in front of the other...mmm, I like the wiggle...now stop, and look in the shop window, and now back at me...'

I looked back. She was leaning against the wall on one leg, her right knee (closest to me) bent, with her foot against the wall. Her skirt had ridden up a little. She looked gorgeous.

'Penny, you are hot!'

'Thanks darling, I think you are, too. Now walk up near the corner and stand like this'

She started walking towards me, and I turned and obeyed. As I realised what she had asked me to do, I started to get more aroused, but the accompanying feeling of panic served to keep things at bay. At the cafe there was a group of youngish men sitting at the outside table, just opposite where Penny had told me to stand. One of them had noticed me already, and was looking with interest. When I stopped and stood against the wall as instructed, it must have seemed to him that I did it for his benefit, which is of course what Penny intended.

'Is he looking at you?'

'Yes' I hissed.

'Look at him, not at me'

He was probably in his late twenties or early thirties, and he was having a good look at me. Dressed casually, he was dark-haired, clean-shaven and I guess quite handsome. I could almost feel his gaze as he checked out my legs, and my chest. Any moment now, I thought, he is going to check out my crotch then nudge his friends. But of course they way I was standing and with my pleated dress, there was no way he could see anything out of place between my legs. He looked me straight in the eyes and smiled. Automatically I responded, but then pretended I was smiling at something in my phone conversation.

'No - smile at him'. Penny had almost caught up to me now. A lot of things then seemed to happen at once. I gave the guy a sweet smile, he winked at me, I blushed, and I got an erection. Penny came up to me and gave me an affectionate hug and a kiss on the cheek. That did not help matters.

'Penny - I can't stand up straight - I can't move from here!' She glanced down at me and then with one swift movement put her phone away in her bag, zipped it up and gave it to me to hold.

'You naughty girl! - but that is sexy'

She put her arm around my waist and walked me across to the opposite corner. I hoped I wasn't holding the bag too obviously over my crotch. My penis was hard, still held across by my panties, but the end was poking out over my left thigh. As I walked the silky lining of my dress brushed against my glans. There would soon be a damp patch.

The guy at the cafe would have to crane his head around to see us now. The other two were now watching us, obviously enjoying the sight of us being so close. I was excited, but a bit uncomfortable.

'Penny, we should go back now' I indicated the road behind us, which went round the back of Sainsbury's to the car park. Penny considered this.

'Well, Stevie, you've been a very good girl doing what I said up until now, but you've had naughty thoughts, and will have to pay a forfeit'

Penny was obviously enjoying her little games, and although apprehensive, I trusted her and was quite prepared to go along with her suggestions.

'A forfeit?'

'Yes'

I was standing with my back to the cafe and the watching men, she was opposite me and I guess could see them, but she never once looked. I had her undivided attention as she moved closer and put her hands on my shoulders, drawing me nearer. I could smell her perfume and almost felt myself falling into her gorgeous soft velvety brown eyes. Eyes almost incongruous with her soft wavy flame hair. The hair must be a wig, but it was hard to believe. She licked her lips a little, daintily. My erection got stronger. She tilted her head, and instinctively I put my arm around her waist.

'Kiss me' she murmured.

I didn't need the invitation, I was already moving in. Our lips met. Her lipstick was strawberry flavoured. I could taste it and smell it. Our mouths opened and our tongues played in the lovely warm wetness we shared. Her hands had slipped down my back, carefully over the curls down to my waist, and now one crept lower to cup my buttock and pull me close. She was pressing her hips against mine, rubbing slightly sideways and pushing against my hard, hard penis. I could feel the end had got a little sticky. I felt her breasts pushing against my padding and as I felt her bum through her skirt I was pleased to find she was wearing suspenders. She was caressing my butt cheek through my dress now, the silky lining running gorgeously against my shaved skin, and I felt my dress slowly lifting under her fingers, until I was sure the hem was above my stocking-tops. Her other hand dropped down and as I felt the cold air on my bum I realised what she was doing. There was not a sound from the table over the way behind me as she broke the kiss and said sweetly

'This is your forfeit!'

So, I'd had my first kiss with the gorgeously sexy stunning Penny, and mooned at a table of strangers in a cafe, whilst in drag. An interesting evening.

I don't know what they'd seen, I'm sure they thought Penny was a woman, but really not sure about me. Whatever, as we turned and walked away, hand in hand now towards the car park, we got a little round of applause. So everyone was happy.

We stopped when we got to a darker, quieter place, and kissed for a long time. Penny was still drawn to my bottom, lifting my dress again, this time to caress my buttocks for her own (and mine!) pleasure, and as I held her and kissed her passionately, my own hands now under her skirt, enjoying her stocking tops and the way her suspenders pressed into the soft smooth skin of her rounded cheeks, I felt her finger rubbing the fabric of my thong, between my cheeks. She found my butt-hole and started circling lightly and pressing there. The feeling was phenomenal, and I was willing her to take the next step. I wiggled my arse in encouragement.

Just then we heard someone coming. But this kiss was just for us, so we stopped, walking on happily hand in hand again.

Penny had parked just down from me in the car park. We both knew how the rest of the evening was panning out. I pushed her back against the side of her very nice BMW for another kiss, before we got in our vehicles to drive the few minutes back.

'Time for that nightcap?' I said

'You bet - which is your car?'

'You know very well!' I responded. She pushed me away and then led me by the hand to the side of my car, next to a van. We were quite unobserved there. She pushed my quite roughly back against it and, holding both my hands outstretched against the doors, whispered in my ear:

'Do you like that?'

I did.

'Yes.' I whispered back, my erection unbearably strong.

'And this?'

Suddenly she brought her knee up sharply and made contact with my balls. The pain was exquisite, and I fell forward, my head on her shoulders. I almost came.

'Yes' I gasped. She had read me like a book

'oh, yes'. I added, hoarsely

She let my arms go and started kissing me, tenderly. Then her hands reached under my dress to caress my buttocks. Then one finger found my butt-hole and pushed inside. Her other hand was at the front and I felt her fingers close around my balls. Tenderly, at first, and then she gripped them, hard. She was kissing me, passionately, her tongue in my mouth and I could hardly respond. I pressed first against her hips then against her finger. She pulled on my balls. I could hardly breathe. One more squeeze and I would come.

Then she stopped.

She stood up straight, and laughing, she took off her wrap-around skirt!

'My turn!' she giggled 'See you back at the hotel!'

With that she handed me the skirt and walked out into the car park in full view, did a little dance, showing off gorgeous long slim legs in stockings, a beautiful peach coloured thong and suspenders, and her lovely rounded bum. She did the dance for me, but also for anyone else that was looking. Then she was back in her car and gone before I could register what had happened.

I was stunned.

I had never met anyone like her.

----

4. The first night

I carefully got into my car and adjusted my tender testicles into a more comfortable position. I sat there for a few moments trying to breathe normally and willing my erection to go away, but it didn't want to right then. Then I took off my boots. No way could I drive with those on at that moment. Penny had already gone, in a squeal of rubber. I took a more sedate and careful approach at first, my mind still a whirl, but it was not long before my eagerness to hold her again overcame caution and it seemed only a couple of minutes before I was back in my previous parking spot, looking across at Penny sat in her car, touching up her make-up just the way she had done earlier that evening, before I knew her plans. Before I even knew Penny.