Second Chance

She pushed the dress into my shoulder and I automatically took it from her grasp. She smiled warmly. 'Oh and darling,' she gushes, 'I can lend you these shoes and some make-up. In fact Anything you need to look pretty. But I want you to buy yourself a wig, wax your whole body, arch your eyebrows and have your nails professionally manicured and painted.' She held my hand and looked fondly at my short stubby nails. 'These will look breathtaking with false nails and a bright red ... perhaps even matching your lipstick.'

'What!' I gasp, 'how on earth am I going to do all that?'

She smiled and appeared with a bag of make-up. 'That's your problem not mine. All I suggest is that you don't skimp on your effort as a lot hangs on this date. I don't care how you do it. Enlist the help of a girlfriend, embark on a course of feminine erotic hypnosis .. Whatever. AlI care about us seeing the end result. Thats right my pretty, I want to see you as a sexy convincing girl. You can do that for me .. Can't you?

I nod warily with no idea how I could ever look convincing but was committed to doing anything if it would win back her heart..

'So that means we are going out,' I say nervously. 'A real date?'

She laughs 'Kind of I guess .. Just different.. I will pick you up from your flat just like you used to call for me and I will take you out for a meal. During the meal you and I need to talk about us and how it could work.'

This made me smile. At last the ice queen was melting and seemed prepared to forgive and start afresh.

'So is that clear,' she says again. 'I want you wearing this dreamy red dress looking like a sexy convincing girl . Wearing panties, bra, hose wig and full make-up And then and only then if you look convincing I will take you out.'

I nod a little reluctantly.

'Excellent,' she says giving me a gentle kiss on the cheek. 'Do a good job. Don't let me down and I will pick you up a week on Saturday at 7 O'clock.' And with that she made it clear that our time together that night at least was over. While she watched I took off the bra, slipped my jeans and sneakers back on gathered the things and left.

What was I to do? and how was I to do it but in reality my concerns where diminished by the thought of a date with my dream girl and a chance to make amends whatever she was going to put me through.

I spend the following night thinking about what Katy said and even did a dress rehearsal. But this was a disaster. The dress was a surprisingly good fit but I looked a complete idiot. It was my own fault. I wore no panties, bra, make-up or shoes and with my short hair I looked like a guy dressed in drag going out in fancy dress. I looked ridiculous and saw no way of ever looking convincing. And yet wearing her dress was a tremendous sexual thrill and longed to wear everything just as a pretty girl should. I'm not sure what her things did to me but I felt pretty, soft and feminine yet I didn't feel gay or want a man. I still felt very heterosexual and now more than ever wanted to get Katy back into bed to prove to her that i was a man just like Brad. But rather than being a testosterone led assertive guy I felt gentle, emotional and relaxed.

Giving up was not an option. Katy knew I enjoyed wearing her things but I had never dressed completely as a woman and certainly never ventured outside in a dress. She knew I would be finding this difficult and yet also knew I would be unable to resist the challenge which I guess was part of the test.

I decided to ask an old school friend , Sally for help. She was a girl who I had known most my life and we regularly used each other in time of need. She was like a sister to me. She originally said I needed my head tested when I said I wanted to split from Katy.

But still wasnt sure what she would say when I tell her about Katy, the date and why I need her help.

Fortunately her reaction was surprisingly favourable. I asked Sally over the phone and could tell she was laughing. She said she would take me out and get everything sorted.

After taking the mick out of me she said that my devotion was commendable and hoped that Katy appreciated all the effort that I was putting in.

Sally had an aunt who owned a beauty parlour. This made the task much easier but when the Saturday came round and Sally took me to meet her and her team they too laughed when Sally told them my plight. That said they very quickly they got down to business, stripping me down to my panties and making me war a white towelling robe.

They treated me just like a normal girl giving me a full body wax. Moisturising my body, attaching false painted nails and arching my brows. They even lent me a shoulder length blonde wig and after a couple of hours they were presenting me with the robe as a gift and commending me in how beautiful I looked and what a girl i would make later that day.

Sally dropped me back at the flat and told me to relax. She would be back later and help me dress. Alone I daren't do anything to damage me nails. I carefully undressed out of my male stuff as Sally had told me and slipped onto the fluffy white gown. I made myself a stiff drink and padded around nervously unable to eat. Sally came back as she promised to help me prepare mentally and physically. I was in my dressing gown when I answered the door.

Considering Katy wasn't picking me up till 7 O'clock I thought getting ready at 1 O'clock rather early but Sally disagreed. 'We've got so much to do and I think you'll find it's not just the clothes that make the woman. We need to practice on your whole persona. What to say, how to walk, how to flirt. To be a convincing young girl you need to hold yourself correctly, say the right things and walk like a sexy young girl . So come on pour us a glass of wine and let's get you dressed.'

She followed me into the bedroom and watched as I slid a stocking up each leg and fastened them to my suspenders belt.

'Your legs are amazing,' Sally said as I straighten my seams. 'Unbelievable.' Next was the bra. Katy had padded it out with special firm pads that felt very realistic. 'Now,' Sally said lets make up your face and get you dressed so we can you practice being a girl.'

I sat on the sofa as she covered my face with foundation and dusted my eyes with shadow. She lengthened my eye lashes with mascara and painted my lips with a glossy lipstick. 'How do you feel,' she said as I puckered my lips and let the lipstick settle.

I smiled and nodded feeling a little uncomfortable in confessing my true feelings.

'I bought with me a tight pencil skirt and a frilly blouse I thought if you wear this during the afternoon you will get used to wearing a skirt and being girly. We can talk girly things practise your walk and I'll show you how to act so even your mother would think she has a daughter not a son. By the time 7 O'clock comes round you will forget you are a guy and enjoy the night as a girl and who knows you may even get lucky.

After I had pranced about practising my girly walk and mannerisms, had several glasses of wine and practised playing with my hair, looking coy and generally flirting I was done.

Sally unveiled the pretty red dress and helped me into it. Zipping me in and clasping me securely at the back. She brushed my wig and secured it on my head. She touched up my make-up and filled a clutch bag, that she had leant me with some girly things. I squeezed on the high heels and quickly practised another walk.

Perfect ,' Sally said watching me waddle up and down my room. 'You look stunning. A real head turner. Katy will hardly recognise you. How do you feel?'

I looked at myself in the wall mirror and could feel a tear welling up in my eyes. 'Thank you,' I said coming over all emotional. 'I'm not sure what I would have done without you.'

Sally gave me a girly hug, cleared her own throat and gave me a big kiss on the cheek careful not to smudge my foundation. 'It's up to you now.' She finally said, 'I can do no more. You look amazing and Katy cannot fail to be impressed. Me personally, I am amazed how you look.. And don't take this the wrong way .. Ravishing. I don't know about Katy but you'll have trouble keeping the boys at bay talk about her.' I smile sweetly and thanked her for all efforts. At the door she turned to me once more and held both my hands. 'Just enjoy yourself but don't get too carried away. Katy, however much you love her can be a wicked tease. You dumping her taught her a lot and she's no longer the innocent little girl you once knew. Don't let her do anything you don't want to.'

And with that she was gone. I was alone in my flat dressed completely as a convincing girl. I could hardly contain myself with excitement and had to keep popping to the toilet. I felt as if I had been working to this point for so very long I could hardly believe that it had come.

7 O'clock came and went and as I sat perched on a chair in my dress and high heels I began to wonder if I had been duped. Could this girl i loved be so cruel as to make me dress up this way and then let me down cruelly and humiliated. I poured myself another stiff vodka and watched my lipstick mark the glass as I took a sip. On an empty stomach it went straight to my head and I began to feel woozy. I stood up and checked myself in the mirror. Played with my hair, adjusting my hose and smoothed my dress petrified that she may see my panty line.

Eventually the door bell rang. My heart kept and wondered what I should do if it wasn't Katy. I waited a good few seconds before walking to the hall.

I stood trembling at the door but saw her familiar figure through the side window.

'My goodness you look amazing,' she gushed as I opened the door. 'You look incredible. She pushed me inside and kicked the door shut behind her. 'You really do look incredibly hot.' She held me by the hand and dragged me to the bedroom.

She was decidedly casual wearing a pair of tatty jeans and a hoddy but Ii didn't care. Her eyes were bright and she looked high on excitement.

She held me close and kissed me hard on the lips. One hand fingering my waist the other around my shoulder pulling me close. Her kissing got hotter and hotter. Her hand around my neck dropped to my butt and was soon joined by the other. She squeezed my cheeks and began pulling my groin into hers. What happened next was what I dreaded and my cock which had been flaccid all day, woke up and began to stiffen.

'Hello darling,' she says pulling away from me. 'You are pleased to see me. Have you missed me, do you want me to take control or do you like wearing pretty girls clothes?'

She kissed me again but this time one of her hands worked around the front of my dress and began to massage my growing cock. 'But what are we going to do with this naughty thing,' she said. 'It will ruin the line of your pretty dress and potentially give the game away. Im not sure if I can take you out like this.'

'No please,' I say Ive done everything you asked. Please take me out.'

Katy ignored my pleas. 'Who was the last girl you dated?'

I floundered uncomfortable about revealing details about my lack ok conquests. 'Julie,' I quickly said making a name up out of the blue.'

'Perfect,' she said, 'tonight you can be my Julie. I cannot call you by your real name. Not when you are dressed so beautifully. So Julie it is and such a pretty name.'

She pushed me to the sofa and bent me over the back of the chair like a doll. I flopped over the couch my high heels still firmly on the ground. She pulled my hips away from the couch so she could fondle my cock and slowly pulled my dress up to my thighs. She gasped as her inquisitive fingers worked their way into my panties and soon began to fondle me like a girl. And as she fingered me she pressed her own groin into my butt and lent over my back so she could whisper in my ear.

'Tell me Julie... How does it feel to be the pretty girl in a dress while I play with you just like a girl?'

I tried to reply but my blood was rushing to my cock and I had difficulty concentrating as my stomach spiralled with excitement.

She teased me cruelly with her hands around my cock and her actions got stronger and stronger until she was pulling at my cock and pressing into my but with an exciting rhythm.

'Careful of my dress,' I found myself squealy then realising my mistake tried to excerpt some masculinity to get on top of the situation but she was a determined lady and I could tell where she wanted me so fearful of spoiling her advances I went along with her game even giggling girlishly

'What's up Julie do you want to cum in your panties? You naughty girl. I bet you let all the boys have you over the couch before going on a date.'

she teased me more yanking harder and harder.

'I want you,' I mutter. 'I want to be inside you.. I.. I ... I.. I stuttered and before I could say anymore I felt a thousand star explode in my stomach and my love burst out my balls.

But Katy had control and and like it or not I was soon squealing like a little girl as I began to spurt my creamy excitement into her hand and my pretty panties.

'That's a good pretty girl,' she said pumping me dry. 'With that gone I think we can venture outside without any noticeable excitement. What do you think Julie?'

She was right my cock had became flaccid and shrivelled inside my panties so even though my dress was clingy you could see nothing of my hidden surprise.. 'You may want to change,' she said pointing to my groin, 'before it stains, a clean pair of panties will make you feel so much fresher.'

smirked and felt my face redden. I couldn't believe that she had jerked me off bent over a couch dressed as a woman.

'You do have another pair don't you?

'Yes,' I mutter.

'Good then while I wash my hands you change your panties and fix your lipstick and we better be off or they will give away our reservation.'

The drive to the restaurant was relatively uneventful that is to say little was said between us. I made a fool of myself sliding into her low sports car and she couldn't seem to keep her eyes of my knees. I found sitting in the passenger seat with my legs together very unusual. Odd in the sense that I always drive and odd in that I'm normally wearing trousers. The air con was a treat and cool air blowing up my skirt was a treat only a girl can talk about. That said I enjoyed sitting demurely in the car and practiced sitting with my legs crossed, knees together straight ahead and angled towards Katy. She particularly liked me checking my make-up in the vanity mirror.

The restaurant was a romantic Italian full of courting couples in cosy nooks. I remembered it as Katy pulled up in the car park. It was the restaurant we last met in and the restaurant in which I dumped her.

'I thought it was poignant,' she said as I linked arms with her and walked inside, 'a fresh start a new beginning. I even managed to book the table we sat in before.'

I cringed and wondered if this whole evening had been staged to humiliate me.

We were shown to our table like two girlfriends out together. No one suspected a thing. Katy insisted I sat where she sat last time.

'How does it feel?' She giggled after our pasta arrived and we started to eat.

'What do you mean,' I said, 'coming back to this restaurant with you?'

'No stupid wearing that dress and being the girl. '

I cleared my throat and replied in hush tones, 'please don't go on about it. I'm here. I've done it and yes I feel very uncomfortable but I want you to know I would do anything for you. You know that. I so want you back and now realise what we had. You meant so much to me and I threw it all away.'

'Yes you did. You hurt me. I was so upset. With no warning nothing. one minute I thought we were both happy the next, I was in that dress, we were in this restaurant, at this table and you dumped me. '

I grimaced. 'I know I'm so sorry.'

'Well i'm not so sure you are.' She smirked. 'Why don't you go to the ladies and touch up your make-up before dessert?'

'No,' I say not wanting to make an exhibition of myself, 'It's ok,' I say determined not to walk through the restaurant on my own and to the ladies toilet which I wasn't sure was even legal but Katy wouldn't accept no for an answer. 'Go,' she said,' do something to your hair, go powder your nose or whatever I want to see you from a distance and how the other diners react.'

Reluctantly I stood up and held my clutch bag nervously.

My chair scrapped as I pushed it back and all the other diners watched as I weaved my way amongst the tables. Wearing the dress was humiliating enough but it was so bright there was no way I could move without being noticed.

Two lads grinned as I swept past their table my heels click clacking on the wooden floor. I caught their eye. One looked strangely familiar and he smiled as I brushed past and was sure he gave me a cheeky wink.

Fortunately the ladies was empty as I skipped in and darted into a cubicle. I remembered what Sally had said as I bunched my dress up pulled my panties down and squat over the toilet just like a lady.

Katy watched me navigate back to the table and sniffed the air as I walked past. 'I love your perfume,' she said, 'very feminine. What is it?' I replied and blushed but pleased that she had noticed. 'It's these small touches that make a woman.' She remarked.

We chatted and flirted. It was kinda cute it was as if we were on our first date. We may have looked a little strange like two girls but I really didn't care. We were getting on so well I really thought she was accepting me back despite the fact that I was dressed as the feminine girl.

She held my hand across the table and admired my nails. 'You really did it,' she said softly

I nodded and bushed and fluttered my eyelashes.

'I always knew you wanted to wear girls clothes even if you didn't know yourself. And they suit you so much. You have such a beautiful figure, tiny waist, long legs it is such a shame to hide yourself away in drab male clothes. I've always liked a man whose in touch with his feminine side. My current man is a man in every sense of the word and would never wear panties.'

I laugh nervously. 'What are you trying to say?' I ask.

She smiles and waves at the waiter for the bill. 'I'm not saying anything in particular. All I'm saying is that I like you dressed as you are and if you want to see me again you will have to get used to wearing the dress.' Anyhow let's not spoil the moment. What do you want to do next? Go dancing or perhaps back to mine?'

'Normally I would love to go clubbing but I'm not sure if I want to in this dress. 'I don't know how to dance as a girl. and .. well it will be full of guys.'

She laughs. 'You never did dance very well as a guy so I've no idea how you would dance in high heels and a dress. Besides looking like you do you may attract quite a following and I'm not sure if I want to share you just yet.'

I heave a sigh of relieve.

'Come on then my pretty I'm very proud of you so let's get you home.'

I plucked up courage and asked if we could go back to hers.

'My, my,' she smirks, 'you are being brave but sadly I don't think Bret would appreciate you at all. He is staying over tonight and I said I was going our for a girly gossip with an old friend.' She laughs. 'Julie. He is so jealous he didn't believe me.'

I smile but hate him already.

'He was convinced I was seeing some guy so he came along and bought a mate out for a meal. He's here in the restaurant now by the window.'

I almost go sick and try to look casually over to the window in a state of shock and see the black haired guy who I noticed earlier as I went to the toilet. His hair was slightly longer but I recognised him now from her photos.

'Oh my goodness,' I cry, 'does he know who I am?'