My Date

Chapter One

The first date went well.

I met Francesca outside the cinema. She looked exactly as she had described herself. Tall, particularly in the incredible black boots, athletic, with long auburn hair. I was attracted to her straight away, and loved the way she took my arm, smiled and walked with me into the cinema.

We had a few minutes before the film started and so we chatted about ourselves. She told me she'd only just moved into the area for a job in insurance. I soon learned that she shared a flat with her sister Tommi, enjoyed horse-riding and music, and liked Italian food.

I found her smile captivating. I behaved impeccably through the film, even though it wasn't very good. Outside I invited her to an Italian restaurant, but she declined, telling me she had an early start. She did accept a lift home.

I didn't know whether I was being dropped, until she asked me in for coffee. To be asked into her flat was encouraging.

I followed her up the stairs, trying not to stare at her beautiful long legs. If she knew I was studying her, she didn't show it. Finally we were on her floor. She took out a bundle of keys and opened the door.

The flat was spacious with a combined kitchen and living room. I liked the stylish colours and furniture.

'Tommi!' she called. There was no answer.

'My chaperone is not here, so I'll have to trust you to behave yourself.' She patted me playfully on the cheek. 'Come on in.'

I took off my coat and laid it next to hers on a bureau by the door.

'Tea or coffee John?'

'Coffee please. White with no sugar.'

She went behind the kitchen counter and started to make coffee.

'Do you like the flat?'

'Yes it's lovely. What's the view like in daylight?'

She walked me to the window, and even though there was very little light she pointed. 'I can see the sea over there, and over there behind the second hill is the stables where I ride.' 'Shall I show you around? The coffee will be a couple of minutes yet.'

'Please.'

There was a balcony which she said she adored, a bathroom with an L-shaped bath squeezed into it, her sisters room, and finally her room. There wasn't much to see of her room. The only distinguishing things were the king-sized bed and exercise bench in the corner.

'Do you keep fit?' she asked.

'Occasionally. I'm more of a runner, although core strength is important for endurance.'

'Come on. I can hear the coffee dripping.'

We sat relaxing on the couch with cups of steaming coffee. She asked me to help her take off her boots. She said Tommi normally helped her. Of course I agreed. It was an opportunity for contact with her feet and legs.

She put her left leg up on a footrest.

'They are laced up the back. Start at the top.'

They were amazing boots. The bow was behind her knees and the laces zigzagged to just above her heel. When I'd finally loosened the lacing, I gripped the boot by the heel and pulled them off, carefully lowering her foot to the stool.

'Beautifully done.'

She offered up the other boot, and watched me as I worked. She pointed to where I should put them and then asked for me to massage her feet. I worked on each sole in turn, kneading and stretching.

'You can come again!' she said laughing.

When I had finished, or rather when she told me I could stop, I sat next to her and enjoyed the coffee.

'Have you enjoyed tonight John?'

'Very much Francesca.'

'Would would like to see me again, only this time over a meal here?'

'I would. Can I bring the wine?'

We fixed a day for our next date.

'I'm afraid I've got to get some rest, and you'll have to go home.

Chapter 2

The time and day came, Saturday at noon. I knocked on the door. She answered. I offered her the bottle of wine and kissed her on the cheek. She asked me in. It felt like we were old friends already.

Tommi still wasn't home. I was glad. Three's a crowd. We had a lovely meal on the balcony. The sun was strong and the view breathtaking.

Conversation came easily and we talked about all sorts of topics. She was wearing a summer dress and elegant shoes. Her hair was in a bun at the nape of her neck. Around her neck was a thin black choker. Her smile made my day.

Afterwards we washed up together. As she passed me the bottle of wine she slipped, spilling red wine over my shirt and the waist of my trousers.

'I'm so sorry!'

'It's OK. It'll wash out.'

She tried to dab out the stain with a cloth, but soon realised it was hopeless.

'Why don't you use the shower and we'll get these in the machine.'

I was embarrassed, and if anyone was going to have to remove their clothes I wanted it to be her. I relented and took a long hot shower.

When I had finished my clothes had been collected. There had been a bathrobe on a hook on the door, but it was gone.

'Francesca. Is there anything I can put on in the meantime?' I shouted through the door.

'What would you like John?'

'Do you have a robe?'

'Tommi has one, but she wouldn't appreciate finding a guy in it.'

'What about some shorts?'

It went quiet and then the door opened slightly. Her hand came through holding black shorts. When I took them from her I realised that they weren't exactly running shorts. They were black cotton knickers.

I tucked myself into them and reluctantly stepped through the door. Francesca looked impressed.

'Did you expect me to have male clothes in the house! Anyway, your clothes will be fifty minutes and then fifteen in the dryer. You look good John.'

I felt so vulnerable.

'Shall we look so something more suitable?' She walked me to her room and opened the large wardrobe. She flung other knickers and g-strings onto the bed.

'Any of those?'

'No.'

'Come on John! Smile! Let's have some fun while we're waiting.'

She stepped forward and pulled down my knickers, inspecting my naked body. Her hand brushed across my chest, stomach and hips before reaching my thighs. She didn't touch my cock, which was standing hard and erect, or my testicles, but swept round to my buttocks and down the crack to lightly touch my hole.

Chapter Three

'Would you like to play a game with me John?'

'Do I have a choice!' I said with a thin smile. Naturally I was nervous. A guy wants to be in control.

'When I was younger I had a doll. I'd dress her up. Now I'm a little older I'm expected to put those childish games away, but I miss them.'

She kissed me on my mouth. Her hands were pulling me to her chest. I'd have said anything to please her.

'Will you help me?' she whispered.

I nodded. She rewarded me with another deeper kiss, and then a playful smile.

'You shave, and I'll lay out some things. Hurry now!'

I did as I was told at the sink in the bathroom. She inspected me, took the razor to my buttocks, back and neck, rinsed me, and handed me a tub of cream. 'Rub in as much as your skin will absorb. It'll sooth your body.'

As I worked, she worked on my hair. I didn't have much length to it, but she tidied, brushed and trimmed it.

'Why are we hurrying?'

'Because Tommi is back at six, and I want you all to myself.'

Finally she was happy with my skin and hair.

'Have you ever worn stockings before?

'No.' I lied. I had tried women's clothes before, but never found any satisfaction in it. This little adventure was an answer to an old fantasy, and I was determined to enjoy it.

She rolled each stocking up my legs. The stocking belt was a beautiful elegant piece, with four straps hanging down to accept the stockings. The colour of the stocking belt and knickers was powder blue with white lace trim. The knickers were quite large to accommodate and hide my cock. There was a pocket inside that held my shaft tight against my belly. The bulge was still visible, but only up-close.

'You have a great body for this John. Fit but not too muscular. Your Adam's-apple is too prominent , but I can hide that. Your face and hair are perfect.'

'The corset is next.' She showed me the corset. It was not dainty. It was a long, heavy, ribbed piece of material. It would stretch from my crotch to my armpits and lace all the way up my back. The breast shapes were part of the corset.

She laid it opened-out on the bed and I laid on top of it. It wrapped around me. The lacing started in the middle, but there were separate laces at the neck and between the legs.

It took so long to lace it, with Francesca working harder and harder to squeeze any flexibility out of my body. I felt it squeeze particularly at the waist. She commented on my hourglass figure, and even told me she was jealous of my waist.

'Have you dressed a guy before?' I asked.

'Yes I have, but you are far prettier.'

I wasn't used to being called pretty.

'How often?'

'We're nearly done. Stand up if you can.'

I used my arms to struggle to my feet.

Chapter Four

I repeated the question as she knelt at my feet, offering up black patent leather shoes to first my right and then my left foot.

She took my hand and led me around the room. It was like walking on stilts, but I quickly began to master it if I moved slowly and smoothly. Is this why models walk the way they do?

'I've had plenty of practice, particularly on my brother, Tom.'

'So Tommi is Tom?'

'Used to be. He liked it so much he burned his own clothes, got a new job and new friends. You'd have to look at his passport to know.'

'Any other family around?'

'We don't see much of Dad any more, but Mum comes to stay quite often.'

'I'm sorry to pry, but what did your Dad think when Tom changed?'

'I don't care. And Tom didn't change, he just hadn't realised who he was. Well done. You're getting the hang of heels John.'

'It's not what I expected of a second date!'

We laughed easily together. I overbalanced and fell into her. She took my weight in her arms easily and pushed me back to a balanced position.

'Shall we pick a dress together?' she said enthusiastically.

'We've come this far.'

She already knew which dress she wanted me to wear, and I went with her decision. It was a off-the-shoulder black dress that slipped over my head and covered the corset. It showed my new figure perfectly, but Francesca insisted that wide black belt around my waist would make it even better.

It was a two inch leather belt that fastened at the back with twin straps and mechanical catches. If a weight-training belt could be made to look feminine, it would look like this. She was delighted that I got to the first hole on the strap and the catches clicked shut.

'Do you dare to walk outside with me John?'

'How far, where to, and do I have to use the stairs? I really wouldn't want to be recognised.'

'With make-up and one of my wigs, your closest friend wouldn't recognise you. Don't worry about the stairs; there's a lift at the end of the corridor.'

My wig was long and black. The plucking of my eyebrows and application of make-up did nothing for me, but she obviously enjoyed it. It all took about half an hour.

In the lift we were alone, but once on the pavement we were passing people. I didn't know whether I was being stared at. Francesca insisted they couldn't care less and for me to talk to her and keep my eyes forward. I did as I was told and tried to trust in her.

'You're doing so well. I'll buy you a coffee.' She pointed to an outdoor table of a coffee shop and told me to sit.

I must have sat like a man, because she quickly showed me how to sit, crossed legged with toes pointed. Posture was not a problem as I was held tight and straight by whalebone and leather.

As we drank she took my picture with her phone and sent it to Tommi. She told me about the sissy dressing-service business she ran with two friends and about the website where my picture would go.

Inside I wanted to panic about a photograph being taken and published, but I tried to reassure myself that nobody could recognise me like this. There was after all, nothing I could do about it.

Chapter Five

We arrived back at her flat. She was full of praise and kept telling me how pleased she was with me.

All I cared about was relieving my bladder! I asked her if I could use her bathroom and for help freeing my cock. She laughed and said I should learn to do it myself.

In the bathroom I eventually managed to unlace the corset at the crotch, peel down my knickers and relieve myself. As I waited for the stream to subside I wondered what she meant by saying 'You'll have to learn'. Would I be wearing this regularly?

Francesca opened the door as I was washing my hands.

'Thank you for the coffee.' I said, looking for something to say.

'That's OK. It was my pleasure to walk you and show you off. I'm going to have a shower before work. Will you be a sweet thing and tidy the kitchen for me?'

'Yes, of course.'

'Wonderful. The lunch plates are in the sink for washing and then wipe down all the oven and all the surfaces.'

She patted my bottom as I left. 'Oh. One more thing. That dress you're wearing is very important, so look in the bottom draw, find an apron and put it on.'

The bottom drawer held a few kitchen towels and white aprons. It was a very French maid type cotton apron which you tied with bows at the neck and back. There was a lot of cord, so the bows turned out to be quite large.

I set to work, and listened to the singing coming from the shower. I really was getting the hang of moving in heels!

When she came out of the steam-filled bathroom in a towel, I couldn't help staring.

'Are you finished your chores?' she asked sternly

This game had moved into a new phase. I was being dressed, paraded and put to work by her. Her tone had changed as well, from playful to commanding.

I wanted to escape back to my comfort zone, but didn't know how.

To be Continued...