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He chuckled. "Not so keen to parade yourself in the street, huh?"
I shrugged.
"OK, well, get what you need out of the drawers there."
"Perhaps you'd, uh, would you like to perhaps come over for dinner tonight?" I asked.
He thought about it, then said "Sure, but I hope that you'll be dressed appropriately."
"Appropriately?" I said, unsure.
"Yeah - I mean it's nice when you're all dressed up like a slut," he said, running his eyes over my soiled outfit. "But I reckon you might need to find something nicer to wear for dinner."
"OK," I said. "Well, come round at 7.30 and I'll do my best."
He went out, shutting the front door, and I did my best to clean up and find some clothes to put on. As I showered, I wondered at the situation. He'd seemed incredibly aggressive towards me that first night, but it seemed hat now I was co-operating with him, he was behaving in a much more pleasant fashion. What kind of guy was Gary? I had no idea. He seemed to get off on dominating me though, and right now I wasn't complaining. I just had no idea what I was going to do when my wife arrived home - which was only four days from now.
I made my way home and rang work, telling my secretary I'd come down with flu and thought I might be out of action for a few days. Then I set about raiding Sam's wardrobes for everything I could find. Until now, I'd always stayed away from her things, fearing that I might be caught out by the odd stain, stretch or ladder. But right now I didn't care. Over the course of the day, I assembled any number of possible outfits, before settling on a black dress which was stretchy enough to squeeze comfortably into, with a pair of sheer stockings and black heels. I took some time to run a shaver carefully over my legs to keep them as smooth as possible.
- 3 -
When the doorbell rang, I met Gary with a big smile. I'd done my makeup as best I could - a better effort than the previous day - and splashed on some of Sam's perfume, too.
He raised his eyebrows in surprise. "I didn't realise you were dressing to go out!" he said,
"Err... no we're eating here - I just thought you wanted me to dress nicely tonight?" I said, uncertain.
"Hell, why waste a good outfit!" he said. "Come on!". Before I knew it, he'd grabbed me by the hand and was towing me outside towards what I assumed must be his car. I was too stunned at the time to realise he must have driven it around the corner to my house deliberately. He opened the passenger side door and bundled me inside, slamming the door. I was grateful to realise the windows were tinted.
As he started the car and pulled out into the street, I summoned some courage to protest. "Gary, please," I said, "I can't go out in public like this. Can't we please go back home?"
He looked over at me. "What's the problem? You've got your dress and makeup on. You look like a hot date to me - hell, I'd do you!". He laughed at his own joke, and I felt myself blushing despite the situation.
Then to my relief he smiled, and said "Don't worry - I've brought some things to help you out." He pointed to a small sports bag in the footwell, which I opened to discover contained a wig of short, silky black hair, and two squishy items that I suddenly realised were fake breast inserts.
"I'm taking you to a restaurant where they know me well, and we've got a private dining room. So just keep your head down while we're getting seated and I'm sure nobody will notice."
I spent the trip there using the small mirror in the passenger sun shade to try to position the inserts and wig to maximum effect, but by the time we pulled up, I wasn't convinced I looked like anything but a guy in women's clothes. Gary seemed more impressed though, remarking that it was such a fine effort I needn't bother ducking my head. And as we entered the restaurant, to my horror he took his time greeting the owner and several waiters, introducing me as his new girlfriend Jane, and generally making it impossible for me to hide. But to my surprise, they greeted me warmly and didn't appear to notice anything amiss - the owner Geoffrey even giving me a peck on the cheek!
We were finally steered towards a small private dining room at the back, which had a small couch-style seat for me, and a comfortable chair for Gary. Geoffrey introduced our waiter, Charles, who was a tall, dark-haired young man with muscles rippling under his black t-shirt. I couldn't help feeling a bit weak looking at him, and wondered if this was what women felt when they talked about going "weak at the knees". Perhaps I was only imagining it, but I could have sworn he was checking out my legs and backside as he got us seated. Water and bread were served, but I took the first opportunity possible to slip out to the bathroom to check my outfit. I almost used the men's by mistake, before tottering into the ladies and checking in the mirror to see that my wig and makeup were OK. To my surprise, I was starting to see why nobody had commented - in the mirror I saw a young woman; perhaps not the most attractive, but with a certain cuteness about her. I was actually looking far more like 'Jane' than 'John'! I carefully checked my inserts were sitting correctly in my bra, then smiled at myself in the mirror and practised a little wink. The noise of someone approaching the door startled me though, and I quickly left as an older lady opened the door and walked in.
"Ah, here she is!" said Gary as I returned. Charles was discussing the wine list with him, and they appeared to be on very friendly terms already, though Carlo called him "Mr. Davids", which I realised was Gary's last name. "Jane, I was just saying to Charles here that he has a very Italian look about him - don't you think?".
"Mmm-hmm," I nodded, not daring to try to actually sound like a woman.
"Well I couldn't help asking him, and it turns out I'm right - tell her your real name, Charles."
Charles laughed. "It's actually Carlo. But my mother wanted me to fit in at school, so..." he shrugged.
"Do you like Charles better, honey? Or Carlo?" asked Gary. I glared at him, realising he was trying to force me into talking. I took a quick swig of water to cover my mouth, and mumbled "Carlo".
Gary laughed. "See! I told you. Jane has a real thing for Italians you know."
"Oh really?" chuckled Carlo, raising an eyebrow. If I'd been uncomfortable before, I was now bright red with embarassment, and wished I could disappear into the seat cushion.
"Well, I'll be back shortly for your order," said the waiter, and thankfully left.
Gary continued to chat to me as if nothing had happened, and as the meal progressed, he plied me steadily with wine and good conversation, and I actually started to relax and feel comfortable playing the part of Jane once more. Before I noticed it, I was completely drunk, and staggering into things as I got up to visit the bathroom again. Gary was clearly enjoying himself too, taking every opportunity to touch my legs under the table, and make completely inappropriate comments to Carlo. I couldn't h
