Cancelled Date Night Ch. 01

Dave was starting to get anxious. The tv was on in front of him but he barely registered what was on the screen. His eyes spent most of the time glancing desperately at his phone on the armrest next to him, yet every time he unlocked it the same disappointing clock face shone back at him. No new messages.

Sarah was now an hour and a half late. It wasn't too unusual for her to be late but the fact that this was their date night and she hadn't even text to let him know what was up had Dave incredibly worried. Dave knew he was a worrier but he also knew his girlfriend and if anything she hated people worrying over her.

His mind was running through all the horrible things that could have happened for a third time when he heard a key in the door. His heart almost leapt out his throat and a hot surge of relief surged from his toes up to his head.

His relief however was swiftly replaced by annoyance. Now that he knew everything was ok, he was free to let himself feel anger at Sarah's lack of communication. jumping up from his seat and went to confront her in the hall.

The anger didn't last long though, as soon as he saw Sarah's face he knew she was sorry. Her stressed and weary eyes gave him a puppy dog look that melted any frustration he was feeling.

But before either of them could say anything a man followed Sarah through the door.

'Oh hey Colin, I...'

But he obviously didn't feel like chatting as he pushed past Sarah and ran upstairs without so much as a second glance at Dave. His head was in his hands but it was pretty clear that he'd been crying pretty heavily. Dave directed his confusion towards Sarah;

'Look I'm sorry sweetie. I'll explain later I promise.'

She gave him a desperately apologetic look and ran upstairs after Colin. Dave stood in the hall staring up at the empty staircase for a few seconds before giving a defeated sigh and wandered off to the kitchen. It looked like he'd have to make his own plans for the night so he grabbed himself a beer and browsed through his dvd shelf for a mindless action film that Sarah would hate.

Colin was a work friend of Sarah's. He was a nice guy and Dave usually got on well with him but he could be an awful drama queen at times and as he and Sarah were "besties" it usually fell to her to pick up the pieces. Dave was well versed in the procedure at this point, as this type of thing had started to happen quite frequently since Colin officially came out, so he knew the rest of the night would be a write off.

He was 5 minutes into "Shoot 'Em Up" when Sarah returned down. Dave felt two hands creep down his shoulders and cross over his chest. A warm cheek pressed up against his ear and he turned away from the ridiculous action scene to be greeted by a strong, passionate kiss. The angle was a bit awkward for Dave but he wasn't going to object while Sarah's tongue danced cheekily around his mouth. It was a good deal longer than their usual kisses and it had done a considerable amount to improve Dave's mood but he still decided to tease Sarah a bit for what she had done to him.

'Finally decided to give some attention then?'

'Oh baby, I'm so sorry. I really am. I should have called.'

'It's ok I'm just teasing you. I'm just happy you're ok. I was getting pretty worried.'

'Oh no I thought you might be. I really did try to get in touch but you know Colin when he gets going, you can't take any attention away from him or he'll go into hysterics.'

'Looks like a pretty bad one this time.'

Sarah sighed deeply and rolled her eyes.

'Yeah. The chap is not right at all these days. I thought things would get a lot better for him when he finally came out.'

'Sometimes it's not all that easy it seems.'

'I guess not. Well I better get the wine and head back before he feels abandoned on top of everything.'

'Wine? This must be a bad one then.'

'Yeah I think we can consider the night a bust I'm afraid.'

'I kind of anticipated that.'

Sarah suddenly dropped her lighthearted tone and looked into Dave's eyes with sincerity.

'I will make this up to. I promise baby.'

'Oh yeah? You'll watch a dumb action flick with me for next date night then?'

'I was thinking dumb action flick with a hint of blowjob actually.'

Dave nearly spat out the sip of beer he'd just taken. Sarah was never usually that blunt about sex.

'Tha'...that...will do nicely.' he stammered, trying to come across as casual. Sarah walked off giggling at his utter failure to do so.

Dave could hear her bare feet stick ever so slightly to the wooden floor as she made her way to the kitchen. He leaned back in the chair and admired her as she swayed out of the room. She had changed into her pajamas since she'd come in, just an old tshirt and a pair of cotton shorts but she still made it look sexy as hell. Both were slightly too small meaning even from behind you could catch a glimpse of her unsupported breasts trying to swing beneath her shirt with each step and the shorts came only covered half her ass so Dave was treated to an ample view of the flesh atop those smooth bare legs.

He continued to appreciate her through the kitchen door as she grabbed two bottles of wine from the shelf, gave an adorably valiant effort at a sexy model spin and blew Dave a kiss before skipping back up the stairs.

Dave's cock stirred in his jeans and he had to concentrate pretty hard on what Sarah had said about making it up to him to calm it back down again.

Dave was beginning to doze off mid way through his second action movie when Sarah returned. He could tell straight away that those two wine bottle must have been mostly emptied. Sarah was even less inhibited than earlier, she strode into the room she climbed up on Dave's lap. Kneeling astride him, she grabbed his head and gave him another long, hard kiss.

Dave's cock immediately swelled and Sarah must have felt it as she started to grind on his crotch. To his frustrated dick this felt amazing, even through his jeans. Dave grabbed Sarah's waist tightly and started to grind back. Their kissing intensified and Sarah's hands started to wander around Dave's chest. A low moan escaped Sarah's mouth and this seemed to bring her out of the passion and back to reality. Dave's cock nearly cried out as she stopped her grinding and sat back on his knees giving him and even more apologetic puppy dog look than earlier.

'Im sorry baby. Got a bit carried away.'

Dave knew her too well. He wasn't getting any tonight. He wanted to scream out in frustration but he knew it wasn't Sarah's fault. The situation with Colin must be pretty serious if she was this horny and still denying them both release. He buried his frustration and tried to be supportive.

'That's ok. I see you've changed, are you two heading out?'

With Sarah's bold entrance he only just noticed her change of attire, She had obviously spent the last few hours dolling herself up. Her hair was washed and straightened, styled so her chestnut fringe crossed over her left eye. Her makeup had been touched up to add thick black eyeliner which contrasted nicely with her deep crimson eyeshadow and matching glossy lipstick. Her pyjamas had been replaced with a black lace corset, done up tightly so her cleavage strained against straps, aching to be set free. A black frilly skirt took the place of her shorts though it didn't cover much more of her ass, leaving a good portion of skin between its hem and the top of her thigh-high stockings. The heels which completed the outfit were so high Dave was impressed she managed to get down the stairs in them considering her tipsy state.

'Hehe. No. Do you think I'd go out dressed like this without you? I actually came down to talk to you about this. I have a big favour to ask.'

Dave gave her a look that said, 'Oh really?'

'I know, I know. I'm sorry. I'm asking a lot of you tonight. But this is really important. Please.'

Dave chuckled, 'Of course sweetie, anything.'

'Well don't commit to anything before you've heard me out.'

She paused for a second and Dave noticed that she actually looked a bit nervous. He was starting to worry about what was going on.

'So Colin up there is really in a bad way. He's been having a fairly shit time of it for a while. It's pretty obvious that coming out didn't bring him the relief and happiness that we all thought it would and he's just confessed why to me. It turns out that what was making him unhappy wasn't hiding his desire for men but actually hiding his desire to be a woman.'

'Sorry, his what?'

'Well he says he thought when he started sleeping with men that would help him feel feminine but it obviously didn't do enough for him because he was still unsatisfied and deeply depressed. He was more confused and unhappy than when he tried to be straight because he had hoped coming out would finally mean he could be happy. He tells me he finally worked it out a few weeks ago, he tried dressing up and when he saw himself in the mirror everything just felt right for once.'

'Dressing up? What do you mean?'

'Sorry I meant in women's clothes. Apparently his sister left some at his place and he got curious one night. He says he realised he had always been a woman deep down and that's why he's been so unhappy, what he saw in the mirror never reflected how he felt he should look. He's been dressing more and more since and last night he finally plucked up the confidence to go out in public.'

Dave guessed what had happened before Sarah said anything.

'Oh...'

'Yeah.' she nodded her head looking glum and angry at the same time, 'He got a less than polite response apparently.'

'That explains the wine then. But what's this got to do with me? You said you needed a favour?'

'Yeah...so I thought the best way to cheer him up would be to have a girly night and show him some tips, tricks, styles you know all that girly stuff you have no interest in.'

Dave nodded. It made sense, even as a straight guy he could tell always tell that Sarah had a flair for all that stuff. It was just a hobby to her but she always seemed to know exactly what to do to perfect whatever look she was going for. Most of the time Dave couldn't tell exactly what she had done differently, just that the end result was that it all just worked and she looked amazing.

'Anyway we got a little tipsy and decided to doll ourselves up, to put my advice to the test. Hence...'

She motioned to her outfit and Dave's eyes lingered for a second on that amazing cleavage before returning his concentration to what she was saying.

'The thing is, Colin is very happy with the result. He says its way above anything he managed to achieve by himself. I've sent him into the bathroom to try a few finishing touches himself. But my plan is to try and coax him into coming down here. I snuck down to tell you first to make sure you were ok with it but more importantly to prepare you for the shock because I think the confidence boost he would get by showing off his new look would do wonders but too strong a reaction from you might destroy him.'

Dave felt bit uncomfortable. He wanted to help Sarah, and Colin for that matter, but this seemed like it would be an extremely awkward situation and Dave did not flourish in those kinds of environments.

'So what? You want me to act like everythings normal?'

'Well no because then he'll know I talked to you. You should act shocked but pleasantly so. And maybe give him a bit of attention you know how he loves that.'

Dave sighed. This was definitely going to be awkward.

'Ok I'll try my best. But you know how awful I am with this stuff.'

'Don't worry, you'll do great.'

There was some movement upstairs so Sarah jumped up and started to head back upstairs. Before she reached the door however she turned back and said;

'Oh yeah don't forget to start referring to him as a girl now that'll do wonders for the confidence. I think he's going to go by either Collette or Colleen so keep that in mind.'

And then she was gone. Dave tried to settle back into the movie but he was all tense and nervous now. It wasn't that he had a problem with the transvestite thing just the thoughts of having to compliment a guy always made him cringe. Also he was awful at lying and, though he had faith in Sarah's abilities, Dave had seen a few drag queens before and they didn't give him much hope for the outcome.

Sarah was going to have to pay him back big for this one.