Craig - Cover

Craig

by Its a skirt, not a kilt

Copyright© 2020 by Its a skirt, not a kilt

Fiction Sex Story: Desperate to own a wedding dress, Craig decides to buy one second hand from the local classifieds. Things don't quite go as he envisioned they would.

Caution: This Fiction Sex Story contains strong sexual content, including Ma/Ma   Reluctant   CrossDressing   Fiction   Anal Sex   .

Craig scanned Scot-ads. Several of the advertisements caught his eye. “Maggie Sottero, size 14, strapless, princess style £300” I don’t think so. “Ivory wedding dress. Designer by Debenhams, plain bottom half with train. Needs dry cleaning hence £100” Hmm possible. “Ivory wedding dress, size 14 good condition, detailed bodice with train £60” It was a local number. He pulled out his mobile and dialled the number. It was picked up on the fourth ring.

He was so nervous he could hardly keep hold of the phone to his ear. It felt as though he had a snooker ball lodged in his throat.

‘Hello?’ Asked a tired sounding woman.

‘Hi, errr’ He hated how nervous he sounded. ‘I’m phoning up about the advert you have in Scot-ads. The ivory wedding dress? Is it, umm, still for sale?’

There was a pause at the other end of the line and Craig almost hung up there and then as his bottle rapidly disappeared.

‘It is.’ Another long pause. ‘Are you looking to buy it?’ The voice sounded a little sceptical, so Craig plunged on with his pre-planned cover story.

‘Yes, I’m, err, I’ve been invited to a party, the theme being movie characters, and as a dare, stroke, laugh, I said I would go as “The Bride” out of Tarantinos “Kill Bill” films.’

‘Oh, right. Sounds like fun.’ The voice on the other end of the line changed tone from dubious scepticism to one of amusement.

‘Yes, well. I was slightly drunk at the time.’

‘Ahhh.’

‘Indeed. But I said I would, and, well, I like to think I’m a man of my word.’

There was more laughter from the other end of the connection.

‘I know. Drink is evil.’ Craig laughed as well, relaxing. This isn’t so bad.

‘So, are you going to go full hog then?’

‘Excuse me?’

‘Makeup, stockings, garter, something frilly underneath?’

‘WHAT!!! Hell no!’ Peals of laughter greeted his outburst from the woman at the other end of the line.

‘Why not?’ Asked the almost hysterical woman. ‘You can’t wear a wedding dress without stockings and a garter. It’s traditional!’

‘There is no way I am going to walk into a shop and buy ladies underwear. This phone conversation is embarrassing enough!’

More laughter from the woman.

‘This party sounds like fun. What’s the address?’

Craig wasn’t sure if she was joking or not and decided to play safe with a non-committal grunt. The conversation was starting to get out of control. The whole idea had sounded like a good idea at first, now, he wasn’t so sure. He needed to regain his focus and the reigns of the conversation.

‘So, what time can I come round tonight and see it? Seven too late?’

‘Sevens fine, I’ll be out, but my husband will be in. I’ll leave the dress out and warn him someone’s coming round to have a look. Got a pen handy?’

Craig replied yes and she supplied him with an address in Mannofield. He thanked her and hung up. He was shaking all over with adrenaline and sweating profusely.


Pulling into the first available car space that he saw, Craig took several deep breaths in a futile effort to try and steady his nerves. For the hundredth time since he had got into his car, he debated whether or not he had the courage to even ring the doorbell. The only thing that stopped him from turning the car around and heading back to his flat, was the pay off. Almost since he had started to dress in women’s clothing, he had fantasised about wearing a wedding dress. Over the years, he had managed to buy or ‘acquire’ various skirts, dresses, and underwear, but the first time he had plucked up the courage to walk into a bridal shop, he had almost passed out in shock when he had seen the prices on the dresses. It had never occurred to him until now, to look for vastly cheaper second hand dresses.

Think of the prize. Walk in, pay for it, and walk out. It won’t take more than a few minutes and you’ll never see them again. Come on! Get a grip! He checked the pocket with the cash and opened the car door, desperately trying not to think about what he was doing. His nervousness was so great, that he managed to forget to even lock his car. A disastrous mistake had he parked in Torry.

The house number was proudly displayed on a wrought iron gate leading up to a typical granite walled semi-detached house. The front garden either side of the path was immaculately tended.

Deliberately denying himself the chance of even more second thoughts, he stabbed the doorbell as soon as he reached it.

Feeling immensely guilty, he furtively looked around as he heard a door open inside the house and footsteps approach.

A security bolt was undone and the door was opened, framing a nondescript man, clean shaven in a shirt (collar undone, no tie) who looked to be in his mid-forties.

‘Yes, can I help you?’

‘I’m here about the, ummm, wedding dress.’ Craig felt his face start to turn a rather embarrassing shade of red.

‘Oh right. The wife did mutter something about that before she left. Come on in.’ He stepped back, turned and was about to walk back into the hose before he paused and turned back to Craig. ‘Sorry, where’s my manners. I’m Brian.’ He held out his hand. Craig took it and they shook.

‘Craig’ Supplied Craig as he withdrew his hand from the shake.

‘The dress is through here. Going to a party are you?’

‘Umm, yes.’

‘Word of advice. Don’t get married,’ Brian laughed ‘You still get to go to parties, but they aren’t as much fun as they were before you got hitched. And it seems as though you spend longer waiting for your wife to get ready than you actually spend at the party.’

‘I’ll keep that in mind.’

‘Just through here.’ Brian led him into what was obviously a guest bedroom. The dress was laid across a bed lacking sheets, displayed in all its wonder. It was stunning.

One glance was all it took for Craig to decide he was buying it. He had thought about maybe attempting to haggle the price a bit lower, he couldn’t really afford the money for the dress as it was, but after seeing it, decided that the dress was more than worth the asking price.

‘Try it on, see if it fits.’

‘Okay’ replied Craig, not really aware of what his mouth was saying, as all his attention was captivated by what lay across the bed. A door shut behind him. Startled, he looked around. He was alone.

Alone with the dress.

He reached a trembling hand out and gently touched the material of the dress. It felt so smooth, so sexy, so inviting.

For the first time, he noticed a note lying on top. He picked up the note; ‘I just couldn’t bear to think of the dress not being worn properly. I was going to throw out the basque anyway as it is old and –’ The words ‘it no longer fits’ were hastily scribbled out ‘- I no longer have a use for it. You can have the stockings and lingerie for free; all I ask in return is that you wear them with the dress.

PS And that you send me a picture LOL :) ‘

Craig moved the dress aside. Underneath, was a plain white padded basque, matching panties and a pair of white lace top stockings. There was also a lacy garter. The basque and pants were so old that they were no longer their original bright white and were now a slightly dirty looking yellowish colour. But Craig didn’t really care about that. In fact, there was something decidedly sexy about them and the fact that they used to be worn by an actual flesh and blood female.

He felt dizzy, not quite in charge of his facilities. This was more than he had ever dreamed of. He desperately wanted to get back to his small cluttered flat as soon as possible. His gaze was continually drawn back to the dress displayed so provocatively in front of him.

Okay, just for a moment, to see if it fits.

He slipped off his jacket and trainers and released the belt buckle on his jeans, only intending to try on the dress over his T-shirt and boxer shorts. But the note teased him. She had a point, the dress deserved more. His T-shirt ended up on the bed as he wrapped the basque around his chest and started to fasten the hooks and eyes together. Craig had to breathe in and suck in his stomach to get the hooks and eyes to connect.

 
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