Jack's Transformation

by Keeley

  

The night before had been a disaster. Both Jack and Sally had both had a few drinks and when she suggested he should dress up for sex in her lingerie he'd lost it and walked off. They'd only been together for a couple of months and their relationship was the best Jack had ever had and now he was worried he'd ruined it by his actions.

He hadn't heard from Sally and didn't really know what to say if he contacted her. His overreaction wasn't something he was proud of. It wasn't anything he'd been asked before and wasn't anything he wanted to discuss with anyone else either male or female.

He eventually got the courage to call Sally but only got her voice mail. he left a message apologising and asking what he could do to make it up to her.

10 minutes later he had a text message come through from Sally - "Show me". What did that mean but after some thought he guessed it was to do as she'd asked the night before. He didn't feel comfortable with it but if it was the only way to get her back what could he do?

After much deliberation, involving tossing a coin to make his decision for him, he eventually decided that he would do it but he couldn't just go round to her place and go upstairs and put her bra and knickers on. For one it would be too easy and not really appease her and two it probably wouldn't fit. Why hadn't he said that last night he thought to himself. That meant he had to go out and buy somthing himself.

He apprehensively waslked in to the nearest department store and as he approached the lingerie section he could feel himself going bright red with embarrassment. It didn't help that he was the only male in the area. As he moved towards the first row of bras he senses that everyone was looking at him. He was desparate to get out of there but he couldn't just pick up the first thing he saw as Sally only wore very sexy lingerie and would expect the same frm him. He tried to remain as inconspicuous as possible as he looked through the racks. He finally found something that he thought Sally would like and although he hated to admit something he thought might suit him. As he tried to find the matching knickers in the same size he began to get aroused which wasn't helped when one of the assistants came over and asked if he was ok. He stuttered a "yes, fine thanks" and went back to trawling through the knickers until he found a pair that he guessed would be the right size. The excitedness he'd began to feel had died down so he thought it would be best if he went and paid.

As he made his way over to the till, his phone beeped "Show me - and not just lingerie".

He instantly started to feel red cheeked again working out that lingerie alone wouldn't be enough. But what would be - make up, a dress?

He found a basket and put his lingerie in before making his way to the dresses. If it was hard buying lingerie, it was going to be even harder buying a dress. After all, men often bought lingerie for their partners but dresses need to be tried on which he was afraid he would need to do. After a little bit of thought he decided to go for a shortish party dress and knowing he little choice made his way towards one of the assistants. He told her he needed a dress for fancy dress party but had no idea what size. She looked him up and down and pulled out a size 12. " Try that, it may be a bit tight but you look slim enough to give it a go and the padding from the bra in your basket should help give it a little shape". Walking over to the changing rooms he'd never felt so embarrassed in his whole life. He dived into the changing room and undressed. Remembering what the assistant had said he guessed he should put the bra on first. He unhooked it from the hanger and tried to work out the best way to put it on when he heard "Do you need a hand?". As much as he wanted to say know, he needed help and he hesitantly said yes. The assistant walked in and asked him to put his arms up. She pulled the bra on and hooked him in and although it was bit tight he didn't feel too bad and as he looked at the reflection in the mirror began to feel aroused again. Not wanting the assistant to notice he said "Thanks for that, I should be fine now" and she left him ready to try the dress on. He pulled it over his head and lthough he the zip was little awkward at the back he felt relatively comfortable and as he looked in the mirror he had to admit his figure looked pretty good which seemed to arouse him even more.

After getting changed back he put the dress in the basket, went over to the cosmetics area and selected some red lipstick and went to pay. Luckily it was the same assistant who'd helped him with the bra so he wasn't as embarrassed as he thought he was going to be even when she suggested that he should get some stockings as well.

Finally he made his way home. After a quick shower he started to get himself ready. He pulled the bra on and after a bit of fumbling me managed to hook it up. Necked he pulled on the matching knickers and he had to admit they were very comfyand again he started to get aroused. Maybe this wouldn't be so bad after all. Next he put the dress on and as he pulled up the stockings the feeling of arousal was intensified. What was happening? He applied the lipstick and decided it was time to go. Luckily he could get to his car without going outside so noone would see him. He drove the 5 miles over to Sally's place and parked in the drive. Unforunately the cover of a garage wasn't available this time. Plucking up the courage, he got out of the car, still in a state of excitedness and walked up to her front door and knocked.

Whilst he waited at the door it seemed like an eternity. The breeze began to blow under his dress and it appeared to make the silky knickers brush against his manhood. At the same time he could feel the bra almost piching at his sides and the dress clinging to his skin. The feeling gave him a huge rush and before he knew it he had a huge erection. Seconds later the door opened. Sally beckoned him in and closed the the door behind him.

"So who's a pretty girl then, and by the looks of things this girl is enjoying being pretty". He looked down and started to blush. His erection was very evident through the tight dress. He started to wish he'd bought a pair of tighter knickers rather than the silky French pair he had on. He didn't know what to say. His decision to march out last night had looked like a bad one for more reasons than one although by the smile on Sally's face maybe it wan't so bad after all. She came up behind him and unzipped the dress. Slowly she pulled it down taking time to rub her hands against his bra and then on to his backside before gently stroking his stockinged legs.

He felt his balls tighten and had to work hard to contain his excitement. She came back round to the front and took off her jumper, unzipped her skirt to reveal a very skimpy lingerie set which he hated to admit wasn't as nice as the one he had on. She walked towards him and kissed him full on the mouth. He could feel a dampness in his knickers but for some reason he was unable to react to her promptings. She took his hand and guided him upstairs and in to the bedroom.

As he entered he noticed that the assistant from the department store was lying on the bed in the same lingerie set as he had on.

Jack didn't know whether he was dreaming. He closed his eyes and opened them again. Sure enough the assistant was still there lying on Sally's bed. He hadn't paid much attention to he in the store, mainly through his embarrassment but as he looked at her now she was absolutely stunning and certainly filled the bra a lot better than he did. He couldsn't comment on her behind but he was looking forward to comparing that as well!

Whilst he was thinking of seeing her arse, Sally started to explain.

"This is Claire. She's an old school friend which I experiemented with when I was younger. I bumped in to her last week and it was those memories that gave me the idea of dressing you up".

The thought of Sally and Claire experimenting was driving him wild and he moved his hand down to touch himself and the feeling was only improved as the soft silk rubbed against his balls. Before he knew Sally had moved his hand away.

"You'll have to wait for that. As I was saying, i bumped in to Claire a couple of weeks ago when I was meeting you after worter work. When you decided you would join in I was pretty sure you'd go to that store so I asked her to keep an eye out for you as I sent her a picture. When she saw how excited you were in your bra she asked if she could join in."

With that she let go of Jack's hand and walked over to the bed and started to kiss Claire. They then moved in to the 69 position and pulled down each other's knickers and started to perform oral pleasure. The whole time Jack's balls were getting tighter and tighter. Eventually Sally beckoned him over. He slowly walked over and she pulled down his knickers and started sucking on his very erect penis. Amazingly he managed not to explode there and then.

Just as he was about to climax, Sally stopped. "Not quite yet darling. I know you've been through a bit of embarrassment today, but by the look of it it's all been worth it but you need to learn that what Sally wants sally gets and it's not after a sorry, so before we let you finally enjoy the night you're going to come out as one of the girls with me and Claire for the night. Don't worry, I've got you a wig and we'll make you up a little bit better than you managed. After that, well then you'll be rewarded, so pull up your knickers and put your dress back on and we'll get you ready."

Jack desperately wanted to say no and was about to do so when Sally we ntto a draw, pulled out her digital camera and took a quick photo.

"If you think about saying no, then we'll have to circulate this."

He wasn't used to being domineered but felt he had no choice but to do as he was told. "OK I'll come out with you but you need to delete that afterwards" he said as confidently as he could. "certainly darling. Now we'll have to get you a different pair of knickers as those look a little damp and show your excitement about wearing lingerie a bit too much. She went to her draw and pulled out a lacy pair of short style knickers. "These should hide your embarrassment".

He took off the silky pair he had on and replaced them with the lacy pair and was astonished how good the lace felt to the extent he wished he'd tried on his sisters when he was younger.

Sally beckoned him towards her and sat him down on a chair. "Keep still and we'll have you made up in no time. Claire, can you get my make up bag from the bathroom?"

Between the two girls he was made up in no time. Before he was allowed to look he was told to put his dress back on which he did a lot easier than he'd managed earlier in the day. "Claire, did you manage to find any heels in size 10?." "The biggest I could find that would go with the dress were a 9 but she should be able to squeeze in to them". Claire pulled the bag out from under the bed and gave Jack the pair of heels which with a little bit of effort he managed to get on. Sally pulled a long blonde wig out from the cupboard and placed it on to his head. After a bit of manoevering it was in place and he was allowed to look at his female self. "What do you think" Sally asked. He walked to the mirror and the reflection coming back at him was one of a very pretty lady. If he didn't know he'd fancy her he thought to himself.

"As a reward, you can stay here and watch us get ready". He sat down and they began to undress each other and kiss each other all over again. Now he was all dressed up he couldn't touch himself how he wanted to but he was enjoying the little show none the less. Eventually they stopped and got themselves ready and they were ready to hit the town.

"Before we go what do you want us to call you" Claire asked. Jack's initial thought was to go with Jackie but that might be a bit obvious if they did meet anyone he knew even if he was looking away. "I'll go with Amy" he replied.

As Jack walked out the door a taxi was waiting for them. On one hand he was relieved as although he'd managed to walk relatively easily in the heels so far he didn't fancy a long walk in them. On the other hand it was the usual taxi company that he and Sally used and he was worried that he'd be recognised straight away.

As they got in, the driver thankfully paid little attention and just asked where they were going to. The journey was a short one and the whole time Sally spent talking to Claire which Jack was quite relieved about. He was almost expecting them to talk about "Amy" the whole way there.

After they paid the taxi driver they went in to the nearest bar and to Jack's horror were greeted by a group of Sally's friends.

"Hi everyone, this is Claire and Amy. Before you ask, we're all dressed up as we've been out for dinner with Jack and Claire's and Amy's boyfriends. It was some important work do".

Sally's friends introduced themselves and then the moment Jack was dreading came, when one of the friends asked "where do you know Sally from". It wasn't a probmlem coming up with an answer, it was doing so in a voice that wouldn't give him away. Although he didn't have a particularly deep voice it would still be obvious unless he disguised it somehow. Then to everyone's surprise he just came out with it. "I'm not Amy, I'm Jack. I'm dressed like this because I lost a bet". What was he thinking, but it was too late now. "Well you make a very pretty girl Jack, I'd never have known" she replied. Sally just smiled at him.

It soon became the topic of discussion and he had to admit he liked being the centre of attention of all these women. Every so often Sally would stroke his stockinged legs and his arousal would becme obvious but strangely he felt comfortable. Where the night was heading he had no idea but at the moment he was going to enjoy it.

It soon became his turn to go to the bar. He went and ordered doing his best to put on a feminine voice. Avoiding eye contact he picked up the tray of drinks and walked back to the girls where Sally made her next announcement. "We've decided, you're coming out as Amy every Thursday now, oh and before you say anything, it's in your best interests to say yes"

  

  

  

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