The Shopping Trip                by: Annalise Barker

 

Part Two

Paul went white. It was bad enough when he was 10 years old, but he was 29 and had a good job as a solicitor. What was she thinking? What happened to the old adage ‘Blood is thicker than water’? "Of course not. Are you mad?"

"Actually it was a rhetorical question," said Joanne. " I’ve already told the girls what we are going to do and they think it’s a great idea. They don’t know why you’ve accepted to do it, but they think you’re very brave. In fact Cathryn said that she wished her ex-boyfriend had had the bottle to try something like this." Paul was feeling sick to the stomach, but he knew what Joanne could be like if she did not get her way; although she was not mean, she did have a wicked sense of humour, and might have just mentioned their childhood games to one of his colleagues in the legal profession. " What about the lads that are arriving tomorrow?"

" Actually they’re not coming. Cathryn really wanted you to come, but she thought that if we told you it was just a girls’ trip, you might decide not to join us."

Paul was stuck. What choice did he have? Before he could think about it anymore, there was a quick knock and the door opened. Standing in his room at the foot of his bed were Cathryn, Louise, Emma and Sarah. " Paul, this is so great that you’re doing this," said Louise. " Cathryn always said you were a good sport, but this is fantastic. We can have a really girly weekend together, but first we must get you something to wear."

At that, each of the girls in front of him pulled out from behind their backs various items of clothing. Sarah brought out a short pleated purple skirt and standing next to her, Emma showed Paul a pair of black patent court shoes. " Apparently we are the same size," she said. Joanne had one of her silky cream blouses and Louise gave Paul a pair of sheer stockings in a beautiful lilac colour. " What am I supposed to do with them?" Asked Paul.

Then Cathryn stepped forward and sat on the edge of the bed. " I thought you might like these." In her hands she had three of the most beautiful, feminine items of women’s lingerie that Paul had ever seen. All were in the same gorgeous lilac colour as the stockings that Louise had given him. There was a silky lace-trimmed bra, a lacy suspender belt, and a matching pair of silk panties. Paul’s emotions were mixed. He loved the lingerie, and thought the other clothing was beautiful, but he would rather see any one of these pretty girls in front of him wearing them rather than him. But he had little choice. Joanne began to usher the girls back out of the room, but Cathryn stayed behind. "It’s alright Jo, I’ll help him." Joanne smiled, nodded and left the room, shutting the door behind her.

"So, what shall we call you my pretty Paul?" said Cathryn.

"’Paul’ would be fine, if it’s all the same."

"No, I don’t think so. We will be out shopping, skating, dancing, going to a show, visiting art museums, and you will be a girl for all to see. Now are you sure you want us to call you ‘Paul’ when we are out doing all these things? Your choice, but I think you’ll get some funny looks."

"Eh, ok, I see what you mean. How about ‘Paula’?" suggested Paul.

"I suppose… but I think we can find something better than that, something that reminds you are a girl every time someone calls you. How about ‘Lisa’ or ‘Sally’ or ‘Lucy’?"

"Ok, ‘Sally’ could work."

"Great! ‘Sally’ it is. I am so pleased you are getting into the swing of this. You have no idea what you are letting yourself in for. Girls have so much more fun than boys. You’ll remember this trip for the rest of your life, I promise."

With that, Cathryn handed Paul a tube of cream and told him to go and shower, and to use the cream to remove his body hair. Ten minutes later Paul re-entered the bedroom with a towel wrapped around his waist. "No, not like that. Like this." Cathryn took the towel and re-wrapped it higher up so that it covered his breasts. "That’s how us girls do it," she said. Then she sat him down and started to blow dry his hair. "Isn’t it lucky that you already have hair a bit like a girl?"

"No I don’t," complained Paul.

"Actually you do, and it will look even more so by the time I’ve finished with it." As Cathryn had now removed the mirror, he had no way of telling.

"Now I think it’s crunch time. That is my favourite set of lingerie, so be careful when you put it on." Paul reached for the lacy bra first and had problems straight away.

"Turn it around first. Attach it at the front, then move it round," she advised. Once this was in place, Paul selected the suspender belt. He had had plenty of girlfriends before, so knew this had to go on before his knickers. He couldn’t believe he was thinking these thoughts. Then he picked up the silky panties. As he started to pull them up his legs, he felt the soft material slowly glide over his smooth thighs, and could barely believe the sensation he was feeling. Cathryn sensed what was going on. "Enjoying that Sally?" Paul blushed like a girl, but didn’t reply. Next came the stockings from Louise. Paul rolled the first stocking as he had seen girlfriends do countless times before. As he started to draw it up his hairless leg, his stomach knotted up. This wasn’t how it had been when he was 10, was it? He knew he shouldn’t be having these feelings – this felt really good, and it was showing in a physical way. Cathryn was smiling. "I think the answer to my last question is ‘Yes’"

She pushed him gently backwards onto the bed and climbed astride him. Very gently she slid the silk panties down to his knees and unhooked the suspender belt. Bending forward, she took the tip of his cock into her mouth and grasped the rest with her left hand. The other hand moved up and began caressing Paul’s nipples through the silk bra. Moving slowly with each hand, she brought him to the point of climax until he was crying for her to finish the job. The gushing warm fluid filled her mouth and she swallowed time and again until they both collapsed on the bed exhausted. "I don’t know what you just did exactly, but I have never had oral like that, ever," gasped Paul.

Twenty minutes later they were both showered and back to the state where they had been earlier. Paul finished putting on the luxurious lingerie set, and thankfully most of his physical urges were rather more subdued this time. Cathryn handed Paul the silk blouse from his sister and then the purple pleated skirt that Sarah had brought. He slipped them on and fastened them up. The final item was the black court shoes from Emma. When Paul looked down he saw that his legs had subtly changed shape. There was only a 1" heel on the shoes but the difference was amazing. Next came the make up; a luscious red lipstick, blusher, mascara and a lilac eye shadow. A little spray of her favourite perfume, ‘Tommy Girl’ and Cathryn stood back and admired her handiwork. "Wow! You look fantastic! Gorgeous! If your sister didn’t know what we were up to, I bet even Jo wouldn’t recognise you. I’ll tell you what – let’s go down to the lobby and wait for the girls there."

"Can I see what I look like first?" Jo picked up the mirror and placed it on the dressing table. "Ok, prepared to be amazed," said Cathryn. Paul opened his eyes and looked. It was a vision of beauty that was gazing back at him. He had never even dated anyone that was so good looking. Cathryn opened the bedroom door and beckoned her new friend to join her. Paul knew he had no choice, so followed Cathryn out into the corridor. Luckily she had a spare winter coat, a long black wool number, so Paul draped that over his arm and went downstairs.

When the girls came down, they saw Cathryn sitting on her own. Paul was standing near the check-in desk. "Paul will be down in a bit – he’s just finishing off."

"I can’t wait to see the result; what does he look like?" said Joanne. "I’m feeling a bit guilty now for suggesting this; people are going to be staring at my baby brother all day - a stupid boy dressed in girls’ clothes."

"Excuse me, is that seat taken?" asked the pretty blonde English girl.

"Well actually my brother is coming down in a minute………" Joanne stopped in mid sentence. "No… It can’t be... Paul?"

"No, it’s Sally actually."

All the girls were in shock, not quite able to believe their eyes. "You look like a girl, a real girl!" said Emma.

"You’re gorgeous, feminine, sexy!" exclaimed Sarah.

"I have the sister I’ve always dreamed of," uttered Joanne, still amazed at the transformation. "We should have done this years ago. You look fantastic."

"Right, enough of all this adulation for my pretty, feminine charge. It’s time that us girls hit the town and bought this special girl some clothes of her own. All suggestions welcome. GAP first, then Victoria’s Secret, Bloomingdales, then who knows… Come on my pretty Sally, lead the way."

Before they even got out of the hotel lobby, a tall handsome businessman was walking ahead of them and held the door open. "Ladies first," he said, looking at Sally up and down as she slipped on her new coat. Sally blushed again which pleased the man no end. "I don’t believe it," whispered Joanne, "We’ve been here less than 24 hours and out of four gorgeous girls, it’s my brother that pulls the hunk." "Sister," reminded Cathryn, "She’s your sister now, and don’t forget it!" As Sally took her first tentative steps out into public, the first thing she felt was the chill winter breeze against her stockings, swirling around under her short skirt. It was cold, but it felt fantastic. Maybe this was going to be a good trip after all.

 

To be continued………?

 

 

 

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© 2001 by Annalise Barker. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.