The Shopping Trip              by: Annalise Barker

 

Part Three

"So what is the plan girls? I hope you haven’t got anything too nasty planned for me," asked a slightly concerned Sally, newly transformed from Paul by his sister Joanne.

They started walking down the sidewalk towards Central Park, a short distance from the hotel. Sally was now walking arm in arm with Cathryn on one side and Joanne on the other. " Well I think to start with we should just get you used to wearing your new clothes. I guess they must feel a bit strange," said Cathryn. Before she had time to answer, Joanne began to talk. "Listen Paul. I’m starting to feel a bit guilty about what I’ve done. You have never been anything but a loving, caring brother to me, and now look what I have inflicted on you. We are in a foreign country, a strange city, and you are stuck with a bunch of five girls. Not only have I got you here under false pretences, telling you that we would be one big group of girls and boys, I have done to you something which no sister should ever make her brother go through. Although I did deceive you, I honestly didn’t think I would be in this situation, having forced you to be a feminised girl for the duration of the trip. Don’t get me wrong, when I look at you now, dressed up, I think you look absolutely gorgeous, better than I could have ever imagined. But nevertheless I am so sorry for having forced you into doing this. Will you ever be able to forgive me?"

" Jo. Okay so you did get me here by lying. I am still not exactly chuffed about what happened at Customs. You were not exactly my favourite person in the world when you told me what you had in store for me, and even less so when all you girls came into my room with your various items of clothing for me to put on. No, I was not happy, but here I am on the edge of Central Park dressed from head to toe in women’s clothing; very sexy women’s clothing. It’s a done deal. It’s hardly something that any of us can pretend has not happened, so if it makes you girls happy I can do this for a few days. Anyway, how many guys of my age can truly say they have had such an insight into the way girls really behave when they’re not around."

" Are you two girls quite finished gossiping?" quipped Cathryn. They were walking through the edge of Central Park by this time, kicking what was left of the autumn leaves, heading towards Fifth Avenue, the mecca of expensive shops. The park was quite busy, and they passed a number of people are walking the other way. Sally was just trying to soak up this whole new feeling. Her mind was still spinning. She watched some of the girls that walked past in the other direction. A few glanced over and cast their eye over Sally, walking at the front. She thought she detected a jealous look, but surely that wasn’t possible. I mean she was a he, Sally wasn’t a girl, she was a boy. She was also starting to get confused. Back at the hotel was confusing enough when she was dressed in the beautiful lilac lingerie having oral sex with Cathryn, but now she was getting catty looks from girls for looking so pretty. By the time they reached Fifth Avenue, her head was really spinning.

Questions were buzzing around the group as to where they should shop first. Louise and Sarah wanted to head straight for Gap, while Joanne and Emma preferred Nike Town. "I’ll stay with Sally and keep her company while you girls go and give your credit cards a hammering," said Cathryn. They all said their goodbyes and agreed to meet back at their hotel at 6pm. "Right, what are we going to do with my beautiful charge?" asked Cathryn, already knowing the answer to her question. Straightaway she hooked her arm through Sally’s, and led her across the street towards Victoria’s Secret. "Look Cathryn, this is really sweet of you and I do appreciate the thought, but if you do what I think you’re planning, this is going to cost you a fortune."

"Enough! I know that you know what I do for a living. Well let me tell you that a barrister working in the City does not get paid peanuts. What you’re doing is not only amazingly brave, I think it’s fantastic, and I think I’ve proved that to you already. I really like you, and although I have always secretly fancied you, seeing you like this drives me wild. Consider this my treat. When we return to England, it’s up to you what you do with the clothes. Personally, I would love to see Sally again, but I understand if that’s not possible. But for now, lets both enjoy the situation. Just relax. As you said before, this is an insight into how girls really think and behave, so savour it." She then marched Sally straight into the lingerie shop. " If you are going to be dressed like this for a few days, you will need some more underwear, and I have a few things in mind," Cathryn said with a glint in her eye.

With an experienced eye, she estimated Sally was an English size 12. First of all she selected a beautiful black satin bra and thong set with matching suspender belt. Next came a white silk Basque with underwired bra cups. This came with six suspender straps instead of the usual four. Cathryn laughed to herself thinking of how much difficulty the old Paul had had with his first attempt at suspenders. She thought that if this was her Basque, she would like to wear it without any panties, but all things considered, this might not be such a good idea for Sally. Next to the Basque display was a choice of matching knickers from which she picked a fabulous pair of lacy briefs. Lastly Cathryn went over to a fantastic display of Bodies. These sleek all in one numbers covered all the right bits, and just looked so glamourous. She selected a lilac number as she remembered the look on Sally’s face when she had first set eyes on the lingerie set that Cathryn had bought her. Then without a second thought, Cathryn turned back to the display and picked out a second Body for herself. She selected a pale blue colour, but this time in one size smaller. Next she moved over to the area selling tights and stockings. Of course they were in the USA, so it was all panty hose, not tights. " I could never imagine being a boy," she thought to herself. " They haven’t a clue of all the wonders that they are missing out on. Silky underwear, sheer lycra tights and stockings, beautiful dresses and skirts. I really feel sorry for them." Cathryn picked out a selection of tights and stockings. Sally and her were not too dissimilar in size, so if she didn’t use these, then Cathryn could always take them back to England. She picked three pairs of tights, one black, one skin coloured and one champagne coloured. She got the same colours for the stockings, with the addition of a bright red pair, just in case she felt naughty later. All of them were extremely sheer, seven denier, with beautiful lace tops to them. Cathryn was very pleased with her purchases.

Meanwhile Sally had just been wandering the shop. She was still in awe of all the fabulous things, but was as much people-watching as anything else. There were almost exclusively women in the shop, so it gave her a chance to watch their behaviour and learn from it. She saw how they walked, how they stood, and simply how they conversed. She had never thought before just how different women were from men, how they moved, talked, and even how more aware they were of the people around them. By this time Sally was getting used to the fact that apart from the odd catty glance, no one was giving her a second look. Everyone just took her to be a girl. If anyone had said to Paul the previous night, that he would be completely dressed in women’s clothing, walking through Central Park, and buying lingerie at Victoria’s Secret, he would have been more than a little incredulous.

"Come on then, we have shopping to do. Next stop is Bloomingdales." With the carrier bags swinging by her side, Cathryn walked outside and straight away hailed a cab. Sally was impressed. Paul had tried that many times before in London, and it had always annoyed him when the taxi drove straight past him and stopped at some pretty girl standing just up the street. Now, as Sally, she loved it, and for the first time she began to realise that there was a hidden power in being female.

On entering Bloomingdales, the first department they reached was the cosmetics and perfume department. It was huge! Without another word, Cathryn marched Sally straight over to one of the counters, sat her down on one of the high stools and asked one of the overly made up sales assistants if they could try out some of their products. Sally expected to be charged for such things, but Cathryn, with experience born of being 30 years female, knew that these assistants would bend over backwards if that they thought they could get a sale. Twenty minutes later the two girls were a vision. Sally had watched in amazement as the woman had trimmed, filed, polished and finely painted her nails in a bright red colour. Then it was the turn of her face. The assistant had applied the light foundation followed by some subtle blusher to highlight her cheekbones, already quite prominent for a natural male. Some light brown eyeshadow had been delicately brushed across both eyelids, followed by a fine black eyeliner. Finally the woman painted Sally’s lips with lipstick in a luscious crimson, specially picked out by Cathryn. Even the application of the lipstick felt wonderful to Sally’s newly female lips. It felt so soft, and it even smelt great. Never in all her life had she been pampered like this, pampered like only a girl can be. When the woman showed Sally her reflection, she almost fell back off the stool. It was a truly gorgeous woman looking back at her. The transformation was extraordinary. It had been good before, but this was something special. When Cathryn saw her, she obviously thought so too, as it was several seconds before she could get her words out. When she did so, she was gushing in admiration. "Now we must try to find you some clothes that will match just how beautiful you look." Sally couldn’t help but blush, which delighted both Cathryn and the cosmetics assistant, but for very different reasons.

On the second floor they found the women’s department. Both girls were awe struck. There were designer labels for as far as the eye could see, quite a few of which even Cathryn had never heard of. " Where shall we start?" asked Cathryn. " I’d quite like a long dress, something a bit classy, if we are going out to the theatre," said Sally.

"Wow, I didn’t actually expect you to answer that, but I love it that you did. You’re really getting into the swing of this aren’t you my girl?" Cathryn was in seventh heaven. She had secretly carried this fantasy with her since she was at university. During her time in the hall of residence in her first year, they had had a clothes swapping party, where the adjacent boys’ hall came over and borrowed their clothes for the night. She had been paired with another law student called Stephen. Cathryn had deliberately chosen something short and sexy for him to wear, and although initially reluctant, he had slipped on her black clingy micro dress without too many complaints. She had padded out one of her favourite bras for him, made him wear her opaque tights and even given him a pair of lacy panties to put on. Once he was fully made up, together with a wig she had borrowed from the Drama Society, he looked stunning and got a lot of favourable comments from girls, and boys who would be girls. When the end of the night came, and it was time for them to swap back, Cathryn had seduced Stephen. They had wild sex all night long, but Cathryn never gave him the opportunity to get out of his female clothing. The sex was great, the best she had ever had, the best Stephen had ever had too if his screams of delight were anything to go by. When she went looking for him a few days later, a friend of Stephen’s told her that he had decided to swap universities. He had never given a reason to anyone, but just left overnight. Ever since then Cathryn had never told anyone else of her fantasy in case she scared them off like Stephen had been.

The next two hours were like a dream. There were so many beautiful clothes: skirts, blouses, glamourous evening gowns, short cocktail dresses, businesslike dress suits, kinky club wear, sports clothing including gym skirts, leotards and ballet tights just like Joanne had forced him to wear all those years ago. But now it was different. Sally was really beginning to enjoy this. She knew that this was not normal behaviour for 29 year-old male solicitors, but as the old saying goes, you only live once, so why not enjoy it, and she was certainly starting to.

After a couple of hours, the two girls had picked out a number of gorgeous creations to try on, and headed for the changing rooms. The assistant counted the number of items each had and showed them through to the changing area. Unlike normal shops, Bloomingdales had individual walled rooms for each customer, with lockable doors. The store was quite busy with the lead-up to Christmas, so the assistant was grateful when Cathryn suggested the two of them squeezed into one room.

They hung the new garments on the pegs around the room and began to strip down to their underwear. Neither girl could keep their eyes off the other, but it was Sally that said they should behave and try on the clothes. Cathryn picked out a long, glittery evening dress to try on first, while Sally selected a medium length, figure hugging, lacy purple cocktail dress. Cathryn was ready first. " What do you think?" she asked. "You look amazing. To die for," replied Sally. "Well don’t do that just yet, I want to see how fantastic you look in your dress." Sally bent over and began to pull up her slinky dress, and in doing so Cathryn could barely contain her urges looking at her shapely bottom clad in silk panties. "Could you zip me up please?"

Cathryn obliged and when Sally turned round and faced her, both girls knew what would happen next. Both were gorgeous, and both fancied each other like crazy. Knowing that they would have to pay for the clothes if they damaged them, each undressed the other carefully and sensually, without a word passing between them, until there they were standing facing each other in just their lingerie. They moved closer, their breathing becoming heavy. The smell of the different perfumes mingled in the air between them, and when their painted lips finally met, the feeling was electric. In no time at all, they were down on the heavily carpeted floor, Sally on her back with Cathryn on top in charge. Her hand snaked downwards, stopping first to caress Sally’s nipples through the soft material of her bra. The reaction she got was favourable, with Sally’s nipples hardening under the delicate touch. Her back arched against the carpet, but her ecstasy rocketed when Cathryn’s hand reached her silky panties and began to rub the erect member through the material. Sally tried in vain to reciprocate, and please Cathryn in the same way she was pleasing her, but the ecstasy she was feeling left her with no thoughts but to lie back and receive. For her part, Cathryn was enjoying giving. She had dreamt of such things for a long time and was relishing this moment. She kept Sally on a knife-edge for some time, releasing her hold at just the right time, then starting again before Sally had caught her breath. Finally, she allowed Sally to reach climax, after first slipping off her panties, and again taking her cock into her mouth. Sally was writhing as Cathryn sucked every drop that she was given. Both were exhausted and collapsed next to each other. Even though she was dressed as a girl, Sally had still thought of herself as a male sexually, but now twice in one day she had been the receiver, not the giver; the female, not the male of the pair. She strange thing was, that as when wearing the feminine clothes, she also enjoyed being ‘taken’ by Cathryn, enjoyed the loss of control, because that’s what it was – Cathryn had been in charge of their sex, totally and completely. It wasn’t an aggressive thing, but it was certainly in both of their minds, which was where it counted.

They lay there for a couple of minutes before a sudden knock at the door brought them suddenly to their senses. "Are you girls nearly finished in there? I don’t want to rush you, but we have quite a queue of other ladies out here waiting to use the room." "We’ll just be a few more minutes thanks," replied Cathryn.

They hurriedly got dressed, with Sally smoothing out her pleated skirt in front of the mirror. Cathryn helped her touch up her make-up, and they both gathered up all the clothes they had brought in to the changing rooms. "All these other clothes are pretty much the same size so let’s just buy them all," said Cathryn. Sally knew better than to argue by now, so followed her to the cash till. Ten minutes later they were outside the front of the store, with one credit card far closer to its limit than a short time earlier. "Time is ticking on, and it’s a fair way back to the hotel with all these bags, so I think it’s your turn to hail a cab," suggested Cathryn. Without hesitation, Sally stepped up to the edge of the sidewalk, and before she had even put her arm out, one of the famous yellow New York cabs was pulling up next to them. " I think it was you’re short skirt and fantastically sexy legs that sealed that one," Cathryn laughed.

Back at their hotel, all the other girls were in their rooms. Joanne was sharing a triple room with Sarah and Emma, while Cathryn had a room with her sister Louise. All four girls were in the triple room when Sally returned with Cathryn. "So how did you get on? My, what have you two been buying?" asked Louise. All six girls spent the next hour showing each other the various purchases that they had made, and all were suitably impressed with the selection of clothing that Sally had returned with.

"Girls, I think it’s time that we got ready to hit the town. What are we waiting for? Let’s go and beautify! The New York boys won’t know what’s happened to them when they get a sight of the English girls in town!" exclaimed Joanne.

 

 

 

*********************************************
© 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.