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"Thanks Tammy. I look forward to that" said John, using his practiced 'Trisha voice'.
When John got to the room, he was impressed. Having traveled on business for years, he had seen more than his share of hotel rooms. But this was nice. More of a suite. Jacuzzi tub, three TVs, king sized bed, couch, desk, view of the grounds, large rooms, walk in closet....much nicer than anything he ever had stayed in before. This was plush.
From having traveled with Loraine, John knew enough that women want to unpack as soon as they can, so that their clothes don't get too wrinkled from being in the suitcase. Upon unpacking, John discovered why. The fabrics in his new wardrobe sure seemed to wrinkle easier than his men's clothes. He had to iron several of the pieces to make them look good, and he carefully hung everything in the closet.
John also laid out all his makeup on the vanity in the bathroom, just like he had see Loraine do at hotels, so that the maids wouldn't be suspicious either. As a finishing touch, he had bought a box of tampons and several maxipads which he placed in plain view too.
John took the purse that he had bought online, and loaded it with money, lipstick, nail polish, tampons, coin purse, phonebook/planner, and a few other odds and ends that he imagined that every woman would have in her purse. He put the purse over the crook of his arm, like Loraine did, and headed down to Tammy's office. He would have to make sure that he kept the purse with him everywhere he went, just like the girls did.
"Welcome!" said Tammy cheerfully. "Lets start out with a tour of the grounds. Come with me."
They got into a golf cart, and Tammy drove along the paved trail, pointing out things to Trisha. The cart zoomed along, and for the first time, Trisha felt the wind under her skirt. It was a pleasant feeling, and one that actually aroused John. But he had taken that into account too.
When John had found the web site that helped men look like women, he had read about dietary supplements that contain naturally occurring substances found in plants, that act like estrogens in the human body. Many women took them as they reached menopause to help their hormone levels. The web site said that men who wanted to be women took them too. The web site said that one of the effects of large amounts of estrogen in the male bloodstream, is that it disrupts the hormonal balance and makes it difficult to get an erection. So John had gone out and purchased several of these supplements, and had been taking high doses of them for weeks. And when he stopped taking them, he'd go back to normal.
At his age, it was harder and harder to get hard in bed anyway, so between that and the supplements, he had little to fear from giving himself away be becoming aroused. The padded panties he wore also had pads in the front to help hide it as well. So even the breeze tickling him under his dress didn't make him get hard.
"...those are the tennis courts.." continued Tammy, "...and those are the riding stables. But if you just want to relax, we have six pools, each with its own bar. All food and drinks are included with your package, so feel free to partake. There are massages available at pool side, as well as this building here, where you can get your hair done, get a makeover, or get your nails done."
"I just put on a new color last night" said John, holding up his fingers.
"Ooh, that's a nice one for you, but look at your cuticles! They're a mess. When's the last time you had a manicure?"
John froze for a moment. He hadn't thought to get a manicure before he came here. He didn't know how to care for your cuticles, or even what they were (other than something to do with fingernails!).
"Um, you know how it is for a busy modern woman" he said. "There is never time to take care of yourself."
That was a line that Loraine had often used on him, when she nagged him for something. Tammy smiled at him and nodded.
"Oh, don't I know. Between your husband, your children, the house, there is always something that needs to be done. And you put yourself at the bottom of the list. Don't feel bad, most women are just like you."
She put her hand on John's as she said this. If John had been dressed up as a man, he would have taken it as a sign of flirting. He had to remember that he was Trisha now, and it was just a friendly gesture from another woman. In fact, Tammy had seemed to accept him more as a woman now, if there had been any doubts at the outset based on his appearance.
John looked down at his smooth legs, and his cute shoes. It was so strange to see two firm mounds on his chest poking out, or to feel a flowing dress around his body. The illusion of being a woman was very strange to him, but it wasn't unpleasant. He decided that if all the girls accepted him as one of their own like Tammy had, then perhaps he would even get to learn more about Loraine, and what made her tick. He just didn't understand her sometimes.
"And what about weight loss? You're supposed to come out of here thinner and trimmer. You haven't shown me that yet" said Trisha.
"Well," started Tammy, "you will have to wait for that. The first week here is for fun and relaxing. After one week, then you will get your treatment, and lose all the weight you want."
That sounded somewhat mysterious to John, but it was clear that she wouldn't say anything more. So he just listened as they completed the tour.
When the got back to Tammy's office, John selected a list of activities to do that seemed to match Loraine's interest list. He wanted to be close to her, so he could see what it was that she was up to. And keep an eye on those cabana boys that he thought she was seeing on the side.
The first thing that he had selected has horseback riding. John knew that Loraine loved horses, so he figured that she would want to ride them. Since he as a beginner, there was a class to learn the basics. They gave each of the girls in the class a fancy riding outfit, with white pants, red jacket, a cute cap, and long black boots. They were also given sports bras to keep their boobs from bouncing around too much. John's realistic boobs jiggled when he walked or moved, so he needed a sports bra too. They went into their changing rooms, and emerged with their matching outfits.
"You look cute!" said one girl to John.
"So do you!" he said, returning the compliment, like he saw the girls on the TV do. He looked around, but there was no sign of Loraine. He sat through the instructional part of the class, then the all went out to take turns riding a very gentle horse in circles, while a trainer held it on a reign. Riding on their own would come later. As John waited his turn in line, all the girls chatted. He was one of them now, so he made sure to throw in a few things, like they did. He looked around, and spotted Loraine riding by on the track!
She had on a riding outfit too, just like he did. But she was very good on a horse, and galloped by at a high pace. He looked at her, and she must have saw him, but she showed no recognition that the person she had glanced at was her husband. He had fooled her! Good.
"I can see you staring at that woman" said one of the girls. John thought his cover was blown. He started to blush.
"Don't worry, I'm jealous of how she rides too! Maybe we'll be that good when we're done here."
"I sure hope so!" said John. "My name is Trisha, nice to meet you."
"I'm Tiffany. Nice to meet you too."
They chatted until it was John's turn to ride. It was fun and exciting, and after only a few minutes, he could understand why Loraine loved horses so much. He was only going at a walking pace, in a circle, with a trainer holding the reigns, but he immediately understood the fun it would be to run at a full gallop, the wind in your face.
After lunch, John played golf, and sure enough, he spotted Loraine a few holes ahead. He was wearing a cute little white outfit, with a visor, skirt, matching top, and a pink trimmed vest. It was fun to hit from the red tees, instead of the gold tees in the back. He took a smaller swing, trying not to look manly as he hit the ball. To his amazement, his smaller easier swing actually hit the ball longer and with more control than his normal huge rip he took.
It was hard not to say anything when his playing partners did things like throw a ball from behind a tree, and not count it as a stroke, or to improve their lie in the rough. Since he wanted to fit in, John did a few things like that himself. He even took a ball out of a sand trap, and put it by the green.
"I hate sand traps" he lied (he was actually very good hitting out of sand). "You can tell a *man* invented this game, putting those things out there."
"Oh yes!" agreed Tina. The girls chatted, even when someone was putting. John had to not let this bug him either. But he was surprised to find that by being more relaxed and casual about the game when playing with the girls, that it kept him loose, and he actually played very well! When he was serious about the game with the guys, it just tightened him up.
John joined his playing partners pool side for drinks and snacks afterwards.
"Why don't we take a dip in the pool" suggested Kim.
"Not me" said John, using a line he had practiced in case such a situation arose. "I'm to embarrassed to be seen in a swimsuit. Maybe after we loose some weight around here I can pull out the bikini. But I'm not going into he water looking like this."
"I know what you mean" said Sandra, "I love to get sun, but I feel so fat that I'm embarrassed to wear a two-piece."
"Oh you're not fat" said John. "You look just fine."
"Thank you for saying that, but I feel fat" she said.
John knew better than to argue with a woman on that point. Loraine didn't listen to reason either, and when she thought her thighs were fat or something, no amount of logic would convince her otherwise. John decided to use another line that he had often heard from his wife.
"Its not fair. Men don't care, and go swimming even if they're fat and bald."
"Right on sister!" said Tina, and they started talking about men.
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