Chapter 1 - Dan is Coerced into a Girls' Club Cruise
Dan was looking forward to a vacation with some of his girlfriends and their partners. Sheila had suggested a cruise to the Caribbean. The three women, Olivia, Toni, Sheila; had arranged everything and asked who he was going to bring. Dan didn't have a girlfriend and was a bit shy. He didn't want to admit he didn't have someone, so he made up a story that his girlfriend was on a business trip. The girls all knew he didn't have a romantic life and had a crush on Olivia.
Olivia thought Dan was cute, but a bit pathetic. She enjoyed bending over his desk with a low-cut blouse and walking around with tight jeans. He often ended up heading to the bathroom after her visits. All the ladies snickered behind his back as they saw his tiny hard on that was showing as he headed to the toilet.
Dan was oblivious to the women's ploys and gossip. He considered himself to be a fit, but small man who had a great smile and nice long hair, and therefore was attractive to women. He was a bit short at 5 foot 5 and a half inches, and he had a slight build due to his running for exercise. He clung to that extra 1/2 inch as though that made him more attractive. He watched his weight and worked hard to maintain 135 pounds.
Olivia was an attractive, busty lady who was 5 foot 7 inches. She thought the ladies should play a little game with Dan. She suggested to Sheila and Toni, that a get-away with Dan could be fun. They thought it was a great idea and they got together at Sheila's place. The wine was flowing, and their ideas got a bit more outrageous as the evening progressed.
Toni was in IT and had access to Dan's email at work, and during regular security scans she found a work email with his personal email address and password. After a few glasses of wine, Toni decided to login and read a few emails. She let out an "oooohhhh" and started giggling. Olivia and Sheila asked what was so funny. Toni turned her laptop around and showed so of the porn that Dan was sharing with a couple of friends, and some links.
A lot of pictures and videos looked just like Olivia, but there were a few videos with transvestites and even some gay sex. The ladies immediately knew they had a perfect opportunity for a lot of fun. They schemed a trip where they could isolate Dan and take advantage of this porn information. Sheila came up with a plan for a two-week cruise to the Caribbean, with one night of 'treat' your body to a make-over.
The ladies invited Dan out to lunch, and all of them were wearing short skirts with low cut tops. At lunch, the ladies made sure to rub up against Dan to start the teasing and conditioning. As expected, Dan immediately got aroused. They got him a bit tipsy with chocolate martinis, to make sure they could push him along with their plans.
Dan didn't really have a chance. The women made comments about what they would be doing. They started talking about what skimpy clothes they would have, and how they always got so horny at beaches with all the men with tight swimsuits. They booked the cruise while at lunch, and they made him buy a spa session on the first day of the cruise. They made him promise to let them pick out his clothes for the cruise and what services he would get at the spa. Dan initially resisted, but Olivia pushed her bust up against his upper arm and whispered in his ear that she was really looking forward to this adventure. She felt him shiver with aroused excitement and she whispered, please Dan, I will make it worthwhile. You are going to love it.
As Dan entered his data for the cruise purchase into Toni's laptop, Toni had keyboard recording turned on. Once they all finished booking, they toasted, and the women shared secret smiles.
When they returned to work, the women put plan Make-Over into action. Sheila cornered Dan in the hallway and said she noticed alcohol on his breath. Dan stammered, "but we all had drinks at lunch". Sheila used her stern human resources voice and said all of them had virgin drinks, but you had alcohol in yours. Dan immediately turned red and asked for mercy. Sheila was insistent that Dan go with her to her office. Dan was literally shaking in his shoes. Once they were in his office, she had him take a breathalyzer test. She told him she would keep this confidential, if he followed her instructions. Dan had no chance, and he agreed. He was surprised when she handed him a form, and she said he had better just sign it and go back to his desk.
Dan only had a chance to see a few words and he was a bit confused about him agreeing to follow all instructions given to him by the women in the office, and to pay for all clothing, training equipment, and other services needed for his conversion. Dan assumed this must all have to do with drinking too much alcohol, so he was only slightly worried.
Sheila sent a text to her other conspirators; the Make-Over planis in play. Olivia and Toni were both laughing openly when Dan returned. Dan was distracted by the meeting with Sheila, so he ignored the laughing. But the ladies knew what had happened to Dan, and they pressed in on to the next stage of the plan. Olivia came over to his desk and leaned in, to provide a full view of her ample bust, and she said; "Dan, remember that we will pack for you for the cruise." Dan was still a bit in shock from what had just happened, and Olivia's beasts were right in front of him, so he just said, yea, sure. Olivia then said, "I assume small men's sizes are right for you, and you have size 6 men's shoes." Dan mumbled. Yes, that's about right.
As he was leaving the office, Sheila called him over. Dan, I will be sending you some training exercises to do over the next month. I want you in top shape for the cruise. You are to follow the training without adding or subtracting exercises. Are you clear with these instructions? Yes Sheila. Good boy. Also, you will have a strict diet, and you will weigh in every third day. You will take a picture of your weight, and you will send it to my private email address that is on this paper. OK Dan? At first Dan wanted to resist and ask why, but he figured that this wasn't too much work, and he grudgingly agreed.
That very night, Dan received an email from Sheila with instructions all the women worked on together. Everyday, Dan was supposed to do light weight lifts with 20 repetitions for one set the first week, then 2 sets the second week, and so on until the cruise. The exercises were toe raises to strengthen his calves, squats and lunges to work the thighs, and upward leg presses to work the butt. His upper body work was used to lengthen his muscles, not to increase size. He did leg raises and crunches to work the core. Three times a week he was required to do yoga and three times a week he was required to do cardio. Twice a day he had to do stretching exercises including several deep squats, legs up over his shoulders, and legs spread as wide as he could.
Dan's nutrition was set to have him lose 3-4 pounds per week. This was going to be the most difficult part of his new routine. Every night, before bed, he needed to drink a special protein shake that the ladies had spiked with hormones and diet control pills.
At first, Dan tried to just follow the script, but by the third day, he was sore and starving. Dan figured he could just cheat a little, so, he had some ice cream and cookies. The next day, Sheila called him into the office and showed him a video of him in his kitchen, and yes, he was eating ice cream and cookies. Dan stammered, "hhoww did you get that." Sheila had him sit down and she walked slowly over to him, she grabbed him by the hair in the back of his head, she leaned down and whispered into his ear, you have now 2 marks against you; drinking and now splurge eating. Trust me, you don't want three marks, or you will suffer the consequences. She then slapped him forcibly on his cheek, and Sheila was a pro at inflicting painful slaps. Dan winced at the blow and felt tears form in his eyes. Sheila reached down and used her finger to take a tear drop from his cheek and she pressed it up against his lips. Lick my finger, slave boy. Dan was not thinking, and he licked as instructed. Sheila then yanked him to his feet and said get out of my office, and don't you dare tamper with my cameras. Before I forget, no lunch or dinner for you today.
Dan stumbled out the door went straight to his desk. He wasn't sure what to do. She had a camera in his apartment. How many did she have.... Should he report her to the authorities, no, she had him for driving while under the influence and working while intoxicated. Better to just take it, like he always had as a boy growing up. Suddenly he realized she might have a camera in his bedroom, did that mean she was watching him jerk-off to porn? No, she wouldn't......             dare do that. He would check when he got back to his apartment. How did she get access? Then he realized that he left his keys in his desk drawer at work and she could have made a copy. Damn, this was getting bad.
Dan got used to the work outs and lost 4 pounds the first week and 3 pounds each of the next three weeks. Each weigh-in on the third day, he sent a picture of his weight. Sheila called him into her office after each weigh-in and she congratulated and encouraged him to keep going. Sometimes she would even give him a hug. Her firm breasts were bigger than he realized, and she casually let her thigh press against his thigh. Dan always got aroused and it encouraged him to lose weight to get her caresses and smell her perfume. She loved the power she had over him. He was such a perfect submissive target.
During the second week, Sheila called Dan into her office and gave him a pair of men's shoes with one-inch heels. They were nice leather and had some sparkles in the laces. Sheila told him she thought he needed to upgrade his game, and the women would love them. Plus, it would make him taller. Dan was amazed, these were shoes he had wanted to get but felt self-conscious. Dan put them on and thanked Sheila. Sheila told him to expect some other items soon. She told him to wear the shoes whenever possible.
When Dan returned to his desk, Toni and Olivia, gushed over the shoes and how tall and pretty he looked. He wasn't sure why they said pretty, but he never got compliments, so he let it go. He felt empowered, a new feeling for him.
The following week, Sheila again called him into her office, and she gave him a pair of boots with 2 inch heels, and pants and a shirt. Sheila told him to go to the restroom and change. Dan immediately liked the look of the boots, but the shirt was a button-down pink shirt. The jeans looked strange and he was just about ready to say something, and Sheila noticed his hesitation. Sheila walked up to him, grabbed him by the hair and she slapped him just like before Sheila said in a stern voice, don't ever think about questioning me. Now go change, nowwww.
Dan scrambled to his feet and quickly left the office. As he entered the restroom, he saw the red on his face from the slap, and the tears forming in his eyes. He was in shock, but figured he better change quickly. He took off his shoes, shirt and pants. Then he put on the shirt, but its buttons were on the wrong side. Dan figured it must be foreign made. The pants were much harder to put on. They were skinny leg jeans and the crotch was very tight. He got them on and attached the belt that was kind of pretty for a man's belt. Then he bent down to put on the boots and was very glad he had lost so much weight. Otherwise, he wouldn't have been able to put them on and zip them up along the back. He stood up and looked at himself in the mirror. He couldn't believe it, but he liked the look. Something about pink seemed to make him look good and the extra high boots made him feel like a man.
This time, the ladies really fawned over him. Olivia gave him a big hug and seemed to reach down to his ass before disengaging. Naturally, he got a quick arousal and before he could sit down, Tony also gave him a hug. Except this time, she really groped his ass and slid her leg between his thighs. She gave him a small bite on his ear and said, I can't wait for our cruise together. Dan was pulsing in his tight jeans as she disengaged. Dan turned bright red and sat down at his desk. He was worthless the rest of the day. He couldn't believe that he had 3 women who found him attractive. He might even get lucky.
The day before the cruise, the ladies went shopping online. First stop was Nordstrom. They went to the petite women's section. They knew that they would need to start slowly with some men's clothes and then work up to the little black dress and lingerie. They purchased some tight jeans, some tights, several panties and thongs, a bikini, some tight-fitting tops, a few different bras, some lingerie, women's workout wear, a few women's shorts that could double as men's, and a couple of men's things to start the day. A pink speedo swimsuit, and some small men's shirts (pink and flowery Hawaiian). Then they turned to shoes, they picked out some pink crocs, a few low heel shoes and two pairs of high heels. When they checked out, they used Dan's credit card number that Toni had recorded on her laptop. Since this was a rather high price, Sheila texted Dan to expect some bill today on his card, and to approve anything requiring approval.
