A NEW CAREER
Chapter 4

Two days later Annie saw Milo. "What time do you want me tomorrow?" she asked and he told her right after school. "Who will I be modeling with?" she continued.

"You will be modeling with one of my best boy models, Craig. You'll like him. He's a year older than you and has been modeling for me for three years, so he knows what he's doing," Milo answered.

"A boy? Where will we be changing?" Annie questioned.

"Same place you always do," he smiled. A shocked look came over Annie. "Don't worry. All you have to do is face away from him. He'll be doing the same thing. The only thing he might see is your butt, which isn't a big deal. Remember modeling the panties? In some your butt showed, right? It's part of modeling," he explained. She still looked concerned. "If you don't want to do it I can find another girl. I thought you'd want to. It will take about three hours and it pays $225," he offered.

Annie thought. The idea of taking her clothes off in front of a boy she didn't even know scared her. She had done it with Milo, but somehow this seemed a lot different. It was a lot of money though and she knew it would help out. "No, I'll do it. See you tomorrow," Annie relented.

She spent the evening convincing herself everything would be fine. Milo had already seen her completely naked. At least this boy would only see her naked from behind. Annie wasn't really comfortable with that, but she rationalized, as Milo had told her, it was part of modeling, so she could live with it.

School the next day was only a half day. Annie hadn't told Milo that, she had forgotten, but decided to go to his apartment early hoping he would be there. She knocked on his door and when he opened it he was surprised to see her there. "I forgot to tell you I had a half day at school today, so I thought I'd come early. Is that OK?" she asked.

"Sure, come in," he smiled. "I've been thinking. I know you really didn't want to be naked in front of Craig. We need to make sure you look good in the clothes, but maybe we can cover you some. Would you like that?" Annie smiled and nodded. They walked into his studio and he picked up an envelope, opened it, and showed her two flesh colored small disks. "Know what these are?" he asked and she shook her head. "They are called 'pasties' and cover the dark part of your breasts and your nips. It's not much, but better than nothing? Take off your top and bra, if you're wearing one," he instructed.

Annie felt a little odd just taking her top off, but there was no reason not to. Milo had seen her naked many times already. She lifted her top, tossing it onto a nearby chair. She wasn't wearing a bra, so was now naked above the waist. Milo stepped up to her and placed the pasties on her breast. Annie looked at them. They were almost like round band-aids. "They don't cover much," she giggled.

"I know. They are mainly so your nips don't poke out and show when you have a top on," he commented.

"Um... Do I wear anything on the bottom? You've already seen me anyway, but..." Annie blushed.

"No. It will be the same as last time. The only difference is Craig will be here too. That means he might see you, but you are going to see him as well. Will you be OK seeing all of him? You know it's all part of modeling, right?" Milo asked.

Annie thought for a moment. She had never seen a boy in person although she had seen pictures. The thought of seeing him naked intrigued her, but she was nervous about him seeing her. "He might see me naked?" she questioned.

"Yes, he might. You will probably... No, you will see him naked. When boys model for me, they wear a 'cup'. To put that on they have to get naked and you will be here, so you will see him. Want to see what a cup looks like? I can show you one," Milo offered and Annie nodded.

He walked to a chest of drawers, pulled out something, then returned to Annie. He then showed the cup to Annie and explained how it was worn. He told her it was to protect a boy if he was to get hit, but explained he used them so there was no outline showing a boy's parts. To Annie it sort of looked like a thong for boys, except there was two straps in back instead of one.

"So I'll see him in the cup, but he'll see my... um... he'll see all of me?" she asked.

"No. He has to take everything off to put on the cup. It doesn't go on over underwear or anything. There are a few retakes I need to do from his underwear modeling. He will take off everything he is wearing, get completely naked, then put the cup on. The cup is worn under the underwear. You will see his boy parts. Are you old enough to handle seeing him?" Milo explained.

"Yes! Of course I am," Annie snapped, reacting to his comment about being old enough.

"Good. You are old enough to be seen too. I have told you it is part of modeling," he told her, but was interrupted by a knock on the door. Milo left, then returned with a boy following him. "Craig, this is Annie, the girl you'll be modeling with today. Annie, Craig," Milo introduced.

Annie looked up to see a very nice looking boy. She suddenly covered her chest remembering she was only wearing pasties on top. "Oops," Annie muttered as her face turned red.

"Shall we get started? Looks like you could use a relaxing pill, Craig?" Milo questioned and Craig turned slightly red, but nodded. "I'll get one. Take off your jeans," Milo told him, then left the room.

Craig undid his jeans, then pushed them down. Annie was shocked he was just taking them off in front of her, but couldn't turn away. Her eyes widened as he stood back up wearing only his underwear and his erection was painfully obvious under them. "Sorry. I can't help it. It just gets like that when I pose with a girl. That's why the relaxing pill," he muttered.

"It's OK. No big deal," Annie responded trying to sound mature, even though she was utterly shocked seeing him. She had never seen a boy in person who was naked let alone hard. Annie felt sorry for him though as he was obviously uncomfortable.

Milo came back and sat on the couch. "Ready?" Annie watched, surprised Craig walked to Milo then sprawled out across his lap like he was going to get spanked. Her jaw dropped when Milo reached for Craig's underwear and pulled them to his thighs. He then took something that looked like a toy syringe, but it was all smooth, and put a small pill into the top of it. He opened a tube, squirted a clear substance onto his fingers, then coated the tube with it.

He held the toy syringe in one hand and with his other hand parted Craig's ass cheeks exposing his asshole. Annie watched in horror and fascination as he pushed the toy into the boy's ass. Craig didn't move though. After a few seconds, Milo pulled out the syringe, took a tissue and wiped the excess clear stuff from Craig's ass, then pulled his underwear back up.

Craig stood up like nothing had happened. By this time Annie was actually shaking from nervousness. "Looks like you could use one too, Annie. Take your shorts off. I'll be right back," Milo suggested.

"No! I'm fine," Annie gasped. "I don't need anything."

"You do need something to relax you. Don't worry. It will not hurt you at all. If you don't believe me, ask Craig. You just saw him get a pill. I'm going to get one. Take your shorts off," he instructed, then left the room.

"He's right. It doesn't hurt at all. It relaxes me so I can pose better too. I guess it's a little embarrassing. It was for me at first, but not anymore. I hardly even feel it when he puts it in," Craig explained.

"Really?" Annie questioned and Craig nodded. "It doesn't hurt?" she continued and Craig shook his head.

Milo returned ending the conversation between Annie and Craig. "You still have your shorts on. Take them off so we can get this done and start working," he ordered.

Annie thought for a moment, then dropped her shorts. It felt strange having Craig see her in just panties, but she knew that and more was going to happen. She was nervous about the pill. The pill itself didn't bother her, but having it put into her ass. She trusted Milo though, so bent over his lap and waited.

Her face turned red when he pulled down her panties and she knew Craig could see her bare ass. Her face turned redder when she felt his fingers part her ass cheeks and something go into her ass. Craig had been right. It didn't hurt at all, but she knew something went into her ass. A few seconds later the probe was pulled out of her ass and Milo pulled her panties back up.

Annie stood up and her hand went to her ass almost to check it. She knew he put something into her, but couldn't feel anything. "Let me show you what you'll be modeling today," Milo stood. He walked over to the tables on either side of the stage they posed on and began showing them the clothes. As they went through the outfits, Annie felt her body relaxing.

"OK, let's get started. Put on your first outfit," Milo announced as he finished up showing his models the outfits. "Craig, put on your cup and Annie, take off your panties," he added.

Annie watched in amazement as Craig took off his shirt, then dropped his underwear. She stared at his cock, now hanging loosely, in plain view, not hidden from her. He didn't even try to hide himself. Without even thinking she pushed her panties down while she continued looking at him.

Craig picked up his cup and slipped it on, covering his boyhood from her gaze. As he covered it dawned on Annie she was naked, except for the pasties, and facing him. He was looking at her pussy. She blushed and turned, grabbing the shorts that were part of the first outfit and put them on.

They started the shoot and Craig and Annie changed outfits quickly. Craig was covered, so he just changed. Annie wasn't wearing panties, so tried to keep her back to Craig as she changed. It didn't really bother her that Milo could see though. There wasn't really anything he hadn't seen many times already.

Her next outfit was a pair of leggings and a shirt. Not really thinking about it, Annie stepped into the leggings and started to pull them up. She only had them at her hips when Milo said, "Stop!" She looked up as he walked over to her. She had her back to Craig, her side towards Milo, but he placed his hands on her hips and turned her to face him, then pushed the leggings down to her thighs.

Annie blushed slightly knowing Craig could see her pussy, but strangely she didn't seem to care. "When you put on something thin and tight, like leggings, don't pull them up from the waist. You'll stretch them out and they won't look right. Pull the legs up, like this," he instructed as he grabbed one of the legs stretching it up, then grabbed the other and pulled that one up too. The top of the leggings were still hanging down, so she was still exposed. "Once you get the legs up, then pull the top part up. That way everything fits properly and they will look better, understand?"

"OK," Annie muttered, her pussy still not covered.

"They should be snug here," Milo began again and brought his hand up between her legs and pressed against her pussy. "You don't want them to droop down," he told her as he pulled the top part of the leggings up, finally covering her. "Understand what I am saying? See how they fit now? ...nice and snug between your legs?" he asked and Annie nodded.

Annie looked up at Craig, knowing he had now seen her pussy for sure. He showed no reaction and seemed to be just waiting for her to finish dressing. They continued to model, but Annie didn't intentionally try to hide herself from him any longer – he had already seen her. Most of the time she had her back to him when she changed, but if he did catch a glimpse of her it no longer mattered.

They continued modeling for another hour or so and Annie, as well as Craig, were getting tired. They had just taken off their outfits and grabbed the next one when Milo suggested they take a break, pleasing Annie. She dropped the outfit and walked over to the couch with no pants on at all. Craig followed her and sat down next to her. "Um... Would you mind if I took off my cup? It's getting uncomfortable, like all hot and sweating."

Without any thought, Annie shook her head. It surprised her when Craig stood, then pushed down his cup, revealing his cock and balls to her. She couldn't help but stare as he rubbed his boyhood, then sat back down next to her. "You don't mind me seeing?" she asked.

"No... You seem cool with it. Some girls kinda freak out, but you're different. A lot of girls would have gone nuts when Milo pulled down your leggings, but you just stood there. Do you mind me not having anything on?" he questioned. Annie shook her head. Her eyes were glued to his boyhood though. "Do you mind me seeing you?" he asked.

The question shocked Annie back to reality and made her think. She knew she shouldn't let boys see her, but Milo had because she was modeling. She was also modeling with Craig, so rationalized it was the same thing. It wasn't like she was just pulling her pants down so he could look. "I guess not," she smiled.

"OK, let's finish up," Milo announced as he walked back into the studio. Craig stood and pulled up the cup as Annie watched. They then went back to work.