I met this young guy, Cameron, by accident and somehow developed a budding relationship with him. Read chapter 1 for details. Cameron's sister, Collette, was presenting a plan for him to apply at an upscale restaurant to be a waitress since waiters did not do as well in tips. Cam resisted the idea at first, but Collette told stories about how they used to play dress up in their mother's clothes. Also, Collette and friends made him up for a Halloween party to pass as a girl and no one knew the secret. Collette shared that Cam was not that opposed to the idea and seemed to enjoy himself at the party.
Collette was sure he was a virgin. I was pretty sure myself because even though he wanted to be with me, he never made any attempt at sexual overtures. When they showed up at my place Friday evening, I had pizza, wine and soft drinks. Collette had a suitcase full of cosmetics. First, we all ate some pizza, but everyone was anxious to begin his transformation.
Collette sat him on a stool under bright lights and began spreading out her supplies. She already had Cam shave his face very closely. He barely had any facial hair as it was so applying foundations was going to be easy. She had the latest spray applicators and the base went on easily. She plucked his eyebrows and gave him a nice lift. For now, we were going to use just mascara on his lashes and see how it turned out. Collette was planning on false eyelashes if we were successful in the makeover.
She was quite skillful as she began applying the subtlest touches to his face. I could see that cosmetology was her real talent. In fact, Collette had told me that she could have gone to Hollywood as a makeup artist if she wanted. Her dreams were a bit larger than that. She did moonlight at a couple of the larger department stores as a cosmetologist.
She had Cam's skin tone matched exactly when she was finished, and his neck blended into the face perfectly. Cam did not have a protruding Adam's apple otherwise this would never work. After we applied the mascara and eyebrow lines, he was into the pretty girl that Collette had described. Eye shadow and lipstick were subtle and understated. His ears were already pierced, and we added some slightly dangling earrings. Collette had borrowed a brunette wig from her department. She would have to return it but for our preliminary run it looked great.
It would have been nice if his hair was long enough to style. We stepped back and admired our work. From the neck up, Cam would fool anyone. He looked in the mirror and was also astonished how he looked.
"Cam, my brother," Collette said, "You look like the sister I never had. She told him to take off his clothes and we would see if we could get his ID that night.
"I'm not taking off my clothes."
"The hell you're not. I am not going to go through all this again just to get your ID picture. Here, switch clothes with me. They were not that far apart in size actually. My jeans would probably be too long for him since I was already a couple of inches taller. Collette pulled her jeans off and then her top and bra. She had a very nice B cup and a beautiful curvy ass. She let him keep his underwear on but made him strip everything else off.
He wore regular briefs and I was totally shocked when he pulled his pants down. It looked like Cam was sporting a very nice cock. It was not as big as my ex-boyfriend, but most guys weren't. I did not comment, but Collette did.
"Ok, wow, Cam. You better hide that thing somehow before getting into my jeans."
Cam turned red, but I was quite surprised that he was that well-endowed. Collette hustled him into her bra and top. She swapped shoes with him and then put on his clothes. Even though Collette had dressed casually, the clothes were still feminine.
"Shit," Collette said, "We don't have time for nails, but it doesn't matter just yet. Let's go. Rita told me where to go to get the ID. It is not a driver's license, but it looks like an official ID. They just need a picture of your face."
We jumped in the car and Collette directed us to a special shop behind a shop. The guy got all the information and said that he would have the ID ready the next morning. His height and weight were accurate, and we changed his name to Camille Johnson. For once it was good to have a common name.
Collette told us that we would need to come up with an outfit for him to wear on his interview. She had a nice skirt and top and we would stuff a bra for him. We were going to improvise a little butt padding and Collette thought that she might be able to borrow something from the theatre arts department. Cosmetology and arts worked together frequently.
We spent the next morning getting Cam ready. Rita was going to get the manager to see him around noon. At that time, we dropped his masculine name and started calling him 'Camille'. We wanted to get him used to the name and get in character. First thing was of course to have him remove all his hair from legs and underarms. I worked on his voice while Collette re-created the beautiful girl from the night before. Collette's B cup would have to do for now and we stuffed some tissue just enough to make his 'breasts' stand out.
Then it came time for the skirt, but Collette told him he would have to shed his briefs. He resisted but we talked him into wearing a sexy pair of my panties. His cock was hard and bobbed up and down. Collette noticed and tried not to comment. It was every bit of seven inches and moderately thick. He was uncircumcised. I looked him in the eye and he blinked.
"Camille," I asked, "What are we going to do about that?"
He was red in the face but did not answer.
"Don't ask me," Collette shouted.
I told him to come to my bedroom and he could relieve himself. I wanted so badly to suck his cock but decided that I had better not take his mind off our business. I led him to the bathroom and rubbed his butt. He knew the drill and began jacking off that beautiful cock. The head came into view as he moved his hand up and down.
"Oh, Camille," I said, "What a beautiful cock. I would love to have that shoved up my wet pussy."
I touched his arm as he stroked away. I then reached my hand down to the head and smeared his precum around the top.
"Uuummmh, so wet. That is so sexy. Make that thing cum so you can fit into your panties. I guess it didn't take you long to get into my panties. I can hardly wait for the real thing."
That was it. He blasted jet after jet into the sink. I got a washcloth and when he finished ejaculating, I cleaned the head of his cock off. I then tucked his softening member into the panties.
"We are almost ready to go now."