Andi woke Jack up at 6am, knowing that it was early enough that none of the other girls on the floor would be up yet. Typically on weekends Jack showered on his own floor separate from Andi, and the two would then grab breakfast. Today Andi wanted to continue to perpetuate Jack being a little girl for her, plus she had another plan for the shower.
Andi gave Jack a robe and explained that they were up early so no girls would see him slip into the shower with her. Andi and Jack climbed into the shower together and Andi washed herself while Jack watched. The whole time Jack watched his girlfriend lather her huge tits in soap all he wanted was to touch them, but he had rapidly realized that Andi was going to do what she wanted, and that if he wanted to do anything he would have to ask, and he would have to earn the privilege.
After Andi finished showering she moved Jack under the stream of water. Andi bathed him, spending extra time stroking his cock, and teasing his asshole with soap. After she finished washing him Andi produced her razor, and then a second one for Jack.
"Watch how I shave my legs, and then shave yours just like I do." Andi said.
Jack did not want to follow this order. He started to object and as he did so Andi brought a finger up to his asshole and slid just the tip of her nail in and said "my little bitch is going to be a good girl, and good girls are always clean shaven, and if my little girl is a bad girl then she won't cum the rest of the weekend."
The feeling of Andi's finger inside of him made Jack want more, so he complied with what Andi ordered. After his legs were shaved smooth Andi shaved his already trimmed pubic hair bald, and then shaved his armpits, and what little chest hair he had.
When Jack's skin was totally bald Andi said "now that's a cute little slave that I can make into my personal doll later!"
Andi turned off the shower, both she and Jack put their robes back on, and the two went back to her room to dress. Andi told Jack to be patient while she got everything ready for him. He had no idea what was coming, but knew better than to ask.
Andi again went to the Rubbermaid tub from yesterday, and pulled a small brown box from within it. Andi was dead serious about Jack cross-dressing. First she pulled a silicon Breast Form from the box, then a bra, and a skirt, and finally a tight fitting blouse.
Andi told Jack to stand still while she used an adhesive spray, and double sided tape to secure the fake breasts to Jack's chest. Once his fake tits were on Jack was told to dress himself the rest of the way. Once he was dressed in the skirt and blouse Andi gave Jack a thorough look over before sitting him down in front of the dorm's vanity mirror. While in front of the mirror Andi spent a full half hour applying differing amounts of make up to Jack. The end result made Jack look like a real passable girl. To cap it all off Andi put a dark black wig that came down to Jack's shoulders on his head.
As he looked in the mirror Jack hardly recognized himself, but thought that he looked very pretty. Andi then did her own make up and handed Jack a pair of flats to wear.
"I want you in heels, but I'm hungry and don't want to wait to teach you how to walk in them, and I also really don't want you to snap your ankle walking in them when you have no idea how to." Andi said. "Let's go get breakfast, and then we are going to get pedicures, and then we'll teach you how to walk in high heels like a real girl!"
Jack started to speak, and Andi cut him off reminding him he was a girl now and needed a girl's voice.
Jack again tried to speak, and this time succeeded in using a higher pitched feminine voice "Thank you Mistress" was all he said.
After breakfast Andi forced Jack into a bathroom stall with her to eat her out. Jack kneeled on the floor of the bathroom with Andi's leg propped above him. Andi quietly moaned and said to Jack "it is so fucking sexy to see you dressed up like a little slut. Oh fuck baby you have no idea what all I have in store for you today."
Jack continued to eat his girlfriend's cunt, finding himself insanely turned on by being called a slut, and by how much Andi liked him to be dressed like a girl. He did his best to bring Andi to a quick orgasm because while he liked how he looked and felt dressed like a girl he was terrified that someone was about to walk in on them at any moment. After ten minutes Andi came and stood Jack up. Andi adjusted his wig, kissed him deeply, and the two then went to the mall.
Jack loved having his feet pedicured, but was mortified when Andi also told him he was getting a manicure. He couldn't hide that, but Andi assured him that at the end of the weekend she would wash it off of him.
After the mani-pedi session the two spent the full day shopping, and teaching Jack how to be a real girl. Jack had never been as turned on in his life than when he caught guys checking both him, and Andi out.
By three in the afternoon Andi and Jack were back in Andi's room. Andi told Jack she was impressed with how good he had been all day, and that he was going to get a really specially surprise now. Andi bent Jack over his desk and moved the thong he was wearing to the side. Jack felt the familiar tingling of lube and Andi's finger working its way inside of his asshole, and he let out a long moan. Then, Jack felt a large plug fill his asshole, bigger than what he had been fucked with previously. At first he grimaced, and then became very accustomed to the plug inside of him.
Once the plug was inside of him Andi again teased him with a long strip show, occasionally stopping to rub his balls through the thong. Just before Andi removed her bra she told Jack to cover his eyes, and then put her panties over his eyes so he couldn't see even if he opened them.
A minute or two passed and Andi said "get on your knees, not on all fours, just your knees." Jack quickly complied, and Andi said "now open them" Andi said as she removed the panties.
In front of Jack stood his girlfriend with a large, very realistic looking, strap on cock. Jack knew from looking at it that it was larger than the plug that was in him now, and knew that Andi was not going to be gentle with it.
Andi stroked the cock in front of Jack's face before slapping him a few times with it and then growling "suck my cock Jackie."
Jack complied immediately. He bobbed his head up and down just like Andi did on his cock, but he was not even remotely close to taking the whole thing down his throat. After ten minutes of him sucking her cock feebly Andi showed signs of disdain. Andi put her hand on the back of Jack's head and began to viciously throat fuck him, forcing the entire cock down his throat and only moving two or three inches of it at a time while he gagged and nearly threw up twice.
Eventually Andi stopped, and she smearing the saliva soaked cock across Jack's face repeatedly. "Don't worry baby, eventually you'll become a really good cock sucker for me" she told him.
Andi then without warning slapped Jack hard across the face, pulled him by his hair to the futon where she laid him on his back. Andi then grabbed several pieces of rope and bound Jack's legs into the air as if he were sitting down.
"Beg me to fuck you Jackie. Beg me to fuck you like a good little girl." Andi told him.
"Please Mistress" Jack began in his best little girl voice "please fuck me like a good little girl, I really want your cock inside of my virginal asshole, please Mistress please fuck me."
"I don't know maybe I should fuck you rough like a little slut, that's what you're dressed like isn't it." Andi said.
Jack had seen himself in the mirror as Andi moved him to the futon, his mascara had begun to run, and the lipstick he was wearing had smeared, he did look like a slut. "Yes Ma'am I look like a slut, but I'm your good little girl, please fuck me like a good girl, and not like a rough used up slut."