High School Sweethearts Pt. 02

Story Info
Andi and Jack's weekend progresses on Saturday.
2.8k words
4.09
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Part 2 of the 3 part series

Updated 06/08/2023
Created 07/14/2016
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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."

Andi removed the large plug from Jack's ass while she lubed up her strap on, "oh fuuuuck Mistress oh god I need a cock in me, I miss that plug Mistress I need your cock please." Jack shrieked out.

"Now that sounds like a slut, not a good girl" Andi said with a grin as she slid the cock into Jack's asshole.

Jack could only moan as Andi began to fuck him. At first Andi worked slowly being fairly gentle with him, but within ten minutes Andi had applied more lube to her cock, and to his asshole and was roughly fucking Jack.

As the pounding got rougher Andi was brought to two of her own orgasms as the strap on base rubbed her clit. She was quickly brought to a third when Jack started saying "I'm a slut Mistress Andi, I'm such a little anal slut, I need to cum, your anal slut needs to cum, please Mistress, please let me cum."

Andi grabbed Jack's cock with one hand and cupped the other over his cock head, and said "I'm going to catch it all in my hand, and if you get even a drop of cum on that cute little skirt I bought you there will be hell to pay."

Jack nodded, and within seconds was begging to cum in Andi's hand, Jack came multiple loads at once, and it was too much for Andi's hand to hold. When he finally stopped cumming he opened his mouth and Andi held her cupped hand underneath his lips and he licked up all of his cum.

"Good girl" Andi said "but unfortunately you came so much that some did land on my cute skirt I bought for you."

"I'm sorry Mistress, you're just so good at fucking me, and I was so horny from being dressed like a whore for you all day." Jack groveled.

Andi removed the cock from inside of Jack and he let out a moan of disappointment. Andi began to stroke his cock as it went soft, and said "no more orgasms for you today, actually none for twenty four hours." As she said it she made a calendar event in her phone and showed Jack. "and given what I have planned for tonight, that'll be really sad for you."

Andi fixed Jack's makeup, and touched her own up and the two went to a movie, and then dinner. After dinner they went back to Andi's room where Andi again inserted a plug into Jack's ass, this time it was slightly smaller and Jack was relieved by this.

For about a half hour they just watched TV together, and then Andi's phone rang. She was on the phone for less than two minutes and only said "hey" and "okay I'll come get you."

"Stay here Jackie, this is your next surprise for the night." Andi said.

When Andi came back into the room she was accompanied by a guy that Jack recognized, but did not know.

"Jack this is my friend Jared, and he's going to teach you how to suck cock properly." Andi said in a matter of fact tone.

Jack was shocked, and couldn't respond before the man stepped in front of him and began to kiss him. Jack tried to back away but Jared stopped him

"Jared finds the cross dressing thing to be very sexy, and he knows that I want you to explore your bi-side a little bit more." Andi said as Jack relaxed slightly.

Jared stripped to nothing and Jack was in awe of how muscular the man was. They were about the same height, but Jared's frame was that of a linebacker, not a track star. When Jack's eyes left Jared's chest, and wandered down to his cock he was somewhat relieved to find that the man was no bigger than he was, and actually may not have been as thick.

"Get on your knees" Andi whispered into Jack's ear.

Jack quickly complied with his girlfriend's command. Jared stepped forward, and moved Jack's head toward his cock. At first Jack resisted but as he did so Andi stepped behind him and stepped lightly on his balls.

"It's really important to me that you become a really good cock sucker" Andi said as she stepped down harder "so do what Jared makes you do, and I'll be really happy, but if you don't I'll be really upset, and the pain you're currently feeling will be nothing compared to how I exhibit my displeasure."

Jack grimaced through the pain, and became more receptive to Jared's motions. Jared never did speak, he just moved Jack's head, or his own cock around and let out moans that told Jack when he was doing well. Jack loved looking up and seeing the muscular man's eyes rolling backward slightly. Jack swirled his tongue around the head of Jared's cock and Jared then began to buck his hips forward, throat fucking Jack lightly. Jack took a deep breath through his nose and swallowed the entire cock into his mouth.

"Oh fuck, that's way better than I was expecting." Jared moaned.

"What a good little sissyslut you're becoming." Andi said through a deep moan.

When Andi spoke Jack realized he had totally forgotten that she was in the room, he had become totally entranced by Jared's body, and cock. Jack's eyes shot over to look at Andi who he saw was fucking herself with a long glass dildo while she watched him suck cock.

Jack kept going, bobbing up and down on Jared's dick, and as he did so he began to work his hands into the equation more as well. Jared responded incredibly when Jack deepthroated him, swirled his tongue around the entire cock, and fondled his balls all at once. For fifteen more minutes Jack sucked to the best of his abilities, and finally Jared seemed to lose all control, he forcefully grabbed the back of Jack's head and began to throat fuck him like Andi had before. Jack didn't gag this time because Jared wasn't big enough to cause that, but he did start to get incredibly turned on being used like this. After another five minutes Jack felt Jared's balls tighten, and he knew was about to happen, Jared came hard down Jack's throat.

Jack didn't gag but wanted to as the load of cum filled his mouth. He swallowed quickly, and was then shoved backward hard and to the floor. While on the floor Andi again mounted his head and began to grind her pussy up and down Jack's face. Jack held his tongue out and moved it as quickly as he could over Andi's clit, and inside of her cunt. In no time at all Andi had the quickest orgasm she had ever had. She rolled off of Jack, and thanked Jared.

Jared just smiled, dressed and left. When he did Andi started teasing Jack.

"You were such a good little cocksucker and then a good little pussy eater. I think Jared really enjoyed you. It helps how passable you are, just like a real girl." Andi said mockingly. "You're a better fit as a girl than you've ever been as a man, you're much sexier looking in the clothes I buy for you now than the old t-shirts and jeans you used to wear."

Jack took the verbal mocking, and was incredibly turned on at the same time. He wanted to cum again, but he knew not to even ask. To his surprise Andi started to jerk him off, and for ten minutes played with his cock, while rubbing the outside of his ass. But when his balls tightened Andi abruptly stopped and just laughed.

"Nope nope nope, you've still got 18 hours to go." Andi cackled at him.

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NEthingGozeNEthingGozeabout 1 year ago

she has turned him quickly

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