Simon saw Jasmine enter his family’s restaurant confirming that he hadn’t somehow been imagining the events of the day before. All night he had been worrying that what had happened the day before was too good to be true and the super sexy and kind Jasmine would never show up in his life again. He had expected to be alone for the rest of his time in high school and had only hoped to find someone interested in him when he went to college, but the way Jasmine treated Simon made him feel like there was a chance.
Simon was still guarded though and even as the door bell rang and the tall tanned blonde walked in, a part of Simon’s mind filled with dread as the other part of it soared with hope. He had been hurt, some physically but mostly mentally by the kids at his school, so trust was hard for him even if he really wanted to trust Jasmine. This uneasiness for trust almost ruined the date as while Simon was looking over Jasmine’s new outfit and admiring the two basketballs that stretched the sweater she wore, Simon noticed a prominent bulge in her tight jeans. The object hidden there was unquestionable and Simon was about to turn on the smiling girl? That was waving at him from the front of the restaurant, but Simon caught himself. He thought about how that jerk Jared would have certainly insulted the girl about her body and make insinuations about her being a slut or something. Simon didn’t want to be like Jared and with a more open mind Simon could admit that the bulge actually looked rather attractive on Jasmine. It did nothing to detract from her feminine looks and it even made her look cooler and confident with how prominently she displayed.
As Simon got over his initial thoughts about the amazing girl that had come here to meet him, he began walking towards her. Jasmine didn’t wait for him to make his way to her and rush to him and hugged him, pressing her breasts into him like the day before.
The hug was broken off before it got awkward and Jasmine asked if Simon was ready to go. He replied that he just had to put some things away then they could leave. Jasmine offered to help but Simon said it wouldn’t take too long and rushed off to finish his chores.
“Damn did he see my cock. I could swear he looked straight at it. Must have seen it, but he said nothing about it. Oh I hope it didn’t disappoint him the little guy. Maybe I should ask him if he’d want me to get it replaced. Wait what am I thinking, I need to get him to replace his” thought Jasmine as she waited for Simon to return. It wasn’t a long wait and the two were soon heading out the door and officially beginning their date.
The first stop they went to was the school. They had been able to walk there from Simon’s place in around 10 minutes so they had chatted on the way there. During the chat Jasmine tried to pry into what Simon liked to do and when he had nervously began talking about a Japanese comic he was reading she accidentally let slip that she was also reading that comic. Jared would have never admitted that to Simon and Jasmin had initially thought I wouldn’t fit the act she was playing, but when she saw Simon’s elated face after the slip, she knew that it would be alright.
By the time the two made it to the school they were laughing with each other about their favorite parts of the comic. Seeing the school made Jasmine remember that she would have to get the school to change her paperwork tomorrow. The school had a unique policy for students that went to the transformation clinics but wanted to keep their change a secret. For permanent transformations the name on the records would change and publicly the new form would be introduced as a transfer student while the previous form would have been said to have changed schools. For temporary transformations it would be fairly similar except the old form would be said to have needed to take the online classes that the school provided so that if the transformation lapsed the old form could return while the new form would have been said had to move.
Simon lead Jasmine around the outside of the school pointing out the different buildings but they soon left the campus and caught a bus that took them downtown. While they sat and waited in the bus they continued their conversation about the comic and other comics and games they enjoyed. By the time they exited the bus both of them were surprised by how similar their interests were.
Now downtown Simon guided Jasmine around pointing out different places like a karaoke parlor, an arcade, a roller skating rink, and finally the large mall that had the main movie theater inside it. They were walking through the mall and Simon was pointing out a board game and tabletop games store when Jasmine noticed a women’s clothing store and remembered Bailey’s suggestion.
“Hey Simon I kind of need to stop by that store over there to pickup some new clothes if you don’t mind coming with me” said Jasmine pointing out the store she just saw. Simon looked and blushed a little but said he would go with her and the two walked over.
Upon entering the store one of the clerks clocked Jasmine’s huge tits then her bulging crotch and walked over to the pair.
“Hello there how may I help you. Do you need your measurements done, a specialty panty set or does your boyfriend want to try on some of our crossdressing selection. We don’t judge.” Said the clerk smiling at the two.
“I um. I mean I need, but we’re not, but we. ahrrg. I need bras and maybe those panties” said Jasmine falling over her words at the beginning before collecting herself at the end.
“I’m sorry that was too much on my part. Let’s get your friend seated over by the changing rooms then I can get your measurements done and find you som bras to try on.”apologized the clerk before leading them deeper into the store. Simon was sat down on a bench by the clerk and told to wait just a moment before she took Jasmine into the changing rooms.
“If you could take that sweater and bra off I can get your measurements done” said the clerk while Jasmine was in a curtained booth.
“They’re off. What now” said Jasmine before yelping as the clerk came through the curtains and wrapped a measuring tape around her chest.
“Wow these are some impressive tatas you’ve got yourself here. So did you get them this morning or yesterday” asked the clerk adjusting the measuring tape to get a proper measurement.
“How did you know that” said Jasmine surprised at how fast the clerk was at figuring out her secret.
“Oh honey I know perfectly what a boy with new breasts looks like. My boyfriend wanted me get get a pair like these but I said he had to get a pair first before I expanded mine. He did just that an ended up liking them so much so that he got jealous when I said I would make mine bigger.” Said the clerk as she finished off the measurements. She then wrote them down and gave Jasmine some recommendations on how to pick out bras then left. Jasmine gaped at the measurements that she was given and almost left the changing room with her tits still out.
Clothes back on Jasmine left to find some bras to try on and saw Simon patiently waiting for her. Rather than leaving him there while she searched Jasmine had him come with her and find a pair that he wanted her to try on. Simon had tried to protest but gave in after Jasmine insisted.
The selection of bras that actually came in her size wasn’t huge but it was greater than Jasmine had expected. She was able to pick out five styles that she liked and found the specialty panties meant for 7 inch cocks when she had picked up the panties she had been elated when Simon had seen them and had nervously said that he thought they would look good on her.
“He saw them and he wasn’t disgusted. He even complimented them. He must really like me. That’s so sweet” thought Jasmine forgetting her plans entirely for that moment.
When it came to finding Simon’s choice Jasmine teased him when he stopped in front of a sling bikini display but said she would try it on if he really insisted. Simon blushed but didn’t take her up on the offer instead he picked out a nice black set with some lace detailing on the top rim.
With the underwear chosen Jasmine grabbed some shirts and some skirts then made her way back to the changing rooms. She swapped into a new outfit with one of her more plain bras and left to show Simon. He was back on the bench and smiled when she returned, complementing her and the outfit saying how it fit her perfectly.
Jasmine’s next outfit was more revealing with the shirt she had on only buttoned up part way showing her dark red bra peaking out from below it. Simon still complimented her but looked much more nervous about it.
The third outfit broke Simon as the shoulderless shirt she wore clearly had no bra underneath it and it sat so low Simon was amazed he couldn’t see her nipples at all. Simon moved his hands to his crotch to cover a bulge of his own that had started to form during the last outfit.
“So what do you think, I like the colors but maybe it’s too tight” asked Jasmine in a teasing tone, noticing that Simon was covering himself. Remembering an old meme Jasmine thought of a way to tease Simon further.
“What’s got you so worked up over there Simon. There must be something that’s gotten you so hard over there” said Jasmine before pausing for a second.
“Oh is it these. My boobies. My massive fucking titties. My super stuffed up milkies. My honker bonk... pfffts. I’m sorry I can’t. Your face it’s so red” said Jasmine breaking into laughter.
The look that Simon was giving Jasmine was priceless as disbelief showed across his face at the fact that one of his favorite memes had been performed live solely for him by a girl with a dick who he was starting to develop feelings for. He wanted to laugh, to turn away in embarrassment, to come back with a witty retort, but Jasmine’s laughter won out and he joined her.
Simon was still blushing red as a beet when the laughter died down and was pushing down on his lap covering his bulge.
“Ok Simon thank you for being cool with that. Now why don’t you come back with me and I can help you deal with that.” Said Jasmine indicating his lap.
“Wait you can’t mean, but I’m just a nerd and we just met” said Simon some of the blood draining from his face as the realization of what was being offered hit him.
“Don’t say that Simon. You are really sweet and want to repay you, but if you really don’t like it we can stop” said Jasmine in an earnest voice unlike her earlier teasing.
It was too much for Simon and he put his mistrust aside and in barely a whisper asked her to lead the way.
“Fuck fuck fuck. Why did I say that. What am I doing. Shit why does he have to be so nice to me. Why did I have to go tease him like that, that stupid cute dork. Wait I can make this work. He’s got to have a small dick. Even if he’s average he’ll be smaller than me. I can just tell him that because he’s smaller he should be the girl in the relationship. He’s going to be so hurt I can’t. No start thinking about him like that. I have to do this” thought Jasmine as she lead Simon to the changing rooms.