Jon and Susan walked to Karyn's house from school. Susan was chatting away the whole time and Jon tried to keep up. Whenever he spoke he was reminded about his new way of talking but he was starting to get used to it. He even tried really hard to lower his voice back to his normal tone but it didn't work. He sounded like he was trying to do an impression of a girl. But Susan didn't seem to notice anything wrong so he eventually gave up trying.
As they walked he stole a few glances at Susan and remembered how intimately he had gotten to see her in the changing rooms in the mall earlier that week. He remembered how we cited he felt at the time, getting to see Susan's panties and bra straps and getting to touch her in such an intimate way. He presumed he would be paying her back today, having no doubt that Susan would expect him to get dressed with her present. He was thankful that when Susan looked at him she saw Karyn as otherwise it would be very embarrassing for him. He'd never live it down if Susan, or anyone else for that matter, saw him as he really was but wearing a bra and pair of panties.
When they arrived at Karyn's house, Jon got the keys from his backpack, as his clothes didn't have any suitable pockets on them. He wasn't fully up to speed on the schedule of the rest of Karyn's family and he hoped the house would be empty. Unfortunately for Jon when they entered he heard Karyn's mom in the kitchen. She came out to meet them and said, "Hi girls. How was school. Long time, no see, Susan." They both said hi back and then Susan embarrassed Jon by telling Karyn's mom why she was there. Karyn's mom got very excited. She had often wondered about Karyn and Jon and she really liked Jon. She told the girls to go up and get started and she'd bring them up some snacks in a while. Jon was a bit embarrassed now. He didn't want the whole world to know he was going on a date and it was even weirder for him that everyone who did find out was more concerned about what he was going to wear and how cute he could look to impress his date.
Susan excused herself at the top of the stairs to go to the bathroom which gave Jon a few minutes to breath. He went in to Karyn's room and threw his school bag in the corner. He stood and admired Karyn's reflection. He needed to see her female figure and large breasts to remind himself of how everyone else perceived him now. It would take some of the embarrassment out of getting dolled up in front of other people if he could keep picturing himself as a girl.
Susan didn't take long and soon joined him, demanding to see the dress he planned on wearing. Susan sat on the bed while Jon opened the closet to get it. He held it up for her to see and she complimented it but said she wouldn't give it her final vote until she saw it on him. Jon just stood there, not sure what to do. He hoped Susan might leave the room but instead she just leaned back on his bed and said, "C'mon girl, what are you waiting for. Get those clothes off and put it on." Jon gulped a little bit and having no other option decided to get it over with. He gently placed the dress over the back of a chair and removed the clothes he had worn since Gym this morning. He stood now in only a pair of panties and a bra. He felt ridiculous but a quick glance at Karyn's sexy reflection in the mirror gave him the confidence to continue. He lifted the dress up to put it on when Susan told him to stop. "Aren't you going to change your underwear Karyn? You'll have a lot more confidence if you wear something sexier underneath." Susan sat up and opened an underwear drawer. She pulled out a matching dark blue bra and panty set. They were very frilly and made of very thin material. She handed them to Jon and resumed lying back on his bed.
Jon pulled down the panties he was wearing, finding it amusing that Susan had no idea that here he was, standing in front of her with his penis dangling between his legs. He pulled on the new panties and tucked himself in before removing his bra. Susan gave a little giggle when Jon was topless. "You're so blessed with those big boobs of yours Karyn. I'd kill to have a pair like them." As she said this, Susan reached down and gave her own boobs a gentle squeeze. Jon tried not to stare and instead, using his practice from the last few days quickly covered his chest with the new bra. He felt a bit less exposed now. He grabbed the dress and put it on over his head, letting it fall down below his waist. Susan demanded he give her a twirl and he obliged. As he slowly turned he caught site of Karyn in the mirror and had to admit she looked amazing. Susan agreed and gave the dress her approval.
Jon, naively thought that was that and he was ready to go so he was surprised when Susan told him to take the dress off again so he could get ready properly. Not wanting to look foolish Jon just went along with her suggestion. Susan suggested he take a quick shower while she looked through his makeup to work out the best options. Jon took the dress off and made his way into Karyn's private bathroom,leaving the door open as Susan was still chatting away to him. He once again removed his bra and panties, placing them carefully on a shelf before hopping in the shower.
