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32. Dress up

31. Hot and heavy with Laura

30. Finishing school

29. Gym class

28. School morning

27. Waiting for Karyn

26. Bathroom break

25. More girly

24. Karyn in control: 3rd changes

23. Jon gets home

22. Bumping into Laura

21. More shopping

20. Bra shopping

19. Jon learns more

18. Bathroom break

17. Catching up with Karyn

16. Flirting in class

15. Late for school

14. Covering up

13. Slippery slope

Dress up

on 2022-12-10 18:04:31

2569 hits, 261 views, 5 upvotes.

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As their passion started to dissipate Jon and Laura just lay in silence for a while. Laura was the first to speak and she told Jon how impressed she was by him. She admitted he wasn't her first but said none of the other guys she was with had made her feel that good. Jon, a little embarrassed, admitted that he'd been a virgin up to this point. He didn't say it but he couldn't help thinking how he'd never imagined his first time having sex would be with him as a girl and having glesbian sex. But either way he was counting it as losing his virginity and his body was still tingling a bit from the intense pleasure he had just experienced. Laura got up from the bed and pulled her panties back on and Jon did the same. Neither bothered with any other clothes just yet, being happy to sit around in their bras and panties.

Talk soon turned to the party. It seemed to be the hot topic among everyone in school. Laura said she couldn't wait. She was meeting with a few girls before hand to get ready together and they'd be travelling to the party as a group. But she was very excited to spend her night with Jon. Jon wondered if hid guy friends were doing something similar. He would have to text Pete to find out. He didn't think they'd be getting ready for the party like the girls would be but it would be cool to hang out with the guys and go to the party together.

Jon watched Laura's panted butt as she walked over to her closet and turned back holding the dress she was going to wear. Her smile turned into a grin as she walked over to Jon and held the dress up against him. She said, "You know what Jon. I actually think this dress would fit you. Ha. Imagine if you showed up at the party wearing a dress. What would people think?" The idea seemed a lot more far fetched to Laura than it did to Jon. "She doesnt find me wearing lingerie to be funny so why would a dress be?" he thought to himself. He just laughed off her suggestion but she wouldn't drop it. With a bat of her eyelids and a smile she spoked softly to Jonnand said, "While we're alone Jon, would you please try it on? Just humour. It will be our little secret. I find the idea so hot. It really shows a guy is comfortable in his masculinity if he is willing to push boundaries a little bit. And after what we've just done I've no doubt you are as masculine as they come but what say you slip it on, just for a laugh."

Jon could tell Laura found the idea of him wearing a dress to be a bit taboo and that it was a turn on for her. And as he looked down at his breasts, nestled comfortably in his bra he thought what the hell. Its only a small step further than what he's been wearing the last few days. Pretending to put up a fight he reluctantly took the dress from her and tried to figure out how to put it on. Laura took it back from him and walked around behind him. "Put your arms up," she whispered in his ear. Her excitement was evident in how she whispered. Jon copied and she put the dress up over his arms and let it drop down. The feeling of the soft material gliding down Jon's smooth, curvy body felt incredible and he felt himself tingle with excitement. His nipples sprang to attention and pressed into the padded cups of his bra. Laura adjusted the dress around Jon's thin waist and narrow hips. She stood back to admire it and asked Jon to give her a twirl which he happily did. The dress sat mid-thigh on him and as he twirled it swished up and around his legs before dropping back down. Jon was conflicted. He didn't want to give away that he enjoyed the feeling but with his new body it actually fit him perfectly and was very comfortable.

Laura walked in a circle around him and ran her hands around his waist before dropping them down to his butt. She couldn't contain how hot the sight made her and she pounced on Jon and started to kiss him again. Between kisses she told Jon how hot she thought he looked. She told him that guys really got the raw deal when it came to clothes. "Your clothes are so boring", she said, "if you wore dresses all the time I'd have easier access to your pussy, like this". As she said that she ran her hand up under the dress and caressed Jon's vagina through his panties. Jon's breathing got heavy and he thrust his crotch towards her hand, wanting to continue. Before they could continue an alarm went off on Laura's phone and she stopped what she was doing.
"Shit, I guess time flies when your having fun. My parents will be back in about twenty minutes. I set that alarm to remind you. You'd better get out of here before they get home. We can continue our fun at the party on Friday. Except I'll be the one in the dress and you can reach under to play with me. You'll be stuck in your usual boring pants."

Jon quickly removed the dress and handed it back to her before pulling on his pants and top. He didn't want to have to face Laura's parents so he quickly grabbed his stuff and after one last kiss said goodbye and headed home.




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