Standing naked in Karyn's room Jon really didn't know where to start. He stole a quick peek at Karyn's naked body in her mirror but he kept control of himself and looked away before he got too distracted. The luxury of being able to see Karyn's naked body in all her glory whenever he wanted was something Jon was sure to miss when the wish ran it's course but he told himself that if the two dates went well maybe he'd get to see more of her naked body in the future.
Deciding to start with the basics Jon decided that to make the date special he would need to wear some nice underwear. Thinking about the kind of underwear he would like to see Karyn wearing he opened her underwear drawer to see what options were available. Most of Karyn's underwear was fairly plain but at the back he found a few sets that he would consider more girly and sexier. He settled on a matching pink set. The panties were very lacy with a floral pattern embedded in the lace. There was a frilly edge all the way around the waistband and a delicate little bow sat right in the middle. Jon thought to himself that he would love to see Karyn in something so delicate and sexy and decided to go all out. The panties came with a matching bra. The bra was just as delicate and had the same floral lace design on the cups with matching frills along the two straps.
Building up some courage Jon got started. He put his arms through the bra straps and pulled the cups up tight against his chest. He reached behind his back and closed the clasp. As usual the bra sat fairly flat on his chest but a quick look in the mirror showed him that it did wonders for Karyn. It held her chest tightly and pushed her breasts together to form a huge cleavage. He knew that he'd turn more than a few heads with his breasts on such prominent display.
Turning next to the panties, Jon stepped into them and slowly pulled them up. He was loving the feeling of the silky fabric running up his smooth legs. Pulling the waistband up over his hips Jon let them sit into place. They felt surprisingly comfortable. His penis was snuggly sitting in the front and they held his butt very well, giving it a bit of a lift.
Trying to keep his mind on the task at hand Jon avoided the mirror and opened Karyn's closet. Again he saw lots of the clothes he was used to seeing Karyn wearing, jeans, t shirts and the like. All fairly plain. Pulling these out of the way he saw several dresses hanging at the back. He could tell that they had not been worn much, probably only when Karyn's mom had insisted she wear them.
Finding a very classy looking black dress, Jon again imagined seeing Karyn show up for a date with him in such a dress and knew he had to wear it. Taking it off the hanger he studied it closer. It was very soft and delicate with a small lace trim at the hem along the bottom and again around the sleeves. The sleeves were very short and looked like they would only come an inch or two down from his shoulders.
Being clueless Jon was not very sure of how to even go about putting it on. He rolled the bottom up and put his head and arms through sort of like putting on a t-shirt. He then let go of the bottom and let it hang down. It felt very strange to him. It was like wearing a really long t-shirt. He was relieved to find that the top of the dress was fairly modest. It covered most of his breast with just a small bit of skin visible below his neck.
He was very curious to see how it all looked so he closed the closet door and with his eyes closed he turned to face the mirror, wanting to get the full effect. Opening his eyes his breath was taken away. Before him he saw Karyn standing, wearing a very sexy dress. The dress showed the smallest hint of cleavage. Below her breasts it clung fairly tightly to her small stomach before flowing out at her hips and sitting just above her knee. He turned from side to side and saw how the dress floated and hopped around with his movement, showing a little bit more of Karyn's smooth legs before settling back into position. There was no denying it, Karyn was a real knockout.
Mesmerized by the mirror Jon couldn't stop his hands from moving up and rubbing at the bra he was wearing beneath the dress. He saw the incredibly sexy sight of Karyn doing the same and rubbing at her breasts which jiggled a little at her touch. Losing all track of his hormones Jon felt his erection spring instantly to life. His reflection of course showed no sign of it but looking down he could see his penis causing a huge tent to form at the front of the dress. He knew no one else would see it and if he was going somewhere without Karyn he wouldn't have to worry about it but Karyn still saw him as himself so the thought of her seeing this was very embarrassing. Hiking the front of the dress up, Jon saw the tip of his penis poking out from behind the waistline of the panties. Reaching in and taking hold of it, he did his best to tuck it to the side and try to hide any visible sign of it. Dropping the dress back into position he was fairly satisfied that it wasn't too noticeable. He would have to do his best to keep his arousal under control. A task which he knew would be extremely difficult when he fondly remembered the kiss he and Karyn had shared earlier.
As he pondered this dilemma Jon had a brainwave. He had seen various pairs of pantyhose in the back of Karyn's underwear. Hoping that the elastic of the pantyhose would help to keep his erection smoothed down he reached for a pair and tried to figure out how to put them on. Remembering from movies and tv he sat down on Karyn's bed and rolled them up into 2 small socks. He put one foot in and rolled the material up to his knee before adjusting his legs and repeating the motion on his other foot. Standing up, he hiked up his dress and pulled the pantyhose all the way up. The waistband sat a bit higher than the panties. Looking down at his penis he was satisfied that this might do the trick. He was still rock hard but with it tucked to the side and with the tightness of the pantyhose it wasn't very obvious. He dropped the dress back down into place and there was very little outward sign of his arousal. He walked back and forth across the room to get used to the feeling. It was the most bizarre thing he had ever felt. His smooth legs rubbed back and forth across themselves and sent some very erotic feelings all the way up his legs. Even without the wish in effect Jon was feeling very feminine. He began to sway his hips as he walked back and forth and he kept stealing glances at the mirror. The sight of Karyn, with her legs encased in nylon and her dress swishing back and forth was pushing his arousal to the limits.
Finally coming down from his little high he was satisfied with the outfit. He hoped Karyn would appreciate all the effort he was going to. He took the outfit off and carefully placed it all back into Karyn's closet. He hadn't realised how long he had spent at this and it was getting late. Deciding to get some sleep Jon took off the underwear, finally freeing his penis and went to find something to wear to bed.
