Sorry it took a bit to get to the final piece.
The last bit of excitement is getting her into some clothes. Having come here with just a couple of bags she didn’t exactly have a lot of selection. The dress she was wearing was perfect, but after a shower she really wanted something clean and the only other dress she had was fancy and definitely did not look comfy. She had me pull out a skirt but changed her mind as soon as she saw it. When she did the apartment swap with Jo they each left their stuff behind, so that opened up another possibility. I know Jo well enough that I am sure she won’t mind if we look through her things and she reluctantly agrees. So for the next 20 mins it’s like we’re a couple of girls clothes shopping. I fear that I’m treading a little to close to friend-zone but with nudity on the horizon, I keep treading. She is not real excited about any of the options and is about the settle on a tube skirt that she can just wear with one of her t-shirts. I try to sell her on a dress that is tight on top but gets loose at the waist, thinking it would be easier than a tight skirt to flip up and avoiding incidences like the one with the jeans. I’m holding it out for her and she asks, “Can you pull out that blue thing?” and points. The pointing brings about a fantastic wardrobe malfunction as the towel slips. She catches, but not soon enough. She has it pinned to her ribs with her casts and her boobs, which I hardly got a chance to see before, were finally on full display. When she realizes she can’t shuffle the towel up she drops to a squat. With the boobs now successfully hidden by her knees, I am looking straight down at her back which quickly draws my eyes toward the beautiful heart shaped bum cheeks pointing out behind her. It’s a great sight but I manage to look away before she looks at me and says, “Don’t look!” even though she can see that I’m not. I can’t help but laugh. In a semi-exaggerated plea she says “Don’t laugh at me!” but she is already laughing herself. I ask if she want help with the towel but she directs me to put on the dress instead. She says, “Don’t look.” again and I half-avert my eyes as she does some awkward hops to spin around in squat position before standing up. Now this action certainly did not do much to preserve her modesty. In fact, it had very much the opposite effect. The only problem was that I was too close and almost looking down on her. If I was lower or further back it would have been quite the view.
She announced that she was ready, which I already knew from peeking. I asked if I should get a bra or panties. “Just the dress!” Being naked, she said with some urgency. I slipped it over her head and drank in the sight as I pulled it down. It fit fine, I think it was supposed to be tighter up top, but Jo is a little bigger than Caroline. I thought it looked great but was very happy to hear that she didn’t like it so we would have to keep trying. She mentioned the tight stretchy skirt again so I reminded her about how the jeans failed her and that it should be easy to flip up. It turns out she was thinking the same thing and proceeded to show me how the current dress might fail. She showed me how she would hook her arms under the hem and lift. She clearly did not know how high she was lifting it, but it was still 2 inches shy of where I wanted it to be. Despite my distraction I saw her point, the loose material would flop around and it was hard to get it all up at once. I remembered seeing one that might work but I never pulled it out because I thought it would be too small. But now that I saw this dress on her I knew Jo was a little bigger so it must be bigger than I thought. On the hanger it looked way to small but obviously meant to stretch. Having done this before we easily found a rhythm where she turned around, raised her arms and I pulled off the dress. The new dress was much more fun to put on as the tightness required me to pull in a lot more places. The best part was when her hands were up, and the top of the dress was still above her head covering her face and the bulk of the dress was bunched at the top of her chest. I had started the same way you might pull on a sock by bunching up the material in your hands, but now I had to pull from the hem to finish the job. I fidgeted with the material near her armpit to find the hem and at the same time I could not help but poke my head around front for a peek. I did not risk looking long but it seems I have a near photographic memory when properly motivated. The material felt quite restrictive when it was bunched but stretched freely when it was spread out, so it slipped on nicely. It was basically like a fitted tank top that just kept going. I’d guess the material was cotton and it had some vertical corrugations that allowed it to stretch in the right places without being baggy in others. She joked about that process being less than graceful, I retorted by saying I don’t put on a lot of dresses.
It stayed friendly and fun but, sigh, that was the last time I saw her naked. I kept thinking of all the things I could have done differently but sometimes I wonder if it wasn’t for the best. I’ve spent way more time fantasizing about this than I have with any “successful” conquests.
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