Kristen Tests Her Boundaries

Kristen stood at the doorway opening on to the roof of her apartment building, thinking about how she had come to this point. She and her husband had made a bet on the NCAA men's hoops final, with an agreement that the loser would perform some embarrassing stunt chosen by the winner. She had decided on making Dave run around the block in his swimsuit yelling "Virginia sucks!"; she knew making him badmouth his alma mater would aggravate him more than the choice of attire. Until the closing seconds of the game she was quietly enjoying the image of his penalty and thinking she might even buy him a speedo for the occasion. She was also wondering how it would feel to have to do something like that herself, thinking if Dave had his way she'd probably be in a thong!

When Virginia pulled out the win, her plans for Dave's embarrassment vaporized and she reluctantly asked what he had in mind for her. His initial plan had stunned her - he wanted her to run from the stair at the rear of their building to the front and back, around 200 yards altogether, while NAKED! Dave didn't think this was too extreme, having gone streaking in college and even making a visit to a nude beach before they met, but Kristen had never done anything remotely like that. Her time at the gym had earned her the firm butt, toned legs and taut belly Dave loved; good genes were probably responsible for the full, firm breasts he also loved. Despite this, Kristen thought of herself as average looking, certainly not any kind of hottie. Dave knew better, and had often told her so.

Kristen told Dave she hated to back out of a bet but she didn't think she could see herself doing exactly what he wanted, though she might feel safe enough to give it a try if there were clothes set out on the roof as a kind of backup. Dave thought about it for a minute, then agreed, as long as he could pick out the outfit and set the clothes out for her. Kristen agreed to his proposal, but made him promise that the outfit he chose would provide adequate cover if she needed it. His only other request was that the clothes should all be worn in their normal arrangement.

The plan had seemed reasonable enough when they were discussing it in their living room with a couple of glasses of wine, but now that Kristen was standing on the stair landing slowly unbuttoning her one garment, a long raincoat, she was pretty sure this was the worst idea ever. She tried to peek around the edge of the open door and study the sightlines to see exactly where she might be seen from once out on the roof, shaking a little as she thought about her next step. Only when she thought about how much she would hate to back out of a bet and considered how Dave had assured her that he placed boxes of clothes at regular intervals was she finally able to swallow her fear and unbutton the last button. Kristen shrugged the coat off and handed it to Dave, telling him she was ready to go through with what she had been calling his "perverted little plan". She wrapped her arms around him and gave him a long, passionate kiss. Even though they knew nobody could see them they both were pretty turned on by standing at an open door making out while she was naked. Eventually they broke their embrace; despite her terror Kristen was getting into the spirit of the occasion, giving Dave's rapidly swelling dick a squeeze through his shorts as she stepped out the door.

Once Kristen left the shelter of the stair tower behind, she felt her heart racing and she was shivering so hard she practically couldn't walk. It occurred to her that she didn't think she could remember ever shivering with the temperature above 75 degrees, then it occurred to her that one thinks of weird things when one is naked out in the open on a rooftop in the city. After a few more random observations on her situation she set off for the front of the building, which seemed impossibly far away at the moment. Looking around as she went, she spotted a cardboard box 30 or 40 feet ahead, around midway between the buildings on either side.

After what felt like the longest 40 foot walk imaginable she reached the box, which had her initials on it; this had to be one of the packages Dave had promised to leave for her. She looked around to see whether she was in any danger of being seen yet, and discovered that now that she was well away from the back of the building, there really wasn't anywhere with a view of her position; the two buildings at either side of hers were several stories taller and had no windows facing her location and the buildings across the streets at the front and back of her building were enough lower than hers that they would only be able to see her when she was near the very edge. She realized a little late that while she was completely safe now, her emergence from the stair tower and initial "deer in the headlights" moment once she was out on the roof would have been easily seen from most of three buildings across the street from the back of her building! The realization produced another shiver; she wondered if it was possible she was actually enjoying this?

"Time to see what Dave has left for me" she thought; though feeling surprisingly comfortable at the moment considering that she was naked, she still wanted an option to cover up. She had a mix of emotions once she saw what the box held; some fear, annoyance and a fair bit of excitement at seeing one of her favorite pair of calf high boots. Nothing else. Looking ahead she saw a line of identical boxes, evenly spaced and leading to the front of the building. She considered ending her jaunt there and then; clearly Dave wasn't providing as much cover as she had hoped for. Then the thought of what she might look like strolling across the roof naked except for some boots and her awareness that nobody could see her right now anyway took over; she took the boots out of the box, slipped them on and zipped them up. "Off to see what's in box number two." she thought, her smile growing as she headed off.

About halfway to the next box, Kristen realized she hadn't looked back to the stair since she had left it behind. She stopped and turned around, and was happy to see Dave waving at her. Without thinking, she cupped her breasts and gave them a squeeze as a reward for his attentiveness and laughed out loud at his slack-jawed expression.

Reaching box #2 Kristen had another look around; there were still no good views other than for Dave, who was still standing at the stair wearing a broad smile. She opened the box and found more cover than she expected; Dave was certainly full of surprises. Neatly folded in the box was a lightweight gray sweater. Though it was almost long enough to cover a short skirt it was well short of being able to hide any skirt Kristen ever wore. Short as it was, in her current state she thought it looked like a pretty conservative item. She was amazed to find herself a little disappointed to have so much fabric at her disposal in this fairly safe spot, but thought it might be handy as she got closer to the front of the building. She put it on but didn't bother closing it in front. Off to box number 3.

Reaching box number three after what could only be described as a leisurely strut, Kristen checked her surroundings again. As much as she was beginning to enjoy this jaunt she didn't think she could be so bold if she had a serious chance of being seen, The change in location allowed a taller building a couple of blocks away to be seen past the edge of the building to the left of where she was standing. "Should this be the end?" she wondered, then decided the new intruder into her walk was probably far enough away to not be worth worrying about.

"Time to see what Dave thinks I should be wearing now" Kristen thought as she opened box 3. A blouse, another surprise. It didn't really cover anything she couldn't hide by closing her sweater, but she put it on anyway, which required getting the sweater off first! She had another shiver as she briefly again stood naked, except for the boots. She tied the tails in front ,which in combination with the wide open sweater left her still completely exposed below her breasts, It occurred to her that she was now at least potentially, even if at a pretty long distance, being watched by strangers. Kristen was still nervous, but also intrigued by the possibility, pausing to study the visible windows for signs of life. She realized that she was slightly disappointed to see none, and wondered what was coming over her, but only for a moment; it was time to get to box 4.

Box 4 was slightly more than halfway to the front edge of her building, so Kristen made another assessment of how visible she might be. She was comforted but also a bit disappointed that nothing had changed much yet, though she could now barely see the edge of another tall building in the next block to her right; since the part of this building visible so far was a blank wall she thought "no windows, no worries!" and turned her attention to box #4.

"Jeans? Really?" said Kristen. It seemed Dave may have overestimated her fears, but she realized she had sounded pretty nervous about this and was getting ever farther from the safety of the stair. She took off her boots, pulled the jeans on and put the boots back on. It occurred to her that the outfit she now had on was basically safe to wear on the street, and she was saddened to think that her wild walk was getting to be so tame, and even sadder that Dave thought she wasn't bold enough to meet his challenge. "Oh well. Lets see what's left in the other boxes" she thought. She was now close enough to see that there were 3 more to go.

Box 5's location would have sent Kristen into a low level panic just a few minutes ago; the distant building on the left and particularly the one across the street on the right seemed a lot closer, and a few windows on the one at the right in the next block were now in sight, which meant there was at least a slight chance she would be seen. Since by now she was pretty modestly dressed, and about to retrieve even more clothing from the latest box, it occurred to her that there really wasn't much very interesting for any onlookers to see anyhow. After all her previous nervousness she was surprised to notice a growing feeling of, unlikely as it seemed, disappointment at the possibility of not being seen nude by some random stranger.

Opening box 5 changed everything. Literally. The contents of the box: a peach colored leotard Kristen had forgotten she even owned. The snaps were at the shoulder, which meant to put it on Kristen would need to remove every last single thing she was wearing. She looked again at the neighboring buildings and couldn't decide if Dave was terrible or wonderful. Wonderful won out as she convinced herself that all those people behind all those windows likely had other things to do than keep watch over the roof of her building; their loss, she thought as she removed the sweater, and kind of a shame, she thought to herself as she removed the boots, the jeans, and after a brief hesitation, the blouse, putting just a little more sway and tease in getting it all off than the task needed. She told herself that she was doing it for Dave's enjoyment even though she was pretty sure at least some of the theoretical anonymous window people might now be closer to her than he was.

Once Kristen finally got everything back on and her breathing came back to normal, she took a few minutes to process what had just happened. Incredibly, she had just performed a weird sort of striptease, getting completely NUDE, in broad daylight, with NO idea who might be watching. She thought seriously about leaving the last two boxes right where they sat. A little inner voice was telling her, screaming at her really, that she was getting out of control, but the cautious inner voice had now been joined by a voice from another side of herself. After a minute or two the new voice, aided by her curiosity to see what the boxes held, and more importantly what the view was like from their locations, won the argument. On to box 6.

Upon reaching box 6, Kristen did her now familiar study of the sightlines to her position. As expected, everything was getting riskier, though she thought in reality the distances weren't much closer and there were just a few more windows not blocked by her building's neighbors. It couldn't hurt to just look in the box could it? She opened it. "Damn, Damn, Damn!" said Kristen, thinking she should have expected something like this; Dave had dug up a shelf bra from the back of her lingerie drawer, the only one she owned, bought for their honeymoon. Thinking back to the last time she had worn it and realizing that the way it left most of her breasts uncovered and out on display must have made a lasting impression on Dave, Kristen smiled and felt warm all over.

Whatever the fond memories the tiny garment held, Kristen was having another heated internal debate with herself; to do what was needed to be able to put on the bra, she'd be giving any onlookers an encore striptease performance, all to put on a filmy excuse for a garment which hid nothing. She was shocked that Dave obviously thought this was a pretty hot idea, but way more shocked that she did as well. To even be considering this next step was way out of her normal comfort zone, but judging by her blushing face and the state of her nipples, which could soon literally be getting their moment in the sun, she found a previously unexplored corner of her psyche was up for it.

Deciding to go for at least this one step forward, she set out to give Dave a show to remember, along with, well, who could say who else might be watching? She could hardly believe it, but having come this far she really hoped she really did have an audience, and not just Dave. As before, everything came off, this time a little more slowly and with some gratuitous stroking, cupping and caressing along the way. Despite the fact that she could have put the bra on without completely removing the leotard, it somehow ended up around her ankles! She gave her nipples particular care once the bra was on, Eventually she was fully covered again, and thinking over her options.

With only one box left, she didn't want to walk away from this challenge. But. That box was pretty damn close to the front of the building. So far the only people to maybe, possibly, see her performances would have been a long way off, which wouldn't be as true at box #7, which was no more than 8 feet from the edge of the roof! She now saw that the building directly across the street was shorter than hers, but not by very much; anyone watching from the top two stories would probably be able to see every inch of her body above the knees, just a couple of sidewalks and a narrow street away. She could walk away now, but having come so far she needed to at least know what she was walking away from, so she headed for the last box. Her inner debates about whether or not to proceed were getting to be shorter with each new challenge.

Before looking in the box Kristen looked around to see how well she could be seen from the various buildings nearby. The situation was worse than she had thought. The two distant high rises were closer and had more windows in sight, and the one across the street did indeed have a couple of floors with prime viewing opportunities; Kristen had already factored these conditions into her thinking and was trying very hard to convince herself that more windows with a view of her didn't necessarily mean anyone happened to be looking. She wished she could know if anyone was watching her, and wondered if knowing would make it impossible to continue, or impossible to stop!

The real problem with this spot was a bunch of previously unseen balconies on the building right next to hers on the right. They were only about 6 feet deep so they hadn't been in sight until Kristen got near the edge of her building, but several of them on floors near the level of her roof would have a spectacular view, less than 30 feet away, of anything she got up to, or more accurately down to. She sort of hoped for something like a hat or scarf to be in the box. Sort of.

Before opening box 7, Kristen told herself she still had a choice to open the box or not, but deep down realized that given the way she felt after her actions at the last couple of boxes, she really didn't want to stop; she ripped the box open and saw two items. Her hand shaking, she pulled the skimpiest thong panties she had ever seen from the box. They were all but transparent, and the one new item of clothing in her whole adventure. She silently thanked Dave, then studied all the balconies she could see.

Kristen told herself she couldn't possibly repeat her last performance here, with this little distance and no barrier at all between her and the closest members of her so far theoretical audience. She took a good look around at all the surrounding vantage points and could barely stop shaking. Eventually she remembered the other item in box 7; she reached in and pulled out her phone.

Dave had apparently spirited it out of their apartment while she had been getting ready for this escapade, and had sent her two texts during her trek. The first text was a long series of heart emojis, the second just one word - "selfies?" Thinking Dave would have seen her pick up the phone, she texted back a reply; a long line of heart emojis, followed by a plea for him not to call right now, telling him she needed to think for a minute. She figured there was no harm in granting his request for selfies in her current state, though she was fully aware that those were not what Dave had in mind. She took a half dozen from a variety of angles, sending them to him with a note asking if this was what he wanted. "You are all I could ever want and more than I deserve xxoxxo" he texted back.

The time spent looking around, taking photos and texting began to relax Kristen a bit. The windows across the street showed no sign of activity, and more importantly no one had appeared on any of the four balconies next door. Her new internal voice, the one who first appeared about 250 feet and a half dozen boxes ago and always urged the most daring choice in any situation, was sounding more and more persuasive. Kristen's usual cautious voice had run out of new reasons not to do this, and the longer no one showed up on the balconies the more this final striptease, possibly toned down a bit in light of the location, seemed to Kristen like something she might be able to handle.

Kristen found that deciding to proceed didn't completely silence the alarms going off in her head, but the first few steps would not be too scary; for part of her "act" she would be reasonably decent, however odd a partly dressed young lady on the roof might be. She set up her phone to record, but NOT transmit video; she told herself she wanted Dave to be able to see her performance up close later, but the tingle adding a camera to the proceedings gave her was at least as much of a reason.

Kristen began by letting her long sweater slide slowly down off her arms and pool on the roof; consciously or not she was now making even the "safe" part of her act erotic. Next was her blouse, untied then slowly slid off one shoulder, then off the other to land on the roof next to the sweater. Bending over and wiggling her butt a little, she unzipped each boot, then lay on her back and raised one leg at a time and slid off her boots. More than half way done, she blew her phone a kiss for Dave.

Down to just three bits of clothing but still outwardly completely decent, Kristen now changed her routine in recognition of her more vulnerable position; she still thought she could continue with this show but had decided to cut down or maybe even eliminate the time she would be completely naked and on view to God only knew how many people. Kristen was trying to think of a way to not quite go naked but still provide Dave with a hot show.