The Dare MD Ch. 05

She moved languidly toward the floor-to-ceiling windows, a wine glass in her hand. She looked at the traffic below, the low buildings along the river, the office buildings nearby, and the hotel across the way. There were still a few people in some of the offices, and some in their hotel rooms, sitting, unpacking, getting ready to go somewhere. She took a sip of the wine and put it down on the low table off to the side.

She leaned closer to the window and put up her hand as though to wave to anybody who might be watching. She noticed at least one man at a window across the way.

He may be watching . . . or not, or at least not yet. The sun was still fairly bright, and all the lights in the room were on, in addition to panel lights for the camera that Sterling was operating behind her. It would not be hard for anybody to see her.

She ran her hands over the pullover covering her tits, down her stomach, around her waist, and then down her legs, bending over slightly till she took hold of the tight skirt and pulled it up slowly, gradually exposing her black tights, the built-in garters, and her bare skin rising to her bare pussy. She held the skirt there for a moment, feeling the tingling excitement running through her exposed skin as she sensed that two, maybe three men across the way had stopped what they were doing and were looking over at her.

She let the skirt go and smoothed it down over her legs, then slowly-every move was slow and purposeful-brought her hands up to lift her short-sleeve pullover. With one graceful move, she pulled it over her head, letting her long auburn hair cascade down over her shoulders. She held the sweater for a moment before dropping it, then brought her hands up to cup her exposed tits as she stared directly across the street at one of the men watching her. He did not move, and she swore she could feel his shallow breath as he gawked at her. She smiled.

She ran her hands up into her hair and pulled it off to the side, then let it fall down over her shoulders. She moved her shoulders back and forth, very gently, very slowly, letting her little tits shift. The other two men that she could see were still at their windows, watching, transfixed. Maybe there were others too.

Moving her hands over her tits and down her stomach, she turned slightly to one side and let her fingers drift into the waistband of her skirt. She continued turning as her hands moved around the sides till they got to her ass. She bent forward and pushed down on the skirt, letting her hands ride over her soft, round ass and down the textured stockings till the skirt fell to the ground.

An electric rush shot through her, challenging the quiet, languid mood she had created. She was totally nude, except for stockings, within sight of complete strangers, uninvited and unknown. Even though she kept the slow pace as she stood, her heart was pounding, her breathing was fast and shallow, and her head was spinning. Nonetheless, she turned toward them, resting her hands on the window, and stepped wide, her knees slightly bent, to give them the best chance of seeing her meaty pussy lips. She sensed that Sterling was filming close, letting the camera gaze over her skin, the hair over her shoulders, her fat little ass. She began swaying in front of the windows, watching the men from a distance as they watched her. With a slight dip of her head, she stepped over to the table to pick up her wine, raised the glass toward them, and turned to walk toward the bedroom. She saw that Sterling was taking close aim at her pussy and ass as she walked by.

Somehow, she felt bolder when she got into the bedroom. Standing at the same floor-to-ceiling windows, she danced sensually and slowly, brushing against the sheer curtain along its side. From the slightly different angle, she was not sure whether the three men were still watching, but in her mind she was dancing for them, offering her little tits, her fat little ass, and meaty pussy for their pleasure.

After a few minutes, she drifted away from the window over toward the bed. Standing next to it, she bent down gracefully, sliding her hands along the texture of her stockings, down one leg, up the next, Sterling following her delicate fingers as they traveled over the intricate design of the mesh. She sat down and reached for the straps of her shoes, played with them, then slowly undid one, then the other. She lay back on the bed, raised her legs in the air, Sterling following every graceful move, and rolled over onto her side.

The camera followed her fingers as they traced the contours of her body, riding over the tiny mounds of her tits, drawing circles around her nipples, then running down along her stomach. She lay back slightly and opened her legs, letting Sterling get a good view of her open pussy. After a short time, she rolled forward to close them, then rolled back to open them again. She knew he was getting a closer look than she had ever allowed on this site, and her heart was racing, but she kept her pace, slow and languid. She reached one leg down to drag a pillow from the bed and pull it between her legs, just enough to give herself a little cover.

After another playful minute, she lay on her back, slid her fingers under the garter belt of her stockings, curled up her legs, and slowly slid them off. She pulled them off each foot, stretched out each leg in turn, and tossed the stockings off the side of the bed. She was totally nude, nothing to hide behind, and Sterling was slowly scanning every inch of her bare skin as she rolled over onto her stomach, spread her legs slightly, and pushed her ass slightly into the air.

This was where her dare would end for her public posting. After a pause, she reached her hand between her legs and up toward her pussy to start the bonus for the fan who had come up with the idea. With one finger, she stroked her pussy lips, already wet from her exposure to the city, separating them, and then gracefully slid one long finger inside.

She sighed as it went in, not just at the sexual tingle, but also at the knowledge that this would be the first time that a stranger, somebody she would never meet, was to see her fingering herself and getting herself off. And if she decided to offer it for special sale, there would be several strangers. The thought sent another rush through her as her finger slid in and out of her wet channel.

Soon she slid in a second finger, and the added thickness was leading her to writhe and twist her hips. She and Sterling had agreed that she would stay on her stomach for this bonus video and that, as she stroked herself with her fingers, he would record different parts of her body, so they could create a beautiful erotic video, not just a blatant look at finger-fucking. As much as she wanted to roll over and pound her pussy with her fingers, she kept control, trusting in Sterling to get good pictures.

When her body began quivering, though, she knew that she would not have much more control. She let out a long, quiet moan to let Sterling know that she was about to cum, and she sensed him moving to the side of the bed where he could be pointing the camera right up between her legs, straight at her pussy. With her thumb pressing on her clit as she stroked her fingers in and out, her hips began shaking and her pussy clenching around her fingers as the orgasm flowed from her pelvic area through her body and arms and legs. Her hips bucked three times with decreasing strength as she gasped in response. After the last one, she let her legs relax and her hips settle down onto the bed. She ran her hands up through her hair as though to capture the fleeting sensations of the orgasm, then let herself rest and drift into a slight doze.

SHE AWOKE WHEN SHE FELT THE BED SHIFT slightly, followed by Sterling's light touch along her legs, moving up from her feet to her hip. Next came his lips on her butt cheek, teeth biting gently, then kissing their way up her back. Slowly, more and more of his body came in contact with hers, till he was close to covering her, from his feet against hers, his hands on her shoulders to support his weight as his torso rested along her back. She felt his cock stiffening against her thigh and its head just resting against her pussy lips. She slid her hand under her stomach until she could just reach the tip with her fingers. Just that touch was enough to trigger another surge against her thigh.

She shifted slightly, and he lifted himself so she could turn over. He lowered himself back down onto her, and she guided his cock to her pussy, still wet from her previous efforts, now throbbing again at the prospect of his cock inside her. She always got a thrill when she held him in her fingers like that, the contrast between the spongy head and the stiff shaft, the blood pulsing in his veins. There was another thrill when she stroked his stiffness against her own soft wetness, and he responded by pushing forward to the tight opening that stretched as his cock pushed in, and her lungs filled with a gasping intake of breath as her body reacted to his invasion.

Slowly and gently, in and out, his cock filled her warm, wet cunt on the way in, then her thick pussy lips gripped his rod on the way out. The slow rhythm sent sensations through both of them. After a few minutes, he pulled his legs up under her, so he could sit up and slide in deeper. He took advantage of his upright position to squeeze her tits and tweak her already hard nipples. She moaned as he increased the pace of fucking. Then with a practiced move, he slid his arms under her back and lifted her, rocking back on his heels till they were upright, and she bore down on his rigid cock with the pull of gravity. She dug her fingers into his back, gripping hard and moaning in response to his ever deeper penetration.

Moving one leg at a time, he shifted to the side of the bed and stood up. Bearing her weight on his legs, he shifted around so he could lie back down with her ass facing the window. Not that anybody would be able to see them at that angle. The evening had grown darker, and fewer lights were on in their room, but the mere possibility that they could be exposed gave them both an extra thrill.

She stayed pressed down on his cock till he smacked her ass and pushed up with his hips. Then she lifted her hips, sliding herself up the length of his cock, squeezed her cunt muscles around the head, and slid back down. At first, she picked up speed, riding him up and down with a fast rhythm, sending new waves through the engorged veins in his thick rod. Then she slowed down and tightened her cunt muscles around his cock, dragging her thick pussy lips along the rigid shaft. She knew that alternating in this way would push him toward the edge. His moans were getting louder and less controlled, and his grip on her arms was getting tighter, almost painful. And then, when she thought he was getting close to bursting, she pushed all the way down, squeezed her cunt as hard as she could, and just gave short thrusts, almost bouncing, till he let out a loud gasp. His body shook, and she felt his cock swell and explode inside her. His gasps accompanied each burst, and he was bouncing his head against the bed. This pushed her over her own edge, and her body quaked against his. Finally, he threw his arms around her and pulled her head down to his. She nestled her face into the crook of his neck and kissed him intensely and passionately as his orgasm slowly dwindled, and he gradually went limp.

After a few minutes, she rolled over, and they just rested there for a while.

THE SITE WAS JUST STARTING ITS FIFTH MONTH. Andrea recognized a number of regular fans, most of whom made compliments to her posts and a few of whom had started to recommend dares. Most of these were pretty straightforward, like going through a drive-through with just a thin shirt on, changing panties in a public area, and even taking off her thong in a restaurant, under the table, and leaving it with the tip. She had also taken bolder steps on her own, such as flashing her ass and pussy after that restaurant dare and posting a video she had made earlier, where she played with her pussy lips on a park bench. A couple of fans had made outrageous requests that she immediately turned down, but a few others were beginning to make some bolder suggestions.

The window strip dare had come from a fan who went by the name of baudelaire49, apparently a fan of French literature. He had made some nice comments on some of her earlier posts and had proposed a neat grocery shopping dare that involved exposing her tits and ass when she bent down; he said this was based on an incident earlier in his life. The window strip idea, though, came from a story he had written and published on an erotic literature site. He said he had loosely based the main character on her. She had liked the story, and she and Sterling thought the balcony scene would be a good way to push her boundaries, really challenge her to go outside her comfort zone.

Editing the long video from that session turned out to be more of a challenge than she expected, mostly because she kept getting so turned on watching herself strip that she frequently stopped to get herself off. When that happened, she lost track of what she had planned next steps had to go back a little to find her place. This became even more of a challenge when she got to the bonus scene, where she was watching herself masturbate. But with a couple of late-night sessions and one full weekend, thanks to Sterling taking the children to see his parents, she finally finished editing. "Nice job," Sterling said when he looked it over.

She posted the dare, her longest yet at nine minutes, early in the evening, with a longer than usual introduction:

"This dare was a super turn on. On a business trip, we had an amazing room with a great view. As the sun was setting, and with all the lights on, I stripped fully nude at our floor-to-ceiling windows. From what I saw, three guys across the street saw pretty much the whole thing and maybe others too. This was crazy fun. I went waaaay beyond my normal limits and shot a bonus scene of myself getting off and cumming for the fan who gave me the idea. I'll probably never post it, since it's way outside my comfort zone...but it's reallly hot. Maybe some day, for a price? ... I don't know. Anyway, enjoy, like and comment!"

She knew the uploading would take a while, so she went down for dinner. After the kids were in bed, she went back to the computer. The video was live, and she already had a couple of likes and comments.

Then she wrote a message to baudelaire49, asking if he had seen the post and if he was at his computer. About twenty minutes later, he answered that he could be there around ten o'clock. She spent the next hour half-heartedly working on some other videos and pictures. She got more nervous as time passed. Not just because the bonus video was such a departure for her, the first time she had exposed herself like this. She also felt close to a few of her fans, including him, and she just really wanted him to like it.

Shortly before ten, a message popped up on her screen: "Are you there?"

"I am," she replied. "Have you seen the post?"

"Yes, I scanned it. It looks beautiful. Are you going to send the bonus?"

"I wanted to be here when you first saw it. Are you ready?"

"Sure." She clicked the button and sent the video on its way.

There was silence, then he wrote, "Processing."

"So nervous," she replied, and they lapsed into some more silence.

"Got it," he said after a couple minutes. "Watching now."

She fidgeted in her chair and began lightly rubbing her pussy through her panties as she waited for him. The bonus was five minutes long, and it felt like an hour. Then a message popped up.

"My god, that was glorious. So beautiful!" She felt a rush of relief and excitement that he had liked it, but she wanted to know more. "Can you talk some more," she asked.

"The pace of both pieces was just perfect, slow, graceful, nothing rushed. Even when you slid your finger into yourself, it was ... elegant, it felt like. Very sensual, erotic. And the camera movements, particularly when it moved over your ass and down your leg, then shot up toward your pussy from your feet. Really, a work of art."

She was so relieved that he liked it and that, as she said to him, it came across as something erotic rather than pornographic. They chatted a bit more, and he ended with, "Just beautiful. I may just watch it again. And again ... And again..." After he signed off, she went to find Sterling. She wanted to share her joy at this new direction with him.

AT AROUND 1:00 IN THE MORNING, she woke up, still resting next to Sterling. She listened to his quiet breathing for a few minutes, enjoying the warmth and smell of his body, then slid to her side of the bed and got out. She picked up a short robe, threw it over her shoulders, and headed to the guest room.

When the computer came to life, she was pleased to see a couple more comments on her long post. There was another message from baudelaire49, once again praising the pace and camera work of the bonus. Then she opened the next file in the video folder.

The file flickered to life with a camera view of the floor-to-ceiling windows in their hotel room. It was the next morning, and the camera was on a tripod, closer to the floor. The image wobbled a little as the camera was adjusted, then Sterling's bare legs came into view, with the tip of his cock at the top of the frame. He made a few more adjustments, then turned and walked toward the window. Then her bare legs came into view, followed by her fat little ass and her hands cuffed behind her. As she moved toward the window, it became apparent that she was on a leash, being led by Sterling.

He made her kneel at the window, now filled with early morning sun. The leash was hooked to a thick choke collar with the word WHORE in bold letters. Her hair was pulled back in a ponytail, and her eyes were covered with a mask.

He dropped the leash and left her there, completely naked on full view for anybody who might chance to look her way.

Watching this on her monitor, Andrea leaned back in her chair and started playing her fingers over her pussy lips. She remembered the feeling of knowing she was on display, but not certain whether anybody could actually see her. She watched as Sterling came back into the picture and stood right in front of her, loosening and shaking his cock. She remembered sensing his return, followed by the surprise when he first smacked her cheek with his cock. She opened her mouth to take him in, but instead he kept hitting her and stroking himself to get hard. As soon as she closed her mouth to wait, he pressed the head against her lips, and she opened up to take him in.

As she watched him fuck her face, Andrea slid two fingers into her sopping wet pussy. She loved the feel of his hardening cock in her mouth, feeling the textures and ridges of the head and veins as he fucked in and out between her lips and on her tongue. In the office, she moaned as her fingers rubbed the front of her cunt wall as she watched herself gag when he pushed deeper into her throat than she expected. Sterling gave her a moment to recover, then pushed his way back in, challenging her to take him deeper with each thrust. And in the office, Andrea slid further down into the chair, rubbing her thumb along her clit as now three fingers pumped into her cunt. Her gasps and moans obliterated the low sound coming out of the monitor.

On screen, she gagged a couple more times, then he pulled out and stoked his cock until he shot a heavy load of cum onto her face and tits and stomach. His loud grunts mingled with her sudden gasps in her chair as seeing him cum pushed her over the edge into her own orgasm.