The Dare MD Ch. 02

In the first few weeks after her naked dash out of her office, Andrea, a local family doctor, tried a few other dares, sometimes on her own, sometimes with her husband Sterling. On one of her weekday morning jogs, she wore a strapless halter top that she could pull down when she was sure she was alone and let her little tits bounce free. She also bought some tighter shorts that left half of her butt cheeks exposed. Another day, Sterling went with her and took pictures of her jogging topless and then posing naked by the side of the road.

On a nice weekend, the whole family, along with the nanny, went to the park. Sterling had persuaded her to wear a lightweight jumper with nothing on underneath. While the nanny took the children to the playground, he and Andrea walked along some of the emptier pathways leading away from the busy park. He stayed behind her and filmed upskirt glimpses of her naked bottom. When they reached a secluded section with a bench, he persuaded to sit and pull the top of the jumper down so she could play with her tits. After a while, he started photographing and filming her efforts. When he suggested she pull the bottom aside and play with her pussy, she hesitated. "What are you going to do with these pictures and videos?"

He shrugged. "Keep them to watch later. I don't know, maybe we can post them somewhere."

She was startled and covered herself. "We can't do that. I can't let people see me doing this sort of thing!"

"We'll keep it anonymous, edit out your face. You'll be safe. This is just for our fun."

She looked at him for a moment, seeing that quirky smile that always got to her. She smiled back, then spread her legs, propping up on the bench, and pulled the crotch of the jumper aside. While she kept looking around to make sure nobody could see her, she ran her fingers lightly down along her prominent pussy lips. With a few strokes from side to side, she loosened them and began spreading them open.

The cool air felt nice on the soft folds, perhaps as they were starting to get a little wet from her touch. She used fingers from both hands to spread the wings apart, and she was rewarded with Sterling's rapt attention. She knew he loved to see her play with herself like this, and being outdoors added a special treat to it. She lightly touched her clit with one finger, and a thrill went through her whole body. Sterling seemed to have a quiver of his own, maybe shaking the video picture.

Then she saw somebody turn the corner of the pathway leading to the bench, and she closed her legs and pretended to take an interest in something on the ground, so she could pull the jumper back over her tits. When they had passed, she stood up and held out her hand to Sterling. "Let's go back to play with the kids. I think that's enough for a first day out."

That night, as they lay in bed snuggling against each other's nakedness, Sterling told her about an incident from long before they had met. "I was in the checkout line at the grocery store, and in front of me was a woman in a loose sundress. Every time she bent down to get something out of the cart, her dress fell forward, and I could see her bare tits and all the way down to her panties. I want you to do the same, except no panties."

Andrea rubbed her hand over his chest, relishing the ups and downs of his torso. "I have just the dress for that. I haven't worn it in a while, but it's loose and will hang down when I bend over. Plus, it's got buttons down the front." She moved herself on top of him, pressing her naked body against his, running her hands through his hair, and kissing him deeply and long. She soon felt him growing between her legs, just as her pussy was getting west, and it was not long before he was inside her. Any other ideas or conversation threads were lost for the time being.

They chose a Tuesday evening for their grocery store visit and a store well out of town, to reduce the likelihood of running across anybody they knew, particularly any of Andrea's patients or Sterling's law clients. When they got to the store around 8:30, she was surprised and a little nervous about the number of cars in the parking lot. They backed into a space at the end of the lot, bordered by some trees and bushes. Before they headed into the store, Sterling undid two buttons from the top of her dress and two from the bottom. Not enough to expose her -- yet, he thought -- but enough to start raising the stakes. She gripped his hand nervously as they headed to the store.

Sterling mounted his small camera onto the shopping cart, nestling it against the backpack he had put in the child seat, so it would not be too obvious. Andrea was pleased to see that the store was not all that crowded, despite the number of cars.

They started in the produce section. Andrea bent over the layouts of fruits and vegetables, and Sterling took some pictures. Every now and then, when she was sure nobody could see, she flipped up her skirt and gave him a shot of her ass.

Next to the produce section were the deli, cheese, and prepared foods counters. These got Andrea to bend over to point to things she wanted, but Sterling was disappointed at how little reaction he was getting from the people behind the counter. As they worked their way toward the first aisle, he decided she needed to be a little more daring. Before they turned the corner, he undid another two buttons from the top.

Andrea was a little more nervous as she made her way down the aisle, full of health foods. Her dress opened nicely when she bent over to put in a couple cans of soup, and she was willing to spread her legs when she knelt down to get something off the bottom shelf, and to lift the back of her skirt and flash her ass as she sashayed down the aisle. She still turned away or covered herself when another shopper turned into their aisle.

When they turned into the next aisle, Sterling pulled her aside and said, "Go up to that woman, and ask her about something on a lower shelf. Bend down in front of her, and take the box to show her."

Andrea was nervous as she approached the woman. "Excuse me," she said. "Do you know anything about this dressing?" She bent down to pick up a bottle from the lower shelf, and the top of her dress fell a little more open as she stood up, exposing a bit more of her little breasts. The woman looked flustered, and said no she didn't, then turned quickly and walked away. Andrea turned to Sterling, who shrugged and said, "better luck next time," as he drew close to her.

There was a man in the next aisle, and he seemed to find several ways to say that he did not know anything about the soup that she had picked off the bottom shelf, though he looked very happy at the prospect of helping her out. She and Sterling chuckled as they rounded the corner to the next aisle. The next few times she tried, Andrea had better luck picking candidates who could be fun, and she got more into the game, to the point where Sterling was having a little trouble keeping up with her.

They were alone in one of the frozen food aisles, and Andrea played with exposing her tits with the freezer doors open. A couple times, she pressed her bare tit against the inside of the door, giving herself goosebumps and leaving a nipple print on the inside. The frost had built up on one of the doors from her holding it open so often that she almost got caught when a store employee rounded one corner, coming to stock the shelves, and a customer came round the other corner.

Beyond the frozen food section, the store became somewhat of a warehouse with stacks of paper towels, toilet paper, and other household supplies. These aisles lent themselves to a different kind of fun. At one point, Andrea stepped in between the stacks and lifted up her dress for Sterling to film and get some pictures of her naked body. In another stack, she pulled him in with her, and they kissed and felt each other up. He managed to undo two more of her top buttons and one down below, while she reached in and stroked his cock, commando inside his sweatpants. When they stepped out, her dress was open to below her little tits, so it would not take much to expose her, and his hardon was pressing out against the leg of his pants.

"I'm going to have to hide behind the cart till this settles down," he laughed as he started to push the shopping cart down the aisle. She danced down the aisle in front of him, spinning around once and pulling the dress open to flash her tits for the camera. She laughed, pulled her dress back together, and spun around to turn back around the corner, starting her way back to the center of the store.

As Sterling started to follow her, he heard her give a little yelp. When he rounded the corner to turn into the next aisle, he saw her standing across from a cart being held by a slightly older man smiling at her. She seemed flustered as she turned toward Sterling. "Um, this is . . . " she stammered and waved her hand toward the other man.

"Hi, Bill Berman," the man said with a relaxed smile. "I work with Andrea at the practice."

"He's the head doctor," Andrea managed to get out before stepping back toward Sterling. "This is my husband," she said with a gulp.

"Hi, Sterling Crawford," he said and stuck out his hand, taking care to stay behind the cart as best he could. The two men shook hands, while Andrea stood off on the side, looking somewhat shell-shocked.

"Have you come up here before?" Bill asked. "It seems kind of far away for you."

Sterling shrugged as he made up a story. "We were visiting some friends nearby and decided to give it a try. We'd heard good things about it. How about you?"

"I moved up here a year ago when I split from my wife." He laughed. "It took me a while to figure out how to cook for myself, and I got in the habit of organizing my shopping one night a week. Figured Tuesday was the slowest night." He started moving down the aisle. "I'm not really the head doctor, I've maybe been there longer than the others, and one of three partners. But Andrea's pretty close to getting to the partner level."

Andrea was walking next to Sterling, trying somewhat to hide behind him. "We'll see," she laughed, trying to get over her nervousness in her colleague's presence.

"You know what?" Sterling said, stopping the cart. "Don't we need some tissues? Can you get some over there, honey?"

She bit her lip. She was sure he had no idea whether they needed tissues or not. He just wanted her to walk over and pick something off the lower shelf, so she would expose herself to some degree. She discreetly smacked his arm and headed out across the aisle, crossing in front of Bill's cart. He stopped and watched her go, bend down, get a box of tissues, and drop them in her cart. She saw that he was watching her, though she could not read the expression on his face. She was not sure whether he was disapproving or taking time to enjoy the sight of her tits.

Sterling moved on down to the end of the aisle, then headed toward the center of the store, skipping the frozen food aisles. Bill seemed to be following right along.

In the next few aisles, Sterling found something else for Andrea to pick up, usually from a lower shelf, though sometimes from a higher one, giving her a chance to expose her butt. Bill kept pace with them, sometimes getting something for himself, usually from a lower shelf so he could presumably get a glimpse up the lower part of Andrea's dress.

At first embarrassed by having exposed herself to a colleague who probably had the power to discipline or even fire her, Andrea found herself getting turned on by Bill's steady attention to her. She started chatting with him, about his separation, learning to be newly single, how his children were doing with the divorce, what he liked to make for dinner. She even suggested a couple of foods that would be easy to make. Sterling managed to continue discreetly taking pictures and recording her.

When they got to the checkout line, Sterling maneuvered himself to go ahead of Andrea, yet leave her in front of the cart, so she would have to bend over to take the groceries out and put them on the belt. Every time she did so, of course, her dress fell open, giving Bill, who was next in line, a clear view of her tits and stomach and maybe all the way down to her pussy. He made no effort to look away.

When they had paid and packed everything up, Andrea waved to Bill and said she would see him the next day. On the way out of the store, Andrea took two bags, while Sterling had one, so he could handle the camera. She led the way back to the car, swishing her dress as she strode across the parking lot. When they crossed into a pool of light, she lifted it over her ass. She even managed to spin around once, letting the whole thing spin around, since she had unbuttoned the last of the buttons, and the dress was flying free. When they got to the car, she popped the trunk, which slowly opened, and she turned to Sterling as she lay her bags onto the floor of the trunk and lifted the dress off of her shoulders, exposing herself completely naked.

He put his bag down and tried to prop the camera somewhere, then wrapped his arms around her as they hid between the car and the trees along the road. "You've gone crazy," he said as she lifted up his t-shirt and slid her hands down inside his sweatpants. She pressed her naked body tightly against his, kissing him wet and deep, and feeling his cock throbbing against her leg.

He turned her around and bent her over, and she braced her arms against th3 floor of the trunk. He shoved the dress up to her shoulders so he could see her back and fat little ass in the dim light from the street lamps. He ran his hands over her well-muscled back and reached around to grab her bare little tits. She moaned as he squeezed her and pressed himself against her. He pulled her up a little, keeping one tit covered and running his other hand down her stomach until he reached her generous pussy lips and stroked along them. She gasped louder as his fingers delved between her folds of tangled flesh, making them wet and sending waves of pleasure through her body.

She reached back to find the waist of his sweatpants and push it down as best she could over his ass, brushing her fingers against the cool skin of his hips. It was his turn to moan, and she maneuvered the band of the pants down over his ass and down his legs till his cock sprang out and bounced against her bare legs.

They heard cars on the other side of the trees along the parking lot, but they didn't care. He bent her forward till she reached the floor of the trunk, then slid the end of his cock up and down between her wet, throbbing pussy lips till he found the opening and slid himself deep into her cunt. She groaned as he filled her, his cock growing as he plunged inside her, then slid back and forth. He loved looking at her fat little ass as he fucked her and seeing her thick pussy lips wrap around his thrusting shaft. Bending over her, he reached around to grab her tits and tweak her nipples, triggering more squeals of pleasure from her as she pressed back against his thrusts.

Before too long, his cock erupted inside her, and he yelled in relief as he filled her. Her arms collapsed, and she put her head down to receive all of him. He squeezed her butt cheeks as the last of his cum pulsed into her, then slowly he let his cock slide out and he watched his cum drip out of her swollen pussy, letting his own last few drops land on her leg, cold dots in the night breeze.

He pulled up his sweatpants, then helped her stand and guided her to the passenger seat. "Keep your dress open, and prop your feet up on the dashboard for the ride home." She looked at him in a daze, smiling, then climbed into the seat and put her feet up, as directed. He handed her the seatbelt and went around to his side. They drove out of the parking lot without being observed, and when they got onto the local highway, she started rubbing her mound, pressing against her clit and pussy lips. He glanced at her the first time she moaned and smiled. It was a nice long ride, should give her plenty of time to cum and provide him with some entertainment as well. Much better than the radio or a CD.