The Dare Md

Andrea parked in the far corner of the sporting goods store parking lot, as instructed, and waited. As the minutes passed, her nervousness increased, but she had been told to wait, so she did.

Ten minutes later, another SUV pulled up next to her, and her colleague, Dr. Bill Berman, leaned out the window. "Ready?" he asked with a big smile on his face. She grabbed the backpack on the passenger seat, got out, and walked around to the other side of Bill's car.

When she got in, she handed him her car key and backpack, which he put in the back seat.

"Thanks for letting me borrow the camera overnight," he said as he backed out of his parking space. "It helped me get familiar with it."

"Where are we going?" she asked when he turned out of the lot and away from the main road.

"Farm country," was all he said as they drove along. Andrea was too nervous to say anything further.

IT HAD BEEN HER IDEA to have a member join them on an out-of-town dare. When that did not work out, she and Sterling kept toying with the idea. One night, as they were lying in bed, she impulsively said, "What about Bill Berman?"

Sterling was gently rubbing her pussy at the time. "Do you think he would do it?" He pressed just a little harder, and Andrea sighed.

"I think so," she said, writhing just a little. "I mean, he's already seen me naked, and I've seen his . . . " She was going to mention having seen him masturbate, but Sterling's touch broke her concentration.

"And what about you? Do you want him filming you naked?" She moaned as he kept drawing circles over her pussy, pressing more firmly with each stroke. She twisted against him as he brought her to the edge of orgasm, then relented. "Well?" He asked again when she had relaxed. She moaned in reply and took his cock in her hand. Soon they were both distracted from further conversation, completely focused on making each other cum.

In the morning, she said she would bring up the idea with Bill. It took her more than a week to finally get over her fear and ask him, and it took a few more days for him to agree, after asking her several times whether she was sure about this. When he finally agreed to do it, she asked him to write up a scenario that she could follow. "I want you to challenge me," she said, "push me past my boundaries, my comfort zone." She leaned forward and whispered. "I want you to make me your whore."

Bill sat back in his chair with that somewhat opaque look he got when he was considering a question. Then he gave her a half-smile and said, "Okay."

That night, after Sterling had fallen asleep, Andrea lay in the dark, thinking, "What the fuck have I just got myself into?"

AS BILL DROVE ALONG, she pulled the scenario out of her backpack to read it over one more time, even though she could probably recite it from memory. She looked at it, but could not concentrate, so she tossed it onto the floor. Finally, after riding in silence for a while longer, she asked the question that had been puzzling her for a while.

"Why won't you tell me the screen name you used to sign up for my site?" Bill gave a small chuckle and kept driving. "I offered you a discount," she added, "but you'd have to tell me what name to give it to."

"Does it bother you that you don't know? After all, no other member knows who you are, so far as I know. And you don't really know who any of them are."

"I thought we might be different."

"We are different." He laughed again. "You know more about me . .. and have seen more of me than you have any of your other members. Or our co-workers, for that matter. Do you begrudge me one little secret corner where I can play out my own fantasies?"

She smiled. "Just like you're playing out these fantasies today?"

"You opened the door, and I walked in."

She sat back, not quite sure that conversation had soothed her nerves. She rode the rest of the way in silence.

AFTER ANOTHER HALF-HOUR, Bill turned onto a small, half-paved road running between two fields, then onto a dirt road. He soon pulled off to the side to park, and they got out. He got the backpack out of the back seat and pulled a shirt out of it before slipping it onto his shoulders. He got the camera from its own bag in the back and turned it on. "Ready?"

She nodded. He focused the camera on her and said, "Go."

She pulled off the shirt she was wearing and tossed it into the back seat. She cupped her little tits in her hands and turned toward the camera. She had a temporary tattoos of the word WHORE posted over her left tit and SLUT over her right. Over her navel were the words DADDY'S LITTLE SLUT. These were part of the package he had prepared for the scenario, aimed at turning this dignified, married doctor colleague into his own little whore.

She was about to reach into the back seat to pick up the shirt he had tossed there when he said, "Put this on first." He handed her a leather collar with the word WHORE in silver block letters. He kept the camera on her as she reached behind her neck to secure it. He scanned the collar and her tits and stomach, then said, "Okay." She reached into the back seat and pulled out a black tank top with DADDY'S FUCKTOY written in white script. She pulled it on and ran her hands down the front to smooth the material over her tits, pinching the nipples as she did so.

At his signal, she turned and headed down the path. After a couple minutes, he said, "Shorts." Without breaking stride, she unbuttoned the white jeans shorts, pushed them down her legs, and kicked them to the side. She was wearing a tiny thong that allowed him to focus on her tight little ass as it twitched its way along with every step. He had not had much chance to check out her ass when she stripped in his office so many months ago. He appreciated it on the videos she posted on the site. Now he was glad to have his own private live view.

"Turn around," he called out. She did a quick turn and kept walking backwards as she played with the waistband of the pink thong announcing DADDY'S LITTLE CUM SLUT. She lowered it once or twice, just enough to give a hint of her pussy, then laughed and turned around to continue back down the path, now getting narrower and overgrown.

After a turn, Bill called out, "Top." He saw a slight stiffening in her back and hesitation in her step, then she lifted off her tank top and tossed it onto a tree branch. She danced around a little, turning to face the camera and squeezing her tits. She took a few steps back, turned, and rocked her ass back and forth while Bill filmed. She pulled the waistband of her thong out to the sides, lowering it left and right to tempt him with glimpses of her pussy. She laughed and danced further down the trail.

Even though she came across as happy and carefree, she was trembling inside as she got closer to the ultimate objective of this escapade. She wanted to do it, to get naked and play with herself in front of her colleague, but the thought continued to make her stomach tighten and her pussy quiver. She was biting her lip when Bill called out her next instruction.

"Thong."

Andrea froze for a split second, then slid her fingers behind the rear of the waistband and pulled it slowly over her ass cheeks. Then she turned to face the camera, knowing that Bill was zooming in on her as she lowered the thin cover down past her pussy, then all the way down to her knees, where she let it fall to the ground. She stood up, trembling inside, as he pulled back to get a complete view of her totally naked body. "Leave the sandals," he said.

With a sigh and a smile, she stepped out of them, then turned and walked to the end of the trail, twitching her ass for the camera. She grabbed a thin tree trunk and used it to swing herself around, spreading her legs and doing an impromptu pole dance for the camera. Bill zoomed in on her and followed her as she shifted back and forth, giving him a clear view of her pussy and ass as she swayed from side to side.

Finally, after a couple minutes, he called to her. "Come get your things out of the backpack." Shifting the camera from hand to hand, he slid the straps off his shoulders. He kept the camera on her, even holding it over his shoulder so he could capture her face and tits as she fussed with the bag and pulled out a blanket and her little bag of toys.

"There's a soft patch of ground just past that tree," he told her.

As she spread the blanket where he indicated, she gave him flashes of her ass and pussy. She realized that she was losing some of her nervousness and getting more into playing the game she had requested. When everything was spread out, she looked at him.

"Sit on the blanket and show me how much you love that big dildo," he told her.

Angela smiled as she picked it up. He had bought her this new dildo, thicker, longer, and more anatomically detailed than the others she owned. The shaft was a medium brown, with thick veins running the full,length of it, and the head was delicately sculpted in a slightly pinkish brown. She held it in one hand and stroked it lightly with the other. The feel of it was also amazingly lifelike.

She could tell that Bill was nervous as well, even though he tried to sound strong and mean as he gave her directions. She knew that was not in his nature, that he was pushing himself to play the role she had asked for, that of a demanding whoremaster pushing her in unfamiliar and uncomfortable directions. Knowing that he was nervous in his way helped her feel more confident as she held the cock up to her mouth and licked the full length of it.

She raised her eyes toward him as she slowly and sensually dragged her lips along the slightly pinkish head. She noticed a stiffness pressing against his shorts. Has he gone commando, she wondered as she slid the cock further into her mouth. She gagged when it went deeper than she had expected, and she was rewarded with another bounce inside his shorts. Oh, Doctor Bill, she thought with a quiet giggle, you're a naughty boy.

She ran her tongue along the veins molded into the thick shaft and gagged a few more times when she pushed it deep into her throat. Then she turned around onto her hands and knees, her ass to the camera, dropped the dildo, and picked up the vibrator. She turned it on the low setting and started rubbing it along her pussy lips. Bill shifted his position so he could get her in full view, from her bare feet to her shoulders, and a clear shot of her pussy.

After Andrea had loosened herself up with the vibrator, she took the dildo, rubbed the head between her wet pussy lips, then set the base on the ground and positioned herself so she could slide down onto it. She began riding it, going deeper and moaning more loudly with each thrust. As Bill crouched down, he realized that his cock was getting harder and slipping out of his shorts. Maybe it was not such a great idea to go commando, he thought as he struggled to keep Andrea's ass and pussy in the picture frame.

Andrea was now riding the dildo hands-free, pushing down almost to the base with a deep moan, then sliding halfway up. She realized that her nervousness had dissipated and that she was feeling a thrill throughout her body at being naked and exposed—and fucking herself—in front of her colleague. She turned her head over her shoulder and called out, "Talk to me, daddy. Tell your whore what to do."

It took Bill a second to remind himself that part of his role was to be a mean whoremaster. He called out, "Ride that cock, bitch!" After she rode it a few more times, he added, "Get on your hands and knees and crawl around with that cock still in your cunt."

She leaned forward and started to crawl around, the dildo wobbling as she moved. When she had her back to him after a couple of circles around the blanket, he said, "Hold like that. Spread your ass for me, you little whore." She hesitated for a moment, then put her head on the ground and brought her hands around to grip her ass cheeks and spread them. That gave him a perfect view of the dildo hanging out of her pussy, pulsing up and down, and her cute little asshole winking at him above it. He knew she was uncomfortable with showing her ass that way, and he lingered on the view before he told her to move on.

She crawled around a couple more time, then rolled onto her back and lay flat, stretching her arms and legs out to the corners of the blanket. She was smiling broadly at the joyful, sensual feeling of her total exposure and at the sight of Bill's cock throbbing against his cotton shorts, happy in the knowledge that she was doing that to him.

She reached down to slide the dildo out of her cunt and bring it up to her mouth. She looked right at the camera lens as she slid her tongue to lick her juices off the sculpted veins. "Do you want me to fuck myself for you, daddy?"

The answer came out more as a sigh, "Yeeesssssssss," as he glued his eye to the viewfinder to make sure he was catching all of her. His cock stiffened even more as she dragged the tip of the dildo over her chin, between her perfect little tits, along her tight stomach with its stretch marks and slight wrinkles, down to her pussy, spread wide between her open legs. She reached down with her other hand to massage her pussy lips a bit, then spread so could slide the dildo back into her greedy cunt. She moaned and writhed as the thick rod pressed against her cunt walls, the molded veins triggering waves of sensations that shot throughout her body. As her right hand kept the dildo in motion, her left hand felt around till she found the vibrator. She turned it on and rubbed it along the sides of her pussy and onto her clit. Her body quivered with each pass of the vibrator along the swollen labia clutching the dildo as it moved in and out.

"Fuck that cunt, you married whore!" Bill's outburst surprised both of them. He was about to apologize when Andrea rolled in his direction, pounding the dildo even harder, as it glistened in the sun from the juices pouring out of her. He had crouched down so he could see all of her as she got more frenzied in her fucking. He was not aware that his cock, now rock hard from watching her, had completely slipped out of his shorts. Even his balls were exposed to Andrea's gaze, firing up her passion even more.

She dropped the vibrator and pulled her legs up and out, rolling back onto the blanket as she did so. Holding her legs wide with her arms, she used both hands to pound her cunt with the dildo, using the full length to drive herself to new heights of passion and sensation. She had never felt so free, so totally liberated from any fears or restrictions. She was growling, close to roaring, in her fervor, totally oblivious to her surroundings as the waves of orgasm built out from her center to take over her whole body. Just as it was about to reach its peak, she brought one hand down to rub her clit, to concentrate the energy even more.

And then it exploded. She fell backwards, her legs fell open, and her body was writing and twisting with each new wave as she continue to rub circles around her clit. Her body thrashed with each wave, like a sheet being shaken out, until little ripples ran through her, making her flinch lightly as she lay on the ground. She was smiling, gasping in utter delight, beginning to feel the sun through the leaves touching her energized body. When she thought she had finished, she pulled the dildo out of her swollen, wet pussy, and she shook again, one last wave sending her legs kicking out. Then she collapsed flat onto the ground, sighing, smiling, laughing in delight at a phenomenal orgasm. Just splendid, she thought to herself as she drifted off into a light doze.

When she opened her eyes, Bill was staring at her. He was amazed not just at what she had done, but also at the look on her face, a look of total serenity. This was totally unlike the Andrea he had known professionally for the past few years. That Andrea had always had a serious, guarded side to her personality, even when she was being sociable and funny. This one, though, spread out totally naked before him, recovering from a wild orgasm, seemed totally free and at peace.

She rolled onto her side, still smiling at him. For her, the smile was more than a sign of complete satisfaction. It was her joy at seeing the bulge of his cock, still a bit stiff, pushing against his shorts. She reached out to touch his leg.

"Ssshhh," she said when he flinched at the contact. She shifted around onto her stomach as she's lid her hand up to take gentle hold of his cock. With her other had, she pushed the shorts out of the way and reached up to cup his balls as the cock stiffened under her stroking. She crawled forward a little so she could brush him against her cheek. He moaned and mumbled what sounded like her name, and she felt him twisting under her touch as she kept on gently stroking his stiff, sweaty rod and massaging his balls. He leaned further back onto his arms, helping her expose his cock even more to the sun and her touch.

As she brushed him against her cheek, she debated with herself whether she should kiss him or suck his cock. She certainly thought Sterling would get a kick out of her reaction to seeing Bill's hard cock in reaction to her exposure, because she knew she would tell him everything. She was not sure, though, how much he would like her taking another man into her mouth without his being there. They had done that once before briefly, with another couple, but never on her own. Maybe he would approve and just fuck her even harder when she told him, but she was not sure.

"Oooo fffuuuuccckkkk,"Bill groaned, and she realized he was about to cum. She stroked him harder and faster, turning slightly to be more in line with his cock. And then it came, the first stream of white cum shooting out of his tiny hole right at her cheek. Just as she flinched at the warm stream landing on her, the second shot came out and landed across her eyes, then the rest on her chin and chest. She giggled at the warm splashes across her face and the cum running down her chin and tits. He fell back a bit further as his orgasms died out, and the last few drops leaked out onto her hand still wrapped around him. When she was able to open her eyes again, she saw a drop oozing out of his tiny hole, and she reached forward with her tongue to catch it, brushing gently against his cock head in the process.

She fell back onto the blanket, letting go of his cock as her hand drifted down his leg. He shifted to relieve some of the strain on his legs and turned to look at her, wondering at the cum dripping down her face and amazed at what had just happened.

SUPPOSE, THOUGH, WE TURN THE CLOCK BACK A BIT to when she reaches up his leg. Instead of just touching his cock, suppose she sits up a bit and runs her hands up to the waistband of his shorts.

"Wha . . . " he starts to protest, and she shushes him as she pulls the shorts down and slides her hands over his bare ass. In amazed compliance, he shifts around to help her and soon he takes them off. She has her hand around his cock, still stiff from watching her and now getting thicker under her touch. And instead of brushing it against her cheek, she licks it and then lies back, opening her legs and pulling him toward her.

"Take off your shirt," she whispers urgently as she strokes his throbbing cock head against her swollen, wet pussy lips. His eyes widen in amazement as he feels the soft slickness of her folds against his cock and, as though under a spell, he pulls his shirt over his head and leans down toward her. As he feels himself pressing against the tightness of her cunt muscle, her legs wrap around him as she rotates her hips upwards, and he is inside her. "Andrea," he sighs as he slides inside the slick wetness of her already loose cunt. She puts her arms around his shoulders and pulls him down, even as she tightens her legs around his waist, locking him into position. His hips start pulsing out of instinct, sliding his cock in and out of her. He hears her gasping and moaning right next to his ear, and his own voice is uttering growls of urgency and satisfaction. He buries his face into her neck, surrendering to the fierce passion aroused by this beast under him. And he is hers, ready to give himself completely.