Molly Entertains (I Dare You)
Molly's unhappy about having Adrian for the afternoon. Then she meets him...
Molly was pissed. “How did I get talked into this?” She thought as she pulled on her tight jeans and sucked in her breath so she could close the zipper. As reluctant as she was to keep this appointment, it had taken her longer than normal to get going. Now she was running very late and was fumbling around her bathroom in a half-hearted attempt to look presentable before she went out.
Her vibrant and usually smiling features required little in the way of enhancement, a little lipstick and some eye-liner was all she used today. Her teeth were white and straight, her nose perhaps a little on the large size, but very acceptable. Her bright eyes appeared to be constantly searching out mischief from above her high cheekbones and her face radiated fun through its covering of soft skin that appeared to stretch beautifully across a layer of remnant puppy fat that kept her looking younger than her twenty-seven years.
Running her hands through her expanse of curly brown hair, she elected not to spend any time trying to subdue its wild spirit today. Glancing lower in the mirror, she conceded that she would have to find a shirt though. A simple white bra struggled to hold her heavy round breasts and Molly gave them both an encouraging bounce with her hands. They sure were a pair to be proud of, but today she had no interest in advertising them. Hurrying to her closet, she selected an oversized green linen shirt that was appropriate for the afternoon’s duties and did it’s very best to hide her voluptuous figure.
After one final check that she was at least presentable enough for a casual afternoon off coffee shops and sightseeing, Molly grabbed her denim shoulder bag and dashed out of her apartment; pissed, resigned to a wasted afternoon and just wanting to get the whole thing over with.
This was all Joanne’s fault. Her friend had called her up and called in a favor earlier in the week. Joanne’s cousin was in town on business, would be around through the weekend and at a loose end on Saturday. Joanne and her boyfriend had long-standing plans for the day and she pleaded with Molly to meet with her cousin and entertain him for the day, for the afternoon at least. Molly resisted, not wanting to give up a whole afternoon and not really feeling hospitable to the opposite sex right then – yet another guy who was all trousers and no manners was recent history.
“Hey, it’s not like he’s some ugly geek who smells or something.” Joanne continued her selling of the task to Molly.
Molly didn’t care. Even if he looked like a male model and acted like a perfect gentleman, she was reluctant, to say the least. Eventually she gave in and agreed to show him around for the afternoon, mindful that it was Joanne who helped her decorate the apartment when she moved in. No way was she going to make a big effort though, no way.
Despite arriving at the coffee shop where she was supposed to meet him five minutes later than agreed, Molly was first to arrive. It was just another reason to view the afternoon with frustration. Resigning yet again to make the best of things, she ordered a drink, sat down at a table near the window and idly smoldered at her situation.
He turned up seventeen minutes late. Molly didn’t notice him at first; mainly because she’d imagined him as a nondescript, weak-featured, business traveler. When he stooped at her table and enquired, “Molly?” it took her a few moments to adjust her image of him in her mind. He offered his hand and a warm smile. “ Adrian .” He introduced himself. “I recognized you from that lovely hair. Joanne said I couldn’t miss you.”
Rather than rush off and get himself a coffee before his joined her, Adrian slipped his athletic frame into the chair next to Molly and comfortably thanked her for giving up her time to entertain him. His dark blonde hair was gelled and carefully disheveled, his shining blue eyes were assured, but not smug, and his hands looked strong as they rubbed his thighs gently through the denim of his very tight jeans, showing maybe just a hint of nerves at meeting her. Molly found herself staring at his jeans while his soothing voice said something or other about whether she wanted another coffee or not.
“So, what would you like to do this afternoon?” Molly asked when she’d gathered herself from the unexpected appeal of Adrian . “We can pretty much do anything you want.” Molly didn’t offer any overtones in her offer, but she sure was thinking them. It’s amazing what a good looking smart guy can do for your demeanor.
“Joanne mentioned your hair, but she didn’t warn me you were so attractive.” Adrian smiled, self-consciously. “I wouldn’t mind just sitting here all afternoon, watching you smile.”
Molly flapped her eyelids with a cartoon-like motion. Her heart jumped just a little and her imagination continued down a path that she hadn’t expected for this afternoon. “We could… but all that caffeine would give me the shakes and I’d have to run to the washroom every few minutes.”
She offered to take him to a movie, drive him out to a large shopping mall, view the local architecture or visit the zoo. While Adrian listened to the options Molly got the impression that she hadn’t quite hit the mark yet, but she was also running out of options. “We could go for a walk along the river. If you like, it’s quite a nice day.”
“You know,” Adrian smiled warmly, “after being locked away in an office block all week… that sounds like a pretty good idea.”
A few minutes later they finished their drinks and stepped out to the warming afternoon sunshine. Molly led the way to the riverside and down to the walkway that lead along the waterside and eventually out of town. Adrian walked casually, holding his jacket over his shoulder and contentedly enjoying his surroundings. Molly had not only warmed to her companion, but was feeling a familiar heat rise within her every time she snuck a look at Adrian ’s muscular body and sharp features. From dreading the afternoon she had quickly moved to wonder if she couldn’t engineer extending their “date” to cover dinner… at least.
For his part, Adrian was quietly smitten by Molly’s fun conversation, not to mention the voluptuous body that her shirt couldn’t hide and was encouraging his imagination to run wild. Whilst her face smiled so naturally and so vivaciously at him, other elements of her body were becoming less subtle now, her tight ass and wonderful boobs virtually screaming at him. Joanne sure hadn’t warned him how attractive Molly was. Interestingly, all she had warned him about was that he shouldn’t make any bets with her or dare her to do anything.
“So,” he looked over with a mischievous grin, “why would Joanne warn me not to dare you to do anything?”
Playful annoyance crossed her features and she shot the look across to him, “she said that?” Adrian nodded slowly, enjoying that he might have found a fun nerve. “I guess she means that I have a reputation for being a little daring at times, and not losing many bets.”
“Like what?” He probed immediately.
“Oh, you know…” Molly tried to sounds vague while she searched her memory for an appropriate item to tell him about; something non-incriminating. It wasn’t an easy task. “Mainly girl’s-night-out stuff, just for a laugh.”
“Oh, okay.” Adrian nodded. “I’ll have to remember not to dare you then.”
It was Molly’s turn to nod knowingly. “Good call, because I’d dare you back. That would be a condition I’d insist on. So you’d need to be prepared.”
“Yeah,” Adrian considered, “and I might not want that!”
Molly asked him about his job and he tried to talk her through what he did without boring her. He admitted that he worked long hours during the week and seldom had time for a social life. Molly took that to mean he was unattached and gently dropped into their conversation that she’d had a long run of failed dating experiences with males of various ages afflicted with various significant flaws. An hour after their walk had begun the path was no longer the paved sidewalk it had started as and their surroundings were all green and alive, as opposed to the concrete and brick of the town. This did not go unnoticed by Adrian .
“I dare you to go behind those trees, take your panties off, then come back and put them in my pocket.”
While the words were pretty much out-of-the-blue for Molly, she smirked when she heard them and her face showed no sign of shock whatsoever. “You understand there’ll be consequences?”
Adrian nodded. “I thought we could at least inject a little fun into the afternoon.”
Without another word, and holding his gaze as long as she could, Molly turned away and walked about thirty feet to the semi-cover of a couple of bushes. She glanced over her shoulder to check her position, then pulled her jeans apart and kicked off her shoes.
He watched as much as he could see as she took the dare. He saw her stoop at one point and then caught the amazing sight of her pulling the jeans off her foot. His pulse rate started increase quickly, the excitement and anticipation was incredible. He watched closely, just in case he could see her bare legs or even her ass, but Molly was tantalizingly discrete as she pulled the jeans back on without revealing any more.
Molly’s face was smug as she walked back towards him with a cocky gait and a pristine pair of white panties in her hand. Never letting her eyes leave his, she used both hands to open his pants’ pocket and stuff the warm panties inside. “Happy now?” She asked.
Adrian nodded, “Very.” He turned and restarted their walk. “Do I get to keep them?”
Molly sniffed at first, and then giggled, “Perv. Sure, call them a souvenir from this afternoon. You can think of me whenever you… erm, look at them.”
As they continued casually along the riverside, Molly let his anxiety rise, knowingly. She continued their small talk, asking about his hometown and some of the places he’d visited on business. Her comeback dare came abruptly in the middle of his telling her about a trip to San Francisco . “You can walk over there and take your underwear off.” She pointed to an open area that led to some trees that were over a hundred yards away.
Adrian took a deep breath and turned away, both enjoying the exchange and the excitement of their game. He walked no more than twenty yards and then, with his back to her, slipped off his pants, followed quickly by his underwear. As he pulled his jeans back on, he was careful not to catch his erection in his zipper.
Molly smiled as she watched Adrian bend over and slip his pants of, revealing a pale but very tasty ass. When he walked back to her he offered his white underpants. “You want these?”
“Hell no.” Molly giggled. “You can put them in that trash can.” She pointed at a black container at the side of the path. “In fact, let’s just make that part of the dare. If that’s okay?” She chuckled and walked off.
Adrian had no option but to do as he was instructed, and then walk behind Molly for several steps while he caught up with her. It was tempting to continue walking behind her though, enjoying in her thighs and ass cheeks as she moved along.
“So,” Adrian caught up with her, “are we even and done with the dares, or should I offer you another challenge?”
“Up to you really.” Molly’s voice was matter-of-fact, but the smile on her lips was encouraging, to say the least.
“Okay then. I dare you to take off your bra.” Adrian waited no time in keeping the game going. “But you have to let me watch. Close up.”
Over the next minute Adrian was too obsessed by the images in front of him to thank his cousin for warning him not to dare Molly. He should have thanked her though, because he’d never seen anything quite like it as his companion slowly unbuttoned her shirt and slipped it off her shoulders. Molly watched Adrian ’s face, seemingly unconscious to any other prying eyes that may have been around them on that public path as she reached behind her and unclasped her bra.
Adrian ’s jaw slackened considerably as the bra fell away and revealed her magnificent breasts. Large, round and peaking with perfect dark nipples, he gazed as they wobbled and swayed with her every move. They looked so heavy, yet somehow defied gravity and protruded outwards more than they sagged downwards. His instinct was to reach out and take them in his hands, but he remained rooted to the spot, mesmerized.
Molly threw her bra to him and he caught it without taking his eyes from her breasts, then she started to pull her shirt back over her shoulders and button it up again. “You can keep that too if you want.” Molly giggled as she covered up.
He knew he should say something, or at least be capable of saying something, as Molly turned and restarted their walk but for the first time in a long while, Adrian was dumbstruck. As he fell into stride with her he was excited, amazed and strangely comfortable with this amazingly sexy and fun woman next to him. And now it was her turn to dare him… an anxiety he could feel all over as their silence hung somewhere between his hard on and her smirk.
Of course, Molly knew this. She knew he was waiting her next instruction and delighted in holding back far longer than he could possibly expect. Molly loved such playful expectancy before sex. She also knew about the bulge in Adrian ’s jeans and looked forward to finding out a little more about that.
Without a word of explanation, she led them off the path and into a patch of mature trees that offered some shade from the warming afternoon sun. Seeming not to be particular about where she sat (which was far from the truth as she chose a very secluded spot), Molly slumped down against a thick oak tree and looked up at the dolefully obedient puppy Adrian had become in the last twenty minutes.
“Okay, let’s have it.” Figuring he knew what was coming next, he tried to sound confident, but failed. “What’s my dare to be?”
Molly let him stew for a few more seconds before answering, “I dare you to find out if I’m as excited as you obviously are.” She nodded playfully at his bulge.
Adrian took another long look at Molly’s gorgeous figure before slipping down to his knees beside her. “I guess I should be happy that I don’t have to wrestle with your panties as well. You could almost call it good planning.” He laughed nervously as he tugged at her zipper and pulled the waist button of her jeans free. Glancing up at her content face, he started to slip his fingers beneath the denim and towards the hidden delights of her pubic area. He felt some soft hair first, then slowly moved further inside. Molly’s skin temperature immediately started to rise as he found her hot and already damp pussy lips. Wriggling a finger, he slipped it inside her a little and felt a rush of moisture envelop him. He smiled widely and looked down at his half-hidden hand. “Certainly feels like we have an excited situation here. Wonder what we should do about that?”
Before he could look up to see Molly’s face again her fingers were taking their own initiative and pulling urgently on his belt. He rubbed her vigorously while she freed him from his jeans, his finger slipping up and down the length of her slit, already coated in her excitement and running easily between her lips. Her hand found him with a firm grasp and he felt his cock spring out into the fresh air. He was right, the lack of underwear helped. With his free hand, Adrian cupped one of her breasts through her shirt, marveling at its weigh and the warm softness of it. Already her nipple was proud and easy to find with his fingers.
His cock felt new, hard and warm in her hands. She stroked him gently feeling his contours and judging his excitement while she explored her latest toy. “Stand up.” She urged. “I want to see this better.”
Once Adrian was on his feet, Molly pulled away his jeans while he loosened his shirt. He watched her smile as both of her hands wandered over his very hard and upright cock. “Nice.” She giggled, testing his balls for size. He was about seven inches, nicely thick all the way along his shaft and he had a sleek dark pink head that was throbbing nicely with the excitement. Molly loved looking at a new cock and admired Adrian ’s as he twitched and pointed straight up, parallel to his belly. Her hands glided easily along him, softly encouraging his excitement and pleasing her.
He wanted to stand there and let her bring him to climax there and then. Her fingers were working softly between his balls and his thighs, sending pulses of pleasure all the way up his length in ways way no one else’s fingers ever had. Looking down he watched as she concentrated on her close up view if him, licking her lips and enjoying every movement she made for him. Then he caught a glimpse of her heavenly cleavage and felt an urgent need to change position.
She offered no resistance as he eased her shoulders up to stand before him and allow his fingers to work her shirt open. When the last button was undone he slipped a hand inside and felt the soft flesh of her wonderful boobs for the first time. Molly brought her mouth up to his and offered a long, deep, kiss that accompanied his exploration perfectly. As his fingers found her nipple and squeezed a little more excitement out of it she found him with her hand and resumed her long and gentle strokes.
He slipped out of her fingers as he knelt in front of her, pulled away her jeans and got his first view of her beautiful and welcoming pussy. He slid the palm of his hand up the inside of her thigh as she flicked her jeans away with her foot, his fingertips not stopping as they pushed at the flesh of her mound. She was nicely trimmed, with her lips bare, wet and protruding. Adrian ’s hand pulled gently at her lips, bringing some pink into view and begging his tongue to taste her. It was impossible to resist.
He craned his neck to get the best angle into her while she lifted a leg for him. Molly’s breathing suddenly deepened as she felt the soft probing tip of his tongue push into her. He pulled her open wider and licked up and down her before plunging again, as deep as he could and pushing his nose into her clit. He reveled in all of her as he twisted and turned his tongue to taste her, smell her and make her wriggle with pleasure. “Oh God.” Molly moaned.
Adrian was enthusiastically continuing his job, reaching around with his free hand to push his fingers through the back of her thighs and tease her perineum. For several minutes, Molly could only encourage him by running her fingers through his hair. As she felt those deep familiar stirrings she could easily have simply stood there and let him make her cum, but she wasn’t about to waste the delectable-looking cock she knew was waiting for her.
“Lie down.” She pushed his head away gently. “I need to feel you inside me.”
Adrian quickly threw their clothes together on a rough blanket and lay back for her. Molly straddle him and looked down smiling, giving him the most wonderful view. “This has certainly turned out to be a more interesting afternoon than I was expecting.”
“Sure has.” Adrian agreed as she lowered herself to sit on his belly.
He felt the direct heat of her wet pussy as she squelched down on him and reached behind her back to take hold of him. As he looked up to her beautiful face it struck Adrian that he’d never been with any woman whose sexual pleasure was so evident on her face. It was an incredible turn on just to watch Molly in action, never mind experience her.
Molly shuffled herself down his body a little and allowed her knees to swing upwards, so she rested her feet on the ground, not her knees; as they would be in a “normal” straddling position. This allowed her to push up from him easily and pull his cock under her. Her hands were assured in their movement as she positioned him and her eyes didn’t leave his, seemingly enjoying the intense feelings she had stoked in him.
Without undue delay Molly guided the head of his cock to her slit, removed her hand and slid effortlessly down his pole, her sheath providing all the lubrication required. Adrian felt her warmth engulf and grip him wonderfully. His eyes closed as a wave of pleasure ran through his body. Molly smiled at the reaction, and then allowed her own eyes to close as she sighed at the sensations of him filling her up. “God, that feels good.” She whispered, as much to herself as to Adrian . She leaned forward and rested her hand gently on his chest, allowing her large round breast to swing down and towards him.
As she eased up and slid back down on him for the first time Adrian couldn’t resist bringing his hands up to cup her breasts and feel their considerable weight in his fingers. The sight of his thumb and forefinger pulling and twisting on her already hard nipples was almost as exciting as the feelings she was inducing in the rest of him as she worked her wonderfully tight pussy up and down his cock.
Molly sure knew what she was doing. Using her feet to move up and down on him meant that she was better able to pinch him inside her, making her feel tighter than any pussy he’d ever known. Each time she drew off him he felt his cock being pulled with her and each time she sunk back onto him she pushed hard, making him feel like he was deeper inside her than he ever thought possible. Still working her nipples in his fingers, he looked up to see the pleasure on her face as she licked her lips with a slow circle of her tongue and moaned unconsciously.
“Touch me.” Molly half-whispered, half-commanded.
Adrian reached under her dangling breasts and quickly found the top of her soaking pussy as it continued its slow rhythm of pleasure on him. As soon as he felt the swollen bud of her clit he knew why she needed him to touch her. Molly moaned louder now and managed to grind her clit on to his fingers as she rode him. Forgetting his own pleasure for just a moment, he was mesmerized as her breathing lost its regularity and the moaning got louder. She stopped breathing altogether and thrust down one final time before exhaling violently and letting her full weight collapse on him. “Oh fuck.” She panted as her pussy muscles contracted and relaxed repeatedly with the powerful climax. Adrian worked his fingers slow and firm against her as her body shuddered and then shivered, wringing ever last moment of pleasure for her he could.
When she opened her eyes she looked down at with a wild, fiery look that told him instantly that he wouldn’t need to ask if it was good for her.
It was no hardship for him as she lay on him and recovered, his cock still sheathed in her slick furnace and her gorgeous breasts pressing into his chest where she’d fallen on him. Adrian ran his hands all over her back and down to her ass cheeks, caressing and soothing her post-orgasmic bliss.
When Molly did recover, she was eager to make sure he got as good as she had. “Shall I kneel down for you?” She giggled as she kissed his mouth with a series of small pecks.
“Mmmm.” He approved, thinking of how it would look to see himself sinking into her. “I think I need to fuck you now.”
“Again?” Molly’s face recovered its impish grin as she slipped off him and waited for him to kneel up so she could assume her position for him. “Or did I just fuck you?”
The sight of Molly on all fours, offering up her pussy for his pleasure, was easily the most welcome thing Adrian ever saw. Giving himself a few gentle strokes while she got comfortable, he reached out and rubbed her still wet and heated pussy with his fingers. The sight of his fingers disappearing inside her turned his cock into a magnet attracted to her red hot sex and he eased himself towards its goal. Placing the head against its soft target, he used his hand to rub it up and down between her swollen lips. Adrian ’s eyes were glued to his own cock as he pushed gently and it disappeared under her ass and into her pussy.
No matter how much he wanted the moment to last forever, it was inevitable that he felt his body start to tingle with just the first few thrusts into her. Adrian reached forward with one hand and found her waving breast. Her nipple was hard and easy to find. He squeezed it between his fingers and felt her push extra hard back onto his cock. He sighed as the tension gently rose all over him, delighting in having Molly’s sexy body at his disposal and providing such pleasure.
As soon as Molly reached back and started to stroke his waving balls with her hand he knew there was no more holding back. Straightening up, he moved his hands to hold her hips and control the long thrusts he was relentlessly pounding her with. Molly glanced over her shoulder and smiled knowingly as she cupped him and pulled gently on his balls while he plunged in and out of her. He was staring straight into her eyes as his blood came to a boil and carried the rush of orgasm all through him. He closed his eyes and inclined his head backwards as the climax took control of his muscles and tightened them as spasms of pleasure began to pump cum from the balls Molly was pulling on exquisitely.
It was only after the fourth jet of cum shot into her that his breathing restarted; a gasp at first while Molly milked the final drops of cum from him and then deep, relieved, gulps of the fresh air. Molly was still looking over her shoulder at him, still loving every moment of the pleasure she’d created for him.
He held her loosely in his arms as they slumped and enjoyed the moments after their first coupling. Molly’s soft skin felt good next to his as the sheen of sweat that he’d generated started to cool down in the afternoon breeze.
“I suppose you’re going to want your underwear back now?” He let his hand caress her bottom gently while he spoke.
Molly was looking up through the branches and leaves of the tree they lay beneath and Adrian more felt her smile than he could see it. “I don’t think so.” She giggled. “You can keep them.”
“Thanks.” He laughed. “You can be sure I’ll enjoy them.”
“Anyway,” Molly continued, “I’m not expecting to need then for a while yet.” Her hand started to slide down his torso.
She turned over and raised her head over him so she could kiss him while her hand played with his soft but recovering cock. Breaking the kiss, she smiled down at him.
“What is it?” He asked.
“Oh, nothing.” She pulled a little harder as she felt the effects of her touch stiffen him. “I was just thinking how I really wasn’t looking forward to this afternoon.”
Adrian smiled back. “I dare you to keep doing that.”
She gave him an impish look that he was beginning to recognize. “Looks like you’re getting the hang of this game.”