A Lady's First Time

When he'd first stepped into the bathroom, it had been Daniel who had stared back at him in the mirror. Now, the face that smiled back was almost complete, and Cassie was nearly ready to go.

First had come all the undergarments -- the satin panties that felt oh so right, then the bra that had given the first hint of a bust line. Over that had come the girdle and then the bodysuit, aimed to turn a v-shaped physique into a more hourglass-like figure. Then the real fun had begun. The charcoal skirt came to mid thigh and slid easily over freshly shaved legs, smooth as silk, and the dark red cashmere sweater leant a softness to the strong upper body, disguising broad shoulders while accenting the cinched waistline.

Makeup was a breeze now, after having gotten professional assistance to learn the tricks of the trade, so base, blush, eyeliner, shadow, brow pencil, and mascara were flawless. Only two steps remained. The lipstick was a deep red to match the sweater, and the lips became an accessory unto themselves as the color coated them and showed them to their full pouty, heart-shaped advantage.

Finally, it was time for hair. Daniel's family and friends would have thought he'd lost his mind if he'd ever grown his hair out, even to shoulder length. It had never been his style. But it wasn't Daniel who would be going out tonight, and the wig would suffice -- auburn hair that flowed past the collar bone in waves, falling a few inches below the shoulders. It was a good wig, costly, and worth every penny. It looked real.

With the outfit complete and the makeup in place, Cassie came into being, and she smiled at herself again, pleased with the transformation that had been accomplished in such a short time. Low black heels completed the look, and Cassie flipped off the light and left the bathroom, collecting the makeup in one sweep of a hand, dumping it all into the knock-off Coach bag she'd bought just the other day with this date in mind.

As Daniel, he'd tried not to think too much about the plan for this Saturday night, feeling uncomfortable with it and not wanting it to interfere with his job. After all, they'd just broken ground on the new building a few days ago, and he needed his full concentration, with no distractions. But when Cassie came out to play every evening, she'd reveled in the thought of this, her first night with a man, something she'd desired for so long and had, until now, only dreamed of.

She frowned and stopped walking, needing to adjust her tuck job one more time before leaving the house. It wouldn't do if things were hanging out down there; she had to be ladylike. Satisfied and confident with the positioning of everything, she moved on, grabbing her keys from the hook by the door and checking herself one last time in the mirror in the entryway. Nodding with approval, she left the house, glad she lived away from the crowded suburbs so she didn't have to worry about neighbors seeing her.

As she drove to the restaurant -- a long drive, since she didn't want to be near her home base -- she considered the possible events of the evening with anticipation, nerves fluttering in her stomach. Adrian was a wonderful man, or so he seemed. She'd met him online three weeks ago, and they'd chatted for hours. They'd even had several phone calls now that had resulted in phone sex, and it made Cassie very happy to be able to make Adrian cum over the phone. But it hadn't been enough, not once they'd exchanged photos.

Adrian had been full of praise and admiration, telling her how beautiful she was, and it had made Cassie glow. His picture had made her mouth go dry as well. He was incredibly handsome, lightly tanned with light blue eyes surrounded by laugh lines, dark brown hair with the first touches of gray at the temples, and a body to die for with a solid chest, flat stomach, strong arms, and thick legs. It was the nude picture, though, that had really done her in. His cock was perfect, straight, tall, thick, and ready to go.

Cassie had dreamed of touching it, tasting it, feeling it in her ass, for several nights now, and her anxiousness had become almost too much to bear. She was so glad the time had finally arrived.

Still, she was concerned that something would go wrong, and she hesitated before getting out of the car at the restaurant, trying to convince herself to calm down. Finally, she stepped out and hurried toward the door, smiling at Adrian, who stood just inside, wearing khaki pants, a white button down, and a blue sport coat. He was classically handsome and greeted her with a kiss on the cheek before offering his arm and leading her to the table.

He was a real gentleman, and he complimented her several times during dinner. Cassie didn't eat much, too nervous with too much anticipation for what would come after to be able to finish even her small salad. Finally, dinner ended, and Adrian asked if she wanted to follow him back to his place. Did she ever! After a quick trip to the ladies' room to assure that everything was still tucked in place, Cassie followed Adrian to the parking lot and got in her car, following his Navigator through several lights and down several residential streets until he stopped in front of a modestly large house.

He helped her out of the car and took her hand, leading her up to the house. Cassie couldn't remember anyone ever having treated her like such a lady. It was all she'd wanted from the time she was just a young boy. Well, almost all she wanted, anyway, she thought as he opened the door and led her through the foyer into the living room. He offered her a glass of wine, but she declined, too excited to drink anything.

Adrian apparently sensed her eagerness, coming to her and wrapping his arms around her waist as he leaned in for the first real kiss. It was wonderful, feeling the strength of his lips against hers, tasting his tongue as it explored her mouth, feeling his hands roam over her back and then lower to grab her ass. She let out a little cry of surprise when he did that, smiling with pleasure.

He didn't speak as he took her hand and led her down a hallway and into his bedroom, stopping in front of the bed with a look of question in his eyes. Cassie just shook her head and reached out to him again, letting him know there was no need for hesitation. She was ready, and she wasn't shy. She moved into him, pressing her body against his, and she sighed when she felt a hardness beginning to grow between his legs pressing against her.

This time, she initiated the kiss, testing because she'd never kissed a man before, and she wanted to make sure she was doing it right. He seemed to be enjoying it, his hands landing on her shoulders and clinging. She took that as encouragement and grew bolder, stepping back a bit to make space between them without breaking the kiss. She reached into that space and felt for that hardness, the cock that was so excited, growing so large and erect inside his khakis.

Her eyes widened at the feel of it in her hand and the noise he made, a sort of strained groan that she thought was pleasure. Without hesitation, she reached for his fly, unzipping it and greedily plunging her hand into his jockeys. She wanted to feel the real thing, and her breath caught in her throat, ending the kiss, when her fingers closed over the warm hardness of it.

She simply held it for several long moments, feeling it grow, feeling the pulse throb within it, taking pleasure from his excitement, wonder filling her eyes as she looked up into his and saw the heat, the flame of desire there. When she spoke, she kept her voice soft, feminine, reminding herself that Cassie was, above all, a lady, no matter how much lust coursed through her system.

"I want it in my mouth."

Adrian's eyes widened for just a moment, then a salacious grin crossed his face, and he reached up with his fingertips to smooth them over her lips. "It's a beautiful mouth. I'd love to fill it."

His words were kind and gentle, and she adored it. Smoothing her skirt over her ass and the back of her thighs -- like a lady -- she knelt in front of him on the floor, watching as he pulled all that strong, masculine hardness out of his pants. It was impressive, long and hard, and for a moment, Cassie was daunted, wondering how she would go about getting all that cock in her mouth. Then, she set aside her worries and focused on the task with all her might.

She wrapped her hand around the base of him and squeezed gently as she wrapped her lips around the head of him and slid them down the length of his cock until they touched her hand. He moaned above her, and she cut her eyes up to his face to see his expression. His eyes were wild with passion, his face tense with desire, and it excited her beyond belief as she slid her mouth away from her hand and back over his head. She smiled at the bits of red lipstick smeared over him and reached her tongue out to lick it off.

He touched the top of her head with the barest whisper of his fingertips, and she could feel him caressing the wig. In that moment, she knew she wanted to grow her hair out, no matter what anyone thought or said, so she could feel him -- or others -- touch her own hair. The thought of the intimacy made her more eager, and she shoved his cock back in her mouth with greater fervor, bobbing up and down several times before letting the head slip out so she could run her tongue along the length of him, all the way back to the base where it met the rest of his body.

It was amazing to feel it in her mouth, the smooth, hot skin, the hardness of excitement, the occasional twitch when his control began to slip. She could have finished this right here and now, kept going until he came in her mouth so she could swallow all that wonderful, white fluid for the first time. But that wasn't what she wanted, not this time, and so she reluctantly pulled back, covering him with both her hands and caressing his cock gently between them.

Again, she spoke with a soft, higher pitched voice that she'd been practicing for weeks. "I want you inside me."

Adrian's lips were slightly parted, and his eyes were unfocused. His breathing was labored, coming in short gasps, and his hands were clenched into fists at his sides. He took a moment to sort of shake himself and bring himself back to reality, and he looked down at Cassie. "I can't wait to be inside that sweet ass of yours."

As if to punctuate his words, he reached down, pulling her to her feet, and grabbed her ass with both hands, squeezing hard as he crushed his lips against hers. Oh yes! a voice inside her head screamed. This is what she'd fantasized for years, since she'd first seen her older sister kiss a boy. She'd wanted to do it, too, to get lost in that intimate contact, and what would follow. This was her dream.

Still holding her by her arms, Adrian turned her to face the bed. He placed one hand on her back and began to push, bending her over so her feet were on the floor and she had to brace her arms on the mattress. She felt the excitement build almost to the point of explosion as he pushed her skirt up around her waist and reached between her legs to unsnap the crotch of her bodysuit. A wave of nerves flooded her briefly, still a bit unsure of the logistics of how this was going to work, but she put it out of her mind, telling herself she'd figure it out and make it work.

With the bodysuit unsnapped, Adrian tugged on the girdle and panties, and Cassie reached back to help him. As the panties slid down, she came untucked and had a brief moment of panic, then reached around to cup herself and hold herself out of the way. There, that worked.

Before she even had time to process the thought, Adrian's hands closed over her bare ass cheeks, squeezing again, then pulling them apart to spread her open for him. "So beautiful," he whispered, and a thrill of pleasure ran down Cassie's spine, making her shiver with delight. Then, the tip of his cock touched her, just a brush as he tried to position himself to enter her, and a whimper escaped her lips, a cry of ecstasy and disbelief rolled together.

She couldn't believe this was going to happen for her, and she was so anxious, so full of need that it almost hurt. Finally, Adrian seemed to be pleased with his position and pushed against her, entering just the very tip of his head into her, bringing a gasp to her lips and a moan to his. "So tight," he commented as he pushed a little harder, a little further.

The feel of him inside her ass, even just this much, was incredible, like nothing she'd ever felt before. Sure, she'd played with vibrators for years, trying to achieve satisfaction and preparing for the day that this fantasy might come to fruition, but it wasn't the same. This was so very much better, so much sweeter, and though she wanted to be patient, she found herself wiggling, trying to push herself against him so that his cock would slide deeper inside, faster.

"Patience, honey, you're so tight it's going to take a few tries," he cautioned in a quiet, soothing voice. Honey, he called her, and that sent her through the roof with happiness. She stilled for him, waiting as patiently as she could as he eased himself back out and then started again, making it maybe half an inch deeper this time. He repeated the motion over and over, and each time, there was a slight discomfort, followed by a glorious wave of pleasure.

Cassie began to moan, and the moans turned to words. "Yes," and "just like that" and "oh, God!" And then, somehow she knew, he was almost in all the way. She'd felt every inch of that cock work to gain its space, and now she couldn't wait anymore to finish it. She wanted every last bit of it inside her now. As he slid out one more time, she reached back to stop him, with his head still buried inside her ass.

"Adrian," she moaned, stopping him, and he froze. Her voice was breathy, and she could feel him tense. That made her smile, and she turned her face to the side so she could cut her eyes back at him as she said, "Finish it. Take it all the way. I need it."

She felt a shudder go through his whole body and writhed a bit as that shiver continued through his cock still partially inside her. He reached down to her and smoothed his hands over her ass, cupping it lovingly, gently, caressing it. "So beautiful," he repeated, and he placed his hands on either side of her hips.

She knew what would come next, and she braced herself, one hand pressed firmly on the bed in front of her, the other cupping herself to make sure that nothing fell in the way. His grip on her hips tightened, becoming almost painful, and she took a deep breath, then screamed with a mixture of agony and ecstasy as he shoved himself all the way inside her ass. The sensation was amazing, and her whole body went slightly limp for just a moment.

His seemed to do the same above her, then his hands grew firm again, and he began to move in and out, rougher now, the front of his groin slapping against her ass as he buried his cock deep inside her over and over again. It felt wonderful, better than she could ever have imagined, and his grunts of pleasure echoed her moans and whimpers as he moved in and out of her.

He moved faster and faster, and she prepared herself, thinking he was getting ready to come, but then he stopped, pulling out completely, and one hand smacked her ass cheek. She turned her head as far around as she could without getting up, looking over her shoulder at him.

"Turn over on your back," he said, his voice gruff. She didn't hesitate; above all else, Cassie wanted to please this man who was making her feel so wonderful. She took a moment to try to decide what to do with the parts of her anatomy that didn't belong but decided she could treat it all the same way on her back as she had on her stomach.

As she lay back, she cupped the limp bits of herself and pulled them up out of the way, covering them with her hand. Adrian moved up so his knees were braced against the mattress, and he bent down to grab her ankles. He pushed her legs back so that her knees were almost in her face, then raised her ankles so they rested on his shoulders, her legs high in the air. It was an unfamiliar position, but it helped her hide the parts that didn't need to be there and gave him easy access to her ass.

She looked down at his cock again before he entered her, and had a moment to wonder that something so large and perfect had been inside her, was going to be inside her again, and she was ready when he pressed into her, not taking his time to ease in bit by bit again. It wasn't necessary; the lubrication was still there, and Cassie had already been prepared.

The different angle caused a different sensation, and Cassie closed her eyes as Adrian took on a new rhythm, buried deeper and not pulling out as far with each thrust, making the movements small but deep rather than shallow. It felt incredible, and it made it easy for Adrian to move faster, pound harder, without giving time for recovery between each thrust. He meant to drive her crazy, Cassie thought, and then realized that he was beginning to lose his careful rhythm.

He was almost done, she thought, and a small wave of disappointment threatened to ruin her mood. Then, he leaned forward, placing his hands on the edge of the bed to brace himself. That folded her legs backward just a bit, and it changed the angle of his thrusts just enough to make Cassie scream with pleasure at the new feeling. He gained momentum again, rocking hard and fast, almost to the point that it hurt, but that only served to heighten Cassie's pleasure.

Between her legs, she looked up at Adrian's face, and his eyes, which had been closed, popped open, meeting her gaze and holding it as he kept pounding his cock into her ass. She felt like smiling, but she couldn't seem to move her lips or anything else for that matter, lost in the feel of him inside her.

His body began to have small shockwaves rock through it, barely visible, but Cassie could feel them, and she reached for his hands where they rested on the bed, moving them to her hips, one at a time, never releasing her hold on the things she wanted out of the way.

When both his hands were on her, he added even more force to his thrusts, and Cassie felt as though his cock was touching places inside she hadn't thought it was possible to reach. Suddenly, his whole body shuddered with the force of an earthquake, and she could feel cum, hot and wet, spill inside her, squirting over and over, and she gasped at the way it slid into her, filled her ass. She loved it, more than she could ever have believed, and she closed her eyes, soft cries escaping her lips as Adrian convulsed over her, his cock spasming inside her as he finished spilling himself.

Finally, he pulled out of her, collapsing onto the bed next to her. She lay there next to him for several moments, and he didn't move. Then, he rolled to his side and leaned in to kiss her, gently, chastely on the lips. She smiled and excused herself, ready to go into the restroom and clean up.

Inside, she wiped everything down from between her legs, removing all the sticky liquid that had leaked out of her ass where he had come, then pulling up her panties and girdle, retucking everything properly. She snapped her bodysuit back into place, touched up her lipstick, and returned to the bedroom to find that Adrian had simply pulled his pants back up and zipped them shut.

It was time to go home, and that was disappointing, but nothing about the night had been a disappointment, so she smiled and said goodnight. He kissed her at the door, told her what a wonderful time he'd had, and tucked her hair behind one ear, away from her face, so he could caress her cheek. "You are a beautiful woman, Cassie, and I hope we can get together again soon."

Cassie nodded eagerly and smiled brilliantly at him, so glad that he could look at her with such adoration in his eyes. "I would love that." She turned to leave, slid into her car, turned the engine over, and pulled away from the house.