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17
Her Date Night [F30s, M30s] [Long build up] [Seduction] [Wholesome]
Author Summary
EroticaByEmily is in Wholesome
Post Body

He had been watching her for half an hour. No, not watching. Studying her. Observing her. From the moment he'd first seen her standing at the bar, he had been cataloguing every detail and planning his approach.

She wouldn't be an easy catch, he knew. He'd already seen her politely but firmly turn down two others with their glib lines and offers of fresh drinks.

She was in her late 30s, or possibly well aged 40s. Her hair was freshly styled and her makeup painstakingly applied. That was enough to tell him she was here for a date. The way she kept looking at her phone and then to the door told him that the date was late or not coming, and hadn't bothered to let her know.

Every so often he saw her touch the middle finger of her left hand, as though playing with a ring that wasn't there. He ruled out an affair. People sneaking around didn't arrange to meet in such a public place, and certainly didn't leave the house dressed as she was. Recently divorced then? Her dress looked new, but it was a style that was a couple of seasons out of date. So she didn't get to wear it often. Could this be the first time she'd worn it since breaking up, and this her first date?

She had been nursing the same drink the whole time, and he saw the subtle signs that told him she was getting ready to leave. It was time for him to make his move. He stood, collecting the remnants of his own drink and walked slowly towards the bar, angling just past her. It was all about the timing now. She drained the last swallow, put her glass on the bar and turned to leave. Crashing into him and sending his glass to shatter on the floor. Exactly as planned.

"Oh my god! I'm so sorry!" she exclaimed.

He played his part well. "No, no, my fault entirely" he said, bending down to collect the shards of broken glass. Carefully he let one cut his finger. It was barely a pinprick, but by squeezing the skin around it he was able to get enough blood out to make it look worse. "Ouch!" He held the bloodied finger up as if inspecting it, making sure she had a clear view. "Oh! let me help you with that" she said. She rummaged in her purse and pulled out a tissue, and holding his hand steady she quickly wrapped it around his 'wound'. He noticed that she kept holding it for a little longer than she needed to. That was a good sign.

"Now I feel terrible. Let me get you a drink to make up for it?"

"if you insist" he said with a smile "but only if you're having one too"

"Well I was about to leave, but I don't suppose it would hurt"

With the drinks ordered, he led the way back to his table. He knew she would follow, it would be impolite for her not to, and he'd seen enough to know she wouldn't dream of doing anything that could be considered rude.

"So far, so good" he thought to himself. He was feeling quite smug. They'd interacted, she felt a measure of obligation towards him, and now he had her in the relative intimacy of his corner booth. It was a good start, now he just needed to build on it.

He was charming and witty and kept the conversation light, gauging her mood as she became more relaxed, laughing naturally at his jokes and starting to talk more about herself. Picking his moment carefully he said "I apologise if this is too forward of me, but I can't help noticing you're a bit overdressed for this place" She paused, and he held his breath, worried he'd moved too soon. She sighed, and he pretended not to notice the way her chest moved under the dress, then she admitted that she was there for a date, only her second since splitting with her ex.

"Do you want to tell me about it?" It was one of his favourite questions. In his experience they always wanted to talk about it. Even if 'it' was somewhat ambiguous, their subconscious turned it into something they wanted to talk about. With her, it was no different. She started speaking and it was if a dam had burst. Once she started, she didn't stop.

He heard all about her ex. How she'd caught him cheating, catching him in the act "with the cleaner of all people, but at least they used the spare bedroom". She told him about a disastrous double date her friend had set her up with, and that this was supposed to be her first real date on her own. He let her pour out all her anger and resentment. The worse these people looked, the better he seemed by comparison.

He steered the conversation to this evening's date with a carefully loaded question "so that guy who stood you up, what was he planning to do with you tonight?"

"Nothing too fancy, there's a Greek restaurant near here, we were just going to have dinner and see what happened"

He knew the place. Pretty quiet, not expensive and the food was good. "Well why don't we go there instead" he suggested. "You shouldn't miss out, just because he's an idiot" She laughed at that, and agreed it sounded like a great idea.

It was only a short walk, and they talked the whole way. He laid his hand lightly on the small of her back to steer her around a corner, resisting the urge to drop it lower to fondle her rounded ass. She was opening up to him, but it was still too soon for anything so direct.

There were plenty of tables available at the restaurant and they were soon seated. Together they scoured the menu, laughing as they each struggled to pronounce dishes. Since they couldn't decide what to have, they ended up ordering Meze, which was described as 'a selection of dishes from the menu'.

As the variety of dishes arrived, she leaned forward and in a loud whisper told him "I like to try new things sometimes" He recognised it for what it was, a bold attempt at flirting from someone who was a little out of practice, but he was too mesmerised by the amount of cleavage on display to think through his answer. "There's a couple of things on the table that look delicious" He hadn't meant to say it aloud and his heart raced as he lifted his eyes to her face. She looked down at herself and leant back in her seat, but then laughed, saying quietly "Maybe for dessert"

The meal ended all too soon. As they waited for the bill he asked "What would you like to do now? I could escorts you home if you'd like, or..." He hesitated, looking for a way to say what he wanted delicately. "Or what?" she prompted with a smile "or my hotel room has coffee in it. Probably" if in doubt, fall back on the clichés. She smiled and took hold of his hand. " 'Coffee' sounds delightful". He could practically hear the quote marks in her voice.

The taxi ride to his hotel was short but intense. They sat together in the back seat, holding hands, their thighs touching. Their whispered conversation was filled with innuendo and short laughs. Any pretence of being chaste was gone. They both knew what would happen once they arrived at the hotel, and this interlude only served to heighten the tension between them. They shared their first kiss of the night, a kiss full of restrained passions and promises of what was to come.

The door was barely closed before she pounced on him, her body pressed tightly against his, her hands clawing at his shirt and then ripping it open and sending buttons flying across the room. He was taken aback by the sudden ferocity but he quickly matched her, yanking down her dress to expose the milky white flesh of her breasts, barely restrained by her quarter cup bra.

His hands reached behind her, searching for the clasp. She pushed him away laughing as she unsnapped the front fastening and let the bra fall to reveal her large pink areolae and equally oversized nipples. He wasted no time dropping his lips to them, sucking each one into his mouth, swirling his tongue over and around the sensitive flesh. Her hand gripped his hair pulling him in closer as she let out a gentle moan.

She released him, pushing him back against the door and dropped to her knees in front of him. She had no difficulty in unbuttoning his trousers, letting them drop to his ankles, quickly followed by his briefs. His hard cock sprang out to meet her. She took it in her hand and let her tongue slide slowly up and down his thick shaft. As her tongue reached the head and tasted his salty pre-cum, it was his turn to gently moan with pleasure.

Her lips wrapped around him, her head bobbing as she started to suck him in earnest. Her hands stopped him thrusting into her - she wanted to set the pace - but he had no complaints as she worked him deeper into her throat with each movement of her head. Between moans he managed to urgently gasp out "stop!". He could feel himself close to cumming, and he didn't want the night to finish that quickly.

They paused long enough to finish undressing properly and he led her to the bed, gently but firmly pushing her down. "I think it's only fair that I have a turn" he said, kneeling beside her. He kissed her lips while his hands massaged her full breasts, his thumbs working over her nipples. With one hand still toying with her breast, he let the other glide slowly downwards, across her slightly rounded stomach, through the thatch of neatly trimmed hair, finding her wet core.

His fingers teased over her folds, sliding into her slit and penetrating her. She gasped as she felt his finger probing inside her, spreading her legs wider and lifting her hips. A second finger followed, pumping slowly in and out. He noticed how her breath quickened, her moans coming faster as he maintained his slow pace, curling his fingers to brush against her G Spot.

He kissed his way down her body, following the path his fingers had taken, before his tongue fluttered against her clit. The wetness of her pussy told him her moans were genuine. The movement of his fingers inside her sped up and he added a third. Her hips were rising and falling in time with his thrusts. He knew she was getting close now and just needed something to push her over the edge. He closed his lips around her swollen wet clit and sucked hard.

As her orgasm subsided, he sat up and withdrew his fingers, raising them to his mouth to lick them clean of her juices. She smiled up at him "Wow that was so good!" He lay down beside her, pulling one leg up to rest on his hip, her other leg sitting between his. With a slight change of angle, his cock was pressing against her wet lips. "Are you ready for more?" he asked. For an answer, she pushed back against him, the head slipping easily inside her.

They moved together, him thrusting forward as she pushed back, their combined efforts sending his cock deep into her pussy. He didn't know if he was fucking her, or if it was her fucking him, but it didn't really matter. They were fucking, and it felt good. She rolled onto her side, keeping him in her and he felt himself able to drive deeper, the entire length of his cock filling her with each thrust.

She was getting close again, he knew. Before she reached that point she drew away, pushing him over onto his back. She knelt astride him and took his cock back into her pussy. "I want you to cum with me" she growled as she started to ride him, her hands on his chest and fingernails digging in slightly. With each thrust of her hips, her breasts bounced in front of him. He reached up and gripped them tight, kneading the tender flesh as he lifted his hips to meet hers.

He felt her tense around his cock as her orgasm hit, her body arching backwards as she kept grinding on him. He'd been holding himself back, determined to make the night last, but feeling her squeezing around him was too much and he was cumming, shooting inside her over and over again.

She had just finished getting dressed after her shower and was fumbling in her purse. She pulled out her wedding ring and put it back on her finger. "you know you almost blew it, the amount of times I caught you staring at my tits" she said

He laughed "well can you blame me? You've got a great rack... For your age" She threw a fake punch at him as she laughed.

"Besides, do you know how hard it is to pick someone up in a bar?"

"It didn't seem so difficult to me" she replied. "Maybe next time you should try chatting me up then?" He said with a grin, putting his own ring back on.

"Me pick you up? Too easy!" she laughed again. "I'd just need to do this!" She lifted the clean t-shirt, flashing her breasts at him. He had to admit it, she had a point.

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6 months ago