When Harry Met Sally - First Date Sex
Sally sat nervously at the bar in her black satin midi dress, her heart racing as she waited for Harry to arrive. She had been looking forward to this date for weeks, but now that it was finally here, she couldn't help but feel a little bit nervous.
After matching with Harry on one of her dating apps, they’d seemed to hit it off rather quickly, and found many common topics to talk about, such as their interests in hiking, reading, and craft beer. Granted, those weren’t obscure hobbies, but the additional pro of chatting with Harry was that he seemed interested even in hobbies that they didn’t have in common, and would also respond thoughtfully to her texts.
If a picture paints a thousand words, then that’s about 5,000 words to say that the man was smoking hot. If he isn’t a catfish, Sally added mirthfully in her head.
As the server set a glass of water down for her, Sally spotted Harry approaching her table. Okay then, so not a catfish. Harry had the classic smoldering and mysterious look (Sally’s ideal type) mixed in with a subtle hint of intelligence in his wire-framed glasses that only added to his appeal.
As he leaned over to give her a hug, Harry said in a low voice, “You… look just as cute as I thought you’d be.”
“You’re doing pretty well yourself. Just as advertised in that beach pic of yours,” she replied with a quick wink. Of course she had to make a reference to that topless photo of Harry by the beach.
Harry laughed and shrugged, looking almost shy. “I guess we already make an attractive pair, huh?”
Sally could not help but grin. Her gaze met his and in that moment, Sally had a good feeling that tonight would go well.
Minutes passed like seconds and Sally found herself feeling more and more relaxed. She was certain that it had nothing to do with the craft beer that she and Harry were sampling. Seasoned bar hoppers, they were both pretty much still sober, and Sally thought it was better this way as they could really enjoy each other’s presence.
Harry had a way of making her feel comfortable, and before she knew it, they were talking about everything and anything, from their families, to work and even date experiences.
“What’s the worst date you’ve been on? ” Sally asked curiously.
“There was this once where my date bailed midway and left me with a $300 bill to foot on my own. That was not fun for my wallet.”
“Well, I can assure you, this date is going too well for me to wanna bail, and,” her voice lowered as she leaned in, lips beside his ear, “we’re going dutch, baby.”
She leaned back, both of them bursting into laughter at her joke.
“Now, Sally, that’s the hottest thing anyone’s ever said to me.”
Sally couldn't ignore the flirting. She’d been on multiple first dates that have ranged from neutral to terrible, with some positive experiences, but this one with Harry was by far a standout. He would lean in close to her when he spoke, and she couldn't help but playfully touch his arm or lean in to whisper something in his ear.
Each time they touched, she felt a tiny shiver run down her spine. She knew Harry felt the same way; she could see it in his eyes when he looked at her. She’d already caught his eyes running down the length of her body more than once.
Their chemistry was undeniable, and Sally didn’t want the night to end so soon. She wondered if he felt the same. As his fingers grazed her arm again, she felt sure he did.
Before they knew it, the bar was taking last orders. Sally knew she had to make a move first. Taking a breath, she asked, “You know, the night’s still young. Wanna head over to my place for a nightcap?”
Harry took her hand in his, his thumb tracing soft circles on the back of her palm. “Of course, I’d love that.”
On the cab ride back, the pair fell into a comfortable silence, though the air was thick with sexual tension. Sally ran her fingers slowly along the length of Harry’s clothed thigh, almost teasingly. In response, Harry tightened his grip on Sally’s thigh, fingertips digging slightly into the soft flesh as he glanced sideways at her. Harry’s eyes were clearly glazed with lust.
Thankfully, the cab ride was a short one. As they stepped into the elevator to head to Sally’s apartment, Harry placed his hands on Sally’s shoulders, gently nudging her against the wall. Just like the movies, Sally thought as he bent down to leave a trail of kisses along her jawline. Her eyes shut briefly as she soaked in the sensations, each kiss making her tingle with excitement.
It took Sally all her willpower not to start undressing Harry there and then. Her heart fluttered with excitement as she led him to her apartment. Once the door was shut and locked behind them, it was her turn to pin him to the wall.
“Ooh, you’re a strong one.” Harry remarked with a grin.
Chuckling in return, Sally leaned up, joining her lips to his in a fiery kiss. Harry parted his lips readily as Sally squeezed his hips, rolling hers against his in encouragement. Their tongues danced together, swirling around each other as Harry and Sally drank in each other’s desperate gasps and moans.
The grinding and French kissing combined aroused them both to no end. Within seconds, Harry was the first to pull back. With a deft movement, he grabbed Sally’s arm and walked into the living room, guiding her firmly to sit on the couch.
Harry himself positioned himself in front of Sally on the floor, fingertips trailing up each leg. When they met the hem of her dress, Harry pushed it up in a slow motion till Sally’s milky thighs and pelvis were exposed.
“May I?” He asked, as a finger tucked itself around the waistband of Sally’s black lace panties.
As soon as Sally nodded, Harry tugged her panties down, exposing her completely to him. She was, as expected, soaking wet. Harry felt himself getting harder by the second, though he wanted to focus on her pleasure now.
With his arms tucked around Sally’s legs he pulled her hips closer to his face, so close he could smell her sweet arousal. Wasting no time, he pushed his face between her legs, his tongue beginning to search for her clit. His fingers parted and teased her wet folds as his tongue swirled around her clit mercilessly.
Sally’s mewls of delight spurred him on. Her right hand found its way to Harry’s head to hold him in place. Her head tossed back in pleasure, she cupped her breast with her free hand, fingers teasing her nipples through her dress. Every now and then Harry glanced up at Sally. The sight of her coming undone was such a turn on. Harry quickened his ministrations, his tongue flicking more rapidly in pace with Sally’s gasps.
Soon, he felt her tense up as though she was about to climax, leading him to pull away.
“Not so fast, missy.”
She growled in mock frustration, but like Harry, she knew how she wanted the night to end. As Harry undressed and put on a condom – where did that even come from, she wondered – Sally wriggled out of her slip.
Pushing him down on the couch, she climbed on top of him, straddling his hips and grinding against the length of his cock. He was pretty well-endowed, and she could tell that he’d feel so good inside her.
As her lips met his for another kiss, she sank herself down on his erection. The way he filled her up perfectly made her moan. Even the angle at which they were fucking felt magical to her. As he thrust his hips up to meet her, the head of Harry’s cock continued pressing all the right spots inside Sally.
She positioned her hands on Harry’s chest for balance, but each movement seemed to inch her closer to orgasm, and her nails began digging slightly into his muscular pecs. Rocking her hips back and forth, Sally felt herself melting right into the heat and their combined desire. Every thrust seemed to hit her G-spot, and she was dizzy with ecstasy.
“Fuck, Harry, there.” As she edged closer to her climax, Harry felt Sally’s inner walls contracting erratically around his hard length. He was giving her just what she wanted, where she wanted it, and knowing she was close drove him mad with lust.
As they synced their movements and tightened their arms around each other, both of them came loudly, their hips coming to a still as their orgasms washed over them. In its wake, Sally rested her head on Harry’s chest, letting her breath slow down gradually. It was still kind of sweet (and hot) that neither of them had pulled away, that they were still connected.
Harry patted Sally’s bare ass playfully.
“So I guess this means we’re on for a second date?”
Sally lifted her head and rolled her eyes at him.
“Of course, smart ass.”