How well Jacob and Emily's Third Date go?

Jacob looked for what felt like the hundredth time in the mirror. He wanted to look good, but not stiff. He was wearing a grey sport coat and pants, with a white button up underneath.

Was the jacket too much? Too late, the Uber had arrived. He combed his hair back one last time and headed out of his second-floor apartment to the street, getting into the back seat of the Civic.

He fidgeted with the hem of his jacket as the driver pulled out into traffic. Jacob felt a trickle of sweat run down his back.

C’mon you got this. She really likes you, and she’s so fuckin cute.

He checked his phone for last minute messages. Nothing.

She’s not going to cancel; she wants to be with me. Just got to be casual, and chill and it’ll be cool.

Jacob tried to relax. He thought about their last date. He thought about sitting on the park bench with Emily at the end of their last date, the warm evening sun on his skin, making her auburn hair shimmer. He thought about when they kissed, their tongues swirling together, her hands wrapped around his neck, and his on her thigh. The way his hand brushed her breast.

Fuck, be chill Jacob. What’s it been? Six months since Samatha?

He shifted uncomfortably in the seat, then he checked his jacket pocket for the condoms he already knew were in there.

Chill. You’re here, act normal. Don’t expect anything.

The cab pulled up and Jacob exited, thanking the driver as he stepped out. Walking past the full patio, Jacob entered the restaurant.

“Hi there, welcome, would you like a table?” Asked the hostess when Jacob walks in

“I have a reservation actually, in ten minutes, I’m a bit early… For Jacob, it’s uh, at seven,”

“Ah I have you here, for two, perfect, right this way,” she says, leading him to a table. He sat facing the entrance of the restaurant.

He waited, checking his phone again, no messages, ten minutes early, as intended.

“I there, my name is Brad, I’ll be your server today. I see you are still waiting for your guest; would you like me to get you a drink?” asked the waiter.

“Sure, I’ll have a scotch on rocks and when my guest comes in, please bring her a gin and tonic.”

“Absolutely sir,” said the waiter, walking away.

Remembering her drink is a classy move, now chill.

He had just got his drink when he saw Emily walk in the restaurant, stopping briefly to talk to the hostess. He rose to greet her, and she waved and headed to the table.

Her blonde hair trailed long down her shoulders, shining in the dim lighting of the restaurant. Her red knee-length cocktail dress swirled as she walked, with a light and bubbly stride. She carried a little black purse on a wristlet.

She’s so cute goddamn. Chill.

“Hi Jacob,” she exclaimed, walking over to hug him. “You look great!”

Her hug was tight. She smelled like lavender and a perfume he remembered from last time. As he embraced her, he felt her breasts press up against his chest. Her hand lingered on his hip.

“You uh, you look beautiful Emily,” he said as they broke their hug. She responded by giving him a quick kiss, almost out of nowhere, before sitting with a giggle.

I hope she didn’t notice my hand shaking.

“A gin and tonic for the lady,” said the waiter with her drink, “I’ll give you some time with the menus.”

“I hope you don’t mind, I um ordered you a drink. I remembered you liked G and T...” He said, stuttering somewhat.

Was that a mistake? I don’t want to seem like I’m getting her drunk. Shit.

“That’s so nice, thank you,” she said, taking a sip.

“So uh, how are you?” Jacob asked.

“I’m great, really excited to see you Jake,” she said.

Jake? Ugh, lucky she’s so hot. Fuckin hate “Jake.”

“Me too. Uh to see you I mean, haha.” He responded, forcing a laugh. Emily ignored, or at least pretended not to notice his awkwardness.

The conversation and dinner were pleasant. Jacob, in spite of his nervousness, found talking to Emily easy, like they’d known each other for ages. They ordered some glasses of wine to go with their dinners, enjoying the romantic ambiance.

At one point they overheard the dad of a married couple with kids tell off some drunk people behind him. Emily made a scandalized face to Jacob.

“Someone’s in trouble,” she whispered with a smile, making Jacob laugh through a mouthful of chicken.

Jacob felt like dinner was going well. He wasn’t as chatty as he’d like, he was never good at small talk, but Emily was happy to steer the conversation at times. She was bubbly, confident and light.

What does this chick see in me? Whatever, just be glad she does.

They ordered a double fudge cheesecake slice for dessert. While they waited, Jacob saw her hand on the table and reached out taking it in his. Her hands were small, soft. She squeezed his hand back, smiling. He felt her leg slide over to his, her bare calf running up the side of his pants.

“O-M-G, this looks so good Jake,” she said, as the cheesecake arrived. She took a bite and sighed with delight.

“I guess so eh?” said Jacob, enjoying seeing her enjoy the cake so much he barely noticed the ‘Jake’ that time. Feeling confident, he continued, “Is it a ‘better than sex’ cake or a regular one?”

Ugh why Jacob why? You were on a roll, that was terrible.

“Well… it’s pretty good cake…” laughed Emily, not missing a beat. “I guess it depends on the sex,” she added with a smirk, looking right at Jacob.

This was the first time, besides their making out session last time, that she had been so overtly sexual with him. Her leg travelled moved a little more under the table against his.

They enjoyed the cake and flirted. When the waiter came by Jacob took care of the bill before Emily could say anything.

“Aw thanks Jacob. You don’t have to dote on me you know, I don’t mind splitting bills.”

“No it’s fine… It’s worth it to enjoy your company,” he said, pausing for an awkward dramatic effect. She giggled, reaching out to touch his hand.

I’d do anything for that laugh. She’s so great.

“So uh, Emily, want to split and Uber? My place is on the way to yours, right? We could like, hang out or something.” Jacob could feel his hands shaking.

Smooth Jacob, real smooth.

“I’d love to,” Emily responded quickly. She took his hand in both of hers, “are you ready to go?”

“Yes, um yes,” responded Jacob, standing awkwardly fast, something Emily noticed, but didn’t comment on.

At least she’s still smiling.

Emily stood up and grabbed her purse from the seat next to her. Moving over to Jacob’s side of the table, she said, “let’s go,” and gave him a quick, kiss on the lips, then she giggled seeing his somewhat surprised expression.

As they walked out, hand in hand, Jacob fumbled with his phone to punch in the Uber order. He entered his address as they stepped out into the warm evening.

Don’t assume don’t assume don’t assume.

“I, um, do you want me to put in a second stop or…?” he asked, his heart in his throat.

Emily didn’t respond immediately. She moved closer to him, threw both arms behind his neck, and started to kiss him, pulling herself against his body.

“One’s good Jake,” she whispered between kisses.

He frantically tapped on the screen to order the Uber, which, mercifully, wasn’t too far from the restaurant. As soon as it was ordered, he pulled her in by the waste and kissed her deeply, exploring her mouth with his tongue.

Her mouth was warm, and insistent. Her breath smelled like cake and wine. They were so preoccupied with each other they didn’t notice the Uber until the notification pinged in his pocket.

Jacob held the door for Emily as she got in, taking the opportunity to eye up her cute little ass in her dress. He barely had the door closed before she was pulling him into another kiss. As the Uber drove and streetlights flashed across her, he could see a warm flush on Emily’s face.

His hand on her waist moved up to her ribs, subtly brushing against her breast. She moved his arm back down a little without breaking the kiss.

Too fast, too far Jacob, chill.

“Have fun you two,” said the Uber driver with a smirk as they arrived at their destination. The two thanked him for the ride and got out of the car.

They kissed again outside the apartment, this time much more vigorously than before. Emily’s hands wandered to Jacob’s ass and pulled him in to each kiss.

“Take me upstairs Jake,” she whispered in his ear. His neck hairs stood on end when she said it, her warm breath on him. His hands began to shake.

“Right this way…” he said, awkwardly, motioning her to the door.

Right this way? Bruhhh.

He unlocked his door and invited her inside. The apartment was small, but tidy. He’d planned it that way, he figured no chicks like a dirty apartment, so he straightened it out before the date.

Thank God I don’t have roommates. OK, no pressure no pressure.

“Hey, would you like something to drink, tea? Or…” He didn’t finish his thought. Emily was in front of him, pulling him into a kiss.

She stopped kissing him just long enough to say no, before sliding her tongue in his mouth. He could feel an erection growing in his pants.

“Take me to the bedroom Jake,” she whispered, her voice pure sex.

They burst into the bedroom, kissing as they did. She started unbuttoning his sport coat, sliding it off of him. Then she started working on his shirt buttons, exposing his bare chest. As he stripped it off, she backed up enough to let him watch her unbutton and slide the cocktail dress of her shoulders, down to the floor, where it landed in a pile.

Holy shit she’s gorgeous.

She stood there in nothing but black lingerie. Her slim figure pale in the dim light of the bedroom. She walked slowly back over to him, accentuating the sway of her hips as she did. Wordlessly, she started undoing Jacob’s belt, kissing him a little as she worked the fly. Her warm hand on his stiff boxer clad cock felt amazing.

He started trying to undo her bra, clumsily. She giggled a little and stepped back, undoing it herself and letting it drop to the floor.

Oh my god it’s happening. She’s so fucking hot.

Her tits were round and perky, with erect light-coloured nipples. She rubbed them slowly for his benefit. She started pushing his pants down, brushing her nipples against his chest hairs as she did, making him shudder with anticipation.

“I want you Jake,” she whispered into his ear before backing over to the bed. She hooked the strap of her black underwear with her fingers and pulled them down to reveal her smooth, shaved pussy.

He knelt on the bed, leaning over Emily, partially to kiss her, but also to reach for his sport coat. As he pulled the condom out of his jacket, Emily worked the boxers he was wearing down, making his hard cock spring out.

“Hmmmmhm, nice,” she hummed as she started to stroke him, smearing a dab of pre-cum around his cock. His hands were shaking as he pulled the condom out of the wrapper.

“I want you inside me Jake, I want you so bad,” she moaned, laying back on the bed.

Jake pulled the condom onto his erect cock and took a second to admire the view. Emily was laying there, hips gyrating slightly, a hand on her left breast, pinching her nipple, her other gently teasing her pussy, which shined with her wetness.

She moaned as her fingers explored her pussy lips, “mmhm, make love to me Jacob, I want you so bad,” she sighed, opening her legs for him as he climbed between.

“Are you ready?” he asked poised. She took his penis in her hand and guided it inside herself as an answer. Tilting her head back with pleasure as he pushed into her slick entrance.

“Ohhhh yeah Jacob, nice and slow for me baby,” she moaned. Emily was so warm and tight, with each thrust, she moaned and pushed against him, pushing him deeper than the time before.

Jacob leaned back so he could admire the view, and slow down; he wanted this to last. He thrust slowly, watching his cock slide into her, then pull most of the way out, seeing her juices left on the condom. Each thrust caused an ‘ah’ of pleasure to escape her lips. Each, slightly louder, longer, and more insistent than the last.

“Oh god Jake, oh god it’s so… it’s so ahhh good,” she cried out, digging her nails into the skin of his back, pulling him into her as he thrust. He was getting close now, he could feel the pressure building inside him. His heart was pounding in his chest.

Emily wrapped her legs around him, pulling him deeper inside her.

“I think I’m gonna, oh GOD yes Jake I think I’m gonna cum,” she moaned, “ahhh, oh god Jake cum with m-eeeahhh.” Each thrust she pulled him deeper; her nails dug a little deeper into his back. The walls of her pussy clamped down in pleasure on his shaft.

“Ah fuuuck yeah,” he grunted out, feeling himself twitch inside her and fill the condom.

“Yesyesyes baby ahhhh,” screamed Emily under him, staring up at him as their shared orgasms swept though them both.

Jacob kept thrusting, unwilling to pull out of her sweet little pussy until he couldn’t keep going anymore. He collapsed down on her and she wrapped her arms around his neck and kissed him, holding him inside her still.

I never want this feeling to stop.

“That was wonderful Jacob,” Emily sighed as he slid out of her and into the bed beside her. He popped the and disposed of the condom in the wastebasket, then rolling back over to her. He admired the naked woman in his bed, flushed, happy and wet, staring at him with a blissful expression of after-glow.

Well done buddy.