A Romp in the City

Kate and Isla were on a girl's trip to New York City and after a few hours of wandering around the cold, windy city and a few stops into whatever bar looked appealing on their haphazard route, they ended up at a wine tasting in Chelsea. After their five glass tasting, they decided to venture to a different bar within the same massive winery. Kate sidled up to the bar - this one with a view of the Hudson, taking in her new surroundings, squinting and maybe stumbling a bit as she did. She turned to her friend saying "the bartender is cute." She couldn't help herself and didn't care if he heard.

He was cute, but certainly not the type she normally went for - slighter than the sturdy men she typically liked with one ear full of earrings and a mop of messy dirty blonde hair on his head, not to mention she could tell there were multiple tattoos under that black button down.

She put on her flirtiest smile and grabbed a stemless wine glass on the bar within reach that contained the lids to lots of pretty liquor bottles. "This lid is pretty." "It goes to a bottle of elderberry liqueur. Would you like a sample?" "Of course," she said. "I'm Kate." "Gabriel." the cute bartender said with a smile that reached his hazel eyes.

Next thing she knew, Kate and Isla had spent all afternoon sitting at Gabriel's bar, drinking everything from Cabernet to shots of well tequila to fancy elderberry and whatever cocktails. After getting up at 3:45 am for a 6:30 flight to New York, Kate realized she hadn't eaten anything since half a bagel from an airport Starbucks at 5 am. Isla wisely ordered them a pizza, likely realizing the same thing Kate did.

The afternoon continued to pass in a blur. After some liquid courage, she asked Gabriel where the sexiest places in New York City were. What she meant by that, she had no idea. All she knew was that she needed some fun - whether that was watching or participating. She also knew there was a huge kink community in NYC. With a wink and a grin, he told her about a bar in Brooklyn where patrons could really let loose. It became clear to her that this guy was a little kinky, but she wasn't exactly sure what his preference might be - men, women or both. He did give her his phone number, but that didn't necessarily mean he was interested.

Eventually Kate and Isla left, promising to reach out later in the night. They headed to finally check into their cracker box sized hotel room located close to Times Square. "Fuck," Kate thought. "I should have booked us a room at a boutique hotel in SoHo." They were both exhausted and it was barely 8 pm. They decided on grabbing burgers at the Shake Shack around the corner and calling it an early night - vowing to take NYC by storm tomorrow.

Kate woke up early the next morning with a horrible headache. She checked her phone and realized at some point she texted Gabriel. She must have fallen asleep before he responded when he got off around 11. She also texted one of her guy friends back home in Cincinnati that she "freed the nipple" at Shake Shack. She cringed reading that very weird text. "This is why one should never look back at drunken messages." she thought.

Once Isla started showing signs of life, they both got ready and headed out for the day. They took an Uber to lower Manhattan and hit all of the tourist destinations. Kate had been to NYC a few times, but Isla hadn't, so she was just going with the flow, open to where the day/night took them. At some point she texted Gabriel again- playing it off like she was continuing their conversation from last night. He was working until 11 again that night, but was game to meet after. Typically, she would never have considered meeting anyone that late, but they were in the city that never slept after all.

After accidentally flirting themselves into an uncomfortable situation with a few waiters in Little Italy, Kate and Isla decided to take an Uber to Brooklyn and wait for Gabriel to get off on his side of the East River. He said he'd be back that way eventually after having a drink with a few friends. As she was sitting at a dive bar in Williamsburg, Kate started having second thoughts. She was tired anyway and Isla was clearly really drunk after all those free drinks in Little Italy. She turned her phone off and threw it in her purse, determined to ghost Gabriel. Isla went to the bathroom and when she returned, Kate was going to suggest they go back to their hotel, or at least to Manhattan.

Before Isla got back though, Gabriel walked in the front door of the mostly empty bar. There was nowhere to hide as Kate realized she told him what bar they were at an hour ago. She tried to play it cool, like she wasn't totally ignoring him. He was wearing all black and rocking a crossbody aka a fanny pack. She shook her head and laughed. Definitely not her type, but it was a look that worked for him, plus he smelled amazing- like cashmere, cedar and fresh rain.

Isla came back from the bathroom, raising her eyebrow in Kate's direction as she took a seat on the other side of Gabriel. He ordered them a round of drinks - an espresso martini for Isla, a Jack and ginger for himself and a vodka seltzer that tasted like Pine Sol for Kate. After a few more rounds, somehow the topic of sex came up- like it normally does when two people who are attracted to each other are drunk. He told her he was a pleasure dom. His goal in every sexual encounter was always to pleasure his partners. She knew what a dom was of course. Kate was a dominant person by nature, but she loved to submit in the bedroom. He asked her what she was into, but even knowing he was kinky, she was afraid to tell him. How do you tell a stranger you want to be fucked in public, double penetrated by two men at once or held as a sexual slave by a sadistic lesbian? Instead she managed to slur that she had recently gotten a Brazilian wax. At that, he leaned in and kissed her - hard. What. The. Fuck.

This stranger stuck his tongue down her throat in a dive bar in Brooklyn. And she didn't stop him. Isla winked and made herself scarce. So they just kept kissing.

It was clear that he was as intoxicated as she was - luckily. She could spin this the next day as a silly mistake. The three of them relocated to a different bar and she immediately went into the bathroom. When she came out, there he was pushing her back in. Thank god for complicated (but sexy) bodysuits and being on her period, because if not, she would have let him fuck her right there- risking a disease that you probably can only get from a dive bar toilet. Because of this, she refrained from reaching between his legs and seeing what he was working with- part of her was afraid of what she would find anyway.

"You have a fantastic ass, and you're a phenomenal kisser." Gabriel told her. She snorted in response. "Clearly you don't know how to take a compliment."

It's not that she didn't know how to take a compliment, but it felt weird being complimented by a stranger, one who she also learned was more than a few years younger than her. At 33, Kate had a few wrinkles between her eyes and needed to lose 15 pounds (in her opinion), but she knew despite those things, with her bright blonde hair that fell slightly below her shoulders, aquamarine eyes, straight white smile, huge tits and charming personality, she was still hot AF.

She had no idea where Isla was, but looked at her phone, which at some point she had turned back on and noticed it was 3:45. In the morning. "Fuck we have to get out of here." she thought through a haze. Meanwhile, Gabriel kept kissing her.

Eventually she got them both out the door and ushered Isla into an Uber, giving Gabriel one last kiss. She fell asleep realizing they never made it to the kinky bar.

Kate woke at 9 am feeling absolutely terrible. She laid in bed until 11, when she had to check her and Isla into their flight home for the next day. Then she forced herself up in search of food, and more tampons. Isla didn't look like she had any plans of moving anytime soon, so Kate ventured out grabbing them each a slice of pizza and a Dr. Pepper, coming back a little reenergized after scarfing hers down. She showered and got ready for the day, having no idea when Isla was planning to move.

She heard her phone ping, realized Gabriel texted her saying his lunch plans fell through and asked if she wanted to get together. She looked at Isla again, snoring away and texted back "Sure, care for a walk in Central Park?"

She arrived first and decided to take a little nap in the grass - it truly was a beautiful day. She didn't know how long she waited until Gabriel showed up, grey sweatpants and all. What was it about a man in grey sweatpants? "Sorry I look like this, I just finished teaching a class." he said, kissing her hello. She forgot he was a dancer in addition to being a bartender. At the same time, they both said "Shall we get a drink?" They found a bar around the corner and next thing she knew she was three Aperol spritzs in, agreeing to go back to his apartment in Brooklyn. She justified it by saying that she wanted to experience the Subway, but was too afraid of getting lost to test it out on her own.

They got back to his apartment and went up to check out Gabriel's private rooftop right as Isla texted her that she was finally up and moving. Jesus. It was 5 pm and she was just now getting out of bed? Kate told Gabriel that she couldn't stay long because she needed to get back to Isla. "Then we should get started I guess." he said, pulling her down onto his lap as he sat on a lawn chair that had seen better days. "I'm on my period!" she blurted out. "I'm not a teenager. Blood doesn't gross me out." he retorted.

Oh. My. God. This was really going to happen. They went down to his bedroom and he pushed her down on his bed, kissing her hard as he did so. He struggled to figure out her wrap shirt so she pulled it off for him, cursing herself for wearing a beige bra. He pulled her bra off with ease, freeing her large, thankfully tan due to a quick tanning mouse application the night before she left for the city, breasts. Her nipples were already hard in anticipation. He looked at her with lust in his eyes, pulling one into his mouth, biting down hard and sucking. It hurt, but felt so good. She hadn't had a man suck her tits in so long, but she wasn't a stranger to pain. In her 20s, she loved when her partners used nipple clamps on her. Gabriel moved onto the other breast, tugging on her left nipple with his teeth while he palmed the right. After what felt like an eternity, he stood up and looked at her. She was bare from the waist up, but was still wearing her black jeans and shoes. "Take my pants off." he said roughly. Somehow, his shirt was already off. She didn't remember when that happened.

She tugged down his grey sweatpants, then his boxer briefs. Holy. Shit. His dick was huge. And beautiful. If a dick can even be called that. It was a smooth, long, thick and his public hair was trimmed to the perfect length. "Do you like sucking cock?" he asked, bringing her back to reality. She muttered a yes and took him into her mouth, a little nervous, not remembering when she last had such a well endowed partner.

She went through her typical dick sucking moves. She knew she was good at this. She took him deep into the back of her throat. She couldn't fit all of him in her mouth, but she felt his cock's head touch the back of her throat just as he hissed in pleasure. He pulled out of her mouth and pushed her down again, pulling off her boots, socks and jeans, until she was only in a pair of neon green underwear- again she cursed her choice in undergarments.

As she laid on his bed, he laid himself on top of her, so his dick was level with her mouth. She took him once again, but this time he slid her underwear to the side. "What a pretty pussy." he said. "You remember something is in there, right?" she retorted, not knowing how to take the compliment to her vagina. "I do." he said as he rubbed her sensitive clit with one hand, while working his cock into her mouth, likely just to shut her up. As she alternated between sucking Gabriel's dick and moaning in pleasure, he worked on her clit with his index finger, building her up to a release. "Are you going to be a good girl and cum with my cock in your mouth?" She nodded yes and then felt two fingers enter her...alongside her tampon. He thrust his fingers in and out, as he moved his mouth down to lick her clit. She was trapped under him and could no longer concentrate on pleasing him. She spit his dick out of her mouth and screamed. He rolled off of her and she asked where the bathroom was. He pointed her in the direction and she stumbled down the hall in only her undies. She couldn't remember if he had roommates, but if he did, they were about to get a show.

After she took her tampon out, buried it in a wad of toilet paper and pushed the bundle to the bottom of his trashcan, she went back into his room. "Do you have a condom?" she asked, hoping he wasn't one of those guys who didn't use protection - though she had a feeling this wasn't the case. "I do. Are you ready?" he said. "Yes." was all she could pant in reply. He pushed her down until she was on all fours on his bed, rolled on the condom and lined himself up behind her. She was nervous about his size, especially because they were starting from behind. She wouldn't have a chance to get used to his length and girth. He entered her and she squealed, pulling forward in a halfhearted effort to get away from the extreme fullness she was experiencing. He pulled her back, pushed her down so she was flat on the bed and slammed into her, keeping his right hand firmly pushing down on her upper back as he did so. She wasn't even sure the sounds she made were human. Pain melted into pleasure then back into pain as he slapped her right ass cheek hard 5 times in succession. "That's going to leave a mark tomorrow." she thought. Then he stuck a finger into her asshole, adding a new sensation to the experience. "Is this okay?" he asked. "Absolutely." she breathed.

As she was getting used to the sensation of being doubly penetrated, he adjusted them so that she was now on top. She rode his cock as he put his hand around her throat, moaning her name. Then he pulled out suddenly, muttering something about the condom rolling down. As she looked down, she saw her blood all over the condom and his lower stomach. He didn't seem to care as he rolled off the condom and pushed her down once again. "Are you a squirter?" he purred in her ear, inserting God knows how many fingers into her pussy before she could reply.

Yes, yes she was a squirter. Luckily he had laid a towel down under them at some point - likely because of her period- so there was no need to worry about ruining his sheets. She screamed as she squirted all over his hand and the towel. He didn't give her a moment to pull herself together before he moved to her clit, asking her once again if she would cum for him. This time, she was ready and came soon after he started rubbing her most sensitive part with his finger. She saw stars as she screamed his name, her orgasm coming too soon. He gave her a moment before entering her pussy again with his fingers, making her squirt even more.

Once she had nothing left to give, he rolled on another condom and entered her from behind once more. He spanked her twice- this time on her left cheek and pulled her hair, jerking her head back hard. She could tell he was close by his breathing and the way he was speeding up his rhythm. "Come for me." she said. "Are you ready?" he asked. She nodded yes, and selfishly she was. She'd already gotten off and at this rate, she wouldn't be able to walk tomorrow, plus she needed to get back to Isla.

He came with a final thrust. She didn't know why she did it, but she immediately got up and started getting dressed. She was not hanging around for post-sex cuddling, plus she realized he was actually really sweaty. In reality though, she thought that if she stayed longer she would end up begging this man to fuck her again and she was already afraid of her attraction to him. She texted Isla that she was on the way and pulled up her Uber app. Gabriel walked her downstairs and out of his apartment, asking if he would see her again before she returned to Cincinatti. "Probably not." she answered honestly, kissing him goodbye.

She played it cool, but internally she was a mess. That might have been the best sex she ever had and she was walking away from it. But what else could she do? She was never going to see this guy again. Best not to get attached.

She texted him something about seeing a cute park down the road and they continued to chat a bit, but not much, avoiding talking about what they did. They both knew their very brief, but intense fling was over.

The next day, she boarded Southwest flight 576 back to Cincinnati. When she landed, she deleted her text thread with Gabriel without saving his number, took a deep breath before walking outside with her luggage, and got into her husband's car.