A Collection of Firsts


**AUTHORS NOTE: This is a work of fiction featuring characters all over the age of 18.

This story also contains a detailed act which some individuals may be decidedly un-into. If you suspect you might be offended by this (although I really did attempt to handle it in a loving way, I swear) then please, feel free to pass.

Otherwise, enjoy!


“Thanks,” Gemma smiled as the hotel bartender placed the small wedge of salad in front of her. She took a sip of her water, still adjusting to the anxiety and excitement of dining alone.

It was her first time.

She’d booked the trip as soon as Evan announced he was leaving her and moving in with the most recent of his several affairs. She had expected his guilt at ending their marriage to shrink him, to calm him with shame, but it had only inflamed his attitude towards her.

He had screamed, punched a hole through the kitchen wall, dumped all of the blame and anger onto her as she stood small and scared behind the counter. He’d complained that she never fucked him enough, that she would never do any of the things his new girlfriend did. Gemma tried timidly to note that he had never asked her to, at which point he accused her of being too uptight and selfish to bother with.

She’d never considered herself to be either of those things, so the accusation that she was a cold and uncaring person stung in a way that only words from the man you love can.

No. The man she loved.

Past tense.

Gemma was shocked by how easily she’d fallen out of it. It had been declining so slowly over the past six years that she’d failed to notice it at all, but sure enough, inch by inch, day by day, she’d been unwittingly creeping out of love. Maybe Evan had sensed this, and in the end her detachment only made him angrier. He wanted her to shout and wail, to break a glass. To show how much she wanted him even when he didn’t want her back. Instead, she quietly booked the first flight she could find to another city and wished him luck with his promising new fucktoy.

She didn’t mourn his loss, but she did mourn the loss of her time. A vacation felt like a way to start fresh. To try something unfamiliar.

To explore life again.

Finally alone in a new city, Gemma was cutting her salad into bitesize pieces, slowly dragging a fork through the decadently creamy dressing, when a man pulled out the barstool beside hers and sat down.

He smiled and nodded.

“Hey,” he said with a small wave.

Gemma swallowed abruptly. “Hi.”

He was blatantly attractive, wild curls kept short at the side and longer on top in an attempt to tame them, eyes that looked both inquisitive and amused. His smooth skin practically begging to be touched. She put him at somewhere in his twenties, having clearly chosen a seat within her proximity due to the crowd at the bar more than a desire to be near her. After all, she must have had almost a decade on him.

“Oliver,” he announced, even though she hadn’t asked.

“Gemma,” she responded, perking up a little bit. God, he smelled good.

“I hope that’s not your entire dinner,” he laughed, looking at the palm-sized lettuce covering her plate.

“And if it is?” She raised an eyebrow suspiciously at this stranger now assessing her dietary choices.

“What?!” He practically cried, “But the chef here is so great! It’s why I always come back. I mean don’t get me wrong, I’m sure that dressing is goddamn delicious, but a side salad? For dinner? It’s just too sad.”

“Well, god forbid I look sad on vacation,” Emma smiled, setting down her fork. “What should I have ordered? What are you getting?”

“Oh, definitely the octopus. I wouldn’t usually recommend it most places, but it’s like, sinfully good here,” he responded, hand to his chest like the memory of its flavor had made his heart skip a beat.

Octopus? Not happening. Wasn’t the whole point of their tentacles to grasp onto things? Gemma imagined swallowing a bite and the invertebrate’s arm latching on, choking her. Gagging her with vengeful undead suction.

“I don’t think I can eat anything that smart,” she shrugged.

He grinned.

“It’s fine, only the dumb ones get caught. You can try some of mine.”

There was something about his confidence that was genuinely charming, inviting her to play along as opposed to showing off. And she didn’t mind the company, dining alone didn’t have to mean dining silently, after all.

The conversation followed easily, and he eventually asked how her vacation was going. Somehow, his disarmingly funny and sincere manner, along with the fact that the bartender clearly knew him, made Gemma feel comfortable enough to confess that she was traveling by herself for the first time. She’d only vacationed with friends or family in the past, occasionally with Evan before all of his weekend trips became suspiciously solo, booked under the guise of extended business. His Friday to Sunday fuckfests, apparently.

How stupid she’d been.

Oliver was genuinely sympathetic, having recently gone through a shitty breakup mecidiyeköy escort of his own, a generous spirit concretely taken advantage of. They gave a small cheers to their respective misfortunes, though neither seemed to care much in that moment, too excited and pleased by the connection they’d found in minutes with a stranger.

His octopus arrived and he asked for an extra fork.

Oh shit, Gemma thought. He was serious.

“Come on,” he urged her. “You’re on a roll! First trip solo, first time dining out by yourself. Why stop there?”

He handed her the fork, his eyes sparkling, bright and encouraging. Try something new, they said.

“Alright,” she sighed, cutting off a tiny piece. She slid it into her mouth, then began chewing cautiously.

It was delicious, coated in some type of marinade that she savored on her tongue before biting down again. The octopus was lightly crispy outside, tender in the center, and significantly less chewy than she had imagined.

She brought her napkin to her mouth, her eyes wide in surprise.

“That did not suck,” she laughed.

“See,” Oliver announced, beaming, “I told you! I’m impressed, I was definitely worried you might hate it. So what else have you never tried?”

Gemma blushed, her mind instantly racing to the inappropriate. It wasn’t her fault of course, look at him. What was she supposed to think?

“A lot of things,” she finally answered, hesitantly. “Too many.”

“Oh yeah?” He asked mischievously. “Like what?”

Was he flirting with her? If he wasn’t so young she would have sworn he was flirting with her. She wasn’t unattractive, she’d dated easily before Evan but it had been such a long time since she’d flirted with anyone. What if he was just being nice? She should probably answer with something safe, veering on the side of caution rather than risking embarrassment.

“It’s stupid, but I’m going on a tour tomorrow. I’ve never actually taken a tour of a city before.”

What an idiotic answer. She wanted to cover her face, almost wishing the octopus had choked her after all.

“I’d be happy to show you around if you’d like.” He didn’t laugh at her, in fact he sounded nervous. Almost self-conscious. Was he afraid of her reaction?

Well, wandering around an unknown city with a total stranger would certainly count as something new, Gemma thought. So would getting murdered.

“You could meet me,” he added quickly. “All outdoors, public areas. Only what you’re comfortable with, and if I’ve freaked you out I totally apologize! That was not my intention.”

“Honestly?” He added, pausing. “You’re really stunning and I’d just like to see you again. We can make a game of it, trying new things. An adventure.”

Gemma’s heart skipped a beat. Had anyone ever called her stunning before? She didn’t think so. Certainly not anyone so memorable.

“Ok,” she smiled, cheeks pink, trying to keep it from spreading across her entire face. “Tomorrow afternoon?”

“It’s a date,” he grinned. Gemma’s first one in years.

“Can I push my luck?” He held his breath shyly.

“You can try,” Gemma laughed. What else could there possibly be?

“Have you ever been on a motorcycle before?”

Gemma shook her head no, she had not. She’d occasionally wondered what it might feel like, being the girl on the back of a bike, or hell, riding one alone, but she’d never known anyone who owned one.

“Would you like to?” Oliver asked. “Just around the block or something? Look, I’ll even leave my phone and wallet at the bar as collateral. Mae will watch them so you know I’m not gonna kidnap you. Probably. I mean there’s a 95% chance we make it back without even getting pulled over. Great odds.”

Gemma laughed again, “Alright, sure. But you should maybe grab your license for that 5%.”

He looked thrilled, sliding his ID from his wallet before pushing the rest across to the bartender, Mae, who agreed to stash everything until they came back.

Gemma walked out to the lot with him, breathless. She’d worried that her skirt might be a problem but he assured her that it was fine and that she’d be behind him anyways. He handed her his helmet and although she felt a little goofy, she was terrified enough that she wanted to be safe.

“Ok,” Oliver said, “You’ve got this. Let’s cross some shit off that list.”

She climbed onto the back of the bike and wrapped her hands around his ribs, feeling the tightness of his muscles, surprised by how hungry she was to touch more. She gave him a small squeeze to let him know she was ready, and he started the bike.

Gemma didn’t know whether to squeal or scream as they zipped down the mostly empty streets. They could only go so fast in the city, but to her they might as well have been on the autobahn, the neon lights of closing shops a blur as they passed by. She held on tight, her heart pounding beneath her breast. Fearful that they’d topple over at each turn.

It was her first trip alone and there she was, racing through town on the back of a motorcycle şişli escort with an extremely charming, intensely handsome stranger.

Life was fucking strange and beautiful sometimes.

He took her back to the hotel after their brief, exciting jaunt, and Gemma dismounted carefully, her legs shaking and weak from the adrenaline. Oblivious to the fact that she’d surely flashed him her underwear when she climbed off.

“That was incredible!” She gasped, handing Oliver his helmet.

He walked her back to the bar to collect his belongings, agreeing to join her for one last drink so she could wind down.

They finalized plans to meet the next afternoon and finally, reluctantly, Oliver wished her a good night.

Gemma smiled.

She could barely remember a better one.


She went back to her room after he’d left, closing the door quietly behind her, her whole body aching. She didn’t bother switching on the lights or closing the curtains, the room dimly lit by the soft glow of the city.

Gemma didn’t know the last time she’d been this aroused, so alarmingly wet. She’d been squirming discreetly by the time the tab was closed, eager to get back upstairs so she could be alone.

Oliver had turned on a light in a place she’d forgotten, and all she could think about was how badly she needed to get her fingers between her legs.

Well, maybe not all she could think about.

She tossed the comforter aside and lay down across the sheets, lifting her skirt and pulling her panties down beneath her ass. She didn’t even bother to undress, she couldn’t waste that kind of time.

Her fingers gently parted her lips, her inner folds completely slick with her fluids. God, if he only knew. She moaned quietly as she pushed two inside of herself, pretending they were his. Wondering how she might feel to his fingertips, to his cock.

She drew her fingers back up to her clit and began masturbating furiously, tilting her head back, flushed, cumming harder than she could even remember.

Two minutes later, she did it again.

She undressed for bed afterwards, pausing to examine her nude body in the mirror, imagining through her reflection the way she might look to someone else. It wasn’t so bad. She’d kept in shape despite being rarely touched by Evan, and her breasts, while not impressive in size, had been gratefully ignored by gravity. She found herself wishing her ass was a little bigger, but maybe it didn’t matter. There was no guarantee that the date would progress into night, or that Oliver would touch her at all.

She fell asleep naked though, optimistic. Desperate to feel and be felt by someone new.

Hoping that it would be him.


She woke up slowly the next morning, fingering herself more lazily this time, gently teasing her nipples, running her hands along her body. She might need to buy a vibrator at this rate. It wasn’t a bad idea actually, having planned to spend a vacation alone, and her luggage was sorely lacking in any kind of lingerie or sexual accessories in case she didn’t.

But what had she always wanted to try?

She felt overwhelmed by the question, confused by her suddenly raging libido. When had it shut off, exactly? Did it happen suddenly or slowly, a casualty of Evan’s emotional neglect?

And how did Oliver turn it back on, volume blasting, so damn easily?

Could he turn it even higher?

Jesus. She was going to need to find a sex shop. But first, a shower and some coffee.


Gemma left the hotel with her hair still damp and headed towards the cafe. She ordered a small black coffee and a French pastry, then sat outside to relish them both in the morning sun, the beams on her face a silent promise of more heat to come.

Good, she thought, bring it. She knew it was still miserable back in Chicago and she was in no hurry to return.

The store was a walkable distance in nice weather, an upscale lingerie boutique she’d found in the business district which also specialized in some higher-end toys. Certainly an interesting start to her day, if nothing else.

A soft bell chimed when she entered the shop, and she took a deep breath, overwhelmed by the displays of silk and satin, lace bodysuits and negligees. Some of the outfits covered nothing at all, simply accented what you wanted to show with thick bands and clasps. The mannequins wore these with pasties, fabric circles covering their sculpted nipples.

That might be a bit much for a first date, Gemma thought, although she was a little turned on by the idea.

A glass display case held various toys and other accouterment, a perfectly curated selection of vibrators and dildos. Gemma asked to see one of the smaller ones with multiple settings, discreetly charged by USB. She gulped when the sales associate told her the price, but fuck it. How much money had Evan spent on his women? How much was his latest charging for her flexible and eager services? Gemma deserved to treat herself to something fun.

She excitedly consented to the vibrator, and continued moving through the case. It contained a small assortment of anal plugs in a few sizes, some matte, some metal. One had a fluffy tail sure to make the wearer resemble a couture sex rabbit, if that was your thing. It wasn’t Gemma’s.

Or, rather, she didn’t know if it was. Gemma had never tried anything in her ass before. It wasn’t that the thought of anal disgusted her or that she felt judgmental about it, in fact, the idea of something that vulnerable kind of turned her on, but it seemed to involve a level of trust that she’d just never felt with Evan. In retrospect, she probably should have considered that a sign.

“May I see those?” She asked the associate, pointing to a silk blindfold with matching ties. They were smooth and black, the mask accented with lace. It was beautiful. She’d never been tied up before, and wasn’t sure how he’d do it. He could bind her wrists together, or maybe tie her arms to the bedposts? She’d splurged on a nice hotel known for its eclectic style (and apparently, its incredible chef), and was fortunate enough to have a bed that might allow for a little fun.

“I’ll take these too,” Gemma smiled. She could always use them one day, if not today. Her world was becoming wide open again. She glanced over at a small tube of lube and added it to her growing pile as well, just in case her newly discovered flooding shyly ceased running for the actual event. She didn’t really know what to expect, although it had certainly not been an issue during the last 14 hours. She’d been in a chronic state of arousal since dinner.

Gemma browsed through the paddles and crops, wondering how it might feel to get spanked by each, then carefully thumbed through the racks of lingerie, appreciating the delicate fabrics and shades draping from their hangers. The single pieces were gorgeous, but she wasn’t sure how you had sex without taking the entire outfit off, which seemed like a bit of a waste for something so lovely. She eventually settled on a few bra and panty sets, one in emerald lace, the other in sheer black, then added a silk halter slip with a matching thong.

She eyed the harness bras again on her way out, the idea of being so overtly displayed yet hidden beneath the dark nipple coverings adding to the heat steadily building between her legs. Screw it, why not? She thought, and had the clerk throw one of those in her bag too. Maybe one day.

Back at the hotel, Gemma immediately unpacked her purchases, running her fingertips lightly over each item. She charged the vibrator first, eager to test its power against her clit, for the throbbing within her own small button to be released, sent out in waves through her body. Tiny spasms rocking through her with each contraction. She wanted to imagine Oliver’s curls between her legs as she did it, or to picture his hands running along her back, gently biting at her neck while she rode up and down on his lap, filling herself with his young cock.

Jesus, who had time to wait for a charge. She pushed her new presents aside and went at it again on her stomach this time, hips slightly raised as she moved her fingers along her cunt. Whispering his name as she came.

Was this who she was now? Someone who masturbated twice before noon?

How was she supposed to function this way?

She squinted at the dimly flashing light of the charging toy, knowing damn well she’d probably get in a third before their date.

Hey, she thought, with more excitement than shame at her sudden awakening, it’s my vacation.

She’d earned a little self-care.


It was just after three when she met Oliver outside the park. Gemma pressed her dress down as the light breeze teased its hem, then smiled when she caught his eye and he began walking towards her. He was wearing a short-sleeved shirt and carrying a thin jacket, and she blushed when she looked at his toned arms, wondering what it might feel like to wrap her hands around them, or to have them wrapped around her. Lifting her body. Pinning her beneath him.

They exchanged an awkward hug, excited to be together again but both unsure exactly what that meant. A mutual, silent hope hanging in the air between them- the three letter word that neither would say, writing itself in cursive over every thought.

They walked together through tree-lined streets, bracing for unleveled cracks in the pavement, branches dripping with moss overhead. He told her the history beneath the city’s foundation, stories of the architecture above it, rumors of hauntings within. Tales of plagues and prostitution, wars and money, both new and old. The city was loaded with history, and she was as enthralled with its narrator as she was with the world around her, even though she suspected him of some humorous embellishment. Hell, he could have been making half of it up and she wouldn’t have cared. No tour could have been better.

Oliver stopped for coffee at a local cafe and ordered her a style specific to the city itself, a type she’d never tried before, and a trio of fresh, pillowy donuts buried in powdered sugar. She took a small bite and smiled, dabbing at her mouth, both embarrassed and charmed to be eating something so messy with him. Having her dessert first. They didn’t finish the plate though, there was too much more to try.

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