A Gamer Walked into a Bar

A pair of bright sapphire orbs followed as John moved through the ‘car’, his gaze drawn to them. He couldn’t help but notice the very slight signs of age or weariness that showed around her eyes. The rest of her face, however, though definitely mature, was still wrinkle-free and had a slight glow to it.

His approach caused her pink lips to curl into a warm smile, which brightened her face more. Her hair was around neck length, and to call it unkempt would be unfair; it was obvious that it was more controlled chaos, there were no split or stray hairs, but it was styled in a messy fashion.

She looked to be in her mid to late thirties; unsurprisingly John couldn’t maintain eye contact and instead his gaze dropped. Her cleavage barely peaked over her scalloped hemmed shirt. When she saw John’s eyes, her smile turned coy, and she straightened her teal jacket.

Curiously this didn’t hide her cleavage but instead framed it a little better without showing more. John’s eyes quickly darted up as a blush crept onto both of their faces.

“Uhm, s-sorry,” John stuttered, as he abruptly sat.

She let out a short, soft chuckle. “Don’t be, if I didn’t want you to look…” she leaned forward, hooking a finger down the front of her shirt and pulling it further down, allowing John to see more of her soft marble mounds, “I wouldn’t have beckoned you over.”

John let out an awkward laugh as he blushed deeper and rubbed the back of his neck.

“No need to be shy. I’m sure we both know why you’re here. I know this place used to be quite popular with younger men but it’s been quite a while since I’ve seen any in here.” She stretched her hand out palm facing down, which John awkwardly took and shook. “I’m Diane, it’s a pleasure.”

“I, uh, John. I’m John,” he managed, trying to take a deep breath without her noticing. ’Come on, John, you’ve spent a week talking to women and stuff, you even just got a point into charisma, you can do this.’

“Maybe I should stop being so forward here, I get the feeling this is the first time you’ve done something like this?” she asked.

John let out an awkward chuckle. “You’d think that… it’s been a bit of a wild week…”

She smiled with amusement. “Oh? If it’s been that wild, why’d you decide to come here? I assumed you’d come to have an older woman take you to bed for the night, but if it’s been that wild, what could an old woman like me offer?”

“What? You’re not old, you’re gorgeous… In all honesty, we’ve been out all night and we thought it might be interesting to see what might happen,” John confessed.

Diane blushed and took a sip of her brightly coloured drink. “We?”

As if on cue, a voice came from behind him, “John? Where’d you- oh, there you are!” Her arms draped around his neck as she leaned on his shoulder. “Oh, so you decided you were interested in someone after all?”

Ellie slid into the booth, bumping John further in. Looking at her, Ellie had changed into a nice set of black trousers, a wine-red shirt and a pair of flats. Though it wasn’t as extravagant as the dress she’d changed out of, she still matched John’s semi-formal style.

Diane raised an eyebrow. “A friend of yours?” she asked.

“Girlfriend, actually. Wow, you’re stunning,” she said to the woman opposite, before looking over at John. “Why is it that you always seem to pick such gorgeous girls?”

“I, uh, well,” John stammered.

“I’m ever so sorry, I didn’t realise he was spoken for. I, well, I should probably leave the two of you. It was nice meeting you,” Diane said, beginning to pack her bag.

Ellie held her hand out. “Whoa, slow down. There’s nothing to apologise for, and there’s no need for you to leave. We didn’t exactly come for the overpriced drinks or the train-themed bar. We thought that an experienced woman might be a great way to round out our night.”

Diane blushed. “Oh, uh, I see. I’m sorry, but I don’t think I’m what you’re looking for. I, well, I don’t know how I feel about being with another woman, and I’ve never shared a guy before, I think it’s a bit out of my comfort zone,” she confessed.

Ellie hummed and took out her phone. She looked at John. “Cyn messaged me saying that she was willing to meet up, by the way. But it would be such a shame for you to pass up an opportunity to have the company of a woman as beautiful as this one, especially after you’d gushed about mature women all night.” She looked back towards Diane. “I’ll have to leave, but would you be interested in getting to know John a little more?”

The confusion on Diane’s face turned into recognition. “Oh, I see… Well, I can’t say I’ve been in this position before, the only time I’ve been in a remotely similar position was when I’d found out a guy was cheating after the fact…”

Ellie reached over the table and held the woman's hand. “Our relationship is a little open, we have rules for our other partners. I would have a request though, I’d love to see some pictures or anything like that since I won’t be a part of it and if you decide you’d want to have some more fun another time, consider including me.”

Then she added, “That’s a request, not a demand. If you aren’t comfortable I won’t **** it on you or threaten to withhold John:”

The older woman still seemed a little conflicted and thought for a moment. Ellie stood and put her phone into her pocket. “Well, it was nice meeting you, but I’d better get going though or I’ll leave my friend waiting,”

Diane nodded. “Uh, it was nice meeting you too… I, uh, suppose?”

John shuffled across the seat, following Ellie until she stood, turned around and placed her hand on John’s chest. She leaned down, kissing him on the lips. John let out a content sigh and Ellie pulled back. “I’ll talk to you later, and see you tomorrow. I love you.”

“I, uh, love you too…” John hesitated. Ellie winked at him before opening the door, blowing a kiss and waving as she left.

“That was… new,” Diane intoned.

John rubbed his face, groaning quietly. “I'm… sorry about that. I promise I was literally just about to tell you about her before she showed up. I don’t know how she manages to make things more awkward sometimes…”

Diane relaxed a little and giggled. “It was abrupt, and something I wasn’t expecting. Never had a girl wingman her own boyfriend before.”

“Yeah, it’s… well, it’s not exactly what I expected from the relationship. It wasn’t something I was entirely comfortable with either, to begin with. I guess you could say she’s pretty convincing. That’s not to say she’s peer pressured me into anything,” John divulged.

“Wait, so, you’re not the one who wanted it like that?” Diane asked, seemingly dumbfounded.

John rubbed his neck. “Before Ellie, you could say my idea of a relationship was idealistic. I’d pictured myself only being with one girl and that she’d probably be the girl I’d marry and have a family with. After meeting Ellie though, I’ve gotten into a relationship that I’m sure most guys would kill for. She’s not interested in other guys and she’s not quiet about her interest in me being with other girls or sharing. It’s been a wild ride.”

Diane laughed. “It sounds quite the adventure.” Her smile dropped and she cleared her throat. “I… I know I came on to you, and I’m sure I came off as quite aggressive, but this isn’t something I usually do, either. It was the last thing on my mind, really, but it’s been a long time since I’ve had… a male companion.

“I have picked up a couple of guys at bars in the past. Though never from here, those were a long time ago, right after I’d gotten divorced. I’m sure the guys before thought I was just an easy lay. Back then they weren’t wrong, I was a little raw from everything that happened between my ex and I. I was basically just using them to try and feel better but I’m not exactly young, and after having kids, my body isn’t exactly desirable.”

“What? No, you’re absolutely gorgeous, you’re a total MILF,” John blurted out.

Diane’s smile grew. “A MILF, eh?” She leaned forward again taking another sip from her drink. “Sorry about that, I’m a little stressed from work and I guess my drink isn’t helping me feel any more attractive or useful…” She took another breath before shaking her head. “Anyway, back to something a little less sombre. You’ve been talking about mature women all night?”

“I, uh, well… I don’t know if I’d say that… it might have come up once or twice,” John stammered. “I mean, it well, uh, I wouldn’t say all night…”

“Just some of the night then?” she teased, taking another sip of her drink and finishing it off. She closed her eyes and her chest puffed out as she took a deep breath. “Okay, I think we should go before I change my mind.”

She stood and opened the door walking out but holding it for John to follow. He jumped out of the booth and followed, feeling slightly awkward and nervous. “I, uh, if you’re not comfortable or anything, we can go our separate ways…” He hesitated.

She didn’t say anything and began walking; John couldn’t tell if that was an answer in and of itself, and if it was, he wasn’t sure what it meant, so he cautiously followed. After passing two shop fronts, Diane stopped and turned around.

She took a step towards John. There was a pause as she took a breath. “I… Kiss me,” she requested, taking another hesitant step forward. She stood roughly his height, so her soft bust pressed against his chest.

John swallowed as his nerves heightened, he was being put on the spot and by someone he didn’t really know; not only that but it was to do something John deemed quite intimate. His eyes were locked onto her lips as he swallowed a second time.

He slowly lifted his hand, cupping her jaw and gently running his thumb back and forth against her cheek. She smiled, closed her eyes and leaned against his hand letting out a sigh.

’Am I actually doing this? She’s just a random woman, not only that… but she’s around my mom’s age…’ he thought, his eyes once again drawn to her lips. This time images of his mother came to mind, Brenda’s full figure and her soft-looking lips. The picture of his mother standing in her lingerie wearing an apron at breakfast at the beginning of last week was clear in his mind. He shook his head. ’Fuck, what’s wrong with me? I need to get that out of my head and focus. It’s not the first time I’ve kissed someone, it’s not even the first time today…’

He took another breath, banishing the stray thoughts running through his head, and he leaned forward until their lips met. Upon contact, Diane let out a light moan. Her hands glided up John’s body, under and behind his arms until her hands rested on his shoulder blades.

John rested his free hand on her hip in order to guide her with him as he slowly backed up against the wall; he kept his shoulders and back away from the wall, ensuring he didn’t trap her arms or hands. Diane eagerly followed as she enjoyed the kiss the two shared, moaning quietly. John’s hand trailed behind her, stopping at the small of her back. He tightened his grip a little pulling her body closer to his.

After a little deliberation, John slowly parted his lips, which his hot mature partner mimicked. They both let out lusty moans as their tongues intertwined.

They continued to make out and Diane pressed herself against John, but he pushed back, taking pleasure from leading the kiss; his hand moved down and he placed it firmly on her ass, making her smile.

A voice caused John to gently push Diane back, and after they’d parted, John noticed the couple who had sat across from him and Ellie had exited the bar too, had passed the two and were now a couple of stores ahead. Diane giggled and leaned in to give him a peck.

“Wow, it’s been quite a while since I’ve kissed anyone like that. This might sound corny, but I feel like a teenager again,” Diane said, panting.

“I don’t think you’re feeling like a teenager, I just think you’re feeling sexy, and you definitely should because you’re gorgeous,” John reassured.

“Oh wow. Now that was corny,” she laughed, “but kind of a romantic statement too. You could be right, though, it’s been an extremely long time since someone has made me feel sexy.”

She smiled and took hold of John’s hand. “Let’s go. I’m feeling quite confident that I need and deserve to feel hot.”

The MILF and John followed the couple from the bar in silence for a block, before turning down another street, allowing them to walk together in solitude.

“Uh, so… I was wondering, where are we going? I’ve never done this before, are we getting a hotel or motel room or something?” John asked.

Diane took a breath of night air. “No, if I wasn’t getting a good vibe from you or I thought you might be a bit of a creep, I might, but I’m feeling fairly confident, so I’m just taking you home with me.”

“Oh, right. Uh, is your kid like not at home or something?” John spoke without thinking.

She let out a pleasant giggle. “Don’t worry, neither of them will be a problem. My daughter is at a friend's house, and even if she wasn’t, she’s a typical teen, the only way I can get her attention is to either go into her room or phone her because she has headphones on twenty-four-seven.

“My son will be at home, but his living space is in the basement, so we have two full floors between us; not only that but the basement has a concrete ceiling. If it was earlier in the night, I’d be more cautious because he’d have waited up to say good night, but after about eleven he basically locks himself in down there.”

“Oh, well. I can’t argue with that and I’m sure it’d be much more comfortable at your place than at any dingy hotel. So, uh, what are your kids like then?” John asked, more to be polite than any kind of curiosity.

“My eldest is around your age, he’s a lovely boy but he does remind me of my ex-husband quite a bit, though luckily the good parts. My daughter is five years younger, and she can be a handful, though I can’t say I was any better when I was in my teens. I hope you don’t mind but that’s about as much as I’m comfortable sharing,” Diane divulged.

“No, that’s more than reasonable, I didn’t mean to pry,” John said, rubbing the back of his neck with his free hand.

She smiled and hummed as the two walked the streets. After a few blocks, they came to a bus stop which John tapped to gain the new location.

Fast Travel Location Acquired

Springfield Town Centre

“I hope you don’t mind getting the bus, I walked from work to the bar because I knew I’d have a drink,” Daine apologised. “Don’t worry, I’ll get the fare for both of us.”

John smiled. “Don’t worry about it, I’d have been getting the bus myself anyway.”

She smiled and leaned in, pressing her hand against his chest and kissing him. The kiss escalated into a second make-out session, only broken up by the sound of an engine getting closer. The two turned to see the bus and Diane held out an arm.

The ride was uneventful, other than Diane blushing and smiling the whole way while leaning over to kiss John.

“Oh, this is us,” Diane said, taking John’s hand and standing. On the way past the bus stop, John tapped it.

John raised an eyebrow when he didn’t get a notification, but then realised where he was. He could see his house from where he stood, the lights were all out and the car sat in the driveway.

Diane laughed, snapping his attention back to her. “Is that a little OCD thing? Tapping the bus stop, I mean, you did it to the bus stop before we set off and again just now.”

“Oh, yeah, I guess you could say that,” John stammered.

“Aw, that’s endearing. Oh right, it’s this way, just a little walk so it shouldn’t take too long,” Diane said, taking John’s hand and leading him in the opposite direction from his house.

The two walked in the cool night air. They walked through a few different streets until they reached the houses that were a little larger than his. They weren’t huge in comparison, but it was still a noticeable amount. They walked through the neighbourhood before Diane stopped them at the foot of one of the empty driveways. She looked at John and smiled before leading him up the path and into the house.

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