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This is my first post chapter one of an in progress about a long term erotic affair. Comments and suggestions are most welcome!
Emily smoothed her dress as she climbed from the car. She looked around nervously, scanning the parking lot for familiar faces. Then she breathed deeply, tried to get control of her racing heart, and stepped into the busy Starbucks.
This was her first inperson meeting with the man she’d been texting with for the past two weeks. She scanned the room and thought she spotted him. A tallish guy in his 40s with brown hair, he was dressed casually but neat. He said his name was Greg, but she wasn’t totally sure. She’d gone by Ms. M until just a few days ago when she decided it was safe to share her first name, so who knew whether he was using his real name.
He was sitting at a small table occupied with his phone, so she took a beat to quickly think through all this one more time. Part of her was screaming “This is crazy, Emily! Get back in your car and delete Snapchat”, but another part a part that had only recently come alive was daring her to go just a little further and see where it led. That second part kept winning out, and she didn’t necessarily regret that.
“Here goes,” she whispered as she crossed the room. As she approached, she smiled brightly. “Hey,” she said, “I think you’re Greg and if you are, then I’m Emily.”
He looked up and she was immediately struck by his deep blue eyes and a glowing smile.
“Emily,” he said as he stood and pulled a chair out for her, “it’s great to meet you in real life.”
*****
This all started with a spontaneous decision in the aftermath of a stupid break up about a month earlier. At this point, she felt that Todd could go fuck himself, but she also was a little lonely and a lot reckless in the aftermath of his bad decisions and meanness. After a quick download of a hookup app and a few right swipes, she was awash in a sea of dick pics and scammers.
Only a few matches escalated to messaging, and none of them ever got to the point where she shared real contact information. Emily wasn’t sure what she was looking for on the app maybe just some attention, or a little flirty banter, or for someone to validate that she was beautiful. Most of what she got was… well, gross. Contact had consisted of a lot of dick pics, both hard and soft, a few messages that promised to ram or stuff or jam stuff into her “dripping snatch”, and a couple of ones on the margins guys wanting to be pissed on, or to buy her panties, or to cheat in front of their wives, or worse.
Greg showed up just as she was getting ready to delete the app. He was no Casanova, but his messages were normal and maybe a little bit sweet. His second message to her began with “I’m not even sure what I’m looking for here and am probably going to delete the app.” After a half a dozen DMs, they’d taken the conversation to an anonymous messaging service and just chatted. Not really about , although that was an undercurrent. More about what they did for fun and what movies they liked… the kind of stuff that normal people talked about. He was attentive, asked lots of questions, and was a little nerdy. And it was good.
Four nights ago was Saturday, and that’s when things escalated… fast. Emily had a glass of wine before signing on and she suspected that he was probably doing the same, although she imagined him with a beer. She clearly started it, asking him the most daring place he’d ever had (a beach was the answer). This had gone back and forth, getting a bit more intimate with each question. After a second glass of wine, she sent him a carefully cropped picture of her lifting up her bra to expose a breast. Rethinking her choices, she’d signed off shortly after. Part of her wanted to delete the app right then, but the new, more daring part led her to keep going just a bit further. What harm could be done?
The next night was Sunday, and when she timidly signed back on, it escalated again, and this time without the wine. After some more or less innocent chat, she sent a topless shot followed by one of her panties. As the night wore on, they texted about what they would do to each others bodies, and against all better judgment she sent him another carefully cropped photo of her body, fully nude, her legs spread, and her very wet pussy swollen and exposed. That was a first for her, and her anxiety was off the charts. He went radio silent for about ten minutes. Well, she thought, I guess that settles that.
And then a text:
“I hope it’s ok, but I just masturbated to that last picture. I couldn’t help myself.”
She swallowed hard and thought about how to respond. The smart thing the responsible thing would be to sign off, block him, and never look back. Instead, she responded:
“I wish I could have seen that.”
“I was hoping you’d say that.”
Thirty seconds later, there was a text with a short video clip attached. She opened it and watched. It was a thirty second shot of him from the chest down, stroking and shooting. He was in good shape not exactly a six pack, but a nice dad bod. His cock was nice too, although she was almost too embarrassed to admit it. She guessed it was six or seven inches long, circumcised, very hard, with well trimmed pubes and shaved balls. He was already close when the video started the head was throbbing and she could see the glisten of precum as his hand fucked the head. She could hear his deep breathing and a primal groan as he went over the edge, shooting several thick strands while his dick pulsed. She’d watched guys masturbate before, but this was a huge turn on. But it was also a step in a new, and potentially unwelcome, direction. She needed to think.
She sent him a kiss emoji. “That was nice,” she wrote, “but I need to think about some stuff.” And then she signed off.
What the fuck, her mind screamed. She’d seen this guy cumming to her nude pics before she’d even seen his face.
She knew that this was out of character, potentially dangerous, but it also felt good. Since the first flirty texts with him, her body had felt electric. As her mind raced through various possibilities, she found herself distracted by the ache between her legs. Still nude, she was wet and horny as fuck. Fuck it, she thought, and ran her fingers across her swollen clit. Within minutes, the waves of a strong orgasm broke upon her as she imagined riding Greg, her faceless Snapchat buddy..
When she woke up the next morning, she texted him right away.
“I didn’t make a video, but I wanted you to know that I masturbated to you last night. I think I’m ready to take this into the real world, if you’re interested…”
*****
Back in the coffee shop, the more she interacted with the real version of Greg, the hotter he seemed. He was a bit older than her 30 years, but very handsome and in good shape. His closely cropped hair was going slightly gray at the temples, as was the neat and short trimmed beard. And his eyes, oh boy… she could get lost in those deep pale blue pools.
They made small talk for a bit, flirting but also staying far away from their recent texts. It was a little surreal, making ordinary conversation with a man whom she’d seen masturbating just a few nights before and whose video had brought her off in record time. She told him about her freelance writing job, and he shared a bit about his work as a teacher. Greg had been divorced for about a year and, although she didn’t pry, she gathered that it was messy and that his reemergence onto the dating scene was slow, careful, and defensive. He had a good sense of humor and the conversation was effortless and fun. All good for a first date, and she wished it could go on a bit longer. But, in a terrible piece of planning, she’d scheduled a Zoom call with a client at one. Part of this was defensive on her own end, the call serving as a preemptive trapdoor out of the date if things hadn’t gone well.
“So,” she said, “I’m going to have to get back to my work. But this was nice and if you’re up for it, maybe we could meet up again. For longer?”
He smiled, “absolutely. If you hadn’t asked, I would have.”
“Excellent. Any ideas when or where?”
“How about dinner Friday. There’s a nice brewpub called Logan’s on the east side of town. I don’t know if you like beer or not, but the food’s good and it’s quiet but nice.”
“Haven’t been there, but it sounds good.”
“Great. Meet you at six?”
“Six would be perfect.”
They both stood. Awkwardly, betraying his slight nerdiness, Greg extend his had for a shake. She ignored it, leaned in, and kissed him on the lips. Electricity jumped through her body. She kissed him again, and this time he pressed his lips against hers, a deep, y kiss. Probably too much for a Starbucks at lunch time, she thought.
When she started to turn to go, he gently placed his hands on the side of her head, gently stroking her hair and then running his had gently down her neck to her shoulder and her back, pulling away slowly and sensually at her waist.
“Really looking forward to it,” he said.
*****
Once back in the car, it took her a few minutes to regroup and put herself together. Her heart was racing again, but this time not with nerves, but with the thrill of just having had an amazingly y kiss with a guy that she was deeply into. It was probably a good idea that she scheduled a meeting, she thought, because I really easily could’ve ended up in bed with that guy today.
As she started her car, her phone buzzed with a text alert. She grabbed the phone and saw it was the Snapchat app, which meant it was Greg. Probably texting a sweet goodbye… or maybe dumping her.
The actual message made her gasp and her heart missed a beat.
“I feel bad that I had all the fun the other night. If you’d like me to make it up to you, I’ll be in the Starbucks bathroom for the next five minutes. You don’t have to do anything. Just let me take care of you. And, no worries if you need to think things over again. I will see you Friday either way.”
She closed her eyes, and breathed deeply. This was an instant turn on… more so than probably anything that had ever happened to her. Her mind raced, imagining meeting him in there, hiking her skirt above her waist and peeling off her black bikini briefs… spreading herself on the edge of the sink while he put his head between her legs and used that amazing mouth… In her mind’s eye, she saw her collapsing in a quivering orgasm and then tasting herself on his lips.
But then sane, respectable, and responsible Emily took over. The last couple of weeks had already taken her out on the thin edge of something, and this was too much, too soon. She sighed regretfully, still thinking about what it would be like to have this beautiful man eat her out in a Starbucks bathroom.
“I want to,” she wrote, “but I’m not ready. Soon.”
In just a few seconds, he responded. “I get it. Thought it couldn’t hurt to ask, though. Lol. Offer stands when you’re ready” followed by a kissing emoji.
She replied with a kissing emoji of her own, and prepared to leave. The phone buzzed once more.
“I hope you’ll take care of yourself as soon as you can, and that you’ll be thinking about me when you do it.” This was followed by a devil emoji.
She laughed out loud. Unconsciously, her right hand had slipped into her lap, her fingers gently caressing herself. Through her dress and panties, the touch felt far away and vague, but she knew that at the earliest possible opportunity, she’d do exactly as he suggested.
ero
