The Curse of the Casual, Sexual Encounter: Part I

Anna Broderick Sinclair
9 min readNov 25, 2021

“You have soul ties with the people you sleep with and even when you are no longer in bed with them, they remain in your head. Your thoughts are consumed by their absence in your life. We feel disconnected from something when we give away our most prized bodily asset to a person that can’t even spell our last name correctly” — Chris Marvel, author of Love Laws: Rules of Love and Relationships in the 21st Century

Hot. Steamy. Seductive. Adventurous. Dangerous. Tempting. Enticing. Sexy. Alluring. Raunchy. Tantalizing. Suggestive. Shameless. Erotic. Carefree. Fun.

These are words used to describe not just one, but several casual sex encounters. However, there is usually one casual sex encounter that leaves one wanting more. Perhaps, more so than any other casual and sexual encounter from the past. Why is that, though? And, why is it that one person wants it more so than the other?

In most cases, between a male and a female, it is usually the female who is left wanting more. However, it is not so much the sex the woman wants. Instead, it is more so the connection. This happens very often, especially after just once or twice of having had sex. I still see this happening to women today. And, whenever they are left hanging, they not only are left wanting more but they are also left thinking about that person. Specifically, that person they consented to having hot and steamy sex with. That person they thought they would talk to on a regular basis, but didn’t. That person who hasn’t gotten back to them in over a week or two. That person who has been wrapped up on the other person’s mind ever since. It is a fixation that has become difficult to simply let go of. The fixation is being run through the other person’s body almost like some sort of drugs. The weakness has reached a level of vulnerability so high you wonder if you’ll ever see that person again, or even communicate with them through digital means.

It easily turns into a trap. The sex is so good, yet you want more but you still can’t get more. You want more than just the sex. However, the other person just isn’t in for the ride. You feel confident and convinced that you will not only see the person again, but also get to spend time with him or her. All the amazing and fun times you visualize having with that person never come to fruition. The hurt, overthinking, and extreme fixation all come trotting along.

You know how and why I know this? Because I have been through this reality several times. Including, most recently. And, it’s left me feeling nothing but extremely vulnerable and at unease.

October 29th, 2021: Two days before Halloween, I had planned to have a completely relaxed and easygoing Friday. The day before, I had experienced physical and mental burnout. My burnout was a sign that I needed to slow down and take it easy, so I decided to really look after myself and make some lifestyle changes. That Friday, before going to a live music event later in the evening with my friends, I went to have lunch with a dear friend of mine at our go-to spot. As my buddy and I were having a good time, a man walks in and recognizes me.

He points at me and says, “You went to my high school, didn’t you?”

I say, “No, I didn’t. You maybe remember me from a different school, though.”

“Hmm, you look familiar though. Anyways, sorry.”

“All good.”

However, I take a closer look at him and it hits me. I did go to school with him. It was one year’s worth of middle school, not high school. Not only did I remember his name, but I also remember how loud and eccentric he was. I even remember that I lent him money once and he never paid me back. Oh, well. We were just kids at the time. It was nearly fourteen years since I last saw him.

November 4th, 2021: I come across his Instagram profile and instantly add him as a friend.

“Was it you I mistook for someone I thought I knew?”

“Yep, we did go to the same school though — when I was 12.”

“Haha, see I was right. So, now I don’t look like a complete moron.”

“I was in middle school when I met you, not high school.”

“Ahh yes, now I remember. I hope I didn’t appear to be a complete weirdo.”

“Not at all! I took a closer look at you and went, “Wait a minute, I went to school with that dude. That’s Justin.” “

“Phew! Remembered my name! Impressive.”

“I was even surprised myself that I still remembered your name. Middle school was so long ago lol.”

“Very long time ago. So, what do you do now?”

“I freelance. What about you?”

“Ah nice. I’m a yacht captain.”

“That’s amazing, look at you!”

As the evening approaches…

“What are your weekend plans?”

“Well, I’m meant to go with a friend of mine to a brunch tomorrow to watch her perform. What about you?”

“Oh, very cool. No plans, yet.”

“Well, we could do something once I am back.”

“Ok, good to know. What mischief are you up to, tonight?”

“Was just out at dinner with a friend of mine. I had gluten-free beer for the first time. That was my only mischief lol.”

“That’s a thing?”

“Apparently. Doesn’t taste bad, actually.”

“Fair enough, sounds interesting.”

“Indeed. It does taste interesting.”

“So, are you seeing someone?”

“Nope, not seeing anybody. Just making the most out of the single life.”

“Well, lemme know your plans tomorrow and we can see :)”

“Sure thing.”

Brief pause

“How long have you been single?” he asks me.

“Would say for about six months now.”

“Ah nice! Well, been single four years myself.”

“That’s not bad. I once went on for that long, as well :)”

“What’s your type?”

“Well, apart from a guy who looks after himself — honesty, transparency, and communication which is a huge thing for me. As the saying goes, communication is a lubrication.”

“Never heard that before, but I actually quite like it.”

“Let’s just say I’m sexually open. Meaning, super transparent when talking about sex and intimacy.”

“Oh, gosh! So saying your voice is sexy AF okay?”

“Yeah, of course. No harm in that.”

“I’m the same! But never had someone who was open about it.”

“I hear you. Well, you’ve got me.”

“This is so refreshing because, no lie, I’m quite a sexual guy. Do you like talking about sex or are you just open to it?”

“Both.”

“Omg, I haven’t spoken about sex in four years! Haven’t even had sex in four years. What turns you on?”

I fall asleep because it gets late. However, I respond the next morning.

“Yep, I passed out lol. That’s alright. I’ve met men who’ve said they haven’t done it in three years. Plus, you’ve got really good self-control.”

“Haha, I’m going to explode with whoever I have sex with next.”

Responding to what turns me on.

“I suppose being a good kisser is one of them.”

“That’s a given. What else?”

“Passionate and rough sex.”

“Well, to be honest, I’ve now woken up with major morning wood.”

“Masturbation helps. It’s good for you.

“Yeah, I do it twice a day. How often do you masturbate?”

“On a daily basis, thanks to my toys.”

“But, before you get to sex. Like, has a guy taken you out or something? What gets you wet?”

“Well, I haven’t been taken out on a proper date by a man in ages.”

“What? Really?!”

“Yeah, no rush for it though. Hopefully, it happens again at some point. Oh, and foreplay is what supposedly gets me wet.”

“Well, maybe I can take you out if you’re interested. And, oh my goodness, I am so horny. Is it just me or does talking to me make you horny, too?

“Oh yes, I would really love it if you’d take me out. For sure.”

“On a scale of 1 to 10, how horny are you now?”

“I’d say it’s between an 8 and a 9.”

“Good :)”

Brief pause.

“I feel like I am asking all the questions.”

Looking back, I probably should’ve asked him several questions. Such as, “What are you looking for? Looking to date again?”

“No worries. Feel free to ask away.”

“You in bed or are you up and about?”

“Well, I am about to get ready. I am pretty much half naked in my seat.”

“That’s hot! If I was there right now, I’d be on my knees eating you out.”

“That, I love. I enjoy giving oral sex, as well. Oh, and I swallow.”

“Omg, I am rock hard. Shit, you swallow?”

“Always.”

“Do you squirt? Damn, I’m thinking about all the things I’d do to you half naked on that chair.”

“I’ve actually never squirted. I’ve cum, but I’ve never squirted.”

“I bet you taste so good. I think you should slowly spread your legs and slowly rub your clit.”

Brief pause.

“What’s your Whatsapp?”

Every time I remember that question, I get uncomfortable.

After exchanging Whatsapp numbers, our texts via Instagram still get a bit flirtatious. It’s because I show him visuals of me having a good time at brunch that day and how I look.

“Either way, you’ll still see me in my outfit lol.”

“Dangerous. That’s very risky.”

“Why?”

“Guess you’ll have to wait and see.”

“Awe yeah. Anyways, I’ll be arriving at my place in about 45 minutes.”

“Ok :)”

The Whatsapp texts were a bit raunchier. However, I won’t lie. They did get me really excited and optimistic. I even thought to myself, “Hey, maybe that guy is actually interested in me.” That was all before noticing that he may have actually blocked me via Whatsapp. Fucking coward.

“What are you wearing for brunch?”

“Smart casual. A top, skirt, and vans.”

“I like it! Lucky you’re not in a car with me haha.”

“I might be up your skirt. Take a pic.”

“Someone’s horny lol.”

“Haha, is it that obvious? Are you not?”

“I control it lol.”

“Haha. Well, you are around people. I’ll control it for now too, then.”

Few hours later.

“How’s it going?”

“It’s going alright.”

“Send a selfie. Oh, and I’ll also be free at around 7.”

“Cool, we can do something then.”

Brief pause.

“So, you live with fam then?”

“Yep. It’s crazy expensive to pay rent here. I mean, majority here live with their fams. What about you?”

“Yeah, true. I live alone.”

“That’s nice. You’ve got all the privacy in the world for self-pleasure.”

“Exactly! How do you feel being watched as you masturbate?”

“I’m alright with it. I’ve done it a few times during sex.”

“That turns me on like crazy. I love watching.”

“I love being watched too.”

“Do you like risky play?”

“Sure, have done that several times as well.”

“You like it?”

“Don’t mind it, as long as I don’t get caught lol.”

“Yeah, ofc! The rush is maybe getting caught. Where have you been risky?”

“I’ve done it in cars several times.”

“Fuck, that’s hot! You got me stroking myself here for you. I’m guessing you’ve been fingered while the guy drives.”

“Indeed, I have.”

“Do you cum from that?”

Brief pause.

“Sorry, please tell me to shut up if I’m bothering you or asking too much.”

Looking back, I probably should’ve said, “Nah, you’re good. I just hope I am not overwhelming you as it’s been four plus years for you.”

“Not at all, you’re good lol.”

“Haha, just not used to someone as being as sexually open as me.”

“It took me time to develop and find that here too, so I totally get it.”

“So, you have a few guys you talk to?”

“Not really, to be honest. Most of them are just down to fuck and nothing else. Which, I find pointless. Sure, I can be casual but at least also have normal conversations. Not be a booty call.”

“Agreed! When did you last have sex?”

“Well, it was on Sunday but it was super quick. Nothing serious. Just some fun and risky play.”

“Did you enjoy it?”

“Meh, I was neutral about it. It’s whatever.”

“Do you like the guy to take charge and be somewhat in control?”

“Oh yeah, definitely.”

“So if maybe you weren’t in the mood but then I started teasing you, you wouldn’t mind it?

“Not at all. I’d probably get in the mood a little.”

“You should come to mine and masturbate. You can be in a bed and be as loud as you want.”

“Awesome.”

“Does this talk make you horny or is it just me?”

“It sort of does, actually. It’s not just you.”

A few hours pass by.

“So, what you wanna do?”

“Maybe meet up someplace.”

“Any ideas where?”

“Sure, someplace close to you works.”

“Whatever is easiest for you. If you need to go home first, I can pick you up.”

“Sure thing, will keep ya in the loop.”

About 45 minutes pass by.

“Hey dude, I’m back. We can meet up now.”

“Where do I pick you up?”

“I can drive, it’s no issue.”

Up to you, as I don’t mind picking you up.”

“Does to the moon and back sound good? That’s a spot not far from either one of us.”

“Sure.”

“See you soon.”

This is the end to Part I. However, Part II will not take long to complete. Stay tuned.

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Anna Broderick Sinclair

My purpose is to encourage authenticity & open-mindedness. A safe space. This is how we will all reach our full potential, and create a more humble environment.