September 10, 1995

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Another heavy sigh escaped my lungs. I've been sitting cross legged  on my bed for the last few hours just staring at my computer screen from across the room. I got as far at the sign on screen before I walked away from the machine like it had burned me. On Monday morning I had woken up a hungover mess. By midday Ally had finally emerged from her room and asked me how my Sunday night chat had been...I didn't remember chatting with him at all. Out of curiosity I logged in and checked my chat history. I thought I was done being sick, but as my eyes scanned over our words I felt bile rising in my throat.

Closing my eyes I let my head fall back against my bedroom wall as I felt embarrassed all over again just thinking about reading those words. In my drunken haze I'd told this stranger something I've never been brave enough to talk to my boyfriend about. Over the course of the week I considered everything from starting a new account with a new screen name to just never using the internet again. Now here I was on Sunday night, no new screen name and still wanting to log on. Hell, I even want to have my normal Sunday night chat, as long as we could pretend last week didn't happen.

I kept trying to tell myself that this guy, Jamie, didn't know me, but it was obvious that he did to some extent. Rubbing my eyes as if that would make this all go away I thought about how he knew me well enough to know that I would be embarrassed by what happened.  But embarrassed didn't even begin to cover it. Humiliated. Mortified. The fact is that now me and some random stranger in the Midwest know that I've never had an orgasm.

"Fuck it." Mumbling to myself as I left my bed and sat in my computer chair. "Why should I care what he thinks?" Talking myself into being braver than I really am. My stomach flipped as I clicked the sign on button and quicker than ever my screen came to life.

SixStringGuy: Hello Sydney!

Grumpybluebear: Hi Jamie.

SixStringGuy: Getting on a little later than usual tonight.

Grumpybluebear: Yeah, just been busy. Had a lot on my mind.

Here it is I thought to myself. This is when he's going to bring it up. This is when things are going to get awkward.

SixStringGuy: Me too. I bought a ring.

And just like that the conversation turned and I realized that maybe my drunk musings weren't his biggest concern.

Grumpybluebear: so you decided you want to get married. Congratulations.

SixStringGuy: I thought I'd decided, but I keep having second thoughts.

Grumpybluebear: Why?

SixStringGuy: it's gonna sound stupid.

Grumpybluebear: I don't care. Tell me what's up.

SixStringGuy: you see where I'm from I'm sort of well known and I'm afraid she wants to be married to the image more than me.

Grumpybluebear: so, you're afraid she wants what your strip club empire can give her more than she wants you? Is that it?

SixStringGuy: sort of. I don't want to make the wrong decision. If we do this I want it to be forever.

Grumpybluebear: have you talked to her about your apprehension?

SixStringGuy: are you really suggesting I tell my girl I'm not sure if she loves me or my money/image/status?

Grumpybluebear: why not?

SixStringGuy: Wow! You really do have a lot to learn about relationships lol.

Grumpybluebear: but if she really loves you wouldn't she want to hear about your fears and concerns? Wouldn't she want to make sure you're going into this without second guessing anything?

SixStringGuy: maybe.

Grumpybluebear: that's all I'm saying. If she doesn't care about your worries then that would be a red flag to me.

He was quiet for a long time. I waited patiently for anything to come from his end of the conversation. This was the awkwardness of online conversations. There was no way to push the conversation along without coming across as pushy, but after a over 10 minutes of waiting I stopped caring.

Grumpybluebear: you still there Jamie?

SixStringGuy: Yeah. Thinking.

Grumpybluebear: You alright?

SixStringGuy: I don't know if I can give her what she wants. Getting married won't change who I am or my business or how that effects my daily life.

Cocking an eyebrow at the screen I started to wonder what his business really was. It seemed like he was only giving me enough information to make me ponder more questions that I knew he would never answer.

Grumpybluebear: then you need to explain that to her.

SixStringGuy: Maybe. Anyways, your boyfriend visits next weekend?

Grumpybluebear: you have a very blunt way of telling me you're done with a topic :|

SixStringGuy: I know. So how are you gonna handle that visit?

Grumpybluebear: I'm gonna ask him flat out how long he's been cheating on me.

SixStringGuy: and what about when he lies to your face and tells you he's not.

Grumpybluebear: what makes you think he'll do that?

SixStringGuy: he just will. Trust me. You need to be ready for that. Don't let him catch you off guard by playing innocent.

Grumpybluebear: I'll have to give that some thought.

SixStringGuy: I want to ask you a question Sydney, but I don't want you to get upset or run off.

Grumpybluebear: What?

SixStringGuy: It stems from our conversation last Sunday.

My face heated up just reading those words on my screen, but a part of me wanted to suck it up. I was curious what he could want to ask and the greater challenge would be if I could muster a response without running away.

Grumpybluebear: :/

SixStringGuy: Don't give me that look mama. No one made you tell me the things you did last week.

Grumpybluebear: I'll try not to run away, but I can't promise.

SixStringGuy: Have you told Him that he's never made you come?

Grumpybluebear: none of your business.

SixStringGuy: so that's a no.

Grumpybluebear: so your just going to guess at the truth based on my refusal to answer you???

SixStringGuy: Am I wrong?

My cheeks felt like they were on fire and I could only imagine this is how embarrassed I would have felt had I been sober during our conversation last week. But there was something else, something I hadn't expected. Just the idea of chatting with him about this was making me wet. Maybe it was the idea of discussing sex with a relative stranger or maybe it was because he was the only person who had ever expressed an interest or maybe it was something else completely.

Grumpybluebear: no

SixStringGuy: why didn't you tell him?

Grumpybluebear: I don't know. It never came up.

SixStringGuy: Did You ever talk about sex?

Grumpybluebear: :|

SixStringGuy: You have to be able to talk about sex mama. If you can't talk about it then it will never be any good for you ;)

Grumpybluebear: ok that's it I've got to go. I didn't run away, I'm just slowly walking out of the conversation this time.

SixStringGuy: ok Syndey. You should look back over my last message from last week and do that again ;) Sweet dreams mama.

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