Why not to drink wine alone in a hotel room.

Alright, so it's been a while. How many men/encounters have I not shared?

3 guys

Multiple encounters

One of which took place at a local historical site after having to relocate from another historical site after being too loud while being fingered and getting yelled at by some old lady.

But that's not the really good story.

This is the good story:
I was bored and was between guys and so I decided to do an experiment.
I had heard that girls who post craigslist ads get A LOT of emails and so I wanted to post one to see how many dick pics I would get. I posted a vague ad with no pictures and got just under 100 emails in one afternoon.
It was ridiculous. So many pictures of penises.
A few, like 4, of the guys seemed to be actually interesting people and they sent me normal photos of themselves so I emailed with them for a bit until the 4 narrowed down to 1 guy.
I decided I would meet this guy, who comes into my city for business trips once a month, for a drink and see how that goes. I met him at the hotel bar and we had a few drinks and decided to go up to his room. In his room he had wine and so we drank that and chatted for a bit. Eventually I got impatient so I made the first move and quickly things were starting to heat up.
After a bit of foreplay he was on top of me pumping away and then he stopped moving.
He had a pained look on his face so I asked what was wrong and he mumbled something I couldn't make out.
So I just kind of continued to lay there for a couple more seconds trying to figure out what the fuck was going on when all of a sudden he started to cry.

His tears were falling onto my boobs. He was still on top of me with his dick in my vagina. I had no fucking idea what to do!

I said "I have to go" and he mumbled something about feeling guilty because he has a wife and kids. He finally rolled off of me and sat, whimpering, on the edge of his bed while I threw on enough clothing to be decent and grabbed my shit and RAN AWAY. I finished getting dressed in the hall/elevator.

After that we had no contact. I eventually kind of forgot about it, or blocked it from my thoughts.

Until tonight. I got these emails from him:  

Email 1
Hi There,
I have been looking for you. We hooked up a while back, at the Delta...........well not much of a hook up as I chickened out after the first round. Anyway, I have been wanting to make it up to you, and to be honest, I want to have more fun with you. If you are up for giving me another shot, and you have some free time tonight, then drop me a line. I am over at the Radisson. I have a couple bottles of wine in the room and would love your company.
I hope you are up for it.

Email 2
Come on, let's give it another go around. I know that while it was brief, I enjoyed every second of it. You were impressed with how deep I was able to get inside of you. Come on over for a few drinks and if you want, some fun.

With which I responded
I'm not sure if you feel like you have to prove something to me by finishing fucking me but I am really not interested. At all. I was entirely put off by our encounter and have no interest in giving it another go with you.

Email 3
I am very sorry to hear that. I was not looking to make anything up to you, rather I was looking to have the first encounter that we should have had. I do apologize for how it went down. I do feel bad and wish that it would have gone better. Is there anything I can do to change your mind?

Email 4
Look I was ashamed and embarrassed that I came so quickly when we had sex. That is the reason that I got scared and backed down. I am not proud of this, actually I find it down right humiliating. I am sorry that I left you with such a bad impression of me. I am truly sorry and I do hope that you can forgive me. I do wish you all the best in life and in your future. If there is ever anything I can do to make this up to you, to show you I am sorry, just let me know.

These emails were spaced hours apart, meaning that he probably spent his night drinking the wine he mentioned and writing me emails. So that's unfortunate. I am very thankful that he doesn't live here so there is little chance of me running into him.

Male Friend's Night Out

Context: This is a SMS conversation between myself and the male friend mentioned in my previous post. He's happy to be single again because he gets to tell stories like this one.

 

Male Friend: funny story last night

Zima: oh, good.

Male Friend: went to celebrities (gay bar on davie). Predictably it was about 50% straight chicks. Chick comes up to me and says "why does everyone keep saying happy birthday. This is a wedding veil. NOT a birthday veil!"

Male Friend: girl proceeds to complain that guys are hitting on her, and that they should respect her upcoming wedding by not hitting on her.

Zima: ...and you fucked her?

Male Friend: Soon we are on the dance floor making out and she's rubbing my bone

Male Friend: it's about 1:30 and she's "do you want to go back to your place?"

Male Friend: I'm like sure, let's go grab a cigarette outside first

Male Friend: we go outside. I say "close your eyes. I want to kiss you."

Male Friend: closes her eyes. I pimp-slap her and call her a whore. Then I get into a cab and drive away

Question:

When you run into a one night stand that you met at the bar while drunk and then proceeded to spend the majority of the next day with, is it okay to pretend you don't know them when you run into them months later?

Or am I just really weird and awkward?

But I guess he is awkward too.

Male Friend's POV on Dumping a Terrible Girl

"Breakups feel bad. It's like... having your asshole pit bull put down. I mean, sure, it bit your kid but you still feel kind of shitty after. And the sex. I'll miss the sex."

What Separates Men From Boys

The following is an excerpt from a text conversation I had earlier with a guy I was seeing for a few weeks. The back story: he's great on paper -- smart, funny, has a great job, owns a car. In practice however, he's rather timid, somewhat shy, and incredibly awkward, which I found endearing... until I didn't. He has a big dick, he lasts a long time, and he knows how to use it and his fingers, but not once in the handful of times we had sex did he so much as attempt to take his mouth anywhere below my chest. He also nearly cried when there was a little blood on the condom once. Definitely wasn't going to work.

Last night he started asking me for dating/girl advice, as when I broke it off with him I told him "I think that you're perfect for someone, it's just not me," and as all nice guys do, he wanted to stay friends. He's tried a bit of online dating that's led to nothing, and he doesn't really know how to approach women IRL, but he says that with his new great job, he's finding himself wanting to settle down more and more, (keep in mind, still lives with his parents. Settle in the basement? I don't know.) He's also decided that he wants to date older women. Right.

I gave him some tips, and then went to meet my friend for a few drinks. He texted me more while out, and eventually I felt that this was the appropriate response:

Me: Alright, I'm going to give you the best advice you'll ever get: IF you are going to try dating older women you're going to need to get over your fear of blood, and you're going to need to start going down on them - and I mean that honestly for your own advancement, and in no way as an insult.
Me: Not necessarily at the same time.
Him: I had 2 gut-wrenching experiences in that department, so I'm not sure
Me: In which department?
Him: Going down...
Me: So? You think your spunk tastes like jolly ranchers or something?
Him: I don't know.
Me: Well, it doesn't.
Him: Okay
Me: It separates the men from the boys. And women want men. Otherwise you may as well stick to dating teenagers.

You know that thing...

...where you finally getting around to sleeping with that guy from last summer and then he's like, "Btw, I know a bunch of your close friends."

and by "know a bunch of your close friends" he means he once slow danced with your (soon to be!!!!!) roommate at a junior high dance and got a boner.

I've realized...

I realized this weekend that I was not very honest with myself and it took a little reflection to catch on.

I spent the entire weekend hanging out with awesome people but I kept finding myself distracted but my lack of contact with D&D and I now understand that this casual arrangement is really not working for me.

I went from a relationship that smothered me to the total opposite where I felt kind of lonely most of the time. D&D is so hot and cold. Awesome when we were alone together but not so great otherwise.

And why should I settle?!

So Sunday, after I got home from a night of partying with new friends, I sat down at my computer and with determination I emailed 30+ men.

I emailed men that i thought were meh and I emailed men that I may have once considered out of my league.

I sent them all the message "Hey, would you like to grab a drink sometime?"

Within a few minutes i got a response from a guy who I wasn't super excited about but he seemed friendly and upbeat. He asked if I had any plans that night and we agreed to meet for tea in half an hour.

I had to hustle to get my cute on as I was in sweats with no makeup on...

When I showed up at the cafe he was way cuter than his pictures! He was dressed well and was really friendly and chatty right away.

We had no problem talking for over an hour and then agreed to go for a walk. Since we were in my area he let me talk the lead on our route and I directed him to a park because I have a thing for swings.

We hung out on the playground for a bit until it started to rain really hard. By the time we got close to my place/his car we were both SOAKED. Since I was damp and it was late-ish on a Sunday night I decided it was an okay time to call it a night.

I hugged him goodbye and we made vague plans to meet later in the week. As I was walking up to my house he shouts "WAIT! I have a song I recorded that I want you to hear!" Of course I agreed to listen to it and it was super cute. He also played me some other songs that one of his bands recorded and we continued talking for a bit.

Eventually we had to relocate to sitting on my stoop because the rain was coming down so hard and we ended up chatting for another hour.

In the end we agreed that he will take me out for dinner on Friday night.

I'm super pleased by this random turn of events and I'm really interested to see how things go with this guy.

FINGER CROSSED!