This all happened when I was sober.

Let me preface this story by saying that before this summer my sex life was slow. No...slow isn't the right word....It did not exsist. I had started working really hard at online dating and decided to try to whore it up a little and see what happened.

One night Houston and I were chatting and she kind of dared me to have sex with four different guys this summer, and I agreed. NOW I realize that four does not seem like a big number. I could have had sex with four guys in a week EASILY because getting laid is easy, but I didn't want to just have sex with anyone. I wanted to feel it out and meet up for a drink and find guys who were worthy, which is funny because I realized how rare that is.

Until this weekend I was up to three guys, all of which I had seen more than once. I had had sex almost once a week and was fairly content with my progress, but I also felt a sense of urgency because Houston was leaving town to go to school in a week and that was my deadline. So I kicked the online thing into high gear.





Last night I did something that I would never have imagined would happen in my bed EVER. I am in shock at myself for my behavior, but also impressed, and maybe a little disgusted. Oh my god. I can't decide whether to brag or feel shameful....I have noooo idea....

Last week I had started texting this boy named Jesse. He texted me quite a bit from the begining which was sort of clingy but I didn't mind because it gave me something to do while at work and he seemed nice. We had agreed to go for drinks on Monday night.

Monday night rolls around and he texts me all day that he is nervous and excited. I didn't really feel anything going into this date...I had already kind of realized that I wasn't interested but I wasn't going to write him off without giving him a real chance.

We met at 9:30 at a local lounge and he was kind of awkward but I had no problem keeping the conversation going. I knew I wasn't interested, but I had my goal of four men on my mind and I guess I let that dictate my actions for the next part.

We decided to go for a walk after having a couple of drinks and I suggested we go to a park because I felt like going on the swings. On the way to the park he insisted I hold his hand and he stopped a couple of times to kiss.

When we get to the park I go for the swings right away. He was such a poop and was all awkward and embarrassed about swinging. So I just ignored him for a while and swung as high as I could. Then he suggested we go sit on a nearbye patch of grass.

We sit down and he starts at it right away. I just let him do his thing, which was licking under my chin. He also did this thing where he opened his mouth as wide as he could and stuck his tongue out as far as it will go, and then he crammed it down my throat. I would never like to experience that again.

At one point while he was kissing my neck he moved towards my ear, and the next thing I knew he had his tongue in my ear and was tongue fucking it. It felt very wet and all I could think about was how I looked forward to using my q-tips when I got home.

Then I made the mistake of agreeing to bring him home.

I know I should have let it end in the park, and I really have no explaination for why I let him come back to my place.

He insisted on having the lights off and he refused to take off his socks. He went at my boobs like a baby, as though he was expecting them to start lactating. He licked me down like a cat, but never once went between my legs (he licked my face from neck to forehead with a very wet tongue). He must have never heard of the clit. He had no idea.

When he had sex with me he could have been using his pinkie finger...it was small. It was thin and it was short. I used my hand on myself and eventually pretended to get off because I just wanted it to be over.

After he pulled out I felt sorry for how shitty he was and I went down on him. THIS IS THE MOST HORRIFYING PART: I was sucking his little dick, which I could fit in my mouth no problem, and I barfed. I barfed on his cock and he has no idea. It wasn't much and it happened right as he started to ejaculate so I just used kleenex to wipe everything up.... And then I tried not to laugh hysterically.

As soon as the mess was cleaned up I said something like "I don't mean to kick you out, but I should get to bed." I got dressed and escorted him out.

Now, what I haven't yet mentioned was that all while this date was happening, I was already planning what I could do to make this night better.

As of Monday morning I had been texting another guy who didn't seem like my type but was nice and funny. I knew Guy #2 was off work and would be coming through my area of town around midnight and so when I went to the washroom right before Guy #1 and I were leaving the bar I texted him and suggested a walk...

In the parking lot just as I was about to get inside Guy #1's car, Guy #2 called. I answered and made plans to see him when he got to my area. Guy #1 could have heard...I don't know. After I hung up I told Guy #1 that it was my roommate.

After Guy #1 left I immediately ran upstairs and finished barfing. I am all class. I know this. Then I brushed my teeth and my hair and touched up my makeup and left to meet Guy #2, who was waiting for me.

As I was orchestrating all of these events, I couldn't help but laugh at my behavior. What I did last night was something that would have made my jaw drop had any of my girlfriends done it. I kept stopping and laughing at myself.

Guy #2 was shorter than I expected, probably my height of 5'8 or 5'9. He dressed kind of gangsta, but all his clothes were new and clean. The conversation was easy. We didn't even have to think about it.

He told me about how he works at group homes for troubled teens and that he got into it because he was and addict and came from a broken home with a junkie mother. He also told me about how his fiance and 1 year old daughter died in a car accident 6 years ago. About how he was homeless because he hit bottom after that. And a million other sad things. He was the most positive and well-adjusted person I have ever met. He could take any situation and talk about how he took something positive from it.

We strolled around for an hour, stopping to sit on random benches. Eventually, on a bench in a churchyard, we started making out. He was good. I spent a little time batting his hands away because I still had this idea in my mind that I hadn't decided to meet up with him for sex. I know that it was something I kind of wanted, but I was in denial and insisted that I did not behave like this.

Eventually I relented, and I was glad I did. We got a little carried away and he ended up missing his last bus home. I invited him over, not because it would have been a drag for him to get home at this point, but because I did find myself drawn to him.

Over the course of the night we had sex four times, and it was awesome. It was so relaxed and we laughed so much. He showed me all the tricks he could do with his body, such as when he had a hard on he could make it dance and bob up and down. It was so hilarious and I laughed so hard at it, which made it go soft again. Then he made it talk to me. He could also bend his fingers back until they almost touched the back of his hand and he could pop his eyes out of their sockets...which I would NOT let him show me. He had lots of scars on his body because he was run over by a car as a child.

He also tans, which I made fun of him for even though I tan too. We compared tans and laughed at ourselves for being so vain.

I feel a little guilty for being dishonest with him about Guy#1 when it seems like he was willing to to tell me anything...but I do not regret my choices. I see no point in regret, especially when I made the sober decision to do this.

I didn't sleep until he left at 6:30 this morning. We were both so tired but neither of us could sleep because we both had too much to say.

Mr. A

Back when I was thinking about making a profile, a friend told me that the best method for online dating was to ignore all of the messages from dudes that initiate conversations. I was told that I should focus in on the profiles I found most interesting, and then send an email to those boys, and those boys only.

I obviously did not heed this advice at all.

Now, a few months in, a few dates in, but ultimately still nowhere in terms of finding anyone that I have any real connection with – I decided that it was mafukkin time to put my big girl pants on. It was time to BE THE INITIATOR!

I knew exactly which boy I wanted to email, but I was nervous. I practiced on some other profiles that were sort of interesting first, building up my nerve.

For lack of a better term, I’ve been profile stalking Mr. Adventures for several months. Before I uploaded pictures and made a real profile, I noticed his. He seemed perfect: a mix of tall, dark, and sexy-ugly. There was even a picture with a beautiful and rugged beard. I instantly had a boner for him.

Then, just before I put up pictures, he took down all of his photos. His profile was still there, but I figured that zero pictures = not currently looking.

I waited…

I didn’t really mind, to be honest. I hoped that his majestic bearded mug would return eventually, but I in the meantime I had no shortage of potential suitors to comb through.

Recently he uploaded photos again (not the bearded one! Womp Womp), and I resumed admiring his profile regularly.

One day, after reading a blog about being PIMPIN’ and taking charge of your life, I experienced a surge of confidence and fearlessness that provoked me to send Mr. Adventures an email.

Muffy once described his profile as: POW POW POW EVERTHING ANYTHING POW!!! I wasn’t sure what the hell to write in the email. He mentioned his love of adventures several times in his profile, so I asked him to regale me with his favorite Winnipeg adventure story. I figured that we could exchange stories and then I could suggest exchanging more stories over coffee.

Much to my delight, that is exactly what happened! Here is harshly summarized synopsis:

Coco: Tell me an adventure story!

Mr. A: AN ADVENTURE STORY! Imma hint at another story too. Your turn!

Coco:  AN ADVENTURE STORY! TELL ME THE OTHER STORY!

Mr. A: THE OTHER STORY! (it was super long and hilarious)

Coco: OMG THAT WAS AMAZING. Imma tell you more stories over coffee?

Mr. A: okay!
Coco: HERE IS MY PHONE NUMBER

Mr. A: HERE IS MINE

We planned to meet on Thursday after Folk Festival.

I was really nervous. Like, super fucking nervous. I had somehow gotten this man, who I had lusted over for months, to go on a date with me. AND SO QUICKLY! I avoided my previous method of having a phone conversation pre-date.

On Thursday we met at a coffee place. He texted me about an hour before to make sure we were still on. I appreciated that since I had been the INTIATOR the whole time. It was nice to know he might be even a tinge worried I’d bail. I told him to get his drink to go b/c we were going to go for a walk. He was early and sitting outside when I arrived.

He was wearing sunglasses and a straw fedora hat. I couldn’t really see his face for the first half of the date, and I worried that he was an ugly-ugly. We walked to a water fountain on Corydon and chatted. The conversation flowed pretty smoothly, although he went on mega tangents that were sometimes hard to follow.

Through a combination of a poor choice of hairstyle (bangs fully down), nervousness, and the heat wave, I soon became a disgusting sweaty mess. I was sure that I was bombing the date and that he was super grossed out by me. I was wearing a low cut top and I hoped that maybe my boobs were distracting him. I still wasn’t sure if I should care or not, since I was on the fence regarding whether or not he was an ugly-ugly or not.

We made it back to where we started and I freshened up in the restroom of a café. Then I suggested that we go to the park to check out the spinny chairs. He was game.

In the park, he twirled on the chairs for an amount of time that would have made me throw up. He loved it! When he calmed down, he asked me if I had plans for the rest of the night. I said I didn’t. Then he asked me if I had eaten dinner. I said that I hadn’t (I had been too nervous!!!). Then, much to my surprise, he asked me if I wanted to grab a bite.

I was delighted, but still unsure what he really looked like.

We headed to a local pub. We sat down and he went to the restroom. On his way back he sneakily bought me a beer that he had mentioned he thought I’d like on the walk. When he got to the table I suggested we move so that he could watch the game. We were both wracking up mega brownie points.

At last he removed his shades and hat. SEXY-UGLY FO-SHO! We shared nachos (he ate all the cheese!), told each other stories, and laughed and smiled a whole bunch. It felt easy and simple. It felt like one of those first dates that happens to girls you know, but never to you. It was textbook. And when the noisy nature of the bar forced me to lean in closer, I was pleased when I caught him occasionally and sneakily looking down my shirt.

I offered to go Dutch for the nachos, which I’ve since been told was very cool of me. We paid and left the pub and I veered us towards my apartment. Near my place he asked, “Am I walking you home?” and I said, “Yes, I tricked you into it.”

In front of my building I told him I had a fun night and that I’d like to see him again. He said that he’d like to see me again too, and then asked how long I’d be away for. He mentioned that he didn’t have his schedule for the next month and didn’t know when he’d be free, but then I think he realized it might have sounded like a brush off and told me that I should text him.

I was going to go in for the handshake, but before I could, he stepped towards me, said “oh, you’re going in for the hug!”, and hugged me. I wrapped my arms around him and breathed in his chest. Wonderful. And then we said goodnight.

Although it was a very nice date, I am not exactly all-a-flutter about it. Was the conversation really fun and easy? Yes. Was there chemistry? I’m not sure. At the end, I didn’t want him to kiss me, but I did like the hug.

I worry that he's secretly a big loser. 

A week later, while I was out of town, I texted him about something boring just to stay in touch, and because he had been all “text me!”. His responses weren’t revolutionary by any means, but he responded – so that’s something.

We are going out again on Monday to Folklorama. I hope he has grown a luscious beard in my absence.