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Making Sex Make Sense

A few months ago, a good friend of mine & I were at a bar having a drink. As usual, our conversation eventually wandered over to the topic of Sex:

“It took me a while to really understand Sex. I was having sex but I didn’t really GET sex. I had to sleep with a few different people before I really started to enjoy myself”

I can’t remember who actually said this (many martinis were involved at this point), just that we both AGREED.

I’ve always wondered what it would be like to be one of those people who has sex for the first time with their soul-mate. They end up having amazing chemistry with this person & they fall in love & stay together & never look back as they walk off into the sunset towards a life together filled with love & orgasms & interesting conversations. Cue movie credits.

Obviously, I’m not one of these people (If I was, this blog wouldn’t exist)

I always knew that SOMEDAY I would have amazing, mind blowing sex. It just didn’t happen for me right away. My experiences with relationships and sex have involved A LOT of trial and error.

Because I’m in the mood to do some over-sharing today, lets take a look at the evidence:

Guy #1: I won’t tell you the full-story of how I cashed in my V-Card. Instead, here is the Coles Notes version: It happened with my first real boyfriend in High School. The experience was sweet & loving but also awkward, bumbling and most of all painful. I felt like my insides were being pried open by the jaws of life. Luckily though, it only lasted about 60 seconds. After it was over, I remember staring at the ceiling thinking:

“So, THIS is what I have been waiting for?”

(honestly, I would love to meet a woman who’s first time was a mind-blowing, awesome, multiple- orgasm filled romp. Maybe that’s an oxymoron?)

Guy #2: This is the guy I started dating near the end of high school. I was really into him. We spent most of the summer after Grade 12, lying on his bed, fooling around. There was a lot of kissing, touching and…orgasms. And as you probably guessed, the orgasms turned me into a bit of a dum dum…enough to overlook stuff like how we had nothing in common (besides enjoying making out with each other) and that he had a speech impediment that made words like “sailboat” come out sounding like “twailboat” (oh the things you don’t notice when you’re permanently lip-locked). Despite all the fooling around, I made him wait 4 months to actually sleep with me. When the special night arrived, he climbed on top of me, pounded away like a rabid jackrabbit and passed out 3 minutes later (HUH?). My thoughts at that moment were:

“I waited 4 months for this?!”

Guy #3. He was older, devastatingly handsome, and much more experienced than I was. Thanks to this guy, I discovered that sexual positions OTHER than missionary weren’t just stuff from the pages of Cosmopolitan magazine, but stuff people actually did in real life. WHO KNEW. We ended up having sex in many new & exciting ways in many new & exciting places (we both lived at home, so actually having sex in a bed was usually off limits). Our little adventures were thrilling but, most of the time I didn’t really come. Sure there would be flutters of pleasure & those little blips of orgasms, but never anything like the earth-moving-mind-altering-OMG-I-found-the-BIG-O-all-consuming-waves-of-pleasure that I had heard existed (also thanks to Cosmopolitan). Partly, I think this is because I was so enamored with this guy that the following soundtrack would always be playing in my head whenever we were having sex: OMG, I LIKE HIM SO MUCH AND HE’S SO HOT AND I CAN’T BELIEVE WERE ACTUALLY DOING THIS TOGETHER OMG HE CHOSE ME TO DO THIS WITH AM I DOING THIS RIGHT? WHY ISN’T HE MAKING EYE CONTACT? I distracted myself to the point where it was like my body forgot to come. The other part of this was that he never tried to please me. He was a selfish lover. I realized this many years later when I slept with him again as an adult.

Guy #4. FINALLY GOOD SEX. With this guy, the emotional & the physical finally connected and there were orgasms… pretty good ones. The only problem was that I was dating a closet case. Even though the sex was actually pretty good, getting him bed was a struggle. We’d only have sex once every three weeks if I was lucky. Which, as you know is not enough-especially when you’ve just started dating. Most of the time I was left feeling like a cat in heat, scratching my nails on the wall of my poorly lit basement apartment. When I expressed my concerns, his response was:

“I’m OK with you sleeping with other people if you want”

(Not exactly what you want to hear from the guy you’re supposedly in love with)

What this really means is “I want to sleep with other people, but I just don’t have the balls to tell you this”.

Eventually, I did take his advice & slept with someone else (As did he: the cute guy in his acting class)


Guys #5-#7 were a motley crew of individuals that included a guy I’ll call “THE BITER”, a cute French Canadian (more jackrabbit action) and a guy who wanted to try out “moves” he’d learned from an “instructional porn video”. This didn’t go over well. To borrow a line from Seinfeld, “it felt like I was being probed by aliens”


Which brings us to Guy #8. Have you ever met someone that you have been, instantly, insanely, attracted to? Yeah, that’s #8. We met on the eve of my 21st birthday at a bar I used to go to. One minute we’re dancing together, the next we’re pressed up against the packed bar, making out passionately, his hands reaching up under my skirt.

him: “Can I take you home?”
me: “I’m not that kind of girl. I don’t do those kinds of things”
him: “Ok, well do you want to come outside and have a cigarette with me?”

So, I followed him outside into the alley adjacent to the bar. He never ended up smoking the cigarette. Instead, the kissing continued. Then he kneels down, pulls my underwear down & begins going down on me, while my back is pressed up on the graffitied wall of the alleyway. Barely Concealed by the darkness from the passers by on Queen St: ORGASM. It was totally sleazy & inappropriate & hot.

him: “Can I take you home now?”
me: “No. How about this: I’ll take YOU home. My turf. My rules. And I’m NOT sleeping with you”

We spent the next four hours in my bed, mostly with his heads between my legs.

I counted the orgasms 6….7….8……….9

(where did he learn to do this?!)

When the clock struck 6 am, he resurfaced for air. Out of breath & exhausted I said to him:


We finally had sex. We came together as the sun rose over Toronto.

I was THAT KIND OF GIRL after all.



The year I spent trying to date Mr. Magic Tongue, was a total disaster. Outside of the bedroom, he was completely wrong for me. I just didn’t see it. The Sex had turned me into Blind Dum Dum in love. But, that’s beside the point. What’s important to understand about this experience is that it changed me. I became confident in bed, I learned to express myself and ask for what I wanted & finally I understood what it was like to be consumed in that I -need- to-have- you- I- don’t -care- if- we’re -in- an-alleyway- or- on -top -of- a -washing- machine- we -need- to- have- sex -right- now -kind -of passion. Take THAT Cosmopolitan magazine!

Years later, I slept with Guy #3 again. I remember he was on-top of me, doing what I like to call “slow-mo jackrabbit action” aka “barely moving” . Frustrated, grabbed his ass & called out:


His eyes nearly popped out of his head, he looked at me and said,

“You’ve CHANGED”
“Yeah, I’m no longer 18”

I had changed. Although #3 didn’t fully appreciate this, I’m sure the guys who came after him (no pun intended) did. The transformation into the sex-blogging-lingerie-loving-self-proclaimed-brazen-hussy I am today was already on its way.

By the time I got to Guy #13… Well, I won’t tell you what happened there YET, but I’m pretty sure we broke a few laws the first time we hooked up.

The rest is history.

All these stories come full circle back to a conversation I had recently with another friend. She said to me:

“I feel kind of embarrassed about the number of people I’ve slept with”

I used to feel the same way too. I used to beat myself up about it. Call myself a slut. But, as I’ve realized, negative self talk gets you nowhere. Somewhere around the time when I moved in with my boyfriend, I decided to say FUCK IT and decided that my “number” no longer mattered. Looking back on the past, I realize that my “number” (which I’ll never reveal but I can say doesn’t stop at 13) matters less and less. As long as you’re taking care of yourself, respecting yourself & the people around you what’s the big deal? What’s the point of constraining your own sexuality because you feel like you need to fit in with some arbitrary definition of what’s a socially acceptable number of people to have slept with? Because you know what? That number doesn’t exist. Why make yourself feel bad? If I had decided to stop sleeping with people at Guy #3, or #5 or worse #7 (that video he watched should really be banned. for reals) because I was afraid of being labeled a “slut” and instead thought I should just “wait for the right person”, then I would have missed out on a lot of the experiences that have made me who I am today. The irony of this all was that I WAS “waiting for the right person”. He just didn’t come along for a very, very long time.

If you’re still waiting, or trying to make sense of it all: don’t worry. Sometimes it takes a long time to get things right. It did for me. Take a deep breath. Re-Group. Hug yourself. It will all work out. And in the mean time, don’t be afraid to embrace your inner Brazen Hussy. She’s a lot of fun.

{Today’s photo is from We Heart It. And no, I don’t condone wearing socks in bed. ever.}

Can anyone else relate to this?


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