Enter Emily, literally.

{Undated. This one is weird. I know that Emily and my first time was during her relationship with Gord before they broke up. I just have no idea where it fits into the timeline. This entry follows the last on on the same page of the journal but it starts with the words ‘the next day’. The last one ends with ‘(3 weeks ago.) Hard to follow. This little asshole has really pissed me off by not recording dates. Hard to believe this person grows up to love history. Pffft! )

{Amendment: Moved back a week to March 23 due to the discovery of the March 25th letter.}

The next day, after school, she {Emily} comes over for the ride home. We start to fool around {on the couch downstairs. We agree that my bedroom would be more appropriate.} and things go really far and we go all the way. I was safe and wore a condom, but we made love. {I don’t even ‘make love’ to my wife. We fuck like normal people.} It was the most beautiful experience of my life, I loved it. {As I recall now as soon as Emily put the tip of my penis against her opening I started feeling like I was going to cum. I could take pride in that I made it inside for three pumps but it was exactly what you’d expect a boys first sexual experience to be. Emily was sweet of course. I only think about it as lame now that I’m a man. As a boy she made me feel like a God. I was glowing when I told Jeff 2 hours later.}

{I am minimizing this experience out of embarrassment but this was a flood of firsts for me. When we were fooling around and her bra came off that was the first time I’d seen a bare breast in real life much less touched it or put it in my mouth. Also, more memorably, when she took her panties off, while I was putting on the condom, it was the first time I’d ever seen a vagina in real life. In all honesty I could have probably cum right there if I stared at it too long. It was a truly overwhelming experience. I could not have asked for a better first time or a better first time partner. Though later in these journals I will show resentment for Gord and the fact that he was her first, the 35 year old me recognizes that her quiet confidence and understanding in these moments, the moments I define as perfect, were only possible because she knew what to expect. Now to more sad stuff.}

We did it again the next day {In the exact same pattern. Making out downstairs. Moved upstairs. Had sex. I can’t remember if I made it more than 3 pumps though… I’d like to say at least 4 but that’s optimistic.) We both regretted it. It had turned from a beautiful loving thing into a “that was fun let’s have sex again” thing. {Yeah! Dude. C’mon they can’t all be your first time.}

Neither of us regret the act we just regret how quickly we let it happen again. {That’s fair especially considering Emily is still with Gord at this point. She must have been going through so much I can’t imagine.)

The experience between us needed to happen. Over the last few months the sexual tension between Emily and I has been mounting and we would have exploded if this did not happen.

After the two times I expected a relationship naturally but she needed time still to get over Gord.

She saw him twice shortly after they had broken up. I never trusted her and bitched at her, but I trust her now. {Sadly, no you don’t. You’re an insecure 17 year old. It’s not your fault though.} I hate all of her guy friends but I love her enough to see past that.

Right now we are not on the greatest of terms because we are fed up with the situation.


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