Love, Sex, & My Ex Contest Winner - Week 6

The Love, Sex, & My Ex Contest is not dead! I will be posting one story each day this week to get caught up, so check back tomorrow for Week 7's selection. And now, on to this week's winner...

Don't Date Your Boss
by N. North

When I was in my mid-twenties, I worked at a restaurant while finishing school. I had a bad attitude about waiting tables but an IQ over 75, so the owner promoted me to part-time manager. The full-time manager, "Darren", and I carried on a friendly flirtation, and, once I was promoted, decided to try dating. Try dating. Not fall deliriously in love, get married, procreate and live happily ever after, no. Date. Within days of us taking this leap, the entire restaurant knew we had become romantic and instantly looked at us like we were a couple. Darren included.

After a week and a half went by, Darren and I slept together for the first time. Big mistake. Not only was the sex less than satisfying (read: no milk and cookies for me), but, while the man was still inside of me, he felt the need to tell me HE LOVED ME! Let me just say that ten days into dating and first time coitus is NOT the time to share this sentiment. I thought only psycho females pulled sh*t like this. Unsure of how to respond and in a panic (remember... I was in my mid-twenties and had a penis inside of me), I replied, "I love you, too." WHAT ELSE WAS I SUPPOSED TO SAY? I was pinned underneath the guy.

It gets better.

Did I mention that having sex with Darren was like being fucked by a balloon animal? Yeah, it was. Also, it seemed that Darren missed health class the day they taught condom application. During our three attempts at sex, he used what I call the "sock method" to put on the condom—he'd unroll it completely, bunch it up between his thumbs and forefingers, and proceed to "shimmy" down it onto his pecker, much like how one puts on a knee-high sock. The difference between the two, however, is that shimmying on a sock doesn't leave a big air bubble at the end like shimmying on a condom does. And no, the added length and girth of the air bubble didn't enhance the experience, I assure you.

After the three attempts at sex, I dumped Darren without explanation. Looking back now, perhaps I should've communicated my true feelings to him, explained the errors of his ways, drawn him a diagram—whatever. The bottom line is, don't date your boss, because if you think the sex is bad, dumping him is worse.