Relationship blunders : the gross, the bad, and the ugly




The grandfather grope

In high school I was dating (as my Italian mother would say) “a nice-a Italian

boy.” He was my first “serious” boyfriend, so you can imagine the cheesy puppy love: walking me to my bus at the end of every day and sneaking into portables to make out.

As our relationship proceeded for the next couple of months we were convinced it was love. Mind you, our relationship only lasted six months total but it was high school, and it was serious. As a mandatory request from Italian mothers, it soon came time to meet the families.

His Nonno (grandfather) owned a shop in the local mall so it was a very casual introduction. Once we got past the double-cheek kisses, his Nonno asked him for some help around the shop. As we walked towards the back room, I felt a tight squeeze on my right butt cheek. Mortified, I turned around to smack my boyfriend, as that is not something I would want his family to witness.

But, wait a second. My boyfriend was on my opposite side, meaning he would only have access to the left cheek. So who was on the right? Yes, it was his Nonno. My boyfriend’s 70-something-year-old Nonno had managed to grasp the perfect cusp of my right butt cheek.

So as I refer to it today, the “Awkward-Nonno-Right-Cheek-Butt-Grope” remains both a mystery to my ex-boyfriend, and a fond, long-lasting memory to his grandfather, no doubt.

The missing miniskirt

We’re probably all familiar with the chaotic mess of clothing that results from sexual debauchery, but sometimes cleaning up can have its own surprises.

My girlfriend and I had driven her parents’ car out to a vacant suburban parking lot to do the deed, and afterwards had to collect the many layers of clothing we’d stripped off in the process (it was winter, after all). After nearly half an hour of looking under seats, between seats, and in any interior compartment imaginable, it seemed that her miniskirt had vanished.

We drove back to her parents’ driveway, wondering all the while what would happen if the lost article were found in the morning, and upon arriving decided to continue the search. We gutted the car—all doors open, trunk popped, flashlights employed—and found nothing. Exhausted (by this time, it was past 3 a.m.) and stupefied, we were about ready to chalk the event up to mystery when, scratching our heads outside the driver’s side door, my girlfriend noticed the skirt—pulled up over her stomach.

The curious case of the bump

As a girl who doesn’t mind being set up by friends, I was pleasantly surprised when a friend told me over the phone that she has this perfect guy that she’d like to set me up with. I quickly agreed to the date and was excited when he was at my door the next day to take me out.

Looking him over, he had nice hair and some nice muscles, but I couldn’t help but notice the slight bump he had on his cheek. I was about to ask him if a bug had bitten him or if something had hit him, but decided not to in fear that would be rude. The date went by very awkwardly as he tended to fidget a lot and go to the washroom more than any normal male would. I was pretty happy when we decided to call it a night. As we were sitting in his car and I was getting ready to say the usual bye and thank you spiel, I accidentally knocked over the mug in his car. Reaching forward to pick it up, I end up hitting him on his right cheek, slamming into his bump. Next thing I know my cheek is covered in liquid and I realized at that moment that I had ended the night with popping my date’s zit.

The naked surprise

I was hanging out with friends at a bar one night when I noticed this really cute girl sitting alone, reading a book. She was dressed in a tight outfit and her body was smoking. As the night progressed, I got up to talk to her and we actually hit it off. After a few drinks, she asked me if I would like to come over to her place and like any male would, I said yes.

Once we were at her apartment, we started making out on her couch and having a fun time. It wasn’t until a few minutes later she grabbed my hand and took me to her bedroom to finish what we started. She sat me on her bed while she said she was going to freshen up in the bathroom and all the while, I quickly dug into my jeans to find a condom. As the door opened, I was absolutely speechless. The cute red-head from the bar was completely naked except for the huge strap-on she had sitting on her waist. Needless to say I ran out of there quicker than I’ve ever ran in my life.

There will be blood

My girlfriend and I were making out in the time between the break in our classes and the moment her parents came home from work. I was fairly confident in my makeout skills (I no longer licked her teeth by accident), and I believed it was time to take things to another level.

A naked level.

With the grace of a knocked-over vase, I attempted to undo her blouse with my mouth. I thought women wanted men who opened things with their teeth. I swooped my head down to begin the seduction.

But I ended up headbutting my girlfriend in the nose.

She bled through a toilet paper roll, and said her stomach hurt. I imagined what my mugshot would look like. Then we continued making out.

We took it upstairs since if this was gonna happen, it needed to happen immediately. I was rebounding from assault to sex.

I decided to pull off another porno move; I was gonna give my girl oral. After trying to remember what the internet taught me, I dove in head-first.

And I tasted blood.

It turns out that her “stomach pains” were menstrual cramps. Surprise! It left a bad taste in my mouth. I ended up being a virgin for a few years more.

A POW-erful impression

I met my ex on the second day of frosh week walking towards the food line.  I saw her walking ahead of me, and, eager to impress, came up alongside her.  Magic being a hobby of mine (and the closest thing I had to a pick-up at the time), I went to try and conjure a coin out from behind her ear.  It was the first time I had attempted the maneuver while walking, and in my nervousness, I misjudged where her head would be.  End result:  I walked up to her and smacked her across the face.  After a moment of stunned silence, I could do nothing but run.  We ended up together for a while. Moral of this story?  Everyone loves a magician.

About the Author

By Excalibur Publications



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