Two-For Tuesdays: The Oral Conundrum – How I’m Slowly and Unintentionally Ruining The Confidence of Every Woman I Sleep With

There have been two times in my life where something so horrible, so mortifying, so absolutely embarrassing has happened in my love life that I’ve walked away from it fearing that I’ve completely scarred my intimate partner for the rest of their life and shattered their ego forever. Being that the most recent one occurred within the last several days, I decided to do a two part piece about how I’m slowly and unintentionally ruining the confidence of every woman I sleep with.

March 25, 2012
In probably one of the biggest transitional periods of my life, I had been carrying on an all but secret physical relationship with a woman who I had previously dated for an extended period of time, but had opted to take away the actual emotional side of the equation. Win/win for me really.

In the midst of the birthday weekend of one of my close friends, who’s couch I happened to be living on at the time, I received the usual and standard booty call text and, despite the massive party going on around me, I opted to greet the invitation with open arms. So, armed with a bottle of Jack Daniels and an enormous capacity for poor decision making, I hopped on the horny train and proceeded into a night of seemingly endless fornication and raucous debauchery. In retrospect, it was probably one of my favorite intimate experiences of my life; however, it would be met with sheer disaster soon enough.

After we passed out in a mess of of sweat, alcohol, and various other bodily fluids, I awoke in the morning to the pleasant surprise of some morning oral, which I of course welcomed with open arms. What a great way to start a day! Not only that, but she was really going for the gold. A for effort; however, we were about to have a very big problem.

You see, my beautiful young snowflakes, my enthusiastic partner, while motivated and talented, had failed to take into account two very important factors in her quest for morning satisfaction: The fact that she had drank a half a bottle of whiskey with me only hours prior, and the overestimation of her body’s natural gag reflex, two factors which led to the quick demise of what should have been a wonderful way to wake up.

So, when I leaned my head back in veritable hungover bliss and felt a rush of warm fluid wash over my skin, followed by the smell of stomach acid and the sound of her choking out the horrified words, “Oh my… oh my God” only to lean back down and realize that I had just been vomited on, there weren’t a lot of words I could muster up that could really give the situation any redemption.

I paused for a moment, truly allowing myself to process and understand what had just happened, before trying to calm this poor girl’s horrified crying by saying, “It’s alright. It happens. We’re just going to pop into the shower now, rinse off, and then never ever utter a word about this ever again.”

After our shower, and an extremely awkward goodbye, I proceeded to take my walk of shame, right to the bar, where the birthday boy and his friend from out of town had already been for two hours, and day drank like a champ to help me process the shame for the remainder of the afternoon. This, the end of what had previously been a healthy, pleasant, and mutually satisfying arrangement until that point.

For the love of Christ.

February 14, 2014

Valentine’s Day. It’s a wonderful time for those who have lovers, and a bitter and troubling time for those that don’t. Personally, I’ve never been very big on the “holiday” at all, but taking into account that my most recent relationship had reached some difficult times, I opted to try and make it special this year to make an attempt at salvaging the partnership. My attempts, however, were unfortunately futile, as that partnership has now ended. Fortunately, the event did leave me with one final hilarious story, which I will detail now.

The two of us had both been struggling to keep things going amidst a perpetual wave of fights and rough times, and we really wanted this particular evening to be something special, one final effort to see if we could still enjoy and love one another. To set the mood, I had made a reservation at a fancy restaurant in the city, one that set me back a few hundred bucks when all was set and done. It was actually really wonderful: A bottle of wine by candlelight, three amazing courses, and a pleasant vibe. We even had champagne and toasted, “To us.”

By the time we got back to her apartment, we were both drunk on both the mood and the wine, and it was time to get down to business. We hadn’t really been intimate that frequently in the previous couple of months, and she’d been expressing great concern with me about that fact, worrying that it would lead to our demise and that I didn’t find her attractive anymore. That fact was really driven home when she emerged from the bathroom sporting some new lingerie, lit a candle, and made it abundantly clear that the time had come to consummate the evening. She really looked amazing and, for the first time in a while, I was genuinely turned on.

As things got down to business, I began to perform my manly duties, opting to first do a little bit of “pre-heating” if you will. Now, this is something I normally don’t really enjoy doing, or have ever considered myself all that good at, so when she began to moan in pleasure and give me direction, I was extremely eager to do a good job; however, one of my oldest bad habits would momentarily lead to the demise of the whole evening.

One problem I’ve always had in times of intense physical behavior, whether it be in the bedroom, working out, at one point even singing, is that I tense up my muscles in the pursuit of strength and all around forget to breathe. So, in the midst of her passionate moaning and instructions to keep going, this bad habit took its vicious hold, and I proceeded to pass out, right there, in between her thighs, awoken moments later to her shaking my head and screaming, “Babe!? Babe! John!? Are you okay!???”

As I regained my consciousness and realized the absolute absurdity of what had just happened, I rolled over on my back onto the bed to collect myself and wallow in the fact that I had just failed this poor girl as a lover and likely traumatized her for life.

Wouldn’t it be perfect timing that, at that very moment, as we tried to get past the embarrassment of the situation and make sure I hadn’t had a legitimate health situation, her roommate, who had just arrived home, would knock on the door of her bedroom to thank her for the Valentine’s Day gift she had left for her.

So, there it was, our perfect night, the moment we had both worked so hard to make happen, what I had spent close to $300 on, what she had gone out and bought some new sexy lingerie for to revitalize our love life, this thing that we both placed so much emphasis on, culminated in her roommate standing awkwardly outside of her bedroom door to the unfortunate sounds of muffled laughter coming through it just moments after I’d lost consciousness face first in her genitalia.

Just ridiculous.

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