Tag Archives: bad sex

The Bad Date Chronicles – 15 Second Man Edition

Gentleman...start your...oh..

Yes, the title means exactly what you think it does.  15 Second Man was the catalyst for this post.  Here is the rest of the sad, sad story.

15 Second Man was my 2nd (but sadly, not last) foray into the wilds of Craigslist.  There  was no picture attached but the ad was so charming I was willing to take a chance.  It was a send-up of the old Dr. Seuss One Fish, Two Fish book and consisted of about 20 really funny, thought-provoking questions.  Of course, possessed of a strong wit and a love of answering questions about myself (I have answered absolutely every question on OKCupid) I had to respond.  He seemed to really dig my answers and we exchanged numbers after some really entertaining emails.

Don't tell me you wouldn't hit that

Due to scheduling conflicts, we weren’t able to get that first date on the calendar for almost two weeks.  In the meantime, we had frequent communication, texting every day and talking on the phone almost every other day.  We sent photos of each other back and forth and to my surprise, he was attractive!  Definitely on the larger side but in a very cute, Man vs. Food kind of way.  Things got hot and heavy pretty fast.  The back-and-forth quickly devolved into full-on sexting and even phone sex, all before we had even met!  One day, we clocked in at almost 600 text messages sent back and forth.  Needless to say my productivity level at work plummeted. We were both almost drunk on anticipation of meeting each other, finally, in person.  Would the chemistry be there?

The night of the date finally arrived, and to this day, I can’t recall every being this nervous about a first date.  It felt like so much was riding on it, that I would be beyond embarrassed if this person, whom I’d already been pretty intimate with, would turn out to have no interest in me or vice versa once we actually shared the same space.  I was beyond relieved when I first caught a glimpse of him at the door of the restaurant.  He was adorable. And he seemed to think exactly the same of  me.  The butterflies and nerves quickly departed as we settled in at the table for some drinks and dinner, to be followed by a trip to the bowling alley.  The date couldn’t have been more perfect.  We were clearly digging each other, and having a great time.  When, a few hours later, he pulled me in for a kiss in the elevator of his building, I though I had died and gone to wherever it is that all good sluts go to when they die.

Despite the undeniable sexual chemistry, we actually “negotiated” what was allowed and not allowed once we got down to business.  We both agreed that we didn’t want to rush into sex, that we wanted to give it time for something to really develop before we took that step.  It was perfect!  All too perfect!  And then…I understood why he took the nuclear option off the table.

Cut to his bedroom.  We’re kissing.  Passionately.  Like in the movies.  And I don’t mean the kind you can get from Netflix.  Being the surgeon that he was, he was very, very, VERY good with his hands.  Being the feminist I am, I decided that he deserved some reciprocity.  The equipment was impressive.  Far from the smallest but not too far off from the biggest I’ve encountered and of a perfect girth.  I was literally chomping at the bit to get to work on this thing.

I’m no surgeon, but I’m pretty good with my hands as well.  I didn’t realize I was THAT good.  A mere 30 seconds after first contact, Old Faithful erupted unexpectedly and way ahead of schedule.  I was stunned – this had actually NEVER happened to me before, although I told him otherwise.  My years of high school theater served me exceedingly well that night.  I was kind and reassuring and all of those things you need to be in order to preserve the fragile male ego after is has suffered such a…blow.  Took my time saying goodbye and departed for the night with a very nice goodbye kiss. Continue reading


The Bad Date Chronicles – Mr. SportsCenter Edition

Stop smirking Neil. It’s not funny.
Last winter, I met a gentleman on a popular dating website.  Let’s call it … snatch.com.  On paper, everything seemed great.  Tall, dark, and handsome with a job, a car and his own place.  We exchanged a few witty emails back and forth and quickly progressed to a few light-hearted and flirty phone conversations.
The day of the big meeting was right out of one of those dreadful Katherine Heigl rom-coms, and I just ate it up.  Imagine, if you will a gorgeously chilly, crisp winter day in San Francisco.  The location – Union Square.  Christmas shopping was in full swing and the square was full of shoppers clutching their packages, tourists lined up at the Powell Street cable care turnaround, festive music wafting from the department stores.  We walked towards each other from opposite ends of Powell Street, on our cell phones when we saw each other across a crowded city block.  Eyes locked, shy smiles of recognition and relief lit up our faces as we walked towards each other, closer and closer until, as if drawn together by magnets, we half-jogged into a warm embrace.
He was more handsome than his online pictures, incredibly tall with mesmerizing green eyes that I just wanted to hibernate in for the winter.  Equally stunned by my appearance as I was with his, we ducked into a charming little dive bar and took a seat in a booth near the back.  The waitress came to take our order, and we blurted out the exact same drink order in unison.  Laughing, we looked at each other in astonishment and I was convinced right then and there that he was THE ONE.  The next few hours passed like moments as we sat in the cozy booth, kissing, my legs draped over his, talking about our lives and how neither of us could believe that this was actually happening!
Sadly, the time came for me to return home, and hand-in-hand we walked the few blocks to the train station.  Embracing tightly and sharing just one last kiss, we made plans to see each other the next week.  We kept in touch with a few brief calls that week, and my excitement mounted and the anticipation of spending the night with this man kept me alternately blissed-out and irritated at how long the week was taking.
The big night had finally arived.  Decked out in my black knock-off Herve Leger, hair and makeup perfect, I headed over to his house for what I believed was going to be an absurdly romantic evening.  He however greeted me at the door with a look of supreme annoyance, a ripped up white t-shirt, and ill-fitting boxer shorts.  He ordered me to sit on the couch while he finished writing an email in the other room and when I didn’t immediately comply, he raised his voice and repeated himself.  Stunned, I plopped down on the couch waited.  After a few minutes he came out and sat next to me.  “Are those fake eyelashes you’re wearing?  Take those off they freak me out.  And while you’re at it, take off all that makeup .  I hate that.” Continue reading

Follow

Get every new post delivered to your Inbox.

Join 80 other followers