Welcome back to our Friday feature on BCP, “The Best Sex I Never Had: Sad Tales of Tail,” in which we invite our readers to submit their most humiliating, pathetic, and just-plain-awful sexual experiences for public consumption. Seriously, email us! It’s like a group therapy session with 1,000 of your closest friends. You’ll feel so much better after you share. If you would like to contribute, see the rules for submission at the end of this post.

Losing your virginity is generally awkward and uncomfortable in the best of circumstances.  Today, The Mayor of Bethville bravely shares her own stab at deflowering, and finds herself in a situation in which “I’m sorry” just isn’t enough.  Another promising start quickly unravels, after the jump. 

The Mayor of Bethville writes:

It was a super-hot and extremely humid day in July.  And I had a date with this guy.  We had actually gone out just the night before, had a crazy-awesome makeout session, and decided to continue the next day.  So, we went to a movie and had lunch.  And I KNEW I was going to seduce him.  Why?  Because I was still a virgin and feeling extremely shitty about it.  Plus, his apartment was close by.

So he was all, “I have air conditioning,” and that was all he needed to say to get me over there.  In retrospect, I was soooo easy.

Anyway, we start making out.  I’m terrified and a little baffled as to what I was supposed to be doing, as my only real experience was in administering blue balls.  At some point, I was naked and I felt something poking around down there, but I could not tell if it was a finger or a penis.  Turns out, it was a finger.  And when I got a look at the penis, it was totally limp.  Limp like an overcooked noodle.  The fingerbanging went on for about ten minutes, and I was starting to chafe.  I said, “Hmmm… that’s not doing it for me.”  So he went down on me for a while.  I got off.  He got up and went to get a glass of water.  Still limp.

He came back to the bed, laid down, and turned on HBO.

We laid there for two hours watching Napoleon Dynamite.  He would get up once in while and over to the window, naked, to smoke a cigarette.  Finally, I was like, “Should we try again?”  Because like hell was I leaving there without a proper screw, after all of my effort.  So we fooled around.  Nothing.  I went down on him.  Nothing.  We tried missionary.  We tried doggy.  We tried everything, and he just kept falling out.  By that time, it was midnight, and he wanted to watch Independence Day.

So I was like, “Yeeeeeah, guy.  I gotta go home,” and started to leave.  And this was where things got awkward.  He kept apologizing.  Profusely.  Again.  And again and again.  And I kept saying, “No, it’s totally fine. There will be other times.”  Because I did like him and I did want to see him again.  I felt really bad, but what could I say?

Everything I knew about that type of situation I had learned from watching Friends, which was entirely unhelpful.  He insisted on walking me to the subway.  Once there, I kissed him…. on the cheek and ran away.  Because during the entire two-block walk, he continued with his steady stream of apologies and possible explanations as to why…

I never saw him again.  Poor guy.

Can you top Bethville’s story? Is that good sex compared to what you’ve been through? If you’d like to contribute a sad tale of tail, please email: tarred.and.tailfeathered@gmail.com. Keep it short, sweet, and as explicit as you like. Include your preferred pseudonym. Please also be factual – this is not “Penthouse Forum.” And that’s it! We can’t wait to hear the gory details, so get to it. They’re posted in the order in which they’re received.