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First Time For Everything: Two Blowjobs In One Day

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First Time For Everything

Once upon a time in 2005, there was a young lady in her mid-20′s who lived in a faraway land known as New York City. This young lady was single and, as a result, was in constant pursuit of a man to be her boyfriend. She searched far and wide throughout the land for a proper companion. Eventually, many years later, she would find one to call her own, but in 2005 she was rifling through as many men as were available, ready, and willing. In the summer of 2005 she was balancing two different gentlemen, and it was in said balancing act that our fair maiden accomplished the near-impossible – the arguably slutty, the inarguably promiscuous – and put two penises into her mouth in one day.

Two different penises, that is. Just so we’re clear.

I was three months out of a long-term relationship in which, although there were redeeming aspects, our sex life wasn’t one of them. I emerged single and ready to party. No. Not “party,” actually. It was more that I was ready to “par-taaaaaaaay.” I would par-taaaaaaay safely, of course, but par-taaaaay nonetheless. It was in this frame of mind that I meant Jordan* and Hector.* Jordan I met at the local coffee shop. I would often go there to write, and over the course of several months we engaged in a lot of eye contact. One day, Jordan finally struck up a conversation.

He opened with, “Hi. I always see you here,” which gave me the opportunity to come back with the equally snappy, “I always see you here!”

He invited me to join him and I did. We chatted about all manner of things including Adidas brand footwear and the then-current trend of leggings-as-pants. Toward the end of our chat, Jordan invited me out for drinks. We went later in the week, and when the date was over, we made out. Jordan and I went out several more times, until eventually Jordan came home with me for drunken intercourse. All in all, the drunken intercourse went well. I could have done without the part where he asked me if I liked sweating – “Do you like sweating? Oh man, I love it. I love gettin’ all, like, slippery ‘n sh*t” – but otherwise it was normal and fun in all the ways I’d hoped. Over the course of the weeks, we continued to see each other.

Now, Hector I’d met through work. I was waiting tables at the time at a certain restaurant where he worked as a line cook. I had always found him terribly attractive. I found him so attractive, in fact, that I was able to ignore his dreadlocks. I don’t know about you, but I can really struggle with dreadlocks. I always found them unconditionally unattractive. That is, until I met Hector. On him, they sort of worked. And then! Then one day Hector showed up to work, and he had cut off his dreadlocks! Honestly, I don’t think I’ve ever been so attracted to someone in my whole entire life. I am embarrassed to tell you – but tell you I will – I threw myself at him. I soldiered right on over at the start of my shift, and I said, “Hector! Hey! How are you! What are you up to after work?”

And Hector smiled – he was also always very friendly – and said, “I’m not doing anything! Let’s go out for drinks!”

Here it bears mention that I don’t usually score such attractive men so effortlessly. What I think happened was this: Hector, like me, was just out of a relationship, and presumably looking to fill his time. That’s my theory on how it came to pass as smoothly as it did.

Hector and I went out for drinks later that night, and when it was all said and done, I just couldn’t help myself: I invited Hector home with me. Now, I’ve got no problem with casual sex, certainly, but even I don’t like to bring someone home on the very first date. In my defense, however, I was dealing with some high, high-level attraction, and also I knew him. We were co-workers. He wasn’t just some stranger on the street.

All bedroom business went just as well as I hoped it would, and when Hector left in the morning, he gave me the pleasant but predictable: “We should do this again sometime.”

“Indeed,” I said, “we should.”

As the weeks went on, I continued dating both Jordan and Hector. And because I tended not to see one or the other of them more than once a week – things stayed causal with both gentlemen – none of it ever felt all that risqué. UNTIL.

I had a Monday date scheduled with Jordan, and a Thursday date scheduled with Hector. This seemed reasonable enough to me. But then Jordan called to see if we could move Monday to Tuesday. I could, so I said sure. And then Hector called to see if we could move Thursday to Wednesday. Again, I said sure. I didn’t think all that much about any of it, because at the time of the reschedulings, everything was still a ways away. It wasn’t until the Wednesday morning after my Tuesday night date with Jordan, that I woke up with Jordan in my bed. And this, of course, was after doing all the things that people do when they’re in bed with a member of the opposite sex. We’d done it in the night. And we did in the morning too. And that’s when I thought, Oh, jeez. I’m seeing Hector tonight.

So then Hector came over that night. And I did it with him too.

And so it went: Jordan at 9 a.m. on Wednesday. Hector at 11 p.m. on Wednesday.

Did I feel disgusted with myself when Thursday rolled around, when I finally had time to think it over? I’d be lying if I said it didn’t. But I also felt sort of, like, weirdly impressed. If you can simultaneously feel slutty and powerful, I think that that is how I felt. If nothing else, I can resort to the whole “You only live once” way of thinking. If nothing else, it’s something to check off the fuckit list.

* Names have been changed

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