Foreplay: People Pleasing Turns into a Tragically Awkward Experience in a Sea of First Times

Dear Cards,

Kitty here! While describing my first kiss might seem a bit juvenile for a sex column, I want to share the story of how mine turned into an excruciatingly awkward blowjob, and unpack how absurd it is that I felt the need to negotiate losing my virginity.

First of all, let me get this out of the way: I had my first kiss at 15 years old. My parents have made fun of me for this, but they could never understand how a pandemic affects an adolescent’s milestones! While they were busy going to makeout parties in their middle school friends’ basements, I had to sit six feet away from any boy I invited to our house. Once the masks came off and my braces were a thing of the past, I was determined to suck face.

I decided to go for a family friend of mine (typical). He and I grew up together, so I felt comfortable asking him if he wanted to come over and play Mario Kart. We were sitting on my couch and, as you’d expect from just about any high school boy, it didn’t take long for him to bring up the topic of kissing. He revealed that his first kiss was a summer camp fling, and at that point I was feeling like a pretty late bloomer. Then, when I told him I had never kissed a boy, he proposed the idea of us “practicing on each other.” Smooth, right?

For some ungodly reason that had to be related to my underdeveloped frontal lobe, I could not conceive of kissing this guy while sitting next to him; it seemed physically impossible. So, I boldly hopped up from the couch and proceeded to straddle my childhood friend. After talking about it logistically for way too long, he finally leaned in, making that face guys make before they go in to kiss you (you know the one). I don’t need to explain how bizarre kissing feels the first time you do it, but let’s just say it caught me so off guard that I pulled away and said, “Woah!” Nice one, Kitty. Very attractive.

After “practicing” for a little while, I could tell I was doing something right based on how his body was reacting (if you catch my drift). After what felt like 5 minutes, the guy pulled away and said, “I have a condom if you want to… you know.”

Penis havers, take note: it is important to know where to bring condoms, and when to mention that you have one in your pocket. Sure, it’s better to be safe than sorry, but I’d argue it’s pretty wild to mention that you have one only 5 minutes into the other person’s first make out, amidst Mario Kart music at that. As you can probably gather, I was not ready to have sex.

I felt this weird sense of obligation, as if agreeing to kiss him meant he inherently had the right to penetrate me. His comment seemed so out of character, and served as my introduction to the power horniness has to cloud the brains of men. For some reason, I thought it was better to lie than to admit I didn’t feel comfortable having sex with him.

“I’m actually on my period, but I could give you head if you want?”

He was thrilled. Shocker! He pulled down his athletic shorts, revealing the first penis I had ever seen in person. It looked like a sea monster, and somehow I was supposed to fit it into my mouth. 

It was a tragically awkward experience. Honestly, I think it’s pretty hard to give a bad blowjob, but I was so focused on getting all of it into my mouth that my tongue wasn’t even part of the equation. Plus, he started pushing my head, which made me gag and feel like some sort of amateur porn star. While I was physically there, kneeling before my couch in broad daylight, my mind was in a completely different place; I couldn’t wait for it to be over. 

Luckily, it was a pretty brief ordeal. What felt like an eternity was at most 18 seconds, and I knew it was over when I noticed a foul warm mass in my throat. Since I had been gagging, I almost thought I threw up in my mouth. When I looked up and saw his blank expression, however, I realized he had finished, and THAT was what semen tasted like.

Naturally, I couldn’t bring myself to swallow. While I probably thought swallowing semen could get you pregnant at the time, the main reason I spit it out was because it tasted so vile I was afraid it would burn a hole through my stomach. Closing my mouth tightly, I stood up and bolted to the laundry room to spit his semen out in the sink. Yikes.

When I came back, I apologized to my friend for running away. He was very nonchalant about the whole thing, which freaked me out. I thought I was crazy for perceiving my first kiss (and blowjob) as a big deal.

In hindsight, I wish I had told him I was hesitant to go further than kissing that day. I was initially excited, but when things started moving too fast, I sacrificed my own comfort to protect his feelings.

I may have been a sophomore in high school, but stories like this are extremely common whether it is someone’s first sexual experience or not. If your partner shows any signs of hesitation when engaging in physical intimacy, it is crucial to check in on them regardless of what they have already agreed to. Open communication and consent between all parties is vital, and your well-being should be prioritized above all else.

Thank you for sitting through this painful read, and I hope you enjoyed indulging in the bleak world of adolescent sexual exploration! If you have any essays, questions, comments, or anything you’d like to share, please consider submitting on the anonymous form below to be featured in a future Foreplay article!

Stay safe and sexy,

Kitty