Dating : My Cherry Popped On My Boss’s Couch

SEX

And other mishaps + lessons from losing my v-card

I was 19 years old, on my way to another one of my boss’ after-work get-togethers.

At the time, I was in college and working as a waitress at a restaurant — one of my favorite jobs I’ve ever had. My coworkers were all around my age, the work was easy, and everyone got along really well — making for lots of boozy memories made together outside of the restaurant.

And for some reason — I found myself frequenting these hangouts over the college frat parties I’d been used to…willingly.

This particular night, it was Valentine’s Day. But, I was a single college girl, just ready to have some drinks with my friends.

Little did I know that I’d be losing my virginity on my boss’s couch later that night.

So, the culprit? His name was Joe. He was a line cook, who started harmlessly talking and joking around with me…a lot at work. He was also seven years older than me.

‘The whole package’ I’d insist if you’d have asked me back then.

Being the hopeless romantic that I was, I had a knack for finding the best in any male that showed an interest in me. And Joe was no different.

Sure, he was a college-dropout cook at a mediocre restaurant that was hitting on someone seven years younger than him…but, we’ve all got our flaws, right?

Unfortunately for me, Joe’s baggage and minor “flaws” didn’t end there.

The night of the after-work-that-happened-to-fall-on-Valentine’s-Day-party, I indulged myself in a few glasses — okay, the whole bottle — of pink Moscato.

With both alcohol and sugar rushing through my veins, I could feel my drunken attraction towards Joe building. With flirtatious comments going back and forth all night, I couldn’t help but wonder if he was ever going to make a move.

We’d sit next to each other on the couch, and he’d shyly graze his rough hands up and down my thigh, giving my skin goosebumps to the touch. We were partners for every single drinking game we played. Towards the end of the night, we were holding hands and wouldn’t go anywhere without the other.

Towards the end of the night, I finally got my wish.

The whole party had disappeared as it neared midnight. My boss had drunkenly passed out in his bedroom. It was just Joe and me left in my boss’s living room.

We sat on the couch, watching T.V. and cuddling. Finally, he looked at me and said, “I’ve wanted to kiss you for so long. Can I?”

I grabbed his face with both of my hands and brought it towards mine, initiating a make-out session that would quickly escalate into me losing my virginity.

Each kiss was completely cosmic, taking both my mind and body to another dimension as he slid down my panties, kissing my legs while his mouth headed straight towards my pussy.

After getting the best oral of my life and with granted permission, he slowly entered me. “Ummm, ouch? Is this supposed to hurt?” I thought to myself as I laid on my back like a lifeless fish, gazing into the eyes of someone I thought I might have real feelings for as he took away my innocence.

I woke up between the hours of 5 and 6 A.M. in a hungover, brain-fogged confusion.

I looked down the couch. There he was, sleeping ever so peacefully. He was so incredibly handsome. He also took my virginity. I couldn’t stop thinking about it, no matter how painful the first time was. I imagined times two and three could be much, much better.

I looked down at my body, and noticed blood laden all over my boss’s white couch. “Fuck,” I thought to myself. I guess that’s what they call the infamous “cherry pop.”

I ran into my boss’s kitchen in a panic, hoping I could get out the stains to avoid any embarrassment. As I grabbed a paper towel, Joe’s phone lit up on the kitchen counter.

“26 Missed Calls from Nikita”

“What the hell?” I thought to myself. I looked over at him at the couch, still fast asleep. If there’s one thing I know to be true, older men never have passcodes on their phones. I opened it up and headed straight for the text messages.

Mortified, I found exactly what I thought I would: a long stream of angry text messages from Joe’s girlfriend, wondering where exactly he spent his Valentine’s Day evening.

“Fuck,” I thought to myself, yet again. I was the other woman, and I didn’t even realize it.

I headed back to the couch and threw the phone at Joe, unlocked, opened on his text messages with his girlfriend.

He jumped awake, confused at first. And then he looked at his phone, and back at me. “I’m so sorry I didn’t tell you, Kelsey.” Classic.

I felt so naive and completely stupid. I was really starting to catch feelings for this bozo, and as it turns out — I was just a side piece because he was bored of his girlfriend.

“I thought you had feelings for me. I thought this was going to turn into something…” I stated, words shaking.

“Kelsey, this would’ve never worked. You’re young, you’re pure…you have so much to learn. I’m literally on house arrest right now. You don’t want to get involved with someone like me.”

Well, I wish you would’ve said that before you stuck your penis in my vagina, you idiot.

After further inquiring about the house arrest statement, I found out that Joe had just been put on house arrest because he punched a minor at a bar. Not to mention the slight fact that he was breaking house arrest by spending the night at our boss’s house.

Shockingly enough, it wasn’t the first time he’s had legal trouble.

• Never mix work with pleasure, no matter how hot they are.
• You don’t have to lose your virginity to that special someone, but at least make sure they’re not a complete piece of shit before you do it.
• At some point or another, we’ve all been the other woman/man — even if we didn’t know it. Don’t bog yourself down with shame if it’s happened to you.
• If you see one red flag, don’t ignore it because there’s probably a million more where that came from. Listen to your gut.
• Older men aren’t always more emotionally mature.
• If the men you’re dating have time to punch minors in the face, there’s a 99% chance that they’re not dating material.