I'm Not Good At Casual Sex So I Bought Gifts For My One Night Stand

My belief system of waiting to lose my virginity had landed me with a total loser for almost three years, so maybe it was time to try the complete opposite. I enjoyed sex. Why shouldn’t I have more of it? With a variety of people?

Nov 25, 2013 at 5:00pm | Leave a comment

It took me until I was twenty-three years old to lose my virginity.  A mix of Catholic and Jewish guilt (I’m a Cashew-half and half) coupled with the fact that the name Danielle translates as “Judged By God” and that I paid VERY close attention in health class during the sexually transmitted diseases slide show.  But lose it I did, along with my heart to a guy five years older than me in age, light years ahead of me in sexual experience but with the attention span and emotional intelligence of an eight year old.  

After emerging from the rubble of that mess, I found myself completely unsure how to go about pursuing a new relationship. Did I want another serious boyfriend? Should I date casually? Sleep around a little?  

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What’s a girl to do to try to expand her sexual horizons?

My determination to set a new romantic path sparked from the need to ignore the part of me that still hurt.  The wounds that I had long since been pretending didn’t exist because the amount of time that had passed since the break-up felt far too long to still be in a grieving period. And somewhere in the back of my mind was that old adage, “The best way to get over someone is to get under someone else.”  

My belief system of waiting to lose my virginity had landed me with a total loser for almost three years, so maybe it was time to try the complete opposite. I enjoyed sex. Why shouldn’t I have more of it?  With a variety of people?

And yet I still wasn’t sure I had it in me to pull off the total anonymous stranger one night stand. So I called this guy Brian one Friday night. We had accidentally made out once at a very drunken happy hour and he was very seductive towards me, but I had always resisted. He worked for a company that did a lot of business with mine and occasionally even popped up in my office for meetings. But this was the new me. A little reckless and a lot bold.        

“Hi Brian, it’s Danielle. How’ve you been?” I asked when he answered the phone.

“Oh hey! I’m good. Long time no talk. What are you up to?”  He only sounded mildly surprised to hear from me, which emboldened me further to ask him what his plans were for the weekend. “Tomorrow I have to go to my cousin’s wedding, so I’m just laying low tonight. Do you want to come over? We can watch a movie and I just got Guitar Hero.” I nodded to myself.  This was obviously code for casual one night stand sex. All systems go.        

“Sure, sounds fun, how about I come over around 8:30?” After we coordinated time and he gave me his address, I set to work getting dressed. I couldn’t do thigh highs and garters, some things needed to be reserved for boyfriends, I decided. And maybe a little too obvious? But did obvious matter if you were solely focused on it being all about sex? I finally settled on a hot pink lace matching bra and thong, my tightest jeans, black tank top, leather jacket and black fuck me boots.  

On my way over, all of a sudden I realized I hadn’t brought anything. Is it rude to not bring a bottle of wine to your one night stand’s house? I had no idea. Hastily I made a u-turn back to my local liquor store and once there was again at a loss. What to bring? Beer? Scotch? Champagne? Shit. I decided a bottle of Pinot Grigio was a safe choice.

When I arrived at his place I realized I was shaking a little, and when he opened the door he was perfectly cool and casual which made me even more nervous. He smiled at me and then made a face.  

“Why’d you bring wine?” He looked at me with an odd expression and I immediately realized that yes it is weird to bring a bottle of wine to your one night stand’s house.  

“It was just lying around my apartment,” I lied.

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Should I have just shown up with a scarlet letter F on my chest?

After he gave me the tour, we ended up sitting together very closely on a small black leather loveseat. Less than ten minutes into the movie, he casually placed his hand on my thigh and I looked at him. He raised his eyebrows. I’m not sure who moved first but three seconds later we were making out like crazy. Ten minutes after that, he scooped me up and carried me down the hallway to his bedroom. Five minutes after that, we were having sex.

I did not have an orgasm, which he didn’t seem to notice. But my period showed up, which he did notice. Two days early and all over his light grey sheets. I was mortified. As if I was in middle school getting my period for the first time wearing white shorts in gym class during a game of dodgeball kind of mortified. He laughed it off with a “you owe me a set of sheets” comment before going to his closet and getting me a pair of sweatpants and t-shirt for sleep.  

When I woke up the next morning, I could hear him singing in the shower and I smiled. Then I frowned. No. One night stands don’t lounge in bed. They get up, get dressed and leave. Which is exactly what I did. I was a few minutes into my drive home when my phone rang. Brian.

“Danielle, where did you go?” He asked when I picked up.  

“I’m going home.”  

“Oh. Everything OK?”

“Yup. Great sex. Thanks. I like to leave on a high note.”  I asserted. He laughed.  

“Ok, can’t argue with that. I’ll see you on Monday, I have a meeting in your office with one of your bosses.”  

“OK, bye.” I hung up. This casual sex thing really was no big deal. I should have been doing this all the time.

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Success!

Later in the day, I was doing some gift shopping in the Home section of T.J. Maxx when his words floated back into my head. “You owe me a set of sheets.” I really did probably ruin them, I hedged. Perhaps I should buy him new ones. After perusing a couple aisles, I found a set that closely matched the grey as I remembered it and added them to my basket. They were only twenty-two dollars, I reasoned. It wasn’t like I was purchasing a thoughtful gift. It was a joke more than anything else.  

On Monday I met him down in the lobby after his meeting and presented him with the sheets.  

“What is this for?” He asked, looking totally confused.  

“You know, you said I owe you…so here you go.  New sheets.”  I couldn’t understand why he wasn’t sharing in the hilarity. He stared at them and then looked at me.  

“Umm, I’m sorry. I guess I thought because of how you called me on Friday, that you didn’t want to…I mean what happened was great but I…well…are you looking for a relationship?”  

“Oh no!! Not in the slightest!” I rushed to reassure him. “No strings attached buddy.” He blew out a sigh and I found I did feel just a slight twinge of annoyance that he seemed a bit more blasé than I did.  He didn’t need to sound SO relieved. “But seriously, take the sheets because I feel bad about what happened.” Brian’s face took on a panicked look now.  

“I can’t Danielle. My girlfriend would ask too many questions about where they came from.” 

So my second foray into the world of sex yielded another guy who was comfortable with being unfaithful. Which means there’s really no need to fight my nature to want a more meaningful connection with another person. Either way isn’t wrong or right or will prevent me from being hurt. And it’s okay to embrace my feeling that sex can and should mean something. Whether it’s just the result of an insanely heated attraction or because I really want to wake up to that person every day for the foreseeable future. There’s a place for both.      

But I am going to be much more prudent for whom I decide to buy presents.