One Night Stand or Something More

One Night Stand or Something More

I hadn’t gone on a date since Jeremy. If you didn’t read my last post “I Fall in Love With a Guy in a 4 Year Relationship” Jeremy is a guy I met in my last semester of college. I lost my virginity to him and we had a “situationship” for about 2 months. For the most part, it was sweet but I couldn’t ignore the fact that he had a girlfriend. Things ended between us a couple of months ago but I haven’t been able to get over him or open my heart to someone new.


You might hate me for this but Jeremy and I still text now and then. Nothing sexual just about school and life. Until recently he ghosted me.


After 5 months of no dating or sex, I decided to go on Bumble and try again with someone new. That’s when I matched with Bennet. He was a bit older than me, tall and strong with ruffled, wavy orange hair, a bit of aftershave, and glasses. So more or less an older more rustic version of Jeremy. But he’s what I needed… at least for the night.


We decided to meet at a local bar for a couple of drinks. I promptly walked inside and ordered a gin and tonic eyeing the deer head covered in string lights and vintage red velvet walls. He texted me that he was outside on the patio and I squeezed my way past the stench of desperation, sweat, and booze.


Outside, everyone was smoking cigarettes, sipping amaretto sours, and hoping their makeup wasn’t running. Gossiping about coworkers and old friends eyeing people in the crowd to take home for the night. But their voices vanished, the air became cool and crisp, and it was just me and Bennet sitting at a small table by sycamore trees and lights in mason jars. Now it’s important to note this isn’t a love story. But every time I go on a date or hook up with a one night stand I get a taste of what it’s like to be in a relationship. A sample if you will. It’s nice to feel apart from the crowd of 20 somethings, to feel safe that you’re with someone else. And no longer in the hunt to find someone new.


He was a beer guy sipping on a PRW as I played with my straw in what was left of my gin and tonic. For a good half hour, we made small talk rubbing our knees together underneath the table. The whole bar staring at us. Whether it was guys who wanted to fuck me or girls who envied the attention he gave me and I couldn’t lie, I liked it. He ran a finger on my hand and asked me if I wanted to go back to his place. A smile curved up the side of my cheek and I nodded.


We walked to his apartment passing by brownstones and eyeing the moon floating over a chappel hidden under streams of dark grey clouds. I interlaced my hand with his.


“Wow,” said Bennet, “Your hands are so cold.”


He circled his thumb in the center of my palm like Jeremy used to. It made me shudder as I reminisced about our nights together.


“Yeah, sorry,” I said stepping back into reality.


We heard a couple of purrs and noticed a black cat a couple of feet in front of us. We kneeled down and pet her as she brushed up against us. We laughed and Bennet picked me up and kissed me. Wrapping his arms around my waist as I ran a hand on his cheek.


“Bold move,” I said with a smile.


We got back to his place and didn’t waste much time. I mean it was a one night stand after all. He led me to his room and kissed me, leaning me against the door to shut it closed. I stood on my tippy toes wrapping my arms around his neck. He took me over to the bed and ripped off my shirt. I knelt on his lap pulling his sweater over his head. Running my nails up his arms as he moaned.


He kissed me and wrapped me underneath him. Pressing his body on top of me kissing me everywhere. He unzipped my jeans and pulled them off my legs. Kissing my inner thighs. He pulled off my panties with two fingers and melted down to my pussy moaning in amazement and delight. He went down on me struggling a bit at first to find my clitoris.


He stepped off to the side and took off his jeans and Calvin Klein briefs. He was very well endowed which was funny to me. Guys with big dicks are like big dogs, shy and lanky. Whereas guys with small dicks are like Chiwawas feisty and overconfident.


He grabbed a condom and knelt in front of me poking his cock inside of me. I was still a bit tight so he went down on me again. He knelt up and fingered me with his thumb watching my body shudder as he jerked off.


He knelt up and pressed himself inside me. Sighing before falling on top of me and going all the way in.


“We’ll go slow first,” he said.


He slowly stroked himself inside me and I was scared it would hurt but it felt good. He grabbed a hand over my head and kept going slow as I moaned. Usually, I feel the need to say something sexy for the guy but all I could do was softly moan for him. Is this what casual sex was? Is this what it felt like to enjoy casual sex?


He started going a bit faster spreading my thighs open and running his hands down my back squeezing my bum. He reached a hand to the back of my neck softly choking me as he fucked me.


I ran my nails down his back up to his bum. Softly scratching up and down. He grabbed my hands and put them back over my head.


We kept going until he finished and he took himself out of me and laid next to me wrapping me in his arms.


“Thank you for being so patient with me,” I said.


He laughed and ran a hand down my cheek.


“You shouldn’t have to thank me for human decency.”


I turned my head towards him and hugged him. He wrapped me closer to his chest and kissed my forehead.

One Night Stand or Something More

No one had ever said that and it’s true. After all of my negative experiences, Jeremy felt like this knight in shining armor when in reality he was giving me the bare minimum. And when I told Jeremy how grand and wonderful he was he ate it up. Bennet didn’t. Bennet let me know I deserve respect, that I should never feel thankful for respect.


He fucked me again wrapping his body around me, letting me know for the night I was his. When he finished he ran his hands over my breasts, down my waist, and legs. He spread my pussy a bit rubbing my clitoris continuing to caress my body. He kept telling me I was sexy, that my body was his. He ran a hand on my cheek running his fingers through my hair.


He pulled my thighs towards him, picking me up on his lap. He kissed me and held my breasts pressing them up and down, whispering for me to stay. He lied me back down on the bed spreading my legs feeling his pussy.


I told him I had to get going and he called me an Uber. He dressed me putting on my panties and shirt.


I searched for my jeans and he motioned me to come to him. I wrapped my arms around his neck standing on my tippy toes and he ran his hands down my waist grabbing my bum.


“We need to do this again,” he kept saying.

One Night Stand or Something More

I nodded and pulled up my jeans. I’d be lying if I said I wasn’t over Jeremy but right now, Bennet is what I need. It’s nice to have someone to cuddle with and fuck every now and then. And it’s strange because for the first time I don’t have any feelings, it’s just sex.


I was expecting Bennet and I to only have that one night but we’ve talked about meeting again soon. I mean it is cuffing season after all. I’ll keep you posted on where things go but I’m happy with it just being friends with benefits. I’m planning on moving soon and in no way am I over Jeremy so, for now, this satisfies my basic needs.

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What Girls & Guys Said

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  • I have a tv crush on Kit Walker & Violet 😛🤓 ( I know they are from different vignettes)

  • I think this is going to evolve into an amazing friends with benefits relationship for you. The sex you described sounded awesome, and you both seem to be on the same page.

  • Make sure he knows what you want, he may want more.

    • He knows we talked about this the second time we met up