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One Night?


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This is a true story.

I was young, in my early twenties.  I was inexperienced, I had only been with two guys before.  Both had been boyfriends.  I was just out of a two-year relationship.  My roommate at the time was a bit wild and was encouraging me to try new experiences.  She was shocked that I had never had a one-night stand.

I was very insure at the time. Guys hit on my all the time.  But I had never been the one to pursue or hit on a guy.  I was too timid (no pun intended).

My roommate talked me into going to this little dive bar that had a live band.  It was a bit of an older crowd than the bars or clubs that I was used to.  She was friends with some of the regulars at this bar. When we got there, we found a table and started in on drinks.

My roommate told me that there were a lot of hot guys around and I needed to pick one to be my first one-night stand.  I was emboldened by her encouragement.  I was so nervous, but I told her I would try if a guy caught my eye.  We sat there for a while, and I had a second drink.  She was coaching me with how to approach the guy and start a conversation.  She got up and danced with a guy she knew.

I felt a bit bolder by the alcohol, but I was only slightly buzzed.  I locked eyes with a guy sitting with two others at the bar.  He was my type, dark brown hair, and dark eyes.  My eyes darted away when he smirked at me.

I took another sip of my drink and glanced back at him.  He was talking to his friends.  I watched my roommate still dancing with her friend.  Then I glanced back at the guy.  His friends had moved to play darts and he was now sitting alone.  He was watching me again.  I took a deep breath, stood up and walked over to him.  He smiled as I approached him.

I said hi and asked if he wanted to dance with me.

He said, “I don’t dance.”

My heart sank.  I had struck out so fast!  I was so disappointed and didn’t have any game to try and play coy or think up something else to say.  I said, “Oh, sorry!  You have no idea how much it took me to come ask you.”  I turned around and walked quickly back to my seat.  I was startled when he sat down at my table next to me.  I had not realized that he had followed me.

“I was only saying no to dancing, not to talking to you.”

“Oh”, was all I could manage.  I could feel the blush on my face.

We talked for a bit.  His name was Steve.  He told me that he was in the Air Force and he and his friend had ridden their motorcycles to town to visit another friend.  He was pretty talkative, which helped put me at ease.  He was about twelve years older than me.  I had never dated anyone more than four years older than me at the time.

I really didn’t know what I was doing or how to even approach a one-night stand topic, or even if I should.  Hell, I didn’t know how this worked.  

My roommate came back to the table, and I introduced Steve to her.  He called over his two friends and we all hung out for at least an hour.  My roommate was not shy, so she had no problem chatting up Steve’s friends. 

The conversation went to motorcycles, and I said that I had not been on one before.  The rest of the group looked shocked.  Somehow, we all ended up outside and I got on Steve’s bike behind him.  He explained to me about leaning into the turns and such.  My roommate got on behind one of his friends and we went for a short ride around the neighborhood.  It was thrilling and a bit scary…I mean, I didn’t know this guy and I had my legs pressed against him and my hands held his waist tight. 

When we got back to the bar, we said thanks for the rides and my roommate mentioned that we should get home.  She went back in the bar to say goodbye to her friends.  Steve asked if he could see me again.  Um…wait, was I not giving off one-night stand vibes? 

I mustered up the courage to ask him if he wanted to come back to my apartment and watch TV or something.  I felt like I was watching myself as I was saying the words.  I was hoping he didn’t say no like he did to the dancing.

He seemed happy about me asking him, if not a little surprised.  My roommate came out of the bar with the friend she had been dancing with.  So, the four of us headed to the apartment.  My roommate and her friend headed to her bedroom.  Steve and I hung out in the living room with the TV on.

Again, I didn’t know what to do.  So, I just sat next to him and watched TV.  We talked a little more about Steve’s work in the Air Force.  It was very confusing for me, anytime I was alone with a guy my age he would have already tried to at least kiss me or grab my boob or something.  Not Steve, we just kept talking with the TV in the background.

I finally turned to him and said, “Do you want to kiss me?”  I was immediately embarrassed by my question, but he just smiled at me.

He pulled me closer and kissed me.  From there things started to move more quickly.  He was skilled at kissing.  My hands were exploring his shoulders and chest.  He felt like he definitely took care of himself. 

He pulled back and asked if we should move to my bedroom. 

We went into my room and closed the door.  We began kissing again.  He started removing my clothes and backing me up to the bed.  Within a few minutes, we were both naked.  As this was only the third cock I had seen in person, I did stare.  He was longer than my last boyfriend had been, but about the same girth.

He asked me, “Do you like what you see?”

My gaze flew up to his and I could feel myself blush again. I nodded and he chuckled and said, “Good.”  I was not confident enough to ask him the same question.

We both got on the bed, and he began kissing me and running his hands over my body.  He touched my breasts, but he didn’t grab or squeeze as I was used to.  He was more patient, and it felt like he was not in any rush.  This was such a different experience than I was used to. 

I was on my back, and he moved down my body and kissed me.  He took a nipple in his mouth and sucked and nibbled gently.  Then he repeated the action on the other nipple.  I was getting so aroused and couldn’t help but arch towards him.

His fingers went to my slit, and he stroked me.  I could tell I was very wet by how smoothly he was able to stroke me.  His finger circled my clit slowly.  Then he slid that same finger inside me.  He looked me in the eyes and said, “Fuck, you're tight.”

My inexperience had me wondering if that was good or not.  But I stopped thinking as he began to fuck me with his finger.  I just grabbed on to his shoulders and rode his finger.  I could barely control my hips.  He bent down and started kissing me on my mouth again.

His finger felt so good, but I was started to feel desperate to have his dick inside me.  I pulled away from his kiss and said, “Please.”  I didn’t know how to ask for what I wanted, but he seemed to get the idea.

He pulled his finger out and got off the bed.  I wondered for a second if I had said the wrong thing, but then I saw him pull a condom out of his wallet from the pocket of his pants.  He looked over at me and help up the condom and I smiled at him.

He climbed back on the bed and rolled the condom on.  He was kneeling between my legs, and he began stroking my pussy again.  He then shifted himself and me to where my legs were spread, and his cock was at my entrance.  He was still in a kind of kneeling position.  He rubbed his dick against my opening and then pushed forward slowly.  I thought it was so sexy how he was watching himself enter me.  He worked his way into me slowly, taking his time.  When he was deep inside me, I felt so filled up.  All I could do was make little moans.

Then he lifted my legs up on his arms and started stroking in and out of me deeply.  It felt so good, but it almost hurt when he went really deep.  He fucked me like that for what seemed like a long time.  He started fucking harder and I could tell he was getting close to coming.  I was having a bit of trouble getting out of my head about the whole situation.

He let one of my legs lower and he moved a hand between us, and started rubbing my clit. 

Oh hello!  That felt so good.  To feel him deep inside me as he stimulated my clit was a new experience for me. The two guys I had been with had paid little or no attention to my clit, I am not sure they knew what it was.  I could feel an orgasm approaching.  He started murmuring dirty things to me that were non-sensical, but I found it sexy that I could have this affect on him.  All the sudden, my orgasm was there and I tried not to cry out too loud .  He quickly followed and gave a grunt and thrust deep.  I could feel his body tremble a bit.  Then he collapsed on top of me.

When he recovered, he took care of the condom and then laid back down on the bed.  He watched me for a bit and ran his hands over my body.  Then he said he was going to head back to his friend’s house.  He put back on his clothes and I put on sleep shorts and a t-shirt.

When we were both dressed, I walked with him to the front door.  He asked me for my phone number.  I gave it to him, and he left after kissing me quickly.  As I was going back to my room I started wondering if I should have given my number.  Was there a one-night stand etiquette?  I really wasn't very good at this.

The next afternoon, Steve called me.  He was still in town and wanted to take me to dinner.  I ended up going and having sex with him before he went back to base about 45 minutes away.  He called once more, but then I never heard from him again.

So, it wasn’t exactly a one-night stand, but it was my first experience of having sex with a guy the first night we met.


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1 hour ago, NeverSuspect said:

Very nice story :) You sound like you were a very sweet innocent little thing 😉

"Was", yes. 😆

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I find myself scrolling through all the “sexy stories” to find yours. They are so well written and so hot. I had some one night stands in my twenties before marriage and this took me back to all those butterflies. Plus, with the Air Force reference, I can only think of all those amazingly hot guys in the Top Gun movies. Whew! I need a cold drink and some new batteries tonight. Thank you again for your stories. 

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18 minutes ago, Katie Did It said:

I find myself scrolling through all the “sexy stories” to find yours. They are so well written and so hot. I had some one night stands in my twenties before marriage and this took me back to all those butterflies. Plus, with the Air Force reference, I can only think of all those amazingly hot guys in the Top Gun movies. Whew! I need a cold drink and some new batteries tonight. Thank you again for your stories. 

Thank you! 😊   I appreciate your feedback.  I am so pleased you enjoy my stories.

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