Unforgettable Night

by Jack

What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Denver
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Entrepreneur
What’s your current relationship status? Single
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 0

Unforgettable Night

How long ago did this hookup happen? 12 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup?

I met K randomly at a party. Little did I know that the random encounter would turn into one of the most memorable moments of my life.

A little about me. At the time, I was a regular college guy. I had a great group of friends, did well at school and I was athletic. I worked hard at my studies and also enjoyed the typical college activities. One thing that I did not have much experience with was intimacy with women. I had the odd girlfriend here and there and was not a complete virgin sexually but never had gone all the way. Not sure why exactly but I always felt a little self-conscious about it. I wasn’t a shy person, but I guess the time was never right. At the time I found it a bit embarrassing that I had not had sex by the time I was in college. That all changed when I met K.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had been partying with friends earlier that day, it was our school’s annual homecoming football game, and it was always a time where the whole school took the time to celebrate the weekend with lots of keg parties, etc. I wouldn’t say I was drunk, but I was definitely buzzed as I was walking home. I had intended to go back to my place for a quick shower before heading out that night.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end?

I was walking down a street where multiple parties were occurring when a girl from my program yelled out to me from a balcony. I didn’t know her well, so I was a little taken aback that she noticed me from a distance. She told me to come in and join the party. Normally I would have just said hello and went on my way, but I decided to go in just for one drink. As I entered the door, I was greeted by the girl who yelled out to me, and she handed me a beer. She was very drunk and being overly friendly. We had a brief discussion and then she decided to introduce me to a few of her friends that were standing in a circle just chatting.

That’s when I met K. I noticed her immediately. I have always had an affinity towards curvy full figured women. Not sure why but that is where my attraction has always been. K was exactly my type; she was about 5 foot 7, had an hourglass figure and a killer smile. She also had beautiful red hair and freckles. Another huge turn on for me. I tried to contain myself as I introduced myself. I shook hands with K and felt a spark instantly. I wasn’t sure if she felt that spark, but I noticed her eyes look me up and down which made me feel amazing. I joined the circle and started making discussion with the group. I had eyes on K the whole time as her beauty enthralled me. She was confident, sexy and very down to earth. My heart was racing as I spoke to her, but I remained calm and tried to be as confident as possible. After about 10 minutes of talking, the conversation started to get sexual as the group was talking about wild sex stories they had in the past.

I was relatively quiet at this point given my limited experience. Not sure if it was fate, but the group broke off into separate discussions, and I was now alone with K just talking one on one. She told me that she was single and ready to start dating again as she had recently broken up with her long-term boyfriend just a few months prior. I listened closely, and I had my full attention focused on her. Our bodies got closer and closer together as we spoke. She looked me directly in my eyes and asked, “so what would you say your type is?”. I have no idea why but at that moment I decided it was time to make a move. I leaned over so I could whisper in her ear and said, “someone exactly like you.” She blushed and said, “I think you are my type too.” She reached out for my hand, and we interlocked our fingers for a brief moment.

I asked her what her plans were for the rest of the night and she mentioned she was going to go to another party but was hoping for something a little more interesting. I told her I was also planning for the same and was on my way to my place to shower and head back out. K was a confident type of girl and leaned over to say “showering alone?”. I was a little surprised by the suggestive comment and said back “maybe you could join me.” She smiled and nodded. At that point, I wasn’t sure what was going to happen next, but I was ready just to let things unfold with no expectations…

K told me to meet her outside in 10 minutes and told her friends she was going to have a smoke and take a break from partying for the night. I immediately left and waited eagerly for her outside. Time moved so slowly as I waited, but exactly 10 minutes later, K tapped me on the shoulder and asked if I wanted a cigarette. I didn’t smoke, but I decided to take one as I wanted to keep the momentum of this moment going. She lit our cigarettes and asked me how far my place was and if I lived alone. I told her I was a quick cab ride away and my roommates would be gone for the night. She kissed me passionately and said, “let’s go get cleaned up and hang out.” I hailed a cab, and before I knew it, we were at my front door.

I let her in and asked if I could take her coat. She removed her jacket and took a seat on the couch as I fixed us a drink. All I had was whiskey, and to my surprise, she was a fan and took it down faster then I did. We were both buzzed but not so drunk as to be sloppy.

“How about that shower?” K said. I smiled as brought her up to my bedroom. We started making out passionately and fell on my bed. I was fully erect at this point which K noticed immediately. She removed my pants and shirt resulting in me wearing nothing but boxers. She told me to start the shower, and she would be there in one minute. I ran over to the bathroom, started the shower and got in. I heard K enter the bathroom. I asked her if she was coming in as I heard her clothes being removed and falling to the floor. She pulled back the shower curtain, and that’s when I saw her beautiful freckled body completely naked. I nearly came just from the sight. She put one foot in and then the other. The shower was small, so our bodies were pressed together. She grabbed my cock and started jerking it as we made out. I grabbed the body wash and started rubbing it all over our bodies as we kept touching each other and enjoying the moment. She kissed my chest and slowly moved down toward my cock. She looked up and me just before she placed my throbbing manhood in her mouth. To this day, that was the most intense blowjob I have ever received. I asked her if she wanted to move to the bedroom and she enthusiastically agreed. We toweled off and walked slowly back to the bedroom. She asked if I had any protection and I remembered I had a few condoms on my bedside table. At that moment I knew I wanted this to happen, but I didn’t want her to know it was my first time.

I grabbed the condom and quickly put it on. I took a deep breath and slowly entered. It felt amazing and very right. I took it slow initially and was very passionate with K. She moaned with pleasure and then turned over saying that doggy was her favorite. I obviously obliged. I couldn’t get over how sexy she was as I slowly thrust in and out. She asked me to slap her ass to which I did, after about 10 minutes I was reaching the end. I told K I was about to come and she said… “on me baby.” I removed the condom and for some reason positioned my dick close to her mouth. She opened wide and devoured my cock as I came hard in her mouth. It was intense, and she swallowed. We laid back and cuddled. I had just made love for the first time and wanted to go again but also wanted just to be next to her. We laid back and made out for an hour until we both fell asleep.

I woke up first and thought that everything was just a dream, but there was K next to me, she woke up shortly after I did and smiled. “That was amazing,” she said and then asked me how I felt. I told her that last night was something I’ll never forget. She jokingly said that I must say that to every girl. I laughed and decided to tell her that she was my first time. She didn’t believe me at first, but eventually, she understood. “Now I can be your second time too,” K said as she moved towards my cock. We fucked twice more and then again that night. It got better and better. This continued for two months. We never discussed becoming a couple and were basically friends with benefits.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Wish we still kept in touch but she moved schools.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? My roommates told me that they came home that night and heard K and I having loud sex. K met them the next day. They were happy for us.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Making love to someone who is exactly what you want. Best first time experience ever

What was the WORST thing about this hookup? Nothing at all

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I gained a lot of confidence and have had many partners since

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

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