#19 One Night Stand (My Worst Sexual Experience To Date)

One nights stands are kind of a hit or a miss in terms of the overall sexual experience. I myself believe you’re going to have better sex if you know your partners body. However, just like everyone else if sex is on the table and you’re horny, you’re most likely going to act on those urges and that is the case in this story. I never expected this to turn into a one night stand, but I couldn’t bring myself to see her again and you’ll soon find out why. I was concerned about telling this story for quite sometime because I don’t like to talk bad about my partners, but this was truly my first and only one night stand.


It started like most other girls I’ve met; through an online dating website. This girl messaged me and I thought she was cute, we’ll call her “K”. “K” and I texted back and forth for quite a while and she seemed like a great fit for me. Not only were we into similar things and she had a high sex drive. We sent photos back and forth, flirted and even sext a few times. I thought I had met my match because she seemed to be into everything. I was ecstatic and we set up a first date and joked about how we wouldn’t be able to keep our hands off one another.


The day came and I drove to meet her; she thought it would be more of a traditional date if I picked her up at home instead of meeting up somewhere. I agreed and after some trouble with my GPS I found her house. She was waiting outside for me in her driveway. “K” looked nothing like her photos; she was much heavier than I expected which wouldn’t have been an issue had she just sent me more recent photos. I shook it off, smiled and let her in. I could tell she was nervous by the way she could barely bring herself to look at me. I tried to ease the tension by joking around how my GPS got me lost. Finally she started laughing and making fun of me as well; I had no idea what I was in for.


I didn’t know the area and it was a nice day so I suggested going for a walk. “K” directed me towards a nice nature trail that lead out onto a boardwalk. We walked and just talked, but talking soon turned into her saying borderline insulting things. At first it was playful, but everything she was insulting by picking apart my job to her claiming “I must not have hung out with the popular crowd back in high school”. I’m up for some playful ribbing, but the jabs came the entire time we were out. Eventually our walk came to an end and she said “this was fun, you can take me home now.” Keep in mind we had only been out for about an hour and I was relieved that the date was coming to an end.


I drove her home and parked in the driveway, she climbed out and then said “are you coming in or what?” I genuinely thought that was the end of the date. I was ready to call it a day and go home, but my penis lead my lips to say “yeah, sure.” This was the first time I let my penis lead me into a shitty situation. We went in and she gave me a tour, no one was home. She lead me into her bedroom and we laid down on her bed. You’re probably thinking it is about to get hot and heavy because that is what I thought too. Well she turned on her DVR and put on an episode of Keeping Up With The Kardashians she hadn’t seen yet. I remained still in the bed regretting every decision I had made up to this point.


There was still hope, I wanted to make the best of the situation and leaned over and kissed her. “K” said, “It’s about time” and then went back to watching her show; paying no attention to me. I couldn’t believe what was happening, she was interested, but she wasn’t interested. I just rolled back over and continued watching the show that I could care less about. Once the show came to an end, she put on an episode of The Simpsons. I stretched and said I should probably get going soon; anything to leave. She says, “come spoon me”. I came up behind her and kissed her neck and spooned her; sliding my hand up to her breast before she slapped it away. I figured that was clearly a no go, but literally a few moments later she took my hand and placed it on her breast. I squeezed a little and she giggled and pulled my hand off her. Who is this girl? I thought, this is so strange.


“K” rolled onto her back and spread her legs; inviting me in. I didn’t want to get slapped away again so I just sort of stared at her. She asked what I was waiting for and I asked if she really wanted to do this. “K” nodded her head and I pulled off her jeans and slid down her underwear. She playfully closed her legs so I could see her private area. I spread them apart and went down on her. I rolled my tongue over her clit and then slid my fingers inside her. She moaned and said “you sure found the right spot fast.” I felt reinvigorated as if this maybe this wouldn’t be as bad as I thought. Suddenly she stopped me after only a few minutes of going down on her pushed me away saying she was too sensitive and couldn’t take it anymore.



There was one issue, I was only semi-hard at the time and she asked me to fuck her. I told her I wasn’t hard yet and she told me to take care of it. Now this is rare, for example now with “J” I can get hard just from her kissing me or a gently touch on my thigh. I got hard enough by stroking myself with no help from her; she just laid there on her back still and her shirt on. I took off my clothes and slid into her and for the first time ever I was dead fished. When I say that, I mean she just laid there and did absolutely nothing as I fucked her. She didn’t even make a peep and when I looked up at her she looked as though she was going to cry.


I asked her is she was okay and she told me not to stop. Well a girl looking like she was going to cry during sex isn’t a huge turn on and I could feel myself fighting to remain hard. Finally I couldn’t do it anymore, I was getting no pleasure at all from fucking her. I rolled off her and she never asked why I stopped mid-sex. I know what you’re probably thinking, was this girl a virgin? That would explain so much, but she claimed to have been with eleven different guys. That did seem a lot for someone who didn’t seem to know how to have sex, I guess I’ll never really know.


There was nothing that was going to stop me now, I needed to get out of there. I threw on my clothes faster than I ever have. She watched me and said it was “good”. I just smiled and nodded my head before heading towards the door. “K” walked me to the front door still pants-less and hugged me. She said she had fun and wanted to see me again which was weird considering the way she was acting. I hugged her back and said I would talk to her soon. The most pleasure I received that day was the relief I felt when I was alone in my car. I drove home replaying everything that had just taken place over and over again in my head; it felt as though I was stepping out of the twilight zone.


I’ve heard of good one night stand stories and bad, unfortunately mine fell into the bad category. Actually mine may need a category of it’s own like the “WTF” category. Just a little update, we did talk again the next day and both agreed it would probably be best if we went our separate ways. She took it rather well, maybe she thought I was a bad lay which was fine by as long as I didn’t have to go through another experience like that again.


Until next time, happy cumming,


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