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So I was 23 and covid did hit in 2020, I just started studying at high-school half a year before, we now had online courses and I was using dating apps and social apps to maybe find my first love in that weird situation (had been using those apps before, since all my fields of interest are heavily male-occupied, but without real luck, and still virgin)
So one day I wrote a random post on one app which was like "yeah this is who I am, anyone interested in getting to know each other and maybe get together?", to which a few girls replied, I think I continued writing with two or three, but except for one, the conversations would die at some point.
The last one wasn't the most entertaining conversation I've ever had in my life, and I did put some work in to keep the conversation going, since I liked her way and also still was kinda desperate for love and obviously also sex. So after a month of just chatting I finally got around to asking her for a date, to which she happily agreed.
So the day came, I was really nervous and (I think because of that) when showering and preparing in the morning, suddenly, with one move, my back started to hurt badly. I did go through my options and also messaged her to kinda cancel the date, but then a few minutes later I just thought "fuck it, it's not thaat bad, let's go" and told her I'd still make it.
So, I got there, we did meet at a local sea, pretty casual. Had a great talk, but nothing more. Afterwards I still knew somehow that I wanted her.
We then met up another time for a bike ride and after that we switched up our dates to be at her place. I was always so nervous because I had next to no experience with dating, girls, and so on. I still prepared for the eventuality of having sex, but would really not be starting any of it. But with more dates at her place and the summer getting hotter and hotter, she got flirtier each time and "because it was so hot" she argued we should put off our clothes, which then at some point ended up in us two being naked. She looked me in the eyes and asked me if I wanted to do it, and obviously I wanted her.
So we switched to the bedroom, I fell a bit behind when getting there because I was so nervous. She was laying there on the bed, naked, her legs already spread for me to enter, but put out a condom for me and told me that I had to put it on myself since she didn't like to do that part.
So, me being nervous as hell, opened up the packaging and put on the condom, which resulted in my boner to die. She laughed it off and still waited for a bit, but I didn't manage to get properly hard again. So we just cancelled that and she told me it was fine and we continued watching a movie.
I was pretty embarrassed by that event and kinda thought that she would cancel the dates maybe, but she was fine with it when we messaged later, so we had the next date, where we were going into it again, and at some point she told me that we could also leave the condom away if that would help me.
I asked her if she was on birth control herself, to which she said no. We then even had a short talk about her eventually getting pregnant from me and her keeping a child if she would get pregnant, but I was in a financially stable situation and her as well. So with me wanting to get laid and us both being horny, I decided to leave the condom away.
So we continued on and after we both ended up naked again, switched to the bedroom, she had me lay down on the bed and slide onto me, then guiding and putting my dick into her, which was a fantastic moment, and she fucked me raw. It was fantastic her riding me, one of the most intense moments of my life. At some point I was going to cum, told her and she was just smiling at me and continued riding. This was so hot, my dick just pulsated and shot all cum I had into her.
After that, she stopped and smiled at me with that specific grin, still sitting on me and still having my pulsating cock inside her, with my cum flowing out of her, running down my dick and onto the bed sheets. We stayed like that and talked about my first time sex. Later we stood up and showered together, her cleaning herself from my cum under the shower was so sexy.
This continued on with several dates and also later as we officially got together, where I always would put my semen into her. Sometimes she would send me a message from work or elsewhere, telling me how she could feel my cum still flowing out of her hours later, turning her panties into a soaking mess.
She never got pregnant until we decided to use birth control months later, probably for the better, even though I get hot thinking about the possibility that it could have happened.
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