This happened many years ago. But when I was younger my best friend’s sister was always around. She was super annoying. We grew up around each other. When I went away to college and she stayed in our home town I didn’t see her or even think about her for a while. Then I moved back home for a little while.

While I was away she had developed into a hot tight bodied 18 year old with smallish perky tits and a petit ass. We started messaging each other and one time when I was over at my friend’s house and he went to take a shower his sister had these little terry cloth booty shorts on. We started kissing and I slipped my finger up her shorts leg and started rubbing her pussy. She moaned and I felt her pussy get super wet.

The next time we were alone together I was trying to go further and she told me she was a virgin. I said that’s ok. We don’t have to have sex. We did fool around some more and I could tell she wanted to do more so I pulled my cock out and she sucked it for a while. I didn’t cum because it wasn’t a good blowjob. She’d never given one, but it was hot to just have her put her mouth on my cock.

So finally, one day my parents are gone at work and I’m at home. She comes over and we have free reign now. We make out, I start fingering her until she’s dripping wet. I pull out a condom and ask if she wants to have sex. She nods nervously. I put the condom on and lay back on top of her. (Keep in mind I’ve only had sex like 4 times before this so I’m no pro either)

So it’s awkward sweaty young bodies slipping around on each other. I place my cock head right on her pussy and gently push as I look into her eyes. I ask if she’s ok. She’s clearly feeling a little pain, but wants to keep going. I push a little harder feeing resistance until I feel my head break through and slip in. She gives one of those yelps that’s also a moan. I don’t know how else to describe it. But it makes me feel like I hurt her so I stop. She says it’s fine and to keep going. I push further until my cock is all the way inside her. She’s holding on so tight to my back I can tell it hurts, but I begin to pump in and out slowly.

Now I can tell she’s feeling better so I keep going. I kiss her deeply as I feel my balls tighten up. We hold each other as I push my cock deep and my dick pulses and fills up the condom. I moan as I finish and kind of just lay there a moment breathing. We both don’t really know what to do afterwards so we just get dressed and she heads home. We never had sex again because we really didn’t want to be together and she didn’t want to keep having sex with someone she didn’t want to be with.

But years later after she was married I remember meeting her husband and thinking it was hot because he knew I took her V. And he had to just sit there and talk to me like it never happened.