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The first(ish) time
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The first(ish) time Someone asked that I write about how I went back to boys in high school and lost my boy virginity... Truth is, I never left the boys. I was getting naked with girls, but boys were still there. It was just all oral (and that one horrible anal incident...). Seriously, if I had a dollar for every dick I've sucked, I would definitely have at least $100. Might have as much as $150. I got to a point where I stopped keeping count. Kind of the way I am with the guys I've fucked... Anyway - it got out in high school about my oral prowess. The interest generated from that alone... If I had sucked every dick that wanted it, I'd basically just subsist on cum. So, I had to be very selective. Much like I am with my partners now... There was one guy that I wanted to do all the things with. We were friends for a long time, but never did anything. We got close once, his dad busted us in his bedroom under the sheets. We were very innocently chatting, but it was very slightly going in the one direction. He was feeling my boob up subtlety over my clothes. And his dad literally broke the door down to get in. He made us both go<b> downstairs </font></b>to hang out in the living room with him. When I went to the hall bathroom at one point, I could hear his dad talking about being safe and not wanting to ruin this sweet girl's life. I agreed completely, so I left not long after. A couple years later, we were still friends and would talk late at night sometimes. One night we were talking because he was upset about something or other. I was trying to calm him down, but he was not having it. He asked me to come over so we could talk. It was maybe 11 at night on a Thursday, but I always liked sneaking out. So, it didn't take me much convincing. The plan was I would go to the side of the house his room was on to let him know when I got there, and then he would come out. I get there, he comes out to meet me. He's still all pissed off and I just hug him because what else is there to do? He squeezes me super tight back and I get the butterflies, hard. He then asks me (while we're hugging) if I could spend the night. He swears he can get me in without his parents knowing. ... I definitely wanted to. I had all the feelings for him for so long. But I also didn't think I should because of the obvious reasons. I was quiet too long and he said something like not for sex, just to cuddle. And I didn't have to stay the whole night, just until he felt better. I agreed to that. Which was how I wound up in the bed I was in 2 years before, under the covers once more. We were laying on our sides chatting about whatever. He even brought up the time his dad busted the door down. I honestly don't remember how it happened, but we started kissing. I love kissing, I could make out with someone for hours. But, I could tell he didn't want to stop there. He had already pulled my shirt off and he kept messing with the top of my jeans. I wasn't looking to take my pants off though, so I just took my bra off to distract him. The plan worked, but only for a little while. He went right back to my pants before too long. He started pleading with me a little, saying he's wanted to be with me for years. I'm totally ready to say yes, but I bring up how scared I am about getting pregnant. He lets me know he's got condoms (he was also a virgin, but had them just in case) and says he'll even pull out with the condom on. He really didn't even need to convince me so hard, I still distinctly remember how badly I wanted to have sex with him that night. He takes my pants off, fingers me with my panties on for a bit, makes it abundantly clear he doesn't do this much, then he takes his pants off. I move to suck his dick because that's what I know best but he's like no, I won't last long. Well, alright then. He puts the condom on like a pro and I take my panties off. He gets on top of me and I guide his dick to my pussy. He has a few misfires, but gets the hole eventually and he eases in slowly. I was definitely expecting some feeling like "I am a woman now", or that it would hurt, but neither of those things happened. Don't get me wrong, I really enjoyed the feeling I got, but it didn't make me feel different at all. It was just natural. He did pull out when he came (which was in no time) and then he cleaned up after. We were both awkwardly like well what now? after. I left shortly after because we both had school tomorrow/that morning. I didn't see him at school because I rarely did, I took AP classes and he didn't. Then that night, he called me. Saying he wanted to be with me and that he made a mistake not getting with me sooner. But, that was pretty much the end there. I was moving away in 2 months (to Colorful Colorado) and I was still desperately in love with this girl I'd been seeing off and on, so there was zero point in pursuing things with him. I did see him once more at a going away party for me a week before I left. We just kind of avoided each other the whole time. He hugged me goodbye when everyone else was saying bye, I still had the butterflies, but that was that. But there you are. The boy that convinced me to give it up didn't even really need to convince me. |
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Ahhhh.... Interesting. Thanks for the post. And the thing about my oral prowess is still true in case you were wondering... Noted.    
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10/9/2017 7:33 pm |
Interesting post. If I had to choose and could only ever do one sex act in the future, yep it'd be oral. Now would it give give or receive?
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10/9/2017 7:33 pm |
Good write wonder twin.
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