Where it happened: My Basement
Langauge: English
Sex: Female
Rating: 5
Category: Straight
I definitely don’t regret my first time… even though my boyfriend and I both got in big trouble for it afterwards. It doesn’t matter.
It happened in February and my boyfriend and I had been dating since the end of November. We were pretty quick. The second time we ever made out, he fingered me. About 2 weeks later (at tops) we both did oral on the beach in like 40 degree weather..naked. But those are both very different, interesting stories. My first time isn’t as insteresting but I’ll try to remember everything. (By the way, it’s almost April now.)
Okay, this is how it happened…
It was a half day of school. It was a Tuesday. Him and I went out to eat at around 11am and then went back to my house by about 12pm. We were in my basement watching TV and mainly just laying together kissing and occasionally messing around like usual.
At one point, while he was fingering me, I got extremely horny.. because you know.. he was hitting “the right places”. We had almost had sex a couple of times, because he’s slept over before and we’ve been home alone once or twice. We had never bought condoms until recently. So now the desire was even stronger and there really wasn’t anything stopping us. I made him stop fingering me because I didn’t want to get off and I didn’t want to get horny enough to actually have sex.. because it was already pretty tempting. So I gave him a blow job and didn’t finish it.. I asked him if we could have sex. He asked me if I was sure several times, he was more scared then I was. I asked him if HE was sure.. and he said definitely. Before we started getting ready to do anything, he was laying on me or i was laying on him, i can’t remember, and his heart was beating soo fast. I wasn’t THAT scared. Ha.
He’s a senior in highschool and I’m a freshman. He was a virgin too. He had turned down several of his other girlfriends for some reason, he is very attractive and he’s smart. Good catch on my part. But him and I are a lot alike. We’re both super smart, like all honors, GT, or AP classes, plus debate. And we’re both attractive. I’ve actually turned down a fair share of guys as well. But back to the story…
We got up and got the condoms out of my purse(his parents are super strict and religious so he made me keep the condoms with me). We were on the couch again trying to put one on and the first one we messed up. So we had to get out another one and we managed to do it right. haha. so finally we’re ready. I always thought that I would wanna be on the bottom my first time but I tried being on the bottom and for some reason, it scared me more.. So I got on top and sat on his stomach and we reassured each other a couple more times that we were ready. So I sat up and him and I tried for probably 5 minutes to get it in but we just couldn’t, plus it was hard to lay like that on the couch and do it. So we moved to the floor. I tried the bottom again but made him switch me almost immediately because it scared me. We tried again to get it in but couldn’t and I agreed to let him try to be on top. But by now he wasn’t hard because of his nervousness. I got off him and he started to jack off. The condom wouldn’t stay on with his penis soft so we took it off and I gave him a blow job long enough to get him up again. New condom. Then we tried again.. with me on the bottom. I was scared on the bottom but I didn’t care this time. I helped him put it in slowly. It really didn’t hurt at all. He had already broken my hymen about a month earlier fingering me and even THAT didn’t hurt, the only way we knew it broke was because it bled a little and he couldn’t feel it in there anymore. But he slowly slid into me and once it was all the way in he asked me if I was okay. I was fine so he slowly began going in and out. We kept eye contact all the time. I love how I’m comfortable enough to look straight at him when we’re messing around. I could never do that with anyone before, I felt stupid. But anyway, we stayed like that for awhile and eventually he got faster and faster. It felt really good but not as awesome as I thought it would. Later, when I admitted that, he said he had felt the same way. But anyway, he asked if I wanted to be on top now, and I agreed. So he pulled out and I got ontop of him. I easily slid down and our hips met. I started moving up and down.. in and out. Everytime he went into me it felt awesome. It felt a lot better this way, he said the same thing. And by the look on his face, it was pretty obvious. 😉 I eventually started moving faster and faster and his grip on my hips tightened and he began moving me too. We were constantly stopping to check and make sure the condom was still on. Finally, he started biting his lip and scrunching up his eyes. (He looks soo cute, haha! but i make fun of him for that face!) I kept going faster and faster. Finally he finished. I didn’t have an orgasm but I definitely had a lotttt of fun. It wasn’t awkward at all, even through all the problems we had just trying to get ready to actually have sex, we’re just soo comfortable around each other. We didn’t get to do it for very long because he had to leave for work soon, and we didn’t get to spend time together after it because he had to go to work at 3:30pm. But we hugged and kissed and I’m really glad that my first time was with such a great guy. He took all the wrappers and condoms with him in his pocket to throw away somewhere other than my house, because my parents had been home that whole time. So he dropped me off with my brother(he’s 12) while I waited for my friend to go to her house on his way to work. He was a little late but he said that it was a good reason. Haha. He gave me flowers that he had bought a few days earlier but I hadn’t gotten to see him on Sunday or Monday so he finally gave them to me that day. I brought them into the place where my brother was. Those flowers are still living… I’m looking at them right now. 🙂
Anyway, we send text messages to each other all the time and we’ve even sent pictures a couple times. So he got in trouble for something a few days later, which was my brothers fault, because him and i never get in trouble. but his parents took his phone away and found pictures.. and worse.. text messages referring to us having sex. so they figured out that we had done it and they CALLED MY PARENTS TOO. they took his car away after that. we haven’t been able to hang out in over a month and so we’ve only had sex once. he got me caught for a dirty note i wrote once too. haha, man, AND our parents only found out about MY pictures, because i’m smart and they didn’t get a chance to find out about the ones he sent. plus, his parents hated me from the beginning, and parents usually love me. but they didn’t like me because i’m 2 years younger than him.. which reallllyy doesn’t matter. all of my other boyfriends have been older than me by at most 3 years. but we’ve gone through a lot of issues with our parents, but him and i get along great, we really don’t have big fights or anything. we’ve been through a lot and if we got married there really wouldn’t be many other problems that could come up.. trust me. haha.
but we’ve stuck together through all of it. i like him a lot and he’s very important to me. he recently told me that he loves me and that he’s never liked another girl more than me. and he’s only loved one other girl before, and he was with her for 2 years. i’m not sure yet if i love him. i feel so safe with him and warm and stuff but i don’t know for sure yet. we’re gonna be together a long time. 🙂
but that’s my story. i don’t regret doing it, i never will. i only regret getting caught. we’re still in trouble and he’s in florida right now on spring break, i completely trust him and he trusts me. i don’t know why anyone waits to have sex, it didn’t complicate our relationship and if anything, it made us closer. i didn’t get pregnant and he didn’t leave me the next day. ladies, i guess you just gotta pick a good guy.
🙂 thanks for listening. i always promised myself i’d write on here once it happened. haha!
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