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A lot of my relationship with her beforehand was me thinking about losing my virginity, which certainly didn't help. We had been dating for four years.

It hurt for her at first. I wish it didn't. But we did what we could — we were comfortable with each other, so we were both patient. I think it was a better experience for me than it was for her.

We had spoken about it for months. Finally, it happened one night in her bedroom when her parents were out. We made sure to use a condom. Even though I'm no longer with her, I have no regrets about it because at the time, it was right.

I do, however, wish we hadn't built it up to be something that it really isn't and wish we hadn't treated it as a massive milestone.

It was the first time for both of us. It was after school on a Friday. We made plans to meet at her parents' apartment in the city.

When I got there, the lights were dimmed, candles were lit, and she was in lingerie. She told me she wanted it to be special for the both of us. The experience was amazing, and there's never going to be another time like it.

I was with the person I loved the most and couldn't have asked for it to be any better. We were together for a year or two and I loved her.

At the time, I was nervous — like, what if I'm not big enough or what if I finish too quickly? But I enjoyed the experience.

It was a rush of emotions. We had been dating for about four months. After kind of a lot of convincing on my part, she agreed to have sex.

At the time, I was thrilled. It felt almost as good as I expected it to. A bit awkward, sure, but worth it. I definitely have regrets now, though.

She wasn't ready for it and it put a permanent stain on our relationship, which went on to last three years. I will always regret not waiting until she felt more comfortable.

We were working on a summer play together, and there was definitely some will-they-or-won't-they chemistry between us.

We hung out a few times, and eventually, the subject of sex came up in conversation. I said that I was a virgin. She said she was fine with that, even though she wasn't a virgin.

We actually had sex during her period, but I didn't really mind it. I was pretty happy afterward as most guys are , but I wasn't going around boasting or anything.

Our relationship eventually turned rocky — pretty typical for a high school relationship — but I'd like to think we're friends now.

I try to keep in touch. It's a fairly simple concept, but when it's your first time, everything is difficult.

I was I was in a long-distance relationship with a girl I hadn't actually met in person up until that point. We didn't really know each other physically, and that probably contributed to the awkwardness.

I don't have any regrets, but it could have turned out better. I could tell she was getting frustrated with how I was performing, even though I told her it was my first time.

I was pretty nervous. There was a girl in one or two of my classes, but she wasn't my girlfriend. We were basically strangers.

Hooking up with her felt great because I could talk about it with my friends and feel good about myself and feel like the 'cool' one.

But it was super awkward, and if I could do it all over again, I certainly would have waited a bit longer — at least to be with someone I really liked.

She was great — funny but shy, cool but aloof, and she liked all the same music I did. One night, when it was pouring rain, she came over.

She couldn't get a ride, so she walked three miles. That made me think maybe she wanted to have sex, which was absolutely terrifying. We had never done that before.

We're both shaking — her from the freezing New England rain, me from pure fear. I'm pretty sure I used some stupid line, like, 'We should get you out of those wet clothes' or 'Let's warm you up, babe.

Eventually, I got it on. I came immediately. It was so brief, I honestly still felt like a virgin. A few weeks later, we had sex again for a more respectable amount of time.

I remember she said, 'OK, now I feel like I've had sex. I had hooked up a couple times with a girl who was a year older than I was. She asked me to pick her up at a party.

I didn't really know what her intentions were, but after she got in the car, she told me to park at a nearby park. We got in the backseat of the car and then things just escalated pretty quickly from there.

I was happy to get it over with, especially since a couple of my friends had already lost their virginity. Recommended Videos. He fucks me and cums on my pussy and tits.

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