All my Firsts [MF] [Virgins] [Long]

This is going to be a little tame, but hopefully some of you will enjoy it all the same.

I started dating my girlfriend in February a couple years ago. For a senior in high school, I was shockingly inexperienced. Holding hands was a big deal for me! It’s not that I had any moral hangups, I was just nervous and shy to a fault. As a result, the physicality in our relationship developed at a snail’s pace, but that meant I got to savor every milestone.

Our first kiss came more than a month after we started dating. We were sitting together at a mutual friend’s house and somehow one of us worked up the nerve to ask. We kissed once, then kissed again for longer. Her lips were wonderfully soft. While the kiss was far from passionate, there was an intimacy in the gentleness. That night, she texted me and said it was the most “comfortable” kiss she’d ever had. See, I wasn’t her first boyfriend. Her ex, however was quite terrible in bed (as well as being terrible in a lot of other ways). That simple complement gave a sorely needed boost to my self-confidence.

Over the next several weeks, we had almost daily make out sessions, but we didn’t get any further. I desperately wanted to feel her breasts, but was far too terrified to ask for fear that she might think I wanted to push things too fast (in hindsight, that was pretty stupid). I remember feeling he bra strap on her back through her shirt and being ready to burst. She also wanted to feel me, but went about it differently. She would reach her arm low across me hoping it feel my bulge on her forearm. I, of course, was afraid she was merely trying to support herself and didn’t want to feel how hard I was, so I rolled my hips back such that she couldn’t feel anything without being really obvious.

Well, one day my friend said to me that my girlfriend was wondering why I hadn’t tried to move past kissing. I took that as my queue to try something, and I came up with a plan. I decided the easiest way forward for me would be truth or dare with her, so when we got to my house that day and found ourselves alone I asked her if she’d like to try it. She said yes! We climbed into bed and began asking each other questions and asking to touch each other’s bodies. I felt her breasts over her shirt. We even both took our shirts off! (I’m shy about my chest though I don’t really have anything to be ashamed of. I’m 5’11” and thin, but toned) She left her bra on, but as she lay on her side facing me I caught a glimpse of her nipple, which made me even more excited than I already was. She has these lovely, perky b-cups that are just big enough to grab onto and have some fun with. On one of her turns, she asked to feel my ass, which she’s always had a thing for. On another, she finally felt my erection over my underwear. Finally, she had felt it, which was a huge relief for me since it meant I no longer had to worry about her finding it accidentally. Unfortunately, I didn’t get to feel her that day since she was on her period. To get any farther, we would have to wait.

Not for long though… That Friday night I drove her home, but instead of dropping her off, she had me park a block away from her house. We climbed into the backseat to make out and we started getting handsy. We kissed passionately, feeling each other over our clothes. She rested her hand on my crotch, then she put it down the front of my shorts, rubbing my hard cock. I worked up the nerve to ask her if she was still on her period. She wasn’t! She then guided my hand down to the her wetness. She was soft, warm, and dripping. I rubbed her opening and circled her clit a few times before slipping my index finger inside of her. We continued to kiss passionately as she moaned softly. We didn’t have much time though, so we had to stop ourselves. I drove home with a substantial wet spot in my underwear from all the precum, and finished myself off as quickly as I could. I didn’t know at the time, but she had done the same as soon as she got into her room.

It didn’t take long for us to progress even farther. Later that weekend she and I were at my house with some friends. We got bored of cards and decided to watch some TV. My girlfriend had other ideas though. We pulled up Malcolm in the Middle on Netflix. Now, she and I have seen every episode, so it’s not like we were going to miss much. I still wasn’t prepared for her to ask me if I wanted a blowjob though… Now, at that time I was paranoid about making a mess or leaving any evidence, so paranoid that I didn’t want to use the bed. Instead, I opted to get my first ever blowjob in the bathtub. We went to the bathroom, locked the door, removed our clothes, and positioned ourselves in the bathtub. It was cramped and kind of uncomfortable, but both of us were still very excited. When she finally wrapped her mouth around me, I couldn’t believe how great it felt. Every movement sent little ripples of pleasure running through me. Just because it felt amazing didn’t mean I finished quick though. I was lucky enough to have my ecstasy drawn out. She bobbed, sucked, and licked and I loved every minute of it. We did experience a little hiccup when the episode ended and our friend asked what we were up to. Thankfully, my girlfriend is a quick thinker. She lied and told him that I was helping her unclog the toilet (of all the things she could have said). With our friend seemingly satisfied with that excuse, she went back to work on me, and it wasn’t long before I was having my first orgasm from someone else. I gave her plenty of warning, but she kept right on going as I writhed in pleasure, taking every last drop of cum and swallowing it. I asked if I could return the favor, but she didn’t want to. She did let me kiss her though.

We didn’t get past oral for a while. We even settled into a little routine. We’d cuddle, then I’d finger her, fondle her breasts, and kiss her while she rubbed her clit. This was the only way to get her to cum at the time since she had given herself death grip from years of masturbating using the same technique. Then, we’d switch, and she would suck me off. She got better and better each time, and the amount of time it took for me to cum went down from 20 minutes to about 5. The strength of the orgasms didn’t decrease though!

We did that for a while until we finally got the opportunity we had been waiting for to finally go all the way. My parents went out to lunch a half hour’s drive away (we usually fooled around at my house because my parents are more liberal, plus I have find my friends on them so I know when they’re coming home). Naturally, we jumped on each other as soon as they walked out that door. For a little while though, the clothes stayed on. That gave my parents time to get nice and far away, eliminating that source of anxiety for me… of course, it was also good foreplay. We kissed, cuddled, and fondled each other until we were finally ready. Gradually, the clothes started coming off. Soon, we were cuddling naked. Then I asked if I should go get a condom. She nodded, and off I went. I had some in my closet. The first kind I tried was enormous and didn’t fit right (I didn’t pick it out). Seriously, that thing literally fit my foot better than it fit my dick (we tested later). The second one was normal sized, and fit much better.

Now, it wasn’t her first time, so we decided that she should go on top to start off. I lied down on the bed, she got on top of me, rubbed herself a few times with the tip of my penis, got it all lined up, and slowly moved down. It had happened! At that point, I was guaranteed to at least not die a virgin! And oh it felt nice. Sure, the condom limited some of the sensations, but I didn’t care. This was still sex! She began to move on top of me while I kissed her and played with her breasts. Soon, I was moving too. After a little while, I got a little confidence, and asked to try going on top. That took a little getting used to, but eventually I figured out. After a little of that, she turned over and guided me into her from behind. I prefer the leverage and the angle from behind and, based on her moans, she was enjoying herself too. However, it does leave a little to be desired in terms of intimacy. We tried using the edge of the bed, she went back on top for a bit, and then I got back on top of her. I put her legs up over my shoulders and leaned forward, pushing her knees almost to her shoulders. When I started to thrust into her again, we both knew we had figured something out. With her in that position, I could push down into the bed and let her spring back to me, which allowed for more speed and fun. After a few minutes like that, giving her everything I had, I was ready to cum. I kept pounding into her as I lost control and filled up the condom, collapsing on top of her.

When it was all over, we cuddled, cleaned up, and cuddled some more. In the end, though I know that I could have lost my virginity much sooner if I had worked up the nerve, I’m glad I waited. While there was some awkwardness figuring out how to do everything, I felt completely comfortable with her. And that’s really important. My first time went off without a hitch and I haven’t felt even the tiniest hint of regret. I knew I wasn’t going to be great, so I wasn’t too disappointed that she didn’t cum (don’t worry though, we figured the right position for that a few months later). I had a really great time, and I think if you ask her she’ll say she had as much fun taking my virginity as I did losing it!

Source: reddit.com/r/gonewildstories/comments/695agd/all_my_firsts_mf_virgins_long