There’s always time to get it right
Virginity is a complicated concept.
Which is not so surprising, because sex is quite complicated and not so simple.
And yes, I know a lot of people think it’s really obvious. You are a virgin until the moment a cock is thrust into the warm embrace of your pussy.
But I don’t know, it never seemed that clear to me.
Like okay, sure. Once you put it like that, you’re probably not a virgin anymore. I can make it.
But what about pounding on a guy’s knee until you come? This seems like a very big leap forward in your sex life.
Then there’s your first time playing with someone’s cock. Or the first time you part your lips and put your mouth on one. If that doesn’t count as fucking, it’s at least fucking next door.
And then there are the ladies, who I happen to be extremely attracted to.
When you mess with another girl, where is the end? At what point does it stop being a pillow fight gone too far and turn into a proper grown-up slumber party?
It can’t just happen when one of you pops the strap. At that point you may already be married and trying to spice things up.
So yeah, it’s kind of a confusing idea.
But I think I’ve nailed it – at least for me, personally. If I look back at my own personal history, I would say that I have lost my virginity a total of three times.
They were all moments when I felt like I had reached some major sexual milestone.
It all changed me in some very important ways.
And they were all things I did for the wrong reasons.
I was young and stupid so I didn’t lose any of my virginity because I felt horny and ready. I didn’t because the sex stars had aligned and all was well.
I did it because I had a scarcity mindset about sex. And like any other kind of scarcity mentality, it meant I didn’t always make the best decisions.
Losing my Traditional Virginity
Being a virgin at sixteen isn’t really a big deal. But it sure looked like one to me.
For whatever reason, I realized it was a problem I had to deal with. I couldn’t finish high school and still be naked – that would be kind of embarrassing.
The clock was ticking and I was convinced I only had one shot. And that shot happened to be the soft-lipped boy who agreed to go steady with me.
You see, I didn’t have the best self-esteem back then. So I was shocked that no man liked me – and such a good kisser, no less. And I was convinced that if I lost him, I would probably end up alone until high school was over—perhaps forever.
I knew I would let him hit it sometime before graduation. I just wasn’t sure when.
But then he decided he was done with me and started flirting with one of my friends.
I felt him slipping away, so I played the only card I had left. I told him we can have sex.
And because one bird in the hand is better than two in some other virgin’s bush, he stuck it to me—so much to stick it in me, anyway.
I actually wasn’t ready. I was more nervous than excited. But at least I knew I wasn’t going to the dance just yet hoping someone would get rid of me.
It wasn’t horrible as hell. It was uncomfortable. There wasn’t nearly enough excitement. And zero romance, because there usually isn’t much of that when you’re fucking someone so they won’t leave you.
But it still felt good. Once he was inside me, I understood why sex was worth obsessing over.
I just didn’t know that sometimes it was worth the wait. Because it didn’t have to be surrogate sex with someone who didn’t really love me, as much as I loved the fact that I did.
Losing my Anal Virginity
There was something exciting about being the girl who did butt.
Not because I wanted to brag about it or anything – although yes, I might have done that a few times.
It was more that I found the idea very hot, vaguely kinky and kind of mean. Like my sexual journey wouldn’t be complete until someone had my ass really well.
And it didn’t take long for that to happen. But you probably should. Because, like many women before me, I gave my ass to the wrong man.
But I didn’t realize it at the time. Because I was still young and wide-eyed, and he was so attractive and sweet to me.
For a while anyway.
Our little honeymoon period faded away rather quickly. The super loving guy I was crushing on had turned chillingly cold. The undivided attention he gave me virtually disappeared.
And he stopped fucking me in a way that made me feel like I was floating on a soft cloud. Instead, he started getting upset with me for not fucking him the right way.
Because I had two little tiny borders at the time.
I was happy to suck him – like, really happy to please him with my mouth. But I didn’t want him between my lips and I certainly didn’t want to swallow his load.
I also knew that eventually I would rip up my back, thrust my bare ass into the air, and beg him to slide his cock into it—gently, slowly, but all the way to the base of the shaft, please. Just not yet – I didn’t feel ready to do more than fantasize about it.
However, he didn’t want to wait. She kept teasing me about it – really charming behavior, I know. And the longer the time went by without me swallowing it or letting him knock on the back door, the colder he grew on me.
And look, these days I know emotional manipulation when I see it. I can stop the love bombing once the fuse is lit.
But then, I was just scared. I thought I’d scored a great guy and was about to lose him – all because I’m no fun.
So, I decided to have some fun.
After learning zero lessons from my last serious relationship, I decided to let him kick my ass. And suddenly he was sweet and loving again. Go figure.
And it went like it usually does when you have anal sex that you don’t really want.
It was uncomfortable. He was not considerate or kind to me. I wasn’t turned on at all.
The only thing that helped me cope was the butterflies in my stomach – the feeling that he finally loved me again, that he was going to stay and that things were going back to the way they were.
And I guess in a way they did – they went back to the way they were before I met him. Because he still kicked my ass even after I let him.
I came out of that relationship with a little more experience. I learned about a few red flags. And even though I wasn’t one when I met him, I definitely felt less of a virgin after getting it from every angle.
Losing my Bisexual Virginity
I was only 19 but I felt like I had already done it all.
Hand, mouth, butt stuff. I was in the middle of a two three. I had sex outdoors, dangerous semi-public sex, and the guy who ran the local sex shop always recognized me.
But the thing is, I did all this with kids.
A lot of it was fun and exciting, but it still didn’t feel completely complete. Because I was also really attracted to women and had a really strong desire to explore that side of myself.
There was just one problem. I had already met the love of my life. For real this time. Not just some jerk who gave me hormonal butterflies, but a guy who treated me so well I ended up marrying him.
Which was great. Except I felt like my window for experimentation had closed.
I would never date girls, kiss girls and sleep with girls. I locked with a dude and locked well. It’s not like I was going to leave him or anything, but he still really surprised me.
Fast forward to my next birthday and things got kind of weird fast.
It was a really small celebration. Just me and my boyfriend, my friend Abby and her boyfriend, some cake and lots of cheap drinks.
It happened once when we were all good and bad. Abby put the moves on me – and she wasn’t subtle about it.
Things were about to fall apart. Like literally, we were less than half an hour away from falling into each other.
So I had a choice to make and I had to make it quickly.
Abby was cute and I really liked her. Although not in this way.
I was worried it would make things awkward between us too.
And I didn’t think there would be two men involved the first time I matched with a lady.
But that was it. This was my chance to hook up with a girl before I ended it with Mr. Austin and began my long and happily married life.
So I let Abby put me through the motions. I also put some back for her.
And I wish all of this had led to group sex that was as hot as a foursome should be. But mostly, it was uncomfortable.
I was drunk and clumsy. I was nervous the whole time, and not in an adorable way. And because we started our little pussy party without really talking about it, I was never quite sure what the guys were going to do – I don’t think they knew what to do.
So the kids watched. They joined hands, but only danced with the girls who came.
Abby and I made it, we played with each other’s tits and I licked each other’s pussy like it was a normal thing we did every drunken night.
Then Abby and her boyfriend got into a bit of a fight. Things became tense, uncomfortable and very quiet. They called a cab, probably fought harder when they got back to their place, and I spent the rest of the night processing everything that had just happened.
I was friends with Abby for a while and then we drifted apart. But because I panicked and decided to let her wake me up that night, she will always be my first.
There will always be more sex
I ran in all my first times.
None of these happened because I was turned on, felt ready, and found the right person.
It all happened because I felt like my options were running out.
I had this big lack mindset about sex because on some level I felt like I didn’t deserve it. I was convinced that I wasn’t cute or charming enough for him to cut me loose. Every time it happened, it felt like a fluke.
When a guy liked me or a girl made the moves, it surprised me. So I stuck with it, because I was always worried that it might be my last real shot.
It would be my last chance to get laid before I became a college-age virgin. And yes, of course now I realize how hot that is. But at the time, it kind of scared me.
It would be my last chance to keep a guy I thought was completely out of the league. Who knows, maybe even my only chance to get my ass – and I didn’t want to die without trying it at least once.
And quite possibly my one and only shot at burying my face between a girl’s thighs.
So, I went because I was kind of scared. This is not the best reason to fuck anyone, let alone for the first time.
And I kind of wish I could go back and tell myself that.
Because there’s always more sex to come—especially if you’re actually making an effort to have some. There’s no reason to jump on a bird like it’s the last one you’ll ever see.
I tricked myself into having great experiences for the first time. Instead of filling my bank with my hot stories that I can still masturbate to, I just did things that I kind of regret.
And I was completely and utterly wrong. Because there was a lot of good sex ahead, with more to come. All I needed was to put up with the right person at the right time.
If you enjoyed this article, you should totally check it out Sexy Semi-Nude Ladies (Legwarmers, Fancy Hats and Goth Cowgirls) episode of my dirty and intimate sex podcast, Pillow Talk with Emma Austin!
