Personal Sexperience & Life Lessons

My first time wasn’t very glamorous. I was 15 years old and had been dating my boyfriend (we’ll call him Justin) for about a month. He was the first one to ever get past first base – in fact we rocketed from first base to third without much preamble. I liked him, I trusted him, but I didn’t love him. We had fun and we cared about each other, but I didn’t love him.

One day we were getting hot and heavy and our clothes ended up strewn all over the floor. He was hard, I was wet, and we were grinding against each other. Then somehow it just ended up inside me (I should mention here that I accidentally broke my hymen when I was 8 due to a gymnastics mishap). We both looked at each other, wide-eyed and unsure, before lust overcame us both and we just went with it.

I didn’t particularly enjoy it – I was caught up in how weird the sensation felt. Once Justin was spent inside me (we didn’t use a condom), we kind of lay there together not speaking. It wasn’t awkward or uncomfortable, we just had no idea what to say. We hadn’t discussed sex, nor had we planned for anything to happen. It was accidental sex.

I’d had opportunities before but they never seemed like ideal situations. I wasn’t someone who expected roses and candles for my first time, but I trusted my instincts. I wasn’t mad, sad, or upset in any way that my first time wasn’t special. I felt different afterward. It took me a good two days to really process what had happened, and get used to the idea of no longer being a virgin.

Now, with 20 years of hindsight, I have much more perspective on things.

I don’t regret dating Justin, nor do I regret that we were intimate. I do wish I had waited to have actual sex, because 6 months later I could have shared that gift with my first real love. Justin and I will always have that connection of being each other’s first. Although we remained friends on and off for another ten years, we are no longer in contact; I can’t help but wish I’d given that gift to someone special. It is an incredibly personal thing to give someone your virginity.

I’m also incredibly grateful that the lack of condom didn’t lead to pregnancy. I was VERY lucky in that regard.

Some people say giving yourself at any time is special, whether it’s the first or not. Some hold sex as a sacred thing to be shared only when truly in love. I’ve even met someone who couldn’t physically be with someone unless there were strong feelings between them. I personally don’t subscribe to that philosophy.

The best sex you can have is with someone you love, that much I won’t debate. Being able to fully trust someone and let go in a supportive environment makes everything that much more potent. Sex is at its finest when you know your partner is genuinely interested in pleasing you.

But you can still have a lot of fun without an emotional connection. It won’t be the same level of deep satisfaction – it may get you off, but it won’t fulfill you to the core. And sometimes that’s okay! I think having mediocre or less satisfying sex is good, in a way, because it helps us to appreciate the good stuff even more by comparison. And being able to fulfill your particularly lewd/kinky fantasies is immensely pleasurable. Most of us have a sexual bucketlist, and not all items can be fulfilled while in a relationship. Experimenting is great, expanding your horizons can be fun, and experience helps us fine tune our technique as we learn from others. Sex is awesome.

In the 20 years since Justin, I have had a full spectrum of amazing and horrifying experiences. I have learned a lot and tried many things, pushed my limits and pursued challenges. And I have gained a lot of perspective about sex, relationships, and everything in between.

Here is a list of conclusions I’ve drawn from my experiences:

  • Unless you know with absolute certainty that your relationship is monogamous without cheating, always use a condom. ALWAYS. STIs are common and very annoying. Most of them are easily treated but they’re a huge hassle. It’s a good idea to keep condoms with you at all times in case you need one.
  • NO MEANS NO. Never let someone talk you into something that makes you uncomfortable. If they try, get up and walk away. There are plenty of other people who will be respectful of your limits.
  • The best lovers are those who want to please you more than they want to be pleased. Someone who genuinely enjoys giving pleasure, and even gets off on doing it, is usually great at what they do. ALWAYS reciprocate the attention they give you.
  • Sex is only good when there’s communication. Don’t be afraid to say if something hurts, or if they’re doing it wrong. Talk about your needs, desires, and hot spots. Everyone is different and most people want to learn how to please you. If they’re unreceptive, walk away.
  • Similarly, let your partner know when they’re doing well. Moans and groans go a long way.
  • TRUST YOUR INSTINCTS. If a situation/person/activity makes you hesitate, then get out of it. Your subconscious brain can pick up on subtle cues that the conscious brain often ignores or minimizes. Your gut always knows best.
  • NEVER openly criticize someone’s body. You’re lucky you get to see it at all. If you think there’s something to be concerned about for health reasons, be tactful and respectful in mentioning it.
  • Try not to compare different partners. Everyone is unique and no two experiences, even with the same person, will be exactly alike. Comparisons don’t serve any purpose except to make us critical and judgemental.
  • Penis size matters a lot less than most people think. I’d rather be with a man who’s smaller but talented than with some hung idiot.
  • As long as they’re legal, safe, and consensual, explore your fetishes! Don’t feel guilty for having them – no one has to know but you and the person you play with.
  • The number of partners someone has had does not reflect who they are or their level of skill. Someone can have 100 partners under their belt and still be a terrible lover. Also, just because someone has had lots of partners, it doesn’t mean they don’t have standards. Numbers don’t really mean a whole lot in the bigger picture.
  • The brain is the largest erogenous zone. Example: I find a hearty philosophical debate more of a turn-on than dick pics. Stimulate the mind, then stimulate the body.
  • There are many different types of sex. Each has an appropriate time and place.
  • NEVER CHEAT ON YOUR PARTNER. They will always find out one way or another. The satisfaction you get from a night of passion isn’t worth the heartache you cause someone you care about. If you’re tempted to stray, sit down and figure out why that is. Cheating is often reflective of a deeper issue in the relationship, which isn’t necessarily about sex.
  • It’s a fact that you will be rejected far more than you will succeed; learn to shake it off.
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