5 Things Dating Older Guys Taught Me

I lost my virginity at the age of 17 to a boy who was 21. What’s weird about this is that it seemed late at the time. Mentally, I think 17 was the perfect age for me to lose it. As a twenty year old, I shudder when I hear of a girl younger than 17 losing it.

Back in the day, while I was focusing on my career, my friends back home were losing their virginities like it was a competition. Boys seemed like distractions to me and I didn’t want to become attached to anyone the way my sister had when she lost her virginity. Of course, there were a couple underage, alcohol-infused nights where I would hook up with a boy and give him a handy/blow job or let him go down on me but I never let it go any further. A month after I turned 16, I went home with a 28 year old who thought I was 18. I had been teasing him at a bar where I met him so he was really confused when I wouldn’t let him fuck me. Rather than admit my purity, I told him I just didn’t fuck the first time. I left his house at 2 AM after he had fallen asleep and luckily never heard from him again.

I became jaded about love at the age of 17. I had experienced everything else that came with adulthood except for sex. I had been living on my own in Europe and working from 3 AM to 7 PM then going out to get drinks or go to bed. I felt so grown up yet so innocent. I had a big Tokyo trip coming up so I decided to go home for a week and see my family during Thanksgiving. I met a boy and we clicked so I decided he would be the one taking my virginity. He was 21. While we were rolling around in the sheets, he went to put it inside of me and saw me flinch. He asked what was wrong and I decided to be straight up since he would be “the one”. He was shocked because I acted like I was so experienced and “mature”. I told him that I had been too busy with a career to date boys but now I just wanted to “get it over with”. And we did. And that shit hurt.

I left a couple days later to return to my Los Angeles apartment like I had accomplished something huge. I sauntered around and wondered if anyone could sense that I was no longer a virgin. The boy and I kept in touch over texts but I knew nothing was going to come of it. What weirded me out the most was that I didn’t feel anything after we did it. It was purely carnal with no emotional attachment. I had come to the realization that I could have sex like a guy and I LOVED IT.

The boy asked if he could meet me in Tokyo and stay for two weeks. I shrugged and warned him of the late hours I worked. He said it was fine and booked his ticket. A couple weeks later, we reunited and spent 14 days having sex and exploring my favorite city. I liked him a lot but when the airport shuttle bus drove away, I walked home listening to my iPod and mentally preparing for tomorrows editorial shoot.

I met an English man a month later. He had curly brown hair and a lovely smile. My friends thought he looked nerdy but I thought he was gorgeous. We hooked up one night and it dawned on me that I didn’t even know how old he was. I laid next to his sleeping body trying to assess him. I decided he must’ve been 23. We hung out that day when he revealed to me that he had just turned 30! I was shocked that I had sex with a 30 year old but then it started to make sense why he was so good in bed. Again, no attachment. Sweet.

I began having sex more and more when I went back to LA in May. I did it to feel pleasure and I didn’t care if the guy called me at all. I didn’t want them to most of the time. I was an 18 year old who viewed sex like it was sport.  (MOM, STOP READING HERE) By that August, I had slept with six different guys. None of them younger than twenty-three.

Then, I met a boy that I wanted to date. He was 25 and we saw each other for three months. After we parted ways, I decided to never date anyone under the age of 25 again. The next three years were filled with boyfriends and lovers, each changing my life for the greater good in some way by introducing me to these things:

1. Adulthood.

A certain boyfriend and I would lay in bed together while he would be working on his laptop every night for an hour. At first, I would feel annoyed that he chose work over me but then I understood it was his job. It was what paid for his lavish apartment and dinners out with me. He liked to introduce me to fine cuisine, buy me books, and show me “the real LA, not all of that West Hollywood shit”. He encouraged me to always be on top of my game with modeling and to not party so much. I learned to enjoy having a glass of Sauvignon Blanc and listening to him tell me the secrets of the universe rather than getting smashed at a club.

2. Emotion.

It was a man who taught me that showing emotion was okay. When I would cry in front of my brothers as a child, I could always sense that they were uncomfortable so it became stuck in my mind not to do so. I had always hid my true feelings and never cried until one day, it just poured out of me. This man held me while I cried and told me that it was okay to feel things. At the end of it, he looked into my bloodshot eyes, put his hands on my puffy, tear-stained cheeks, and whispered: “I want you to feel everything with me”

A boy won’t be there for you when you cry but a man will.

3. The Ins and Outs of Sex.

Men taught me my A-Z’s about sex: positions for my pleasure, making love vs. fucking, what men truly want in bed. When I was 18, I briefly saw another guy who was 16 years older than me. One night, we were at a bar together when he asked me if I had ever made love before and I shrugged and said I didn’t know the difference. His response?

“I’m going to show you the difference.”

We went home and he made love to me for what seemed like many blissful hours before we passed out entangled in each other. Anytime I tried to go faster, he would bring me back to the moment and teach me to truly connect. We stared into each other’s eyes the whole time. It was unlike anything I had ever experienced before. The next morning, he told me he was going to show me how to “fuck”. And he did.

4. The Fact That You Can’t Change Men

I lived on and off with the boyfriend of one year. He always told me that I was the one and wanted to marry me, often joking about just “going to the courthouse and getting it over with”. I sometimes felt suffocated but I thought that was normal when you’re with someone for such a long time. I decided to spend a couple months in New York and told him I would be back. He wasn’t too happy about this but I decided to go anyways. When I was away and able to reflect on our relationship, I thought of all the things I couldn’t stand about him and what I wanted to change. Eventually, I did come back to LA and I was quickly hit with the realization that he was invariable and gave up on us.

5. What I Want In A Future Husband.

I know you older twenty-somethings are condescendingly shaking your heads at that sentence coming from a twenty year old. I would understand that if it was someone who had a normal teenage experience, but I didn’t. Although that last relationship entailed quite a bit of heartbreak, I’m so happy for it. He was like a test-run. All of these men were test-runs. These guys showed me what makes me happy and what doesn’t.

Now, I am six months deep into a relationship with the best man by far. My boyfriend and I always kid that we were virgins when we met because of how fast we fell in love and how we have a rule not to talk about exes. What’s funny is our past exes molded us into who we are now and subliminally led us to each other. For that, I am forever grateful.


Megan Kennedy

One thought on “5 Things Dating Older Guys Taught Me

  1. Reblogged this on When you have it all and great sex! and commented:
    Jen is away for the weekend at a women’s faith conference and I thought I would reblog this as I found it interesting, especially since I am several years older than she is….Im anxious to have her read it when she returns home and comment on Megan’s thoughts and experiences. Thanks Megan!

    Liked by 1 person

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