The Singlehood Series: I’ve Cheated On Every Boyfriend I’ve Had And I Don’t Regret It

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I started dating when I turned 18. Before then, I was a virgin and I barely knew anything about relationships. My first boyfriend was significantly older than me but he fell madly in love with me and in turn, I grew to love him. He treated me like a princess. However, for the first few months of our relationship, we hadn’t slept together. I thought he was being a gentleman since he knew I was still a virgin. When I joined campus, reality hit hard. Sex was the norm and my roommates were all sexually active.

Don’t get me wrong, I wasn’t a saint either. I’d go out to party with them but I’d return to my hostel the same day. They, on the other hand, would come back the following day and talk about the guys they were with. I used to find it so fascinating how comfortable they were talking about their sex life. After two months of living in the hostel, the pressure started getting to me. I used to go to my boyfriend’s place every weekend that I wasn’t home but temptations were still there during the weekdays. So, I decided to lose my virginity to my boyfriend, someone who I had feelings for before I lost it to a random university guy.

Let’s just say, my experience was seriously underwhelming. I stayed up that night wondering what the fuss was all about.

“This was what my roommates were so obsessed with?” I kept asking myself.

Now that I had lost my virginity I felt more at ease with exploring my sexuality. And after my disappointing experience, I wanted to know if that was all it was about. During our many partying sprees, I bumped into an old friend who had recently joined our campus. He was slightly behind since he had to do a bridging course. We clicked and the sparks flew instantly. We ended up partying together frequently and one night, we slept together. It was different with him. It was like he knew everything he was supposed to do.

I was still pretty naïve and the fact that I had cheated on my wonderful, loving boyfriend stressed me out. So, I decided to come clean and tell him what had happened.

“Babe, I did something wrong.” I started.

“What did you do?” he asked looking up from his laptop.

“I met an old friend. We went out to party and I slept with him.”

He went silent. I could see the pain, heartbreak, and sadness in his eyes which brought me to tears. Somehow, seeing me cry made him forgive me and I promised never to do it again. But I didn’t stick to my promise. Barely two weeks after coming clean, I went out again with the guy and we slept together again. It soon became a regular thing that I didn’t even bother telling my boyfriend. I just liked sleeping with this other guy. Eventually, I decided to end my relationship with my boyfriend because I wasn’t being faithful and it wasn’t fair to him.

Though we continued partying and sleeping together, the other guy wasn’t keen on being in a relationship so I had to end things with him as well. A month later, I met a new guy whom I liked and we started dating. This is by far the longest relationship I’ve been in. We dated for three years and everything was perfect. I never cheated, not even once, until I heard rumours that he was being unfaithful. This was probably the first time I was in love with someone so I wasn’t quick to react. I confronted him about it though.

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“Is it true that you’re cheating on me?”

“I would never cheat on you…” he said then paused, “but there’s a girl who invited me to her place. We didn’t do anything but she wanted to.”

At that point, it didn’t matter whether he cheated on me or not. I couldn’t shake the thought out of my head and it only tore us apart more. During the holidays, I ended up sleeping with one of my neighbourhood friends. The relationship ended after we cleared campus and though we tried to rekindle it, I had completely checked out of it.

From then, it became the norm for me to cheat in all my relationships. Even when I was madly in love with the man, I’d still cheat on them. They say that your first relationship sets the tone for all your other relationships. I don’t know how true it is but I couldn’t stay faithful in relationships even if I tried.

In my latest relationship, I was in a full-on entanglement. I had met someone who was, in my books, the perfect guy. He was good-looking, rich, smart, and a gentleman. Why would I cheat on a guy who had all those qualities? But I did. Shortly after we started dating, he introduced me to his best friend. He lived in the same building as my boyfriend so he’d come over to the house often. We were friendly with each other but we never flirted. However, there was a strong sexual tension between us. He wasn’t much of a talker but he used to look at me in a very lustful way.

My ex used to work a lot and some days, he’d come home in the wee hours of the night. We had a good sex life but it wasn’t consistent. The more me and his best friend spent time together, the more he got comfortable with me. Before we knew it, we had sex. My ex found out about it and let’s say, he didn’t take it very easily as the rest of the other exes. There was drama but as per usual, we broke up.

I decided to take a break from relationships to really figure out if I have a problem with being faithful or maybe it was just a phase. However, I don’t regret cheating on my previous boyfriends because, at the end of the day, I truly learned about my sexuality. Now I know what I like and what I don’t. I can say I’ve had a pretty good sex life.

Check out these stories

I Had An Affair In Advance To Avoid Being Hurt By My Husband Who I Suspected Was Cheating On Me

The Condoms In The Drawer

Our Friendship Turned Into A Competition & Then She Stole My Man

When You Find Him Cheating

She Got Caught Cheating On Her Office Boyfriend

I Found The Other Woman Driving My Car

He Shared My Nudes On Social Media After We Broke Up

After 2 Years Of Raising My Daughter I Found Out I Wasn’t Her Father

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The singlehood series is a collection of real-life stories and opinions from different people. It looks at the current world of dating in Kenya and experiences that people have gone through. The views and opinions expressed here are those of the contributors and do not necessarily represent or reflect the views of