I’m Cheating On My Boyfriend With His Dad’s (Much Older) Best Friend… And It’s Hot

It was never something I obsessed over, or even let myself think about more than once. But my boyfriend's dad's best friend was different.

By Anonymous

Updated 11 years ago, September 29, 2013

I used to think of myself as a good girl, pretending to be bad when I was small, knowing I couldn’t ever do anything bad — or so I thought. That was before puberty, before I had my unhealthy relationships, and before the standard mixture of teenage complexities set in. When I was thirteen, I was a virgin, but promiscuous. I cheated on a casual boyfriend with his best friend — he was really the one I wanted. Then, I thought I’d redeemed my so-called ‘evil’ ways and become a whole, pure person.

I never knew how difficult it was to trick yourself.

A few years later I’ve been in a loving relationship for quite a while. Then, he cheated. I forgave him. He cheated again months later; I forgave him again. He told me he’d cheated five times. I forgave him. I knew things would be different — it wouldn’t happen again. I was the one comforting him, and I would never think of cheating on him. He’s the guy who I’ve waited for my whole life. He’s the one I gave my virginity to. I love him, I really do. I want to be with him my whole life. Every day, I think about how our life will be together in the future.

But then his dad’s best friend came into the situation. He’s eleven years older than me. Which is right split between his Dad’s age and mine. He was attractive.

Of course I’ve seen attractive people before, older men. Of course I’ve been around them, of course I’ve had brief little fantasies about them. But it was never extensive — never more than a mannequin with their name coming to my room late at night, filling my mind for a split second. It was never something I obsessed over, or even let myself think about more than once.

But my boyfriend’s dad’s best friend was different. I was instantly flirtatious when I saw him, putting on a pitch-perfect innocent best-friend’s son’s girlfriend who just happens to wear a little less-than-conservative clothing whenever he’s around. I became the secretively seductive faux-niece.

It was pretty normal, just casually being a good little girl for quite some time. Then, at one point, my boyfriend and I were in a major slump. We were fighting a lot and he was being mean to me — he would get mad and would tell me what I can and can’t do, and try to control me. I’d agreed to all of his conditions, but after a huge fight, I stopped caring. I stopped caring about obeying his little, ridiculous commands. I wasn’t allowed to look at other guys. I wasn’t allowed to have guy friends. And I wasn’t allowed to look at porn.

So that night I watched it for five hours.

And guess who I couldn’t stop thinking about? His dad’s best friend.

I told myself I knew I’d never cheat; I’d never hurt my boyfriend like that. But the next day, he was all I could think about.

The day after, I was planning. I didn’t know if he actually would let me go through with it, but I’d thought he would. I justified it all by telling myself that my boyfriend had cheated multiple times and I’d never done him wrong, so getting secretly even would just satisfy a saddened spite. I wouldn’t ever tell anyone, and I’d keep myself from telling him whenever I felt guilty.

I told my boyfriend’s dad’s best friend that I needed to talk to him later. I’d sneak out to where he was staying, very nearby our house and talk to him. He told me if he was asleep to kiss him on the cheek to wake him up.

I went there at 1:30 in the morning. He was shirtless in his bed, pretending to sleep. My blood was pounding. I could feel it in one specific place. He told me to lay down next to him and talk to him quietly, so nobody would hear I was there. I told him I felt really bad because I’d been having fantasies about someone else, even though I’ve got my boyfriend. He told me that that’s normal because I’m young. I told him the bad part was who they were about. He asked, and I said him.

It escalated from there. He asked me how prepared for this I was, I told him I had a condom in my bra. He said “Good girl,” and I was tingling everywhere, practically purring. He told me “Not saying this is going to happen, but if it were to, it will never be spoken of again.” So I took a vow of secrecy as it started to happen, and afterward, he told me he’d do it all over again. I told him I’d do it any time he’d like, and went back to my house and spent all night awake in my bed, covered in chills from how amazing it was.

I tried to feel guilty, because I knew I should, but I didn’t. Two days later, when my boyfriend and his parents weren’t home, he told me that he was coming over. I loved every minute of it, and we came up with a code word to know when I needed to be waiting for him. I haven’t seen him in a while, but he showed up at my boyfriend’s house yesterday and there was a lot of tension. Hopefully I’ll get it again soon. It’s sad because I like his girlfriend, but then again, I don’t care. I’ve stopped feeling anything other than lust and satisfaction in the fact that I can get whatever, whoever I want. I’M the heartbreaker this time — not him.