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This happened three weeks ago and I still don’t know how I feel about it.
I’m 19, Singaporean Chinese, dating a guy (26) who works at a tech startup in one of those WeWork-style offices. His boss is this Australian guy, probably 40, divorced, expat lifestyle, lives in a serviced apartment near Clarke Quay. My boyfriend has been into cuckold porn for as long as I’ve known him. At first I thought it was just a fantasy, but he kept pushing for the real thing. Said it would be “different” with someone I didn’t know, less complicated. He suggested his boss—I thought he was joking, but he was serious. Apparently they’d talked about it after drinks. The boss was interested. I agreed because I was curious, honestly. The age gap, the power dynamic, the fact that my boyfriend wanted it, it all made me feel reckless in a way I liked.
We arranged it for a Friday night. The boss’s apartment. My boyfriend wanted to watch from the start, but I said no way, too weird. We compromised he’d hide in the walk-in closet, leave the door slightly open. He could see but wouldn’t be seen. The boss was professional about it at first. Offered me wine, made small talk about my boyfriend’s performance at work. Then he just… took charge. Kissed me hard, pushed me onto his bed, pulled my dress up. He was rough in a way my boyfriend never is. Confident, almost arrogant. I kept looking at the closet door. I knew my boyfriend was there, probably hard as hell, watching his boss take his girlfriend. The boss went down on me and I moaned louder than I needed to, knowing my boyfriend could hear. When he fucked me, he made me say how much bigger he was than my boyfriend. I didn’t know if it was true but I said it anyway. He finished inside me. I’m on the pill. After, he went to shower and I opened the closet door. My boyfriend was shaking, eyes red, pants around his ankles. He fucked me right there on the boss’s bed, reclaiming me, asking me over and over how it felt, if I liked it, if I wanted more. Now his boss gives him “special projects” at work. My boyfriend thinks it’s a sign of respect. I think the boss just wants another round. He texted me directly last week. I haven’t told my boyfriend.
Is this crossing a line? Or is this just how these dynamics work?