I was handcuffed when I lost my virginity

NSFWFirst Time

I'm 35 now, but I first had sex when I was 19, with my now husband. He's not the only person I had sex with, since we broke up and got back together a few times before we got married, but he was my first. I was 19 and he was 29, and I was at a party at the medical school connected to where I went to college. I had kind of sneaked in because I liked the idea of meeting a doctor or two. And I ended up going to med school myself, so it was also good to talk to people who were residents.

He was gorgeous from the moment I saw him. Muscular but not bulky, great thick brown hair, not overwhelmingly tall, and brilliant. I had handcuffs with me because this was sort of a halloween party and I was sort of dressed like a cop, but nobody else was in costume and I just took my fake badge off when I got there and then I was just dressed in a black skirt and top. I'm not good at costumes lol.

I didn't have the courage to just walk up to him but he walked up to me, which was fantastic lol. We chatted for a bit and I kept touching his arms and his chest and basically throwing myself at him. He found the cuffs in my bag and was teasing me with them, asking if they were for me or for him. I clarified that they should go on me and he put one on my wrist and then asked if I had the key and I said it was a little late but I did. He asked when I should be let out and I said tomorrow morning.

He smiled big and said well now. I shifted so I was sitting on his lap and pulled the other cuff over my other wrist. He asked if I thought they should stay on all night. I said yes of course.

Then I thought about it - I overthink - and I said well, you'll have to take them off to get my top and bra off. And he smiled and said oh, you're going to be naked?

And I said I hope so.

His hand was on my thigh and it slid up a bit and brushed against my underwear and therefore pussy. I remember that clear as day. That made it much more real. I kind of panicked and said um so you should know that I've done other things but not that One Big Thing but if I'm handcuffed it's not like I could say no, so...

He said not saying no wasn't the same as saying yes and I think I fell in love then and I said yes, I'm saying yes. And he smiled.

And I did keep the handcuffs on - in front of me, behind me, over my head, attached to his bedframe, attached to his shower - until the next morning.

That's a good memory.

Posted Jun 3, 2026, 11:45 PM UTC

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