I’ve been thinking about writing this post for a long time, but didn’t want to share it until I could be sure that someone reading could potentially take something from my worst sex ever. It’s also important to note that I’ve published this with the knowledge and consent of the person I’m writing about in this post.
Content note for vomit and cowardice when it comes to setting boundaries.
Let’s start by saying that the sex itself was great. The guy with whom I had my worst sexual experience was excellent in bed. Kissing him felt dirty, sitting on his face felt divine, and straddling is lap and spitting on his cock for lube as he jerked himself off was delicious. I also threw up on his dick because I’d been choking on it, trying to impress him.
Which is how I learned that I’m totally comfortable with sex having to stop so the guy I’m fucking can clean my vomit off his dick. A useful lesson, but not the only one I learned from this particular fuck.
So, why has it stuck with me as my worst sex ever? It’s because I was too cowardly to have the conversations I needed to feel comfortable fucking him. I was ashamed that I needed to talk about the sex we were planning before we fucked – and not just in the hot, hurried, how-hard-can-I-make-him sexts we were exchanging. I wasn’t brave enough to start the more serious conversations though, to ask him about safe sex, his STI status, his limits when it came to me calling him a pretty little slut when my dildo was inside him.
I knew his relationship was open, but I didn’t know if his primary partner knew I was at his house to fuck him that afternoon or they operated on a ‘don’t ask don’t tell’ system of non-monogamy. I didn’t know if I was allowed to talk about the sex, or openly flirt with him, when I had dinner with both of them in town that evening. Would she mind if I slipped off my shoe and pressed my foot against his crotch while we ate? Would he?
We’d discussed me topping him, and the idea of tying him up was incredibly hot. In practice, though, I didn’t know how to dominant this gorgeous, intimidating guy who was ten years older than me and had infinitely more sexual experience. I couldn’t summon the confidence to order him to his knees and eat me out while I told him in explicit detail how I was going to spank and tease his ass.
I hadn’t told him that while it wasn’t important to me to come during sex, the post-fuck analysis is important to me. I want to talk over the sex I’ve just had, to be reassured that I didn’t push too far as a dominant, or been too passive as a submissive. I want to get feedback and give compliments and bask in the afterglow of a fuck knowing I haven’t fucked up.
I didn’t tell him, and because I didn’t my first real adventure in casual sex went terribly.
I also only told him about my vaginismus when I was already on the bus across the city. While I’m adamant that PIV sex doesn’t have to be on the table in any sexual encounter, it is often assumed that when a cis man and a cis woman fuck some element of vaginal penetration will be involved. But the fact I hadn’t told him that he wouldn’t be able fuck my cunt was a sign that I was scared that asking any of my questions would mean he’d no longer want to me.
He would have, of course. Knowing him better now, he’d have not only been up for sharing the information I wanted but would have admired my confidence in being able to ask for what I needed. Even if that did mean we had to keep our clothes on for five minutes before the fucking started. Initiating conversations like this are hard. His consent to fuck me was never in question, but I didn’t know if I had consent to ask him my “silly” questions. After all, are you allowed to demand communication from a casual fuck?
Yes. Or at least, it’s totally reasonable for you to have that as a prerequisite for fucking someone. I won’t have sex with someone for the first time unless we’ve talked through a Yes/No/Maybe list and discussed safe words as well as ideas for filthy fucks. Even for a vanilla hook-up, I want to discuss what would happen if we wanted to stop fucking mid-blow job, or how they like their clit to be touched.
So I had sex that was wonderful but left me feeling pathetic. I bit down my questions, until they bubbled out of me later along with tears that were his first indication that I hadn’t been comfortable with anything we’d done. Of course, I don’t blame him for not realising that I’d been hiding my own humiliation at the idea I needed to talk.
He saw me cry, and I snuck out of his house stupidly early the next morning so I wouldn’t have to face him again. It’s taken me two years to be able to look back at the second person I fucked without burning with shame.
With two years hindsight, I look back at me then – blushing as he opened the door to me while naked apart from my panties – and want to scream at myself. Set your boundaries, I’d yell at my younger self. Tell him what you need. Have that difficult conversation. It’s taken two years to stop hating myself for not being braver.
Of course, I’ve fucked him since that awful experience. I know, through a mix of probingly horny questions, flirty conversations and sexting sessions, much more about their limits. I’ve talked to them about their relationships, their boundaries, and their kinks. The sex we’ve had – at a mutual friend’s dinner party, or in the toilets where we really shouldn’t have been fucking – has felt much lower pressure. I’ve had fun, and I’ve been playful. I’ve been proud of what I’ve learned from my worst sexual experience.
Today, I know I could take one appraising look at his dick bulging against the satin and order him to make me a cup of tea before I fucked him. I could get the information I needed by, if not while being flirty, asking outright with an endearing earnestness that I make for with the enthusiasm with which I give head. Today, I’d be brave enough to start that conversation if I needed to.
My worst sex ever happened because I was too scared to talk to the person I was fucking, and this is my promise to myself that I won’t fuck up fucking with that same mistake again.
Want to encourage me to keep exposing my soul and sharing my most vulnerable sexual experiences? Please show your love by buying me a coffee – I’ll raise a festive Starbucks in your honour!