Sex & Dating

Ask a (S)expert: “My First Time Having Sex Was a Flop... Can You Help?”

Welcome to our new series led by Gigi Fong, Hypebae’s in-house sex and dating editor.

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Ask a (S)expert: “My First Time Having Sex Was a Flop... Can You Help?”

Welcome to our new series led by Gigi Fong, Hypebae’s in-house sex and dating editor.

Welcome to your new safe space and Hypebae’s first-ever sex and dating column, Ask a (S)expertThis new weekly series is led by Haitian-Chinese and LA-based sexpert Gigi Fong, our in-house sex and dating editor.

Gigi is a former sex worker, boudoir artist and podcaster now hosting safe spaces for the Hypebae community. She specializes in all things sex-positive from unconventional dating to pleasure for lovers of all identities. To have your questions answered, visit our dropbox below and anonymously send your intimate inquiries ♡


“I’m 23 years old and I recently lost my virginity, however things didn’t work out the way I expected to. Now I’ve decided to give it another try with a different person but it just seems as if I can’t feel pleasure and it’s mostly painful to the point I can’t even bare it most times. I read online about arousal non-concordance and I’m wondering if that applies to me. I always start liking the person but after a while it becomes this weird memory that whenever it pops into my head, I get horrid goosebumps through my body. I’m worried this might make things impossible for me to ever have a relationship where I truly enjoy sex and don’t end up somehow resenting them for forcing me to do it. I’ve considered whether or not I’m asexual but I do have that time of the month when I’m particularly hot but it comes and goes and I really don’t know where I’m standing anymore. I’d really use some help cause I realize I’m hurting in many different ways when I shouldn’t. Could you help?”

Hey bae! Congrats on exploring sex for the first time! Before we dive in I have to offer some consolation: a lot of our “first times” SUCKED – and not in a good way. Just like trying anything new, you can experience anxiety, fear and confusion which all contribute to an odd first time. I love that you are doing the work to understand what made it terrible and how you can elevate sex in the future.

How to deal with painful sex:

For starters, experiencing pain during sex occurs with over 75% of vagina owners — virgin or not. During your first penetrative experience, your vaginal muscles are stretching more than they ever have which can cause pain. It’s best to practice a lot of foreplay and outercourse to give your vagina enough time to lubricate and relax for penetration.

If you’re still experiencing painful sex after exploring penetration, I would read our guide to painful sex and also explore  The Pelvic People’s buffer ring which helps moderate penetration depth. There are many products that assist with relieving pain from CBD sex serums that increase arousal and relax the vulva to buffer rings that reduce penetrative pain. Similar to celebs like Meghan Trainor, some people have partners that are more well-endowed which leads to uncomfortable sex. If you feel like your lovers are penetrating you to deeply, buffer rings can help.

Exploring Asexuality:

As for asexuality, this refers to experiencing little to no sexual attraction to others. Does this resonate? It seems like you are able to get aroused with others, however, your body and mind are struggling to sync up and allow you to feel pleasure. More specifically, you may be experiencing performance anxiety due to it being your first time.

Keep a Pleasure Journal:

Ultimately, I’d recommend visiting your physician to rule out deeper issues regarding painful sex, such as endometriosis and other known diagnoses that lead to pain. Unfortunately, visiting a physician is not a one-size-fits-all-solution, just as Emily Sauer, founder of The Pelvic People, shared in her interview. Most women find themselves having to advocate tirelessly to be believed — medical gaslighting is real.

So, first order of business is documenting each symptom of uncomfortable sex you feel. The best way is to keep a pleasure journal. Write down what types of foreplay you dabbled in, from oral to fingering, and then detail how wet you felt, relaxed, etc. Also, make sure to document the level of pain on scale of one to 10.

This information will help your physician monitor your symptoms and show intention — aka they’re less able to blow you off because you’re documenting each step. If you do feel blown off in the treatment you’re given or not, make sure to ask the doctor to put in writing that they refused to assist. That usually does the trick.

Wishing you the best of luck, bae!

Happy f-cking!

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