Jessica Simpkin

The archive

Writing

First-person answers to the questions people actually type into Google. One story, then the useful bit.

Showing posts tagged first time · All writing

Threesomes and ENM

What to Expect From Your First Threesome (Less Porn, More Pausing)

What to expect from your first threesome. Jessica's first-time essay.

25 August 2026Jessica Simpkin

Dating and first times

First Time Sex Nerves, Even When It Is Not Your First Time

First time sex nerves: what Jessica does with the shake, the overthinking, and the silence.

27 March 2026Jessica Simpkin

Dating and first times

First Time Sex With a New Partner, Even If You Are Not New to Sex

First time sex with a new partner: nerves, bodies, and Jessica’s first-night checklist.

19 March 2026Jessica Simpkin

Dating and first times

How to Have Sex for the First Time Without Treating It Like an Exam

How to have sex for the first time: nerves, logistics, and Jessica’s own clumsy first.

28 February 2026Jessica Simpkin