Category: Dating & Hookups

Cum together while I clench my cunt. 2

Cum together while I clench my cunt.

“His pants don’t come off until I orgasm,” I say in my Pillow Princess par­a­digm. Sometimes, though, he cums while his pants are still on, too. Sometimes, we both fin­ish at…

3 Types of Submissives Who LOVE Cock Cages! 3

3 Types of Submissives Who LOVE Cock Cages!

Why male chasti­ty is more ver­sa­tile than you might think “I want to drink cum out of your ass with a straw,” ini­ti­at­ed a new naughty chat cus­tomer. Oh, you’re one of…

All-Around Horny, External Safety, and Internal Stories 4

All-Around Horny, External Safety, and Internal Stories

Am I con­sti­tu­tion­al­ly wired to be hornier than the aver­age woman, or is there a “nur­ture” com­po­nent at play? Today, we exam­ine some of the exter­nal fac­tors influ­enc­ing a wom­an’s…

Are Creampies a Kink? Why Are People Into Them? 5

Are Creampies a Kink? Why Are People Into Them?

On today’s episode of pas­sion­ate (but play­ful) shit­post­ing seman­tics: are creamp­ies a kink? Cue Carrie Bradshaw typ­ing at her Macbook with the voiceover, “And I couldn’t help but won­der…” Some of my…

Diary of a Sex Educator: my job and my dating experiences 6

Diary of a Sex Educator: my job and my dating experiences

I want to find a sanc­tu­ary in my long-term part­ner. That applies dou­bly when you’re in a polar­iz­ing career field. Sometimes, being a sex edu­ca­tor can put me in uncom­fort­able situations…

"Pillow Princess": 5 Ways I'm Reclaiming the Title 8

“Pillow Princess”: 5 Ways I’m Reclaiming the Title

The orgasm ratio between me and my male part­ners is eas­i­ly over 10:1 — 10 of mine for every one of theirs. I’m hav­ing a good time, and so are they.…

Q&A: What's it like to be a male escort? 9

Q&A: What’s it like to be a male escort?

For me per­son­al­ly, [being a good man] means fac­ing and resolv­ing bias­es that I may have regard­ing the idea of gen­der equal­i­ty and help­ing oth­er men resolve them, too. Guest writer…

7 Questions to Unfuck Your Love Life & Yourself 10

7 Questions to Unfuck Your Love Life & Yourself

Can you jour­nal your way to a more ful­fill­ing, bet­ter love life? I cer­tain­ly think so. It takes a degree of intro­spec­tion to dis­cern one’s own: Life goals and core val­ues Motivations under­ly­ing their tendencies…

I'm Ready to Start Dating. Now What? 12

I’m Ready to Start Dating. Now What?

I went on dates with 22 men with­in 13 months between rela­tion­ships. People get exhaust­ed, just hear­ing that sta­tis­tic. While meet­ing peo­ple to date is often sim­ple, it’s not nec­es­sar­i­ly easy — I…