Last week, I stick my finger up a guy’s ass during a blow job. He likes it so much our next date is buying a strap-on together. There’s more to the story but I think it’s easier to just get the important part out in the open.  Talking about sexual exploration and actually trying new things are completely different actions.  After many years of sexual repression, I’m making an effort to talk less and do more.

I first heard about pegging on Tinder.  After some drunk, heavy-handed innuendo messages, some random 30something guy swept me off my feet with this line:
“I am into queer, fem things like pegging, is that at all interesting to you?”

People label me as queer.  Apparently it’s the cliche my outer shell most resembles.  My identity is as fluid as the androgyny I embrace, so I don’t necessarily call myself queer.  Physically I’m an attractive woman, mentally I’m a fem-dom and emotionally I’m a confused teenager.  I’ve met a few people similar to me and the majority use queer in their profile description.  I haven’t quizzed anyone specifically about their sexual identity but I can tell they don’t judge me for my choices.  That’s a great start.

The candid nature of pegging guy’s proposal appeals to my curiosity, even if the resulting conversation gives him all sorts of wrong ideas.  I ask him questions as if he’s my freelance sex therapist.  He blathers.  I never say anything directly about pegging him but he pretends I do.  Gotta give him credit though, not all men will beg a woman to fuck them in the ass sight unseen.  He is extra-excited at the thought of being my first.  Bless his heart.

After that enlightening conversation, I bring up the idea of ass play with someone I’m actually attracted to.  One of my friends-with-benefits touched on the topic with me in the past, so I don’t need to look far.  I casually mention pegging and he perks up like a Pomeranian in front of a pizza.  He confesses to his personal research into this.  He mentions doing preliminary “tests” at home.  I giggle while demanding more details.  He said, “I got three fingers up there during a shower the other day.”

I blush deeply and say, “Okay.  But you’re buying the gear.”

“Deal,” he grins.