A pegging story for Anal August

Pegging is one of my favorite topics (although I have a lot of favorites 😉 ) It’s something I write about, teach about, and love in my personal life, too. Sometimes my personal and professional life overlap – especially when I’ve got new toys to test out. Sending a picture of toy I want to try is my version of a (consensual) dick pic, and it hasn’t failed me as a pick-up line yet.

When Tantus sent me the Curve, I knew I’d be having some fun with it. The trick was waiting for the right opportunity.

That opportunity came when I met someone at a sex club who was interested in pegging. I’d actually taken a different date to the club, but that’s another story… one you can watch online here.

When my first date left I was immediately approached by another man. I’d never actually done pick-up play with a stranger at a sex club before (and haven’t again since) but our conversation went very well and I was eager to salvage the evening. When we had the safer sex talk I explained that I’d only be comfortable with gloved hand sex and to my delight that was fine with him. When we entered a private room and started playing he confessed that he’d always been interested in pegging. Well, I couldn’t resist a big cheshire grin spreading across my face and I told him he’d come to the right gal. I didn’t have any toys with me that night but I used my hands and we had a great time.

A few weeks later when the Curve arrived I knew exactly who to text. I sent a picture of my new toy to the man I met at the club and asked if he still wanted that pegging date. He was surprised and delighted by the proposition and asked, “Are you going to blog about this?” The answer, of course, was yes.

When he came over we had another negotiation and agreed to stick to hands and toys again. We had a lot of fun rolling around and warming him up, though he was eager to try the big toy. Because we were going to be using a silicone toy, I made sure we were using water based lube. While I feel strongly that lube makes everything better, it’s absolutely essential for anal play.

I slid into my harness and mounted the Curve. I always love the feeling of putting on the harness and I especially like the look on the face of whoever is waiting for me in bed.

The Curve isn’t small, so it won’t be a good first-time toy for everyone, but it was a huge hit with my date. The intense curve of the toy (where I assume it gets its name) is ideal for hitting a prostate. We tried a full range of positions, starting with missionary with the assistance of a Liberator wedge and then switching to doggy style. I particularly love the role reversal elements of throwing a cis-man’s legs over my shoulders during pegging and I think it can really add to the experience for some people to be in positions that contribute to a feeling of vulnerability. When it comes to doggy-style with a strap-on, one fun trick is that you can turn the dildo around so that it’s still aiming at the prostate.

Finally, I suggested he get on top so that he could play with having control over speed and depth. While at first skeptical, this position really ended up blowing his mind. And for my part, this is one of my favorite positions with any partner because I love being able to lay back and enjoy the view, as well as having my hands free to touch my partner’s body.

Overall, both the pegging experience and the toy were a huge hit. I even received what must be my first ever testimonial for my personal sex life, “Wanted to thank you for our time the other night. It has been a fantasy of mine for a while and the whole process from beginning to end was very enjoyable. I learned a lot about myself and I’ll feel much more confident expressing my needs and wants with my next partner.” To be perfectly honest, that got me a little choked up. That’s certainly the goal I’m striving for in all my intimate encounters.

 

Want more butt stuff? You can check out my Strap-On Megapost, my recent article for Kinkly on oral-anal safety, and also my Kinkly piece, The Ultimate Guide to Having Anal Sex.

You can also check out the sale Tantus is having right now on butt stuff and other fun items here. The sale runs from August 17-19 but if you miss it, don’t despair! You can always get 15% off on Tantus products by using the code STELLA15

This post contains affiliate links, but all opinions are my own.