A few months ago, I was out with friends, men and women, and we got to talking about sex. What else is new? When groups of friends have a couple three glasses of wine, sex is surely going to become a topic. One of my girlfriends, Beth, mentioned that she was curious why men would like (and she whispered the word) pegging. While I was engaged in the conversation, my ears perked up because pegging is one of my favorite bedroom games. Especially taking a newbie down their first pegging experience.

Beginning the Discussion of Someone’s
First Pegging Experience

Lots of giggles ensued and you could almost see the guys clenching their buttholes. 

Beth began asking questions. “Why would someone want to be pegged?”

I answered, “Well first, not only are men pegged, but women are, too.” They all knew I was lesbian, but hadn’t thought about women wanting to be fucked in the ass as well. “Oh yeah, women love anal play, too!” 

“Seriously?” a couple of the guys and gals said all together.

“Seriously,” I replied. “But for argument’s sake, let’s just talk about guys having their first pegging experience. It’s good to limit the topic a bit.”

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“So the anus is a delightfully sensual place to play. There are tons of pleasurable nerve endings in that area and once you get past the shame from when we were younger and the embarrassment that society brings along, those nerves fire yummy endorphins for you to experience. And yes, at first it can be uncomfortable, but anyone who is regularly fucked in the ass will tell you that the discomfort (or pain) lasts for a short time. Afterwards, it begins to feel quite yummy.”

What About, You Know…

I answer, “Prepping is in order. I will leave you to Google how to prep for a pegging session, but it isn’t anything worth worrying about. Know that after preparation, there is nothing to be concerned about. And if you are still worried, lay down dark colored towels, use condoms, even gloves if you want to. I swear, it is allllll worth it for the fun!”

Lube, Lube, and More Lube

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“Oh!” I begin. “I want to talk about lube for a minute.” 

By now, the whole table is all ears. I’m loving giving this lesson in the middle of a noisy restaurant.

“You can never use enough lube. If you think you have enough on the condom or dildo, you need to double it. You can also lube the asshole and that helps, too. Make sure you use the right lube for the job.” I toss in, “The fuck-job.” 

They all laugh. Earlier, the giggles were more nervous. Now they were all ears and the laughter was more genuine.

“With latex condoms, don’t use anything with oil in it… no lotion, Vaseline, or oil-based lubricants. Use water or silicone-based. My personal fave lube for anal sex, especially for someone’s first pegging experience, is silicone lube. Water lubes dry up fast, but silicone lubes last a good long time. You want to keep adding lube as you go along, too. As I said, you can never have enough lube for pegging.”

Get to It Already!

Now that I had everyone’s rapt attention, they wanted the down and dirty, so to speak.

“But I haven’t talked about dildos or harnesses,” I protest.

“For fuck’s sake, Daphne, we understand that part. If we don’t, we can ask you for recommendations later. Get on with it,” Beth whined.

“Well, once y’all have prepped, laid down towels… which are great anyway because of the copious amounts of lube… then the fun begins. You take your boy toy and make him get on all fours. Later, you can try different positions, but seeing what you are doing, girls, is important these first few times. Guys, it helps if you aren’t nervous as all get out. Relax however you can.” wink wink

“Then after you do the lube ritual, you hold that dildo… chick dick… and circle the rosebud (everyone giggled) with the head of the cock until you see it relax. Once that happens, you begin to push in. S l o w l y. Watch the anus open up as you gently push in. Go at the speed of your lover’s comfort. You guys have to promise not to tell her to stop. If your man starts to balk, grab his dick and stroke him for a bit. That will shut him right up.”

“Get that dildo alllll the way in and then stop moving for a moment so he can acclimate to the new sensation. Once you see his asshole relax a little, then start to fuck him. Slow and easy at first and when he begins to moan… and he will… then a little faster.”

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“You guys will fucking love it! I promise. Once you get over your nervousness and relax your love hole, you will appreciate the experience so much you will begin begging for it.”

I look around and everyone is leaning in, listening closely.

“Hey, what if, when we leave here, we go to a Toy Store and I fit you gals for a harness and pick out dildos that you guys might like.”

I watch as all hands go up, asking for their checks.

Once we are at the store, we head right for the dick and harness section. I know then that the rest of the day is going to be a fucking great one.