Pegging, Prostates and Anal with Guys

Posted by Dangerous LillycloseAuthor: Dangerous Lilly Name:
Email: dangerouslilly@gmail.com
Site: http://dangerouslilly.com
About: I am not your average girl. I swear like a sailor. I cook like a domestic goddess. I fuck like well…not a porn star, just someone who truly loves sex and pleasure. I love sexual exploration, kinks and learning about others' kinks. I can also be the most ADHD-mess of a girl you've ever seen; I'm impulsive, scattered, crazy and have the attention span of a gnat. Run to catch up to me some days, and wait for me on others.See Authors Posts (8)

Young & Stupid

Long ago and far away, my now-husband and I first played around with his ass. If I recall correctly, the first time was quite unremarkable and was little more than an exploratory teasing session that kept going. He seemed to really enjoy the sensations and was comfortable with it. The next time had purpose, and I brought out my smallest dildo. While I played with his ass and his cock, I witnessed a level of pleasure that I had never seen him reach before in my presence. When a glorious orgasm finally burst forth, with my dildo firmly up his ass, we were both in shock and awe. And then confusion. What did that mean?

I was young and stupid and I freaked out a little bit, thinking that maybe his liking anal play also meant that maybe he was……gay?

Like I said, I was young and stupid, and uneducated. I had never heard of a straight man enjoying anal play before.

Enter Aneros

After that first freaked-out discussion, couples-time anal play wasn’t brought up again between the two of us for quite some time. However, he had quite liked it, so he eventually sought out more information himself. Enter the Aneros line of prostate toys. Back then they had fewer choices, but nonetheless the site was extremely informative about the wonders of the prostate and the boundless joys of exploring it. Through this site and the forums, hearing from actual guys, it becomes very clear that anal play hasn’t got a damn thing to do with one’s sexual preferences. Duh!

Reading that site was like a light bulb being turned on. My previous misconceptions were gone and I was eager to explore it with him again. We bought one for him, and we continued to use the dildo and sometimes the Aneros toy. I learned that I quite liked being able to give him that much pleasure!

After my education, from then until present times, I encourage all my male friends and ‘friends’ to relax about exploring their ass. I feed them the safety information, I show them toys, and assure them that not only gay cowboys like having things up their butts. Granted I don’t bring this topic up with just *any* male friend, for example, none of the ones I work with!

The Fumbling Domme & the Too-Small Harness

Not too long after Hub and I began our initiation into the world of prostates, I had started seeing a guy who was sexually submissive. I was really very new to the BDSM scene, but I quite liked this person and thought “if this is what gets him off, I want to explore it too!” and away we went. He is the first guy I ever “pegged”.

Well, to be accurate, I should say that I TRIED to peg him. Oh it failed. It all failed so miserably.
During our first encounter with the intentions of butt sex, he brought along a harness that he owned and had been used by a previous girlfriend. Said previous girlfriend weighed about 100 pounds less than me and of course this wasn’t one of those really-and-truly-one-size-fits-all harnesses. Thankfully he was blindfolded as I fumbled with putting on the damn harness. I hadn’t a clue how to properly go about it, but I quickly figured out that the first problem was that it was just too small for me. But hey, he was blindfolded and so I let him believe that I was all suited up – it added to it, mentally, for him.
Let me interject here to beg of those interested in pegging their boyfriends to PLEASE educate yourself on safety, proper ways to ease into pain-free pegging, and so on. When I think back now to all of the mistakes he and I both made, it’s quite embarrassing actually.

For our future encounters, I didn’t want to admit to being too fat for the silly harness so I researched other options and I happened upon the Feeldoe. The intentions of the Feeldoe are good, but again there were a few caveats and research points that I didn’t delve into. The first being that I didn’t know just how much size matters when it comes to the butt. The second is that the Feeldoe isn’t the greatest choice for pegging, because the resistance in anal means that you have to have PC muscles tighter than a steel bear trap to keep the pony end of the dildo inside of you. Once again I saved face with a blindfold – he couldn’t see all of my behind-the-scenes/butt fumbling and so when I resorted to just using it as a standard dildo, he didn’t really know. Of course, it also turned out that the Feeldoe I purchased was just too big for his butt to manage, and so it never was meant to be for us.

Prostate vs Pegging

Knowing what I know now, reading the harness reviews that I have, I know that there are indeed very comfy harness options for a gal my size. But I see pegging and prostate play as two different classes. Just like penetrative sex and g-spot play can be really different. Pegging (and dildos in general) are more about the “fullness” sensation in the ass and against the prostate. The pegger can also be the one in control, but the pegee doesn’t always have to be submissive. Pegging requires a man with a more open mind – any latent homophobia will rush to the surface if he’s not open.

Prostate play is less about thrusting and fucking than it is just pure pleasure and manipulation of the prostate. It can easily be either just a solo masturbation act or a partner activity. Prostate play can involve toys (proper ones, please!) or just fingers.

Myth Busting – How to make men understand that liking anal play doesn’t make them gay

There’s really only so far a girl can go here. I’ve educated a few men in my time to realize that anal play doesn’t make them gay. And of course there are others that I just am never going to get through to. Education, reading the experiences of other straight men and their partners, talking about it with your guy and slow consensual playtime can all go very far. If there is a level of trust there he might agree to trying it out with you, but don’t be surprised if his society-driven mental blocks keep him from fully appreciating it.