I love strapon play and find pegging to be pleasurable and not painful. However most of the online descriptions show it to be a form of pain or punishment.

Im curious about how others feel when they do it?

I am an absolute strapon fanatic and I've never used it once as a punishment (and I've been pegging people for +6 years).

I've never wanted it to feel painful. It's just not the activity I think of when I think of punishment. Strapon, in my opinion, is an intimate and primal act, and an epitome of role-reversal.

I do know people that do it as a punishment activity though, so to each their own

For me, the only punishment I intended to dish out with strap on was humiliation and objectification. It could get a little dicey punishing someone's anus internally. Strap on, when done correctly, should hurt just a little at first and then get to the point that it becomes physically pleasurable. I went from the perspective that for a straight man to enjoy a dick in his bum, even to the point of having a release, would be humiliating. Kind of like the blend of sweet and sour.

For me Cheyenne has hit it -- strap-on is very much humiliating and degrading to me, and that's the element of punishment funishment. I enjoy that aspect of it, and totally understand it as fantasy punishment, the same way forced pussy worship is not really forced (wink wink!!), etc.

I do not feel pain during strap-on -- in fact, pain is definitely something one usually shouldn't feel, I'd say. Probably not a good sign, in most cases. However, strap-on does feel extremely intense to me. I mean, really intense. That intensity translates to the same expressions you might see in a video clip -- I'm pretty sure my entire head turns red, my eyes bulge, I make silly sounds, etc. LOL ... it's intensity, not pain, but someone watching could interpret it according to however their fantasies dictate

I think video and online based descriptions make more sense when you can figure out whether the perspective is one of male fantasy perspective (in which case, strapon is punishment) vs a technical or non-prurient discussion

Interesting perspectives. Thanks for sharing. I feel a lot like DommeLynx. its the primal act of intimacy and role reversal that i enjoy.

Never really thought if it as humiliating although i can see how it could feel that way.

I view it as all these other guys are missing out getting pegged by a beautiful dominant women

I feel my biology cheated me, because I feel absolutely nothing good from pegging.
A bit of discomfort to start, but then it turns into nothing. No pleasure whatsoever. I feel god played a joke on me with my biology in many ways, and that's just another one in a long list.

Complete pleasure but you have to know how and what to do. When I first started out, i tried for 2-3 years before finally getting it. It takes an ability to relax and allow the body to comfortably receive it and in that way it's the ultimate form of surrender. Take it and you feel pleasure. Try to resist and it's painful. I love it both physically and psychologically.

I'm a big anal top. I love it.

I've been fortunate that a few subs who had bad first experiences with Dommes who didn't know how to top and have allowed me to reintroduce them to it and ended up finding it very pleasurable.