Pegging

Physical pleasure
In terms of physical pleasure, a woman's genitals may get direct stimulation from the base of the dildo, or in the case of a double-ended dildo, from vaginal (or internal) penetration. A woman can use a secondary vibrator, between the dildo and her genitals, to get pleasure from pegging. Men may find stimulation of the anus, rectum, and especially the prostate, pleasurable. During anal sex, male pleasure can be particularly derived from the prostate, which can lead to an orgasm and ejaculation Some men enjoy masturbating (or being manually stimulated) during pegging. Triple-ended dildos provide both vaginal and anal stimulation of the female partner.

Psychological pleasure
Advice columnist Dan Savage wrote that he believes all men should try pegging at least once, as it may introduce them to a new enjoyable sexual activity and illuminate them to the receiver's perspective in sex.

https://en.wikipedia.org/wiki/Pegging_(sexual_practice)

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Who know? Might be fun, but I fail to see any pleasure in it for the woman, so why would she?
 
http://www.cosmopolitan.com/sex-love/news/a33467/sex-talk-realness-what-men-think-about-pegging/

Sex Talk Realness: What Men Think About Pegging

"Letting my girlfriend f*** me in the a** didn't make me feel any less masculine."

What's it like for a man be penetrated by a woman? Cosmopolitan.com spoke with two anonymous men about pegging — a gender-flipping sex act in which a woman has anal sex with a man via a strap-on dildo.

Have you tried pegging with a serious partner or in a casual relationship (or both)?

Man A: Only with a serious partner, and only with one partner at that — a long-term girlfriend.

Man B: I've tried pegging in both contexts. My first time was completely casual with someone I met in FetLife [a social networking site for people interested in BDSM, fetish, and kink]. My second experience was with someone from FetLife whom I dated for about six months. Sadly those have been my only two experiences of pegging thus far.

What tools or toys did you use?

Man A: We purchased a leather strap-on harness and a couple of silicone dildos — one approximately the size of my own penis and a smaller one as a starter peg. Also a giant pump bottle of water-based lube.

Man B: My first time was with a 10-inch dildo. I had my own toys that I had used on myself before though, including a 7-inch vibrator.

And whose idea was it — yours or theirs? What made you want to try it?

Man A: My idea. I'd heard about Bend Over Boyfriend [a series of sex education videos on pegging], and I was in a loving relationship with a very adventurous partner, so I knew I could indulge every curiosity that struck me — as long as I bought the toys. Clearly lots of guys enjoy being anally penetrated; I didn't want to miss out on the fun!

Man B: Both — we met for that purpose [of pegging]. I have always been curious about being penetrated. I have been playing with myself anally since I was about 19. Pegging has been a fantasy of mine since at least the age of 21, when I first heard about it.

What did you do to prepare?

Man A: We watched the aforementioned Bend Over Boyfriend video, talked it out to make sure we knew each other's expectations, and got shopping advice from a clerk at Good Vibrations in San Francisco. On the first night we tried it, we made sure we had plenty of champagne on hand, to relax.

Man B: I used my vibrator prior to the experience to make sure it didn't hurt. I also used an enema to make sure all was clean.

Were there any challenges once you got going?

Man A: None that I can recall. She paid close attention to my words and signals, so that I wasn't overly uncomfortable or in pain. We took our time. The only challenge was on the third or fourth night we tried it, when we used the larger dildo. That was just too uncomfortable and painful, which led to some funny teasing from my girlfriend about her being too big for me.

Man B: The first time yes, because not enough lube was used.

Who enjoyed it more — you or your partner?

Man A: I think she enjoyed it more psychologically and I enjoyed it more physically. She had more of an ingrained gender-flip fantasy, and I was more just curious to experiment. We were definitely both into it.

Man B: The first time she did, as she did not use enough lube. However, with my second partner, it was completely mutual.

What did you like most about pegging?

Man A: During one of our sessions, I was on top and straddling her, and she was bucking her hips while stroking my dick, creating a combined sensation I'd never felt before or since. As a bonus, I could see the passion on her face and her nude body, which was not possible when she was taking me from behind. That was pretty much the peak of the experience.

Man B: It was great. I love the idea of being submissive and having a power exchange. Plus, it just feels good.

What was it like playing the role of the penetrated person?

Man A: The role reversal was very exciting. We're steeped in a culture of prescribed sexual roles for men and women, so it's a thrill to break the "rules" and experience things that most people don't dream of trying. Letting my girlfriend fuck me in the ass didn't make me feel any less masculine or her any less feminine, but it did allow me to feel a vulnerability I was not accustomed to, since she could easily hurt me if we weren't in tune. It was also a way to trade perspectives for a bit, which is always eye-opening.
 
I don't have any personal fantasies about being pegged by a woman.

But if the woman I was with was really into it I wouldn't have any objection to trying it.

Same.

I'll add that I've always found the look of a woman wearing a strap-on kinda hot.
 
Who know? Might be fun, but I fail to see any pleasure in it for the woman, so why would she?

There are types of dildos that stimulate the woman, so there is physical pleasure to be had. Case in point, have a gander of this video especially the end:

https://xhamster.com/movies/6776815/she_came_so_hard_while_fucking_me_with_strapon_pls_comment.html

There's also the psychological pleasure that can come from role reversal, which pegging is a form of. Like most things in life, it will appeal to some and not others. In reality it's just another form of sexual expression between a male and female, not limited by the societal pressures that a male is always the penetrator and the woman the penetrated. It's not even strictly an act of dominance or submission, unless the participants play it that way.

I think the biggest hurdle is the stigma of a male enjoying anal play. Nothing about anal stimulation unto itself means anything in terms of sexual preference, but it's still viewed as a 'gay' act. I once thought the same, 10 years ago, but I've discovered the wonders of prostate stimulation and I'm here to tell you, there's POWERFUL, leg-shaking orgasms to be had from it. But to each their own...

My wife and I have discussed it, haven't gone through with it yet but its not off the table.
 
Never had my wife fuck me before but she has inserted fingers and toys in me. Pretty sure that I would love to have her fuck me as well. Shit, one of my fantasies is having a cock in my ass while she is riding me!!