Pegging

[sexybeast03]

I have a fantasy about being tied down, completely helpless while I get pounded in the ass by a mistress. Only after a long while letting me cum by pumping my dick while ramming the strap-on even deeper in me. First I have to serve her my making her cum with only my mouth.

I have tried bringing up something like this with my wife but she is very vanilla. So I wanted to hear if anyone have experience with this and how it turned out.

 

[Britva415]

Definitely have experience with this. You can't do it with someone who's too vanilla to be into it. They won't enjoy it, and they won't be into it enough for you to enjoy it.

So when you say you tried bringing it up, I assume that what you mean is she said "no." Right?

If what you're asking is how to get her to say "yes," you probably can't, and even if you could, see above.

 

[delphi604]

I have a fantasy about being tied down, completely helpless while I get pounded in the ass by a mistress. Only after a long while letting me cum by pumping my dick while ramming the strap-on even deeper in me. First I have to serve her my making her cum with only my mouth.

I have tried bringing up something like this with my wife but she is very vanilla. So I wanted to hear if anyone have experience with this and how it turned out.

Sounds wonderful. Haven't tried it. Yet.

 

[Naughtyboy1974]

I have a fantasy about being tied down, completely helpless while I get pounded in the ass by a mistress. Only after a long while letting me cum by pumping my dick while ramming the strap-on even deeper in me. First I have to serve her my making her cum with only my mouth.

I have tried bringing up something like this with my wife but she is very vanilla. So I wanted to hear if anyone have experience with this and how it turned out.

I always had a fantasy of my wife pounding me as a role reversal to show me what it’s like to rammed. Like your wife my wife has never been interested in it, but does come up when talking dirty during sex but that’s as far as it goes.

 

[Bigbackpack]

There’s a girl at work who everyone knows is into kinky stuff including pegging.. I often think about her doing that to me. We could have some fun together!

 

[BrandonF8]

I have a fantasy about being tied down, completely helpless while I get pounded in the ass by a mistress. Only after a long while letting me cum by pumping my dick while ramming the strap-on even deeper in me. First I have to serve her my making her cum with only my mouth.

I have tried bringing up something like this with my wife but she is very vanilla. So I wanted to hear if anyone have experience with this and how it turned out.

Care to chat

 

[40sBiCuckCple]

I think I won life’s lottery when my wife married me. She knew I was bi and promiscuous, and I knew all the same things about her. By the time I was thinking about her pegging me, she had already bought a strap on and 2 different size cocks to fit it. We already had the velcro restraints. I never even had to ask, she told me what she was going to do. I willingly submitted. Life is good!

 

[Dearelliot]

I think the threat of it from a femdom might be better than the act itself. I worry about how much it might hurt.

 

[BillyWalrus]

I think the threat of it from a femdom might be better than the act itself. I worry about how much it might hurt.

Not really. Being fucked is the best especially by a real cock on a beautiful woman.

 

[kccasey]

I think the threat of it from a femdom might be better than the act itself. I worry about how much it might hurt.

It does not hurt at all, feels fucking wonderful.

 

[Dearelliot]

I know a tall thin professional lady in South Jersey who does this, as a matter, her ad is posed with her naked, wearing a strapon...I been wanting to see her for other reasons and discounted this fetish but might now consider it

 

[Burstplayer]

You'll never know until you ask.. I thought it was the longest of long shots when I sent the wife an LIT story on first time pegging. She said sure. She'll try. And we were off and running. The issue has now become it's clear I like it a bit too much and it's put an air of uncomfortability to it now for me actually. Especially, since i've come out as BI to her.

 

[leftwantingmore]

I think the threat of it from a femdom might be better than the act itself. I worry about how much it might hurt.

Relax, be well lubed, take long slow breaths. Soon, nothing but pleasure, pure pleasure.

 

[leftwantingmore]

You'll never know until you ask.. I thought it was the longest of long shots when I sent the wife an LIT story on first time pegging. She said sure. She'll try. And we were off and running. The issue has now become it's clear I like it a bit too much and it's put an air of uncomfortability to it now for me actually. Especially, since i've come out as BI to her.

Honesty does come with risks, Honesty is always a leap of faith, seems to me.

 

[TheIntrepidBoyager]

I love it!

(Writeup, Not pics) https://theintrepidboyager.blogspot.com/2025/08/the-working-stiff.html

 

[Thespian1]

I have used dildos, of course, but I would love for someone to take me slowly, penetrate me deeply.

 

[Fifemarriedsub48]

I would love to be tied up/in a
Bdsm dungeon and used by 1 or more females with strapons.

 

[lindi_85]

Genuine question and asking for a friend…
How would this friend broach this subject with her partner who she suspects may be bi or gay without scaring him? I suspect this friend isn’t into the act itself, rather exploring something she suspects may interest him but would never ever bring up for himself.

 

[Thespian1]

Genuine question and asking for a friend…
How would this friend broach this subject with her partner who she suspects may be bi or gay without scaring him? I suspect this friend isn’t into the act itself, rather exploring something she suspects may interest him but would never ever bring up for himself.

Hello lindi_85. If it was me, I would feel very relieved if my partner would openly talk to me about her suspicions. I would suggest for your friend to lovingly approach the subject with her partner.

 

[OddLove]

I've been single for almost eight years, I think... and I fell Out of love with someone after we started getting more serious and had vanilla sex. Once they said any sort of kink was a hard 'No' for them I literally had nightmares about having vanilla sex as a 'chore'. Something I had to perform in order for them not to be angry at me. Something I had to do regularly in order for them to feel loved and appreciated on a deep level. And I'd be faking my interest the entire time. Which is a horrifying thought.

I also don't have a problem being single and I don't have any strong desires for sex. I'm not sex repulsed or anything, I'm just not interested. It's fun within kink, but without kink it's just awkward and like, I honestly just don't get it. But yes. I've had experience with a partner not being into the things I'm into, and the relationship ended pretty quickly after finding out a future with them would be only vanilla sex and absolutely no kink for the rest of my life.

It's hard to describe to others, but I'm sure some people here would get when I say 'Kink is my sexuality'. Like I'm not into sex unless it's kinky, BUT I am into kink even if it doesn't involve sex. So if I were in a situation where I loved someone so deeply and they weren't into kink, I'd have to just tell them I'm not into vanilla sex.

I'd be more comfortable with helping my life partner find a play partner or just having a sexless relationship than I would be with having vanilla sex, so in that sense, I have to respect others hard 'No' when it comes to kink, cause it's probably just as uncomfortable and strange in too them as vanilla is to me

 

[TheIntrepidBoyager]

Genuine question and asking for a friend…
How would this friend broach this subject with her partner who she suspects may be bi or gay without scaring him? I suspect this friend isn’t into the act itself, rather exploring something she suspects may interest him but would never ever bring up for himself.

Have you ever played with his ass during sex? If so, how did he respond? If not, it can be a good test. Rubbing a dick-shaped vibrator, playfully at first, in his cock is a good start. And easing into some naughty talk during sex is good too.

My point being to get some signals before diving in.

 

[TheIntrepidBoyager]

Genuine question and asking for a friend…
How would this friend broach this subject with her partner who she suspects may be bi or gay without scaring him? I suspect this friend isn’t into the act itself, rather exploring something she suspects may interest him but would never ever bring up for himself.

To expand on my previous post... If he really does have such orientation and would never bring it up, it most likely means he fears rejection. He could fear his own reaction to having to confront it but I would suspect rejection is a major concern too. So, your role would be to remove or minimize that fear and instill a sense of acceptance.

Are you okay with either of those potential outcomes (bi or gay)? Would you be into pegging? You have to be in the right place yourself first.

 

[lindi_85]

Have you ever played with his ass during sex? If so, how did he respond? If not, it can be a good test.

I’ve not been too keen but have introduced a butt plug a few times with success. Sex with me doesn’t usually interest him.

Rubbing a dick-shaped vibrator, playfully at first, in his cock is a good start. And easing into some naughty talk during sex is good too.

My point being to get some signals before diving in.

Thank you. Some good ideas.

To expand on my previous post... If he really does have such orientation and would never bring it up, it most likely means he fears rejection.

I have no doubt. He’s never going to admit to anything other than being 100% straight.

He could fear his own reaction to having to confront it but I would suspect rejection is a major concern too. So, your role would be to remove or minimize that fear and instill a sense of acceptance.

Hence my questions.

Are you okay with either of those potential outcomes (bi or gay)?

It would make sense and allow him to live his best life and as a result allow me to too.

Would you be into pegging? You have to be in the right place yourself first.

It holds no interest for me whatsoever, however, I want him to be happy and if I can support him to understand himself and his needs surely that has positives for both of us.

 

[sexybeast03]

For me this is as much the fact that the lady is in charge and calls the shots. Also the topic was pegging it could just as well being a 69 tied up.

 

[cdstefi]

It does not hurt at all, feels fucking wonderful.

Depends how the dildo hits you. We have a 7" Feeldoe and have tried it doggystyle before but the tip bangs up against my sigmoid just before it's fully in (bend in the colon) and that doesn't feel nice.

If I ride on top it seems better and doesn't get that hard-stop sensation, either the position allows better penetration angle or it might just be me feeling I'm in control of things. Whatever, cowgirl for me!