Real Men Submit! Why Pegging Redefines Masculinity
Making Him Take It Like a Man During Pegging Play
Let us get one thing straight. If he thinks he is a real man, there is one ultimate test he still has not passed.
Not how much he can lift.
Not how many beers he can chug.
Not even how many women he has bedded.
No. The real test is this.
Can he spread his cheeks, whimper your name, and take it like a man when you strap it on?
Welcome to the most delicious role reversal you will ever command: pegging.
Pegging as the Final Frontier of Manhood
For generations, society has been pretty boring about what makes a man. Men penetrate. Men do not get penetrated. Anything else? Taboo.
Well guess what. Taboo tastes better when you are the one feeding it to him.
Pegging slices right into the most fragile parts of that old, crumbling idea of masculinity.
It says, in no uncertain terms,
You want to be strong? Good. Then prove it.
You want to impress me? Then take it deeper.
It is not just kinky. It is downright revolutionary.
And it is sexy as hell.
Set It Up Like a Dare
The hotter the build-up, the sweeter the victory. Frame it like a gauntlet you are throwing at his feet.
“Sure, you say you are tough. But can you handle me inside you, filling you until you are begging for more?”
Dare him. Tease him. Mock him if you want.
He may be able to wrestle a tire or build a deck. But can he clench his jaw, moan your name, and keep his ass pressed open while you grind into him?
That, my dear, takes a real man.
Warm Him Up, Melt Him Down
You could be nice and start slow. Fingers, plugs, teasing. Whisper instructions in his ear while he grips the sheets. Make him work for every inch.
Or you could be a little wicked.
Press the head of the strap-on against him. Just barely inside.
Stop.
Wait.
Make him feel the power building behind you. Make him ask for it.
“Tell me you are ready to be my good boy. Tell me you want to feel what a real man feels.”
Pegging is not just penetration. It is a psychological striptease, peeling away all the layers of ego until he is raw, vulnerable, and absolutely yours.
Praise the New Man You Have Created
When you finally bottom him out and feel his body surrender, reward him.
Stroke his back. Grab his hair. Kiss his neck. Growl in his ear.
“That is it. That is how a real man takes it.”
“Look at you. Taking all of me. Brave boy.”
“Strong enough to submit. That is my man.”
You are not just using him. You are forging him. You are burning away everything weak and shallow, and leaving behind something tougher, sexier, and so much more real.
Spice It Up Even More
Want to really twist the knife in the hottest way possible?
Make him wear your underwear while you fuck him. Your old panties, your lace bra. Whatever makes you laugh and moan at the same time.
Blindfold him and make him beg for every thrust. Let him feel completely at your mercy.
Give him a spanking if he clutches or whines too much. Remind him who is doing the real hard work here. Spoiler: it is you.
Assign levels to his performance. Bronze if he lasts five minutes. Silver if he begs. Gold if he comes from prostate stimulation alone.
No matter what, make sure he knows he is auditioning for the role of your personal pegging champion.
The Real Manhood Test
Here is the truth.
Masculinity is not about who gets to thrust and who gets to gasp. It is about who is strong enough to trust, surrender, and endure.
Taking a strap-on like a man means trusting the woman wielding it.
It means submitting to pleasure, to vulnerability, to the wild unknown.
And believe me, when he passes this test, you will see him in a whole new way. Not smaller. Not weaker. But more.
So grab the lube. Buckle the strap. Grip his hips.
And when he looks back at you with that sweet mix of terror and lust, just smile and say,
“Ready to be my real man, baby?”
Then ruin him for anyone else who thinks masculinity is about who is on top.
Excellent piece!! My Dommes and I agree with all.
I favor the phrase “forging a new man.” Sometimes it is a hammer forge, isn’t it?
This year my group is pushing boy development to a new level: to fist all 6 of them by Halloween. krissi had been pacing the pack, regularly taking Jeannie’s wolf penis, but I’m told that Janice has quietly made great strides with Patrick; that this week he graduated from a Snug Plug 6 to 7, for all-day wear. We measure them (using graduated cones: a dilator for anuses and a long one (from Analconda) … so that development is not only the “gatekeepers” but all the way “forearm” deep.). Next measurement is next weekend; so we’ll see.
Excellent goal! How fun to have six to work on at once – I’d line them all up and move from one to the other… see who sings the loudest! 🙂
I will say, you are giving them more time than I would!
If a sub wants to give me is body, that ass is going to take whatever I want it to. Sure, if he’s new to it we’ll take some time, and I’ll work upto my hole stretcher after a couple visits.
Trust me, if he wants more after the first time I fuck him, he’s going to do some self-stretching training between sessions! 🙂
Good luck with training your men – my advice, go for it! Give him the full fist – maybe even surprise him and do it for the first time in front of the others. Show them it can be done!
We’ve lined them up many times. It’s fun. And fun for mind fucks: lay the made-up straps to their fronts, beginning with one of what they expect, then next to it bigger, and next to it bigger still, till we have however many for each Domme present.
Super Bowl Sunday we had 6 Dommes on 4 boys. The last two dildos were really big. While Domme 1 began taking them, they watched the rest of us putting on the others: anticipating what was coming.
Then we asked if they’d like them lubed and when they gave the expected head nod, we presented our cocks to their mouths.
Then we all fell-in, in order., side-by-side, offering the next boy in line the option of re-lubricating the cock that just opened up his buddy.
We aren’t overly aggressive – it’s about stretching and strengthening for long-term and extended use.
For example, at krissi’s punishment, his “nightcap” was Jeannie taking him – for the enjoyment of everyone – 12 Ladies were present – when he was bound to the sawhorse ,with her wolf penis, for about 10 minutes. (That time, it was lubricated with more than saliva)
As for investing time, this is part of the great advantage to having a pack: charting the growth of their assholes is fun. I post a copy of the graph on my refrigerator; shows a full year of regular measurements, all boys compared with one another. It’s fun to confront “laggards” and challenge them to offer a plan for how they will catch up.
To your point about making boys watch the achievement of another; you might re-read the conclusion of krissi’s punishment.
Patrick, tony, and kevin were present – to help rig krissi – and they watched Jeannie go at it with that (fabulous) wolf penis.
In her accounting of that evening, Janice (Patrick is her’s) noted that it wasn’t lost on them what they have coming.
P. S. Krissi’s punishment was on Thursday evening. On Friday he had a doctor’s exam and then Ihe drove me to my former college roommate’s place for the weekend. His penis was out of commission from whipping and his body was heavily welted and bruised.
But his holes were still in great shape.
And his attitude.
The holes were used heavily, Fridays, Saturday, and Sunday.
As I said: long term and extended use.
Autumn, I think Meghan makes her point well – she is training her men for long term, extended use. Sometimes it’s better to be careful with our toys so we can keep playing with them, over and over, without having to go get another.
Although I will admit, sometimes it can be incredibly satisfying to just use a boy up entirely. It’s just not sustainable! 🙂
Great post, Miss Autumn! Love how You redefine masculinity toward trust and surrender, submitting to vulnerability. Provides a different perspective and illuminates how pegging can fit so well as a Femdom practice that is satisfying and empowering for both Dommes and subs. Thanks for posting!
And? Have you ever demonstrated your masculinity and surrendered your ass to your Domme?
Yes Miss Autumn. Though it’s been quite a while though.
I must say Miss Autumn I love the writing style on the is post, I’m in awe, envious, terrified and turned on all at the same time!
I longingly wait for the day I can prove my worth in this way to my significant other, alas I think it might be a fair bit longer to wait though.
Thank you for sharing!