Today we are handing over the reins to our experienced friends Emma and Bill. They have been here on our blog before sharing their most intimate adventures and I invited them back again to talk to us about pegging. Have fun!
Hey, it’s Emma here. Recently we did something amazing, it was a journey for both me and my cuckold husband and I wanted to share it with you, people who understand our lifestyle and those of you just curious as to what happens when you mix pegging and cuckolding together. It’s no longer just p-spot pleasure, it’s converted into something far more exciting for us both, and today I am going to try and explain how that went down.
How I Started Pegging My Cuck Husband
I did get some tips from the femdom queen, I wanted to bottle up that perfectly crafted dominating hotwife essence that she has and pour it all over my hubby. My husband enjoys being a cuckold, he thrives from the humiliation of it and we even got to the point where he was cleaning up my bulls cum and licking it all up so I knew it wasn’t going to be terribly hard for him to be pegged by his wife. He is pretty accepting of most things and as a loyal cuckold, he just wants to please.
I found out my hubby enjoys three key things:
- Watching me have sex with men who are usually better in bed than he could ever dream of being.
- Being softly humiliated, he doesn’t like anything too harsh, but he likes the raw truth, especially if it has anything to do with his small cock. He also enjoys cum clean-up and knowing I have had a better time than I could have had with him.
- He enjoys his butt being played with and the power switch dynamic. Me being a hotwife is something he loves and he always urges me to be more full-on with it so I knew that pegging was going to be my chance.
My husband Bill is a manly man and spends most of his time being dominant in his work life. However, He loves getting into the bedroom and feeling that pressure is taken off of him and he has to just accept his fate and be a good boy about it. My hubby isn’t really a full-out sissy, he doesn’t really find men attractive, he just enjoys seeing me with them and being a good cuckold. Something he does like however is being fucked and treated like a woman.
Teaching my Cuckold Husband how to take a nice big dick
I wanted my husband pegged, I couldn’t stop fantasizing about it and when I went to him with my fantasy and ideas he was willing to try it out.
I wanted to make sure that if we were going to try the whole pegging thing I wanted it to be on my terms, I wanted him to submit to his hotwife and not say a word about it and leave everything up to me. I knew he wanted this too, he is a simple cuckold after all and being told what to do and how to do it is part of his kink.
He Didn’t Want To Use A Realistic Dildo (At The Start)
He wanted a nondescript dildo, something that didn’t look like a cock but unfortunately for my cuckold husband, he shouldn’t have said this, because at that point all I wanted was to see him use a big, veiny, realistic dildo and I knew now I was going to make it happen. I guess it’s all part of the training for my silly cuck.
His Butt Was Too Tight
I have a tight butt, but Bill’s couldn’t even fit my smallest dildo (length: 6 inches – circumference: 5 inches), inside of him. We had prepped properly, we were having great sex but the small dildo just wouldn’t squeeze in and this wasn’t going to do if he was going to be pegged by me.
What’s funny is that my husband thought that he would never have anything bigger than a butt plug in there :’), A few days later we tried again after I had done some more thorough research and found out how to warm his ass up even better. I made sure to really take care and make sure that he was turned on enough and relaxed enough to take it in.
It took 15 minutes, lots of lube, a little fingering, and a butt plug and he was finally able to take my dildo and now he can fit in my biggest ones without any resistance in his now not so tight little ass.
He loves the pleasure from these dildos, they give him some intense stimulation, and practicing like this first has really shown me the rhythm he likes, how long it takes him to cum and all of the things he likes me to do. Once he had taken my biggest dildo I knew it was time, to begin with, the pegging and so did my little cuck.
Buying a Bigger Strapon
He had no idea my plan was to have him take a really big cock, he thought we were going to start with a small dildo when I pegged him but I had other plans and I wanted to see if I could get him up to 8 inches (spoiler, I did).
My strapon cuck loved being railed by me, he enjoyed the domination, humiliation, and how it made him feel. The dirty boy didn’t even realize how big the cock he was taking was, his ass just opened up for me and I slid right on in there.
If you want to know the strap-on I used, just ask me in the comments and I will give you some recommendations.
Turns Out My Hubby Is A Cum Slut
I got ahold of a few dildos just to make sure we had everything we needed in preparation for my hubby becoming a pegged cuckold.
We tried an ejaculating dildo, I wanted to mimic the sensations of cumming like a man, treating my hubby as a little slut and it turns out he loves the way cum feels inside him.
When I made the dildo shoot its load my hubby couldn’t get enough of it, he liked to be degraded with the cum by having it in his ass, on his face, or all over his back. He loved to feel like a cum rag and pegging him was proving to be a better adventure than I had even envisioned.
I’ve Never Heard A Man Cum This Hard
Once we had broken the pegging seal, we couldn’t stop, he loved it. He enjoys thicker dildos (the ones that would stretch him out), he loves deep thrusts that fill him up, he likes being told what to do (for instance: get on all fours you worthless cuck), I make him spread his ass for me, I spit on his asshole, I finger it like he is a little slut, usually, whilst I lick, stroke or grab ahold of his cock/balls and he loves it when I’m in full control of him and pleasure. I mentioned before that he enjoys light humiliation but when I am wearing my pegging sex toy and I am pegging my hubby he loves to feel like a little cum slut being ravaged by a big cock.
My Man Was All Tied Up And Blindfolded and Ball Gagged
We had the most incredible night, I got some restraints and a ball gag to shove into my hubby’s mouth, I lit some candles and I knew tonight was going to be the night I would break him.
I took all of the control out of his manly life and now it was my turn to be in control of every part of him. I took inspiration for this sissy husband training from an article I had read, my husband didn’t really fall into the sissy category but I wanted to use some of the same techniques and make him feel as submissive as one. Seeing him ball gagged and tied up was a thrilling experience for us both and seeing him on all fours just ready for my cock was filling me up with bull-inspired desire and dominance.
My Favorite Part…
I did this during that night but now it has almost become a ritual I do it that often because it is my favorite part. I grab his balls and the bottom of his shaft and just squeeze while I peg him in doggy style. The second I feel his cock start to cum, I squeeze tight with one hand and hold him in place with the other while I fuck him really hard.
I will share a few more of my cuckold husband stories here if you want to read about how Bill progresses onward.
The Dirty Things I Whispered In His Ear While F**king Him
While he was tied up and helpless I whispered some filthy things into his ear and sometimes said some things out loud rather than bending down and giving him the grace of a whisper. Pegging dirty talk really adds to the experience, especially if your hubby is a cuck like mine.
The pegging dirty talk I use on my husband:
- Oh, hon is your little cock getting hard down there? I can’t tell.
- It’s funny, it took me fucking you with a big dick for you to finally see how worthless your tiny dick is and see why I love such a big one.
- I hope you’re ready for your little boycunt to be stretched out, you anal slut.
- ‘Wow, you’re a little slut, aren’t you?’ I then I make him nod and agree.
- Little cucks like you deserve to get pounded like this, don’t they?
- My cock will stay hard forever so I can fuck you for as long as I want.
- You’re just my little cock warmer cum toy.
These are some of the things I make him do when he is being pegged by me, his hotwife:
-When he’s not gagged I make him beg me to fuck him harder with my dildo.
-When he is about to cum, I tell him that I’m about to cum in his tight ass and to say my name again and again.
-I make him nod and agree to all of the things that I say to him, for example: ‘You are a little bitch aren’t you?’ and he nods along.
-I make him suck my cock clean before or after we have used it.
I Wasn’t Always Like This
At the start of our marriage, I enjoyed sex, then we went through a quiet phase where we didn’t really have much sex, I got shy and lost my confidence about it and a lot of our lust went.
Our lust came back when we learned to communicate and talk about our fantasies, it took a while, but once my hubby hinted that he would like to open things up and he started encouraging me to explore my fantasies, that’s when I got more confident and we got to the point where we spend 98% of our time being a loving married couple, who are soul mates, but that other two percent is spent with him taking orders, getting fucked like a good boy and watching me get fucked by the kind of guys I thought were make-belief.
Tell me below in the comments how you got into cuckolding, I love hearing people’s different stories on how they realized it was the lifestyle for them. Also, don’t forget to join us inside the Cuckin membership for even more.
Tell Me What His Fate Should Be In The Comments
Write one of the following sentences in the comments and you’ll decide my hubby’s next adventure for him:
Locked Up In A Cock Cage: Lock him up inside of a chastity device, only his ass is accessible and even then I won’t let him cum, he must just feel my dildo in his cock warming hole and face the reality of being just a cum slut.
Pegging Only Relationship: I take away traditional vaginal sex and use my hubby as a hole of pleasure for my dildo only.
Sloppy Seconds: He is only allowed inside of me on nights I’ve been shared with another man.
My Bull Gets A Turn: My bull gets to use my pegging dildo inside of my hubbys ass.
Let me know!
I couldn’t decide between locked up or sloppy seconds but I have decided on: Sloppy seconds for sure!! That would be hell for some but heaven for us cucks.
I Love the way you think, wish my wife was like you.
hugs, sissymaidwannabe
His Fate Should Be:
Pegging Only Relationship: I take away traditional vaginal sex and use my hubby as a hole of pleasure for my dildo only.
It’s clear that all of the options should be the answer. After a while in chastity (I have been in for pretty much my whole marriage), pegging/anal sex is sooooo much more intense than traditional sex and feeldoes (Spelling? The dildos that provide the dominant with satisfaction as well) can be very intimate. Two years ago, my Master and I had missionary style anal sex that is still my favorite sex anything we have done.
#2 you don’t really need that little cock anymore anyways.
Pegging only relationship? NO. Never stop have sex with your husband. As a cuckold, I would NEVER stand for that. The rest is fine. As far as chastity cages are concerned, I don’t think they should be on 24/7, days, weeks, or months at a time. I only thing a few people do something like that. I serve a Mistress that pegs me and she only has me wear a cock cage while I serve her.
Pegging Only Relationship:
omg loved it made me cum hard
Lock it up. It’s small and useless anyway
Let your bull have a chance!
I loved reading all the dirty things you whisper, so hot. He’s a lucky guy, the humiliation aspect gets me crazy!
I’d love to see him anal only and possibly on hormones for a few months to see if you both love him being feminized. He will not like it at first but then omg the quaking O’s.
For me and my ex wife it was her looking for a smaller male member. She had been raped multiple times as a child so my 11.25inches could never fit from all her scar tissue. She made me feel so bad about needing sex over the 20 years. Then I found out she was putting hormones in my food, I did not resist it. She had been giving me hormones so long to try an repress my male needs that I had grown to fit a C cup bra. But I was so in love I let her start putting makeup ,heels and various clothing on me. Since I was work from home I naturally started dressing feminine all the time. She started pegging me and would tell me that once I had a boyfriend I would be such a good fuck toy. This went on for close to two years when she said that there was nothing male left in me. She said my sweat smelled like a womans.so she started sucking a guy a work and he took her virginity the same night she sent a gay friend to our home and told him everything that made me hott. He took my virginity if you don’t count the peggings. She told him to tell me as i was about to cum from anal that o should enjoy being fucked tonight because my wife was getting cock at the same time. He said she wanted to coordinate us both becomming women at the same time.she and I met young and I had never had sex with anyone before. The hormones is what made it all so explosive for me . I never felt males attractive before. Appreciated the 3 hour guys but was never my thing until this happened. It was so smoothly executed the way he got me ready. Understand I was so afraid to be looked at that way.anyone finding out omg no. Yet what I did not realize was everyone that saw me knew anyway my chest went from a chicken chest to an C almost D cup from the hormones. They were and still are my weakness. If my nipples get touched my ass pulses with spasms that I can’t stop. It’s like I’m drugged I can not resist more then 20 or 40 seconds. I release far more powerful now with climax.it makes the oral release I use to demand from my wife seem really worthless. Though i now respect her mind blowing bj techniques,it was an art to her.The hormones made the difference.my ex left me shortly after that because she got pregnant. I thought omg I’m so happy for her that she can finally have sex and be a mom. So please consider hormones if you plan to take him along a very exciting path into feminine submission. After all 3 to 6 months won’t kill him but it could his seed but I swear I would not change a thing I’m so happy and content with the naughtiness of a otter and the peace of a princess.
Bull gets a turn.
Chastity by far. He should have already been locked up nice and tight in your cage so you are free to fuck him and cum inside him and have all of the nasty, amazing, creampie sex you can handle. He knows his place already as your pegging cuck, ensure he can’t do anything but please you at all times. Once he learns to cum in chastity from your fucking him he won’t ever want to cum any other way, believe me!