Pegging

For me it really drives home the submission to my owner

 

My mistress sort of coaches me as she's doing it saying things like "good boy" and "you're doing good" when she gets the tip in. I fall for it everytime and am so overwhelmed I think she's kind of like a very kind nurse. Then she'll go deep or thrust fast and shout at me to relax and I think, "oh yeah, she gets a kick out of torturing me. That's what this is." Like it's the first time the thought even occurred to me. She pushes me to safe word out for a break, leaves me in the spreader bar, then goes back to "c'mon you can do this" and it starts all over again. A very small effort pushing forward can completely overwhelm me to the point I'm almost passing out and can't even think straight to remember the safe word. She thinks all of this is funny and funnier still that I want to do it again if it's been a while and I've forgotten just how terrifying the whole experience is. I bought massive dildos and a very wide beaded one for her harness which seemed like a good idea at the time.

Physically it is kind of possible to relax to take it but when I am actually genuinely scared of my mistress I tend to clench up which is extremely painful. She both loves me and loves torturing me at the same time so the experience has mixed emotions for me.

 

Submission and helplessness are my main emotions. But, Mistress is OCD and therefore requires an enema before any anal activity, so the process of my being pegged actually starts hours earlier and therefore the anticipation builds, as does my humiliation as She reminds me of my position as I'm instructed to "hold it" in for what seems like forever!

 

In the beginning it was the ultimate expression of my submission. However, now it is a very pleasurable thing for us. She usually orgasms and I don't always orgasm but get all kinds of pleasure from it. It is our only form of penetrative sex as PIV is no longer an option.

 

I find it humiliating when she has me bent over, and says "right now pull those cheeks apart so that i can get some lube on", i pull my ass cheeks wide, she lubes me up and her strapon and then gently pushes her cock in to its hole.....when she gets to thrusting really fast and talking dirty to me it makes me feel very submissive, and she'll say "i bet you wish this was a real cock dont you?".....and although i'm hetro, i sometimes wish it was !

 

I have briefly enjoyed a kind of lovemaking pleasure when she has started off with normal sized dildos, about my size if I wasn't in chastity. She sees this as strictly warm-up time and if she senses I'm enjoying it too much she upsizes to one of the punishment dildos which I can only enjoy in a masochistic way no matter how long we do it. I think maybe she has a deep seated fear about a male enjoying anal or just likes to see me squirm and moan. The sessions usually end with her cuddling me while I'm shaking from adrenaline and actual shock. This is a very special and intimate moment that I would not experience if I wasn't dating a sadist. Sometimes I can feel overwhelming feelings of love and bonding after pain sessions and I quickly forget that she went for a few more thrusts AFTER I safe-worded which is fine because I agree to that treatment.

 

It seems that it is still the ultimate expression of your submission. Just with a little different nuance.

 

Once in a while She will use a large dildo to give me a punishment pegging. I try to be a good boi and avoid those.

 

I have thankfully never received a punishment pegging. Mine are always about pleasure and it seems with each time we do it I feel better and better. I usually can't keep from moaning, sometimes too loudly. I would imagine it is the closest feeling a guy can have compared to a woman receiving really great dick. Mentally I love my wife being in that power position and I especially like that she suggested it this past weekend over PIV (and told me I was staying locked). That's a new development for us.

 

Punishment pegging is not as bad as I paint out. When you are truly being tortured = you are experiencing pain above your threshold and continue to experience it when your brain is screaming out that you should be doing everything you can to stop it... you are the most alive you can be. You are living in the moment and all thoughts and worry cease. Your ego and body cease to be, even the humiliation of your predicament fades to nothing, and you become the pure pain in the part of your body that is being stretched, crushed outwards really. Your body has been invaded by someone you think you know but can you ever really know and trust anyone other than yourself? Afterwards you can't even control that part of your body, it's paralysed. You think it's damaged forever. While you're feeling this you'll likely be showing your gratitude to the girl who did this to you and got aroused while doing it. As bad as it is, a few days later when she suggests it again you say Yes.

 

When Mistress gets me going really well, I involuntarily begin the "push back" as She thrusts. When She senses that, She knows that I am enjoying myself and tells me what a horny slut I am - and I am in no position to disagree with Her!

 

Sorry- but there is not where I want to experience pain. Just not my thing, but no judgement. I prefer losing my ability to walk from the euphoria of not being in control as the pleasure waves overtake you....

 

What goes through my mind…..I love that my Wife is taking me, dominating me, giving me pleasure while I’m completely submitting to her. It used to embarrass me a little when we first started pegging, but not too badly. We’ve always been into anal play from early in our marriage at 18, but sometimes when she’s got my legs pushed back and looks into my eyes, I get slightly embarrassed still.

There isn’t anything I don’t like about it, it feels
incredible, the submission turns me on, and when she fucks me for an extended time I get into a headspace zone I can’t even describe, then when it’s over she’ll hold me tightly against her breast and I feel totally content. She can really fuck me into deeper submission.
It’s extremely intimate, and seeing her cum while she’s doing it is incredible too.
I just wish she would do it more often than once every week or two, she is trying to do it more consistently as she knows it’s good for my proper Subby mindset.

 

That's cool and probably best in your case not to let curiosity get the better of you and to not own that large toy. Giving pain can be as addicting as receiving it and now I do feel obliged to receive this knowing how happy it makes my mistress. I think it's easy to have pain play dismissed as fantasy so I wanted to explain how for me it's more complex than just something I would refuse or avoid at all costs.

 

I'll start with many years ago when we first started pegging, before chastity and even our BDSM phase. She would always tease me when fingering my ass on how I seemed to like it and one day she was going to get a dildo and fuck me in the ass kike a gay boi. A few month later, she had me shower and told me to wait in the living room for her and to get ready. So I got the towel and covered the couch and waiter for her to shower to come in and play. This time it took her a little longer and for some reason she was wearing a robe.

She walked up behind my head and bent over and grabbed my wrist and handcuffed me to a rope going over the back so my hands were pulled up over my head. She reached over and grabbed the kube bottle and squired some lube onto her hand and started rubbing my ass and then inserted a digit into the hole, I was kind of surprised when she inserted a second and then pumped lube onto her two fingers and worked my ass a little more,

She withdrew her finger, wiped her hands off and then got on the couch down by my legs and had me bend my knees up. She pulled the top of her robe off and place each of my ankles over each of her shoulder and grabbed the lube bottle again. When she pushed the robe all the way down for the first time I saw the didlo in the harness and she started to lube her new cock. I remember how my cock got rock hard and my breathing changed and the next thing you know she has the head against my hole. As she started to push in I felt the pressure and then a slight bit of pain came over. She stopped and waited and when I seemed to relax, she started pushing again. That cycle continued a few times and the next thing I know I felt the chrome of the ring against my ass and she was all the way in.

Suddenly she chucked, my rock hard cock was now a soft and spongy and I was embarrassed. She made fun of me that I was no longer a man because my cock was soft and she started to slightly pull out and back in again. The feeling was incredible and she chuckled more when I started to moan as I enjoyed the feeling. She was in total control and started telling me she knew a guy who was gay and maybe would be interested in giving me the real thing since I seemed to like getting my ass fixed. The one thing that was amazing, she fucked me for about 10 minutes and started to play with my cock. While I got some firmness I never got real hard and when she was jerking my cock and her strokes increases, I shot a load when I actually hit my own chin with me cum.

Now when she does me Its usually on my hands and knees and wearing my cage. The pegging is now more dominance over me and while she may occasionally fuck me until I expel fluid, she no longer jerks my cock off. I still moan and grown from the feeling of some pleasure, but know I in for a pounding when she grabs hold of my shoulders and pulls back. There is the occasional times she will lay on her back and have me mount her cock, that is when I know who is the boss.

 

As soon as I told my madam I enjoyed anal she asked to fuck me, the idea of penetrating a man really excited her, she couldn’t even wait to order a strap on! She used her dildo on me that night,
We both love the role reversal of it, madam loves acting like the men do in porn films, slapping my ass, telling me to beg for it, calling me slut,slag,whore, fag/faggot and so on, and then when I do spurt, she will ridicule and humiliate me for it! It’s amazing!

 

This is exactly me too. Always clean out ahead of time. That starts my anticipation. Sometimes Mistress/Wife will just decide to use a large plug or vibrating plug just to tease. We also have a motorbunny we both use that is pretty intense.

Then there are times when Mistress/Wife decides to use the thrusting machine toy on me. Its real close to real pegging and bonus...she controls the speed and time. Never gets tired that way.

 

I think we are having two different convos. I certainly do love properly applied pain. I just am vehemently against pleasurable actions causing pain. PIV should not cause pain. Oral on a woman should not cause pain, a BJ should not cause pain and anal for a man should also not cause pain. I could never imagine exploring how I could make PIV painful for my wife. It is alien to me.

 

It has been yrs when I was pegged and I did enjoy it. What i loved about it was being something new and different. I enjoyed giving the dildo a bj and hearing her say things like suck it and grab my head and being on my knees. When pegged I was on he edge of bed and on my back. I was not in chastity at that time. If ever happens again I would love to try other positions and see if I could orgasm and maybe her. I wold not be doing this for any kind of pain

 

What goes through my mind when I get pegged is how lucky am I. I love everything about it. Nothing to dislike.
What makes it hot is the good feeling but more importantly the total submission.

 

Whoa, who's talking about pain toward females? As my message above states clearly my mistress and I only do pain pegging when she's topping and I'm bottoming to which we both consent. More than that, I need it sometimes and for the first time in my life have found someone I can trust and love enough to do it with me.

 

Listen, I think you're right in general to say that a man shouldn't feel anal pain. What she does to me, for me, it transcends the sensual world. I trust her to not kill me or injure me and that hasn't happened yet. I can't recommend what we do. I'm working through issues of being jaded with life's experiences. Perhaps I've gone off topic here but torture, real torture as in non-consenual for a time reminds me I'm alive and that somehow everything is better than those moments of pure pain. Everything is full of colour after.