Please help with pegging advice

[Lockedwithlove]

I'm hoping some of you more experienced members can help me out and especially key holders too. My KH and I have been practicing MC for the better part of 6 months now. Things are going slow but it's been great for both of us and I would certainly say it's improved our relationship. I think maybe why our progression with MC is a little slower is because I couldn't wear my device for more than 2 or 3 days at a time because I would get mild edema at that point and it would have to come off. Which has been fine because my KH likes to play with me and give me a release at that point anyway. So by no means is what we have "traditional" chastity because of how often I'm let out. I'm hoping that with my adjustments made to my current device, plus I ordered a couple of steel knockoffs with a more open design that me being able to stay in longer will drive my KH's dominant side. I've brought this up in the past to her way before we started MC but I want nothing more than for her to peg me. She already knows she's in charge in bed. I follow only what she wants and tells me to do so that's already established. I've explained to her that I want to feel what it's like to be in the traditional female position so I know what it's like to be penetrated by my partner and fucked good by her. She is reluctant to try this but seems to be opening up more to the idea. I hate to be annoying or pushy about it because I don't want to top from the bottom. Does anyone have any suggestions, advice or ideas that I could relay to my KH to make her more comfortable with the idea of pegging? I'm not exactly sure what she's opposed to unless she's just nervous about trying it because of expectations. I know it doesn't gross her our because sometimes she like to finger me if she really horny. Anyway any help would be nice. Thanks!

[Thomas Sub]

One blog I found which is written for the female Domme's point of view and really makes pegging look sexy is a tumblr site called onthekneesnow.

[Formyowngood]

My kh Pegs me regularly. But before all that came about I found that she her self liked to have her ass played with "lightly". Meaning, orally and pressed on with a finger, and sometimes actually penetrated..... Well with a newer larger toy and playing a bit more deeply, I took her with out asking.... Although she didn't fight me, she wasn't too happy that I did it like that... That's how it all started. She let the dead horse lye... And one day, I was told that we were going to have a very nice time... I came home, and directly was told to take a shower, and be laying on the edge of the bed face down, DONT ASK QUESTIONS....I was caged.... I though I was going to milked as she has done before... And that's how it started.... Little did I know that she had bought her own strap on and dildo just for this day. Now... My kh LOVS gay men and gay porn.... So she is "a natural" at it...

[Lockedwithlove]

My kh Pegs me regularly. But before all that came about I found that she her self liked to have her ass played with "lightly". Meaning, orally and pressed on with a finger, and sometimes actually penetrated..... Well with a newer larger toy and playing a bit more deeply, I took her with out asking.... Although she didn't fight me, she wasn't too happy that I did it like that... That's how it all started. She let the dead horse lye... And one day, I was told that we were going to have a very nice time... I came home, and directly was told to take a shower, and be laying on the edge of the bed face down, DONT ASK QUESTIONS....I was caged.... I though I was going to milked as she has done before... And that's how it started.... Little did I know that she had bought her own strap on and dildo just for this day. Now... My kh LOVS gay men and gay porn.... So she is "a natural" at it...

I think my KH is more afraid not doing it correctly or is worried in some way she'll disappoint me. She had taken several toys and a dildo to me before but not very often and I usually have to get her very horny to be in the mood for that and then I have to ask her to use a toy. Although if she uses her fingers on me I don't have to ask, she'll just do it. I wouldn't call my wife a dominatrix but she's a strong woman and takes charge when she's in the mood to. I feel like I'm asking her the equivalent of her asking me to go down on her, which consequently I love doing. I just wish she'd give me a direct answer on why it's so problematic for her so we can work around it. I just don't understand why she's so reluctant. She has actually wanted me to play with her ass more. Last night after some incredible sex she actually told me she wished I would've put it in her ass. She told me that if I ever asked her too she would say no, that it is just something I'm going to have to try with her when I get her turned on enough. It just drives me nuts because I would lick her ass and penetrate her ass and do literally anything she wanted, so why is she so hesitant to penetrate me with a strap on after she's willing to finger me. im just confused....

[WET_MANGOS]

What ever you do don't be pushy, if you are there's a chance she will start to hate it because of your pushing. My wife peggs me every other Wednesday and it's working for us, but only after years of ups and downs over it. The biggest thing you have to understand is that for most women there is not one thing that then gain by doing it. You can say the dominance she will have over you doing it , the power over her man and yadayada but really that's all the man's fantasy. My wife was more comfortable with it all when I sat on her instead of her being on top, it's less of a domanating thing but it takes some pressure off of her and puts you in control of penatration. I'm sure your wife dosent want to hurt you and taking some control will help ease her way into it
Do you have a strapon? If not go pick one out together, it can be fun. Just talk to her about it but don't pester, if she dosent like it just hope shes willing to do it for you. And if it does happen to do it if you liked it or not (because it wasn't like your fantasy) best tell her you enjoyed it and thank her by doing something REALLY SPECIAL!!

[Lockedwithlove]

What ever you do don't be pushy, if you are there's a chance she will start to hate it because of your pushing. My wife peggs me every other Wednesday and it's working for us, but only after years of ups and downs over it. The biggest thing you have to understand is that for most women there is not one thing that then gain by doing it. You can say the dominance she will have over you doing it , the power over her man and yadayada but really that's all the man's fantasy. My wife was more comfortable with it all when I sat on her instead of her being on top, it's less of a domanating thing but it takes some pressure off of her and puts you in control of penatration. I'm sure your wife dosent want to hurt you and taking some control will help ease her way into it
Do you have a strapon? If not go pick one out together, it can be fun. Just talk to her about it but don't pester, if she dosent like it just hope shes willing to do it for you. And if it does happen to do it if you liked it or not (because it wasn't like your fantasy) best tell her you enjoyed it and thank her by doing something REALLY SPECIAL!!

That's really good advice, I'm trying not to be pushy about it, I just want her to talk about it with me and be more open to the idea. Just like when I asked her to put me in chastity she clams up and has a hard time talking about it. I get a better response from her when I email or text her my thoughts. I just want her to try this at least once with me. As far as how it benefits her... You could argue it's like oral sex. I went down on her for almost an hour last night and brought her to an amazing orgasm. Now I love going down on her but one can argue that I'm not get anything out of it other than making her extremely happy. Sure, it makes me rock hard and I love rubbing my face in her pussy but its not getting me off by doing that to her, it benefits me by putting her in a great mood and making her happy. So even with the premise of MC in mind and understanding it's all about her, it's also all about compromise. Am I in the wrong mindset on this. I would do literally anything she wanted me to if I knew it made her happy.

[WET_MANGOS]

First let me start by saying this. we are roughly the same age, into the same kinks and wife's are vanilla or were anyway any KH in my book has left vanilla some time ago, any way if you think like I do this will be good advice.

If I thought licking my wifes vagina was all for her pleasure i would be lying to myself. Sure she gets all the sexual gratification, but I get the privilege of licking her wonderful vagina, when I say privilege I mean this falls into my kink in more ways than one. I get that body worship feeling of making her happy by doing something that's focusing all of my sexual energy to her I also get to taste and smell her most private place WITCH I LOVE! If she told me she didn't like getting her vagina licked anymore I would be sad. Those feelings I'm talking about may not be true for your wife because being controlled may not be her kink. Because pegging may not turn her on (Example) pretend your wife came to you and said you know what really gets my juices going, a good bellybutton fingering. Sure you would indulge her because your a naturaly kinky person aND you get off on giving your wife pleasure. But bellybutton fingering would do nothing for me in bed and wouldnt turn me on at all. And every time you tried to get busy with her she would be all like no don't lick my pussy give me that bellybutton fuck haha. It would get old so fast because it dosent turn you on and this is how my wife feels when it comes to pegging. Even today the only reason she does it is because its something I desperately want. It satisfies me so I can in turn gratify her.

This is where a super romantic date comes into play. If your wife is vanilla like my wife then she likes to be swept of her feet like mine does. If I could do it all over I would. Tell her that it's what you really want. get ready to do it like go get the hardware (strapon) with her. Then sweep her off her feet!!! I'm talking flowers date night something really special to really get HER ! Going then when you get home if she dosent want to peg because she was so turned on by all the romantic lovey dove stuff bring her to pound town and make her scream. Then next day after everything is said and done that's when you tell her that thinking about her pegging you was what motivated you to sweep her off her feet and want to give her every thing she wanted. Same idea with chastity really lock my penis and ill be a better husband. Peg my butt and ill be a better husband.

Me and my wife on the other had have it on the calender for a few reasons first is that we know it doesn't turn her on so she's never thinking of it and when I always am it gets on her nerves when I ask all the time when. Second now it's set when it's going to happen I can be ready for it, sometimes my wife would start a pegging session when I was just thinking we would have sex and I would have to turn her down because I wasn't ready for it. Ya got to be clean for your lady because anything nasty likr ehem poop! Huge turn off must avoid at all costs. Long story short we have found something that works for us but it was a lot of work and in the end we are really happy both of us !

[Lockedwithlove]

Well I have to say everything actually worked out! I used my usual method of emailing Mrs. M to explain my desire for pegging, it's easier for her to take in what I'm asking her when she can read and re-read what I've said, plus I'm more articulate in typed form versus just trying to explain myself to her. She gets shy about these types of subjects and who wouldn't who was new to it, but it makes me nervous and shy too and then we both stop talking about the topic whatever it may be. After I verbally asked her about chastity she wouldn't really discuss it with me, it's not that she didn't want to or was repulsed by it she literally has a really hard time talking about these things. I waited a week for her to bring MC up again after she said she'd think about it. So I emailed her which allowed me to lay everything out so she could take it in and really think about her response. She was much more open to chastity and agreed it could be fun after that. Now she loves MC and there's no going back (of course I don't want to either). So once everything was confessed to her and I agreed to literally do anything and everything Mrs. M wanted, she agreed that pegging would be part of our play. It was actually a huge turn on that she is going to assign me tasks and chores, she gets final decision on what we watch on tv or movies but in the end it's a double positive for me because I want to feel her dominance. I spent all day yesterday cleaning the house and doing what's he asked and then some. She was very pleased by the time she got home and I could tell she was quite happy with our new arrangement. Funny thing is, I wanted her to give me chores and rules when we started chastity but she didn't really want to. Things have certainly changed over the last 5 months and I'm starting to see a more dominant woman and I love it! I hope she will enjoy pegging me, I think when we get into. She even joked with me this morning that she was going to wear a suit and high heels I would wear my leather apron (I have it for work so I don't get burned when I'm heating metals). So I'm really excited to see what's to come of this. Thank you everyone who posted because you all had some useful information and advice.