How many people here has tried pegging

Anyone who has actually been pegged knows that too much too fast can be very painful, length or width/girth. Also you dont always get hard or "drip". I/we have been trying for a sissygasm ir hands free orgasm for a 2 years and i do a lot of stretching on my own. I will post pics of the dildo's we use. A normal sized dildo doesn't give me much stimulation. Getting fucked by a real cock would be really Hot!
Starting to work on depth so i can start to take them deeper..... View attachment 1232977
Here are 3 of the ones we use alot, the shortest on the left is smooth but thick and stretches my asshole nicely... It bottoms out and feels mostly good. The clear one starts out thinner and is easier to start with... The black one is thick and long but too veiny and hurts. I can take it about 1/2 way down. The goal is to learn how to go deeper and take the entire length. Then move to the final and biggest one... Huge and smooth. Have get the correct pic type.... 5 minutes
 
Here are 3 of the ones we use alot, the shortest on the left is smooth but thick and stretches my asshole nicely... It bottoms out and feels mostly good. The clear one starts out thinner and is easier to start with... The black one is thick and long but too veiny and hurts. I can take it about 1/2 way down. The goal is to learn how to go deeper and take the entire length. Then move to the final and biggest one... Huge and smooth. Have get the correct pic type.... 5 minutes
Here you go
 

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What do any of you do to prep for getting pegged? I would guess it's difficult to be spontaneous, you'd have to know you were going to get it other wise it could get messy. Do any of your wives/gf's want to peg you often (at their request) because they are so into it?
 
What do any of you do to prep for getting pegged? I would guess it's difficult to be spontaneous, you'd have to know you were going to get it other wise it could get messy. Do any of your wives/gf's want to peg you often (at their request) because they are so into it?
Sitting on the toilet right now cleaning and getting ready for pegging later... Doing a "deep" cleaning that can take a long time depending on how deep you can get water past the 2nd sphincter. Butt, if you are going to go deep past the 2nd sphincter you have to be clean. She does not have any friends that she shares our sexual escapades with... But that would be fucking hot!

I agreed to be sub to her for 7 days which ends tomorrow. She has either pegged me or had me stretch my ass and send pics to her every day...
 
Sitting on the toilet right now cleaning and getting ready for pegging later... Doing a "deep" cleaning that can take a long time depending on how deep you can get water past the 2nd sphincter. Butt, if you are going to go deep past the 2nd sphincter you have to be clean. She does not have any friends that she shares our sexual escapades with... But that would be fucking hot!

I agreed to be sub to her for 7 days which ends tomorrow. She has either pegged me or had me stretch my ass and send pics to her every day...
Do you think 7 days will be the end of it? Has she had enough pleasure from being in charge to keep it going? Has she ever been sub to you? Do you think she would like for you to wear/use the strap-on on her?
 
Do you think 7 days will be the end of it? Has she had enough pleasure from being in charge to keep it going? Has she ever been sub to you? Do you think she would like for you to wear/use the strap-on on her?
Lots of great questions..... We each put 10 ideas into 10 envelopes... We have been taking turns drawing one if the others envelope.... This was my second one... I told her i wanted to be her sub for 7 days. I think she drew back in Early feb. But we had covid then she had issues with an irresponsible 26 year old. Life has been throwing us a lot of curve balls. So finally we started a week ago Sunday night. She has me put my cage on at 7 am and has been hiding the keys and removing it about 6 pm. Most night she has me go to the master and present myself to her... I get an inspection and maybe more. I have gotten 1 spanking, 60 swats with a large wooden paddle. The last 10 hurt like hell, but i was being punished for not getting my cage in in time. She also rewarded me Wednesday night by having me roll a die 3 times, tied me to the bed and edged me 32 times then gave me a very intense but torturous orgasm.... She is out visiting kids now and has been teasing me about how many edges she us going to give me... 56 is my record in one session... I love it as she ties me spread eagle to the bed and edges me with her hand, mouth, pussy and pocket pussy. Its fucking hot!
 
Lots of great questions..... We each put 10 ideas into 10 envelopes... We have been taking turns drawing one if the others envelope.... This was my second one... I told her i wanted to be her sub for 7 days. I think she drew back in Early feb. But we had covid then she had issues with an irresponsible 26 year old. Life has been throwing us a lot of curve balls. So finally we started a week ago Sunday night. She has me put my cage on at 7 am and has been hiding the keys and removing it about 6 pm. Most night she has me go to the master and present myself to her... I get an inspection and maybe more. I have gotten 1 spanking, 60 swats with a large wooden paddle. The last 10 hurt like hell, but i was being punished for not getting my cage in in time. She also rewarded me Wednesday night by having me roll a die 3 times, tied me to the bed and edged me 32 times then gave me a very intense but torturous orgasm.... She is out visiting kids now and has been teasing me about how many edges she us going to give me... 56 is my record in one session... I love it as she ties me spread eagle to the bed and edges me with her hand, mouth, pussy and pocket pussy. Its fucking hot!
She had been Dom to me before, but really is more of a natural sub, but together we are working on her growth as a Dom. She can be very creative, beautiful and has huge breasts... Pic below... Oh and one time while Domming me in the past she mounted a dildo on me and rode it till she orgasmed... Like it was my cock. Hot
 

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Lots of great questions..... We each put 10 ideas into 10 envelopes... We have been taking turns drawing one if the others envelope.... This was my second one... I told her i wanted to be her sub for 7 days. I think she drew back in Early feb. But we had covid then she had issues with an irresponsible 26 year old. Life has been throwing us a lot of curve balls. So finally we started a week ago Sunday night. She has me put my cage on at 7 am and has been hiding the keys and removing it about 6 pm. Most night she has me go to the master and present myself to her... I get an inspection and maybe more. I have gotten 1 spanking, 60 swats with a large wooden paddle. The last 10 hurt like hell, but i was being punished for not getting my cage in in time. She also rewarded me Wednesday night by having me roll a die 3 times, tied me to the bed and edged me 32 times then gave me a very intense but torturous orgasm.... She is out visiting kids now and has been teasing me about how many edges she us going to give me... 56 is my record in one session... I love it as she ties me spread eagle to the bed and edges me with her hand, mouth, pussy and pocket pussy. Its fucking hot!
Sounds very, very exciting! It also sounds like she is taking pride and pleasure in seeing you excited and thrilled with your sub. You are blessed to have such a fun and an uninhibited wife!
 
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Yup ... and loved it. Right on Sgt Ray, ya gotta be clean back there. Starting with small dildos and then gradually working up to something bigger is a must. Anal sex shouldn't hurt. If it hurts, stop!
 
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Sounds very, very exciting! It also sounds like she is taking pride and pleasure in seeing you excited and thrilled with your sub. You are blessed to have such a fun and an uninhibited wife!
Yes we have lots of fun and I have enjoyed stretching my sexual boundaries and his ass. Took a bit to learn rhythm, etc but now it's one of my favorite activities.
 
I enjoy it as often as possible - love to see him in manties and watch "my cock" fill him up. Here is a small example from today. We are working on stretching and getting him to take bigger and deeper. Can't wait for the day I can spit roast him with a real cock. Haven't decided which end I want to be..... he does have great oral skills as well
 

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Now THATS a Dildo! And u want to spit-roast him and make him suck (ur boyfriends?) cock?
Thats outrageously cuckolding him! Perfect..

Noticed u used the term 'manties', very creative & piling on the humiliation.

Had a GF who used to enjoy pegging me a lot.
She used the term "mangina" instead of ass.
Told me she was going to make my asshole
into a vagina, thus the Mangina.
Smart, sexy, talented Lady.
 
Now THATS a Dildo! And u want to spit-roast him and make him suck (ur boyfriends?) cock?
Thats outrageously cuckolding him! Perfect..

Noticed u used the term 'manties', very creative & piling on the humiliation.

Had a GF who used to enjoy pegging me a lot.
She used the term "mangina" instead of ass.
Told me she was going to make my asshole
into a vagina, thus the Mangina.
Smart, sexy, talented Lady.
She refers to my ass as her asspussy when she us fucking me or fisting me. Did you notice the stand has rings on it so i can be locked to it... We have not done that yet ... Oh and i do have good oral skills ask her about the multiple orgasms and squirts she had after we finished with the dildo..
 
Now THATS a Dildo! And u want to spit-roast him and make him suck (ur boyfriends?) cock?
Thats outrageously cuckolding him! Perfect..

Noticed u used the term 'manties', very creative & piling on the humiliation.

Had a GF who used to enjoy pegging me a lot.
She used the term "mangina" instead of ass.
Told me she was going to make my asshole
into a vagina, thus the Mangina.
Smart, sexy, talented Lady.
Hmm "mangina" has now been added to my vocabulary. Yes, I try to make sure he knows his place as my toy to be used. Verbal humilation seems to get him in the right mindset. That is one of many we use and they have gotten progressively larger over time. I believe he posted a picture of the BBC that is our end goal. Thank you for the replies and compliments. Taking control of his sexual needs definately makes me feel sexy (and naughty)