Pegging/strap-on Sex

Chanceorlando

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Okay...my girlfriend was watching porn and discovered pegging/strap-on porn and now wants to try it with me. I try to be open minded, but the biggest thing that's been inserted in my ass is her pinky when she was blowing me and even that was a little uncomfortable. I'm not one of those guys who think its "gay" to do this....mostly worried it will hurt like hell and not be any fun at all. To be fair (letterkenny reference) she has let me fuck her in the ass and I'm not a small man, but I wasn't expecting that to turn into "tag" you're it...lol. Have any of you guys experienced this...how did it feel...how did you prepare? Did you like it...hate it? Should I buy something and practice before? I don't want to end up crying like a little girl cuz it hurts so bad...lol. Honestly, I'm kind of terrified, but I also want to be a team player and make her happy. Advice??
 

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Hey! I recently discovered anal play over the past year, I regret not exploring this sooner. I will say that it is (for me) the best orgasm you will ever have!!!
As you said, and I agree, it would be smart to get yourself some lube and small anal toys to insert and slowly work your way to. Larger size that makes you happy. Practice and relax, take it slow and enjoy…it will hurt before it feels fucking amazing! You can also try prostate vibrators too!
 

Chanceorlando

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Hey! I recently discovered anal play over the past year, I regret not exploring this sooner. I will say that it is (for me) the best orgasm you will ever have!!!
As you said, and I agree, it would be smart to get yourself some lube and small anal toys to insert and slowly work your way to. Larger size that makes you happy. Practice and relax, take it slow and enjoy…it will hurt before it feels fucking amazing! You can also try prostate vibrators too!
Thanks for the response.....think I'll try that...don't want to ruin the experience by screaming in pain the first time she tries it...lol
 

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Being that it was your girlfriend who brought it up and seems to have the enthusiasm here, I think it'd be prudent to get some sort of equivalent exchange going to keep her honest. Obviously the prospect of getting pegged makes you uncomfortable(as well it should given an eager and possibly overzealous penis non wielder wants to enter your rectum), and nothing in your original post implied she wants to try for less than selfish reasons....so I'd request a sexual act that you enjoy that she would find uncomfortable, not anal because that'll just be motive for reciprocation, but something that challenges her held notions of femininity...
Personally I'd go for a MFF threesome, she wants to peg me, then do it while I'm inside another woman, otherwise it's back to pinky town..lol
 

Chanceorlando

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Being that it was your girlfriend who brought it up and seems to have the enthusiasm here, I think it'd be prudent to get some sort of equivalent exchange going to keep her honest. Obviously the prospect of getting pegged makes you uncomfortable(as well it should given an eager and possibly overzealous penis non wielder wants to enter your rectum), and nothing in your original post implied she wants to try for less than selfish reasons....so I'd request a sexual act that you enjoy that she would find uncomfortable, not anal because that'll just be motive for reciprocation, but something that challenges her held notions of femininity...
Personally I'd go for a MFF threesome, she wants to peg me, then do it while I'm inside another woman, otherwise it's back to pinky town..lol
In her defense she's always been a team player....meaning if I've asked, she's complied...that's why I feel compelled to give her what she wants...just scares me...lol
 
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NudeDude71

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Okay...my girlfriend was watching porn and discovered pegging/strap-on porn and now wants to try it with me. I try to be open minded, but the biggest thing that's been inserted in my ass is her pinky when she was blowing me and even that was a little uncomfortable. I'm not one of those guys who think its "gay" to do this....mostly worried it will hurt like hell and not be any fun at all. To be fair (letterkenny reference) she has let me fuck her in the ass and I'm not a small man, but I wasn't expecting that to turn into "tag" you're it...lol. Have any of you guys experienced this...how did it feel...how did you prepare? Did you like it...hate it? Should I buy something and practice before? I don't want to end up crying like a little girl cuz it hurts so bad...lol. Honestly, I'm kind of terrified, but I also want to be a team player and make her happy. Advice??
My current wife and I have enjoyed pegging from time to time (with a strap-on). Other times, she uses her finger(s) on me. It's definitely a thrilling and erotic experience. Your body will accommodate fingers and even larger strap-on's... Just need to give is a little time and lots of lube.
If your wife is interested, tell her you need to "work up to it". Go to a sex shop (or look online) together for smaller, thinner dildos. They even have Anal Training Kits including varying sizes of inserts to warm your body up.
On a very personal note, cleanliness is critical. Message me if you want tips on this or other questions related to pegging.
And finally, relax your mind and your body before and during the experience. You are NOT "Gay" for wanting to experience your own body's pleasures and capabilities. And, BONUS points for having a girlfriend to enjoy it with.
Have fun with it!
 

Chanceorlando

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My current wife and I have enjoyed pegging from time to time (with a strap-on). Other times, she uses her finger(s) on me. It's definitely a thrilling and erotic experience. Your body will accommodate fingers and even larger strap-on's... Just need to give is a little time and lots of lube.
If your wife is interested, tell her you need to "work up to it". Go to a sex shop (or look online) together for smaller, thinner dildos. They even have Anal Training Kits including varying sizes of inserts to warm your body up.
On a very personal note, cleanliness is critical. Message me if you want tips on this or other questions related to pegging.
And finally, relax your mind and your body before and during the experience. You are NOT "Gay" for wanting to experience your own body's pleasures and capabilities. And, BONUS points for having a girlfriend to enjoy it with.
Have fun with it!
Thank you for the info
 
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jojored473

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My fiancee and I have played with idea but My biggest worry is that I have Zero experience with anal and I have read a lot on the subject but I cant get past the idea of what comes out of there. LOL Possible residue and smell concern me in the sense of in the heat of the moment. I know that you can prepare but it seems like that would take away the spontaneity of it.
 
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Chanceorlando

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My fiancee and I have played with idea but My biggest worry is that I have Zero experience with anal and I have read a lot on the subject but I cant get past the idea of what comes out of there. LOL Possible residue and smell concern me in the sense of in the heat of the moment. I know that you can prepare but it seems like that would take away the spontaneity of it.
Have you ever had anal with a girl? She probably prepared and it didn't ruin it.....just saying..my concern is more pain that what comes out...lol
 

Mister2101

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My current wife and I have enjoyed pegging from time to time (with a strap-on). Other times, she uses her finger(s) on me. It's definitely a thrilling and erotic experience. Your body will accommodate fingers and even larger strap-on's... Just need to give is a little time and lots of lube.
If your wife is interested, tell her you need to "work up to it". Go to a sex shop (or look online) together for smaller, thinner dildos. They even have Anal Training Kits including varying sizes of inserts to warm your body up.
On a very personal note, cleanliness is critical. Message me if you want tips on this or other questions related to pegging.
And finally, relax your mind and your body before and during the experience. You are NOT "Gay" for wanting to experience your own body's pleasures and capabilities. And, BONUS points for having a girlfriend to enjoy it with.
Have fun with it!
Well said.....and very good info. When done right....start small and let your ass get used to being penetrated......no rushing....plenty of lube....relax your mind, body, and breathing.......you'll love it......orgasms are so damn powerful......