So, up until two days ago, my KH would never think of anything anal. However, we stopped at a "marital aide store", in which she purchased a mini-bullet vibe and a strapon. Thursday night, we played around a little, me still caged. I have enjoyed a little back door play in the past, so this did feel good. She lubed up and just teased me a little, then we went to bed.
Last night was a different story. After some making out, biting, face slapping, and spanking, she told me to get on all fours, then put my face down and not to say a word. She took off my cage and I got hard immediately. I felt her lube me up and her wiggling around getting the harness on. Up until this point, I have only had a finger and the first inch of this toy in my ass, ever. This toy is not small, about 8 inches long and an 1 1/2 inches in diameter, two places that are flared a little more, and a curved tip. She slowly worked it in. After about ten minutes, she had it buried. It was uncomfortable, but I felt so full and good. She then fucked me with it, adding lube ever so often. The pulled no punches, going at different speeds, making full then short strokes. It was something like I never felt before. All the time she was scratching, biting, and smacking my ass, telling me how much of a good little bitch I was. This went on for about an hour, seriously I was facing a clock.
Then she had me turn over. As I did, I noticed the towel under me was soaked right under where my penis was. On my back, she took the dildo off the harness and put it back in me with just her hand. She gave me two minutes to cum, but I didn't take but a minute as it had been six days since my last O. When I asked her for permission, she said go, but took the dildo and pushed in on my prostate hard and held it there during my O, and then grabbed my cock and gave me some post orgasm torture while still holding the dildo in place. It was the strongest orgasm I have ever had, but I had almost no ejaculate. I assume all had been milked out during the first hour. The POT was crazy and I was in tears. I'm sore this morning, but can't wait to do this again.
Anyone want to share thier first time?
My first prostate milking
- notbeinfringed85
- Posts: 193
- Joined: Sat Feb 22, 2014 4:28 pm
- Location: USA-KY
Re: My first prostate milking
I am planning something very similar to this soon. Thank you for sharing your feelings and experiences because I wasn't sure how aggressive to be. I think I would not have done as much until I read this.
Royal Princess of Southwood kept happy by my caged Court Jester.
- notbeinfringed85
- Posts: 193
- Joined: Sat Feb 22, 2014 4:28 pm
- Location: USA-KY
Re: My first prostate milking
I'm a bit of a maschosist, but remember to be careful with him. I'm sure I could have safe worded, but my lovely wife did allow me time to adjust, which is necessary. This all put me in a great head space, because seeing so happy afterword and all the cuddle time after that, there is nothing I won't endure for her. It doesn't matter if I give up orgasms, endure some pain for her pleasure, or let her use my body for her enjoyment, I feel that we are closer than ever before. I'm hers, and I am not ashamed.
Re: My first prostate milking
That goes without saying. I know through experience how uncomfortable and painful it can be. We have a safe word, in fact two, one for "give me a second" and one for "stop completely".
Lots and lots of lube will be involved as well.
Thanks for your input and feel free to offer any other suggestions as I am a very new KH.
Lots and lots of lube will be involved as well.
Thanks for your input and feel free to offer any other suggestions as I am a very new KH.
Last edited by hiskh on Tue Apr 01, 2014 4:11 pm, edited 1 time in total.
Royal Princess of Southwood kept happy by my caged Court Jester.
Re: My first prostate milking
Hot scene.
Though that's a prostate orgasm, not "milking" - there isn't an orgasm associated with milking, the ejaculate just dribbles out.
Though that's a prostate orgasm, not "milking" - there isn't an orgasm associated with milking, the ejaculate just dribbles out.
"Some people need to be caged before they can be free." - Anon
- notbeinfringed85
- Posts: 193
- Joined: Sat Feb 22, 2014 4:28 pm
- Location: USA-KY
Re: My first prostate milking
If that was a prostate orgasm, I'd trade all regular ones for that. During the first part, I had that feeling if having to piss, but obviously didn't. I did notice a lot of fluid that I had expelled, but I couldn't see when it was happening. I assume that was kinda like milking. Am I right? I'm new to this also and could use some advice too. I'm at home today and have been working like a dog cleaning and doing some home mantaince. I also should be done with a piece of furniture I'm building her, so if I'm lucky, I might have a new experience to share tomorrow. 

Re: My first prostate milking
Yeah, a prostate orgasm is a VERY intense experience. Prostate milking is quite intense too, but not entirely pleasurable. Here's a post I made last month that has some good image examples that shows the difference: http://chastityforums.com/viewtopic.php ... 635#p91149
"Some people need to be caged before they can be free." - Anon
- Locked by LRC
- Posts: 1034
- Joined: Tue Jan 18, 2011 1:45 am
- Location: Midwest, USA
Re: My first prostate milking
Try comparing these two;
MILKING - http://www.xtube.com/watch.php?v=hWSyM-G144-
ORGASM - http://www.xtube.com/watch.php?v=R9jgq-G153-
As an extra, I found this while looking, she's using a pencil. Keep this one away from your KH
http://www.xtube.com/watch.php?v=grGQS-J552-
MILKING - http://www.xtube.com/watch.php?v=hWSyM-G144-
ORGASM - http://www.xtube.com/watch.php?v=R9jgq-G153-
As an extra, I found this while looking, she's using a pencil. Keep this one away from your KH

http://www.xtube.com/watch.php?v=grGQS-J552-
Current device - MM Custom
Previous devices - CB2000, 3000, 6000, 6000s, Curve
Previous devices - CB2000, 3000, 6000, 6000s, Curve
- locked4her55
- Posts: 2236
- Joined: Sat Feb 25, 2012 10:23 pm
- Location: Massachusetts, USA
- Gender:
Re: My first prostate milking
Was that a #2 pencil?Locked by LRC wrote: As an extra, I found this while looking, she's using a pencil. Keep this one away from your KH![]()
http://www.xtube.com/watch.php?v=grGQS-J552-

Ok, I get the point.


Happily secured since 4/2010 
Have worn CB3000, CB6000s, MM Jail Bird & Watchful Mistress,
DHgate A271 & 273, DHgate Full Stainless Steel Belt & DHgate HT nub
Currently wearing A273

Have worn CB3000, CB6000s, MM Jail Bird & Watchful Mistress,
DHgate A271 & 273, DHgate Full Stainless Steel Belt & DHgate HT nub
Currently wearing A273
Re: My first prostate milking
Thanks for the idea!
Royal Princess of Southwood kept happy by my caged Court Jester.