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On Saturday Morning I woke up with the usual torture that one experiences when in chastity. The dreaded morning hard on. Does this ever go away?

Mistress M was scheduled to go to a pool party where she intended to get fucked by some real men.

We talked for a while about rules and limitations. She told me that she locked in a 90 Day Chastity Contract I could accept online at http://www.ilovechastity.com/chastity_contract

It is an interesting system they have but I do not recommend it. The one thing I did not like was the fact that I was offered the choice to accept the contract without showing me the details of the contract. In order to see my Chastity Contract I had to accept it first. Now do not get me wrong there is a certain thrill in accepting a chastity period that you have no idea what you are accepting but it would be nice to know.

Well, we all know that I accepted and was presented with a 90 Days Until release count down timer.

Wow, 90 days. Well a month would be better but it could have been longer.

I informed Mistress M that I had signed the contract and she was delighted. She said that she wanted a 6 Month Chastity Period but that was not an option, and a Year seem unrealistic (for now). Holy shit! 6 Months! She also informed me that there was always the option to add more days onto this agreement. Such a nice feature.

So the plan was for me to spend my first full day in chastity home alone while Mistress M went to the lake and after pool party with the intention of getting fucked well and often. I should mention that this was a lifestyles party so the likelihood of her accomplishing her goal was very high.

Mistress M informed me that when we went to the store to get my padlock she was going to get me a butt plug. When we completed our conversations, Mistress M asked an innocent seeming question that changed my life again. “Is there anything else I should know, Good Boy” She asked.

Well, My Male Chastity Contract requires me to tell her everything so I confessed that I enjoyed anal play and I already had a few expensive butt plugs and we probably would not need more. Did she want me to tell her about what I has so she could determine if we needed more?

Mistress M directed me to tell her about the butt plugs but she was not happy about having me use a plug that I had used with someone else. She wanted her own. Well, we are lucky there, Mistress. I have 4 butt plugs and I have only used two of them with others. Oh Good Boy you were such a fool.

Below is a copy of the email and pictures I sent to Mistress M describing my butt plugs.

Good Boy, “I also enjoy wearing a butt plug. For over 20 years I have cum every time I had one in. But when I do it too masturbate it is in done and out in 15-20 min. Wearing one for 8 - 22 hours makes the torture of chastity 100 times worse and better if I am plugged while locked. I think it would drive me insane if done for very long.”

Mistress M, “Good boy for sharing. You know when we go shopping for your lock, you will be buying a new butt plug too that you will use for me. Not one you’ve used for anyone else. One that you associate just for me.”

Good Boy, “I do have plugs. Expensive $100 glass works of art. I may not need more.

Mistress M, “Maybe we won’t need to buy one. Maybe you send me pic of ones you have and periodically I will define which one you are to use.

The Butt Plugs

I own four plugs that are works of art. The smallest is actually retired.

It is a little over 4" long and 2" at it’s widest point. I purchased it in 2009 I think and only played with it myself for years. Until 2011 when I got my new small plug.

When I first put this in I thought it would team me apart. I kept it in for seconds. Over the years I learned to take it relatively easily. In 2014 last year I dabbled at being a dom and being a sub. I met a mistress and we played two times in a month. During that time for a week she forced me to wear the 2" plug for 8 hours a day. I loved it and performed the task with no trouble at all. I actually missed the plug when it was out. It did not work out. She was a true Dom and I was not a true sub. Chastity and Anal play was about all I liked. I did not like getting spanked and hot wax - fuck that never again! This plug I cannot wear for long term play. It just pops out. This plug is no longer made.

The second plug the Large Sexy Spades. It is easily found on any sex toy site even Amazon. When you look at the basic specs it appears not much different than the Retired Plug but oh it has some amazing qualities that make it particularly good for training a boy pussy. It is a little over 4 ½" long and 2 5/8" at it’s widest point. Not much bigger. But when you look at it notice how it does not taper smoothly over the entire 4 inches like the first plug and the shaft is not a tiny ½".

No this beauty goes from 0 to 2 5/8" inches in the first 2" inches of the plug. It is sudden and mind blowing. When you ass snaps closed over the shaft is does not every really close. The shaft is a full 1 ½" thick. Your ass remains open almost as wide as the original plugs widest point. Oh my God!

I dated a woman for 3 months before she learned of my chastity / butt plug fetish. She was the first to combine the two into amazing torture. She made me wear a chastity device for two weeks and wear the 2 5/8" plug for 22 hours a day with a maximum of 2 hours before it was reinserted.

I was horny and frustrated every day for two weeks. This would drive a man crazy if done for months.

The Medium Plug can only be called Medium for two reasons. One, I have a larger one and two the Sexy Spades trained my boy pussy so well that the 2 5/8" plug fits easily in and out with no effort at all.

I am going to skip around a bit here and go to Mistress M’s reaction to the first two plugs. Understand that she knew about all 4 when she made her plan but I am going to take the opportunity here to show you the first two plugs and the video Mistress M directed me to make and post.