What are your favorite chastity memories?

The gathering that was held where Mistress Watchful attended.
It was so cool to meet the founder of this site and to be with all of the other subs in chastity serving the ladies.

Being used for one of the demos was the highlight of the event for me.

 

There are threads about the gatherings.
You have to look way back.

Not many details were posted. But there are a bunch on the excitement and about the planning. I think a few post event.

Back around 09 or 2010 or 2011

The events were coordinated by one of the former moderators who was a lovely Domme. Mistress Watchful came in from the UK. We had people come to one of the big lakes here in Va from Atlanta, Wisconsin, Delaware, and several others. A house was rented and we all brought food.

Lots of socializing, play, discipline, and demonstrations. Sadly they’re no longer held as they’re a bunch of work and expensive to put on. People don’t realize what’s involved with putting on a major event.

Anyway if you search you can find it. But I don’t have time to look for it. Also if you look at posts from that timeframe you’ll see how we were a close bunch of friends.

 

Mine took place the first summer when we really started to play with chastity and had many first experiences. We started really using my plastic cage Memorial Day weekend and were spending the weekends naked outside by the pool and hot tub. The cage required removal every few days for a good cleaning and after a long swim, so our experience was a bag of mixed results.

Toward the end of July, the cage started to separate and developed other fractures along the seams and end. Not sure if it was the UV rays from the sun or the chlorine from the pool or a combination of both. We were looking on line and saw this cheap knock-off on one of the sites(my avatar) and decided to order it and try it out. It came on the mail by the end of the week and overall looked pretty good.

The first time trying it on was a bit of fumbling and stumbling before I was able to clip in the mounting pins without pinching skin. I kept it on for an hour, took a swim, and dried off. My wife loved the look especially the sunlight reflecting off the metal. I took it off for a bit and we fooled around a little (without an orgasm) and I took another swim. This time when I dried off I put the cage on for another hour or two. We started to make out again and my wife pushed my head down and had me lick her to orgasm. When it was my turn for some fun, she took the keys and threw them into the deep end of the pool and told me if I got them out in under a minute I could have some fun. By the time I found my mask, jumped into the pool, 70 seconds passed, the first of many denials.

That night we had some great sex, I even got to have two orgasms that night. The next day was Sunday and we kind of repeated what took place the day before and had fun and excitement with her denying me during the day and at night pleasure. Over the next two weeks I extended my time in the cage slowly and was able to go 24 hours caged without release. It was a Friday night and we were planning on spending the weekend at the pool, all my yard work was done during the week. On Friday night my wife had me get my cage and put it on and once locked she took the keys and locked them into her work safe.

Saturday was interesting, several times my wife climbed on me during the day and we made out like teenagers. We had a great day at the pool, a nice dinner, and after showers it was bed time. My wife climbed on me and we started to make out and after a few minutes she scooted up the bed and placed herself over my mouth and held onto the headboard while I licked her. It was a earth moving orgasm that went thru her body, when she finished she toppled over like a falling building. I could feel and then see the skin of my cock pressing thru the bars of the cage and was dumbstruck when she told me good night.

Sleeping that night was fitful, the nighttime erections, the dreams, and the frustration hit me like a freight train. Sunday at the pool was one of torture for me, my wife knew what I was feeling by my attitude and she took full advantage with the extra swing in her steps and rubbing my arm, leg, back, and caged cock during the day. The rest of the day played out the same and when we got into the bed it played out like the night before. However, this time she reached over to her draw and pulled out the key to my cage. She had me stand next to the bed and inserted the key and turned the lock, my cock was so swollen thru the bars it took a few minutes to get everything off. My wife took my cock in her mouth and bobbed on it a few times and then as it slipped out of her mouth she grabbed it in her hand and started to pump me.

I once had a 3 sum with my wife and her hot bi girl friend and fucked them both and had one of the greatest orgasms ever. That was nothing compared to this one, 5 tugs on my cock and my first stream shot over her head and landed on her back and the bed. My second stream hit her straight in the eye, and the third one into her mouth. The rest dribbled out and down around her hand and fingers. We got up, took a shower, and changed the sheets on the bed.

As we were getting back into bed, my wife had me put my cage back on and hand her the keys. She was going to lock them up in the safe in the morning when she started work and for shooting her in the eye and temporarily blinding her, I was going to remain locked until the next weekend which was Labor Day. I could say no, but we would never do chastity again. My cock remained locked for the week and she let me out on Monday for fun and it was great. Over the next month we dabbled and played, even bringing chastity into our bdsm play. This was great until September 30th and my wife found out about Locktober and life has been quite different since then!

 

This is a second marriage for me . Second for my wife also, although she also lived with 2 different guys after her divorce.
We decided before marriage that it would be a cuckold , hotwife , chastity relationship. Shortly after marriage my wife invited her sister over for dinner. My wife , again before marriage decided that her sister would be an emergency key holder. She had told my sister about the arrangement before we married, so there would be no surprise later.
So after about a month of marriage Sara invited her sister over for dinner. After dinner my wife who has a flat for the dramatic , had written vows for us to take , my sister in law and I . They went something like in the absence of my wife my sister in law is in complete charge . She will hold a key, in the unlikely situation where the device needs to be removed, it will be her decision. There was a candle lighted my sister in law and I held hands . My wife had me strip , showed her sister how to lock and unlock the cb6000s. Let her try a few times . I then presented the key to my sister in law.

 

My birthday was going to be on a Saturday . I came home from work on Friday night and she was waiting by the door with 2 overnight bags packed . I asked what was going on and was told to be quite and put the bags in the car. I worked construction and was dirty and wanted a shower bad and said so. I was told,not one more word. So I put the bags in the car and got in to drive, but no she was driving . About 15 minutes later we show up at this motel for lovers. She got out of the car I was told to stay, when she went and got a key to a room.
Once inside she told me to go and take my shower . Which of course I did. While in the shower she took the clothes I had on and locked them in the car. After my shower she said everything you want or need is your overnight bag. Surprise ! Not one piece of clothing . The bag was full of her toys . Paddles,crop,cuffs, all of her dildo and vibrator and rope.
I was nude until late Sunday evening and was totally exhausted by that time. I really don't think I sat down for a few days after that . Not once did I come out of the cage.
Ps. I missed work on Monday . Was my best birthday ever .

 

Favourite chastity memory?
Her wide, wide eyes the very first time she saw me wearing it.

 

We were only a month or two in. Had tried several cheap cages and were zeroing in on a cage that could be worn longer term. I was all excited about our new game and was absorbing everything I could learn about chastity. So I presented a draft of a chastity contract and told her we needed to negotiate terms. She blew up - big time. "I dont need someone, or some contract, telling me what I have to do. You say you love me and trust me. You already know how much I love sex. I doubt I could ever go a week without. But if we are going to go on one more minute with this game, or with our relationship for that matter, you are going to accept only one rule, and that is that I make the rules, period". We talked a bit more about how I could still have my rules about other things but chastity wise I have zero control or say. I finally pledged agreement. Things started changing immediately after. She kept it fun. Very fun. But sure as time moves on she kept (and keeps) tightening her grip on me, reminding me of that moment often.

PS: she didnt admit until a few months later that she had read up on this for years and planned and scripted that moment from the beginning. I cry "unfair" then she holds out the key reminding me that "a promise is a promise".