The Journey Starts!

December 11th, 2022. The chastity journey began.
I’ve been in the BDSM lifestyle for 20 years and swinger lifestyle for about 12. Done with swinging and have the most awesome woman in my life now and have no desire for another woman and wouldn’t want to share her with anyone else. The BDSM/Kink is in my life to stay.
I started playing around with chastity about 5-6 years ago. Only locking up during a scene, or just a daytime, weekend thing. It started piquing my interest in the last few months like it never has. My amazing girlfriend lives about an hour and a half away. We see each other about once a week, or every other week depending on our schedules.
I had 5-6 cages that I’d use. None of them were comfortable enough for long time use. Until I got my Cellmate 2 short. Her and I had talked about her using the app to lock me up and keep me locked until she wanted me out. I knew the cage was comfortable to wear daily and she downloaded the app, registered, and I was locked for 12 days the first time. Sexual frustration and extreme arousal was on my mind solidly after the first day or so.
My sexy Goddess Kitty had my cock locked and was hesitant to keep me locked until we saw each other again. She teased me a few times during that time on the phone and through text. She said she might let me out of my cage on that 12th day which was Christmas. I was allowed out that afternoon after I had massages her feet and legs. I was a dripping mess after touching her and she wanted to ride me. The feeling of sliding inside her wet pussy after 12 days of zero “good” sensations was absolutely driving me crazy. It felt sooooooo good. I came kind of quickly, but it was an intense O. She let me stay free until after we had sex again. She did request that I lick her pussy till she came. She ended up having 3 oral orgasms and 2 during PIV. We both commented on how intense the sex was yesterday and I’m pretty sure that kind of solidified her being on board with chastity. One of the best presents I’ve ever received. I’m utterly, and madly in love with this woman, then she makes my biggest fantasies come true. I am so thankful.

 

Thanks. No idea where it’ll go from here but she’s definitely warmed up to the idea. I’ll try to keep up with this journal along my journey. With her personality, I don’t see it going to a FLR, D/s dynamic, but we’re both switches, so I see some power struggles in the bedroom and a lot of good spanking for both of us. It’s exciting to imagine the possibilities. You never know!

 

12/27 update.

My girlfriend lives an hour and a half away. We take turns visiting each other. I’ll be heading there this weekend for the New Year. I am in my cage 24/7 when we’re not together. She’s very new to chastity and she’s on board, but I can tell she hasn’t realized what’s in it for her. So, I bought her a book. It comes highly recommended from folks on FL. Im going to give it to her and ask if she will at least open it and start it. Hoping it’ll open her up to all the possibilities. I don’t want to top from the bottom. I just want her to understand the dynamic and give her ideas on what directions she can go in. I’ll tell her, you’re in control. You can choose where we go from here.

Being locked has definitely made the sex 10 times more intense and much more of a close bonding with each other. We were talking about that on the phone the other night. We are only about 2 1/2 weeks in and we can both tell a difference, which is a wonderful thing. After last weekends orgasms I gave her orally I think she might expect it more often. Which I’m very happy about. I love pleasing her.

 

Oops. I thought I attached the pic. Here it is.

 

Thank you. I hope you have a happy New Year.

 

1/2/23 update

New Years weekend was spent with my KH. I got there about 5 on Saturday evening. She asked me to bring the two new cages I got last week so she could see which ones she liked on me best. We cooked some dinner, had a few drinks and decided to stay in and watch a movie. She asked me to rub her feet, which I did for about 45 minutes. After the movie she asked to see the cages, at which time she pulled out a new one she ordered as well. One would not fit at all. The ring was just too small. Second one had a urethral tube and she said no way. Then I tried on the nylon one she bought and it was a great fit. She took the keys and said I won’t need them till she’s ready for some D. Well, it came off about 30 minutes into me giving her oral. Then she rode me for about 45 minutes after taking the cage off. She really loves how much I drip now when I get turned on. After a shower the cage went back on and we crashed. I did give her the book I bought and she said she would dive in when I wasn’t there. Sunday, into Monday morning she left me locked up as well. This morning before I left for work she asked me to put my Cellmate 2 back on because she likes to be able to see if I unlock it. I’m bringing my keypod next time so she can lock the key in there for emergencies. She was actually into having me try on new cages and tease me in each for a boner check. It’ll be two weeks till we see each other. I’m pretty sure I’ll be locked up tightly till then at least.
It was a great weekend. Lots of cuddling and cooking great food.

 

Girlfriend just text me and asked if she could book a massage for me. The big chain massage places are all booked up for at least a month. She went online and choose one that is rumored to be a “happy ending” massage parlor. She even picked out the female masseuse. I’m locked in my Cellmate 2 and she wants me to go caged. I’ve heard they always do a table shower prior to the massage. I’m nervous and excited. This will be the first time someone outside of me and my KH knows I’m locked.

 

Thank you. My fantasy is becoming reality. I am trying my hardest to not “top from the bottom”. Just making the tools and knowledge available if she wants it.

 

I’m naturally a pleaser, so I really do enjoy helping her with anything she may want. I am slowly seeing changes and couldn’t be happier about it. She gets a foot and leg massage every day. It’s a turn on for me just running my hands up her thighs and rubbing her pretty feet.

 

1/3/23

My KH setup a massage for me last night after work. It was not the least shady place I’ve gotten a massage. It was an Asian massage parlor. I got there, an older woman greeted me at the desk and a few moments later a pretty woman asked me to follow her. We get back to the room and she told me to get undressed and lay face down. I covered myself with a towel and she came back in. She starts on my back with some oil and then she went to only using one hand. She was texting someone during my massage. She started rubbing my legs and then up to my butt. She took the towel off and sat on the table. My legs were spread and she started rubbing my inner thighs. Then she asked me to roll over. She saw my cage clear as day. She said, “what happened”? Her English was not that great, but I told her my girlfriend locked it and only she has the key. She asked me where to get one so when she gets a good man she can lock him up. We had some laughs and then she took her top off and started riding my cage while straddling me. She sprayed my hands with sanitizer and asked me to touch her. I asked her to just stop right there. I told her I love my girlfriend and just came for a massage. (Worst massage ever). I got home and told my girlfriend about it and we laughed pretty hard. My back was bothering me and she was trying to be nice. Going to a real masseuse tomorrow evening. It was great entertainment and something we can joke about for years to come.
On a side note she started reading the chastity book I got her. Hopefully she continues to read it.

 

1/6/23 update. Got my new cage yesterday. I asked if my gf could unlock me so I could do a cleaning and try on my new cage. She granted me that as long as I sent her a pic of the new cage on. I got cleaned up and put it on, snapped a few pics and sent them. She decided I need to wear this at least overnight. She did a video call and made me put the keys in the Keypod. She then said it looks much smaller than the other and she liked that she can see more with this cage. I’ve been in it since yesterday. This is part of the conversation we just had.

 

1/7/23

I’ve been unlocked for about 24 hours. Slowly stretching my PA piercing so I can use the PA puncture on my cage 8. I edged for a few minutes today and leaked like a faucet. I had to stop because I could feel myself getting very close to going over that edge. Back up to a 4 ga on the piercing. Should be able to get the 2 ga in and caged up sometime tomorrow.
The most exciting part of the day was when my KH told me she finished the book I got her. She had questions and we talked about a few things and went about our day. This evening we were video chatting and she said with a devilish smirk that she can’t wait to make me her bitch. I was both turned on and excited with a touch of nervousness.

 

1/16/23 update.
So, things have progressed for sure. We entered “hardcore” mode on the keypod and my Cellmate 2. Meaning I cannot just remove the keyholder and open if needed. So now I carry the keypod with me everywhere I go in case of emergency. I’ve been in the Evotion cage 8 for about 2 weeks now and loving it except for nightly errections. They seem to wake me every two hours.
I made a trip to her house this weekend. We went out for dinner then came back and had a few drinks to unwind. I gave her a 90 minute massage which turned into some amazing oral for her which resulted in a few orgasms for her. Then I suggested the strapon while still caged. She had two huge orgasms with that. She really enjoyed it. I almost came from it. Then she had to unlock me for PIV. I didn’t last much longer after she had another O. She left me unlocked until this morning (Monday). She absolutely loved the strapon idea, so I see that happening more in the future.
It was a great weekend.

 

I think she’s hooked.