So for the next week or so I wore a chastity cage. I hated it. Everything about it. I hated how it felt all day and night. Nighttime was the worst, since normal nocturnal erections couldn't happen (which worried me), and sleeping was difficult. I woke up angry and tired every morning. But the absolute worst part was having to sit down to pee. This was embarrassing on a whole new level...it didn't turn me on or make me feel like I was part of something fun and sexual. So, that was my first week in chastity.
Through the week, Rebecca would occasionally text me to ask how "it" was going. I would typically respond with a short message, like "I really don't like it" or "not great". She wouldn't respond directly to those, but instead change the topic. I was convinced that when we got together next I was going to get the key from her and take it off. I didn't care about the consequences, I hated it. And, if she couldn't respect that, I wouldn't want to be with her anyway. This is what I thought.
Turned out, the following weekend we had plans to be together was suddenly canceled because she had to take a last minute flight to visit her family--her grandmother had fallen and was in the hospital for a few days. So, I was stuck in his cage for another 3-4 days at least. I asked her if I could drive by her place before she left to get the key and she pleaded with me to just keep it in for a few more days. I agreed.
That Friday night I received a long text from her that read:
"Hey John, just landed. I'll call you once I'm settled. I was thinking on the plane and I want you to know that I know this has been hard for you but you're doing a great job and I'm very proud of you. I PROMISE it will get easier...I know it's weird but it really really really makes me happy and it makes me feel closer to you. You're seriously so attractive and fun and caring... my heart gets beating so fast when I'm with you. When I finally get back I will reward you :) I want us to make love. Over and over again. Love you, John. With all my heart."
Just the previous Sunday we had both proclaimed our love to each other. I can't lie, her text made me feel so good. She really was perfect for me. I know I talk only about the sexual part, but outside of that we were excellent. We loved all the same kinds of activities, similar world views, had great friend groups. Not to mention that I'd never been with someone as attractive as her. My buddies joked that she was out of my league.
So, after receiving that text I met up with a few friends and had some drinks and decided to stick with it. Of course, I questioned that decision as soon as I found myself back at home after a cab ride sitting on my bathroom toilet to pee. I was semi-drunk. I don't know why but this time I felt my dick getting hard (or trying to) as I flushed the toilet. I wasn't sure why, but I think it was from the feeling of being submissive. Having to sit and urinate made me feel submissive but why? Well, because that's what women do. But women aren't weaker. I suddenly recognized my own bias. Maybe this was Rebecca's point? She was an attorney and was a bit of an outspoken feminist of sorts. She was very smart, so I wouldn't put it past her to have been intentionally making this a lesson. In any case, my dick pushed hard against the pink plastic cage. I wanted to cum so bad. I don't think I had gone this long without an orgasm since I was 14. Well, that night I got my wish.
Not exactly the perfect wish, however. I got my orgasm, just not in the best way. I woke up from a dream around 3am and was shaking a little - I had had an orgasm in my dream! I never had that happen before. Usually right before I'd be close to cumming in a dream is just wake up hard. This time I woke up from dreaming about fucking Rebecca and I actually had an orgasm. I laid still with my eyes open. I felt cum coming out of my dick, but it felt different-more like peeing with a good sensation. I brought my hand down and was quickly reminded that my cage was on. So I gad an orgasm without even having a hard on? all around my cage and on my sheets was drenched in cum. I got up and turned the light on. A huge stain of cum was on my bed and some was dripping down my leg and out of my cage. I couldn't believe it. It had felt great but also very different.
I cleaned up the sheets and took a shower. I kept ruminating about what happened. I guess I had so much cum built up that my body felt it was time to go. I remembered that Rebecca told me to text her whenever something like this happened so I did:
"Hey love. You told me to text you if I ever had an orgasm without you. Well I can't believe this but I actually had a wet dream lol. I've like never actually had one of those."
I laid back in bed and go my surprise I got a quick reply.
"Hey!!! I forgot to turn my phone off and heard your text. Thank you for telling me...and I'm not mad or disappointed at all. These things happen when your cummies are all backed up :) clean up and get some sleep. Can't wait to talk to you later in the morning, love. And I can't wait to make love to you when I get back. Our first time!"
I hated when she said "cummies" but I was glad she wasn't mad.
The next day we talked. To my disappointment, she had decided to stay the whole week to help with her grandmothers transition. I secretly rolled my eyes when she told me. Another damn week in this fucking cage.
I walked around that weekend furious. I thought about getting some tools and just breaking the cage off. I actually sat down thinking. Would Rebecca REALLY get mad? I mean, come on. Ultimately this was all some crazy sexual game right? If I told her it was hurting me or something I couldn't imagine she would actually be angry. How serious was she anyway? I honestly wasn't sure. She seemed pretty damn serious in the moment. I sat and contemplated for about an hour. And then it hit me: we were in love and had now been together for a few months, and guess what? We had never actually had intercourse. That's why she said making love when she gets back will be our first time. Of course, I was well aware of this fact. It was odd and it pissed me off. But what hit me was the level of seriousness it implied. If she was doing this all for a bit of a fun sexual game, she'd still want to actually have sex. I sighed. Ok, John. One more week.
And, as it turned out, things did get better. I even told Rebecca that it wasn't as bad as last week. The toilet sitting still bothered me, but I started to sleep better (unfortunately no more wet dreams) and during the day I had started to forget it was there unless something made my dick want to get hard. I still didn't love it, and I was dying to cum, but it really stopped being so bad.
Finally, after 2 weeks, we got back together at her place. We had dinner and wine and talked about her grandmother and work and everything else. It was great to see each other. We missed each other like crazy, as young lovers do. Then, as the night wore down, her tone changed. We were kissing and she said into my ear:
"Ok little one. Go into my room and strip." I did as she told me. I could feel my dick pressing so hard against my cage trying to get hard that the skin of my penis was bubbling outside the cage vents.
She came into the room and I stood there naked. She was wearing a low cut summer dress. She looked down at my cage and then bent down and wrapped her hand around it.
"I'm so proud of you John. I know it was so hard but it made me SO happy. Now let's give you a little break." And with that she took out the key and took off the cage. I was instantly hard.
"Wow John! I don't think I've seen it this hard before." She gave me a big smile and then took her dress off. She undressed completely and told me to fold her clothes, which I did. She didn't do anything weird. It felt normal. She then crawled into her bed and patted the side next to her.