Ryan:
I think calling it a journey is a very good term. We started having conversations but we didn't know the words to communicate, but we listened to each other, and we decided to not be afraid of mistakes. I came across sissy porn online and I was infatuated with the idea. I showed Isabelle the porn and that I wanted to try it. After lots of talking we decided that I would dress up as a sexualized girl on the weekend, wear chastity, and Isabelle would be in total control of sexual encounters when we played. It turns out the fantasy of being sissified was a lot more fun than real life.
Isabelle:
That's all true. I did not get any joy out of dressing Ryan as a girl. It was frustrating teaching him to do makeup, and it was insanely difficult to find sexy women's clothes that would fit him. I did really like controlling our sexual relationship, and I did like the feeling that came from knowing Ryan freely gave up control of his genitals to me.
Ryan:
Yeah, getting clothes was really hard, and I could never really figure out how to do makeup. All that aside I didn't enjoy being a girl. It wasn't me. That said, the fantasy is still interesting, and I still love when Isabelle teases me about being her sissy bitch. I did find I loved being in chastity. I trust Isabelle with everything, always have. Giving her control of my body just seems natural. And it made our sex lives a lot more interesting for both of us.
Jessica:
Wait a second, most people wouldn't think chastity cage and better sex would happen. You have to explain.
Isabelle:
Well you have to understand, at that time, all the sex both of us really knew about was penis in vagina (PIV) sex. We had a lot of fun with that, but we didn't know about the spectrum of sex acts. It turns out Ryan has a really small penis. My G spot is not very deep and can be hit with someone with a small penis if they know where to position themselves. The problem is, it is hard if not impossible to do more adventurous sex acts with a small penis.
Ryan:
Yes, that's right. I felt very frustrated that I couldn't do any of the fun things we were thinking about trying. However, when I was in chastity, a whole new world opened to us when I had no choice but to use my fingers and mouth. We also found chastity cages that have strapon inserts. After learning some new skills, I was able to please Isabelle and experience all these fun new positions.
Isabelle:
Yes, Ryan was pretty darn quick at learning how to lick pussy like a champ, and with the strapon on the cage, I was finally able to fill my pussy with cock, that first time was mind blowing. Ryan could never do that alone, but with a chastity cage and strapon, I was able to fill filled
Ryan:
I suppose I could have learned all that without the cage, but the cage forced the issue, I had no other options when locked up. Of course, I did really like giving up control, that was and is such a turn on for me.
Jessica:
So you both decide sissy play wasn't good for you, but you did decide you both liked chastity play. What happened next?
Isabelle:
Like you said, we both did not like sissy play, but we did like chastity play. So we decided to add chastity play as a regular part of our sex lives. We both were enjoying that Ryan would be locked in chastity when we were having sex, then he would get released at other times. As time progressed, I found I really liked taking charge of our sex lives.
Ryan:
And I loved it when Isabelle took charge. I don't say I let her take charge. I don't have the authority to let her do anything. I think we both knew that we were both happiest when Isabelle decided if and when we would have sex.
Isabelle:
When we were having vanilla sex and neither of us really took charge, we had sex maybe weekly. As soon as I took charge and we added chastity play, both our libidos skyrocketed. We were having sex three or four times a week. As time moved on, I started to realize that we had to stop intimacy and take the time to put his cage on and then continue whatever intimate act we were doing. I shared my concern that was starting to become a frustration.
Ryan:
I heard her frustrations and I noticed that too. Neither of us had an answer right away, but we both knew we wanted chastity cages to be part of our sex lives. I thought and did some research online, and found out about long term chastity. When I first read about it, the thought scared me. I was happy being caged while I was having sex, but I liked being free too. Or at least I thought I liked being free. I think it was more that I didn't want to fully submit to Isabelle. When I thought about it more, it was that decision that lead me to want to control my own orgasm, and I didn't trust Isabelle enough to give up my control full time. After I had that epiphany, I had a hard conversation with Isabelle.
Isabelle:
We actually talked about long term chastity for a long time. We talked about Ryan's fear and lake of trust in me. As we talked, I felt very hurt, but I was able to forgive Ryan. I think being able to forgive is a part of accepting that we can make mistakes on a journey like this. We decided the next step for Ryan was to stay in chastity full time for a week. Since Ryan was use to wear a cage, and we had one that fits, it was a good next step.
Ryan:
Isabelle had set some ground rules that I fully embraced. I was not allowed to take the cage off, unless it was an emergency. Isabelle also thought it would be fun to make cleaning my cock and cage an act of submission and humiliation. My normal shower routine kept me fresh and clean, but the cage really need to be taken off every three days for a more thorough cleaning of the cage and my cock.
