[Chosen_Jackal] Pinch me, is this really happening?

[Chosen_Jackal]

Red pointed out a typo. I wrote miming when I meant milking and now she’s playfully threatening to just mime doing stuff to me! Oh lord!

[Tongue+groove]

Hahaha I saw that but I also know I typo at times also and auto correction gets me too.

The way Miss Red is handling it is awesome. I think it was mr Pickle who was given a dildo that he could Jack off while locked. The things these kh’s come up with sometimes. They are exciting creatures!

[Chosen_Jackal]

It’s been a bit gloomy in this journal lately so let’s make this more about the sexy and fun stuff.
Red and I’ve talked a bit more to understand each other better and this has resulted in more attention for us both.
Yesterday was such an amazing day to me.
After she came home from work she was all over me with affection.
Lots of kissing and small touches in naughty places.
The feeling that ran trough my body when she kissed me deeply and passionately while fondling and squeezing my balls at the tame time is almost indescribable.
I’ve also enjoyed kissing Red. She’s a very good kisser and I’ve never felt that I’m on her level in that department.
Now however, I actually get literally weak in the knees and a physical shiver runs throughe when she kisses me passionately. I emit small moans of pleasure that I have no control over.
This woman has me completely under her spell with such a simple act.

We watched the last two episodes of a show we’ve been watching last night and I gave her a good and deep foot massage with proper oil and everything. After that she caressed my nipples as we lay beside each other and I felt sexual tension build in my body. I’ve never been very into having my nipples touched before, but after starting with chastity it’s like my entire body is super sensitive.
I can’t say for sure, but I feel I could have reached som sort of climax is he’d gone longer and more focused. I sure hope to find out some day.

She told over breakfast yesterday that she needed to be fucked properly, and I knew that meant it was time for the big strap on dildo. So when we went to bed I was a little ahead of her and got ready as I waited for her to come join me.
She smiled when she saw and commented how cute and eager I looked.
She then surprised me and unlocked my cage.
I was hard immediately, and the size didn’t between my dick and the 10 inch girth dildo was both hot and humiliating at the same time.
She took both the dildo and me in her mouth and I felt so teased.

I took her with the big dildo while me dick was free but unable to get to any place it could get any pleasure. She used the small bullet vibrator on her clit and came hard. I swear she’s so incredibly sexy when she cums and it feels so much better and giving to me to watch her have an orgasm than to have one myself.
This where we usually cuddle a bit before she tells me to lock back up, but she surprised me again by saying "your turn".

I’ve dabbled a bit with sounding for a short while and bought several sounding rods. From 6 to 12mm in thickness.
I remember how she was almost shocked by what she saw when I showed her the first porn clip where a guy got jerked off while having a sounding rod deep inside his penis.
She almost reacted like I was a freak for getting turned on by that.
Now I know the idea has had time to mature in her head because she’s brought up that she’s curious about it a few times and we’ve even tried it once before, but just for her to see how it’s done.
Last night she said bring me the rod and I brought out the 8mm rod (the largest size I can comfortably take without issue).

She inserted the rod and let it slide deep within me before she moved it slowly up and down. The feeling of being jerked from the inside is incredible.
She also jerked me slowly with her other hand, changing speed and positioning of her grip constantly to keep me on the edge for a long time.
I wasn’t allowed to cum and she was clearly enjoying keeping me edged.
I came close several times and I’m pretty sure a good load would’ve dribbled out if I wasn’t so thoroughly plugged.
She gave me more attention than would’ve thought (she’s been a bit selfish in the bed lately ) and finally she said we’re done.
I got locked back up and spooned her amazing body as we went to sleep.

Today I’m feeling like the happiest man on planet earth and more in love with my amazing woman than ever!

[Tongue+groove]

Oh my what an evening. A few things if I may. Yes watching your lover orgasm is the greatest show on earth. And secondly I’ve been jerked and sounded one time. She couldn’t help but feel like she was hurting me, she just couldn’t get into it. On that note I have found that with sounding when i get into the prostate I will go soft and can come multiple times. But if i stay in the shaft and stroke then i get super hard to the point that the sound is difficult to remove without relaxing a bit (mine is a 10mm).

Here’s my reason for comment. If I sound myself to super hardness it’s like being on viagra, it takes forever for me to go soft. What was your experience like getting back in lockup.

FWIW I haven’t sounded since chastity.

[Chosen_Jackal]

Red isn’t comfortable with going too deep yet, so we didn’t go further than the base of the penis yesterday. I also had the ring on so I felt it restricting how far the sound could go.

That said, having the sound in makes me rock hard, but it doesn’t take any longer than usual to go afterwards. Whenever I’ve experimented with prostate play through the butt I’ve also gone soft.
Red has only pegged me once and she was concerned I didn’t like it since I got soft when she did so, but I assured her that it’s normal and has nothing to do with how much I enjoyed it.

I actually hope she’ll get back to pegging me again, but she said she felt strange after the first time. I will have to talk to her about it.

[Tongue+groove]

Oh to be pegged. Unfortunately it’s way too risky since my proctocolectomy.

Some advice on sounding your prostate. Have plenty of protection down. As for me I will ejaculate urine uncontrollably, multiple times. Another reason for drinking lots of water. And when I do finally allow myself to ejaculate semen I will have no sexual desire for as much as a week easily. I get a serious drop. If you’re willing to pay that price and she wants to be involved then I would have her just watch the first few times, because making that bend in the urethra to approach the prostate is a crucial move. Don’t use a small sound for this, it needs to be good fitting.

And the last step of entering the prostate should only be done by you. Once you’re in, guide her hand. Keep it gentle and hang on for the ride. When your prostate expels it will push the sound out, let it do this, then reinsert again. It’s very exhilarating and risky too.

Play safe.

[Chosen_Jackal]

The last time I played with my prostate I felt the usual build up and suddenly pee started to come out in the steadiest stream I’ve had since I was sixteen

I had to change the bed sheets and everything.

I’ve never tried stimulate the proster through the urethra and bladder but now I’m certainly intrigued!
Red will have to let me out for this though, so… Red? If you’re reading this, pretty please?

[Chosen_Jackal]

Great day yesterday. I got to hang out with Red for most of the day and it really showed me how much I’ve missed being around her lately. She’s entering the busiest time of year for her work and I know she’ll have to prioritize work for the next couple of months. We’ve talked about this and after we started this new lifestyle I feel a greater need for emotional connection than earlier. I told her I was afraid of feeling like I’m not prioritized. I also realize at the same time that this is a me problem and that I need to work on how I process these emotions.

I’m dedicated to doing as much of the house chores as I can so she doesn’t have to expend her energies on this and hopefully have more energy and want to spend it on us.
She’s been amazing this weekend and we’ve cuddled and talked, had amazing sex and just enjoyed each other.
The new dildo arrived yesterday and it seems to be a success. I believe Red enjoys it even more than the previous ones and she agreed that she doesn’t have much need for my penis anymore.
She actually told me today that she’s a bit afraid that any normal penis will feel like a disappointment from here on out.

I’m staying locked.
Red doesn’t have a set date for when I’m getting my next release, but we’ve both agreed that it will be a long time.
My longest period of being locked is 18 days so far and we both believe we could extend that significantly.
I’m really excited to see how long she’ll keep me locked. I’m also feeling the need to cum already so it’s going to be interesting. I enjoy the frustration. I enjoy being horny for Red and willing to do anything for her just to feel how good it is when she’s happy with me.
I’m also extremely turned on by how comfortable she is by receiving pleasure without giving the same back. I know she felt guilty about this in the beginning, but she’s come a long way in a relatively short time.

I’ve thought about how I most enjoy receiving pleasure myself.
I loved how Red turned the attention towards me after she had her orgasm this Friday and edged me while I had a sounding rod in my penis.
But when I’m servicing her I’m so focused on her that I don’t fully feel like I can concentrate on receiving pleasure myself. It’s like my mindset is fully submissive and I actually struggle with accepting it.
I think I would be better able to focus on the act if she told me that now it’s about me and I would just accept whatever she decides to do to me.
It’s almost like I need to be mentally prepared for receiving attention and pleasure in order to fully appreciate it?
Am I the only one that feels this way?
Input and feedback from those that have ane thoughts on the is appreciated.

[Tongue+groove]

Am I the only one that feels this way?

No. I have discovered that even if I’m unlocked I can barely get hard while pleasuring her. It happened last night as I will post in my journal a little later.

The mental state of fulling giving to her, totally destroys all selfishness of receiving. And like you and others have said, there’s more pleasure in watching her enjoying the moment than anything else.

The problem is convincing her of this. Mrs. G continues to ask if I’m ok with being denied.

[Chosen_Jackal]

I have the same issue. I’m so conditioned to thinking that my penis is irrelevant to her pleasure at this point that I sometimes struggle to get hard.
Like last night.
I used the new dildo with the strap on harness on Red and I was extremely turned on. She was so goddamned sexy, but I was completely soft in my cage.
It’s almost like my penis has learned to stay out of it.

But when she teases me by grabbing my balls or pulls me close for a deep tongue kiss I get instantly hard.
It’s such a mind fuck