Male Chastity “Pointers”

[This blog was inspired by @Pasttime and @BigGlansDC, thanks!]

@Pasttime expressed an interest in male chastity and our wearing of “chastity cups”. I thought this would be a good time to express some of my opinions (as a sort-of refreshed “training session”). Here goes…..

This “chastity play” is always voluntary, and unlike other chastity “devices” where a keyholder allow access to orgasms, this activity is totally under our control. Whether and when we wear a “chastity” jock/cup is entirely up to us. How long we wear it is also up to us.

Selection Process
I have discovered over the years that there is a wide range of “fit” options when selecting a jockstrap/cup. Some are tighter, some are looser. Some cups are big, some are small. I would suggest buying a few different brands since all of them will “fit” differently. (In actuality, there are not a lot of cups on the market). Currently, my favorites are Mueller FlexShield and XO ProCup.

What Do the Cups Do?
{Normally, the jockstraps with hard cups are worn by men to protect the male genitals during contact sports like baseball. Using these cups for “chastity play” is an entirely different use for them. I will explain the secondary use in this blog.}

The consolations of a jock and cup on cold winter’s nights

Hi guys,

I haven’t had an Aneros session for nearly three weeks now. Activities and concerns distracted me from having one during the holidays. Intense winter cold imposed itself for nearly a week now which dissuaded me from sessions. A snowstorm along with intense cold this weekend will not loosen their grip for at least a few weeks at the earliest.

@goldenboy’s wearing a jock and cup to bed most nights has been a real inspiration for me to do the same. O how sweet it is to wear a jock and cup to bed on cold winter’s nights!

@goldenboy enjoys wearing the Shock Doctor Ultra Carbon Flex Cup along with its jock to bed many nights. He calls it his chastity cup. This athletic cup has nearly the same dimensions as the BIKE CUP Supporter Unit no. 85 of which I have quite a few in my collection. The BIKE CUP was a real hit among athletes participating in contact sports the middle to late 1980. Both the Shock Doctor Ultra Carbon Flex Cup and BIKE CUP have nearly thick rubber gaskets which prevent chafing on the groin area of athletes. Hence both cups are comfortable to wear, not only on the playing field, but also during everyday wear, and even in bed at night.

Both athletic cups are especially hot for Kegeling in, certainly in bed at night. It is so sweet to diddle yourself while doing some Kegels in a cup on cold winter nights in bed. Take care!

Pleasure generating pleasure

Recently, the Aneros stroking my prostate has been so pleasurable in itself that I haven’t found the need for audio files like I always do in my previous sessions. The pleasure causes the PC muscles to contract and moves the Aneros to stroke the prostate and the cycle keeps on going.

The pleasure from the Aneros combined with erotic fantasies and circling around my nipples has been enough to tip me over to orgasm. This lets my body determine when it wants the orgasm instead of letting the audio dictate when I should receive pleasure.

I also noticed that my porn consumption has decreased because I realise that if I ejaculate, the session comes to an end. I would rather enjoy a longer and relaxing Anerosession than a rapid masturbation session and worry about ending it too quickly by ejaculating.

Adjusting to a more sane routine

Saturday, January 12, 2019 12:21

So my journey is just a little over a week old, and already I have had incredible, previously unknown experiences. I definitely see this journey lasting the rest of my life, and transforming and aiding many life experiences as well as my orgasmic life.

Obviously, it also has its challenges. This week it has almost entirely taken over my life. Between reading the forums, writing on the forum, having Aneros experiences, and experiencing Aless almost all day long, I can hardly think about anything else. I make my own work schedule and I have a lot of private time, so it can be easy to postpone or procrastinate on other things. I’m very glad I had some appointments this week, or it may have totally lost myself in the euphoria.

I have also had some physical warning signs this week, especially after using the Aneros for any protracted time. Particularly after one protracted and very physical session, I experienced abdominal pain and extreme fatigue, which made me feel kind of dysfunctional. At the end of the session I had probably the biggest ejaculation I have had in a very very long time, so I’m sure that was a factor. I’ve also had headaches after two longer sessions, which I’m quite sure were brought on by the massager. Lastly, I also have some lingering dull pain in my rectum following the longer sessions. I’ve been able to convert these in my mind to pleasure, so they are not much of a problem. I think of it as longing, which actually might be the case. Lastly, the device and the forum have been “robbing” me of a lot of my sleep, so I know I am not well rested.

Wake Up Call

Well…its been 5 days since my last ejaculation. Also 5 days since my last bit of prostate play. Between work and just being tired…just havent had a chance to explore with myself. Well this morning I had an opportunity. The wife left for work early and it was just me and the dog. Started to look at some pics on Reddit and that got me warmed up pretty quickly. Today showed a lot of growth in my prostate stimulation journey. Once I got to the state of pure arousal…I pretty much stayed there for 30 mins and the only reason why it didn’t last any longer was because I needed to walk the dog.

30 mins of pure tingling sprinkled with very intense super-Os that made my head spasm. Thats actually the tell tale sign I am having a super-O. My head shakes involuntarily like I am having a seizure, my toes curl and relax without me really doing anything, my body is rigid but doing like the most minute spasming. It all feels like an exquisite rumble emanating from the center of my body. Most of the time my cock is rock hard but sometimes it starts out super soft and then the longer I am in the state my cock just rises. It’s such a good and relaxing feeling.

Starting Again

Two years ago, I bought the set of four Peridise massagers with the full intention of using them for anal health, pleasure, and prostate stimulation. In my first session back then, I used the second-smallest Peridise. Against all reason, I decided to go to town. Lots of flexing, breathing, and clenching for an hour and a half. It felt good at the time, but the next day, there were awful health repercussions – they were horrific enough that I gave up on any anal use at all; outside of normal bodily functions. It was a bit crushing, as previously, my anus had been a source of great pleasures.

Fast-forward to now. Taking a lot of advice to heart, I decided to go slow in reclaiming my body. For the past year, I’ve been gently reintroducing my anus to stimulation and penetration using my finger or small, smooth toys. Finally, I felt like I was ready to try the Peridise again. It was really nerve-wracking at first, but using yoga breathing techniques helped keep my body and mind at ease.

Read up on the Aneros forums about how to use the Peridise – supposed to start with the largest size, and work your way down as you tone your anal muscles. It looked small enough. Followed the directions in the box (relax, practice contractions with no device in, then lubricate). Used a gloved finger to apply ID brand lube (an old favorite) to outer anus, massaged some around, then eventually inside. Applied generous amount to bulb on largest Peridise, then all over the shaft.


So it’s been maybe a month since the last time I played, but man was the craving there. Same set up as always, helix syn, porn, and my trusty hash oil pen.

Pretty normal session, aside from the fact that I was very horny from anticipation. The porn choice I selected is arguably more tame than what I’d normally watch, but how my body was feeling watching it you’d probably wouldn’t be able to tell the difference. I’ve found that I prefer watching something more audible (lots of moaning, screaming, etc) is way more stimulating while playing since I might not be watching. About half an hour in I decide to hit the vape pen and it really gets things going. About another half an hour goes by of riding the wave up and down and I had another wet orgasm. Instead of stopping the session here, I decided to keep riding it out for another 10 minutes since I was still feeling it.

I got up to clean up and take a shower and this is where things got interesting. As I was washing my hair I would close my eyes and I when I did it almost felt like everything was on a slant. I was having some audio hallucinations as well, must have been spilled over from the porn I was watching. There was very much an enlightened/euphoric feeling I was having while showering, and feeling very self aware of all the sensations while I was showering. If any of you are experienced with psychedelics, this was very similar to (if not exactly the same) as the “peak”. For the rest of the day I was feeling insanely horny, probably tugged it out 5 or so times haha.

Close call

Last night I had started with ET and switched to Max T after about an hour.
Rolled on my side with knees up high when I had almost a soft thrumming in my head with an undulating blue gray canvas display in my visual cortex. This was followed by a rapid series of porno images rolling through my mind. Very strange. I was awake so this wasn’t dreaming.
Lasted maybe 5 or 8 seconds.

It was all very subtle and I wanted more, but it faded out.

Fun in the shower

1/10 10:15 a.m.

Ok, there’s more. Sorry to be writing so much, but it’s so much fun I really want to share. And I think maybe writing about it is fun as well.
After I got done writing my previous post I needed to go up and shower to get ready for an appointment. My rectum was missing Syn a little, so I decided I would try inviting Helix into the shower with me. I grabbed the massager, lubed my hole and canal and then lubed up Helix. She wanted to play with my perineum and scrotum before she went inside, so I let her do that and then directed her in. Ahhhh. Going in and coming out is one of my favorite parts. I really didn’t expect much; I just thought she would lay in there like when I was sleeping. However, as I started to shower, the motion moved her around and gave me the most wonderful sensations. Then (as I’ve heard others say), POW! – pow!, pow!, pow!. She was fucking me powerfully. Not sure I had even experienced auto-fucking before this point. I was vocalizing, dancing, trying different positions to optimize. The party lasted my whole shower (which are longish). When I was done showering I thought it would be efficient to bring her out into the open and clean her up. When I took her out I lingered when the largest part of her was near my inner sphincter (I think). Exquisite pleasure! Thanks, helix, for the fuck. I owe you.