Professor Sierra Gives a Guest Lecture on Prostate Milking
Hello to all you subbie scholars and sissy students! Today I am going to address a simple question…
Prostate milking: Health regimen or guilty pleasure?
The answer is that it’s both.
Whether you are a seasoned anal expert, or a tentative anal explorer, this lesson should help shed some light on an age-old practice. I truly believe that every man should have a clear understanding of his sexual anatomy. Yes, the prostate is one of your sex glands, boys. So sit back and enjoy Sex Ed 101 with Mistress Sierra: Prostate milking for beginners and beyond.
Um…what exactly is the prostate?
Did someone sleep through most of their high school biology classes? Naughty, naughty.
The prostate is a small exocrine sex gland that produces a slightly alkaline fluid that comprises a large portion of the male ejaculate. The prostatic fluid combines with fluid from the seminal vesicles and sperm from the testicles to produce semen, which is ejaculated through the penis during orgasm. The prostate is essential for reproduction and sexual performance. Isn’t science sexy?
Ok, so where is this thing located?
The prostate is actually not very difficult to stimulate. You just have to know where to go. If you insert your finger into your anal canal – using plenty of lubrication, of course – and curve it slightly toward your cock, you should feel a small, walnut-sized gland just beneath the lining. You can massage, or “milk”, the prostate by gently rubbing your finger in a side-to-side motion.
And why would I want to do that?
Two reasons. First, routine massaging of the prostate can produce enormous health benefits. It stimulates blood flow and allows the prostate to flush out accumulated fluid, preventing a multitude of problems including erectile dysfunction (no one wants that!) and an enlarged, painful prostate.
Second, there are a multitude of benefits for your sex life. Prostate milking can be an extremely pleasurable experience, often resulting in a highly intense orgasm, often without even stimulating your cock. Routine milking of the prostate can also lead to larger erections, longer erections, and better orgasm control. And for a chastity slave locked up for prolonged orgasm denial, it is often the only form of release that is allowed.
Ok, you convinced me to give it a try. Now what do I do?
Now this is the fun part!
If you have never done any kind of anal play, or even if your anal experience is limited, you will want to start out slow. And by slow, I mean small. Don’t go out and buy yourself a giant 12 inch dildo and expect to milk yourself with it!
You can milk your prostate yourself, or entice your partner to do it for you. You would be surprised at how many women love this sort of play, it is an incredible power surge. Lie down on the bed, make sure you are as relaxed as possible, bend your knees, and spread your legs. Apply a generous amount of lubrication to your finger and slowly insert it into your ass. Now, curve your finger slightly toward your cock. Feel around for the prostate, it is about the size of a walnut and has a squishy consistency. Now stimulate, very gently, side to side. Feels amazing, doesn’t it?
From here, you can decide how much stimulation you would like. You can experiment with different techniques and toys, like dildos and prostate stimulators. That’s all part of the fun! Don’t be afraid to really let go and enjoy yourself. The more you can allow yourself to get lost in the sensation, the better it will be. And if you’re lucky, you just might work your way up to being a bottom bitch for your strap-on wielding Mistress!
And now for your homework…share your very first anal experience (or fantasy) with Ms. Harper and I in the comments section…and the more details, the better!
Class dismissed….
Professor Sierra
Thank you so much for letting me be a guest on your blog, Ms. Harper! As you know, I am such a fan of your blog – it is always so informative and so sexy! I just love how you describe the way you use subtle nuances and suggestions for semi-public humiliation in your last post. And, thank you for reciprocating and posting an awesome article on Tag Team Humiliation on my blog 🙂
You know you can come post here anytime! Your insights about prostate milking are spot on, and I adore your in-depth exploration of all things ass. 😉 Bring your sexy self back any time you feel like it!
My penis almost no longer erect for women but for crossdressing and thinking I am tranny so shall I try to treat that or I live as a woman?
If you are trans, the only ‘cure’ is to live as the gender you identify as. So, maybe try living as a woman for a while, and see if you feel happier that way. If you find that you still think of yourself as a man, or would be happier living as a man, switch back. 😉
Well you said the more details the better so here it goes! First experience was when I was 25. Typical 25 year old not long out of college and a couple years into my first job. Had always liked assertive strong women but had no experience with Dommes. She was an attractive lady 10 years my senior whom I would cross paths with professionally a few times a month. One day she came into my office when it was pouring outside and her white linen top was soaked through! Of course I was a gentlemen and offered her a couple of spare hand towels from the store room but I couldn’t not look at her breast!
It was late with only us there and I had the radio playing and the Eve 6 song “Inside Out” was playing. I was singing along sort of under my breath and mouthed along with the line “tie me to the bedpost”. She perked up and said I wouldn’t mind seeing you tied to my bedpost. So I sort of laugh and think nothing of it afraid or to shy to seize that oppurtunity. We finish our business and she ask if I would like to come by her place later for a drink and of course I say yes.
Well about one bottle of wine in she tells me I look tense and like I could use a massage to relax. She sits behind me and starts rubbing my shoulders which felt wonderful under her magic hands. The massage got more and more sensual and she helped out of my shirt saying we needed some oil. I had a nice buzz and was absolutely putty in her hands at this point. She had me on my stomach working my back and then said lets get you out of those pants. So now I’m down to my boxers and the tent I was pitching was obvious. She just looked down and said “Nice”! I think we can do away with these now too! So I’m completely naked and she’s still clothed. A little CFNM although I was oblivious to the term or that it was a thing at the time. I just knew this sexy lady had me turned on like never before and this WAS NOT like the normal 20 something old girls I was used to hooking up with!
Next she had me back onto my stomach and started kneading and squeezing my butt cheeks. She would sort of spread them apart making me feel a little exposed but obviously turned on. She would then trace her fingers down my outer thighs down to the back of my knees and back up the inside of my thighs in which I would just stick my bum up a little so she could reach under and give my cock a light stroke. She would quickly glide back down to the balls and focus on that area in-between gradually spending more and more time near my ass asking me how it was feeling to which I could only moan in gibberish telling her all she needed to know no doubt! Then she started to circle my little virgin rose bud with her finger seducing my ass to the point I was sticking that ass in the air wanting more like a shameless whore in which she obliged and slowly worked her finger in and around.
It was done all so slowly and sensually I never had a chance to protest and didn’t want to. She expertly seduced my ass like a pro. After a long while of this she invited me back to her bedroom where she finally took her clothes off and we started making out on her bed. I was ready to consummate this friendship but she had other plans! She then cooed in my ear saying that she really wanted to tie me to her bedpost and I was helpless to say no. Out came the silk scarves and I was blindfolded and indeed tied to her bedpost.
I had never been so aroused and hard in my entire life. It was exhilarating! She teased my entire body in so many ways and to this day I do not know what all she was using on me. I didn’t even know the term Tease & Denial but that is exactly what she was doing to me! It went on for a couple hours and she did indeed ride my face to many orgasms as well. Then I feel something much bigger than a finger probing the opening of my ass. She slowly worked it in asking how I was along the way. It felt fucking amazing and then it started vibrating as well! I was a complete mess at this point and then felt her warm tongue licking and flicking my cock. She gave me the most incredible blow job while slowly working that vibrator in and around. Finally my body spasmed and she removed my cock from her mouth and jerked me off while working that vibrator and I came like I had never before. Earth shattering, moaning, crazy intense orgasm like nothing I had ever experienced. I didn’t see it but could feel the ribbons and ribbons of cum shooting out of my cock and it went on for what seemed like ever.
When I finally came down she removed my blindfold and asked me if I had ever cum that hard to which I replied not even close and she said it was one of these most spectacular eruptions she had ever witnessed as well! I was blown away and not sure what to think of that experience but knew I wanted more. Sadly I only saw her a few more times as she moved across the country shortly thereafter. She did mention that I should read “The Claiming of Sleeping Beauty” by Anne Rice. Looking back it’s obvious she was a Domme but this was in the early stages of the information age of today in which there is so much out there.
What ever feelings she brought out in me I knew I needed more of it and shortly thereafter I found the website CockControl while trying to research what it was I experienced with this women. This was back in the day Ally just got started with the old Red & Black website. So yeah from then on I became a complete and helpless little Tease & Denial pet as well as Buttslut. The way she introduced me to it I had no chance and of course the many amazing Mistresses of the Empire have only continued to exploit and encourage my ass since!
Currently I am in chastity for Ms. Hunter and tomorrow will be breaking my previous record of 2 months! I often wonder if I had not had that experience with that amazing lady if I would have realized I had an inner submissive side as well or discovered how amazing ass play can be. Women like her and the amazing Mistresses of LDW don’t exactly grow on trees! Hell maybe she is an LDW Mistress now I don’t even know…lol
As we say in Australia, you lucky bastard!
So.. it’s been a while since anyone has commented on this buttt… (no pun intended) I haven’t done this with my boyfriend yet but he has mentioned it a few times. I think we will have to get a little more comfortable before we try it but he has bought a few toys to try it out himself. I think eventually it will happen!