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Tips on Prostate Orgasm?
#1
So I bought a prostate massager a month ago. I've used it about 8 times for about an hour each time. It is not top of the line by any means. It does vibrate though. Each time I've used it I feel like I'm getting closer to the ultimate goal of orgasm. It feels great even not having the big O but I want to experience it so bad. Everything I read from people who have achieved it have said how incredible it is. 

Today I was so close I was shaking. It was amazing and by far the best day yet. Since I'm new to this I was wondering if any of you had any advice or techniques you could share? Also, I feel like each time my prostate is dropping easier and it takes less time to get it feeling really good. It's almost like exercising I guess. I used it yesterday and had an ok session. But today as soon as I stuck it in it was like the prostate was ready for it and it immediately felt great. So does it continue to get easier the more you do it or is that just in my head? Thanks for any and all feedback.
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#2
You may be too casual about this, and you may be overdoing things (8 tries in 2 weeks?).  This is not about masturbation, wanking, or jerking off, this is about your first sissygasm, when you achieve the special gentle emissions that are your reward and your confirmation of your femininity.  It was when I reached this goal that I knew I was no longer a man (if I had ever been one).  I am a sissy.

I recommend making everything about this wonderful transformation special and precious.

First, pick a special day (certainly no more than once a week!) and mark it on your calendar.  Every morning put an 'X' on your calendar as you march through the days to your special day.  Have I mentioned no jerking off?  Every 'X' marks one more day you haven't debased yourself acting like a man.  Think of yourself as in chastity even if you don't have a cage, though a chastity cage would be better.

You need a special box or place to store everything you will use on your special day, and you should check it every day.  And you need a special place.  If that place is your bed, then clean and pretty sheets should be in your box, along with a pretty nightie, perhaps.  Your toys, your perfume, your lube, your music, wipes, a blanket perhaps, everything is in your box.  Soap, razor, enema, all in the box.

When your special day arrives, remove everything from your special box and arrange the contents where needed, at your special place or next to your tub or wherever.  Your special CD is playing, you're almost there.

You'll need to sissy douche to clean your sissy pussy, then a bubble bath so you're clean and smooth all over, and when you're made up and perfumed and wearing your special nightie, your ready for a final inspection of your special self and your special place, and then you're ready to proceed.

This is pretty much how I was instructed to prepare for my special times, though brief.  Individualize your own special ritual, since you are your own special sissy approaching and finally becoming your very special self.  Remember, if you don't make it this time, no wanking!  No nasty male completion.  You are special.  You are a sissy.
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#3
(01-19-2017, 02:54 PM)Sissy Renee Wrote: You may be too casual about this, and you may be overdoing things (8 tries in 2 weeks?).  This is not about masturbation, wanking, or jerking off, this is about your first sissygasm, when you achieve the special gentle emissions that are your reward and your confirmation of your femininity.  It was when I reached this goal that I knew I was no longer a man (if I had ever been one).  I am a sissy.

I recommend making everything about this wonderful transformation special and precious.

First, pick a special day (certainly no more than once a week!) and mark it on your calendar.  Every morning put an 'X' on your calendar as you march through the days to your special day.  Have I mentioned no jerking off?  Every 'X' marks one more day you haven't debased yourself acting like a man.  Think of yourself as in chastity even if you don't have a cage, though a chastity cage would be better.

You need a special box or place to store everything you will use on your special day, and you should check it every day.  And you need a special place.  If that place is your bed, then clean and pretty sheets should be in your box, along with a pretty nightie, perhaps.  Your toys, your perfume, your lube, your music, wipes, a blanket perhaps, everything is in your box.  Soap, razor, enema, all in the box.

When your special day arrives, remove everything from your special box and arrange the contents where needed, at your special place or next to your tub or wherever.  Your special CD is playing, you're almost there.

You'll need to sissy douche to clean your sissy pussy, then a bubble bath so you're clean and smooth all over, and when you're made up and perfumed and wearing your special nightie, your ready for a final inspection of your special self and your special place, and then you're ready to proceed.

This is pretty much how I was instructed to prepare for my special times, though brief.  Individualize your own special ritual, since you are your own special sissy approaching and finally becoming your very special self.  Remember, if you don't make it this time, no wanking!  No nasty male completion.  You are special.  You are a sissy.

Thank you for this wonderful reply. I have been seriously considering purchasing a prostate massager, but had not thought about it as my initiation into sissyhood. I mean, i am a sissy, but i have never experienced the gentle emissions of a sissygasm. Now i am anxious, and a little nervous, to try. I have experimented with (or have been subjected to by males and one Female) sissy plugs, sissy douches and enemas, dildoes, and digital entrance into my sissy pussy, but never prostate massage and sissygasm. Did it really make you feel like you were on a new and absolutely real plain of sissiness? I would love that! 
May i contact you for more help if i need it in order to make this experience extra special.?
Sissy to sissy, i thank you.
Heart kerri  Heart
Angry "Why you naughty little sissy!!! Bring me a fresh diaper and then fetch the paddle!!!"  Angry
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#4
To put it simply, it completed me.
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#5
Thanks for that beautifully written post Sissy Renee. I will definitely follow your instructions the next time I try. I can't wait to one day have my first sissgasm!
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#6
For an interesting and informative take on how a loving Mistress trains her sissy, I recommend Lady Lubyanka's thoughts.  The topic is covered from the sissy's anatomy to her fluid milky results.  You will note she is kept chaste while she is being trained, demonstrating one of the benefits of being caged. 
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#7
My husband can attest to the intense pleasure this activity can produce, though he has never had to perform on himself. I'm all too willing to take charge of that activity. But judging by his responses, it is most certainly intense.
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#8
I had a girlfriend a while ago who would massage me like this. But she'd only do it if I had a pair of her knickers on for her to reach inside. So it always made me feel incredibly sissyish.
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