Monday, April 2, 2012

Sissy Masturbation and Milking

It has been a very long time since I played with myself using the method I'd used for so many years.  Specifically, like most other men, I would grasp my penis in my right hand, wrap it around the penis and begin stroking up and down.  Sometimes I would also hold a soft pair of panties in my hand to provide a different sensation.  But for the most part the grip, motion and sensation was the same.

All that changed a few years ago when Diane had a different plan for me.  There would be no more "closed fisted pumping" for this sissy. 

Instead, Diane's milking would consist of softly running her fingers and massaging the underside of my cock, with special attention to the area directly below the head.  Sometimes, she would also grip it a bit more firmly by securing it with her thumb as well.  From that point on, I was told that I would no longer be able to use the closed fisted method, instead rubbing my cock with middle and pointing fingers on my right hand.  It was what Diane called the "sissy masturbation" technique.   No doubt, it is much more feminine and sensually soft than what I had done before.

Two things happened in the past couple of weeks that reminded me of the change and prompted me to write about it.

First, I had struck up an online conversation with another sissy who is in a very similar situation as I am, living as a sissy wife for his dominant wife.  Surprisingly we discovered that our masturbation techniques were very, very similar.  My friend "D" also finds this method to be much more feminine and like me, suffers the embarrassment of having to do this in front of his wife.

The second incident which prompted me to write about it happened a few days ago when I read a post on the Chris Bellows Bedtime Reader blog.  Chris Bellows is a nom-de-plume for an erotic writer whose works focus on pretty hard core D/s with plenty of Female Domination.  I think he's a very creative writer and I suggest you check out his blog.

The post I read prompted me to go back and look at an earlier posting it referred to which had a link to a very erotic video of a Mistress milking a male.  The method by which she performed the task was shockingly similar to what Diane uses on me.  It's a sensual process (not always slower though depending on my state of arousal and her verbal teasing) for both parties, particularly compared to the way I used to masturbate.

To paraphrase Diane,  "The hard pumping with your full hand is the way real men masturbate, not sissies."  It's one of many ways she likes to point out that I'm different.

I'm sure most men prefer the more common method, but for sissies like "D" and I, sissy masturbation fits us so femininely well.


  1. That is a very hot video. My wife did something similar to me a while ago. She very rarely gets me off, but that time, it was great.

  2. Wow, what a great video!

    Has Diane ever used any toys to masturbate you?

  3. Wow Wow A hot video indeed. I have to agree with you that it is quite the sissy and feminine way to play with yourself!


  4. The video is really sissy!
    I once saw a video similar to this where it had the sissy aimed down and squatting over the toilet, so the sissy cream could go where it belonged, as far as they were concerned.

  5. Terri,

    Thanks for sharing the video, that was very erotic. I have watched it several times (I only wish I spoke German) and love the obvious connection she has with the male.

    I am not sure I could ever get to the point where just that sort of rubbing would do it for me, though the thought of mistress denying me any other contact until I could orgasm from such limited touching, is very hot.

    I love your blog.


  6. Thank you. i can only cum when something is moving up and down in male pussy hole. if i have a hard time gettin g cockette up i have to use the techique you described but normally i am not allowed to touch cockette

  7. terri- Thank you for sharing. My wife has not done this to me, but I see your and D's points on this... it IS much more feminine. The video of course proved it. Much more of a feminine way to be aroused, isn't it? My little clitty is tenting in my panties!

  8. Dear Terri,

    Well, you inspired me. After reading this post and viewing that video (many times) I decided to touch myself with only my first two fingers. This was a huge change for me. I began masturbating at the age of 3 or 4 and I have always humped myself against a pillow or comforter. That said, after a work week of denial, I was rather easily able to orgasm(twice) by touching "missy" with just my first two fingers.

    I was a little surprised I could undo 40 years of conditioning, but delighted to feel more feminine.

    Take care,


  9. Which brings to mind using a vibrator...exactly as a Woman would rubbing it on the underside. Talk about feeling more Feminine! The orgasm is usually mind blowing and the ONLY way my Woman will masturbate me. It's wonderful knowing I am doing something that millions of Woman are doing in the same exact way.

    1. Very nice idea Marysgirl!


      sissy terri

  10. Nice. I discovered that point below the head recently when rubbing my cock with middle finger.

    I also tend to put my other hand's middle finger in between the butt cheeks from behind (instead of from between legs), and then move my ass up and down to feel the finger moving between the cheeks, and i also rub the surface of my hole in the same position.

    Feels good when doing it when standing with legs open or when positioned in doggy style.

  11. I've masturbated this way my entire life. It just came naturally.

  12. i love my cum... the longer the tease the more there is. yummy.

  13. wifey released me from my belt this morning to find an almost instant erect one... its been so long. since i will be serving at her pool party today she said i should rid myself of my embarassment before donning my microkini and heels. she insisted however on applying icyhot with no other stimulation... mmmmm

  14. Video was removed :-( You should find another one for your recent readers. Thanks.