from Sandra

Dear Helga,

I had written to you earlier describing my use of chastity training with my dear sissy husband Chrissy. As I mentioned in that letter, not only has Chrissy been petticoated and kept in a chastity 24/7, but I also used the chastity device in such a way that he has been conditioned to be unable to get an erection, rendering the poor little thing quite impotent (which had been my goal, of course).

As I also mentioned in that letter, I do subject Chrissy to a regiment of occasional prostate milkings - which, for a couple of reasons, he finds rather unpleasant. One reason is that he reports that the feeling itself is simply odd. Not at all like an orgasm, but instead, just a bit uncomfortable. However, the major reason for his dislike of his milking sessions is that he finds them so humiliating.

Of course, for a sissy husband to be as deprived as he is of any sexual pleasure, the experience of being milked is quite inherently demeaning and humiliating - reinforcing his lowly status within the marriage and serving as an abject reminder to him of his lack of any semblance of masculinity. But in addition to that, my poor hubby almost always is milked in front of, and for the amusement of, my friends.

You see, I'm an avid bridge player, and at least once per week my women's bridge club meets at my home for an evening of socializing and cards. Usually this involves myself and seven other women. Chrissy, of course, is assigned sissy maid duty for these evenings - cleaning the house, preparing hors d'oeuvres, greeting my guests as each one arrives (always with a proper curtsy), taking drink orders, and so on. About once per month, we take a break during the evening so that my friends can watch as I milk Chrissy.

The signal that a milking is going to take place is when I instruct Chrissy to go get my rubber gloves and the lubricant. The poor dear always gets a crestfallen look at that point, and he has been known to beg and plead with me not to shame him by milking him in front of my friends, but needless to say, his pleadings always fall on deaf ears.

When he returns, and while I put on one of the gloves, he obediently spreads a layer of newspapers on one of our coffee tables, then compliantly gets on the papers on his hands and knees and pulls up his skirt to above his waist and then pulls his panties down to around his lower thighs. I then unlock and remove his chastity, and while my friends watch, I play with his limp little sissy clit, showing them all how small he is and also how completely unable he is to achieve an erection of any kind. Although they have all seen this demonstration a number of times, my friends never cease to find it both fascinating and surprising, and they love to tease my poor hubby about both his lack of size and his inability to get hard.

After playing with him for a couple of minutes, the milking itself begins. My friends typically crowd around the table to get a good look as I insert one finger deep inside his sissy pussy. I've learned over time exactly where to exert some pulsing pressure, and it is usually a matter of only about half a minute before some milky liquid begins to seep from the tip of Chrissy little sissy clitty - at which point, the laughter from my friends begins anew.

And as shameful as those evenings are for Chrissy, the ones he dreads the most are the milking evenings when, rather than the milking taking place in front of my bridge lady friends, it takes place in front of some of my femdom lady friends and their submissive husbands. I'm quite active in the local femdom female-led marriage community, and a few times each year I will invite some of the couples from that community to come to my home for some instruction in the use of petticoating, sissification, and extreme chastisement. Typically, the women in these relationships have already firmly established their position of dominance and authority, but now are interested in the possibility of transforming their husbands into their sissymaids.

When Chrissy greets them at the door with a curtsy, and then when they see how deeply effeminate and obedient he is, the women are always quite impressed -- while their husbands often become somewhat fearful and anxious as they realize that what they are seeing is what their own fate is likely to be. And that anxiety only intensifies as I make Chrissy show them his chastity -- and as I then remove it to show them the effects of his impotence conditioning. Indeed, it is not unusual, at that point, for one or more of the assembled submissive husbands to fall to the floor at their wives' feet to tearfully beg that their wives not sissify and chastise them the way I've done with Chrissy. And their tearful pleadings usually intensify - and at the same time the laughter on the part of the wives grows louder as well - when I proceed to subject Chrissy to a milking in front of them. I really should make a video of one of these sessions - with all the women watching in laughter-filled amazement while the males are agitatedly crying and pleading - and as the liquid drips from my poor Chrissy's limp little peenie!

Thanks for this opportunity to relate some details of my life with Chrissy.

Best wishes

Thank you for your letter Sandra. This milking with witnesses is a perfect example of your power, not only to your sissy but for your friends, and the occasional terrified husbands to see and I thank you for sharing it with us.


Return to Index
Letter 6