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.

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Another Cuckolding Discussion

Last night, Diane was in one of her more Dominantly amorous moods.  She wanted sexual relief and she wanted it in a specific way.  We made our way to the bedroom earlier than usual and I got into one of my prettier nighties in preparation to please her.  We don't have traditional male-female sex.  I pleasure her orally only, and she penetrates me anally when she so pleases.

This post isn't about the sex we had last night, although it does play an important part in setting the stage for the discussion that followed.  When I began pleasing Diane last night, I could tell that she was already highly aroused; if not physically, she was mentally into it already.  As a result, she achieved her first orgasm in not time and insisted on another.  The second came much quicker than her typical "follow-up" orgasms come.  Clearly, she was quite horny last night.

A few minutes later as we were relaxing (I still without relief) Diane mentioned that Brian, her old friend she had met and danced with at the wedding we went to last Saturday night, had emailed her and invited her to lunch some time next week.  The company he works for has an office in the city where Diane works and he could easily schedule some visits there she said.  Immediately, my mind played tricks with me as I connected her quick orgasms with the possibility she was fantasizing about Brian.

She teased me while asking "You wouldn't mind now would you?" in a rather joking and sarcastic tone.  Leaning over, she caressed my penis through the panties I had on.  "I'll send you the email tomorrow so you can read it.  I'd like your opinion on it" she said.

I asked her why she needed my opinion.  "You know, tell me what you think.  Does it sound like more than just a lunch invitation?  Use some of your feminine insight and tell me how you would take it" she said. 

The more she talked, I got harder.  She continued to tease.  As aroused as I got, part of me is afraid of moving forward.  I suppose it is a natural reaction.  Just like the reaction I had to her teasing me and fondling my cock.   Eventually, I came in my panties and had to change them.

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