Dear Diary – Day Twenty Seven

Oh my, what’s going to happen?

All I can keep thinking of is...

Dear Diary – Day Twenty Six

Having been pronounced fit to stand trial I was brought before Mistress Eleanor’s court.

The charge was simple.  I was accused of being a sissy.  Hearing this I almost felt relief and when asked how did I plead I, perhaps a tad too proudly, pronounced I was a sissy.  Thinking that would be the end of it I was surprised when Mistress Eleanor announced that we would be the judge of that.

The first witness was Maid M.  She confessed that she used to like teasing me by working around in just her bra and panties and chasing me and trying to kiss me.  I smiled at the memory and then cringed as she said how disgusted she was that I had taken her light blue panties and fishnet stockings and worn them.  How did she know that?

The next witnesses were a set of girls who complained about having to wear uniforms that were either see through, especially when wet, or that had skirts that the wind would blow up with unrelenting ease.  Again a smile came to my face as I remembered the happy days, but again it turned to horror as they each said how violated they had felt when they saw me looking up their skirts and dresses.  I thought I had been discrete, but obviously they had seen me.  I had kept careful records of what colour panties they were wearing each day.

Next came my first wife.  She told the court how much she loved me, before going on to say how I had never been able to give her an orgasm.  I was about to say that was because she never let me go down on her, but I knew I was not allowed to speak.  I felt bad knowing how inept I had been as a lover.  It then got worse as my first wife recounted a string of sexual perversions I had indulged in.  I was shocked by the detail she went to in describing them. I also realised she had not told anyone till now.  I felt bad.

Then there was Miss H who said how said how grateful she had been that I had let her stay with me.  I knew not to smile as I guessed what was coming although how she’d known about me wearing her bra and panties when she left for work each morning I couldn’t fathom.  I’d been so careful to take them from the dirty laundry basket.  Miss H also told the court about how I would lift up her skirt causing her deep embarrassment and humiliation. 

Then came M&M who had more tales of skirt lifting, knicker sniffing and pantie wearing.  I had to take their word for it as I am sure I would have done it if I had the chance.  

By now I just wanted to crawl under a rock and hide.

Then there was Mrs S who said how nice I was, but now that she’d heard these other testimonies she changed her mind and said I was a vile, disgusting creature.

At this stage I thought I was getting off lightly, but then had to listen quietly as my ex-wife went through a very, very long list of my failings on the domestic front.  I thought this was most unfair, but she had evidence to back up each claim and I was totally damned.

Next and in what I thought was highly improper and irregular, the jury, which consisted of all the ladies who had given evidence, were asked to give their verdict.  Without a pause and in total unison they said guilty. 

Judge Eleanor said clearly I was a sissy, but much worse, a depraved, perverted, disgusting, miserable slimy wanker.  I blushed red and wanted to apologise, not that it would do me any good, too late now.  Still, I felt it could have been worse, they didn’t know about Ms J, Ms D, Ms P or others.

Judge Eleanor announced that my sentencing would be tomorrow.  

Let me guess, it’s going to involve being strung up by my balls.  

It’s a fair cop. 

Dear Diary - Day Twenty Five

Stuck in this hospital bed there is not much I can do.  My arms and hands are so fixed that I can’t even reach my little bit, not that I would ever dream of touching it or diddling my little clitty, but it would be nice to know that it’s still there.

All I can do is worry.  What if my little itty bitty clitty never works again?

It was while I was worrying about never being able to enjoy a good wank, that a lady doctor came in.  Her face was covered in a surgical mask and I immediately thought the worst, but she held a clipboard rather than a scalpel.

After a few pleasantries, obviously keen to demonstrate her bedside manner, she got down to business.  “Time for some tests.”

I gulped, not wanting to be tested out of fear of failure and its consequences.

The bed was adjusted so I could observe the bandages being removed.  I closed my eyes tight.

Latex gloved hands manipulated my flaccid member, pulling it out, pushing it back, peeling away my foreskin, so that when I opened my eyes my clitty was there for all to see.  

It seemed smaller, if that was possible, and though it looked red and raw it didn’t hurt.  I looked expectantly at the Doctor hoping she would say something positive.

“Okay, I’m going to ask you to imagine some situations and will note your reaction.  Ready?

“Yes Ma’am” I replied, hoping that my politeness would get her on side and give me a chance at getting favourable results.

“A young woman is naked before you, expecting sexual intercourse.”  I tried imagining this but it was impossible.

After a minute the doctor let out a sad sigh.  “A woman is performing oral sex on you.”  Oh, that would be nice, but try as I might I just couldn’t imagine it being true.

The doctor's concern was evident in her voice as she said “What if you perform oral sex on her?”

Oh!  A slight twitch.

“Ah ha” exclaimed the doctor.  She then said “imagine watching the woman having sex...”  Twitch.  “With a black man...”  Twitch.  “The woman is your wife.” Twitch.  “You are serving as their sissy maid.”  Twitch, twitch, twitch!

“Very good.”  I could see I was almost fully erect.  Maybe I was just pleased with making the Doctor happy.

“Well” she continued, after making some notes “looks like you’re ready to be strung up by your balls.”

What?

Help!

Seeing my look of horror the doctor merely pointed at my clitty which was fully erect, as hard as can be, just like a little pin.  I think she was smiling.