The Sugar Plum Fairy a New Sissy makes Her Debut

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Sissy Stay Up Stockings

 

I  call this sissy Sugar Plum. I’ve had many

Sissy Silky Panties

sissies throughout the years and have given them sweet sissy names. You must earn a special sissy name from me. No two sissies are alike. Some women like to give them girls name and although this is ok, I prefer something “special” and unique.

Sugar Plum contacted me on Nite Flirt wanting to experience control from a dominant mistress. He asked for strict sissy training and to explore his passionate need for submission. He wanted more then just sissy phone sex. He wanted/needed to feel owned and appreciated.

This was his first email:

“Initially I see my first call as a strict orientation session setting your expectations. As we grow in this relationship, I see what you describe in your blog of taking a man through humiliation outings very exciting. I also would like to experience your evaluating my behavior and disciplining me for correction and better behavior before/after/during sessions. I also confess that i do masturbate and desire to cum, but when it is allowed, i feel more satisfied by being punished before and after the experience (e.g. with spanking and forced clean up by eating it.)”

Sugar Plums Bra

But he also wanted an ongoing relationship and someone who would push his limits. Of course Sugar Plum is a married closet sissy.

After our first conversation I sent Sugar Plum on a shopping assignment to get panties, bra and stockings. The pictures prove that he did so. At first he chickened out and I almost dropped him. But he quickly got back on track and complied.

Sugar Plum had to wait several days, actually a week with no cummies! I did not let Sugar Plum have an squirty on our first call because I wanted him to earn it. Can you imagine how frustrated this sissy was???? Would you be?

The Sugar Plum Sissy Fairy Date Night

So tonight the Sugar Plum calls for our special date night. His wife was out of town and he had all of his pretty little things. I instructed him to dress in the items you see here in this post. He was sooooo nervous and a bit crazy from the days events. After he settled down and we shared some lighthearted banter and depth breathing I had him  stand in front of a full length mirror and look at himself. He then pulled the front of his panties down and tied up his pee pee and sugar plums. He had to also put ben-gay on them. Ouchie! Oh wait! There was the spanking! The naughty little bitch was 30 minutes late for our date!!!!!!!!!!!!!!!!!

hairbrushes and wooden spoon

So we had to get punishment out of the way first! With that big fat hairbrush we spanked that sissies ass 40 times until he was hot and sore! Bad sissy making Mistress wait!

Ok, then we went over to the bed to relax, feel the stockings and panties, get nice and hard, touch and pinch nipples until the sissy was very hard! Then up on your knees! We whacked the sugar plums with this small wooden spoon just to make sure the sissy knew who was in charge and that the stupid stick and plums were MINE! We then folded and fucked a pillow while the sissy watch me play with my pussy wishing he had a big enough penis to fuck me. He licked my pussy and imagined having a sweet pussy like mine. Too bad girlie, you don’t!

After almost 20 minutes of torture and the sissy screaming to squirt I made him stop and smack the plums again with the spoon. lol-  I know its evil but the bitch has to learn a lesson. Its mine., Its that simple. THEN finally we resumed but the only way the sissy could squirt was if he lapped it up cleaning his own mess! He did it! Therefore earning a new sissy name and allowed to cum again into his panties as long as he wears them all night long.

Do you think I was too hard on this sissy? What should we do with him next?



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2 Comments

raven On February 10, 2013 | Reply

Would love to see pic of him wearing the bra, panties, stockings, etc. No face need to be shown. i think the next step is for him to be fucked in the ass while on all fours. He needs to buy a dildo and suck it like a real cock , then, after any punishment you adminsiter to him, fuck himeslef with the dildo.

    Natalie On February 10, 2013 | Reply

    Perhaps we can make that happen

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