The Training of Sissy Paula Ch. 5

After the fuckings I had gotten from Max my asshole was so stretched, I had to wear diapers all the time.
Mistress Carolyn used this to her advantage.
She had a few men that liked sissy babies.
The men would bring me all sorts of little sissy clothes.
Dress me up and have me nurse their cocks as if they were bottles of milk.
One day a new man showed up, he wanted to do some role-playing. He gave me a made up report card and had me dress in an outfit for a toddler.
Frilly pink panties, over my diaper, and pink rubber panties, a pink dress with puffy sleeves and white lace all over, pink buster brown shoes and little bootie socks which were pink with lace.
I went up to him with the report card.
Oh my sissy Paula, what will I do with you?
F - in every class.
Honey bring me the big paddle for our little sissy.
Yes dear.
Mistress Carolyn was playing the part as honey.
Here you go dear.
Down with them panties sissy.
Yes sir.
Call me daddy, you naughty little sissy.
Yes daddy.
I think 100 licks for each f- should get you acting right in school.
Let’s see 6 classes all f-.
Oh I just thought of another punishment to go along with the spanking.
Carolyn please get me a big bowl of ice cubes.
You got it dear.
O.K. sissy I am going to insert all the ice in your asshole, and by the time I am done spanking you it should be melted.
Get the penis gag Carolyn.
Here you go.
Remember this sissy, I used it on you the first night me met.
Now look at you, your a pro at taking it all down your throat.
The panties came down, along with the diaper, and plastic panties.
He slowly inserted one cube at a time having me count out loud and thanking him for the attention he gave my asshole.
The ice was packed into my asshole.
Bet that’s cold.
Yes daddy it is.
Well after this paddle starts you want be thinking about that asshole full of ice.
He tied my ankles to the stool he was sitting on, then he tied my wrist to the hook in the floor.
My ass was high in the air as I lay over his lap.
He didn’t hit hard at all, but after 600 licks it did sting some.
He put my diaper back on me, then he told me to go make Carolyn feel good with my tongue.
He rested for a while as i licked Mistress Carolyn to orgasm. My tongue got a long work out as I licked and sucked Mistresses pussy to 3 climaxes.
He slipped his hand into my diaper and started fingering my butt hole.

The session was not all that bad, and he even made me cum in the diaper.

He worked his hand up my anal passage with ease.
Soon after he managed to move around so that his cock was at my mouth.
I sucked on the head of his cock for about 5 minutes, then I began licking up and down the base to his balls.
Umm sissy paula that feels wonderful.
I didn’t say anything,my mouth continued to pleasure his hard rod, bringing him nearer to his goal of feeling my mouth with his sticky cum.
He thrust all the way down my throat and started humping my face as if he were fucking a wet pussy.
His cum went in my mouth, and on my face.
Mistress came over and gave me a big kiss on the lips.
She and I kissed for about 5 minutes, exchanging the cum back and fourth between us.
Daddy went to get something from his car.

It was the most beautiful dress I ever saw.
Pink and frilly lots of petticoats, and puffy sleeves. He also had matching shoes for the outfit.
O.K. sissy were going out to dinner tonight.
Yes daddy was all I said, I knew there was no need in protesting the idea he had in mind.

I put on the outfit.
Mistress Carolyn helped me with makeup.

The diaper and plastic panties still on me also.

Once we sat down 3 friends of his took a seat.
Paula your meal is under the table dear.
O.K. daddy.
I slipped under the table and unzipped the first man i got to, pulled out his cock and began sucking him. He started peeing before I knew what was going on, I gulped and gulped to swallow it all, Didn’t want to smell like a toilet.
He pushed me away.
I had an idea that i would be drinking all their piss.
I unzipped the next mans pants and soon he was filling my mouth with pee as well. When I got to Mistress Carolyn she told me to go to the restroom.

I was nervous as I went to the restroom, seemed like all eyes were on me.

Paula you will put this sign on once you get in the men's restroom and kneel in the stall and wait for your first golden shower.
For now thought I have to piss also, and your mouth is the toilet tonight.
By the time we get home that diaper should be full.
After drinking her pee, I went to the men’s room and put the sign on.

It read :
sissy paula needs a bath and a snack.
Piss on her and cum in her mouth.

Daddy came in and put a hose down my diaper and ran it over to the urinal, he put a funnel on the hose and hooked it to the urinal.

Now don’t let know one get any pee in that diaper sissy.
He laughed as he went out of the rest room.

Soon a man came in and started peeing on me.
He pressed his cock to my lips and pushed all eight inches down my throat.
Umm I have not cum in about a week.
He gave me the biggest load of cum I had ever had.

Well this went on for about 4 hours.
I walked out of the toilet dripping wet, with a soggy diaper.
I had to ride in the trunk.
That was a wild experience I will never forget.