Aunt Diana Ch. 1

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"It's Okay Aunt Diana," he said, obviously nervous.

"So good that I think you deserve a reward." Diana reached down and pulled Aiden's blue panties down. He gasped as his hard cock bounced right up in front of him.

"You've just been hard all day, haven't you? Dirty little pervert." Diana giggled, her cheek against Aiden's. "That's how I know I was right. You like being my little girl, my sissy. You need some release, though. Touch yourself for me, touch yourself for your godmother. Here." Diana dipped a hand into the tub and dribbled some of the warm soapy water onto Aiden's throbbing erection. "Now do it."

Aiden was breathing hard. He hesitantly reached out grabbed himself.

"Good boy," Diana said. She was close enough that she knew Aiden must feel her breath on his cheek. She began to whisper into his ear and rub his shoulders as he jerked himself, slowly at first and then more rapidly.

"Yes, Sweetheart. Very good. You're my good little Sissy,aren't you? You love wearing my panties and my bras and my high heels. And cleaning for me and doing whatever I say. I love those things, too. I love seeing you all dressed up and bossing you around. I can't wait get on the phone tonight and tell your mother all about what we've been doing, all about her sissy little son. Yes, there you go, keep pumping, baby. Maybe she'll come over, too, and we can both boss you around. Then you can be my sissy and your mommy's little sissy. I know she always wanted a daughter. Mmmm I can tell you like that. It was her panties you were stealing, little panty sissy boy. I'm your godmother but she's your mother after all, I can't compete. She loves you, you know. That's why she sent you here. Oh, yes. If you're lucky we can all dress up, the three of us, me and you and your mother. Would that be nice? All of us in lacy thongs and matching bras. I'd like that, yes I would. Cum for me, Aidy, my little sissy girl. Cum for your godmother, there you go. Cum for Mommy."

Aiden moaned as he came, his whole body shaking, jizzum all over the linoleum floor. Diana laughed and kissed him on the cheek. "Look at this mess, Sweetie! You'll have to clean this up, then you can jump in and use my bathwater. It should still be pretty warm. When you're finished I'll give you another nightgown you can wear." She kissed him on the cheek again. "And since now I know you're masturbator you'll have to stay in my bed with me tonight. Can't have you doing this on your own, no, your mother would not approve. Don't worry, though, it will be fun. We can have great girl talk in bed."

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33 Comments
wiggle1wiggle18 months ago

I want some more chapters YEAH!!

Big_Mike_1966Big_Mike_19669 months ago

I want to hear more please!

gaiperegaipereabout 2 years ago

I hope to Chapter 2 soon! Love the first chapter!!

AnonymousAnonymousover 2 years ago

I am so disappointed that there isn’t another chapter in this story. Back when I was a teen and wore my mother’s clothing I dreamed of getting caught. I can picture myself in Aiden’s high heels. I would love to have had an Aunt Diane.

NitpicNitpicalmost 3 years ago
How

How does she find a pair of shoes to fit him,let alone with four inch heels?.

Fuzzy_KbearFuzzy_Kbearabout 3 years ago

I'm Sorry...

I didn't even make it halfway down page one. He's 19, which means he should be out of high school, and even if he's not, he has more choices, than comply or military school. I know it's a story and all but realism has too count for something here. too many of these types of stories have characters that just except their "fate". But, If he's is confused, worried, ashamed, etc. He would fight back, it's human nature. I understand that would take longer and all, but at least it would be more realistic. 1 dimensional characters, like this lack the depth and realism to allow the readers to truly get into the story.

AnonymousAnonymousalmost 4 years ago
Keep writing. love the cross dressing in front of auntie.

Aunt Diana is very good working with him. She needs to switch him to satin bra and panties and a full silk slip. A dress with his heels and a nice shoulder length wig would add to his excitement. Love my satin stuff, and my nice 40C bra. Feeling the straps over my shoulders and tight around my chest gives me a thrill and my own panties for stuffing the bra. Putting a girls shirt over the bra is heavenly.

AnonymousAnonymousalmost 6 years ago
Oh My How Delicious !!!

I've just read two of your stories and so hoped to find more maybe chapter's 2 or 3 , I do so hope that you will find the time to write some more of the scrumptious tales that you have started . Thank You for your time and craft .

Hugs

Kathryn... xxx

FaggotFredCUMPIGFaggotFredCUMPIGover 7 years ago
ohh boy

i wish the aunt of mine who introduced me to sex at a very early age had used me like this. of course i didnt know i was a sissy back then. of course the only thing i would be allowed to use to clean up my mess, would be my tongue and mouth. the way i clean up my messes now, on all fours, face in the puddle and my ass in the air!!

AnonymousAnonymousover 7 years ago
loved it

very very well written and incredibly exciting to a sissy boy like me

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