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Friday, July 03, 2020

Remembrance: Tina

I’m in a different part of town, but still familiar with the area.  I look back and make sure my car is locked.  It’s the summer after graduation, and my parents are both at work for the day.  This is as safe as I'm going to be.

I see a couple walking towards me up ahead.  My heart starts racing.  I take a deep breath to calm my active mind.  I glance down at my white tank top with spaghetti straps and tiny pink shorts.  

“There’s no way a boy would wear this,” I think.  I remind myself that I CAN pass in public with my naturally small frame and long hair, currently held in back by a clip.  

I force myself to remain calm as the couple passes me.  They talk to each other without giving me a glance.  

I breathe a sigh of relief!  I was wondering if I was crazy to go out like this during the day.  First test - passed!

Then it happens.  I feel a hand on my butt.  My heart skips a beat as I nearly jump out of my skin!  I look over to see a middle-aged woman attached to the hand.

mature woman grabs sissy's ass

“I thought that was you, Johnny*,” she says casually.  “I like those shorts on you.  They’re very cute!”

“Oh, hi Mrs. Pendleton.  You scared me!”  Mrs. Pendleton was the mother of one of my classmates, Sam.  I feel my face begin to flush, and wish I could magically go back home.

She laughs.  “Yeah, you could say I’m a bit surprised too.  Then again, you never know what you’ll see on your lunch break, huh?”  She looks at me thoughtfully as I scramble for an excuse.

“You know...I was just...I’m doing an experiment for...”

“Oh, honey, don’t even bother.  It’s clear to both of us what’s going on here, isn’t it?  Don’t worry, your secret’s safe with me.  I promise not to say anything to your folks.”

“Thank you, Mrs. Pendleton,” is all I can manage while staring at my feet.

“Oh, please, call me Tina.  You know, Johnny, you really should come over swimming at our house sometime this summer before you all go off to college.  I know I’d enjoy having you over, and I’m pretty sure Sam would too.”

I can’t believe my ears!  Mrs. Pendleton just caught me cross-dressing in public, and now she’s inviting me over to hang out at her house?!  What's going on here?!

“Y-yeah, sure.  I’d like that,” I stammer.  My nerves are still frazzled. “Well, I’d better let you get back to work, Mrs....I mean...Tina.  It was nice to see you.”

“Nice to see you too...Joanna?” she asks with a smile.  “Seriously, don’t be a stranger this summer,” she says with a wave, before heading back the way she came.

I immediately went back to my car and drove home as fast as possible.  Tina kept true to her word about being quiet.  I never did make it over to the Pendleton’s that summer.   But every now and then I wonder what it would’ve been like!

* All names have been changed to protect the privacy of individuals

Friday, June 19, 2020

Free will?

She suggested I grow my hair out.
She dared me to try on her panties.
She taught me how to fasten a bra.
She showed me how to apply makeup.
She convinced me to go to the party.
She helped me to my knees.
She told me I was next.
I chose to take him in my mouth.

sissy blowjob

Tuesday, June 16, 2020

Hotel rendezvous


"Hey babe!  How's your book?" she asks me.

"Pretty good...sorry I lost track of time.  I have one page left, then I'll swim some more."

"Glad you like it.  Say, I was just chatting with those guys behind me.  I think I made them uncomfortable, because I called them out for staring at my chest.  Pretty funny, huh?"

"Yeah, hilarious," I reply sarcastically, still not thrilled she wore her bikini instead of her more modest one-piece.  It meant she was feeling frisky and seeking attention from men.

"Then I laughed and told them I wasn't offended.  I asked if they thought I was attractive, and told them to rate me on a scale from one-to-ten.  When they answered, I asked if they'd fuck me.  You should've seen their faces!"

"Are you serious?!  They said yes, right?"

"Of course, silly!" she replies.  "Then I said I'd really let them, only if I could watch my husband suck them off first.  That's when they hesitated.  But once I pointed you out over here with your bikini and smooth body they agreed."

"So now what?" I ask, glancing in their direction.

"I gave them my hotel key and told them to meet us in 15 minutes.  Gather your stuff, we're heading to the room!"
hotwife in bikini