8 XXX : and dresses

Got a cute denim dress (sissy)

imgur.com category @deerbutt

I did something I don't normally do. I dressed up in my mommy's clothes. Might pursue this a bit further.

imgur.com category @diapers182

Princess in her pink polka dot dress. [OC]

imgur.com category @Mr_Clemens

Here is me in my black dress! Enjoy

imgur.com category @DiaperHawk

Forced into a dress over the weekend. Eep

imgur.com category @metzgerite

I dressed up like a little princess today

imgur.com category @JMstories

Here's my first attempt at an adult toddler dress (with ruffles!)

imgur.com category @lizab-FA

Little Pink Dress!

imgur.com category @DiaperHawk

Baby Mint Dress w/ SuPeR PettiCoat!

imgur.com category @DiaperHawk

Red dress

imgur.com category @slatestorm

the "well" dressed girl on her bike

imgur.com category @[deleted]

Well-dressed.

imgur.com category @devilbunnies

Black dress rider

imgur.com category @unicycleoptic

Doll dress in shades

imgur.com category @unicycleoptic

red bra, red dress, damn oh man she looks her best

imgur.com category @[deleted]

Pull up dress

imgur.com category @rulebot

Mom and the groceries

imgur.com category @wuxu

Mommy started to notice that her lingerie had smears of cum inside them. It made her so wet she wore them like that to bed and let me sleep beside her.

imgur.com category @weiner__dog

My mom is 40 and still wearing bikinis, not that I'm complaining

imgur.com category @somerandomer

Mom finally found a bra that fits comfortably and is excited to show it off

imgur.com category @wuxu

I got home and found mom waiting for me like this... lets be serious, you would have made the same choices

imgur.com category @somerandomer

I would always point to things on the bottom shelves and tell mom "I'd bet you'd like this"

imgur.com category @fappaccountt

Mom said she needed me to get the next size up in the shirt she was trying on. I asked why and she sent me this: "See? It's too small, I can't even get it all the way down!"

imgur.com category @ohmyunf

Netflix and mom

imgur.com category @wuxu

Mom is embarrassed because her skirt accidentally got caught on her chair and revealed a bit of her leg

imgur.com category @wuxu

Helping mom with her computer and she doesn't realize that you can see down her top

imgur.com category @wuxu

Mom's top button accidentally pops open and she doesn't realize it

imgur.com category @wuxu

Mom asked me if tan lines are in this year. I asked her what kind and she gladly showed me.

imgur.com category @ohmyunf

After driving mom to the fifth clothing store in a row I say I'm bored of shopping. Mom decides to give me a little bribe. "You can only look at them for five seconds" Mom says. "And then you have to drive me to another mall. Deal?"

imgur.com category @wuxu

Mom and the mouse in my apartment: A story in 6 pictures

imgur.com category @wuxu

Mom is drunk and walks into the wrong bedroom

imgur.com category @wuxu

I think it was this exact moment me and mom knew it would be more than just harmless flirting

imgur.com category @somerandomer

Mom calls me into the department store changing room to ask my opinion on a pair of jeans and tshirt. "Why do you keep looking at the tshirt," she asks. "Does the colour not suit me?"

imgur.com category @wuxu

Mom lost a bet with me and has to pose in her underwear outside. "I stand in front of the window but not outside!" Mom says. "I can't believe I'm doing this! Don't tell anyone!"

imgur.com category @wuxu

Even though it was meant to be my parents weekend away, me and mom made the best of the motel.

imgur.com category @somerandomer

I went downstairs in the middle of the night for a snack and Mom had just gotten back from the bars with a young new "friend"

imgur.com category @fappaccountt

Mom agreed to show me her wedding outfit, and I loved every second of it

imgur.com category @somerandomer

2 moms in robes and socks (x-post /r/TheSockDrawer)

imgur.com category @MmmMmmPorn

Mom was complaining of the poor support her new bra gave her. "Take a photo of it and I will personally send it to the company," I advise her.

imgur.com category @wuxu

Mommy knows you had a long day. Come lay down and suck mommy's milky nipples.

imgur.com category @weiner__dog

Mom and I relaxing on a secluded beach during holiday

imgur.com category @fappaccountt

Mom agreed that we could share the jacuzzi to wash the chlorine off after the family swim. I pulled out a camera and she laughed before saying "No more pictures!"

imgur.com category @ohmyunf

Mom asked if I want to join her for a swim or if I want to just sit back and enjoy the view

imgur.com category @[deleted]

Mom didn't expect me to be up so early but she said it was okay and that she still wanted a hug, anyway.

imgur.com category @ohmyunf

Mom spilled wine all over her clothing and quickly removed it. I stopped by for my weekly visit at that precise moment.

imgur.com category @wuxu

It was almost like mom was enjoying me looking at her, and was encouraging it

imgur.com category @somerandomer

Mom keeps a couple of spare twenties down her bra, and she always gives me one when I come over. "Now don't look!" she says.

imgur.com category @wuxu

The driver's door is jammed and I have to climb over mom to get to my seat

imgur.com category @wuxu

Bought a new fan for my room and mom is always using it to cool off

imgur.com category @wuxu

Mom is a little tipsy and forgets to change out of her swimsuit after a dip in the pool

imgur.com category @wuxu