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Description:

Horsey is too cool for feelings.
safe1971851 artist:stoic5605 rainbow dash259364 oc836746 oc:anon13059 human202851 pegasus406786 pony1323737 blushing238720 cute236284 dashabetes10962 dialogue80195 embarrassed13604 female1603565 holding hooves2081 human on pony hoof holding85 mare618478 raised hoof59860 shaking1742 shipping229782 simple background501449 spread wings75452 talking8583 tsunderainbow487 tsundere3253 white background130295 wings175140 wobbling136

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Background Pony #A895
She’s afraid of Anon embarrassing Her.
 
anon lets go of Dashie’s Hand
 
Why’d you stop holding my hoof?
 
You just told me too?
 
Rainbow Dash cries
Background Pony #7C3B
The style reminds me of mcsadat, but I can’t find a proper source to be sure. Desuarchive’s oldest post is from April 2014, but the filename (1393474880317.png) suggests that it was previously posted on February 2014, maybe on a different imageboard.
Background Pony #A61A
Anon just doesn’t know how lewd that act is considered to be in pony society.