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Description:

Horsey is too cool for feelings.
safe1974609 artist:stoic5605 rainbow dash259681 oc838198 oc:anon13070 human204292 pegasus408142 pony1327013 blushing239231 cute236817 dashabetes10992 dialogue80501 embarrassed13635 female1606214 holding hooves2084 human on pony hoof holding85 mare619836 raised hoof60012 shaking1746 shipping230132 simple background503248 spread wings75680 talking8612 tsunderainbow488 tsundere3263 white background130765 wings175774 wobbling138

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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.