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Description
(You know instead of first contact. Fine. I'll stop with the bad puns now.)

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It was a warm day, comfortable outside enough that we did not feel bad walking around in our hero costumes. I felt her weight shift onto my arm. Her fingers played with my hand as we bounced off each other; it was so wonderful that she felt comfortable enough to play with me like this. It still felt like something was missing though and unless I'm reading things wrong she might be ready for more. "Hey Iron," All Might began. She looked up at him as she made a noise. He stepped in front of her, took her hand in his and tried interlacing a few fingers. "I know you aren't entire comfortable or used to being hugged a lot or just generally being touched a lot but I am. And if want to please feel free to ..um.. reach out to me," All Might tried to offer as his words started failing him. He felt her squeeze his hand. His attention returned to her; her expression was not as playful as a moment ago but was still softer than he had seen in a long time. "I just wanted to let you know, you are in control."
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All Might and Iron Maiden have been doing the hugging 'contest' for a while and he had been starting to stay over longer so he wanted to encourage her to progress at her speed concerning physical contact. As well as let her know it was all right to touch more than his hand. ^u^ While Iron does like to hug she never had anyone who was willing to hug such a heavy weight for so long. Vampi is the only other person who does more than greetings hugs or pat on the back interactions. (Oh BTW Krissy totally started this train of thought as well as the fanfic because she brought up the kiss; causing my brain to think of everything they did before hand to work up to it.)

Try, Try Again‘Three times. Three times!’ All Might’s brain screams internally. He tried to kiss Grizel three separate times and for some reason each time he failed. Each moment was perfectly fine; some would say they would be fitting of first kiss stories. It was their first official date at sunset, they were lying on the floor together after a patrol when he found out one of her hero secrets and she looked so radiant glistening next to him, and he had wiped a spot of food off her cheek while on a walk in the park. For some reason though every time he felt like his chest or head was about to explode when he just inches away from her lips. Every time his face ended up redder than any costume he has ever worn, his head ends up buried on her shoulder in a tight embrace instead, and he feels more flustered than the first time he tried to hold her hand.
Now is another chance. They had just gotten into bed together. They are having a nice little talk about how things went that day. She
Toshinori Yagi aka All Might from My Hero Academia/ Boku No Academia by Kōhei Horikoshi
Iron Maiden aka Grizel Siller by lady-blackwings
Tools used: Clip Studio Paint and Wacom Tablet

Description
(You know instead of first contact. Fine. I'll stop with the bad puns now.)

----
It was a warm day, comfortable outside enough that we did not feel bad walking around in our hero costumes. I felt her weight shift onto my arm. Her fingers played with my hand as we bounced off each other; it was so wonderful that she felt comfortable enough to play with me like this. It still felt like something was missing though and unless I'm reading things wrong she might be ready for more. "Hey Iron," All Might began. She looked up at him as she made a noise. He stepped in front of her, took her hand in his and tried interlacing a few fingers. "I know you aren't entire comfortable or used to being hugged a lot or just generally being touched a lot but I am. And if want to please feel free to ..um.. reach out to me," All Might tried to offer as his words started failing him. He felt her squeeze his hand. His attention returned to her; her expression was not as playful as a moment ago but was still softer than he had seen in a long time. "I just wanted to let you know, you are in control."
-----

All Might and Iron Maiden have been doing the hugging 'contest' for a while and he had been starting to stay over longer so he wanted to encourage her to progress at her speed concerning physical contact. As well as let her know it was all right to touch more than his hand. ^u^ While Iron does like to hug she never had anyone who was willing to hug such a heavy weight for so long. Vampi is the only other person who does more than greetings hugs or pat on the back interactions. (Oh BTW Krissy totally started this train of thought as well as the fanfic because she brought up the kiss; causing my brain to think of everything they did before hand to work up to it.)

Try, Try Again‘Three times. Three times!’ All Might’s brain screams internally. He tried to kiss Grizel three separate times and for some reason each time he failed. Each moment was perfectly fine; some would say they would be fitting of first kiss stories. It was their first official date at sunset, they were lying on the floor together after a patrol when he found out one of her hero secrets and she looked so radiant glistening next to him, and he had wiped a spot of food off her cheek while on a walk in the park. For some reason though every time he felt like his chest or head was about to explode when he just inches away from her lips. Every time his face ended up redder than any costume he has ever worn, his head ends up buried on her shoulder in a tight embrace instead, and he feels more flustered than the first time he tried to hold her hand.
Now is another chance. They had just gotten into bed together. They are having a nice little talk about how things went that day. She
Toshinori Yagi aka All Might from My Hero Academia/ Boku No Academia by Kōhei Horikoshi
Iron Maiden aka Grizel Siller by lady-blackwings
Tools used: Clip Studio Paint and Wacom Tablet