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It all started with a deep cut v-neck, back in 1984. In a lighter shade of blue than the rest of the suit. We still see that basic form in the Nightwing suit today, whether it is the variant with a lighter colour (generally blue) in a v-shape over the chest, shoulder and back or as a stylized bird.

The v-shape started to take the shape of a bird on the Nightwing suit in 1997, in The New Batman Adventures (a continuation of Batman The Animated Series). 

(If you know of any model or facts that I’ve missed, don’t hesitate to let me know so I can update!)

The original suit, fondly nicknamed “discowing”. When Dick took it on for the first time, he had an inner monologue about how the name and the costume are based on Batman and Superman but also his parents and Kory/Starfire. Tales of the Teen Titans # 44. By Marv Wolfman, art George Pérez, Dick Giordano and Mike DeCarlo. (July 1984)

This is from an interview with Marv Wolfman, on 13thdimension.com, about why Dick became Nightwing: 

It was fairly simple, actually. I got a call that (DC) really would like Robin back in Batman, and they wanted Robin to be younger. Again, because Batman really needed a partner. The nice thing was that Teen Titans—which I was still on at the time—was way outselling Batman and I really wanted Dick Grayson and I really loved the character. We had aged him, we had made him a real leader, we had done a whole bunch of things with him, and I didn’t want to give up Dick Grayson. And it suddenly struck me — I don’t even know what happened because it was unprecedented in comics — I said, “Why don’t I keep Dick Grayson and you create a new Robin and make that a big to-do in Batman … while we have Nightwing.

After eight years, the “discowing” suit was replaced by one with less light blue and more yellow, not unlike the original but without the collar and deep neckline. It also had a bat-like emblem on the belt. The uniform was (in-universe) designed by Mirage impersonating Starfire/Kory, who also cut Dick’s hair to go with the 90′s, over his mild protests. (It’s been a long time since I read NTT from this era, so I can’t remember if the yellow between the arms actually functioned as glider wings.) New Titans vol 1 # 88. Written by Marv Wolfman and Lein Wein, art Tom Grummett, Al Vey, Ian Akin and John Statema. (July 1992) 

This model didn’t last long – Dick scrapped it in September 1995, in the first issue of the first Nightwing (mini) series. His decision to leave the hero business lasted about ten minutes, I guess. Nightwing vol 1 # 1. By Dennis O’Neil, art Greg Land and Mike Sellers. (1995)

Dick’s third model, the black and electric blue “fingerstripe” suit was, in-universe, designed by Harold Allnut who lived in the Batcave and worked as Batman’s all round mechanic and technical guy. Dick would stick with this design until he became Batman in 2009. Nightwing vol 1 # 2. By Dennis O’Neil, art Greg Land and Mike Sellers. (1995)

The actual designer was Brian Stelfreeze, who made this model sheet.

He finds it rather funny when he first sets it up; he’s quite proud of the pun although Dick just rolls his eyes. But the title doesn’t really matter - what really matters is the contents.

In the beginning the folder contains, quite literally, dick pics. Specifically, dick pics from Dick.

When they first start fucking, they do a lot of sexting. Their schedules are busy and they live in different cities, and when Jason casually mentions that his favorite thing to do on an evening alone is to jack off while picturing Dick naked, Dick is very insistent that Jason needs some proper material.

That’s when the pictures start coming through.

Dick sends Jason an intimate photo probably once every three or four days when they’re apart, and it’s always something a little different. Sometimes it is a shot of his dick, hard and leaking which makes Jason’s mouth water, or sometimes it’s a shot of his ass which makes Jason salivate just as much.

Sometimes it’s a full body shot - usually with Dick naked, but sometimes in lingerie, and Jason has to admit he’s impressed by the amount of creative thought that goes into each photo.

Jason reciprocates, of course. He is a gentleman. And a gentleman shares a picture of his own dick when his boyfriend sends him sexy photos.

And that’s when Jason realises that he thinks of Dick as his boyfriend.

Jason knows that Dick is his boyfriend when his Dickpics folder starts to contain more sentimental photos than sexy photos.

Photos of Dick fully clothed but looking happy doing mundane tasks. Photos of Dick just smiling goofily at the camera. Photos that Jason doesn’t really jack himself off to, but photos he likes to look at for long periods of time nonetheless.