- Anything Goes -
Straight Male / 33
Trying To Help Out A Coworker
So I work with this guy, it's just us two in a shack at night for our shift. He's in his forties and hasn't had a girlfriend since grade school.
He claims it's by choice and he has no use for women. But everyone knows he couldn't get a girl if he wanted to. He has zero social skills and definitely isn't pleasant to look at. He's also an upright douche to work with.
I have this app, you add photos and it turns it into color by numbers pixel art. I got him hooked on it too, though he just uses the in app images provided.
I have an attractive female friend who sends me pics of her that she wants me to color on the app. I do it in stages and send her screenshots as they go, I'm not sure what she uses them for. For example if she's wearing a dress, I'll just color the dress and send a screenshot like that and it can look like something out of Sin City. It's cool looking. But she does send them in various states of dress-undress.
Now for the goods.
He usually shows me what he's working on, so I decided to show him a safe-for-work pic of my friend I was working on.
He thought it was really cool, and started asking a bunch of questions. I kept my answers vague and just said she sends them to me because she likes how I color them.
Well, she sent me a set of pics to do one night.
In the first, she had some pretty deep cleavage going on but I figured it was safe enough to show him when he asked.
He got more excited than I bargained for, so I showed him each stage of color I did and then the finished version as well.
The second pic, she had her shirt pulled aside and you could just barely see some of her areola. I transferred it to the app, and as long as I didn't color her areola you couldn't really tell it was showing. But you COULD tell a lot of her chest was exposed.
When he asked, I hesitated but showed him. His excitement escalated.
At this point a thought crossed my mind.
He's literally a 40 year old virgin and a lot of times me and the other workers joke about getting him a prostitute to see if it would chill him out.
I could tease him with these, but how far do I go? Would he turn me in at work?
I didn't show him the finished version but I showed him the first few stages of color, so he wouldn't notice the areola.
The next in her set, her shirt was pulled to both sides, showing both areola. I handled this the same way.
I thought he'd cream his pants from excitement.
The next pic, one of her breasts was fully exposed, so I didn't show him that.
I found an older pic and made up a story about telling her she needs a brighter background and that she sent me a pic of her in a towel in her bathroom to troll me because of how bright the background was.
I did show him all of those stages.
He said: "I dare you to tell her to use different colored shower curtains in the background to add color.
He apparently thought this was a hilarious response.
I looked through the pics from that time and saw she had sent one where she had opened her towel but was standing sideways, showing bare skin from the knee to the jaw, but the towel covered anything technically NSFW. You could see some side-boob and the side of her ass and hip though.
I told him I sent his response and she responded with a troll pic back. I explained it's TECHNICALLY less revealing than a swimsuit so it was okay to show, and I did show it.
His excitement grew. He was happier than I'd ever seen him.
I asked if he had another response for her.
He said, "do themed shower curtains and dress to match," laughing as if he'd just made the best joke ever.
I looked back at the pics and smiled.
There was one where she dropped the towel and just covered her breasts with her hair.
I said "she sent another troll response, but it shows even more..."
He didn't really know what to say but he was clearly interested so I showed him.
I explained that the shower curtain had no theme so she was wearing nothing.
He freaked out and the biggest smile I'd ever seen crossed his face.
Our shift ended after that, and it left me torn. I won't see him for 5 days so I'm looking for advice here.
Do I play it safe and quit while I'm ahead?
Or...
Do I find an excuse to SEND him the pics he's seen because I bet he'd "use" them at home if he could.
Or....
Do I take it further and lead into nudes...
He claims it's by choice and he has no use for women. But everyone knows he couldn't get a girl if he wanted to. He has zero social skills and definitely isn't pleasant to look at. He's also an upright douche to work with.
I have this app, you add photos and it turns it into color by numbers pixel art. I got him hooked on it too, though he just uses the in app images provided.
I have an attractive female friend who sends me pics of her that she wants me to color on the app. I do it in stages and send her screenshots as they go, I'm not sure what she uses them for. For example if she's wearing a dress, I'll just color the dress and send a screenshot like that and it can look like something out of Sin City. It's cool looking. But she does send them in various states of dress-undress.
Now for the goods.
He usually shows me what he's working on, so I decided to show him a safe-for-work pic of my friend I was working on.
He thought it was really cool, and started asking a bunch of questions. I kept my answers vague and just said she sends them to me because she likes how I color them.
Well, she sent me a set of pics to do one night.
In the first, she had some pretty deep cleavage going on but I figured it was safe enough to show him when he asked.
He got more excited than I bargained for, so I showed him each stage of color I did and then the finished version as well.
The second pic, she had her shirt pulled aside and you could just barely see some of her areola. I transferred it to the app, and as long as I didn't color her areola you couldn't really tell it was showing. But you COULD tell a lot of her chest was exposed.
When he asked, I hesitated but showed him. His excitement escalated.
At this point a thought crossed my mind.
He's literally a 40 year old virgin and a lot of times me and the other workers joke about getting him a prostitute to see if it would chill him out.
I could tease him with these, but how far do I go? Would he turn me in at work?
I didn't show him the finished version but I showed him the first few stages of color, so he wouldn't notice the areola.
The next in her set, her shirt was pulled to both sides, showing both areola. I handled this the same way.
I thought he'd cream his pants from excitement.
The next pic, one of her breasts was fully exposed, so I didn't show him that.
I found an older pic and made up a story about telling her she needs a brighter background and that she sent me a pic of her in a towel in her bathroom to troll me because of how bright the background was.
I did show him all of those stages.
He said: "I dare you to tell her to use different colored shower curtains in the background to add color.
He apparently thought this was a hilarious response.
I looked through the pics from that time and saw she had sent one where she had opened her towel but was standing sideways, showing bare skin from the knee to the jaw, but the towel covered anything technically NSFW. You could see some side-boob and the side of her ass and hip though.
I told him I sent his response and she responded with a troll pic back. I explained it's TECHNICALLY less revealing than a swimsuit so it was okay to show, and I did show it.
His excitement grew. He was happier than I'd ever seen him.
I asked if he had another response for her.
He said, "do themed shower curtains and dress to match," laughing as if he'd just made the best joke ever.
I looked back at the pics and smiled.
There was one where she dropped the towel and just covered her breasts with her hair.
I said "she sent another troll response, but it shows even more..."
He didn't really know what to say but he was clearly interested so I showed him.
I explained that the shower curtain had no theme so she was wearing nothing.
He freaked out and the biggest smile I'd ever seen crossed his face.
Our shift ended after that, and it left me torn. I won't see him for 5 days so I'm looking for advice here.
Do I play it safe and quit while I'm ahead?
Or...
Do I find an excuse to SEND him the pics he's seen because I bet he'd "use" them at home if he could.
Or....
Do I take it further and lead into nudes...
# 73507 - by Behind_the_mask / September 15, 2024
