I'm a teamlead for an IT-Provider, i manage 7 employees in my department.

We all have a very close relationship, it's cliche to say, but we are like a family, as we often spent some time together after work, visit each others birthday parties and talk and support each other in private matters too.

Most important for this story is my youngest and most talented employee, Josh.

He's 25, Neurodivergent (aspergers), and a little genuis, who can work as much as the other 6 combined when he's excited about a challenge. He has a hobby of collecting anime figurines, some of which can be rather NSFW. He's allowed to have those at work too. He sometimes, "jokingly" refers to me as mom because i guess he sees me as a bit of a motherly figure.

Two things happened end of last year.

For one, he became a bit depressed and for another, he had asked me for a raise.

As for the former, i know from many conversation that he struggles a lot in social settings, that he has few friends, and never had a girlfriend in any way. I know he eventually managed to ask a girl out he had a crush on but was rejected rather hurtfully.

As for the raise, he had told me he was looking to buy a very expensive anime figurine that he wanted, and that he needed the money for it sooner rather than later for a preorder. And personally speaking, he most certainly deserved the raise too. Unfortunately, corporate did not allow me to give him one for the time being due to cost saving policies.

So in between some conversations, i asked him to show me the figurine he wanted. As i was planning to buy it myself as a christmas gift to him.

So to my surprise, i was confronted by a picture of a character looking a lot like myself in a very lewd pose and dress. I couldn't help but blushing and asked him why he wanted that one specifically, and he told me he was a big fan of this character precisely because she reminds him a lot of me.

Even though saying that, given the nature of the figurine, felt quite inappropiate, i also thought it rather heartwarming to see his affection for me, or a stand in for me. He told me that he likes my motherly attitude so much because his own mother never cared about him for "being different".

Anyways, so for christmas i surprised him with this figurine after our xmas party at work.

He quickly unboxed it and placed it on his desk and we chatted a bit.

We talked again about hos this figurine reminded him of me, and given the nature, i asked him if that meant he was also thinking about me in such clothes as her. He became very red and embarassed, probably realizing that i made this very obvious connection, but eventually he admitted that he was thinking about me like this, and apologized almost teary eyed.

I told him that that's okay, that such feelings a normal and nothing to be ashamed of.
I tried my best to make him feel alright about it. He opened up to me and told me he was almost always thinking about me when he was masturbating.

And so, i asked him if he would want to masturbate to me. He was extremely embarassed again and rejected the thought outright, but i told him it was okay. After a little back and forth, he eventually chose to trust me. He unzipped his pants very slowly as tho he still wasn't sure if i was being serious, but eventually, he started to enjoy himself slowly, until he came.

After he was done, i kissed his forehead, called him a good boy, as i had the feeling its the kinda thing he would like, and we both went home for the day.

Eventually he approached me later on about doing this again. And i allowed it. It became a regular thing, and eventually, i took his virginity.