I should have known that Jess had some sort of weird question for me when she asked me over to an isolated corner of the office, but just outright asking that took some courage. "You... want to know if I'm gay?" I repeat back to her, not quite sure if I misunderstood her.

With a bright smile on her face, she nods. "Yeah! I mean, you get asked out by girls around the office all the time, and you never accept any of them. Plus, you've got that look that totally sets off my gaydar! You have to be gay!" she replies, full of confidence.

A dejected sigh escapes my lips. I know she's not the most socially educated type, but that is just downright rude. "You know, I should be gravely insulted by this, and the only reason I'm not is that you're correct. So what of it?" I ask her, worried about just what will come next.

Eagerly, she starts digging in her pocket, then pulls out her phone and shows it to me. "This is Damian, my brother. And I want you to try and seduce him, because my brother going gay would be the hottest thing in the world," she says, unaware of just how crass what she saying is.

But it's not like I can just shut her down outright, that's not conducive to a good workplace climate, so I give that picture of him a look. And honestly... he doesn't look half bad. Kinda cute. Maybe I should give this a shot after all. "Well... I guess I can try. So what's the plan here?" I ask, assuming that she probably has everything planned out already. Sure enough, she has.

"Oh, it's easy. Since Damian is out of shape, I got him to sign up for the gym you go to, and he'll go there tonight. Just keep a look out for him, snap him up, work your charm and get him to invite you home. I have a bunch of hidden cameras set up to record you. Then, all you have to do is get him into bed..." she explains, way too eager, given what she's telling me to do. How does she know what gym I go to again? And hidden cameras? Oh, whatever. I can tell that letting her down will lead to disaster, so I'll just have to go for it. Maybe it'll work out.

So I tell her I'll try, the day passes quickly, and soon enough I find myself at the gym, waiting for Damian to show up. After a few minutes, I spot him at one of the exercise bikes, huffing and puffing as he struggles to pedal. Seems like he doesn't quite know how to work the equipment, which should give me a pretty quick in with him. Walking up to him, I give him a simple smile and a "Hey there, you're new here, aren't you?", which gets us talking pretty quick. He seems really happy when I show him how to use the bike, and as I chat with him, I get the impression that he couldn't be more different from his sister. She's brash and has no concept of just what is appropriate to say in polite conversation, whereas he seems really shy and super aware of his social awkwardness, which leads to him being really polite and grateful. He's so much more enjoyable to talk to, and he's nice to look at, too. Sure, he's kind of a string bean and could use some exercise, but that can be worked on. I doubt he's ever gotten used to the idea of someone attractive just chatting him up, so he gets flustered in a cute way.

I spend the next hour together with him, helping him out with exercise equipment and generally showing him the ropes, which he is really thankful for. Eventually, my thoughts drift to how I'm going to get him to invite me to his place, like Jess told me to do, but I get an idea. "Say, Damian, do you have problems with your back or shoulders hurting at times?" I ask, knowing that he's a programmer and therefore almost certainly has some trouble with his joints. Sure enough, he nods. "Well, I'm something of an amateur masseuse, and my friends tell me that I can clear knots in your back up with ease. So if you want, I could come over after our workout and give you a massage. I promise you'll really enjoy it," I explain.

Damian's expression goes through several different moods, but eventually settles on a soft smile. "Yeah... I think I'd enjoy that," he replies meekly. Bingo, I've got him to invite me over. Everything's going great so far, and I get the feeling it's going to be really fun massaging this awkward nerd. I can already imagine the noises I'll get out of him...

After some more reps, we finish up our workout and get ready to head out. Since Damian's place is very close to the gym, the two of us just walk over there and head inside. Damian barely manages to cross the living room floor before collapsing onto the couch. "Oh, you're gonna be feeling it in the morning for sure, but that's just a sign you've pushed your body and it's trying to get used to that, so it's a good thing. But I think you can really use a massage now. So, you wanna go for it?" I ask him, stepping up behind him and gently touching his shoulders.

He looks up behind himself to make eye contact, and after a short silence, he replies with a simple "Yeah," and nods.

"Well, we should probably do this somewhere where you can lie down, so can you make it to your bedroom? Or should I carry you?" I then ask with a confident smile, trying to put him at ease.

Again, there's a pause, and a blush rises to his cheeks. "Um... would you really carry me?" he asks in return, an odd sort of hopefulness in his voice.

"Sure I would! C'mere," I reply, stepping in front of him and picking him up into a bridal style carry, which has him blushing even more and looking away from me. He's just so adorable and lovable right now, I can't wait to make him happy with a massage. I let him direct me to his bedroom, and when we arrive there, I lay him down on his stomach on the bed. "Now, this would go even better without your tank top on. Would you mind if I took it off?" I ask, hoping he's fine with it. And thankfully, he shakes his head, letting me slowly pull off his tank top. With his shirtless back revealed to me, he looks almost frail, like I could just snap him in half, so I'll have to be careful. And knowing that Jess is watching my every move through a hidden camera somewhere and probably salivating right now, I place my hands onto his back.