When We Role Play… (27)

Wolves and Hybrids….

Your boss invites you to a sports retreat with him and his son.
Your boss goes to a late night dinner on “business” and leaves you behind with his son.
You leave the room and when you come back…
…you see this in your bed…

He happens to be 16 and is trying to have you fuck him before his father gets back.
He has been desperately trying to get that dick.
So, he decided to play hard ball. 

WHAT HAPPENS NEXT?

25 thoughts on “When We Role Play… (27)

  1. Illegal. That’s a no go for me. But I’m with Man… Jamari, you’re the perfect age for me. But as a Virgo I’m competitive yet pleasing by nature, you couldn’t turn me out. Might be fun to try tho. 😉

  2. Listen to Old Head. Never mix business and sex. Repeat. Never

    Besides dude is too young.

    If I came in and that ass was up I would have had told him to put his clothes back on (while I watched of course), had a heart to heart talk with him explaining why it wouldn’t happened, and gotten the fuck out quick, fast and in a hurry.

    Immanuel
    http://www.dlconfessionssequel.com

  3. Random and Ramrod are on point. Mixing business with pleasure is dangerous, just like doing it with neighbors. Both are NO-NOs. You would definitely be setting yourself up for blackmail and to be blackballed in your career by your boss after he would fire you; and, depending on his son’s age, possibly doing something extra legal to you. Also, the son could be 25 or 35 and the boss could know he was gay. As the bosses son, he would still be off limits. However, to be honest, with that last scenario, I’d could succumb. It’s in a wolf’s nature to smash ass.

    Something similar happened to me. A colleague’s lover made a serious pass at me when my colleague was out of town. Before I had learned that this person was my colleague’s lover, I had noticed him around and wanted to hit it and he probably sensed that. But, when we were introduced by my collleague, I said to myself, “Whew! Saved by the bell”! My response to the lover when he approached me was very polite but firm. I told him I would not be able to live with myself considering my longstanding friendship with my colleague, were we to do something. He accepted that but still puts out feelers, and I always parry them by playing dumb. By the way, I would never tell my colleague about this.

    1. Sounds like your colleague’s lover wasn’t stupid. He knew you wanted to smash, so he wasn’t gonna waste any time making a pass at you. I think that’s it’s weird how some people pick up vibes and others don’t.

      1. I agree; it’s an awesome gift. I think — i’m generalizing here — those of us “in the life” might be better at clocking because we early on develop the skill of checking out other brothers without letting them know we’re doing it, particularly as we’re feeling our way. It’s like we’ve got the antenae out there, trying to detect the slightest clue.

        One problem, however, is that so many of us want to conceal any hint that I think, in the course of the day, we pass each other like ships in the night.

  4. Besides being too young, if you give in and hit that ass, you set urself up for blackmail if the child isn’t mature enough. when he doesn’t get his way he could inform his father that you took advantage of him, see where I am going with this?

  5. Hell no.
    Never mix business with pleasure.
    More than that, he’s a baby.
    I wouldn’t even deal with him if he was 18-19. Men are still pretty damn underdeveloped then. Even 20.

  6. Nawl, son. He’s underage & he’s the boss’ son? That a recipe for disaster. I would likely have a talk with him about what he’s doing, cuz if I’m not doing him – someone will. Hopefully if he feels he can talk to me, things will be cool.

  7. Dude is a minor and I’m not down with that. I’m only a few years older but still. I would tell dude to get dressed, sit him down, and have to talk with him about this lifestyle.

      1. If he was 19, I’d wear that out. And if his dad walks in, he can get it also if he looks anything like him.

  8. I would close the door and head back to my room. If he was 18-21 it would be no problem but seeing that that’s my bosses son and he still in diapers I’ll go for saving my job and freedom

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