Surprise your roommate (gay/bisexual male)

Before you even open your eyes, you hear the familiar slapping of flesh and smell the telltale notes of arousal that you've woke up to every day of the semester so far. Your roommate, Steve, is convinced that you sleep through his early-morning masturbation sessions, and until now you've never had any reason to correct that notion.

Slowly, as usual, you turn your head gradually toward his side of the room until you can see the motion of his hand under his tented sheet and the adorable way he bites his bottom lip to keep his panting quiet. You can't resist slipping your own hand into your boxers and gripping your growing erection, wishing you could match his pace or, better yet, trade hands with him.

But wait a second.

If that dream was legit -- and for some absurd reason you're convinced that it is -- you totally could do that if you want. Well, if Steve wants. After a few deep breaths to still your nerves, you sit up in bed and said;

"Would you rather we jerk each other off, or suck each other's cocks?"

"What the hell, dude!" Steve shouts, frantically covering himself under his blanket and curling up a bit. After a moment, the shock wears off and he finally seems to process what you actually said, thinking about it for a while. "Oh, uh... I'm not gay, so I guess let's just jerk each other off?"

You jump out of your uncomfortable dormitory bed and shimmy off your old, well-worn boxers while Steve throws his blanket aside to reveal that he's completely naked underneath. His body is incredible. He's fit but not buff, exactly; his chest is firm in a smooth, slender way, and there's clearly some power in those toned thighs and calves. The cock between them is even nicer than you'd imagined; about 5 inches long and thick enough to really fill your hand as you settle in beside him.

"It's so warm," you whisper, "and the head is throbbing already. You've been going for a while, huh..?"

"Y-yeah..." Steve admits, nervously fumbling for your dick but refusing to look directly at it. "Twenty, maybe thirty minutes, I guess?"

You guide his hand to your shaft and help set pace before leaving him to stroke it on his own.

"You've got a lot of work to do to catch me up, then. It's only fair if we cum at the same time, right?"

"I-I guess, yeah..." Steve glances back and forth between your dick and his. "I thought it would feel more like stroking my own..."

"It's so much more exciting this way though, right?" You touch his cheek with your free hand and make him look you in the eye. Your faces are just inches apart. "Holding someone else's pleasure in the palm of your hand. Feeling him throb with desire for you. Letting him give all that pleasure right back to you."

"I-I'm getting close," Steve gasped as you stopped stroking and rubbed your thumb over his swollen purple head. "REAL close."

"Hold on, baby," you nod, pressing your forehead against his. "I'm almost there. H-how do you want to do this?"