Rough ofcourse

You press down on Jack's prostate Hard and hear him grunt in pain. You keep up the pressure but he keeps sucking Jennies strapon.

You decide to add something and move more of your hand up his ass. Soon you´re about 2" past your wrist. Then you pull back to your hand, and repeat. With every stroke, you give his prostate a hard squeeze.

Jack unloads in Jennies throat, bu Jennie hasn´t cum yet. You get an idea.
"Jennie, come over here and fist andrew for me while I take you strapon."

Jennie smiles a naughty smile
"Sure."

Jack looks at the strapon as if it was the tastiet lolipop in the world as its taken from his mouth. You strap on the dildo and help Jennie insert her fist up Jack's ass. She´s got thinner hands but this only lets her get in further than you. You get down in front of Jack and guide the strapon to his lips. He immediately resumes his fervent sucking. He doesn´t even protest when you grab the back of his head and push the strapon down his throat, making him gag.
"Look at me Jack, I wanna look you in the eyes as you become my Fucktoy!"

Your language surprises you but Jack does as he´s told and looks up with his horny eyes.