Ask to feel them

"I'll need to use my hands to examine them more closely," you try to sound scientific, but you really just hope you don't sound creepy.

"Oh, well then please proceed, doctor," responds Anna. She giggles a bit as she does so, clearly picking up on your nerdy attempts to be official. She was never into roleplay before, but maybe now is your chance.

"I'll need to take you to the examination room," you say, and you stand up, grabbing her hand and leading her to the bedroom.

"Lie down on your back and hands at your side." Anna is surprised that you can actually muster authority, but she complies.

She lays down on the bed, and as she does so her tits fall a bit to her sides. It's a bit warmer in the bedroom, but her nipples still stand at attention, waiting for your examination. Is it from the cold or is she just that turned on? You're positive that it's both.

You climb onto the bed with Anna and straddle her body, giving you the perfect angle to examine her breasts. There's a moment where you think you hear her moan, but then it's gone. As you lean over her body to grasp one tit in each hand, your raging cock begins to press into the fabric of the boy shorts. The material is incredibly thin and you can't help but imagine her lips parting around your cock as it pushes more and more against her body. This time, Anna definitely moans.

With a breast in each hand, you begin to circle her nipples with your thumbs. You flick across them, and each time they return to attention, awaiting further instructions. You turn your hands so that your fingers trace around the outer edges of her tits until they find their way underneath each in the crevice where breast connects to chest. Your fingers trace upward now, pulling up a bit as you do so. Each breast lifts slightly in the air before crashing seductively back into her body, bouncing up and down seemingly for hours. You then pinch each nipple, causing Anna to whimper in pleasure and pain, and you pull up again. This time you lift each breast as high as they can go and you can see the pain forming on Anna's face. Just before she protests, you release, and each breast once more does its dance.

"I have concluded that they are indeed slightly bigger than before," you announce.

Anna is still trying to catch her breath after your rough handling of her nipples.

"Any other conclusions, doctor?" she finally manages to ask.

You sit up and look over her entire body once more. Looking down at her boy shorts you notice that there's a tiny hint of dampness where her lips push against the fabric. This whole day has left you with masturbation material for weeks, but should you push things further? You could probably stop now and go back to Penny without too much worry. After all, playing with some tits is hardly cheating.