Yes, she should

Maybe this was your chance. You looked at Lily, "well, do you want to try it?"

She looked shocked, "John, I just met you! I don't think we should..."

Maybe just one little push for Lily, "I think it would be okay for us to experiment together."

"I guess, but I'm not really sure... where to start."

"How about we start with this?" You leaned across to Lily, and gave her a light kiss.

"Thanks for being so patient with me, John."

"No problem," you assured her, "we can take all the time you want."

Emma jumped in, "no, gawd... get to it already!" You and Lily both laughed at her impatience.

You looked back to Lily and leaned in for another kiss. You reached for the bottom of her shirt, and pulled it over her head. Lily looked a little unsure, but looked down at herself and then up to smile at you.

Emma moved over to the chair to give you some room, but was obviously eager to have a good view of the proceedings.

You reached behind Lily, undid the clasp of her bra, and gently pulled it over her head. As you had suspected, a padded bra had been doing a lot of work. Lily's breasts were tiny, with lovely dark nipples.

"They're too small," Lily said sadly.

That attitude was unacceptable, "I think they're beautiful Lily. All boobs are good boobs," she giggled in response.

You added, "how about I show you how much I like them?" She was still leaning against the headboard, but you grabbed her feet and pulled her back. She laughed with surprise, but was left lying down with her head on the pillow.

You crawled beside her and ran your hand from her stomach, up to one of her lovely tits. They were definitely small, but felt great. They felt even better when her nipple started to respond to your touch.

You leaned down and kissed your way along the same path. When you got to her nipple, you heard a sigh from Lily. Her tits were small, but very perky, and you spent some time enjoying her firm nipples in your mouth.

Your hand slid down, tentatively exploring her pussy through her shorts. You expected some kind of reaction, but got none.

You looked up to see Lily looking down on you with a look on her face that you could only describe as a silly little grin. "You okay, Lily?"

You got the silly grin and subtle nod in response.

After spending some more time playing with her, you felt her squirm under your hand. You looked up to see the grin, "should we get these clothes out of the way?"

Grin. Little nod.

You knelt beside Lily to pull her shorts and panties off. She wasn't very hairy, but what she had was natural.

You laid back down beside Lily, giving her a soft kiss, but leaving your hand to explore her now-exposed pussy. You moved your mouth back down to her nipples. Both of you seemed to be enjoying that.

After a few minutes, you felt her start to get wet.