I slid a second finger into her ass and she started to push down on them. Now I knew for sure that she wanted more. I liberally lubed her tight hole w...th a good anal lube and the lubed the dildo up.I placed the dildo against her puckered hole and asked, “Are you ready for this?”She said, “Yes, I want to feel it in me!”I started to apply pressure and ever slowly the head of the dildo started to slide in, I was watching her face to make sure that I was not hurting her, She grimaced as the head. We sat and watched TV and I looked over to see she was shaking and nearly crying. I gave her a hug to comfort her and she laid her head on my shoulder and gave me an odd sort of look and told me I was a kind-hearted young man. My folks came home just about then and she jumped away from me, but stayed for tea and they walked her home and got her door open for her. Not long after, my Dad had a week's business trip to New York and took my Mom along. They asked Cheryl if she would keep an eye on me. "I want someone to ask me for a date; I'm too old to be asking a guy out." How about a girl?" she grinned."Huh?" I said, surprised. "I like women still, but I don't think I have the courage to ask one for a date. Rejection feels terrible." I'd go out with you," she said. "In fact, let me go home and change, and you and I will go dancin'. It's time you had a date."I perked right up, smiling and grinning. "You mean it?" I asked."Wear something slinky," she said.She gathered her things and left,. Again she was aware of his submissive watching her, whether it was with interest or, another emotion she could not quite identify, she was not sure. But this submissive intrigued her, what was she thinking as she watched the evening unfold in front of her, watching, yet not participating.Finally she was allowed to move out from under the table, clear away the plates and take a drink of water. She served the dessert and knelt at his side. This time he stroked her hair gently and patted her.