New job and celebration

Monday was great. At lunch, Kevin was eating with Grace when Maria emailed him, introducing herself as his new boss, meaning he got the job. He was excited. Grace seemed even more excited. She invited him to her place after classes. The rest of the afternoon went well since he was happy about the job. He had been derailed in the summer and now he was already building back up. He would start work tomorrow, and it would basically be a long training cycle. Even Grace was still training.

After school he went over to Grace's place. Her mother was at work and her father was away on business, as was typical, her sister was away studying at a different school and living there.. She took him up to her room. Her parents had a lot of decorations from the motherland around the house but Grace's room didn't have any of that. That made sense to Kevin.

Grace brought him inside. and sat him on the bed.

Grace: Ok, I have a surprise for you since you got the job.

Kevin: What kind of surprise?

Grace: I think you will like it, but tell me if you don't, we can totally do something different.

Grace stripped down moving like a mock strip tease. She wasn't very good, but that hardly mattered to Kevin. He thought this was the surprise. Then she turned around and bent over and gave her ass a smack.

Grace: How would you like to take my ass? I've seen how you look at it.

Kevin: You have a great ass, but have you done this before?

Grace: No, but that makes it special right?

Kevin: Ok, but we need to be careful.

Grace: I've already done preparation today, but I didn't have time to stretch it out.

Kevin: Ok, let's take it slow.

Grace: Ok, I knew you would like it.

Grace started to stroke Kevin's dick with her hands, then mouth. Once he was very hard, she put a rubber hat on it and brought some lube. She got on her elbows and knees on the bed and Kevin approached her from behind. She breathed in sharply as he put some cold lube on her butthole. Then he started with his finger and Grace took it well. He went with two and she was uncomfortable but adjusted. He wanted to get in before he went soft and started slow trying to introduce the tip with a new application of lube. Grace grunted and winced as the tip went in. She was clearly not enjoying it.

Kevin: We can do something else if it hurts.

Grace: I knew it would hurt, that's ok, please keep going.

Kevin went a little deeper and thought he heard Grace whimper and sob.

Grace: Please keep going.

Kevin went a little further until her was halfway and started pumping. He saw a tear drop. Grace seemed to be hurt and he slowed down.

Grace: Keep going.

He did and got into a rhythm. As he was feeling it he went deeper and deeper. Grace was grunting and making painful noise but urged him on. He kept going and came. Grace seemed relieved when he took his cock out of her ass. and wiped her eyes.

Grace: Congratulations, you earned that.

Kevin: Are you ok?

Grace: Yes. It hurt, but I'm ok. You deserved that and I wanted to give it to you.

Kevin: It's a job sure, but it seems like my job means a lot to you.

Grace: I worked hard to get a job there. And I work hard, but you always help me in class and that helps me. My mom has worked there for years and it was still hard for me to get a job there. I'm a straight A student. You must have really impressed them and I don't think that should go unrewarded. Besides, I've always wanted to try anal but never had a boyfriend. I guess I should have prepared more though.

Kevin thought Grace and Penny should compare notes. How hot would the two of them be doing anal training together?

Kevin: I appreciate that. I really enjoyed it and it means a lot to me you would do that.

Grace: I'm glad you liked it.

Grace smiled a big smile.

Grace: Kevin, this means a lot to me too. I put myself out there. Vulnerable. I think a lot of boys might have shot me down because I'm awkward and don't know how to be sexy. But I need to get ready for my shift and my mother will be home soon so you had better go.

Kevin: Grace, don't be so hard on yourself. You are great.

Kevin kissed her and left.