Finishing the school day

Tom takes Jill’s hand and they leave the classroom to find their friends; along the way they pause as he grabs and kisses her. They continue walking and Tom asks Jill to slip the ‘homework’ lists that he made to the other girls.

They find them on the oval and get bombarded with questions about what happened after Dennis got kicked out. Tom briefly explains what happened, glossing over the topic by saying that they were discussing different skirt lengths and what the headmaster will allow.

Tom notices Jill pull the other girls aside and them whispering together before handing them each a copy of the list. They slide the lists into their bags and rejoin the boys.

The rest of school settles into a realm of normalcy, except whenever possible Jill and Tom are sitting and talking together. After school ends Tom and Jill go for a walk, so they can get a couple of minutes alone to talk without anyone being able to overhear.

“Tell me about the picture you sent me last night, why did you take it in the middle of the library, and you didn’t go somewhere more private, like a bathroom, or even wait until you got home?”

Tom was expecting to see Jill blush again. He is surprised to see that there is only a slight rosiness to her face. It seems Jill is losing some of her shyness over the afternoon. Jill stops walking and thinks about how to answer the question.

“I guess there was a couple of reasons, the first was that I was sending it to you, and I felt I could trust you. I think if it was one of the others that won, and I would have sent a pic that would not actually show anything, you know arms across the body to hide everything, or maybe a side or a back shot.

Another reason is that since I was going to send a pic showing my body, I wanted to push myself a little to be more daring. I was originally going to take a shot in the bathroom but decided to go bold and do something no one would expect. And I guess that brings me to the last reason, to shock you and try and get you to see me different.

I guess it worked, since I got a date tomorrow, but I was so embarrassed this morning. Not knowing what you were going to say. I nearly skipped school to avoid you.”

“I am glad you didn’t skip school. And yes, your pic did work, it shocked me. The bet last night started because the guys were giving me shit about my sister. So, I decided to turn it back and choose the sexiest girl I could think for each guy. I will admit when it came to sexiest, I was arguing for Phil’s sister Tina. With her being best friends with my sister. I have had a crush on her since I was little.

When we started talking about you, I was arguing that you might be the prettiest, the main argument against you was that since you don’t try to dress sexy it is hard to tell. We know you have a good body from when you dressed more casually and from sports and that your face is beautiful, it was just that you didn’t stand out compared to the others. When I got to all the pics, you stood out as clearly as both the prettiest and the sexiest.

Now, I am glad that you didn’t standout before, and that I don’t have to fight half the school for your attention. I am guessing that is going to change soon. You seem different this afternoon, and since people have seen us together now, the guys in school are starting to really look at you, when they didn’t before.”

“Yeah, I do feel a bit different. I have noticed the eyes of people this afternoon. At first, I hated it and wanted to hide but having you next to me helped. Strangely what helped the most was seeing you grope the other girls and still choosing to ask me out. It gave me confidence, you had felt up all these girls and even Miss Shelley who I felt are sexier than me, but still you wanted me.”

“I didn’t grope anyone; I was simply performing necessary tests to best choose clothing for my party” replied jokingly Tom. “Ok, I might have pushed things a little, but everyone seemed to be having fun. Especially Kate, I always knew she was a bit outgoing, as you two always had the contrast of the shy girl and the bubbly girl, but I didn’t expect out of everyone that she would be the one to want to push things.

Speaking of you watching me, ahem, ‘inspect’, the girls, how are you feeling about it in terms of us dating. I have a strange feeling that I might get myself into more situations like that, maybe even further. I like you and want to date you but I we are only 18 and there is a lot I want to experience. Like your fantasy of serving someone and doing stuff in front of people. I won’t tell you much about the other girls’ fantasies but there were elements of voyeurism and sharing. After reading them, if I get the chance, I want to try some of the things you all wrote. But I wouldn’t want to hurt my girlfriend.”

Jill was stunned. She wasn’t expecting Tom to have thought so deeply, even she hasn’t processed everything yet. She was still in bliss of Tom asking her out and has not had the chance to process what it all means. Tom grabs Jill into a light hug, to hold her and display his desire for her while he remains quiet to allow her to think.

Her instinctive reaction is that Tom as her boyfriend should no longer want other girls. Then the image of watching him play with Miss Shelley’s body jumps to her mind, her there taking pictures of it. The taboo of it, Tom involving her, asking her opinions and making her part of the game as if she was his partner.

Then it clicks for Jill. “As I said, seeing you with the others gave me confidence, knowing that you choose me overall. Then I remembered lunch with Miss Shelley, that was really exciting. The most important thing was that you involved me, I felt like I was your accomplice in doing something we shouldn’t be doing, but we were doing it together. I liked that feeling.

Of course I would want you to myself, but there is also something about doing stuff together. I will need to think on this more, and I think that over time as we date, we can work it out. Lets just say I am not opposed to you having some fun as we start dating. As long as I still feel that I am the one you choose that you want to be with.”

Tom hugs her harder and tells her “I do want to be with you, that is why it is important that I am open with you. Like, how I have to go home now, as my mum and Mrs Willis, as well as Tina and Lisa are waiting as they are going to give a little fashion show, as they also are part of the bet. Obviously, there are going to be things I cant tell you all the details, and you may not want to hear some details, but I want us to work and I know that I cannot keep too many secrets. I don’t want to decide anything today, We have our first date tomorrow and I get a personal fashion show from you as we go shopping, there is also my birthday party that I feel could get a bit wild. So I want to leave everything open until next week as we settle into our new normal.”

Jill agrees, they continue walking and the conversation goes back to more normal topics. They get back to school as Jill is going to the library again.

Tom gives Jill a kiss and tells her “I want you when you get home to think about your fantasy, after todays actions lets change it a bit. I am having a dinner date with someone when my maid spills my drink. I punish the maid as in your fantasy and they get under the table again. After they give me a blowjob, I direct them to apologise to my date for disturbing our dinner. They crawl over to her, slide up her dress and part her knees.

Tomorrow on our date I want you to tell me who it is my date, who is the maid, and how far the maid is willing to go to apologies. Does she masturbate the date, eat her out. Does it stop there, or does it continue after the maid apologies.”

Tom can see Jill processing the story, he leans in and kisses her again and gives her a small spank. “See you tomorrow, and don’t forget your homework assignment”