Ann was 18 but she got along well with adults and kids. This is why she was a popular babysitter. Sue and Dan had two kids; Diane was 18 years old and Mike age 1. This was a big gap between the brother and sister, even though Diane watched her baby brother many times for like one to two hours, she just never watched him longer then that. Diane’s parents (Sue and Dan) heard so much about Ann they hired her to baby-sit Mike if they were going to be gone longer then a few hours. Ann (17) and Diane (11) soon found themselves more like sisters and while Ann watched Mike, her and Diane would play games and talk.
Diane would get into her mothers make-up and put some on while her mother was gone, Ann seeing went to Diane and asked if she could help her put it on, Diane was excited about this because she loved the way Ann wore her make-up.
After Ann did Diane’s hair and make-up, she then found a beautiful short dress of her moms and she put it on. Ann thought it was great how Diane felt so beautiful just from having her hair and make-up done; Ann said you now look just like a model. Diane expressed to Ann that some day she would love to be a beautiful model. Ann said” I’m sure you will be if you put your mind to it, it will come true”.
Diane found herself using more and more of her mom’s make-up and going thru her mom’s clothes. Of course they were too big for her never the less it was fun to dress like mom. Ann started to baby-sit more and more and Diane’s parents felt more comfortable leaving them over night with Ann babysitting.
Ann enjoyed chatting online with others and she started to use the computer at Diane’s house. Diane being close with Ann started to sit in the same room with her while she chatted online.
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Diane and Ann started to chat with some of the guys online, and one of them suggested that Diane should play dress up with her mom’s clothes like she had done many times before. Without thinking, Diane changed into one of her mom’s skirts and blouse. I looked so funny in it, because of how big mom’s clothes were. Ann saw that Diane did not put a camisole under the blouse and she could see Diane’s training bra. Ann told the guy she was chatting with he suggested that Diane should pretend to model the clothes, he sent Diane and Ann some pictures of girls modeling clothes and Diane decided that it would be fun to do that.
Then the man said that Diane should model in her underwear. Diane said “NO WAY” Ann said that no one but her would see. When Diane was not going to do it, the man sent them a picture of a girl Diane’s age that was modeling in her underwear. Seeing that others do it, Diane didn’t think it would hurt and she took off moms skirt and blouse.
The man said that Ann should do it too so that Diane would not feel alone modeling. Diane saw that Ann had very pretty matching panties and bra; she wished that she had a pair like that. Ann took hers off while Diane turned her head away, but Ann said it was ok for her to look, so Diane turned back and watched Ann undress. Ann found some sexy lingerie in Diane’s mom’s drawer and she put them on, while Diane put on Ann’s matching purple bra and panty set. Ann’s panties were a little big but not as big as her mom’s so they looked cute on her anyway. Also, Ann had on a padded size “B” cup and it made Diane look like she had boobs and she was excited about that.
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Ann noticed that Diane kept rubbing her hand on the bra cups, she had to tell her how beautiful she looked wearing her underwear. The man kept sending other pictures for Diane to model after, and for every one that was sent Diane made that pose while Ann watched and told the man what Diane was doing.
This soon became a usual activity when Ann came over to baby-sit.
Not only did Diane look forward to having Ann over but Ann also looked forward to them weekends too. The would get back on line with the man, he would send more pictures of girls, and Diane would pose like the models in the pictures, before long the man said that we should try posing naked, and send some pictures of girls posing naked. Ann said it was ok so Diane posed naked this time, after awhile he sent some pictures of girl models posing together and touching each other. He said we had to practice posing like that to be a good model. Ann said she was game for it, so I said I would do it too.
First it was just holding each other, and then one was of girls kissing while wearing their underwear. Ann and Diane posed as the girls did in the pictures and found it was not so bad kissing another girl.
The hard part was when one girl had her hand inside the other girls panties, Ann quickly made that pose with Diane and put her hand in Diane’s panties and Diane was so scared she did not know what to do. Ann asked her if she wanted her to take her hand out. Diane knew it felt good she could not say a word, so Ann kept her hand there and started to move it around and feeling her down there even more.
Ann could feel that Diane did not have much hair to speak of down there she started to rub and wanted to get a closer look, Ann put her face closer to Diane’s panties and did like one of the picture showed. Ann put her mouth down there too, Diane was now truly scared but new it felt good, she just laid back and let Ann blow warm air and lick thru her panties.
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Since then Diane has been thinking a lot about how it felt and finds that looking at other girls makes her think more about what happened and she now can not wait for the next time Ann comes to baby-sit her baby brother.
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