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Dear Diary I: Acceptance

High School Sweethearts: The dream relationship lives!

The Prom: It’s the second most important day in a young girl’s life. If he doesn’t find that key he might experience the most important day as well.

The delightfully devilish smile was the inspiration for this caption. I could see myself having fallen for that deal when I was in school.

Anonymous said:can you do a caption of juno temple in school uniform keeping a boy in chastity and making him her homework slave?

Spring Break Week: Spring Break may be over but your chastity is just beginning!

The first appearance of the beautiful Bianca Beauchamp. Fun fact: Mrs Beauchamp wanted to become a teacher and was just modeling for some quick Canadian bucks on the side, but her school insisted that she had to decide between modeling and teaching, since

When Lovecraft’s stories about the ancient tentacled monster Nyarlathotep got an adaption as a Japanese anime series, there obviously was just one important question: should the crawling chaos be depicted as a highschool girl? Or as a middle school

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I thought you had a thing for the school girl look. So now will you agree to wear that little chastity device and give me all the orgasms I want?

Your Goddess knows that if she didn’t keep your little member securely locked away in chastity, you would be constantly diddling yourself like an immature school boy who just found a secret stash of his uncles Playboy magazines. At the end of the day,

High school girlfriends, become wives if you give them the key to your chastity belt before you go to college.

She loved her school teams. But the smile was for one special someone.Every time she performed a cheer she knew for certain what was happening to his pubescent penis.The game day spikes had been one of fellow cheer leader’s ideas.Sharing chastity, tease

I know you are trying your best to get me to give you detention again.Here is what I don’t think you completely understand…If you get detention again I will not be taking the cage off your little problem maker. I will just be adding time to its detention.

I guess what they taught me in business school was true.What is measured is improved.But I like to think the floggings and chastity time also contributed to our team’s improved results.Do any of you want to disagree with me?

Amy’s niece had suspected Amy kept me locked in a cock cage since she moved in at the beginning of the school year.On weekends I truly believe her greatest joy in life was to bother me until a little wet spot appeared on my trousers.She and Amy thought

Sending you to cosmetics school was an excellent investment. I love that you can do my makeup every morning before I go to work. Tell you what, if I get at least five compliments I won’t whip you tonight. | Caption Credit: Crystal Chastity

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