Painful anal sex story

I started working as a legal intern, not even a junior attorney, at the law firm of Verbreennung, Stechen, and Wunderhintern in the fall after my graduation from law school. The dress requirements were strict. Women were to dress in a manner that emphasized their femininity. But the dress code emphasized dressing like a professional woman. Women were to wear dresses or skirts and blouses.
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Not Taking it Up the Ass Ruined My Marriage (and Five Other Stories About Anal Sex)

Ok, so this man was 20 years older than me, which may seem like quite a stretch but we were just suited to one another. He was married but no longer with his wife, instead of going through the divorce process they just decided to stay married and friendly with one another. He was totally honest with me from the moment we met inside an upmarket bar in the centre of the city. We talked for ages sitting on the high bar stools and straining to hear one another over the music. As the night went on we decided to head back to his apartment, it was a bright apartment with an amazing open plan design. He had the most magnificent oak bed with beautiful white bed sheets, we talked over a glass of red wine and then he stripped my clothes off and took me into the bedroom.
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My First Time Anal Experience

It was going to be another dull, dull night in my really dull but very cheap apartment. I may have blown the manager a few times when I came up a little short on the rent, but he must have blown the building safety inspector daily to keep that shithole from being condemned. The only thing good about living in such a one bedroom nightmare was I never got the urge to clean it. I took the affirmative position. Even as a kid I seemed to like to stick various objects up my bum.
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Note the first: CN for true stories of dubious consent, sexual pressure, cheating, unpleasant early sexual experiences. Note the second: For outside-of-UK readers: 16 is the legal age of consent in my country. I am fifteen and a virgin.
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