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.I was in heaven, I bobbed up and down on it loving the full feeling in my young ass and jerked off all over the tub!! From that day forward that bottle was in my ass almost daily, I found out I could clean my ass out with an old bottle full of water as an enema, I’m smart and horny like that!! After I left to boarding school I kinda forgot about anal until my first marriage and that starts a next chapter!! Extra Supplement: My First two “almost” gay experiences!!#1I’m a sophomore in HS in the Caribbean and on a scuba diving trip on another island. After our first day of diving we head to a bar for dinner and drinks, this was ‘81-‘82, no law and certainly no drinking age lolWe start playing quarters with some guys off a charter boat and get hammered. I say I gotta go and one nice looking guy says he will help me back to the hotel. We head back to my room and on the way he asks if I’m into guys and gropes me! I’m stunned, I’ve fantasized sure but taking it to the next level was crazy!!. “That might be interesting, I’ve always thought that he was a bit of a dirty old man.” Sherri didn’t seem to be protesting at all. She logged in to her work email and scheduled an appointment with Robert.Monday morning we met with Robert. He was both the owner of the company and my wife’s direct boss. They were 2 of only 4 people who worked in the office area, most of the employees worked either in the field selling, or in the warehouse.“Wear one of your schoolgirl uniforms, complete with knee socks. Skip the bra, I want glimpses of your nipples pressing against your shirt.”It was a good choice. Robert could hardly take his eyes off Sherri the whole time. I made my wife explain.“I learn from my mistakes best when I get spanked hard for making them. I’ve known this all my life, but recently I admitted it to my husband and hope that his punishments will help me become a better person, wife, and employee.”Robert’s mouth hung open as his listened intently.“Please keep a list of all my.
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