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Never one to turn down a free holiday i said it would be a great idea. My one stipulation was i wanted my own room, to which dad said just as well because that was my stipulation too. So off we went for a 2 week trip to Jamaica all inclusive. Couldnt of been happier if im honest. After a long flight and long bus ride from the airport we finally arrived at our hotel. It was late at night and we were all tired. We checked in and were given our room keys, it was then i noticed that dad had screwed me over, they were in a top suite and i was in a normal room. I wasnt too fussed really as it still had all the mod cons and i was alone to enjoy some me time with my dildo and clothes i had packed with me. Got to my room and pretty much went straight to sleep. I was woken next morning by my dad telling me that there was a managers meeting in the lobby with intro drinks. I got ready and met them in the lobby. That was the first time i got a look at the manager who i would later know as James.. Ashleigh couldnt help but jump though as she felt the cold lube make contact with her body. Ashleigh was unable to place the feeling, or even interpret it as she felt the finger run circles around her last virgin hole. She knew some girls who had lost their virginity in this office, she was glad she hadnt, but still couldnt have imagined that shed lose her final virginity here. As she tried to contemplate her situation some more she missed that the finger had stopped circling until she felt a sudden surge of pressure. The girl let out a cry as the finger pushed into her ass and heard a laugh coming from in front of her. Looking up again she saw that Headmaster Carlisle was overjoyed with delight. Hmm, I think Ill have to put Ashleigh on my graduation list, if she continues to look as amazing as she does right now. A sigh and a cringe escaped from the president. The headmaster didnt get to take advantage of the girls in quite the same way that the sponsors did, but he did get to.
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