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After our meal at night we went down to the beach which wasnt a wise move wearing heels although after I took them off I was fine. We sat on a sun lounger on the beach watching the sun setting and thats when I decided to ask him. I explained to Mark that Ive loved doing different things with him and that I had experienced alot while seeing him however pointed out there was one thing I had wanted to do... anal sex. I saw Marks face and he looked a little put off. I kept on going telling him that I had experimented on my own but would love to even try it with Mark as I trusted him. Mark then eventually spoke up and claimed he had done it before and the previous partner had found it sore and painful so he didnt want to do it incase he hurt me. After a bit of back and forth discussion I eventually won Mark over to at least attempt it. Excited by the development we both went abck to the apartment. On the way he mentioned lube however I had secretly brought some knowing I was going to ask. Accurately striking the erotic ‘ball’ that Georgia would present as she bent for her caning really shouldn’t pose a problem for him. “Well, so, I guess if you pull down your knickers and bend over the desk, I’ll get on with giving you the twelve cane stokes then,” said Luke slightly nervously.Georgia laughed, “Oh come on Luke, I thought you were more adventurous. If we’re really going to do this properly, we need to role play it, make it seem real, after all, you are dressed for the part, Mr. extremely handsome Headmaster.”Luke again blushed, his usual confidence with the opposite sex somehow challenged by Georgia’s unexpected request. Had she simply been angling for a fuck he’d have willingly obliged without hesitation, after all, it was only a couple of weeks since he’d done a valuation at a former hotel and ended up in a four-poster bed shagging the pretty, young estate agent who was there to let him in. “Okay Luke, I’m ‘Head-garl’ and you’ve sent for me because I’ve caned another.
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