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Guilty pleasure: island massages

Omg! I was reading other confessions and one reminded me of something from MANY years ago. I think I was about 15 at the time. My parents forced me to go on vacation with them to some island. They had activities planned for every day, all day. I wasn't interested and just hung back at the resort pool. The second day by the pool a slender black dude came to get my drink order. He must've thought I was older because when I asked what they had he named alcohol drinks to me and I got one. They were sweet and I didn't think they packed much punch so when I was on my third one he asked if there was anything else I needed. I said I didn't know what he meant (because I really didn't). He named off some mostly boring sounding things but then he mentioned a massage. I said sure! why not! He said he'd arrange it and asked if I wanted it in my room, the spa or in a cabana by the beach. I got the cabana. Shortly. he pointed me in the direction of a cabana. I went inside and another black dude said for me to undress and lie facedown on the padded table. I did and put a little sheet over my **. He totally slathered me with oil and rubbed my back then on down to my feet. He moved my legs apart and came back up the inside of my thighs and near my **. Then he was rubbing my ** cheeks and sliding his fingers over my crack and ** until he was sexually rubbing my ** and I'll never forget being shocked by him spreading my ** cheeks and sliding a ** inside my **. I was young and naive and didn't know what was going on so I wasn't going to say anything. It felt good and I was definitely tipsy and went with it. He had me turnover on my back and asked if I wanted a sheet covering me and I just said whatever you do and he kept it off. He told me to close my eyes and he put a warm wet cloth over my forehead and eyes. Then he started rubbing my shoulders and went over my little ** quickly, then my arms and back to my ** where he massaged them for a very long time and played with my ** (gave me chills beyond the breezes blowing through!) before doing my stomach, down my legs and back up to my **. He went straight for putting his fingers in me and I now know that he was basically ** f**ing me! By the time he finished, I felt like I couldn't move. He said relax and let him know if I needed help to the pool or my room or whatever. I ended up getting a massage everyday. The small talk was rare and it was clear he thought (or pretended) I was older. The massages concentrated more and more on just my ** organs and he used his mouth a couple times on my ** and **. (I don't think he took my virginity!) My parents never knew until they were going over the charges and were surprised I had gotten massages. I thought they'd be angry but didn't suspect a thing out of order. I never told anyone and it faded from memory until I was in college and my friends and I talked about an island vacation but for the life of my I couldn't remember where we went. I asked my parents but they took so many cruises and island trips they didn't remember. Mannnnn, I wish I could go now. I would appreciate it much more than I did then!!

Jul 13

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