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Cabana Boy  

Ladyjazz48 76F
25 posts
2/26/2019 3:04 pm
Cabana Boy

A number of years ago I won an all expenses 4 day trip to Barbados. It was at the Ritz Carlton and came with a $400 room voucher. The other amenities were zip lining, golf, outrigger rides and a full body massage in a private Cabana right on the beach. I'm sure you can guess which activity I chose?

As I entered the Cabana room I could already feel the Caribbean vibe through the kettle drum music and a display of tropical fruits on the table. There was an array of sparkling fruit drinks like papaya, guava, pineapple as well as wine spritzers and sparkling champagne. Being the diva I am I took a flute of champagne from a tall dark skinned man. He smiled showing me his perfectly white teeth and deep dimples. He said his name was Winston. I said 'really? as in Churchill?' He grinned and said 'yes mum, one and the same' He was kinda shy when he asked if I wanted a deep tissue or moderate and would explain the deluxe if I still needed more attention. I said deep tissue isn't my speed so let's go with a moderate and see how it goes. He gave me an extra large towel and stepped out as I disrobed and lay face down with my face in the well.

Winston returned and said 'Ok I will begin with a light touch and then use the oils. Do you have a scent preference? We have, rose petals, gardenia, jasmine, lilac, lily..I stopped him and sent let's go with Jasmine. Starting with my ankles he worked my calves and kneaded them gently. I could feel myself drifting to sleep as the music played and the ocean waves crashed. After what seemed like 15 minutes I felt his hands on my shoulders working towards my buttocks. When he stood next to my head I could see he had large relaxed penis through his sparkling white shorts. He was muscular and I commented on his stature. You must work out a lot I asked, your thighs are incredible! He smiled and said, not really mum. I do play a lot of rugby and do free style swimming in the hotel pool.

He stepped away from the table and selected a bottle of the oil and soon I felt him rubbing my calves again. This time he was further up my thighs with the oil. He was getting very close to my groin area. I felt myself getting aroused and my pussy getting wet. Then he whispered in my ear 'mum would you like the deluxe?' Oh, now I know what he meant. I whispered back, yes please give me the complete deluxe.

Once again he stepped away from the table and removed his watch. As he turned back I noticed his penis was very much bigger and outlined nicely crosswise. He saw that I was ogling his cock and smiled shyly. He asked if I liked what I saw and I nodded. Then he re-positioned his cock and let the tip peek through a little. Wow, it was a very long one! He wasn't wearing shorts shorts, but those long ones so his cock peeking out had to be huge! I put my head back down and felt the towel come off and again felt his hands working my torso. Then he worked on my ass slipping his fingers between my crack. His fingers were slippery with the oil and as my nipples hardened and pussy getting wetter! I felt him pull one of my knees up so as to enter my crack easier. Soon I felt him massaging my clit with his thumb. I though he was going to make me cum until he started rimming my asshole with his other hand. I was so lathered in oil I thought I might slip off the table. I wanted to turn on my back and spread eagle for him. He said 'sorry mum, it is discouraged as is me removing my clothes. What? oh man I wanted Winston to fuck me right now!! lol

Don't worry he smiled, I will take care of mum. Once again he was at the table this time he had a piece of the mango that was sliced lengthwise. He started to run it down my lower back and before I knew it had inserted the fruit in my cunt. With his thumb he continually caressed my anus. He removed the fruit and sucked and ate it up and said' yes Mum, is quite sweet and ready. He slid his long finger into me that one you flip the bird with. It was all the way to his knuckle and he was thrusting quickly in and out all the while rubbing my asshole and slipping in another finger with his other hand! I could barely handle it, with his hard dick in close proximity the oil, the Jasmine scent. ahhhhhhh cumming I managed to say in deep whisper. After a few minutes I felt him with a warm wet washcloth as he cleaned my pussy.

He stepped out as I dressed and noticing his tip jar I slipped in 2 twenty's. Winston returned and asked if I would like a visit tonight? Hello yes of course I would. I started to give my room number but he said I have it on the voucher mum. Can I visit around 9:00? I agreed to the time and returned to my room.

The first thing I did was run a nice warm<b> bubble bath </font></b>to wash off the oils. Then I took a late afternoon nap and later ordered a fish dinner from room service around 7:00 PM. I tried watching the local TV stations but the girl was anxious looking at the clock. It was finally 8:45 so I slipped on a sexy lingerie with cutouts where the nipples poked out. I could already feel my cunt starting to drip and then I heard a soft knock.

Winston was in some grey Bermuda shorts and a soft white shirt and with his shy smile says 'good evening mum' so polite these islanders are. I gave him a sheepish smile and said I kinda started without you. He gave me a quizzical look. I explained I was quite wet already. He laughed out loud and started to remove his clothes, as I started to do the same he said, please don't. You are quite lovely mum. Now that he was undressed I could see his beautiful cock. Wow, 10" and throbbing with thighs that could crack walnuts. He laid me back and stroked my thighs through the lingerie and he smiled and said yes lovely. Then I felt him part my thighs and put his face under the lingerie as his tongue tasted my wetness. He delved in deeply and made this humming sound in enjoyment. Before long my knees were up as his face was fully engulfed in pussy juice. Wow, I climaxed quickly. He wanted to penetrate me, but I wanted to see and taste his cock and balls.

Starting with his ball sack I suckled them in my mouth then slipped a few inches into my mouth. I took as man inches of him that I could handle. I asked him to kneel in front of me and treated him to a good asshole rim job. He moaned loudly as I licked his ass and stroked his 10". Before long he flipped me over and with his cock smacked my cunt and teased me. Then I got on all fours my go to position for big cocks! Winston didn't need to tease me, he pushed right in and I felt at least 8" of his cock in me! Ahhhhhhh I groaned but he pulled out before I could cum. Then he sat on the settee and had me straddle him. I felt all of his cock deep inside of me to the hilt. I moaned half in ecstacy and part in pain. His thumb was in my asshole as I rode him up and down. He caressed my nipples with his tongue as I popped up and down on his generous erection. His cock was smothered in pussy juices as he slammed deeply in me. Winston was moaning hard and then 1 final thrust as he exploded his hot cum in my walls. He had a big wad and I was drained and could feel his cum slide down my thighs. Would mum like to rest before we go again? yeah mum needs a breather. So once again he cleaned me up then we laid in a spoon fashion with his cock nestled between my butt cheeks. Every so often his cock would stiffen as it got near my asshole, but I knew this wouldn't happen. LOL too much cock. but Winston did pleasure me and left around 1 AM. On my last day he came by my room to say farewell and gave me an oral send off. Great trip!!


Paulxx001 67M
22642 posts
2/26/2019 11:52 pm

Well.. that's a totally hot story with a great picture, as well. I won't describe the effect it had on me.... you can imagine... 😱
However... even if I stretch my little fella.. he won't get to 10 inches. That's impressive.. lol 😊😘


RobK2006 56M
5998 posts
2/28/2019 11:02 am

Loved the lead up with the massage and you checking out his cock. Ten inches! And the way he massaged your pussy and asshole. I loved visualizing you with so much massage oil between your legs. Glad you got to get fucked by him later on. Amazing that you straddled him and took him so deep in your pussy. Your post made me hard!


logjam4u 54M
39 posts
3/5/2019 12:28 pm

nuttin like a mature beautiful lady


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