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Family Trip To Jamaica - S01 E06

Story 1 year ago

Family Trip To Jamaica - S01 E06

Read Story: SEASON 1 EPISODE 6

"Have fun everyone and grab some more wine. Remember, it doesn't have to be perfect, but make sure to get his ahem strength to full effect.

30 minutes is a long time, but it went by surprisingly fast. Each time I would start to lose my erection, Paul would dutifully give me a few professional pumps and I would be good to go again. He seemed to really love his job as I got a few pumps when I was still pretty hard. I had to hold myself back from cumming each time, not so much from his touch, but what it felt like to be touching while being watched. All around the room, most of these amateur painters were here not for love of craft, but because they enjoyed nudity. They were staring at my fit chest, the muscles in my legs, and at the length and thickness of my cock. It made me feel strong and desired. I Imagined they were just as tumed on as I was. And in the case of one painter, a man in his mid 40's with gray but fashionably styled hair, I knew he was turned on by how he couldn't help but give himself and idle stroke now and again. Between this and the cam sessions, I'm realizing I'm a bit of an exhibitionist.

I rejoined Lily when the time was up, and surprisingly didn't feel the need to immediately put my shorts back on. "Well I owed you, so there it was. Let's see what you drew," I said, trying to be as casual as possible.

Lily was blushing but trying to play it cool. I could tell she didn't want to betray that she actually might have enjoyed watching me up there in the nude. "I'm not much of an artist so I could only guess what Paul meant by capturing your strength. She turned the canvas to me, and it was pretty clear what she thought strength was. While you make out out my form, the one clearly defined part of the image was my dick coming out of a mess of black hair.

"Oh man. Is that what people see when they see my dick? Is the hair that bad?"

"I don't think it's bad. I actually...thought you have a nice di...penis." Lily said shyly, blushing the whole time.

"He does, and you're a lucky girl to have that to play with said one of the lesbian women with a funny wink on the way out of the room.

The whole way back to the resort room I felt really uncomfortable.

A mix between feeling a horny high from being on display and

getting stroked for half an hour without release, and feeling self conscious about having so much pubic hair. All this time being single recently has made me forget the importance of

manscaping. Lily noticed that I was off when we got in the room,

and in what seemed like a sudden rush, poured herself a doubleshot of rum from the minibar and started furiously rummaging through my things.

"Where is it?"

"What the hell, where is what!?"

"Ah ha!" Out came my electric shaver, and I started to put two and two together. Lily offered: 'Listen, I think it looked fine, but if you are going to be so annoying about it, then let's just shave it off. Get in the shower."

Let's? I was about to tell her I could do it myself, but the tension in my balls stopped me and forced me to follow her to the bathroom.

"Ok, it's no big deal right? Just drop your shorts and I'll make sure to make your dick something you can be proud of." Lily seemed determined to cheer me up, and I do think a little buzzed from the art wine and tequila shots. It was probably the tension built up all day, but I offered no protest.

I slid my shorts off, revealed my semi hard dick to my sister. Her face was stern with concentration as she approached with the shaver, but her nipples were hard as rocks, and made my dick twinge. "Ok, good," she said noticing the movement. "I think it will be easier if you are hard." Again, she was approaching this like we were solving a problem together, but I was beginning to feel like she was getting into this. I decided to push my luck.

"Well, can you help with that?"

My heart stopped and it felt like an eternity of dead silence. When I looked up, Lily's face had changed. Her eyes softened and her face exuded desire.

"Oh. Does my little brother want his big sister to make his cock hard? Mmmmm. I couldn't take my eyes off you giant dick in class. Come on, can you show me your strength again or should I call Paul?"

My stomach turned with anticipation. "Why don't you make it hard for me."

"Does my little bro like this?" And with that she toyed with the string on her bikini. Although I had already had an eyeful of her tits earlier, the way she was speaking was making me feel hungry for anything she would give me now. I was instantly rock hard as she slipped her top off, revealed her stiff, tiny nipples on her perfect pale breasts.

"Knew that would work!" She laughed. "I was pretty good at talking dirty with Derek, and he liked some kinky role play stuff. Not the first time I've been the slutty sister."

'Does my little bro like this?" And with that she toyed with the string on her bikini. Although I had already had an eyeful of her tit earlier, the way she was speaking was making me feel hungry for anything she would give me now. I was instantly rock hard as she slipped her top off, revealed her stiff, tiny nipples on her perfect pale breasts.

'Knew that would work!" She laughed. "I was pretty good at talkin dirty with Derek, and he liked some kinky role play stuff. Not the first time I've been the slutty sister.'

"What the fuck? Was that all an act?" I was a little hurt, not going lie. Not hurt enough not to still be turned on by her bare breasts that she was now covering with one arm (somehow this was also super hot).

"Hey man, just getting the job done." And with that she walked ove and turned the shaver on to start trimming my balls. "Not the first time I've helped someone shave either. With the penis out of the way, she made quick work of my balls. "And now for around the shaft. "

There must be something int he water (or rum) in the resort because without a moments hesitation, my sister put her hand around my dick and moved it down and out of the way to facilitat her work. An electric shock ran through my entire body. I couldn't believe my sexy sister was holding my dick, while topless. I tried t keep still, but could feel my body instinctively trying to rock my hips and pump myself in her hand.

'Lily...I....'

"Shush. I'm almost through."

'No, I..." More waves of pleasure rippled through me as she shifte her grip and gave my dick an unintentional squeeze. The warmth and pressure of her grip and she intense eroticism of being touched by your sister. I couldn't stop it. Before I could utter another word, streams of pent up cum shot onto my sister's chin and chest, pooling between her perky, perfect tits. I don't think I've cummed so hard or felt so fantastic in my life. My knees buckled and I held onto a towel rack to keep from falling. After the waves of pleasure ended and I settled into the after-cum drowsy feeling always get, I was suddenly reminded of how this happened. With sudden guilt and fear I looked down at my sister, still topless on her knees and who seemed to be frozen. The look on her face wa of shock to be sure, but not disgust.

She slowly stood up and, careful not to drip any cum on the floor, walked into the shower. "Well come on and help me clean up, little

brother." It was as if those words were now a command I couldn't disobey and I dutifully joined her in the shower and helped her wash the cum from her tits. She seemed to enjoy the command she had on me, and I enjoyed the work. When we were done, we dried off and she looked at me, saying "You owe me another one, little brother. Now get dressed."

Of course I listened. The girl just gave me the orgasm of a lifetime. In my drowsy stupor, I'd kill someone if she asked me to. We got dressed and didn't say much for about 15 minutes.

Lily spoke first. "Lets see what mom and dad are up to. Hopefully dad is in a better mood than before and mom will be happy we are getting along so well." We knocked on the door and mom let us in.

Sure enough, dad had a big smile on his face and looked just as contented as did in that moment....

To Be Continued...

Previous Episode

Family Trip To Jamaica - S01 E05

Next Episode

Family Trip To Jamaica - S01 E07

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