This experience relates to a few years ago when I went on a trip with some family members to Hawaii. My grandmother had inherited a sum of cash and decided to treat my sister, 17, my brother, 14, and myself to a week in Hawaii. We left with the intentions of vacationing and enjoying ourselves for that week, and I had no plans for anything sexual aside from trying to sneak in some jacking off if I ever had the chance so I wouldn't be horny as hell all week.
The first few days were filled with stocking up on food and native fruit, sight-seeing, beaching, and souvenir buying before some rest and relaxation. About halfway through the week, the teenagers were still up watching t.v. and playing cards when our grandparents announced that they were retiring to bed for the night. My grandparents take sleeping pills, so once they fall asleep, they sleep heavily until the morning.
After a few more rounds of cards, we stopped for a while to watch a show, and then resumed. The rounds started to get a little boring, which I think my sister noticed. She casually suggested that we play strip poker. I was a bit tired, and I almost didn't catch it, but once I formed the thought, I was wide awake. I had seen neither of my siblings naked, nor jacked off with them, but I had jacked off with a friend on a few occasions beforehand. This proposal was going to be interesting, for my sister would be the first real pussy I would have seen up close.
After a second of thinking of the possibilities, I agreed, and started to shuffle the deck. We both looked to my younger brother, who was red in the face, and looking back and forth between us. We told him that our grandparents weren't up, that they had taken their pills, and it was just us.
After a few moments of awkward silence, he quietly nodded his head, and we started. I had no intention of losing on purpose or other things as I have read on this site, but to just play as I normally would. My sister lost first, I don't know if she planned it, or if it was the game, but off came her shirt, leaving her boobs covered by a strip of lace. her boobs were nice and full, and I could see her hard nipples poking at the fabric. I lost next, leaving me in a pair of shorts, with nothing underneath (I like that best). I am a swimmer, so my body was for the most part toned and tanned.
My brother ended up losing the next few turns, and he was now down to a pair of boxer-briefs, trying to sit in a way that we couldn't see his dick. When he lost the next hand, he reluctantly pulled down his underwear to reveal his five and a half inch dick, with a few hairs coming in above his shaft. He, like myself, was circumcised, so his head was swelling as his dick was engorged. My sister's eyes were glued, in which time I took to looking at her hand, and announcing that she had lost. Her bra came off and my eyes went up to her boobs, perfect in color, her small nipples perked up.
There was a short silence, in which my dick had grown stiff, and finally I broke it.
'I'm sorry guys, but I gotta jack off.' My sister's eyes widened, and she stood, looking down at us on the floor.
'Well seeing as Brandon is already naked, and you're getting naked, I might as well take these off.' She said, removing her thong. I was now looking directly at the first pussy I ever saw, and it was perfect. She had a small, trimmed bush of hair. She sat back down on the couch, and spread her legs apart, running her finger up and down her lips.
My shorts quickly came off, and my sister was staring at my cock. I kept it shaved, personal preference, which she made a comment to with another about myself going commando. I wrapped my hand around my cock, and started to jerk off, trying not to moan too loudly although my grandparents weren't waking up anytime soon. I opened my eyes after a few seconds, and saw Brandon leaning back against a chair, fondling his balls and rubbing his cock slowly, and my sister with her fingers in her pussy. That sight sent me over the edge, and I shot several ropes of thick cum, landing on my chest and neck.
My sister soon came, along with my brother. This experience gave way to more, outside of Hawaii. There was another during our trip, two days later, but that story is for another time.