“Ok, let’s see how brave you are, but remember, if you do this dare, it’s my turn next, and I promise I won’t wimp out.” I told her it was ok if she did, but I was ready for mine. I really thought she was going to tell me to take off my pants or something like that, but instead she said, “I dare you to take off my top.” I was dumbfounded, my sister wanted to show me her tits. I just stayed there looking at her. She turned around to show me the hook in the back.
I reached up and unhooked it, then I slid the straps over her shoulders. She pulled it off and turned to face me. Her tits were amazing. Not big, but certainly not small. I’m not much of a judge, but after seeing enough porn, I would say they were B cups. She smiled and said, “bet this isn’t the way you thought tonight would go, huh?” I slowly shook my head, but I never took my eyes off her tits. They were half in the water and half out, but I noticed her nipples were really hard and I assumed it was the cool water doing that. She said, “How do they look, like you imagined?”
I said, “Yeah, their amazing, but what makes you think I have been imagining them?”
Mary said, “Oh come on, you’re 18 and always horny, I know you thought about me once or twice while jerking off, and If I’m being honest, I’ve done the same thing thinking about you.” That really got my dicks attention. Here was my sister, this hot older woman, telling me she masturbated thinking about me, Wow!
I said, “Since you’re being so honest with me, then you’re right, I have thought about you when, well you know.”
Mary being the ball buster that she is said, “No, I’m sorry, I don’t know, what you mean, can you please say it.” She had such a cute look on her face when she said it that I had to answer.
I said, “Ok, I sometimes think about you when I’m jerking off, happy?” She just smiled.
She said, “ok, it’s my turn and I’ll take dare, just to be fair.” I didn’t know what to make her do, I was really in deep thought when she said, “come on, there has to be something, I promise not to wimp out.” Before I had the chance to say anything, she said, “Fuck it, I dare myself to take off my bottoms.” She reached down and slid the bottom of her bikini off. I was dumbfounded, I was in the pool with my older sister, and she was naked.
I said, “Are you sure it’s only an edible that you ate?” She laughed and swam away, once again showing her ass, but this time, it was her naked ass.
She swam around for a little while and when she finally swam back to me, she said, “Look, it’s only us here, and I know from our talks that we’ve both been very lonely, right? Now after all these years, we finally have each other, and if this is a little out of the normal, who cares.” Then she said, “loose the trunks, and I’ll come out of the water, so you get a better look, deal? I loved the idea because all I could see was partial tit and not much more, she was underwater. I reached down, slid my shorts off and threw them on the pool edge.
I watched as my sister swam over to the stairs and slowly walked out of the pool. She walked around to where I was and stood at the edge looking down at me. She said, “So, what do ya think, not too bad for an old lady, right?” She was absolutely right. Her body was amazing! She didn’t have an ounce of fat on her and her tits were still pretty perky.
I said, “I need to see all the way around to make my final decision.” She gave me a nice turn, walked over to the lounge chair and crawled onto it with her ass facing me. I could see the lips of her pussy as she crawled, and then she turned over and laid down.
She said, “Now you’ve seen it all, what do you think?” Then she said, “Oh wait, sorry, you didn’t see this.” She raised her knees and opened her legs for a couple of seconds to give me a direct view of her bald pussy. Then she said, “Ok, now you’ve seen it all, so what’s your opinion of me?”
I said, “Your body is fucking killer, I guess you use dad’s gym a lot.” Then I said, “I could look at you all night.” She gave me a big smile then another quick look of her pussy.
Mary said, “Ok, it’s my turn for a show, get out of that pool. I need to see how you have grown since I last gave you a bath about 15 years ago.
I asked her, “Are you a little aroused right now?” She said she was, so then I said, “Well, yours doesn’t show, but mine does.”
She smiled and said, “Oh I’m counting on it, I don’t want to see him asleep, I want him wide awake.” My nervousness faded a little and I walked up the stairs. I walked around to the lounge where she was laying and stood right in front of her. She said, “Shit, you’re little dingy grew quite a bit since you were 3.” Then she said, “And I do mean quite a bit, your cock is huge.” Now I felt a little embarrassed, but I continued to stand there. Mary said, “Are you still ok?” I assured her that I was, and then she said, “Good, because I really need to do this.”
I watched as she opened her legs and started rubbing her clit as she looked at me standing there naked with a huge hard on. She said, “your body is fucking amazing, I need to give you a nice warm oil massage, would you be up for that?” It was hard to find my voice, I was watching this hot, 55-year-old woman, who happens to be my sister, masturbate in front of me.
But I did, I said, “Why would I say no to that?”
Then she said, “ok, we’re going upstairs and doing that, but first I want to watch you jerk off, will you do that for me?” I nodded my head and then she said, “but don’t cum, I’ll take care of that later, ok?” As she finished that sentence, she pushed her middle finger inside her pussy and looked right at my cock. I held my cock and started to stroke it slowly as she watched. I did that for a little bit, but I needed to do it faster and harder. As I picked up the pace she yelled, “Don’t cum.” I slowed down again and finally stopped. If I didn’t, I would have covered her in cum. She smiled again, got up and said, “follow me.” We walked upstairs to the master bedroom.
As we went in, Mary said, “Lay face down on the bed, I’ll get the oil.” I did as she asked, and she came back a few minutes later with the oil in a cup of hot water. I watched as she opened her nightstand drawer, reached in and grabbed a vibrator. She laid next to me and said, “turn away from me, I’m gonna take care of myself while we wait for the oil to warm up, but I don’t want you to watch, just listen, ok?” I turned my face away from her and her the click and buzz of her vibrator.
It was killing me not to watch her, and my cock was starting to grow uncomfortable underneath me I laid there listening to her breathing get heavier and heavier as she let out small moans. Suddenly I heard her let out a loud, “Ohhhh.” and I knew she was having an orgasm. It took everything I had not to turn and watch, but I kept my head turned away. I heard her click off the vibrator and a few seconds later I felt warm oil dripping on my ass. She started to smear it all over going between my cheeks and brushing my asshole. It felt amazing and her hands were so soft. She said, “Thanks for giving me some private time, I’ll let you watch next time, and by the way, that’s gonna be real soon because of this tight ass of yours.”