Senior Siblings Ch. 01

Life's been pretty good to me and now that I'm in my sixties I often look back on all the good times with family and friends. I've been blessed with kids and grandchildren, and I enjoyed a long happy marriage before I lost my wife a few years ago. Now I spend about half the year in Florida and the other half up north near my kids. Life is good.

Last fall I invited my sister to join me for an extended visit in the south and she happily agreed. Her kids are grown and her husband is gone so she has no commitments. She is two and a half years younger than me. I got to my Florida house is September and she joined me October first.

Sissy (my pet name for her since we were kids) is a bit of an uptight person and I knew it would take a while for her to get into the slower, more relaxed pace I enjoy living in Florida. I decided I would invite her to join me in activities but let her take life at her own pace. I enjoy boating, fishing, cycling, and I exercise for about an hour every morning after a leisurely breakfast. I also like people watching on the beach at least once a week.

After a couple of weeks, I could already see Sissy relaxing and calming a bit. She exercised and walked daily to stay in shape, and she looked pretty good for her age. I think she could pass for fifty. At 5 foot 6, she's about ten inches shorter than me and pretty slim with cute little B cup tits.

She was enjoying reading and sunbathing by the pool and I had to keep reminding her to apply the sunscreen. I explained to her the need for SPF50 if she was going to do this often, even though the pool was screen enclosed. Her skin is surprisingly smooth and soft for her age and I enjoyed applying sunscreen for her but she kept me limited to her back.

At the beginning of week three of her stay, Sissy told me she didn't want to wear out her welcome and she was going to book a ticket home. I asked her why she was thinking of leaving and what she was going to do in the cold up north. She admitted that she loved it here and just didn't want to impose. It took a while, but I finally convinced her I truly enjoyed her company and it was much better than being alone (for both of us), so she said she would think on it for another day or two.

The next day after dinner and a couple of glasses of wine, she asked me a question and asked me to be completely honest with her: "What does my presence here keep you from doing that you would be doing if I wasn't here?"

I let the question sit for a few minutes as we watched the boats going by on the canal only fifty feet away. It was a pleasant evening with a light breeze and the stars were just coming out. Finally I said, "Okay, if you want me to be completely honest, there is one thing I would be doing if I was alone, that I do miss. But I need to pour us each another glass of wine before I share it."

A few more boats passed on their way home, a bit of wine and relaxation, and I started, "I need to begin by telling you a story that you might find a bit surprising. It's about a habit that we developed over several years of marriage and travel to the Caribbean, then we continued here in Florida. It started a long time ago in St Martin and other islands that we visited once or twice a year when I convinced Mary to go to nude beaches."

Sissy sat up in her chair with a jolt and said, "Are you telling me you and Mary went nude in public?"

"Yes, that's where it started, when we were in our late thirties."

"What do you mean 'started', are you saying you're a nudist?" as she started laughing hysterically.

Fortunately, it was pretty dark by the pool so she couldn't see me blushing in embarrassment by her reaction. I said, "Okay, forget it, it's not that important." As I began to sulk.

After she got over her laughing fit, she said she was sorry but she never imagined that from me or my late wife because she saw both of us as so straight-laced. To which I said, "Look, it's not like we went to orgies or something, we just like being naked. You ought to try it, it would be good for you, you're the one that uptight!"

This wasn't going the way I had planned and I felt bad for saying that. I apologized and suggested we forget the whole thing. To which she apologized and said she was just shocked but really wanted to hear the rest of the story, but first she needed to pour us each another glass of wine.

I spent the next hour filling her in on the details of our progression from topless beach to nude beach, to full nude resorts where we only dressed when dining on the "prude" side. We socialized, played water sports and games, met new friends and felt so free and relaxed, all while nude. And we had great sex because we were always energized and aware of our bodies. And yes, every size, shape and age go nude, not just the "beautiful people".

When she finally stopped asking questions, I filled my wine glass and told her I was going in the spa and enjoy the stars. At the spa, the only light was from the sky, so I discretely dropped my shorts and sunk into the warm water to relax. Sissy went inside to change into her conservative one-piece bathing suit and joined me in the spa.

After a few minutes of enjoying the night sky, she said, "You make it all sound so innocent and relaxed."

"That's because it is. Unless you want to make it into something more, which is completely acceptable also," I said. "Don't get me wrong, I also enjoy looking at attractive bodies, both men and women. And my mind does wander, so did Mary's. At night we would share our thoughts about who we found attractive and why. That lead to some great sex."

Sissy fidgeted nervously and took a sip of her wine. After several minutes of silence she asked, "What do you think of my body?"

I immediately knew my response had to be well thought out and expressed properly to reduce the risk of offending, but still being honest.

"Honestly," I said, "you are in your sixties but from what I've seen of your body, you could easily pass for fifty. You take good care of yourself and exercise, and you should be proud of what you've got."

Another fifteen or twenty minutes passed with neither of us talking, just taking in the beautiful night. I yawned as I stood up and grabbed a towel to dry off. I turned to face my sister and said, "I'm going to bed, good night." As I stepped out of the spa I remembered that I was naked but figured it was too dark for her to see much anyway.

I woke the next morning to another beautiful day in Florida, threw on a pair of gym shorts and headed to the kitchen. Sissy had already made the coffee and was out by the pool as the sun rose. She had on her standard oversized t-shirt and grey cotton shorts to give her that overall frumpy look. Soon after I sat down Sissy asked, "What did you mean when you said I was uptight?"

I took a couple of sips of my coffee as I carefully considered my response so I wouldn't hurt her feelings. "Like I told you last night, I think you look great for your age, and you should show it off a little bit. You might enjoy the looks and compliments you'd get from others if they could see a little bit of your body."

"What do you mean see my body?", she asked, a little indignant.

"I don't want to hurt your feelings but you dress pretty conservatively and you have a body that deserves to be shown off, even at your age. How you present yourself will also change your own opinion about yourself." I suggested.

The conversation continued and she seemed genuinely interested in what I had to say. I carefully pointed out her "frumpy" style of dress and how it hides her beauty. Well, I guess she took my suggestions to heart because I saw her online shopping later that day and packages started arriving within a couple of days.

She soon caught my attention with a pretty bikini under a semi-shear coverup. I was already in a lounge chair by the pool, and I couldn't believe my eyes. She was even better looking that I suspected. Her beautiful, smooth skin was pristine. Probably because it had never seen the light of day.

"Wow! You are gorgeous! You look awesome, I can't believe you've been hiding that body from the world all this time," I said with all sincerity. This made her blush, and it took a bit to convince her I was dead serious and not just giving her a line.

I enjoyed several fashion shows in the coming week, and I started to get excited each time a new delivery driver showed up at the door. Sissy was really getting into this and enjoying herself. She even had her hair and nails done and I convinced her to treat herself to a massage, something she had never done.

One morning Sissy was at the coffee pot pouring herself a cup with her back to me. She had on one of her new shear cover-ups. She turned away from me and headed to the lanai as I poured my coffee. It took a couple of minutes before it dawned on me that she had no top on under her coverup. I just smiled and didn't say anything, trying not to make a big deal about it. She was testing out a new experience and I didn't want to screw it up.

After coffee, we each went about our morning routines and around noon we joined up back at the pool for a dip before lunch. Sissy had again donned the morning outfit of bikini bottom with shear coverup and no bra. I was already in the pool when she arrived and I tried not to stare as she nervously unbuttoned and removed her shirt, dropped it on the chair and turned to face me as she enter the pool.

She moved quickly down the steps and sunk into the water as she looked at me and blushed. Smiling, I said, "it's been a long time since I've seen such pretty little titties. I'll say it again, you really are beautiful. And you have nothing to embarrassed about."

She soon relaxed and swam for a bit but seemed hesitant to come out of the water. "Are you up to sitting by the pool for lunch like we usually do?" I asked with a smile.

"What if a boat goes by?" she replied.

"Then you simply, nonchalantly cover yourself or turn away for a minute. Nobody will notice anything if you're discrete and nonchalant." With that we took our usual chairs facing the pool and the canal beyond.

Over the next few days nothing more was spoken about it and Sissy was becoming more and more comfortable being topless around the pool and in the house. On day five she didn't even put a top on when we sat down to dinner. She had truly adopted the topless lifestyle. On day seven of her new-found freedom, she almost went for her neighborhood walk topless, catching herself as she was walking out the front door. When she did wear a top, she didn't bother with a bra. Her little titties didn't really need anyway, even at her age.

The next day we were getting ready for a dip in the pool when she said, "I'm okay with you not wearing a bathing suit. I know you'd much rather go nude."

That's all the encouragement I need. I checked that no boats were coming by and dropped my shorts right there in front of her. I grabbed a towel to hold in front of myself as I walked to the pool and then dropped it to the side as I went down the steps into the pool.

I'm pretty tall so standing in the shallow end the water only comes up to just below my crotch, leaving my cock exposed until I walked in deeper. Sissy didn't take her eyes off me until I was up to my neck in the water. With a big smile I couldn't resist saying, "I'm okay with you not wearing a bathing suit too, I know you'd much rather go nude."

She just laughed and said, "In time." But she surprised me again when she came back from doing a lap with her bottom in her hand and threw it on the pool deck.

By this point I was getting more and more of those tingly excited feelings just like when my wife first exposed herself on the beaches in the Caribbean. I'm pretty sure my sister was getting the same feelings. It's like you're being naughty and you know it, but you really don't want to stop. It makes you feel like a kid, even in your sixties.

The next night it was my turn to make dinner. I made grilled salmon, roasted potatoes and a nice green salad. I paired it with a couple of bottles of a nice Chardonnay. The evening was a little cool so we both put tops on and dined in the lanai, watching the last of the boats coming back in from their day on the water. The spa was heating up and I was looking forward to a relaxing evening under the stars.

After dinner I wanted to catch up on a few emails so I filled my wine glass and went into my office. Time passes quickly when I'm on the computer and before I knew it I had been there an hour when Sissy showed up at my office door and said, "Hey, are you going to stay here all night?"

I turned to look at her and was shocked to find her standing in the doorway with the second bottle of wine in one hand and her glass in the other. And she was completely naked with a big smile on her face. Wow, what a transformation. What had I created? Not only was she embracing a nudist lifestyle, but she was also so much happier and more relaxed than I had ever seen her. She turned and led the way to the spa as I followed while stripping and grabbing a couple of towels.

We poured ourselves another glass of wine and sat back in the warm water to take in another beautiful night. I told Sissy about the change I had noticed in her and, after a few minutes of thought, she said, "You know, I can't remember when I have felt so happy and relaxed. It's so freeing to be naked, I wish I had discovered it sooner."

"And you know what else makes me feel good?", she continued, "I love the smile on your face when you look at me naked. And I'm pretty sure I've seen you lick your lips more than once when you are looking at me."

Now it was my turn to blush, fortunately it was too dark for her to see that. I didn't know what to say. I had no idea my enjoyment of her was that obvious.

By now she was getting a bit tipsy so I didn't want to say or do anything that we'd regret later, but apparently she was beyond that concern. She put her wine glass down and stood up in the spa. The water came up to about her belly button. She took a few steps closer to me and placed her hands on her hips as she began to sway to the music as she slowly slid her hands up her belly and cupped her little tits.

"I guess you really do like my little titties, don't you?" she asked as she pinched her nipples and twisted them between her thumbs and forefingers.

I knew I shouldn't, but I couldn't stop myself. I stood up and moved close to her. She moved her hands to my chest and nipples which were right about mouth level for her. I placed my hands on her shoulders then slowly down her back, pulling her closer to me as I did. She had reached down and lifted my cock so it was now pressing against her belly as we held each other tight.

I reached down and grabbed her ass cheeks and lifted her up while she wrapped her legs around my hips. Her face now at my level, our lips met and then our tongues began to dance with each other.

The urge to continue was overwhelming but I somehow found the strength to break off the kiss and say, "Sissy, not tonight. I want you to be sober so we both know what we are doing. Please don't be upset." And then I kissed her again before putting her down in the water.

We sat together in the spa for a few minutes more when she finally said, "Thank you for saying 'I want you'. And I think I need to go to bed."

I sleep in the master bedroom, a large sliding door opens onto the lanai. The door to Sissy's room is about ten feet away from mine. We usually sleep with the bedroom doors open to get good air flow. Sissy went to her bed as I closed up the house for the night and went to my bed, and just laid there thinking about what had just happened. I had no idea if this was a onetime mistake helped along by too much wine, or if we were headed down a path that we both wanted and could live with.

About fifteen minutes after I had turned out the lights, I heard some sounds coming from Sissy's room. I froze and listened intently. Her breathing was getting louder and faster and I was getting hard just listening to her. I started stroking myself as she continued. I could believe this; here I was jerking off to the sounds of my sister masturbating in the next room!

Within a few minutes I heard muffled moans as she unmistakably enjoyed a very strong orgasm. I couldn't believe she had just masturbated to what sounded like a great orgasm. Just the thought of it sent me over the edge as I shot my load on my stomach.

I was up first the next morning and made the coffee. Just as I was pouring myself a cup, Sissy came prancing into the kitchen as happy as a lark and as naked as one too. She walked right up to me, grabbed ahold of my gym shorts and pulled them down to my ankles with the declaration that "from now on this is a naked house!"

As she poured herself a cup of coffee, she added, "Oh, and I believe being naked is the one thing you said you'd miss with my staying here. So, problem solved! And I want to stay for the winter. That is, if you will have me." She smiled mischievously with the last sentence.

Clearly, wine wasn't the only motivation last night. She was a downright horny woman. I had a hard time getting my head around the whole thing. Not that I was at all hesitant, just shocked by my baby sister and the speed of her transformation. It was like she was dancing on a cloud. I was happy just because she was so happy. And we obviously had a lot of territory to explore ahead of us.