Grandmother's Lessons Pt. 01

I had just turned 18 and had finished high school via home schooling by my parents. They both worked as missionaries throughout my entire life, moving every five or six years. My mother taught me my school lessons the entire time as we weren't often near an English speaking school.

Now it was my time to begin college but my parents were to continue their foreign work, so I had to part from their company as well as their oversight. Problem was, I had been brought up in a mostly sheltered environment and they weren't sure I was ready for the "real world" of life in the States. So, what was to become of me?

Finally my father got into contact with his mother, despite them not being terribly close these past eighteen years. I was not privy to their conversations of my going to live with my grandmother, so I wasn't aware of my parents hesitancy of turning me loose to my grandmother. As I had only met her two or three times my entire life, I was unaware of why they were hesitant. But as I had no other relatives, it was either her or I would continue to live with them in third world countries, forgoing further education.

At last the decision was reached, agreements made and I was told to pack all of my belongings to take with me. As we had lived extremely basic, all I basically had were my clothes and a few books. My mother escorted me to the bus station and I could tell she was uneasy about the arrangement but didn't know why.

While we waited on the bus, my mother began to tell me some about why they had such a hard time with this decision.

"John", mother began, "your grandmother is a bit of loose cannon when compared to your father and I. While we lived to serve, she took a much different path in life. Oh, there's nothing evil or mean about her. It's just that she sees things much, much different than your father and I. While your scholarship covers your schooling costs, we cannot afford to house you on what your father gets paid. Your grandmother has graciously allowed you to stay with her while you're in school. But if you're ever to decide to leave, for any reason, then just let us know. We'll figure something out eventually."

Mother had a look on her face while telling me all this, a look I had never seen before. It was as if she wanted to tell me more but didn't know how or (probably) was told by my father to not tell me any more. But I trusted her and my father, so I got on the bus when it was called. We waved to each other as it drove, with me wondering how long it would be before I could see them again. I knew we would write but they were headed somewhere to interior Africa, where mail service was going to be iffy, if not rare.

I slept most of the way on my trip, only waking when the bus got close to my destination in South Florida. I knew grandmother lived around the Palm Beach area, but that was about it. I looked forward to being in Florida as well as being able to spend some time on the beach for the first time in my life.

Once the bus arrived at the station, I gathered my gear and headed inside the terminal. I didn't have a picture of my grandmother, so I wasn't quite sure how we would recognize each other. Thankfully, that wasn't an issue as she recognized me.

"John?" a woman asked. "Are you my grandson John?"

I turned to look and almost dropped my things. In front of me stood a remarkably good looking woman, barely older looking than my own mother. She was a tall woman, about five foot ten, with blondish hair and looking extremely fit and slender.

"Yes, I am John. Are you my grandmother?" I asked this good looking woman.

She laughed and came forward and hugged me. Due to her height, we were virtually eye to eye. She hugged me tightly, pressing her body right up against mine. I became acutely aware that I had never been hugged so tightly by a woman in all my life, much less one so good looking. I became aware of a stirring in my groin, something I was becoming more aware of as I got closer to eighteen. I hugged her back politely, unsure of what the proper thing to do would be with my penis enlarging as it was.

Grandmother let loose of me but held my arms in her hands as she looked me up and down. While I had filled out due to hard physical work while living in underdeveloped countries, I was not quite so advanced on my social skills.

Finally she loose of my arms and smiled, putting me greatly at ease. How could I be uncomfortable with such a good looking woman smiling at me? Turns out, I couldn't and immediately relaxed.

"Let's get you stuff and be on our way, shall we?" she said. So we grabbed all my bags and off we went to her car. She walked me out to the parking lot, just chit chatting about my trip and so forth, not really saying anything important. When she stopped at her car, I noticed it seemed to be very nice car, based on what little I knew about cars. We quickly piled everything into the trunk and we both got inside. She quickly got us out and onto the road.

"I'm sure we both have a million questions about each other" she said. "How about I go first and tell you about me and then you can ask what you want then?" I just nodded in reply, anxious to hear what she had to say.

She began her story: "I had your father when I was only eighteen. I married an older man whom was quite successful in business but had never had time for a wife and family prior to me. We were quite happy until he died a few years ago. I'm afraid your father and he didn't see eye to eye on his wealth nor how he acquired it. I guess that's what drove him to missionary work. We remained in touch all during your childhood but of course with the distances involved, I never got to see you but rarely. I look forward to making up for lost time now that you're staying with me."

I remained silent, doing the math in my head. She had my father when she was eighteen, my dad had me when he was twenty. Wow! Grandmother wasn't even forty! No wonder she looked like my mother's older sister instead of her mother-in-law!

In no time at all we had arrived in a well to do neighborhood by anyone's standards. Grandmother pulled into the garage and let the garage door down. We gathered up my bags and shuffled into her house.

"Follow me with your stuff, I'll show you which bedroom is yours. I'll put you right next to mine so we can peek around the door should you need anything." Again, all I could do was nod as I wasn't sure what to say or how to act in such nice surroundings. I decided I was going to enjoy such luxury after living in primitive conditions all my life.

My bedroom was very spacious, with a nice bed and furniture. Grandmother helped me unpack, sort my clothing and get squared away. Once all that was done, she again took charge, sensing I was out of my element and thus out of sorts.

Taking my arm, she said, "How about I give you a tour of the house, let you get a feel of it?"

Without waiting for a reply, she walked me over to the bathroom that connected to my bedroom. It was larger than some of the homes I had lived in as a kid.

"This is obviously the bathroom. My bedroom is on the other side, through the other door there. I wanted you here in case you needed anything and to make you as comfortable as possible. We'll just share the bathroom as we need to unless you want to do differently?" she said.

She then walked me through the rest of the house, something that took close to an hour as she explained the things she thought I needed to know. Finally, we arrived at the den. She walked me through the sliding glass door to the backyard, where she proudly showed me her swimming pool. My eyes were as round as silver dollars at this feeling of excitement that grew within me. I had always wondered what it would be like to live like this and now I would get to know!

"How about a swim? Are you up to that after your trip?" she asked.

I replied, "It sounds like a wonderful idea, Grandmother. But I'm afraid I never learned to swim due to never having a safe place to do so."

Grandmother just shook her head. "I knew your father made sacrifices doing his work but I wished he hadn't made you do them as well. Oh, well. What's done is done. How about this? Slip on your bathing suit and we'll just wade around for a bit, enjoying the warm water?"

Again, I shook my head in puzzlement and said, "Sorry. I'm afraid I don't even have a bathing suit. Shorts either for that matter. I always wore long pants no matter the weather or time of year. Modesty and all that, father always said."

Grandmother rolled her eyes and muttered some things I couldn't quite make out. Then she stepped back a bit and again looked at me up and down. "Hmmmmm. We're about the same height. Obviously you're filled out a bit more than I am but you're still a bit slender. I have an idea if you don't object?"

I wouldn't object to anything at this moment, all I wanted to do was get into that glorious looking swimming pool and begin to enjoy it!

"Sure, grandmother. Anything you want is fine with me. I place myself in your hands and abide by your wishes" I replied.

"Super!" she said. "Let's go back upstairs and see if we can't get you something to wear so we can both enjoy the pool."

Grandmother grabbed me by the hand and led me back upstairs to her bedroom. It was every bit as nice as the rest of the house and just a bit larger than mine.

"Stand right there and let me see what I can do for you" she said. She then began rummaging inside one her dresser drawers until she exclaimed, "Aha! Found it! I thought I still had it."

She pulled out what turned out to be one of her old bikini bottoms. The only reason I knew what it was is I had seen pictures of bikinis in some of the old magazines Americans had left behind during my postings.

She instructed me to go into the bathroom and take off my clothes and slip the bottoms on. She would change into her suit as well. So off we both went to change.

I stripped off my clothes, again feeling a bit excited with what I was doing. Not only was I getting to finally get rid of wearing long pants all the time, I was getting to wear something that was pretty minimal in terms of amount of material.

I looked at the suit after I had stripped down, unsure of which way to wear it. Finally I located a tiny remnant of a white tag, so I thought that would go in the back. I also noticed there was no lining what so ever in the suit. It was basically nothing more than a super thin fabric with an elastic waistband. I just shrugged, slipped it on and thought grandmother knew what she was doing.

As I pulled it up, I immediately felt a surge of sensations. The suit cupped my groin snuggly, giving me a feeling of a caress. I had always been taught to not to touch my privates unless I was washing or peeing, so this was extremely exciting to me. I again felt a wave of heat flow through my groin, something I had felt before but didn't know how to handle.

I glanced in the bath mirror before I came out. I saw the suit fit me like a second skin, wrapping both my crotch and my butt. I didn't know if it could be any more thinner and still be able to be worn. I wondered how it would look when it got wet? Ah, who cares? No one was here except for grandmother and me anyway.

I re-entered her bedroom just as grandmother was slipping her top over her head. I really hadn't thought about announcing my return and just blundered back in. I had a fleeting thought that had I not stopped to look in the mirror, I might have caught her topless! Whoa! Where did THAT thought come from I wondered?

"John, be a dear and tie my suit string" said grandmother. She was holding the sides of the strings with each hand, her back facing me. I walked over to her, noticing that her suit bottom was just as thin and snug as mine was. I could faintly make out the crack of her butt as well. This again led me to wonder what her suit would look like once it got wet?

I dutifully tied her suit top strings together in the back, redoing it on her direction as she said it was too tight the first couple of times I tied it. When it was done to her satisfaction, it hung very loosely in the back, allowing her front to shift easily every time she moved. I tried not to look too obviously, but being this close to a gorgeous woman in a small bikini for the very first time was a bit unnerving.

Finally we were done and again grandmother took my hand and led me out to the pool. She walked me down the concrete steps into the water, still holding my hand. As the water came up to our waists, she turned to me. I was looking everywhere but at her face, noticing how flimsy her bikini top was as she moved.

"John", she said. "How about I teach you a few simple things about swimming to start? Maybe floating, that sort of thing?" I just nodded again, too tongue tied to properly reply.

Grandmother led me out into slightly deeper water, now almost chest deep. I glanced down at the front of my suit & couldn't believe it! It was virtually transparent! It was almost as if I had no suit on at all! I could easily see my pubic hair, my penis, everything! I stole a quick glance at the front of grandmother's suit bottom. Same thing for hers! Wow! My first look at a female's pubic hair and it was my grandmother's!

I looked back up at grandmother's face and she had a devilish grin. "Having fun so far?" she asked. "So am I" she said.

"Ok, I'm going to float you onto your back but I'm going to support you until you learn how to do it by yourself. Just kick your legs straight out and hold them out."

With that, she scooped my legs out with one arm while holding my up out of the water with her other arm. She slid her hand to the bottom of my butt once my legs were out straight, holding me afloat. I was acutely aware of her warm hand on my butt, something I had never experienced before. I wasn't sure, but I almost thought she had grasped my butt with her hand!

As she supported me, I noticed other things as well. For starters, my suit was totally transparent. I may have well had nothing on at all. Another thing was, I have the beginnings of a first class erection. I knew what it was as I often had them when I first woke up in the mornings, but this was the first time I had gotten one in response to a female touching me. It began to strain the front of the suit, creating a noticeable bulge.

Grandmother still maintained her grasp on my butt cheeks while holding my neck with her other hand. She pulled me close to her, allowing my side to be right against her, no space at all between our bodies. If it was possible, my penis began to get even harder! What was I going to do, I wondered?

Grandmother began to speak to me in a soft, flowing voice. "Just relax, John. Enjoy the water as it flows around us. Close your eyes, just pretend you're floating in a cloud."

Hunh, some cloud, I thought. Pressed up against a gorgeous woman while I had an erection AND wearing a suit you could see through? But still, it WAS an incredible feeling. I slowly relaxed, enjoying the warm water enveloping my body, wondering if the softness of her body pressing mine was something she was aware of?

We slowly drifted around the pool in this position, I relaxed as I listened to her melody of words. All the while I never felt her hand leave my butt cheeks.

"Ok, John" she said. "I'm going to adjust my hold a bit and lets see if you can float a bit. She let loose of my neck and shifted her hand that was on my butt. But rather than removing it, she simply moved it to another hold! Now her hand spanned my but crack and I felt her thumb slip between my cheeks, sliding up to touch my ball sack! Holy cow! Was I dreaming or imagining this?

Apparently not, as she snugged her thumb even deeper into the crack of my butt. I felt her wiggle her thumb, striving to have it gain a deeper resting place. I felt it rest directly on my sphincter, igniting feelings in me that I never dreamed existed! It felt WONDERFUL! I let out a sigh as I felt her thumb begin small circular movements directly on my sphincter! If I died right then, I would die happy!

As a reflex, I spread my legs a bit. This allowed her thumb better access, something I hadn't thought about but never the less enjoyed. Grandmother hadn't spoken since she did her hand shift, perhaps she was focusing on her efforts?

Grandmother continued her thumb's massaging of my sphincter, the pressure a bit more insistent now. I was torn between the relaxation of the warm water and the excitement that her thumb was giving me.

She then whispered in my ear. "John. I just had an idea. Since it's so warm here in the water, how about we just slide your suit all the way off? Would that be okay with you?"

"Oh, yes, grandmother!" I replied.

Holding me back under with one arm so I wouldn't sink, she removed her thumb from its fun. She used that hand to slide my suit down one side and then the other. My erection popped up and out as she slid the suit over it. Neither of us commented on it, she just continued to slide the suit down until I kicked it completely off.

I again let my legs drift apart as her hand returned to it former position, her thumb firmly against my sphincter. She again began her rubbing motions, slowly but a bit more firmly this time. I wasn't certain, but I almost felt the tip of her thumb begin to enter me!

Then the uncertainty disappeared as grandmother slid her thumb gently into my opening! I arched my back and gasped in pleasure. I had NEVER felt such pleasure in all of my life. I wanted this feeling to never end!

"Do you like this, John?" she asked as she finally buried her thumb to the hilt in my butt, holding it in place while giving me a chance to process the intense feelings it was generating.

"Oh, yes, grandmother! I'm enjoying this very much! How did you learn to do this?" I asked.

She slowly began to slide her thumb in and out of my butt as she began to explain. "Your late grandfather was a fan of having me to this to him. We often played this way with each other, but he taught me how to do it to him first. I became quite fond of it, seeing how much pleasure it gave him when I did it. It seems you too are enjoying having it done. Is that right?"

I couldn't answer, all I could do was moan in response. I had no idea my butt could derive such pleasurable feelings! I wondered if anyone else had ever experienced such pleasure before?

Grandmother kept working her thumb in and out, moving at a steady pace, keeping me at a high level of excitement.

She again whispered in my ear, "Would you like me do something else that's even more enjoyable, John?"

For the life of me, I couldn't begin to guess what would feel even better than this, but I again bowed to her experience. "Oh, grandmother, you can do anything you want to do!" I said.

Grandmother had slowly moved us back over to the concrete steps while talking to me. She slowly slid her thumb all the way out of my butt, leaving me with an empty and neglected feeling. She helped me stand back up next to the steps.

"Don't worry, I'll continue in just a moment. Sit up on the side of the pool and put one leg on each side of me" she said.

I quickly went up the steps and got into position as she requested. She had me scoot forward some, so that my butt was halfway off the side of the pool. I realized she did this in order for her to regain access to my sphincter.

By now my erection had reached a point I had never felt before. I thought I could drive a nail through a board with it, it was so hard.

Grandmother told me to lean back and use my hands to support myself. She then took her middle finger instead of her thumb and placed it on my sphincter. I felt the tip firmly against my opening and was ready to hunch down on it if she didn't quickly insert it!

"John, I want you to look me in the eyes. I want to see the pleasure when I start again."