Grandma Knows Best

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Double Penetration

Whatever merit this story has is solely due to the herculean efforts of Literotica editor Maximus The Mad. The failings are completely my own. All characters portrayed in this story have reached the age of 18 or well beyond.

Page 1

Graduating from high school and not having any other plans for my summer vacation, I convinced my parents to let me accept my grandmother’s invitation to work the summer helping her on what was left of the old family farm. Her regular summer helper had graduated from college and moved away. There was lots to do on the farm in the summer and I was pretty sure I would be paid generously for my labors. My father helped persuaded my mother to go along with the idea. He assured her that the experience would make a man out of me. It wouldn’t have been my first choice on how I wanted to spend my vacation, but it was my only choice. I really didn’t have any other options.

On the plus side, I had just turned 18 and figured hard work would help me build my muscles which were starting to pop when I posed for the mirror. I was also hoping a toned bod would improve my chances with the coeds when I started college. The school year quickly came to an end and before I knew it, my parents and I were in the car driving up to the farm. After lunch, my parents took off and my summer experience began. I felt a twinge of sadness watching their departure.

My grandmother was in her mid-sixties and looked every bit her age. She lived in the country and was a widow. The burdens of farm life had taken its toll on her. For one thing, she was rail thin. When I looked at her hands, they appeared little more than finger bones wrapped in blood vessels and sinew with a thick skin vacuum sealed around them. Her hands were dark from the sun, but not bronze. They were a deep yellowish color resembling chicken skin but darker. She usually wore jeans and the pant legs always seemed baggy on her. Her hair was grey but it was a composite gray. Some hairs were black and the others white. I would say it was about 70 percent white. It was short and formed tight natural curls around her head. There was never any effort to style it or improve her appearance with makeup. Her face had no attractive features and the lower part of her face protruded slightly forward. Farm life was arduous and she had all the physical characteristics of one who had spent years at hard labor.

Morning came far earlier than usual when my grandmother woke me up at 5 am. She had warned me the day before but the reality hadn’t sunk in until being shaken awake while it was still dark. Animals had to be fed, eggs collected, stalls had to be cleaned and fields had to be tended to. The farm’s chief source of income was from the sale of vegetables and eggs. There was a chalkboard sign that was periodically placed on the roadside advertising what was available. On Saturday mornings, these eggs, vegetables and frozen meats from the occasional slaughtered hog or lamb were sold at a stall in the city farmer’s market. Grandma had her regular customers who counted on her natural organically-grown products.

Thursdays and Fridays were devoted primarily to harvesting the corn, strawberries, asparagus, peaches, tomatoes and greens. Early Saturday morning was spent loading the pickup and setting up for business by 8:30 in town at the farmer’s market. Grandma enjoyed interacting with her customers, many of whom had become her friends over the years. The clientele were largely middle class people interested in wholesome food and they didn’t mind paying for it. There were a fair number of Volvos, BMWs and Mercedes in the parking lot. I worked hard to help out as I gained some sales proficiencies. It was a very hectic few hours until we closed up shop at noon. There usually wasn’t much left to take home so it was donated to the local homeless shelter.

There were some cute girls working in the other booths that I hoped to get to know better. There was one customer, Tammy Williams, who looked like a movie star. She was tall bout 5′ 10″ with striking looks and beautiful red hair. She was possibly in her mid-forties and an absolute knock out. I looked forward to meeting her each week. She was very friendly and addressed me by name and insisted I call her Tammy which made me comfortable talking with her.

As quickly as we set up, we just as quickly packed up and left. The rest of the day would be fairly low key. We always stopped at the Cracker Barrel restaurant for lunch on the way home. Farm life was becoming routine for me and I was enjoying it more and more, however there was one thing I lacked and it was a social life.

I never worked so hard as I did that first week. Each evening Grandma and I watched TV for a while after dinner and we were in bed by nine. I think I was asleep before my head hit the pillow. At five the next morning my grandmother would be shaking me awake. It seemed as though I had just closed my eyes. The only exception to this routine was Sunday when Grandma told me I could sleep as late as I wanted.

When Sunday morning came, I finally stirred to life around 9 in the morning and started stretching and yawning. My hands gravitated to my morning xnxx woodie which had been neglected for a week and was screaming for attention. On this first Sunday, my arm was hitting its stride as I closed my eyes and concentrated on the task at hand. Nature was in control as the launch sequence began. I was in the final count down when grandma came in the room to call me for breakfast. As I scrambled to cover up, she quickly backed out of the room with a quick “Sorry” and was gone. I didn’t come out of my room until noon and didn’t know how I was going to deal with the situation.

There was no explaining that grandma didn’t see what she saw. I just planned to face the music and apologize. Grandma was fixing lunch in the kitchen still in her nightie. I bit the bullet and joined her.

“Grandma,” I said, “I want to apologize for what happened this morning.”

She quickly replied, “No you won’t. What you did was perfectly natural. Everybody does it including me. You have to understand, we live on a farm. There’s no room for modesty on a farm. When you reach in a cow’s birth canal to pull out a calf or when you’re in the field and nature calls, you squat and do your business. On hot days, I’m prone to taking a quick dip in the pond and can’t be concerned about appearances. We’ve got to sort this out so we can work together and not be self-conscious. When your grandpa and my boys were here, we never had this problem and I’m sure you and I won’t either. I’ll give a little thought about how we can get past this. Meanwhile, get ready for lunch.”

I was incredibly relieved.

The week flew by and we were coming home from the farmer’s market and I was looking forward to lunch at the Cracker Barrel. I was anxious to tell my grand mom that I had arranged for a movie date that evening. Grand mom knew the young lady and her family and approved. During lunch, our conversation took a more serious turn. She explained that now that I was socializing, I had to understand that she was a very private person as are most farmers. Essentially, she wanted it made clear that we did not discuss our private affairs with others.

She continued, “On the subject of our farm life, I’ve given some thought about dealing with issues of modesty that can interfere with our normal business. Tomorrow is Sunday and this Sunday is going to be a no-clothes day.” She must have seen the expression on my face as she quickly added, “Don’t give it any mind, you’ll do just fine.”

Sunday came and, as usual, grandma woke me up. By the time I was coming to my senses, I saw her slipping out the door. She wasn’t wearing any clothes and I got a glimpse of her backside as she left. I had been hoping that she wasn’t serious about no-clothes day. I joined grandma for breakfast wearing jockey shorts.

As I gazed at my naked grandmother, she took one look at me and sternly said, “No clothes day means just that, no clothes.”

I took my place at the table and slipped off my shorts while seated. I was pretty much concealed by the table. Grandma was frying eggs at the stove. I couldn’t help staring at her. Her backside wasn’t at all boney as I has suspected. It drooped a little but had a cute quality. She was very thin but there was a small flap of belly that hung down at her waist. Perhaps the best adjective to describe her body form was wiry. Her abdomen bulged out slightly like she was a tad pregnant and her crotch was dark with mostly dark black hair with some white mixed in. Her breasts were droopy hanging down to her upper belly. They were somewhat flat but not all the way. Each breast looked like a scrotum with a single testicle the size of an orange hanging in it. The nipples faced forward and were dark and looked firm. It was hard not to stare and while they didn’t excite me, I longed to feel them out of curiosity.

Breakfast was served. Conversation was strained. Grandma tried making small talk but it was like trying to ignore the elephant in the room. Grandma asked how I enjoyed my eggs and then cleared the table. I just sat at there.

Finally, she said, “Robbie, I want you to join me in the living room. I thought we could watch a movie together.”

I joined her on the couch where she indicated where I should sit. She was thumbing through a bunch of DVDs and didn’t pay much attention to me. She put on a DVD and she returned to sofa so we could watch the show together. I was really jolted when the movie started. It was hard-core porn with two men and two women.

Grandma told me, “I figure the quickest way we can get past this modesty issue is to watch this move together and masturbate in each other’s presence.”

Masturbation was the furthest thing I had on my mind at this moment. Grandma went right to work. She produced an eight inch dildo and lubed it. She explained that at her age, a little lube was helpful. She slid forward on the couch, raised and spread her legs a bit, turned the vibration on and then slowly slipped it in her dark hairy pussy. She had a contented look on her face. I couldn’t believe my eyes. It was surreal. I had never been with a naked lady before much less a sexual performance. I was totally transfixed.

Grandma brazzers saw the cushion I had placed on my lap and turned to me and said, “Ditch that pillow and get to work or I’ll start wanking that wiener for you.”

Actually, I was getting ready to do the deed myself as the movie was incredibly erotic and grandma’s performance were taking effect. I took hold of my dick and slowly started moving it around as the sensation in it began to build. I was dividing my attention between the movie and grandma who was thrusting the dildo in her pussy with one hand and rubbing her clit with the other. The movie was stimulating, but grandma was far more interesting and she was real and right next to me. It didn’t take long for me to get hard and I slowly started to stroke my dick. I really didn’t want to shoot my juice in front of grandma and I was hoping she’d finish her business and leave.

Grandma was really going at it and was quickening her pace. Then she started moaning. Her moans began coming more frequently and louder. I noticed that she was breaking out in a light sweat and she began to frantically work her clit. Then she threw her head back and let out a loud “Yowl” and began slowing down then ceased her activity.

She turned to me and said, “That was a good one.”

She wiped her face and then her pussy with a towel she had brought. She sat up and looked at me.

She said, “You’ve got a good-looking dipstick there and if you don’t want to the job, I will.”

I began to apply myself more fervently to the task at hand. I didn’t think I would be able to shoot with my grandmother watching but I did. The first shot went over my shoulder. The next three spurts landed on my chest and belly.

Grandma seemed thrilled with events.

She excitedly said, “That first one was a three pointer.”

Then she began cleaning me off. I would have thought she’d leave that task to me but she didn’t. She spent a good bit of time on my dick and nuts. She first used a wet washcloth then a towel and really worked on my equipment making a number of complimentary remarks about its appearance. It was the first time another person had ever touched me. I liked it. It felt much nicer when someone else handled me there.

I thought that we would get dressed after our morning session, but that was not to be. We spent the rest of the day together naked. I was amazed because grandma was right. My modesty was gone and I actually enjoyed walking around with my dick flopping around. Grandma gave me a goodnight hug that evening and her breasts pressed against me. I felt her nipples against my chest and they were hard.

As I entered my bedroom, she said, “No need to close your door anymore.”

I did jerk off again that night with the door open and I secretly hoped my grandmother would walk in. I felt in amazingly good spirits and had a great night’s sleep. I looked forward to the dawn.

The next day went very well. I felt in high spirits and the day flew by quickly. I worked harder than ever and enjoyed it more. It was amazing the way my outlook had changed. That evening at dinner I asked my grandma if I could ask some personal questions.

She replied, “Ask away, no secrets here.”

“Grandma, I noticed that you didn’t have any tan lines on your body. Do you sunbath naked?”

She replied, “Sometimes I do. In the heat of the afternoon, I often take a dip in the pond and dry off in the sun without clothes. You should try it.”

“I have another question. You said that there was no modesty in your family. Did you wear clothes at home when your whole family was here?”

“Of course, we did. However with five people using one bathroom, sometimes you had to poop while someone else was in the tub. Also running in and out of the bathroom in the mornings, we couldn’t take time to dress in the bathroom, so we just walked around in our underwear. We were all used to it.”

“Didn’t grandpa object to your children seeing you half naked?”

“Not at all. We were a close family. I was very close to my boys and grandpa understood that. You learn about your bodies and life early on the farm. We were well acquainted.”

I asked, “What do you mean?”

“We were a close knit family and helped one another.”

“Are you saying you had sex with them?”

“I adored my sons and when they became adults and needed me, I was there for them.”

“You had sex with my father?”

“Let’s say when my boys turned 18 and left for college they left as men.”

“What about grandpa, didn’t he want you too?”

“Of course he did. He was a wonderful lover, he screwed me like nobody else could. To say I miss him is an understatement. I call my favorite dildo Raymond in his memory.”

My head was spinning. For one thing, I was a virgin. No one had been looking out for my sexual maturation. I couldn’t shake the thought of my father having sex with his mother and considering it perfectly natural. There was a lot more to my grandmother than I ever dreamed. She may have lived in the sticks but she was anything but provincial when it came to sex. Grandma saw me dealing with these revelations sikiş izle and got up from the table and came over to me. She was smiling and gave me a big kiss on the cheek and embraced my head. My face was squeezed against her breasts as she rocked a little and then released me.

She still had a big smile on her face and said, “Robbie my boy, you’re going to be all right” and then she left.

I did something I never would have done before this summer. Without my grandmother’s encouragement, I sat down on the sofa and took my rock hard woodie from my pants and wacked off with visions in my head of my father screwing his mother. My orgasm was quick. I sat for quite a while without moving just resting my fingers in the puddle of sperm on my belly. Grandma walked in and came over to me surveying the situation. She looked at my limp dick and little pond on my belly and smiled and said, “That’s my boy” and ruffled the hair on my head. We both smiled at each other.

Grandma asked, “What were you thinking about when you were choking that chicken?”

I never heard that phrase before but then again, life with her was full of learning experiences.

“I was thinking about you and my father and him making love to you.”

She smiled and asked, “Was there a time when you may have seen yourself in your father’s place?”

I looked at her and thought.

“I don’t know for sure. I may have.”

Page 2

I couldn’t believe the conversation I was having. What’s more, I couldn’t believe how comfortable it was to have such open and honest discussion. I had indeed come a long way.

Grandma gave me a little kiss on the cheek and said, “Let’s get ready to turn in. Tomorrow’s a big day.”

I felt an enormous affection for my grandmother. I was really learning to love her.

Farm life was becoming so agreeable, I started thinking about pursuing it for a career. When I told that to my dad, he seemed to take a dim view of it, but said if I were serious, I should pursue an agricultural degree. My grandmother thought that I needed more time to learn about farm life before I made any serious decisions. As I learned more about farm life I became a genuine help to my grandmother. She told me that, thanks to my efforts, production and income had never been better. I started seeing myself as a farmer and I liked it.

We celebrated my grandmother’s 66th birthday with a special dinner. Grandma baked a chocolate cake and we opened a bottle of champagne to party. We had a grand time. There was much storytelling and laughing. We moved to the living room and plopped on the sofa. Grandma suggested a movie and fished out a DVD to watch. It was the porn movie that we had watched before. We nestled in with our glasses of champagne to enjoy the show. This time I wasn’t in a state of shock and was able watch it more carefully. The actors were beautiful with gigantic dicks and breasts. There wasn’t any foreplay. They went right to business at hand and could screw forever before they climaxed. Grandma had snuggled next to me and we shared our ribald observations.

One of the girls took hold of her own giant torpedo-like tit and started sucking on her nipple. I let out a “Whoa” in disbelief.

Grandma turned and said, “I can do that.”

She unbuttoned her blouse and took hold of her left tit (as usual she wasn’t wearing a bra) and brought her nipple to her mouth where she sucked away.

“Grandma” I said, “That is really hot.”

“You think so? Grab the other one.”

I was a man on a mission. I never moved so fast in my life. I took hold of her tit and brought the nipple to my mouth in a heartbeat. It was the first tit I had ever touched let alone sucked on. Grandma had let go of her tit and cradled her hands around my head while I sucked. The nipple was hard when I first started and hardened even further. I could feel it crinkle and tighten up, Grandma gently rubbed my head and moaned softly.

I was so engaged in what I was doing that I didn’t immediately realize that grandma was gently massaging my nuts. I was rock hard and my dick felt like it was a foot long and was glowing with pulsating heat.

I looked at grandma and said, “Oh grandma.”

Grandma moved her hand to my dick and began slowly stroking it.

I said, “Oh grandma” again and then again and again as I felt the impending eruption.

Granny quickened her stroke and I came with an explosive eruption of white hot sperm. The effect was so strong, I felt a little dizzy. It was intoxicating.

Grandma said, “You lay down here and I’ll get a towel” and off she went.

I had apparently dozed off, probably for no more than for a few minutes. I woke up with grandma’s tits dangling over my face. She let them bounce against my lips and I started alternately sucking and massaging one and then the other. I was in heaven. Grandma laid next to me on the couch while I ministered to her breasts. Apparently, I woke up refreshed because my dick was fully revived. While grandma was fondling me, she began telling me how lucky I was to have such a beautiful love muscle. She had me cleaned up and was rubbing my dick against her face and was kissing it all over. I thought she might give me my first blow job, but she slid on top of me and straddled me sitting with her bare pussy right on top my aching penis. She slid up and down over my dick with her lubed pubes.

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