DISCLAIMER
: All characters engaged in sexual situations are at least 18 years old.
I was devastated when my parents were killed in a head-on crash. I was sixteen at the time and, fortunately Grampa Joe and Nana Helen Jackson took me in and took over from my parents. At eighteen, I was a bit small and shy. I had a very hard time with relationships, especially with girls. I admit to being somewhat of a geek and graduated Valedictorian of my class.
Let me introduce myself. My name is Donald and like I said, I was small. I stood at five foot three and weighed maybe a hundred twenty pounds. The one part of me that was not small for my overall size was my cock, a cock that had never ever been touched, except by myself, since I was old enough to take care of my own body. It had to be about six or seven inches long and as big around so my fingers couldn't touch each other when I was holding it. My dark hair and brown eyes set off a "baby face" that seemed to scare the girls away—almost as if they were afraid to be caught robbing the cradle.
The one million dollars of insurance money from my parents' deaths insured I had the funds to go on to college in the fall so, with my grades, I had decided to attend a good Ivy League college in up-state New Hampshire.
Then tragedy happened: Grampa died of a stroke two weeks after my graduation from high school when I was eighteen. I heard much later that he had died while he and Nana were having sex, but who am I to judge—I'd never had sex and only knew what I had learned in sex-ed and biology classes. As they say, I had a lot of book learning but no experience.
Naturally, Nana took his loss very badly, much as I had when my parents were killed. She started drinking more alcohol than I had ever seen her drink and was depressed from morning until night, or so it seemed.
About a month later, I was reading in bed. As I was reaching over to turn off the touch lamp, my bedroom door opened. Nana was standing there I a nightgown that barely hid her crotch. I'd seen her in it before, so no big deal, right? Except this time, she wasn't wearing panties.
"Donny, are you still up?"
"Yes Nana. I was just getting ready to turn off my light."
I had noticed that her words were a bit slurred, but thought nothing of it at the time as she had been slurring her words often since Grampa died. She came into the room and sat on the side of my bed within inches of me. She reeked of alcohol and some other scent that I didn't recognize but seemed to be coming from between her legs.
"Do you think I'm pretty, Donny?"
"Yes, I do. Why do you ask?"
"Pretty enough to attract a young man?" Where was this going, I wondered?
"I guess so. Why?"
"Are you attracted to me?"
"You're my grandmother. I think you are as pretty as you need to be to get anyone you want."
"You didn't answer my question. Are you attracted to me?"
"Yes, but, like I said, you are my grandmother and I am not supposed to think of you that way."
"How come you don't have a girlfriend?"
"None of the girls seem to like me. I'm small and nerdy and they seem to like the big guys that are into sports like football and basketball or even soccer."
"Well, you do know that there are some girls that like smart fellows like you, right?"
"Yeah, I guess. I just haven't met one yet."
"Yes, you have. You've met me, haven't you? I like a guy that is smart instead of brawny. I've been watching you since you came to live here, and I have liked what I have seen."
I had always considered a woman as old as my grandmother to be much too old for me, but she had a point. The younger girls went for the jocks and left guys like me beside the road without a thought. I took another look at my grandmother and decided that, yes, I was interested, but how would I let her knew without making a fool of myself?
Nana was five foot four and probably a hundred ten pounds with smallish, perky breasts, a pleasant face, blue eyes, blonde hair down to her buttocks usually tied-up in a pony-tail, and wide hips. All this was based on observation—book learning, not experience. All-in-all, a nice package, and she had the experience that I did not. I was beginning to think that it would be a win-win proposition for both of us—damn my analytical mind!
"Would it help if you saw what you are going to get?"
"What do you mean, Nana?"
"Just what I said." She stood up and clumsily lifted her nightgown over her head. For the first time in my life, I saw a totally naked woman. I took in the view and was amazed when I felt my cock begin to harden without me even touching it.
"I can see 'he' likes the looks of me." My cock now was almost totally hard and tenting the front of my pajamas.
"Yeah, I guess he does."
"Take him out and let me see him."
"Are you sure, Nana? I don't think Grampa would approve."
"Your Grampa isn't here, is he?"
"No, Nana."
"Then take him out and let me see him. I need him deep inside me. I'm a horny bitch that needs a good fuck."
"Nana, I don't know what to do with a girl. I've never even kissed one, except for you, of course."
"Then, I'll show you and teach you everything you need to know." She had continued slurring her words as she took another big swig out of the whiskey bottle in her hand. She staggered the two steps and sat down beside me once again reaching out to take my cock in her hand. "Oh, he feels nice! Just what Nana needs right now to plug her horny cunt."
She put the whiskey bottle down on the floor, leaned into me on the bed the bed, and gave me a kiss that seemed to go on forever. I could smell the whiskey on her breath and taste it on her tongue when she pushed her tongue deep into my mouth. The kiss and the alcohol literally took my breath away.
Nana reached for the waistband of my pajamas and started pulling them down. She ran into the obstacle caused by my rock-hard cock, but finally pulled the pajamas down, exposing my cock to her view.
"Oh, my God! If I knew what you had there between your legs, I would have done this as soon as you turned eighteen—even before Joe died! He was a good fuck, but he didn't have what you have between his legs. Your cock is beautiful—and, big!"
My cock had swollen beyond its normal seven-inch length and was dribbling a lot of pre-cum from the single eye at the tip.
"Donny, I've got to taste you, NOW!" As she said this she bent over and her mouth enveloped my cock. I could feel her teeth scrape the side every time her mouth went down and the tremendous suction as her mouth retreated to the tip of my cock. I had never felt anything like it, but instantly I was hooked on receiving oral sex. This went on for another couple of minutes before I could feel the tingle in my balls that meant I was going to cum, and cum soon.
"Nana, I'm going to shoot any time now."
She kept sucking and I exploded what felt like a huge load into her mouth. Nana never stopped bouncing her mouth up and down my cock until the last spurt had been swallowed.
"Now, Donny, that was delicious! We're going to have to do that again. Do you always shoot that much cum? You just lay back and let me get you inside my cunt."
With that said, she climbed on top of me and inserted my still semi-hard cock into the hole between her legs—the one I had only read about in sex-ed and biology. If I thought the oral sex with my Nana was good, her cunt took me to new heights, hardening my now somewhat sensitive cock back to its full length and rigidity.
