A grandson's tribute to the one who led him gently to manhood.
My grandmother, Sylvia, just passed away recently and I wanted to write down my memories of a most important time I spent with her, a remarkable and pivotal period in my growing up.
My grandmother, Sylvia, was my stepfather's mom. My own parents were divorced when I was just four and my mother remarried when I was about seven. My step-grandmother was a very classy lady, quite pretty and trim, who had been a judge's wife until he died of a heart attack about three years before my mother married her son.
My grandmother took to me and I took to her, we just clicked, if you know what I mean. So, I spent a lot of time at her house, often overnight, sometimes with cousins, sometimes by myself.
Her house would probably be called a mansion, it was large, three stories with many bedrooms. I always enjoyed staying overnight because I could pick out a different bedroom each time. She would always read me stories and as I got older, eight, nine, ten, even eleven, she would invite me into her bed, especially if there was a storm or if we had watched a scary movie or were reading a scary book.
We always had lots of fun, I got lots of hugs and snuggles, she often mussed my hair, whispered nonsensical things in my ear, tickled me until I cried for her to stop. Of course, as I became twelve, then, entered my teens, my overnight stays became less frequent.
Then, at my fifteenth birthday party, she whispered in my ear, "I want you to come over and stay the weekend, Howie, I have a special present just for you." Well, she had always chosen presents for me with great care, always something I've wanted and then cherished.
So, she picked me up Friday evening and took me to a very nice French restaurant and as we were waiting for our food to be served, I sat there looking at her. I was now fifteen, girls and women were of avid interest, I had several teachers, in fact, that I always watched with great relish, and I was struck by how attractive my step-grandmother was. Her face was quite pretty and she had a very nice figure with a nice, trim shape.
Mrs. Thomson and Ms. Lanier were my two favorite-looking teachers and my grandmother resembled Mrs. Thompson quite a lot. Their figures were very similar, all curves and full-breasted. I also had several friends whose moms I paid close attention to, my favorite MILFS, one, Andy Rhine's mom, she was really nice. I'd seen her in a short skirt once and that was the day that I became a 'leg-man,' for sure.
So, not surprisingly, I sat there appraising my grandmother's figure, she was dressed, of course, very nicely, her hair and face perfectly done up, a dark skirt and jacket, trim at her waist, the jacket revealing to my view a good bit of cleavage that was especially enhanced whenever she reached for her wine glass. A jeweled pendant nestled between her breasts and I kept watching it move within her cleavage as we ate our supper.
I'm probably a pretty typical male of age fifteen. The expanse of open cleavage was making its presence felt right where one might expect and this was giving me erotic, yet very uncomfortable, thoughts and feelings. It was somewhat unsettling.
As I had my dessert, she asked me, "Are you all right, Howard?" as she followed my eyes down to her pendant cradled between her ample breasts and I think she realized what was the center of my rapt attention. She looked back up, smiled, and picked up the thread of our earlier conversation.
Then, standing outside as we waited for her car to be brought around, she held my arm close to her side.
"I'm so proud of you, Howie, you're so handsome, really becoming such a man. You must have a girlfriend or two, surely?"
"No, not really."
"Oh, that's so hard to believe. As handsome as you are. Then the girls your age are all fools. They should be fighting over you. I certainly would. Oh, yes," and she leaned over and gave me a soft kiss on the cheek. And, we talked about this and that all the way to her house as I sat partly sideways admiring the view below the pendant.
When we got to her house, I went in and turned on the television, flipping through the channels as my grandmother went up to change. We usually tried to find something with suspense or horror, even if some were rather corny.
As she came in, she said, "Oh, I got us some videos, they're on the table over there."
When I turned to get them, I looked over and saw her standing in the doorway. She had changed into a tight pair of jeans and a tanktop which was lowcut and fit snugly with the same necklace and pendant nestled warmly between her lovely, soft breasts.
I took out a video and got it started, not wanting to stare but so wanting to get another look at my attractive and, I must say, sexy, grandmother. She came over and sat next to me.
"Howie, I couldn't help but notice that you were looking at me in the restaurant, mostly at my breasts."
Oh, my god, she did notice. I'm sunk.
"Uh, um, well, it was the pretty necklace you had on, um, this one," as I nodded toward her chest, my face burning.
"Well, I think we both know what you were looking at and it's okay with me, after all, I've raised two sons, I know how boys change as they grow up, how they start looking at girls and women. It's rather a complement, actually."
I looked rather sheepish as she scooted right up next to me.
"Do you like the way I look, Howie?"
I nodded and she said, "I don't mind if you look at me, Howie. Here, it may be easier if you first look into my eyes," as she put her hands on my face and tilted me up to look into her eyes. Then, she slowly lowered my face to her nose, lips, chin, then, again, to those lovely, large breasts.
She held my head tilted down, my focus on her cleavage, and asked, "Would you like a closer look?"
I nodded my head and she guided me closer until my nose was touching the pendant.
"Would you like an even closer look, Howie?" she whispered and I nodded again.
With that she reached across and pulled off her top and sat before me in her bra. I know now because I've looked, my grandmother's bra size was thirty-six DDD, yes, very ample and barely contained in an ivory lacy bra overflowing its top. She pulled my face to her and I just closed my eyes and inhaled her light perfume and savored the warmth and softness burying my face in heaven.
I sat there with my face in her breasts as she reached back and unhooked her bra and let it drop down. My face lifted up slightly and she put a hand under her right breast and lifted it slightly to my lips.
"Here, Howie, for you," and I began to suck as I felt her nipple harden between my lips as she softly stroked my cheek and hair.
My head was spinning. I couldn't believe that I'm doing something sexual with my grandmother, well, my step-grandmother. But, I also couldn't believe how hard my dick was. I had the erection of a lifetime.
As I softly sucked her breast, I felt her hand rest on my pants, right on my erection. What was happening, I thought, what was happening? As I sucked, her hand began rubbing along my erection, then her other hand began undoing my belt, then unbuttoning my pants and sliding the zipper down.
This was really happening, really. It was no dream. Then, her hand slowly slid into my pants and found the front opening of my boxers. Once inside, she curled her fingers around my erection. My heart was racing, my breathing fast. As she began to move her hand up and down, my heart felt like it was skipping every other beat. All I knew to do was to keep sucking.
"It's all right, Howie, everything's fine. Grandmothers are here to help their grandsons grow up, become men. Let's go to my room, dear. We can be together like when you were younger, you can come to my bed and I'll hold you close, I'll give you what you want." and we got up and she led me down the hall to her bedroom.
She held my one hand, my other was holding my pants up and after we were in her room, she pulled off her jeans and then her panties and started to get into bed. There were no lights on in her room, just the light coming in from the hallway.
"Come, Howie, undress yourself and get in."
As I slipped between the covers, she reached out to me and pulled me close then reached up and brought my head down to her breasts. I again began sucking them as I felt her hand again wrap around my penis, pulling it back and forth. After a few minutes, she turned facing me, put her arms around me and rolled onto her back carrying me with her.
I was now on top of her and, as she spread her legs, I was also between her legs and I realized exactly where my dick was now. She spread even further, reached down, positioned my cock right at the entrance to her pussy, then, with both hands, gripped my hips and pulled me into her, wrapping her legs up around me holding me tightly, my penis inside her.
"Just be still, Howie, be still and just enjoy our being together."
As she held me, my dick inside her, I felt her begin to tighten, then contract her pussy abound my, oh, so excited, dick, her muscles deep inside her the only movement in the room.
We were completely quiet, not moving, except for deep inside her and the feelings were exquisite, they just swept me away. All my attention and concentration was on my penis deep inside being slowly, gently yet firmly caressed over and over.
Then, suddenly, all my muscles tensed, I froze, my back arched forward, pushing deeper into my grandmother's depths as I was overcome by a rapturous feeling of release, awash in the most pleasurable feelings I had ever had. It was the single most wonderful experience of my life.
She hugged me to her tightly.
"Was that good, Howie?"
"Oh, Grandma, it felt wonderful. I must have, um, you know, uh, my, uh, sperm, I think. Was it okay to do?"
"Oh, Howie, it was lovely. I couldn't be happier. It was your semen, Howie, what you probably call 'cum.' It felt wonderful, so nice and warm, down deep inside me. Thank you, you've made me very happy," and she held me close.
I lay there, so happy, so contented, in her arms, my dick still inside her, still hard, realizing that this was sex, this was fucking, this was what all my friends talked about all the time.
"Howie," she whispered, "You still feel hard inside me, why don't you try pulling out some, not all the way out, then pushing back in, just do that over and over."
I began doing it as she had said and the feeling was incredible. Oh, so wonderful.
"Yes, yes, Howie, that's very nice, oh, yes, you make me feel very good doing that. Does it feel good to you?"
"Oh, Gram, this is better than anything. I'm feeling like I did a few minutes ago, it's just wonderful."
"Mmm, oh, Howie, just go a little faster, dear, just, mmm, yes, wonderful, perfect."
My dick was tingly and feeling wonderful and my grandmother was moaning and groaning obviously in pleasure from my making love to her.
Then, my body seized again, I thrust forward and rapture took over my body as my cock emptied once again into my grandmother's depths.
"Oh, Howie, how wonderful, more love from you, dear, more inside me, how I love that."
She held me to her for a few minutes as I still slowly went in and out of her, then she rolled us over so she was up over me, my dick still in her, and she began moving herself up and down on me as her breasts swayed back and forth to the rhythm of her motions.
It wasn't long until I had my third ejaculation of the evening, deep inside my grandmother as she pushed down hard on me as I began to spasm and clench as my orgasm took me over.
She still kept rocking slowly back and forth, it still felt good, I was still hard inside her. She bent over more, dropping her large breasts onto my face and I was able to get my lips around one nipple and suck as she fucked me up and down.
"Mmm, Howie, I want you to cum one more time inside me, just let me make you happy."
She continued to rock back and forth as I sucked her nipple, my cock just in heaven.
"Oh, I think it's going to happen again, I feel…UHH, UHH, UHH, oh, oh."
"Mmm, yes, Howie, that's what I want. Put all your love inside me, just where I want it. It feels good, doesn't it?"
"Oh, yes, this has been wonderful. I can't believe we're doing this. It's the best thing that's ever happened to me."
She bent lower and kissed me softly on the lips, my dick still inside her.
"Now, you can make your grandmother very happy," and she got up over me, holding the headboard and lowered her pussy right over my face.
"Howie, would you mind putting your tongue up into me, up in my pussy? I just love it so when it's done to me."
"Oh, yes, I'd love to, anything that makes you happy," even though I had never done anything remotely like this before, she had already made me so happy, I was willing to do anything for her. She lowered herself down until a few pubic hairs touched my mouth and she stayed right there as I licked my tongue across her pussy and poked my tongue into her and twisted it around.
"Put your tongue inside me and suck on me, Howie, it feels so good," and as I did that, I felt her shudder and tremble, then my mouth filled with liquid, her juices mixed with a great deal of my own cum.
"Just go ahead and swallow, Howie, it's our own love juices, our love made it."
I did swallow it all, though some did get on my face and neck, but I also kept sucking on her as I poked my tongue up into her. She moaned, then shook again, and once more, flooded my mouth with her juices. As I swallowed, she lowered down slightly as I kept sucking and she was scooting herself around my mouth in small circles, then groaned and more juices flooded out of her and into my mouth.
She then raised up a bit and more juices dripped down on me covering my face and neck and hair. Then she got down next to me and we held each other for a long time. She whispered that we needed to clean ourselves up and we went into her bathroom where she filled her big bathtub with warm water, added bubble bath salts and we both got in and soaped each other and enjoyed each other, then rinsed off, toweled each other dry and returned to bed to sleep naked in each other's arms, my head resting against her breasts. It was lovely.
We really didn't sleep straight through, she would wake me up by stroking my dick and she would keep doing it until I cummed again. Then, she would massage my cum all around my dick and balls, rubbing it in like it was a special lotion. It felt so good and she must have done it four or five times during the night. I was the happiest boy on earth.
As we awoke in the morning, she hugged me to her warm, naked body and covered my face with kisses. We got up, put robes on and went to have breakfast in the kitchen.
"What about the birthday present you mentioned, the one at your house, Grandma?"
"Howie, I gave you your present last night, that was my present to you, sweetheart."
"Oh, I thought you meant something wrapped up and all. But last night is the most wonderful night I've ever had, I still can't believe it all happened. It was really wonderful, you made me very happy. I never expected you to do something like that. I love you, Grandma, I love you so much."
"I love you, too, Howie, I gave you my body's love last night. I wanted to make us both happy."
"I'll always remember it, my happiest night."
She stood up, took my hand and led me back to her bed again, where we relived the evening before once again. We spent most of the day in bed together, naked under the covers, sometimes fucking, sometimes just snuggling, always feeling each other's warmth and presence.
Then, around six, we both got dressed, she ordered us a pizza for delivery and we put on a scary movie to watch. About a third into the movie, the pizza came and we ate until the movie ended. Then it was off to bed together again.
Again, another night filled with sex with my grandmother. She sucked me several times, I ate her out several times, I fucked her twice and we drifted off to sleep with her waking me a few times to either do me by hand or with her mouth.
Even though my penis was pretty sore by this time, I wasn't about to let a little pain interfere with the joy my cock was going through.
We spent much of Sunday morning in bed together, a lot of it with me laying opposite her with my head between her legs and my dick being sucked on and on.
She took me home after lunch and I went up to bed and slept happily and peacefully until the next day. My grandmother's present has been the most treasured of my lifetime.
Since my fifteenth birthday, I would spend the night at my grandmother's house, in my grandmother's bed, learning more and more about her and about life.
Thank you, Grandmother Sylvia. I'll love you forever.