Free Story – Deflowered By a Widow

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It took his buddy’s hot grandma to pop his cherry.

When I was younger I had a good buddy named Eddie who lived with his widowed grandmother, a lady about 50 I’ll call Vivian.

She was a slightly plump woman, with graying hair and sparkling blue eyes and a ready smile. She had a big wiggly ass, meaty legs and hips, and huge tits which seemed to jiggle when she walked. Sometimes Vivian was not careful how she sat, and I have gotten some pretty good looks under her skirt. Boy, she looked nice and warm and white up in there too.

One day I walked home with Eddie and we sat down to watch some TV for a while. Anyway, I needed to go and take a leak. So I went to the bathroom and just pushed open the door, and then I stopped and stared, my heart leaping.

Vivian was standing there, having just emerged from the shower. She was bare-assed naked, drying herself. My mouth agape, I took it all in: her melon-sized tits; the big light-brown nipples; her full creamy-looking thighs and hips; her great forest of thick, dark hair nestled at the center of her thighs.

“Oh!” she said softly. It was not a sound of embarrassment; it was simply a sound of surprise at being interrupted. Almost lazily, she drew the towel around herself and hid behind it.

“‘Excuse me, Vivian,” I stammered, backing away, my face hot. I went back to the living room and sat down again. “I just walked in on your grandmother,” I told my friend. “She was undressed.”

“Oh, don’t worry about that. I’m sure she’s fine,” he laughed, not even looking away from the TV.

When Vivian came into the room she was fully dressed. She kept glancing over at me and grinning, not a bit embarrassed; and to her amusement I kept getting redder.

A few days after that I was over at Eddie’s again. When he left the room for something, Vivian used that time to come up close to me, her big boobs nearly touching my chest. “You’re really cute, Dave,” she whispered. “You’re such a nice-looking young man. You do things to me…”

Then one day Eddie went away for a month, and the first Saturday he was gone I got a call from Vivian.

“Dave, Eddie’s gone away for a while and he forgot to carry out that bundle of junk in the basement,” she cooed into my ear. “Would you be kind enough to come over and take it out for me? Just come on in.”

Before I could hang up the phone jumped in my car and raced over to her house. I went in and found the house quiet. I stood for a few seconds, not knowing what to do. Then I heard her call my name.

“I’m in the bedroom, Dave. Lock the door behind you and come in here for a moment,” she said.

I did as I was told and went to the bedroom doorway and peered in. I saw Vivian in bed, the covers just barely hiding her big brown nipples. And they were sort of drawn to one side, allowing one bare hip and the entire length of one creamy leg to show. Obviously, she was naked under the covers and did not mind that I knew it.

She beckoned to me and I went to the bed. My dick was already growing hard and was beginning to glow. She took my hand and I sat down by her naked hip. I gulped hard, fighting to keep my eyes on her smiling face. I was still a virgin, having never even seen a naked woman in the flesh.

“You seem to be a bit nervous, Dave. Are you okay?” she murmured.

I gulped again, shaking my head, suddenly unable to speak. I looked down quickly, then back up. Both big light-brown nipples were peeking out; I had to tear my eyes away from them. Apparently Vivian had not noticed the slight slipping down of the covers, yet I could not be certain. I wanted to look at her ample breasts.

“Such a handsome young man,” she was saying, her hand caressing my thigh, dangerously near my bulge. “I bet the girls fight over you all the time.” Her voice dropped to a whisper. “I bet you have fucked every girl in your neighborhood.”“

“No I haven’t, Vivian,” I said admitted. She would laugh if she knew that I was a virgin.

“Never?! She exclaimed. “You’re a virgin?”

I gulped yet again, and nodded. I felt her fingers close over my bulging cock and I jumped, gasping, my own hand flying down to hers. She chuckled softly, her eyes dancing.

“Well, well,” she cooed, squeezing gently. “Something has grown all big and hard and throbbing, hasn’t it?”

Then I felt her undoing my buckle, felt the release of my zipper. She reached into my jeans and drew out my rigid, throbbing, surging cock, holding it in her gentle hand, smiling.

“Oh, how sweet it looks, Dave,” she said. “How big and hot.”

I was on my feet and she was sitting there. I was stark naked! She was ignoring the fact that the covers were gone and that she was also nude. She was sitting on the edge of her bed, her eyes racing here and there over my body, devouring me, oohing and ahhing to herself.

Then my hair stood on end as her hot, wet mouth closed over the head and sucked firmly. My knees nearly buckled as she released the suck, only to draw hard on it again with her lips. Then she let go of it and lay back, her huge tits draping themselves over her chest.

“I’m going to suck the knob off that thing, baby, but first I want your cherry,” she grinned. “Lie down with me.”

Suddenly I was in her arms and she was raining kisses all over my fevered face, panting and whispering all kinds of nasty things to me. Her fingers raced here and there, over my back, over my ass, fondling my balls, my dripping cock.

At some point I began to return the caresses. I ran my hands over her smooth back, over her great tits, her arms and legs, then rubbed and petted her big hairy cunt, feeling the long lips and equally long crack. I played with her big bare ass, and then hurried back to her pussy again.

Her legs were open in welcome to my curious fingers. I moved down her naked body, heading toward her pussy with my eager face. I had no idea what I would do once I got there, but I knew that I had to taste her pussy. I had to!

“Oh no, you don’t, sweetie,” she panted, pulling me back up. “I intend to show you all about eating pussy, but that comes later. Right now I want you to fuck me. I want that dick of yours so badly it hurts. Now, come over here and get on top of me.”

I crawled on top of her and between her wide open thighs. I think I was still in a state of shocked disbelief as her fingers closed around my dick, guiding it toward her big cunt. For the first time in my life I felt my cock go sliding down into a wet, slippery vagina, skinning itself all the way back.

Again my hair tried to stand on end as I felt it going deeper and deeper into her scalding cunt. I felt it pulsating warmly along the length of my tool, felt her big satiny thighs clasping my waist, her belly pressing mine, felt her warm breath puffing into my face. At last I felt my mound crushing against her big furry one.

“There,” she breathed, her big arms hugging my neck. “Doesn’t it feel good, Dave?”

“Vivian!” I wheezed. “I can’t take this!”

“Does it feel like you want to squirt, baby?” she whispered, her eyes shining up at me.  “Go ahead then. Don’t even try to hold back. Just let it go, honey, let it go. Don’t even try to hold it. Oh, yes, yes! That’s right, honey. Oh, yes, honey, let it go. That’s right, baby.”

It had come over me almost before I knew it. There was the swelling, the sudden gushing, jerking and shooting directly into her belly while I lay stiffly between her great thighs, gritting my teeth, fighting to keep from going insane.

“Now, wasn’t that fun?” she whispered, beaming happily up at me.

I grinned back, gulping once more. I had fucked her! I had fucked Vivian! I had actually come inside her! She saw my intrigue, my delight, and laughed softly up at me.

I spent about five hours with Eddie’s grandmother that Saturday, and neither of us bothered to put on a stitch of clothes. I fucked her again a while later and she let me lick her pussy for a few minutes to satisfy my curiosity. Finally I fucked her a third time, then drove homeward. I was elated! I pooped my cherry!

As the days passed I continued to visit Vivian. She taught me the fine art of eating pussy, and I fell in love with that. She showed me the wondrous sensation of getting my dick sucked until my hot semen jetted into her hungry mouth. And we fucked and fucked. I really enjoyed fucking her because of the way she would pant and squirm under me. It was real easy to make her cum; she would go off like a volcano at times, crying out and sobbing.

She even let me stick it up her big ass a few times, and laughed softly when she felt me spurting into her asshole. “My god, is that thing always hard?” she chuckled one time when I whipped it out and shook it at her.

It was about a week before Eddie returned from a summer job out of town when I took a ride over to visit Vivian for one of the few remaining times. My mother stepped out onto the front porch, and asked me where I was going. “Over to see Eddie,” I replied nonchalantly.

“But Eddie’s been away for nearly a month, David,” she said. “And Vivian’s been alone all that time.”

I mumbled something and drove off, my face warm for some reason.

“Have fun,” my mom called softly to me.

I glanced over my shoulder to see her standing there, her fingers pressed to her lips to hide her laughter. My face really did flame then. She knew why I was going over there! She had probably known all along, too.

Soon enough Eddie came home, and I never got to be alone with Vivian again. But, I will never forget her and the things she taught me.