M/F ~ Age Gap ~ Older Man/ Younger Woman ~ Forbidden Sex

I want my dad’s best friend to pop my cherry

All I can think about is letting him take my virginity… even though he’s over twice my age and my dad would kill us both if that happened!

It was the middle of the night, but I couldn’t sleep.

Somehow, despite my best intentions, I could never stop thinking about Jonathan Warner, and tonight was no exception.

He was my dad’s best friend, over twice my age, and completely off limits to me, and yet I wanted him so bad it hurt.

He was so handsome, with sprinkles of gray in his hair and beard, which gave him this wise and experienced look. He seemed like a man who was in charge, and I really wished he could take my virginity. He was probably very experienced and could show me things beyond my wildest dreams.

I rubbed my breasts as I thought about Jonathan kissing me tenderly. He was so tall that I’d have to go up on my tiptoes just to reach his lips.

Yet I knew that that was nothing more than a distant fantasy because my father would probably kill Jon and me if we were ever together and he ever found out. I shuddered at the thought.

I reminded myself that Jon was completely off limits. He had known me since I was born and was like a second father figure to me, especially since my mom had left when I was young and it had only ever been just my dad and his best friend and me.

Not only that, but Jonathan also didn’t seem to have a problem finding women to be with. My father said he was a womanizing player, and I knew he would be so mad at his friend if he thought he was corrupting his little girl… even though I was an adult now, if just barely, having turned eighteen a few months ago.

Jon seemed like he might have been bad news — any father’s worst nightmare.

And yet, I was a strong woman.

Couldn’t I handle him?

Would it be so bad to spend a night in his arms? To have those strong, chiseled pecs pressed against up against me tightly? Maybe his big hands grabbing my ass and squeezing it?

I smiled at the thought of resting my head on Jonathan’s chest as he carried me into my bedroom. I bet I would feel as light as a feather in his arms, despite the fact that I was a plus-sized girl.

Jon would set me gently on the bed, reaching down to pull on the zipper of my dress. He would smile as the zipper slid down, revealing my bare breasts and the bottom of my stomach.

“I always knew you were a beautiful woman,” he would say. “Now I can see your assets for myself.”

He’d slide a hand under the fabric of my dress and over my collarbone to my shoulder, helping me take off one arm of it and then the next. The dress would get pushed down to my waist, allowing him to see every inch of my breasts as they were revealed to me.

I’d try to cover myself briefly, but he would grab my hand.

“No. Let me see what’s mine.”

I’d lay back as Jon ran his finger over the curves of my breasts up to my pointed, hardened nipples. When he finally pinched my rosy buds, they would be so sensitive from the anticipation that I would gasp.

I bet I would love having my nipples pinched by him. Just the thought of it made my core tingle and tighten.

“Are you wet for me?” Jon would ask me and I would nod.

“Yes, Sir.”

“You can call me Daddy,” he would say. “After all, I’ve always taken such good care of you, haven’t I?”

“Yes, Daddy,” I would say. “And I want you to keep taking good care of me... in bed.”

And then to prove it to him, I’d slide a hand down between my legs to play with my pussy.

Jon would grin.

“Let me see,” he’d say, and then he’d help me pull my dress all the way off.

With my body nude and my fingers pushing in and out of my pussy, I’d look up into his eyes and show him exactly what he did to my body and how he made me feel.

“What a pretty pussy,” Jon would say. “Is it all mine?”

“Yes, sir,” I’d gasp. “I’m still a virgin. I’ve been waiting for you. Saving my cherry for you this whole time, so that you could pop it when I turned legal.”

Then Jon would start pulling off his own clothes, and I would hold my breath as he pushed his pants down his towards his hips. Then his cock would come into view.

It would be so big, with a red, mushroom-shaped head leaking precum. Just the sight would leave me gasping.

“Do you want this?” he’d say, wrapping his big hand around it and stroking its smooth skin.

I’d nod eagerly.

“Do you want me to push this big dick of mine into that tight little virgin pussy of yours?” he’d ask.

The dirtiness of his words would make me wiggle my hips.

“Yes, I want that so badly, Daddy.”

“Show me how much you want that,” he’d order me.

I’d open my legs to show him my folds and how my fingers were rubbing my clit.

“Show me more,” he’d say again.

I’d push my fingers into my tight cunt, deeply enough to hurt, before pulling them back out. They’d be covered with my juices.

Jon’s eyes would light up. He’d grab my hand, pull it to his mouth, and suck my essence off my fingertips.

“Mmmm. Sweet.”

Then with my hand still caught in his, he’d push between my legs, lining the fat head of his dick up with my opening and sinking in just a bit.

It might feel like too much at first. He would be huge and hung, and I would be so tight. I was barely even able to imagine how he would push his big cock inside of me.

Jon would kiss my hand and say, “Just relax, Baby Girl. The more you calm down, the easier this will be.”

With those words, he would slowly push in a little more.

I’d watch his face, concentrating on how his eyes fluttered.

“Good girl. You feel like heaven,” he’d whisper. “Warm, wet heaven.”

Then Jon would push his dick into me a little further.

“Ahhh,” he’d groan, his eyelids fluttering again. “I’ve never felt anything so tight.”

As his big cock pushed even further up against the walls of my pussy, I’d twist and writhe. It would make me feel so full.

But when he started to pull out again, my hips would jump like my body couldn’t stand the loss. And my juices would flow freely down over my pussy lips.

“More?” Jon would ask.

I’d throw my head back, nodding it at the same time. He’d accept my yes and push back into me, filling me further this time. I’d claw at the sheets, overpowered by the tension running through my core.

“I’m going to take you,” Jon would say. “Baby girl, I’m going to fill you with my seed and mark you as mine.”

“Yes, please, Daddy, please cum in me,” I’d gasp, my eyes rolling back as he pulled out again.

The veins on his dick would act like ridges running down the length of the insides of my pussy. I’d be able to feel every inch of him moving in and out of me, the rubbing sensation feeling like nothing I had ever experienced before.

I’d be so wet at that point that our movements would make a slapping sound. His thighs would slap against mine as the base of his groin would hit my pelvic bones. In theory it should hurt, but in practice, somehow, it wouldn’t.

Instead, there would be a medley of tension and electric zaps running through my body. My pussy would tighten, feeling every thrust of his cock while he pounded it senseless, until we were both gasping.

“I’m ready,” Jon would gasp. “I’m going to fill you up now. And when I do, you’re going to cum for me, Baby Girl.”

“Okay, Daddy,” I’d say.

Suddenly, he’d lean forward and grunt. I’d feel his cock expand deep inside my pussy, pushing me past my limits and then my insides would be filled with his warmth.

His cock would throb and pulse, pushing me further towards the edge of my own orgasm.

The whole world would stop then. Everything would come down to a physical sensation that would start in my pussy and then would wash over my whole body like a wave of intense pleasure.

I’d see stars. My body would be too warm — like Jon’s cum was washing through me, almost like a high.

Hot and sweaty, Jon would kiss me on the forehead.

“I’m going to take you every day,” he’d tell me. “I’m going to use that pretty, curvy body of yours whenever I want, however I want, for my pleasure. And you’ll want me to, right? You’ll let me?”

Still feeling out of it from my orgasm, I’d just nod. There would be no reason to argue because I’d know that I was his.

Back in reality, a wave of drowsiness washed over me, probably from the wide range of emotions I had felt all day.

I sighed deeply into my pillow, glad to finally have sleep coming to take me to a blissful paradise, which would no doubt be full of dreams about Jon.

The End… of just Part 1 of my erotica serial here on Medium called “My Dad’s Best Friend Pops My Cherry.” To continue reading the serial, click here for Part 2, which is called “I Want to Pop My Best Friend’s Daughter’s Cherry.”

Or click here for the Table of Contents and reading order for all stories in the series.

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