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

My Father’s Best Friend Took My Virginity

And I think my dad might have caught us in the act!

I had been fantasizing about my father’s best friend Jonathan so much lately that I knew I had to make it a reality or I’d be driven insane.

So, the next time I saw him, which was at a family event, I invited him over to my house afterwards.

And he said yes!

I couldn’t believe this was actually going to happen.

While I was in the car, I kept thinking that I should call the whole thing off, as I pondered how crazy this idea really was.

What was I thinking?

I knew I was playing with fire. But at the same time, I really didn’t care. I wanted to see where things could go between us.

I was taken aback by my boldness in having Jon follow me home, but my curiosity had gotten the best of me.

When we pulled up to my house, I looked around and made sure my dad’s car wasn’t parked there. When I saw that it wasn’t, I went inside and nervously paced around until Jon knocked on my front door lightly.

Then, I let him in and shut the door.

As I locked it and bolted the top so that nobody could get inside without me letting them in — especially not my over-protective father, who had the habit of trying to come over unannounced — my heart was beating so fast I thought it might explode.

This was the first time that Jonathan and I had been alone like this since I became an adult. Although he had helped my father raise me as a child after my mother unexpectedly passed away, once I turned of age, my father tried to keep him away from me because he said he would make a move on me.

If only he knew how much I wish he would!

And now it might finally be happening.

“Nice place,” Jon said when we got inside, sweeping his arms in a circle that encompassed the entire house.

“Thanks,” I said, my voice almost a whisper.

I didn’t want to mention that my dad had bought it for me, because that would put a damper on the mood and might kill things between us all together.

I was playing with fire, being with Jon when he was over twice my age, and my father’s best friend. He might kill us both if he were to find out!

But hopefully he wouldn’t.

And I guess that was a risk I was willing to take, since I was here with him now despite the danger of getting caught.

The room was completely silent as we stared at each other. I couldn’t help but be taken in by his beautiful gaze and dazzling smile.

Jonathan was everything that I could have ever wanted in a man. He was handsome and charming and right now he was making me feel like I was all that mattered to him.

I felt that I had always wanted him, ever since I was young, but I had never thought I could actually have him. So, my dreams really were coming true.

“Can I see the bedroom?” he asked, his voice at a low growl.

I could feel myself starting to get wet just at the sound of it. I couldn’t wait to see what more could happen between us as I nodded silently and shuffled down the hallway to my bedroom.

“Here is it,” I said, looking around at my plain room. “It’s not a lot to see, but here’s my room.”

Jonathan’s eyes were glued to me as he stared at me from head to toe. He moved in closer to me, traipsing confidently across my bedroom until he had me in his arms.

He kissed me as he laid me down on the bed, leaning on top of me so that I could feel every bit of him on me. His dick was hard against my leg.

My heart started beating fast as we writhed on the bed, making out like teenagers. Jon got to his knees and started helping me out of my pants.

Next, he quickly took off his clothes, standing in front of my bed. I could see his chiseled abs and broad chest and sculpted arms. He looked like a model as he stood in front of me. I pulled off the rest of my clothes, revealing my curvy body and ample bosom.

He grunted as he took in every inch of me before leaning in and touching me. His hands felt like electricity coursing through my body. Jon had a soft touch at first, as he rubbed my breasts softly.

He took my hard nipples into his mouth and lapped at them hungrily. I wrapped my arms around his neck and moaned, pulling him closer.

“Wait,” I said breathlessly. “I need to slow down.”

Jonathan frowned, stopping what he was doing.

“You okay?” he asked, his voice very concerned. “What’s wrong?”

“It’s just that….” I began hesitantly. “I’ve never done anything like this before with anyone. I’m… umm… I’m a virgin.”

His eyes widened incredulously as he stared at me in disbelief. He let out a chuckle as he shook his head.

“Are you serious?” he finally said after a few moments. “You mean to tell me that no one has shown you how fulfilled you can be? No one has ever pleasured you?”

“No. I mean, don’t get me wrong. I’ve done…stuff,” I admitted. “I’ve just never gone completely all the way.”

I stared down embarrassingly. I didn’t want to draw more attention to the fact that he was so much older than me, or that his experience was so much more than mine.

“It’s okay,” he said, putting a hand under my chin and lifting my head. “I’ll be gentle. And I’ll teach you how to do it.”

“That sounds like a good plan,” I told him, as I thought about him training my body in bed just like he trained me on the racecourse.

He started kissing me again as he rubbed his large hands all over my body, making it look and feel small in comparison, even though I was a plus-sized girl.

Next, he began to rub between my thighs until his fingers were nestled between my legs. He parted my legs and opened my pussy, then gasped with delight at what he saw.

I glistened from excitement, my pussy dripping wet between my inner thighs.

“That’s so fucking hot,” he said. “I love how wet and ready you are for me.”

I nodded, not afraid to admit that I was because it was clear that he was just as ready for me, too. His dick was as hard as a rock.

I put my hand down and felt his throbbing member. My fingers looked small as I wrapped them around his huge shaft. I didn’t even know that a cock could be this big!

I gulped as I thought about how it would feel inside me… and whether it would even fit.

Would it hurt too badly? I wondered.

But I trusted Jon and I wanted to experience him in my pussy. I could tell he would make me feel amazing, just by the way he expertly fondled the outside of it, running his fingers around my clit before putting them in and out of the hole, making me even wetter.

I ground against his fingers, letting him fuck me with his hands. I could feel my pussy gripping his finger as he pushed his way inside me.

“Fuck yeah,” he groaned. “Your little pussy feels so good. I want to show you how good I can make you feel.”

Next, he inched down until his mouth was on my clit, sucking and licking every bit of it. I felt I had been shot up to Heaven as his tongue stroked it and his lips wrapped around it while he continued fingering my hole.

“Oh, Jon, that feels so good…” I started to say, but I was soon overtaken by an orgasm.

“Ohhhh!” I cried out, as my hips writhed around and a wave of pleasure rode through me.

“There you go,” he said, in between sucks, licks, and little nips of my pussy. “Cum for me, Jane. Just like that.”

“Ohhh, yeah, Jon!” I called out, as I was at the peak of ecstasy.

My juices were dripping into his mouth and his palm, and he was eating me up like I was a delicious treat. Once my orgasm finally subsided, I lay there panting regretfully, wishing it could last forever, but I could tell that he was about to give me another one. And another one.

“Good girl,” he said, after he finally pulled his mouth away from my pussy. “I knew if you relaxed and let go, you’d enjoy it. Don’t be afraid to open up to me and let me all the way in, okay?”

“Okay,” I told him, thinking that he really didn’t have to ask me twice.

I had been waiting my whole life for this and I wanted to feel every little thrill with him as much as possible. I loved how I could let loose and let out my inner slut for him — the man I had known forever and had wanted for almost that long.

Jon got on his knees on top of me and pushed his big dick up against my wet pussy. I opened up as wide as possible to let him in, but his cock stretched my walls to their limit.

I gasped as I gripped his shoulders, bracing myself as he pushed himself deeper and deeper inside me.

It hurt only for a second and then I felt satisfied being completely filled up by his huge girth.

“Is that okay?” Jon asked me, and I loved the care and concern I heard in his voice.

“Yes,” I told him. “It feels good.”

“Good girl,” he said, stroking my hand. “I knew you could take my cock. It’s big but you were nice and ready for it because you wanted it so badly, didn’t you?”

“Yes,” I admitted, as I sighed in pleasure. “I’ve always wanted it and I’m so glad it’s inside me.”

“You’re glad your daddy’s best friend is finally filling you up with his big dick?” he asked me excitedly.

I hadn’t thought it possible to get any more turned on, but now I was.

“Yes,” I admitted. “I love how you stuff me full.”

“I know I’m a lot older than you and I’ve known you your whole life,” he said. “In fact, I was kind of like a second father figure to you early on, so I wasn’t sure if you’d ever let me fuck you.”

“I wasn’t sure you would want to because I was so young and off limits,” I told him. “But that’s kind of what makes it even more exciting. Daddy.”

I felt embarrassed at first, not sure why I’d let that word slip out of my mouth. But his cock got even bigger inside me, and I could feel it throbbing, so I knew he liked that I’d called him that.

“Oh, that feels so good, Daddy,” I said again, and it caused him to push his big dick even further inside me.

“Good, baby girl,” he breathed as he stroked it in and out of me, caressing my face and dipping his head down to lick my nipples one at a time.

He didn’t miss a stroke as he gripped my hips and pushed himself deeper and deeper inside my tight pussy walls.

I moaned softly, having another orgasm and enjoying the sensation of his large dick pummeling me as he went harder and faster.

I could tell he was completely turned on as he picked up speed more and more, ramming his dick as deep inside me as he could.

“Oh, yes, Daddy, fuck me hard! I love it!” I cried out.

I pushed back against him, circling my hips to match his pace as I came again and again.

“Yeah, you love how I pummel your tight little cunt,” he shouted. “And you want more and more of my big dick in your little pussy, don’t you, Baby girl?”

“Yes, Daddy, yes!” I kept crying out.

My pussy was slippery and wet against his throbbing hard cock. He turned me over onto my stomach, pushing his dick between my ass cheeks until he found my cunt again and then he pushed his way inside me, inch by inch.

I came for what felt like the hundredth time. I loved the feeling of pleasure that flowed through my veins.

He moaned as my pussy gripped his member. I buried my head into the pillow and bit my lip, stifling a scream.

My pussy felt tender and sensitive with each stroke. I gripped handfuls of the covers, getting on my knees so I could rock back and forth to match his movements.

“I’m about to cum,” he announced, rocking me back and forth, pounding my pussy for all it was worth. “Right in your hot, tight little cunt, Baby girl.”

“Yes, Daddy, cum in me!” I called out, wanting his seed deep inside me.

Soon, I could feel him pulse and then I felt his load exploding inside me, making me cum again, too. I felt my pussy walls convulsing against his dick as he slammed into me again and again and we both grunted and moaned.

He sputtered his hot cum inside me as I came all over his hard dick.

“Good girl,” he whispered, nearly breathless. “That’s my Baby girl.”

Afterwards, as I lay on the bed, having collapsed from being out of breath myself, I couldn’t help but smile with happiness.

Being with Jonathan like that made me feel surer than ever that he was the one for me. I was glad that he was teaching me everything there was to know about life. He had taught me how to have sex, for my very first time.

And perhaps he also could teach me about love. For some reason, I was convinced that he could do that and more.

But then another thought seemed to invade my happiness. I knew that there was no real way for us to be together.

If my dad were to catch wind that any of this was happening between us, he would be sure to kill Jonathan and disown me.

I loved my father and didn’t want to see him so upset. I frowned disappointingly as I looked over at Jon.

“What’s wrong?” he asked, as if he were reading my mind.

“I just don’t see how we can be doing anything like this,” I said, hoping that he could read between the lines.

He stared at me, prepared to say something in his own defense, but then stopped himself. He hung his head in shame, nodding as he stared at me.

“Yeah, you’re right,” he said. “I’m sorry. I was being very selfish. You are so fucking sexy, and I just had to have you at least one time.”

I looked back at him in shock.

One time?

Was that all he wanted from me? I couldn’t help but wonder.

Maybe my dad was right and he was just a womanizing player. Now that he’d gotten what he wanted from me, he would be done with me.

“No, it’s not like that,” he said, waving in the direction of my head as if he could read my thoughts and was chasing them away. “I just mean that we probably should make this our one and only time that we do something like this. We got lucky and had a few secret, super hot moments, sure. But what happens if someone finds out about this? What happens if your father hears about this?”

I nodded in agreement and told him that he was right and that we shouldn’t try to push our luck anymore.

But then as I walked out of the bedroom and into the kitchen to grab a cup of water for both of us, I heard a horrific sound at the front door.

Someone was knocking!

I looked out the window, hoping it was a lost delivery driver. But I had no such luck.

It was my dad. My car was outside, so he knew I was home. And Jon’s was here, too!

Fuck.

He tried his key, only to be locked out by the chain.

Jon and I had been caught after our very first time together!

We didn’t even have any time to follow up on our promise to stop doing this before my dad found out… it was too late.

Wasn’t it?

I couldn’t see a way out of this mess, but I had to try to think of something.

Maybe Jon could help.

I could feel my blood beating in my ears as I tried to think fast about what I should do.

Because if it all came down to my dad finding out about us like this, then I was pretty sure the world as I knew it would come crashing down on me for good.

The End… for now.

Thanks for reading Part 4 of my erotic serial called I Want My Dad’s Best Friend to Pop My Cherry.

Click here to continue to Part 5.

To get caught up from the beginning, click here for Part 1.

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

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