A Familiar Encounter Pt. 01

This is a story about a meeting with an old friend, we'll call her Sophie. In fact, this girl was the first real crush I ever had on someone. The crush dated back to middle school, when she was completely out of my league, but gave me some excellent opportunities for flirting training. I even remember the first line I said to her in an attempt to woo her. The reality of the situation didn't change, though. She was out of my league and we never turned into a thing.

Several years later, when both of us were graduating out of college, Sophie and I connected again through socials. If I'm being real, subjectively, it was no longer the case where she was out of my reach. Not that she had gotten any uglier, respectfully. But I had levelled myself up. The only issue was, she had been in a long term relationship with some singer guy.

She was no longer the type of girl I'd generally be into, though, which is why it really surprised me to find out how excited I still felt looking at her. The chemistry we still had despite not having been in touch for years and our history had me borderline craving this woman. The fact that she asked me to show her around town to my favourite food spots when she visited had me imagining all sorts of hypotheticals.

But, more than anything, I respected this girl. So when she asked me again if we were going out for dinner, I modestly planned a casual and platonic evening out to reconnect with a friend. I offered to pick her up from her hotel and take her to an Italian place that I loved. I had no intentions of impressing her so I dressed simple -- smart shorts and a classy polo shirt.

To my very surprise, when I pulled up next to her hotel, she walked out the door...

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"Hiiii! It's so nice to see you after so long. I forgot to ask you about the vibe of the place we were going to and wasn't sure how to dress so I decided to rather be over-dressed than under-. Where is it that we're going exactly? I'm starved." She blurted it all out in one breath, then looked at me with her large doughy brown eyes and puffy red cheeks.

The woman was flustered. That, coupled with what she was wearing, left me stunned, questioning the platonic nature of the evening that I had decided on. Sat next to me was the curviest little girl in a low-cut black dress that barely covered enough of her bottom when she sat down in my car seat.

I've gotta say, I was proud of myself for not stumbling over every word when I replied, "Heyyy! It's great to see you too. We're going to a simple little trattoria so being under-dressed will definitely not be one of your worries tonight. However, I will have a hard time choosing a table where the waiters won't be tripping over things because they're too busy staring at you."

As if her cheeks could've gotten any redder and her breathing any heavier, she shyly giggled.

My line-of-sight was interrupted by the seatbelt she pulled across her body, covering the distinct arcs disappearing into her dress that I had unknowingly been staring at. I could tell that she wasn't wearing a bra. That made two flustered people in the car.

My eyes widened and lept back up to her face, where I discovered the coyest of smiles that I definitely was not expecting to find. Why was she so fine with me staring at her breasts!? If anything, she seemed happy about it, like she was glad her plan was working.

Still flustered by getting caught staring at her, I shoved the car in drive and pulled out onto the road.

"So, how was the journey? Did you make it to the city safely?"

"Oh yeah, Josh (her boyfriend) and I got here quite early this morning. We slept in for most of the day, except lunch, which to be fair we also had in bed. I only got out around 5 to get ready for our evening."

5 PM!? It was half past 7. She spent over two hours getting ready to spend an evening with me!? No kidding, she looked it too.

"Oh wow. I didn't realise Josh was in town too."

That's right, I only realised as I said it. I had no idea Josh was coming with her.

"Yes he made plans last minute. He's got an aunt who lives in the city who he's meeting tonight."

"I see. I was just gonna ask if he wanted to join us too."

No I wasn't. While I was trying to convince myself that I had no intentions of treating Sophie like a date, the last thing I wanted was to meet the man she was actually dating.

The next 20 minutes involved some light chit-chat that I barely remember. All my brain was picturing was her tight dress climbing up her tender, thick thighs realing more and more of her body as it jostled around in that seat. How I got us safely to the restaurant without losing focus on the road crashing is beyond me.

"This is it! I love this place. They make their food with so much passion."

Once we reached, I quickly jumped out the car and ran around the back where she wouldn't be able to see me tuck away my excitement.

I walked over to her side, but found her still sitting inside the car. I opened the door and asked "You alright?"

Mid-sentence, I saw her hand reaching out the door. I held it gently as I watched her pull herself out the door. My every attempt at keeping this evening platonic was already being shot down by Sophie. Honestly? I was starting to love it.

Instead of dropping her hand once she was out the car, I held onto it while I closed the door for her. I even walked her to the restaurant with her soft hand in mine. It made her smile so cute.

"Reservation for __."

The waiter guided us to our table. I even sat her into the 'girlfriend booth' AND ordered wine immediately.

I don't think Sophie had taken her eyes off of me for even a second since she stepped out of that car. It was her soft yet intense gaze that hadn't changed the tiniest bit since school. The only difference was, this time, it was screaming "I want you."

I sat down in my chair, let out a gently sigh, and stared back into her eyes.

We were still playing the platonic part. So after a few seconds she blushed and finally moved her eyes to the menu.

"So, what do you recommend we get?"

If it were truly up to me, I'd throw you onto the table and have you right here.

"They have the fluffiest and lightest pizza I have ever had. Their rissotto is also great."


"Mmm sounds delicious. But let's just order a pizza and keep it light. Although I wouldn't mind an extra bottle of wine."

Light on the food and heavy on the booze? Of course.

The waiter brought the first bottle when she came over to take our order. And the second bottle 5 minutes after we finished our pizza.

By the time we finished our last glasses, her feet were tangled up in mine and her fingers were brushing up against my hand every minute.

"You really glowed up after high-school. I'd have loved to watch it happen through the few years at college."

"It was quite the journey. But I'd rather have you focus on the results anyway."

"It's quite difficult to NOT focus on the results, if I'm being honest."

I couldn't hold back. This hot, innocent, crazy little chick that I had been so into couldn't keep herself from flirting with me. But, like I said, I still respected her and didn't want to assume; I still wasn't sure where this evening was gonna go. So I excused myself to the men's room for a moment, and paid the bill on the way out.

If the tension between us really was gonna continue rising at the same rate, I wouldn't wanna be unprepared. So I locked the door to the washroom and dropped my shorts to the floor. My cock whipped out like a spring and laid twitching on the sink. I didn't want to waste the precum that had been dripping out all through dinner so I covered the tip of the shaft and gave the rest a nice clean. Fitting back into my pants was a struggle.

I walked back out into the restaurant to find her fixing her makeup and adjusting the way her breasts sat in that dress. Walking up to her, I offered my hand again, "Let's get out of here."

Trying to not suggest anything, but hoping to god she would, I asked, "Would you like me to drop you back to your hotel? Or shall I take you on a nice drive around the city?"

"I think we both know that neither of us want you to do either of those things."

I looked over at Sophie to find her biting her lower lip.

I sincerely asked, "What about John?"

"John... isn't at his aunt's."

"What do you mean?"

"John... is at the hotel...

with his hands tied to the bed, wearing only my underwear,

his stupid little cock fighting against the waistband of my panties,

thinking about what you might be doing to me right now."

I was speechless. I was wrong about thinking that the tension would continue to rise at the same rate, it just shot through the roof and out my pants.

Out of all the hypotheticals I had imagined, this was an even bigger fantasy,, coming true.

"I want you to have me. I want you to have your ways with me. I know about all the sexual frustration that must have built up inside you for me over the years. John has struggled to satisfy my needs. And since I saw you again, all I have been able to think about is how much bigger and better you might be than him. I want you to show me."

That was it. The next thing I remember, we had parked up in a dark alleyway. Sophie was climbing over into my lap.

Her breasts heaved over right in front of my face. I grabbed her plump thighs with the tighest grip possible. I looked up to her lips and caught one between my teeth. She let out a moan that released all her frustration. Her breasts pushed into my neck, resting on my chest.

As I bit and kissed my way down her neck, her hands shot for my shorts. Instead of pulling me out the top, she pushed the fabric of one leg over to yank my cock out.

Her dress had already climbed up over her ass on its own. She straddled my rock hard shaft and pushed it up against her pussy. The underneath of my shaft came into direct contact with her vulva, making me realise that she really wasn't wearing any underwear at all. She stroked my head with her fingers as she rubbed my length against her lips.

Meanwhile, my lips had found their way into the slit in her dress and onto her nipples. She really did have some stunningly large areolas, but they sat perfectly in proportion to her huge tits. My exploratory hands, nibbles on her breasts and the friction against her pussy was making her moan her lungs out. Her wetness had slowly covered the entire length of my shaft in her juices.

Her moans and merely having her fingers wrapped around my cock were driving me crazy. I slapped my hands onto her asscheeks, lifted her up and positioned her entrance right over my tip.

I paused. The car was filled with our heavy breaths. The windows were covered in the mist of our breaths. Sophie stared into my eyes with anticipation.

"Are you ready?

There's no going back."

Sophie grabbed my face with her yearning hands.

"Make me your woman."

I dropped her onto my lap, my length penetrating deep into her loins. She let out a painfully ecstatic shriek as her eyes rolled back into her head. My eyes slammed shut and I unleashed a growl loud enough to be heard back at John's hotel room.

I opened my eyes again to find Sophie staring into me with more passion than ever. She looked at me like I had just caused a miracle.

Without wasting another second, she started grinding and jumping up and down on my lap. My cock was hitting spots that hadn't been touched in years.

For a while, the chemistry between us vanished. She was riding me like her toy and I was watching her in pure joy. Her perfect breasts bounced around in front of me, hitting into each other and occasionally slapping me in my face. Her moans echoed in my ears. Her thick body danced on top of me like I was her stage and her my ballerina.

As I was admiring her art, her whole body began to tremble on top of me. Her moans somehow got even hotter and she shuddered as she had her strongest orgasm in years on my cock.

"Sophie... stop

Sophie you're gonna make me cum

SOPHIE I'M GONNA FUCKING CUM."

Her eyes slapped open, the chemistry was revived and she shouted at me, "DO IT. FUCKING CUM INSIDE ME."

Before I could react, before she even finished her sentence, I was shooting my load as deep inside her as I could, growling like a fucking dog. I felt my fluids drip out of her pussy and down my balls. She didn't stop jumping. After what felt like a dozen pumps of my cum inside her, she slowed down and came back to her senses.

I felt more turned on than ever. Despite having blown the largest load of my life, the fact that Sophie was sat on my cock with my cum inside her made me so incredibly horny.

I grabbed her by her neck and threw her onto her seat, her legs still all over me. Her tits looked stunning, falling into her face as she laid almost upside down.

I commanded her to move to the back of the car. "My turn to dominate you."

Sophie eagerly complied.

Before she could climb all the way back, I slap-grabbed her ass and made her scream. I shoved my face between her cheeks and ate her out like I had wished at the start of the dinner. I licked between her lips and sucked on her clit as her juices and my cum dripped down my beard.

I pulled back to let her fall into the back seat, and then followed her there. She laid on the seat with her legs spread wide, and I got onto my knees to continue enjoying my meal. One of my hands reached up to massage her breast while the other explored her insides.

"More fingers."

It didn't take long before her legs fell from the roof of the car onto my shoulders and her body started convulsing from another orgasm. She squeezed my head with her thighs and her hand reached out to try to get me to stop. I fingered her through the entire orgasm, slowing down and stopping right after.

"The way you moan my name drives me crazy. I'm gonna make you cum on my cock again. But this time, you're only allowed to scream my name once you start cumming."

"Yes sir."

I positioned my tip at her opening and stared into her eyes.

"Fuck me silly."

She didn't have to tell me. I watched her bite her lips at each of my stroke, struggling to keep herself from screaming out my name.

Her breasts jiggled at my command.

To watch her squirm under me was everything.

"Fuck."

"Cum for me."

"FUCK.

I'm gonna cum so FUCKING HARD."

"That's right. That's my good little girl."

As her body shook under me for a third time and she screamed my name, a smile crept up onto my face. I was going to remember this view forever.

I slowed down, gently pulling out of her, still hard as a rock.

"This erection isn't going away till you're in my sights."

Sophie blushed.

"Let me take you home."

"I have a better idea."