I felt very emotional coming back to my hometown. I left as a bullied outsider and now I've come back as a successful businessman.
I was returning to town to attend a friend's wedding so I decided to turn it into a road trip with my brand new Lamborghini. It absolutely guzzled fuel so right outside town I had to stop and buy some more.
When I walked in to pay I was absolutely shocked. My high school crush was behind the counter. Jemma was the hottest girl in school and damn she aged well. She had her long platinum blonde hair tied up into a ponytail and she stared me down with her dark hazel eyes.
“Number 6 please mam” I said.
She punched in the number on her computer and said: “Do I know you sir?”
“I had a feeling I recognised you when I walked in. My name's Billy, I think we went to the same high school”
“Of course Billy! Oh my Lord, I haven't seen you in gosh thirty years”
“Yeah I left town after graduating…”
I could see across her face memories coming back, I guess she remembered why I left town in the first place.
“Oh Billy, you never deserved what happened to you. Those bullies were all scum”
“It was a long time ago and I've grown since then. So what have you been up to?”
“Ohhhh you know, I got married to Tony Booker, had a few kids and never left town haha”
Somehow my high school crush ended up marrying my high school bully. Just another reminder that life is inherently not fair.
It was at this moment I noticed some of Jemma's assets. Despite the fact she was wearing a sweater, I could tell Jemma had some tig ol bitties and she propped them up by crossing her arms.
“Ohhh my gosh Billy, is that your car?”
She pointed at the black Lambo outside.
“Yeahhh I just bought it last week for this wedding I'm going to but I don't know if I like it”
Jemma's demeanor grew warmer and I swear she poked her chest out a little more.
“Well I like it, it looks very swanky. Hey, are you doing anything tonight? We should catch up over dinner”
The proposition shocked me.
“Yeah that sounds great”
“The Sicilian Italian Restaurant at 8?”
“Oh wow are they still around, yeah that sounds good”.
Later that evening, I arrived at the restaurant and Jemma was already there. When I saw how she was dressed, I was a bit more sceptical of her intentions. She wore a tight fitting strapless black dress that was very busty, while her platinum hair was let down and flowed across her shoulders. Her red lipstick was paired with massive hoop earrings and last but not least – she wasn't wearing a wedding ring.
We talked some more and it's crazy how well we got along. Despite it basically being a first date, I felt completely at ease. Then Jemma started asking more prying questions.
“So how did you get so much money that you could afford a Lambo?”
“Well at uni I started working for this start up and they gave me equity in the company instead of a salary, then a company bought it so I got a ton of cash for that. I just invested it in my friends start ups and they did well so I did well…”
“So how much do have” Jemma asked hungrily. Her hazel eyes betrayed her true intentions. She was tired of living in a small town, working in a gas station, envious of other people's lives that they showed off on social media. She probably saw me as a lottery ticket, her way out of her shit life and she knew she had the body to achieve that. Only issue for her was that I've dealt with many gold diggers in the past and the desperation to exploit another person, is always blatantly obvious.
“Enough” I said and smiled.
“We should get out here, do you have a hotel or something?” Jemma replied.
We got into the Lambo and I sped off. When we stopped at a traffic light, I noticed Jemma wriggling in seat.
“Oh that's better” she sighed and when I looked over, she had released her double D's from her bra. Then she flopped her tits out and was gently cupping them.
I'm not going to lie – I got hard straight away.
“Okay so I'm going to speed to the hotel as quickly as I can” I said.
“No, you should definitely take the long way” she replied as she started stroking my pants. “Keep your eyes on the road haha” she joked as she unzipped my pants.
She pulled my dong out, gave it a kiss and then started sucking it.
“Oh fuck” I murmured as she bobbed her head up and down. It was hard to focus on driving but I did my best.
“Has anyone told you, you have a pretty cock?” Jemma laughed.
We got to the hotel and we stumbled out of the Lambo, looking disheveled. Jemma popped her tits back into her dress and I quickly did my pants up.
There was no real point though because the second we got into the room, Jemma's big tits were out again and in my face. She straddled me and grinded her hips against me as I explored her bust.
With one hand she unzipped my pants and took my cock out while I hiked her dress up and pulled her panties to the side. She sat on my cock and immediately went crazy on it. Proper pornstar theatrics; bouncing, grinding, fucking just the tip, then slamming all the way to the bottom. The whole time she was trying to suffocate me with her massive tits. I wrapped my hands around her and then spun us around so she was lying on her back on the bed. Then I started pounding her mature pussy and she melted into the bed. It was super fun to watch her tits do circles as I fucked her into the bed.
“You like watching my titties?” Jemma asked.
“I do, I wanna fuck em” I replied.
“Maybe later, give me some doggy first” she turned over and stuck her round booty into the sky.
I didn't hesitate, this was the ass I was obsessed with as a teen. I caressed it with both hands, then jiggled it a little and then plunged my cock into her hungry puss. I didn't hold back. It was like all the anger, all the resentment I held for my hometown, the bullying, the isolation and pain was all released in this one moment. The little devil on my shoulder reminded me that I was fucking my high school crush, the girl who ended up marrying the fucker who bullied me relentlessly. Yet here I was, pounding her big booty.
“Ohhhhhhhhh fuckkkkkkkk, please don't stop pleaseeeee”
Jemma was fucking me back now, burying my cock as deep as possible. And then she stopped bouncing back and started shaking. But I didn't stop and kept fucking her as she was quivering all over.
“Fukkkkkkkkkkaaaaaahhh” she screamed into the pillow as I kept fucking her ass until she bounced off it. I stood there proud, as she was shaking on the bed.
“Oh fuck, I forgot what a proper fucking feels like” she murmured.
I sat down on the chair in the corner, with my dick still super hard.
Jemma came over and knelt in front of me. She started sucking my cock, murmured “thank you” with my dick in her cheek. Then she popped off my cock and wrapped her soft big bust around it.
“Is this what you wanted? You wanted to fuck my big titties?” She stared into my eyes as she rubbed my cock. Her dirty talk was sending me over the edge.
“I saw how you stared at my titties. Don't they feel so goooood? If you want they can be your titties, I can be your little secret slut? Yeah you like that idea” She moaned as she sped up the tempo.
“You could fuck em whenever you want – ahhhh!” She shrieked in excitement as I nutted all over her breasts. I shot like six ropes as she kept grinding. It felt amazing. Jemma just smiled and dipped to the shower. I went to shower after her and when I came out she was gone.
The next day I went to the wedding and it was amazing. I had a great time with friends I hadn't seen for years. I felt like the home coming king.
At night I checked my phone and saw Jemma added me on Facebook. I mulled over accepting it but decided to just let it sit there. The next day I drove home and reflected on the weekend. It was hard not to feel happy. I saw old friends, partied hard and fucked my high school crush. I knew Jemma wanted to reach out to me, maybe even try and get me to pay for her tickets to come out to visit me. But I felt content and didn't want anything else from Jemma. The hometown chapter of my life felt closed and I moved on.