Give her your number

“Here is what I’ll do,” you calmly say as you take your wallet out, “I don’t want to freak you out, you’re a gas station cashier who is drop-dead gorgeous, I’m sure creeps come up in your business all the time. I’m gonna give you my number, so that if you want to reach out to me, the power is in your hands. I’m gonna be in Southold this weekend for a wedding, hopping bars all the while I’m sure. That’s not too far away right?”

“Not a lot of guys pull into my parking lot with a lady going down on him, and then proceed to give me their number while buying condoms to fuck the lady with,” she smiles, “but you are definitely cute, and I think it’s really cool that you are giving me the power to chose here. I was getting kinda nervous.” She pulls out her phone and hands it to you to it to create your contact.

You are surprised, “you knew about the girl in my car the whole time?”

“Uhh yeah, your windows aren’t tinted. I’m Ashley by the way.”

“It’s really wonderful to meet you, Ashley. I’m Bill.”

You create your contact, hand her back the phone, and go to pay for the stuff. You grab it, say your goodbyes, and stroll out the store.

As you walk out you see a police car pulling away from where you had parked.

You run over to see if Jenn is okay. You get there to see she’s pacing back and forth.

“What happened Jenn?”

“Bill! I got a ticket for public nudity! Where were you??”

“I couldn’t find the right condoms at first, I had to ask for the cashier to get them out of the back. I’m so sorry Jenn.”

“It’s okay, Bill. It’ll be fine. It’s not too much money anyway. Let’s hit the road, I need a drink.”

“Not in the mood anymore?” You ask hopefully.

“Not right now, but holy shit Bill the policewoman was so hot. You would’ve definitely tried to hit that. Maybe tonight we could mess around with some handcuffs?”

You are ecstatic. You gave a hot chick your number and your ex is still gonna fuck you tonight. What a car ride.

After about another half an hour, you arrive at the house. It's huge. Like get-lost-in-your-own-bathroom huge. It's three stories, right along the shore of the Long Island Sound, with a beautiful front lawn and driveway. There's already at least eight cars in the driveway, so you don't worry about blocking anyone in; you'll just move it if need be.

"Holy shit, Bill, this is amazing!" Jenn says

"I knew this family was loaded but I did not expect a house like this."

The two of you grab your stuff from the trunk and make your way up to the front door just as the sun was beginning to set. You ring the bell and can hear some voices coming from inside. The door swings open and Claire Jefferson is behind it.

"Bill!! Oh my god it has been too long!" she exclaims as she pulls you in for an enormous hug. Claire is Alex's mom. She is the ideal MILF: mid-40's, brunette, thin waist, thick ass, nice round C cup tits. Because you and Alex have been friends for so long, you've been oogling over her mom since you hit puberty.

"It's so good to see you Claire!" you grunt as she squeezes the life out of you, her tits pressed up against you, smelling full of wine. "This is my, er, girlfriend Jenn. Jenn, this is Claire, Alex's mom," you say as you gesture them towards each other.

"Oh Bill she is beautiful! Great job!" she said with a wink towards you, "So nice to meet you Jenn!"

"Come in both of you, everyone's inside! They'll be so happy to see you!" Claire said as she began walking into the house. You can't help but stare at her fat ass rocking back and forth down the hall.

“God damn that’s a nice ass,” Jenn whispers to you, just as transfixed on the sight

You enter the kitchen to see it full of some of your closest friends and their relatives. "Bill!!" they shout in unison as you walk in. One by one you greet everyone in the room.

First and foremost, there's Jim and Alex. You've known Alex since the fourth grade and you basically grew up among her family. You never saw her as anything but a best friend throughout middle and high school, and when she started dating Jeff, you couldn't have been happier. While she did grow into a truly gorgeous woman, you haven't felt anything for her more than a silly crush. Jeff is your closest confidant. You met in seventh grade playing on the school basketball team and you soon became inseparable. When you went to college, you made sure you picked a school close to where Alex and Jeff went, so you could see them as much as possible. You became used to being a third wheel, and they were always encouraging with your relationships. In fact, they're the only people at the wedding who know that you and Jenn aren't still together. Alex called you a week before the wedding and told you that she would talk you up to every eligible woman that would be there this weekend.

Next, there's your dad, Paul, and his wife, Isabelle. Your mom left you and your pops when you were three, causing your dad to become pretty depressed most of your young life. He had several girlfriends in and out, and he finally became truly happy when he met Isabelle about three years ago. He wasn't a wealthy man by any means, so you were pretty sure she was no gold digger, but she was only a few years older than you. And she is smoking hot. Isabelle is at least a nine, and flaunts all she got. She's a classic 'dumb blonde' and she gets really slutty when she is drunk, but you suspect her and your father have an open relationship. After all, he is thirty years her elder.

Next you see Lexi, and your heart stops. Wow did she grow up. Lexi is Jeff's little sister, four years younger than you. She was always a bit nerdy and was always too young but she made it very clear that she was in LOVE with you. In the few times you have seen her since high school, she seemed disinterested in you, at times even resentful. But today she is happy to see you, and now you're certainly happy to see her. The blonde curly hair that once grew into a huge mane was now long golden curls that draped a smooth, bright-eyed face. She looks more attractive than you had ever noticed, and soon you're thinking if you had somehow missed this glow up.

Jared and Jack are hanging out behind the big crowd, but you couldn't miss them. These guys were two great friends from the high school basketball team and you haven't seen them in ages. Jared brought his new girlfriend, Samantha, and Jack is with his girlfriend, Victoria. Victoria was a crush of your's in high school, years before Jack and her got together. You had even shared a few moments in a few bedrooms at a few parties in high school.

There are others there, but none who really mean as much to see as the first few.

Then, at the end of the greetings, you see her. Anya. Your ex from high school. The two of you were in love as soon as you started dating, as many young romances do. She was one of the hottest girls in school and you started dating when you were a junior and she was a senior. When she went to school, she pledged herself to you and swore she would never cheat. Of course, it was college, and by the time you visited her for the first time in November, you found out she had cheated on you. Thus began a year-and-a-half long on and off again relationship that burned and sank to the bottom of the ocean. It was one of the most painful experiences of your life, and you have avoided her ever since. But now she was here, as you knew she would. She was still a good friend of Jeff and Alex's. She still looked stunning, a redhead with freckles and an ass to die for. Her thin physique somehow supported her wide hips that hypnotized men through any layers of clothing. You politely say hello and introduce her to your 'girlfriend', and she seems to be happy you even acknowledged her. She introduces the two of you to her fiance, Eric. Fiance. Great. You remember Eric. He was one of the guys you were sure fucked Anya that freshman year of college, but you never found out the truth. He doesn't seem to recognize you or even car who you are.

As you sit down with some freshly poured wine, suddenly another ring of the doorbell. Claire excuses herself to get the door, a job she seemingly has appointed to herself.

This woman is someone new to you. She is a beautiful young black woman with long flowing jet black hair and a pretty large rack. She's wearing a short skirt and a tank top that leaves little to the imagination. Your interest piques immediately. Alex rushes over to hug her, and then introduces her to the guests.

"Guys, this is Eva, my maid of honor!"

Then it clicks, this is the Eva that you have heard so much about from Jeff and Alex. She still lived in the college town that her and Alex went to grad school in, so you never got the chance to meet her. And that you now regret.

As everyone resumes mingling, Jenn is already deep in conversation with Jeff, the two of them always got along so well. He was sure she was the one for you.

But now, you gotta decide who to strike up a conversation with.