The time I (kind of) became a sugar daddy and then my friend insisted her best friend and I hook up

This is a long post that mashes together two related stories. This post is broken into multiple parts and continued in the comments. I debated posting as it's kind of embarrassing to admit to some of what is in here but whatever. Hope you enjoy it.

A few years ago I was in the midst of a particularly long dry spell. It had been a long time since I'd hooked up with anyone and even longer since I had had a date or been in any kind of fulfilling relationship. I was definitely feeling down in the doldrums.

I had been hanging out with my friend Rachel who I had known since highschool. She had curly, blonde hair and very pale, freckled skin. She was fit with large boobs (either large C's or possibly D's) and a smile you'd find in a toothpaste commercial. Rachel was a bit wild when we were younger. We had a little history together but that was several years in the rearview. Still, we were always very flirty in a sexual way with each other. Since Rachel and I were spending a lot of time together she got to hear a lot of my self pitying and complaining.

I'll admit that I had, on more than one occasion, hinted with Rachel about the possibility of us hooking up. Rachel did agree that I needed to break out of my slump but shot down my attempts at breaking out of it with her.

One night we met up for drinks at a pub that had keno. For those that don't know, Keno is a number game where you pick your numbers and if they come up in the game you win money. I put down the money, let Rachel pick the numbers, and agreed to split any winnings 50/50. Over the course of the evening we got a little drunk together. Rachel was wearing a flowy low cut blouse that showed a lot of cleavage.

"We just need to find you a friend with benefits," Rachel said as if we were now a team in solving this problem.

"I agree but you keep turning me down!" I teased.

"Not me, dork!" Rachel replied.

"Then who?" I asked.

"I don't know. I'll have to think about it," Rachel said with a contemplative look on her face.

"But hanging out with you has set my standards too high!" I teased again. Not my smoothest line but I was drunk.

"Oh shut up, doofus," Rachel replied dismissively.

"It's not my fault you're the hottest chick I know," I insisted.

"Well you will just have to lower your standards a little," Rachel shrugged.

As the night went on we got really drunk. Rachel didn't have a boyfriend but she started getting lots of texts as the evening wore on. After some prodding I discovered Rachel had a special relationship with an older man. Rachel was in her 20's and this guy was apparently in his 50's. I also got the impression the guy was married because she wouldn't give me much info about him aside from not so subtly bragging about how rich he was.

"So what? Is he your sugar daddy?!" I asked in a faux disapproving tone.

"Kind of!" Rachel laughed. "He bought me this," Rachel continued, highlighting a tennis bracelet on her wrist that looked expensive.

"Awww," I whined, playfully, "I want to be your sugar daddy!"

"You can't afford me," Rachel winked.

"So wait… is this an actual sugar daddy situation? Like is he paying you for sex?" I asked.

"No, stupid! I'm not a hooker!" Rachel replied, defensively.

"But would you be with him if he wasn't rich?" I prodded.

Rachel's delayed response spoke volumes.

"You big hoe!" I teased when Rachel tacitly acknowledged she wouldn't be seeing this guy if he weren't rich, "Why not let ME be your sugar daddy?"

"I told you, you couldn't afford me. And… he has a REALLY big dick," Rachel explained. I found it hot that Rachel was openly talking about some guy's dick.

"Well I have a… medium sized dick," I replied.

Rachel snorted in laughter, almost spitting out her beer.

"Ok ok… My buddies and I play this game all the time. How much money would it take for you to have sex with a guy?" I asked.

"You play this game all the time?" Rachel replied.

"All the time. I'm probably the least expensive of my friends," I joked.

"So do I get to choose the guy?" Rachel asked.

"No! That would defeat the point of the game!" I explained.

"For sex? I don't know… like a million dollars," Rachel answered.

"Oh please. A million dollars? You're supposed to give a real answer. Are you telling me that if someone honestly offered you… I don't know… ten thousand dollars to have sex with you, you wouldn't do it?" I probed.

Rachel considered the question for a moment, "Not for ten grand. Maybe for like… fifty."

"Fifty grand?! Well you are WAY more expensive than I am," I laughed.

"What would YOU charge to have sex with a guy?" Rachel asked.

"I'd at least have to be able to pay off my car. I'd cost less than half what you charge," I admitted.

The older guy kept texting Rachel and I was getting a little annoyed at him interrupting us.

"What does he want?" I asked.

"He wants me to come over but I told him I was out," Rachel answered.

Continued in the comments…