The Side Project
Copyright© 2026 by The Side Project
Chapter 4: Reed
Fiction Sex Story: Chapter 4: Reed - A couple of normal, if irreverent, middle class guys get the opportunity to answer the age old question: What would you do with your life if money was no object? A collaborative writing project written from multiple character perspectives.
Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Romantic Lesbian Heterosexual Fiction Humor Cheating Group Sex Anal Sex Analingus Cream Pie Exhibitionism Oral Sex Squirting Voyeurism Slow Illustrated
Money Can’t Buy You Happiness. But It Can Make it Easier to Fuck Hot Chicks.
“Hi, the bartender says I have you two to thank for my free Cosmo, so thank you,” the woman who had approached us said.
“My pleasure,” I said, maintaining eye contact. One thing I had learned over the years was that when meeting a woman in a setting like this eye contact was important instead of just ogling her. “What’s your name?”
“I’m Ashley. Y’all?”
“Reed.” I extended my hand and shook Ashley’s. Kyle introduced himself and did the same.
“So buying the whole bar a round? Quite the move,” Ashley observed.
“I landed the craziest parlay bet ever, I felt like a little celebration,” I lied to her.
“Oh, that’s super cool, very generous of you to share your windfall,” Ashley said.
“Generosity is definitely one thing I’ve learned from Reed,” Kyle said. He was slipping into wingman mode, probably had already texted Lexi he was coming over.
“That’s a nice quality. I like generous men,” Ashley said, her tone was definitely suggestive. Getting this girl back to mine was not going to be hard.
“So what has you flying solo and dressed to the nines in a bar like this?” Kyle asked. We were both wearing dress shirts since we had been at a nice steakhouse, but we were the minority in terms of how well people were dressed. Ashley was easily the best dressed woman in the place.
“Just needed somewhere to blow off a little steam, had a terrible dinner date, needed a stiff drink before I called it a night,” Ashley explained.
“Well feel free to have more than one as needed,” I offered.
“His generosity knows no bounds,” Ashley said and giggled lightly.
“Common side effect of a bottle of wine apiece at dinner and us being on our second round of cocktails,” Kyle said.
“Oh, where did you guys get dinner?” Ashley asked. I named the place and saw her eyes ever so slightly widen. She knew it was not cheap.
“Well it sounds like you’re primed to make some bad decisions then,” Ashley said, saucily.
“I think that depends on how you define bad decisions,” I told her. “I’m not exactly risk averse.”
“Do you think another Cosmo would be a bad decision?” Ashley asked.
“Depends on whether you’re going to order another crummy one from this sports bar or let me make you one properly back at my place.” I made my move.
Ashley smiled. “I can only imagine a man of your generosity has the highest quality ingredients.”
“I can assure you, he only makes top shelf cocktails,” Kyle said.
“Well then, I think the only bad decision would be not to accept your invitation,” Ashley said. I ordered a rideshare home, finished my drink, fist bumped Kyle, and we left the bar.
The ride back to my place was only fifteen minutes, and the pretense of getting to know Ashley lasted maybe two of that. She mentioned being a pharmaceutical sales rep, hocking some new cholesterol drug that she seemed to have as much passion for as I did. So as she talked, I slid my hand up the generous amount of thigh her little black dress left exposed. She turned her head and flashed me a look that showed no resistance or surprise.
“What do you do for work?” Ashley asked, sliding over close to me.
“Does it really matter?” I said.
“Nah,” Ashley said and moved in for a kiss.
She tasted like booze but had soft lips. Her tongue darted in and out of my mouth. I was too busy letting my hands roam to realize she wasn’t a great kisser. I felt the bump of her bra as my hand slid up her back. My other hand sought the warmth between her thighs, but I was gentlemanly. I didn’t push it too high toward the junction between her legs, though I could feel heat radiating from it.
Before we knew it, the rideshare had pulled up to my apartment. I told the driver the gate code, and Ashley straightened her dress and hand-brushed her hair. We got out and walked up to the second floor. We didn’t talk, but Ashley slipped her hand in mine as we made the trek. It was a pleasant, cool night, one of those rare times to enjoy the Houston weather. I slipped my key in the door and opened it. By the time I turned around after locking the deadbolt, Ashley was nearly plastered against me. Her arms engulfed my neck and pulled me into her. She still wasn’t a good kisser, but she seemed eager enough, and that had to be worth something.
I made a move to direct her toward the bedroom as we made out. If she stopped me, I’d offer the drink. She didn’t. The dance to the bed was slow but persistent. By the time Ashley felt the mattress behind her, she didn’t even blink. She sat down on it, putting her at eye-level with my crotch. She went straight for my belt, unbuckling it, then undoing my pants and pushing them down, along with my boxers.
Fuck, I thought, this absolute smokeshow is going to just give me head without even making small talk. What a find!
She stroked my cock a couple times, but it was more than ready for action. Then she gave the tip a tentative lick. Her tongue was very wet. She took my head in her mouth, then slid down another inch or so. Then she pulled back. This promised to be fantastic, teasing head, I thought.
Then she took my cock out of her mouth and stroked it a couple times. Then put a couple inches in again briefly, then stroked me again. It dawned on me finally that, no, Ashley wasn’t into giving head. This was terrible. I was going to go soft if she kept this up, and I didn’t want things to get awkward. So I did what any gentleman would. I grabbed her hands and pulled her up. I wrapped my arms around her and kissed her neck. She gave a soft moan. I found the zipper on the back of her dress and pulled it down. The wispy black fabric easily fell to the ground, revealing black, lacy lingerie underneath. I unsnapped her bra, and I had to admit it. Her tits were glorious. Round and delicious, with dark, hard nipples. She glided her panties over the swell of her hips and stepped out of them. I invited her to lie down in bed.
This was my go-to move. I had gotten enough compliments on my oral skills that I felt confident it was my best way to win over any female company. I took my time working my way down Ashley’s body. Her tits were worthy of more attention than I gave them, but I had a singular purpose in mind. I settled between her thighs and began to explore her soft, feminine folds with my tongue. She ran her hands through my hair, pulling it a little too roughly, as I pushed past her labia and into her honey pot.
Although, I had to admit that it was less of a honey pot than it was a vinegar pot. Ashley, whether it be through a lack of attention to hygiene or genetic misfortune, didn’t have the most attractive taste and smell. But objectively she was a hottie. So I powered through for a couple minutes to get her truly warmed up.
“Do you have a condom?” Ashley finally said, as if reading my mind.