8- My High School Sweetheart’s Little Sister -pt. 8 (Practicing with Stacy / Poolside) by JadeGrey

A few minutes after I hung up the phone rang again, but this time it was Ken telling me the project I was working on had to be put on hold. He couldn’t have timed it better. I was out of the door in minutes.

My heart was beating hard as I drove towards Stacy’s. My dick was getting hard too, in anticipation of just seeing these two in their bikinis, let alone thinking about what might happen. I thought about stopping home to grab some swim trunks, then thought it would be better to ‘forget’ them. I had picked up a pack of Trojan condoms, after throwing away the cheap rubbers I bought at the 7-11 that broke last time.

.

——————————— Listening In ————————————

I pulled in their drive and parked on the side. I realized they weren’t expecting me to be here so early, so I quietly let myself in through the side gate and went around to the back by the pool. I could hear them talking, and stopped short when I heard both of them shrieking.

“OH MY GOD! They are SO HOT!!”

Stacy squealed, “Jordan! He’s such a dream… what I would do with that boy…”

I finally realized they were talking about the new ‘boy band’, New Kids On The Block, playing on the radio. I didn’t like the bubblegum music, but young girls went crazy over them.

“Ha! I’m sure you would do whatever he wanted! If you only got the chance to let him!”

“I WOULD! I would deep-throat that dick like I did with Jeff. He wouldn’t expect THAT from this innocent little girl!”

“What? Stace! I thought that hurt you! You were almost crying!”

“No… It didn’t hurt… not really. I just never did that before and I was scared! It was actually pretty hot… ya know… that was really naughty! …and Jeff said it was the best blowjob he ever had!”

“Oh my God, Stace… you made me think I really hurt you!”

“No… I was just scared. I’m not scared anymore. Maybe Jeff would like another one tonight?”

…….this immediately triggered my dick

“What the hell, Stace! Jeff’s MY guy! I’m open to sharing, but you’ve been able to do stuff with him I can’t! He popped your cherry!”

“God! I hate that saying…”

“Well- it’s true, whatever ya wanna call it. He was supposed to make love with me… I’m so mad at my body. Tiny little tits, and a kitty so small I don’t think I’ll ever…” Cindy’s voice trailed off, and there was a bit of silence.

“I wanted to talk to our doctor about it, but I can’t think of a reason to tell him why I… ya know… why I want to be larger… especially at my age. And what if he told my parents? Oh my God.”

“Have you tried to… um… kinda… stretch it out? I mean… don’t you use your fingers down there?”

Cindy laughed, and sounded a little embarrassed when she finally answered, “well, yeah… but I only rub the top.”

Stacy didn’t sound embarrassed at all. “You never go inside? That’s like the best part! I’m pretty sure that’s actually how I ‘popped my cherry’, as you call it.”

“What- really? With your fingers?”

Stacy laughed, “Well, with actually with my hairbrush”

Cindy gasped and blurted back at her, “A HAIRBRUSH?!?! What the Hell?”

“No… not THAT part… the handle. Oh My God, Cin…”

“Oh… I guess that makes more sense.” Cindy giggled at her comment.

“I’m gonna grab more margaritas. Be right back.” I heard Stacy walk across the patio to the family room. I thought of walking in, but I wanted to hear more of their conversation. Also, the thought of Stacy masturbating with a hairbrush gave a major hard-on that would be hard to hide.

A few minutes later she walked back out. I could hear things being set down on the patio table, and glasses being refilled.

“Carrots? I thought you were getting chips.”

“Did you want chips? I can get chips if you’re hungry. The carrots aren’t for us to eat.”

There was a moment of silence, then Stacy started laughing. “The carrots are for practice!”

“Practice? What do you… STACE! Are you… oh my gosh…”

“I’m just here to help my bestie! Do you have a better idea?”

…… is she suggesting what I think?

There was a bit of silence, then I heard Cindy giggle. “Oh My God, Stace…these are all peeled… and…” her voice trailed off.

I knelt down and crept forward as quietly as possible to get a look. I was able to get below a shrub at the corner and see them.

“You’ve been PLANNING THIS! Stace… you little… oh my god… “

“What are friends for?” Stacy laughed and took a gulp of her drink. Then she handed Cindy her drink, “Here, I think you need a refresh.”

Cindy was shaking her head, but smiling. She grabbed the glass from Stacy and took a few big gulps from her margarita. They were both wearing tiny string bikinis, and were all oiled-up for the sun. Stacy was sitting on the near chaise with her back to me, and Cindy was sitting on the far chaise near the pool. She leaned forward and looked closer at the tray.

“Oh My God… these are all peeled, and all different sizes… Stace, you are definitely NOT a good influence.” Stacy laughed again.

Cindy pushed the carrots around on the tray, “None of these are as big as Jeff… well, maybe that one… at the big end, maybe. Didn’t that hurt? I mean… you said you played with your hairbrush, but…”

Stacy grabbed one of the carrots and held it up. It looked like a pretty large one. “Well, yeah… it did hurt a little at the beginning. But it felt good at the same time. The longer he worked that big thing into me, the better it felt. And after he really started pumping, and you were.. you were touching me and I was… you know… FUCK! …it was fucking crazy! I have never felt like THAT before.” Stacy laughed again, “I think about it all the time… my hairbrush is all about worn-out now!”

Cindy laughed and shoved her friend, “Gawd! You are such a perv!”

I watched Stacy put down the large carrot and pick up a smaller one, about the size of her finger. She reached out with one hand to Cindy’s knee, “Open your legs…”

“Jeeze Stace! Now? Right here? And that thing is all dry… it’ll probably turn my kitty all orange!” Cindy was trying to look shocked, but she was laughing when she said it.

“No.. it’s not gonna turn you orange. Here… watch.” Stacy stood up, her back towards me, and pulled her little bikini bottoms down below her knees.

…….Jesus, she has a nice ass

Cindy stopped laughing and stared at Stacy’s crotch. Stacy squatted down a little and spread her knees apart. I could see her one hand reach between her legs and spread her lips apart. She took the other hand and guided the small carrot up between her legs. Cindy just stared, mouth gaping open. I did the same, my dick hardening in my pants.

Stacy pulled the carrot out, “See? Nothing turned orange.. and it’s not dry anymore”, then she motioned for Cindy to move her legs apart. Cindy’s knees fell open a little. She was still staring at Stacy’s crotch.

…… I flashed back to our game of Truth Or Dare

Stacy pushed Cindy’s knees further apart and reached down between her legs. Cindy just stared with her mouth open. From where I was I couldn’t quite see, but I assumed Stacy was pulling her bikini to the side. Her other hand, the one with the carrot, disappeared between Cindy’s legs. Stacy dropped her head closer to Cindy’s crotch, and I heard Cindy gasp.

Leave a Comment