High School Archives — Page 69 of 805 — NSFW story

I used my FWB’s toys to cum while watching her nephew. They both have no idea. [FM]

*I’m not exactly proud of this, it’s pretty inappropriate and out of character for me but it’s been two months and I can’t get this out of my head. So I will write it out as best as I can. Fuck. Ok.*

Chelsea asked me to house sit for 3 weeks while she’s in London for work, it was one of the easiest yes’ of my life. She wanted me to take care of her plants and kitty Frank, who I’ve bonded with and cuddle most nights. As I’ve stated previously our relationship is confusing. I sleepover a couple times a week, go out on dates, shop, and workout together with no title. It’s not that we don’t talk about being a couple, considering we act like it. But Chelsea suggests we take things slow, especially since she’s a lot of “firsts” for me. She travels a lot for work, it’s go with the flow type of vibes. Cool. Read more »

Tail Butt Plug, Costume Party, and [M]y [F]irst Anal Fuck

My dad is a CEO, but his motto is that money is fleeting, skills are not. He and my mom made sure I could take care of myself in any way necessary. Sure, he is comfortable monetarily, but we’ve always lived below our means. Status never meant anything. Except for meek, socially anxious Wren in high school.

One skill I was taught when growing up was how to sew. And I’m pretty good at it, if I do say so myself. To this day, I wish there was a picture of the costume I made for the Halloween party we attended senior year. Rather than buying one, I chose to create one. And I was fox. In costume and look. We were both 21.

The only thing was that it required a little modification. I already had the white thigh highs and arm compression sleeves, the black gloves, and black shoes. I only had to buy the orange leotard, ears, and the tail. The latter of which is where the modification comes in. It wasn’t any tail, but a Fox tail butt plug. But with the skills I had learned, I was able to fit it through the clothes easily and to look like it was part of the get up. Read more »

Catching Up: Part Six 21+ [M40/F37] [Straight Sex] [Interracial] [Cheating] [Busty] [Huge Boobs] [Playboy Bunny]

Chapter Six: A Weight Off

I got into work the following day, still sore all over. Muscles ached that I never even knew I had, but it was a good sore. It meant that I had put my body to the test, and it had passed. I thought I would still be in bed after yesterday’s game, but I was reporting to work here.

“Rod!” Jackson yelled from down the hall.

I looked around and saw that everyone was frantically running back and forth. “What’s going on?” I asked.

“You have no idea the morning we have had,” Jackson said as he walked with me to his office. “You had a game yesterday with some of your old friends?”

“Yeah,” I said as I sat down.

I didn’t think anything of it. It was a good pickup game, nothing big. We used to do it all the time when we were in college and even in high school.

“What’s the big deal?” I asked.

“Big deal,” Jackson said as he smiled back at me. “The big deal is some of your old friends are retired sports stars,” Jackson said. “The big deal is some of those students that were watching put videos online, Snapchat, Tik Tok, Facebook, you name it, it’s all over the place.” Read more »

Plugged In 21+ [M42/F40] [Straight Sex] [Quickie] [Busty]

“Have a good day, honey,” my wife Holly said as I descended the stairs.

“What? No goodbye?” I smiled at her.

“Sorry,” Holly said as she rushed toward me. “Have my head in the clouds,” she said as she kissed me on the cheek. “Have to take the kids to school. Be safe!”

I nodded and picked up my briefcase, and the to-go breakfast Holly had packed for me.

Being the police chief had its advantages; today was one of those days.

“V.R.,” I said as I got to the downtown laboratory.

“Yes,” the lady said standing in front of me said.

“Virtual Reality,” my assistant said to me.

“Yes, I know what V.R. stands for Thomas,” I barked back at him.

“How does this help my officers?” I asked. “We have in real life situations, how is this going to simulate that?”

I had other chiefs with me from different cities and nearby states.

Supposedly this company was trying to get us all to start using this technology to help eliminate some of the accidental police shootings. Read more »

[FM] My last night as a sugar baby, ever

This is exhilarating! I want to keep this up a little longer. Like I said on my last post, I worked as an escort and a sugar baby all through my late teens and twenties. A few years ago I got out of the biz, if you want to call it that, and now I make a living mostly from my investments. This is the story of my last night as a sugar baby.

Some people asked me to describe myself last time, so I will. I’m thirty six years old now and for a long time I struggled with not being so young anymore. But even though I weigh more than I did when I was a twentysomething, I still work hard to keep in shape. I’m curvier now than I was then, but thanks to the gym I make it work for me. My hair is long and chestnut brown, the same color as my eyes. My eyelashes are my best feature while I have clothes on. When I was a teenager I struggled to stay as skinny and small as the other girls, so I appreciated when bigger butts and tits came into vogue. After so many years dressing to impress I usually wear athleisure clothes unless I’m going out with friends or on dates. Read more »

Monthly Session

It had been a month. A month since I felt his touch. A month since I felt his lips. A month since his voice in my ear sent chills down my spine.

I parked in the driveway and turned off my car. I dropped my keys getting out and only then, reaching to pick them up, did I realize my hands were shaking. God, I was excited. The proverbial kid at Christmas, so eager for the gifts he was about to give me.

I rang the bell and waited for him to answer.

He opened the door wearing dark denim jeans and a button down shirt the color of sunsets. He smiled and I felt my body clinch. “Hello Princess. Do come in.”

Fuck! His voice. Deep and somehow both soft and commanding at the same time. I stepped inside his layer and he closed the door behind me. The lamp in the corner was on, R&B that took me back to high school played softly on the soundbar. He moved up behind me, close, but didn’t touch me. I could feel his sexual energy like a phone on silent vibrating on the bed. “It’s good to see you again.” That’s what he said. What I heard was “I’m going to make you my slave.”, and I was okay with it. “Have a seat.” Read more »

[FM] my sisters friend

It was a cold day at the airport, as I waited for my mom at the airport. I was very excited to be back home as it had been quite a long time since I had seen everyone. I had landed quite late, and it had begun to snow. I decided to wait in the airport just able to see the front to see when they were coming. I then got a message that they were rolling up right now. It wasn’t hard to tell it was them; the parking lot was empty. I ran out, opened the back, and began to throw my things in the back. “shit it’s cold,” I moaned as my mom and siblings came out, Quickly giving each one a hug before we all hopped in. How’d you like flying in this weather my mom asked while laughing. “Eh, it was interesting, definitely a hard landing,” I said while warming up my hand with the heater vents. We began to drive out of the parking lot as she started to tell me about how life was in our small town. Read more »

10 Year Reunion: Cheerleader in the Locker Room [FM]

Last year was our 10 year high school reunion. Despite moving back to our hometown to take jobs at my dad’s company, this would be the first time in years we had seen these people. Some by choice, some by accident. Either way, it was kind of exciting.

Steven had been out of town at one of the company’s distribution centers; he would come later straight from the airport. I understand as little about his job as he does about mine in finance so I still don’t quite know what he was doing. I did know, however, after a week away just how I’d welcome him home. The reunion provided the perfect opportunity.

Even 10 years later, walking through the halls of the school reconnected me with the innocent head cheerleader that once roamed them. At 28, I could do what I wish she could have then. All I had to do was put up with small talk until Steven arrived.

Unfortunately, Ben was there. I had cut him off that day 7 years before, but because we weren’t friends on social media and I came alone, he immediately decided I must be single. He had also just recently gotten out of jail for sexual assault, shocker. He commanded all my attention and I couldn’t break from his advances until I felt a familiar hand around my waist. Read more »