High School Archives — Page 365 of 805 — NSFW story

[m]y first sugar daddy experience via “whisper”

This happened in 2014, when I was in my mid-twenties. Just as a way of introductions and context, I live in Australia (Melbourne, at that point in time), Asian, and blessed with neither a chiselled body nor packing a massive cock. That being said, I’m confident and do okay with picking up ladies – but that’s another story for another time.

This story is really how I started getting hooked into the idea of sugar daddy-ing, and I’ve had quite a number of stories which I’m happy to share further if that’s of interest.

You might remember the good old days of “whisper”, the app where people make confessions and you can actually message them with a hope of a reply. One fine afternoon, while I was at work (I was working as an analyst), I got bored and started scrolling through the app in the toilet when I came across a local post that read “really want that dress, maybe I should try being a sugar baby”. Being the horny bastard that I am, I cheekily replied “well, I hope you’re at least 18, otherwise you might get people in trouble”. Read more »

Converting The Feminist Ch5 [mf][bondage][gag][anal]

Four days had passed since I chose to stay with Blake. Things were getting better, thus weakening my resolve. Blake still did things both childish and made me think he was an asshole. Every day, I got progressively more freedoms. The first day after Tyler visited, I woke up uncuffed. Originally, I thought Blake simply forgot. It wasn’t until the next day that I started to suspect he would not have me cuffed to the bed every day.

Blake didn’t give me complete freedom. Every day, I woke up locked in the same room. Sometimes, Blake would sleep the night with me. He let me out of my cell every day, but only when I could be kept close. Dresses, blouses with skirts, heels, heavy makeup; I had become the stereotypical poster girl of femininity.

Sexually, Blake was amazing and devilishly evil. When he fucked me, it was wonderful. It was never just sex. If I said or forgot to say something he didn’t approve of, I was quickly gagged. Ball gags, tape over my lips, cloth shoved in my mouth, ring gags; I never wore the same gag twice in a row. Read more »

We Sisters in the Time of COVID19

This is a story set during the Corona Virus outbreak in 2020 (for future readers). Everyone was self-quarantined — even if healthy – and all social functions were shut down until further notice (which had not been lifted at the time this story was written).

Fuck! My senior prom was canceled as was my sister’s Spring Fling Ball at college. The Corona Virus quarantine had kept me home from my last semester of high school and my sister had to move back into our room from her college upstate. My parents were both working from home as their respective companies had closed the offices until the all clear was sounded — which was for some undetermined date in the who-knows-when-future.
So Kristy crowded back into my room, or I guess, “our” room, after unloading all her stuff out of my Dad’s car in the driveway last week. Mom thought it was fun to see her girls back together again after only a few months of my older sister’s freshman year at Roane State. I hate to say it but I didn’t like it at all. Oh, I like — love — my sister but I had gotten very used to having the room all to myself. So I had to clear all my stuff back into the shared quarters of closets and bureaus and night tables to make room for Kristy. Read more »

I [F] put on a show for my neighbor

This happened a year ago when I was 19 and visiting home from college but I thought you would all enjoy!

My parents have lived in the same house for the past 30 years but five years ago there were a few months where a lot of families moved in and out. A couple in their 40s moved in right next door. The man was a professor and the woman worked in finance so they seem pretty straight edge.

I saw them a few times while i was in high school but never paid any attention. During winter break my sophomore year I went back home for an entire month. Now I can spend all day masturbating so if given the opportunity I will. During this month my parents had to visit family in a different state so I had the house to myself for a long weekend. I religiously spent my time just alternating between all my toys. During this period I would also always run into my neighbor while getting the mail so I would chat for a bit and started to think he was kinda hot. Read more »

Just Friends [Gentle Femdom] [Loving] [Humor] [Facesitting]

He was her best friend. And now, suddenly, she was owning him like this. She had never been so… felt so… powerful. How did they end up here? How did she end up on top of him like this… rubbing him like this… moving her body in ways she never had before…? She had nearly forgotten through all the pleasures.

 

Darren had been her good friend for many years. Through high school. Through college. Now they were roommates with other mutual friends.

And through all of that time, Isabelle had repressed her feelings for him. She’s lost count of how many nights since the day they met, she masturbated to the thought of him. And her fantasies increased in intensity over time. She would often think of him tied up. At her mercy in many different situations. Many of them were dark… that she had stolen him away completely, keeping him locked up somewhere no one could find him. She felt strange… felt bad for thinking such things. After all this was Darren. The guy who helped her through multiple breakups. The friend who she loved to talk with for hours about life and video games and whatever other nerdy, mutual interests they had. Read more »

[MMF] Finding [M]yself Post Divorce

I married young and sexually inexperienced. I stayed married to a woman for 15 years who grew increasingly distant emotionally and sexually. The last several years were a dead bedroom, leaving me a lot of time to contemplate what I had missed out on experiencing in my late teens and 20s.

We eventually ended things. I was torn between feeling bad that I couldn’t make it work, and being exited to go out and have new experiences.

There were a few phases along this path where I was definitely feeling bicurious. In the past I knew a few people could sense it too. At one point, a couple – who were acquaintances – put feelers out while I was still married. I turned them down thinking things would change at home. By the time I was divorced, they had moved out of state.

So two years ago, I started posting in a few r4r’s here. I wanted to find a bi-couple who we’re really into each other but also loved to share each other. Read more »

Our Sex Life – Part 2 Exploration [FM][FF]

This is part 2 of a series about my wife and my sex life from the start of our relationship. Check out our profile for part 1!

After the “spandex night” described in Part 1, she and I spent many more nights together trying not to cross any lines. One day she texted me that she wanted to come over after class to do homework and I replied that she could, but that I couldn’t stop thinking about the spandex night and I wanted to get myself off to it. She thought that meant she shouldn’t come over but I quickly clarified that she was still welcome to keep me company during as long as she didn’t see anything. When she arrived I was already naked under my sheet and she crawled into my lofted bed next to me. She lay seductively on her side glaring into my eyes and told me to keep going. I grinded against my bed with her running her hands over the sheets until finally I came hard. One night not too long after that day I remember we were spooning in bed and she was wearing soft pajama pants. She quickly noticed my hard dick pressing against her ass and she started to slowly rock her hips against me. As if to call her bluff, I at one point reached down and grabbed one side of her pajama pants and gave them a gentle tug, partially exposing her ass slightly covered by a lacey thong. To my demise her pants quickly slid back into their resting position. She must’ve been feeling particularly frisky that day because she reached down with both hands, raised her hips off the bed, and slid her pants off altogether, returning to the spooning position. This sent a warm wave of lust over me and I turned her face down and grinded against her ass until I came in my boxers. Over the next 6 months we slowly crossed more lines until finally we gave in and started dating (and fucking). She was not my first, but she was the first girl that ever made me cum while having sex. Read more »

i’ve [f]19 been flashing my neighbor (m 40) since covid and now i want to fuck him

yeee

ive posted this on sluttyconfessions 2 days ago but some of you told me to post it here as well so yeah…

I’ve been flashing my 40 year old neighbor since covid now. Ever since the pandemic started, i stayed at home more often because school was mostly online. my neighbor also had to stay at home for the most part because he was a high school teacher so it was all online classes. we wake up at the same time in the mornings because we both have to be ready for our classes and my room is directly across from his room. normally he would wake up a lot earlier than me for school (around 5am) and he would be out of his house by 7. however now because of the pandemic he wakes up the same time that i do and i spot him in his room sometimes. he is a single dad with 2 children who are cute af tbh. i sometimes babysit them for some extra money if i have the time. Read more »

My Sorority Girl

Hi everyone! I’m Jennifer Johnson, a dark erotica author. I wanted to share this story with you. I’m very proud of it and I hope you enjoy. It’s basically about a role-play that turns into a schoolgirl orgy!

**This story is a request that has been bumped to the front of the line in exchange for payment. Thank you so much for your support! I truly enjoyed writing this story for you.**

**Someone said: First, thank you so much for all the amazing stories ? I was wondering if you would write a story that’s been a huge fantasy for me. Currently I’m living my best slutty life with four partners who I love and who love each other. I’m in my late thirties and all of my partners, and their husbands or wives are all either my age or a decade or so younger. I live in a college town (ASU) and my neighborhood has a lot of students, in fact the house behind mine is a two story full of sorority women. Sometimes whenI fuck, I forget to close the blinds. My fantasy is imagining those young women watching; learning what good, real dominate, body positive, toy positive, fucking looks like. Naturally I’ve also masturbated imagining one of them getting up the courage to ask for a demonstration. Thought it would make a really hot story.** Read more »