High School Archives — Page 169 of 805 — NSFW story

[MFF] My first threesome with my girlfriend and a girl I’d cheated with

*I received a barrage of messages after posting my previous story, asking for this one. Honestly, some of your responses turned me the fuck on, so I had to write this down now (and promptly rub one out after). If you’d like to read the original, click here:* [*fucking my roommate’s gf while my gf slept upstairs*](https://www.reddit.com/r/gonewildstories/comments/ry1qo6/mf_hot_tub_fun_with_my_roommates_girlfriend/?utm_source=share&utm_medium=web2x&context=3)

As you can tell from the title, it wasn’t an ideal situation from a moral standpoint. Cheating is wrong, and I’m an asshole for it. If you haven’t read/don’t feel like reading the previous post, here’s the TL;DR. I fucked my roommate/close friend’s girlfriend after we hung out in the hot tub, while he and MY girlfriend were sleeping in their rooms upstairs. It was the only time we hooked up and I thought it’d never happen again. But man, did I fantasize about that ass on a regular basis.

Another long one, so buckle up! Skip down if you just want the good stuff, I won’t be offended ;)

***Important Characters*** Read more »

Haley’s Choice (Part 1) [F/F]

Mistress Laura was the kindest sort of cruel woman. She was a sadist of the darkest kind, and she was rich enough that she could afford to find beautiful, young women who would indulge her awful fantasies. Usually, these were simple exchanges. Some poor, desperate woman drowning in student loans or medical debt would seek out the Mistress, and she would agree to get an embarrassing tattoo or undergo some horrible torture in exchange for having her financial burdens lightened. Laura called herself a philanthropist. Her extravagant wealth put her in a position to help women who needed help, and she was more than happy to do so. All she asked in return was to have her fantasies indulged. To get a bit of pleasure from the exchange. One night of kinky, often painful, always humiliating lovemaking later, and the girls were free to go. Read more »

[FM] How this painfully shy virgin finally got fucked.

I’m taking a break from my Sophie saga as things are still developing there (in a good way); I want to give it some time before posting another update. For now, here’s the story of how I lost my virginity…

I was invisible in high school, which suited me fine because my conversations with people usually ended with me anxiously bumbling random words as I desperately searched for the nearest exit. My motto for those awkward teenage years was simple: *it was better to be thought a weirdo, than to speak up (or stand out), and remove all doubt.*

So I did my best to blend in and go unnoticed, and I was pretty good at it too, probably because I was average in every way: short, but not too short, with boring brown hair and moderately fashionable clothing that wasn’t too colorful or flashy (for some reason I really liked Taupe tones back then). I was the living embodiment of teenage camouflage, perfect for a shy and awkward teen. Read more »

Ugly Duckling [F20] is sold by her bully to a much older stranger. [FM]

Hi, I’m back! In the last story I shared, I started my 2-year long enslavement by my master, Mike, my high school bully. Now, I want to give a fair warning this time. My sex life with my bully was a BDSM dom/sub relationship. I never did anything against my will and did say no to him from time to time, but frankly, I had way more fun when I said yes. I did most of what Mike wanted and I loved it, when I’m degraded, insulted, and ordered around I feel like I’m at my most calm. I know that may sound weird to some, but I spend a lot of time overthinking things and questioning myself, so it’s such a wonderful break to be controlled, I can just turn my mind off and feel great and please others.

***Fair warning, the following story contains these kinks: Cheating, submission, rimming, degradation, insults, prostitution (?), age gap, unattractive male partner.*

*TLDR:* I fuck an old unattractive stranger for an unknown exchange of goods or services. (I was going to make this a shorter story, I don’t know why it got so long. So many memories came flooding back to me)** Read more »

[MF] I Want My Stepsister Part 1

My father married Ashley’s mother when I was in junior high school. My dad had been single for several years after my mother passed away from cancer. It had been a tough time for both of us but we were able to come out of it. When my dad started dating Jenny, I thought she was kind and she really seemed into my dad. I liked how much she truly made an effort to get to know me. She wasn’t trying hard to be my friend or put on an act to impress my dad. She was very genuine.

When I first met Ashley, I did not know what to make of her. She was two years older than me and seemed to be put out by my presence in her house. Our first meeting was one of few words and avoidance. We had a hostile relationship for some years with both of us ignoring each other. I would snap at her if she touched my things and she would push me if we walked by each other in the hallway. I couldn’t stand her for many years. Read more »

The Hidden Box!

I laid the pictures out, side by side, on the edge of my parents’ bed. My cock was already hard enough to pound nails. It took a while to dig them out each time, but it was totally worth it.

I can’t even remember what I’d been looking for, or maybe I’d just been snooping. Either way, I’d been in my parents closet when I shouldn’t have been. I’d thought it strange there was a cardboard box hidden under a stack of my dad’s sweaters. Obviously, I couldn’t leave it alone. Opening it changed my life.

There’d been some letters on top. Each had my mom’s familiar curly handwriting. As I pulled out the stack of them, the pictures hidden underneath captured my attention. Later, when curiosity got the better of me, I did read what she’d written.

My dad had been given an amazing opportunity shortly after I’d just started my first year of grade school. His boss had asked him to oversee a major expansion for the company out west. The project kept him gone for over a year. The letters and photos were from his time away. Read more »

Married Indian MILF is Humiliated in public [looking for someone to continue the story]

Indu was a fine married mother with curves to die for. She was Indian, and as such, had deeply tanned skin with jet black hair that accentuated her beauty. She had full, slightly pouty lips and large, natural breasts which she covered up in a conservative white blouse. Her wide hips and round ass caught the attention of men in her denim jeans. At 44, she could certifiably be called a MILF.

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Indu was shopping at the local mall for new outfits for the summer. She was looking at various tops when she noticed that a young boy was eying her closely. He looked to be barely old enough to be out of high school, if even that. He was white and had a sleazy look to him, the type of kids she would warn her own about. He was lean and muscular, with what looked like a bulge in his shorts. She walked over to look at various kinds of legwear, and she noticed the boy stealthily following. She picked up a pair of short shorts, thinking how slutty the dirty girls were who wore clothing that showed so much skin. She was curious how they would look on her though. As she spaced out, she accidently knocked some clothes down. She bent over to pick them up and saw the boy from earlier staring dead at her round backside, and noted that his bulge got bigger. Indu was curious about this boy now. She had never thought of herself as “sexy”, and yet this boy was clearly interested. But that sort of thing wasn’t allowed in her culture, not to mention she was married with children and much too old for the boy. Read more »