Tag: High School

I [f]ace-fucked [m]y 20-year old tenant after she wrecked my wall – part 2

Seems like plenty of people enjoyed the first part of my first night with Maddy, so I wrote up what happened next. Found a good stopping point, there’s a third (last) part that I can try to write up this weekend.

[Part 1](https://www.reddit.com/r/gonewildstories/comments/grusxx/i_facefucked_my_20year_old_tenant_after_she/)

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By the time I made it back to the Redding house, both spots in the driveway were occupied. “Great, a full house” I thought to myself. I decided to stop by my shop (where I also live, another story for another day) to clean myself up, and grab as many tools and supplies I had laying around so I could make the Home Depot trip as quick and inexpensive as possible.

I jogged up the steps with my small tool bag and drywall piece and knocked on the door. The door swung open and I was greeted again by Maddy, this time in dark sweats and a baggy t-shirt and had the name of the university printed across her chest. An image of her tits, wet with her own saliva, flashed in my head. Read more »

My wife’s sister (M/F)

Erick and his wife Sylvia had met when they were very young, and he was quite inexperienced. They fell deeply in love and like many couples, experienced an excellent honeymoon phase that burned hot and unfortunately fast.

Adrianne was Sylvia’s younger sister. Erick noticed early on that they looked quite alike. Still, Adrianne was shorter, a darker complexion in both hair and skin, and her eyes were more black than the deep dark brown of his wife. The most significant difference much to Erick’s delight was that Adrianne had an impressive massive rack that dwarfed her older sister’s solid C cup. These C cups were not apparent. Several times her wife joked about how her sister had been blessed with the most chest.

“what no way!” Erick would say. “Even bigger than your peak mommy titty milk titties?”

Sylvia rolled her eyes. Even with the weight gain from being pregnant and the swelling of her breasts while breastfeeding, they still never got as big as her little sisters.

“Fucking perv.” Read more »

I [f]ace-fucked [m]y 20-year old tenant after she wrecked my wall

**Disclaimer** This is a ton of set-up for a relatively short encounter. I included all this backstory because it sets up a bunch of other stories that I can write out if there is any interest. I threw some asterisk down where the fun stuff starts.

I am currently (in 2020) renovating the bathroom in one of my houses, and I just finished moving a light fixture and installing a drywall patch… which reminded me of a series of events that took place at a rental property that I own. This experience happened about 4 years ago when I was 28.

Both of my parent’s died in an auto accident when I was 20 years old, and in a final act of love and support, they left me – their only child – with no debt, a good chunk of assets (their house that was mostly paid off, their retirement fund, etc.), along with a little over a million dollars in life insurance. Read more »

The Hot Tub [MFF]

It was a Tuesday afternoon, the summer of my high school graduation. I was going about my usual day woke up late, cooked an over medium egg and coffee with light cream. Suddenly I feel my phone start to blow up, I check the messages and its my childhood friend Kayla. She only lives about 2 hours away from me now, after my parents moved us in middle school. She states her regret in not being able to help me ring in my 18th birthday the “proper way” what ever that means. She also said she will be coming to visit a friend of hers tomorrow and wants to come over for a few to catch up. I have not seen her in almost a year so I’m very excited by the idea. I gladly accept her offer and tell her she more than welcome over for dinner. Truth be told I have no right inviting her over, my parents are currently out of town on a friends week at the cabin, and my sister stayed at college over the summer. Never the less I invite them over. Seeing as the only thing I can actually cook well is a fried egg and toast, it’s looking more like pizza is on the menu for tomorrow. The day finally arrived I truthfully had no real expectations of that night just some pizza, catching up, and I guess making a new friend. Kayla texted me saying shed be here at 6:00 PM. As per our usual agreement Kayla and her friend pulled up around 6:35 PM casually late as always. Kayla was a light skinned girl, stranding about 5’2” thick curly black hair, light brown eyes, she had some great curves too, and medium sized breasts. Her friend was the polar opposite. Pale as the driven snow, long straight blonde hair, standing easily 5’10” pushing 5’11”, slender, with maybe a B cup to boot. Kayla walks in and throws her arms around me squeezing me tightly. ‘Bro!” she exclaims “I’ve missed you, how have you been?” Before I can get a word in edge wise she introduces her friend. Her name is Alison, I couldn’t help but notice her shorts being a little too tight on her. Giving me a slight view of the outline of her plump pussy, I look away quickly as to not raise any flags. To answer Kayla’s earlier question, I fill her in on the details of the past few months. I’ve graduated high school, and I have my sights set on starting at a community college before applying to State. We catch up for about an hour before Kayla asked if my parents still have that hot tub. They did in fact still have it, I asked if they brought swimming suits and they both smirked saying no. Alison chimed in “ we do have on something close though… if your ok with that?” she grins knowing my response already. “Of course, that’s fine!” my response sounds almost desperate and the two girls giggle as we walk to the hot tub. I grabbed some towels and drinks for us, whatever beer dad had left in the downstairs fridge. Read more »

The Glory Hole

A glory hole is a thin hole in a wall or other type of divide where a man inserts his penis to achieve sexual gratification. It’s anonymous, it’s mysterious, and it has one purpose. The purpose is for one person to orgasm, and the other to achieve the power of making someone orgasm. Unlinke sex, the glory hole does not care much if you are hot, attractive or lean and muscular. It’s a simple cock through a simple hole. With sex you try to have stamina, last a long time and have mutual pleasure. With a glory hole, speed is a skill and with great speed it allows the other party to reap the reward, a warm, salty load of cum as their trophy. Read more »

[MF] Finally fucking my best friend

Emma and I didn’t really know each other well until our final year of high school together. My girlfriend at the time told me that Emma fancied my best friend, so I passed on the message and they started dating. We would hang out together all the time, often just me third wheeling the two of them, but it was my best friend and Emma and I were getting closer so it just felt natural.

Cut to after uni, I have long since broken up with my girlfriend and eventually my two good friends did as well (it was messy, though I’m still good friends with both of them). Now Emma and I spend a lot of time together. Visiting each other in our respective cities, spending time together at Christmas back home, going to festivals together. She is a very sexual person and we spoke in depth about our sex lives and who we were dating at the time, and even though I find her very attractive, neither of us felt compelled to make anything happen. For years we would share a bed after a night out, share a tent and get changed in front of each other, but nothing would happen. Read more »

The best, and the worst sex of [m]y life

This happened over 10 years ago.

I just got into the university and my friends and I drove a couple of hours down to this house party in a smaller town not too far from where I live.

The house was located at this farm, and the house was so large, it could’ve been a motel or so (if I remember it correctly, there were over 10 bedrooms) and the lounge area (there were multiple lounges) I hung out was possibly as big as the flat I was staying at the time.

My friends have told me, before we got there, that it was a party hosted by a group of farm girls and practically we were the only guys (and his other friends) who will be there while the rest of them will be the girls.

A little note, I was the only short, chubby and awkward Asian guy (sadly, this hasn’t changed much) among all African men, who were, without being objective, quite good looking and fit guys (I don’t have any reservation of commenting on physical attractiveness of men. It is what it is, come on now). Read more »

[MF] My boyfriend rode my strap-on like a fucking cowboy and I loved it

Seems like you guys like hearing about my boyfriend’s ass! Thank you all so much for the kind words and the awards(!!!). No thank you to the multiple people who have messaged me asking if they can fuck Henry. WE ARE IN LOCKDOWN, FOLKS. He isn’t going to open his asshole for randos from reddit in the middle of a pandemic. Also his ego is massive now from all the attention so thank you for making me deal with that ? Should I be offended that nobody has messaged asking to fuck me? Don’t answer that.

ANYWAY, since you all like reading about our pegging adventures more than our PIV sex, I figured I’d give you another story. But first I have to provide some background: I hate the cowgirl position. It’s a thing. Nobody’s ever broken up with me over it, but I’ve had partners in the past get very frustrated that I’m unwilling/incapable of riding them for hours. I’m definitely not a pillow princess, but there’s something about being on top during vaginal sex that makes me feel unattractive and unfulfilled. I’ve never been able to finish when I’m riding someone. Read more »

Paging Dr. Richards (FM)(Medical)

First Gyno Visit

((I was commissioned to write a story and decided to adapt it for here. Hope you guys like it!))

Elle was to be in her senior year of high school and had just turned eighteen over the summer. Fall was now rolling in and she was heading back class in roughly a week meaning there were lots of things to be done in preparation. She would be picking up her books, shopping for her new uniforms, and attending a plethora of doctor’s visits for routine check ups and vaccines. Anxiety pitched as the days drew nearer and she wondered if this year would be better than the last.

The girl in question was shy, but pretty in a non-threatening girl next door sort of way. Her body was sun kissed and berry brown from spending most of the summer at the beach with her family – all save the parts covered by her bikini which stood stark white in contrast. Her nose was graced with a scattering of freckles and soft green eyes stared out from beneath thick lashes that kissed the apples of her cheeks whenever she blinked. Golden brown hair hung in unruly curls that cascaded down the middle of her back. Her style was bookish and meek. Large glasses sat perched upon the button nose with round wire frames, white keds adorned her feet – the style of the day when not in school was frequently jeans and a t-shirt. Read more »

Childhood friends reunion [MF]

Me and Aurora have been close friends since middle school, she was Italian but her parents moved to the US when she was only a few years old. We were best friends but lost contact going to different colleges, and, because she wasn’t on Instagram or any social network and barely used a phone or a computer it was difficult to stay in touch but we kept calling each other once every two months so I wasn’t surprised when she called me: she was supposed to tell me when to go and how to dress up for her birthday party the next day. What did surprise me was what she told: her boyfriend broke up with her a couple hours before so she didn’t feel in the mood for a party. I was shocked: they always seemed the perfect couple!
I was also a bit disappointed, this party was the occasion of seeing each other in person after almost ten years.
I must admit that not being able to meet her was what depressed me the most: back in high school I had a big crush on her and apparently time hadn’t changed that.
I decided to shoot my shot and go to her regardless of the party being cancelled; besides I had already booked a room in an hotel and the suitcase was ready, I just had to pack her gift.
The next morning I woke up early and got in the car, ready for 8 hours of driving. Read more »