*Let’s not waste any time. My name is Jeremy and you’re here because you want to hear the story of how I fucked my mom’s best friend’s daughter in the ass. Here we go.*
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Tag: High School
I [F] an affair with my former “coach” [M] that carried on for years…still in platonic contact with him today!
I’m not sure if this is even the right place for this, but it doesn’t seem right for relationships and it doesn’t fit in confessions, so here we are… I’ll give more details if that’s what’s asked. I’m a first time poster here so be gentle… ?
When I was in junior high and high school I had a, for lack of better terms, a coach (not a teacher/not a sports coach – something else without giving everything away). He was talented, smart, funny, handsome, and obviously MUCH more mature than the boys my own age. (Duh, teenage me! He’s 18 years older than you!). We bonded over the 3 years he was my “coach” as he was the only member of the coaching staff who believed in me and really mentored and encouraged me. My parents worked a lot, so he would also drive me home and we would chat and bond over classic rock and music. As far as I know, he could never tell how big of a stupid school girl crush I had on him. He eventually got fed up with the rest of the coaching staff’s BS and abruptly quit, which left me angry, heartbroken and feeling abandoned. I didn’t speak to him for years! That is until I was about 22 (maybe 6-7 years later) when he reached out to me out of the blue and apologized for leaving the way he did and told me how much he had missed me. We agreed to have lunch…then dinner and the next thing I knew we were carrying on what felt like a platonic/teetering on romantic relationship. Then he tells me… he’s still married… ?, but being that I was a rebellious 22 year old, I didn’t give AF and we carried on an affair off and on for the next 5.5 years!
Most nights we would meet and go to dinner and fool around in his car. Even today when he occasionally gets drunk, he’ll remark about how incredible my tongue felt or how good I was at giving head. To this day, I’ve never had anyone touch me with their hands or tongue and satisfy me the way he could.
He was miserable, bless his heart, and so was I! He claimed at the time that he couldn’t divorce his wife because he still had 4 young children at home, which at the time I was skeptical of, but he did divorce her as soon as his youngest turned 18, so maybe he wasn’t a complete lying sack of crap. Anyway, our time together was always so fun and wonderful, the physical stuff was amazing and it seemed to fill a need for the both of us. We always stayed in platonic contact, but were “there” for each other when the other needed. It was a strange unspoken understanding. He and I have stayed in contact even though we haven’t done anything physical in many years. I still occasionally go watch him perform with friends and have even met his new wife. I used to feel a little guilty about the whole thing, but looking back, not so much anymore. I’m not sure that we can/would ever go back to the way we were, but I can’t deny that even after all these years and such a big age difference, I still find him all around incredibly attractive. I even find myself completely turned on when he greets me with a hug and kiss on the cheek on the rare occasion (maybe 2-3 times a year) that we see each other. Hell, I get completely turned on just reminiscing this…
I have only a couple friends that have even the slightest idea about this and it felt SO good to get it all off my chest!
Trying New Things [MF] [oral]
In the days before swiping, I made a profile on an online dating website.
I was in a six-month rut, coming off a particularly strange relationship where I unintentionally started a love triangle that didn’t end in my favor. (They’re happily married now, congrats.)
Following that relationship ending, I put myself out there emotionally. I made myself vulnerable and wanted nothing more than a _relationship_. Sure, sex would be great, but what I truly longed for was someone to go on dates with, watch movies with, just hang out with.
I had a couple of friends that I thought were cute. I had crushes on them. The time of crushes, how innocent. The slight nervousness, the uncertainty of what could happen next. Back then, and maybe still now, I thought it was best just to be candid. I told my crushes how I felt, and they didn’t feel the same. The rut continued.
That’s when I made the profile. Everyone on the dating site was someone I knew from high school. I didn’t message a single person—the thought of dating someone I was aware of from high school filled me with dread. I turned off my profile.
[M]y Best [F]riend Part 3: Summer Vacation [Long]
Sorry, another long one. Sexy stuff separated out. Again, on mobile. Yada yada yada
Graduation had come and gone. Summer vacation had begun. Emmy was preparing to go to a state college an hour away to major in nursing. I was headed to a technical college to become a mechanic. That summer was kind of like a last hurrah before entering the real world, as it is for many high school graduates.
Our parents were well off, but they lived well below their means. For our graduation present, though, our parents planned a week long Mediterranean cruise. Vacations are still about the only thing they splurge on, and even then they like joint vacations where they split the cost. They aren’t stingy by any means but ended up making sure Emmy and I weren’t spoiled and that we knew the value of a dollar.
Emmy and I got a scare, though, when our parents announced that we’d have our own balcony room. For a brief moment, we shared a look of “do they know?” until they explained that somehow her grandparents managed to have their room transferred to us and that we were adults and they weren’t wanting to deal with us coming and going. They were pretty liberal in that sense.
Wasted [m]y 20s just [f]ornicatin’
I have a few stories from my youth. I’ve enjoyed reading the stories posted here and can only lurk for so long before I gotta give back to the community. I’ll give you some set up and then sexy parts. I will be retelling these as accurately as I remember… there may be some gaps and there may be some unsexy parts. Just a heads up. Also fair warning, I used to think I was a writer.
Story #1 is about 15 years ago.
I worked with Claire at our part-time job; she was working while finishing her senior year of High school, and I was just working there while I wasted my 20s partying and hooking up.
WARNING this story includes cheating.
At the time, we were both in relationships with other people. This was not the first time we’d hooked up; we’d tried dating earlier in the year but it didn’t work out and we’d since set up a pretty beneficial friendship. In retrospect, she was crazy about me and I did not treat her as well as she deserved.
I [M] ended up fucking my new roommate [F] after hanging out at the Strip Club. And Damn did I regret it.
I used to live in a five bedroom apartment in a big city. We had a rotating company of roommates, many who I found through Facebook connections and your occasional Craigslist hit. It was co-ed but everyone range between 23-33. It was a diverse group of people and while it may seem crowded, we actually all barely saw each other half worked in the service industry, while the other half worked on their residency in the nearby hospital. We were all friendly but there was an unspoken rule of “try not to fuck your roommate, physically, financially, emotionally etc.” I was the only one on the lease so everyone pretty much paid me so I was responsible for also vetting prospects. A roommate was leaving to work in a lab two hours away so I had to fill the spot. There were some great prospects but I posted a search on FB and someone had recommended a friend of a friend named Sarah. Coincidently, I’d work on a project in which Sarah was assistant number two to the principle talent and we had some brief interactions. She’s the quintessential “Chill girl” her hobbies included smoking weed, knitting and listening to music. Physically, I’d say she’s 5’6 tan skin, small b cup breasts and a gorgeous robust bootie. Her celebrity doppleganer would most aptly be 75% Aubrey Plaza.
Pro Boner [Fiction] [MF] [Oral]
This is a short story I wrote a couple months back that is an adaptation of a Super Deepthroat dialogue of mine that I also wrote. I do hope you’ll all enjoy reading this one (written from a female POV):
First, there’s the knock at my door that almost makes me fall from my chair, and then there’s that same monotonous tone from my secretary.
“Mrs. Blair, your client is ready. Shall I let him into your office now?” she asks from behind my closed door. *Ugh, great. Naptime just has to be over, doesn’t it?* I think to myself in my sleep-deprived stupor. An hour ago, I was doing research for around six different cases before dozing off.
“Uh, give me a moment, Linda. I just need to clear some things up first,” I drowsily reply, almost slurring. After a couple more seconds of shut-eye, I finally force myself to get up. I’m really going to miss laying my head on my cool desk.
[F4A] Currently wearing nothing but a brass toe ring… and seeking the writer of my dreams.
Yes before you ask, I am a proud gamer girl and adore 2K, get to know me further and maybe I’ll share my gamertag!
So my title rings true, I’m currently sitting haplessly across my bed in my childhood room as my parents watch a re-run of Wheel of Fortune downstairs… and I am as bare as the day I entered this world… well, save for the brass toe ring given to me from an ex from high school.
I may seem young, naive even but I am far from anything you’ve ever seen or known, and once this tongue begins talking, you’ll give me anything I want and you’ll do it with a sly grin on your face. Plus I’m young so that’s appealing too, right?
My ask is simple: I’m a huge fan of erotica, not roleplay or telling me how you’re “gunna fuq me”. No, I’m talking about long, eloquently written tales meant to dazzle the mind and excite the extremities…. and I want them to be written all for me, based on the fantasies in my head. I want every environment richly detailed in luscious paragraphing, down to the last crack in the floorboard. I want every character fleshed out for pages until we get to the dimple above their buttocks, and I want everything described in the most expensive vocabulary that will have my toe ring slip off before the night is through.
Revenge Fuck Boss Wife pt 2. [MF]
Part II
I step out of the shower, my body is bright red. I must have been in there almost forty five minutes, scrubbing away the combination of Rebecca and my juices. I always take very hot showers, my dick is soft and my balls loose, saggy, drained. This is the most I have fucked in one day since my High School days. After I dry myself off I walk to the bedroom, my phone is flashing blue. I opened the homescreen and saw a message from Rebecca. A video link is in our messages, my dick twitches. I click the link and it enlarges to cover my entire screen. I sit on my bed and press play.
Southern Chick and her Slutification
Note – The story is written from the point of view of the dom.
It had been almost 4 months since we started dating. Who knew this gal I’ve had a crush on since high school would one day be my girlfriend. The last year of our college and we had both gotten pretty busy.
She’s your typical midget ,long brunette hair ,40DD breasts and a butt so round and perfect , you’ll fall on your knees on having seen it. Dark blue eyes like Alexandra Daddario .All in all ,a simple girl from a humble background.
Football helped me maintain my athletic physique throughout college and a thick juicy cock always helped .I got my fair share of action but it was different with Betty. Yeah ,her name’s Elizabeth ,and only I get to call her Betty. Betty is the kind of girl with whom if you to spend time ,you would loose track of everything ,I loose myself in her , she’s so beautiful and so warm ,I to thrive in her presence, and that’s very rare.
Last week she won a prestigious fellowship and we decided to celebrate it .An old money background and generous parents equal a penthouse in Manhattan ,Lucky me right?