Tag: High School

My First Time: Anal [MF]

*Context: Based on the the DMs and questions I’ve been getting – which I fucking love by the way – I started thinking about writing a series of posts about my first times. E.g. my first blowjob, first time having sex, first threesome, etc. I can’t post things here that happened when I was under 18, so I’ll probably write those up and post them elsewhere, maybe on my Patreon.*

*(I’ve previously written about my first time with a girl, which was in college, and my first time touching a boy, which was in high school so I posted to Patreon.)*

*You know me… my name is Riley. I’m 26 years old, and a bit of a girl-next-door type. Specifically, I’m a 5’4” brunette with brown eyes, I wear my hair long, a bit past shoulder length, and I stay pretty toned with cycling classes. I’m no supermodel, but I’ve never had trouble attracting a guy (or even a girl).*

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In between my senior year of high school and college, I was dating a guy named Taran. He was tall, like 6’4”, lean, and played on the basketball team. White guy, smarter than your typical athlete, but just into having a good time. Read more »

19 [F] college student taught a highs school lesson

*Little description details, Cooper is a 27 yo high school teach that I found on tinder. About 5’10 black hair, muscular, overall sexy as fuck.*

Cooper and I exchanged numbers and within a week are planning to meet up at his house after I finish my evening class. We had been texting every day, with each text seeming to get dirtier and dirtier. We shared with each other what we were in to and that I enjoyed being a bit submissive while he was more into dominating, so our tastes worked out perfectly.

The day finally came that we were planning to meet for the first time in person, and let me say I have never felt more excited for something in a long time. The whole way over to his house I could feel myself getting wetter and wetter thinking about finally getting fucked by Cooper. I decided to surprise him by wearing my hair in pigtails while wearing a short t-shirt dress with no bra and thigh high socks, which I knew he loved from previous pictures I had sent him. Read more »

That time I banged my Ex and GF in a threesome[MFF][Group](Long)

[M27]This is by far my greatest/ favorite sex memory. I relive it a lot to cope with my current DB situation. I’m gonna give a little bit of a backdrop/history before going into my story if you’d like to just skip to the good stuff go down to the ~>.

I’m male, 19 at the time, about 6,2 and weighted around 240Lbs. I wasn’t the most attractive person at the time. I was your typical teenage boy. Lots of time spent watching porn and day dreaming about sex and my wildest fantasies. I came from a broken home and I hung out with a bad crowd. We weren’t ideal citizens. I had fooled around with tons of women before I actually had sex. Late bloomer. I lost my virginity to one of the the females in this memory. We will call her Arya. We both had birthdays in August so we were 18. Nice tight ass and solid D cups. We had dated our senior year of high school. Every day after school she would suck my cock while I fingered her pussy. It was hard for us to have sex, we both had younger siblings so we were never truly alone. We actually had to schedule the day I lost my virginity around our parents work schedule(Funny story for another time). We ended badly as I found out she was entertaining other men. Read more »

Banged the [F]oreign artsy girl from high school when we were in college. She then danced under the stars with my cu[M] dripping down her body.

So I’ve been following this sub for a long time and have noticed a lot of stories in the last two months sounding like cheesy made-up porno scripts. This one is 100% true as I couldn’t make it up if my life depended on it and it’s the only one I’ll write. Read more »

[mFFm] The Tutor pt. 12

Chapter 12
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The ride to Meredith’s house was subdued as Alicia silently considered the meeting with her lawyer, Jennifer Litaly. She worried that the clinical recounting of her fight with Megan on Friday night might have wounded her friend. She squeezed Megan’s hand and ran her thumb over the back, hoping the gesture conveyed the love and forgiveness she felt.

Megan parked in front of the house and pulled Alicia’s hand up to her lips to kiss it. The love Alicia saw reflected back at her stilled her worries.

“Ready for another night of tutoring?” Alicia asked over a sigh.

“Let’s get this over with,” Megan grumped playfully.

Carlos opened the door when Alicia knocked, his expression showing frustration. “Hey, come on in.”

After glancing around, Alicia sensed something was off. “Is Meredith here?”

“No, she had to take Fee and Liz home,” Carlos said as he closed the door.

“I thought they were gonna study with us this week?” Megan asked as Adam walked up from the kitchen.

Adam crossed his arms over his chest to glare at Megan. “Apparently your Dad has a problem with them being here with you two. Mom drove them home to have a word with your mom before she heads to class tonight.” Read more »

[MF] Fucking My Friend’s Sister While Watching Hallmark Christmas Movies

I don’t have a lot of friends. Honestly. I can count my friends on one deformed hand that only has three fingers, so I try my best to keep them in my life. For example, I’d never risk a losing a friend by fucking his 19-year-old sister on the family couch late at night while watching a shitty Hallmark Christmas movie. THAT WOULD NEVER HAPPEN!

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Oh wait, it did. Last week, I was visiting an old friend from high school. We are both 26-years-old now, with jobs and we live in different cities, so we don’t see each other much. We were both in our hometown last week, and since his family is wealthy, we usually hang out at their home. We drink, play pool and chat. This friend, we’ll call him Trevor because I feel like all rich people are named Trevor, has a little sister named Trevorina. She’s 19 and was home from college. It was the first time I had seen her in three years. I don’t even have her added on Facebook, so when I say I haven’t seen her in three years, I mean it.

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“I want you to spank me… with your belt” [Mf]

I’ve told a couple stories about the kinda crazy Korean hipster girl I dated on and off. Now I think I’ll tell some about Stephanie, the hottest girl I ever dated, who had some kinks of her own.

Stephanie was a 5’7 blonde who’d been a high level ballerina in high school and had modeled a bit in college. She had long legs, small perky tits, a perfectly toned stomach and almost no ass. She was way way out of my league but somehow, we dated for a long time.

Generally, our sex life was pretty vanilla, but occasionally she’d bust out with some deeply kinky shit. This was one of those times.

It was late and we’d come back from a party. I’d gotten her out of her clothes as soon as we’d walked into my room, and I was running my hands all over her gorgeous body while she rubbed my cock through my jeans.

“I want you to do something”, she said.
“”What?” I answered
“I want you to spank me” she said

Without hesitation I smacked her ass, I’d done this plenty of times before, but this time in response she grabbed by cock even tighter and said Read more »

[MF] A novel way to begin a relationship

This is the interesting tale of how my current relationship began. While it’s only been officially been going on a month, it’s unquestionably one the healthiest and sexually satisfying relationships I’ve ever been in.

Bear with me in this story, it’s a slow build. I promise it’ll be good though. It’ll be a long one.

**The characters:**

Me – 34 year old male. Average height. Thick built. Barrel chested. Decent amount of muscle. But some fat. Not in great shape, but not in poor shape either. I’ve been described as rather dashing, but I think they were trying to flatter. All in all I’m a not-unattractive nerdy guy with a great smile and good hair.

EM – 28 year old woman. Slightly taller than me. Often the most attractive woman in the room. Dirty Blonde hair. Curvy without being heavy. Perky D-cup breasts. Long legs. Amazing ass. Just an all around bombshell.

**The Setup:**

Since 2017 I’d been living a poly lifestyle. It had started with an open relationship (which ended early 2017). I’m active in the BDSM community as a switch. I’ve kept a fetlife for quite a while. And did most of my dating through OkCupid and Fetlife. Read more »

My gf surprised me by fucking my ass after a wedding [FF]

This ended up being waaay longer than planned so I tagged where the sex begins (although there’s a lot of foreplay/ sexual teasing throughout the entire story so you might be missing out if you skip!)

The night started out with so much potential for drunken sexual shenanigans. My girlfriend Leah and I were headed to a wedding with her high school friends who were a crew who liked to get pretty wild. I was eagerly awaiting this night’s arrival, since weddings always have a certain playful vibe to them which I knew would make Leah and I pretty frisky, so there was a good chance that we’d fit in a round or two of satisfying sex at some point throughout the night.

Before I get too far into describing the event, I’ll provide a little visual of the two of us. Leah is absolutely stunning and sooo so hot. She’s 27 years old, around 5’10 with light shoulder length brown hair, big blue eyes, and a killer jawline. She has DDD boobs, a perfect squeezable ass, and long, athletic legs that would make anyone drool. I’m 24, 5’5 with similar hair, C boobs, and a round ass that commonly takes all the attention from people who I fuck. I would say I give off a cute vibe, while Leah is undeniably hot. Leah is more of a veteran than me in the realm of sexual experiences, but I like to think that I make up for it in enthusiasm. As a couple we have such a unique energy in the bedroom, which makes for an extraordinary sex life. Read more »

The worst thing I [m] ever did [f]

When I was in high school I had an on/off relationship with a girl named Jessica. She was a very pretty, athletic girl from a wealthy family. Think college soccer player; slim with an ass you could bounce a quarter off of. For visual I was 5’9″, 160 lbs, around 9% bf, shaggy brown hair, and 7″ for those that care. Her family loved and trusted me and we still talk occasionally to this day. The problem was Jessica was absolutely crazy. She strung me along, fought about everything and overall was a drain on me life. When I was 19 she had broken up with me in a particular fit of crazy and burned all the belongings she had of mine. About a month after that her family offered me a good bit of money plus access to their sweet house and liquor cabinet for a week while they were on vacation to housesit. Read more »