Vacation after high school [MF][Cuckolding][a little MFF and FF]

Well I am posting this primarily as a reminder for myself. So here goes.

In my country it is customary for the whole class to go on a trip together after finishing our version of high school. So normally you are 18 or 19 when you take the final exams and go on that trip.

Imagine, if you will, the state of affairs. For most of my class mates it was the first vacation without parents, teachers etc. And since all of us had just passed the most important and difficult exams of our lives to that date, everyone was in the mood to celebrate. All this meant was, there was a bunch of drunk teenagers enjoying their freedom. Except for some floundering first tries in younger days, people had no significant experience with sex and the only reference material people had was porn. So with restraint approaching zero and not knowing any better, the people in my class were quite a lot more liberal regarding any sexual experiences during that time. I ended up sleeping with half the girls in my class and with more than one memorable story.

Far Away At Willoughby Academy (Part 4) [MF][Fsub][Mast][Oral][Handjob][Sex][Anal][Buk][Reluc][Exh][ENF][College][SciFi][AltReal]

**Far Away At Willoughby Academy (Part 4)**

The common room wasn’t busy, but there were still about a dozen other girls lounging on couches and chairs, all first years based on their pajamas and piping. None of them seemed shy that their nipples were visible, and in a few cases, their pussies, since some of them were sitting with a leg draped over a chair or couch.

“Is it always this…um…” Regina paused. “Informal?”

“You’re free to be naked down here if you want, though you’d probably get cold. I mean, we keep the temperature a bit warmer here on our side of the dorm, but seriously, my nips have been stiff for two days now.” Regina glanced at her roommate, seeing she wasn’t exaggerating, then, when she saw what was on the TV and went white.

“What the hell?” She hissed. “You’re watching porn?”

“Watch the archaic the swearing, dummy.” Kiera said, leaning in to whisper. “And no, that’s Grey’s Anatomy. Dr. McSomething-or-other…I don’t really follow the show…is just fucking one of the new interns. She’s got some nice tits, though.” Kiera offered.

“But they’re, like, actually fucking. Like, that guy’s a famous actor, and that’s his penis…actually penetrating that woman.”

Far Away At Willoughby Academy (Part 3) [MF][Fsub][Mast][Reluc][Exh][ENF][College][SciFi][AltReal]

**Far Away At Willoughby Academy (Part 3)**

True to her word, Kiera left her at the uniform shop, which was a small stand-alone building across the quad from the student union building. The sign on the door read they were open until nine during orientation week, and it was nearly eight. She stepped inside, small bells above the door jangling, and seeing a handful of mannequins wearing uniforms, a few different styles, the colored banding obviously indicating upperclassmen–maroon for her, green for second years, blue, and gold for juniors and seniors.

“You’re out late to still be in uniform.” A young woman said coming out from the back of the shop. “If you’re looking for some last-minute tailoring, Gunderson has already gone home for the day, though I’m expecting you’re here to buy something, considering the time. Most people don’t show up and hour before closing for window shopping, not if it means walking half-way across campus in nothing but stockings and heels. What do you need?”

“Well, um,” Regina cleared her throat, speaking up, “I, um, need enough uniforms to wear all week, I guess, or, well, I don’t know how many, and the school-issued pajamas, I guess…I, um, didn’t know that we were supposed to buy them.”

Far Away At Willoughby Academy (Part 2) [F][Reluc][Exh][ENF][College][SciFi][AltReal]

**Note:** Nothing new to offer, but thought you might enjoy a little more of this story. Fair warning, not a lot sexy stuff yet, still building the world.

—-

**Far Away At Willoughby Academy (Part 2)**

Auditorium B wasn’t nearly as busy as the one where class registrations were held. It made sense, since you only need to pick one extracurricular activity, compared to five classes. She wandered around the large room, looking at all the displays for various sports, crafts, computer programming, astronomy, but she decided on swimming. She was a good swimmer, at least, and it was basically an exercise class with no real competition. She Kiera again shortly thereafter, and approached the girl, this time armed with a little more information.

“Hey, Kiera, did you pick something?”

“Yeah, swimming. How about you?”

“Actually, the same. Um, I actually don’t know the schedule for today, is there something next?”

“Naughty girl, naughty boy, it could happen?” [mf]

To preface: This story is from some years back. I was a junior in college and life was great. The setting? winter break and I was back in my hometown. My only real goal for the break was to see which girls from my high school I could sleep with. College really is the best time of your life..

On this particular night, it was cold and windy, and there was not much going on. So, like any horny young college guy would do, I decided to make some moves on social media.

A little about me. I’m an attractive guy who likes to exercise. This was especially true back then. I was definitely one of the attractive ones back in school and never had a problem getting girls. (I don’t say this to brag, but I want to give you an accurate picture as you read along). I’ve always had a nice face, strong jawline, and short hair, which works well on me.

Home (not so) alone

I’m home early. I open the front door and walk into the living room where I expect you to be waiting, but find it empty. I can hear the bed rocking upstairs and quietly make my way to our bedroom door that you left cracked. Peeking through I see you wearing nothing but one of my shirts as you lay on your stomach, hands between your legs. Your body moves and sways, lifting your ass into the air enough for me to see your sticky fingers, wet with your own pleasure. Some swirl over your clit, making you moan while others are inside of you, getting to feel your sweet warmth all around them. I can feel my cock throbbing in my pants as they get tighter around me. I keep watching you gasp for air and play with your glistening slit as I silently unbuckle and take my pants off, taking a few seconds to stroke myself. You’ve never let me watch you jill yourself before. I take the scene in a bit longer until I can’t stand it anymore. Taking my shirt off as I enter the room, the creaking door finally makes my presence known. Your gasp as you roll over is of shock rather than pleasure as you use one hand to cover your pussy and the other covers your lips. I can see from the foot of the bed your hard nipples peeking through the shirt and how wet you’ve accidentally gotten your lips with your hand over your mouth. “How long have you been home??” You ask, still out of breath and with your hair a mess. “Long enough to know you want the real thing.” I tell you as I get on the bed, crawling over you. You take my hard dick in your hands, still wet from yourself as you lean up to kiss me. The taste on your lips is a teaser to what I really want. I kiss down your body, pulling the shirt off of you and kissing your perfectly tense nipples until you run your fingers through my hair and I continue until I get to where we both want me to be. You moan and arch your back as my tongue finds your clit. I love the squeak you make as I taste from the bottom of your opening, in and through your lips, before going back and plunging it into you. Your nails dig into my head as I eat, lick, and suck your wet pussy. Your legs are shaking around me as you try to hold out just a bit longer, savoring it until your body ripples with satisfaction. The smell of sweat and your deliciousness is like a drug as I crave more. You roll me under you and I feel your warm mouth as you let your teeth drag just ever so slightly up and down my shaft. I let out a sigh as you go all the way down, letting me feel the back of your throat. Your hands caress my sack, making me squirm. I can’t keep track of how long you’ve been sucking and looking at me with those begging eyes, but it never feels like long enough. I try to hold back one final time before letting go and letting it happen. I moan loudly as I cum in your mouth, feeling it soak around the tip of me before you swallow it and drag your teeth off of me one final time, making me exhale and shiver. You lay next to me, my shaft in your hand as you make sure I’m recovered enough to finish the job. Your tongue fights with mine over whose mouth we’re going to share in a sloppy, high school style makeout. I know you can feel me throbbing again. Your mouth was incredible, but I know your snatch is heaven. As soon as I can get done thinking it, you’re already on top of me, leaned back, showing off your perfectly smooth and absolutely soaking pussy. I can see a dribble of you running down your leg. Fuck, you want to feel me. I want to feel you too. Before you do, you take me in your hand and tease yourself with the head of me. Long, slow, agonizing strokes up you and then back down, only barely letting the tip hint at entering. “Fuck baby, please…” I gasp. You sort up and onto me as we both moan in unison. Your hot snatch stretches around me, squeezing juices out of you that rush down us. I can watch your lips gripping me hard as you bounce up and down on me. Your perfect breasts hang and bounce in rhythm with your hips. My hand find them and play with your nipples, garnering a few light “oh” sounds from your open lips. Your hands drag across my chest, leaving red marks where your fingers dig in as you change to gyrating on me, rubbing your clit against my pelvis. I put my thumb on it as well, applying a gentle pressure that sends stars through you. You slow and press harder, pacing yourself. I didn’t come here to pace. I came here to fuck. Hard. I roll you off of me and get off of the bed, pulling you to me. A smile spreads across your face as you realize what’s happening. I lift your legs over my shoulders and plunge deep into with a single thrust, hearing how wet you are as I take you with deep, hard strokes. I catch your gasps in your throat as my hand clenches around it. Fuck you’re tight. Watching your grip squeeze around my cock and feeling the heat of inside you just makes me fuck you harder. My free hand tortures your clit again, making you move all sorts of ways until you buck beneath me and I feel you tighten even more around me, constricting me and feeling even better than before. I drive myself in hard one last time before cumming with you, feeling my hot mess fill you up and even come out of you some. I pull myself from you, your lips not wanting to let me go. My cum drips out of you with your own letting it slide down across your ass. Next time I’ll have to save myself to have some fun in there. Until then though, we needs towels. And a shower.

My First Time: Someone Watching Me Fuck [MF]

*I’ve started writing a series of posts about my first times. E.g. my first blowjob, first time having sex, first threesome, etc. A lot of things I’m not allowed to post to reddit, so I’ll post them here to Patreon as exclusives for my Patrons.*

*And 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).*

College continued to be an adventure for me. Intellectually, socially, and (yes) definitely sexually. After my first time with a girl (during my freshman year), I was hunting almost non-stop for new and exciting experiences.

Most of the time though, I didn’t seek them out. They just happened, and I could only look back on them and think, “wow that was hot.”

This is one of those times.

[MF][Str8][oral][swallow] Golf Course Fun

This is a flashback to an experience I had with my girlfriend in high school. Bored one weekend, she said we should take a drive. Next thing I know, we are sneaking onto the local golf course well after dark. She leads me to the green on a short par 3 and starts using the pin as a stripper pole. Shortly after, her tits are out and she’s on her knees ready to take my member in her mouth. After a few minutes, we are both butt naked and having sex. We did missionary, cowgirl, and doggie with her holding the pin in her hand. About twenty minutes went by and I couldn’t hold back anymore. She again took me in her mouth and I came so hard and much that it ran out of her mouth and onto her face and chest. She rubbed it on her tits while smiling up at me. Then we cleaned up and were on our way. To this day, it’s the best orgasm of my life. Ask me anything.

[MF] Twenty Years Later…

We exchanged a sly smile as we spotted each other across the bar. Lauren had that same cheeky smile she had in high school, replete with those freckles and dimples. She tipped her martini glass in my direction to motion cheers from afar, and I responded by touching lips to the edge of my whiskey glass for a brief moment, before returning with a similar gesture.

And then I blew her a kiss – just like we always did when whenever she got off the bus home we shared.

Back then, we never made anything of it. Just on the bus cutesiness, is how I always perceived it. Then it struck me, as I autopiloted with this deeply set muscle memory … that maybe it actually meant more than that to her. Time stopped as this hit me. My mind burned with the possibility, and cursed at how potentially oblivious I had been for so long.

I then decided that, well, it was a good a time as any to settle such a thought. Only feigning hesitation for a moment, I boldly strolled to her side of the room.

The spontaneous threesome (the story of my second threesome with my high school crush) [MFF]

-So this is the second part of my story regarding myself, my once high school crush, now fuck buddy, Nat and our experiments with threesomes. If you haven’t already done so, I strongly recommend reading the first threesome story I posted. I grants a whole lot of context. With that said I hope you enjoy.-

EDIT: Dear God this is a long one. I’ll mark where sex starts.

Despite the excitement I’d felt at Nat’s pronouncement, after our first threesome, that ‘it was my turn next’ she seemed hesitant when I brought it up the next day.

“So you’d be up for a threesome with another girl?” I asked the following evening
“Errrm…. yeah I…. I guess. If it were a girl I liked.” She responded in an uncharacteristically shy tone.

Nat was never shy. About anything. ANYTHING. She was flirting with me after not seeing me for YEARS 10 minuets into our first conversation. She fucked me in the beer garden of a local bar the first time we met up. She was no shrinking violet. That made her shyness all the more puzzling. I spent the next week trying to coax her out of her shell over the issue and eventually succeeded by reminding her that she could choose ANY girl she liked. That seemed to exited her.