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no regrets

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22 minutes ago inno regretsbyAnonymous

Her Roommate’s Panties

When me and my now-wife Alicia first started hooking up, our sex life was a marathon. We’d meet up to fuck multiple times a day, and go round after round after round. When our lunch breaks would line up, we’d hightail to her college apartment so I could rail, spank and eat her before sending her off to her next class.

But she absolutely loved having sex in places where she could be caught…especially around her apartment. Alicia lived with four other girls. And she took every opportunity she had to have me fuck her on the floor of the living room, or suck my cock on the girls’ shared leather sofa, or have me lick her pussy on the kitchen counter.

But Alicia’s favorite thing to do was get fucked in her roommates’ bedrooms. If she knew we had the place to herself, or even if it was just late at night and one of her roomies were gone, she’d sneak me into their beds and ride my dick. I quickly learned that the taboo of it all turned her on, and the risk of being caught fueled her wildness... continue reading

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Okay, so I have a colleague. He’s 23, for context, I’m 37. Whether it’s at work or the few occasions we’ve trained with each other in the gym, we’ve got this thing going of picking out our favourite hotties.

I work somewhere with a crew of people that’ve been there forever, we know each other’s lives inside out (sex lives included) and the boundaries are low. You could say unprofessional, I’d opt for fucking loose and mega fun instead.

So, the Christmas Secret Santa is a fun one each year. 8 of us did it this year and I drew him. From working with him in the Summer, I learned how much of a boob man he was. I have DDs but keep them covered at work with a jumper or baggy t-shirt. No bra season was a big turning point as I’d tease him about seeing braless customers at the counter.

My plan was simple – I wanted him to see my tits. I also want to sleep with him.

Anyway, how could I do it? Since I was away this year and couldn’t make the Christmas meal, I considered sever... continue reading

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TL;DR: Had an orgy with my single mom friends, dressed as Santa and brought a special gift for them to enjoy resulting in numerous orgasms.

Since my wife's passing and being inducted into the secretive single moms' club, I've made it a yearly tradition to treat them to a flirty Christmas party that usually devolves into some sexual fun. The tricky part is finding time when we can get babysitters for our kids, but when we do, things happen on a moment's notice. Unlike in the summer, when I'd host them out at my wedding venue, for nights like this, I invite them over to my house, which makes it easier to stay warm.

Another part of the tradition is getting to play Santa for all of them. Initially, the agreement was that I'd help them get toys for their kids, and vice versa. What I didn't tell them was that I also got gifts for them. It's never anything special, usually some makeup, perfume and maybe a sex toy. Anyway, we had our fun on the 21st. I got a couple of food platters and dre... continue reading

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This story takes place a couple of years ago. I was working in Europe and, being an expat and not having many friends in place, I started bouldering as a way to make new friends. I would usually climb on the same days every week, and as expected, see some regulars.

Among the people I met, there was Alice. Alice was a very pretty Irish-French girl : white skin, freckles and an angelic face. She was on the petite side and had a very toned body from bouldering and volleyball.

I think we quickly became friends as we were one of the few English-speaking climbers in the gym. I never asked her age at the time, I only knew that she was in the last year of high school and clearly off limits for me.

Knowing this, I’d do my best to not look at her body… but sometimes my horny mind wouldn’t resist, and I would end up peeking, especially when she was wearing shorts.

Anyway, a couple of months after our friendship started, my company wanted to move me to London, and I wasn’t saying no s... continue reading

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DISCLAIMER: This is a repost of a post I made months ago. I have made tiny edits for clarity. Enjoy. ;)

A few months ago, I was supposed to go run some errands with my MIL. We had set a time early in the morning but things weren’t working out for her so she said she would call me when she was finally on her way.

So I just laid in bed cuddling my hubby. He was REALLY hard this morning. And although I really wanted to fuck him, I just played it cool and didn’t try to start anything since I would get that call at any moment.

Anyway, she calls and tells me she’s 10 mins away. So I rush out of bed. I’m just wearing a t-shirt and some VERY short shorts. I quickly take off the shirt and put on a bra. I dump out the clean laundry basket on the floor to try to find clothes to put on. I’m on the floor looking, when my hubby gets out of bed and goes over to where I am. I can see his super noticeable boner through his thin sleeping pants. No boxers. He gets to me and just whips out his cock, gr... continue reading

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About a month before starting university, we had a mandatory orientation on campus, which included an overnight at one of the dorms. The orientation was all the usual ice breakers and expectations setting that you might expect. We were grouped by major so we'd meet people we would have classes with. In my group of mostly guys, there was one girl who stood out. Leah was a petite redhead dressed in shorts and a tank top (it was hot as hell in July) with a little scar on her cheek. She laughed at one of my jokes, we locked eyes at some point and it was on.

We spent the rest of the day together, getting to know one another. There was undeniable sexual tension and I'm sure it was noticable by our groupmates. While we kept things PG during the day, we were stealing touches and glances throughout.

That night, there was some pre-programmed "club" night at the student center. Most of our groupmates and a bunch of the overall orientation undoubtedly found a party or something to attend, but... continue reading

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My dads friend Cody has been flirting with me since I turned 18. One time he called me an adorable princess when my dad was in the other room.

He knocked on the door when my dad wasn’t home and said he was letting my dad borrow whatever a wiggle tool is and get something from the garage. I let him in and went back to my room. I was actually watching porn and was really wet. I closed out the porn on my computer and went to leave when I saw him appear in the doorway.

“What’s the pretty dress for?”

I was selling my failed prom dress on fb marketplace and it was hanging up on my mirror.

“That’s my prom dress. I’m selling it.”

“Oh why? I bet you look so beautiful in it.”

“I only wore it there for 20 minutes because a teacher complained it was too short and they sent me and three other girls home.”

“Really? That’s hilarious. Now I want to see you in it.”

“I bet you do,” I teased.

“Sorry, you get me worked up. Don’t tell your dad I said that, please.”

“Ok, don’t tell hi... continue reading

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A roundtable evening drinks outing unearthed deep desires between 5 of us. My youngest friend there was 23, while the oldest was 42. Somewhere in the middle of that, at 29, was Sienna.

Sienna wasn’t as sexually experienced as some. Having had two long term relationships, she felt ‘vanilla’. I wasn’t happy with that. This is my friend who’s here expressing urges to seek out more cock, filthy one nighters, and to embrace her submissive kink.

Sienna wanted more and I wanted to help make it happen. She deserved it.

I figured it’d be sex toy shopping or helping her put together a dating profile.

Instead, her gushing confession of really wanting to try anal, sparked my interest. I couldn’t give it to her, but my boyfriend could.

Near the end of the night, I asked what she was going to do to achieve that. Sienna didn’t have an answer. I had this idea and I decided to not beat around the bush.

“If I had a guy, would you like an introduction? You know, for your goa... continue reading

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Obligatory 'this is an old story but I wanted to share it anyway' Just for some background, my best (f)riend who we'll call 'Emily' we grew up together in the same town from the age of about 10. Our respective grandparents were friends ect.. Anyway, very average friendship for a lot of our teenage years going out shopping and whatever together. Her mum would tease us constantly about being a couple ect. and while I did think she was very pretty. We were very different people personality wise, I was a lot more introverted back then to what I am nowadays where she was very extroverted.

By around our mid to late teens, we'd both moved away to different areas with our parents, but we both made efforts to catch up/ go shopping, talk to each other about our relationships ect. we was about as close as friends as the opposite sex could be at least imo. However as the years went by we'd drifted apart, I'd gone away to university and she was working here & there.. but still kept in contact... continue reading

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Over 15 years ago, I had a pool at my house, and I could tell that summer had begun when I got a call asking, “Aunt Cate, can we use the pool?” And then I would have a half dozen or more kids running around the house until the end of summer. Eric was one of my nephew’s closest friends during that time. They were practically joined at the hips until Eric’s family moved away. They kept in touch for a while, but unfortunately, my nephew and Eric fell out of touch.

Almost 10 years later, I had moved as well. I was living alone, in a completely new city. I was in a supermarket one day when someone called my name. I turned to find Eric’s mum. We got to talking and I found out that they lived just a couple of doors down from my place. By then, my nephew was living on the other side of the country, so I helped him and Eric reconnect. They ended up making plans to meet during the coming summer, and even organised a small reunion with their old friends. I suggested hosting it at my place since... continue reading

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When my daughter was in third grade, her teacher (25F) was a complete smoke show. Thin, blonde, beautiful, great figure, but what really mattered to me was how sultry she was. She just had that aura that drips sensuality.

When I’d pick my daughter up, her teacher would often be there in the pickup line and give me these long, unflinching looks like she wanted to consume me. When we’d talk, she’d always greet me with this extremely flirty “Hiiiiii \[my daughter\]’s dad 😏”

When the school year ended, I found her on social media and sent her a DM. We started chatting and ended up meeting for a walk in the woods. The talk was extremely spicy but we didn’t touch each other.

A week or two later, I asked if she wanted to go clubbing together and she asked me if I could pick her up. When I got to her apartment, she texted and asked if I could come up and help her choose an outfit before we went out.

She tried on a few things for me as she drank wine and talked. Eventually, she asked for a... continue reading

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It's October, which means Halloween and playoff baseball, so I figured it's as good a time as any to tell the story of the first time I hooked up with my first college girlfriend.

It was my freshman year of college in 2013, and I was not adapting very well to being in a new state. No friends, not doing well in any classes, and just generally coasting through life. I had this one boring as hell political science course where the professor mostly just read news headlines for an hour then dismissed us, so I spent most of the classes scrolling through Reddit on my phone (yes, I've been here that long!). Honestly, I don't think I looked up from my phone long enough to be able to tell you what any of my classmates even looked like.

Halloween rolls around and I still had nothing going on. I was 3 states away from anyone I knew well enough to call a friend, so there really wasn't any parties to look forward to. As a result, I didn't feel the need to buy a costume or anything. Still, I wanted... continue reading

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This story takes place many years ago in 2013. I was 18, just graduated high school, and was on my way to move to Tennessee and play baseball in college. My sister had just graduated college and was hosting a party at our parents' house. At the time I was a completely different person from who I am now - I was mostly pretty introverted and didn't really go to all that many parties, especially full of people I hadn't met before. My last girlfriend and I had also just recently decided to break up since we were going to be moving states away from each other, so I was pretty much just in the mood to sit in my room and play Halo all night.

"Come hang out for a bit," my sister urged. "I'll even let you drink, but don't tell mom and dad."

Even as a youngster I knew that a drink or two was enough to change that introvert into an extrovert. Eventually I learned how to do it even without alcohol, but at the time I figured I could get one beer in me early and feel comfortable enough to go for a... continue reading

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I sat back on my couch the other day and saw that I had a text out of the blue from an old college hookup, Tasha.

It read: “I was just thinking, you have a glorious penis,” and immediately I was hard as a rock.

\*

I met Tasha in the college gym about ten years ago, helping her up after she accidentally triggered the emergency stop on her treadmill at the gym, lurched forward, and fell over. Fortunately, only her ego was harmed, and she seemed grateful for the hand.

“I’m Tasha,” she said, “And I promise this never happens.”

“I’m Marc,” I said, then grinned and took a calculated risk, “And I don’t know… it seems like a good way to meet a guy.”

She laughed, I was in, and we both proceeded to cut our running short and grab smoothies at the cafe next door.

Tasha was… fit. At 6’2”, she was nearly as tall as I was, and she boasted a tight ass and some perky, probably B-cups. You could tell this was a woman who took fitness seriously, and found out later that she was actually on the... continue reading

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So my girlfriend and I just got back from a trip with her family. It was crazy! For weeks before, we were hyping it up. Her sisters gave us our own room, and we were already planning how much we were going to fuck — bed, sofa, chair — the whole deal. No need to hold back, no need to stay quiet.

Then, a few days before the trip, plans changed. Some younger family members decided to tag along. Suddenly, instead of having the room to ourselves, we had company. At first it was a huge letdown — all those fantasies we’d built up felt like they’d been taken away. But I told her, “we always find a way,” and sure enough, we did.

First night

When we checked in, it was the two of us plus them sharing the room. Luckily, they decided to head down to the lobby to catch up with the others. The second the door closed behind them, I looked at my girlfriend and she already had that smirk — we both knew. Clothes came off fast. I had her on the bed, me standing at the edge, fucking her hard in missionar... continue reading

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TL; DR: Today, my yearly road trip has begun, and I have three cosplayers joining me. Zoe, Kristen, and Rebecca. The plan is to go across Canada and take some erotic pictures at some of my favourite spots, but first, we stopped in a quiet parking lot with a view and had our first in-person orgasms with each other, before going to McDonald's for brunch.

The planning is finally over, and today my yearly road trip & photoshoot vacay has begun. For context, every year I take a road trip across Canada with three "models" and do some erotic photoshoots with them in my favourite spots, but there's always some theme or improvational roleplay I have them do, cuz I got bored of doing just naked girls in the wild. The roleplay concept we're rolling with is three thieves cursed by a relic that filled them with insatiable amounts of lust. It's a silly-sounding concept, but like I'm working with what I got.

My models, well, they're actually cosplayers I met at a comic convention last yea... continue reading

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I learned in my 20s that guys never forget the best blowjob they ever had. Proof of that is horny texts after the fact, comments years later and mid-sex dirty declarations, which I LOVE btw.

I tell this story with a smile. I really get off on giving good oral, so I thought I’d have fun with it. Everybody won in this story. Here’s how it unfolded.

In my mid-20s, I was hitting bars and clubs 2-3x a week. I was incredibly flirty. I’d meet people regularly – friends of friends, random hook ups, guys I’d studied or worked with, men from the gym.

A guy called Scott came home with me one night. I’d heard he had strong stamina from a friend who’d been there. I suggested leaving the bar early, and before I knew it, I was sucking his dick in front of my new mirror that was stationed behind my ass.

Key to victory: show off your best asset, whether it’s boobs or booty. They’ll cum quickly.

Spoiler alert: I made him cum within 3-4 minutes. My grip was firm and slobbering al... continue reading

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my friend just got dumped, and we were at my place with a few others, getting drunk and joking around. his ex had told me and my other girlfriends his dick wasn’t even that big, and i, being a dumbass, accidentally humiliated him by spilling to his guy friends.

hiss face goes red, and i realize i fucked up, embarrassing him. i felt a little guilty after so i decided to make it up to him in a way that’d definitely cheer him up.

i pulled him aside to my bedroom to apologize, but words weren’t cutting it. i was buzzed, horny, and thought, fuck it, i’ll make him feel good. i pushed him onto the bed, unzipped his jeans, and pulled out his cock.**..thick, veiny, getting hard fast. AND HEY IT WASNT EVEN THAT SMAL**L! infact, it was a pretty big dick

i looked up, said, “wow its actually big. sorry for being a bitch,” and wrapped my lips around the tip, tasting his precum. he groaned, “fuck, anna,” as i sucked deeper, my tongue swirling the head, spit dripping down his shaft.... continue reading

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I’d just gotten back from a BBQ, still in this flimsy floral sundress I love. It’s light, breezy, and just barely covers anything. My FWB was already at my place, scrolling through his phone on my couch when I walked in. He looked up, and his eyes, usually so chill, just ignited. He took me in, from my bare shoulders to where the fabric floated just above my knees. A slow smile spread across his face.

"Well, hello there," he murmured, his voice a low rumble. "That dress... it was made for trouble."

I felt a blush creep up my neck. "Is that so?" I tried to sound playful, but my heart was already starting to thump. He stood up, closing the distance between us, and laid his hands on my hips, pulling me close. I could feel the heat radiating off him.

"Yeah. It's screaming for me to just lift it up and get a taste," he whispered, his lips brushing my ear. The directness made my breath hitch. I mean, we've done it plenty of times, but there was something about the casualness of that desir... continue reading

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With my best friend, we have a thread where we swap nudes and explicit videos. It’s our thing, a private game we’ve kept going for years.

One day, I had a twisted idea, a pussy photo contest. We’d vote, “like” our favorites, and eliminate the rest. Simple, just for fun, at least on the surface.

I gathered about twenty close ups from Reddit, scrolling late into the night to pick the best ones. And I don’t know why, but I had this crazy, perverse thought, slipping in a photo of my girlfriend among the others. Just one. Like a secret dare. Of course, he had no idea.

The moment I hit send, a rush of adrenaline hit me. This wasn’t just sharing porn anymore. It was crossing a line, mixing two worlds that should never touch. And that’s exactly what made it even hotter.

As the contest went on, her photo started making it through, round after round. Other girls got eliminated, but hers kept surviving. Every time a little heart popped up on her picture, my own heart pounded harder in my chest... continue reading

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