Last night we (f)ucked up (long) [m/f]

A bit of context: I've been dating my wonderful boyfriend since April. The sex was amazing right off the bat and has only gotten better and better. We've gotten to experimenting with some new things and recently discovered that I like butt stuff.

So we're snuggling on the couch when he suggests that I put one of my buttplugs in. I am more than happy to oblige and soon he's teasing me a little by pushing on it, stroking my thighs, etc. We take it to the bedroom where he continues to push on the plug, but a little harder, and I'm loving it and he's getting into it and all of a sudden–

schloop

— he (unknowingly) pushes the plug all the way in. And I mean, it's up there really good. And it's not in there straight, because that would be too easy and painless. No, it somehow got jammed up in there diagonally. So I jump up and run to the bathroom with no other explanation than "OhGodOhGodOhGod", each step more painful than the last. He realizes what's happened and is freaking out right along with me, standing in the doorway as I'm in the throes of a panic attack, adrenaline rushing, legs shaking, three fingers jammed up my asshole desperately trying to dig the thing out, and…

Fun rough sex

This happened about 4 years ago with an ex girlfriend of mine.

To give you some background at the time I was 26 and she was 23. We both really enjoyed working out so as such were very fit. She was on the shorter side- around 5'2" with lighter green eyes and dark brown hair and around 110lbs. She was very lean but still had a shape to her. I am 5'10" athletically built with a solid chest and shoulders. Back then I had quite ripped abs….not so much anymore unfortunately.

Anyways, one night we were having dinner and of course a few glasses of wine. We had been dating for about 4 months at the point so we're getting pretty open with each other.

Being young, fit and relatively new to each other our conversations often turned to sex and this night was no different. We started sharing our fantasies and discussion what we both had always wanted to do sexually etc. Her #1 ended up being to be tied up during sex. Mine was to share her with another guy in a mfm threesome. She started asking about that and we got away from hers.

meeting for the first time [MF] [First Person]

I'm disappointed because you can't come see me as we initially planned, and I'm trying to manage my feelings. I try to let myself feel the disappointment, temper it with rational thoughts. I'm concerned because negative feelings often turn to apathy, and I want to hold onto this. I don't want to tell you I'm disappointed because I'm not sure it's appropriate for me to care, and I don't know if you, like me, get weary when someone cares too quickly. As a compromise to myself, I jokingly say that we should meet in Havana instead, a throwback to my initial message to you. You say, "make it Kingston, and we'll take a puddle hopper." So we do, and you fly the plane. I don't know where or how the arrangements were made for the plane, but it's just me and you.

I'm fixated watching you push buttons and move levers on a dashboard that looks vast to me, but your movements seem effortless, like a musician at a piano. You're wearing cargo shorts, and I'm fighting the urge to slide my hand up your thigh. I want to feel your cock in my hand. I want to learn how to move my hand precisely to make it bulge. I want to see how my hand looks wrapped around it, whether my nail polish goes well against color of your skin. I want to watch droplets of cum form around the tip; and I'm biting my lip, thinking about licking those droplets off.

(M) wife watched me (f)uck the Latina of my dreams and then licked my cum off her pussy.

A few weeks ago my wife Anna and I had a get together at our friends Jackson and isabelle's house. They are another young couple and that my wife and I have had a couple of swinging experiences with. Needless to say we are close friends. We were planning to get together shoot off left over firework s from the 4th of July, barbecue, and have some drinks. About a dozen or so of us were there. 4 married couples and the rest single friends.

Everyone was congregated in the backyard grilling, sitting around eating and drinking while we waited for dusk in order to begin the fireworks. Anna and I split up as I grabbed a beer and headed over with the guys at the grill and she took a seat on a lawn chair with some of the ladies. About a half hour into the festivities I was chatting with a couple I had not yet met when Isabelle's closest friend Keri showed up. Keri is a stunning Latina with long dark hair, and skin. She is around 5'4" and curvy with a huge ass and modest B cup tits. Something about Latinas gets me and Keri is no exception. She had on cut off shorts that showed the bottom of her ass cheeks and a tight yellow shirt with a black bra on underneath. It was instant excitement when I saw her. Because Keri is so close to isabelle and is one of the very few people that know about my wife's swinging/open relationship. Anna had encouraged me to get Keri involved in our exploits before but I had no idea how she felt about it and left it alone.

curvy redhead [f]ucks [m]e all weekend

J was a bit younger than me. She was 23 and had hips and breasts that were sexy, full, and firm. She danced and coached gymnastics but her body's natural curvy shape was what remained in my memory. Curvy is often shorthand for overweight. In her case, this was not true at all. She was fit but she never felt fragile. It's shitty writing but true in her case that she was built for sex.

I had met her through friends. We had met at brunch and hung out for a bit at my friends place. We never managed to really get together before I moved to another city. Not really sure why. Maybe she was seeing someone. It didn't really matter to me.

She texted me a couple months after I moved to a city on the northeast USA. I had gotten a small but nice place in a great neighborhood. We were exchanging notes about random stuff and being in the city. She had never visited before. We talked about that and her being done with school for the semester. I asked her if she wanted to come. I was fortunately in a great place financially and I offered her the plane ticket as well. It was a pretty reasonable fare. So fuck it. Life's short.

Schoolgirl, Part Five [MMMMMMf]

Okay, back to present day, guys.

It was months ago but Aly remembered that pivotal day with Mr. Hale and the water bottle as she waltzed down the hall of her now former high school. School was technically out but several teachers still hung around to clean up, mark final grades or prep the syllabuses for their summer classes. Mr. Hale was in the last category. Aly was glad, because that meant he’d still be teaching at the school for several hours for most of the summer, giving her ample time to keep trying if today was for some reason a fail. Of course, in her sexy little white dress, Aly didn’t anticipate that. Today was going to be the day. She was going for the win and whether it was in the bathroom, the book closet or bent over his desk, she was going to get Mr. Hale to fuck his cock inside her. But she was shocked at what she saw when she walked into his classroom.

Canadian Wild Girl [FMF] [exh] [voy] [oral] [public]

It was a boring Saturday night, and Sam had nothing to do. She felt like going out, but wasn't a fan of dressing like a slut. However, she still wanted to be ready for action, just in case. Putting on a little pink g-string and black bra, Sam wore her modest red dress that was full sleeved and up to her neck and a pair of knee-high black boots. Feeling like she accomplished both of her goals, she set out for her nearby bar, The Globe.

When she got there, there was a camera crew for Canadian Wild Girls, a Girls Gone Wild style show where they film amateur girls and give them stickers or t shirts in exchange for the girls flashing them. "God, you must be desperate to flash for a shirt!" Sam thought to herself as she noticed some other girls there flashing their tits to the camera crew. Rolling her eyes, Sam went to the bar and ordered a long island iced tea.

Weekend with /u/highavailability, part 2: shooting loads, a double entendre…with a few pictures

Saturday morning, we slept late. We always seem to sleep in the spoon position. His arms totally envelope me, and it’s the most secure and comfortable feeling. I don’t remember what time we woke up, but I definitely remember how. I felt HA’s rock hard cock poking into me. Apparently, he had been awake for at least a couple minutes because it was already covered in lube when I felt it slight effortlessly into me. I gasped into full consciousness as he pulled me close and thrust in balls deep…slow at first and then with increasing ferocity. I looked back at him over my shoulder, told him to kiss me and then to cum for me. He started to shake and hold me so tight that I knew it was coming even before I felt the first hot waves of cum erupting into me. There’s nothing I want more than to wake up just exactly like that every fucking morning…or at least on the weekends.

Finally, we willed ourselves out of bed, showering and getting dressed before venturing out for coffee. I make it sound like this was a quick process, but in actuality, it take me a solid hr to get ready to venture into public. HA is sweetly tolerant if not mildly amused by this.

The whiskey bottle diary, first entry part1. [M][MF] [mF][str8] [VOY][ORAL][MAST]

The whiskey bottle diary, first entry.

I walk a fine line between living a good life, doing all the right things, morally and expectation wise, and living totally free. I enjoy being the guy that does his best to take care of business and make sure the people who need me have their needs fulfilled and more. But it's a struggle for my spirit, that just wants to fly.. down every new road, into the unknown or even the partially known.. just to see what's down there. It's adventures like that, that drive me through the ordinary and mundane cycle of work eat sleep pay bills be broke do chores. The difference now is that I'm older and care a lot more about everything in the regular world that's going on around me. So my adventures are more refined, and direct to the things I want to explore. This is a story of one of those things. It gets a little uncomfortable at the end, so I ask that you, the reader, keep an open mind and understanding of how things ended up the way they did.

Now sit back, relax.. while I pour myself a shot of whiskey and tell you my story..