Affairs of a Lifetime – Martinique

Lis (short for Lisolette) tightly squeezed my right hand with her left, her eyes wide open as her hips bucked wildly, screaming "don't stop, please don't stop!" Pulling her hips to him tightly, he kept fucking her through her first orgasm in over six months, ready to take her over the top again.

Lis had been divorced for three months. A former client of mine, we had become rather close friends over the past couple of years. She had called me just three days ago when she found out that friends of hers had to give up a short trip they had planned to Martinique and offered her two seats on the plane and use of a small cottage on the island. Lis really wanted to get away for a couple of days, her divorce being finalized, and truthfully, I also needed a short break. The next thing I know, I'm looking out the window of a Gulfstream IV and the island of Martinique, beautifully surrounded by the blue/green water.

Posting my non-redditor friends first [F/F] experience with her best friend.

The keys rattled in the doorknob as she struggled to turn the handle, completely distracted by the gentle hands clutching at every part of her body. She shivered, mostly from the cold, but also from the excitement of a new experience. Eventually the door flung open and they fell in, one landing on the other. They giggled in unison before helping each other up.

They stood for a moment, gazing into each other’s eyes. Rose could feel the liquor’s effect on her brain, just slightly, but she knew this was what she wanted. She smirked at her friend, a look of lust spread across her face. With a rush of movement, Amber had her pushed up against the wall. She kissed her passionately as her fingers ran through Rose’s curly, golden hair. Rose was in awe of this beautiful woman who stood before her. She had always been envious of her voluptuous friend, whose hair was lusciously bronze and her body, a perfect hourglass. Now, however, it merely turned her on, not a single jealous thought entered her mind.

Vacation Experience [M/F]

Well this isn't nearly as exciting as some of the stories I read here but I can promise that this one is 100% true.

My family always goes on vacation upstate to one of the great lakes. This is usually during mid-summer, about a week long, and has always been a chance to catch-up with family; mostly our out-of-state-cousins. We don't get to see them often, and for this reason, we usually only spend time with them and generally ignore any non-family.

Well a few summers ago this was not the case. Schedules didn't match and they couldn't come up at the same time as us. There is not much to do up there and to pass time I started to make friends with some of the other vacationers.

Unfortunately at the time of this story I am 22. I say "unfortunately" because I there is literally nobody else there in their early 20's, so there were not a lot of potential friends to be made.

(M)(F) she saw my post and sucked my cock.

So today while at work I received a message from Kari, the young lady from my previous story. It was a picture of her tight shaved hole with a caption "saw your story on Reddit and now I'm wet." I returned the favor with previously taken dick pic and offered to help satisfy her.

We agreed to meet during my lunch break at her apartment nearby. I practically ran up the two floors to her place and she opened the door half topless wearing only jeans. I expected there to be some making out but she grabbed my belt pulled me inside and went straight to her knees. She undid my pants as I threw my shirt and tie to the side and my erect dick popped out onto her cheek.

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…

Loving Anal (f)or (M)y birthday. [Long]

Details changed slightly, written with omniscient narrator POV. Hope you enjoy my re-telling as much as I enjoyed the actual encounter!

In her mind, nervousness mixed with excitement and self-consciousness as he poured the oil out on his hands. Her skin was already slick with previous applications, and while she liked the feeling of his large warm hands easily gliding across her, she still couldn't help but feel vulnerable. Perhaps even a little silly, especially in this position. She giggled as she thought about all the girls in the class doing "happy baby" next to her, and knew that the next time she did this in class, her mind would come back to this moment. Feet up in the air with hands grabbing toes, her naked torso slick with oil; Her vagina and, even more naughty, her ass on complete display for her man at the end of the bed. She still didn't feel comfortable in this position, but oh, the way he looked at her when she did it made her want to pull him in for a deep kiss.

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.

[M]eeting my hospital nurse while he’s o[f]f-duty.

I may have mentioned it before in one of my stories, but I'm a pretty…well, I'm sickly. I've been immune-compromised for about as long as I can remember because of a sickness I got when I was little, and I tend to get hospitalized rather frequently. I'm in an out of the hospital. The doctors and nurses there knew me from when I was little, and they're more of a family to me than my actual family. With mom and dad always gone, I'd come to know my surgeons, nurses, aids, and orderlies as the family I never had.

One of the nurses I grew up with was named Daniel. He was around 23 or 24, only a couple years older than I was. We met when I was five. He himself was being hospitalized as a cancer patient, while I was hanging around the visitors' waiting area because my grandma was getting her own check up. He'd snuck out of his room and we'd started playing – until his nurse ended up dragging him back to his room. From then on, I would visit the hospital more often, particularly his room, especially on weekends. He was like a brother to me. He'd help me study, we'd play together; he was one of the reasons why I wanted to be a doctor in the first place. Daniel finally left the hospital, cancer-free, when he was around fifteen. Thankfully they'd given him homeschooling (or hospital-schooling?) so he wasn't too far behind in school.

(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.

That time I [f]ucked a Tinder guy whose profile only said “British.”

[NOTE: This is my first time posting here! Apologies in advance if my writing style is more rambling/bloggy than titillating; this entry is lifted directly from my diary. I just wanted to share one of my most fun sexual experiences with you all. Quick description of me, to make the story easier for you to picture: 25, Asian, tall, curvy, tan, long wavy black hair.]

Brendan's Tinder profile contained only one word: "British."

And I thought, "Why not?"

I've always found it dumb how Americans would fall for anything if it was said in a British accent, but I can't lie, I was intrigued. I'd never known or spoken to anyone British in my life before, much less fucked one.

To be fair, that wasn't the only reason. I only make decisions this risky when everything lines up exactly the right way. Were one of the following factors missing, I might not have responded to Brendan at all:

  1. British.
  2. Tall.
  3. Blond.
  4. Looked good in a suit.
  5. Here on holiday.
  6. Fancy hotel room.
  7. Timing was convenient. I was going to be in DC dancing with my friends late into the night, and his hotel was fairly close by.