My paid sexual encounter with a 69-year old woman

I will start from the beginning.

I have always been attracted to the idea of paid sex with a stranger that I just met for the first time, but have never lived out the experience. The appeal is tied the thought of having an encounter where there are truly no strings attached and the whole reason for being in the same room is to simply have sex. There is also an "I'm in charge of this." edge to the fantasy that is not something that ever happens in a normal sexual exchange.

I recently had a small financial windfall and decided that it was time to live this fantasy for real. Just the act of making the decision to do it was enthralling. The next step was to "shop" for the woman I would hire, and the task was akin to being a kid in a toy store with a wad of money. I know that doesn't really paint me in a positive light, but it's what it is. Just the act of looking was a fun and extremely satisfying activity.

[Str8] [m] [f] [oral] [preg] First Erotic story thingy…

Alright so I’m sitting in class, staring at this hot babe name Bailey. Man she is a 5:4 slim cheer girl wearing a see through turquoise shirt and some skin-tight spandex. Through her shirt you can see the light blue bra she is wearing, but only in the back, the shirt is more opaque in the front. As she is leaning over her desk you can see her small A cup boobs hang over her desk. When she gets up and walks you can see her cute bubble butt move side to side. Begin fantasy fanfic thingy Finals have just finished and the bell rang. I walk over to Bailey’s desk and say, “Hey Bailey, let me show you something real quick. “OK…” She says in an unsure voice. We walk out of the classroom as people are leaving, luckily she follows. Now kind of pissed she says “Alright seriously, where are we going.” “Bailey, let me be honest with you. I want to have sex with you. I know I know, if this were real life you would slap me, but can you just play along for the story.” We just kind of stare at each other awkwardly for a sec, and then she finally speaks up and says something I will never forget: “You get one shot, impress me.” Scene change I open the door and let Bailey go through like a gentleman, she quietly thanked me. Luckily the library was relatively empty, and an old dozing librarian was the only one keeping tabs on the place. Bailey and I run to the back holding hands and find the perfect place. In the back corner of the library there was an area with a long wooden table and some chairs. Finally in privacy we embrace, our lips hugging together like they were made for one another. We break contact, and then unable to resist we meet again. This time our tongues found one another and did a dance wrapping and twisting around one another. My erection stood out proudly, poking Bailey in the stomach but she seemed not to care. While exploring each other’s mouths I put my hands to work, dropping them down to feel her glorious ass. Grabbing with both hands I spread her apart, her spandex easily stretching along. For some reason I couldn’t help but grind against her. Surprisingly she gladly obliged, getting up close with her hips and moving up and down against my member while continuing to make out with me. With a strength I have never seen of her, she pressed me up against the walls and grinded her ass against my throbbing dick. By now I have grown to a full size of 6.5 inches, pretty good for a 15 year old. Bailey looked at my raging hard on and bit her lip. “Do you want me to take care of that for you?” All I did was nod, and she immediately dropped on her knees. She carefully took her fingers and undid the buttons on my pants, and then zipped down my fly. With a little tug, my pants fell, and she was left face to face with my member outlined in blue briefs. Fast at work she tugged down my briefs and my erection sprang loose. “Um, I’ve never done this so don’t be too hard on my dick sucking skills” We both laughed for a bit,but soon she went right back two it. As if trying not to wake a sleeping baby, she slowly and quietly moved towards me. She then simply kissed the tip , and then started licking the head around in a circle. A sudden jolt of pleasure ran up my spine as she did this. Slowly making larger and larger circles until she just ended up putting the head into her mouth, going in, and out. Getting deeper and faster each time. Simultaneously she used her left hand to stoke my balls. Faster and faster she went until I thought I couldn’t take it anymore but then, it stopped. Right as I was about to release my load she stopped. “My turn” She said triumphantly with a big smile. Maybe she gets a kick out of giving guys blue balls or something, I’m not sure. In a violent fasion, I picked her up and lied her across the table. Standing to the side, I took my hand and placed it on her left breast. Through the fabric and her bra I carefully stroked her nipple, doing the same with the other hand and breast. I than grabbed her transparent shirt and softly lifted it over her head, exposing in full her light blue bra in full. I took my fingertips and grazed them against her stomach, from her belly button up to her chest, putting the right amount of pressure so she could feel my cool nails against her warm skin. Feeling as if I tortured her enough, I reached under her back and unclasped her bra. I pulled it off, as soon as I did so her face flushed red with embarrassment. As if reading her mind, I comforted her by saying “Don’t be embarrassed, you look beautiful.” And I was not lying when I said that. She had silky white smooth skin with close to no imperfections. Her outey belly button hung out, surrounded by rock hard abs that put me to shame. Her breasts were like small mountain peaks, her small A-Cup breasts bulging outwards. On top she had small pink nipples, pointing straight up and aroused from for-play. Looking to make her happy I took my tongue and started to lick around her left breast, making the circle smaller and smaller with every rotation. Eventually I made it to the center where I engulfed her breast in my mouth, sucking and flicking her tipple with my tongue. Not wanting to leave her right breast hanging, I rubbed it with my hand. I than switched, continuing this process for the next five minutes. Like a chess player, I planned my moves carefully, leaving a trail of kisses all the way down to her spandex. Hooking my thumbs underneath I lifted them off, leaving her in a single florescent pink thong. I slipped the thong off, revealing her flower. A perfect pussy in short, golden blond pubic hair, with pink lips that were slightly bulging from arousal. Getting hornier by the second, I was impatient and did not feel like waiting. Instead of eating her out, I climbed up on the table. I slowly brushed her lips (lower) with the head of my penis. Like a painter painting a masterpiece I stroked back and forth. I carefully pushed through her lips. (Panting heavily) “Alex Alex Alex, … i’m still a virgin.” “Don’t worry” I smiled, “I am too.” With those words I penetrated through her hymen, making her grip the table tightly and scream out in pain. A tier ran down her cheek onto the ground. “Is this OK?” I said going at a slow pace. She nodded, still a bit traumatized. Suddenly their was a splinter, and the table legs broke in half, causing the two of us to fall on the ground. Both hot, sweaty, and naked we started to laugh at the sad and awkward situation. Like the horny guy I am, I got back up, helping her up too, and leaned her up against a chair. I re-inserted by dick inside her and I started bounding at her again. Faster and faster I went, I grabbed and squeezed her boobs in the process. I trusted in and out, her tight pussy like a rubber band around my dick. The situation intensified until together, we both came. “Wait did you have a condom on?” She asked feeling my juices inside of her. “Ummmm…” To be continued…

The Best Drunken Mistake I’ve Made- Part 2

(If you haven’t read the first part of my story the here is the link. Sorry it took so long for me to write this. I got nervous at how many people liked it and almost didn’t post this. I’m glad I am now tho.)

The next morning was more comfortable than I ever could have imagined. You would’ve thought Davey, Scott and I had been having sex for years. They both were completely unafraid to talk about it and there was absolutely no shame being thrown around at all. When Kyle finally came out from his tent from his tent the first Davey immediately yelled across the whole camp ground “DUDE, KYLE! We totally got fucked up and had a three way last night!”. We all started laughing uncontrollably. “No way!? That makes so much sense! We could totally hear you guys and had no fucking idea what was going on!”. The fact that our entire group was able to laugh about such an intense experience goes to show how open and carefree this group was. Not only that, but on the first night the tone was set that anything could happen on this trip, and you were going to be greeted with laughter instead of judgment.

Going to the dick exchange – Part 1: testing the waters (f/M and other people)

First off: some parts of this might come off as a little braggy. Let me assure that that's not what this is about, it's just how that experience came to be.

So this is about my wife and me and how we started swinging. We are in our early 30s, have been together for well over 10 years and are both presentable looking people but no models. She has long red hair, is quite busty (D cups) and has curves in all the right places. I am a worker, so muscles but not very defined, sadly.

We have a good thing going on in the bedroom (among other places), we know what the other likes, dislikes and outright refuses to do and we respect each other. But as the years go by, things start to slow down and even the most fun part of our relationship became quite the routine.

So we both start talking about it. I'd like to spice things up with other positions, places and techniques, she also has her wishes. "I'd like to have a really rough fuck one day!" was one of the more blunt statements issued during one of out post coital talks. "I can to that, you naughty little thing!" – "Well, there's the problem: YOU can't."

Couples camping with college friends [oral][swing][MFMF]

It had been almost five years since we had gone on a trip without our children, and my wife Shannon was very excited to get away with her best friend Sarah from college. Her friend's husband, Mitch, and I James,got along well and enjoyed similar hobbies so a weekend in the woods with them was going to be a blast.

In college we all enjoyed outdoor trips, mostly car camping with the girls, this time our plan was to hike 15 miles in to a secluded lake with a small water feature where we could set up camp. This meant everything we were bringing had to be carried between the four of us, which meant we were packing as light as possible.

Submissive girl worships evil villainess [FF][bdsm][Fantasy][Fsub][sm]

I scurried through the brothel to the secret room underneath, an inconspicuous base of operations for the rebels fighting against the Queen's tyrannical rule. They had welcomed me in months earlier, but now the trap was ready to be sprung. Having convened an urgent meeting, duping them with lies about having critical information, I found the rebel commander Jake, surrounded by his officers, waiting for me. Excellent, I thought to myself. He was tall and fit, a self-righteous crusader on behalf of those oppressed by the Queen's reign of evil. Even his sanctimonious presence filled me with loathing and annoyance.

"Ellen, where have you been?" Jake asked me.

Backstabbing your ugly face, I wanted to reply, but instead I gave a lie about sleeping in.

Suddenly, screams broke out from outside the room. The thought that the Queen would be rid of these contemptible pests because of my betrayal filled me with excitement. Her minions surrounded the brothel, killing anyone who resisted. They stormed through the door and closed in on us. We were encircled. I looked at the crass faces of the rebels, they were in complete disbelief. Satisfaction. Finally, these stuck-up hooligans will get the punishment they so deserve.

My First Threesome/Swap (m/m/f/f)

This is my first post here but I felt compelled to share what I feel is probably the hottest sex story I have or at least the one I was thinking about a lot tonight.

My girlfriend Anna and I have been together pretty steadily. We were on again off-again through high school and got together again for good when i was a sophomore in college. She is pretty much the perfect woman in my eyes. She is blessed with a naturally curvy body, 36D/28/38 and has an amazing large ass that fills out all the fancy lingerie nicely. Needless to say she look amazing in a thong. She likes to dress punk/emo/hipster with the big glasses and the flannels and her hair is always dyed a bright red. Anyway, on the surface the two of us have one of the most boring relationships you can think of with the whole high school sweetheart thing but as we've gone through college we have gotten more adventurous and into more interesting things and it all started with this story.

My Little Orgy: Hitachi Orgasms Are Magic! (9M/5F)

So I've been lurking this sub for quite a while hoping that one day I'll be able to tell a real story worthy of the Halls of Gonewildstories. And by Odin's beard that day finally arrived!

For a bit of back-story my part of this journey started a few months back when I stumbled across a post about a successful Redditor orgy in my general vicinity. Seeing as how orgies and group sex in general is a huge fantasy of mine I could not pass up the opportunity to try and get involved. I know that as a single male the odds were stacked against me, but like a certain scoundrel smuggler I never worry about the odds. I messaged the Queen Pervert who organized the event and much to my joyful horniness she replied with an invite to the next event. A few months later, after a few false starts due to flakes/fakes, I found myself in a nice hotel suite with thirteen other beautiful Redditors. And I must say, between my now two Reddit meet-ups (first being completely vanilla) I feel like I can confidently say you all are some consistently attractive people!

Chapter one teaser: (anita cain) His Ultimate Fantasy

His ultimate fantasy by anita cain CHAPTER ONE TEASER

CHAPTER ONE:

Claire is naked laying there in the balcony floor with her best friend’s four fingers deep, intoxicated, and to spice things up there was a hunk watching. She couldn’t be happier. Her moans became more intense as Sarah rubbed her clit as she carefully inserted her thumb.

“I love her big pussy” Sarah said as she rubbed her own clit.

“May I join?” Jeff asked as he grabbed his button on his pants.

Both girls looked at him and grinned. As Jeff undressed Sarah couldn’t contain herself. She smell that pussy long enough. She inserted her tongue with her fingers. While rubbing Claire’s clit with her other hand. Jeff slowly walks closer and closer to them rubbing his hard cock. Claire looked at him lustfully as her eyes invited him. He kneeled down next to her slapping her in the face with his dick. The sensations that was running through her body was uncontrollable. Her mouth watered with the thought of it. The thought of that huge cock inside her did things to her she had never felt before.