Watching [M]y Roommate Have Some [F]un

I shared this story in a PM with someone who liked my first one and wanted to hear about another voyeur experience. This happened a few years ago, and had never been told to a soul before. Enjoy!


A sound stirred me from the hazy confines of half-drunk sleep. I knew what the sound was as soon as I heard it again.

The night had taken our group of friends from bar to bar; new friends were made and others wandered into the night. My roommate, Sam, made one of those new friends. She was blond, short, and possessed of generous curves. Her face dimpled when she smiled and her eyes were blue like mine. She made me wish I was single. I stole glances at her as Sam worked his charm, I could tell she was into it. More drinking, wandering, and eventually five of us pile into a cab. The details at this point are blurred. Two friends crash out on my futon downstairs, I fall into my bed, and through my door I can hear Sam take the giggling blond (Ashley? Alison? Something with an A) into his room next to mine.

Sleep.

I dom’d a guy (and I liked it). [F/M]

So I originally posted this as a storytelling/re-enactment type thing to /r/gonewildaudio but after only 24 hours I was so mortified by my acting skills that I took it down. It's a story I often chuckle to myself about though so I think worth sharing. And I can explain so much better in this format.


There's a long backstory to this one that gives it context. If you're just looking for the sex get to scrolling.

This takes place while I was still in grad school, after my epic summer away that started with The Rugby Player I'd decided to try to settle down, stop having random sex, and if I recall "He's Just Not that Into You" was really gaining popularity. The movie had probably just come out and all my girls were locked into the lessons in the book. So when I met this guy, let's call him Colin (not his name), I was resolved not to play the silly dickmatized girl. It also helped that I was salivating over a completely different guy at the time, a singer in a band, so I wasn't all about hooking up with Colin, at least not in the beginning.

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.

True Story. (m)e taking her (f) shopping

This was last Summer, so I need to try this again….

I put an ad on Craigslist looking for someone to take for some sexy shopping. The idea is I would meet her at the mall, we would shop as if we were boyfriend and girlfriend, which means I would pick out skimpy outfits for her to wear, maybe feel each other up while we shop, etc.

A few responders were asking what I would buy for them. This was not an invitation for prostitution. I was not looking for a professional, but I would possibly purchase some sexy panties etc. for fun.

I finally had a real non-working woman respond. She was a little bit older, but looked pretty good in her picture.

When we met, she told me to let her know where I parked because she had a surprise for me. I thought this would mean I was actually about to meet a guy or was being setup by a guy who would drive by to see me waiting and somehow get a kick out of it. This has happened to me often.

Settling the Score [MF] [Tickling] [Oral] First post – would appreciate feed-back

He'd been working on the Jones estate for a few weeks now as a laborer, landscaper and handyman. It paid decently well, and Mercedes Jones was in the habit of making sure the people who worked for her husband were well fed on hot days. She often fixed them lemonade or coffee and brought pastries out on breaks. Mark liked her well enough (more than well enough, really, which was a distraction), but her husband was another matter entirely.

Short-tempered, picky and very much a micromanager while he was at the house, he didn't seem to believe that anyone he'd hired could do the job he wanted of them. Mercedes (or Merry, as she preferred to be called) always tried to talk him down if he was being nasty, but he didn't seem to listen to her much either. Mark never saw him raise a hand to her, but his biting remarks often left Merry shaken. She put on a brave face but Mark could see she wasn't happy while he was home. Fortunately, he was often away on business trips. Mark detested him, but not only for those reasons.

[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…

[F/18] – Family Vacation: How I hooked up with my step-brother in the hotel room

We just came back from a weeks vacation in California, and I'm still shaking every time I think of what transpired. Let me give you all a few visuals and background. I'm 18, my step-brother 19, and my dad has been married to his mom for 7 years. Basically, I've known him a good chunk of my life. He's very attractive. A little over 6 feet tall, lean but a little muscular, dirty blonde hair, and perfect blue eyes. If you're wondering about me… I'm 5"4, brown hair, brown eyes, kind of pale, skinny, and most guys would call me either average or a little above average probably. Nothing super crazy. Also, nothing at all has ever happened sexually between us up until this vacation. Not even flirting or hints.

Mark Figures It Out [MM][Anal]

The throbbing beat of the subwoofers made the gin and tonic in Toby's glass quiver in time with the music. He sipped again as his eyes scanned the room for fresh meat. The new semester always brought in guys looking to find out if that twitch they got glancing around the communal showers in high school meant something. And Toby considered himself the best person to answer all their questions.

One guy caught his eye because of the timid way he approached the bar. He was in good shape judging from the way his tight jeans and UCF soccer jersey outlined his muscles. Toby stepped closer before anyone else could and leaned against the bar next to him without getting too close. He drained his gin and tonic and put the glass down hard.

"Boris! Can I get another gin and tonic?" Boris the bartender was only wearing a bow tie and tight leather pants. Despite his cut, muscular body he was currently off the market dating the owner. Such a pity.

"Can I get a bud?" The soccer jersey guy asked.

"You have to ask louder than than," Toby said as he leaned closer, then turned to face the bartender again. "Hey Boris! Add a bud to my tab."

That time I sucked my older coworkers dick [M/F]

So, in my early twenties I started working in a clerical position at the local megacorportion. This was a seriously low level job, menial filing and data entry. My desk was in an area with all the IT people and me, being a bit of a nerd, got along really well with my coworkers.

There was this older guy, Mark, who was in the upper management of the IT department. Like one of those things where they have a fancy title but are stuck in the cube farm with the rest of us plebs. Anyway, I was really attracted to Mark from the very first. He was in his late 30's, tall with dark hair and light eyes. He was a fitness fanatic and had that lean runners build that I love. It is really unusual for me to be attracted to someone his age, but damn if I wasn't completely turned on by him. He had this sexy, low voice and had this great dry, sarcastic humor. Unfortunately, he was also married, so I didn't put too much thought into it.

My Real life sexual encounters.

First up is my first lesbian experience.

So I decided to do a post on my first "Girl/girl" experience. Well not my first girl, girl experience but full on Sex I guess. I was a lot younger and skinnier when this happened! (before my training days) But it was one of my best memories and even though I love cock. I still love to play with a good pair of tits or dominate a small petite woman.

So before getting into the good stuff, let me just give you a short "how did we get here?"

A good friend of mine and I used to have what we called "dk Tuesdays." Basically it was our way of making a simple "weekend style drinking" acceptable for a Tuesday. Yep, we all have our excuses. Our goal on dk Tuesday was to get shitfaced dk and whatever happens on dk Tuesday stays with d***k Tuesday.

So here we go: It was just another d***k Tuesday, and my friend (who I should mention has lesbian tendencies) and I were prime for it. We'd pregamed at home with a few Little King's and a bit of 80s music. I was only a few minutes from downtown and the art gallery was on in Columbus, so we walked our way into town.