Gentlemen are dead [MF]

[MF]

It was just an usual cold and typical friday evening in which me and my two best buddies went to our favorite bar to drink some beer and play some darts. Around just the same few old creeps of always who almost lived in the bar, showered in beer and cried about their past. I was not in the best mood since that sames’ weeks’ monday I had gone through a hard break up. Throwing big words around about how gentlemen, like me, just get used like toys and how I would from now on become a fuckboy and bang the first sexy chick to enter the bar.

Losing my virginity to Jennette McCurdy’s long lost twin [MF]

Been a long-time reader of GWS and I’ve been in a bit of a dry spell recently. I’ve decided it’s time to give back. [Skip past the break for the good stuff!]

I didn’t have a whole lot of self confidence until very recently. About 2 years ago, I lost around 45 pounds over the course of 3 months on a keto diet. I’ve done a great job of keeping it off, and it’s done wonders for my dating life. I had a few opportunities for relationships in the past, but I never took it to the next level until last June, just before my 26th birthday. I’m a 5’8″ slim guy with a very angular face, brown hair, and blue eyes. My friends would describe me as nearing hipster fashion, but not quite. I have a 6″ dick that’s a little thicker than average.

I was poking around on various online dating apps, but I didn’t really ever make it past the 3rd or 4th date. I also didn’t really know when to escalate things to the sleeping over phase until this happened. Usually, I’m the first to message a girl. I was pleasantly surprised when my PoF inbox had a message from a bombshell. We’ll call her Monica.

[M]idnight [F]uck

(First post, so lmk what you think!)

Edit: We’re both college kids

One night, I was staying over at my gf’s house. We had fooled around a little before bed, but it was nothing serious. We made out and groped a bit, and then we spooned and fell asleep. At some point in the night tho, I woke up. It was hot in the room, and I was sweaty. I didn’t know what time it was. All I did know was that I was hard, I was horny, and I needed to have her right there and then.

I lightly nudged her so that she was laying with her back on the bed. She had a large shirt on and no bra, so I fondled her chest and, starting at the neck, kissed my way down her body. I pulled her shirt up a little, and kissed down her stomach going ever so slowly so I didn’t wake her up. Eventually, I made my way down to her crotch. Her panties were on, but she was already wet. I could smell her sex. It drove me crazy, and next thing I knew, I had my face buried in her panties. I just rubbed my face up and down, teasing her pussy. This is where she started to wake up.

[Mf] The unattractive girl who made me question everything.

During my years of promiscuity I have been with just about every type of girl. Skinny, medium, very very large, 10 inches shorter, 3 inches taller, drop dead gorgeous and hard to look straight in the face. But I have always been a firm believer in we are all beautiful in our own way, and on top of that, we all deserve orgasms. We deserve to have fun. So the only thing that would get me to say no thanks was if she openly admitted or I even heard she may have an STD. All that said this story is about the most unattractive girl I have ever been with and how my body boggles my fuckin mind.
I was young, probably 18 or 19. She was at least 18 but no car and strict parents. We were very much just a late night booty call so I honestly never saw her in the daylight. But I did not need to.
Now I will try to describe her but let me just say I am not trying to be mean and I am not a shallow person by any means. I had 4 different booty calls with her until she told me she didn’t want to anymore.
So this girl was average to a little thicker weight. Dark hair that looked like she did not brush it often. Thick bushy eyebrows. A little acne. Somewhat big teeth. Large breasts probably D cup. Dark nipples. Trimmed but not shaved pussy. She also usually smelled like bar soap. Which is better than smelling bad but never had like a typical deodorant or perfume that a girl of that age would wear.
She always made me eat her out and make her cum that way first. Also always made me wear a condom. Which not everyone did so I didn’t unless it was requested.
We always had our sessions in the back of my SUV with the seats down in a parkinglot directly across from her house. She would sneak out her window and run across the street and just climb in the back. We would kiss and I would reach into her pants. She was always soaking wet. Her pussy tasted so good too I loved eating her until she soaked my lips. But then….
Now when it comes to sex I don’t typically last a very long time. I’m good for a solid 15-20 min. Give or take depending on other factors but on average. What saves me are 2 things 1.) My pussy eating skills and 2.) My lightly fast ability to reload and be ready to fuck again in maybe 2-5 minutes.
However with her it was different. You would think well this is the most unattractive girl he’s ever been with so it must have just been pound town for ever. It was actually the exact oppose. She is the only, the ONLY, girl this ever happened with and I still have no idea as to why but, once my cock was wrapped up and I press the tip to her opening, I already felt my balls tighten.
I pressed myself inside her looking at her face which was not a face that I did not find attractive in the least. As soon as my cock was balls deep inside – I would cum. Every. Single. Time.
I can’t explain it. I was hardly even attracted to her body nevermind anything else. She wouldn’t stroke my cock never mind suck it. I was basically just being used as her personal breathing dildo which may actually be why I found it so fuckin hot. But, every time, I came within the first thrust. I filled the condom as I pumped in and out hoping she couldn’t feel the spurts inside her or my cock pulsing like crazy. I would keep fucking her. As hard and fast as I could until I started going soft. Then I would try and go slower and get hard again but it didn’t work so at that point I would fake an orgasm and the pull right out.
This means our sessions lasted maybe 5 minutes. She got increasingly more and more annoyed, rightfully so. Until she finally said naw I’m all set “I need a guy who can satisfy me.”
That shit hurt because I pride myself on the amount of girls I’ve satisfied and to the extent that I’ve done so. But for some reason this girl, the most unattractive I’ve ever been with, made me cum quicker than I’ve ever made myself.
The human body and mind are strange places.

Unexpectedly fucking [m]y [f]riend at a Halloween party

Apologies ahead of time for a ton of background and a complete inability to write dialogue!

In college I had a friend named Caroline. Caroline was a very intelligent, loquacious and outgoing girl. She could always bring me out of a lowly mood and was always a welcome addition when a group got together to go out drinking at the bars. On top of her great personality, Caroline had an amazing body. She had green eyes, jet-black hair and skin that was extremely smooth and pale in a very appealing way. She also had smaller breasts that I can only imagine were maybe B cups (not that that’s a bad thing) but her ass was amazingly sizeable and round and she liked to joke that it was her one redeeming feature. I highly disagreed with that. She had several features that made her extremely physically appealing. Nonetheless, for some reason it really turned me on that she knew she had a nice butt and was proud of it. She always wore skirts, dresses and tights that accentuated and showcased her lower half. One time she came to a study session for a test in a class we shared wearing those tight Nike Pro shorts. I maintain to this day that her wearing those shorts is the reason I got a D on that test (insert joke about her getting the D).

Made my brother watch [group]

A lot of people have asked me if any of my family members were ever involved in my adventures and I usually kept them out of everything I had going on. Sure I used to roam around the house in my underwear to piss off my father when mom was gone. Well at least he acted pissed which just made me wear even more revealing underwear.

I think my brother had a pretty good idea of what I was doing. I tried to hide my slutty side from him but there was one evening when he just had to watch me have fun.

He was having three of his friends over from out of town. I knew one of them was pretty cute and I was hoping the other two would be passable as well, because I was planning on royally pissing of my brother.

The four of them were in our garden house where we had our infamous pool table. I know the guys were already hanging out in there for a good two hours. Having a couple of beers and playing pool.

[MFM] Craigslist Encounter #1

This is the first time I participated in a threesome with a couple from Craigslist.

I had posted an ad similar to the one I mentioned in my #2 story. I was just looking for a couple who wanted to be watched. I got a reply from a couple who was interested. We exchanged pictures and stats and they were already at a hotel and wanted me to come over as soon as I could.

They were pretty straight-forward with what they wanted, they wanted me to go into the room, watch them, direct, all while jerking off. I liked the idea and agreed to meet them. I was pretty nervous since I hadn’t met anyone through Craigslist before, let alone be a part of a threesome.
When I arrived at the hotel, I was still really nervous, I text them that I was there and they replied for me to come right in, that the door was open. But still being nervous, I asked them to come to the door instead.
A couple seconds later, the girl answered the door, naked. She was a curvy girl. Not typically the kind of girl I’m attracted to, but I honestly wasn’t there for attraction, I wanted to experience being with a couple. She invited me inside the room. It was a small room, a queen sized bed, a small table with 2 chairs, and a door that led to a bathroom. Her boyfriend was sitting on the bed, cock out, and was wearing a hoodie.

Let Me Whisper In Your Ear [mf] [exh] [oral]

Wrote this a while back for a prompt on r/DirtyWritingPrompts about a girl who secretly longs for her male best friend to leave his abusive girlfriend. Enjoyed writing it, so I thought I’d post it here. It’s in two parts, so scroll to Part 2 for the good part if you want. Contains extreme vanilla, some light exhibitionism, and 4700 fucking words.

—-

## Part 1

“So then what happened?” Sarah asked distantly as she leaned forward over the table, quietly hoping that Reed would notice the soft brown cleavage crowding its way out of her sweater.

“Then she just… kicked me out,” Reed explained meekly. He shifted the ice pack around his matted brown hair and slouched into the cafe booth, melting into the vinyl. “Shoved me outside and threw my stuff out and locked the door.”

Tay’s Tea Cafe was a popular college spot, especially since the campus library was always overfull and didn’t serve boba milk tea until 2AM. Every night was full of freshman vampires right up until last call, all coming in to cram or sober up. The dark beech walls and white tabletops glowed under the soft pendulum lights scattered throughout the room at different heights, like stalactites in a dim wooden cave. But there was a quiet, more private area behind the cashier with booth seating separated by frosted glass dividers where people could self-pity in peace, so of course that’s where Sarah had found Reed.

Backpacking with his sister Part 2 [FM][Inc][Outdoor]

Link to first part in comments

The chilly morning cold slowly pulled Brian out of his sleep, but finding his naked sister cuddled in his arms next to him fully woke him up in an instant. He sat up straight, trying to understand what had happened and how they could possibly get themselves out of this mess. Failing to come up with anything he sank back, letting out a sigh and running a hand through Lucy’s hair. She was as beautiful asleep as she was awake, the short brown hair soft to his touch as much as her cheek.

Running his fingers over her cheek woke her up, an equally relaxed and exhausted smile creeping over her face. He wanted to pull his hand back, but she grabbed his wrist and pulled him closer.

Her head turned slightly as she looked at him with one eye still closed. “Good morning.”

Brian chuckled and leaned in to kiss her neck. “I didn’t just dream last night, did I?”

Lucy turned around, locking her arm around him and pulling him in for a kiss, their lips meeting hungrily.

Then she pulled back and giggled slightly. “Does that feel like dreaming?”

Backpacking with his sister Part 2 [FM][Inc][Outdoor]

Link to first part in comments

The chilly morning cold slowly pulled Brian out of his sleep, but finding his naked sister cuddled in his arms next to him fully woke him up in an instant. He sat up straight, trying to understand what had happened and how they could possibly get themselves out of this mess. Failing to come up with anything he sank back, letting out a sigh and running a hand through Lucy’s hair. She was as beautiful asleep as she was awake, the short brown hair soft to his touch as much as her cheek.

Running his fingers over her cheek woke her up, an equally relaxed and exhausted smile creeping over her face. He wanted to pull his hand back, but she grabbed his wrist and pulled him closer.

Her head turned slightly as she looked at him with one eye still closed. “Good morning.”

Brian chuckled and leaned in to kiss her neck. “I didn’t just dream last night, did I?”

Lucy turned around, locking her arm around him and pulling him in for a kiss, their lips meeting hungrily.

Then she pulled back and giggled slightly. “Does that feel like dreaming?”