[M]4[F] I was 17, she was 33 and married…First time I fucked my GF’s mom

I’ve never told anyone this story, but when I was 17, my ex-GF’s mom seduced me.

It started on a ski trip with her family. She had been a cheerleader in high school, and was a tall, voluptuous blonde and I was a straight A student athlete, with a ripped body and huge mane of hair. stayed up late watching a movie, and everyone including my GF went to sleep early. We drank wine together and sat close to each other on the bed, and I’ll admit that I had a hard on all night long. I was so naive that I figured she wouldn’t notice it if I kept my shorts covered up under the blanket, but a few times I had to use the bathroom, and it just wouldn’t go down.

That first night, we sat next to each other for several hours, and in spite of her finishing off a good portion of a bottle of wine, we never touched. We just talked, pretended to watch a movie and talked some more.

I was a kid from a large family, starving for attention, and she showered it on me.

The Warden of Superjail [Slavery] [MM] [Asphyxiation] [Thigh strangulation]

I was minding my own buisiness as usual. I never get outside my house much, but I needed to collect groceries so I could sustain myself. I’d had no sleep and I was all sweaty because I’d spend most of my nights fapping to nerdy men and stories of nerdy men choking people to death between their thighs. There is something about nerdy men that just rocks my socks off, so as I was grocery shopping, I could not help myself when I walked past the isle with chicken thighs, legs of lamb and pork rind – they immediately materialized themselves as the thighs of a nerdy gentleman in my mind – thighs ripe and thick – perfect for strangulation!

I got my groceries and it turns out I forgot all my goddamn money because my mind was so occupied about nerd thighs! I saw the woman at the counter eye me, as if she knew I was contemplating something and that she’d cop me when it turns out what I’m doing is now amounting to shoplifting.

Asian Hookers [MF]

During my time in the military I got to travel all over Asia. I banged a lot of hookers as it’s pretty common in most countries there. I’m a decent looking guy and had no problem getting regular girls too, but the whole sex trade is shoved in your face in some these places. It’s easy to indulge, especially after a few drinks. Thought I’d highlight 3 of my most memorable experiences from some different countries.

**Thailand**

Having two cute, petite Thai girls take turns sucking my dick. All the while they would be making out with each other and switching between licking, deepthroating, jerking me off, and sucking my balls. Very sloppy and deep. They were an amazing team. **I came in one of their mouths, which she swallowed. The other one sucked it for a little while after I came and then they both cleaned me off with a hot towel and we all fell asleep.** This was part of a multi day bender, where me and my friends had a hotel suite and would spend most of the days drinking, and most of the nights fucking hookers. I had 2 threesomes and the double BJ with those 2 girls in one night. You can live like a king in Thailand for cheap.

How I [23M] got into a sexual relationship with my roommate [28F] [MF]

Before we get into the story, a little bit about myself – I am 23 and recently moved to Chicago from New York.
Now since i just moved to Chicago, I found this okay-ish apartment in my budget . But the reason i chose this was because of the people that lived in it . I met them and we felt connected vibe instantly. I live with one girl, who is 28 year old and she has a boyfriend who comes over regularly and another 23 year old guy.
So this story starts a month and a half into after I moved in.
The girl, lets call her Amber, and her boyfriend – lets call him Sam – they both share an open relationship. But its different from the actual open relationship, and by different i mean they only sleep with someone else when one of them is out of town or is going to be busy for a few days or weeks. A fact which i learned in a very awakening moment. In the most literal sense.
So one night I wake up to take a piss and i come out of the room to go to the washroom which comes after the living room – while my room opens directly into a part of the living room. And as i open, i see Amber naked on the coffee table with a guy on top of her , who is not fully naked, he is though only wearing a T-shirt. Since our house is out on the main street, the street lights come in through the window and just lit up enough of the room to be partially visible.
Amber has always been a moaner, and someone who talks a lot of dirty while moaning. I could always hear her demanding Sam to fuck her harder and demanding him to fuck her pussy in a sentence such as “fuck that pussy hard. Make that pussy squirt”
She is also loud during that, and unapologetic about it. During the first day we met, while i was still prospecting about it , she said,
“Before we go forward, i should tell you me and Sam have a lot of sex – and by lot of sex i mean pretty much every night. And i am a moaner . So hope that not disturbing for you.”
I thought how loud or how much sex would they have honestly. But spending the first night itself, i was proven wrong. Now probably my other roommate probably doesn’t get her moans that much, cause his room is farther away from her, but for me she is right next to me – sharing a wall.
The first night I unpacked and slept on the bed thinking I’ll finally catch on some sleep with a full day of moving, and as i lie down on my bed, i start hearing the dirty talk of how she wants to suck the life out of his dick and the slurping noises begin followed by loud gag reflexes and his moans.
Now i wont lie, the fact that i am so near to someone having sex, with every sound being very audible, it made me feel as if I was part of a threesome where i am only watching them get down and dirty.
But i am still prioritising on my sleep even though at this point my dick is slowly getting hard. But then i reach the point of no return. And that is when he starts going down on her and she starts moaning.
Now i have heard my fair share of girls moaning . But this was something different. It was almost like i was listening to a porn movie . The moans were amazing. It only took me a second after the first moan i heard to get rock hard.
She kept saying “lick that pussy lick that pussy good. Put all your tongue in it”
And before i knew it , i was holding my 8 inch rock hard dick in my hands. Hearing her moans put me into a place where i did not realise when i had started jacking off. But she wasn’t done, this moaning went on for another solid 15 minutes before she exclaimed, “i am gonna fucking cum!! Open your mouth!! drink that fucking cum”
At this point even I noticed my pre-cum to ooze out now. I was really turned on. I wanted to cum. And i did pretty quickly once he started fucking her. And her moans and dirty talk reached to another level.
Now they must have had a good solid 40 mins of fucking before he came on her boobs (she kept repeating that for the last 5 mins when he exclaimed ‘i am gonna cum’)
And it got really hardcore in those 40 mins .. the bed was shaking she was moaning a lot- the pace never got slow, he only kept going faster and only stopping (i am guessing) to change positions.
I remember i came twice that night . Once when they were having sex and one after they were done and they slept but i was still very hard as i w take out to moans from my head . So i jacked off again – and that was the first time I fantasised of how her body would be . I did notice the hourglass figure when i came the house first time , and i also noticed the noticeably bigger than average boobs she had and the tight round ass she walked with. And this night was first of many (and by many i mean every night) that i jacked off her moaning first and then second time fantasising that i was the one fucking her.
Before moving here, i hardly masturbated once or twice a week, but now a month into living here, i was masturbating twice every night.
So now when i saw her on that coffee table with her legs wide open and her hands holding her boobs and playing her nipples with one hand while rubbing her clit with the other while the guy fucked her as hard as he can, i got an instant boner. While i am a guy who loves to sleep naked, i wore a pair of boxers when i got out of the room to take a leak. And as i saw her boobs, and her hard nipples, there was a huge tent formed on my crotch and as she noticed me and my tent, while i noticed her big , 34D full boobs jiggle up and down with the motion of the thrusts, i quickly noticed she saw me enjoying the view, so i quickly went to take a leak and once i took a leak i noticed to hear the moans again. Till now she wasnt moaning, which cleared a confusion that i had over the month that maybe she is faking it with her boyfriend of how big he was and how hard he was all the time, and that how much cum he was shoot. But now i realised that she was faking it in this moment and not before .
And now that i had seen her boobs and she was moaning, i was rock hard again, and i felt that i had to jack off . So did, i couldn’t hold my cum too much this time, the image of her boobs moving up and down and the fact that she was looking at my boner was too much for me.
While i walked back, i noticed he was done and he was lying on top of her and she moved her to see me as i was walking back to my room. I noticed her eyes went down to my half hard boner as i walked to my room and gave her a smile before going in, and she did the same.

The best part of waking up

You’re not awake yet. Your eyes are still closed and you feel warm, safe, and rested. That’s not all your feeling though. There’s a light drizzle of finger tips running up and down your back. Occasionally they stop, draw little circles, and move on. It feels wonderful. The best alarm clock ever.

Slowly you’re becoming more awake and more aware. The sun is shining in through the windows, but your eyes are still closed. Your lover continues tracing the outline of your body and occasionally tickles the side of your thigh. You can feel the tip of his cock pressed against your stomach. You know what he really wants and you don’t mind.

His finger tips trace their way to your hips again and you roll away from him. Drawing his hand low across your belly. He adjusts to your new position and continues tracing.

Over your hips, along your side, up to the side of your breast. It tickles and you struggle to keep the stoic face you imagine you have. His fingers continue up to your neck line then across over your breast to your sternum. Then trace down. Across your belly. Circling your belly button. Down further and further.

[M]y [F]irst escapade with my boss – part 2

[Here](https://www.reddit.com/r/gonewildstories/comments/a1liij/my_first_escapade_with_my_boss/?st=JP36BZSY&sh=33ce3d2c)’s the beginning of this story.

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I was growing impatient and after what seemed like forever I heard a voice saying “push the button”. I was stomping my feet like a spoiled child waiting for the elevator to stop on our floor.

“So eager for what’s to come, are we?” I could sense the smile on his face as he said that.

“And what would that be?” I asked in a mocking tone trying to act casual after my feet gave my excitement away.

“We’ll see when we get to my car. If we even make it there.”

Fuck. I knew he said that on purpose just to get my heart pumping.

We stepped inside the elevator and he walked behind me. As the doors shut I froze. I was prey.
He leaned over smelling my hair and then my neck. I shut my eyes trying to contain myself and breath normally.

I [F] took one of the biggest dicks I’ve ever had [M] 2 nights in a row

Met up for drinks at the bar next to his office and we hit it off immediately. Great conversation, tons in common, just having a fantastic time. Next thing I know, we’re in his office making out then I’m sitting on his desk getting my pussy sucked. Definitely a bucket list item crossed off there. He stands back up and we start making out again while he fingers me and I’m just gushing all over his desk.

I’m a generous lover so I decide it’s my turn and I get on my knees. I pull his boxers down and this dick so so big I gasped. He was kinda shy about it and I would have NEVER guessed it was so big. He was humble as hell. Well, I’m in awe but I’m gonna give it a go so I take the already-rock hard dick and work my mouth onto it. I could barely get my mouth around it and I definitely could not take it to the the balls. I was proud of how far down the shaft I could go, though. Every time I try to deep throat it, he grunts and gets extra hard. Apparently he doesn’t get it sucked a lot. I understand why.

The Drive [MF]

One of the problems with living in a small town is that everyone knows what you’re up to. It makes it kind of hard if you want to maintain a “good reputation” but also have a wild side. Good thing though about a small town, is there is usually lots of space to sneak away to and not be caught.

It was one of those summer days that you just don’t want to end. We had been out just enjoying the warm sunshine. A little hiking, some ice cream, some swimming and now we were driving home to our little subdivision. I decided to take the long way home because it’s a scenic drive and I just wanted some more time in the sun.

When you’re driving country back roads, there’s only one way to do it – windows down and music up. We keep going down all these curvy back roads and are enjoying the scenery and the breeze. My wife looks at me and says, “It’s a little warm”. I thought she meant she was hot, not just stating that it was too early in the year to be that warm.

[M]y [F]irst escapade with my boss

This is the first part of my first story here. The next one gets a lot more interesting ;)

I’ll never forget this one Friday night when the company threw a big party at this fancy place uptown. A lot of my coworkers showed up, more than I expected. But I was there to flaunt my curves in this gorgeous, silky, emerald green dress that I put on for the first time, for one person in particular and that was the CEO. I know, I aim too high.

Why the CEO? Let’s just say he saw something in me the second he first laid eyes on me (needless to say, the feeling was mutual) and has helped me a lot professionally ever since, but he always had boundaries.
This only made me want to get closer to him furthermore. And even though he had the same attitude towards each and every coworker, I’m pretty sure there have been rumors about us messing around.
But truth is, it never got further than stupid kinky jokes and a subtle look every now and then.
There was a lot of sexual tension between us. I‘m a slim, young, witty, attractive woman and he is a freaking god. He‘s a tall, big guy, with dark hair and beautiful blue eyes framed by a pair of flawless thick eyebrows. He was the alpha male. He would blend in immediately in any group and you could easily see all the other guys shifting their attention towards him, feeling a little bit insecure.

Cheating with the boss’ secretary [mf]

*Disclaimer: If you want to judge me in this story for cheating or anything else, please send me a detailed direct message explaining your issues. (That way you can waste your time and I can laugh while I ignore it.) In all seriousness, I was in a weird place at this time in my life, had a drinking problem, and as a result did a lot of bad, destructive, unkind and risky things. I’ve since cleaned up my life (for the most part) and have tried my best to be a better person and make amends. And as you’ll see in this story, I experienced at least a little bit of karma as a result of this incident anyway. Anyway, here goes.*

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This is a story about loneliness, desperation, bad decisions, and karma. But it’s a story of, objectively, one of the more erotic experiences of my life. So I thought I’d share it here.

At the time this story happened, I was in my mid-20’s and working at a small startup company in New York City. My job was in marketing and general operations, but it was small enough that everybody knew each other, even across departments. And, as happens often in startups, we developed a nice camaraderie with each other over time.