Category: gonewildstories

The measure of 2 lovers is how they respond when you… | Part 2 [MFM with DP, Squirting]

Part One

So now I have Andrew underneath me and Jason behind me. They start muttering about lube to each other and I know what will happen next. Even with my body being totally relaxed from the multiple orgasms I've now had, my brain is a little nervous.

Just before, I'd managed to have two cocks in my pussy (which, for the record, I'm told is generally pretty tight). But this is again new. After a bit of pressure, I was being double penetrated.

I wasn't sure what to expect – it was an amazing feeling of fullness. The guys got their rhythm and I just let myself go into the sensation of it all. I have no idea how long it is before Jason cums in my ass and he pulls out. Andrew tells me he wants my ass so he can feel Jason's cum inside of me.

Okay, sure. I don't want to stop any of that.

Jason goes to my bathroom to clean up. Andrew does his thing. It feels damn good. He is smacking my ass and telling me how much he loves my hips and ass and tells me to please never lose weight. He doesn't cum and then as Jason is coming back into my room, he asks him where there is a washcloth and towel since he wants my pussy again. Read more »

Worst prostitute ever! Part II [m/f]

As a prostitute you get lots of bad advice from a lot of different people. From how to deal with the customers, to how to handle money. You always needed to consider who it was coming from, whether it was other prostitutes, the agency, drivers or doormen. Women in the business that were very keen to offer advice, I suspected were doing it to mentally reinforce their own decisions.

Some women prided themselves on how they tough they were with the clients, enforcing limits and demanding certain standards of behavior from them. In my experience it never worked, they inevitably struggled to retain clients, they’d fall out with the agency and would end up being strung along without getting the hours they wanted.

Your hours quickly became the focus of your work. The agency in quite a smart way had side-lined the issue of money. Most prostitutes will have a list of services and charges, we didn’t. We all provided the same services, though some more enthusiastically than others. The client paid a flat rate per hour to the agency who in turn paid us, usually again by the hour. Read more »

The measure of 2 lovers is how they respond when you… | Part 1 [MFM with DVP]

What is the worst thing that has ever happened to you during sex?

Have you ever had a threesome with two members of the opposite sex?

Any of you have that worst thing happen DURING a threesome?

You getting where I'm going with this? Good.

Let me break it down for you.

Jason, who I have known for over a year, has been a steady presence but infrequent lover. Jason and I have always talked about a mutual desire for threesomes. Jason happens to be bi-sexual. Or at least, he will have sex with guys when there is a group involved. I don't know if he's ever had sex with a guy on his own, but I know he and a previous girlfriend would "play" on a regular basis with another couple.

So his strong preference was for the two of us to play with another couple. I wasn't quite ready to share my bits with another woman, so he agreed to start with a man only.

We got together a few weeks ago and he told me he'd found our third – we'll call him Andrew. He showed me a picture (attractive and intense looking). Andrew happens to also be bi-sexual. He and Jason have fucked each other before. Read more »

[m/f] after my wife’s first date; or how I learned to stop worrying and love the smell of dirty panties.

I've done some shit in my life. I've slept with women who were married and cheating on their husbands. I cheated on my first fiance, a lot. I've lied. I've stolen. I've done shit I'm not proud of. But I always felt OK about myself. Yeah, I did those things, but I'm a better person and put it behind me.

My wife and I are in an open marriage. She's started seeing another guy. They have a blast while she's there, then we have really amazingly awesome sex when she gets home from her dates. I've always had a thing for her smell, even before this. I'd hug her and inhale deeply, either at the crook of her neck or the top of her head, and she'd always ask "What do I smell like?" to which I'd always answer: "My wife."

Then she started seeing this guy. He makes her smell different when he has her. His pheremones and cologne all over her when she gets home. The smell and taste of him in her mouth, or in her pussy when I go down on her when she gets home. It turns me on a lot. Read more »

My two threesomes and my double vaginal penetration experience (m/m/f)

I've never really seen myself as a threesome person honestly until recently. So it was kind of weird the first time it happened with me. I apologize for the length, this is two separate stories so that's why it's long! The second part of it is my double penetration experience, the first one is just use having our first encounter. I didn't realize how long it was until I submitted it, sorry!

I was sitting with my boyfriend Kyle and his friend Rob, we were at my apartment drinking and having fun when the conversation turned a tad bit sexual. We started getting into me and Kyle's sex life and what we liked doing. Kyle is bi so we talked a bit about that as well and Rob seemed curious. We talked about threesomes and Kyle mentioned he liked the idea and I shrugged, sure why not. We kept drinking and finally we started joking around, daring each other to do things. Finally Kyle dared Rob to kiss me, I giggled and Rob came over and put his arms around me and gave me a big peck. But he never really broke the kiss, it was starting to get a bit awkward, either you stop kissing at that point or you go further with the kiss. Read more »

Fro[m] hook-up to personal [f]uck toy

Not a native English speaker but this isn't Shakespeare so what the hell. Also, I suck at formatting.

A few weeks ago I met this girl on OKC. She was married but looking for a side gig since her hubby was regularly seeing other women, too and it seemed like she wanted to do some catching up. We hit it off pretty well and while we kept most of our privates lifes to ourselves, we quickly seemed to click on a sexual level and talked/sexted in explicit detail about how our first encounter should look. We met shortly thereafter and had hours of amazing, very rewarding sex but at that point I had no idea how much better things were going to get. Read more »

I’ve (m)ade a huge mis(t)ake

So I got drunk. Really drunk… The kind of drunk you don't wanna be, because you make stupid mistakes. This mistake was the worst I've made. I just broke up with my girlfriend of a year and eight months. Why'd you break up you may ask. Well we all got drunk and fucked her best friend beside her while she was asleep. That was shitty, but it led me down a rabbit hole of whoriness I've never experienced. About a week after our breakup, I had been looking at craigslist casual encounter ads. Sure, I thought, I could fuck one of these people. I had always thought about fooling around with a guy, and I even emailed a couple guys but chickened out at the last minute. But then I saw a transexual post. I have been curious about trans girls for awhile now, and my drunkeness made me more ambitious. She was a bigger african princess it would seem. She wasn't really a princess, more of a hooker, as I paid her money to have sex with me. So I texted this chick. She seemed nice. Wanted $100 for a half hour of fun time. I told her I would get the money and meet her in a few minutes. I drive to her apartment, (this is all with me being VERY drunk btw, I probably wouldn't have done this sober) and wait for her. She shows up and we walk upstairs to her apartment. We walk in and I notice her place doesn't look too great (considering the area of town we're in). There's a black leather couch and an area rug. Random paintings are hanging on the wall. As I said before, I am very drunk, so I excuse myself to the restroom. I relieve myself and look in the mirror. "You're about to have sex with a transexual." I said excitedly. I have fantasized about this for years and never thought this would come true. I enter her bedroom and she asks for the $100 we had previously mentioned. I gave her the money and she pulls out a condom. She places it on my cock and takes off most of her clothing. I can see her sexy black cock and wish I could be playing with it, but I want her to play with me first. She begins to suck on my dick like there's no tomorrow. It feels amazing and I almost cum as she laps up my cock. She tells me to fuck her from behind. I oblige. I stand up and she assumes the position. I lick her asshole real quick and try to enter her. Something's wrong… I can't get inside of that beautiful tranny. I try and try again to no avail. She asks what's wrong and I say it's probably due to my drunkeness. She says don't worry and has me lay down and starts sucking me off again. By this point I am discouraged and can't get hard anymore. I try to fuck her sweet ass once more but cannot muster up the hardness to do her. I admit defeat and tell her I'm so sorry. She tells me she's worried I am mad her, which is the complete opposite, as I wanted to fuck her so badly. I realize that buying a transexual hooker, while it's sexy in my fantasies, is probably not what I actually want to do. She understands and we say our goodbyes. Everything in me wants to fuck the shit out of that bitch, but I can't bring myself to. Whether that's the alcohol or the straight talking is beyond me… I guess I'll understand tomorrow. Thanks for reading, this literally just happened. Sadly I'm out $100 but maybe that's a lesson learned. Don't try to fuck tranny hookers! Maybe that's the lesson…

[m/f] Truth or dare turns into public oral fun

You guys seemed to like my last story so I'll post another story.

Another friend of mine (fwb) were playing a game of truth or dare on MSN Messenger (now you know how long ago this was). She came over to my place for drinks and well…alcohol + sexual tension + truth or dare = some crazy things.

And obviously because it happened so long ago, not all the dialogue is word for word but I tried to keep it close.

"What?!" I exclaimed in shock.

"That's right, cmon, do it," she said with a grin on her face. "I kept my end of the bargain."

We were playing truth or dare. I had just dared her to walk outside on my balcony which overlooks a busy road in Toronto and strip down to nothing. I couldn't believe she did it.

She now sat there on the couch, completely naked, with her arms folded just barely covering her small tits, legs crossed, just waiting. I had chosen dare and she wanted to up the ante.

"Alright alright!" I unzipped my jeans and pulled out my cock. I was a little turned on by her daring act so I was already sporting a half-chub. Read more »

Finally fucked the guy I was lusting after for months (MF)

This happened a few months back, last September to be exact, but I'm just getting around to writing it now. Better late then never right?

Anyway, I remember how it began so clearly. I was scrolling through my facebook newsfeed one night when I came across a picture of the most beautiful guy I have ever seen. Perfect medium length brown hair, brown eyes, probably around 5'10, muscular, 21yrs old, and Italian. Exactly my type. Myself, I'm 20, 5'5, thin but curvy (32C, size 2, large butt), reddish brown hair, hazel eyes. I creeped on his facebook only to discover that he was in the fraternity my sorority hung out with often. Since I had just recently joined this sorority, this is probably why I hadn't noticed him at events. By the time I saw this facebook picture, it was about to be summer break. So I made a promise to myself that once the fall semester came, I would make every effort to socialize with him and see where it went. Read more »