Category: gonewildstories

2nd Meeting With My Long-Distance FWB, Part 1 [True Story] [MF] [Cheating]

(You can find the story of our first meeting [here](https://www.reddit.com/r/gonewildstories/comments/7snluo/first_meeting_with_my_longdistance_fwb_fm_true/) and [here](https://www.reddit.com/r/gonewildstories/comments/7su3ew/first_meeting_with_my_longdistance_fwb_part_2_fm/) I hope you enjoyed reading them. A little background reminder — Marie and I are both in our 30s, both married, live on opposite sides of the country, but met via tumblr and have since created quite the naughty little fling.)

So after our successful first meeting, we grow even closer, for obvious reasons. We both stop chatting with anyone else that we used to talk or fool around with on tumblr or elsewhere. Our focus is solely on each other, when it comes to our online play. And now we’re just trying to find a way to see each other again. Sure, we were both nervous and feeling guilty, but the attraction and sexual connection was apparent for us both.

So fast forward three months from our first rendezvous… I have to take a minor road trip for work, and we decide she should fly out to meet me. She tells her hubby that she has a “work trip” for the weekend. (Thankfully she works in a field that would have her traveling, and often on weekends, as do I). This time we are going to spend two nights together, and instead of a boring old hotel, I spring for a cabin. You know the type — big mountain cabin with game room, hot tubs, great views, nice kitchen, etc… Read more »

I lost my virginity to a [M]IL[F]…part 2

In case you didn’t catch the [first](https://www.reddit.com/r/gonewildstories/comments/7t5iun/i_lost_my_virginity_to_a_milfwell_at_the_time/?st=jcxa7fmz&sh=f87bfab1) part of my story.

For the sake of using the word “she” to many times in the post we’ll just call her Amanda. Well as I mentioned before Amanda and I hooked up a few more times and she would teach me new techniques, positions and let me try different things. It was great. The more time we spent together the more I could tell she was hiding something though. One time I was fucking her doggy style with one hand pulling her head back by her hair while I slapped her ass with the other. (These were our advanced courses) Anyways, the phone rang and to my surprise she told me to stop so she could answer it. Amanda hung up the phone, said “fuck get dressed, my roommate will be home soon” and we left the house before anyone arrived. The next time we met up, I got in her car and she was wearing a very thin sundress and showed me she wasn’t wearing any underwear. I couldn’t wait to get back to her house, only she said we weren’t going to her house. This was my first experience with sex in public. We pulled off on a private road and as soon as the car was in park she was unzipping my pants, she told me she wanted to feel me get hard in her mouth, which took all of 4 seconds. Amanda moved over and straddled me and began riding my cock while I unbuttoned her dress so I could get to her amazing tits. She came fairly fast and finished me of with a blowjob and we got out of there before anyone could catch us. This would be a little foreshadowing for events to come with her. Read more »

[MF] Saw my boss with a coworker

I work at a grocery store and there’s this girl I work with that has a great fat, curvy ass. I heard she got into trouble with my boss and I’m walking by his office when I see his face buried in her fat ass, eating her pussy. I could tell he blackmailed her because I could tell she was trying not to cum, but he loved her ass in his face and wanted to get her off. I hear him saying “cum for me baby, don’t fight it” and she couldn’t resist anymore and starts shaking her big ass and squirts all over his face. I don’t know what to think

[MF] Halloween Hookup With Longtime Friend.

I had known (for privacy I’ll call her Jamie) since my Junior year of college. We were both political science majors at our very very (can’t stress very enough) conservative school. She made an impression the very minute I had laid eyes on her.

She was a Freshman in one of my intermediate Government courses when I saw and interacted with her first. I knew she was a freshman because she wore it on her face, also was in a class of people that I knew either through interaction or just in passing. She had long blonde hair, the deepest blue eyes I’ve seen, was around 5’2″, and was super skinny not a lot of curves. She looked very shy but still looked like she wanted to talk to someone. I sat next to her for one very obvious reason but the second was I wasn’t very popular among my classmates as I was the only “Liberal” in a very big sea of conservatives. I sat next to her and I introduced my self as a typical college guy, “Sup I’m Jack” (Super smooth). She responded, “Hey I’m Jamie! Nice to meet you”. She was very warm but concise in a way that you knew she wasn’t everything she seemed on the surface. We got to talking about current events and political issues making very clear that I’m most likely not like everyone else in the class. She said to me “I think you’ll probably be my only friend in the class”. She was correct we didn’t exactly gel well with everyone else. That class was where we called ourselves the “Resistance” (before it was cool) and we formed a pretty close friendship. Read more »

Fucking Daddy’s potential business partner [FM]

Ever since I was about 14, Daddy occasionally brought me along with him to business meetings where he was trying to land a client. I never really understood what he did but he said he wanted me to learn about this stuff. I always liked it. He said I brought down the formality of the meetings which let him connect easier with the potential client plus I loved meeting new people. I always had a bubbly, jokey personality. I’m quite good with people and as I got older I started to realise that my personality combined with my (admittedly) good looks and petite body was a very strong pull with clients. From about ages 15 onwards I started to understand my affect on men more and more, in school and in these meetings. Guys would come in disgusted by the idea of working with Daddy and leave happily partnered. Daddy’s always very authorative, convincing and kind, I put most of the deals made down to his business skills but occasionally I see a tingle in the clients eyes that made me realise what he was actually being seduced by. Read more »

[F] My second (and favorite) blowjob

*This is the continuation to [this](https://www.reddit.com/r/gonewildstories/comments/7sk31f/f_the_second_blowjob_i_ever_gave/) post, in which me and my then-boyfriend made out and he fingered me for the first time until I came.* ?

As I roughly pushed Steven down on the bed, I could see the mixture of surprise and heat in his gaze. Having came from his fingers just minutes ago, I felt a sense of boldness and empowerment that I hadn’t before. I felt like there were no more secrets left between us, and I could finally open up and show him sides of myself that not even I had been aware of. It was intoxicating.

“You like being pushed around like that?” I purred, crawling naked up to where he lay. His eyes widened, and out of the corner of my eye, I thought I saw his cock twitch.

“By you?” He said, playing along without missing a beat. “Definitely.” He reached out to touch me, but I slapped his hand away. Pinning him down against the bed like he had done to me earlier, I moved to straddle him. We both let out a moan as our bodies touched and our hips aligned. Read more »

Window of opportunity [MF]

Good things take time.  Great things happen quickly.  Knowing when the latter has become the former is a truly an art form.

This is what I knew about Elena…  She was cute, she lived near me, she had an on again/off again relationship with some guy I didn’t know, and she was cute.  While I have hooked up with women from every stage of relationship from just dumped to just married, not all situations are created equal.  I find that women in relationships often have a lot of baggage, and it is not always worth dealing with.  Frequently it is, but in Elena’s case, I just wasn’t that into her.

Yeah, she was cute, and we always had a flirtatious relationship.  But she wasn’t a head-turner, she wasn’t especially smart, and she often complained about her boyfriend.  Enough for me to roll my eyes whenever she’d bring it up, but not enough to stop me from talking with her when I got the chance.  But when I found out that he was out of the picture, I knew that I had to take the initiative. Read more »

Some kind of Sugar High. [FM]

I decided to keep sharing, after all. <3

——
It’s the day after he takes my virginity. We’re both in bed, I’m slipping in and out of sleep, John keeps me in his arms, holding me as I rest my head on his chest. I feel more than safe.

I wake up again with the sound of rain and the smell of cigarette smoke. He’s fully awake now, sitting on the edge of the bed, wearing only black boxers. I’m completely naked and when he notices I’m awake, lying on my stomach, he puts the cigarette out and leans over me, brushes the hair out of my face and plants a kiss on my cheek, says “Good morning, Sweetheart” and then playfully smacks my ass cheek. I yelp and giggle, curse him out as he chuckles.

I head over to the bathroom to splash some water on my face and brush my teeth. When I come back he hasn’t moved from his spot and is eyeing me like a hawk. I play it cool, but make sure to stretch my arms up so he can get a perfect view, especially of my breasts. Read more »

Drinks and a Show [MF] [Exhibition] [Cheating]

**PART ONE**

Back in high school I knew a girl, let’s call her Ashley. We were maybe 15 at that time, but don’t worry we’re 19 by the time this all happened. We weren’t really friends back then but I knew some people that knew her. She was a nice girl but we didn’t run with the same crowds. Nerdy, but also kind of a goth. At age 16 I left that school for another one and we didn’t talk much except occasional Facebook comments. I still lived in the same town though and a year or so after high school I ended up going with some friends to her apartment for drinks. She was pretty. Quite tall with long hair dyed several different colors. Ears pierced in about 10 different places. Tongue ring. Hourglass figure.

The night drags on and everyone else leaves. I’m a bit drunk so ask to sleep on the couch, which Ashley allows. We’re both drinking and eventually decide to play a card game. We start by playing War and then move to blackjack. I suggest that blackjack is pointless if we aren’t gambling. Ashley asks what we could gamble and I try articles of clothing. She smiles and agrees. Read more »

Cheating with my friends girlfriend [mf]

Several years ago a friend of mine was dating this girl, Courtney, for a few months. Meanwhile I had a long term relationship going on that wasn’t going too well and we started spending more time apart. I first met Courtney the same night my friend did when she approached him/us at a bar. One thing lead to another for him and they started dating then living together. The three of us would still hang out together from time to time, which resulted in my having her phone number because she was more apt to look at while at a bar then my friend was. Read more »