Category: gonewildstories

Finally [F]ucking [M]y High School Crush, Part 2

Wow. I want to thank everyone who enjoyed [Part 1](https://old.reddit.com/r/gonewildstories/comments/ekjpu1/finally_fucking_my_high_school_crush/), and for liking my writing, my story, messaging me about your experiences with your own high school crush (shoutout to you all!) and letting me know I should write this next chapter. Unfortunately, part 2 doesn’t end well, but hey, that’s life. All I ask is that you try and remain respectful (but this is Reddit, so that won’t happen). If you’re only interested in the sex feel free to skip to **THE SEX STARTS HERE** , for everyone else, this is for you.

I got home Saturday night and was glowing in my post sex high. I couldn’t believe what I had actually done. The sex was incredible, and I felt like I had climbed a mountain and was admiring the proverbial view from the top. We set a time for next Saturday, as we were both busy with work and school, and we figured we would start again where we left off, this time with the Titans-Ravens game. Neither one of us are Titans or Ravens fans, and we had discussed beforehand that we wouldn’t be upset missing part of the of game to focus on something “more interesting”. As planned, just before the game I showed up at Ally’s with a pizza and “prepared to watch the game”. Her roommate was out of town so it would be just us, meaning we could finally really explore each other’s bodies. Read more »

My girlfriend told me to date my old female coworker [FMF][Threesome] part 3

Coming back from winter break, we didn’t know what to expect. Before us all leaving we started hanging out together, and now after nearly a month apart from Iris, many questions started creeping back into everyone’s head.

The first night back with Iris in nearly a month and neither of us exactly knew what to expect. We had a rough month apart, we rarely got along during that time. We had so much to digest and work through that at the end of the first night of us being together, I was almost certain our undefined relationship was over.
We didn’t see each other for a few days after that first night.

On a Tuesday night, Kate and I decided to invite Iris over and watch a movie with us. Iris and I were alone at the start, but we had some tension. In that hour that we were alone, Iris had already put her mouth around my cock. She was just getting a taste of what she had missed at that time we were apart.
Kate joined us a bit later and we started up the movie. We were all laying on the bed. Kate on one side, and Iris on the other. Kate was encouraging me that night to touch Iris more than usual, to go for more too. Read more »

[MF] That one night with Leigh

When I first got out of college I worked at company of young, fun, partying kids. Most of us were right out of school and in our first jobs. I had an on-going FWB with someone at the company at the time, and she was amazing (I’ve written about her here before) but I had always had a crush on Leigh.

Leigh was stunning. Beautiful face, perfect body, incredible huge tits and shapely ass, 6 foot tall, blonde, right out of Ole Miss, and so out of my league. She had an older boyfriend who clearly had money as she lived a much nicer lifestyle than we were getting paid. But she was really cool, really fun, and I had an instant crush on her moments after I met her.

The whole team did happy hours and late night clubs quite often. When Leigh wasn’t with her boyfriend she was with us. It was always a group, we always were partying, and the hook-ups were legendary. Often if we had SOs they would join and Leigh’s BF often did. Read more »

I [f] let [m]y childhood bf play with my pussy with a vibrator, while his friend waits in the living room

So I have a bf but we aren’t speaking right now.
My childhood boo whom I haven’t seen in year is in town. He came over my place with his friend to hang out but you could tell there was a lot of sexual tension between us. We had previously made out the week before.

So we’re in my living room watching tv and he starts kissing on my neck, and playing my my nipples . I was getting aroused but I didn’t want to fuck him.

I took him to my room to show him a vibrator that I had just bought, he asked if he could play with my pussy with it. I said no but he could watch as I play with myself.

I took off my shorts (I wasn’t wearing panties) and started playing with my pussy with the vibrator, he had this intense look in his eyes and was watching me.
He moved closer and started kissing me, it was so hot. So I passed him the vibrator, he starts teasing me with it and playing with his cock with the other hand.
I’ve always wanted to do that so I was so turned on, he came up and kissed me while continue to okay with my pussy. I was ready to cum so I took the vibratory from him and started playing with my self. I know where my spot is so I was ready, he played with his dick as I squirted all over my bed. Read more »

The first time I screwed the innocent girl from work [FM]

I was going through a rough patch with my girlfriend a few years ago, we just weren’t clicking, and so decided to take a break (complicated by the fact that we still lived together). I was confused and upset, and really didn’t know how to deal with my emotions or the situation in general. I was finding it hard to concentrate at work, missing deadlines and generally underperforming, but thankfully Krys, someone slightly more junior than me, was picking up the slack.

Krys and I had gradually got closer since she joined six months previously; I had coached her through a bad breakup with an emotionally abusive guy at the time, and as she was my assigned project analyst, we worked together and sat together every day. Not my usual type, Krys was tiny – 5ft 1, 100lbs (45kg), and was almost too skinny. She had a-cup breasts, but a juicy butt considering how skinny she was. My favourite things about Krys though were her round dark brown eyes, her button nose, and some naturally slightly plump lips. The sort of face you could stare at for hours. Basically, really cute, if not slightly skinnier than I would normally go for. Krys loved animals, and whilst being shy, she genuinely cared about everyone. One of those people who is just a really amazing person. Read more »

My first anal [MM]

I never thought of myself as gay, even now after having sex with a man, I still don’t check out other men on the street, BUT, in the last couple of years I’ve become obsessed with trying gay sex. I wanted to be fucked. I wanted to give blowjob. All of it. It’s come to a point when I don’t even masturbate without a toy in my ass while imagining a dick in my mouth. So I guess I’m bi, since I still love boobs and pussy.
But I live in a small town, trying it was impossible. So when I was told I’ll go on a three day business trip in my country’s capital, I knew I can’t pass that opportunity, I immediately started browsing the classifieds.

First day there, after work in my hotel room, I chose an add, a student, just the body shot, normal, average looking guy, called him and we set up a meeting for tomorrow evening. I was super nervous the whole day! Almost called it off, but then I remembered how long I’m fantasizing about it and said, fuck it, I’m going through with it. What happens, happens! Read more »

[MF] I tried to have an honest date not end in sex, but alas, anal

When my FWB list had dried, hookups were not available, and I was getting slightly tired of the entire game I tried to have an honest date. I reworked my dating sites to find long term relationships and wanted to give a go at honest dating. I’m serious, I sought out what seemed like dating material.

I messaged her and she messaged back and we flirted and had a good rapport. She was short, chunky MILFy body and was a super devout Christian with a whole bunch of ways to say that she wasn’t seeking sex. Now I know when one protests too much it’s to hide their true intentions. But for this instance, I was naive. We didn’t even share any sexy pictures, just clothed ones. Her neighbors were having some sort of garage party and she invited me over. Read more »

[MF] The pregnant FWB

The best friend with benefits fills a Reuleaux triangle of friendship, hotness, and availability. When you find all 3 or what you would go without is the best case for anyone. When I was alone and on the prowl I wanted to find a dependable girl that would come over when we felt the urge to release and didn’t get super attached.

Whisper put us only a quarter mile away, she lived in a house just right down the road. We started immediately exchanging dirty pics and sexy talk. She was a white girl, bbw with DDs , thick thighs, a fat ass and wide birthing hips. The body made to just get pregnant over and over again. When I had her over for the first night I had her pinned to my wall and ravaging her body with my hands tearing at her clothes to get her naked. Her skin was so pale and soft, her tits big and plump ass just begging to be grabbed. She loved being handsy and was at least forward with our agreement that we weren’t exclusive and she had a goal: someone was going to get her pregnant. Luckily I had condoms and put one of those life savers on and went to town. She had this cute moan and would barely get words out as we had sex and finished. We laid in bed after that first time and just bonded a little, the friend portion of our little arrangement. She did have to go back to her house, as her parents were still watching her first kid and didn’t want to make it seem like a dick appointment was more concerning than being a mom. Read more »

Generous roommate (24F) shared her boyfriend [FM]

It was my first time staying with a roomate. I did not have much money back in the day as I was studying full-time without any grant and worked part-time as I refused to go too much into debt. My previous landlord wanted to increase the rent too much and, as a result, I moved.

To be completely truthful, in addition to the place being dirt cheap (partly due to having a roomate, partly due to the low price she asked – a third of what I was paying before), I got along with the person well. She was someone I had met a year prior in one of my class and she was very similar to me, personality-wise. Simply said, she was a total slut like me, except she was a in long-term relationship.

When I learned her previous roomate was moving and she was looking for a new one, I didn’t hesitate. I would save money, be closer to school and hey, having a roomate seemed like a cool experience. Read more »

Finally acting on [m]y yoga [f]etish

They say yoga makes people feel calm and relaxed, but for me it does the opposite – no matter how hard i fight it, it turns me on. There’s something about feeling every part of your body bend and stretch, in control of every taut muscle, luxuriating in a body I ignore most of the rest of the day at my desk job. At the end of every session I lay down on the mat on my back and the strangest thing happens. It’s like all the sensations built up over the hour gather down by belly and tingle in my pussy until I’m hot and starting to get wet. It takes a lot of mental energy not to squeeze my thighs together and snake my hand down into my tight yoga pants – especially in yoga classes, when a man with yoga-toned arms and a sweat-slick body is usually laying close enough to reach out and touch. Read more »