12:34 am: “Are you still awake? Come take me out for a drink!” [m/f]

Friday nights were never my strong suit, honestly. I was always tired from the work week and never could bring myself to hit the town hard. This particular Friday night wasn’t much different – I had a beer with a coworker and then went home. I was in the process of brushing my teeth and getting ready for bed when my phone buzzed.

Alaina was texting me. This in itself was not unusual, we had been close friends for a while at this point. I had been harboring a crush on her for most of that time, as well.

Me, and pretty much every other guy who ever met her. She was 22, tall with a toned, athletic body from years of playing every sport under the sun; her breasts were tiny, small enough that she frequently wouldn’t even wear a bra in public (although I like them like that) but she brought some glorious curves through her hips. She had flowing golden hair that framed her infectious smile and a personality like sunshine. Bubbly and vivacious, she would hug strangers hello and dance the night away with anyone and everyone.

A memorable weekend of exploration. My second time. Her first. [M/F]

My second ever sexual experience. I didn’t really know what I was doing at the time, but it ended up being a very memorable weekend of exploration.

This happened some time ago. I was a shy hyperactive guy in University and “Riya” (not her real name) was a cute nerdy girl on a student visa from India. Somehow, my awkward self managed to attract her and we had been dating for a few weeks. We were a very mismatched couple. I’m lanky and thin, but I’m still quite big as I’m about 195 cm tall (6 feet 4 inches and a bit). Riya was anything but big. She was barely 150 cm (just about 5 feet) with her hair done up. She was tiny compared to me. Riya was also a virgin and I might as well have been.

At this point I had only had sex once, about a year prior, so I could barely keep my hands off of my new girlfriend. Although, for the first few weeks we were together she was very coy and didn’t seem to want to go beyond light petting and kissing. Anyway, we couldn’t really find any alone time (as we both had room-mates).

Sharing a Monster Cock with my Friend [FFM]

Early into my junior year of college, I was watching Dirty Dancing and drinking box wine with my friend, “Nicole”. Nicole had just broken up with the guy she had “dated” since high school and needed some consoling. I say “dating” in quotes because she had basically been serially cheating on him for at least two years. Her ex was really straight edge: no drinking, no drugs, judge others about it, and not even religious. Nicole was not, so she would just get drunk on weekends and hook up with various guys.

 

Her “boyfriend” finally got wise and broke up with her, and Nicole took it hard, ergo the night of Swayze and Fran. Despite cheating on her ex **A LOT**, she wanted to get back at him. Now Nicole was short, maybe 5’2” but hourglass curvy, pale with big green eyes, and a huge mane of fiery red hair. Think Lindsay Lohan before cocaine, but with bigger hair and bigger boobs. She didn’t need to try to be able to hook up with whomever she wanted. *I just want to send him a pic of me fucking a giant dick* she says to me at some point.

First time sucking cock (m/mm)

I’m a 26 year old male and was 22 at the time when it happened. First post but thought of this story and figured you guys might like it.

Ive always been straight but with a little bi curiousness in me. I loved watching straight porn but always could appreciate a good hard cock.

One day I’m watching a girl sucking a cock and moaning and I just thought okay “I WANT THIS!”

I went to my local craigslist and put up an ad amd,someone messages me. He’s an older guy but was extremely nice and his cock was the perfect 10/10. He said let’s meet at the local theatre. I work there and we can be alone.

I’m on my way nervous and hard as hell. My erection wouldn’t go away but I was so nervous.

As I’m pulling in I park a bit away and check my phone. I’ve got a text saying “wait my friend,just showed up and won’t leave”

I start to worry what if he doesn’t leave or he catches me (not that it would have mattered but in my heightened staight it felt like the police might as well have been there)

Fucking my girlfriend on top of a mountain [M21/F21]

I’m going to give a bit of context, so if you want to skip that and get down to the juicy stuff, look for the row of asterisks (********).

I’ve been together with my girlfriend Rebecca for about five and a half years now, we got together about halfway through our final year at high school and immediately formed a connection so strong that we decided it was worth the risk to go to the same university and move in together once we graduated. Neither of us had been in a particularly serious relationship before; I had had three previous girlfriends, none of whom lasted more than a couple of months, whereas she had one that went nearly a year, but at any rate, we were both virgins when we got together (second base was as far as I had ever gotten, third for her). That didn’t last long.

FFM – sex, drugs, and my first threesome

A few years ago I was dating a very lovely young lady, for the sake of this story we will call her Carolyn. Carolyn was my ex-girlfriend’s best friend, and we had been good friends throughout my relationship with my ex, but when that relationship ended Carolyn swooped in and claimed me for her own. I wasn’t complaining, Carolyn was 5’2″, 95lbs with 28H breasts and the tightest, tiniest pussy I’ve ever experienced. She was a goddess, and little did I know she was a freak too.

Once during my relationship with my ex, she told me about a time her and Carolyn got drunk together in the hot tub and Carolyn started asking weird questions like “don’t you think girl’s bodies are so sexy?” and “have you ever considered being with a girl?.” After some more of these questions, my ex was getting a little nervous and then suddenly she felt a hand on her inner thigh. She didn’t know what to do, so she started talking about something trivial. As she talked, the hand moved up her thigh and under her swimsuit and began rubbing her clit. My ex freaked out, got up, and left, and her and Carolyn never spoke of it again.

[M/F] Cheating Wife from Craigslist in Austin, Texas

I’m not particularly proud of this story, but it was hot and so much fun. I have one of those problems that most of the readers in this subreddit do. High libido, but to the point where you can’t think straight unless you get some kind of sexual release.

 

I had been super into facial abuse videos and was looking for a willing partner. So, naturally, I posted an ad on Craigslist to try to find a woman willing to let me destroy her throat and make her mascara runny. Yeah it’s impossible. Anyway, after posting my ad, I noticed a post from a girl that was 26 years old that was into kinky rough fun. 99% of ads on Craigslist are fake. If you’re there long enough (read 10 minutes), you know how to spot them. Her’s was legit, and I messaged her telling her about my own facial abuse ad. She read my kink list and said “YES Please”.

 

I hit a girl, I liked it [FFM] [amateur BDSM]

If you are anything like me and sometimes like to skip straight to the part about the sex, I’ve marked where it starts **in bold**.

Hello again, dear reader. I thought you might like to know that as I write this story, I have a blue dimente princess plug deep in my ass, with [these panties](http://kisskill.com.au/products/addict-knicker).

This is a story about my grad school colleague and longtime rival [Grace](https://www.reddit.com/r/gonewildstories/comments/50x05k/fucked_my_grad_school_colleague_and_long_time/). For those who haven’t read my previous posts, I’m brunette, 5’10”, wear a UK size 8, have a big, round, high ass and average sized, perky tits with pierced nipples. James is blonde, 6’3, thin and muscular, heavily tattooed and has a top knot and a beard. Grace is blonde, skinny, around 5’7”, has short hair with an undercut and facial piercings.

James suggested to Grace that she come over and see us last Sunday afternoon. She arrived wearing a baggy black muscle tee, high-waisted black skinny jeans and doc martens. We acted like friends and not lovers, hugging briefly, kissing on the cheek. I wondered whether the other night was a one off, whether she just wanted to be friends.