Category: gonewildstories

[FF] [anal] The Best Bet I Ever Lost (part 1) (long)

Ok, so! My weekend. Wow. I’m just now not quite so sore.

First, I’ll post our descriptions again so you don’t have to dig to get a visual:

Me: Hi! 5’0″ (wife says I’m actually closer to 4’10’, but fuck that bitch and her lying tape measure! 5’0″!), 36D-30-40, hair midway down my back, still bright anime red. Gonna prolly go back to blonde when this fades. Brown eyes. 21 years old.

Wife (Jade): 6’0″, 40F-30-44, long jet black hair down almost to her butt, hazel eyes that sometimes just turn brown on me. Dunno why. Haven’t figured out the pattern. It’s freaky. 34 years old.

So, it all started Friday night, before the snow rolled in. We had all our supplies (food, candles, toilet paper, lube, you know, the essentials) and we were snuggled up by the laptop browsing on Adam & Eve for what our next extra $50 was gonna go to.

At some point, for no reason whatsoever, Jade tells me that when I use a vibrator in her ass, she usually orgasms from it.

I’m like “No fucking way. Not possible. It’s a mindgasm, not a real orgasm.” Read more »

[MF] An Unlikely Casual Encounter, at a Conservative University

*A few years ago, I was a Junior at a very religiously conservative university; the kind of school where housing forbids the opposite sex from being in your bedroom. Sadly, I didn’t have that “traditional” university experience that so many have, and my mildly introverted personality certainly didn’t help matters, but there was this one girl, and I’m going to tell you about the night we met. There is no penetrative sex in this chapter and it takes a while to develop, so if that’s not your thing I warned you, but it was the most unexpected sexual encounter that happened to me during my 4 years at university.*
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It was December. I was out of town staying with relatives for winter break. A classmate of mine sent me a text asking if I wanted to meet up with her to watch the basketball games on campus. I was two hours away, but she was cute, we had a good team, and I had nothing going on – so why not? I got in my car and headed up to my apartment on campus. Two hours later, I was just entering town and she texted me, “I’m really sick. I can’t make it. Sorry.” Read more »

[Funny] [MF] “I don’t kiss during sex but can you give me head?”

I wanted to share my story about the weirdest encounter that I have experienced in my sex life. After recently becoming single, I have been dating on the online app Bumble for about 4 months. I started messaging this guy through the app and we planned to meet up in person. He wasn’t super talkative over the app but I figured he would be more social in person. On our first date, we didn’t have much in common and he wasn’t attempting to engage in conversation that much. Somehow he assumed this was a good thing, as he texted me after the date to ask if we could go out again. I listened to the advice of my friends that told me that this guy could have been shy during the first date and that I should give him another chance. On the second date, this guy was still uninteresting and not talkative at all. I wish that the date ended after dinner but sadly it did not. At this time, I didn’t have sex for three months (it was a dry season…) and I invited this guy back to my apartment. I figured that if this guy was boring, that perhaps he could be a good lay?
This is where shit hits the fan. I go into the bathroom and prep myself for seduction mode (brushing teeth, checking makeup, etc). I come out of the bathroom and sit beside the guy on my bed. As I lean in for a kiss, this guy pulls away. I’m super confused at this point and ask him whats wrong. This guy says (actual quote) “I don’t kiss during sex but can you give me head?” Read more »

Threesome weekend [MFM]

A few months ago I shared a story of a failed threesome with my buddy and his GF on this sub. I received a lot of negative feedback due to the fact I had a SO at the time and was cheating. I have since parted ways from the girlfriend and after several months the opportunity for another threesome arose. This is that tale. Names changed of course.

This past weekend found me crashing Saturday night at Mike’s house so we could get an early start on our first skiing trip of the year. I arrived about 9pm with two six packs and the intention of kicking it and drinking some beers. Mike and I cracked the first brews and sat in the kitchen catching up on the usual business, when Molly appeared naked in the doorway. Molly is about 5′ 3″ 115lbs with tiny tits and a firm round ass, a very athletic build.

We spent about 90 minutes just chilling at the kitchen table polishing off the 6pk and talking about everything from the mundane to the more risqué. I had a gentle buzz going from a couple high ABV craft beers when I excused myself for a cigarette. I returned quickly from the Arctic blast that was outside and found the kitchen deserted. The fun part of this story starts right about here. Read more »

[Group] A very special New Years Eve Party – Part 1

At the end of my last post I promised to tell you more tales from my time in the Med if that’s what you wanted. Thanks for the great comments and I promise I will but first I HAVE to tell you about what happened this weekend. It was amazing! (Well I think so at least)

This story is pretty long so I have split it into two parts. I know some people find the backstory/scene setting boring and just want the juicy stuff but to me the backstory is an important part and helps with the build up to the exciting stuff.

One of my wife’s best friends from school lives just two roads away from us with her husband and baby. We see them at least once a week, pre kids we spent much of our twenties hitting the bars, pubs and restaurants of London. These days we normally end up round one of each other’s houses drinking and talking with the kids asleep upstairs, every so often we get a babysitter and head out for the night. Often when we are a few drinks in there is a bit of joking/banter about how everyone must think we are swingers! Read more »

It started in the guard tower [MM]

So this is a continuation of my story of [giving a blowjob in a guard tower](https://www.reddit.com/r/gonewildstories/comments/5l27oa/guard_tower_blow_job_mm/).

So, it’s about time that I mention that the medics name was Jake. He was a common soldier (not fat, not buff, but definitely active) and he was some kind of Hispanic that only spoke English.

I had previously told Jake that he “owed me” and I had no idea what that meant. Like, did he owe me a blowjob? Or something else? I just said it, I didn’t really think about it. But the next night, he and I met in the Motorpool where we believed no one else would be.

It was dark, and we couldn’t see shit. We found a little corner behind a stack of tires where we could hide, with barely enough space for two men wearing combat gear. We very quietly removed our body armor and leaned our rifles against the wall of tires.

On his knees, removing his clothes, Jake started sucking on my dick. I was rock fucking hard, and I thrust into his face as he pulled my pants down around my ankles. Read more »

[MM] My second Grindr experience!

I had been waiting to meet my second hookup for ages. We had been chatting since before New Year’s, but it was right after my [first hook up] (https://www.reddit.com/r/gaystoriesgonewild/comments/5kok12/tired_grindr_for_the_first_time_sucked_a/), and I wasn’t sure I was up to sucking dick again so soon. Finally, we found a time when we were both free, and I headed over to his place. He was pretty attractive, a twenty-seven-year-old black guy with tightly braided hair and a cute smile. He was slim but in great shape, well defined abs and pecs clearly visible in the photos he sent, along with a gorgeous curved ass. His cut dick was large, bigger than the ones I had encountered before, most of which were the same size as mine (just shy of six inches) or smaller. His looked to be about seven inches or so. That actually made me slightly apprehensive – a lot of the pleasure I get from these encounters is giving pleasure to the other guy, and I was worried that if I couldn’t do well with a larger cock than I was used to, he might not get off. Read more »

Beach Day With Friends [Group]

This is a story from this past summer which I finally sat down to tell. I’ll introduce the my friends in the couples we were that day. I’ll note first that we are all reasonably in shape as we like running around outside doing stuff rather than day drinking as some other groups of friends tend to do. Jacob and Stacy are the first couple and while Jacob is around 6’1” Stacy is about 5’4” on a good day. Both are brown haired and brown eyed. Jacob is bit tan since he is a mutt while Stacy I would say is on the fairer side of the spectrum. Next there is Tom and Sarah, Sarah is a dirty blonde, 5’1” and pale skin with green eyes. Tom is brown haired, 6’2”, and also pretty white. Next is Natalie and Me, I’m the tallest at around 6’3”, brown hair (you guessed it), brown eyes, and my skin burns rather than tans haha. Natalie is the tallest girl of the group at 5’7”, and she is an Israeli Jew for her heritage. I think she is stunning if I say so myself. Last is single Andrew, at precisely 5’7” and no defining features he gets a lot of flack from women. He was single at the time this happened, but it was never from lack of trying. Very gregarious with no Napoleon complex at all. Read more »

[FM]Dan, FWB that liked his ass fucked.

Many moons ago I was a young military officers deployed to Iraq. I was attached to a support unit on a base shared by my service and the Marines. On the plane trip to the base I met an admin officer. He was a handsome man. In shape, tall, dark, and very handsome.

We hit it off very well, once we arrived on station we learned that our quarters were very close to each other, about 10 yards apart. It wasn’t long before romance flourished. It started innocent enough. With us relaxing watching TV shows and eating together.

We were nervous about doing much more because we were both officers and that is something that is highly looked down on. So we would spend time together every evening and when we headed to our quarters we would both masturbate as we chatted on our personal lap tops with each other. I never told him, but I had been craving his cock, which I hadn’t seen or touched so much that every night I masturbated over and over again until I passed out from exhaustion. Read more »

[MM] Getting Blown by a Guy For the [first time]

She had been gone for three days – a conference in Vegas. We’d been dating three months or so – not exclusive. I knew she had another FWB on the side. We’d been having sex pretty regularly, usually at her place, sometimes mine if we were in the right part of town. She was pretty, long blonde hair, good smile, the perfect person to occupy my time – and if it looked like it, maybe get into a long-term relationship with. But after her being gone three days and me working, all I could think of sitting at home was my erection.

Sitting in front of the computer, I briefly debated masturbating. I had a nice routine down and after three days, the load would be very satisfying. Browsing over to Random Acts of Blowjob, I saw a few ads for guys seeking other guys. I’d never been directly attracted to guys, but the thought of a blowjob, especially from someone that knew his way around a cock, was enticing. A glass or two of red wine fueling it, I sent a message to the guy. Ten minutes later, I saw an orange envelope. The guy was interested (I provided my location), and wanted to swap Kiks. I sent him mine and got a response soon thereafter. We chatted about experience…he was bi, and had mostly been with girls, but also liked to suck every once in a while. We moved on to pictures. Read more »