Some new years party fun with a new friend (m)(f)

My wife Anna and I decided to attend a new years eve party with some friends. We have a very open relationship, and there were 2 women attending that I had played with previously. Given the hosts of the party were experienced swingers, we were prepared to hang out or hook up if the opportunity arose. We arrived and the massive top floor condo was already full of 20 people or so. Most of them I knew or at least knew of, so we spent the first little while having a drink and making the rounds getting to know some of those we had never met. I headed into the entertainment room to play some video games with some of the guys (I know, stupid move) and my wife went somewhere with the girls. They get crazy when they drink even if they aren't drunk, so usually i just let her do her thing.

NOT a sex story, a story of what ifs and characteristics of a shitty person (me)…

So to start of with, this is my second gonewild (not really) story. As I said in the title, I know I am a shitty person for even having thoughts like this, but hey I thought I would share it with yall and write something interesting, plus this is a throwaway anyways. So clearly I have no one else really to talk to about this, so you guys can comment whatever you like, or whatever you want to share. So basically I am just gonna let you know who these girls are and what I feel towards them. I have alot of gonewild stories of Taylor, and I will write a couple later, and yes they will involve actual sexual stuff.

Freshman Adventures: Spring Break

Spring Break is, ideally, a gigantic powwow of not-yet-adults baring their bodies and rubbing their skin together as it drips with clear ocean water like they are in a Gatorade commercial (and maybe they are), while muffled hip hop surrounds their souls like an ecstatic Stockholm Syndrome and colors flash in the sunlight that never goes away and beer cascades through the air in slow-motion.

But that isn’t what my spring break was, exactly. By the time my bud Dirk and I arrived at the beach in Miami, large swaths of it were closed off, most people had packed up and left, and it was colder than you’d ever think, all because our college lets out for spring about a week and a half later than everywhere else. By the time we got to the beach, we just stood there, staring. Dirk said; “Let’s go to the hotel.” We did, and we slept.

That time I tried anal (m/f)

Hi everyone! I'm back after a few months of being a total whore. A LOT has happened since my last post, so I thought I would pop back in now and then and share some of the happenings. (:

I'd been sleeping with this guy I met on RAOM (Random Acts of Muff Dive). He posted an ad, I responded, and within a few days of talking he was in my bed and between my legs. The voracity in which he ate my pussy was unparalleled by anyone I'd met before. We began fucking a few nights after that, and it has been some of the most fulfilling sexual experiences I've had. We are strictly platonic, and we are very well aware of each other's situations and there is a true level of mutual trust and respect there.

After playing around for a few weeks, he told me he was going to be out of town for an extended business trip. I thought this was a great opportunity to ask for what I've been wanting: anal. He had fingered my ass before, and had rimmed me, too. But neither of us ever really pushed the issue. I texted him and said "so maybe you could fuck me up the ass before you leave? It might be a nice send off, you cumming up my ass and then heading out ;)" he responded with a resounding "fuck yes" and we began talking about how he would go about shoving his cock up my ass.

[M26]et and old [F21]riend at the pub

A few years ago I (m26) had recently split from a long term gf, we had moved into a flat together and as a result of the split she had moved back to her folks and I was on my own. I had a few weekends out with mates to get over that and had people back to my flat for the ubiquitous recently single parties where I had rediscovered the joys of no strings sex, drink and drugs. I was just about over this and wanting to return to normal and thought I would spend an weekend back at the parents in a nearby town just to catch up and reground myself.

I drove to my old local, I had worked there though uni from 19 to 22 and knew all the regulars and older staff pretty well then and lo and behold, nothing had changed too much, some of the older guys had moved on but mostly same old faces same old stools. I bought a few drinks, they were happy I remembered their orders and good time was had by all. Just as I was heading home I noticed a girl I used to work with, she was a bit of a clichéd “little sister” to me when I worked as she was just 16 and a waitress in the restaurant, I had to defender her honour a few times with the drunks and kicked a few regulars out for the night for getting a bit inappropriate. I used to drive her home after her our shift and made sure she got home safe.

(M)y second time with a (T)rans girl

This is a follow-up to my first story. Still a true story, so I apologize in advance if something is less than sensational. This one is a bit longer though.

I left my friend's birthday party in a fog. I had just had the most amazing sexual experience with a trans girl I had met at the party. It was something so unexpected, both for the fact that it happened and because I had never thought of doing anything like that before. Don't get me wrong…I had no hangups about it. No regrets or anything like that. I was just in this stupor from how awesome it was.

I went home that night and couldn't keep the night from replaying over and over in my head. And yeah, I rubbed one out thinking about it. I was still so hot over the situation.

Before we left the party, I got Claudia's number. I definitely wanted to see her again, but also was trying to play it a little cool by giving it a day or two before calling her. The party was on a Saturday and by Tuesday, I couldn't wait any longer and gave her a call. It was a bit awkward because I was thinking the whole time "hey, you remember Saturday when we banged like there was no tomorrow? Yeah, I want to do that again." To her credit, she was really easy to talk to and seemed eager to meet up again.

My (F)irst time with (M)y ex’s best friend

Background: I am 5'4, nice small breasts and an ass that won’t quit. Blond pixie cut, gray eyes, and dick-sucking lips. He’s about 5'8, 7 inches and thick. Foot long mohawk, hazel eyes, and strong, calloused man hands.

I met him about a year ago, when I was still with my ex. In fact, Alex was his best friend. The three of us would routinely go to punk rock shows and binge out on fast food afterwards. After my ex and I broke up, Alex and I stopped talking.

I moved across town recently, and now I live just one mile away from him. We start talking casually about jamming, then somehow it works into talking about his girlfriend at the time. She keeps cheating on him, sending him pictures of it and telling him all about her sexcapades. Which I mean, would be fine if he were into cucking.

“I need to leave her, Andi. But I want to hurt her, first. Like she’s hurt me.” Here’s my in, I think. “With me?”

———————–

Wife put on quite the show for her blind friend [f] [m]

This blind man, an old friend of my wife’s, he was on his way to spend the night. His wife had died. So he was visiting the dead wife’s relatives in Connecticut. He called my wife from his in-law’s. Arrangements were made. He would come by train, a five-hour trip, and my wife would meet him at the station. She hadn’t seen him since she worked for him one summer in Seattle ten years ago. But she and the blind man had kept in touch. They made tapes and mailed them back and forth. I wasn’t enthusiastic about his visit. He was no one I knew. And his being blind bothered me. My idea of blindness came from the movies. In the movies, the blind moved slowly and never laughed. Sometimes they were led by seeing-eye dogs. A blind man in my house was not something I looked forward to.

[M23/F23] Canadian Cum Crossing

About ten miles from the bridge, Jace turned to me and said "watch this." Well, I watched as much as I could without driving right off the edge of the road. First, she unzipped my pants and pulled my cock out of my pants (that's tl;dr version of a lot of butt-wrigling, groping, unfortunate encounters with zipper tabs, and general chaos, eventually resulting in me looking like a flasher looking for a schoolyard).
Her hot breath on my shaft was all I needed to get hard. I gasped, and grabbed tight to the wheel, as she engulfed me completely and then just rested there with the head of my cock deep inside her throat.
"Uh, you're going to have to sit up and straighten my clothes pretty soon," I told her. "We're getting pretty close to the American border. Jace just made an "mmm hhmmm" sound, pushed her head further down, and started sucking and massaging my cock with her hot throat.
I did my best to maintain lane discipline (that's what my 10th-grade driving instructor called it, although I'm pretty sure "deep throat" wasn't one of the items on his "deadly distractions" powerpoint slides). She repeatedly drew her head up until she was just kissing the tip with her sweet lips and then plunged down until I was at the ultimate deepest depth of her throat. Slowly, with every stroke, she picked up the pace, pistoning me in and out of her throat with determination.
I don't think I lasted five minutes- which was good because we were almost at the point where traffic starts to really slow down when I started cumming. Jace pulled off of my cock and pointed it up at her face (I could only see the back of her head at the time). She jacked me hard and fast. The cum flew. I barely kept my seat, much less directional control of my 2,500lb SUV. She took the entire load on her face, using my still-stiff cock to smear it all around.
I started to panic. "Jace! What the fuck! Clean your face off! We're about to go through the border!" Jace just shook her head, making the little strands of cum dripping off her face swing back and forth alarmingly.
I asked, begged, pleaded, but she just sat there, laughing at me with her obscenely glazed face. And then we were at the border. I frantically zipped/tucked/buckled my way to decency.
The young man who ambled over to my car asked all the standard questions. "Nationality? How long were you in Canada? Are you bringing anything back with you? Any firewood or agricultural products?" I answered politely, handed him our passports and automobile papers. He looked at my passport, then my face. Then Jace's passport. Then Jace's-
Slight Pause…
Passport.
Face.
Longer Pause…
"One moment, Sir… Ma'am…"
He retreated into the nearby door and consulted with another border crossing agent. The other agent came out, looked at Jace's passport. Then Jace's face. His eyebrows furled in thought.
"Welcome Home," he said, handing me back our passports. "You may proceed."
Jace teased me by not wiping up her face until we were all the way to our hotel in Niagra Falls. There, she used her finger to collect as much cum as she could (most of it had dried or dripped off, unfortunately), making me sit in the parking lot and watch her eat it, drop by drop.

One of many stories I accumulated during my time whoring around the Army single soldier barracks.

As a civilian I wasn't introduced to the military party life until i was 19 and a girlfriend of mine dragged me along to help me get over a recent breakup I was going through. I was instantly hooked and spent the next 5 years living the wildest lifestyle you could possibly imagine. This is just one of countless stories I have accumulated.

I was 20 y/o and at the time i guess you could say I had a "boyfriend" but I viewed him more as a guy I could go to if I needed something and no matter what it was I could count on him to give it to me without giving him literally anything in return. So one night his roommate was throwing a huge party in their room but my "boyfriend" had duty that night so he would have to miss it.

Around midnight the party hit its peak and as countless faces poured in and out of the room the supply of alcohol only seemed to increase which of course led to my all to common over consumption. Having a year of partying with single military men under my belt had taught me quite a lot but the most valuable thing I learned was this: single military men have money and are all to willing to give it away. So after some trial and error I found my niche; stripping.