gonewildstories Archives — Page 4246 of 5640 — NSFW story

Train Trip, Part 1: One Day in Chicago with a HotOrNot Slut [MF]

So this is going to end up a trilogy. When it took place, it was the summer after I’d just turned 21. I was still living in the tiny rural midwestern town I’d grown up in, and was working at an office with about six employees. I had two weeks of paid vacation that had to be taken separately, because they couldn’t afford to let anybody go for two weeks at a time. Sucked.

Either way, I was still hooking up with my high school sweetheart, a year older, from time to time, and occasionally meeting a slim blond from the Chicago suburbs I’d found on HotOrNot, a year younger, who was happy to drive to meet me and split the cost of seedy motel so we could both be away from our parents and she could get treated the way she needed. It was weirdly romantic, fucking her like I hated her made her feel loved and she was addicted to it, and we’d both been enjoying trying some things out on each other for a couple years now. Read more »

Hallway Debauchery and the Backyard Bonfire [MF]

So, here it goes. My first post. This is a story about my first, and most unforgettable MILF. She’s a legend in my book. I actually plan on releasing a bunch of stories out of all the insane adventures we’ve had, however, this one will have to do for now.

The Introduction (She needs one.)

We’ll call her Q. I, who was 21 at the time of this story, met her while intoxicated at a friend’s birthday get together. Bombay and Pineapple was the drink of choice that night. That’s where the “time traveling” began. A few friends come over and one of our close friends, from elementary school, brings her older, married, sister Q. This woman, about 26 at the time, was stunning. about 5’2”, silky brown curly hair, piercing blue eyes, petite-thick, beautiful size D breasts, and a deviant smirk to top it. From the moment she walked in, my sights set on her and nothing could break it. I flirted with her endlessly and she was just having a giggle at me how much I was working to make her smile. Unfortunately, the Bombay would soon overpower me. I ended up in the bathroom puking and asking for breadsticks repeatedly. When the time travel began to slow down and I caught my footing, she was gone. The next day, I called her sister, told her how much I could not stop thinking about her sister. Asked if she can pass along my number. Her sister calls me within the hour and the rest is history (which we will come back to eventually). Read more »

[MF] Rolling Around with my MILF

Not breaking up my stories…not creating parts 1, 2, etc. Just relating true life experiences with my spectacular MILF. I appreciate all the feedback and love (and the negative shit, thanks for the laugh), feel free to DM me anytime as well.

To recap, her (Molly)…5’6″, 110 lbs, size zero, small perky tits with amazing eraser sized nipples, waxed and smooth as silk, amazing legs and totally rocking ass; me…6’5″ salt and pepper hair, athletic and fit but not ripped, shaved smooth, above average (8″) and thick. I’m a pretty sexual guy (meaning I love rolling around naked with a woman but, I’m also very frustrated as it’s been 2+ yrs without anything in my home life, thus I’m open to new encounters). To pick up my story…

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Molly just smiled at me and as she walked away, her sexy ass swinging back and forth, she said, “Come on baby, let’s go fuck!” Read more »

[FF] getting half naked w my married bi date

The girl I had a date with, let’s call her Leah, and I start texting now and again, the occasional flirty text or innuendo.

We decided the other night to have our second date!
I was nervous but looking forward to it since I hoped our second kiss would be better since we wouldn’t be so shy. And to see if this relationship(?) had legs.

Um..we ended up w our tops off in her car in the theatre parking lot, alternating between making out hard, sucking and playing with each other tits (hers were bigger than mine and amazing) and making each other moan.

But back to the PG stuff.
We sat on a bench in the lobby, and I was taken aback by her prettiness. She had done her makeup and hair, picked a shirt that showed off her cleavage..she almost looked like a different person from our first date. Once the movie credits rolled, I asked her if she wanted to try that kiss again and she smiled and said yeah.
It was so much better. She knew what she was doing, her mouth tasted nice, and her tongue technique was exactly how I like it. Read more »

How my girlfriend made me a dominant [MF]

I have been lurking for a long time on this sub and I think it’s time to tell you a few stories of my own. To start with this is not a one-time tale of the best sex of my life, though I would like to write that too someday. So if you are looking to jerk off to a sex story this might not be a good choice.

At the time of this event, I lived in a small town in northern India and was working with an MNC as a consultant. I have grown up in a relatively small town in India and terms like domination, submission and bonding were never in my dictionary. Until I met this girl we’d call RT. RT was from Delhi and had taken a year off after her graduation to volunteer for a local NGO in the same town I was working at. This was in late 2015. We met socially at an event organized by my friend at his small-time café cum restaurant. She was a little on the chubbier side and had a very cute and innocent look on her face. Read more »

[MMF] Our trip to the sex club

After my previous post I realized I should post this one as well though it might be a bit more tame.

My wife and I were on our vacation which already had an escapade but was doing wonders for our marriage in our sexual reconnection. Two days after the beach incident we were looking for something to do for the night and were not interested in going to a dance club on a Friday night. We had seen the sex club/hotel when booking so we joked about going. This time she was actually interested. Even better it was just a block away so we figured at worst we could get drunk and dance without driving, they advertised a dance party, open pool and fetish night.

We arrived to the friendliest people though it was not as busy as we guessed it would be. While there was a lot of people who kept to themselves there was also a lot of friendly people who noticed we were just vacationers. We chatted and watched, keeping tabs on the creepy single men and laughing at some of the outfits. An older woman became our guide and laid out the rules and showed us around while explaining their reason for coming. Read more »

[FFM] When I was twenty two, I spent about a year as a financially compensated sex slave to a couple over twice my age.

Suffice it to say, that this isn’t about that whole year, just the first night I met them. This happened over a decade ago, but I recently found my notebook from that time and after rereading it, I decided that I feel I could rewrite it well enough to share. I kinda have to share it, because it was one of the craziest and simply most out-of-the-ordinary things I did in my twenties.

Lets just start off by saying that I was and still am an unabashed slut, though I’ve slowed down considerably since that time. As a college dropout, sleeping on friends couches or in one of my numerous fuck buddies’ beds, parties and hookups were basically my whole life at that time. I’m not ashamed of it because I was always going to be a fuckup as far as society was concerned, so I’ve always lived exactly the way I wanted to live. This whole thing started when I met a woman in a bar. She offered to buy me a drink to, and I quote, “Wash the taste out.” You see, I had just returned to the bar after leaving for five minutes to blow some random stranger in the backseat of his car because he was good looking and had bought me a couple drinks. Read more »

[MF] [cheating] Continuing to fuck my coworker on the job

*NOTE: This an ongoing story, please read my previous posts for the the whole story.

After that first time with Hayley there was hardly a work day where we weren’t fooling around in some capacity. We fucked in a few janitor closets, in our work truck several times, and even once on our bosses desk one late night we were alone. The fact we were both cheating on our significant others became our biggest turn on. Well she’d be sucking my dick at a library she would ask how much better she was than my wife or when I’d bending her ass over a desk at some office building and asking if her boyfriend fucked her this good.

The ultimate turn on came when my wife had me invite Hayley and her boyfriend over one night. I grilled up some steaks, we had a few drinks, and played some board games. Hayley and I were on our best behavior and kept the flirting and glances to a minimum. There was one moment we gave in a minute when the four of us were hitting a bong on the balcony and her boyfriend and my wife both went inside, as soon as it was clear I pulled her in and kissed her while squeezing her ass. She sighed into my ear and whispered, “Make an excuse to go outside tonight around 1:00, I’ll be waiting in the parking lot.” Before I could respond we heard my wife on her way back and separated. Read more »

[MF] “So, what do you think?” “About…..” “Fooling around.”

This happened to me about a month after turning 21. I worked weekends at a meat market while I was in college, it was a lot of fun! I learned a lot about grilling, cooking, and selecting a good piece of meat! My boss was awesome! He was very laid back, and was super funny and made the atmosphere there very lively! I started working there when I was still in high school, and he set me up with 2 of his nieces (at different times, unfortunately lol) neither of these worked out, but they were great girls, and dated one for a short period of time. My boss and I became really good friends, and as it approached me turning 21 he kept saying how he was excited to finally be able to take me to a bar. He was in his mid 30s at this time. About a month after birthday finally rolled around he asked me if I wanted to go over to the small town he lived in and go to a bar one of his family members owned. I of course did, (it was a fun little hole in the wall.) We did the normal birthday shots and then had a drink or 2 before they were going to close down. I was bummed because it was so early. What I didn’t know was they close early on that night because there is another little nar across the street that has $1 beer on that night. So, everyone that was at the first bar just walked across the street. We had been at the bar maybe 10 min. And I noticed that I was probably the youngest person there by far. My boss was probably even one of the younger ones. My boss knew a lot of the people (very small town) and was making all talk and introducing me. He told the bartender (a very rough looking and acting lady in her 50s if I had to guess.) That it was my birthday recently so, then she checked id and made a few comments about how young I was, all in good fun, and the other people around the bar had fun with it. After we got a very boss and I went across the bar to play pool. That’s when I noticed a lady that looked to be in her 40s but had a sexiness about here that I couldn’t put my finger on. As we were playing our first game of pool I noticed the bar tender was walking toward me with a beer.”Its from the blonde up at the bar.” “That’s so nice, tell her”….and before I can finish my sentence the lady from the bar is standing hip to hip with me looking up and back at me and says “so, what do you think?” I respond with “about?” “Fooling around” she says. Trying to be on my best behavior I tell her “well, I think I have a girlfriend that wouldn’t like that much.” She immediately responds with “well, I have a husband, have fun with me.” Somehow in my stupid 21 year old brain I accepted that as a good point and said, “okay, where are you thinking?” She tells me to “meet me out back by my van” and describes it to me. I was not waiting long before she came out the door and started kissing me and rubbing the now growing bulge forming in my pants. This goes on for a few min. Before she opens the back door to her van so we can get in the back. Now, we had to get in the very back because the middle row had 2 car seats in it. This made pretty uncomfortable because I started thinking about how wrong this was, and decided I needed to just go back inside. When I told her this, she gave me this look, like, seriously? And just said to let “you’re not going anywhere.” As she locked the doors to the van. She then took my shirt off and started kissing her way down my body. She stopped at my belt and just looked at me and winked and she undid my belt while never breaking eye contact. She teased me so much, just lightly licking up my shaft periodically, and used her fingernail to ever so lightly trace her way up the under side and twisted right before the head of my now throbbing cock with her hand like she was trying to twist off a lid using all 5 fingertips. And then slowly moved her fingers down until her palm was hit she couldn’t go any further down and she did a few other things just to tease and then asked if I wanted to taste her. I took her shirt and bra off, and was very pleasantly surprised. She had great boobs! They were a full C cup with nipples that were just the perfect thickness that made me want to nibble on them. I slowly worked my way down her very impressive body, and put my hand palm first to feel her soaking puffy. I rubbed in slow small circles with my palm for a second. I then slid in my middle finger followed by my right finger and slowly start to massage her g-spot while I explore every part of her tight little pussy with my tongue. As she was getting more and more into it I wrapped lips around her clit and moved my tongue in a way that she said felt like a vibrator. At this time I’m also starting to go faster with hand too, using the 2 fingers. She starts reacting in a way I had never seen. Her legs were shaking, and her eyes were rolling and then it happened…..she squirted all over my face! I had no idea what had happened, but it turned me on so much! I put on the condom and slid into her pussy, it was like it was sucking me in and felt amazing! She started to pull hard on the back of my neck with both hands and looked in my eyes and demanded that I fuck her hard.. I started to go harder and faster than I ever had before and could start to feel my orgasm building. She started yelling out “I’m gonna fucking cum!” And lost all control of her body…..as she is coming back to normal I feel myself really close….and heres the kind comical part. As soon as she got off she sort of pushed me out of her, thanked me for the great orgasm and then I went back into the bar and she left. I have never seen her since, and don’t know her name….my old boss said he still will see her at the grocery in town sometimes…thanks for teaching me a few things! I wish I could have finished lol