Category: gonewildstories

[MF] When good intentions go sideways

During my time, to put it bluntly, as a hoe I wanted to at least try and date. I was naive and took my dating profile to what I thought was “safe territory” : long term dating, ratcheted up the age range, and took off any short term dating. I watched my matches dwindle but one caught my eye. She was a couple years older, loved Jesus, loved him some more, and talked about how she was finding her mister right. Nothing overtly sexual in her profile and she loved going to the gym and bake sales. I messaged instantly and after a bit of back and forth SFW texting we swapped even more SFW pics and then she asked if I wanted to come to a house party her friends were having. Of course I’m game and she says there’s drinking and if I get too tipsy I can sleep it off on her couch.​

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The study session I forgot about [FM]

There is a knock at the door. I don’t answer because I am lying in my bed and masturbating while fantasizing about the guy who lives upstairs. The person at the door is extremely persistent, though. The knocking continues.

“Hold on a second, Jackie” I say as I quickly roll out of bed wondering what the hell my roommate needs right now.

“It’s Andy,” the person on the other side of the door responds. I suddnely remember that Andy and I had made plans to study at my place. Andy is one of the guys in my computer science class. He’s handsome and charming. And best of all, he actually understands what the hell the professor is talking about.

I guess Jackie must have let him in. Fuck. I begin searching for something to throw on and find a pair of gym shorts on the floor. Andy does not wait. I guess I forgot to lock the door. Fuck.

I freeze. My shorts are only halfway on. I have no shirt. He walks into the room and stands at the doorway, moving his eyes up and down my body. Feeling his gaze I pull the shorts on all the way — covering my ass and already wet pussy. Read more »

39[F] met up with a neighbor 25[M] while my husband was at work

A few weeks after my first sexual encounter with my upstairs neighbor Brent and my husband(see previous post),i had been dying to see if i could sneak over to his place when my husband was at work. One night when they were talking in the hallway i overheard Brent say he had the next two days off of work, so i knew since i was off the following day as well id see if i could meet up with Brent somehow. Read more »

Vegas fun.. just the 3 of us [MFM]

So the last time the wife and I were in Vegas it was our anniversary and I had set up an encounter with another male for her , basically some one to help me bring her the most erotic kinky pleasures she could handle or want.

But I did it without her knowing, which was wrong and I would later regret doing it behind her back . The “encounter “ happened by coincidence at a lobby bar and it lead to her decision of it happening or not. She chose to go up to our room with us 2 guys. It was literally all done and planned between us 2 guys within those few hours as my wife and I were driving to Vegas. Told him about her ,how were to meet and that it wasn’t guaranteed. It was still up to her if she wanted to take it further . He agreed and it happened . Read more »

[M]y [f]irst hook-up

If you’ve read my post about ‘Wisconsin women introducing me to the world of sex,’ you know that prior to entering college at the University of Wisconsin, I had never even kissed a girl. I thought I’d detail my first experience with a woman that fateful night in the autumn of 1996 with a Milwaukee gal named Marcie.

This was early in my first semester sophomore year. I had resolved, over the summer, to break my permanent streak of not getting any action. Enter Marcie, a junior from Milwaukee, I met at a local bar my friends and I frequented. Marcie wasn’t beautiful, but she did look like what I could only imagine to be a ‘fun’ girl. Dark, curly hair. A fairly curvy body. I remember she wore brown, polyester pants. Fashionable at the time, if you were around in the mid-nineties, but even then I thought they were unbecoming – kind of like a UPS uniform. Still, I got the impression she’d ‘hook up’ with me, so I started paying for her drinks, and sure enough, when I asked if she wanted to come back to my apartment, she said, “Sure.” Read more »

Cheated At Work [MF]

I was in a relationship for about a year. One day she was talking about how she didn’t like how blowjobs were represented in porn and in general. So I no longer was getting head. This did not set well for me.
After a few months I just couldn’t handle it anymore. I started talking to this girl at work and she kinda become a ear for all my problems. She agreed that my girlfriend was taking it a little to far.
So on the weekends it was just me and two others, including her. We were texting because it was a slow night for us.
We started talking about the fact that I didn’t get any blowjobs from girlfriend and she was kinda joking about giving me one. I said I wouldn’t mind. Her co work went out for lunch and she came into my office. She asked if I could take it out and I was kinda shocked but I was so ready for it. I took it out and she grabbed it. She told me to sit down and she started sucking my dick. It felt amazing, a few months without a blowjob and now I’m getting one at work.
The way her head bobbed up and down, the way she tongued the tip of my cock had me so close to cumming way faster than I wanted to. I remember she tried going all the way down to my balls but gagged, this turned me on even more.
I finally came and she had it all in your mouth. Her cheeks were full. I thought she would swallow it but instead she spit in my trash can. I had to empty the trash can because I share an office with the guy on days.
We talked for a little bit after and she eventually went back to work plus her co worker came back, she totally knew something was up.
I eventually broke up with my girlfriend and actually started dating the girl from work. That was the first time I actually cheated and well I guess it work out.

She Wanted Anal [MF]

So I never really had any woman want me to fuck them anally until I met someone off Tinder. We hung out and one thing led to another but never had sex because I was lazy and never bought condoms but I was meaning to.
One day she came over and we started making our, grinding all that stuff. I started fingering her and she was so wet. I mean drenched. I was making eye contact with her while my fingers were inside. I took my fingers out and started rubbing her asshole. Her juices seriously leaked down to her asshole.
I stuck my finger in her ass and it just went right in. Her juices lubed up her asshole for me. I was surprised that she didn’t yell at me but instead started breathing heavy.
I asked her if I could fuck her in the ass and she said yes! That I got her so horny she wanted it.
She bent over and I my dick entered her asshole. It felt amazing, how tight it was at first and then it just sucked me right in. I kept going until I came deep inside of her.
We eventually had sex at a later date but I always finished in her ass. This was the first time any woman let me do anal.
One time we had a quickie and she was wearing a dress. I, of course, finished where I normally did and later she was talking to a friend in front and of me. Once they were done she said “ugh your cum is dripping down my leg.”
Fuck I miss her and kick my ass every time for messing it up.

[MF] Naughty wife’s wildest day ever with her fwb [FM]

This is our first post here, but this isn’t the story of our first time together so a quick background. We are long time fwb who used to get together when I traveled for work – she was married (now separated).  We have done a lot of exciting things and are very open with each other.  But our
chemistry over the years has remained amazing even when we ended up going a long time before being physically with each other.  One time it was over 2 years, and when we met
up it was instant wild sexual chemistry again. I am quite tall, dark hair, relatively slim, and about 6 years older than her.  She is average height, curvy but just the right amount, with a sexy smile and incredible boobs (38J).  She is an exact mom next door fantasy type.
So a couple of years ago, wehad started to rekindle our fun, and she was super excited.  She was still
married, though they had been on shaky ground for years and had almost zero sexual interaction.  She also had a fwb she had been seeing for a couple of years.  I completely encouraged it; she is so incredibly fun and should have as much sex as she can.  She has an intense mood while fucking and a huge sex drive. 
We had had a couple of great nights in the first month or
two I was there, and we had fantasized about us having a bit of fun when she
had plans to go see her fwb (like making out in her car when she was a block
away from his place).  A kind of secret little tryst before she went to see him. We hadn’t put it into action but teased and had sexting fantasies.  Then we seemed to ramp it up a bit, and she had been especially horny the week leading up to her birthday.  I asked what she wanted to do for fun on her birthday – basically anything we had fantasized about that she wanted to make happen for real. 
She mentioned this fantasy.  I was super into it and also happy to make her birthday hot and wild.
But we absolutely escalated it.  She instead made plans to fuck her fwb in the
afternoon, and I told her to come to my place early in the evening.  She couldn’t wear anything too naughty but had her sexiest lacey panties on and had high heels in her purse to wear for
me. She went over to her fwb, and they had a drink and she immediately she was getting absolutely pounded.  She tends to be directly under him when they finish.  She orgasmed at least 3 times. 
She felt him absolutely explode as she moaned and screamed loudly. She
lets him cum in her as he is snipped.  She loves it so much. I fuck her sometimes bare for a bit but never to
finish.
Then she came over to my place and we started making out and
she coyly told me what had happened, and that there was more.  She had gone home in between, and as she was planning to head out again, she ended up giving her (now ex) hubby a blowjob.  So this surprise turned me on, plus I could tell how pumped up she was.  Her energy was way more intense. We were on the couch and she was stroking me while I sucked her huge tits.  She loves that and
always reacts wildly to it.  I fingered her, and she orgasmed right away.  I took
her to the bedroom, and we had sex in every position.  She loves being taken from behind, and
usually dirty talks and scream from that.  She also rode me for quite a long time. I had to withhold so many times because she had me ready to explode so many times.  I love having her on her back so I can play with her amazing breasts while we are fucking.  She spent a good 5 or 6 minutes sucking my cock while also telling me about her naughty birthday so far.  It drove me even more wild.  I love how she sucks cock; she is amazing at it. She had orgasmed so many times she lost count.  She had even squirted a little bit.  She doesn’t always do that but sometimes does when she is extra naughty.
Finally, she took me in her mouth after we fucked for another 20 minutes and had me explode in her mouth.  So she had cum in her pussy, on her tits, and in her mouth as her birthday presents. She has amazing fantasies but this was definitely her wildest birthday, or any day, ever.

A Young [M] CEO gives me [F] the hottest orgasm in the Waffle House parking lot

Several years ago when I was in university, I matched with an attractive CEO of a young startup who was visiting town for a conference. He was only free for the evening, so we spent the night driving around back roads, innocently chatting and laughing, his hand on my thigh. He was feeling ill, so he dropped me back at my apartment and we promised to stay in touch.

4 years pass. We follow each other on social media, including LinkedIn. I graduated college and find myself working in the same field as him, so whenever he slid into my DMs after a cute IG post, I was excited to chat.

After many years of asking me to come visit him in CA, he mentions that he will be in my town, but he is only free at 6am. Idk about where y’all are from, but the only thing open here is Waffle House, so I pledge to introduce him to this east coast staple.

His startup became extremely successful since I last saw him, and I was excited to talk about what they are going to be changing in the field. We meet for breakfast and had an awesome conversation that I probably should have signed an NDA for lol. Read more »

Cheating In college [FM]

She cheated with a guy named Matt who was given a blowjob(actually two but we will talk about that later) the details of the first are below and is a near replica of what she told me and her best friend about it.

She told me she was working on a chemistry problem set with Matt and another female friend . Eventually her friend left and it was just herself and Matt. She said Matt and her ending up making out on the couch in his dorm and quickly Matt had pulled her shirt down (she didn’t have a bra on ). She was still wearing a skirt and after a few mins of kissing/getting felt up she said she told Matt she had a boyfriend and was feeling guilty and shouldnt have even gone this far. She said she was going to leave but right then Matt pulled up her skirt and pushed her legs apart. He then said “well he’s not here right now and he won’t know”, as he quickly pulled her green thong to the side and started eating her out and he stuck a finger in her while holding her thong to the side. She said she felt guilty but was enjoying having her pussy eaten and fingered. Matt parted her labia and began to kiss and lick her clit .She started moaning which encouraged matt to continue and a second finger joined the first in her pussy. This went on for about maybe 5 or so minutes until she came for him. She said she didn’t expect anything to happen between her legs and then she said well I kinda just let him do it. Read more »