gonewildstories Archives — Page 4075 of 5640 — NSFW story

My quick hookups from Craigslist/Doublelist/apps [MF]

I’ve had a number of hookups from CL, DL and other apps and whatnot. Trying to go chronologically and only hitting on the quick hitters. Have a whole number of ones where it took a while to meet and then was ongoing from there. Those were mostly ones where I met couples for MFM or bull situations, maybe will post some of those another day. Sorry for the brevity on these. I can likely pull up pictures if requested for a few of them, still have most of the old messages.

– I was 23, messaged a woman near my office. She was married, Hispanic, 36 years old, married with kids. She responded back and we were both free at lunch and decided to meet for car sex. An hour later we met up on a random road, found a spot and crawled into back seat of her suburban. She was probably like 5’1”, curvy with a little extra and big tits. She was incredibly nervous and I was decently nervous also. I took off her pants, revealing a nice thong and she was definitely very wet despite being nervous. I finger fucked her pussy and she got going and moved to suck my cock. We ended up banging for a little while, eventually cumming while I was pounding on top of her. We quickly put our clothes back on and left. Never spoke again Read more »

Sex Laughter [MF]

After the previous night’s short fuck without either my wife or I cumming, both of us had our sexual tensions build up through the day. We both grabbed each other in public and made out in front of other folks at the resort. I bet the old folks were all grossed out with our hot make out sessions by the pool with our tongues pushed into each others’ mouths.

I had come up with exactly what I wanted for the night after the kids were asleep. And I kept that surprise from my wife, only hinting that I had a hot night planned for us later. She’d only respond with, “yeah?” and give me that look that just makes me want to rip her clothes off and fuck her right then and there. Finally evening rolled around, and the younger one went to sleep, leaving only the older one to get to sleep. Since the older one had headphones on and was in the other room, my wife and I would have hot and heavy make out sessions with heavy touching and biting. I could tell my wife was ready to take my hard cock at any moment, and certainly I was hard and ready to go. Finally the older one went to sleep and after some time we check to make sure they were both out. Normally this wouldn’t be as much of a problem, but while on vacation with smaller than normal accommodations we wanted to make sure. Read more »

In front of an audience [Very Long][MFF][CUCK]

In my last submission I told how I got into cuckolding. It was not a regular thing at first. And my SO, Olivia, our friends, Ava and Cal, and I swapped or played as a group of three or four just as often as we “roleplayed” cuckolding. With Cal being a dominant and brutal fuck machine making the girls hurt and scream in pleasure. And me being the wimp, who just watches.

Chastity and bi-sexual aspects of cuckolding is something I am not comfortable with or interested in, so those things we never did. But I have to confess that I started to read a lot of cuckold fiction and for whatever reason I have to say, I am into the humiliation, just as much as into the erotic sight, whenever I play cuckold. Don’t get me wrong. I like to play a dominant role to enjoy myself once in a while too.

Unbeknownst to me Cal was having the exact opposite reaction. He really was into the power dynamic, even if it was just a play. Having Olivia and sometimes Ava at the same time in front of me. He wasn’t so much into the humiliation, but the feeling of power. Read more »

the hottest sex I’ve had [MF]

I’m not sure how this story will turn out, as there really isn’t anything special about the sex.

I had a FWB that I had amazing sexual chemistry with. We both enjoyed the same parts of sex and were turned on by each other. She had a fit, petite body but a nice round ass. Just thinking about her ass now makes me hard. She loved my cock. I’m 7.5-8 inches, with a big head and a downward curve. Not the biggest, but big for her.

We had sex several times the night before and both feel asleep naked. I woke up in the morning and saw her laying naked, her breasts uncovered. She looked at me. Without saying anything, I crawled on top of her, her spreading her legs for me. We started to kiss and I could feel myself quickly getting hard. I reached down and grabbed my cock as she spread her legs wider. I slipped inside her and started to slowly fuck her. It wasn’t long before we started fucking hard in missionary. After just a couple of minutes we both came. We smiled at each other and said good morning. Read more »

[MF] Wood in the woods and then in the bedroom

TL;DR A pushing 60 widower tells you about a five year period where, between a bad breakup and meeting his future (now late) wife, had this sexual awakening. This time it came out of the blue and it turned out to be a pleasurable afternoon, evening, and night. Following this a “committed” FWB happened, and there are many stories to share.

I’d met Sally (not her real name) at a mutual friend’s holiday party in Boston. I liked her immediately, but not in a sexual way. The 5’6″ BBW redheaded firebrand told dirty jokes and had this Just A Good Person quality that I took to immediately. Plus we’d both been through breakups recently. For her, a mother of three children, she had just completed a pretty ugly divorce. For me, never married, I’d broken up with my college sweetheart, or I guess you should say that she called me a “loser” repeatedly before having divulged that she’d cheated and that our relationship was done.

[M]y friend’s boyfriend found out that I’m a [T]rans guy… (part 2)

Due to the amount of positive reactions I received after the first story I posted, here is part 2!
I have to admit I was a little nervous before posting here but you have given me so much confidence and I love it. Why should I be ashamed of being a slut right?
Anyways, here is part 2:

If you haven’t checked out the beginning of this story:
I’m a trans guy (I was born female and transitioned to male but I kept my pussy.) and none of my friends know about it. Even my good friend Hannah.
She was dating this guy Ethan who happened to be too hung for her to satisfy sexually. One day he walked in on me taking a shower and it eventually ended up in his cum down my throat.

The days that followed, Hannah confided in me that her relationship with Ethan was getting better already. He was more respectful of her wanting to have sex in a more vanilla way and she felt relieved. I’m not going to lie; I felt pretty bad at first.
Even though she seemed happier I couldn’t help but feel guilty about the fact that I had let her boyfriend fuck my face in her own bathroom. But at the same time that memory kept making me wet and all I wanted was to see him again. Read more »

Giving a ‘straight’ guy his first experience [mm]

I gave a guy his first gay experience once.
tried to tell me he was “straight”, we were on a night out in town and things were just a little bit flirty between us. We’d had a couple of drinks but both decided we want to leave early so shared a taxi.
When we got back to his flat he invited me inside for “a quick drink” – we all know what that means.
We walked inside his building and waited for the lift. Once it arrived we stepped in together and the doors closed. Before i know it he’s kissing me, i can tell he’s enjoying it because i can feel him getting hard through his jeans.

We stop, leave the lift and walk to his flat, into his room. There we start kissing again, and he’s pinned up against the wall.

Our shirts come off, and i start to stroke him though his jeans. By this point i think “fuck it”, get down on my knees and undo his belt and jeans.

I double check he’s okay, and then take his cock out. i stroke it a few times before teasing the tip with my tongue. Kissing the head of his cock i slowly took in more and more in my mouth. Read more »

It’s dangerous to go alone, take this [MF]

Thinking back to my days after college when I was single and would spend most of my time during my night shift job on PoF or Tinder, I recall meeting a short thicc girl named Sarah.
She had small A cup tits but was built like a pear with a nice ass.

The picture that she had as her profile showed off her dark purple lipstick against her pale skin and a heart beat tattoo across her sternum, but the center of the heart beat had the TriForce symbol from Legends of Zelda. My immediate thought was yes I need to fuck a gothy nerd chick ASAP.

Within a matter of minutes of matching we were lining up a time to meet the next day I was off.

Fast Forward a few days and Sarah was driving from an hour away to my apartment to hang out for the night. There was non stop flirting and sexual teasing the days leading up to the night. Read more »