gonewildstories Archives — Page 1318 of 5640 — NSFW story

About that first time [FM]

I know, I was stupid, but like every curious virile teenage guy on the cusp of adulthood, I was impatient to experience it. No, I didn’t want to lose it because I was afraid of being mocked for being a virgin in college; I just wanted to tick it off my bucket list as something to experience.

It didn’t help that I was from a hyper conservative Asian upbringing and two years prior, I decided to start educating myself through porn, building up a healthy amount of unrealistic expectations about sex till I was bursting ripe for a major disappointment.

“One never knows how good or bad the first time will be till he tries” was my thinking, and I was yearning for any opportunity to break away into my first experience. Getting a girlfriend, or finding a hook-up was out of the question for deathly introverted me, so the next logical option was a paid partner. Read more »

I gave my Fiancee’s trainer a facial after her work party. [MF]

Hello again Reddit. Sorry for anyone who has reached out and asked for updates, I’m getting back to all of you but wanted to share a story from a month ago. I finally got to sleep with Alexis who is Taylor’s trainer, this night was built up over close to a year now. This story will be long as usual, but if I didn’t give you the back story and detail it deserves it wouldn’t do it justice.

**Skip for the naughty piece**

Alexis’ gym is celebrating it’s 1 year anniversary and are hosting a work party at this arcade & lounge entertainment place, her roommate bails on the night of and Alexis invites Taylor to go with her. Tay initially agreed to go and was excited for a night out but had to break the news to Alexis that she wouldn’t make it as she was feeling a little nauseous. What she didn’t share was that Tay is pregnant and her body is a rollercoaster of symptoms and emotions. In her absence Taylor offered me to be Alexis’ date and wanted me to have a night out, something neither of us have done for a few months. I worried about her and it being a late night but Tay insisted, I’ve been away working for 6 months so some drinking and socializing with other gym rats sounded awesome. She truly is one of one. Read more »

[M] 20 fucked my female best friend [F] 23 for the first time

We were best friends for about 3 years, without any Type of Sexual Interaction. She has a sexy, slim body with a nice ass and great tits! We were watching a Film together, like usual, and then she started kissing me… one thing lead to another and she was riding my dick. The sex was so good with her and we want to do it again in the future :)

[M]y [F]ortunate Sex Life

***For the sake of anonymity, the names in this account have been altered. All other details are true.***

It was late 2001. I was 24 and enrolled on a series of internet dating sites. I received a message from a woman, Anna, a few years younger than me who had just recently graduated college. She did not have the best profile picture, but I had a pact with myself never to ignore anyone who messaged me. I hated it when I would contact a woman only to be ignored so I couldn’t do it to anyone else. I set up a date, and I was glad I did. Anna looked better in person. She had wide hips and a fairly large ass, but she was also quite tall, so she was athletically proportioned. We had a nice enough date, but there definitely was a disconnect in terms of our loquaciousness. I was always a talky kind of guy; Anna was more on the taciturn side. Still, after dinner she invited me to the apartment into which she had just moved. So new, in fact, that her roommate still hadn’t arrived. We started making out on her couch, and things got pretty intense in a short amount off time. I had two fingers nestled in Anna’s hairy vagina when she asked if I’d like to go into her bedroom. I did, and, again, so new was this apartment that while her mattress had been delivered, she had yet to put sheets and bedding on it. We did not have sex that night, but we did everything but. In fact, with Anna’s upside down pussy on my face, I slid my pinkie finger in her anus. She did not flinch from this and seemed to enjoy it. Anna gave competent head, but my orgasm occurred during a break while she was jerking me off. I distinctly remember cumming on her bare, brand new mattress. Read more »

How many horny daddies on reddit will see me naked in one day ;) [F]

I’m down for anything, baby , make each other feel good . Sexy Creative Mind💦 let’s cum together. kinks Welcum I’m generally quiet and a bit shy. But I’d like to break out of that shell and have fun with someone. So if you’re up to talk about anything and everything dirty and maybe get up to some naughty fun as well hit me up. mmmmm I’m play with my bullet as I type this up 💦👀

He handed me over to his just-turned-eighteen year old brother in some random parking lot for his birthday. [FM]

over the years, there are a few fucks that were just so goddamn hottt that i almost always find myself coming back to cum while remembering them… and there was this one night in particular when a few special men gifted me with my sluttiest experiences ever, pretty much forcing me into a sexual peak at a very young eighteen. it’s been nothing but chasing the dragon ever since.

i met this man one evening when he picked me up while i was walking home, it was well after midnight and i remember this convertible driving by and the man behind the wheel catching my eye. i was walking in the direction he was driving from and he whipped out the fastest, tightest u-turn i have ever seen anyone make, and he came screeching up to my side to offer me a ride – he absolutely could sense the slut within me. i accepted and slid into the front seat, pretty much right into his hands and he furiously finger fucked me before dropping me off at home, just after two a.m. Read more »

[MF] Olivia came on her knees on the floor of the hotel lounge

COVID was nearly the end of business trips, but they didn’t quite die out. Things have started to pick back up for my work in the past month or two, and I recently headed out to another East Coast city for a 3-day business trip. I brought Olivia with me. I’ve written about Olivia a few times before — 24, petite, slender, and beautifully kinky and submissive. She’s in the third year of her PhD program, and her spring break coincided with my trip. I wanted her to be my hotel room fucktoy, and she was happy to fill the role. This took place on the our second night there.

I came back later in the evening, around 10. We had both already had dinner separately, but we met in the hotel bar and brought drinks up to our room. We’ve had a lot of sex in the past few months, and there’s a few rhythms we’ve gotten into that are comfortable but still exciting. Something about Olivia’s effortless femininity and eagerness to be dominated keeps even our routine sex interesting.

My Wife and I Have Our First Time With Our Friends [MF] [MF]

A few people have messaged us asking about the first time we played with another couple, so I figured I’ll write it out and share it here. Maybe if my wife has time later she can share her side of the story.

We’d been friends with Naomi and Tim for years, since our early 20s. I’d always been a bit attracted to her. She’s very different from my wife, physically. She’s tall, hourglass figure, light skin, dark hair. My wife is on the shorter side, petite, with olive skin. All four of us got along really well. In the past few years the sex with my wife has gotten even spicier. After years of marriage, we knew how to turn each other on and were always keen to explore our boundaries.

I don’t remember how it happened exactly, but the idea of showing off to others entered our bedroom conversations. We always got super turned on by teasing each other about showing more skin, or even turning specific people on. It didn’t take long for us to realize we both got extra turned on when thinking about turning on Naomi and Tim. This evolved into roleplaying that we were fucking them sometimes. Something about having that as a dirty little secret always turned us on, and the orgasms when we’d do that were incredible. Read more »

I [m] fucked a rando [f] off a hookup website

One day a while back, I was bored and horny (nothing out of the ordinary). I posted an ad on doublelist, which is a sort of craigslist clone for hooking up. I stated in the post “I won’t cum until you do” because one, it’s true, and two, you gotta stand out somehow. I had a date planned for that night, and eventually forgot all about the post.

I went to see Infinity War with a woman off tinder, and that date was not going well. Her pictures were old and taken at off angles to hide her weight, classic tinder catfishing. She also wasn’t very interesting, but hey I got to see Infinity War.

While walking out of the theater, I check my phone and see I have a message from an unknown number. The text said the following:

“Hey I saw your post on DL! You look hot and I’m going to be in the area tonight if you want to play. Just let me know.”

I quickly respond with: “Sure I’ll be available in an hour, can you send a pic?” Read more »