gonewildstories Archives — Page 2106 of 5640 — NSFW story

The end of the first night with my [M]26 cute redhead coworker [F]20

This is another continuation to my former story located here : https://www.reddit.com/r/gonewildstories/comments/nnxnfi/the_first_time_i_m26_fucked_the_cute_redhead_f20/?utm_source=share&utm_medium=ios_app&utm_name=iossmf

It hit the end of the night and it was around 1am. Emily and myself had been cuddling naked in bed for a while watching a movie when she realized the time and said she had to go home. I offered her to take a body shower seeing as we had just had on and off sex for the last 7 hours but she declined saying she was okay and would just shower when she got home. After a few minutes of not wanting to get up the episode of the show we were watching ended so, she decided it was time. She asked me to hand her all of her clothing so I did. Then she got out of bed and stood up. I sat there watching her get dressed.

She bent over giving me an incredible view of her pussy from behind as she stepped into her thong and pulled it up over her amazing ass. Then slipped into her jeans pulling them up as I got a nice last glimpse of her ass. Then she turned around and just smiled and told me to get dressed so we could go as she put on her bra and shirt. I was turned on again after what I had just watched but I knew she had to get home. So I just slipped on some track pants and a t shirt to be comfortable. Read more »

A Creative [F]emdom punishment she gave [M]e [Long]

After a long hiatus, she wanted me to tell you all about one of her favorite new punishments she came up with. For background context, we both have found that we love power exchange, and she‘s really loved taking control in the bedroom.

Our latest new twist has been chastity play, which has been lots of fun for her…and, let’s be real, pretty fun for me too. After having me wear my cage for a few hours, which turned into a day, then into several days, she decided she wanted me to go an entire week locked up. At first, I was nervous about the idea, but after chatting about it, we decided to give it a try. Part of the protocol for the week included her reaching out to me several times throughout the day for “chastity checks”, and I needed to fulfill the request within the next 30 minutes. Needless to say, I missed a few that week, which leads us to the punishment for not being able to meet her demands. Read more »

An awkward, but enjoyable encounter between between [m]e and a [f]riend

Note: names have been changed to protect the guilty

To put events into context this took place in my final years of college after I had moved into a new apartment with a friend of several months since her prior roommates were moving to other cities. It seemed like a somewhat risky situation since we had already slept together a few times and were for all practical purposes dating at this point.

My friend Kay was a member of a local sorority and as you can imagine shared all kinds details with her friends. One of her sisters, Jen, was a rather open and outgoing girl who clearly enjoyed talking about guys and sex. Maybe it did something for her or maybe it was just the shock value of being so blunt that excited her. Either way I’d have to say I was a bit interested in talking with her and well who knows what else. Read more »

[MF] The college boy and the mature mom (very long)

[Repost from my previous account. I’m going to put up a few of my previous posts to give context to some recent experiences.]

Should probably start with a little explanation. As I was growing up I was tall and gawky with glasses and an overbite. Then I was an athlete throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles), but still understand the perception of not being considered attractive.

This isn’t the first experience I had or necessarily the hottest (though I think it’s pretty hot), but the easiest to write–my first experience with an older woman, which really got me into enjoying older women. I really am into the build-up and noticing details and emotions and hope you are too.

I was a junior in college, fall semester, still living on campus. On Tuesdays my best friend and I had a large open swath of time just after 11am, so we’d usually do something together–go shoot ball, grab lunch, go to a bookstore, lift, etc. For some reason on this cloudy, early October blah Tuesday we decided to go off campus and treat ourselves to that fine restaurant chain known as Chilis. We’re seated at a table next to three women in their late 40’s, early 50’s. My friend and I order our drinks and start looking through the menu. Read more »

Dorm Room Surprises Roomate[18][f]

I hated the start of my Freshmen year with a passion. Our dorms sucked. No privacy at all. They consisted of two, two person rooms with a shared bathroom. No control over who your room mate or suite mates were was also a sore spot with me. I did not go to college with any of my high school friends. So, I was stuck with who ever they assigned me with. The floors were supposed to be segregated by gender. However, our RA didn’t give two shits if we had girls in our rooms at all hours.

On the first day, my room mate and our suite mates got together and talked. It turned out that my room mate, Jeff, had a long term girlfriend, Christy, and both of my suite mates also had girlfriends. I liked my room mate. He was very considerate of our shared space. He would always ask if his girlfriend could spend the night with him in our room. However, the douche bag suitemates never asked us once. Even though we all shared the bathroom that their girlfriends would be using. Read more »

[M] I Pissed Off My Girlfriend, So She Made Me Earn It By Eating Her Ass

It was my final semester at college, and my girlfriend and I had been together for something coming close to 2 years. We had a very “dynamic” relationship; the sex was great and we enjoyed each other’s company, but we probably fought more than was healthy. One night while she was housesitting for a friend, she invited me over for the evening. It was a nice, loft-style apartment, with big windows, a generous bedroom, and a beautiful kitchen/living room. We grabbed a bottle of wine, and curled up to watch some TV together on the couch. As usual, we were quickly distracted from the screen in front of us, my hand wandering down between her thighs to tease her. It wasn’t long before I had my cock out, her fingers wrapped around my shaft as we made out.

We had always talked about how exciting it would be to have a threesome, and in the heat of the moment, I mentioned how hot it would be to have one of her friends there to join us. The comment…. well it didn’t go over so well. 20 minutes later we were laying in bed with our clothes on, all sense of excitement completely wiped away by my poorly timed mouth. Read more »

First Squirting Experience/ Tips on How to Squirt [MF]

I will admit, I was one of those girls who made fun of all the “squirting porn stars” and thought that it was all just a facade. I was like, okay cool, all these girls are peeing themselves or shoving douches up there. Because of their horrible depiction of squirting, I was nowhere near believing it existed.

But boy, was I wrong. Read more »

[F]23 Caught with my pants down at a golf course

As the title implies last week I was ask to go golfing (which I only have a handful of times). Half way through the course my BF says he would love to have a quickie somewhere. After what we thought was a good spot a few holes later I start stroking his cock and sucking on him a little in the golf cart. After a few minutes I pull down my capri’s and my green thong and he slides himself in from behind. I have one foot in the cart the other on the ground. He’s thrusting himself into me pretty good and grabbing my hips for about a 2 minutes or so. All of a sudden this older couple comes out of the other side of the tree line about 30 feet at most away. We both stop immediately and hop in the cart and drive off laughing. All while I’m trying to pull my pants back up. Was decently embarrassing but also exhilarating!

PS. We went back at it and finished about 2 holes later in the tree line. Not caught this time!

I [M] matched with my ex’s best friend [F] on a dating app

I’ve been single for a few years now after I broke up with the most serious girlfriend I ever had, we’ll call her Jenn. She’s a great person, but we were young and I didn’t know what I fully wanted out of life yet, so I left and moved across the country for the last little while. Cut to today I’ve moved back to where we’re originally from, shes in a new relationship and I’m genuinely happy for her.

Being that I’m single, I fired up the dating apps and started swiping. I’ve never really had a ton of success on these apps but with covid, it’s been the only way to meet new people. About a week ago as I was swiping through, I saw a familiar face, my exes best friend, let’s call her Emily. I’d always found Emily incredibly attractive and I’d be lying if I said I hadn’t fantasized about her countless times, but being the childhood best friend of my ex, I thought those fantasies would remain just that. I decided I have nothing to lose and swiped right on her and I went about my day, the next morning I woke up, checked my phone and saw I had a new match and sure enough it was Emily. Read more »