gonewildstories Archives — Page 5555 of 5640 — NSFW story

Cherry Chapstick / Lily Part I (F/F)

Friends, I'm really feeling the ladies this week. So I thought I'd tell you some of my memories of my favorite female partner. Dare I say the one that got away?

This first section is mostly a prelude. There's no sex here but you know I'm good for it in the follow-up.

One of my favorites mentioned chapstick the other day in passing. Any mention of chapstick brings me back to a warm summer night with the girl whose memory haunts me. Lily. Fucking Lily (not her real name).

I was living away that summer. The friend that traveled with me left after a few weeks and I was all alone. The only people I knew were those I worked with or friends that came to visit. So I decided since it was a small town to lurk on craigslist for a while and see if I could find some friends. Wasn't really looking for a hookup, just locals who were like minded.

Lily had posted that she was looking for friends and if something more developed then so be it. I'd responded to a similar post from a guy and I didn't get raped or killed so I figured what the hell. And her picture was so cute, how could I resist? Worst case scenario I'd make a new friend to explore the city with. Read more »

Fucked a milf while working away with help from 50 shades of grey part 2

This is the second part of a story the first part is here

If you don't want to read that I'll give you a recap

I'd been working away and had to stay late with the manager Helen to finish the work. We ended up having sex in the break room due to her reading 50 shades of gray and me being a little cheeky. After that I'd invited her to the digs I was staying for a little more fun!

So I get to the hotel, which turns out to be really nice digs park up the van an go check in. Bonus the room has a double bed! I grab a quick chicken salad from the restaurant an go take a shower. When going through my wash bag I discover a viagra from when I'd been away earlier in the year, confident Helen was going to show up I took it.

I throw some jeans an my shirt on grab a bottle of wine from the bar downstairs an I'm back in the room with 10 mins before our arranged time. I'd text her the room number an hotel name, just hoped she would turn up! Read more »

An Innocent’s Gradual Descent: Sum[m]er [f]un

Heads up, this is going to be a long story with lots of detail. May continue with other memories of Summer later.

The summer before I turned 17 I was a counselor at a summer camp. The weeks leading up to the camp, I got together with all of the other counselors over the weekends to plan some of the events and activities we would be running in a few weeks time. Thats where I first met Summer.

She was a short and gorgeous brunette. She was my good friends cousin and I had been told of her joining out team of counselors. She was a dancer, with legs pale and lean. Her face was round, large brown doe-eyes framed by shoulder length brown hair. She was fit no doubt about it and she had the largest breasts I had ever seen, DDs fit snugly into a rather conservative top. She was the epitome of innocent beauty.

Summer's cousin, Ashley (a good friend of mine), had given me some background in that she had never actually gone to a sleep away camp before but was excited to be staffing one. Summer had moved a couple years prior from South Africa and lived with her family in Colorado. Read more »

Fun with ex [m/f]

Jane and I dated for most of last summer. The physical part was always great, but there were other issues. Eventually I broke it off with her because of our fighting. We remained friendly, hanging out over the winter. Earlier this year, I invited her to an event because I didn't have any one else to take and nothing wrong with the "take someone who looks good in a dress" logic. And Jane looked good in a dress. She's 5'7", mixed white and Latina so she always has a tan and long dark hair. Although petite, she has a great heart shaped ass. A pair of mouthful tits complete a very nice package that she likes to squeeze into a dress. And, not to brag, I don't look too bad in a suit at 6' and working out every day. We drank a bit that night and flirted more than a bit. A couple days later, we fell into a FWB situation. Read more »

That time I had sex on webca(m) for strangers

I was probably less than 6 months into being 18, I'd met this girl who worked at a bar. Her name was Sammy, we had started dating and had been together for a couple of months. One of the girls from the escort agency I worked at, had recommended a cam site (see other post for exciting escort story)

The site was shockrooms I haven't been there in almost a decade don't know if it still operates. How it worked was you were on cam and people would tip you stars that could be exchanged for cash. So Sammy and I get it in our head we were going to try this.

So we set up our 1.3 MP webcam in the corner pointing towards the bed, we are ready to go!

I started out by going down on her, nibbling and lightly flicking my tongue. I was nervous, I'm fairly large at 8.5" and quite thick so I wasn't concerned there. However having a live audience of about 15 people was still foreign to me. I kept going down on Sammy getting her as worked up as I could. Read more »

Fucked a milf while working away with the help of 50 shades of grey

One of my favorite encounters, iv thought about it so many times since, thought I should share it with you guys.

I work as an electrician and was working away snagging problems for a chain of betting shops. I'd been working away for a few weeks driving all over the country and was getting really fed up and generally these shops are in the worst areas too.

I arrived to this shop in Hull in the late afternoon and pretty soon realised this job was going to take more than a couple of hours plus I needed to turn off the power . I called the owner of the shop who said she will come when the shop was closing so I could finish the work.

So iv been going through a bit of a milf loving phase around the time of this story, I'll happily share a few more stories, anyway when the boss (Helen) turns up she is exactly my type, full woman's body a nice big ass and boobs a really cute face, long ish blonde hair an a smile to die for. She looked like she was in her late 30s but was actually 45. Read more »

Sophomore Year (F)un part 4 [fm] long

Tim and I left for the two hour ride ahead of us to his parents lake house. Tim offered to drive so we got in his suv and got on the road. We talked about anything and everything and the conversation of his fantasy came up again and he asked me mine.

I described to him my new found fantasy that Jake had sort of brought out in me. I described to him how I enjoyed giving blowjobs and how being outside or in public turned me on.

The whole time I'm describing this to him I can see him adjusting himself out of the corner of my eye. I decided to tell him how I gave Jake a blowjob in the car and described to him how I snuck my foot into his lap under the table. I looked down at Tims crotch and could see his dick pushing against the fabric of his jeans.

I placed my hand on his thigh and didn't hesitate to run it over his hard cock. I could see him look down with approval so I decided to release his pain and undo his zipper. I reached down his fly and fished out his member until it was exposed and pulsing in my hand. Read more »

Lodge Adventures: Part 3 [Ff/mmm]

This is the last installment of my series about a pretty debauched spring break I had my senior year of college. This is my last story from this week, but I'll probably be sharing some more from the rest of my life soon!

The final night before we leaving the cabin was kind of a bacchanal, everything was packed except only what we needed for the night and a mountain of booze. We had rationed out our alcohol pretty well (even though we’d brought an incredible amount to begin with) and we were trying to finish off everything so we wouldn’t have to haul it back into town with us. This resulted in what I’m pretty sure was one of the craziest nights in the lives of most of the people there. The night started out in an incredibly liberated atmosphere where half the people there had fucked the other half before that moment, and it was amazing the whole thing didn’t actually just turn into a massive orgy, instead of only bordering on one. Read more »

[F]irst time with [m]y best friend

So, this is my first post on reddit (this is my naughty account obviously). Thought I might as well start here. And yes, all of this is a completely true story. I honestly still think about this first time today since it was just that awesome. (names obviously changed for privacy)

Clara and I were best friends and had liked each other for years but never told each other. I would give her friendly tickles, she would casually stroke my leg while we were studying in university. But we were both shy so we never told each other we liked each other and we ended up both dating other people. We kind of were the ones we would go to when we each had sex issues that we wanted to talk about. She would come to me with her guy issues when she wanted to know how to better please a man and I would go to her about how to please women. Years later, we ended up going our separate ways and she moved away from Toronto. We still kept in touch and flirted over Skype but neither of us made the first move. Years later, she came back to Toronto to visit me and stayed with me. We knew she'd be leaving again in a few weeks. And for the first time, we were both single at the same time. Things got really hot. Read more »