NSFW story — Page 8359 of 11466 — collection of stories you shouldn't read at work

First time with another man [MM]

In my early 20s I went through a devastating breakup. My girlfriend of several years admitted to fucking one of my friends. I went into a depression and filled the void with porn and eventually, random sex. I got really into TS and gay porn on top of my regular stuff. I found myself browsing craigslist personals in search of my first gay or trans encounter. Trans was a lot harder to find in my area. This was the days before grindr and I didn’t like the exposure of a dating site.

I found a guy looking for mutual fun in an adjacent city, roughly a 90 minute drive. He was my age and moderately fit. White with brown hair and hazel eyes. Not weird looking, and I really didn’t have a gauge for attractiveness in men. Not feminine at all, which might have helped later, but I didn’t have a lot of options. Most of the guys on craigslist were way older, overweight, and extremely hairy. That’s a hard sell for a guy who’s only been with women. Read more »

Married People Can Have Hot Sex Too [OC]

It had been a long year and we needed to get away. Over the last year we’d had some major blowups and seemed to be constantly arguing. After some soul searching, we decided to stay together and recommit to our marriage. Yet over that year, it had seemed that all the bad feelings and past misunderstandings had dampened our spirits and that our sex was good but lacked passion. Our anniversary was coming up so we decided to have a date night at a local hotel. Why should the cheaters have all the fun and hot sex? If they can meet for sex adventures at hotels and in cars (hell, I even heard about cheaters renting storage lockers to have discrete sex on a budget) then why not married couples?

Starting with the hotel check-in, I knew that there would be something different in the game plan for tonight. My wife had been feeling standoffish and reserved. Lingering feelings of remorse had made her normally extroverted person seem publicly hesitant and uncertain in my presence. She stayed behind me and did not make eye contact with anyone. Was she having a flashback to a prior rendezvous’ with an old lover? Was she feeling some guilt or just distracted by the people in the lobby or just bored with the process? It was clear that we were together but her mannerisms were deferential. Read more »

I’m a straightish guy but I love botto[M]ing for transwomen, and occasionally men.

I’d consider myself straight. I have a girlfriend who I love dearly and have never cheated on. Before we met thoug, I spent years sleeping around. I went through a rough breakup and started watching a lot of porn. Eventually transgender and gay porn. I started fantasizing about tasting cock. At the time, craigslist still had personals and escort pages. I found myself browsing them and masturbating to the ads. Eventually I got up the nerve to try a TS escort. I’d already been with several female escorts so that part didn’t really bother me. I met this trans escort at her apartment. She was a gorgeous athletic latina with a fat cock. I was nervous so she sucked me for a while before I got up the nerve to suck her. I’d had one gay experience before so this wasn’t the first cock is sucked. Afterwards I topped her. I came so hard in her ass and felt so dirty after. Read more »

(31) My first pegging – dommed, dressed up then dicked down [MF]

I would have been 25 at the time, quite skinny, clean shaven with long curly hair. We met on Adult Friend Finder – is that still a thing? – and I had a very bi profile looking for MF couples I could be pals with. There was some success on that front but those are stories for another day.

She was a lot taller, a little older and definitely more experienced than me. She started me off by reading her erotica – there was one particularly vivid one about facesitting and pussy worship that I still think about sometimes. I mean, I think about everything about her a lot but that one bubbles up from time to time and surprises me.

She encouraged me to write erotica of my own and to send it to her so she could get a sense of my fantasies. I had never done this before so had to think long and hard about what I felt was hot and what the gist of my daydreams were. She gave a pretty strict deadline for them and became angry when they came a little later than set – I didn’t realise that was all part of the game. Read more »

It’s so hot in here. [FFM]

It’s been fucking hot in this city over the past few days. The air is unbreathable and no one can get any sleep. I was lucky enough to have a few days off and I left on a short solo trip to the seaside.

A friend reminded me that there is a nudist beach along the coast there. He sent me the GPS location, I looked for it all day in the scorching heat, trying not to get too sunburnt in the process. That fucking beach is somewhere along a coastline of 18km, I could not find it though. It’s a pity, because I really wanted to get naked and get people to look at my boobs and pussy. I wanted to find someone to hide in the bushes in the dunes with and have some fun. But there were mostly families and couples and just normal beaches.

At the campsite people in the tent next to me were having sex before falling asleep. Didn’t sound like great sex and didn’t last long but I listened through and it made me horny. I looked for someone on Tinder, couldn’t find anyone interesting that I would want to swipe right for. Read more »

[mf] how my lifelong friend asked me to fuck her senseless (PART 2)

first of all an enormous thanks for the amount of likes. never expected people to read my experiences, couldn’t believe more than 20 likes!

Also, my apologies for using the term “lifelong friend” for somebody I only known for 6 years. I’ll keep the title to avoid confusion on part 2

let’s get right into it. This one will be a continuation of the events of last story.

Therefore it will go straight to the action. For those who like longer introductions I have lot more stories to share!

but let’s finish this one first! ;)

ROUND 2

——-

I could not believe what I just heard. Not only did I just have sex with my best friend I crushed on for years,
but she was not kidding about what she whispered earlier -‘you’re gonna fuck me all night long till we are too worn out to move’-
Obviously this was a good 10 minutes after the first fuck (sadly I don’t have the refractory period of a God), but needless to say after she said “Ready for round 2?” I’ve never gotten hard again so fast in my life.
She notices me getting hard and approves it with a smile. “looks like you couldn’t get enough of this” she laughs while she turns around, and shakes her bare pussy and ass in doggy position.
“I certainly have not” I respond, finally finding my voice back after being astonished by tonight’s events. “then come get it” she giggles. Read more »

The Runaway [Mf, Rape.]

I wasn’t sure how long I had been walking. I could have measured the distance in how much my feet hurt. I had walked far enough that there were no longer any familiar streets. I only met strangers who couldn’t manage to spare more than a curious glance before their indifference took over and they hurried along with their own busy lives. That was a couple miles and a few blisters ago.

There were downsides to rash decision-making. That, at least, I had finally learned. Now there was time to think – to reflect on the past few months and how the decisions I had made weren’t the wisest. There was time, and the road, and the steady monotony of putting one foot in front of the other. Time to regret, I suppose. Regretting was hard, though, and I preferred to keep things like regret out of mind. There were more important things to think about, like how much my feet hurt or how hungry I was. Perhaps, if I had thought things out a bit more, I would have run away with a bit of money in my pocket. Read more »

The night that started 2 years of sexy encounters with another woman. [MF]

I was 22, 6’2 at the time away from my hometown attending college. During my weekends off I partied hard with a friend of mine (let’s call her Amanda). We are the same age and have known each other since our childhood. There has always been sexual tension between us but was never acted on.

One night at the local dance bar Amanda brought her friend (let’s call her Heather). She was 29 and sexy as hell at 5’4. Tight jeans grabbed her perfect juicy ass and the white V neck tee shirt was displaying her large breasts perfectly in the dance floor laser lights. Lots of drinking led to lots of both of the girls grinding on me. I had a girlfriend but she was 7 hours away and I’ve already been in school 2 months without sex…. I was getting weak.

The night kept getting hotter on the dance floor both girls were trying to outdo each other dancing with me. But all my focus was on Heather. Even with all the sexual tension over the years with Amanda she always felt like a sister to me. Soon the night was winding down and time to head back Amanda’s house I thought… I would always crash there on the weekends in the spare room. But for some reason we ended up at Heather’s small 1 bedroom apartment. I was totally shit faced and remembered nothing of the rest of the night. Read more »

[MF] Fucking her in a dirty bar bathroom

I was going to share a separate story until this happened just under 24 hours ago as I’m beginning to type this.

Last night Lulu tagged along with me and some friends to a bar a few blocks down from our appartment complex. We all waste the night away as we all got tipsy as the hands on the clock went around. In that time Rakeem and I did drunk karaoke to the Spice Girls before I beat him in darts right before I got absolutely embarrassed having being beaten in pool by none other than Lulu. It’s pretty humiliating to lose as big as I did to someone who stood one and a third foot shorter than myself in front of my friends at a packed bar, she playfully taunted me about it the entire night.

The night progressed on as some of my friends dispersed to other nearby bars as Lulu and I hang around right at the place we started at. I throw back a swig of beer as Lulu gives me a devious look. “Hey, come follow me.” She says as she take me by the hand leading me away. The two of us are a little drunk and I’m trying my best not to stumble a bit. Lulu leads me into one of the bathrooms as she locks the door being us two. It then clicked in my head what she wanted to do. Read more »