Straight Archives — Page 2411 of 2451 — NSFW story

My [29F] (f)irst wild fuck with a coworker [37M]

This happened last month. It was the first time I fucked some one without dating. It was also my wildest fuck.

I am 29 and I work in the marketing department of an IT company in the mid west. I broke up last December and I am in my current job for three years. Last June a guy joined the company as Test Lead. He is a single dad, divorced and has a daughter. Our company organizes lot of happy hours and we get to meet every one there. My colleague who is a technical writer introduced me to this guy. They were both working on the same module. The guy was testing the module and my colleague writes training manuals and helps marketing write descriptions. Read more »

The shy, quiet Uni girl, Part 3 (Long) [M/F]

Ok, so a few new developments since the last time I updated.

I was writing in a kind of weird way by talking about things that happened, whilst overlapping with things that were already happening, if that makes sense? I wrote my last one on Friday, but had been seeing her through the week and didn't speak about that, so this will basically catch up this entire week and I'll be back to the present.

We got back late Sunday night from our time away, and I kissed her goodnight as she went into her dorm. I didn't see her Monday until late in the day, because she wanted to catch up on all of the shit she had missed, which was understandable because she was really stressed about it. I was so proud of her for dropping it all and relaxing for a few days, because I know she finds it hard to do. We met up in the common room and we went to a pizza place just down the road, does an awesome Margarita. We held hands all the way there, and because she's pretty short she fits perfectly under my arm, its so great to be able to hold her close to me. Read more »

Update #10 – I [M] fucked my uptight roommate [F]

I didn't speak at all to Bernice while she was away but when she got back from NZ on Wednesday everything seemed normal – there was no mention of the argument we had last week. I got back from work and was just sat in the lounge watching TV when she came through. There was some small talk – I asked how her week had been etc. She surprised me a little by coming and sitting right on top of me and started to tell me how bad it had been. I listened for a bit but she was going on and on about how she hated home and her family and I got bored so I put my hands up her shirt and began feeling up her tits. She didn't really react and just kept talking, even when I pulled off her shirt. We did make out for a bit and I took off her bra and she took off my shirt but then we started just talking again. Read more »

Bad RA. (M and F)

When I was 19 years old, I was an RA for a program that helps high school seniors and juniors from low income backgrounds prepare for college.

One of my favorite student's name was Amalia. A grad from a particularly bad school district, Amalia was smart and funny, a natural leader. She was way further read than I was when I was in high school., but one of those overachievers who seemed unfazed by how much more put together they are than their peers. She was also cute as hell. Only about 5 feet tall with long, black hair she usually kept in a ponytail, big doe eyes, and the biggest, brightest smile I’d ever seen.

It was no secret to any of the RAs or to most of the students that she had a crush on me. I was the only one she ever asked for help on homework, even though she was way better at math then I am. When she was accepted to the most prestigious school in the state, she told me first. And when she broke up with her boyfriend, she cried on my shoulder. And she was constantly flirting with me, waiting for me to be on duty at the desk, changing into short shorts and tight tops when she knew I was around. Read more »

My Girlfriend’s sister wants to get pregnant [m/f]

First of all, sorry about the obvious, obnoxious username. I wanted MisterSister but some motherfucker took it already.

I'm newly graduated from college and I came home to my long distance girlfriend who was going to college local to where we grew up, so she could stay with her family. My gf is a pretty amazing woman, which makes what I've done even more shameful, but I am who I am.

She's [Sandy, like the hurricane] obsessed with getting the best transcript together possible so she can transfer from the local podunk community college to an Ivy League school. Because of this, Sandy is often busy with heavy loads of classes, being treasurer of the school, and working as a vet tech, while I increasingly have to be alone and realize I have no trajectory, post-college. I kind of live at her house most of the time, and though I have a crappy job in food service, most of my spare time is spent dicking around on reddit. Read more »

Becoming a bit of a slut. [f]

Alright so my first post was about being paid for sex from some guy I met on craigslist, but he wasn't the first guy I'd met, just the first that had paid. Oh, and I did end up seeing him again today. I "only" lasted 7 hours and so he didn't pay me the full amount ($700 instead of 1k – a little miffed since last time it was about the same, and originally he said it would only be 5 hours! But hey, still generous). My clit was way too sensitive and I couldn't bear the direct licks he was giving me, so we had to cut the session short. It was more of the same – making out intensely, being eaten out, fucking, cocaine (for him, not me). We did do a few new things: he pulled my hair hard which I surprisingly enjoyed, he got me to sit on his face which would have been nice but at that point I was too sore, and he tried to fingerbang me to orgasm since I told him I have never come from penetration. All in all a good day, but I'm pretty sure I have a cooch contusion and will probably have bruises on my butt again from all his biting. He's asked me to think of something else new that I'd like to try next time. I'm at a bit of a loss, since he's about as kinky as I've ever gotten. I guess I have some time to think about it while I recover! Read more »

[M]y first bisexual encounter [NSFW]

(PMs very welcome)

The situation first started a long time ago when me and my friend were in elementary school. Me and my friends used to have sleep overs and do the whole truth and dare thing, where we would get naked and jerk it, but never anything sexual with each other.

One of my friends was a year older than us, so he hit puberty first and a couple of times when it was just me and him, he would get his dick out and it was much larger than any of my other friend's that i had seen. Nothing sexual happened between us, I was just intrigued by the size of his penis.

One day as a joke he pulled it out in front of me and started stroking it for a few seconds while i just watched. He put it back in his pants pretty quickly. Nothing else happened from there.

Flash forward 8 years, and this scenario had been in my mind for years. I would jack off to this quite regularly, the thought of his hard penis and possibly getting off together. but i had a series of long term relationships so never said a word, and handled them as fantasies pretty well. Read more »

played! [mff] [fixed title]

This story has its genesis in real life events and real people. I've just imagined it going a bit further than it actually did. Enjoy!

I was in my mid-20's, in supreme physical condition, and in a relationship with Cass. Cass was a year younger than me, average height, brown hair, pretty face with an athletic build herself and an absolutely magnificent pair of DD tits that, at her age then, just sat there. She tended to dress plainly and conservatively but what was hidden beneath her clothes was simply incredible!

At this stage of our relationship Cass was, it must be said, sexually unadventurous. After we had gotten to know one another I had revealed some of my escapades in the past – which shocked her somewhat – and I think it wasn't until she really got to know a few new girl friends in our social circle that her mind was slowly opened to new and exciting possibilities. Hearing her friends talk of bisexual experimentation and threesomes she was becoming less shocked and more curious, to the point where she eventually started to bring these things up in our conversations as well. One night Cass had mentioned that she'd be open to the idea of, as she put it, being in the bed whilst I had sex with another woman. Read more »

First Step of Becoming a Real Sissy (M/m) (F/m)

Quick background before any of this. Yes, I identify as a femboy. A sissy. A trap. Whatever you want to call it. I'm bisexual and submissive to both genders with a tendency to fantasize about what I suppose are typical fantasies for someone like me. Well, most are typical. The others are, well, atypical. I'm 5'2 due to some strange twist of genetics, I weigh 120 pounds. I go to the gym as much as I can, though this has left me with a flat stomach and a bubble butt more than it has given me definable muscle. I've got rounded, a pixie cut, and a generally petite figure. To top it all off, I've got a below average manhood topping in at a "staggering" 4.5 inches. Until a few months ago, I was a virgin at 19 and this is the story of my first sexual encounter. Read more »