Fantasy Archives — Page 1050 of 1135 — NSFW story

After a week away from my fiance [mf]

My fiance’s groomsmen took him on a camping trip for his bachelor party a few months before the wedding. While they were gone, he and I were talking about sex a lot via text. The subject of fantasy came up, and we started talking about all of the things we’d like to try. The whole week he was gone, we drove each other wild with stories of threesomes, sex in public, orgasm denial, restraint and more. I was also posting pictures and videos of myself on Reddit, and he was going insane over the messages I shared with him from my inbox.

I’m pretty sure I was dripping wet the entire week he was gone. I bought a new dildo about three days in and fucked myself with it over and over, while wearing the butt plug I had also purchased. This was the week I discovered my ability to squirt.

Finally it was the night he was coming home. We had decided that from the time I picked him up until the time we got home (about an hour), he would be in command and I would do whatever he said. Read more »

[MF] Sex with older, former co-worker

During and after college, I worked at my neighborhood supermarket. After I graduated, it was a much more miserable experience, but you bond quickly with other employees. One of which, was a middle aged single mom that had some similar interests as me. Those interests included sex.

Off the bat, she wasn’t a cougar. Pear shaped body with a sizeable ass, not bad looking, but not exactly pretty either. She was about 17 years older than me. We shared a love of science fiction and fantasy, so we had that go on when we had smoke breaks together. She also had a really blasé attitude towards sex, and would speak casually about it when brought up.

Eventually, I got a new job, and I promised I’d keep in contact with everyone, which was a lie. She friended me on Facebook, and said to hit her up some time. She then would message me randomly, and it became apparent quickly she wanted to fuck. I always had a thing for older women, and it had been a while, so I thought, hey, why not. Read more »

The Royal Garden 04 (spy genre) [MFFFF, bdsm, mdom, fsub, orgy, reluc, fantasy]

My [F] first tranny [TF]

There’s a tranny chaser up in here…

It’s me. I’m the tranny chaser. My entire sexually-active life I’ve had a very distinct interest in all things gender bending, androgynous, trans, drag, and cross dressing. I know very specifically what I’m into and it’s hard to make the stars line up in my favor. But, it finally happened. She contacted me as her male self on Plenty of Fish, which on my profile states I’m into TS/CD so she felt comfortable telling me right from the start she was a cross dresser with interest in going full-time. I’m feeling it. I’ve had men approach me before that cross dress in the bedroom, just lingerie and panties… that’s not my deal. I mean, I like those things too, but I want it to be more than just a sexy bedroom activity. Like fisting, or crying about my dead father. Read more »

Our first threesomes [MMF][MFF]

So my BF and I have been together for 5 years now. I’m 24 and he is 25. We have a very good communication when it comes to sex and in general as well and I would describe our relationship as spicy (from anal to squirting we do everything). He has been the one bringing up most of the topics but I ended up always saying yes and actually sometimes being even more desperate to try. For instance he actually said we should record ourselves but I was the one taking the camera the first time. He said we should put it online and I actually created our amateur account on some famous site. Anyway, that’s not the point.

Two years ago, be brought the topics of sex with multiple partners, that is going for MMF and MFF and even just fucking with other couples. At first I was a bit shocked but then I kinda understood him but the project stayed a project till very recently. Both of us wanted it but both of us also knew we would be jealous and we would not stand it.

But we figured out that we could probably do it anyway. That’s how we proceeded. Read more »

Late 40’s [F] and the college boy [M]: A first for both of us

Just discovered this subreddit recently and I’m a total nube to writing about my experiences–so hopefully these won’t be a waste of your time. Please be gentle!

Should probably start with a little explanation. As I was growing up I was tall, gawky, had glasses and an overbite. Then I was a wrestler 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 I still have the perception of myself as a gawky kid with glasses and can still be somewhat shy until engaged and alternate between overconfidence and no confidence.

I remember hearing my dad and his buddies laugh about how ridiculous and unrealistic “I can’t believe it happened to me” letters that were in Penthouse (or Playboy? Both?) and that’s kind of how I feel about the experiences I’ve been fortunate enough to have–I don’t consider myself overly sexual or deviant, but I’ve somehow managed to have a lot of encounters that, upon reflection, are large in volume (everything from college girls to probably an unusually high amount of milfs/cougars) and kind of unusual (in semi-public rooms, fingering under the covers in front of the girl’s family, threesomes, with food, tying up, and so on) and seem like bs. Read more »

Memories: Emily. Blonde, drunk and willing. I’m only human. [MF]

“If you’re going upstairs, be a dear and help Emily get to her room? She’s wasted.”

I shrugged. “Sure.” I didnt really give it a second thought. Well, maybe I did, but that’s just the way my brain works. I’m not going to lie. Emily is the one every straight guy thinks filthy thoughts about. Blonde. Curvy. A mix of girl next door and pornstar. Too much makeup and just enough skin. So obviously I had thoughts. How could I not?

But they were just thoughts. Even when she had her arm around me in the elevator for support, her firm breast pressing against my side… they were just thoughts. Filthy snippets in my imagination, called upon for masturbatory purposes. Yes, I was guilty of gazing down into the chasm of her cleavage. Yes, I did breathe in her flowery scent. But my intentions were pure. Pure enough.

I took her to her door and waited while she fumbled with the keycard. Leaning against me, giggling to herself. I walked her in, unhooked her arm from around my neck and watched her collapse onto the bed, face first. “Safe and sound.” I muttered proudly to myself as I started to back away. My eyes might have lingered on her pale thighs, her short skirt hiked up just enough to offer a glimpse of that intersection of leg and buttock. Read more »

The time I realised we really werent exclusive part 2 – AKA Shame, sloppy seconds and almost anal [MF]

A continuation of this: https://www.reddit.com/r/gonewildstories/comments/58yu30/the_time_i_realised_we_really_werent_exclusive/

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We went to have drinks with some of her friends in a shitty student flat that night. She’d warmed up a bit, but was still annoyed. Drinking games ensued, so it didnt take long for everyone to get drunk. At some point some random lanky guy arrived. After rolling a spliff that almost knocked me out, he said something about “needing some help” and she got up and followed him. I thought nothing of it.

And then, a few minutes later one of her girlfriends, Fiona, said something. “It’s cool that you’re so cool with it”. I smiled and said thank you, stoned and confused, wondering what I was cool with but accepting the compliment anyway. And then another dude appeared and asked where Darren was. Fiona casually replied “getting his rocks off… they’ll be done soon”.

All the pieces fell in place like a satellite crashing back down to earth. Darren was the sex god in her phone book. Darren was the lanky dude who “needed help” with something. I was apparently cool for being cool with my lady fucking another guy while I sat around in the other room. My head spun. I played it as cool as I could because I wanted to compliment to stick, but it wasnt easy. About twenty agonizing seconds later I excused myself to look for the bathroom. Read more »

[F]inally made a [m]ove on my boss

This is my first time posting here, so be nice. It’s kind of long because there’s a lot of background info and I’ll be honest, the action isn’t nearly as exciting as most of what I’ve read on here. But you be the judge.

I’m a 26 year old woman working in marketing/advertising. Ever since I can remember, I’ve fantasized about hooking up with someone in an authority position over me. I always fantasized about my professors in college, and for the last year I’ve fantasized about my boss.

Andrew is 32 and tall, dark, and handsome. My company is relatively small (only 30ish people), and everyone is pretty young. I’m also the only woman who works there, and luckily I get treated with the same level of respect as all of the men, and none of my coworkers have ever creeped on me or made me feel uncomfortable.

So anyways, my first month working there I decide I’m very attracted to Andrew. I immediately start thinking of him when I masturbate, picturing us on his desk, etc. However, he was my boss and he also had a serious girlfriend so I didn’t think it would ever happen. Read more »