Category: gonewildstories

I think about having children a lot more than I used to…[MF]

I found Erin on AFF. We were both in our early twenties. Before I decided to message her I perused her profile. Her pictures were cute, cute enough to  make you wonder if there’s a real person behind that account. Her blog of experiences in the lifestyle caught my eye. Topics range from ‘what’s it like to be the only unicorn in existence’ and ‘for real single men, get your shit together’.

We started chatting and eventually graduated to texting and then a voice call. I wish I still had the pictures she sent me from our initial chat. In them, she was wearing a black corset and the most adorable velvet choker. She had a little thing for soft BDSM; something I hadn’t explored in the slightest, at the time.

That night we talked on the phone got to know each other a bit. I asked her what she wanted and what she was doing on AFF. Her response aligned with my lifestyle. She pretty much reiterated my response to the same question when she asked over instant messenger: no strings. Purely sexual relationship if we click and like playing together. I don’t think I consciously caught it at the time but in hindsight I have always believed that she wasn’t completely honest with herself or me. – more on that later… Read more »

I [f] have made my dorm mate [f] my sex slave

My entire sexual life, I have been the submissive girl, clean up girl, the mindless fuck toy. And I love it. I won’t give it up. But I’ve never been in a situation where I could be in control. Until now!

I got a new dorm mate last month. And she was a very shy virgin who only kissed a guy once. She never even jilled herself because she was too nervous she’d get caught. She noticed me whenever I would stay over some of my outfits, toys and stuff so she would ask questions. I’d honestly answer.

One night I’m laying in bed and she comes in the bed with me. I turn over and just look at her nervously try to kiss me. I kissed her and it lasted a bit. I asked her what she was doing and she wanted me to show her a good time. I made her strip down for me and I ate her out. I made her sleep naked that night and every night after. She hasn’t broken that rule.

I realized she wanted me to control her. In fact she said once after a couple of nights she wanted me to use her sexually. Read more »

Brewing at the office [MF]

I’m a guy in his early twenties who works with a small team. I’ve always had a preference towards older women, whether that be teachers, friends mom’s, or celebrities. So, when on my first day, I met the woman I was starting with, Marie, a pretty blonde, single 48 year old year old, my head immediately began drifting off onto the possibilities.

Marie and I have developed a very open friendship, talking about sex, porn, and relationships. Lately, things have begun to feel a bit different. Yesterday, she asked about how my sex life has been and I said nonexistent, which leads to today’s event.

Upon walking into the office this morning, I greeted Marie. She immediately groaned a bit so I asked what was wrong. She complained of a painful knot in her neck. After talking for a few more minutes, the groaning continued until I volunteered to help her out.

I stood above her and began massaging her bare shoulders and neck. The groaning turned into moaning. She kept whispering how good it felt and asking for me to go deeper and then mix it up with slowly scratching or tracing my fingers along her smooth skin. Read more »

[M]et up with a [m]arried panty boy

We started texting after some back and forth online. Real texting. Not kik. Because I don’t see the point of app that replicated what my phone already does.

But when you have each other’s number that just adds an extra lair of temptation. When your cock is rock hard and you’re on the edge would you rather text about it…or listen?

It didn’t happen that often. At least not at first. He had to wait until his wife was out of the house. But then we’d start texting.

Sometimes he’d tell me how he fucked his wife. Or I’d tell him about the women and men I’d fucked lately. We’d talk about his fantasy of being cuckolded.

He’d talk about his wife panties. How he liked to stroke in them. How he’d love me to cum in them while he watched.

Sometimes he’d admit he was curious about sucking cock. Or being taken by a man.

The calls were never that long. We weren’t looking to become pals. We both had a need. There was an urgent intensity. Within a few minutes we were jacking off and cumming together. After that we’d quickly get off the phone until next time. Read more »

[MF] I slept with my high school crush…

This one’s going to be a bit long but, hopefully, worth it.

This happened two years ago and to this day it’s been my most fulfilling sexual encounter, if my most shameful.

I was 24 at the time, a slightly bigger guy with a decent build. Enough to give me self-confidence issues but not enough to make me hate myself. I got a text out of the blue from a girl that I knew from high school, we’ll call her Marissa.

Marissa and I had a couple of classes together in high school, and the classes that we did have had very strict seating policies. There was no opportunity to ‘move where you pleased’. But as fate would have it, we ended up sitting next to each other in some fashion in each class.

She was this lanky, awkward girl with the type of hair that looked more at home in the aftermath of an explosion than on a head. It was brown and curly and everywhere. We talked endlessly about anything and everything, and it was a miracle that we were never separated. Read more »

Sharing a FWB for the first time Pt 2 [MFF]

Realized that I never posted the other “part” of our threesome experience.

We had a threesome with another guy & she agreed to another girl. Luckily she was true to her word.

We actually got lucky with another girl we went to school with at the time. Since we were only FWBs, we had agreed that if we wanted to see other people it was fine. I had hit it off with a girl who was a theater geek (Gabby). She was latina, curvy and pretty tall at about 5′ 10″. We had texted back and forth a bit, eventually getting into sexual stuff. She asked what was the wildest thing I’ve done sexually and I admitted to the previous threesome. She was surprised and admitted that she had wanted to try one someday. I jokingly had said “even with another girl?” and she just replied “lol yeah.” At that point, I was convinced we found our 3rd. I mentioned it to my FWB and she didn’t know the girl but thought she was cute enough and was down if we could talk her into it. I was halfway there! Read more »

[F]. A wild 3some, and my first fisting.

I met this guy at a friends party and wet for it off right away. He was from Boston, working in Montreal on a contract. I ended up sleeping with him that night back at my place when he drove me home.

The next day he tells me that he has a girlfriend, but that they are in an open relationship. I didn’t honestly buy it, not did I really care. I wasn’t looking for a bf and in do enjoy my 1 night stands. It’s not the first time that I sleep with married guys, and it never bothered me. In my opinion if they don’t cheat with me, I’ll be another girl.

Anyways, sex was very good with him, so when he asked if we could see each other again, I was fully up for it.

This went on for about 4 months. Seeing him a few times per week. We would go out for drinks, dinner, sometimes it was just sex. Basically a sex friend. He kept taking about his GF and insisted that she was OK with him sleeping around and that in fact he had talked to her about me. Again, I pretty much ignored the conversation. I didn’t need him to justify his actions. Read more »

[MF] Came inside the cutest girl I’ve ever gone out with on the first date part 3 – filled her with cum in the backseat of a rental car

You can find the first two parts here.

This happened this past weekend. I rented a car to go on a hike with some friends, and Elizabeth told me she would be off work late at 11. I offered to pick her up for some ice cream and she was all for it.

I show up and despite it being almost midnight, she still looked really cute in her hoodie and jeans without any makeup. As soon as she gets in the car, she starts kissing me enthusiastically. At this point I’ve gotten pretty good at making her flustered by pulling away, so I do just that. She gives me her normal little pout and we go get ice cream nearby, making sure I tease her with tiny make out sessions in between.

We pull into her work’s relatively empty parking lot and instantly can’t keep our hands off each other. I start massaging her thighs and inch my hand closer to her pussy. She’s more comfortable with me and aggressive this time, and surprises me by instantly undoing my belt and massaging my cock under my pants. I can’t help but moan, which just makes her stroke me faster. Read more »

Had [M]y way with a virgin sissy in a Dallas hotel room

Playing with people on Reddit is damn near impossible. If you find someone near you or just willing to play virtually there is a higher than they flake out than on any other platform. Fetlife or Tinder are much easier. But there are less people on Fetlife and less kinksters on Tinder. So I end up here.

Lena was posting pics when she first caught my eye. This wasn’t the normal guy in panties stuff. These were full blown photo sets from the lips down. Skirts. Blouses. Dressed. Heels Stockings. Lingerie sets with matching garter belts. It showed dedication. I noticed we were in the same city. And so I messaged and we started chatting.

Some elements of her story were typical. She liked to dress up. She was curious about men, but had never been with one in any capacity aside from a little oral exploration, but that was way back in college before she started dressing up.

I was more fascinated by the atypical things about Lena. That she’d first started crossdressing when a girlfriend has requested it. That the woman had taught her how to dress and do makeup. That she’d been fucked with a strap on regularly. Read more »

[MF] The One (And Only) Time I Cheated: Sleeping Between My Ex-Girlfriend And Her Friend

When I was 18-years-old, I landed my first legit girlfriend. I say “legit” because I had dated before, but never started a relationship. Tara was one year older than me at 19 and played tennis at a small college three hours outside our hometown. We had been friends for a year or two and then one day we were like, “Hm. Maybe we should fuck,” and that was the start of a beautifully dramatic relationship. Tara’s best features were her legs and ass. I suppose it was all the tennis. She had smaller than average tits and a pretty standard face. I DON’T KNOW IF THAT SOUNDS MEAN! It’s not meant to be. Obviously I was attracted to her.

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Our one year relationship was a tumultuous one. It was long distance for the most part as she was in college and I was still at home. Admittedly, since I was just an 18-year-old little douche, I was a bit jealous. I thought about all the guys at her college. All the older dudes who were probably more experienced than me. My silly paranoia created a few fights, but I wasn’t the only one adding unnecessary stress to the relationship. Tara had some personality disorder. I’m not going to claim to know the specifics behind it, but her father was a high-functioning alcoholic and her mother was out of the picture. She, understandably, had some issues. Read more »