Category: gonewildstories

Anal Manoeuvres in the Dark vol 2 – I [M] did it again with my colleague [F]

The first story – https://www.reddit.com/r/gonewildstories/comments/56arer/anal_manoeuvres_in_the_dark_how_i_m_fucked_my/

So in the 3ish years since the events in the last post took place, a few things had happened – I left the company, then rejoined at a higher role. I had loved and lost. Kat had been promoted, but had also spent some time apart from her husband. During this time she had put the weight she initially lost back on, but then lost it again and more.

Since I wrote the last story, the thoughts of that night had been bouncing about in my head (that’ll happen when you’re single!). Kat and I had still never spoken about that night, and it got to the point where I wanted to mention it, I just wanted to know what she thought of it or if she even thought of it at all. About 3 weeks ago, the planets aligned and I got a chance. Read more »

[F]irst, [M]aybe Last pt. I

My first post, and part of my backstory is [here](https://www.reddit.com/r/gonewildstories/comments/4mlzi2/my_try_at_bi/).

Caution: this one may be a bit long due to the need for setup, but hopefully you like it….

So this is about “Natalie” and our series of flings that, aside from the first one, were everything I could have hoped for.

I met her on the web, a few years (8) older, short, redhead. About average weight, nice smile, piercing green eyes. One of those times where you’re sent a picture and you think “well, how real/old is this picture?” Our emails/texts were fun, flirty, equal parts of ‘vanilla’ and explicit. So I expected our first meeting to be pretty awesome.

Well… the pics checked out, in fact, one of those “hotter in person” scenarios. Anyway, we met at one of those chain restaurants with the “2 for $xx.xx” type deal. We were at the bar, she got there first and had a male friend with her, just in case *I* turned out to be the crazy one…. Read more »

[MF] How I Got Started With [Cheating]

I LOVE women! To be specific I love the smooth curves and the way a woman tastes when she’s aroused. The first time I cheated was after my senior year of high school and we were all 18. I’m 31 so the new thing back then was the cell phone. Your average flip phone with a shitty camera. This little invention has been my best friend for cheating and keeping it secret!

Senior year I was dating a girl named Kate. It was a lot of fun, she was tall (5’8″), big smile, great boobs and an ass built for a thong! Loved to have sex on her pool table or outside during the summer on the trampoline. However Kate had a lack of confidence and would cry sometimes from being over emotional about us in the future. I don’t deal well with emotions, crying or indecision so I decided to test the waters and see what type of women I could find. Where do you look for your next girlfriend at that age??? It’s school and specifically it was the girl behind me in homeroom and who lived near me. Her name was Jamie; she was athletic, fair skinned and had this blonde hair that smelled like love in a shampoo bottle. What do you do then because Kate also went to the same school and people talk? You enter Jamie’s cell number into your phone and you put her in there as something believable i.e. The Marine recruiter who signed me up. Read more »

Between Classes [MF]

A Race and Gender Politics freshman level class at a large university in the Midwest. Spring semester.
Dennis Tominsky, a freshman nineteen years of age, comes in to class late, as usual. He sits at his regular seat while the teacher glares at him. The teacher continues. Dennis has a smirk on his face and glazed eyes. Yup, he’s fucking high. He’s been baked pretty much since midnight last night, when he had a pot brownie left over from his pal’s party, plus a joint, plus a bowl. He didn’t get much sleep that night. He was engaged in certain other, er…recreational activities.

Dennis doesn’t take out his notebook or anything. He takes his backpack off, but he has an agenda in this class other than studying. He stares straight ahead, still with that smirk, his mind elsewhere, and turns to his right. He looks down his row at—

A fairly attractive girl in a white silk blouse. She wears a brown skirt and leggings. She does take notes. But something happens to her positioning once Dennis walks in. She doesn’t have to look at him to know he’s there. It’s only when she feels his eyes on her that she returns the gaze. She smiles only faintly. There’s a tinge of nervousness in the smile. A tinge of regret even? She goes back to taking notes. Dennis turns away from her. Read more »

[M] I can’t shake these thoughts from this past weekend away with my wife

My wife and I just got back from a 10th anniversary weekend getaway. We went with my friend and his wife who also celebrated their 8th. Theirs is two days apart from ours.

A few weeks back I posted about me catching my wife texting this guy friend nude photos of her that her and I take of her in the bedroom. She’s an attractive woman. Long sark hair green eyes, big breasts, etc. We do it for fun. We fought for a few days on her sending hem to him and things cooled down with it.

Anyway, we all spent the weekend away and had a good time. What came over me in my mind the whole weekend, no matter where we were and what we did, I had constant thoughts in my head of my friend fucking my wife. I know this probably stems from some “fantasy anger” from the pics incident, but I’m not sure. Examples: We would all be sitting in the cabin around the fire on the couches, and i would think about her sucking his cock while i watch. We would be in bed at night after they left to go to their cabin, and I would think about my wife sneaking over there and taking a pounding from him. We go out to breakfast in the restaurant, my wife wore boots and a denim skirt, and i would thing abut him sitting next to her with 3 fingers in her pussy. Read more »

Boss made me his little whore for the night [Group]

I’ve mentioned to my boss multiple times about being in group sex and having people from other rooms watch. He’s called bullshit on it several times and I told him to setup something. That’s what he did Sunday.

He texts me on Sunday and wants to know if I got a couple of hours free that evening to ‘prove myself’ when I find out what it is, I agree and he comes to get me.

Setup was interesting. Two hotel rooms, joined together but a camera in the one I was in to the other room. He took out all the lightbulbs from the room I was in except for the bathroom light. Ordered me naked and turned the AC as cold as it would go. I asked him how many guys and he told me I’ll learn to count.

The rules were to sit at the edge of the bed, looking at the door. When someone walked in, tell them you’re horny and ready to be taught a lesson. I was cuffed in between sessions and if the guy didn’t want to, he didn’t have to uncuff me. I’ve had group sex before, multiple times. I’ve been used as an object for another guy before and enjoyed it. But I was kinda nervous. Read more »

Leslie and Anne at the Lesbian Club [MFf] – BDSM

I liked Anne the first time Leslie introduced me. They are married now and I noticed quickly how different Leslie was with Anne than some of the other gf’s and flings like Diane. With Diane, Leslie was cruel, mean spirited and used my cock like a weapon. Anne came later. With Anne, Leslie dominated her, but treated her like a prize. I played with them much less often than I had with her and Diance and Leslie used my cock as a tool.

I had not done much with Anne. I had felt her a bit and Leslie had made her jack me off at one point, but I hadn’t even gotten a blow job. In fact, Anne could boast that she had never had a penis inside her body. That she was one of the purest lesbians she knew. Tonight would be no different.

As to her “purity.” She teased Leslie about it. She had spunk and I liked that. We’d be hanging out and she’d call Leslie a “stained” lesbian or make fun of the fact that she sometimes fucked me. Of course, Leslie would fire back that one day she’d have me fuck the sub. Still Anne didn’t let herself get cowwed. I was dating Stacy off and on at this time and Anne reminded me of her. Submissive but spirited. I seem to have a type. Read more »

I [F] had sex with my shy boyfriend[M] and his reactions were adorable

My boyfriend and I have been dating for about 9 months. We hang out at least twice a week. Whenever we hangout we spend most of out time cuddling, kissing and talking.
Before I continue, I should tell you a bit about him. He is a virgin and I’m not. I’ve only have had sex once when I was in highschool(The guy went in and pulled out immediately, but I didn’t really feel it, so it doesnt count :p ). He is shy when he’s in public but he’s very sweet and the nicest guy I’ve ever met. He’s always there for me. He’s little nerdy. Whenever we get really intimate he backs off a little. For example, last month we were spooning(Cuddling, no penetration) and I got really close to him but he pushed himself back a little. Whenever he touches my butt by accident, he always says that he’s sorry.

So on to my sex story Read more »

[MF] Me getting fucked in the kitchen [squirting]

It was around 1am on a Saturday night, when my boyfriend [24] and I [23] stumbled in the door from a night of drinking and laughing at a friends house. It was the typical, once a month, spur of the moment get together. Topics included music, sports, arguing over politics, more music, and as everyone increasingly feels the liquid courage in full swing, sex becomes the topic. Anything about it, really- preferences, positions, kinks, jokes, etc.

It always strokes my ego a bit when I over hear my bf talking about our sex life. It’s like getting an A+ on a test you studied hard for. That night, the topic was especially interesting for me because it was about something I had only recently “achieved”; squirting. Hearing him boast about the waterfall that my pussy turned into just merely a week prior was arousing me. Another hour of alcohol-fueled sex talk and I shot him a look. He must have known by the look in my eyes that I was restless to get home. The drive back home is only about 12 minutes, but it felt like an hour and 12 minutes. The combination of the vibration of the car and his hand lodged between my two thighs was making my clit throb. Read more »