Category: gonewildstories

Bestfriends brother took my virginity [FM]

Let’s call my best friend Jemma and her brother, Karl. Jemma has been helping me be more sexual and more outgoing. I did a post on how she helped me get comfortable being naked around others. Her brother would help out and be one of the first people I did stuff with to become more outgoing.

Jemma’s plan from the beginning was to hopefully have her brother take my virginity. While she helped me become more outgoing and got me to use sex toys, she made sure not to do anything that would enter my pussy or ass, so I would be as tight as possible.

At one point of Jemma helping me become more outgoing we decided to make it so I wasn’t a virgin anymore. As you can tell by the title, Karl was the person that I decided to let take my virginity. We did stuff in the past but didn’t have sex, I gave him a bj and a handjob, he ate my pussy and played with my boobs and spanked me. I stripped down and layed down on the bed and rubbed my pussy a bit while Karl stripped down and once he stripped he entered his cock inside my pussy slowly and slowly went back and forth and slowly picked up the pace. He gropped my boobs and we changed positions every now and then. He ended up cumming in my pussy (we didn’t use a condom). After a bit of a break, he put lube on his dick and fucked my ass doggystyle, it hurt but also felt good. He cummed in my ass. Just like whenever I did something outgoing, we recorded it and took photos, and no I won’t share them.

Cheating on [F[ my bf [M] while on vacation

This was a long time ago, but I still think about it regularly!! I needed to get it out of my head, so here it is! Go to the (—–) to skip to the action.

We were in Cuba on vacation. Our friend group (6 of us in total, ranging from 21-25 and 3 boys/3 girls. Two couples, my boyfriend and I and Dave and Maria. The other 2 aren’t relevant to THIS story ;))Anyway, we liked to go to Cuba every summer, since it was so cheap for us Canadians. This was our 3rd year going as a group, so we were all very close and comfortable with each other.

At the time, my hair was like a caramel blonde (typical ABG look these days) and was the fittest I’ve been my whole life. I have an hourglass figure and my body was in great shape during this trip. I’m Filipino/white and have really golden tan skin in the summer.

Some back story… Dave and I had an affair a few years before this vacation. (That’s a whole different story.) But at this point, we were back to being best friends with **no** benefits and generally had healthy relationships with other people and each other. We never talked about what we used to do and obviously nobody ever found out. We were “normal” and acted like so. Read more »

Story time 2 [MF]

When I was in highschool I think it was either grade 9 or grade 10 I had a crush and one day my crush walked into class and she had a BIG red mark on her neck and someone which was one of her friends shouted what happened to your neck did you get a hickey? As she was approaching her to sit down (because they sat next to eachother) And she signaled for her to shhh and I overheard my crush saying that no she just got allergies or sick I forgot which one she said I think she said she got allergies though. And she said it in a decently loud way so others can hear it to so I think she was lying. It definitely looked like a hickey.
Another story time of mines: https://www.reddit.com/r/confessions/comments/ir33ot/story_time/

I [m] secretly know my wife cheats but I like it.

I am married and closeted bisexual. I travel a lot for work. My wife has a high sex drive and is a total slut which really turns me on. She is also really homophobic. But secretly I love playing with another mans dick and tasting cum. I often play with men when I’m away. When I’m traveling she will sometimes gets mildly depressed cause all her sex toys just don’t do it for her after a while (see likes to fuck). This last trip she got a little more depressed that usual but then about a week into my trip she was happy and chipper. I didn’t think a thing of it. When I get home 3 weeks later she is still happy and wants to fuck and I go down on her. As I’m eating her out I tasted a familiar taste. Someone had recently cum in side her. It was so arousing I probably would have gotten off just eating her out. But she was also very stimulated just by me eating her out and orgasmed so many times she was getting overwhelmed and need to stop for a brake in action. When we did start fucking, think of her cheating on me and then letting me eat her out, go me off quick. I’m really enjoying this I can’t wait till my next trip. Eventually I’ll tell her I know but for now i want this to keep going.

[MF] My first date with a stoner chick

This story is from a particularly chaotic phase of my life that led to many bad decisions, also known as my 20s. The story is completely true but certain details may be modified to protect the parties involved and because my memory is shit sometimes. Anyway I met Gina where I meet most women, on the world wide web. She’s the type of girl that has a meme for her profile pic and if you really investigate you can find like 4 pictures of her on the entire internet. Very understated beauty, not really interested in showing herself off. I found that compelling and I also wanted to get laid, so I reached out to her.

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If I could describe Gina as succinctly as possible, I would describe her as a 5’2” petite, Mexican girl with a shaggy, dark pixie cut and the soul of Kurt Cobain trapped inside her body. Her clothes, her hair and her living quarters were all grungy as hell. She looked like she smoked more weed than she ate food. All I knew about her was that she liked to draw intentionally ugly comics and she had the most stunning brown eyes I’ve ever seen. Read more »

My First Time with Wendy [MF]

I met Wendy through an add I posted on Craigslist looking for a friend with benefits. She was newly separated from her husband, but still having sex with him while looking for someone else to transition to. She and I hit it off and soon we were chatting non-stop and had decided to meet. Our first meet up was actually just hanging out and cruising around town. More probably could have happened but were both too nervous to make the first move. Funny/scary moment of the night, she and I were walking around the downtown area and ran into some friends of my wife and I. I introduced Wendy as a friend and chatted for a bit before moving on.

After that first night we both agreed we were interested in more, and would have been willing that night. So we agreed to meet up again with full intention of having some fun. I made up an excuse to leave the house one evening and drove straight to Wendy’s place. I got there and we sat in the couch watching TV for a little while before we started making out. We made out for a while, hands exploring each other’s bodies. I was groping at her tits as she was rubbing my cock through my jeans. Read more »

My first MILF and second married girl I hooked up with, she [F] was 27, I [M] was 34

So I met [this girl] (https://imgur.com/gallery/zr6YAv4) on the whisper app. She had posted about hooking up with some guy at a hotel when she was traveling for work. She told me how she was too drunk to remember much other than him being older than her. We talked for a few days then started taking on Snapchat when we found out how close we lived to each other (within an hour). She told me how she previously had a regular guy she was cheating on her husband with but that he became too clingy so this guy at the hotel was the first she had hooked up with since about a year. I didn’t go into our conversations trying to hook up with her, just talked with her and when she shared a picture I made she to tell her how much I enjoyed them (she started to send nudes, I still have those and may post later). She was always teasing me with her cleavage, pulling her top down while she was sitting at home with her husband, unaware of what she was doing. She had the best tits, I honestly thought they were fake, they were so perfect. Read more »

Spring Break PCB, 15 years ago [MF]

2 years in college for spring break, me and a group of friends trekked 20 hours in a van to spend a week at spring break in Panama City Beach Florida. Prior to the recent local laws, it was THE spring break party spot. We stayed at “the mecca” – Summit Condos– right outside our balcony was the beach stage that had music pumping all morning and afternoon. Next door were the two main attraction bars – I think they each held somewhere around 1000 people each??

The group of friends would rent 2 rooms, 8 people – one for guys and one for gals. Other groups were there too from people from the same university. I stayed in one room and my girlfriend (Sara) stayed in the other. We were great with each other – loved to be with each other, but we were never clingy to one another. We could float around and chat with whoever and there was no jealousy. We really didn’t get too worked up about what the other was doing/not doing. Read more »

My first pickup at a bar [MF]

I walked to a bar near home on a Sunday night, not expecting anything except getting drunk and stumbling home.

By drink number 5 I felt like a cigarette. I got one out and realised I didn’t have a lighter. I looked around and a bunch of rowdy middle aged guys having beers and smoking caught my eye. I went over and asked for a light.

There was an empty seat at their coffee table that I sat myself on uninvited. All of us being pretty buzzed, they didn’t object and we got taking.

Enter their younger, hot female friend and colleague from the restroom. A warm wide smile, petite, long black hair, big but perky tits outlined by her tight tee shirt, slim waist and broad hips, and skinny jeans to match.

They introduced us, she said hi and sat herself right next to me on a massive couch with plenty of room. Our sides and legs were touching. I said good to meet you and we locked eyes for a second before she replied. I knew immediately there was chemistry between us. Read more »

I posed naked for a photoshoot with my husband’s client [FM] 33

My husband is a fairly successful real estate agent. Recently he sold a home to an established photographer who kind of casually brought up the idea of doing a boudoir/nude photo shoot with me as the subject. Somehow he phrased it like he was doing us a favor and somehow my husband was totally onboard with it! Long story short I agreed to it and for several hours one random Saturday I was completely naked for another man. A wealthy, older, attractive man I might add lol.

There was a lot of sexual tension in the room to start with but once the lingerie was completely off he instructed me to put some baby oil on. As I was applying it on my front he took the liberty of getting my backside. I was super surprised and super turned on by his assertiveness. He kind of disguised it all as being part of the photoshoot but as his hands lingered on my butt it was clear what his intentions were. Read more »