Sniffing [M]y [F]riend’s panties led to the dirtiest sex of my life Part 1

Long backstory, skip to ***** for the sex. There will likely be 3 parts to this.

In my opinion, there are two kinds of cheating. The more “understandable” kind is when there’s a dead bedroom, dead relationship, abuse or neglect, etc. Then there’s just people who for whatever reason can’t keep it in their pants. This is sadly the latter in my case, and I make no claims that what I did was right. As such, please leave any moral judgements to yourself.

Description of the players. Me: married with 5 kids. 5’10, average build, shaved head with a closely trimmed beard, average dick. I try to work out, but 5 kids makes that pretty difficult, so rocking a moderate dad bod. Jackie: married mother of 3, hostess for the event. 5’4, petite build and straight brown hair that reaches to just below her shoulders. Small a-cups, but a FANTASTIC ass I often fantasized about.

[MF] Her first big dick blowjob and she loves it

So I was hanging out with this girl, lets call her Dani (real name different of course). I met her at work where we run the bar together and end most nights super late and tired. Dani is a super chilled out cute brunette girl, about 5’8, really nice medium sized boobs and a real peach of a butt, very cute and perky. She was such a guy too, she would always joke around with us at the bar and her vibe was always so appreciated by everyone. I had such a crush on her but I was 20 at the time and she was 25 so I basically assumed that I had no chance with her…

Semi-public sex outside and in a car [FM]

This is about the same guy (m21) from my last post. We were spending the weekend together and like usual, it had been weeks since we had last seen each other so we could not get our hands off each other I’m telling you. We had a dinner date planned for the first night so I (f26) dressed up in a cute thin slip dress that stopped just above my knees and draped over my curves perfectly. I was wearing an equally thin, unpadded bra beneath it which allowed my nipples to poke through both layers of material. I knew my breasts looked good in it (although they look good in almost anything ngl, I have nice tits.) The silkiness of the dress against my skin made me feel so sexy and I debated on not wearing underwear but ultimately decided to wear some since I can get extremely wet. It wouldn’t take much to soak through the dress, especially without the added layer of underwear. My man was dressed in a collared shirt with the sleeves rolled to his elbows (ladies am I right when I say that is a LOOK or am I right??) and a pair of well fitting jeans that brought my eyes straight to his ass. The ass on this man is a gift from the heavens lemme tell you.

[f] Master’s challenge Day 2

Today was 20 minutes of edging and decided to re read a roleplay my master and I had. It was one where he and I were exploring knife play. Oh my god….I was only about 10 minutes in and I felt like I was going to cum so….I turned my vibrator down to the lowest setting I could and barely touched my pussy,but still enough to feel the vibration. I bit in my blanket and continued to do so for the next 10 minutes and I thought I was going to explode. I didn’t though, Day 2 complete. Victory will be mine. Be back for day 3 of my challenge. 21 minutes hehe.

[MF] I’ve been fantasizing about a guy I met before quarantine and it’s driving me crazy

Hi, I’m Andrea or Ann, whichever you prefer :)

I usually keep this stuff in my personal journal but my latest escapade might be exciting enough to post here! Please excuse some of the weirdness and incongruity that might appear, I’m essentially editing together multiple journal entries from different days into one big chunk!

I work in a downtown space that shares buildings with a bunch of other companies so there’s always lots of people around. So I know a few people, recognize a *bunch* of people, but am only familiar with a small group.

ANYWAYS. Who cares.

Just before the virus got really scary, I ran into a new guy at the building that I was *immediately* attracted to. Right away he was bantering back and forth with an easy confidence. Such a turn on. I razzed him about the tie he was wearing and he just immediately played it up and we laughed together. He asked me if I wanted to have lunch with him. Too bad, since I was already having lunch with my mom that day.

[FM] My [18F] first time having someone [22M] fuck me with a strap on [trans]

[I hate writing notes at the beginning of stories, but this one is important. Before you write a transphobic comment questioning or joking about Ben’s gender – don’t. Just don’t. Trans men are men. Trans women are women. Transphobia and/or fetishization will not be tolerated in the comments. I’ll be monitoring them closely, and I will block and report you faster than you can say “[J.K. Rowling](https://www.thetrevorproject.org/2020/06/08/daniel-radcliffe-responds-to-j-k-rowlings-tweets-on-gender-identity/).” Happy to answer questions if they are politely phrased and coming from a place of genuine curiosity, but you have to remember that I am not trans, and I am not representing the trans community. [Here](https://www.thetrevorproject.org/resources/trevor-support-center/a-guide-to-being-an-ally-to-transgender-and-nonbinary-youth/) is a good introduction to being an ally to trans and nonbinary people. Enjoy the story!]

From the moment I met Ben, I thought he was hot as fuck. He wasn’t much taller than I was, but he oozed confidence with every smile. It helped that he always dressed like a French author on a jaunt on the Riviera and generally looked as if he belonged in a black and white film with a cigarette dangling from his lips and a typewriter in front of him. His short blond hair was always coifed, his scruff impeccably trimmed. I wanted to cut my lips on his jawline.

[MF] The Saga of Sally – A Little Hate(love)fucking Between Friends

(Welcome to the Saga of Sally! This is the story of my relationship with a girl called Sally. I recommend you start from the [start](https://old.reddit.com/r/gonewildstories/comments/hsqikr/mf_the_saga_of_sally_cumstained_jeans/) – each piece will link you to next part at the end.

A brief reminder what Sally looks like (there’s a reference photo in the first part): she’s a pocket rocket, thick, redhead tomboyish girl, with an hourglass figure and the thickest ass this side of the Equator according to the Guinness Book of Records inside my head.)

You’re all eager for the next part of these memories. I’ll start with the juicy stuff right away: the Nokia 3310. What a fucking phone that was. I’m sure some of you reading this will only know it as a meme phone, an indestructible machine that could not be beaten but for readers who are my contemporaries you know how this changed the game. The Fucking Game in particular. You could now conveniently message your booty calls and then play Snake while waiting for them. It was a new world. As long as I’m not getting my dates mixed up (which I might be – I’m sorry if you want precise accuracy my memories aren’t that good – I’m working from long ago), both Sally and I had one soon after they came out which was only a couple of months or so before the cum-stained jeans incident. I have a feeling they were expensive when they came out but Sally’s parents were loaded and bought her one. My father was loaded *and* absence often so got me one out of guilt. We had messaged each other plenty in the last month or so, but now Sally was blowing up my phone with messages.

[MF] I (19F) was getting fingered at my birthday party and the guy (21M) had to wipe my juices off his hand to give someone a high-five

It was my 19th birthday and we decided to have a dorm party. Which basically meant we were all going to get more drunk than we did on an average Friday night with a few more people over. There were around 20 of us hanging out.

I was sitting on the couch next to Jake, my FWB at the time. I had on a pair of loose athletic shorts and a tank top. Jake had on sweatpants and a t-shirt. It was a bit chilly so I grabbed a blanket from my room.

Jake’s hands were under the blanket running up and down my thighs. I was stroking Jake’s hard cock through his sweatpants. As we got drunker, Jake slid his hand under my shorts and started fingering me. Gently at first, just teasing my slit. Then his fingers were deep in my pussy and my hand was inside his pants and wrapped around his cock. The whole time, people were coming up to me telling me happy birthday and I had to remain composed and make small talk.

[M] ITALIAN QUADRIPLEGIC USED AS A LIVING DILDO BY THE [F] MILF NEXT DOOR.

Hello folks of the sub! It’s officially time for another crazy sexual story by yours truly, the Italian quadriplegic and his always-ready dick.

If you need any context on myself, my spinal cord injury or my always-ready dick I suggest you read my last entry on the sub, about my new caregiver giving me a handjob ([https://www.reddit.com/r/gonewildstories/comments/fdkwfs/m_italian_quadriplegic_getting_a_handjob_by_his/](https://www.reddit.com/r/gonewildstories/comments/fdkwfs/m_italian_quadriplegic_getting_a_handjob_by_his/)).

But let’s just jump right into it! Today’s story involves a 37 years old married milf who happens to live with her husband and two children just down the road from my house. They moved from a nearby town about 5 years ago, and we have stumbled upon each other quite a few times ever since.

She has immediately caught my attention, and you will agree with me on to why as I describe her to you. She is a redhead, with light freckled skin and long legs. Slim figure, classy attire and high heel décolletés to complete every single outfit I’ve ever seen her in. Rich and bored, she is basically the Italian version of the Beverly Hills soccer mom I’ve always dreamt of having sex with (do Beverly Hills soccer mom even exist?).

I [M] went from getting orally serviced by one of our team’s water girls, to discovering she’s trans [TF], pounding her in the shower and then upwards from there ?

I play competitive soccer full-time for most of the year. It’s a very good gig, all told. There’s a small group of all-purpose team helpers who do stuff like getting water, collecting towels, running “go-for” errands and stuff. All of them are college-age. Two years ago, a new girl started – Leslie. (Not her real name, obviously.) Real pretty, 23 years old (I’m a little over ten years older), short, curly blonde hair, green eyes, and an amazing rack. I noticed her right away.

Everyone on the team is really friendly with the “gofers,” since they’re around all the time. Even the girls are often in the locker room while the guys are in various stages of undress. It’s just how things work. In part for that reason, there are supposed to be strict rules about no fraternizing with them or other team staff. But… that rule goes ignored pretty frequently, which is pretty common with sports teams.

Leslie noticed me, too. She would cheer me on the field, give me eyes off of it. I realized, later on, that she mentioned her hotel room to me a couple of times on away games, and that I should’ve realized what she was hinting at.