Category: gonewildstories

[MF] I just lost my virginity to an older woman. It was awesome.

I’m a horny pervert, but that’s probably normal for guys my age. We all want to fuck. So, I decided to look online since I’m not the most outgoing or anything. I’ve been looking for awhile, and I thought nothing would ever come of it. About an hour ago I lost my virginity to a amazing woman whose about a decade older than me. Now I’m back home, sitting at my computer, a little tired and mostly just thinking “holy fuck” and trying to think of what to write.

To start, I actually never talked to her before meeting her two hours ago or so. This was set up by her friend, a older gentleman who is her dominant. He first contacted me about a week ago or so, and was wondering if I’d fuck a girl while being recorded. Being the horny bastard I am I said yes and then yesterday he tells me he’s got a girl and to come by tonight. She’s 5’ 8” (as tall as me), white, brunette, pretty, and kinda thick (thicc? idk). All I know is she was attractive and wanted to fuck me, the 18 year old virgin. That apparently really turned her on. Read more »

[f] wet dreams

woke up from a wet dream.

in the dream, my parents decided to leave on holiday without me. without them there I was shipped off to my best girl friends house to stay where it’s only her, her dad and her dad’s girlfriend. I didn’t think anything of it because I love her, she’s the best. She makes me jealous of her naturally red hair and she porcelain skin and a narrow hips. I on other hand, have olive skin and mousy brown hair and large d cups and curvy hips. We both however have light freckles.

Anyways, I love spending time with her but I was annoyed and pissed that my parents would leave me behind. Then I found out that my best friend is spending a 2 weeks away with her mom, leaving me alone with her dad and his stupid girlfriend. She’s stupid because all she ever does is spend his money on clothing and spas. Read more »

[FM]/[FFM] – Highlight from our week with another Redditor!

So, it’s a been a while since I posted anything on Reddit, but as those who have read my past stories will know, my GF had a bit of a thing for bringing in other women.
We had a very enjoyable time with one of my GF’s friends just before Christmas, and recently we’ve spent just over a week with another Redditor who was over here for a “Sexual Experience Get Away” and an FFM was on her list.

Now, I can’t post everything that went on over the time we were together, mostly just because it would take too long but I will post a few highlights now and then, I think my GF plans to do the same.
Basically, dedicating that many days to sex forces a lot of creativity, as quite frankly you do get sore and tired but it was still an incredible time.

Now our American friend, who I’ll call Lucy, was a very beautiful woman, who as well as being an incredible professional masseuse, was also a keen Yoga enthusiast.
I often joined her as I too try to do at least 30-60mins of Yoga a day myself, I always do it in just my boxers, Lucy, however, liked to do it completely naked, which was a huge distraction in all honesty. Read more »

I guess I just love older women [MF] [cheating] [MIL]

Truth be told, there is nothing to “guess” about here — I know I’ve always loved older women.

Don’t get me wrong, I love my wife as well. She is a fit, big breasted brunette that never fails to turn heads. Her *mother* though!

My mother in law is a little bit taller than my wife, maybe 5’6, and thin. She isn’t fit as much as she is just one of those women that hit the genetic lottery and has remained slender throughout her life; at 55, she could easily pass for 45. She is divorced and lives alone, and in the years prior to this story she had undergone something of a metamorphosis. Call it a mid life crisis or her finding herself, she suddenly started dressing in skin tight jeans and revealing tops.

It all started with a vintage Mustang. Read more »

[F] Watched my plump prostitute aunt shagging.

Years ago I [F40’s] had to go on a course up in Birmingham. To save a bit of cash I stayed with an aunt. I didn’t know her that well but she happily agreed to put me up for the week.

On the Thursday in the middle of the morning there was a power cut in the training building. After about an hour they decided to abort the morning session and agreed to reconvene after lunch. That gave me a good couple of hours, so instead of kicking about on a desolate industrial estate I decide to pop back to my aunts’ place.

I wasn’t expecting her home so just let myself in and put the kettle on. While I pottered about I cold hear a noise from upstairs. It was a rhythmic creaking noise. I could also hear some groaning.

I switched off the kettle so I could hear better. It was definitely the unmistakable sound of sex. Intrigued and getting turned on I had to investigate. If she had assumed so was not going to be disturbed she might have left her door open. I slipped off my shoes and began a slow quiet ascent of the stairs. As I approached the top of the stairs the sounds grew loader. I could hear her giving proper porn movie encouragement. Read more »

Key West [MF] [FF] [MFMF]

Late 1986. Reneé woke up sick the morning that the test results would come out to find out who made First Class. Pulling the covers over her head she said, “I’m calling in sick”.

“Get up, let’s go for a run”.

“No”

“Wanna fuck instead?”

“I think I fucked myself on that test. The more I think about it the worse I believe I did. Plus they are only advancing the top three percent”.

“Bullshit, you passed. No one knows the paperwork better than you. The Chief over at Base Admin calls you instead of reading through the books”.

“I didn’t pass. I won’t ship over again if I don’t make it”.

“Yes you will. Come on, let’s run. I’ll even keep up with you”.

“You can’t”.

“Let me rephrase that. I’ll try real hard to keep up with you”.

Begrudgingly she got out of bed and got dressed. After stretching we were on our way. She set a brisk pace. We ran silently for a few miles before she said, “I’ll meet you back at the house”, then started to outdistance me. I didn’t even try to catch up. Read more »

[MF] So, here’s what happened with my friend…

Some of you may be aware of [this post of mine](https://www.reddit.com/r/holdthemoan/comments/7tic90/gif_i_was_told_yall_may_appreciate_this_im/) from the other night in r/holdthemoan. I’ve had a few requests for the story of how it went down, so here goes. But know this: I don’t consider myself a prolific writer by nature AND I’m used to telling stories to girlfriends (where you leave out most graphic / explicit detials) so if you have questions, ask away and I’m happy to answer :)

Quick background on why I was so nervous (I’m usually very not) and hesitant to just go try to fuck him:

1) our families go back forever and he grew up with my cousins, so I kinda did too because of holidays, summers, etc.
2) the summer after I hit puberty and while on the way to the swimming pool with a bunch of their friends, my cousins made it abundantly clear that I was off limits
3) I was apprehensive about possibly introducing future awkwardness

And as a side note: in hindsight by thinking about how to put this down on paper, it makes total sense as to why he’s never been flirty with me (see point 2). Read more »

Sexting my online sir during and after a wake. [F][M] [cheating] [pictures]

I’ve been lurking on this subreddit for years but never thought I’d actually post anything of my own. This particular story is going up because Sir asked me to put it all online, and will not respond to my messages until it’s finished and posted. After all of the fun we had last night, I couldn’t wait to do as he asked and post. These are all messages that were sent to me over the course of the night and my responses to them. The pictures I sent to him that don’t have my face are [here](https://imgur.com/a/sapcp). I hope you all enjoy. Read more »

[MF][F] one year to this day my wife and I had our first and only threesome.

It was a Sunday night and my wife and her friend decided to go out drinking. We have always had an relationship where if she wanted to be with someone else she has my blessing. I stayed home to play Xbox and would get updates via text every so often. Being Sunday night not to many men at the bar. So to spark things up I decided “ I will send a dick pic to my girl.”
What I didn’t know was that my wife’s friend had her phone. After some mild embarrassment and flirting I convinced them that they needed to kiss. And so they did. And giggled. Then they got more drinks and I convinced them to kiss each other in the car, which was surprisingly not that difficult to do. Read more »

The absolutely stupidest way I ever got a boyfriend [FM]

Miscreants littered the hallway into the basement that smelled of liquor and sweat. I can’t explain why I was at that party when I was 25, I’d graduated three years ago and I was still hanging out with college friends. Mostly everyone I went to class with moved back, but I still had a job and didn’t want to go home. But the music scene was good.

I won’t name names, but there’s a couple bands that played in my circle that are big enough to still be around. My favorite, well, I kind of miss the way she sang with that heavy voice. She was the closest person to ever make me contemplate my sexuality… But I’m getting too far away from why we’re here.

The cement floor meant one wrong move in that mosh pit would be pretty brutal. I got a bruise on my ribcage from standing too close to a guy doing roundhouse kicks. Not fun. I drank from a clear cup (I think) — and leaned against a wall talking to my friend who was still a Sophomore. It was a good show and later into the night when my ears had taken enough abuse I stepped back outside and onto the lawn. Three or four guys were drinking and laughing. Their bombastic and alcoholic grabbed my attention while I smoked my cigarette. They were all kind of cute in their own way, if I remember, but the one sitting on the bench had flawless, pale skin and these intense eyes that completely ignored me. Read more »