Category: gonewildstories

A Proper Goodbye [M/F] – Update

The summer before my Freshman year of college was full of memories. I had a girlfriend that understood we weren’t exclusive in our dating, I was really enjoying time with my FWB, and there was also the challenge of the chase after a couple other girls that summer as well.

Part of this summer was spending a week with a couple of buddies on a canoe trip in the wilderness. I was working the evening before that trip, and knew I had to be up early the next morning for us guys to hit the trail. Before heading out of town, I wanted to stop in and say goodbye to my girlfriend (Kristi) as well as my FWB (Andi), even though I had already told each of them the that I wouldn’t be able to see them this evening.

*******If you’ve read this part before, and just want the update, scroll down to ******* Read more »

[F]isrt So[m]nophilia Experience

*I haven’t posted here in a while, but I’m hopeful that this story will be worth the wait. Enjoy!*

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My relationship is the most sexually backwards relationship I have **ever** heard of. It’s actually **me** who wants sex, a 23-year-old female with short brown hair, a pretty average build, and what I’ve been told are a “very perky, fantastic” set of C’s. Meanwhile, my 23-year-old boyfriend is content with once a month or less even though I regularly pursue him. It’s the **one** thing about our relationship that I genuinely hate. Everything else is great. We match so well in every department *except* for our sex drives. When it does happen though, boy does it make up for the wait. Read more »

My first experience with a crossdresser [M18, T25]

For this story, I’m returning right back to the beginning. This was about ten years ago, but as with first experiences for many people, the vivid details have stayed with me to this day. I was 18, and at the time had begun partying. I live in a jurisdiction where the drinking age is 18, so as you can imagine, we liked to let loose at the weekends. I don’t drink now, and drank very little alcohol at the time, so my partying usually consisted of me driving my friends to a club, dancing a bit, try to get a girl and then head home. Obviously being relatively sober around drunk girls had its advantages, and many times I had girls hanging over me because I could make them laugh. Or more properly, I could speak coherently, while they couldn’t.

I’d already been into crossdressing porn for a few years. This was 2005, YouTube had only just started, and streaming video was very much in its infancy. In fairness, we already had broadband Internet, so it wasn’t terribly slow, I think in or around 2mbps. Despite that, streaming porn had barely taken off. I constantly fantasised about crossdressers, but usually I could only get that fix by images. Hardcore porn movies mostly featured so-called “shemales” in those days, which weren’t then and to this day aren’t my thing. The odd crossdressing video I could find left me cumming for days. I fucking loved it. Read more »

No More Condoms!

This will be a short story, but I’m pretty happy about it!

About 13 weeks ago I had a vasectomy. My wife and I are done with kids now so it was due.

A few days ago, before work, my wife gave me a terrific blowjob in our bed and just as I was about to cum she slipped my cock out of her mouth and used her hand to bring me to a knee weakening orgasm… Into a little plastic jar.

About 45 minutes later I was handing that jar to a lady at the test lab feeling acutely aware that everyone in the waiting room knew I’d just jizzed in it.

The next day (yesterday) I called the vasectomy clinic to see if they’d received the results yet – they had… I was shooting blanks! We could stop contraception immediately.

Unfortunately I had some work to do that night and when I made it to bed my wife was fast asleep. I didn’t want to wake her.

But this evening I joined her in bed in reasonable time and we soon started to kiss and fondle one another. Soon enough I was hard and she was wet. Read more »

Masturbating in the Uni parking lot.

This took place a few years ago. I had decided to take a couple of difficult classes at a much smaller uni in the same city, as opposed to my regular uni. The reason reason for this was because the class sizes were smaller, I could have greater access to the profs.

This campus was on the other side of the city from where I lived. Despite this, it made more sense for me to drive as opposed to taking the train. It would have been a shorter commute. In those days I didn’t have my own car as I didn’t need one. So my dad used to let me borrow his van.

I loved this van. It was this sleek black Toyota Sienna. We had bought it brand new and it was so roomy! On my insistence, we had gotten all the back windows tinted to a limousine tint so you couldn’t see inside at all. This thing was a beast and I loved it. Read more »

Only in our dreams [M/F]

It started simply enough. Eye contact for a little too long. Sexy jokes. That intoxicating smirk he had. Blushing, just a shade too dark to be purely platonic.

Then one day he came over looking for my husband who was, thankfully, at an appointment with the baby. Who knew when they would be back, but I invited him to wait. After all, we were friends too.

At first we sat on opposite ends of the couch, playing Battlefield and talking shit like we always did. He teased me about losing by default for being a woman. “In your dreams,” I shot back. I’m not sure either of us knows when exactly it happened, but next thing we knew our thighs were practically touching. I could feel the heat radiating off his leg.

I felt myself flush at the realization and bit my lip, hoping he didn’t notice. Why did he have to wear such tight shirts? It was like he wanted me to look. And I did. Every time. Jail had been good to him. Nothing else to do but exercise, I guess. I had missed him though. Read more »

Careful what you ask for… fucking my[21f] ex-bf’s good friend[35m] from prison.

I’m 21 and I broke up with my boyfriend of a year recently. I was feeling petty and called one of his good friends while I was drunk one night. They were friends while in prison, although my ex only did little over a year and this guy did 10 years. He’s much older than me and my ex, he’s 35. So it was the first time we ever really talked, first time we talked on the phone. He gave me his number when I first started dating my ex and told me if I ever needed anything I could call.

He showed up like an hour after I got off the phone with him haha I don’t remember what I even said on the phone but he didn’t waste time getting to me. I was home alone, he immediately showed up and sat on my bed and we talked for half an hour. He brought a blunt and a bottle of wine. Once both were finished he leaned in and kissed me. I pushed him away but he kept coming onto me. I started taking off my pants and I remember him being like “Oh my god, put your pants back on… you’re my man’s girl.” Read more »

[M]y dreamlike experience with a sextoy [F].

Sorry if it sounds confusing, it’s my first post. Hope it’s coherent.
I’m a 36 year old man, brazilian, uncut, around 200lbs and 6′ tall, brown eyes and black hair. Not ugly, but not a model. I was in a kik group a while ago, trying to get laid, as usual, when I see this guy posting to the group “My friend wants to be used tonight. Message me for details”. That immediately caught my eye, of course. It’s something I’d never done, plus, you know, the sex part I was craving.

So I did PM him and he gave me the details. I drove there. Had kind of a hard time finding the place, and because of it, started thinking it was all a prank or a setup. I kept thinking I’d be robbed, or raped, maybe both, and in all scenarios I could think of, I would most likely end up dead or humiliated. But I was too horny. I finally found the place. My heart was racing as I knocked on the door. It opened. Read more »

Getting my Wife Pregnant

I have been thinking about writing this for a while as I enjoy this sub in my dry times and today I thought to myself why not I might as well pass it forward. This is the true story of trying for a third child. There is no anal sex or threesomes or other nonsense stuff as that is just not practical just plain old marriage sex so I hope this is good enough for you.

My wife is pretty vanilla when it comes to sex that is until we are trying for a baby in which case she heats up and she just seems desperate for sex and really horny. I am 40 and she is 37. She has a nice full figure and nice big tits with lovely large nipples. She has a nice full ass and is never shaved, the smallest bush she will have is a few inches of thin landing strip. She knows I like it bushy, there is nothing nicer than licking out a nice wet bushy gash. Lots of you young guys would call her a MILF and she is very very hot. Or sex life goes from rampant for a while to nothing for up to 6 months as being parents can be demanding. We have been together for just over 20 years. Read more »

My most recent time fucking a crossdresser [M28, T19]

I’ve always had a voracious sexual appetite that has led me into the rabbit hole on more than a few occasions. For my first story, I’m going to retell my most recent night with a crossdresser. This happened in February 2016 and is as accurate as my memory will allow.

I’m 29, tall, a fraction overweight, but I would imagine reasonably attractive. I am single, live alone and have no dependants. I did well at school and at university, and have found success in the financial sector. I am not objectively rich, but do make a six figure salary and have the toys to go with it. I only mention that as for the purpose of some other stories, I have managed to use it to my advantage to sleep with women very much out of my league. Sexually I am very much of a hedonist, but in my day to day life I am boringly ordinary. I do not drink, do drugs or smoke. My cock is just a hair over 7 1/2 inches, although it’s not particularly thick. It’s perfectly straight, something that has been commented on by lovers a few times. Read more »