Category: gonewildstories

Fucked a milf while working away with the help of 50 shades of gray part 3

Welcome to the third part of the story.

The previous chapters can be found here and here.

A quick recap if you haven't read them. I was working away and ended up fucking the manager in the bookies I was working in because of her reading 50 shades and me being a cheeky sod. She (Helen) comes to my hotel room that night and we're having great dirty sex, joining the story now, she is bent over on the bed hands zip ties behind her back with her knickers shoved in her mouth!

I force her face back into the sheets as I start pounding her again, her hands tied behind her back, her ass is red from me slapping it, big red hand marks all over it, her moans are muffled by the pants stuffed in her mouth!

I feel her pussy start to tighten, pussy juices in my pubes and running onto my balls , I pick up the pace my balls slapping off her pussy, her whole body starts to shake as without warning I plunge my thumb deep into her exposed ass, I keep fucking her hard while moving my thumb in a swirling motion , her pussy and ass pulsating as this massive orgasm passes over her. Read more »

Sometimes better than a Threesome

I have my fair share of kink in my life, being married to a mostly-gay, sexually dominant belly dancer. But after somehow wrenching my neck today and clearly being in pain, my wife offered a massage.

Twenty minutes of neck work later, I assumed her hands were crawling their way down to rub my lower back a bit (where I usually have pain). And she did, but only briefly. Her hands crept further down, over my butt and down between my thighs.

Here I am now, thirty minutes after that, a very relaxed and happy husband. I've seen a lot, guys, but sometimes no amount of latex-clad butt sex or any number of a wife's beautiful girlfriends can match a non-committal, face-down handjob after a neck massage.

And now she's making lasagna. I fuckin' win today.

So[m]etimes you eventually get to screw your high school crush, and even better, she’s a yoga instructor.[f] [continued in comments]

For my muse who got me to tell a few more stories

Jill was an acquaintance from high school. She was a cheerleader, maybe the most popular girl in four or five area high schools, and a secret crush of mine. When we were in high school, her body matured faster than other girls, other cheerleaders in fact. I can remember when we were at some spring sports event and some guys came up to her and another cheerleader from Jill’s squad. They commented on how the other girl was cute, but that Jill had a woman’s body. She was Filipina, with black hair that was curly in a loose, sexy bob.

Jump forward about 10 years, and Jill’s curves haven’t changed. That amazing athletic hourglass figure with full C cup breasts and long legs that had her at about 5’5”. She was now a yoga instructor on the west coast. She sent me a message saying that she had seen that I was coming to the west coast on business and offered to pick me up and to let me crash at her place for a few nights. Read more »

Worst prostitute ever! [m/f]

He didn't actually use that phrase but he strongly implied it.

Let's call him Kevin. Kevin had been a regular of the escort agency I worked for, long before I arrived and years after I left both the agency and the glamorous world of prostitution, I'm guessing he still is.

The woman that ran the agency loved him. It wasn't just because he was a frequent customer and the amount of money he pumped into the agency, I think it was because he fulfilled her expectation on every level of what her ideal customer would be like.

He was fat (pudgy rather than obese) balding and his 50’s, every woman’s dream, and he just wanted to be our friend. He also wanted to fuck us in the arse and urinate on us, though he was still a good bloke apparently!.

From before we joined the agency we were told we had to provide all the services the agency offered. So while a woman at another agency might not want to offer say, anal sex and her agency might work around it, our agency wouldn’t. In fairness when they were always up front about it. In practice how it worked was that your first time with a new client, if he asked for something like anal, you’d say not now, but once we’ve had a few bookings we’ll do it then. Read more »

Impulsive outdoor breakup sex [F/M]

After getting over the initial shock of this encounter, I realized it would make a very sexy story since I haven't stopped being horny from it for the past 2 days. My [22F] (ex)boyfriend [26M] and I had been dating for about 2.5 years. We have always been semi long distance – we were both in school and 2 hours away from each other. This made it so when we did see each other about every 2 weeks, we typically fucked like bunnies.

Fast forward to our breakup. I have been traveling for about 5 weeks, and before and during my trip, we had been communicating our doubts in the relationship and pretty much hinted at a breakup upon my return to the US. Let's just say a breakup has been a long time coming due to our fighting – we're just such close friends (and not to mention really attracted to each other) that we didn't want to give up our relationship before. On Monday, he drove to see me – since it's summer, I'm in the town where I grew up, staying with my parents until I move for my job in August. With the knowledge that we were about to have a potentially harrowing breakup talk, and the only privacy we had was his car, I was nervous for the encounter. I wanted to boost my confidence, so I put on a new dress that hugged every curve, and was too tight to be able to wear underwear – so I didn't. I thought, "This will show him what he's missing." And I felt very confident in it, always a good thing for a breakup where you don't want to lose face. I had zero expectation of him being horny or affectionate in person since in our talks before meeting in person, he seemed angry and sad. Read more »

Surprise Strap-On / Lily Part II (F/F)

Did I give away too much in the title? Hehe. The prelude is here.

So after that first night Lily and I started dating. Proper dating, we really dug each other. My heart wasn't fully into it though. This was my wild "find myself" kind of summer and I wasn't about to be tied to one person. I was dating a guy too who thought he had my heart and I also had a random hook up here and there. I'm still shocked that I never got caught. I wasn't careful at all. That first night sitting on the balcony with Lily I actually saw the guy walk right below us (holding a ukele of all things – I have random taste in people – and a photographic memory it seems). Another night Lily brought over take out, we watched a movie, and we rolled around in my bed for a while. I wasn't watching the clock because I knew he worked late and by the time I smacked her ass goodbye I realized he would be getting off work any minute. Except he got off early. And literally knocked on my door MOMENTS after Lily's car pulled away. Thank you evil sex demons! That would have been difficult to explain to both of them… Read more »

(M/f) Weekend trip to a Hooters in Oklahoma

This happened back in 2012. I was working as a traveling salesman on the weekends while finishing college, and on this particular weekend I was traveling to Tulsa Oklahoma. This was a 14 hour drive but luckily my buddy had agreed to make the trip with me so it wasn't a solo drive. We will call my buddy Jacob. Fast forward to Friday night after checking into the hotel and we were grabbing some beer and wings at Hooters. Now I am a pretty friendly guy and in no way shy, so I scope out the prettiest hooters girl(imo) and ask her where we can sit to be in her section. We will call her Emily, since that was not her name. Emily has a beautiful face, dark brown hair, nice perky tits, and was extremely friendly. Little did we know at the time Emily was training a new girl that night whose name was Chelsea. Chelsea was this sexy brunette with a skinny frame, full C cups and she had this devious smile about her. After finishing our first pitcher and ordering our food we settle into more drinking and the girls are both spending a lot of time at our table making small talk, etc. I notice that Chelsea is checking me out. Its not obvious but it's there. So I play it cool and after a few more pitchers were ready to leave and she slips me her phone number.. I may have asked for it earlier in the night but I dont remember. Anyway I send her a message after our show on Saturday to see if she was working and when she didn't respond, Jacob and I decided that was a pretty good indication of yes. Read more »

Things I’ve literally f*cked myself with | Or why I should always travel with a cucumber [F40 Masturbation]

In the last several months I've gone on a few trips without any sex toys. Once because I rented a holiday property and it was going to be my Mom, son, a close friend and her kids, and it just seemed weird to pack a vibrator. Another time I was travelling just with my Mom and we were sharing a room. Recently I went to a family member's house and the walls are super thin.

I've subsequently learned that not having a toy is a big mistake. It leads to some pretty raunchy behaviour on my part.

I guess I should clarify that I need assistance to cum through masturbation. Not sure why but my own hands just don't do it for me. Perhaps I could find a lover who could educate me. But until that happens and I'm master of my own domain, I need a toy.

So… at the holiday property one day I found myself alone and desperately horny. I'd been on the naughty online dating site and having some great sexting exchanges and was all worked up. I rummaged around the kitchen, as it held the most promise. One washed cucumber later, I was fixing myself up quite nicely. Except the cucumber was cold. Microwaving it seemed wrong and potentially could end badly. Do they explode in the microwave? I didn't want to have to explain that one. Read more »

My lover gets a home run [M45 F40]

One of my on-again off again lovers was 45 with the cock of an 18 year old and the stamina to match. But the best difference is he had the experience to make him one of the best lovers I have ever had.

His only downfall was he was emotionally unavailable and often bailed on plans. But I was willing to forgive him given how insane our physical chemistry was.

One night I attended a sports event and he showed up to my place afterwards, late as usual. He wasn’t ready when I texted him because he hadn’t showered yet. He told me he had still needed to shave and didn’t want to show up like a porcupine. He’s one of those guys who keeps hair on his body – he trims his chest (and I love the hair on his chest) but shaves his pubic area.

I don’t let him get past the top of my stairs – we embrace and kiss and five minutes goes by before I feel like I can release him and actually let him into my living room.

It was almost 11pm. Read more »

Watching a [m]an and woman [f]uck, and [f]inally joining in (part 3)

part 1 | part 2

So Dan, Kate, and I had all cum. As I mentioned in part 2, we were all lying on the bed, kind of exhausted, and Dan was rubbing my feet. There's not much I love more than a good foot massage, so him doing that after watching them and then joining in for what had been pretty much the best sex of my life, I was in heaven. I felt so relaxed and was basking in that post-sex afterglow.

After a little while Kate asked if I would like to join them in the shower. At fist I said no, because I thought it would be a little cramped with three people and maybe kind of awkward. But then I went to the bathroom, and saw the shower. It was really nice with like stone tile, and plenty of room to fit all of us. So I said sure, why not. We all three got in and took turns standing under the hot water. Dan and Kate had their hands all over each other again, and I let Dan run his hands over my body some, too, mostly my breasts. Read more »