Category: gonewildstories

First Date Lovemaking [Romance] [FM] [Open]

Two years ago, I met a beautiful, tall redhead with wavy hair on Tinder. We started chatting, and realized we live only a few blocks from each other, so we decided to meet up and go for a walk on that beautiful early fall evening.

At the time, I had a pretty swank bachelor pad, walking distance from downtown that my girlfriend had helped me decorate. We had been in an open relationship for about half a year at that point (and still are), but I hadn’t met her kids yet, so opportunities for sex were sporadic.

I grab a bottle of red wine, and head towards her place to meet up halfway. She’s stunning in a pretty sundress, with nice curves (but not fat). We greet each other with a hug, then start our walk to a local park.

We’re chatting, and I point out my place on our way by. We live in a fairly hilly region, and the park is no exception. She had never been to this park – it’s a little tucked away. Read more »

[M]y [F]irst Day as a Chicagoan

Three and a half weeks ago I accepted a job offer in the city, that started the ball rolling of quickly finding a new apartment, in a new city, 2 hours away.

I couldn’t have been more excited though. I was finally going to be living alone again and In the city that has always felt like home. My Sir, having been in the city for 10+ years, was so helpful, making neighborhood recommendations and coming to see apartments with me. A couple of weeks and 6 apartment showings later, I found home!

Being the wonderful person he is, Sir took my first full day in city off work to help get me settled.

And the fun begins.

He surprises me with a bottle of champagne and a pint of my favorite ice cream, but also new toys! Included were: new restraints, a mouth gag, and (my favorite) a butt plug that has balls inside so every time he smacked my ass, I was reminded of its presence. Read more »

Hooking up in college, with the help of a Milf. [MF]

Okay hopefully I will keep this short. Freshman year of college I became friends with a cute girl (Jess) who I just happened to hold an umbrella for her b/c she forgot to bring one. (IK romantic) It quickly became more than friends as we began hooking up 1-2 times a week. Everything is going smooth until the beginning of December when she starts pushing hard for us to become a couple. I was fine with it, she was cute, friendly, smart, the whole works.

Over X-mas break I get invited over her house, we lived only a half hour apart. As soon as we walk through the door, the mom (Let’s call her Katie) almost runs me over, gives me a huge hug (an extremely intimate hug considering we just met). And to put the cherry on top of the awkwardness sundae she feels up my bicep as she is pulling away.

Some background on Katie, divorced from a super-rich, attorney. Total blonde trophy wife, that works hard to stay in shape and young. (Later found out she dated some guy that no homo was sexy and was still in his late 20’s) Dinner was fine except that Katie kept sliding in comments about how attractive I was and how cute we were. Those comments said once are harmless but repeated five times each is creepy. But I shrugged it off at the time. Read more »

[MF] Quick story of the first of many BJs from my ex

My ex, Tina, and a few of our friends were going back to her house after leaving a small city festival nearby. Me and our friend Max were feeling pretty tipsy and were not able to drive home so Tina brought out blankets and spare mattresses so we could sleep it off safely. We all tried to stay up and talk about the festival and watch TV but we were too tired so Max slumped over on their mattress and quickly fell asleep while Tina and I tried to keep our eyes open, but that was proving fruitless, so she turned the tv off and snuggled up to me on our mattress just a few feet away from Max’s.

I was having trouble getting comfortable to fall asleep so I was shifting around trying not to disturb Tina, which turned out to be a lost cause as she turned around to face me, but before I could say anything she kissed me with a quick peck followed by a long, slow, passionate kiss. She had just enough of her strawberry chap stick on for me to get a faint test every few seconds. As we were making out our hands were exploring each other as best as we could without creating too much noise and after a bit more fumbling around, Tina broke our kiss and whispered for me to be quiet and after a quick bite of my bottom lip she slid herself down the mattress, pulled my underwear off and took my eager cock into her mouth as I lay mostly still on my side. Read more »

Pool Party [F]estivities with [M]y Neighbor

This is another tale about Diane.

She and Jack had a pool and would often times, during the summer, invite neighbors over for pool parties. It was on one such afternoon that I found myself waist deep in chlorinated water with a beer in my hand. Jack was manning the barbecue and Diane was playing hostess and all was right.

Diane and I had been fooling around for a few months at this point and neither of us could help stealing knowing glances at each other as she made her rounds at the pool talking to guest, maybe around 30 in all. I wasn’t the only one glancing at Diane though, she was wearing a black and white diagonal striped bikini that was somehow modest and slutty all at the same time somehow. The top was a triangle top that she had jammed her large fake breasts into and the bottoms tied at the sides. They covered most of her ass but there was still some spilling out of the sides of the bikini and it looked as though it was painted on.

It was driving me absolutely crazy. Read more »

[FM] Lunch with my Dom

Yesterday, I visited my dom for lunch. He told me he wanted to fuck me immediately when I walked in the door, so I removed my bra and panties from under my dress in the restroom at work before I headed to his house. He greeted me naked at the door with a hard, lubed cock. He shut the door with one hand and lifted my skirt with the other as he grabbed a handful of my ass. I bent over slightly so he could admire it. He then got behind me and moved me a few steps towards a tall dining table that is near the back door. I leaned over it as he slid his hard dick deep inside me and began fucking me as I moaned and my muscles went temporarily limp from the shiver up my spine as I savored him inside me. Then as the lust rushed over me, my back arched and I bounced feverishly against his thrusts, going weak in the knees and limp again as I came, then back to a wild animal squeezing my pussy to milk the cum from his balls, then limp and screaming again as I squirted. He moaned loudly and then pulled out and came all over my lower back and round ass. He offered to bring me a paper towel so I wouldn’t get it on my dress, but I simply stood up and let my dress fall and stick to my cum-drenched ass, “I don’t mind cum on my dress, baby. You should know that by now.” Read more »

Keeping quiet in the guest bedroom [FM]

[ I read this sub on my main account but never post. I’ve been sitting on this throwaway for awhile and I think it’s time to start sharing :) ]

My boyfriend and I went down the shore this past weekend to visit some friends. We drank a fuckton and ended up sharing a tab of really good acid.

Around 3 am, everyone sits down to watch a movie and I sit on my boy’s lap. He gets a little hard and we start rubbing on each other a bit. Finally, after adjusting himself a few times, he can’t wait.

We go into the guest bedroom next door to the TV room. He immediately turns me around and rubs his cock against my ass. We both get out of our pants as fast and as quietly as we can.

The bed is too soft and squeaky and the dresser is good height but shakes too much. So in order to keep quiet we’ll have to stand in a good spot where the floorboards won’t freak in this tiny bedroom. Read more »

A Day at the beach’s [MFF]

This story is happened about 5 years ago.
I had just gotten out of a long relationship and decided to give Plenty of Fish a try. Low and behold I ran across an old friend from my teens “Rachel”. I remember us having a mutual crush back then but since we were both dating at the time we never got anywhere other than very flirty talking.

I decided to message Rachel via Facebook and ask her to hang out sometime. She responded quickly with a very upbeat hell yes, and invited me to join her and her friend at the beach the next morning.

At this point I was looking forward to rekindling what was a good friendship back again. I showed up to the beach around 9 to find Rachel and her friend already laying out. I was looking forward to seeing how hot Rachel had gotten and was really very wide eyed when I saw her for the first time in 4 years. She was a 5’7” blond with perky B tits and probably only weighed about 115. Now her friend Stacy wasn’t too bad either, short brunet with tits the size of a grapefruit and a tiny body that somehow held them up probably 120lbs at best with at least 5lbs of that being her tits. She was a solid 6 while Rachel was easily a solid 9. Somewhat to my dismay Stacy was the only one wearing a bikini. Rachel was still in her loose fitting t-shirt and some volleyball shorts, you could tell she had a bikini on underneath though. Read more »

She tried to stay good. [MF]

I went to a sex site years ago I did some messaging but actually got connected from the erotic stories posts. I used to write and share stuff there. I hooked up with another sexy story teller. It started with a compliment on one of her stories. She checked out my profile and started complementing me back on my stories.

we chatted on line for a bit back and forth. After a particularly hot cam session we decided to meet up. But the pretense was no sex. I was fine with that based on how we were talking I knew if it was going to happen it was going to happen.

Cue the date. We met at a local pub above a coffee place down town. We had both already eaten and just ordered some appetizers and drinks. (We will call her) Amy and I talked for a bit . She was about 5’5 and in extremely good shape . With the most gorgeous green eyes . Neither of us could stop staring at each other. Amy seemed to snap out of a trance that we were both in. She mentioned no sex again but it seemed like more of a reminder to herself than to me. We decided to get some ice-cream from down the street to cool things down. Read more »

The Halloween Adventure. [FM] [Long]

I have had a lot of sexual adventure over the last 10 years, and would like to get them out there. These stories are in no particular order or time-frame, and are just there for me to get out there and maybe others to enjoy.

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This one is a bit long so I apologize in advance.

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I never actually caught this girls name, so we’re going to call her Katy. You’ll know why when you hear it. I met Katy at a friends Halloween party last year at a party on a lower floor in my condo building.

Katy was already at the party when I arrived fashionably late, already mingling and socializing. I still don’t know who Katy knew, but there was enough people there from enough social circles that it could be anyone’s guess. By the time I arrived Katy was already there, dancing away to the monster mash, or whatever tacky Halloween music was playing. She immediately caught my eye from the moment I walked into the apartment, and I couldn’t take my eyes off her the entire time. I wasn’t really sure what her costume was supposed to be, but I liked it. Katy stood at a fierce 5’9 and was wearing a blue wig that come down to just below her jaw line, a white tank top that she clearly wasn’t wearing a bar with as was evident by the tease of her nipples on her perky C-Cup tits, a ruffly red skirt, blue pantyhose, and bright red heels. Read more »