gonewildstories Archives — Page 3418 of 5640 — NSFW story

The time I [M]asturbated with and then [F]ucked my best friend.

Hey guys, back with another story since you guys liked my last. This one took place during my senior year of college. It was a mellow weekend and there wasn’t much happening on campus. That being said most of my guy friends who I’d drink with every weekend were gone so I was planning on having a chill night maybe doing some homework until Rose hit me up asking to hang just cause her friends were also gone and she wasn’t up to much.

Now me and Rose had been friends since the first day of college since we lived on the same floor but had never had any sexual history. Only a small peck here and there at a party while we were drunk it was a pretty “regular” friendship. The farthest it had gone was us changing in the same room but we’d always just look the other way if it involved us getting naked. Anyways she was gorgeous. About 5’5, white with blonde hair. Had a nice ass with skinny legs and C, borderline D cups above. She was as hot as they come and she was one of my best friends. I’m sure I would have fucked her much earlier but I had a girlfriend and she had a boyfriend most times so we were never really single while the other one was. However, during this night she had gotten out a relationship and it was the first time we were both single in college. Read more »

The gorgeous redhead I didn’t suspect [MF]

I’ve know this gorgeous red head milf for a few years now. Our daughters played on the same soccer team I have coached for just as long. I’ve always had sexual thoughts about her but never acted on it. Hell, never thought she felt the same. Fast forward to a recent night of drinking and texting… which lead to flirty texting. Which lead to the revelation that we were both pretty smitten with each other. Some pictures and videos shared. Mutual masturbation Phone calls made. It was ramping up… move forward to a weekend where things were getting heavy. I was out taking care of some things at petsmart. She was out having dinner and drinks. And drinks. Lots of text flirting and suggestions on what we’d do to each other if we were near each other… I say: “why don’t you meet me in the parking lot outside PetSmart on your way home from dinner and drinks?” She says: “sure why not”. Shit. It’s actually on. So I step outside and move my truck to a quiet dark secluded portion of the parking lot and wait. she pulls up… I move to the backseat of my truck and she joins me. Instantly the lust hits us… heavy, heavy make out session ensues. Like teenagers who first discover sex. That level of make out session. And damn is she good. Her tongue… fuck me. Searching my mouth. Battling with mine. It’s so damn hot. Read more »

Fucking a bridesmaid after the rehearsal [MF]

Backstory:

Recently out of a long term relationship, my friend and his future wife decided to try and set me up with one of her best friends at their wedding. I was feeling a bit down, not really confident in myself and wasn’t really looking forward to the wedding. The week came and a few flights later, I was in town to see my best friend get hitched.

My friends talked her up before I met her; about 5’5”, a little thick, cute and by my friend’s wife’s admission, promiscuous. If there was anyone I was going to get lucky with over the course of the next four days, it was her. Read more »

I had a sex marathon while house sitting with [m]y adorable theater geek G[F]

A little into the year my parents contacted me about house sitting for them while they’re out of town to celebrate their 30th anniversary over Valentine’s Day weekend. Since I attended college a little over a half hour away I was immediately their first choice given my two little sisters attend college out of state. I said it was no big deal and that I’d be happy to house sit for the two nights. I immediately asked Rocky if she wanted to spend the two nights with me there and she happily accepted. We’ve actually been tossing around the idea of moving in together since Rocky’s current roommate (her best friend) Joy will be graduating a year early at the end of the semester so we thought this would be a nice little experiment to test the waters. Read more »

I’ve never enjoyed anal sex, until I decided to [F]uck my own ass

So last night I was having trouble sleeping. I had a stressful day and I laid in bed for an hour tossing and turning before I decided to masturbate, hoping that it would help me sleep.

Things started fairly normal. I got out of the onesie I was wearing, reached down to my pussy and started slowly fingering myself. It took me a while to get into it, as I wasn’t horny before I started masterbating, but after I started playing with my nipples (they’re very sensitive) and found some good porn to watch, I was good to go.

The video I watched was of this gorgeous redhead fucking this INSANELY attractive black guy, and it was incredibly hot. They were both just really into it, and it was very passionate sex, and watching them just really did it for me.

So I’m about 10 minutes into the video, when out of nowhere, the guy starts fucking her ass. The moment he sticks in in, both of them let out these sexy deep moans and I start gushing. He started off fucking her slow, with nice long strokes and she’s telling him how good it feels and I get so turned on by her moans that I want to feel the way she does. Read more »

Second Hiking Sex Experience [MF]

You can view my first experience [in my previous post](https://www.reddit.com/r/gonewildstories/comments/feyeka/first_hiking_sex_experience_mf/?utm_source=share&utm_medium=ios_app&utm_name=iossmf). Other than being 30 at this point, I stayed pretty much the same, but my wife’s body changed, so I’ll describe it below.

She [F] is 5’4”, with brown hair and light skin that tans easily. Her B-cup tits sag a little now that we’ve had kids and she’s stopped nursing and lost the weight (think Natalie Dormer’s tits, particularly in The Tudors), and she has these big, sexy nipples that are so much fun to play with and suck on. Her body is kind of pear-shaped: smaller up top, but it flares out at her waist and her wide hips. She has thick, muscular legs and a big, sexy ass. She doesn’t shave her pussy, though she does trim it. Some guys don’t like a bush, but it drives me wild! She hardly ever wears makeup, which I love. Read more »

The Roomate [MF] 1

Dave watched as fiery red flames engulfed his flat and smoke escaped through his open windows making its way out. Even at a distance he would feel the heat as he wiped of the sweat from his face. The firemen contained the fire before it spread to the neighbouring flats. A short circuit caused the fire, they said. Thankfully there was no one got hurt. Dave was on his way home when he saw the smoke rise up in the air from a distance, atleast a blocks away. And now all he was left with were his gym clothes and his laptop. It wasn’t an ideal male living space but nonetheless, he had lost most of his valuables. His eyes swelled with tears as he thought about how much this will set him back financially.

He needed to find a new place to stay for atleast a few days. He called up his girlfriend, Sarah who stayed with a flatmate Andrea, close to the city university. He quickly briefed her of his situation and a few moments later he was on his way to her place.

His life changed in a day. He had no idea what was about to happen in the coming few weeks. Read more »

How working as a croquet model (kind of) got me laid, and landed me a life long fetish [Exhibitionism][Voyeurism ][CFNM][MF][Masturbation][Cum on clothes]

I just used a version of this story to answer a prompt on [/r/dirtypenpals](https://www.reddit.com/r/dirtypenpals), but since she never got back to me, I thought I would reformat it for this sub instead, as it fits nicely with this month’s theme.

This is kind of a “birth of a fetish”-story, as the events hereafter really stoked my interest in exhibitionism, voyeurism and CFNM/CMNF scenarios.

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When I was a young student at the local university around 10 years ago, I fell into a gig working as a croquet model at the local school of architecture.

I was out drinking one night, when a friend to me about an acquaintance teaching a drawing class, that was mandatory for first year students at the school. She had told him she needed male models – a piece of information he relayed to me as a dare. It paid double the normal rate for the kind of random unskilled labor I did at the time, and since I’ve never been neither shy, nor willing to turn down a dare, I texted the teacher and shortly thereafter started working. Read more »

Finally Living Out My Fantasy: The Tiny Redhead [MF]

I’m a 29 year old mixed black/white guy and was a late bloomer. I didn’t start having sex until just a couple of years ago and to date I’ve only really had about 6 or 7 partners. However despite this I’ve been trying to play catch up so to speak and get more outside my comfort zone. Honestly I’m quite happy with how much I’ve learned and the cool things I’ve gotten to do so far including participating in a couple of threesomes.

Since I never really got to have sex while growing up during high school or college I’m always feeling bumbed out of what those experiences would of been like. Because of this I always had a fantasy of being with a super cute tiny 18 year old or someone who looks like one anyways and just as of this past weekend I finally was able to live that out so to speak. Read more »